JP4140698B2

JP4140698B2 - Phosphoric acid or phosphonic acid derivatives

Info

Publication number: JP4140698B2
Application number: JP2002304196A
Authority: JP
Inventors: 剛秀西; 隆一下里; 太奈良
Original assignee: Daiichi Sankyo Co Ltd
Current assignee: Daiichi Sankyo Co Ltd
Priority date: 2002-10-18
Filing date: 2002-10-18
Publication date: 2008-08-27
Anticipated expiration: 2022-10-18
Also published as: JP2004137208A

Description

【０００１】
【発明の属する技術分野】
本発明は、優れた免疫抑制作用を有するリン酸若しくはホスホン酸誘導体、リン酸若しくはホスホン酸誘導体の薬理上許容される塩又はリン酸若しくはホスホン酸誘導体のエステル、或いはそれらを有効成分として含有する医薬組成物に関する。
【０００２】
【従来の技術】
従来、リウマチやその他の自己免疫疾患等の免疫関連病の治療においては、異常な免疫反応によって生じる炎症反応に対してステロイドなどの抗炎症薬が使用されてきた。しかしながらこれらは対症療法であり根本的治療法ではない。
【０００３】
また、糖尿病、腎炎の発症においても免疫系の異常が関与することは報告されているが（例えば、非特許文献１参照）、［Kidney International, 51, 94(1997);Journal of Immunology, 157, 4691(1996)］、その異常を改善するような薬剤の開発には至っていない。
【０００４】
一方、免疫応答を抑制する方法の開発は、臓器及び細胞移植における拒絶反応を防いだり、種々の自己免疫疾患を治療及び予防する上でも極めて重要である。しかしながら、シクロスポリンＡ（ＣｓＡ）やタクロリムス（ＴＲＬ）等の従来知られている免疫抑制剤は、腎臓及び肝臓に対して毒性を示すことが知られており、そのような副作用を軽減するために、ステロイド類を併用するなどの治療が広く用いられてきたが、必ずしも副作用を示すことなく十分な免疫抑制効果を発揮するには至っていないのが現状である。
【０００５】
このような背景から、毒性が低く、優れた免疫抑制作用を有する化合物を見出すことが試みられている。
【０００６】
免疫抑制剤として、例えば、ＷＯ９４／０８９４３号公報（ＥＰ６２７４０６号公報）、ＷＯ９６／０６０６８号公報、ＷＯ９８／４５２４９号公報に記載されるアミノアルコール誘導体や、ＷＯ０２／１８３９５号公報に記載されるリン酸エステル誘導体が知られている。しかしながら、いずれの公報にも、本発明の化合物は開示されていない。
【０００７】
一方、上記一般式（Ｉ）において、Ｚ＝Ｏである本発明の化合物は、ＷＯ０２／０６２６８号公報において、ヒドロキシ化合物の保護基がリン酸エステル塩残基である化合物として開示されている。
【０００８】
【特許文献１】
ＷＯ９４／０８９４３号公報（ＥＰ６２７４０６号公報）（第３７１頁）
【特許文献２】
ＷＯ９６／０６０６８号公報（第２７１頁）
【特許文献３】
ＷＯ９８／４５２４９号公報（第８１頁）
【特許文献４】
ＷＯ０２／０６２６８号公報（第３４５頁）
【非特許文献１】
Kidney International, vol.51, 94(1997);Journal of Immunology, vol.157, 4691(1996)
【０００９】
【発明が解決しようとする課題】
上記一般式（Ｉ）を有する本発明の化合物が、毒性が低く優れた免疫抑制作用を有し、各種臓器移植又は皮膚移植での拒絶反応、全身性エリトマトーデス、慢性関節リウマチ、多発性筋炎、結合組織炎、骨格筋炎、骨関節炎、変形性関節症、皮膚筋炎、強皮症、ベーチェット病、Chron病、潰瘍性大腸炎、自己免疫性肝炎、再生不良性貧血、特発性血小板減少性紫斑病、自己免疫性溶血性貧血、多発性硬化症、自己免疫性水疱症、尋常性乾癬、血管炎症群、Wegener肉芽腫、ぶどう膜炎、シェーグレン症候群、特発性間質性肺炎、Goodpasture症候群、サルコイドーシス、アレルギー性肉芽腫性血管炎、気管支喘息、心筋炎、心筋症、大動脈炎症候群、心筋梗塞後症候群、原発性肺高血圧症、微小変化型ネフローゼ、膜性腎症、膜性増殖性腎炎、巣状糸球体硬化症、半月体形成性腎炎、重症筋無力症、炎症性ニューロパチー、アトピー性皮膚炎、慢性光線性皮膚炎、日光過敏症、蓐瘡、Ｓｙｄｅｎｈａｍ舞踏病，全身性硬化症、成人発症糖尿病、インスリン依存性糖尿病、若年性糖尿病、アテローム性動脈硬化症、糸球体腎炎、IgA腎症、尿細管間質性腎炎、原発性胆汁性肝硬変、原発性硬化性胆管炎、劇症肝炎、ウイルス性肝炎、GVHD、接触皮膚炎、敗血症等の自己免疫疾患又はその他免疫関連疾患、さらに、真菌、マイコプラズマ、ウィルス、原虫等の感染症、心不全、心肥大、不整脈、狭心症、心虚血、動脈塞栓、動脈瘤、静脈瘤、血行障害等の循環器系疾患、アルツハイマー病、痴呆、パーキンソン病、脳卒中、脳梗塞、脳虚血、鬱病、躁鬱病、統合失調症、ハンチントン舞踏病、癲癇、痙攣、多動症、脳炎、髄膜炎、食欲不振および過食等の中枢系疾患、リンパ腫、白血病、多尿、頻尿、糖尿病性網膜症等の各種疾患（特に、各種臓器移植又は皮膚移植での拒絶反応、全身性エリトマトーデス、慢性関節リウマチ、多発性硬化症、アトピー性皮膚炎等の自己免疫疾患）に有用であることを見出し、本発明を完成した。
【００１０】
従って、本発明は、毒性が低く優れた免疫抑制作用を有するリン酸若しくはホスホン酸誘導体、リン酸若しくはホスホン酸誘導体の薬理上許容される塩又はリン酸若しくはホスホン酸誘導体の薬理上許容されるエステル、或いはそれらを有効成分として含有する医薬組成物を提供することである。
【００１１】
【課題を解決するための手段】
（１）本発明のリン酸又はホスホン酸誘導体は、下記一般式（Ｉ）を有する。
【００１２】
【化４】

【００１３】
上記式中、
Ｒ¹及びＲ²は、同一又は異なって、水素原子、低級脂肪族アシル基又は低級アルコキシカルボニル基を示し、
Ｒ³及びＲa³は、同一又は異なって、水素原子又はリン酸基の保護基を示し、
Ｒ⁴は、水素原子、低級アルキル基又はヒドロキシ低級アルキル基を示し、
ｎは、１乃至６の整数を示し、
Ｘは、エチレン基、ビニレン基、エチニレン基、式−Ｄ−ＣＨ₂−を有する基（式中、Ｄは、カルボニル基、式−ＣＨ（ＯＨ）−を有する基、酸素原子、硫黄原子又は式−ＮＨ−を有する基を示す。）、Ｃ₆−Ｃ₁₀アリーレン基又は置換基群ａから選択される基で１乃至３個置換されたＣ₆−Ｃ₁₀アリーレン基を示し、
Ｙは、単結合、Ｃ₁−Ｃ₁₀アルキレン基、置換基群ａ及びｂから選択される基で１乃至３個置換されたＣ₁−Ｃ₁₀アルキレン基、炭素鎖中若しくは鎖端に酸素原子若しくは硫黄原子を有するＣ₁−Ｃ₁₀アルキレン基、又は置換基群ａ及びｂから選択される基で１乃至３個置換された、炭素鎖中若しくは鎖端に酸素原子若しくは硫黄原子を有するＣ₁−Ｃ₁₀アルキレン基を示し
Ｚは、酸素原子又はメチレン基を示し、
Ｒ⁵は、水素原子、Ｃ₃−Ｃ₁₀シクロアルキル基、Ｃ₆−Ｃ₁₀アリール基、硫黄原子、酸素原子及び／又は窒素原子を１乃至３個含む５乃至７員複素環基、置換基群ａ及びｂから選択される基で１乃至３個置換されたＣ₃−Ｃ₁₀シクロアルキル基、置換基群ａ及びｂから選択される基で１乃至３個置換されたＣ₆−Ｃ₁₀アリール基、又は置換基群ａ及びｂから選択される基で１乃至３個置換された、硫黄原子、酸素原子及び／又は窒素原子を１乃至３個含む５乃至７員複素環基を示し、
Ｒ⁶及びＲ⁷は、同一又は異なって、水素原子又は置換基群ａから選択される基を示し、
置換基群ａは、ハロゲン原子、低級アルキル基、ハロゲノ低級アルキル基、低級アルコキシ基、低級アルキルチオ基、カルボキシル基、低級アルコキシカルボニル基、ヒドロキシ基、低級脂肪族アシル基、アミノ基、モノ−低級アルキルアミノ基、ジ−低級アルキルアミノ基、低級脂肪族アシルアミノ基、シアノ基及びニトロ基からなる群を示し、
置換基群ｂは、Ｃ₃−Ｃ₁₀シクロアルキル基、Ｃ₆−Ｃ₁₀アリール基、硫黄原子、酸素原子及び／又は窒素原子を１乃至３個含む５乃至７員複素環基、置換基群ａから選択される基で１乃至３個置換されたＣ₃−Ｃ₁₀シクロアルキル基、置換基群ａから選択される基で１乃至３個置換されたＣ₆−Ｃ₁₀アリール基、及び置換基群ａから選択される基で１乃至３個置換された、硫黄原子、酸素原子及び／又は窒素原子を１乃至３個含む５乃至７員複素環基からなる群を示す。
【００１４】
但し、Ｒ⁵が水素原子であるとき、Ｙは、置換基群ａ及びｂから選択される基で１乃至３個置換されたＣ₁−Ｃ₁₀アルキレン基、炭素鎖中若しくは鎖端に酸素原子若しくは硫黄原子を有するＣ₁−Ｃ₁₀アルキレン基、又は置換基群ａ及びｂから選択される基で１乃至３個置換された、炭素鎖中若しくは鎖端に酸素原子若しくは硫黄原子を有するＣ₁−Ｃ₁₀アルキレン基を示す。
【００１５】
本発明は、式（Ｉ）を有する化合物、その薬理上許容される塩又はその薬理上許容されるエステルである。
（２）（１）において、式（Ｉ）を有する化合物が、式（Ｉ−ａ）
【００１６】
【化５】

【００１７】
［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ｒ⁶、Ｒ⁷、Ｘ、Ｙ、Ｚ及びｎは、（１）におけるものと同意義を示す。］を有する化合物、その薬理上許容される塩又はその薬理上許容されるエステル、
（３）（１）において、式（Ｉ）を有する化合物が、式（Ｉ−ｂ）
【００１８】
【化６】

【００１９】
（式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ｒ⁶、Ｒ⁷、Ｘ、Ｙ、Ｚ及びｎは、請求項１におけるものと同意義を示す。）を有する化合物、その薬理上許容される塩又はその薬理上許容されるのエステル、
（４）（１）乃至（３）から選択されるいずれか１項において、
Ｒ¹及びＲ²が、同一又は異なって、水素原子、Ｃ₁−Ｃ₄脂肪族アシル基又はＣ₁−Ｃ₄低級アルコキシカルボニル基である化合物又はその薬理上許容される塩、（５）（１）乃至（３）から選択されるいずれか１項において、
Ｒ¹及びＲ²が、同一又は異なって、水素原子又はＣ₁−Ｃ₂脂肪族アシル基又はＣ₁−Ｃ₂低級アルコキシカルボニル基である化合物又はその薬理上許容される塩、
（６）（１）乃至（３）から選択されるいずれか１項において、
Ｒ¹及びＲ²が、同一又は異なって、水素原子、アセチル基又はメトキシカルボニル基である化合物又はその薬理上許容される塩、
（７）（１）乃至（３）から選択されるいずれか１項において、
Ｒ¹及びＲ²が、水素原子である化合物又はその薬理上許容される塩、
（８）（１）乃至（７）から選択されるいずれか１項において、
Ｒ³及びＲ³ａが、同一又は異なって、水素原子、低級アルキル基、低級アルケニル基又はアラルキル基である化合物又はその薬理上許容される塩、
（９）（１）乃至（７）から選択されるいずれか１項において、
Ｒ³及びＲ³ａが、同一又は異なって、水素原子又は低級アルキル基である化合物又はその薬理上許容される塩、
（１０）（１）乃至（７）から選択されるいずれか１項において、
Ｒ³及びＲ³ａが、同一又は異なって、水素原子又はＣ₁−Ｃ₄アルキル基である化合物又はその薬理上許容される塩、
（１１）（１）乃至（７）から選択されるいずれか１項において、
Ｒ³及びＲ³ａが、同一又は異なって、水素原子、メチル基又はエチル基である化合物又はその薬理上許容される塩、
（１２）（１）乃至（７）から選択されるいずれか１項において、
Ｒ³及びＲ³ａが、水素原子である化合物又はその薬理上許容される塩、
（１３）（１）乃至（１２）から選択されるいずれか１項において、
Ｒ⁴が、Ｃ₁−Ｃ₄アルキル基又はヒドロキシＣ₁−Ｃ₄アルキル基である化合物又はその薬理上許容される塩、
（１４）（１）乃至（１２）から選択されるいずれか１項において、
Ｒ⁴が、Ｃ₁−Ｃ₂アルキル基又はヒドロキシＣ₁−Ｃ₂アルキル基である化合物又はその薬理上許容される塩、
（１５）（１）乃至（１２）から選択されるいずれか１項において、
Ｒ⁴が、Ｃ₁−Ｃ₂アルキル基である化合物又はその薬理上許容される塩、
（１６）（１）乃至（１２）から選択されるいずれか１項において、
Ｒ⁴が、メチル基である化合物又はその薬理上許容される塩、
（１７）（１）乃至（１６）から選択されるいずれか１項において、
ｎが、２又は３である化合物又はその薬理上許容される塩、
（１８）（１）乃至（１６）から選択されるいずれか１項において、
ｎが、２である化合物又はその薬理上許容される塩、
（１９）（１）乃至（１８）から選択されるいずれか１項において、
Ｘが、エチレン基、エチニレン基、式−Ｄ−ＣＨ₂−を有する基［式中、Ｄは、カルボニル基又は式−ＣＨ（ＯＨ）−を有する基を示す。］、フェニレン基、ナフチレン基、又は置換基群ａから選択される基で１乃至３個置換されたフェニレン基若しくはナフチレン基である化合物又はその薬理上許容される塩、
（２０）（１）乃至（１８）から選択されるいずれか１項において、
Ｘが、エチレン基、エチニレン基、式−ＣＯ−ＣＨ₂−を有する基、フェニレン基、又はハロゲン原子及び低級アルキル基からなる群より選択される基で１乃至３個置換されたフェニレン基である化合物又はその薬理上許容される塩、
（２１）（１）乃至（１８）から選択されるいずれか１項において、
Ｘが、エチレン基、エチニレン基又は式−ＣＯ−ＣＨ₂−を有する基である化合物又はその薬理上許容される塩、
（２２）（１）乃至（２１）から選択されるいずれか１項において、
Ｙが、Ｃ₁−Ｃ₁₀アルキレン基又は置換基群ａ及びｂから選択される基で１乃至３個置換されたＣ₁−Ｃ₁₀アルキレン基である化合物又はその薬理上許容される塩、
（２３）（１）乃至（２１）から選択されるいずれか１項において、
ＹがＣ₁−Ｃ₆アルキレン基又はヒドロキシ基で1乃至3個置換されたＣ₁−Ｃ₆アルキレン基である化合物又はその薬理上許容される塩、
（２４）（１）乃至（２１）から選択されるいずれか１項において、
ＹがＣ₁−Ｃ₅アルキレン基又はヒドロキシ基で1乃至3個置換されたＣ₁−Ｃ₅アルキレン基である化合物又はその薬理上許容される塩、
（２５）（１）乃至（２１）から選択されるいずれか１項において、
Ｙが、エチレン基、トリメチレン基、テトラメチレン基又は１個のヒドロキシ基で置換された、エチレン基、トリメチレン基若しくはテトラメチレン基である化合物又はその薬理上許容される塩、
（２６）（１）乃至（２１）から選択されるいずれか１項において、
Ｙが、エチレン基、トリメチレン基若しくはテトラメチレン基である化合物又はその薬理上許容される塩、
（２７）（１）乃至（２１）から選択されるいずれか１項において、
Ｙが、エチレン若しくはトリメチレン基である化合物又はその薬理上許容される塩、
（２８）（１）乃至（２１）から選択されるいずれか１項において、
Ｙが、炭素鎖中若しくは鎖端に酸素原子若しくは硫黄原子を有するＣ₁−Ｃ₁₀アルキレン基、又は１個のヒドロキシ基で置換された、炭素鎖中若しくは鎖端に酸素原子若しくは硫黄原子を有するＣ₁−Ｃ₁₀アルキレン基である化合物又はその薬理上許容される塩、
（２９）（１）乃至（２１）から選択されるいずれか１項において、
Ｙが、炭素鎖中若しくは鎖端に酸素原子若しくは硫黄原子を有するＣ₁−Ｃ₁₀アルキレン基である化合物又はその薬理上許容される塩、
（３０）（１）乃至（２１）から選択されるいずれか１項において、
Ｙが、炭素鎖中若しくは鎖端に酸素原子を有するＣ₁−Ｃ₁₀アルキレン基である化合物又はその薬理上許容される塩、
（３１）（１）乃至（２１）から選択されるいずれか１項において、
Ｙが、炭素鎖中若しくは鎖端に酸素原子を有するＣ₁−Ｃ₆アルキレン基である化合物又はその薬理上許容される塩、
（３２）（１）乃至（２１）から選択されるいずれか１項において、
Ｙが、式−Ｏ−ＣＨ₂−、−Ｏ−（ＣＨ₂）₂−、−Ｏ−（ＣＨ₂）₃−、−ＣＨ₂−Ｏ−、−（ＣＨ₂）₂−Ｏ−又は−（ＣＨ₂）₃−Ｏ−を有する基である化合物又はその薬理上許容される塩、
（３３）（１）乃至（２１）から選択されるいずれか１項において、
Ｙが、式−ＣＨ₂−Ｏ−又は−（ＣＨ₂）₂−Ｏ−を有する基である化合物又はその薬理上許容される塩、
（３４）（１）乃至（３３）から選択されるいずれか１項において、
Ｒ⁵が、水素原子である化合物又はその薬理上許容される塩、
（３５）（１）乃至（３３）から選択されるいずれか１項において、
Ｒ⁵が、Ｃ₃−Ｃ₁₀シクロアルキル基、Ｃ₆−Ｃ₁₀アリール基、硫黄原子、酸素原子及び／又は窒素原子を１乃至３個含む５乃至７員複素環基、置換基群a及びbから選択される基で1乃至3個置換されたＣ₃−Ｃ₁₀シクロアルキル基又は置換基群a及びbから選択される基で1乃至3個置換されたＣ₆−Ｃ₁₀アリール基である化合物又はその薬理上許容される塩、
（３６）（１）乃至（３３）から選択されるいずれか１項において、
Ｒ⁵が、Ｃ₃−Ｃ₁₀シクロアルキル基、Ｃ₆−Ｃ₁₀アリール基、又はハロゲン原子、低級アルキル基、ハロゲノ低級アルキル基、低級アルコキシ基、低級アルキルチオ基及び低級脂肪族アシル基から成る群から選択される基で1乃至3個置換されたＣ₃−Ｃ₁₀シクロアルキル基若しくはＣ₆−Ｃ₁₀アリール基である化合物又はその薬理上許容される塩、
（３７）（１）乃至（３３）から選択されるいずれか１項において、
Ｒ⁵が、Ｃ₃−Ｃ₁₀シクロアルキル基、Ｃ₆−Ｃ₁₀アリール基、又はハロゲン原子、低級アルキル基、ハロゲノ低級アルキル基、低級アルコキシ基及び低級脂肪族アシル基から成る群から選択される基で1乃至3個の置換基で置換されたＣ₃−Ｃ₁₀シクロアルキル基若しくはＣ₆−Ｃ₁₀アリール基である化合物又はその薬理上許容される塩、
（３８）（１）乃至（３３）から選択されるいずれか１項において、
Ｒ⁵が、Ｃ₅−Ｃ₆シクロアルキル基、フェニル基又はナフチル基である化合物又はその薬理上許容される塩、
（３９）（１）乃至（３３）から選択されるいずれか１項において、
Ｒ⁵が、シクロヘキシル基又はフェニル基である化合物又はその薬理上許容される塩、
（４０）（１）乃至（３９）から選択されるいずれか１項において、
Ｒ⁶及びＲ⁷が、同一又は異なって、水素原子、ハロゲン原子、低級アルキル基、ハロゲノ低級アルキル基、低級アルコキシ基又は低級アルキルチオ基である化合物又はその薬理上許容される塩、
（４１）（１）乃至（３９）から選択されるいずれか１項において、
Ｒ⁶及びＲ⁷が、水素原子である化合物又はその薬理上許容される塩、
（４２）（１）乃至（４１）から選択されるいずれか１項において、
Ｚが、酸素原子である化合物又はその薬理上許容される塩、
（４３）（１）において、下記より選択されるいずれか1つの化合物又はその薬理上許容される塩：
リン酸モノ 2-アミノ-2-メチル-4-[5-(4-シクロヘキシルブチル)チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-メチル-4-[5-(5-シクロヘキシルペンチル)チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-メチル-4-[5-(5-フェニルペンチル)チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-メチル-4-[5-(4-シクロヘキシルオキシブチル)チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-フルオロフェノキシ)ブチル]チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-メトキシフェノキシ)ブチル]チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-メチル-4-[5-(4-ベンジルオキシブチル)チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-メチル-4-[5-(4-シクロヘキシルブト-1-イニル)チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-メチル-4-[5-(4-フェニルブト-1-イニル)チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-メチル-4-[5-(5-シクロヘキシルペント-1-イニル)チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-メチル-4-[5-(5-フェニルペント-1-イニル)チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(4-フルオロフェニル)ペント-1-イニル]チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(4-メトキシフェニル)ペント-1-イニル]チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(4-メチルシクロヘキシルオキシ)プロピニル]チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(4-メチルフェノキシ)プロピニル]チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(4-エチルフェノキシ)プロピニル]チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(4-メチルチオフェノキシ)プロピニル]チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-メチル-4-[5-(4-シクロヘキシルオキシブト-1-イニル)チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-フルオロフェノキシ)ブト-1-イニル]チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-メチルフェノキシ)ブト-1-イニル]チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-メチル-4-[5-(3-シクロヘキシルメトキシプロピニル)チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-メチル-4-[5-(4-フェニルメトキシブト-1-イニル)チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-メチル-4-[5-(4-シクロヘキシルブタノイル)チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-メチル-4-[5-(4-フェニルブタノイル)チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-メチル-4-[5-(5-シクロヘキシルペンタノイル)チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-メチル-4-[5-(5-フェニルペンタノイル)チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(4-フルオロフェニル)ペンタノイル]チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-エチル-4-[5-(5-シクロヘキシルペンチル)チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-エチル-4-[5-(5-シクロヘキシルペント-1-イニル)チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-エチル-4-[5-(5-シクロヘキシルペンタノイル)チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(4-クロロフェノキシ)プロピニル]チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(3-メチルフェノキシ)プロピニル]チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(3,4-ジメチルフェノキシ)プロピニル]チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(3-メトキシフェノキシ)プロピニル]チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(3,4-ジメトキシフェノキシ)プロピニル]チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(3,5-ジメトキシフェノキシ)プロピニル]チオフェン-2-イル] ブチルエステル、
リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(3-アセチルフェノキシ)プロピニル]チオフェン-2-イル] ブチルエステル及び
リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(4-アセチルフェノキシ)プロピニル]チオフェン-2-イル] ブチルエステル。
（４４）（１）において、下記より選択されるいずれか1つの化合物又はその薬理上許容される塩：
3-アミノ-3-メチル-5-[5-(4-シクロヘキシルブチル)チオフェン-2-イル]ペンチルホスホン酸、
3-アミノ-3-メチル-5-[5-(5-シクロヘキシルペンチル)チオフェン-2-イル]ペンチルホスホン酸、
3-アミノ-3-メチル-5-[5-(5-フェニルペンチル)チオフェン-
2-イル]ペンチルホスホン酸、
3-アミノ-3-メチル-5-[5-(4-シクロヘキシルオキシブチル)チオフェン-2-イル]ペンチルホスホン酸、
3-アミノ-3-メチル-5-[5-[4-(4-フルオロフェノキシ)ブチル]チオフェン-2-イル]ペンチルホスホン酸、
3-アミノ-3-メチル-5-[5-[4-(4-メトキシフェノキシ)ブチル]チオフェン-2-イル]ペンチルホスホン酸、
3-アミノ-3-メチル-5-[5-(4-ベンジルオキシブチル)チオフェン-2-イル]ペンチルホスホン酸、
3-アミノ-3-メチル-5-[5-(4-シクロヘキシルブタノイル)チオフェン-2-イル]ペンチルホスホン酸、
3-アミノ-3-メチル-5-[5-(4-フェニルブタノイル)チオフェン-2-イル]ペンチルホスホン酸、
3-アミノ-3-メチル-5-[5-(5-シクロヘキシルペンタノイル)チオフェン-2-イル]ペンチルホスホン酸、
3-アミノ-3-メチル-5-[5-(5-フェニルペンタノイル)チオフェン-2-イル]ペンチルホスホン酸、
3-アミノ-3-メチル-5-[5-[5-(4-フルオロフェニル)ペンタノイル]チオフェン-2-イル]ペンチルホスホン酸、
3-アミノ-3-エチル-5-[5-(5-シクロヘキシルペンチル)チオフェン-2-イル]ペンチルホスホン酸及び
2-アミノ-2-エチル-4-[5-(5-シクロヘキシルペンタノイル)チオフェン-2-イル]ペンチルホスホン酸。
【００２０】
上記化合物（Ｉ）において、（２）乃至（３）；（４）乃至（７）；（８）乃至（１２）；（１３）乃至（１６）；（１７）乃至（１８）；（１９）乃至（２１）；（２２）乃至（３３）；(３４)乃至（３９）；(４０)乃至（４１）；並びに（４２）から成る群から選択されるいずれか一項を任意に組み合わせた化合物も好適である。
【００２１】
上記式（Ｉ）中、Ｒ⁵及び置換基群ｂの定義における「Ｃ₆−Ｃ₁₀アリール基」、「置換基群ａから選択される基で１乃至３個置換されたＣ₆−Ｃ₁₀アリール基」及び「置換基群ａ及びｂから選択される基で１乃至３個置換されたＣ₆−Ｃ₁₀アリール基」のアリール部分は、例えば、フェニル、インデニル又はナフチルであり得、好適には、フェニル又はナフチル基であり、最も好適には、フェニル基である。
【００２２】
Ｘの定義における「Ｃ₆−Ｃ₁₀アリーレン基」、「置換基群ａから選択される基で１乃至３個置換されたＣ₆−Ｃ₁₀アリーレン基」及び「置換基群ａ及びｂから選択される基で１乃至３個置換されたＣ₆−Ｃ₁₀アリーレン基」のアリーレン部分は、例えば、フェニレン、インデニレン又はナフチレンであり得、好適には、フェニレン又はナフチレン基であり、最も好適には、フェニレン基である。
【００２３】
Ｙの定義における「Ｃ₁−Ｃ₁₀アルキレン基」及び「置換基群ａ及びｂから選択される基で１乃至３個置換されたＣ₁−Ｃ₁₀アルキレン基」のＣ₁−Ｃ₁₀アルキレン部分は、例えば、メチレン、メチルメチレン、エチレン、プロピレン、トリメチレン、１−メチルエチレン、テトラメチレン、１−メチルトリメチレン、２−メチルトリメチレン、３−メチルトリメチレン、１−メチルプロピレン、１，１−ジメチルエチレン、ペンタメチレン、１−メチルテトラメチレン、２−メチルテトラメチレン、３−メチルテトラメチレン、４−メチルテトラメチレン、１，１−ジメチルトリメチレン、２，２−ジメチルトリメチレン、３，３−ジメチルトリメチレン、ヘキサメチレン、１−メチルペンタメチレン、２−メチルペンタメチレン、３−メチルペンタメチレン、４−メチルペンタメチレン、５−メチルペンタメチレン、１，１−ジメチルテトラメチレン、２，２−ジメチルテトラメチレン、３，３−ジメチルテトラメチレン、４，４−ジメチルテトラメチレン、ヘプタメチレン、１−メチルヘキサメチレン、２−メチルヘキサメチレン、５−メチルヘキサメチレン、３−エチルペンタメチレン、オクタメチレン、２−メチルヘプタメチレン、５−メチルヘプタメチレン、２−エチルヘキサメチレン、２−エチル−３−メチルペンタメチレン、３−エチル−２−メチルペンタメチレン、ノナメチレン、２−メチルオクタメチレン、７−メチルオクタメチレン、４−エチルヘプタメチレン、３−エチル−２−メチルヘキサメチレン、２−エチル−１−メチルヘキサメチレン、デカメチレン基のような炭素数１乃至１０個の直鎖又は分枝鎖アルキレン基であり得、好適には、Ｃ₁−Ｃ₆アルキレン基であり、更に好適には、Ｃ₁−Ｃ₅アルキレン基であり、より更に好適には、エチレン、トリメチレン又はテトラメチレン基であり、最も好適には、エチレン又はトリメチレン基である。
【００２４】
Ｙの定義における「炭素鎖中若しくは鎖端に酸素原子若しくは硫黄原子を有するＣ₁−Ｃ₁₀アルキレン基」及び「置換基群ａ及びｂから選択される基で１乃至３個置換された、炭素鎖中若しくは鎖端に酸素原子若しくは硫黄原子を有するＣ₁−Ｃ₁₀アルキレン基」の「炭素鎖中若しくは鎖端に酸素原子若しくは硫黄原子を有するＣ₁−Ｃ₁₀アルキレン」部分は、上記「Ｃ₁−Ｃ₁₀アルキレン基」の鎖端若しくは鎖中に酸素原子若しくは硫黄原子を有する基であり、例えば、式−Ｏ−ＣＨ₂−、−Ｏ−（ＣＨ₂）₂−、−Ｏ−（ＣＨ₂）₃−、−Ｏ−（ＣＨ₂）₄−、−Ｏ−（ＣＨ₂）₅−、−Ｏ−（ＣＨ₂）₆−、−Ｏ−（ＣＨ₂）₇−、−Ｏ−（ＣＨ₂）₈−、−Ｏ−（ＣＨ₂）₉−、−Ｏ−（ＣＨ₂）₁₀−、−ＣＨ₂−Ｏ−ＣＨ₂−、−ＣＨ₂−Ｏ−（ＣＨ₂）₂−、−ＣＨ₂−Ｏ−（ＣＨ₂）₃−、−ＣＨ₂−Ｏ−（ＣＨ₂）₄−、−（ＣＨ₂）₂−Ｏ−ＣＨ₂−、−（ＣＨ₂）₂−Ｏ−（ＣＨ₂）₂−、−（ＣＨ₂）₂−Ｏ−（ＣＨ₂）₃−、−（ＣＨ₂）₂−Ｏ−（ＣＨ₂）₄−、−（ＣＨ₂）₃−Ｏ−ＣＨ₂−、−（ＣＨ₂）₃−Ｏ−（ＣＨ₂）₂−、−（ＣＨ₂）₃−Ｏ−（ＣＨ₂）₃−、−（ＣＨ₂）₄−Ｏ−ＣＨ₂−、−（ＣＨ₂）₄−Ｏ−（ＣＨ₂）₂−、−（ＣＨ₂）₅−Ｏ−ＣＨ₂−、−ＣＨ₂−Ｏ−、−（ＣＨ₂）₂−Ｏ−、−（ＣＨ₂）₃−Ｏ−、−（ＣＨ₂）₄−Ｏ−、−（ＣＨ₂）₅−Ｏ−、−（ＣＨ₂）₆−Ｏ−、−（ＣＨ₂）₇−Ｏ−、−（ＣＨ₂）₈−Ｏ−、−（ＣＨ₂）₉−Ｏ−、−（ＣＨ₂）₁₀−Ｏ−、−Ｓ−ＣＨ₂−、−Ｓ−（ＣＨ₂）₂−、−Ｓ−（ＣＨ₂）₃−、−Ｓ−（ＣＨ₂）₄−、−Ｓ−（ＣＨ₂）₅−、−Ｓ−（ＣＨ₂）₆−、−Ｓ−（ＣＨ₂）₇−、−Ｓ−（ＣＨ₂）₈−、−Ｓ−（ＣＨ₂）₉−、−Ｓ−（ＣＨ₂）₁₀−、−ＣＨ₂−Ｓ−ＣＨ₂−、−ＣＨ₂−Ｓ−（ＣＨ₂）₂−、−ＣＨ₂−Ｓ−（ＣＨ₂）₃−、−ＣＨ₂−Ｓ−（ＣＨ₂）₄−、−（ＣＨ₂）₂−Ｓ−ＣＨ₂−、−（ＣＨ₂）₂−Ｓ−（ＣＨ₂）₂−、−（ＣＨ₂）₂−Ｓ−（ＣＨ₂）₃−、−（ＣＨ₂）₂−Ｓ−（ＣＨ₂）₄−、−（ＣＨ₂）₃−Ｓ−ＣＨ₂−、−（ＣＨ₂）₃−Ｓ−（ＣＨ₂）₂−、−（ＣＨ₂）₃−Ｓ−（ＣＨ₂）₃−、−（ＣＨ₂）₄−Ｓ−ＣＨ₂−、−（ＣＨ₂）₄−Ｓ−（ＣＨ₂）₂−、−（ＣＨ₂）₅−Ｓ−ＣＨ₂−、−ＣＨ₂−Ｓ−、−（ＣＨ₂）₂−Ｓ−、−（ＣＨ₂）₃−Ｓ−、−（ＣＨ₂）₄−Ｓ−、−（ＣＨ₂）₅−Ｓ−、−（ＣＨ₂）₆−Ｓ−、−（ＣＨ₂）₇−Ｓ−、−（ＣＨ₂）₈−Ｓ−、−（ＣＨ₂）₉−Ｓ−又は−（ＣＨ₂）₁₀−Ｓ−を有する基であり得、好適には、炭素鎖中若しくは鎖端に酸素原子を有するＣ₁−Ｃ₆アルキレン基であり、更に好適には、式−Ｏ−ＣＨ₂−、−Ｏ−（ＣＨ₂）₂−、−Ｏ−（ＣＨ₂）₃−、−ＣＨ₂−Ｏ−、−（ＣＨ₂）₂−Ｏ−又は−（ＣＨ₂）₃−Ｏ−を有する基であり、最も好適には、式−ＣＨ₂−Ｏ−又は−（ＣＨ₂）₂−Ｏ−を有する基である。
【００２５】
Ｒ⁵及び置換基群ｂの定義における「Ｃ₃−Ｃ₁₀シクロアルキル基」、「置換基群ａから選択される基で１乃至３個置換されたＣ₃−Ｃ₁₀シクロアルキル基」及び「置換基群ａ及びｂから選択される基で１乃至３個置換されたＣ₃−Ｃ₁₀シクロアルキル基」のＣ₃−Ｃ₁₀シクロアルキル部分は、ベンゼン環のような他の環式基と縮環していてもよく、例えば、シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル、シクロヘプチル、ノルボルニル、アダマンチル又はインダニルであり得、好適には、Ｃ₅−Ｃ₆シクロアルキル基であり、最も好適には、シクロヘキシル基である。
【００２６】
Ｒ⁵及び置換基群ｂの定義における「硫黄原子、酸素原子又は／及び窒素原子を１乃至３個含む５乃至７員複素環基」、「置換基群ａから選択される基で１乃至３個置換された、硫黄原子、酸素原子又は／及び窒素原子を１乃至３個含む５乃至７員複素環基」及び「置換基群ａ及びｂから選択される基で１乃至３個置換された、硫黄原子、酸素原子又は／及び窒素原子を１乃至３個含む５乃至７員複素環基複素環基」の硫黄原子、酸素原子又は／及び窒素原子を１乃至３個含む５乃至７員複素環基部分は、硫黄原子、酸素原子又は／及び窒素原子を１乃至３個含む５乃至７員の芳香族、又は部分若しくは完全還元型の飽和複素環基を示し、例えば、フリル、チエニル、ピロリル、アゼピニル、ピラゾリル、イミダゾリル、オキサゾリル、イソキサゾリル、チアゾリル、イソチアゾリル、１，２，３−オキサジアゾリル、トリアゾリル、テトラゾリル、チアジアゾリル、ピラニル、ピリジル、ピリダジニル、ピリミジニル、ピラジニル、テトラヒドロピラニル、モルホリニル、チオモルホリニル、ピロリジニル、ピロリニル、イミダゾリジニル、ピラゾリジニル、ピペリジニル、ピペラジニル、オキサゾリジニル、イソキサゾリジニル、チアゾリジニル又はピラゾリジニルであり得、好適には、硫黄原子、酸素原子又は／及び窒素原子を１乃至３個含む５乃至６員芳香族複素環基であり、更に好適には、フリル、チエニル又はピロリルであり、より更に好適には、フリル又はチエニルであり、最も好適には、チエニルである。
【００２７】
尚、上記「芳香族複素環基」は、他の環式基と縮環していてもよく、それらは、例えば、ベンゾチエニル、イソベンゾフラニル、クロメニル、キサンテニル、フェノキサチイニル、インドリジニル、イソインドリル、インドリル、インダゾリル、プリニル、キノリジニル、イソキノリル、キノリル、フタラジニル、ナフチリジニル、キノキサリニル、キナゾリニル、カルバゾリル、カルボリニル、アクリジニル又はイソインドリニルであり得、好適には、ベンゾチエニル基である。
【００２８】
置換基群ａの定義における「ハロゲン原子」は、フッ素、塩素、臭素又はヨウ素原子であり、好適には、フッ素原子又は塩素原子である。
【００２９】
Ｒ⁴及び置換基群ａの定義における「低級アルキル基」は、例えば、メチル、エチル、プロピル、イソプロピル、ブチル、イソブチル、ｓ−ブチル、ｔ−ブチル、ペンチル、イソペンチル、２−メチルブチル、ネオペンチル、１−エチルプロピル、ヘキシル、イソヘキシル、４−メチルペンチル、３−メチルペンチル、２−メチルペンチル、１−メチルペンチル、３，３−ジメチルブチル、２，２−ジメチルブチル、１，１−ジメチルブチル、１，２−ジメチルブチル、１，３−ジメチルブチル、２，３−ジメチルブチル、１−エチルブチル、２−エチルブチル基のような炭素数１乃至６個の直鎖又は分枝鎖アルキル基であり得、好適にはＣ₁−Ｃ₄アルキル基であり、更に好適には、Ｃ₁−Ｃ₂アルキル基であり、最も好適には、メチル基である。
【００３０】
Ｒ⁴の定義における「ヒドロキシ低級アルキル基」は、前記「低級アルキル基」にヒドロキシ基が置換した基を示し、例えば、ヒドロキシメチル、２−ヒドロキシエチル、３−ヒドロキシプロピル、４−ヒドロキシブチル、５−ヒドロキシペンチル、６−ヒドロキシヘキシル基のようなヒドロキシＣ₁−Ｃ₆アルキル基であり得、好適には、ヒドロキシＣ₁−Ｃ₄アルキル基であり、更に好適には、ヒドロキシメチル又は２−ヒドロキシエチル基であり、最も好適にはヒドロキシメチル基である。
【００３１】
置換基群ａの定義における「ハロゲノ低級アルキル基」は、前記「低級アルキル基」にハロゲン原子が置換した基を示し、例えば、トリフルオロメチル、トリクロロメチル、ジフルオロメチル、ジクロロメチル、ジブロモメチル、フルオロメチル、２，２，２−トリフルオロエチル、２，２，２−トリクロロエチル、２−ブロモエチル、２−クロロエチル、２−フルオロエチル、２−ヨ−ドエチル、３−クロロプロピル、４−フルオロブチル、６−ヨ−ドヘキシル、２，２−ジブロモエチル基のようなハロゲノＣ₁−Ｃ₆アルキル基であり得、好適には、ハロゲノＣ₁−Ｃ₄アルキル基であり、更に好適には、トリフルオロメチル、トリクロロメチル、２，２，２−トリフルオロエチル又は２，２，２−トリクロロエチルであり、最も好適にはトリフルオロメチル基である。
【００３２】
置換基群ａの定義における「低級アルコキシ基」は、前記「低級アルキル基」が酸素原子に結合した基を示し、例えば、メトキシ、エトキシ、プロポキシ、イソプロポキシ、ブトキシ、イソブトキシ、ｓ−ブトキシ、ｔ−ブトキシ、ペントキシ、イソペントキシ、２−メチルブトキシ、１−エチルプロポキシ、２−エチルプロポキシ、ネオペントキシ、ヘキシルオキシ、４−メチルペントキシ、３−メチルペントキシ、２−メチルペントキシ、３，３−ジメチルブトキシ、２，２−ジメチルブトキシ、１，１−ジメチルブトキシ、１，２−ジメチルブトキシ、１，３−ジメチルブトキシ、２，３−ジメチルブトキシ基のような炭素数１乃至６個の直鎖又は分枝鎖アルコキシ基であり得、好適には、Ｃ₁−Ｃ₄アルコキシ基であり、更に好適には、Ｃ₁−Ｃ₂アルコキシ基であり、最も好適には、メトキシ基である。
【００３３】
置換基群ａの定義における「低級アルキルチオ基」は、前記「低級アルキル基」が硫黄原子に結合した基を示し、例えば、メチルチオ、エチルチオ、プロピルチオ、イソプロピルチオ、ブチルチオ、イソブチルチオ、ｓ−ブチルチオ、ｔ−ブチルチオ、ペンチルチオ、イソペンチルチオ、２−メチルブチルチオ、ネオペンチルチオ、ヘキシルチオ、４−メチルペンチルチオ、３−メチルペンチルチオ、２−メチルペンチルチオ、３，３−ジメチルブチルチオ、２，２−ジメチルブチルチオ、１，１−ジメチルブチルチオ、１，２−ジメチルブチルチオ、１，３−ジメチルブチルチオ、２，３−ジメチルブチルチオ基のような炭素数１乃至６個の直鎖又は分枝鎖アルキルチオ基であり得、好適には、Ｃ₁−Ｃ₄アルキルチオ基であり、更に好適には、Ｃ₁−Ｃ₂アルキルチオ基であり、最も好適には、メチルチオ基である。
【００３４】
Ｒ¹、Ｒ²及び置換基群ａの定義における「低級アルコキシカルボニル基」は、前記「低級アルコキシ基」がカルボニル基に結合した基を示し、例えば、メトキシカルボニル、エトキシカルボニル、プロポキシカルボニル、イソプロポキシカルボニル、ブトキシカルボニル、イソブトキシカルボニル、ｓ−ブトキシカルボニル、ｔ−ブトキシカルボニル、ペントキシカルボニル、イソペントキシカルボニル、２−メチルブトキシカルボニル、ネオペントキシカルボニル、ヘキシルオキシカルボニル、４−メチルペントキシカルボニル、３−メチルペントキシカルボニル、２−メチルペントキシカルボニル、３，３−ジメチルブトキシカルボニル、２，２−ジメチルブトキシカルボニル、１，１−ジメチルブトキシカルボニル、１，２−ジメチルブトキシカルボニル、１，３−ジメチルブトキシカルボニル、２，３−ジメチルブトキシカルボニル基のような炭素数１乃至６個の直鎖又は分枝鎖アルコキシカルボニル基であり得、好適には、Ｃ₁−Ｃ₄アルコキシカルボニル基であり、更に好適には、Ｃ₁−Ｃ₂アルコキシカルボニル基であり、最も好適には、メトキシカルボニル基である。
【００３５】
Ｒ¹、Ｒ²及び置換基群ａの定義における「低級脂肪族アシル基」は、水素原子又は飽和若しくは不飽和の鎖状炭化水素基がカルボニル基に結合した基を示し、例えば、ホルミル、アセチル、プロピオニル、ブチリル、イソブチリル、バレリル、イソバレリル、ピバロイル、ヘキサノイル、ヘプタノイル、オクタノイル、アクリロイル、メタクリロイル、クロトノイル基のような炭素数１乃至８個の直鎖又は分枝鎖低級脂肪族アシル基であり得、好適には、Ｃ₁−Ｃ₄低級脂肪族アシル基であり、更に好適には、アセチル又はプロピオニル基であり、最も好適には、アセチル基である。
【００３６】
置換基群ａの定義における「モノ−低級アルキルアミノ基」は、前記「低級アルキル基」が１個アミノ基に結合した基を示し、例えば、メチルアミノ、エチルアミノ、プロピルアミノ、イソプロピルアミノ、ブチルアミノ、イソブチルアミノ、ｓ−ブチルアミノ、ｔ−ブチルアミノ、ペンチルアミノ、イソペンチルアミノ、２−メチルブチルアミノ、ネオペンチルアミノ、１−エチルプロピルアミノ、ヘキシルアミノ、イソヘキシルアミノ、４−メチルペンチルアミノ、３−メチルペンチルアミノ、２−メチルペンチルアミノ、１−メチルペンチルアミノ、３，３−ジメチルブチルアミノ、２，２−ジメチルブチルアミノ、１，１−ジメチルブチルアミノ、１，２−ジメチルブチルアミノ、１，３−ジメチルブチルアミノ、２，３−ジメチルブチルアミノ、２−エチルブチルアミノ基のようなモノ−Ｃ₁−Ｃ₆アルキルアミノ基であり得、好適には、モノ−Ｃ₁−Ｃ₄アルキルアミノ基であり、更に好適には、モノ−Ｃ₁−Ｃ₂アルキルアミノ基であり、最も好適には、メチルアミノ基である。
【００３７】
置換基群ａの定義における「ジ−低級アルキルアミノ基」は、前記「低級アルキル基」が２個アミノ基に結合した基を示し、例えば、ジメチルアミノ、ジエチルアミノ、Ｎ−エチル−Ｎ−メチルアミノ、ジプロピルアミノ、ジブチルアミノ、ジペンチルアミノ、ジヘキシルアミノ基のようなジ−Ｃ₁−Ｃ₆アルキルアミノ基であり得、好適には、ジ−Ｃ₁−Ｃ₄アルキルアミノ基であり、更に好適には、ジ−Ｃ₁−Ｃ₂アルキルアミノ基であり、最も好適には、ジメチルアミノ基である。
【００３８】
上記式中、置換基群ａの定義における「低級脂肪族アシルアミノ基」は、前記「低級脂肪族アシル基」がアミノ基に結合した基を示し、例えば、ホルミルアミノ、アセチルアミノ、プロピオニルアミノ、ブチリルアミノ、イソブチリルアミノ、バレリルアミノ、イソバレリルアミノ、ピバロイルアミノ、ヘキサノイルアミノ、アクリロイルアミノ、メタクリロイルアミノ、クロトノイルアミノ基のような炭素数１乃至７個の直鎖又は分枝鎖低級脂肪族アシルアミノ基であり得、好適には、Ｃ₁−Ｃ₄脂肪族アシルアミノ基であり、更に好適には、アセチルアミノ又はプロピオニルアミノ基であり、最も好適には、アセチルアミノ基である。
【００３９】
Ｒ³及びＲａ³の定義における「リン酸基の保護基」は、例えば、
メチル、エチル、イソプロピル、ブチルのような低級アルキル基、
２−シアノエチル、２−シアノ−１，１−ジメチルエチルのようなシアノ基で置換された低級アルキル基、
２−（メチルジフェニルシリル）エチル、２−トリメチルシリルエチルのような低級アルキル又は低級アルキルとアリールとでトリ置換されたシリル基で置換された低級アルキル基、
２−（２’−ピリジル）エチル、２−（４’−ピリジル）エチルのようなヘテロシクリルで置換された低級アルキル基、
２−フェニルチオエチル、２−（４’−ニトロフェニルチオ）エチル、２−（４’−トリフェニルメチルフェニルチオ）エチルのようなアリールチオで置換された低級アルキル基
２−（ｔ−ブチルスルホニル）エチル、２−（フェニルスルホニル）エチル、２−（ベンジルスルホニル）エチルのようなアルキルスルホニル、アリールスルホニル又はアリールアルキルスルホニルで置換された低級アルキル基、
２，２，２−トリクロロエチル、２，２，２−トリクロロエチル−１，１−ジメチルエチル、２，２，２−トリブロモエチル、２，３−ジブロモプロピル、２，２，２−トリフルオロエチルのようなハロゲノ低級アルキル基；
ベンジル、フェネチル、３−フェニルプロピル、α−ナフチルメチル、β−ナフチルメチル、ジフェニルメチル、トリフェニルメチル、α−ナフチルジフェニルメチル、９−アンスリルメチルのような１〜３個のアリール基で置換された低級アルキル基、ｏ−ニトロベンジル、４−ニトロベンジル、２，４−ジニトロベンジル、４−クロロベンジル、４−クロロ−２−ニトロベンジル、４−アシルオキシベンジルのようなニトロ、ハロまたは低級脂肪族アシルでアリール環が置換されたアリール基で置換された低級アルキル基、２−ニトロフェニルエチルのような置換基を有するアリール基で置換された低級アルキル基、９−フルオレニルメチルのようなフルオレニル基で置換された低級アルキル基などのアラルキル類；
アリル、プロペニルのような低級アルケニル基、
４−シアノ−２−ブテニルのようなシアノで置換された低級アルケニル基；
フェニルのようなアリール基、
２−メチルフェニル、２，６−ジメチルフェニル、２−クロロフェニル、４−クロロフェニル、２，４−ジクロロフェニル、２，５−ジクロロフェニル、２，６−ジクロロフェニル、２−ブロモフェニル、４−ニトロフェニル、３，５−ジニトロフェニル、４−クロロ−２−ニトロフェニル、２−メトキシ−５−ニトロフェニルのような低級アルキル、アリール基でトリ置換された低級アルキル、低級アルコキシ、ニトロ又はハロで置換されたアリール基；
並びに
アニリデイト、４−トリフェニルメチルアニリデイト、［Ｎ−（２−トリチロキシ）エチル］アニリデイト、ｐ−（N，N−ジメチルアミノ）アニリデイト、３−（N，N−ジエチルアミノメチル）アニリデイトのようなアミド類
である。
【００４０】
「リン酸基の保護基」は、好適には、低級アルキル基、低級アルケニル基または１−３個のフェニル若しくはナフチルで置換されたメチル基であり、更に好適には、メチル基、エチル基、アリル基またはベンジル基であり、最も好適には、メチル基又はエチル基である。
【００４１】
Ｒ⁵の定義における「置換基群ａ及びｂから選択される基で１乃至３個置換されたＣ₃−Ｃ₁₀シクロアルキル基」の具体例としては、例えば、２−フルオロシクロプロピル、２−クロロシクロプロピル、２−若しくは３−フルオロシクロペンチル、２−若しくは３−クロロシクロペンチル、２−，３−若しくは４−フルオロシクロヘキシル、２−，３−若しくは４−クロロシクロヘキシル、２−，３−若しくは４−ブロモシクロヘキシル、２−，３−若しくは４−ヨ−ドシクロヘキシル、２−メチルシクロプロピル、２−エチルシクロプロピル、２−若しくは３−メチルシクロペンチル、２−若しくは３−エチルシクロペンチル、２−，３−若しくは４−メチルシクロヘキシル、２−，３−若しくは４−エチルシクロヘキシル、２−トリフルオロメチルシクロプロピル、２−若しくは３−トリフルオロメチルシクロブチル、２−若しくは３−トリフルオロメチルシクロペンチル、２−，３−若しくは４−トリフルオロメチルシクロヘキシル、２−メトキシシクロプロピル、２−若しくは３−メトキシシクロブチル、２−若しくは３−メトキシシクロペンチル、２−，３−若しくは４−メトキシシクロヘキシル、２−，３−若しくは４−エトキシシクロヘキシル、２−，３−若しくは４−プロポキシシクロヘキシル、２−，３−若しくは４−イソプロポキシシクロヘキシル、２−，３−若しくは４−（１−エチルプロポキシ）シクロヘキシル、２−，３−若しくは４−（２−エチルプロポキシ）シクロヘキシル、２−カルボキシシクロプロピル、２−若しくは３−カルボキシシクロペンチル、２−，３−若しくは４−カルボキシシクロヘキシル、２−メトキシカルボニルシクロプロピル、２−若しくは３−メトキシカルボニルシクロペンチル、２−，３−若しくは４−メトキシカルボニルシクロヘキシル、２−ヒドロキシシクロプロピル、２−若しくは３−ヒドロキシシクロペンチル、２−，３−若しくは４−ヒドロキシシクロヘキシル、２−ホルミルシクロプロピル、２−若しくは３−ホルミルシクロペンチル、２−，３−若しくは４−ホルミルシクロヘキシル、２−アセチルシクロプロピル、２−若しくは３−アセチルシクロペンチル、２−，３−若しくは４−アセチルシクロヘキシル、２−アミノシクロプロピル、２−若しくは３−アミノシクロペンチル、２−，３−若しくは４−アミノシクロヘキシル、２−メチルアミノシクロプロピル、２−若しくは３−メチルアミノシクロブチル、２−若しくは３−メチルアミノシクロペンチル、２−，３−若しくは４−メチルアミノシクロヘキシル、２−ジメチルアミノシクロプロピル、２−若しくは３−ジメチルアミノシクロブチル、２−若しくは３−ジメチルアミノシクロペンチル、２−，３−若しくは４−ジメチルアミノシクロヘキシル、２−シアノシクロプロピル、２−若しくは３−シアノシクロペンチル、２−，３−若しくは４−シアノシクロヘキシル、２−若しくは３−シクロヘキシルシクロペンチル、２−，３−若しくは４−シクロヘキシルシクロヘキシル、２−フェニルシクロプロピル、２−若しくは３−フェニルシクロペンチル、２−，３−若しくは４−フェニルシクロヘキシル、３，４−ジフルオロシクロヘキシル、３，４−ジクロロシクロヘキシル、２，３−ジメトキシシクロヘキシル、３，４−ジメトキシシクロヘキシル、３，５−ジメトキシシクロヘキシル、３，４，５−トリメトキシシクロヘキシル基であり得、好適には、１乃至３個置換されたＣ₃−Ｃ₁₀シクロアルキル基（該置換基は、ハロゲン原子、低級アルキル基、ハロゲノ低級アルキル基、低級アルコキシ基、低級アルキルチオ基及び低級脂肪族アシル基から成る群から選択される基である。）であり、更に好適には、１乃至３個置換されたＣ₃−Ｃ₁₀シクロアルキル基（該置換基は、ハロゲン原子、低級アルキル基、ハロゲノ低級アルキル基、低級アルコキシ基及び低級脂肪族アシル基から成る群から選択される基である。）であり、より更に好適には、１個置換されたシクロヘキシル基（該置換基は、ハロゲン原子、低級アルキル基、ハロゲノ低級アルキル基、低級アルコキシ基及び低級脂肪族アシル基から成る群から選択される基である。）であり、最も好適には、１個置換されたシクロヘキシル基（該置換基は、フッ素原子、塩素原子、メチル、トリフルオロメチル、メトキシ及びアセチル基から成る群から選択される基である。）である。
【００４２】
Ｒ⁵の定義における「置換基群ａ及びｂから選択される基で１乃至３個置換されたＣ₆−Ｃ₁₀アリール基」の具体例は、例えば、２−，３−若しくは４−フルオロフェニル、２−，３−若しくは４−クロロフェニル、２−，３−若しくは４−ブロモフェニル、２−，３−若しくは４−ヨ−ドフェニル、２−，３−若しくは４−メチルフェニル、２−，３−若しくは４−エチルフェニル、２−，３−若しくは４−プロピルフェニル、２−，３−若しくは４−ブチルフェニル、２−，３−若しくは４−ペンチルフェニル、２−，３−若しくは４−トリフルオロメチルフェニル、２−，３−若しくは４−メトキシフェニル、２−，３−若しくは４−エトキシフェニル、２−，３−若しくは４−プロポキシフェニル、２−，３−若しくは４−イソプロポキシフェニル、２−，３−若しくは４−ブトキシフェニル、２−，３−若しくは４−（１−エチルプロポキシ）フェニル、２−，３−若しくは４−（２−エチルプロポキシ）フェニル、２−，３−若しくは４−メチルチオフェニル、２−，３−若しくは４−エチルチオフェニル、２−，３−若しくは４−カルボキシフェニル、２−，３−若しくは４−メトキシカルボニルフェニル、２−，３−若しくは４−エトキシカルボニルフェニル、２−，３−若しくは４−ヒドロキシフェニル、２−，３−若しくは４−ホルミルフェニル、２−，３−若しくは４−アセチルフェニル、２−，３−若しくは４−アミノフェニル、２−，３−若しくは４−メチルアミノフェニル、２−，３−若しくは４−ジメチルアミノフェニル、２−，３−若しくは４−シアノフェニル、２−，３−若しくは４−シクロペンチルフェニル、２−，３−若しくは４−シクロヘキシルフェニル、２−，３−若しくは４−ビフェニル、２，４−ジフルオロフェニル、３，４−ジフルオロフェニル、３，５−ジフルオロフェニル、２，４−ジクロロフェニル、３，４−ジクロロフェニル、３，５−ジクロロフェニル、３，４−ジブロモフェニル、２，３−ジメチルフェニル、３，４−ジメチルフェニル、３，５−ジメチルフェニル、２，３−ジメトキシフェニル、３，４−ジメトキシフェニル、３，５−ジメトキシフェニル、３，４，５−トリメトキシフェニル、３−フルオロ−４−メトキシフェニル、４−メチル−２−メトキシフェニル、６−フルオロ−４−メチル−２−メトキシフェニル、５−フルオロインデン−３−イル、５−フルオロインデン−３−イル、５−メチルインデン−３−イル、５−メトキシインデン−３−イル、５−フルオロインデン−２−イル、５−クロロインデン−２−イル、５−メチルインデン−２−イル、５−メトキシインデン−２−イル、５−ヒドロキシインデン−３−イル、５−ニトロインデン−３−イル、５−シクロヘキシルインデン−３−イル、５−フェニルインデン−３−イル、５−フェノキシインデン−３−イル、５−ベンジルオキシインデン−３−イル、５−フェニルチオインデン−３−イル、５−ヒドロキシインデン−２−イル、５−ニトロインデン−２−イル、５−シクロヘキシルインデン−２−イル、５−フェニルインデン−２−イル、５−フルオロナフタレン−２−イル、５−フルオロナフタレン−２−イル、５−メチルナフタレン−２−イル、５−メトキシナフタレン−２−イル、５−フルオロナフタレン−１−イル、５−フルオロナフタレン−１−イル、５−メチルナフタレン−１−イル、５−メトキシナフタレン−１−イル、５−ヒドロキシナフタレン−２−イル、５−ニトロナフタレン−２−イル、５−シクロヘキシルナフタレン−２−イル、５−フェニルナフタレン−２−イル、５−フェノキシナフタレン−２−イル、５−ベンジルオキシナフタレン−２−イル、５−フェニルチオナフタレン−２−イル、５−ヒドロキシナフタレン−１−イル、５−ニトロナフタレン−１−イル、５−シクロヘキシルナフタレン−１−イル、５−フェニルナフタレン−１−イル基であり、好適には、１乃至３個置換されたＣ₆−Ｃ₁₀アリール基（該置換基は、ハロゲン原子、低級アルキル基、ハロゲノ低級アルキル基、低級アルコキシ基、低級アルキルチオ基及び低級脂肪族アシル基から成る群から選択される基である。）であり、更に好適には、１乃至３個置換されたＣ₆−Ｃ₁₀アリール基（該置換基は、ハロゲン原子、低級アルキル基、ハロゲノ低級アルキル基、低級アルコキシ基及び低級脂肪族アシル基から成る群から選択される基である。）であり、より更に好適には、１乃至３個置換されたフェニル基（該置換基は、ハロゲン原子、低級アルキル基、ハロゲノ低級アルキル基、低級アルコキシ基及び低級脂肪族アシル基から成る群から選択される基である。）であり、更により好適には、１乃至２個置換されたフェニル基（該置換基は、フッ素原子、塩素原子、メチル、トリフルオロメチル、メトキシ及びアセチル基から成る群から選択される基である。但し、メトキシ基については、１乃至３個置換されたフェニル基が好ましい。）であり、最も好適には、３−フルオロフェニル、４−フルオロフェニル、３，４−ジフルオロフェニル、３，５−ジフルオロフェニル、３−クロロフェニル、４−クロロフェニル、３，４−ジクロロフェニル、３，５−ジクロロフェニル、３−メチルフェニル、４−メチルフェニル、３，４−ジメチルフェニル、３，５−ジメチルフェニル、３−トリフルオロメチルフェニル、４−トリフルオロメチルフェニル、３，４−ジトリフルオロメチルフェニル、３，５−ジトリフルオロメチルフェニル、３−メトキシフェニル、４−メトキシフェニル、３，４−ジメトキシフェニル、３，５−ジメトキシフェニル、３，４，５−トリメトキシフェニル、３−アセチルフェニル又は４−アセチルフェニル基である。
【００４３】
Ｒ⁵の定義における「置換基群ａ及びｂから選択される基で１乃至３個置換された、硫黄原子、酸素原子及び／又は窒素原子を１乃至３個含む５乃至７員複素環基」の具体例は、例えば、３−，４−若しくは５−メチルフラン−２−イル、２−，４−若しくは５−メチルフラン−３−イル、３−，４−若しくは５−フルオロチオフェン−２−イル、２−，４−若しくは５−フルオロフラン−３−イル、３−，４−若しくは５−ブロモチオフェン−２−イル、２−，４−若しくは５−ブロモフラン−３−イル、３−，４−若しくは５−メチルチオフェン−２−イル、２−，４−若しくは５−メチルチオフェン−３−イル、３−，４−若しくは５−エチルチオフェン−２−イル、２−，４−若しくは５−エチルチオフェン−３−イル、３−，４−若しくは５−メトキシチオフェン−２−イル、２−，４−若しくは５−メトキシチオフェン−３−イル、３−若しくは４−メチルチアゾ−ル−５−イル、３−，４−若しくは５−フルオロベンゾチオフェン−２−イル、３−，４−若しくは５−ブロモベンゾチオフェン−２−イル、３−，４−若しくは５−メチルベンゾチオフェン−２−イル、３−，４−若しくは５−メトキシベンゾチオフェン−２−イル、２−，４−若しくは５−フルオロベンゾチオフェン−３−イル、２−，４−若しくは５−ブロモベンゾチオフェン−３−イル、２−，４−若しくは５−メチルベンゾチオフェン−３−イル、２−，４−若しくは５−メトキシベンゾチオフェン−３−イル、４−，５−，６−若しくは７−メチルベンゾチオフェン−２−イル、３−，４−若しくは５−ヒドロキシフラン−２−イル、２−，４−若しくは５−ヒドロキシフラン−３−イル、３−，４−若しくは５−ヒドロキシチオフェン−２−イル、３−，４−若しくは５−ニトロチオフェン−２−イル、３−，４−若しくは５−フェニルチオフェン−２−イル、２−，４−若しくは５−ヒドロキシチオフェン−３−イル、２−，４−若しくは５−シアノチオフェン−３−イル、１−，２−若しくは３−ヒドロキシピリジン−４−イル、１−，２−若しくは３−シアノピリジン−４−イル、１−，２−若しくは３−フェニルピリジン−４−イル基であり、好適には、３−，４−若しくは５−フルオロチオフェン−２−イル又は２−，４−若しくは５−フルオロフラン−３−イル基である。
【００４４】
「その薬理上許容される塩」とは、本発明の一般式（Ｉ）を有する化合物は、アミノ基のような塩基性の基を有する場合には酸と反応させることにより、又、リン酸基のような酸性基を有する場合には塩基と反応させることにより、塩にすることができるので、その塩を示す。
【００４５】
塩基性の基に基づく塩は、例えば、フッ化水素酸塩、塩酸塩、臭化水素酸塩、ヨウ化水素酸塩のようなハロゲン化水素酸塩、硝酸塩、過塩素酸塩、硫酸塩、リン酸塩等の無機酸塩；メタンスルホン酸塩、トリフルオロメタンスルホン酸塩、エタンスルホン酸塩のような低級アルカンスルホン酸塩、ベンゼンスルホン酸塩、ｐ−トルエンスルホン酸塩のようなアリールスルホン酸塩、酢酸塩、リンゴ酸塩、フマール酸塩、コハク酸塩、クエン酸塩、アスコルビン酸塩、酒石酸塩、シュウ酸塩、マレイン酸塩等の有機酸塩；又はグリシン塩、リジン塩、アルギニン塩、オルニチン塩、グルタミン酸塩、アスパラギン酸塩のようなアミノ酸塩であり得、好適には、有機酸塩（特に、フマール酸塩、シュウ酸塩若しくはマレイン酸塩）又はハロゲン化水素酸塩（特に、塩酸塩）である。
【００４６】
一方、酸性の基に基づく塩は、例えば、ナトリウム塩、カリウム塩、リチウム塩のようなアルカリ金属塩、カルシウム塩、マグネシウム塩のようなアルカリ土類金属塩、アルミニウム塩、鉄塩等の金属塩；アンモニウム塩のような無機塩、ｔ−オクチルアミン塩、ジベンジルアミン塩、モルホリン塩、グルコサミン塩、フェニルグリシンアルキルエステル塩、エチレンジアミン塩、Ｎ−メチルグルカミン塩、グアニジン塩、ジエチルアミン塩、トリエチルアミン塩、ジシクロヘキシルアミン塩、Ｎ，Ｎ’−ジベンジルエチレンジアミン塩、クロロプロカイン塩、プロカイン塩、ジエタノ−ルアミン塩、Ｎ−ベンジルフェネチルアミン塩、ピペラジン塩、テトラメチルアンモニウム塩、トリス（ヒドロキシメチル）アミノメタン塩のような有機塩等のアミン塩；又はグリシン塩、リジン塩、アルギニン塩、オルニチン塩、グルタミン酸塩、アスパラギン酸塩のようなアミノ酸塩であり得、好適には、アルカリ金属塩（特に、ナトリウム塩）である。
【００４７】
本発明の一般式（Ｉ）を有する化合物、その薬理上許容される塩又はその薬理上許容されるエステルは、大気中に放置したり、又は、再結晶をすることにより、水分を吸収し、吸着水が付いたり、水和物となる場合があり、そのような水和物も本発明の塩に包含される。
【００４８】
本発明の一般式（Ｉ）を有する化合物、その薬理上許容される塩又はその薬理上許容されるエステルは、その分子内に不斉炭素原子を有するので、光学異性体が存在する。本発明の化合物においては、光学異性体および光学異性体の混合物がすべて単一の式、即ち一般式（Ｉ）で示されている。従って、本発明は光学異性体および光学異性体の任意の割合の混合物をもすべて含むものである。
【００４９】
本発明の一般式（Ｉ）を有する化合物は、好適には、式−ＮＲ¹Ｒ²を有する基が結合している不斉炭素原子に関して、Ｒの絶対配位を有する化合物である。
【００５０】
上記における「エステル」とは、前述の一般式（Ｉ）を有する化合物は、エステルにすることができるので、そのエステルをいい、そのようなエステルとしては、「ヒドロキシ基のエステル」及び「カルボキシル基のエステル」を挙げることができ、各々のエステル残基が「反応における一般的保護基」又は「生体内で加水分解のような生物学的方法により開裂し得る保護基」であるエステルをいう。
【００５１】
「反応における一般的保護基」とは、加水素分解、加水分解、電気分解、光分解のような化学的方法により開裂し得る保護基をいう。
【００５２】
「ヒドロキシ基のエステル」に斯かる「反応における一般的保護基」は、例えば、
前記「低級脂肪族アシル基」、クロロアセチル、ジクロロアセチル、トリクロロアセチル、トリフルオロアセチルのようなハロゲノ低級脂肪族アシル基、メトキシアセチルのような低級アルコキシで置換された低級脂肪族アシル基などの「脂肪族アシル類」；
ベンゾイル、１−インダンカルボニル、２−インダンカルボニル、１−若しくは２−ナフトイルのような芳香族アシル基、４−クロロベンゾイル、４−フルオロベンゾイル、２，４，６−トリメチルベンゾイル、４−トルオイル、４−アニソイル４−ニトロベンゾイル、２−ニトロベンゾイル、２−（メトキシカルボニル）ベンゾイル、４−フェニルベンゾイルのような前記置換基群ａから選択される基で１乃至３個置換された芳香族アシル基などの「芳香族アシル類」；
テトラヒドロピラン−２−イル、３−ブロモテトラヒドロピラン−2−イル、４−メトキシテトラヒドロピラン−４−イル、テトラヒドロチオピラン−２−イル、４−メトキシテトラヒドロチオピラン−４−イルのような「テトラヒドロピラニル又はテトラヒドロチオピラニル類」；
テトラヒドロフラン−２−イル、テトラヒドロチオフラン−２−イルのような「テトラヒドロフラニル又はテトラヒドロチオフラニル類」；
トリメチルシリル、トリエチルシリル、イソプロピルジメチルシリル、ｔ−ブチルジメチルシリル、メチルジイソプロピルシリル、メチルジ−ｔ−ブチルシリル、トリイソプロピルシリルのようなトリ低級アルキルシリル基、ジフェニルメチルシリル、ジフェニルブチルシリル、ジフェニルイソプロピルシリル、フェニルジイソプロピルシリルのようなアリールまたはアリールと低級アルキルとでトリ置換されたシリル基などの「シリル類」；
メトキシメチル、１,１−ジメチル−１−メトキシメチル、エトキシメチル、プロポキシメチル、イソプロポキシメチル、ブトキシメチル、ｔ−ブトキシメチルのような低級アルコキシメチル基、２−メトキシエトキシメチルのような低級アルコキシ化低級アルコキシメチル基、２，２，２−トリクロロエトキシメチル、ビス(２−クロロエトキシ) メチルのようなハロゲノ低級アルコキシメチル等の「アルコキシメチル基」；
１−エトキシエチル、１−( イソプロポキシ) エチルのような低級アルコキシ化エチル基、２，２，２−トリクロロエチルのようなハロゲン化エチル基等の「置換エチル類」；
ベンジル、フェネチル、３−フェニルプロピル、α−ナフチルメチル、β−ナフチルメチル、ジフェニルメチル、トリフェニルメチル、α−ナフチルジフェニルメチル、９−アンスリルメチルのような１乃至３個のアリール基で置換された低級アルキル基、４−メチルベンジル、２，４，６−トリメチルベンジル、３，４，５−トリメチルベンジル、４−メトキシベンジル、４−メトキシフェニルジフェニルメチル、２−ニトロベンジル、４−ニトロベンジル、４−クロロベンジル、４−ブロモベンジル、４−シアノベンジル、４−シアノベンジルジフェニルメチル、ビス（２−ニトロフェニル）メチル、ピペロニルのような低級アルキル、低級アルコキシ、ニトロ、ハロまたはシアノでアリール環が置換された１〜３個のアリール基で置換された低級アルキル基などの「アラルキル類」；
前記「低級アルコキシカルボニル基」、２，２，２−トリクロロエトキシカルボニル、２−トリメチルシリルエトキシカルボニルのようなハロゲンまたはトリ低級アルキルシリルで置換された低級アルコキシカルボニル基などの「アルコキシカルボニル類」；
ビニルオキシカルボニル、アリルオキシカルボニルのような「アルケニルオキシカルボニル類」；又は
ベンジルオキシカルボニルのようなアラルキルオキシカルボニル基、４−メトキシベンジルオキシカルボニル、３，４−ジメトキシベンジルオキシカルボニル、２−ニトロベンジルオキシカルボニル、４−ニトロベンジルオキシカルボニルのような前記置換基群ａから選択される基で１乃至３個置換されたアラルキルオキシカルボニル基などの「アラルキルオキシカルボニル類」である。
【００５３】
一方、「生体内で加水分解のような生物学的方法により開裂し得る保護基」とは、人体内で加水分解等の生物学的方法により開裂し、フリーの酸又はその塩を生成する保護基をいい、そのような誘導体か否かは、ラットやマウスのような実験動物に静脈注射により投与し、その後の動物の体液を調べ、元となる化合物又はその薬理学的に許容される塩を検出できることにより決定できる。「ヒドロキシ基のエステル」に斯かる、「生体内で加水分解のような生物学的方法により開裂し得る保護基」は、例えば、
エチルカルボニルオキシメチル、ピバロイルオキシメチル、ジメチルアミノアセチルキシメチル、１−アセトキシエチルのようなアシルオキシアルキル類；
１−（メトキシカルボニルオキシ）エチル、１−（エトキシカルボニルオキシ）エチル、エトキシカルボニルオキシメチル、１−（イソプロポキシカルボニルオキシ）エチル、１−（ｔ−ブトキシカルボニルオキシ）エチル、１−（エトキシカルボニルオキシ）プロピル、１−（シクロヘキシルオキシカルボニルオキシ）エチルのような１−（アルコキシカルボニルオキシ）アルキル類；
フタリジル基；
４−メチル−オキソジオキソレニルメチル、４−フェニル−オキソジオキソレニルメチル、オキソジオキソレニルメチルのようなオキソジオキソレニルメチル基等の「カルボニルオキシアルキル類」；
前記「脂肪族アシル類」；
前記「芳香族アシル類」；
「コハク酸のハーフエステル塩残基」；
「リン酸エステル塩残基」；
「アミノ酸等のエステル形成残基」；
カルバモイル基；
ベンジリデンのようなアラルキリデン基；メトキシエチリデン、エトキシエチリデンのようなアルコキシエチリデン基；オキソメチレン；チオキソメチレンのような「２つのヒドロキシ基の保護基」；又は
ピバロイルオキシメチルオキシカルボニルのような「カルボニルオキシアルキルオキシカルボニル基」であり、好適には、低級脂肪族アシル基、芳香族アシル基又は置換基群ａから選択される基で１乃至３個置換された芳香族アシル基である。
【００５４】
上記「ヒドロキシ基の保護基」として、特に好適には、脂肪族アシル基又は芳香族アシル基である。
【００５５】
「カルボキシル基のエステル」に斯かる「反応における一般的保護基」は、好適には、前記「低級アルキル基」；エテニル、１−プロペニル、２−プロペニル、１−メチル−２−プロペニル、１−メチル−１−プロペニル、２−メチル−１−プロペニル、２−メチル−２−プロペニル、２−エチル−２−プロペニル、１−ブテニル、２−ブテニル、１−メチル−２−ブテニル、１−メチル−１−ブテニル、３−メチル−２−ブテニル、１−エチル−２−ブテニル、３−ブテニル、１−メチル−３−ブテニル、２−メチル−３−ブテニル、１−エチル−３−ブテニル、１−ペンテニル、２−ペンテニル、１−メチル−２−ペンテニル、２−メチル−２−ペンテニル、３−ペンテニル、１−メチル−３−ペンテニル、２−メチル−３−ペンテニル、４−ペンテニル、１−メチル−４−ペンテニル、２−メチル−４−ペンテニル、１−ヘキセニル、２−ヘキセニル、３−ヘキセニル、４−ヘキセニル、５−ヘキセニルのような低級アルケニル基；エチニル、２−プロピニル、１−メチル−２−プロピニル、２−メチル−２−プロピニル、２−エチル−２−プロピニル、２−ブチニル、１−メチル−２−ブチニル、２−メチル−２−ブチニル、１−エチル−２−ブチニル、３−ブチニル、１−メチル−３−ブチニル、２−メチル−３−ブチニル、１−エチル−３−ブチニル、２−ペンチニル、１−メチル−２−ペンチニル、２−メチル−２−ペンチニル、３−ペンチニル、１−メチル−３−ペンチニル、２−メチル−３−ペンチニル、４−ペンチニル、１−メチル−４−ペンチニル、２−メチル−４−ペンチニル、２−ヘキシニル、３−ヘキシニル、４−ヘキシニル、５−ヘキシニルのような低級アルキニル基；前記「ハロゲノ低級アルキル」；２−ヒドロキシエチル、２，３−ジヒドロキシプロピル、３−ヒドロキシプロピル、３，４−ジヒドロキシブチル、４−ヒドロキシブチルのようなヒドロキシ「低級アルキル基」；アセチルメチルのような「低級脂肪族アシル」−「低級アルキル基」；前記「アラルキル基」；又は前記「シリル基」である。
【００５６】
「カルボキシル基のエステル」に斯かる「生体内で加水分解のような生物学的方法により開裂し得る保護基」は、好適には、メトキシエチル、１−エトキシエチル、１−メチル−１−メトキシエチル、１−（イソプロポキシ）エチル、２−メトキシエチル、２−エトキシエチル、１，１−ジメチル−１−メトキシエチル、エトキシメチル、ｎ−プロポキシメチル、イソプロポキシメチル、ｎ−ブトキシメチル、ｔ−ブトキシメチルのような低級アルコキシ低級アルキル基、２−メトキシエトキシメチルのような低級アルコキシ化低級アルコキシ低級アルキル基、フェノキシメチルのような「アリール」オキシ「低級アルキル基」、２，２，２−トリクロロエトキシメチル、ビス（２−クロロエトキシ）メチルのようなハロゲン化低級アルコキシ低級アルキル基等の「アルコキシアルキル基」；メトキシカルボニルメチルのような「「低級アルコキシ」カルボニル「低級アルキル基」」；シアノメチル、２−シアノエチルのような「シアノ「低級アルキル基」」；メチルチオメチル、エチルチオメチルのような「「低級アルキル」チオメチル基」；フェニルチオメチル、ナフチルチオメチルのような「「アリール」チオメチル基」；２−メタンスルホニルエチル、２−トリフルオロメタンスルホニルエチルのような「ハロゲンで置換されていてもよい「低級アルキル」スルホニル「低級アルキル基」」；２−ベンゼンスルホニルエチル、２−トルエンスルホニルエチルのような「「アリール」スルホニル「低級アルキル基」」；前記「１−（アシルオキシ）「低級アルキル基」」；前記「フタリジル基」；前記「アリール基」；前記「低級アルキル基」；カルボキシメチルのような「カルボキシアルキル基」；又はフェニルアラニンのような「アミノ酸のアミド形成残基」である。
【００５７】
上記「カルボキシ基のエステル」に斯かる「反応における一般的保護基」及び「生体内で加水分解のような生物学的方法により開裂し得る保護基」において、更に好適には、低級アルキル又はアラルキル基である。
【００５８】
本発明の一般式（Ｉ）を有する化合物の具体例としては、例えば、下記表１及び表２に記載の化合物を挙げることができるが、本発明は、これらの化合物に限定されるものではない。なお、同一の化合物番号で表される化合物は、ＺがＯ又は−ＣＨ₂−の２つの化合物を示す。
【００５９】
表中の略号は以下の通りである。
Ｂｕ：ブチル基
ｉＢｕ：イソブチル基
Ｂｚ：ベンジル基
Ｅｔ：エチル基
ｃＨｘ：シクロヘキシル基
Ｍｅ：メチル基
Ｎｐ（１）：ナフタレン−１−イル基
Ｎｐ（２）：ナフタレン−２−イル基
Ｐｈ：フェニル基
ｃＰｎ：シクロペンチル基
Ｐｒ：プロピル基
ｉＰｒ：イソプロピル基。
【００６０】
表１
【００６１】
【化７】

【００６２】
【表１】
――――――――――――――――――――――――――――――――――――
Compd. R¹ R² R³ R_a ³ R⁴ n -X-Y-R⁵ R⁶ R⁷
――――――――――――――――――――――――――――――――――――
1-1 H H H H Me 1 -(CH₂)₅-cHx H H
1-2 H H H H Me 1 -(CH₂)₆-cHx H H
1-3 H H H H Me 1 -CH=CH-(CH₂)₃-cHx H H
1-4 H H H H Me 1 -CH=CH-(CH₂)₄-cHx H H
1-5 H H H H Me 1 -C≡C-(CH₂)₃-cHx H H
1-6 H H H H Me 1 -C≡C-(CH₂)₄-cHx H H
1-7 H H H H Me 1 -CO-(CH₂)₄-cHx H H
1-8 H H H H Me 1 -CO-(CH₂)₅-cHx H H
1-9 H H H H Me 1 -CH(OH)-(CH₂)₄-cHx H H
1-10 H H H H Me 1 -CH(OH)-(CH₂)₅-cHx H H
1-11 H H H H Me 1 -4-(cHx-CH₂O)Ph H H
1-12 H H H H Me 1 -(4-BzO-Ph) H H
1-13 H H H H Me 1 -C≡C-CH₂O-cPn H H
1-14 H H H H Me 1 -C≡C-(CH₂)₂O-cPn H H
1-15 H H H H Me 1 -C≡C-CH₂O-cHx H H
1-16 H H H H Me 1 -C≡C-(CH₂)₂O-cHx H H
1-17 H H H H Me 1 -C≡C-CH₂O-Ph H H
1-18 H H H H Me 1 -C≡C-(CH₂)₂O-Ph H H
1-19 H H H H Me 2 -(CH₂)₂-cHx H H
1-20 H H H H Me 2 -(CH₂)₂-cHx H H
1-21 CO₂Me H H H Me 2 -(CH₂)₂-cHx H H
1-22 CO₂Et H H H Me 2 -(CH₂)₂-cHx H H
1-23 H H H H Me 2 -(CH₂)₂-(4-F-cHx) H H
1-24 H H H H Me 2 -(CH₂)₂-(4-Me-cHx) H H
1-25 H H H H Me 2 -(CH₂)₂-(4-Et-cHx) H H
1-26 H H H H Me 2 -(CH₂)₂-(4-CF₃-cHx) H H
1-27 H H H H Me 2 -(CH₂)₂-(4-MeO-cHx) H H
1-28 H H H H Me 2 -(CH₂)₂-(4-EtO-cHx) H H
1-29 H H H H Me 2 -(CH₂)₂-(4-MeS-cHx) H H
1-30 H H H H Me 2 -(CH₂)₂-(4-cHx-cHx) H H
1-31 H H H H Me 2 -(CH₂)₂-(4-Ph-cHx) H H
1-32 H H H H Me 2 -(CH₂)₂-Ph H H
1-33 H H H H Me 2 -(CH₂)₂-Ph H H
1-34 CO₂Me H H H Me 2 -(CH₂)₂-Ph H H
1-35 CO₂Et H H H Me 2 -(CH₂)₂-Ph H H
1-36 H H H H Me 2 -(CH₂)₂-(4-F-Ph) H H
1-37 H H H H Me 2 -(CH₂)₂-(4-Me-Ph) H H
1-38 H H H H Me 2 -(CH₂)₂-(4-Et-Ph) H H
1-39 H H H H Me 2 -(CH₂)₂-(4-CF₃-Ph) H H
1-40 H H H H Me 2 -(CH₂)₂-(4-MeO-Ph) H H
1-41 H H H H Me 2 -(CH₂)₂-(4-EtO-Ph) H H
1-42 H H H H Me 2 -(CH₂)₂-(4-MeS-Ph) H H
1-43 H H H H Me 2 -(CH₂)₂-(4-cHx-Ph) H H
1-44 H H H H Me 2 -(CH₂)₂-(4-Ph-Ph) H H
1-45 H H H H Me 2 -(CH₂)₃-cHx H H
1-46 H H Me Me Me 2 -(CH₂)₃-cHx H H
1-47 CO₂Me H H H Me 2 -(CH₂)₃-cHx H H
1-48 CO₂Et H H H Me 2 -(CH₂)₃-cHx H H
1-49 H H H H Me 2 -(CH₂)₃-(4-F-cHx) H H
1-50 H H H H Me 2 -(CH₂)₃-(4-Me-cHx) H H
1-51 H H H H Me 2 -(CH₂)₃-(4-Et-cHx) H H
1-52 H H H H Me 2 -(CH₂)₃-(4-CF₃-cHx) H H
1-53 H H H H Me 2 -(CH₂)₃-(4-MeO-cHx) H H
1-54 H H H H Me 2 -(CH₂)₃-(4-EtO-cHx) H H
1-55 H H H H Me 2 -(CH₂)₃-(4-MeS-cHx) H H
1-56 H H H H Me 2 -(CH₂)₃-(4-cHx-cHx) H H
1-57 H H H H Me 2 -(CH₂)₃-(4-Ph-cHx) H H
1-58 H H H H Me 2 -(CH₂)₃-Ph H H
1-59 H H Me Me Me 2 -(CH₂)₃-Ph H H
1-60 CO₂Me H H H Me 2 -(CH₂)₃-Ph H H
1-61 CO₂Et H H H Me 2 -(CH₂)₃-Ph H H
1-62 H H H H Me 2 -(CH₂)₃-(4-F-Ph) H H
1-63 H H H H Me 2 -(CH₂)₃-(4-Me-Ph) H H
1-64 H H H H Me 2 -(CH₂)₃-(4-Et-Ph) H H
1-65 H H H H Me 2 -(CH₂)₃-(4-CF₃-Ph) H H
1-66 H H H H Me 2 -(CH₂)₃-(4-MeO-Ph) H H
1-67 H H H H Me 2 -(CH₂)₃-(4-EtO-Ph) H H
1-68 H H H H Me 2 -(CH₂)₃-(4-MeS-Ph) H H
1-69 H H H H Me 2 -(CH₂)₃-(4-cHx-Ph) H H
1-70 H H H H Me 2 -(CH₂)₃-(4-Ph-Ph) H H
1-71 H H H H Me 2 -(CH₂)₄-cHx H H
1-72 H H H H Me 2 -(CH₂)₄-cHx H H
1-73 CO₂Me H H H Me 2 -(CH₂)₄-cHx H H
1-74 CO₂Et H H H Me 2 -(CH₂)₄-cHx H H
1-75 H H H H Me 2 -(CH₂)₄-(4-F-cHx) H H
1-76 H H H H Me 2 -(CH₂)₄-(4-Me-cHx) H H
1-77 H H H H Me 2 -(CH₂)₄-(4-Et-cHx) H H
1-78 H H H H Me 2 -(CH₂)₄-(4-CF₃-cHx) H H
1-79 H H H H Me 2 -(CH₂)₄-(4-MeO-cHx) H H
1-80 H H H H Me 2 -(CH₂)₄-(4-EtO-cHx) H H
1-81 H H H H Me 2 -(CH₂)₄-(4-MeS-cHx) H H
1-82 H H H H Me 2 -(CH₂)₄-(4-cHx-cHx) H H
1-83 H H H H Me 2 -(CH₂)₄-(4-Ph-cHx) H H
1-84 H H H H Me 2 -(CH₂)₄-Ph H H
1-85 H H H H Me 2 -(CH₂)₄-Ph H H
1-86 CO₂Me H H H Me 2 -(CH₂)₄-Ph H H
1-87 CO₂Et H H H Me 2 -(CH₂)₄-Ph H H
1-88 H H H H Me 2 -(CH₂)₄-(4-F-Ph) H H
1-89 H H H H Me 2 -(CH₂)₄-(4-Me-Ph) H H
1-90 H H H H Me 2 -(CH₂)₄-(4-Et-Ph) H H
1-91 H H H H Me 2 -(CH₂)₄-(4-CF₃-Ph) H H
1-92 H H H H Me 2 -(CH₂)₄-(4-MeO-Ph) H H
1-93 H H H H Me 2 -(CH₂)₄-(4-EtO-Ph) H H
1-94 H H H H Me 2 -(CH₂)₄-(4-MeS-Ph) H H
1-95 H H H H Me 2 -(CH₂)₄-(4-cHx-Ph) H H
1-96 H H H H Me 2 -(CH₂)₄-(4-Ph-Ph) H H
1-97 H H H H Me 2 -(CH₂)₅-cPn H H
1-98 H H H H Me 2 -(CH₂)₅-cHx H H
1-99 H H H H Me 2 -(CH₂)₅-cHx Me H
1-100 H H H H Me 2 -(CH₂)₅-cHx H Me
1-101 H H H H Me 2 -(CH₂)₅-cHx F H
1-102 H H H H Me 2 -(CH₂)₅-cHx H F
1-103 H H H H Me 2 -(CH₂)₅-cHx H H
1-104 CO₂Me H H H Me 2 -(CH₂)₅-cHx H H
1-105 CO₂Et H H H Me 2 -(CH₂)₅-cHx H H
1-106 H H H H Me 2 -(CH₂)₅-(3-F-cHx) H H
1-107 H H H H Me 2 -(CH₂)₅-(4-F-cHx) H H
1-108 H H H H Me 2 -(CH₂)₅-(4-Cl-cHx) H H
1-109 H H H H Me 2 -(CH₂)₅-(4-Br-cHx) H H
1-110 H H H H Me 2 -(CH₂)₅-(3-Me-cHx) H H
1-111 H H H H Me 2 -(CH₂)₅-(4-Me-cHx) H H
1-112 H H H H Me 2 -(CH₂)₅-(3-Et-cHx) H H
1-113 H H H H Me 2 -(CH₂)₅-(4-Et-cHx) H H
1-114 H H H H Me 2 -(CH₂)₅-(3-Pr-cHx) H H
1-115 H H H H Me 2 -(CH₂)₅-(4-Pr-cHx) H H
1-116 H H H H Me 2 -(CH₂)₅-(4-iPr-cHx) H H
1-117 H H H H Me 2 -(CH₂)₅-(3-Bu-cHx) H H
1-118 H H H H Me 2 -(CH₂)₅-(4-Bu-cHx) H H
1-119 H H H H Me 2 -(CH₂)₅-(3-CF₃-cHx) H H
1-120 H H H H Me 2 -(CH₂)₅-(4-CF₃-cHx) H H
1-121 H H H H Me 2 -(CH₂)₅-(3-MeO-cHx) H H
1-122 H H H H Me 2 -(CH₂)₅-(4-MeO-cHx) H H
1-123 H H H H Me 2 -(CH₂)₅-(3-EtO-cHx) H H
1-124 H H H H Me 2 -(CH₂)₅-(4-EtO-cHx) H H
1-125 H H H H Me 2 -(CH₂)₅-(3-PrO-cHx) H H
1-126 H H H H Me 2 -(CH₂)₅-(4-PrO-cHx) H H
1-127 H H H H Me 2 -(CH₂)₅-(3-iPrO-cHx) H H
1-128 H H H H Me 2 -(CH₂)₅-(4-iPrO-cHx) H H
1-129 H H H H Me 2 -(CH₂)₅-[3-(2-Et-PrO)-cHx] H H
1-130 H H H H Me 2 -(CH₂)₅-[4-(2-Et-PrO)-cHx] H H
1-131 H H H H Me 2 -(CH₂)₅-(3-iBuO-cHx) H H
1-132 H H H H Me 2 -(CH₂)₅-(4-iBuO-cHx) H H
1-133 H H H H Me 2 -(CH₂)₅-(3-MeS-cHx) H H
1-134 H H H H Me 2 -(CH₂)₅-(4-MeS-cHx) H H
1-135 H H H H Me 2 -(CH₂)₅-(3-EtS-cHx) H H
1-136 H H H H Me 2 -(CH₂)₅-(4-EtS-cHx) H H
1-137 H H H H Me 2 -(CH₂)₅-(3-PrS-cHx) H H
1-138 H H H H Me 2 -(CH₂)₅-(4-PrS-cHx) H H
1-139 H H H H Me 2 -(CH₂)₅-(3-iPrS-cHx) H H
1-140 H H H H Me 2 -(CH₂)₅-(4-iPrS-cHx) H H
1-141 H H H H Me 2 -(CH₂)₅-[3-(2-Et-PrS)-cHx] H H
1-142 H H H H Me 2 -(CH₂)₅-[4-(2-Et-PrS)-cHx] H H
1-143 H H H H Me 2 -(CH₂)₅-(3-iBuS-cHx) H H
1-144 H H H H Me 2 -(CH₂)₅-(4-iBuS-cHx) H H
1-145 H H H H Me 2 -(CH₂)₅-(3-cHx-cHx) H H
1-146 H H H H Me 2 -(CH₂)₅-(4-cHx-cHx) H H
1-147 H H H H Me 2 -(CH₂)₅-(3-Ph-cHx) H H
1-148 H H H H Me 2 -(CH₂)₅-(4-Ph-cHx) H H
1-149 H H H H Me 2 -(CH₂)₅-(2,4-diMe-cHx) H H
1-150 H H H H Me 2 -(CH₂)₅-(3,4-diMe-cHx) H H
1-151 H H H H Me 2 -(CH₂)₅-(3,5-diMe-cHx) H H
1-152 H H H H Me 2 -(CH₂)₅-Ph H H
1-153 H H H H Me 2 -(CH₂)₅-Ph Me H
1-154 H H H H Me 2 -(CH₂)₅-Ph H Me
1-155 H H H H Me 2 -(CH₂)₅-Ph F H
1-156 H H H H Me 2 -(CH₂)₅-Ph H F
1-157 H H H H Me 2 -(CH₂)₅-Ph H H
1-158 CO₂Me H H H Me 2 -(CH₂)₅-Ph H H
1-159 CO₂Et H H H Me 2 -(CH₂)₅-Ph H H
1-160 H H H H Me 2 -(CH₂)₅-(3-F-Ph) H H
1-161 H H H H Me 2 -(CH₂)₅-(4-F-Ph) H H
1-162 H H H H Me 2 -(CH₂)₅-(4-Cl-Ph) H H
1-163 H H H H Me 2 -(CH₂)₅-(4-Br-Ph) H H
1-164 H H H H Me 2 -(CH₂)₅-(3-Me-Ph) H H
1-165 H H H H Me 2 -(CH₂)₅-(4-Me-Ph) H H
1-166 H H H H Me 2 -(CH₂)₅-(3-Et-Ph) H H
1-167 H H H H Me 2 -(CH₂)₅-(4-Et-Ph) H H
1-168 H H H H Me 2 -(CH₂)₅-(3-Pr-Ph) H H
1-169 H H H H Me 2 -(CH₂)₅-(4-Pr-Ph) H H
1-170 H H H H Me 2 -(CH₂)₅-(3-iPr-Ph) H H
1-171 H H H H Me 2 -(CH₂)₅-(4-iPr-Ph) H H
1-172 H H H H Me 2 -(CH₂)₅-(3-Bu-Ph) H H
1-173 H H H H Me 2 -(CH₂)₅-(4-Bu-Ph) H H
1-174 H H H H Me 2 -(CH₂)₅-(3-CF₃-Ph) H H
1-175 H H H H Me 2 -(CH₂)₅-(4-CF₃-Ph) H H
1-176 H H H H Me 2 -(CH₂)₅-(3-MeO-Ph) H H
1-177 H H H H Me 2 -(CH₂)₅-(4-MeO-Ph) H H
1-178 H H H H Me 2 -(CH₂)₅-(3-EtO-Ph) H H
1-179 H H H H Me 2 -(CH₂)₅-(4-EtO-Ph) H H
1-180 H H H H Me 2 -(CH₂)₅-(3-PrO-Ph) H H
1-181 H H H H Me 2 -(CH₂)₅-(4-PrO-Ph) H H
1-182 H H H H Me 2 -(CH₂)₅-(3-iPrO-Ph) H H
1-183 H H H H Me 2 -(CH₂)₅-(4-iPrO-Ph) H H
1-184 H H H H Me 2 -(CH₂)₅-[3-(2-Et-PrO)-Ph] H H
1-185 H H H H Me 2 -(CH₂)₅-[4-(2-Et-PrO)-Ph] H H
1-186 H H H H Me 2 -(CH₂)₅-(3-iBuO-Ph) H H
1-187 H H H H Me 2 -(CH₂)₅-(4-iBuO-Ph) H H
1-188 H H H H Me 2 -(CH₂)₅-(3-MeS-Ph) H H
1-189 H H H H Me 2 -(CH₂)₅-(4-MeS-Ph) H H
1-190 H H H H Me 2 -(CH₂)₅-(3-EtS-Ph) H H
1-191 H H H H Me 2 -(CH₂)₅-(4-EtS-Ph) H H
1-192 H H H H Me 2 -(CH₂)₅-(3-PrS-Ph) H H
1-193 H H H H Me 2 -(CH₂)₅-(4-PrS-Ph) H H
1-194 H H H H Me 2 -(CH₂)₅-(3-iPrS-Ph) H H
1-195 H H H H Me 2 -(CH₂)₅-(4-iPrS-Ph) H H
1-196 H H H H Me 2 -(CH₂)₅-[3-(2-Et-PrS)-Ph] H H
1-197 H H H H Me 2 -(CH₂)₅-[4-(2-Et-PrS)-Ph] H H
1-198 H H H H Me 2 -(CH₂)₅-(3-iBuS-Ph) H H
1-199 H H H H Me 2 -(CH₂)₅-(4-iBuS-Ph) H H
1-200 H H H H Me 2 -(CH₂)₅-(3-cHx-Ph) H H
1-201 H H H H Me 2 -(CH₂)₅-(4-cHx-Ph) H H
1-202 H H H H Me 2 -(CH₂)₅-(3-Ph-Ph) H H
1-203 H H H H Me 2 -(CH₂)₅-(4-Ph-Ph) H H
1-204 H H H H Me 2 -(CH₂)₅-(2,4-diMe-Ph) H H
1-205 H H H H Me 2 -(CH₂)₅-(3,4-diMe-Ph) H H
1-206 H H H H Me 2 -(CH₂)₅-(3,5-diMe-Ph) H H
1-207 H H H H Me 2 -(CH₂)₅-Np(1) H H
1-208 H H H H Me 2 -(CH₂)₅-Np(2) H H
1-209 H H H H Me 2 -(CH₂)₆-cPn H H
1-210 H H H H Me 2 -(CH₂)₆-cHx H H
1-211 H H H H Me 2 -(CH₂)₆-cHx Me H
1-212 H H H H Me 2 -(CH₂)₆-cHx H Me
1-213 H H H H Me 2 -(CH₂)₆-cHx F H
1-214 H H H H Me 2 -(CH₂)₆-cHx H F
1-215 H H H H Me 2 -(CH₂)₆-cHx H H
1-216 CO₂Me H H H Me 2 -(CH₂)₆-cHx H H
1-217 CO₂Et H H H Me 2 -(CH₂)₆-cHx H H
1-218 H H H H Me 2 -(CH₂)₆-(3-F-cHx) H H
1-219 H H H H Me 2 -(CH₂)₆-(4-F-cHx) H H
1-220 H H H H Me 2 -(CH₂)₆-(4-Cl-cHx) H H
1-221 H H H H Me 2 -(CH₂)₆-(4-Br-cHx) H H
1-222 H H H H Me 2 -(CH₂)₆-(3-Me-cHx) H H
1-223 H H H H Me 2 -(CH₂)₆-(4-Me-cHx) H H
1-224 H H H H Me 2 -(CH₂)₆-(3-Et-cHx) H H
1-225 H H H H Me 2 -(CH₂)₆-(4-Et-cHx) H H
1-226 H H H H Me 2 -(CH₂)₆-(3-Pr-cHx) H H
1-227 H H H H Me 2 -(CH₂)₆-(4-Pr-cHx) H H
1-228 H H H H Me 2 -(CH₂)₆-(4-iPr-cHx) H H
1-229 H H H H Me 2 -(CH₂)₆-(3-Bu-cHx) H H
1-230 H H H H Me 2 -(CH₂)₆-(4-Bu-cHx) H H
1-231 H H H H Me 2 -(CH₂)₆-(3-CF₃-cHx) H H
1-232 H H H H Me 2 -(CH₂)₆-(4-CF₃-cHx) H H
1-233 H H H H Me 2 -(CH₂)₆-(3-MeO-cHx) H H
1-234 H H H H Me 2 -(CH₂)₆-(4-MeO-cHx) H H
1-235 H H H H Me 2 -(CH₂)₆-(3-EtO-cHx) H H
1-236 H H H H Me 2 -(CH₂)₆-(4-EtO-cHx) H H
1-237 H H H H Me 2 -(CH₂)₆-(3-PrO-cHx) H H
1-238 H H H H Me 2 -(CH₂)₆-(4-PrO-cHx) H H
1-239 H H H H Me 2 -(CH₂)₆-(3-iPrO-cHx) H H
1-240 H H H H Me 2 -(CH₂)₆-(4-iPrO-cHx) H H
1-241 H H H H Me 2 -(CH₂)₆-[3-(2-Et-PrO)-cHx] H H
1-242 H H H H Me 2 -(CH₂)₆-[4-(2-Et-PrO)-cHx] H H
1-243 H H H H Me 2 -(CH₂)₆-(3-iBuO-cHx) H H
1-244 H H H H Me 2 -(CH₂)₆-(4-iBuO-cHx) H H
1-245 H H H H Me 2 -(CH₂)₆-(3-MeS-cHx) H H
1-246 H H H H Me 2 -(CH₂)₆-(4-MeS-cHx) H H
1-247 H H H H Me 2 -(CH₂)₆-(3-EtS-cHx) H H
1-248 H H H H Me 2 -(CH₂)₆-(4-EtS-cHx) H H
1-249 H H H H Me 2 -(CH₂)₆-(3-PrS-cHx) H H
1-250 H H H H Me 2 -(CH₂)₆-(4-PrS-cHx) H H
1-251 H H H H Me 2 -(CH₂)₆-(3-iPrS-cHx) H H
1-252 H H H H Me 2 -(CH₂)₆-(4-iPrS-cHx) H H
1-253 H H H H Me 2 -(CH₂)₆-[3-(2-Et-PrS)-cHx] H H
1-254 H H H H Me 2 -(CH₂)₆-[4-(2-Et-PrS)-cHx] H H
1-255 H H H H Me 2 -(CH₂)₆-(3-iBuS-cHx) H H
1-256 H H H H Me 2 -(CH₂)₆-(4-iBuS-cHx) H H
1-257 H H H H Me 2 -(CH₂)₆-(3-cHx-cHx) H H
1-258 H H H H Me 2 -(CH₂)₆-(4-cHx-cHx) H H
1-259 H H H H Me 2 -(CH₂)₆-(3-Ph-cHx) H H
1-260 H H H H Me 2 -(CH₂)₆-(4-Ph-cHx) H H
1-261 H H H H Me 2 -(CH₂)₆-(2,4-diMe-cHx) H H
1-262 H H H H Me 2 -(CH₂)₆-(3,4-diMe-cHx) H H
1-263 H H H H Me 2 -(CH₂)₆-(3,5-diMe-cHx) H H
1-264 H H H H Me 2 -(CH₂)₆-Ph H H
1-265 H H H H Me 2 -(CH₂)₆-Ph Me H
1-266 H H H H Me 2 -(CH₂)₆-Ph H Me
1-267 H H H H Me 2 -(CH₂)₆-Ph F H
1-268 H H H H Me 2 -(CH₂)₆-Ph H F
1-269 H H Me Me Me 2 -(CH₂)₆-Ph H H
1-270 CO₂Me H H H Me 2 -(CH₂)₆-Ph H H
1-271 CO₂Et H H H Me 2 -(CH₂)₆-Ph H H
1-272 H H H H Me 2 -(CH₂)₆-(3-F-Ph) H H
1-273 H H H H Me 2 -(CH₂)₆-(4-F-Ph) H H
1-274 H H H H Me 2 -(CH₂)₆-(4-Cl-Ph) H H
1-275 H H H H Me 2 -(CH₂)₆-(4-Br-Ph) H H
1-276 H H H H Me 2 -(CH₂)₆-(3-Me-Ph) H H
1-277 H H H H Me 2 -(CH₂)₆-(4-Me-Ph) H H
1-278 H H H H Me 2 -(CH₂)₆-(3-Et-Ph) H H
1-279 H H H H Me 2 -(CH₂)₆-(4-Et-Ph) H H
1-280 H H H H Me 2 -(CH₂)₆-(3-Pr-Ph) H H
1-281 H H H H Me 2 -(CH₂)₆-(4-Pr-Ph) H H
1-282 H H H H Me 2 -(CH₂)₆-(3-iPr-Ph) H H
1-283 H H H H Me 2 -(CH₂)₆-(4-iPr-Ph) H H
1-284 H H H H Me 2 -(CH₂)₆-(3-Bu-Ph) H H
1-285 H H H H Me 2 -(CH₂)₆-(4-Bu-Ph) H H
1-286 H H H H Me 2 -(CH₂)₆-(3-CF₃-Ph) H H
1-287 H H H H Me 2 -(CH₂)₆-(4-CF₃-Ph) H H
1-288 H H H H Me 2 -(CH₂)₆-(3-MeO-Ph) H H
1-289 H H H H Me 2 -(CH₂)₆-(4-MeO-Ph) H H
1-290 H H H H Me 2 -(CH₂)₆-(3-EtO-Ph) H H
1-291 H H H H Me 2 -(CH₂)₆-(4-EtO-Ph) H H
1-292 H H H H Me 2 -(CH₂)₆-(3-PrO-Ph) H H
1-293 H H H H Me 2 -(CH₂)₆-(4-PrO-Ph) H H
1-294 H H H H Me 2 -(CH₂)₆-(3-iPrO-Ph) H H
1-295 H H H H Me 2 -(CH₂)₆-(4-iPrO-Ph) H H
1-296 H H H H Me 2 -(CH₂)₆-[3-(2-Et-PrO)-Ph] H H
1-297 H H H H Me 2 -(CH₂)₆-[4-(2-Et-PrO)-Ph] H H
1-298 H H H H Me 2 -(CH₂)₆-(3-iBuO-Ph) H H
1-299 H H H H Me 2 -(CH₂)₆-(4-iBuO-Ph) H H
1-300 H H H H Me 2 -(CH₂)₆-(3-MeS-Ph) H H
1-301 H H H H Me 2 -(CH₂)₆-(4-MeS-Ph) H H
1-302 H H H H Me 2 -(CH₂)₆-(3-EtS-Ph) H H
1-303 H H H H Me 2 -(CH₂)₆-(4-EtS-Ph) H H
1-304 H H H H Me 2 -(CH₂)₆-(3-PrS-Ph) H H
1-305 H H H H Me 2 -(CH₂)₆-(4-PrS-Ph) H H
1-306 H H H H Me 2 -(CH₂)₆-(3-iPrS-Ph) H H
1-307 H H H H Me 2 -(CH₂)₆-(4-iPrS-Ph) H H
1-308 H H H H Me 2 -(CH₂)₆-[3-(2-Et-PrS)-Ph] H H
1-309 H H H H Me 2 -(CH₂)₆-[4-(2-Et-PrS)-Ph] H H
1-310 H H H H Me 2 -(CH₂)₆-(3-iBuS-Ph) H H
1-311 H H H H Me 2 -(CH₂)₆-(4-iBuS-Ph) H H
1-312 H H H H Me 2 -(CH₂)₆-(3-cHx-Ph) H H
1-313 H H H H Me 2 -(CH₂)₆-(4-cHx-Ph) H H
1-314 H H H H Me 2 -(CH₂)₆-(3-Ph-Ph) H H
1-315 H H H H Me 2 -(CH₂)₆-(4-Ph-Ph) H H
1-316 H H H H Me 2 -(CH₂)₆-(2,4-diMe-Ph) H H
1-317 H H H H Me 2 -(CH₂)₆-(3,4-diMe-Ph) H H
1-318 H H H H Me 2 -(CH₂)₆-(3,5-diMe-Ph) H H
1-319 H H H H Me 2 -(CH₂)₆-Np(1) H H
1-320 H H H H Me 2 -(CH₂)₆-Np(2) H H
1-321 H H H H Me 2 -(CH₂)₇-cHx H H
1-322 H H Me Me Me 2 -(CH₂)₇-cHx H H
1-323 CO₂Me H H H Me 2 -(CH₂)₇-cHx H H
1-324 CO₂Et H H H Me 2 -(CH₂)₇-cHx H H
1-325 H H H H Me 2 -(CH₂)₇-(4-F-cHx) H H
1-326 H H H H Me 2 -(CH₂)₇-(4-Me-cHx) H H
1-327 H H H H Me 2 -(CH₂)₇-(4-Et-cHx) H H
1-328 H H H H Me 2 -(CH₂)₇-(4-CF₃-cHx) H H
1-329 H H H H Me 2 -(CH₂)₇-(4-MeO-cHx) H H
1-330 H H H H Me 2 -(CH₂)₇-(4-EtO-cHx) H H
1-331 H H H H Me 2 -(CH₂)₇-(4-MeS-cHx) H H
1-332 H H H H Me 2 -(CH₂)₇-(4-cHx-cHx) H H
1-333 H H H H Me 2 -(CH₂)₇-(4-Ph-cHx) H H
1-334 H H H H Me 2 -(CH₂)₇-Ph H H
1-335 H H Me Me Me 2 -(CH₂)₇-Ph H H
1-336 CO₂Me H H H Me 2 -(CH₂)₇-Ph H H
1-337 CO₂Et H H H Me 2 -(CH₂)₇-Ph H H
1-338 H H H H Me 2 -(CH₂)₇-(4-F-Ph) H H
1-339 H H H H Me 2 -(CH₂)₇-(4-Me-Ph) H H
1-340 H H H H Me 2 -(CH₂)₇-(4-Et-Ph) H H
1-341 H H H H Me 2 -(CH₂)₇-(4-CF₃-Ph) H H
1-342 H H H H Me 2 -(CH₂)₇-(4-MeO-Ph) H H
1-343 H H H H Me 2 -(CH₂)₇-(4-EtO-Ph) H H
1-344 H H H H Me 2 -(CH₂)₇-(4-MeS-Ph) H H
1-345 H H H H Me 2 -(CH₂)₇-(4-cHx-Ph) H H
1-346 H H H H Me 2 -(CH₂)₇-(4-Ph-Ph) H H
1-347 H H H H Me 2 -(CH₂)₈-cHx H H
1-348 H H Me Me Me 2 -(CH₂)₈-cHx H H
1-349 CO₂Me H H H Me 2 -(CH₂)₈-cHx H H
1-350 CO₂Et H H H Me 2 -(CH₂)₈-cHx H H
1-351 H H H H Me 2 -(CH₂)₈-(4-F-cHx) H H
1-352 H H H H Me 2 -(CH₂)₈-(4-Me-cHx) H H
1-353 H H H H Me 2 -(CH₂)₈-(4-Et-cHx) H H
1-354 H H H H Me 2 -(CH₂)₈-(4-CF₃-cHx) H H
1-355 H H H H Me 2 -(CH₂)₈-(4-MeO-cHx) H H
1-356 H H H H Me 2 -(CH₂)₈-(4-EtO-cHx) H H
1-357 H H H H Me 2 -(CH₂)₈-(4-MeS-cHx) H H
1-358 H H H H Me 2 -(CH₂)₈-(4-cHx-cHx) H H
1-359 H H H H Me 2 -(CH₂)₈-(4-Ph-cHx) H H
1-360 H H H H Me 2 -(CH₂)₈-Ph H H
1-361 H H Me Me Me 2 -(CH₂)₈-Ph H H
1-362 CO₂Me H H H Me 2 -(CH₂)₈-Ph H H
1-363 CO₂Et H H H Me 2 -(CH₂)₈-Ph H H
1-364 H H H H Me 2 -(CH₂)₈-(4-F-Ph) H H
1-365 H H H H Me 2 -(CH₂)₈-(4-Me-Ph) H H
1-366 H H H H Me 2 -(CH₂)₈-(4-Et-Ph) H H
1-367 H H H H Me 2 -(CH₂)₈-(4-CF₃-Ph) H H
1-368 H H H H Me 2 -(CH₂)₈-(4-MeO-Ph) H H
1-369 H H H H Me 2 -(CH₂)₈-(4-EtO-Ph) H H
1-370 H H H H Me 2 -(CH₂)₈-(4-MeS-Ph) H H
1-371 H H H H Me 2 -(CH₂)₈-(4-cHx-Ph) H H
1-372 H H H H Me 2 -(CH₂)₈-(4-Ph-Ph) H H
1-373 H H H H Me 2 -(CH₂)₃-O-cHx H H
1-374 H H Me Me Me 2 -(CH₂)₃-O-cHx H H
1-375 CO₂Me H H H Me 2 -(CH₂)₃-O-cHx H H
1-376 CO₂Et H H H Me 2 -(CH₂)₃-O-cHx H H
1-377 H H H H Me 2 -(CH₂)₃-O-(4-F-cHx) H H
1-378 H H H H Me 2 -(CH₂)₃-O-(4-Me-cHx) H H
1-379 H H H H Me 2 -(CH₂)₃-O-(4-Et-cHx) H H
1-380 H H H H Me 2 -(CH₂)₃-O-(4-CF₃-cHx) H H
1-381 H H H H Me 2 -(CH₂)₃-O-(4-MeO-cHx) H H
1-382 H H H H Me 2 -(CH₂)₃-O-(4-EtO-cHx) H H
1-383 H H H H Me 2 -(CH₂)₃-O-(4-MeS-cHx) H H
1-384 H H H H Me 2 -(CH₂)₃-O-(4-cHx-cHx) H H
1-385 H H H H Me 2 -(CH₂)₃-O-(4-Ph-cHx) H H
1-386 H H H H Me 2 -(CH₂)₃-O-Ph H H
1-387 H H H H Me 2 -(CH₂)₃-O-Ph H H
1-388 CO₂Me H H H Me 2 -(CH₂)₃-O-Ph H H
1-389 CO₂Et H H H Me 2 -(CH₂)₃-O-Ph H H
1-390 H H H H Me 2 -(CH₂)₃-O-(4-F-Ph) H H
1-391 H H H H Me 2 -(CH₂)₃-O-(4-Me-Ph) H H
1-392 H H H H Me 2 -(CH₂)₃-O-(4-Et-Ph) H H
1-393 H H H H Me 2 -(CH₂)₃-O-(4-CF₃-Ph) H H
1-394 H H H H Me 2 -(CH₂)₃-O-(4-MeO-Ph) H H
1-395 H H H H Me 2 -(CH₂)₃-O-(4-EtO-Ph) H H
1-396 H H H H Me 2 -(CH₂)₃-O-(4-MeS-Ph) H H
1-397 H H H H Me 2 -(CH₂)₃-O-(4-cHx-Ph) H H
1-398 H H H H Me 2 -(CH₂)₃-O-(4-Ph-Ph) H H
1-399 H H H H Me 2 -(CH₂)₄-O-cPn H H
1-400 H H H H Me 2 -(CH₂)₄-O-cHx H H
1-401 H H H H Me 2 -(CH₂)₄-O-cHx Me H
1-402 H H H H Me 2 -(CH₂)₄-O-cHx H Me
1-403 H H H H Me 2 -(CH₂)₄-O-cHx F H
1-404 H H H H Me 2 -(CH₂)₄-O-cHx H F
1-405 H H H H Me 2 -(CH₂)₄-O-cHx H H
1-406 CO₂Me H H H Me 2 -(CH₂)₄-O-cHx H H
1-407 CO₂Et H H H Me 2 -(CH₂)₄-O-cHx H H
1-408 H H H H Me 2 -(CH₂)₄-O-(3-F-cHx) H H
1-409 H H H H Me 2 -(CH₂)₄-O-(4-F-cHx) H H
1-410 H H H H Me 2 -(CH₂)₄-O-(4-Cl-cHx) H H
1-411 H H H H Me 2 -(CH₂)₄-O-(4-Br-cHx) H H
1-412 H H H H Me 2 -(CH₂)₄-O-(3-Me-cHx) H H
1-413 H H H H Me 2 -(CH₂)₄-O-(4-Me-cHx) H H
1-414 H H H H Me 2 -(CH₂)₄-O-(3-Et-cHx) H H
1-415 H H H H Me 2 -(CH₂)₄-O-(4-Et-cHx) H H
1-416 H H H H Me 2 -(CH₂)₄-O-(3-Pr-cHx) H H
1-417 H H H H Me 2 -(CH₂)₄-O-(4-Pr-cHx) H H
1-418 H H H H Me 2 -(CH₂)₄-O-(4-iPr-cHx) H H
1-419 H H H H Me 2 -(CH₂)₄-O-(3-Bu-cHx) H H
1-420 H H H H Me 2 -(CH₂)₄-O-(4-Bu-cHx) H H
1-421 H H H H Me 2 -(CH₂)₄-O-(3-CF₃-cHx) H H
1-422 H H H H Me 2 -(CH₂)₄-O-(4-CF₃-cHx) H H
1-423 H H H H Me 2 -(CH₂)₄-O-(3-MeO-cHx) H H
1-424 H H H H Me 2 -(CH₂)₄-O-(4-MeO-cHx) H H
1-425 H H H H Me 2 -(CH₂)₄-O-(3-EtO-cHx) H H
1-426 H H H H Me 2 -(CH₂)₄-O-(4-EtO-cHx) H H
1-427 H H H H Me 2 -(CH₂)₄-O-(3-PrO-cHx) H H
1-428 H H H H Me 2 -(CH₂)₄-O-(4-PrO-cHx) H H
1-429 H H H H Me 2 -(CH₂)₄-O-(3-iPrO-cHx) H H
1-430 H H H H Me 2 -(CH₂)₄-O-(4-iPrO-cHx) H H
1-431 H H H H Me 2 -(CH₂)₄-O-[3-(2-Et-PrO)-cHx] H H
1-432 H H H H Me 2 -(CH₂)₄-O-[4-(2-Et-PrO)-cHx] H H
1-433 H H H H Me 2 -(CH₂)₄-O-(3-iBuO-cHx) H H
1-434 H H H H Me 2 -(CH₂)₄-O-(4-iBuO-cHx) H H
1-435 H H H H Me 2 -(CH₂)₄-O-(3-MeS-cHx) H H
1-436 H H H H Me 2 -(CH₂)₄-O-(4-MeS-cHx) H H
1-437 H H H H Me 2 -(CH₂)₄-O-(3-EtS-cHx) H H
1-438 H H H H Me 2 -(CH₂)₄-O-(4-EtS-cHx) H H
1-439 H H H H Me 2 -(CH₂)₄-O-(3-PrS-cHx) H H
1-440 H H H H Me 2 -(CH₂)₄-O-(4-PrS-cHx) H H
1-441 H H H H Me 2 -(CH₂)₄-O-(3-iPrS-cHx) H H
1-442 H H H H Me 2 -(CH₂)₄-O-(4-iPrS-cHx) H H
1-443 H H H H Me 2 -(CH₂)₄-O-[3-(2-Et-PrS)-cHx] H H
1-444 H H H H Me 2 -(CH₂)₄-O-[4-(2-Et-PrS)-cHx] H H
1-445 H H H H Me 2 -(CH₂)₄-O-(3-iBuS-cHx) H H
1-446 H H H H Me 2 -(CH₂)₄-O-(4-iBuS-cHx) H H
1-447 H H H H Me 2 -(CH₂)₄-O-(3-cHx-cHx) H H
1-448 H H H H Me 2 -(CH₂)₄-O-(4-cHx-cHx) H H
1-449 H H H H Me 2 -(CH₂)₄-O-(3-Ph-cHx) H H
1-450 H H H H Me 2 -(CH₂)₄-O-(4-Ph-cHx) H H
1-451 H H H H Me 2 -(CH₂)₄-O-(2,4-diMe-cHx) H H
1-452 H H H H Me 2 -(CH₂)₄-O-(3,4-diMe-cHx) H H
1-453 H H H H Me 2 -(CH₂)₄-O-(3,5-diMe-cHx) H H
1-454 H H H H Me 2 -(CH₂)₄-O-Ph H H
1-455 H H H H Me 2 -(CH₂)₄-O-Ph Me H
1-456 H H H H Me 2 -(CH₂)₄-O-Ph H Me
1-457 H H H H Me 2 -(CH₂)₄-O-Ph F H
1-458 H H H H Me 2 -(CH₂)₄-O-Ph H F
1-459 H H Me Me 2 -(CH₂)₄-O-Ph H H
1-460 CO₂Me H H Me 2 -(CH₂)₄-O-Ph H H
1-461 CO₂Et H H Me 2 -(CH₂)₄-O-Ph H H
1-462 H H H H Me 2 -(CH₂)₄-O-(3-F-Ph) H H
1-463 H H H H Me 2 -(CH₂)₄-O-(4-F-Ph) H H
1-464 H H H H Me 2 -(CH₂)₄-O-(4-Cl-Ph) H H
1-465 H H H H Me 2 -(CH₂)₄-O-(4-Br-Ph) H H
1-466 H H H H Me 2 -(CH₂)₄-O-(3-Me-Ph) H H
1-467 H H H H Me 2 -(CH₂)₄-O-(4-Me-Ph) H H
1-468 H H H H Me 2 -(CH₂)₄-O-(3-Et-Ph) H H
1-469 H H H H Me 2 -(CH₂)₄-O-(4-Et-Ph) H H
1-470 H H H H Me 2 -(CH₂)₄-O-(3-Pr-Ph) H H
1-471 H H H H Me 2 -(CH₂)₄-O-(4-Pr-Ph) H H
1-472 H H H H Me 2 -(CH₂)₄-O-(3-iPr-Ph) H H
1-473 H H H H Me 2 -(CH₂)₄-O-(4-iPr-Ph) H H
1-474 H H H H Me 2 -(CH₂)₄-O-(3-Bu-Ph) H H
1-475 H H H H Me 2 -(CH₂)₄-O-(4-Bu-Ph) H H
1-476 H H H H Me 2 -(CH₂)₄-O-(3-CF₃-Ph) H H
1-477 H H H H Me 2 -(CH₂)₄-O-(4-CF₃-Ph) H H
1-478 H H H H Me 2 -(CH₂)₄-O-(3-MeO-Ph) H H
1-479 H H H H Me 2 -(CH₂)₄-O-(4-MeO-Ph) H H
1-480 H H H H Me 2 -(CH₂)₄-O-(3-EtO-Ph) H H
1-481 H H H H Me 2 -(CH₂)₄-O-(4-EtO-Ph) H H
1-482 H H H H Me 2 -(CH₂)₄-O-(3-PrO-Ph) H H
1-483 H H H H Me 2 -(CH₂)₄-O-(4-PrO-Ph) H H
1-484 H H H H Me 2 -(CH₂)₄-O-(3-iPrO-Ph) H H
1-485 H H H H Me 2 -(CH₂)₄-O-(4-iPrO-Ph) H H
1-486 H H H H Me 2 -(CH₂)₄-O-[3-(2-Et-PrO)-Ph] H H
1-487 H H H H Me 2 -(CH₂)₄-O-[4-(2-Et-PrO)-Ph] H H
1-488 H H H H Me 2 -(CH₂)₄-O-(3-iBuO-Ph) H H
1-489 H H H H Me 2 -(CH₂)₄-O-(4-iBuO-Ph) H H
1-490 H H H H Me 2 -(CH₂)₄-O-(3-MeS-Ph) H H
1-491 H H H H Me 2 -(CH₂)₄-O-(4-MeS-Ph) H H
1-492 H H H H Me 2 -(CH₂)₄-O-(3-EtS-Ph) H H
1-493 H H H H Me 2 -(CH₂)₄-O-(4-EtS-Ph) H H
1-494 H H H H Me 2 -(CH₂)₄-O-(3-PrS-Ph) H H
1-495 H H H H Me 2 -(CH₂)₄-O-(4-PrS-Ph) H H
1-496 H H H H Me 2 -(CH₂)₄-O-(3-iPrS-Ph) H H
1-497 H H H H Me 2 -(CH₂)₄-O-(4-iPrS-Ph) H H
1-498 H H H H Me 2 -(CH₂)₄-O-[3-(2-Et-PrS)-Ph] H H
1-499 H H H H Me 2 -(CH₂)₄-O-[4-(2-Et-PrS)-Ph] H H
1-500 H H H H Me 2 -(CH₂)₄-O-(3-iBuS-Ph) H H
1-501 H H H H Me 2 -(CH₂)₄-O-(4-iBuS-Ph) H H
1-502 H H H H Me 2 -(CH₂)₄-O-(3-cHx-Ph) H H
1-503 H H H H Me 2 -(CH₂)₄-O-(4-cHx-Ph) H H
1-504 H H H H Me 2 -(CH₂)₄-O-(3-Ph-Ph) H H
1-505 H H H H Me 2 -(CH₂)₄-O-(4-Ph-Ph) H H
1-506 H H H H Me 2 -(CH₂)₄-O-(2,4-diMe-Ph) H H
1-507 H H H H Me 2 -(CH₂)₄-O-(3,4-diMe-Ph) H H
1-508 H H H H Me 2 -(CH₂)₄-O-(3,5-diMe-Ph) H H
1-509 H H H H Me 2 -(CH₂)₅-O-cHx H H
1-510 H H H H Me 2 -(CH₂)₅-O-Ph H H
1-511 H H H H Me 2 -(CH₂)₆-O-cHx H H
1-512 H H H H Me 2 -(CH₂)₆-O-Ph H H
1-513 H H H H Me 2 -(CH₂)₃-OCH₂-cHx H H
1-514 H H Me Me Me 2 -(CH₂)₃-OCH₂-cHx H H
1-515 CO₂Me H H H Me 2 -(CH₂)₃-OCH₂-cHx H H
1-516 CO₂Et H H H Me 2 -(CH₂)₃-OCH₂-cHx H H
1-517 H H H H Me 2 -(CH₂)₃-OCH₂-(4-F-cHx) H H
1-518 H H H H Me 2 -(CH₂)₃-OCH₂-(4-Me-cHx) H H
1-519 H H H H Me 2 -(CH₂)₃-OCH₂-(4-Et-cHx) H H
1-520 H H H H Me 2 -(CH₂)₃-OCH₂-(4-CF₃-cHx) H H
1-521 H H H H Me 2 -(CH₂)₃-OCH₂-(4-MeO-cHx) H H
1-522 H H H H Me 2 -(CH₂)₃-OCH₂-(4-EtO-cHx) H H
1-523 H H H H Me 2 -(CH₂)₃-OCH₂-(4-MeS-cHx) H H
1-524 H H H H Me 2 -(CH₂)₃-OCH₂-(4-cHx-cHx) H H
1-525 H H H H Me 2 -(CH₂)₃-OCH₂-(4-Ph-cHx) H H
1-526 H H H H Me 2 -(CH₂)₃-OCH₂-Ph H H
1-527 H H Me Me Me 2 -(CH₂)₃-OCH₂-Ph H H
1-528 CO₂Me H H H Me 2 -(CH₂)₃-OCH₂-Ph H H
1-529 CO₂Et H H H Me 2 -(CH₂)₃-OCH₂-Ph H H
1-530 H H H H Me 2 -(CH₂)₃-OCH₂-(4-F-Ph) H H
1-531 H H H H Me 2 -(CH₂)₃-OCH₂-(4-Me-Ph) H H
1-532 H H H H Me 2 -(CH₂)₃-OCH₂-(4-Et-Ph) H H
1-533 H H H H Me 2 -(CH₂)₃-OCH₂-(4-CF₃-Ph) H H
1-534 H H H H Me 2 -(CH₂)₃-OCH₂-(4-MeO-Ph) H H
1-535 H H H H Me 2 -(CH₂)₃-OCH₂-(4-EtO-Ph) H H
1-536 H H H H Me 2 -(CH₂)₃-OCH₂-(4-MeS-Ph) H H
1-537 H H H H Me 2 -(CH₂)₃-OCH₂-(4-cHx-Ph) H H
1-538 H H H H Me 2 -(CH₂)₃-OCH₂-(4-Ph-Ph) H H
1-539 H H H H Me 2 -(CH₂)₄-OCH₂-cPn H H
1-540 H H H H Me 2 -(CH₂)₄-OCH₂-cHx H H
1-541 H H H H Me 2 -(CH₂)₄-OCH₂-cHx Me H
1-542 H H H H Me 2 -(CH₂)₄-OCH₂-cHx H Me
1-543 H H H H Me 2 -(CH₂)₄-OCH₂-cHx F H
1-544 H H H H Me 2 -(CH₂)₄-OCH₂-cHx H F
1-545 H H Me Me Me 2 -(CH₂)₄-OCH₂-cHx H H
1-546 CO₂Me H H H Me 2 -(CH₂)₄-OCH₂-cHx H H
1-547 CO₂Et H H H Me 2 -(CH₂)₄-OCH₂-cHx H H
1-548 H H H H Me 2 -(CH₂)₄-OCH₂-(3-F-cHx) H H
1-549 H H H H Me 2 -(CH₂)₄-OCH₂-(4-F-cHx) H H
1-550 H H H H Me 2 -(CH₂)₄-OCH₂-(4-Cl-cHx) H H
1-551 H H H H Me 2 -(CH₂)₄-OCH₂-(4-Br-cHx) H H
1-552 H H H H Me 2 -(CH₂)₄-OCH₂-(3-Me-cHx) H H
1-553 H H H H Me 2 -(CH₂)₄-OCH₂-(4-Me-cHx) H H
1-554 H H H H Me 2 -(CH₂)₄-OCH₂-(3-Et-cHx) H H
1-555 H H H H Me 2 -(CH₂)₄-OCH₂-(4-Et-cHx) H H
1-556 H H H H Me 2 -(CH₂)₄-OCH₂-(3-Pr-cHx) H H
1-557 H H H H Me 2 -(CH₂)₄-OCH₂-(4-Pr-cHx) H H
1-558 H H H H Me 2 -(CH₂)₄-OCH₂-(4-iPr-cHx) H H
1-559 H H H H Me 2 -(CH₂)₄-OCH₂-(3-Bu-cHx) H H
1-560 H H H H Me 2 -(CH₂)₄-OCH₂-(4-Bu-cHx) H H
1-561 H H H H Me 2 -(CH₂)₄-OCH₂-(3-CF₃-cHx) H H
1-562 H H H H Me 2 -(CH₂)₄-OCH₂-(4-CF₃-cHx) H H
1-563 H H H H Me 2 -(CH₂)₄-OCH₂-(3-MeO-cHx) H H
1-564 H H H H Me 2 -(CH₂)₄-OCH₂-(4-MeO-cHx) H H
1-565 H H H H Me 2 -(CH₂)₄-OCH₂-(3-EtO-cHx) H H
1-566 H H H H Me 2 -(CH₂)₄-OCH₂-(4-EtO-cHx) H H
1-567 H H H H Me 2 -(CH₂)₄-OCH₂-(3-PrO-cHx) H H
1-568 H H H H Me 2 -(CH₂)₄-OCH₂-(4-PrO-cHx) H H
1-569 H H H H Me 2 -(CH₂)₄-OCH₂-(3-iPrO-cHx) H H
1-570 H H H H Me 2 -(CH₂)₄-OCH₂-(4-iPrO-cHx) H H
1-571 H H H H Me 2 -(CH₂)₄-OCH₂-[3-(2-Et-PrO)-cHx] H H
1-572 H H H H Me 2 -(CH₂)₄-OCH₂-[4-(2-Et-PrO)-cHx] H H
1-573 H H H H Me 2 -(CH₂)₄-OCH₂-(3-iBuO-cHx) H H
1-574 H H H H Me 2 -(CH₂)₄-OCH₂-(4-iBuO-cHx) H H
1-575 H H H H Me 2 -(CH₂)₄-OCH₂-(3-MeS-cHx) H H
1-576 H H H H Me 2 -(CH₂)₄-OCH₂-(4-MeS-cHx) H H
1-577 H H H H Me 2 -(CH₂)₄-OCH₂-(3-EtS-cHx) H H
1-578 H H H H Me 2 -(CH₂)₄-OCH₂-(4-EtS-cHx) H H
1-579 H H H H Me 2 -(CH₂)₄-OCH₂-(3-PrS-cHx) H H
1-580 H H H H Me 2 -(CH₂)₄-OCH₂-(4-PrS-cHx) H H
1-581 H H H H Me 2 -(CH₂)₄-OCH₂-(3-iPrS-cHx) H H
1-582 H H H H Me 2 -(CH₂)₄-OCH₂-(4-iPrS-cHx) H H
1-583 H H H H Me 2 -(CH₂)₄-OCH₂-[3-(2-Et-PrS)-cHx] H H
1-584 H H H H Me 2 -(CH₂)₄-OCH₂-[4-(2-Et-PrS)-cHx] H H
1-585 H H H H Me 2 -(CH₂)₄-OCH₂-(3-iBuS-cHx) H H
1-586 H H H H Me 2 -(CH₂)₄-OCH₂-(4-iBuS-cHx) H H
1-587 H H H H Me 2 -(CH₂)₄-OCH₂-(3-cHx-cHx) H H
1-588 H H H H Me 2 -(CH₂)₄-OCH₂-(4-cHx-cHx) H H
1-589 H H H H Me 2 -(CH₂)₄-OCH₂-(3-Ph-cHx) H H
1-590 H H H H Me 2 -(CH₂)₄-OCH₂-(4-Ph-cHx) H H
1-591 H H H H Me 2 -(CH₂)₄-OCH₂-(2,4-diMe-cHx) H H
1-592 H H H H Me 2 -(CH₂)₄-OCH₂-(3,4-diMe-cHx) H H
1-593 H H H H Me 2 -(CH₂)₄-OCH₂-(3,5-diMe-cHx) H H
1-594 H H H H Me 2 -(CH₂)₄-OCH₂-Ph H H
1-595 H H H H Me 2 -(CH₂)₄-OCH₂-Ph Me H
1-596 H H H H Me 2 -(CH₂)₄-OCH₂-Ph H Me
1-597 H H H H Me 2 -(CH₂)₄-OCH₂-Ph F H
1-598 H H H H Me 2 -(CH₂)₄-OCH₂-Ph H F
1-599 H H Me Me Me 2 -(CH₂)₄-OCH₂-Ph H H
1-600 CO₂Me H H H Me 2 -(CH₂)₄-OCH₂-Ph H H
1-601 CO₂Et H H H Me 2 -(CH₂)₄-OCH₂-Ph H H
1-602 H H H H Me 2 -(CH₂)₄-OCH₂-(3-F-Ph) H H
1-603 H H H H Me 2 -(CH₂)₄-OCH₂-(4-F-Ph) H H
1-604 H H H H Me 2 -(CH₂)₄-OCH₂-(4-Cl-Ph) H H
1-605 H H H H Me 2 -(CH₂)₄-OCH₂-(4-Br-Ph) H H
1-606 H H H H Me 2 -(CH₂)₄-OCH₂-(3-Me-Ph) H H
1-607 H H H H Me 2 -(CH₂)₄-OCH₂-(4-Me-Ph) H H
1-608 H H H H Me 2 -(CH₂)₄-OCH₂-(3-Et-Ph) H H
1-609 H H H H Me 2 -(CH₂)₄-OCH₂-(4-Et-Ph) H H
1-610 H H H H Me 2 -(CH₂)₄-OCH₂-(3-Pr-Ph) H H
1-611 H H H H Me 2 -(CH₂)₄-OCH₂-(4-Pr-Ph) H H
1-612 H H H H Me 2 -(CH₂)₄-OCH₂-(3-iPr-Ph) H H
1-613 H H H H Me 2 -(CH₂)₄-OCH₂-(4-iPr-Ph) H H
1-614 H H H H Me 2 -(CH₂)₄-OCH₂-(3-Bu-Ph) H H
1-615 H H H H Me 2 -(CH₂)₄-OCH₂-(4-Bu-Ph) H H
1-616 H H H H Me 2 -(CH₂)₄-OCH₂-(3-CF₃-Ph) H H
1-617 H H H H Me 2 -(CH₂)₄-OCH₂-(4-CF₃-Ph) H H
1-618 H H H H Me 2 -(CH₂)₄-OCH₂-(3-MeO-Ph) H H
1-619 H H H H Me 2 -(CH₂)₄-OCH₂-(4-MeO-Ph) H H
1-620 H H H H Me 2 -(CH₂)₄-OCH₂-(3-EtO-Ph) H H
1-621 H H H H Me 2 -(CH₂)₄-OCH₂-(4-EtO-Ph) H H
1-622 H H H H Me 2 -(CH₂)₄-OCH₂-(3-PrO-Ph) H H
1-623 H H H H Me 2 -(CH₂)₄-OCH₂-(4-PrO-Ph) H H
1-624 H H H H Me 2 -(CH₂)₄-OCH₂-(3-iPrO-Ph) H H
1-625 H H H H Me 2 -(CH₂)₄-OCH₂-(4-iPrO-Ph) H H
1-626 H H H H Me 2 -(CH₂)₄-OCH₂-[3-(2-Et-PrO)-Ph] H H
1-627 H H H H Me 2 -(CH₂)₄-OCH₂-[4-(2-Et-PrO)-Ph] H H
1-628 H H H H Me 2 -(CH₂)₄-OCH₂-(3-iBuO-Ph) H H
1-629 H H H H Me 2 -(CH₂)₄-OCH₂-(4-iBuO-Ph) H H
1-630 H H H H Me 2 -(CH₂)₄-OCH₂-(3-MeS-Ph) H H
1-631 H H H H Me 2 -(CH₂)₄-OCH₂-(4-MeS-Ph) H H
1-632 H H H H Me 2 -(CH₂)₄-OCH₂-(3-EtS-Ph) H H
1-633 H H H H Me 2 -(CH₂)₄-OCH₂-(4-EtS-Ph) H H
1-634 H H H H Me 2 -(CH₂)₄-OCH₂-(3-PrS-Ph) H H
1-635 H H H H Me 2 -(CH₂)₄-OCH₂-(4-PrS-Ph) H H
1-636 H H H H Me 2 -(CH₂)₄-OCH₂-(3-iPrS-Ph) H H
1-637 H H H H Me 2 -(CH₂)₄-OCH₂-(4-iPrS-Ph) H H
1-638 H H H H Me 2 -(CH₂)₄-OCH₂-[3-(2-Et-PrS)-Ph] H H
1-639 H H H H Me 2 -(CH₂)₄-OCH₂-[4-(2-Et-PrS)-Ph] H H
1-640 H H H H Me 2 -(CH₂)₄-OCH₂-(3-iBuS-Ph) H H
1-641 H H H H Me 2 -(CH₂)₄-OCH₂-(4-iBuS-Ph) H H
1-642 H H H H Me 2 -(CH₂)₄-OCH₂-(3-cHx-Ph) H H
1-643 H H H H Me 2 -(CH₂)₄-OCH₂-(4-cHx-Ph) H H
1-644 H H H H Me 2 -(CH₂)₄-OCH₂-(3-Ph-Ph) H H
1-645 H H H H Me 2 -(CH₂)₄-OCH₂-(4-Ph-Ph) H H
1-646 H H H H Me 2 -(CH₂)₄-OCH₂-(2,4-diMe-Ph) H H
1-647 H H H H Me 2 -(CH₂)₄-OCH₂-(3,4-diMe-Ph) H H
1-648 H H H H Me 2 -(CH₂)₄-OCH₂-(3,5-diMe-Ph) H H
1-649 H H H H Me 2 -(CH₂)₅-OCH₂-cHx H H
1-650 H H H H Me 2 -(CH₂)₅-OCH₂-Ph H H
1-651 H H H H Me 2 -(CH₂)₆-OCH₂-cHx H H
1-652 H H H H Me 2 -(CH₂)₆-OCH₂-Ph H H
1-653 H H H H Me 2 -CH=CH-cHx H H
1-654 H H H H Me 2 -CH=CH-Ph H H
1-655 H H H H Me 2 -CH=CH-(CH₂)₂-cHx H H
1-656 H H H H Me 2 -CH=CH-(CH₂)₂-Ph H H
1-657 H H H H Me 2 -CH=CH-(CH₂)₃-cHx H H
1-658 H H Me Me Me 2 -CH=CH-(CH₂)₃-cHx H H
1-659 CO₂Me H H H Me 2 -CH=CH-(CH₂)₃-cHx H H
1-660 CO₂Et H H H Me 2 -CH=CH-(CH₂)₃-cHx H H
1-661 H H H H Me 2 -CH=CH-(CH₂)₃-(4-F-cHx) H H
1-662 H H H H Me 2 -CH=CH-(CH₂)₃-(4-Me-cHx) H H
1-663 H H H H Me 2 -CH=CH-(CH₂)₃-(4-Et-cHx) H H
1-664 H H H H Me 2 -CH=CH-(CH₂)₃-(4-CF₃-cHx) H H
1-665 H H H H Me 2 -CH=CH-(CH₂)₃-(4-MeO-cHx) H H
1-666 H H H H Me 2 -CH=CH-(CH₂)₃-(4-EtO-cHx) H H
1-667 H H H H Me 2 -CH=CH-(CH₂)₃-(4-MeS-cHx) H H
1-668 H H H H Me 2 -CH=CH-(CH₂)₃-(4-cHx-cHx) H H
1-669 H H H H Me 2 -CH=CH-(CH₂)₃-(4-Ph-cHx) H H
1-670 H H H H Me 2 -CH=CH-(CH₂)₃-Ph H H
1-671 H H Me Me Me 2 -CH=CH-(CH₂)₃-Ph H H
1-672 CO₂Me H H H Me 2 -CH=CH-(CH₂)₃-Ph H H
1-673 CO₂Et H H H Me 2 -CH=CH-(CH₂)₃-Ph H H
1-674 H H H H Me 2 -CH=CH-(CH₂)₃-(4-F-Ph) H H
1-675 H H H H Me 2 -CH=CH-(CH₂)₃-(4-Me-Ph) H H
1-676 H H H H Me 2 -CH=CH-(CH₂)₃-(4-Et-Ph) H H
1-677 H H H H Me 2 -CH=CH-(CH₂)₃-(4-CF₃-Ph) H H
1-678 H H H H Me 2 -CH=CH-(CH₂)₃-(4-MeO-Ph) H H
1-679 H H H H Me 2 -CH=CH-(CH₂)₃-(4-EtO-Ph) H H
1-680 H H H H Me 2 -CH=CH-(CH₂)₃-(4-MeS-Ph) H H
1-681 H H H H Me 2 -CH=CH-(CH₂)₃-(4-cHx-Ph) H H
1-682 H H H H Me 2 -CH=CH-(CH₂)₃-(4-Ph-Ph) H H
1-683 H H H H Me 2 -CH=CH-(CH₂)₄-cHx H H
1-684 H H Me Me Me 2 -CH=CH-(CH₂)₄-cHx H H
1-685 CO₂Me H H H Me 2 -CH=CH-(CH₂)₄-cHx H H
1-686 CO₂Et H H H Me 2 -CH=CH-(CH₂)₄-cHx H H
1-687 H H H H Me 2 -CH=CH-(CH₂)₄-(4-F-cHx) H H
1-688 H H H H Me 2 -CH=CH-(CH₂)₄-(4-Me-cHx) H H
1-689 H H H H Me 2 -CH=CH-(CH₂)₄-(4-Et-cHx) H H
1-690 H H H H Me 2 -CH=CH-(CH₂)₄-(4-CF₃-cHx) H H
1-691 H H H H Me 2 -CH=CH-(CH₂)₄-(4-MeO-cHx) H H
1-692 H H H H Me 2 -CH=CH-(CH₂)₄-(4-EtO-cHx) H H
1-693 H H H H Me 2 -CH=CH-(CH₂)₄-(4-MeS-cHx) H H
1-694 H H H H Me 2 -CH=CH-(CH₂)₄-(4-cHx-cHx) H H
1-695 H H H H Me 2 -CH=CH-(CH₂)₄-(4-Ph-cHx) H H
1-696 H H H H Me 2 -CH=CH-(CH₂)₄-Ph H H
1-697 H H Me Me Me 2 -CH=CH-(CH₂)₄-Ph H H
1-698 CO₂Me H H H Me 2 -CH=CH-(CH₂)₄-Ph H H
1-699 CO₂Et H H H Me 2 -CH=CH-(CH₂)₄-Ph H H
1-700 H H H H Me 2 -CH=CH-(CH₂)₄-(4-F-Ph) H H
1-701 H H H H Me 2 -CH=CH-(CH₂)₄-(4-Me-Ph) H H
1-702 H H H H Me 2 -CH=CH-(CH₂)₄-(4-Et-Ph) H H
1-703 H H H H Me 2 -CH=CH-(CH₂)₄-(4-CF₃-Ph) H H
1-704 H H H H Me 2 -CH=CH-(CH₂)₄-(4-MeO-Ph) H H
1-705 H H H H Me 2 -CH=CH-(CH₂)₄-(4-EtO-Ph) H H
1-706 H H H H Me 2 -CH=CH-(CH₂)₄-(4-MeS-Ph) H H
1-707 H H H H Me 2 -CH=CH-(CH₂)₄-(4-cHx-Ph) H H
1-708 H H H H Me 2 -CH=CH-(CH₂)₄-(4-Ph-Ph) H H
1-709 H H H H Me 2 -CH=CH-(CH₂)₅-cHx H H
1-710 H H H H Me 2 -CH=CH-(CH₂)₅-Ph H H
1-711 H H H H Me 2 -CH=CH-(CH₂)₆-cHx H H
1-712 H H H H Me 2 -CH=CH-(CH₂)₆-Ph H H
1-713 H H H H Me 2 -C=C-CH₂O-cHx H H
1-714 H H H H Me 2 -C=C-CH₂O-Ph H H
1-715 H H H H Me 2 -C=C-(CH₂)₂O-cHx H H
1-716 H H H H Me 2 -C=C-(CH₂)₂O-Ph H H
1-717 H H H H Me 2 -C≡C-cHx H H
1-718 H H Me Me Me 2 -C≡C-cHx H H
1-719 CO₂Me H H H Me 2 -C≡C-cHx H H
1-720 CO₂Et H H H Me 2 -C≡C-cHx H H
1-721 H H H H Me 2 -C≡C-(4-F-cHx) H H
1-722 H H H H Me 2 -C≡C-(4-Me-cHx) H H
1-723 H H H H Me 2 -C≡C-(4-Et-cHx) H H
1-724 H H H H Me 2 -C≡C-(4-CF₃-cHx) H H
1-725 H H H H Me 2 -C≡C-(4-MeO-cHx) H H
1-726 H H H H Me 2 -C≡C-(4-EtO-cHx) H H
1-727 H H H H Me 2 -C≡C-(4-MeS-cHx) H H
1-728 H H H H Me 2 -C≡C-(4-cHx-cHx) H H
1-729 H H H H Me 2 -C≡C-(4-Ph-cHx) H H
1-730 H H H H Me 2 -C≡C-Ph H H
1-731 H H Me Me Me 2 -C≡C-Ph H H
1-732 CO₂Me H H H Me 2 -C≡C-Ph H H
1-733 CO₂Et H H H Me 2 -C≡C-Ph H H
1-734 H H H H Me 2 -C≡C-(4-F-Ph) H H
1-735 H H H H Me 2 -C≡C-(4-Me-Ph) H H
1-736 H H H H Me 2 -C≡C-(4-Pr-Ph) H H
1-737 H H H H Me 2 -C≡C-(4-Bu-Ph) H H
1-738 H H H H Me 2 -C≡C-(4-MeO-Ph) H H
1-739 H H H H Me 2 -C≡C-(4-EtO-Ph) H H
1-740 H H H H Me 2 -C≡C-(4-PrO-Ph) H H
1-741 H H H H Me 2 -C≡C-(4-cHx-Ph) H H
1-742 H H H H Me 2 -C≡C-(4-Ph-Ph) H H
1-743 H H H H Me 2 -C≡C-(CH₂)₂-cHx H H
1-744 H H Me Me Me 2 -C≡C-(CH₂)₂-cHx H H
1-745 CO₂Me H H H Me 2 -C≡C-(CH₂)₂-cHx H H
1-746 CO₂Et H H H Me 2 -C≡C-(CH₂)₂-cHx H H
1-747 H H H H Me 2 -C≡C-(CH₂)₂-(4-F-cHx) H H
1-748 H H H H Me 2 -C≡C-(CH₂)₂-(4-Me-cHx) H H
1-749 H H H H Me 2 -C≡C-(CH₂)₂-(4-Et-cHx) H H
1-750 H H H H Me 2 -C≡C-(CH₂)₂-(4-CF₃-cHx) H H
1-751 H H H H Me 2 -C≡C-(CH₂)₂-(4-MeO-cHx) H H
1-752 H H H H Me 2 -C≡C-(CH₂)₂-(4-EtO-cHx) H H
1-753 H H H H Me 2 -C≡C-(CH₂)₂-(4-MeS-cHx) H H
1-754 H H H H Me 2 -C≡C-(CH₂)₂-(4-cHx-cHx) H H
1-755 H H H H Me 2 -C≡C-(CH₂)₂-(4-Ph-cHx) H H
1-756 H H H H Me 2 -C≡C-(CH₂)₂-Ph H H
1-757 H H Me Me Me 2 -C≡C-(CH₂)₂-Ph H H
1-758 CO₂Me H H H Me 2 -C≡C-(CH₂)₂-Ph H H
1-759 CO₂Et H H H Me 2 -C≡C-(CH₂)₂-Ph H H
1-760 H H H H Me 2 -C≡C-(CH₂)₂-(4-F-Ph) H H
1-761 H H H H Me 2 -C≡C-(CH₂)₂-(4-Me-Ph) H H
1-762 H H H H Me 2 -C≡C-(CH₂)₂-(4-Et-Ph) H H
1-763 H H H H Me 2 -C≡C-(CH₂)₂-(4-CF₃-Ph) H H
1-764 H H H H Me 2 -C≡C-(CH₂)₂-(4-MeO-Ph) H H
1-765 H H H H Me 2 -C≡C-(CH₂)₂-(4-EtO-Ph) H H
1-766 H H H H Me 2 -C≡C-(CH₂)₂-(4-MeS-Ph) H H
1-767 H H H H Me 2 -C≡C-(CH₂)₂-(4-cHx-Ph) H H
1-768 H H H H Me 2 -C≡C-(CH₂)₂-(4-Ph-Ph) H H
1-769 H H H H Me 2 -C≡C-(CH₂)₃-cPn H H
1-770 H H H H Me 2 -C≡C-(CH₂)₃-cHx H H
1-771 H H H H Me 2 -C≡C-(CH₂)₃-cHx Me H
1-772 H H H H Me 2 -C≡C-(CH₂)₃-cHx H Me
1-773 H H H H Me 2 -C≡C-(CH₂)₃-cHx F H
1-774 H H H H Me 2 -C≡C-(CH₂)₃-cHx H F
1-775 H H Me Me Me 2 -C≡C-(CH₂)₃-cHx H H
1-776 CO₂Me H H H Me 2 -C≡C-(CH₂)₃-cHx H H
1-777 CO₂Et H H H Me 2 -C≡C-(CH₂)₃-cHx H H
1-778 H H H H Me 2 -C≡C-(CH₂)₃-(3-F-cHx) H H
1-779 H H H H Me 2 -C≡C-(CH₂)₃-(4-F-cHx) H H
1-780 H H H H Me 2 -C≡C-(CH₂)₃-(4-Cl-cHx) H H
1-781 H H H H Me 2 -C≡C-(CH₂)₃-(4-Br-cHx) H H
1-782 H H H H Me 2 -C≡C-(CH₂)₃-(3-Me-cHx) H H
1-783 H H H H Me 2 -C≡C-(CH₂)₃-(4-Me-cHx) H H
1-784 H H H H Me 2 -C≡C-(CH₂)₃-(3-Et-cHx) H H
1-785 H H H H Me 2 -C≡C-(CH₂)₃-(4-Et-cHx) H H
1-786 H H H H Me 2 -C≡C-(CH₂)₃-(3-Pr-cHx) H H
1-787 H H H H Me 2 -C≡C-(CH₂)₃-(4-Pr-cHx) H H
1-788 H H H H Me 2 -C≡C-(CH₂)₃-(4-iPr-cHx) H H
1-789 H H H H Me 2 -C≡C-(CH₂)₃-(3-Bu-cHx) H H
1-790 H H H H Me 2 -C≡C-(CH₂)₃-(4-Bu-cHx) H H
1-791 H H H H Me 2 -C≡C-(CH₂)₃-(3-CF₃-cHx) H H
1-792 H H H H Me 2 -C≡C-(CH₂)₃-(4-CF₃-cHx) H H
1-793 H H H H Me 2 -C≡C-(CH₂)₃-(3-MeO-cHx) H H
1-794 H H H H Me 2 -C≡C-(CH₂)₃-(4-MeO-cHx) H H
1-795 H H H H Me 2 -C≡C-(CH₂)₃-(3-EtO-cHx) H H
1-796 H H H H Me 2 -C≡C-(CH₂)₃-(4-EtO-cHx) H H
1-797 H H H H Me 2 -C≡C-(CH₂)₃-(3-PrO-cHx) H H
1-798 H H H H Me 2 -C≡C-(CH₂)₃-(4-PrO-cHx) H H
1-799 H H H H Me 2 -C≡C-(CH₂)₃-(3-iPrO-cHx) H H
1-800 H H H H Me 2 -C≡C-(CH₂)₃-(4-iPrO-cHx) H H
1-801 H H H H Me 2 -C≡C-(CH₂)₃-[3-(2-Et-PrO)-cHx] H H
1-802 H H H H Me 2 -C≡C-(CH₂)₃-[4-(2-Et-PrO)-cHx] H H
1-803 H H H H Me 2 -C≡C-(CH₂)₃-(3-iBuO-cHx) H H
1-804 H H H H Me 2 -C≡C-(CH₂)₃-(4-iBuO-cHx) H H
1-805 H H H H Me 2 -C≡C-(CH₂)₃-(3-MeS-cHx) H H
1-806 H H H H Me 2 -C≡C-(CH₂)₃-(4-MeS-cHx) H H
1-807 H H H H Me 2 -C≡C-(CH₂)₃-(3-EtS-cHx) H H
1-808 H H H H Me 2 -C≡C-(CH₂)₃-(4-EtS-cHx) H H
1-809 H H H H Me 2 -C≡C-(CH₂)₃-(3-PrS-cHx) H H
1-810 H H H H Me 2 -C≡C-(CH₂)₃-(4-PrS-cHx) H H
1-811 H H H H Me 2 -C≡C-(CH₂)₃-(3-iPrS-cHx) H H
1-812 H H H H Me 2 -C≡C-(CH₂)₃-(4-iPrS-cHx) H H
1-813 H H H H Me 2 -C≡C-(CH₂)₃-[3-(2-Et-PrS)-cHx] H H
1-814 H H H H Me 2 -C≡C-(CH₂)₃-[4-(2-Et-PrS)-cHx] H H
1-815 H H H H Me 2 -C≡C-(CH₂)₃-(3-iBuS-cHx) H H
1-816 H H H H Me 2 -C≡C-(CH₂)₃-(4-iBuS-cHx) H H
1-817 H H H H Me 2 -C≡C-(CH₂)₃-(3-cHx-cHx) H H
1-818 H H H H Me 2 -C≡C-(CH₂)₃-(4-cHx-cHx) H H
1-819 H H H H Me 2 -C≡C-(CH₂)₃-(3-Ph-cHx) H H
1-820 H H H H Me 2 -C≡C-(CH₂)₃-(4-Ph-cHx) H H
1-821 H H H H Me 2 -C≡C-(CH₂)₃-(2,4-diMe-cHx) H H
1-822 H H H H Me 2 -C≡C-(CH₂)₃-(3,4-diMe-cHx) H H
1-823 H H H H Me 2 -C≡C-(CH₂)₃-(3,5-diMe-cHx) H H
1-824 H H H H Me 2 -C≡C-(CH₂)₃-Ph H H
1-825 H H H H Me 2 -C≡C-(CH₂)₃-Ph Me H
1-826 H H H H Me 2 -C≡C-(CH₂)₃-Ph H Me
1-827 H H H H Me 2 -C≡C-(CH₂)₃-Ph F H
1-828 H H H H Me 2 -C≡C-(CH₂)₃-Ph H F
1-829 H H Me Me Me 2 -C≡C-(CH₂)₃-Ph H H
1-830 CO₂Me H H H Me 2 -C≡C-(CH₂)₃-Ph H H
1-831 CO₂Et H H H Me 2 -C≡C-(CH₂)₃-Ph H H
1-832 H H H H Me 2 -C≡C-(CH₂)₃-(3-F-Ph) H H
1-833 H H H H Me 2 -C≡C-(CH₂)₃-(4-F-Ph) H H
1-834 H H H H Me 2 -C≡C-(CH₂)₃-(4-Cl-Ph) H H
1-835 H H H H Me 2 -C≡C-(CH₂)₃-(4-Br-Ph) H H
1-836 H H H H Me 2 -C≡C-(CH₂)₃-(3-Me-Ph) H H
1-837 H H H H Me 2 -C≡C-(CH₂)₃-(4-Me-Ph) H H
1-838 H H H H Me 2 -C≡C-(CH₂)₃-(3-Et-Ph) H H
1-839 H H H H Me 2 -C≡C-(CH₂)₃-(4-Et-Ph) H H
1-840 H H H H Me 2 -C≡C-(CH₂)₃-(3-Pr-Ph) H H
1-841 H H H H Me 2 -C≡C-(CH₂)₃-(4-Pr-Ph) H H
1-842 H H H H Me 2 -C≡C-(CH₂)₃-(3-iPr-Ph) H H
1-843 H H H H Me 2 -C≡C-(CH₂)₃-(4-iPr-Ph) H H
1-844 H H H H Me 2 -C≡C-(CH₂)₃-(3-Bu-Ph) H H
1-845 H H H H Me 2 -C≡C-(CH₂)₃-(4-Bu-Ph) H H
1-846 H H H H Me 2 -C≡C-(CH₂)₃-(3-CF₃-Ph) H H
1-847 H H H H Me 2 -C≡C-(CH₂)₃-(4-CF₃-Ph) H H
1-848 H H H H Me 2 -C≡C-(CH₂)₃-(3-MeO-Ph) H H
1-849 H H H H Me 2 -C≡C-(CH₂)₃-(4-MeO-Ph) H H
1-850 H H H H Me 2 -C≡C-(CH₂)₃-(3-EtO-Ph) H H
1-851 H H H H Me 2 -C≡C-(CH₂)₃-(4-EtO-Ph) H H
1-852 H H H H Me 2 -C≡C-(CH₂)₃-(3-PrO-Ph) H H
1-853 H H H H Me 2 -C≡C-(CH₂)₃-(4-PrO-Ph) H H
1-854 H H H H Me 2 -C≡C-(CH₂)₃-(3-iPrO-Ph) H H
1-855 H H H H Me 2 -C≡C-(CH₂)₃-(4-iPrO-Ph) H H
1-856 H H H H Me 2 -C≡C-(CH₂)₃-[3-(2-Et-PrO)-Ph] H H
1-857 H H H H Me 2 -C≡C-(CH₂)₃-[4-(2-Et-PrO)-Ph] H H
1-858 H H H H Me 2 -C≡C-(CH₂)₃-(3-iBuO-Ph) H H
1-859 H H H H Me 2 -C≡C-(CH₂)₃-(4-iBuO-Ph) H H
1-860 H H H H Me 2 -C≡C-(CH₂)₃-(3-MeS-Ph) H H
1-861 H H H H Me 2 -C≡C-(CH₂)₃-(4-MeS-Ph) H H
1-862 H H H H Me 2 -C≡C-(CH₂)₃-(3-EtS-Ph) H H
1-863 H H H H Me 2 -C≡C-(CH₂)₃-(4-EtS-Ph) H H
1-864 H H H H Me 2 -C≡C-(CH₂)₃-(3-PrS-Ph) H H
1-865 H H H H Me 2 -C≡C-(CH₂)₃-(4-PrS-Ph) H H
1-866 H H H H Me 2 -C≡C-(CH₂)₃-(3-iPrS-Ph) H H
1-867 H H H H Me 2 -C≡C-(CH₂)₃-(4-iPrS-Ph) H H
1-868 H H H H Me 2 -C≡C-(CH₂)₃-[3-(2-Et-PrS)-Ph] H H
1-869 H H H H Me 2 -C≡C-(CH₂)₃-[4-(2-Et-PrS)-Ph] H H
1-870 H H H H Me 2 -C≡C-(CH₂)₃-(3-iBuS-Ph) H H
1-871 H H H H Me 2 -C≡C-(CH₂)₃-(4-iBuS-Ph) H H
1-872 H H H H Me 2 -C≡C-(CH₂)₃-(3-cHx-Ph) H H
1-873 H H H H Me 2 -C≡C-(CH₂)₃-(4-cHx-Ph) H H
1-874 H H H H Me 2 -C≡C-(CH₂)₃-(3-Ph-Ph) H H
1-875 H H H H Me 2 -C≡C-(CH₂)₃-(4-Ph-Ph) H H
1-876 H H H H Me 2 -C≡C-(CH₂)₃-(2,4-diMe-Ph) H H
1-877 H H H H Me 2 -C≡C-(CH₂)₃-(3,4-diMe-Ph) H H
1-878 H H H H Me 2 -C≡C-(CH₂)₃-(3,5-diMe-Ph) H H
1-879 H H H H Me 2 -C≡C-(CH₂)₃-Np(1) H H
1-880 H H H H Me 2 -C≡C-(CH₂)₃-Np(2) H H
1-881 H H H H Me 2 -C≡C-(CH₂)₄-cPn H H
1-882 H H H H Me 2 -C≡C-(CH₂)₄-cHx H H
1-883 H H H H Me 2 -C≡C-(CH₂)₄-cHx Me H
1-884 H H H H Me 2 -C≡C-(CH₂)₄-cHx H Me
1-885 H H H H Me 2 -C≡C-(CH₂)₄-cHx F H
1-886 H H H H Me 2 -C≡C-(CH₂)₄-cHx H F
1-887 H H Me Me Me 2 -C≡C-(CH₂)₄-cHx H H
1-888 CO₂Me H H H Me 2 -C≡C-(CH₂)₄-cHx H H
1-889 CO₂Et H H H Me 2 -C≡C-(CH₂)₄-cHx H H
1-890 H H H H Me 2 -C≡C-(CH₂)₄-(3-F-cHx) H H
1-891 H H H H Me 2 -C≡C-(CH₂)₄-(4-F-cHx) H H
1-892 H H H H Me 2 -C≡C-(CH₂)₄-(4-Cl-cHx) H H
1-893 H H H H Me 2 -C≡C-(CH₂)₄-(4-Br-cHx) H H
1-894 H H H H Me 2 -C≡C-(CH₂)₄-(3-Me-cHx) H H
1-895 H H H H Me 2 -C≡C-(CH₂)₄-(4-Me-cHx) H H
1-896 H H H H Me 2 -C≡C-(CH₂)₄-(3-Et-cHx) H H
1-897 H H H H Me 2 -C≡C-(CH₂)₄-(4-Et-cHx) H H
1-898 H H H H Me 2 -C≡C-(CH₂)₄-(3-Pr-cHx) H H
1-899 H H H H Me 2 -C≡C-(CH₂)₄-(4-Pr-cHx) H H
1-900 H H H H Me 2 -C≡C-(CH₂)₄-(4-iPr-cHx) H H
1-901 H H H H Me 2 -C≡C-(CH₂)₄-(3-Bu-cHx) H H
1-902 H H H H Me 2 -C≡C-(CH₂)₄-(4-Bu-cHx) H H
1-903 H H H H Me 2 -C≡C-(CH₂)₄-(3-CF₃-cHx) H H
1-904 H H H H Me 2 -C≡C-(CH₂)₄-(4-CF₃-cHx) H H
1-905 H H H H Me 2 -C≡C-(CH₂)₄-(3-MeO-cHx) H H
1-906 H H H H Me 2 -C≡C-(CH₂)₄-(4-MeO-cHx) H H
1-907 H H H H Me 2 -C≡C-(CH₂)₄-(3-EtO-cHx) H H
1-908 H H H H Me 2 -C≡C-(CH₂)₄-(4-EtO-cHx) H H
1-909 H H H H Me 2 -C≡C-(CH₂)₄-(3-PrO-cHx) H H
1-910 H H H H Me 2 -C≡C-(CH₂)₄-(4-PrO-cHx) H H
1-911 H H H H Me 2 -C≡C-(CH₂)₄-(3-iPrO-cHx) H H
1-912 H H H H Me 2 -C≡C-(CH₂)₄-(4-iPrO-cHx) H H
1-913 H H H H Me 2 -C≡C-(CH₂)₄-[3-(2-Et-PrO)-cHx] H H
1-914 H H H H Me 2 -C≡C-(CH₂)₄-[4-(2-Et-PrO)-cHx] H H
1-915 H H H H Me 2 -C≡C-(CH₂)₄-(3-iBuO-cHx) H H
1-916 H H H H Me 2 -C≡C-(CH₂)₄-(4-iBuO-cHx) H H
1-917 H H H H Me 2 -C≡C-(CH₂)₄-(3-MeS-cHx) H H
1-918 H H H H Me 2 -C≡C-(CH₂)₄-(4-MeS-cHx) H H
1-919 H H H H Me 2 -C≡C-(CH₂)₄-(3-EtS-cHx) H H
1-920 H H H H Me 2 -C≡C-(CH₂)₄-(4-EtS-cHx) H H
1-921 H H H H Me 2 -C≡C-(CH₂)₄-(3-PrS-cHx) H H
1-922 H H H H Me 2 -C≡C-(CH₂)₄-(4-PrS-cHx) H H
1-923 H H H H Me 2 -C≡C-(CH₂)₄-(3-iPrS-cHx) H H
1-924 H H H H Me 2 -C≡C-(CH₂)₄-(4-iPrS-cHx) H H
1-925 H H H H Me 2 -C≡C-(CH₂)₄-[3-(2-Et-PrS)-cHx] H H
1-926 H H H H Me 2 -C≡C-(CH₂)₄-[4-(2-Et-PrS)-cHx] H H
1-927 H H H H Me 2 -C≡C-(CH₂)₄-(3-iBuS-cHx) H H
1-928 H H H H Me 2 -C≡C-(CH₂)₄-(4-iBuS-cHx) H H
1-929 H H H H Me 2 -C≡C-(CH₂)₄-(3-cHx-cHx) H H
1-930 H H H H Me 2 -C≡C-(CH₂)₄-(4-cHx-cHx) H H
1-931 H H H H Me 2 -C≡C-(CH₂)₄-(3-Ph-cHx) H H
1-932 H H H H Me 2 -C≡C-(CH₂)₄-(4-Ph-cHx) H H
1-933 H H H H Me 2 -C≡C-(CH₂)₄-(2,4-diMe-cHx) H H
1-934 H H H H Me 2 -C≡C-(CH₂)₄-(3,4-diMe-cHx) H H
1-935 H H H H Me 2 -C≡C-(CH₂)₄-(3,5-diMe-cHx) H H
1-936 H H H H Me 2 -C≡C-(CH₂)₄-Ph H H
1-937 H H H H Me 2 -C≡C-(CH₂)₄-Ph Me H
1-938 H H H H Me 2 -C≡C-(CH₂)₄-Ph H Me
1-939 H H H H Me 2 -C≡C-(CH₂)₄-Ph F H
1-940 H H H H Me 2 -C≡C-(CH₂)₄-Ph H F
1-941 H H Me Me Me 2 -C≡C-(CH₂)₄-Ph H H
1-942 CO₂Me H H H Me 2 -C≡C-(CH₂)₄-Ph H H
1-943 CO₂Et H H H Me 2 -C≡C-(CH₂)₄-Ph H H
1-944 H H H H Me 2 -C≡C-(CH₂)₄-(3-F-Ph) H H
1-945 H H H H Me 2 -C≡C-(CH₂)₄-(4-F-Ph) H H
1-946 H H H H Me 2 -C≡C-(CH₂)₄-(4-Cl-Ph) H H
1-947 H H H H Me 2 -C≡C-(CH₂)₄-(4-Br-Ph) H H
1-948 H H H H Me 2 -C≡C-(CH₂)₄-(3-Me-Ph) H H
1-949 H H H H Me 2 -C≡C-(CH₂)₄-(4-Me-Ph) H H
1-950 H H H H Me 2 -C≡C-(CH₂)₄-(3-Et-Ph) H H
1-951 H H H H Me 2 -C≡C-(CH₂)₄-(4-Et-Ph) H H
1-952 H H H H Me 2 -C≡C-(CH₂)₄-(3-Pr-Ph) H H
1-953 H H H H Me 2 -C≡C-(CH₂)₄-(4-Pr-Ph) H H
1-954 H H H H Me 2 -C≡C-(CH₂)₄-(3-iPr-Ph) H H
1-955 H H H H Me 2 -C≡C-(CH₂)₄-(4-iPr-Ph) H H
1-956 H H H H Me 2 -C≡C-(CH₂)₄-(3-Bu-Ph) H H
1-957 H H H H Me 2 -C≡C-(CH₂)₄-(4-Bu-Ph) H H
1-958 H H H H Me 2 -C≡C-(CH₂)₄-(3-CF₃-Ph) H H
1-959 H H H H Me 2 -C≡C-(CH₂)₄-(4-CF₃-Ph) H H
1-960 H H H H Me 2 -C≡C-(CH₂)₄-(3-MeO-Ph) H H
1-961 H H H H Me 2 -C≡C-(CH₂)₄-(4-MeO-Ph) H H
1-962 H H H H Me 2 -C≡C-(CH₂)₄-(3-EtO-Ph) H H
1-963 H H H H Me 2 -C≡C-(CH₂)₄-(4-EtO-Ph) H H
1-964 H H H H Me 2 -C≡C-(CH₂)₄-(3-PrO-Ph) H H
1-965 H H H H Me 2 -C≡C-(CH₂)₄-(4-PrO-Ph) H H
1-966 H H H H Me 2 -C≡C-(CH₂)₄-(3-iPrO-Ph) H H
1-967 H H H H Me 2 -C≡C-(CH₂)₄-(4-iPrO-Ph) H H
1-968 H H H H Me 2 -C≡C-(CH₂)₄-[3-(2-Et-PrO)-Ph] H H
1-969 H H H H Me 2 -C≡C-(CH₂)₄-[4-(2-Et-PrO)-Ph] H H
1-970 H H H H Me 2 -C≡C-(CH₂)₄-(3-iBuO-Ph) H H
1-971 H H H H Me 2 -C≡C-(CH₂)₄-(4-iBuO-Ph) H H
1-972 H H H H Me 2 -C≡C-(CH₂)₄-(3-MeS-Ph) H H
1-973 H H H H Me 2 -C≡C-(CH₂)₄-(4-MeS-Ph) H H
1-974 H H H H Me 2 -C≡C-(CH₂)₄-(3-EtS-Ph) H H
1-975 H H H H Me 2 -C≡C-(CH₂)₄-(4-EtS-Ph) H H
1-976 H H H H Me 2 -C≡C-(CH₂)₄-(3-PrS-Ph) H H
1-977 H H H H Me 2 -C≡C-(CH₂)₄-(4-PrS-Ph) H H
1-978 H H H H Me 2 -C≡C-(CH₂)₄-(3-iPrS-Ph) H H
1-979 H H H H Me 2 -C≡C-(CH₂)₄-(4-iPrS-Ph) H H
1-980 H H H H Me 2 -C≡C-(CH₂)₄-[3-(2-Et-PrS)-Ph] H H
1-981 H H H H Me 2 -C≡C-(CH₂)₄-[4-(2-Et-PrS)-Ph] H H
1-982 H H H H Me 2 -C≡C-(CH₂)₄-(3-iBuS-Ph) H H
1-983 H H H H Me 2 -C≡C-(CH₂)₄-(4-iBuS-Ph) H H
1-984 H H H H Me 2 -C≡C-(CH₂)₄-(3-cHx-Ph) H H
1-985 H H H H Me 2 -C≡C-(CH₂)₄-(4-cHx-Ph) H H
1-986 H H H H Me 2 -C≡C-(CH₂)₄-(3-Ph-Ph) H H
1-987 H H H H Me 2 -C≡C-(CH₂)₄-(4-Ph-Ph) H H
1-988 H H H H Me 2 -C≡C-(CH₂)₄-(2,4-diMe-Ph) H H
1-989 H H H H Me 2 -C≡C-(CH₂)₄-(3,4-diMe-Ph) H H
1-990 H H H H Me 2 -C≡C-(CH₂)₄-(3,5-diMe-Ph) H H
1-991 H H H H Me 2 -C≡C-(CH₂)₄-Np(1) H H
1-992 H H H H Me 2 -C≡C-(CH₂)₄-Np(2) H H
1-993 H H H H Me 2 -C≡C-(CH₂)₅-cHx H H
1-994 H H Me Me Me 2 -C≡C-(CH₂)₅-cHx H H
1-995 CO₂Me H H H Me 2 -C≡C-(CH₂)₅-cHx H H
1-996 CO₂Et H H H Me 2 -C≡C-(CH₂)₅-cHx H H
1-997 H H H H Me 2 -C≡C-(CH₂)₅-(4-F-cHx) H H
1-998 H H H H Me 2 -C≡C-(CH₂)₅-(4-Me-cHx) H H
1-999 H H H H Me 2 -C≡C-(CH₂)₅-(4-Et-cHx) H H
1-1000 H H H H Me 2 -C≡C-(CH₂)₅-(4-CF₃-cHx) H H
1-1001 H H H H Me 2 -C≡C-(CH₂)₅-(4-MeO-cHx) H H
1-1002 H H H H Me 2 -C≡C-(CH₂)₅-(4-EtO-cHx) H H
1-1003 H H H H Me 2 -C≡C-(CH₂)₅-(4-MeS-cHx) H H
1-1004 H H H H Me 2 -C≡C-(CH₂)₅-(4-cHx-cHx) H H
1-1005 H H H H Me 2 -C≡C-(CH₂)₅-(4-Ph-cHx) H H
1-1006 H H H H Me 2 -C≡C-(CH₂)₅-Ph H H
1-1007 H H Me Me Me 2 -C≡C-(CH₂)₅-Ph H H
1-1008 CO₂Me H H H Me 2 -C≡C-(CH₂)₅-Ph H H
1-1009 CO₂Et H H H Me 2 -C≡C-(CH₂)₅-Ph H H
1-1010 H H H H Me 2 -C≡C-(CH₂)₅-(4-F-Ph) H H
1-1011 H H H H Me 2 -C≡C-(CH₂)₅-(4-Me-Ph) H H
1-1012 H H H H Me 2 -C≡C-(CH₂)₅-(4-Et-Ph) H H
1-1013 H H H H Me 2 -C≡C-(CH₂)₅-(4-CF₃-Ph) H H
1-1014 H H H H Me 2 -C≡C-(CH₂)₅-(4-MeO-Ph) H H
1-1015 H H H H Me 2 -C≡C-(CH₂)₅-(4-EtO-Ph) H H
1-1016 H H H H Me 2 -C≡C-(CH₂)₅-(4-MeS-Ph) H H
1-1017 H H H H Me 2 -C≡C-(CH₂)₅-(4-cHx-Ph) H H
1-1018 H H H H Me 2 -C≡C-(CH₂)₅-(4-Ph-Ph) H H
1-1019 H H H H Me 2 -C≡C-(CH₂)₆-cHx H H
1-1020 H H Me Me Me 2 -C≡C-(CH₂)₆-cHx H H
1-1021 CO₂Me H H H Me 2 -C≡C-(CH₂)₆-cHx H H
1-1022 CO₂Et H H H Me 2 -C≡C-(CH₂)₆-cHx H H
1-1023 H H H H Me 2 -C≡C-(CH₂)₆-(4-F-cHx) H H
1-1024 H H H H Me 2 -C≡C-(CH₂)₆-(4-Me-cHx) H H
1-1025 H H H H Me 2 -C≡C-(CH₂)₆-(4-Et-cHx) H H
1-1026 H H H H Me 2 -C≡C-(CH₂)₆-(4-CF₃-cHx) H H
1-1027 H H H H Me 2 -C≡C-(CH₂)₆-(4-MeO-cHx) H H
1-1028 H H H H Me 2 -C≡C-(CH₂)₆-(4-EtO-cHx) H H
1-1029 H H H H Me 2 -C≡C-(CH₂)₆-(4-MeS-cHx) H H
1-1030 H H H H Me 2 -C≡C-(CH₂)₆-(4-cHx-cHx) H H
1-1031 H H H H Me 2 -C≡C-(CH₂)₆-(4-Ph-cHx) H H
1-1032 H H H H Me 2 -C≡C-(CH₂)₆-Ph H H
1-1033 H H Me Me 2 -C≡C-(CH₂)₆-Ph H H
1-1034 CO₂Me H H Me 2 -C≡C-(CH₂)₆-Ph H H
1-1035 CO₂Et H H Me 2 -C≡C-(CH₂)₆-Ph H H
1-1036 H H H H Me 2 -C≡C-(CH₂)₆-(4-F-Ph) H H
1-1037 H H H H Me 2 -C≡C-(CH₂)₆-(4-Me-Ph) H H
1-1038 H H H H Me 2 -C≡C-(CH₂)₆-(4-Et-Ph) H H
1-1039 H H H H Me 2 -C≡C-(CH₂)₆-(4-CF₃-Ph) H H
1-1040 H H H H Me 2 -C≡C-(CH₂)₆-(4-MeO-Ph) H H
1-1041 H H H H Me 2 -C≡C-(CH₂)₆-(4-EtO-Ph) H H
1-1042 H H H H Me 2 -C≡C-(CH₂)₆-(4-MeS-Ph) H H
1-1043 H H H H Me 2 -C≡C-(CH₂)₆-(4-cHx-Ph) H H
1-1044 H H H H Me 2 -C≡C-(CH₂)₆-(4-Ph-Ph) H H
1-1045 H H H H Me 2 -C≡C-CH₂-O-cHx H H
1-1046 H H Me Me Me 2 -C≡C-CH₂-O-cHx H H
1-1047 CO₂Me H H H Me 2 -C≡C-CH₂-O-cHx H H
1-1048 CO₂Et H H H Me 2 -C≡C-CH₂-O-cHx H H
1-1049 H H H H Me 2 -C≡C-CH₂-O-(4-F-cHx) H H
1-1050 H H H H Me 2 -C≡C-CH₂-O-(4-Me-cHx) H H
1-1051 H H H H Me 2 -C≡C-CH₂-O-(4-Et-cHx) H H
1-1052 H H H H Me 2 -C≡C-CH₂-O-(4-CF₃-cHx) H H
1-1053 H H H H Me 2 -C≡C-CH₂-O-(4-MeO-cHx) H H
1-1054 H H H H Me 2 -C≡C-CH₂-O-(4-EtO-cHx) H H
1-1055 H H H H Me 2 -C≡C-CH₂-O-(4-MeS-cHx) H H
1-1056 H H H H Me 2 -C≡C-CH₂-O-(4-cHx-cHx) H H
1-1057 H H H H Me 2 -C≡C-CH₂-O-(4-Ph-cHx) H H
1-1058 H H H H Me 2 -C≡C-CH₂-O-Ph H H
1-1059 H H Me Me Me 2 -C≡C-CH₂-O-Ph H H
1-1060 CO₂Me H H H Me 2 -C≡C-CH₂-O-Ph H H
1-1061 CO₂Et H H H Me 2 -C≡C-CH₂-O-Ph H H
1-1062 H H H H Me 2 -C≡C-CH₂-O-(4-F-Ph) H H
1-1063 H H H H Me 2 -C≡C-CH₂-O-(4-Me-Ph) H H
1-1064 H H H H Me 2 -C≡C-CH₂-O-(4-Et-Ph) H H
1-1065 H H H H Me 2 -C≡C-CH₂-O-(4-CF₃-Ph) H H
1-1066 H H H H Me 2 -C≡C-CH₂-O-(4-MeO-Ph) H H
1-1067 H H H H Me 2 -C≡C-CH₂-O-(4-EtO-Ph) H H
1-1068 H H H H Me 2 -C≡C-CH₂-O-(4-MeS-Ph) H H
1-1069 H H H H Me 2 -C≡C-CH₂-O-(4-cHx-Ph) H H
1-1070 H H H H Me 2 -C≡C-CH₂-O-(4-Ph-Ph) H H
1-1071 H H H H Me 2 -C≡C-(CH₂)₂O-cPn H H
1-1072 H H H H Me 2 -C≡C-(CH₂)₂O-cHx H H
1-1073 H H H H Me 2 -C≡C-(CH₂)₂O-cHx Me H
1-1074 H H H H Me 2 -C≡C-(CH₂)₂O-cHx H Me
1-1075 H H H H Me 2 -C≡C-(CH₂)₂O-cHx F H
1-1076 H H H H Me 2 -C≡C-(CH₂)₂O-cHx H F
1-1077 H H Me Me Me 2 -C≡C-(CH₂)₂O-cHx H H
1-1078 CO₂Me H H H Me 2 -C≡C-(CH₂)₂O-cHx H H
1-1079 CO₂Et H H H Me 2 -C≡C-(CH₂)₂O-cHx H H
1-1080 H H H H Me 2 -C≡C-(CH₂)₂O-(3-F-cHx) H H
1-1081 H H H H Me 2 -C≡C-(CH₂)₂O-(4-F-cHx) H H
1-1082 H H H H Me 2 -C≡C-(CH₂)₂O-(4-Cl-cHx) H H
1-1083 H H H H Me 2 -C≡C-(CH₂)₂O-(4-Br-cHx) H H
1-1084 H H H H Me 2 -C≡C-(CH₂)₂O-(3-Me-cHx) H H
1-1085 H H H H Me 2 -C≡C-(CH₂)₂O-(4-Me-cHx) H H
1-1086 H H H H Me 2 -C≡C-(CH₂)₂O-(3-Et-cHx) H H
1-1087 H H H H Me 2 -C≡C-(CH₂)₂O-(4-Et-cHx) H H
1-1088 H H H H Me 2 -C≡C-(CH₂)₂O-(3-Pr-cHx) H H
1-1089 H H H H Me 2 -C≡C-(CH₂)₂O-(4-Pr-cHx) H H
1-1090 H H H H Me 2 -C≡C-(CH₂)₂O-(4-iPr-cHx) H H
1-1091 H H H H Me 2 -C≡C-(CH₂)₂O-(3-Bu-cHx) H H
1-1092 H H H H Me 2 -C≡C-(CH₂)₂O-(4-Bu-cHx) H H
1-1093 H H H H Me 2 -C≡C-(CH₂)₂O-(3-CF₃-cHx) H H
1-1094 H H H H Me 2 -C≡C-(CH₂)₂O-(4-CF₃-cHx) H H
1-1095 H H H H Me 2 -C≡C-(CH₂)₂O-(3-MeO-cHx) H H
1-1096 H H H H Me 2 -C≡C-(CH₂)₂O-(4-MeO-cHx) H H
1-1097 H H H H Me 2 -C≡C-(CH₂)₂O-(3-EtO-cHx) H H
1-1098 H H H H Me 2 -C≡C-(CH₂)₂O-(4-EtO-cHx) H H
1-1099 H H H H Me 2 -C≡C-(CH₂)₂O-(3-PrO-cHx) H H
1-1100 H H H H Me 2 -C≡C-(CH₂)₂O-(4-PrO-cHx) H H
1-1101 H H H H Me 2 -C≡C-(CH₂)₂O-(3-iPrO-cHx) H H
1-1102 H H H H Me 2 -C≡C-(CH₂)₂O-(4-iPrO-cHx) H H
1-1103 H H H H Me 2 -C≡C-(CH₂)₂O-[3-(2-Et-PrO)-cHx] H H
1-1104 H H H H Me 2 -C≡C-(CH₂)₂O-[4-(2-Et-PrO)-cHx] H H
1-1105 H H H H Me 2 -C≡C-(CH₂)₂O-(3-iBuO-cHx) H H
1-1106 H H H H Me 2 -C≡C-(CH₂)₂O-(4-iBuO-cHx) H H
1-1107 H H H H Me 2 -C≡C-(CH₂)₂O-(3-MeS-cHx) H H
1-1108 H H H H Me 2 -C≡C-(CH₂)₂O-(4-MeS-cHx) H H
1-1109 H H H H Me 2 -C≡C-(CH₂)₂O-(3-EtS-cHx) H H
1-1110 H H H H Me 2 -C≡C-(CH₂)₂O-(4-EtS-cHx) H H
1-1111 H H H H Me 2 -C≡C-(CH₂)₂O-(3-PrS-cHx) H H
1-1112 H H H H Me 2 -C≡C-(CH₂)₂O-(4-PrS-cHx) H H
1-1113 H H H H Me 2 -C≡C-(CH₂)₂O-(3-iPrS-cHx) H H
1-1114 H H H H Me 2 -C≡C-(CH₂)₂O-(4-iPrS-cHx) H H
1-1115 H H H H Me 2 -C≡C-(CH₂)₂O-[3-(2-Et-PrS)-cHx] H H
1-1116 H H H H Me 2 -C≡C-(CH₂)₂O-[4-(2-Et-PrS)-cHx] H H
1-1117 H H H H Me 2 -C≡C-(CH₂)₂O-(3-iBuS-cHx) H H
1-1118 H H H H Me 2 -C≡C-(CH₂)₂O-(4-iBuS-cHx) H H
1-1119 H H H H Me 2 -C≡C-(CH₂)₂O-(3-cHx-cHx) H H
1-1120 H H H H Me 2 -C≡C-(CH₂)₂O-(4-cHx-cHx) H H
1-1121 H H H H Me 2 -C≡C-(CH₂)₂O-(3-Ph-cHx) H H
1-1122 H H H H Me 2 -C≡C-(CH₂)₂O-(4-Ph-cHx) H H
1-1123 H H H H Me 2 -C≡C-(CH₂)₂O-(2,4-diMe-cHx) H H
1-1124 H H H H Me 2 -C≡C-(CH₂)₂O-(3,4-diMe-cHx) H H
1-1125 H H H H Me 2 -C≡C-(CH₂)₂O-(3,5-diMe-cHx) H H
1-1126 H H H H Me 2 -C≡C-(CH₂)₂O-Ph H H
1-1127 H H H H Me 2 -C≡C-(CH₂)₂O-Ph Me H
1-1128 H H H H Me 2 -C≡C-(CH₂)₂O-Ph H Me
1-1129 H H H H Me 2 -C≡C-(CH₂)₂O-Ph F H
1-1130 H H H H Me 2 -C≡C-(CH₂)₂O-Ph H F
1-1131 H H Me Me Me 2 -C≡C-(CH₂)₂O-Ph H H
1-1132 CO₂Me H H H Me 2 -C≡C-(CH₂)₂O-Ph H H
1-1133 CO₂Et H H H Me 2 -C≡C-(CH₂)₂O-Ph H H
1-1134 H H H H Me 2 -C≡C-(CH₂)₂O-(3-F-Ph) H H
1-1135 H H H H Me 2 -C≡C-(CH₂)₂O-(4-F-Ph) H H
1-1136 H H H H Me 2 -C≡C-(CH₂)₂O-(4-Cl-Ph) H H
1-1137 H H H H Me 2 -C≡C-(CH₂)₂O-(4-Br-Ph) H H
1-1138 H H H H Me 2 -C≡C-(CH₂)₂O-(3-Me-Ph) H H
1-1139 H H H H Me 2 -C≡C-(CH₂)₂O-(4-Me-Ph) H H
1-1140 H H H H Me 2 -C≡C-(CH₂)₂O-(3-Et-Ph) H H
1-1141 H H H H Me 2 -C≡C-(CH₂)₂O-(4-Et-Ph) H H
1-1142 H H H H Me 2 -C≡C-(CH₂)₂O-(3-Pr-Ph) H H
1-1143 H H H H Me 2 -C≡C-(CH₂)₂O-(4-Pr-Ph) H H
1-1144 H H H H Me 2 -C≡C-(CH₂)₂O-(3-iPr-Ph) H H
1-1145 H H H H Me 2 -C≡C-(CH₂)₂O-(4-iPr-Ph) H H
1-1146 H H H H Me 2 -C≡C-(CH₂)₂O-(3-Bu-Ph) H H
1-1147 H H H H Me 2 -C≡C-(CH₂)₂O-(4-Bu-Ph) H H
1-1148 H H H H Me 2 -C≡C-(CH₂)₂O-(3-CF₃-Ph) H H
1-1149 H H H H Me 2 -C≡C-(CH₂)₂O-(4-CF₃-Ph) H H
1-1150 H H H H Me 2 -C≡C-(CH₂)₂O-(3-MeO-Ph) H H
1-1151 H H H H Me 2 -C≡C-(CH₂)₂O-(4-MeO-Ph) H H
1-1152 H H H H Me 2 -C≡C-(CH₂)₂O-(3-EtO-Ph) H H
1-1153 H H H H Me 2 -C≡C-(CH₂)₂O-(4-EtO-Ph) H H
1-1154 H H H H Me 2 -C≡C-(CH₂)₂O-(3-PrO-Ph) H H
1-1155 H H H H Me 2 -C≡C-(CH₂)₂O-(4-PrO-Ph) H H
1-1156 H H H H Me 2 -C≡C-(CH₂)₂O-(3-iPrO-Ph) H H
1-1157 H H H H Me 2 -C≡C-(CH₂)₂O-(4-iPrO-Ph) H H
1-1158 H H H H Me 2 -C≡C-(CH₂)₂O-[3-(2-Et-PrO)-Ph] H H
1-1159 H H H H Me 2 -C≡C-(CH₂)₂O-[4-(2-Et-PrO)-Ph] H H
1-1160 H H H H Me 2 -C≡C-(CH₂)₂O-(3-iBuO-Ph) H H
1-1161 H H H H Me 2 -C≡C-(CH₂)₂O-(4-iBuO-Ph) H H
1-1162 H H H H Me 2 -C≡C-(CH₂)₂O-(3-MeS-Ph) H H
1-1163 H H H H Me 2 -C≡C-(CH₂)₂O-(4-MeS-Ph) H H
1-1164 H H H H Me 2 -C≡C-(CH₂)₂O-(3-EtS-Ph) H H
1-1165 H H H H Me 2 -C≡C-(CH₂)₂O-(4-EtS-Ph) H H
1-1166 H H H H Me 2 -C≡C-(CH₂)₂O-(3-PrS-Ph) H H
1-1167 H H H H Me 2 -C≡C-(CH₂)₂O-(4-PrS-Ph) H H
1-1168 H H H H Me 2 -C≡C-(CH₂)₂O-(3-iPrS-Ph) H H
1-1169 H H H H Me 2 -C≡C-(CH₂)₂O-(4-iPrS-Ph) H H
1-1170 H H H H Me 2 -C≡C-(CH₂)₂O-[3-(2-Et-PrS)-Ph] H H
1-1171 H H H H Me 2 -C≡C-(CH₂)₂O-[4-(2-Et-PrS)-Ph] H H
1-1172 H H H H Me 2 -C≡C-(CH₂)₂O-(3-iBuS-Ph) H H
1-1173 H H H H Me 2 -C≡C-(CH₂)₂O-(4-iBuS-Ph) H H
1-1174 H H H H Me 2 -C≡C-(CH₂)₂O-(3-cHx-Ph) H H
1-1175 H H H H Me 2 -C≡C-(CH₂)₂O-(4-cHx-Ph) H H
1-1176 H H H H Me 2 -C≡C-(CH₂)₂O-(3-Ph-Ph) H H
1-1177 H H H H Me 2 -C≡C-(CH₂)₂O-(4-Ph-Ph) H H
1-1178 H H H H Me 2 -C≡C-(CH₂)₂O-(2,4-diMe-Ph) H H
1-1179 H H H H Me 2 -C≡C-(CH₂)₂O-(3,4-diMe-Ph) H H
1-1180 H H H H Me 2 -C≡C-(CH₂)₂O-(3,5-diMe-Ph) H H
1-1181 H H H H Me 2 -C≡C-(CH₂)₃O-cHx H H
1-1182 H H H H Me 2 -C≡C-(CH₂)₃O-Ph H H
1-1183 H H H H Me 2 -C≡C-(CH₂)₄O-cHx H H
1-1184 H H H H Me 2 -C≡C-(CH₂)₄O-Ph H H
1-1185 H H H H Me 2 -C≡C-CH₂-OCH₂-cHx H H
1-1186 H H Me Me Me 2 -C≡C-CH₂-OCH₂-cHx H H
1-1187 CO₂Me H H H Me 2 -C≡C-CH₂-OCH₂-cHx H H
1-1188 CO₂Et H H H Me 2 -C≡C-CH₂-OCH₂-cHx H H
1-1189 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-F-cHx) H H
1-1190 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-Me-cHx) H H
1-1191 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-Et-cHx) H H
1-1192 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-CF₃-cHx) H H
1-1193 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-MeO-cHx) H H
1-1194 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-EtO-cHx) H H
1-1195 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-MeS-cHx) H H
1-1196 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-cHx-cHx) H H
1-1197 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-Ph-cHx) H H
1-1198 H H H H Me 2 -C≡C-CH₂-OCH₂-Ph H H
1-1199 H H Me Me Me 2 -C≡C-CH₂-OCH₂-Ph H H
1-1200 CO₂Me H H H Me 2 -C≡C-CH₂-OCH₂-Ph H H
1-1201 CO₂Et H H H Me 2 -C≡C-CH₂-OCH₂-Ph H H
1-1202 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-F-Ph) H H
1-1203 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-Me-Ph) H H
1-1204 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-Et-Ph) H H
1-1205 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-CF₃-Ph) H H
1-1206 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-MeO-Ph) H H
1-1207 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-EtO-Ph) H H
1-1208 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-MeS-Ph) H H
1-1209 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-cHx-Ph) H H
1-1210 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-Ph-Ph) H H
1-1211 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-cPn H H
1-1212 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-cHx H H
1-1213 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-cHx Me H
1-1214 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-cHx H Me
1-1215 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-cHx F H
1-1216 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-cHx H F
1-1217 H H Me Me Me 2 --C≡C-(CH₂)₂-OCH₂-CH₂-cHx H H
1-1218 CO₂Me H H H Me 2 -C≡C-(CH₂)₂-OCH₂-cHx H H
1-1219 CO₂Et H H H Me 2 -C≡C-(CH₂)₂-OCH₂-cHx H H
1-1220 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-F-cHx) H H
1-1221 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-F-cHx) H H
1-1222 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-Cl-cHx) H H
1-1223 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-Br-cHx) H H
1-1224 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-Me-cHx) H H
1-1225 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-Me-cHx) H H
1-1226 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-Et-cHx) H H
1-1227 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-Et-cHx) H H
1-1228 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-Pr-cHx) H H
1-1229 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-Pr-cHx) H H
1-1230 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-iPr-cHx) H H
1-1231 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-Bu-cHx) H H
1-1232 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-Bu-cHx) H H
1-1233 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-CF₃-cHx) H H
1-1234 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-CF₃-cHx) H H
1-1235 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-MeO-cHx) H H
1-1236 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-MeO-cHx) H H
1-1237 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-EtO-cHx) H H
1-1238 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-EtO-cHx) H H
1-1239 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-PrO-cHx) H H
1-1240 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-PrO-cHx) H H
1-1241 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-iPrO-cHx) H H
1-1242 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-iPrO-cHx) H H
1-1243 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-[3-(2-Et-PrO)cHx] H H
1-1244 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-[4-(2-Et-PrO)cHx] H H
1-1245 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-iBuO-cHx) H H
1-1246 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-iBuO-cHx) H H
1-1247 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-MeS-cHx) H H
1-1248 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-MeS-cHx) H H
1-1249 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-EtS-cHx) H H
1-1250 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-EtS-cHx) H H
1-1251 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-PrS-cHx) H H
1-1252 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-PrS-cHx) H H
1-1253 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-iPrS-cHx) H H
1-1254 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-iPrS-cHx) H H
1-1255 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-[3-(2-Et-PrS)cHx] H H
1-1256 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-[4-(2-Et-PrS)cHx] H H
1-1257 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-iBuS-cHx) H H
1-1258 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-iBuS-cHx) H H
1-1259 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-cHx-cHx) H H
1-1260 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-cHx-cHx) H H
1-1261 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-Ph-cHx) H H
1-1262 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-Ph-cHx) H H
1-1263 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(2,4-diMe-cHx) H H
1-1264 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3,4-diMe-cHx) H H
1-1265 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3,5-diMe-cHx) H H
1-1266 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-Ph H H
1-1267 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-Ph Me H
1-1268 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-Ph H Me
1-1269 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-Ph F H
1-1270 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-Ph H F
1-1271 H H Me Me Me 2 -C≡C-(CH₂)₂-OCH₂-CH₂-Ph H H
1-1272 CO₂Me H H H Me 2 -C≡C-(CH₂)₂-OCH₂-Ph H H
1-1273 CO₂Et H H H Me 2 -C≡C-(CH₂)₂-OCH₂-Ph H H
1-1274 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-F-Ph) H H
1-1275 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-F-Ph) H H
1-1276 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-Cl-Ph) H H
1-1277 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-Br-Ph) H H
1-1278 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-Me-Ph) H H
1-1279 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-Me-Ph) H H
1-1280 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-Et-Ph) H H
1-1281 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-Et-Ph) H H
1-1282 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-Pr-Ph) H H
1-1283 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-Pr-Ph) H H
1-1284 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-iPr-Ph) H H
1-1285 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-iPr-Ph) H H
1-1286 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-Bu-Ph) H H
1-1287 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-Bu-Ph) H H
1-1288 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-CF₃-Ph) H H
1-1289 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-CF₃-Ph) H H
1-1290 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-MeO-Ph) H H
1-1291 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-MeO-Ph) H H
1-1292 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-EtO-Ph) H H
1-1293 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-EtO-Ph) H H
1-1294 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-PrO-Ph) H H
1-1295 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-PrO-Ph) H H
1-1296 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-iPrO-Ph) H H
1-1297 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-iPrO-Ph) H H
1-1298 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-[3-(2-Et-PrO)Ph] H H
1-1299 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-[4-(2-Et-PrO)Ph] H H
1-1300 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-iBuO-Ph) H H
1-1301 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-iBuO-Ph) H H
1-1302 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-MeS-Ph) H H
1-1303 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-MeS-Ph) H H
1-1304 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-EtS-Ph) H H
1-1305 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-EtS-Ph) H H
1-1306 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-PrS-Ph) H H
1-1307 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-PrS-Ph) H H
1-1308 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-iPrS-Ph) H H
1-1309 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-iPrS-Ph) H H
1-1310 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-[3-(2-Et-PrS)Ph] H H
1-1311 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-[4-(2-Et-PrS)Ph] H H
1-1312 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-iBuS-Ph) H H
1-1313 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-iBuS-Ph) H H
1-1314 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-cHx-Ph) H H
1-1315 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-cHx-Ph) H H
1-1316 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3-Ph-Ph) H H
1-1317 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(4-Ph-Ph) H H
1-1318 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(2,4-diMe-Ph) H H
1-1319 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3,4-diMe-Ph) H H
1-1320 H H H H Me 2 -C≡C-(CH₂)₂-OCH₂-(3,5-diMe-Ph) H H
1-1321 H H H H Me 2 -C≡C-(CH₂)₃-OCH₂-cHx H H
1-1322 H H H H Me 2 -C≡C-(CH₂)₃-OCH₂-Ph H H
1-1323 H H H H Me 2 -C≡C-(CH₂)₄-OCH₂-cHx H H
1-1324 H H H H Me 2 -C≡C-(CH₂)₄-OCH₂-Ph H H
1-1325 H H H H Me 2 -CO-CH₂-(4-cHx-Ph) H H
1-1326 H H H H Me 2 -CO-CH₂-(4-Ph-Ph) H H
1-1327 H H H H Me 2 -CO-(CH₂)₂-cHx H H
1-1328 H H H H Me 2 -CO-(CH₂)₂-Ph H H
1-1329 H H H H Me 2 -CO-(CH₂)₃-cHx H H
1-1330 H H H H Me 2 -CO-(CH₂)₃-Ph H H
1-1331 H H H H Me 2 -CO-(CH₂)₄-cHx H H
1-1332 H H Me Me Me 2 -CO-(CH₂)₄-cHx H H
1-1333 CO₂Me H H H Me 2 -CO-(CH₂)₄-cHx H H
1-1334 CO₂Et H H H Me 2 -CO-(CH₂)₄-cHx H H
1-1335 H H H H Me 2 -CO-(CH₂)₄-(4-F-cHx) H H
1-1336 H H H H Me 2 -CO-(CH₂)₄-(4-Me-cHx) H H
1-1337 H H H H Me 2 -CO-(CH₂)₄-(4-Et-cHx) H H
1-1338 H H H H Me 2 -CO-(CH₂)₄-(4-CF₃-cHx) H H
1-1339 H H H H Me 2 -CO-(CH₂)₄-(4-MeO-cHx) H H
1-1340 H H H H Me 2 -CO-(CH₂)₄-(4-EtO-cHx) H H
1-1341 H H H H Me 2 -CO-(CH₂)₄-(4-MeS-cHx) H H
1-1342 H H H H Me 2 -CO-(CH₂)₄-(4-cHx-cHx) H H
1-1343 H H H H Me 2 -CO-(CH₂)₄-(4-Ph-cHx) H H
1-1344 H H H H Me 2 -CO-(CH₂)₄-Ph H H
1-1345 H H Me Me Me 2 -CO-(CH₂)₄-Ph H H
1-1346 CO₂Me H H H Me 2 -CO-(CH₂)₄-Ph H H
1-1347 CO₂Et H H H Me 2 -CO-(CH₂)₄-Ph H H
1-1348 H H H H Me 2 -CO-(CH₂)₄-(4-F-Ph) H H
1-1349 H H H H Me 2 -CO-(CH₂)₄-(4-Me-Ph) H H
1-1350 H H H H Me 2 -CO-(CH₂)₄-(4-Et-Ph) H H
1-1351 H H H H Me 2 -CO-(CH₂)₄-(4-CF₃-Ph) H H
1-1352 H H H H Me 2 -CO-(CH₂)₄-(4-MeO-Ph) H H
1-1353 H H H H Me 2 -CO-(CH₂)₄-(4-EtO-Ph) H H
1-1354 H H H H Me 2 -CO-(CH₂)₄-(4-MeS-Ph) H H
1-1355 H H H H Me 2 -CO-(CH₂)₄-(4-cHx-Ph) H H
1-1356 H H H H Me 2 -CO-(CH₂)₄-(4-Ph-Ph) H H
1-1357 H H H H Me 2 -CO-(CH₂)₅-cHx H H
1-1358 H H Me Me Me 2 -CO-(CH₂)₅-cHx H H
1-1359 CO₂Me H H H Me 2 -CO-(CH₂)₅-cHx H H
1-1360 CO₂Et H H H Me 2 -CO-(CH₂)₅-cHx H H
1-1361 H H H H Me 2 -CO-(CH₂)₅-(4-F-cHx) H H
1-1362 H H H H Me 2 -CO-(CH₂)₅-(4-Me-cHx) H H
1-1363 H H H H Me 2 -CO-(CH₂)₅-(4-Et-cHx) H H
1-1364 H H H H Me 2 -CO-(CH₂)₅-(4-CF₃-cHx) H H
1-1365 H H H H Me 2 -CO-(CH₂)₅-(4-MeO-cHx) H H
1-1366 H H H H Me 2 -CO-(CH₂)₅-(4-EtO-cHx) H H
1-1367 H H H H Me 2 -CO-(CH₂)₅-(4-MeS-cHx) H H
1-1368 H H H H Me 2 -CO-(CH₂)₅-(4-cHx-cHx) H H
1-1369 H H H H Me 2 -CO-(CH₂)₅-(4-Ph-cHx) H H
1-1370 H H H H Me 2 -CO-(CH₂)₅-Ph H H
1-1371 H H Me Me Me 2 -CO-(CH₂)₅-Ph H H
1-1372 CO₂Me H H H Me 2 -CO-(CH₂)₅-Ph H H
1-1373 CO₂Et H H H Me 2 -CO-(CH₂)₅-Ph H H
1-1374 H H H H Me 2 -CO-(CH₂)₅-(4-F-Ph) H H
1-1375 H H H H Me 2 -CO-(CH₂)₅-(4-Me-Ph) H H
1-1376 H H H H Me 2 -CO-(CH₂)₅-(4-Et-Ph) H H
1-1377 H H H H Me 2 -CO-(CH₂)₅-(4-CF₃-Ph) H H
1-1378 H H H H Me 2 -CO-(CH₂)₅-(4-MeO-Ph) H H
1-1379 H H H H Me 2 -CO-(CH₂)₅-(4-EtO-Ph) H H
1-1380 H H H H Me 2 -CO-(CH₂)₅-(4-MeS-Ph) H H
1-1381 H H H H Me 2 -CO-(CH₂)₅-(4-cHx-Ph) H H
1-1382 H H H H Me 2 -CO-(CH₂)₅-(4-Ph-Ph) H H
1-1383 H H H H Me 2 -CO-(CH₂)₆-cHx H H
1-1384 H H H H Me 2 -CO-(CH₂)₆-Ph H H
1-1385 H H H H Me 2 -CO-(CH₂)₇-cHx H H
1-1386 H H H H Me 2 -CO-(CH₂)₇-Ph H H
1-1387 H H H H Me 2 -CO-(CH₂)₂-O-cHx H H
1-1388 H H Me Me Me 2 -CO-(CH₂)₂-O-cHx H H
1-1389 CO₂Me H H H Me 2 -CO-(CH₂)₂-O-cHx H H
1-1390 CO₂Et H H H Me 2 -CO-(CH₂)₂-O-cHx H H
1-1391 H H H H Me 2 -CO-(CH₂)₂-O-(4-F-cHx) H H
1-1392 H H H H Me 2 -CO-(CH₂)₂-O-(4-Me-cHx) H H
1-1393 H H H H Me 2 -CO-(CH₂)₂-O-(4-Et-cHx) H H
1-1394 H H H H Me 2 -CO-(CH₂)₂-O-(4-CF₃-cHx) H H
1-1395 H H H H Me 2 -CO-(CH₂)₂-O-(4-MeO-cHx) H H
1-1396 H H H H Me 2 -CO-(CH₂)₂-O-(4-EtO-cHx) H H
1-1397 H H H H Me 2 -CO-(CH₂)₂-O-(4-MeS-cHx) H H
1-1398 H H H H Me 2 -CO-(CH₂)₂-O-(4-cHx-cHx) H H
1-1399 H H H H Me 2 -CO-(CH₂)₂-O-(4-Ph-cHx) H H
1-1400 H H H H Me 2 -CO-(CH₂)₂-O-Ph H H
1-1401 H H Me Me Me 2 -CO-(CH₂)₂-O-Ph H H
1-1402 CO₂Me H H H Me 2 -CO-(CH₂)₂-O-Ph H H
1-1403 CO₂Et H H H Me 2 -CO-(CH₂)₂-O-Ph H H
1-1404 H H H H Me 2 -CO-(CH₂)₂-O-(4-F-Ph) H H
1-1405 H H H H Me 2 -CO-(CH₂)₂-O-(4-Me-Ph) H H
1-1406 H H H H Me 2 -CO-(CH₂)₂-O-(4-Et-Ph) H H
1-1407 H H H H Me 2 -CO-(CH₂)₂-O-(4-CF₃-Ph) H H
1-1408 H H H H Me 2 -CO-(CH₂)₂-O-(4-MeO-Ph) H H
1-1409 H H H H Me 2 -CO-(CH₂)₂-O-(4-EtO-Ph) H H
1-1410 H H H H Me 2 -CO-(CH₂)₂-O-(4-MeS-Ph) H H
1-1411 H H H H Me 2 -CO-(CH₂)₂-O-(4-cHx-Ph) H H
1-1412 H H H H Me 2 -CO-(CH₂)₂-O-(4-Ph-Ph) H H
1-1413 H H H H Me 2 -CO-(CH₂)₃-O-cPn H H
1-1414 H H H H Me 2 -CO-(CH₂)₃-O-cHx H H
1-1415 H H H H Me 2 -CO-(CH₂)₃-O-cHx Me H
1-1416 H H H H Me 2 -CO-(CH₂)₃-O-cHx H Me
1-1417 H H H H Me 2 -CO-(CH₂)₃-O-cHx F H
1-1418 H H H H Me 2 -CO-(CH₂)₃-O-cHx H F
1-1419 H H Me Me Me 2 -CO-(CH₂)₃-O-cHx H H
1-1420 CO₂Me H H H Me 2 -CO-(CH₂)₃-O-cHx H H
1-1421 CO₂Et H H H Me 2 -CO-(CH₂)₃-O-cHx H H
1-1422 H H H H Me 2 -CO-(CH₂)₃-O-(3-F-cHx) H H
1-1423 H H H H Me 2 -CO-(CH₂)₃-O-(4-F-cHx) H H
1-1424 H H H H Me 2 -CO-(CH₂)₃-O-(4-Cl-cHx) H H
1-1425 H H H H Me 2 -CO-(CH₂)₃-O-(4-Br-cHx) H H
1-1426 H H H H Me 2 -CO-(CH₂)₃-O-(3-Me-cHx) H H
1-1427 H H H H Me 2 -CO-(CH₂)₃-O-(4-Me-cHx) H H
1-1428 H H H H Me 2 -CO-(CH₂)₃-O-(3-Et-cHx) H H
1-1429 H H H H Me 2 -CO-(CH₂)₃-O-(4-Et-cHx) H H
1-1430 H H H H Me 2 -CO-(CH₂)₃-O-(3-Pr-cHx) H H
1-1431 H H H H Me 2 -CO-(CH₂)₃-O-(4-Pr-cHx) H H
1-1432 H H H H Me 2 -CO-(CH₂)₃-O-(4-iPr-cHx) H H
1-1433 H H H H Me 2 -CO-(CH₂)₃-O-(3-Bu-cHx) H H
1-1434 H H H H Me 2 -CO-(CH₂)₃-O-(4-Bu-cHx) H H
1-1435 H H H H Me 2 -CO-(CH₂)₃-O-(3-CF₃-cHx) H H
1-1436 H H H H Me 2 -CO-(CH₂)₃-O-(4-CF₃-cHx) H H
1-1437 H H H H Me 2 -CO-(CH₂)₃-O-(3-MeO-cHx) H H
1-1438 H H H H Me 2 -CO-(CH₂)₃-O-(4-MeO-cHx) H H
1-1439 H H H H Me 2 -CO-(CH₂)₃-O-(3-EtO-cHx) H H
1-1440 H H H H Me 2 -CO-(CH₂)₃-O-(4-EtO-cHx) H H
1-1441 H H H H Me 2 -CO-(CH₂)₃-O-(3-PrO-cHx) H H
1-1442 H H H H Me 2 -CO-(CH₂)₃-O-(4-PrO-cHx) H H
1-1443 H H H H Me 2 -CO-(CH₂)₃-O-(3-iPrO-cHx) H H
1-1444 H H H H Me 2 -CO-(CH₂)₃-O-(4-iPrO-cHx) H H
1-1445 H H H H Me 2 -CO-(CH₂)₃-O-[3-(2-Et-PrO)cHx] H H
1-1446 H H H H Me 2 -CO-(CH₂)₃-O-[4-(2-Et-PrO)cHx] H H
1-1447 H H H H Me 2 -CO-(CH₂)₃-O-(3-iBuO-cHx) H H
1-1448 H H H H Me 2 -CO-(CH₂)₃-O-(4-iBuO-cHx) H H
1-1449 H H H H Me 2 -CO-(CH₂)₃-O-(3-MeS-cHx) H H
1-1450 H H H H Me 2 -CO-(CH₂)₃-O-(4-MeS-cHx) H H
1-1451 H H H H Me 2 -CO-(CH₂)₃-O-(3-EtS-cHx) H H
1-1452 H H H H Me 2 -CO-(CH₂)₃-O-(4-EtS-cHx) H H
1-1453 H H H H Me 2 -CO-(CH₂)₃-O-(3-PrS-cHx) H H
1-1454 H H H H Me 2 -CO-(CH₂)₃-O-(4-PrS-cHx) H H
1-1455 H H H H Me 2 -CO-(CH₂)₃-O-(3-iPrS-cHx) H H
1-1456 H H H H Me 2 -CO-(CH₂)₃-O-(4-iPrS-cHx) H H
1-1457 H H H H Me 2 -CO-(CH₂)₃-O-[3-(2-Et-PrS)cHx] H H
1-1458 H H H H Me 2 -CO-(CH₂)₃-O-[4-(2-Et-PrS)cHx] H H
1-1459 H H H H Me 2 -CO-(CH₂)₃-O-(3-iBuS-cHx) H H
1-1460 H H H H Me 2 -CO-(CH₂)₃-O-(4-iBuS-cHx) H H
1-1461 H H H H Me 2 -CO-(CH₂)₃-O-(3-cHx-cHx) H H
1-1462 H H H H Me 2 -CO-(CH₂)₃-O-(4-cHx-cHx) H H
1-1463 H H H H Me 2 -CO-(CH₂)₃-O-(3-Ph-cHx) H H
1-1464 H H H H Me 2 -CO-(CH₂)₃-O-(4-Ph-cHx) H H
1-1465 H H H H Me 2 -CO-(CH₂)₃-O-(2,4-diMe-cHx) H H
1-1466 H H H H Me 2 -CO-(CH₂)₃-O-(3,4-diMe-cHx) H H
1-1467 H H H H Me 2 -CO-(CH₂)₃-O-(3,5-diMe-cHx) H H
1-1468 H H H H Me 2 -CO-(CH₂)₃-O-Ph H H
1-1469 H H H H Me 2 -CO-(CH₂)₃-O-Ph Me H
1-1470 H H H H Me 2 -CO-(CH₂)₃-O-Ph H Me
1-1471 H H H H Me 2 -CO-(CH₂)₃-O-Ph F H
1-1472 H H H H Me 2 -CO-(CH₂)₃-O-Ph H F
1-1473 H H Me Me Me 2 -CO-(CH₂)₃-O-Ph H H
1-1474 CO₂Me H H H Me 2 -CO-(CH₂)₃-O-Ph H H
1-1475 CO₂Et H H H Me 2 -CO-(CH₂)₃-O-Ph H H
1-1476 H H H H Me 2 -CO-(CH₂)₃-O-(3-F-Ph) H H
1-1477 H H H H Me 2 -CO-(CH₂)₃-O-(4-F-Ph) H H
1-1478 H H H H Me 2 -CO-(CH₂)₃-O-(4-Cl-Ph) H H
1-1479 H H H H Me 2 -CO-(CH₂)₃-O-(4-Br-Ph) H H
1-1480 H H H H Me 2 -CO-(CH₂)₃-O-(3-Me-Ph) H H
1-1481 H H H H Me 2 -CO-(CH₂)₃-O-(4-Me-Ph) H H
1-1482 H H H H Me 2 -CO-(CH₂)₃-O-(3-Et-Ph) H H
1-1483 H H H H Me 2 -CO-(CH₂)₃-O-(4-Et-Ph) H H
1-1484 H H H H Me 2 -CO-(CH₂)₃-O-(3-Pr-Ph) H H
1-1485 H H H H Me 2 -CO-(CH₂)₃-O-(4-Pr-Ph) H H
1-1486 H H H H Me 2 -CO-(CH₂)₃-O-(3-iPr-Ph) H H
1-1487 H H H H Me 2 -CO-(CH₂)₃-O-(4-iPr-Ph) H H
1-1488 H H H H Me 2 -CO-(CH₂)₃-O-(3-Bu-Ph) H H
1-1489 H H H H Me 2 -CO-(CH₂)₃-O-(4-Bu-Ph) H H
1-1490 H H H H Me 2 -CO-(CH₂)₃-O-(3-CF₃-Ph) H H
1-1491 H H H H Me 2 -CO-(CH₂)₃-O-(4-CF₃-Ph) H H
1-1492 H H H H Me 2 -CO-(CH₂)₃-O-(3-MeO-Ph) H H
1-1493 H H H H Me 2 -CO-(CH₂)₃-O-(4-MeO-Ph) H H
1-1494 H H H H Me 2 -CO-(CH₂)₃-O-(3-EtO-Ph) H H
1-1495 H H H H Me 2 -CO-(CH₂)₃-O-(4-EtO-Ph) H H
1-1496 H H H H Me 2 -CO-(CH₂)₃-O-(3-PrO-Ph) H H
1-1497 H H H H Me 2 -CO-(CH₂)₃-O-(4-PrO-Ph) H H
1-1498 H H H H Me 2 -CO-(CH₂)₃-O-(3-iPrO-Ph) H H
1-1499 H H H H Me 2 -CO-(CH₂)₃-O-(4-iPrO-Ph) H H
1-1500 H H H H Me 2 -CO-(CH₂)₃-O-[3-(2-Et-PrO)-Ph] H H
1-1501 H H H H Me 2 -CO-(CH₂)₃-O-[4-(2-Et-PrO)-Ph] H H
1-1502 H H H H Me 2 -CO-(CH₂)₃-O-(3-iBuO-Ph) H H
1-1503 H H H H Me 2 -CO-(CH₂)₃-O-(4-iBuO-Ph) H H
1-1504 H H H H Me 2 -CO-(CH₂)₃-O-(3-MeS-Ph) H H
1-1505 H H H H Me 2 -CO-(CH₂)₃-O-(4-MeS-Ph) H H
1-1506 H H H H Me 2 -CO-(CH₂)₃-O-(3-EtS-Ph) H H
1-1507 H H H H Me 2 -CO-(CH₂)₃-O-(4-EtS-Ph) H H
1-1508 H H H H Me 2 -CO-(CH₂)₃-O-(3-PrS-Ph) H H
1-1509 H H H H Me 2 -CO-(CH₂)₃-O-(4-PrS-Ph) H H
1-1510 H H H H Me 2 -CO-(CH₂)₃-O-(3-iPrS-Ph) H H
1-1511 H H H H Me 2 -CO-(CH₂)₃-O-(4-iPrS-Ph) H H
1-1512 H H H H Me 2 -CO-(CH₂)₃-O-[3-(2-Et-PrS)-Ph] H H
1-1513 H H H H Me 2 -CO-(CH₂)₃-O-[4-(2-Et-PrS)-Ph] H H
1-1514 H H H H Me 2 -CO-(CH₂)₃-O-(3-iBuS-Ph) H H
1-1515 H H H H Me 2 -CO-(CH₂)₃-O-(4-iBuS-Ph) H H
1-1516 H H H H Me 2 -CO-(CH₂)₃-O-(3-cHx-Ph) H H
1-1517 H H H H Me 2 -CO-(CH₂)₃-O-(4-cHx-Ph) H H
1-1518 H H H H Me 2 -CO-(CH₂)₃-O-(3-Ph-Ph) H H
1-1519 H H H H Me 2 -CO-(CH₂)₃-O-(4-Ph-Ph) H H
1-1520 H H H H Me 2 -CO-(CH₂)₃-O-(2,4-diMe-Ph) H H
1-1521 H H H H Me 2 -CO-(CH₂)₃-O-(3,4-diMe-Ph) H H
1-1522 H H H H Me 2 -CO-(CH₂)₃-O-(3,5-diMe-Ph) H H
1-1523 H H H H Me 2 -CO-(CH₂)₄-O-cHx H H
1-1524 H H H H Me 2 -CO-(CH₂)₄-O-Ph H H
1-1525 H H H H Me 2 -CO-(CH₂)₅-O-cHx H H
1-1526 H H H H Me 2 -CO-(CH₂)₅-O-Ph H H
1-1527 H H H H Me 2 -CO-(CH₂)₂-OCH₂-cHx H H
1-1528 H H Me Me Me 2 -CO-(CH₂)₂-OCH₂-cHx H H
1-1529 CO₂Me H H H Me 2 -CO-(CH₂)₂-OCH₂-cHx H H
1-1530 CO₂Et H H H Me 2 -CO-(CH₂)₂-OCH₂-cHx H H
1-1531 H H H H Me 2 -CO-(CH₂)₂-OCH₂-(4-F-cHx) H H
1-1532 H H H H Me 2 -CO-(CH₂)₂-OCH₂-(4-Me-cHx) H H
1-1533 H H H H Me 2 -CO-(CH₂)₂-OCH₂-(4-Et-cHx) H H
1-1534 H H H H Me 2 -CO-(CH₂)₂-OCH₂-(4-CF₃-cHx) H H
1-1535 H H H H Me 2 -CO-(CH₂)₂-OCH₂-(4-MeO-cHx) H H
1-1536 H H H H Me 2 -CO-(CH₂)₂-OCH₂-(4-EtO-cHx) H H
1-1537 H H H H Me 2 -CO-(CH₂)₂-OCH₂-(4-MeS-cHx) H H
1-1538 H H H H Me 2 -CO-(CH₂)₂-OCH₂-(4-cHx-cHx) H H
1-1539 H H H H Me 2 -CO-(CH₂)₂-OCH₂-(4-Ph-cHx) H H
1-1540 H H H H Me 2 -CO-(CH₂)₂-OCH₂-Ph H H
1-1541 H H Me Me Me 2 -CO-(CH₂)₂-OCH₂-Ph H H
1-1542 CO₂Me H H H Me 2 -CO-(CH₂)₂-OCH₂-Ph H H
1-1543 CO₂Et H H H Me 2 -CO-(CH₂)₂-OCH₂-Ph H H
1-1544 H H H H Me 2 -CO-(CH₂)₂-OCH₂-(4-F-Ph) H H
1-1545 H H H H Me 2 -CO-(CH₂)₂-OCH₂-(4-Me-Ph) H H
1-1546 H H H H Me 2 -CO-(CH₂)₂-OCH₂-(4-Et-Ph) H H
1-1547 H H H H Me 2 -CO-(CH₂)₂-OCH₂-(4-CF₃-Ph) H H
1-1548 H H H H Me 2 -CO-(CH₂)₂-OCH₂-(4-MeO-Ph) H H
1-1549 H H H H Me 2 -CO-(CH₂)₂-OCH₂-(4-EtO-Ph) H H
1-1550 H H H H Me 2 -CO-(CH₂)₂-OCH₂-(4-MeS-Ph) H H
1-1551 H H H H Me 2 -CO-(CH₂)₂-OCH₂-(4-cHx-Ph) H H
1-1552 H H H H Me 2 -CO-(CH₂)₂-OCH₂-(4-Ph-Ph) H H
1-1553 H H H H Me 2 -CO-(CH₂)₃-OCH₂-CH₂-cPn H H
1-1554 H H H H Me 2 -CO-(CH₂)₃-OCH₂-cHx H H
1-1555 H H H H Me 2 -CO-(CH₂)₃-OCH₂-cHx Me H
1-1556 H H H H Me 2 -CO-(CH₂)₃-OCH₂-cHx H Me
1-1557 H H H H Me 2 -CO-(CH₂)₃-OCH₂-cHx F H
1-1558 H H H H Me 2 -CO-(CH₂)₃-OCH₂-cHx H F
1-1559 H H Me Me Me 2 -CO-(CH₂)₃-OCH₂-cHx H H
1-1560 COMe H H H Me 2 -CO-(CH₂)₃-OCH₂-cHx H H
1-1561 CO₂Et H H H Me 2 -CO-(CH₂)₃-OCH₂-cHx H H
1-1562 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-F-cHx) H H
1-1563 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-F-cHx) H H
1-1564 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-Cl-cHx) H H
1-1565 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-Br-cHx) H H
1-1566 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-Me-cHx) H H
1-1567 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-Me-cHx) H H
1-1568 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-Et-cHx) H H
1-1569 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-Et-cHx) H H
1-1570 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-Pr-cHx) H H
1-1571 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-Pr-cHx) H H
1-1572 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-iPr-cHx) H H
1-1573 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-Bu-cHx) H H
1-1574 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-Bu-cHx) H H
1-1575 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-CF₃-cHx) H H
1-1576 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-CF₃-cHx) H H
1-1577 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-MeO-cHx) H H
1-1578 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-MeO-cHx) H H
1-1579 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-EtO-cHx) H H
1-1580 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-EtO-cHx) H H
1-1581 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-PrO-cHx) H H
1-1582 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-PrO-cHx) H H
1-1583 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-iPrO-cHx) H H
1-1584 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-iPrO-cHx) H H
1-1585 H H H H Me 2 -CO-(CH₂)₃-OCH₂-[3-(2-Et-PrO)cHx] H H
1-1586 H H H H Me 2 -CO-(CH₂)₃-OCH₂-[4-(2-Et-PrO)cHx] H H
1-1587 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-iBuO-cHx) H H
1-1588 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-iBuO-cHx) H H
1-1589 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-MeS-cHx) H H
1-1590 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-MeS-cHx) H H
1-1591 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-EtS-cHx) H H
1-1592 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-EtS-cHx) H H
1-1593 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-PrS-cHx) H H
1-1594 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-PrS-cHx) H H
1-1595 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-iPrS-cHx) H H
1-1596 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-iPrS-cHx) H H
1-1597 H H H H Me 2 -CO-(CH₂)₃-OCH₂-[3-(2-Et-PrS)cHx] H H
1-1598 H H H H Me 2 -CO-(CH₂)₃-OCH₂-[4-(2-Et-PrS)cHx] H H
1-1599 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-iBuS-cHx) H H
1-1600 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-iBuS-cHx) H H
1-1601 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-cHx-cHx) H H
1-1602 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-cHx-cHx) H H
1-1603 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-Ph-cHx) H H
1-1604 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-Ph-cHx) H H
1-1605 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(2,4-diMe-cHx) H H
1-1606 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3,4-diMe-cHx) H H
1-1607 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3,5-diMe-cHx) H H
1-1608 H H H H Me 2 -CO-(CH₂)₃-OCH₂-Ph H H
1-1609 H H H H Me 2 -CO-(CH₂)₃-OCH₂-Ph Me H
1-1610 H H H H Me 2 -CO-(CH₂)₃-OCH₂-Ph H Me
1-1611 H H H H Me 2 -CO-(CH₂)₃-OCH₂-Ph F H
1-1612 H H H H Me 2 -CO-(CH₂)₃-OCH₂-Ph H F
1-1613 H H Me Me Me 2 -CO-(CH₂)₃-OCH₂-Ph H H
1-1614 CO₂Me H H H Me 2 -CO-(CH₂)₃-OCH₂-Ph H H
1-1615 CO₂Me H H H Me 2 -CO-(CH₂)₃-OCH₂-Ph H H
1-1616 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-F-Ph) H H
1-1617 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-F-Ph) H H
1-1618 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-Cl-Ph) H H
1-1619 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-Br-Ph) H H
1-1620 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-Me-Ph) H H
1-1621 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-Me-Ph) H H
1-1622 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-Et-Ph) H H
1-1623 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-Et-Ph) H H
1-1624 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-Pr-Ph) H H
1-1625 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-Pr-Ph) H H
1-1626 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-iPr-Ph) H H
1-1627 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-iPr-Ph) H H
1-1628 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-Bu-Ph) H H
1-1629 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-Bu-Ph) H H
1-1630 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-CF₃-Ph) H H
1-1631 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-CF₃-Ph) H H
1-1632 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-MeO-Ph) H H
1-1633 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-MeO-Ph) H H
1-1634 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-EtO-Ph) H H
1-1635 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-EtO-Ph) H H
1-1636 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-PrO-Ph) H H
1-1637 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-PrO-Ph) H H
1-1638 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-iPrO-Ph) H H
1-1639 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-iPrO-Ph) H H
1-1640 H H H H Me 2 -CO-(CH₂)₃-OCH₂-[3-(2-Et-PrO)Ph] H H
1-1641 H H H H Me 2 -CO-(CH₂)₃-OCH₂-[4-(2-Et-PrO)Ph] H H
1-1642 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-iBuO-Ph) H H
1-1643 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-iBuO-Ph) H H
1-1644 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-MeS-Ph) H H
1-1645 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-MeS-Ph) H H
1-1646 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-EtS-Ph) H H
1-1647 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-EtS-Ph) H H
1-1648 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-PrS-Ph) H H
1-1649 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-PrS-Ph) H H
1-1650 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-iPrS-Ph) H H
1-1651 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-iPrS-Ph) H H
1-1652 H H H H Me 2 -CO-(CH₂)₃-OCH₂-[3-(2-Et-PrS)Ph] H H
1-1653 H H H H Me 2 -CO-(CH₂)₃-OCH₂-[4-(2-Et-PrS)Ph] H H
1-1654 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-iBuS-Ph) H H
1-1655 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-iBuS-Ph) H H
1-1656 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-cHx-Ph) H H
1-1657 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-cHx-Ph) H H
1-1658 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3-Ph-Ph) H H
1-1659 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(4-Ph-Ph) H H
1-1660 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(2,4-diMe-Ph) H H
1-1661 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3,4-diMe-Ph) H H
1-1662 H H H H Me 2 -CO-(CH₂)₃-OCH₂-(3,5-diMe-Ph) H H
1-1663 H H H H Me 2 -CO-(CH₂)₄-OCH₂-cHx H H
1-1664 H H H H Me 2 -CO-(CH₂)₄-OCH₂-Ph H H
1-1665 H H H H Me 2 -CO-(CH₂)₅-OCH₂-cHx H H
1-1666 H H H H Me 2 -CO-(CH₂)₅-OCH₂-Ph H H
1-1667 H H H H Me 2 -CH(OH)-CH₂-cHx H H
1-1668 H H H H Me 2 -CH(OH)-CH₂-Ph H H
1-1669 H H H H Me 2 -CH(OH)-(CH₂)₂-cHx H H
1-1670 H H H H Me 2 -CH(OH)-(CH₂)₂-Ph H H
1-1671 H H H H Me 2 -CH(OH)-(CH₂)₃-cHx H H
1-1672 H H H H Me 2 -CH(OH)-(CH₂)₃-Ph H H
1-1673 H H H H Me 2 -CH(OH)-(CH₂)₄-cHx H H
1-1674 H H Me Me Me 2 -CH(OH)-(CH₂)₄-cHx H H
1-1675 CO₂Me H H H Me 2 -CH(OH)-(CH₂)₄-cHx H H
1-1676 CO₂Et H H H Me 2 -CH(OH)-(CH₂)₄-cHx H H
1-1677 H H H H Me 2 -CH(OH)-(CH₂)₄-(4-F-cHx) H H
1-1678 H H H H Me 2 -CH(OH)-(CH₂)₄-(4-Me-cHx) H H
1-1679 H H H H Me 2 -CH(OH)-(CH₂)₄-(4-Et-cHx) H H
1-1680 H H H H Me 2 -CH(OH)-(CH₂)₄-(4-CF₃-cHx) H H
1-1681 H H H H Me 2 -CH(OH)-(CH₂)₄-(4-MeO-cHx) H H
1-1682 H H H H Me 2 -CH(OH)-(CH₂)₄-(4-EtO-cHx) H H
1-1683 H H H H Me 2 -CH(OH)-(CH₂)₄-(4-MeS-cHx) H H
1-1684 H H H H Me 2 -CH(OH)-(CH₂)₄-(4-cHx-cHx) H H
1-1685 H H H H Me 2 -CH(OH)-(CH₂)₄-(4-Ph-cHx) H H
1-1686 H H H H Me 2 -CH(OH)-(CH₂)₄-Ph H H
1-1687 H H Me Me Me 2 -CH(OH)-(CH₂)₄-Ph H H
1-1688 CO₂Me H H H Me 2 -CH(OH)-(CH₂)₄-Ph H H
1-1689 CO₂Et H H H Me 2 -CH(OH)-(CH₂)₄-Ph H H
1-1690 H H H H Me 2 -CH(OH)-(CH₂)₄-(4-F-Ph) H H
1-1691 H H H H Me 2 -CH(OH)-(CH₂)₄-(4-Me-Ph) H H
1-1692 H H H H Me 2 -CH(OH)-(CH₂)₄-(4-Et-Ph) H H
1-1693 H H H H Me 2 -CH(OH)-(CH₂)₄-(4-CF₃-Ph) H H
1-1694 H H H H Me 2 -CH(OH)-(CH₂)₄-(4-MeO-Ph) H H
1-1695 H H H H Me 2 -CH(OH)-(CH₂)₄-(4-EtO-Ph) H H
1-1696 H H H H Me 2 -CH(OH)-(CH₂)₄-(4-MeS-Ph) H H
1-1697 H H H H Me 2 -CH(OH)-(CH₂)₄-(4-cHx-Ph) H H
1-1698 H H H H Me 2 -CH(OH)-(CH₂)₄-(4-Ph-Ph) H H
1-1699 H H H H Me 2 -CH(OH)-(CH₂)₅-cHx H H
1-1700 H H Me Me Me 2 -CH(OH)-(CH₂)₅-cHx H H
1-1701 CO₂Me H H H Me 2 -CH(OH)-(CH₂)₅-cHx H H
1-1702 CO₂Et H H H Me 2 -CH(OH)-(CH₂)₅-cHx H H
1-1703 H H H H Me 2 -CH(OH)-(CH₂)₅-(4-F-cHx) H H
1-1704 H H H H Me 2 -CH(OH)-(CH₂)₅-(4-Me-cHx) H H
1-1705 H H H H Me 2 -CH(OH)-(CH₂)₅-(4-Et-cHx) H H
1-1706 H H H H Me 2 -CH(OH)-(CH₂)₅-(4-CF₃-cHx) H H
1-1707 H H H H Me 2 -CH(OH)-(CH₂)₅-(4-MeO-cHx) H H
1-1708 H H H H Me 2 -CH(OH)-(CH₂)₅-(4-EtO-cHx) H H
1-1709 H H H H Me 2 -CH(OH)-(CH₂)₅-(4-MeS-cHx) H H
1-1710 H H H H Me 2 -CH(OH)-(CH₂)₅-(4-cHx-cHx) H H
1-1711 H H H H Me 2 -CH(OH)-(CH₂)₅-(4-Ph-cHx) H H
1-1712 H H H H Me 2 -CH(OH)-(CH₂)₅-Ph H H
1-1713 H H Me Me Me 2 -CH(OH)-(CH₂)₅-Ph H H
1-1714 CO₂Me H H H Me 2 -CH(OH)-(CH₂)₅-Ph H H
1-1715 CO₂Et H H H Me 2 -CH(OH)-(CH₂)₅-Ph H H
1-1716 H H H H Me 2 -CH(OH)-(CH₂)₅-(4-F-Ph) H H
1-1717 H H H H Me 2 -CH(OH)-(CH₂)₅-(4-Me-Ph) H H
1-1718 H H H H Me 2 -CH(OH)-(CH₂)₅-(4-Et-Ph) H H
1-1719 H H H H Me 2 -CH(OH)-(CH₂)₅-(4-CF₃-Ph) H H
1-1720 H H H H Me 2 -CH(OH)-(CH₂)₅-(4-MeO-Ph) H H
1-1721 H H H H Me 2 -CH(OH)-(CH₂)₅-(4-EtO-Ph) H H
1-1722 H H H H Me 2 -CH(OH)-(CH₂)₅-(4-MeS-Ph) H H
1-1723 H H H H Me 2 -CH(OH)-(CH₂)₅-(4-cHx-Ph) H H
1-1724 H H H H Me 2 -CH(OH)-(CH₂)₅-(4-Ph-Ph) H H
1-1725 H H H H Me 2 -CH(OH)-(CH₂)₆-cHx H H
1-1726 H H H H Me 2 -CH(OH)-(CH₂)₆-Ph H H
1-1727 H H H H Me 2 -CH(OH)-(CH₂)₇-cHx H H
1-1728 H H H H Me 2 -CH(OH)-(CH₂)₇-Ph H H
1-1729 H H H H Me 2 -4-(cHx-CH₂O)Ph H H
1-1730 H H Me Me Me 2 -4-(cHx-CH₂O)Ph H H
1-1731 CO₂Me H H H Me 2 -4-(cHx-CH₂O)Ph H H
1-1732 CO₂Et H H H Me 2 -4-(cHx-CH₂O)Ph H H
1-1733 H H H H Me 2 -4-(cHx-CH₂O)-2-F-Ph H H
1-1734 H H H H Me 2 -4-(cHx-CH₂O)-3-F-Ph H H
1-1735 H H H H Me 2 -4-(cHx-CH₂O)-2,3-diF-Ph H H
1-1736 H H H H Me 2 -4-(cHx-CH₂O)-2-Cl-Ph H H
1-1737 H H H H Me 2 -4-(cHx-CH₂O)-3-Cl-Ph H H
1-1738 H H H H Me 2 -4-(cHx-CH₂O)-2,3-diCl-Ph H H
1-1739 H H H H Me 2 -4-(cHx-CH₂O)-2-Me-Ph H H
1-1740 H H H H Me 2 -4-(cHx-CH₂O)-3-Me-Ph H H
1-1741 H H H H Me 2 -4-(cHx-CH₂O)-2,3-diMe-Ph H H
1-1742 H H H H Me 2 -4-[cHx-(CH₂)₂O]Ph H H
1-1743 H H H H Me 2 -4-[cHx-(CH₂)₃O]Ph H H
1-1744 H H H H Me 2 -(4-BzO-Ph) H H
1-1745 H H Me Me Me 2 -(4-BzO-Ph) H H
1-1746 CO₂Me H H H Me 2 -(4-BzO-Ph) H H
1-1747 CO₂Et H H H Me 2 -(4-BzO-Ph) H H
1-1748 H H H H Me 2 -(4-BzO-2-F-Ph) H H
1-1749 H H H H Me 2 -(4-BzO-3-F-Ph) H H
1-1750 H H H H Me 2 -(4-BzO-2,3-diF-Ph) H H
1-1751 H H H H Me 2 -(4-BzO-2-Cl-Ph) H H
1-1752 H H H H Me 2 -(4-BzO-3-Cl-Ph) H H
1-1753 H H H H Me 2 -(4-BzO-2,3-diCl-Ph) H H
1-1754 H H H H Me 2 -(4-BzO-2-Me-Ph) H H
1-1755 H H H H Me 2 -(4-BzO-3-Me-Ph) H H
1-1756 H H H H Me 2 -(4-BzO-2,3-diMe-Ph) H H
1-1757 H H H H Me 2 -4-[Ph-(CH₂)₂O]-Ph H H
1-1758 H H H H Me 2 -4-[Ph-(CH₂)₃O]-Ph H H
1-1759 H H H H Et 2 -(CH₂)₃-cHx H H
1-1760 H H H H Et 2 -(CH₂)₃-Ph H H
1-1761 H H H H Et 2 -(CH₂)₄-cHx H H
1-1762 H H H H Et 2 -(CH₂)₄-Ph H H
1-1763 H H H H Et 2 -(CH₂)₅-cPn H H
1-1764 H H H H Et 2 -(CH₂)₅-cHx H H
1-1765 H H H H Et 2 -(CH₂)₅-cHx Me H
1-1766 H H H H Et 2 -(CH₂)₅-cHx H Me
1-1767 H H H H Et 2 -(CH₂)₅-cHx F H
1-1768 H H H H Et 2 -(CH₂)₅-cHx H F
1-1769 H H Me Me Et 2 -(CH₂)₅-cHx H H
1-1770 CO₂Me H H H Et 2 -(CH₂)₅-cHx H H
1-1771 CO₂Et H H H Et 2 -(CH₂)₅-cHx H H
1-1772 H H H H Et 2 -(CH₂)₅-(4-F-cHx) H H
1-1773 H H H H Et 2 -(CH₂)₅-(4-Cl-cHx) H H
1-1774 H H H H Et 2 -(CH₂)₅-(4-Br-cHx) H H
1-1775 H H H H Et 2 -(CH₂)₅-(4-Me-cHx) H H
1-1776 H H H H Et 2 -(CH₂)₅-(4-Et-cHx) H H
1-1777 H H H H Et 2 -(CH₂)₅-(4-Pr-cHx) H H
1-1778 H H H H Et 2 -(CH₂)₅-(4-iPr-cHx) H H
1-1779 H H H H Et 2 -(CH₂)₅-(4-CF₃-cHx) H H
1-1780 H H H H Et 2 -(CH₂)₅-(4-MeO-cHx) H H
1-1781 H H H H Et 2 -(CH₂)₅-(4-EtO-cHx) H H
1-1782 H H H H Et 2 -(CH₂)₅-(4-PrO-cHx) H H
1-1783 H H H H Et 2 -(CH₂)₅-(4-iPrO-cHx) H H
1-1784 H H H H Et 2 -(CH₂)₅-(3-MeS-cHx) H H
1-1785 H H H H Et 2 -(CH₂)₅-(4-MeS-cHx) H H
1-1786 H H H H Et 2 -(CH₂)₅-(2,4-diMe-cHx) H H
1-1787 H H H H Et 2 -(CH₂)₅-(3,4-diMe-cHx) H H
1-1788 H H H H Et 2 -(CH₂)₅-(3,5-diMe-cHx) H H
1-1789 H H H H Et 2 -(CH₂)₅-Ph H H
1-1790 H H H H Et 2 -(CH₂)₅-Ph Me H
1-1791 H H H H Et 2 -(CH₂)₅-Ph H Me
1-1792 H H H H Et 2 -(CH₂)₅-Ph F H
1-1793 H H H H Et 2 -(CH₂)₅-Ph H F
1-1794 H H Me Me Et 2 -(CH₂)₅-Ph H H
1-1795 CO₂Me H H H Et 2 -(CH₂)₅-Ph H H
1-1796 CO₂Et H H H Et 2 -(CH₂)₅-Ph H H
1-1797 H H H H Et 2 -(CH₂)₅-(4-F-Ph) H H
1-1798 H H H H Et 2 -(CH₂)₅-(4-Cl-Ph) H H
1-1799 H H H H Et 2 -(CH₂)₅-(4-Br-Ph) H H
1-1800 H H H H Et 2 -(CH₂)₅-(4-Me-Ph) H H
1-1801 H H H H Et 2 -(CH₂)₅-(4-Et-Ph) H H
1-1802 H H H H Et 2 -(CH₂)₅-(4-Pr-Ph) H H
1-1803 H H H H Et 2 -(CH₂)₅-(4-iPr-Ph) H H
1-1804 H H H H Et 2 -(CH₂)₅-(4-Bu-Ph) H H
1-1805 H H H H Et 2 -(CH₂)₅-(4-CF₃-Ph) H H
1-1806 H H H H Et 2 -(CH₂)₅-(4-MeO-Ph) H H
1-1807 H H H H Et 2 -(CH₂)₅-(4-EtO-Ph) H H
1-1808 H H H H Et 2 -(CH₂)₅-(4-PrO-Ph) H H
1-1809 H H H H Et 2 -(CH₂)₅-(4-iPrO-Ph) H H
1-1810 H H H H Et 2 -(CH₂)₅-(3-MeS-Ph) H H
1-1811 H H H H Et 2 -(CH₂)₅-(4-MeS-Ph) H H
1-1812 H H H H Et 2 -(CH₂)₅-(2,4-diMe-Ph) H H
1-1813 H H H H Et 2 -(CH₂)₅-(3,4-diMe-Ph) H H
1-1814 H H H H Et 2 -(CH₂)₅-(3,5-diMe-Ph) H H
1-1815 H H H H Et 2 -(CH₂)₆-cPn H H
1-1816 H H H H Et 2 -(CH₂)₆-cHx H H
1-1817 H H H H Et 2 -(CH₂)₆-cHx Me H
1-1818 H H H H Et 2 -(CH₂)₆-cHx H Me
1-1819 H H H H Et 2 -(CH₂)₆-cHx F H
1-1820 H H H H Et 2 -(CH₂)₆-cHx H F
1-1821 H H Me Me Et 2 -(CH₂)₆-cHx H H
1-1822 CO₂Me H H H Et 2 -(CH₂)₆-cHx H H
1-1823 CO₂Et H H H Et 2 -(CH₂)₆-cHx H H
1-1824 H H H H Et 2 -(CH₂)₆-(4-F-cHx) H H
1-1825 H H H H Et 2 -(CH₂)₆-(4-Cl-cHx) H H
1-1826 H H H H Et 2 -(CH₂)₆-(4-Br-cHx) H H
1-1827 H H H H Et 2 -(CH₂)₆-(4-Me-cHx) H H
1-1828 H H H H Et 2 -(CH₂)₆-(4-Et-cHx) H H
1-1829 H H H H Et 2 -(CH₂)₆-(4-Pr-cHx) H H
1-1830 H H H H Et 2 -(CH₂)₆-(4-iPr-cHx) H H
1-1831 H H H H Et 2 -(CH₂)₆-(4-Bu-cHx) H H
1-1832 H H H H Et 2 -(CH₂)₆-(4-CF₃-cHx) H H
1-1833 H H H H Et 2 -(CH₂)₆-(4-MeO-cHx) H H
1-1834 H H H H Et 2 -(CH₂)₆-(4-EtO-cHx) H H
1-1835 H H H H Et 2 -(CH₂)₆-(4-PrO-cHx) H H
1-1836 H H H H Et 2 -(CH₂)₆-(4-iPrO-cHx) H H
1-1837 H H H H Et 2 -(CH₂)₆-(3-MeS-cHx) H H
1-1838 H H H H Et 2 -(CH₂)₆-(4-MeS-cHx) H H
1-1839 H H H H Et 2 -(CH₂)₆-(2,4-diMe-cHx) H H
1-1840 H H H H Et 2 -(CH₂)₆-(3,4-diMe-cHx) H H
1-1841 H H H H Et 2 -(CH₂)₆-(3,5-diMe-cHx) H H
1-1842 H H H H Et 2 -(CH₂)₆-Ph H H
1-1843 H H H H Et 2 -(CH₂)₆-Ph Me H
1-1844 H H H H Et 2 -(CH₂)₆-Ph H Me
1-1845 H H H H Et 2 -(CH₂)₆-Ph F H
1-1846 H H H H Et 2 -(CH₂)₆-Ph H F
1-1847 H H Me Me Et 2 -(CH₂)₆-Ph H H
1-1848 CO₂Me H H H Et 2 -(CH₂)₆-Ph H H
1-1849 CO₂Et H H H Et 2 -(CH₂)₆-Ph H H
1-1850 H H H H Et 2 -(CH₂)₆-(4-F-Ph) H H
1-1851 H H H H Et 2 -(CH₂)₆-(4-Cl-Ph) H H
1-1852 H H H H Et 2 -(CH₂)₆-(4-Br-Ph) H H
1-1853 H H H H Et 2 -(CH₂)₆-(4-Me-Ph) H H
1-1854 H H H H Et 2 -(CH₂)₆-(4-Et-Ph) H H
1-1855 H H H H Et 2 -(CH₂)₆-(4-Pr-Ph) H H
1-1856 H H H H Et 2 -(CH₂)₆-(4-iPr-Ph) H H
1-1857 H H H H Et 2 -(CH₂)₆-(4-Bu-Ph) H H
1-1858 H H H H Et 2 -(CH₂)₆-(4-CF₃-Ph) H H
1-1859 H H H H Et 2 -(CH₂)₆-(4-MeO-Ph) H H
1-1860 H H H H Et 2 -(CH₂)₆-(4-EtO-Ph) H H
1-1861 H H H H Et 2 -(CH₂)₆-(4-PrO-Ph) H H
1-1862 H H H H Et 2 -(CH₂)₆-(4-iPrO-Ph) H H
1-1863 H H H H Et 2 -(CH₂)₆-(3-MeS-Ph) H H
1-1864 H H H H Et 2 -(CH₂)₆-(4-MeS-Ph) H H
1-1865 H H H H Et 2 -(CH₂)₆-(2,4-diMe-Ph) H H
1-1866 H H H H Et 2 -(CH₂)₆-(3,4-diMe-Ph) H H
1-1867 H H H H Et 2 -(CH₂)₆-(3,5-diMe-Ph) H H
1-1868 H H H H Et 2 -(CH₂)₇-cHx H H
1-1869 H H H H Et 2 -(CH₂)₇-Ph H H
1-1870 H H H H Et 2 -CH=CH-cHx H H
1-1871 H H H H Et 2 -CH=CH-Ph H H
1-1872 H H H H Et 2 -CH=CH-(CH₂)₃-cHx H H
1-1873 H H Me Me Et 2 -CH=CH-(CH₂)₃-cHx H H
1-1874 CO₂Me H H H Et 2 -CH=CH-(CH₂)₃-cHx H H
1-1875 CO₂Et H H H Et 2 -CH=CH-(CH₂)₃-cHx H H
1-1876 H H H H Et 2 -CH=CH-(CH₂)₃-Ph H H
1-1877 H H Me Me Et 2 -CH=CH-(CH₂)₃-Ph H H
1-1878 CO₂Me H H H Et 2 -CH=CH-(CH₂)₃-Ph H H
1-1879 CO₂Et H H H Et 2 -CH=CH-(CH₂)₃-Ph H H
1-1880 H H H H Et 2 -CH=CH-(CH₂)₄-cHx H H
1-1881 H H Me Me Et 2 -CH=CH-(CH₂)₄-cHx H H
1-1882 CO₂Me H H H Et 2 -CH=CH-(CH₂)₄-cHx H H
1-1883 CO₂Et H H H Et 2 -CH=CH-(CH₂)₄-cHx H H
1-1884 H H H H Et 2 -CH=CH-(CH₂)₄-Ph H H
1-1885 H H Me Me Et 2 -CH=CH-(CH₂)₄-Ph H H
1-1886 CO₂Me H H H Et 2 -CH=CH-(CH₂)₄-Ph H H
1-1887 CO₂Et H H H Et 2 -CH=CH-(CH₂)₄-Ph H H
1-1888 H H H H Et 2 -CH=CH-CH₂O-cHx H H
1-1889 H H H H Et 2 -CH=CH-CH₂O-Ph H H
1-1890 H H H H Et 2 -CH=CH-(CH₂)₂O-cHx H H
1-1891 H H H H Et 2 -CH=CH-(CH₂)₂O-Ph H H
1-1892 H H H H Et 2 -C≡C-CH₂-cHx H H
1-1893 H H Me Me Et 2 -C≡C-CH₂-cHx H H
1-1894 CO₂Me H H H Et 2 -C≡C-CH₂-cHx H H
1-1895 CO₂Et H H H Et 2 -C≡C-CH₂-cHx H H
1-1896 H H H H Et 2 -C≡C-CH₂-Ph H H
1-1897 H H Me Me Et 2 -C≡C-CH₂-Ph H H
1-1898 CO₂Me H H H Et 2 -C≡C-CH₂-Ph H H
1-1899 CO₂Et H H H Et 2 -C≡C-CH₂-Ph H H
1-1900 H H H H Et 2 -C≡C-(CH₂)₂-cHx H H
1-1901 H H Me Me Et 2 -C≡C-(CH₂)₂-cHx H H
1-1902 CO₂Me H H H Et 2 -C≡C-(CH₂)₂-cHx H H
1-1903 CO₂Et H H H Et 2 -C≡C-(CH₂)₂-cHx H H
1-1904 H H H H Et 2 -C≡C-(CH₂)₂-Ph H H
1-1905 H H Me Me Et 2 -C≡C-(CH₂)₂-Ph H H
1-1906 CO₂Me H H H Et 2 -C≡C-(CH₂)₂-Ph H H
1-1907 CO₂Et H H H Et 2 -C≡C-(CH₂)₂-Ph H H
1-1908 H H H H Et 2 -C≡C-(CH₂)₃-cPn H H
1-1909 H H H H Et 2 -C≡C-(CH₂)₃-cHx H H
1-1910 H H H H Et 2 -C≡C-(CH₂)₃-cHx Me H
1-1911 H H H H Et 2 -C≡C-(CH₂)₃-cHx H Me
1-1912 H H H H Et 2 -C≡C-(CH₂)₃-cHx F H
1-1913 H H H H Et 2 -C≡C-(CH₂)₃-cHx H F
1-1914 H H Me Me Et 2 -C≡C-(CH₂)₃-cHx H H
1-1915 CO₂Me H H H Et 2 -C≡C-(CH₂)₃-cHx H H
1-1916 CO₂Et H H H Et 2 -C≡C-(CH₂)₃-cHx H H
1-1917 H H H H Et 2 -C≡C-(CH₂)₃-(4-F-cHx) H H
1-1918 H H H H Et 2 -C≡C-(CH₂)₃-(4-Cl-cHx) H H
1-1919 H H H H Et 2 -C≡C-(CH₂)₃-(4-Br-cHx) H H
1-1920 H H H H Et 2 -C≡C-(CH₂)₃-(4-Me-cHx) H H
1-1921 H H H H Et 2 -C≡C-(CH₂)₃-(4-Et-cHx) H H
1-1922 H H H H Et 2 -C≡C-(CH₂)₃-(4-Pr-cHx) H H
1-1923 H H H H Et 2 -C≡C-(CH₂)₃-(4-iPr-cHx) H H
1-1924 H H H H Et 2 -C≡C-(CH₂)₃-(4-Bu-cHx) H H
1-1925 H H H H Et 2 -C≡C-(CH₂)₃-(4-CF₃-cHx) H H
1-1926 H H H H Et 2 -C≡C-(CH₂)₃-(4-MeO-cHx) H H
1-1927 H H H H Et 2 -C≡C-(CH₂)₃-(4-EtO-cHx) H H
1-1928 H H H H Et 2 -C≡C-(CH₂)₃-(4-PrO-cHx) H H
1-1929 H H H H Et 2 -C≡C-(CH₂)₃-(4-iPrO-cHx) H H
1-1930 H H H H Et 2 -C≡C-(CH₂)₃-(3-MeS-cHx) H H
1-1931 H H H H Et 2 -C≡C-(CH₂)₃-(4-MeS-cHx) H H
1-1932 H H H H Et 2 -C≡C-(CH₂)₃-(2,4-diMe-cHx) H H
1-1933 H H H H Et 2 -C≡C-(CH₂)₃-(3,4-diMe-cHx) H H
1-1934 H H H H Et 2 -C≡C-(CH₂)₃-(3,5-diMe-cHx) H H
1-1935 H H H H Et 2 -C≡C-(CH₂)₃-Ph H H
1-1936 H H H H Et 2 -C≡C-(CH₂)₃-Ph Me H
1-1937 H H H H Et 2 -C≡C-(CH₂)₃-Ph H Me
1-1938 H H H H Et 2 -C≡C-(CH₂)₃-Ph F H
1-1939 H H H H Et 2 -C≡C-(CH₂)₃-Ph H F
1-1940 H H Me Me Et 2 -C≡C-(CH₂)₃-Ph H H
1-1941 CO₂Me H H H Et 2 -C≡C-(CH₂)₃-Ph H H
1-1942 CO₂Et H H H Et 2 -C≡C-(CH₂)₃-Ph H H
1-1943 H H H H Et 2 -C≡C-(CH₂)₃-(4-F-Ph) H H
1-1944 H H H H Et 2 -C≡C-(CH₂)₃-(4-Cl-Ph) H H
1-1945 H H H H Et 2 -C≡C-(CH₂)₃-(4-Br-Ph) H H
1-1946 H H H H Et 2 -C≡C-(CH₂)₃-(4-Me-Ph) H H
1-1947 H H H H Et 2 -C≡C-(CH₂)₃-(4-Et-Ph) H H
1-1948 H H H H Et 2 -C≡C-(CH₂)₃-(4-Pr-Ph) H H
1-1949 H H H H Et 2 -C≡C-(CH₂)₃-(4-iPr-Ph) H H
1-1950 H H H H Et 2 -C≡C-(CH₂)₃-(4-Bu-Ph) H H
1-1951 H H H H Et 2 -C≡C-(CH₂)₃-(4-CF₃-Ph) H H
1-1952 H H H H Et 2 -C≡C-(CH₂)₃-(4-MeO-Ph) H H
1-1953 H H H H Et 2 -C≡C-(CH₂)₃-(4-EtO-Ph) H H
1-1954 H H H H Et 2 -C≡C-(CH₂)₃-(4-PrO-Ph) H H
1-1955 H H H H Et 2 -C≡C-(CH₂)₃-(4-iPrO-Ph) H H
1-1956 H H H H Et 2 -C≡C-(CH₂)₃-(3-MeS-Ph) H H
1-1957 H H H H Et 2 -C≡C-(CH₂)₃-(4-MeS-Ph) H H
1-1958 H H H H Et 2 -C≡C-(CH₂)₃-(2,4-diMe-Ph) H H
1-1959 H H H H Et 2 -C≡C-(CH₂)₃-(3,4-diMe-Ph) H H
1-1960 H H H H Et 2 -C≡C-(CH₂)₃-(3,5-diMe-Ph) H H
1-1961 H H H H Et 2 -C≡C-(CH₂)₄-cPn H H
1-1962 H H H H Et 2 -C≡C-(CH₂)₄-cHx H H
1-1963 H H H H Et 2 -C≡C-(CH₂)₄-cHx Me H
1-1964 H H H H Et 2 -C≡C-(CH₂)₄-cHx H Me
1-1965 H H H H Et 2 -C≡C-(CH₂)₄-cHx F H
1-1966 H H H H Et 2 -C≡C-(CH₂)₄-cHx H F
1-1967 H H Me Me Et 2 -C≡C-(CH₂)₄-cHx H H
1-1968 CO₂Me H H H Et 2 -C≡C-(CH₂)₄-cHx H H
1-1969 CO₂Et H H H Et 2 -C≡C-(CH₂)₄-cHx H H
1-1970 H H H H Et 2 -C≡C-(CH₂)₄-(4-F-cHx) H H
1-1971 H H H H Et 2 -C≡C-(CH₂)₄-(4-Cl-cHx) H H
1-1972 H H H H Et 2 -C≡C-(CH₂)₄-(4-Br-cHx) H H
1-1973 H H H H Et 2 -C≡C-(CH₂)₄-(4-Me-cHx) H H
1-1974 H H H H Et 2 -C≡C-(CH₂)₄-(4-Et-cHx) H H
1-1975 H H H H Et 2 -C≡C-(CH₂)₄-(4-Pr-cHx) H H
1-1976 H H H H Et 2 -C≡C-(CH₂)₄-(4-iPr-cHx) H H
1-1977 H H H H Et 2 -C≡C-(CH₂)₄-(4-Bu-cHx) H H
1-1978 H H H H Et 2 -C≡C-(CH₂)₄-(4-CF₃-cHx) H H
1-1979 H H H H Et 2 -C≡C-(CH₂)₄-(4-MeO-cHx) H H
1-1980 H H H H Et 2 -C≡C-(CH₂)₄-(4-EtO-cHx) H H
1-1981 H H H H Et 2 -C≡C-(CH₂)₄-(4-PrO-cHx) H H
1-1982 H H H H Et 2 -C≡C-(CH₂)₄-(4-iPrO-cHx) H H
1-1983 H H H H Et 2 -C≡C-(CH₂)₄-(4-MeS-cHx) H H
1-1984 H H H H Et 2 -C≡C-(CH₂)₄-(2,4-diMe-cHx) H H
1-1985 H H H H Et 2 -C≡C-(CH₂)₄-(3,4-diMe-cHx) H H
1-1986 H H H H Et 2 -C≡C-(CH₂)₄-(3,5-diMe-cHx) H H
1-1987 H H H H Et 2 -C≡C-(CH₂)₄-Ph H H
1-1988 H H H H Et 2 -C≡C-(CH₂)₄-Ph Me H
1-1989 H H H H Et 2 -C≡C-(CH₂)₄-Ph H Me
1-1990 H H H H Et 2 -C≡C-(CH₂)₄-Ph F H
1-1991 H H H H Et 2 -C≡C-(CH₂)₄-Ph H F
1-1992 H H Me Me Et 2 -C≡C-(CH₂)₄-Ph H H
1-1993 CO₂Me H H H Et 2 -C≡C-(CH₂)₄-Ph H H
1-1994 CO₂Et H H H Et 2 -C≡C-(CH₂)₄-Ph H H
1-1995 H H H H Et 2 -C≡C-(CH₂)₄-(4-F-Ph) H H
1-1996 H H H H Et 2 -C≡C-(CH₂)₄-(4-Cl-Ph) H H
1-1997 H H H H Et 2 -C≡C-(CH₂)₄-(4-Br-Ph) H H
1-1998 H H H H Et 2 -C≡C-(CH₂)₄-(4-Me-Ph) H H
1-1999 H H H H Et 2 -C≡C-(CH₂)₄-(4-Et-Ph) H H
1-2000 H H H H Et 2 -C≡C-(CH₂)₄-(4-Pr-Ph) H H
1-2001 H H H H Et 2 -C≡C-(CH₂)₄-(4-iPr-Ph) H H
1-2002 H H H H Et 2 -C≡C-(CH₂)₄-(4-Bu-Ph) H H
1-2003 H H H H Et 2 -C≡C-(CH₂)₄-(4-CF₃-Ph) H H
1-2004 H H H H Et 2 -C≡C-(CH₂)₄-(4-MeO-Ph) H H
1-2005 H H H H Et 2 -C≡C-(CH₂)₄-(4-EtO-Ph) H H
1-2006 H H H H Et 2 -C≡C-(CH₂)₄-(4-PrO-Ph) H H
1-2007 H H H H Et 2 -C≡C-(CH₂)₄-(4-iPrO-Ph) H H
1-2008 H H H H Et 2 -C≡C-(CH₂)₄-(3-MeS-Ph) H H
1-2009 H H H H Et 2 -C≡C-(CH₂)₄-(4-MeS-Ph) H H
1-2010 H H H H Et 2 -C≡C-(CH₂)₄-(2,4-diMe-Ph) H H
1-2011 H H H H Et 2 -C≡C-(CH₂)₄-(3,4-diMe-Ph) H H
1-2012 H H H H Et 2 -C≡C-(CH₂)₄-(3,5-diMe-Ph) H H
1-2013 H H H H Et 2 -C≡C-(CH₂)₅-cHx H H
1-2014 H H Me Me Et 2 -C≡C-(CH₂)₅-cHx H H
1-2015 CO₂Me H H H Et 2 -C≡C-(CH₂)₅-cHx H H
1-2016 CO₂Et H H H Et 2 -C≡C-(CH₂)₅-cHx H H
1-2017 H H H H Et 2 -C≡C-(CH₂)₅-Ph H H
1-2018 H H Me Me Et 2 -C≡C-(CH₂)₅-Ph H H
1-2019 CO₂Me H H H Et 2 -C≡C-(CH₂)₅-Ph H H
1-2020 CO₂Et H H H Et 2 -C≡C-(CH₂)₅-Ph H H
1-2021 H H H H Et 2 -C≡C-(CH₂)₆-cHx H H
1-2022 H H Me Me Et 2 -C≡C-(CH₂)₆-cHx H H
1-2023 CO₂Me H H H Et 2 -C≡C-(CH₂)₆-cHx H H
1-2024 CO₂Et H H H Et 2 -C≡C-(CH₂)₆-cHx H H
1-2025 H H H H Et 2 -C≡C-(CH₂)₆-Ph H H
1-2026 H H Me Me Et 2 -C≡C-(CH₂)₆-Ph H H
1-2027 CO₂Me H H H Et 2 -C≡C-(CH₂)₆-Ph H H
1-2028 CO₂Et H H H Et 2 -C≡C-(CH₂)₆-Ph H H
1-2029 H H H H Et 2 -C≡C-CH₂O-cHx H H
1-2030 H H Me Me Et 2 -C≡C-CH₂O-cHx H H
1-2031 CO₂Me H H H Et 2 -C≡C-CH₂O-cHx H H
1-2032 CO₂Et H H H Et 2 -C≡C-CH₂O-cHx H H
1-2033 H H H H Et 2 -C≡C-CH₂O-Ph H H
1-2034 H H Me Me Et 2 -C≡C-CH₂O-Ph H H
1-2035 CO₂Me H H H Et 2 -C≡C-CH₂O-Ph H H
1-2036 CO₂Et H H H Et 2 -C≡C-CH₂O-Ph H H
1-2037 H H H H Et 2 -C≡C-(CH₂)₂O-cPn H H
1-2038 H H H H Et 2 -C≡C-(CH₂)₂O-cHx H H
1-2039 H H H H Et 2 -C≡C-(CH₂)₂O-cHx Me H
1-2040 H H H H Et 2 -C≡C-(CH₂)₂O-cHx H Me
1-2041 H H H H Et 2 -C≡C-(CH₂)₂O-cHx F H
1-2042 H H H H Et 2 -C≡C-(CH₂)₂O-cHx H F
1-2043 H H Me Me Et 2 -C≡C-(CH₂)₂O-cHx H H
1-2044 CO₂Me H H H Et 2 -C≡C-(CH₂)₂O-cHx H H
1-2045 CO₂Et H H H Et 2 -C≡C-(CH₂)₂O-cHx H H
1-2046 H H H H Et 2 -C≡C-(CH₂)₂O-(4-F-cHx) H H
1-2047 H H H H Et 2 -C≡C-(CH₂)₂O-(4-Cl-cHx) H H
1-2048 H H H H Et 2 -C≡C-(CH₂)₂O-(4-Br-cHx) H H
1-2049 H H H H Et 2 -C≡C-(CH₂)₂O-(4-Me-cHx) H H
1-2050 H H H H Et 2 -C≡C-(CH₂)₂O-(4-Et-cHx) H H
1-2051 H H H H Et 2 -C≡C-(CH₂)₂O-(4-Pr-cHx) H H
1-2052 H H H H Et 2 -C≡C-(CH₂)₂O-(4-iPr-cHx) H H
1-2053 H H H H Et 2 -C≡C-(CH₂)₂O-(4-Bu-cHx) H H
1-2054 H H H H Et 2 -C≡C-(CH₂)₂O-(4-CF₃-cHx) H H
1-2055 H H H H Et 2 -C≡C-(CH₂)₂O-(4-MeO-cHx) H H
1-2056 H H H H Et 2 -C≡C-(CH₂)₂O-(4-EtO-cHx) H H
1-2057 H H H H Et 2 -C≡C-(CH₂)₂O-(4-PrO-cHx) H H
1-2058 H H H H Et 2 -C≡C-(CH₂)₂O-(4-iPrO-cHx) H H
1-2059 H H H H Et 2 -C≡C-(CH₂)₂O-(3-MeS-cHx) H H
1-2060 H H H H Et 2 -C≡C-(CH₂)₂O-(4-MeS-cHx) H H
1-2061 H H H H Et 2 -C≡C-(CH₂)₂O-(2,4-diMe-cHx) H H
1-2062 H H H H Et 2 -C≡C-(CH₂)₂O-(3,4-diMe-cHx) H H
1-2063 H H H H Et 2 -C≡C-(CH₂)₂O-(3,5-diMe-cHx) H H
1-2064 H H H H Et 2 -C≡C-(CH₂)₂O-Ph H H
1-2065 H H H H Et 2 -C≡C-(CH₂)₂O-Ph Me H
1-2066 H H H H Et 2 -C≡C-(CH₂)₂O-Ph H Me
1-2067 H H H H Et 2 -C≡C-(CH₂)₂O-Ph F H
1-2068 H H H H Et 2 -C≡C-(CH₂)₂O-Ph H F
1-2069 H H Me Me Et 2 -C≡C-(CH₂)₂-OCH₂-Ph H H
1-2070 CO₂Me H H H Et 2 -C≡C-(CH₂)₂O-Ph H H
1-2071 CO₂Et H H H Et 2 -C≡C-(CH₂)₂O-Ph H H
1-2072 H H H H Et 2 -C≡C-(CH₂)₂O-(4-F-Ph) H H
1-2073 H H H H Et 2 -C≡C-(CH₂)₂O-(4-Cl-Ph) H H
1-2074 H H H H Et 2 -C≡C-(CH₂)₂O-(4-Br-Ph) H H
1-2075 H H H H Et 2 -C≡C-(CH₂)₂O-(4-Me-Ph) H H
1-2076 H H H H Et 2 -C≡C-(CH₂)₂O-(4-Et-Ph) H H
1-2077 H H H H Et 2 -C≡C-(CH₂)₂O-(4-Pr-Ph) H H
1-2078 H H H H Et 2 -C≡C-(CH₂)₂O-(4-iPr-Ph) H H
1-2079 H H H H Et 2 -C≡C-(CH₂)₂O-(4-Bu-Ph) H H
1-2080 H H H H Et 2 -C≡C-(CH₂)₂O-(4-CF₃-Ph) H H
1-2081 H H H H Et 2 -C≡C-(CH₂)₂O-(4-MeO-Ph) H H
1-2082 H H H H Et 2 -C≡C-(CH₂)₂O-(4-EtO-Ph) H H
1-2083 H H H H Et 2 -C≡C-(CH₂)₂O-(4-PrO-Ph) H H
1-2084 H H H H Et 2 -C≡C-(CH₂)₂O-(4-iPrO-Ph) H H
1-2085 H H H H Et 2 -C≡C-(CH₂)₂O-(4-MeS-Ph) H H
1-2086 H H H H Et 2 -C≡C-(CH₂)₂O-(2,4-diMe-Ph) H H
1-2087 H H H H Et 2 -C≡C-(CH₂)₂O-(3,4-diMe-Ph) H H
1-2088 H H H H Et 2 -C≡C-(CH₂)₂O-(3,5-diMe-Ph) H H
1-2089 H H H H Et 2 -CO-(CH₂)₃-cHx H H
1-2090 H H Me Me Et 2 -CO-(CH₂)₃-cHx H H
1-2091 CO₂Me H H H Et 2 -CO-(CH₂)₃-cHx H H
1-2092 CO₂Et H H H Et 2 -CO-(CH₂)₃-cHx H H
1-2093 H H H H Et 2 -CO-(CH₂)₃-Ph H H
1-2094 H H Me Me Et 2 -CO-(CH₂)₃-Ph H H
1-2095 CO₂Me H H H Et 2 -CO-(CH₂)₃-Ph H H
1-2096 CO₂Et H H H Et 2 -CO-(CH₂)₃-Ph H H
1-2097 H H H H Et 2 -CO-(CH₂)₄-cHx H H
1-2098 H H Me Me Et 2 -CO-(CH₂)₄-cHx H H
1-2099 CO₂Me H H H Et 2 -CO-(CH₂)₄-cHx H H
1-2100 CO₂Et H H H Et 2 -CO-(CH₂)₄-cHx H H
1-2101 H H H H Et 2 -CO-(CH₂)₄-Ph H H
1-2102 H H Me Me Et 2 -CO-(CH₂)₄-Ph H H
1-2103 CO₂Me H H H Et 2 -CO-(CH₂)₄-Ph H H
1-2104 CO₂Et H H H Et 2 -CO-(CH₂)₄-Ph H H
1-2105 H H H H Et 2 -CO-(CH₂)₅-cHx H H
1-2106 H H Me Me Et 2 -CO-(CH₂)₅-cHx H H
1-2107 CO₂Me H H H Et 2 -CO-(CH₂)₅-cHx H H
1-2108 CO₂Et H H H Et 2 -CO-(CH₂)₅-cHx H H
1-2109 H H H H Et 2 -CO-(CH₂)₅-Ph H H
1-2110 H H Me Me Et 2 -CO-(CH₂)₅-Ph H H
1-2111 CO₂Me H H H Et 2 -CO-(CH₂)₅-Ph H H
1-2112 CO₂Et H H H Et 2 -CO-(CH₂)₅-Ph H H
1-2113 H H H H Et 2 -CH(OH)-(CH₂)₄-cHx H H
1-2114 H H Me Me Et 2 -CH(OH)-(CH₂)₄-cHx H H
1-2115 CO₂Me H H H Et 2 -CH(OH)-(CH₂)₄-cHx H H
1-2116 CO₂Et H H H Et 2 -CH(OH)-(CH₂)₄-cHx H H
1-2117 H H H H Et 2 -CH(OH)-(CH₂)₄-Ph H H
1-2118 H H Me Me Et 2 -CH(OH)-(CH₂)₄-Ph H H
1-2119 CO₂Me H H H Et 2 -CH(OH)-(CH₂)₄-Ph H H
1-2120 CO₂Et H H H Et 2 -CH(OH)-(CH₂)₄-Ph H H
1-2121 H H H H Et 2 -CH(OH)-(CH₂)₅-cHx H H
1-2122 H H Me Me Et 2 -CH(OH)-(CH₂)₅-cHx H H
1-2123 CO₂Me H H H Et 2 -CH(OH)-(CH₂)₅-cHx H H
1-2124 CO₂Et H H H Et 2 -CH(OH)-(CH₂)₅-cHx H H
1-2125 H H H H Et 2 -CH(OH)-(CH₂)₅-Ph H H
1-2126 H H Me Me Et 2 -CH(OH)-(CH₂)₅-Ph H H
1-2127 CO₂Me H H H Et 2 -CH(OH)-(CH₂)₅-Ph H H
1-2128 CO₂Et H H H Et 2 -CH(OH)-(CH₂)₅-Ph H H
1-2129 H H H H Et 2 -4-(cHx-CH₂O)Ph H H
1-2130 H H Me Me Et 2 -4-(cHx-CH₂O)Ph H H
1-2131 CO₂Me H H H Et 2 -4-(cHx-CH₂O)Ph H H
1-2132 CO₂Et H H H Et 2 -4-(cHx-CH₂O)Ph H H
1-2133 H H H H Et 2 -4-[cHx-(CH₂)₂O]Ph H H
1-2134 H H H H Et 2 -4-[cHx-(CH₂)₃O]Ph H H
1-2135 H H H H Et 2 -(4-BzO-Ph) H H
1-2136 H H Me Me Et 2 -(4-BzO-Ph) H H
1-2137 CO₂Me H H H Et 2 -(4-BzO-Ph) H H
1-2138 CO₂Et H H H Et 2 -(4-BzO-Ph) H H
1-2139 H H H H Et 2 -(4-BzO-2-F-Ph) H H
1-2140 H H H H Et 2 -(4-BzO-3-F-Ph) H H
1-2141 H H H H Et 2 -(4-BzO-2,3-diF-Ph) H H
1-2142 H H H H Et 2 -(4-BzO-2-Cl-Ph) H H
1-2143 H H H H Et 2 -(4-BzO-3-Cl-Ph) H H
1-2144 H H H H Et 2 -(4-BzO-2,3-diCl-Ph) H H
1-2145 H H H H Et 2 -(4-BzO-2-Me-Ph) H H
1-2146 H H H H Et 2 -(4-BzO-3-Me-Ph) H H
1-2147 H H H H Et 2 -(4-BzO-2,3-diMe-Ph) H H
1-2148 H H H H Et 2 -4-[Ph-(CH₂)₂O]-Ph H H
1-2149 H H H H Et 2 -4-[Ph-(CH₂)₃O]-Ph H H
1-2150 H H H H Pr 2 -(CH₂)₅-cHx H H
1-2151 H H H H Pr 2 -(CH₂)₅-Ph H H
1-2152 H H H H Pr 2 -(CH₂)₆-cHx H H
1-2153 H H H H Pr 2 -(CH₂)₆-Ph H H
1-2154 H H H H Pr 2 -C≡C-CH₂-cHx H H
1-2155 H H H H Pr 2 -C≡C-(CH₂)₃-cHx H H
1-2156 H H H H Pr 2 -C≡C-(CH₂)₃-Ph H H
1-2157 H H H H Pr 2 -C≡C-(CH₂)₄-cHx H H
1-2158 H H H H Pr 2 -C≡C-(CH₂)₄-Ph H H
1-2159 CO₂Me H H H Pr 2 -C≡C-CH₂O-Ph H H
1-2160 CO₂Et H H H Pr 2 -C≡C-CH₂O-Ph H H
1-2161 H H H H Pr 2 -C≡C-(CH₂)₂O-cHx H H
1-2162 H H H H Pr 2 -C≡C-(CH₂)₂O-Ph H H
1-2163 H H H H Pr 2 -4-(cHx-CH₂O)Ph H H
1-2164 H H H H Pr 2 -(4-BzO-Ph) H H
1-2165 H H H H Me 3 -(CH₂)₅-cHx H H
1-2166 H H H H Me 3 -(CH₂)₆-cHx H H
1-2167 H H H H Me 3 -CH=CH-(CH₂)₃-cHx H H
1-2168 H H H H Me 3 -CH=CH-(CH₂)₄-cHx H H
1-2169 H H H H Me 3 -C≡C-(CH₂)₃-cHx H H
1-2170 H H H H Me 3 -C≡C-(CH₂)₄-cHx H H
1-2171 H H H H Me 3 -CO-(CH₂)₄-cHx H H
1-2172 H H H H Me 3 -CO-(CH₂)₅-cHx H H
1-2173 H H H H Me 3 -CO-(CH₂)₄-Ph H H
1-2174 H H H H Me 3 -CO-(CH₂)₅-Ph H H
1-2175 H H H H Me 3 -CH(OH)-(CH₂)₄-cHx H H
1-2176 H H H H Me 3 -CH(OH)-(CH₂)₅-cHx H H
1-2177 H H H H Me 3 -4-(cHx-CH₂O)Ph H H
1-2178 H H H H Me 3 -(4-BzO-Ph) H H
1-2179 H H H H Me 3 -C≡C-CH₂O-cPn H H
1-2180 H H H H Me 3 -C≡C-(CH₂)₂O-cPn H H
1-2181 H H H H Me 3 -C≡C-CH₂O-cHx H H
1-2182 H H H H Me 3 -C≡C-(CH₂)₂O-cHx H H
1-2183 H H H H Me 3 -C≡C-CH₂O-Ph H H
1-2184 H H H H Me 3 -C≡C-(CH₂)₂O-Ph H H
1-2185 H H H H Me 2 -(CH₂)₄-(3-F-Ph) H H
1-2186 H H H H Me 2 -(CH₂)₄-(3,4-diF-Ph) H H
1-2187 H H H H Me 2 -(CH₂)₄-(3,5-diF-Ph) H H
1-2188 H H H H Me 2 -(CH₂)₄-(3-Cl-Ph) H H
1-2189 H H H H Me 2 -(CH₂)₄-(4-Cl-Ph) H H
1-2190 H H H H Me 2 -(CH₂)₄-(3,4-diCl-Ph) H H
1-2191 H H H H Me 2 -(CH₂)₄-(3,5-diCl-Ph) H H
1-2192 H H H H Me 2 -(CH₂)₄-(3-Me-Ph) H H
1-2193 H H H H Me 2 -(CH₂)₄-(3,4-diMe-Ph) H H
1-2194 H H H H Me 2 -(CH₂)₄-(3,5-diMe-Ph) H H
1-2195 H H H H Me 2 -(CH₂)₄-(3-CF₃-Ph) H H
1-2196 H H H H Me 2 -(CH₂)₄-(3,4-diCF₃-Ph) H H
1-2197 H H H H Me 2 -(CH₂)₄-(3,5-diCF₃-Ph) H H
1-2198 H H H H Me 2 -(CH₂)₄-(3-MeO-Ph) H H
1-2199 H H H H Me 2 -(CH₂)₄-(3,4-diMeO-Ph) H H
1-2200 H H H H Me 2 -(CH₂)₄-(3,5-diMeO-Ph) H H
1-2201 H H H H Me 2 -(CH₂)₄-(3,4,5-triMeO-Ph) H H
1-2202 H H H H Me 2 -(CH₂)₄-(3-Ac-Ph) H H
1-2203 H H H H Me 2 -(CH₂)₄-(4-Ac-Ph) H H
1-2204 H H H H Me 2 -(CH₂)₅-(3,4-diF-Ph) H H
1-2205 H H H H Me 2 -(CH₂)₅-(3,5-diF-Ph) H H
1-2206 H H H H Me 2 -(CH₂)₅-(3-Cl-Ph) H H
1-2207 H H H H Me 2 -(CH₂)₅-(3,4-diCl-Ph) H H
1-2208 H H H H Me 2 -(CH₂)₅-(3,5-diCl-Ph) H H
1-2209 H H H H Me 2 -(CH₂)₅-(3,4-diCF₃-Ph) H H
1-2210 H H H H Me 2 -(CH₂)₅-(3,5-diCF₃-Ph) H H
1-2211 H H H H Me 2 -(CH₂)₅-(3,4-diMeO-Ph) H H
1-2212 H H H H Me 2 -(CH₂)₅-(3,5-diMeO-Ph) H H
1-2213 H H H H Me 2 -(CH₂)₅-(3,4,5-triMeO-Ph) H H
1-2214 H H H H Me 2 -(CH₂)₅-(3-Ac-Ph) H H
1-2215 H H H H Me 2 -(CH₂)₅-(4-Ac-Ph) H H
1-2216 H H H H Me 2 -(CH₂)₃-O-(3-F-Ph) H H
1-2217 H H H H Me 2 -(CH₂)₃-O-(3,4-diF-Ph) H H
1-2218 H H H H Me 2 -(CH₂)₃-O-(3,5-diF-Ph) H H
1-2219 H H H H Me 2 -(CH₂)₃-O-(3-Me-Ph) H H
1-2220 H H H H Me 2 -(CH₂)₃-O-(3,4-diMe-Ph) H H
1-2221 H H H H Me 2 -(CH₂)₃-O-(3,5-diMe-Ph) H H
1-2222 H H H H Me 2 -(CH₂)₃-O-(3-CF₃-Ph) H H
1-2223 H H H H Me 2 -(CH₂)₃-O-(3,4-diCF₃-Ph) H H
1-2224 H H H H Me 2 -(CH₂)₃-O-(3,5-diCF₃-Ph) H H
1-2225 H H H H Me 2 -(CH₂)₃-O-(3-MeO-Ph) H H
1-2226 H H H H Me 2 -(CH₂)₃-O-(3,4-diMeO-Ph) H H
1-2227 H H H H Me 2 -(CH₂)₃-O-(3,5-diMeO-Ph) H H
1-2228 H H H H Me 2 -(CH₂)₃-O-(3,4,5-triMeO-Ph) H H
1-2229 H H H H Me 2 -(CH₂)₃-O-(3-Ac-Ph) H H
1-2230 H H H H Me 2 -(CH₂)₃-O-(4-Ac-Ph) H H
1-2231 H H H H Me 2 -(CH₂)₄-O-(3,4-diF-Ph) H H
1-2232 H H H H Me 2 -(CH₂)₄-O-(3,5-diF-Ph) H H
1-2233 H H H H Me 2 -(CH₂)₄-O-(3,4-diMeO-Ph) H H
1-2234 H H H H Me 2 -(CH₂)₄-O-(3,5-diMeO-Ph) H H
1-2235 H H H H Me 2 -(CH₂)₄-O-(3,4,5-triMeO-Ph) H H
1-2236 H H H H Me 2 -(CH₂)₄-O-(3-Ac-Ph) H H
1-2237 H H H H Me 2 -(CH₂)₄-O-(4-Ac-Ph) H H
1-2238 H H H H Me 2 -C≡C-(CH₂)₂-(3-F-Ph) H H
1-2239 H H H H Me 2 -C≡C-(CH₂)₂-(3,4-diF-Ph) H H
1-2240 H H H H Me 2 -C≡C-(CH₂)₂-(3,5-diF-Ph) H H
1-2241 H H H H Me 2 -C≡C-(CH₂)₂-(3-Cl-Ph) H H
1-2242 H H H H Me 2 -C≡C-(CH₂)₂-(4-Cl-Ph) H H
1-2243 H H H H Me 2 -C≡C-(CH₂)₂-(3,4-diCl-Ph) H H
1-2244 H H H H Me 2 -C≡C-(CH₂)₂-(3,5-diCl-Ph) H H
1-2245 H H H H Me 2 -C≡C-(CH₂)₂-(3-Me-Ph) H H
1-2246 H H H H Me 2 -C≡C-(CH₂)₂-(3,4-diMe-Ph) H H
1-2247 H H H H Me 2 -C≡C-(CH₂)₂-(3,5-diMe-Ph) H H
1-2248 H H H H Me 2 -C≡C-(CH₂)₂-(3-CF₃-Ph) H H
1-2249 H H H H Me 2 -C≡C-(CH₂)₂-(3,4-diCF₃-Ph) H H
1-2250 H H H H Me 2 -C≡C-(CH₂)₂-(3,5-diCF₃-Ph) H H
1-2251 H H H H Me 2 -C≡C-(CH₂)₂-(3-MeO-Ph) H H
1-2252 H H H H Me 2 -C≡C-(CH₂)₂-(3,4-diMeO-Ph) H H
1-2253 H H H H Me 2 -C≡C-(CH₂)₂-(3,5-diMeO-Ph) H H
1-2254 H H H H Me 2 -C≡C-(CH₂)₂-(3,4,5-triMeO-Ph) H H
1-2255 H H H H Me 2 -C≡C-(CH₂)₂-(3-Ac-Ph) H H
1-2256 H H H H Me 2 -C≡C-(CH₂)₂-(4-Ac-Ph) H H
1-2257 H H H H Me 2 -C≡C-(CH₂)₃-(3,4-diF-Ph) H H
1-2258 H H H H Me 2 -C≡C-(CH₂)₃-(3,5-diF-Ph) H H
1-2259 H H H H Me 2 -C≡C-(CH₂)₃-(3-Cl-Ph) H H
1-2260 H H H H Me 2 -C≡C-(CH₂)₃-(3,4-diCl-Ph) H H
1-2261 H H H H Me 2 -C≡C-(CH₂)₃-(3,5-diCl-Ph) H H
1-2262 H H H H Me 2 -C≡C-(CH₂)₃-(3,4-diCF₃-Ph) H H
1-2263 H H H H Me 2 -C≡C-(CH₂)₃-(3,5-diCF₃-Ph) H H
1-2264 H H H H Me 2 -C≡C-(CH₂)₃-(3,4-diMeO-Ph) H H
1-2265 H H H H Me 2 -C≡C-(CH₂)₃-(3,5-diMeO-Ph) H H
1-2266 H H H H Me 2 -C≡C-(CH₂)₃-(3,4,5-triMeO-Ph) H H
1-2267 H H H H Me 2 -C≡C-(CH₂)₃-(3-Ac-Ph) H H
1-2268 H H H H Me 2 -C≡C-(CH₂)₃-(4-Ac-Ph) H H
1-2269 H H H H Me 2 -C≡C-CH₂-O-(3-F-Ph) H H
1-2270 H H H H Me 2 -C≡C-CH₂-O-(3,4-diF-Ph) H H
1-2271 H H H H Me 2 -C≡C-CH₂-O-(3,5-diF-Ph) H H
1-2272 H H H H Me 2 -C≡C-CH₂-O-(3-Cl-Ph) H H
1-2273 H H H H Me 2 -C≡C-CH₂-O-(4-Cl-Ph) H H
1-2274 H H H H Me 2 -C≡C-CH₂-O-(3,4-diCl-Ph) H H
1-2275 H H H H Me 2 -C≡C-CH₂-O-(3,5-diCl-Ph) H H
1-2276 H H H H Me 2 -C≡C-CH₂-O-(3-Me-Ph) H H
1-2277 H H H H Me 2 -C≡C-CH₂-O-(2,4-diMe-Ph) H H
1-2278 H H H H Me 2 -C≡C-CH₂-O-(3,4-diMe-Ph) H H
1-2279 H H H H Me 2 -C≡C-CH₂-O-(3,5-diMe-Ph) H H
1-2280 H H H H Me 2 -C≡C-CH₂-O-(3-CF₃-Ph) H H
1-2281 H H H H Me 2 -C≡C-CH₂-O-(3,4-diCF₃-Ph) H H
1-2282 H H H H Me 2 -C≡C-CH₂-O-(3,5-diCF₃-Ph) H H
1-2283 H H H H Me 2 -C≡C-CH₂-O-(3-MeO-Ph) H H
1-2284 H H H H Me 2 -C≡C-CH₂-O-(3,4-diMeO-Ph) H H
1-2285 H H H H Me 2 -C≡C-CH₂-O-(3,5-diMeO-Ph) H H
1-2286 H H H H Me 2 -C≡C-CH₂-O-(3,4,5-triMeO-Ph) H H
1-2287 H H H H Me 2 -C≡C-CH₂-O-(3-Ac-Ph) H H
1-2288 H H H H Me 2 -C≡C-CH₂-O-(4-Ac-Ph) H H
1-2289 H H H H Me 2 -C≡C-CH₂-O-(4-CO₂H-Ph) H H
1-2290 H H H H Me 2 -C≡C-(CH₂)₂-O-(3,4-diF-Ph) H H
1-2291 H H H H Me 2 -C≡C-(CH₂)₂-O-(3,5-diF-Ph) H H
1-2292 H H H H Me 2 -C≡C-(CH₂)₂-O-(3-Cl-Ph) H H
1-2293 H H H H Me 2 -C≡C-(CH₂)₂-O-(3,4-diCl-Ph) H H
1-2294 H H H H Me 2 -C≡C-(CH₂)₂-O-(3,5-diCl-Ph) H H
1-2295 H H H H Me 2 -C≡C-(CH₂)₂-O-(3,4-diCF₃-Ph) H H
1-2296 H H H H Me 2 -C≡C-(CH₂)₂-O-(3,5-diCF₃-Ph) H H
1-2297 H H H H Me 2 -C≡C-(CH₂)₂-O-(3,4-diMeO-Ph) H H
1-2298 H H H H Me 2 -C≡C-(CH₂)₂-O-(3,5-diMeO-Ph) H H
1-2299 H H H H Me 2 -C≡C-(CH₂)₂-O-(3,4,5-triMeO-Ph) H H
1-2300 H H H H Me 2 -C≡C-(CH₂)₂-O-(3-Ac-Ph) H H
1-2301 H H H H Me 2 -C≡C-(CH₂)₂-O-(4-Ac-Ph) H H
1-2302 H H H H Me 2 -CO-(CH₂)₃-(3-F-Ph) H H
1-2303 H H H H Me 2 -CO-(CH₂)₃-(4-F-Ph) H H
1-2304 H H H H Me 2 -CO-(CH₂)₃-(3,4-diF-Ph) H H
1-2305 H H H H Me 2 -CO-(CH₂)₃-(3,5-diF-Ph) H H
1-2306 H H H H Me 2 -CO-(CH₂)₃-(3-Cl-Ph) H H
1-2307 H H H H Me 2 -CO-(CH₂)₃-(4-Cl-Ph) H H
1-2308 H H H H Me 2 -CO-(CH₂)₃-(3,4-diCl-Ph) H H
1-2309 H H H H Me 2 -CO-(CH₂)₃-(3,5-diCl-Ph) H H
1-2310 H H H H Me 2 -CO-(CH₂)₃-(3-Me-Ph) H H
1-2311 H H H H Me 2 -CO-(CH₂)₃-(4-Me-Ph) H H
1-2312 H H H H Me 2 -CO-(CH₂)₃-(3,4-diMe-Ph) H H
1-2313 H H H H Me 2 -CO-(CH₂)₃-(3,5-diMe-Ph) H H
1-2314 H H H H Me 2 -CO-(CH₂)₃-(3-Et-Ph) H H
1-2315 H H H H Me 2 -CO-(CH₂)₃-(4-Et-Ph) H H
1-2316 H H H H Me 2 -CO-(CH₂)₃-(3-CF₃-Ph) H H
1-2317 H H H H Me 2 -CO-(CH₂)₃-(4-CF₃-Ph) H H
1-2318 H H H H Me 2 -CO-(CH₂)₃-(3,4-diCF₃-Ph) H H
1-2319 H H H H Me 2 -CO-(CH₂)₃-(3,5-diCF₃-Ph) H H
1-2320 H H H H Me 2 -CO-(CH₂)₃-(3-MeO-Ph) H H
1-2321 H H H H Me 2 -CO-(CH₂)₃-(4-MeO-Ph) H H
1-2322 H H H H Me 2 -CO-(CH₂)₃-(3,4-diMeO-Ph) H H
1-2323 H H H H Me 2 -CO-(CH₂)₃-(3,5-diMeO-Ph) H H
1-2324 H H H H Me 2 -CO-(CH₂)₃-(3,4,5-triMeO-Ph) H H
1-2325 H H H H Me 2 -CO-(CH₂)₃-(4-MeS-Ph) H H
1-2326 H H H H Me 2 -CO-(CH₂)₃-(3-Ac-Ph) H H
1-2327 H H H H Me 2 -CO-(CH₂)₃-(4-Ac-Ph) H H
1-2328 H H H H Me 2 -CO-(CH₂)₄-(3-F-Ph) H H
1-2329 H H H H Me 2 -CO-(CH₂)₄-(3,4-diF-Ph) H H
1-2330 H H H H Me 2 -CO-(CH₂)₄-(3,5-diF-Ph) H H
1-2331 H H H H Me 2 -CO-(CH₂)₄-(3-Cl-Ph) H H
1-2332 H H H H Me 2 -CO-(CH₂)₄-(4-Cl-Ph) H H
1-2333 H H H H Me 2 -CO-(CH₂)₄-(3,4-diCl-Ph) H H
1-2334 H H H H Me 2 -CO-(CH₂)₄-(3,5-diCl-Ph) H H
1-2335 H H H H Me 2 -CO-(CH₂)₄-(3-Me-Ph) H H
1-2336 H H H H Me 2 -CO-(CH₂)₄-(3,4-diMe-Ph) H H
1-2337 H H H H Me 2 -CO-(CH₂)₄-(3,5-diMe-Ph) H H
1-2338 H H H H Me 2 -CO-(CH₂)₄-(3-CF₃-Ph) H H
1-2339 H H H H Me 2 -CO-(CH₂)₄-(3,4-diCF₃-Ph) H H
1-2340 H H H H Me 2 -CO-(CH₂)₄-(3,5-diCF₃-Ph) H H
1-2341 H H H H Me 2 -CO-(CH₂)₄-(3-MeO-Ph) H H
1-2342 H H H H Me 2 -CO-(CH₂)₄-(3,4-diMeO-Ph) H H
1-2343 H H H H Me 2 -CO-(CH₂)₄-(3,5-diMeO-Ph) H H
1-2344 H H H H Me 2 -CO-(CH₂)₄-(3,4,5-triMeO-Ph) H H
1-2345 H H H H Me 2 -CO-(CH₂)₄-(3-Ac-Ph) H H
1-2346 H H H H Me 2 -CO-(CH₂)₄-(4-Ac-Ph) H H
1-2347 H H H H Me 2 -CH(OH)-(CH₂)₃-(3-F-Ph) H H
1-2348 H H H H Me 2 -CH(OH)-(CH₂)₃-(4-F-Ph) H H
1-2349 H H H H Me 2 -CH(OH)-(CH₂)₃-(3,4-diF-Ph) H H
1-2350 H H H H Me 2 -CH(OH)-(CH₂)₃-(3,5-diF-Ph) H H
1-2351 H H H H Me 2 -CH(OH)-(CH₂)₃-(3-Cl-Ph) H H
1-2352 H H H H Me 2 -CH(OH)-(CH₂)₃-(4-Cl-Ph) H H
1-2353 H H H H Me 2 -CH(OH)-(CH₂)₃-(3,4-diCl-Ph) H H
1-2354 H H H H Me 2 -CH(OH)-(CH₂)₃-(3,5-diCl-Ph) H H
1-2355 H H H H Me 2 -CH(OH)-(CH₂)₃-(3-Me-Ph) H H
1-2356 H H H H Me 2 -CH(OH)-(CH₂)₃-(4-Me-Ph) H H
1-2357 H H H H Me 2 -CH(OH)-(CH₂)₃-(3,4-diMe-Ph) H H
1-2358 H H H H Me 2 -CH(OH)-(CH₂)₃-(3,5-diMe-Ph) H H
1-2359 H H H H Me 2 -CH(OH)-(CH₂)₃-(3-Et-Ph) H H
1-2360 H H H H Me 2 -CH(OH)-(CH₂)₃-(4-Et-Ph) H H
1-2361 H H H H Me 2 -CH(OH)-(CH₂)₃-(3-CF₃-Ph) H H
1-2362 H H H H Me 2 -CH(OH)-(CH₂)₃-(4-CF₃-Ph) H H
1-2363 H H H H Me 2 -CH(OH)-(CH₂)₃-(3,4-diCF₃-Ph) H H
1-2364 H H H H Me 2 -CH(OH)-(CH₂)₃-(3,5-diCF₃-Ph) H H
1-2365 H H H H Me 2 -CH(OH)-(CH₂)₃-(3-MeO-Ph) H H
1-2366 H H H H Me 2 -CH(OH)-(CH₂)₃-(4-MeO-Ph) H H
1-2367 H H H H Me 2 -CH(OH)-(CH₂)₃-(3,4-diMeO-Ph) H H
1-2368 H H H H Me 2 -CH(OH)-(CH₂)₃-(3,5-diMeO-Ph) H H
1-2369 H H H H Me 2 -CH(OH)-(CH₂)₃-(3,4,5-triMeO-Ph) H H
1-2370 H H H H Me 2 -CH(OH)-(CH₂)₃-(4-MeS-Ph) H H
1-2371 H H H H Me 2 -CH(OH)-(CH₂)₃-(3-Ac-Ph) H H
1-2372 H H H H Me 2 -CH(OH)-(CH₂)₃-(4-Ac-Ph) H H
1-2373 H H H H Me 2 -CH(OH)-(CH₂)₄-(3-F-Ph) H H
1-2374 H H H H Me 2 -CH(OH)-(CH₂)₄-(3,4-diF-Ph) H H
1-2375 H H H H Me 2 -CH(OH)-(CH₂)₄-(3,5-diF-Ph) H H
1-2376 H H H H Me 2 -CH(OH)-(CH₂)₄-(3-Cl-Ph) H H
1-2377 H H H H Me 2 -CH(OH)-(CH₂)₄-(4-Cl-Ph) H H
1-2378 H H H H Me 2 -CH(OH)-(CH₂)₄-(3,4-diCl-Ph) H H
1-2379 H H H H Me 2 -CH(OH)-(CH₂)₄-(3,5-diCl-Ph) H H
1-2380 H H H H Me 2 -CH(OH)-(CH₂)₄-(3-Me-Ph) H H
1-2381 H H H H Me 2 -CH(OH)-(CH₂)₄-(3,4-diMe-Ph) H H
1-2382 H H H H Me 2 -CH(OH)-(CH₂)₄-(3,5-diMe-Ph) H H
1-2383 H H H H Me 2 -CH(OH)-(CH₂)₄-(3-CF₃-Ph) H H
1-2384 H H H H Me 2 -CH(OH)-(CH₂)₄-(3,4-diCF₃-Ph) H H
1-2385 H H H H Me 2 -CH(OH)-(CH₂)₄-(3,5-diCF₃-Ph) H H
1-2386 H H H H Me 2 -CH(OH)-(CH₂)₄-(3-MeO-Ph) H H
1-2387 H H H H Me 2 -CH(OH)-(CH₂)₄-(3,4-diMeO-Ph) H H
1-2388 H H H H Me 2 -CH(OH)-(CH₂)₄-(3,5-diMeO-Ph) H H
1-2389 H H H H Me 2 -CH(OH)-(CH₂)₄-(3,4,5-triMeO-Ph) H H
1-2390 H H H H Me 2 -CH(OH)-(CH₂)₄-(3-Ac-Ph) H H
1-2391 H H H H Me 2 -CH(OH)-(CH₂)₄-(4-Ac-Ph) H H
1-2392 H H H H Me 2 -O-(CH₂)₃-cHx H H
1-2393 H H H H Me 2 -O-(CH₂)₄-cHx H H
1-2394 H H H H Me 2 -O-(CH₂)₅-cHx H H
1-2395 H H H H Me 2 -O-(CH₂)₃-Ph H H
1-2396 H H H H Me 2 -O-(CH₂)₄-Ph H H
1-2397 H H H H Me 2 -O-(CH₂)₅-Ph H H
1-2398 COCH₃ H H H Me 2 -(CH₂)₄-cHx H H
1-2399 COC₂H₅ H H H Me 2 -(CH₂)₄-cHx H H
1-2400 COC₃H₇ H H H Me 2 -(CH₂)₄-cHx H H
1-2401 COC₄H₉ H H H Me 2 -(CH₂)₄-cHx H H
1-2402 COC₅H₁₁ H H H Me 2 -(CH₂)₄-cHx H H
1-2403 COC₆H₁₃ H H H Me 2 -(CH₂)₄-cHx H H
1-2404 COC₇H₁₅ H H H Me 2 -(CH₂)₄-cHx H H
1-2405 COC₈H₁₇ H H H Me 2 -(CH₂)₄-cHx H H
1-2406 COCH₃ H H H Me 2 -(CH₂)₄-Ph H H
1-2407 COC₂H₅ H H H Me 2 -(CH₂)₄-Ph H H
1-2408 COC₃H₇ H H H Me 2 -(CH₂)₄-Ph H H
1-2409 COC₄H₉ H H H Me 2 -(CH₂)₄-Ph H H
1-2410 COC₅H₁₁ H H H Me 2 -(CH₂)₄-Ph H H
1-2411 COC₆H₁₃ H H H Me 2 -(CH₂)₄-Ph H H
1-2412 COC₇H₁₅ H H H Me 2 -(CH₂)₄-Ph H H
1-2413 COC₈H₁₇ H H H Me 2 -(CH₂)₄-Ph H H
1-2414 COCH₃ H H H Me 2 -(CH₂)₅-cHx H H
1-2415 COC₂H₅ H H H Me 2 -(CH₂)₅-cHx H H
1-2416 COC₃H₇ H H H Me 2 -(CH₂)₅-cHx H H
1-2417 COC₄H₉ H H H Me 2 -(CH₂)₅-cHx H H
1-2418 COC₅H₁₁ H H H Me 2 -(CH₂)₅-cHx H H
1-2419 COC₆H₁₃ H H H Me 2 -(CH₂)₅-cHx H H
1-2420 COC₇H₁₅ H H H Me 2 -(CH₂)₅-cHx H H
1-2421 COC₈H₁₇ H H H Me 2 -(CH₂)₅-cHx H H
1-2422 COCH₃ H H H Me 2 -(CH₂)₅-Ph H H
1-2423 COC₂H₅ H H H Me 2 -(CH₂)₅-Ph H H
1-2424 COC₃H₇ H H H Me 2 -(CH₂)₅-Ph H H
1-2425 COC₄H₉ H H H Me 2 -(CH₂)₅-Ph H H
1-2426 COC₅H₁₁ H H H Me 2 -(CH₂)₅-Ph H H
1-2427 COC₆H₁₃ H H H Me 2 -(CH₂)₅-Ph H H
1-2428 COC₇H₁₅ H H H Me 2 -(CH₂)₅-Ph H H
1-2429 COC₈H₁₇ H H H Me 2 -(CH₂)₅-Ph H H
1-2430 COCH₃ H H H Me 2 -C≡C-(CH₂)₂-cHx H H
1-2431 COC₂H₅ H H H Me 2 -C≡C-(CH₂)₂-cHx H H
1-2432 COC₃H₇ H H H Me 2 -C≡C-(CH₂)₂-cHx H H
1-2433 COC₄H₉ H H H Me 2 -C≡C-(CH₂)₂-cHx H H
1-2434 COC₅H₁₁ H H H Me 2 -C≡C-(CH₂)₂-cHx H H
1-2435 COC₆H₁₃ H H H Me 2 -C≡C-(CH₂)₂-cHx H H
1-2436 COC₇H₁₅ H H H Me 2 -C≡C-(CH₂)₂-cHx H H
1-2437 COC₈H₁₇ H H H Me 2 -C≡C-(CH₂)₂-cHx H H
1-2438 COCH₃ H H H Me 2 -C≡C-(CH₂)₂-Ph H H
1-2439 COC₂H₅ H H H Me 2 -C≡C-(CH₂)₂-Ph H H
1-2440 COC₃H₇ H H H Me 2 -C≡C-(CH₂)₂-Ph H H
1-2441 COC₄H₉ H H H Me 2 -C≡C-(CH₂)₂-Ph H H
1-2442 COC₅H₁₁ H H H Me 2 -C≡C-(CH₂)₂-Ph H H
1-2443 COC₆H₁₃ H H H Me 2 -C≡C-(CH₂)₂-Ph H H
1-2444 COC₇H₁₅ H H H Me 2 -C≡C-(CH₂)₂-Ph H H
1-2445 COC₈H₁₇ H H H Me 2 -C≡C-(CH₂)₂-Ph H H
1-2446 COCH₃ H H H Me 2 -C≡C-(CH₂)₃-cHx H H
1-2447 COC₂H₅ H H H Me 2 -C≡C-(CH₂)₃-cHx H H
1-2448 COC₃H₇ H H H Me 2 -C≡C-(CH₂)₃-cHx H H
1-2449 COC₄H₉ H H H Me 2 -C≡C-(CH₂)₃-cHx H H
1-2450 COC₅H₁₁ H H H Me 2 -C≡C-(CH₂)₃-cHx H H
1-2451 COC₆H₁₃ H H H Me 2 -C≡C-(CH₂)₃-cHx H H
1-2452 COC₇H₁₅ H H H Me 2 -C≡C-(CH₂)₃-cHx H H
1-2453 COC₈H₁₇ H H H Me 2 -C≡C-(CH₂)₃-cHx H H
1-2454 COCH₃ H H H Me 2 -C≡C-(CH₂)₃-Ph H H
1-2455 COC₂H₅ H H H Me 2 -C≡C-(CH₂)₃-Ph H H
1-2456 COC₃H₇ H H H Me 2 -C≡C-(CH₂)₃-Ph H H
1-2457 COC₄H₉ H H H Me 2 -C≡C-(CH₂)₃-Ph H H
1-2458 COC₅H₁₁ H H H Me 2 -C≡C-(CH₂)₃-Ph H H
1-2459 COC₆H₁₃ H H H Me 2 -C≡C-(CH₂)₃-Ph H H
1-2460 COC₇H₁₅ H H H Me 2 -C≡C-(CH₂)₃-Ph H H
1-2461 COC₈H₁₇ H H H Me 2 -C≡C-(CH₂)₃-Ph H H
1-2462 COCH₃ H H H Me 2 -C≡C-(CH₂)₄-cHx H H
1-2463 COC₂H₅ H H H Me 2 -C≡C-(CH₂)₄-cHx H H
1-2464 COC₃H₇ H H H Me 2 -C≡C-(CH₂)₄-cHx H H
1-2465 COC₄H₉ H H H Me 2 -C≡C-(CH₂)₄-cHx H H
1-2466 COC₅H₁₁ H H H Me 2 -C≡C-(CH₂)₄-cHx H H
1-2467 COC₆H₁₃ H H H Me 2 -C≡C-(CH₂)₄-cHx H H
1-2468 COC₇H₁₅ H H H Me 2 -C≡C-(CH₂)₄-cHx H H
1-2469 COC₈H₁₇ H H H Me 2 -C≡C-(CH₂)₄-cHx H H
1-2470 COCH₃ H H H Me 2 -C≡C-(CH₂)₄-Ph H H
1-2471 COC₂H₅ H H H Me 2 -C≡C-(CH₂)₄-Ph H H
1-2472 COC₃H₇ H H H Me 2 -C≡C-(CH₂)₄-Ph H H
1-2473 COC₄H₉ H H H Me 2 -C≡C-(CH₂)₄-Ph H H
1-2474 COC₅H₁₁ H H H Me 2 -C≡C-(CH₂)₄-Ph H H
1-2475 COC₆H₁₃ H H H Me 2 -C≡C-(CH₂)₄-Ph H H
1-2476 COC₇H₁₅ H H H Me 2 -C≡C-(CH₂)₄-Ph H H
1-2477 COC₈H₁₇ H H H Me 2 -C≡C-(CH₂)₄-Ph H H
1-2478 COCH₃ H H H Me 2 -C≡C-(CH₂)₂O-cHx H H
1-2479 COC₂H₅ H H H Me 2 -C≡C-(CH₂)₂O-cHx H H
1-2480 COC₃H₇ H H H Me 2 -C≡C-(CH₂)₂O-cHx H H
1-2481 COC₄H₉ H H H Me 2 -C≡C-(CH₂)₂O-cHx H H
1-2482 COC₅H₁₁ H H H Me 2 -C≡C-(CH₂)₂O-cHx H H
1-2483 COC₆H₁₃ H H H Me 2 -C≡C-(CH₂)₂O-cHx H H
1-2484 COC₇H₁₅ H H H Me 2 -C≡C-(CH₂)₂O-cHx H H
1-2485 COC₈H₁₇ H H H Me 2 -C≡C-(CH₂)₂O-cHx H H
1-2486 COCH₃ H H H Me 2 -C≡C-(CH₂)₂O-Ph H H
1-2487 COC₂H₅ H H H Me 2 -C≡C-(CH₂)₂O-Ph H H
1-2488 COC₃H₇ H H H Me 2 -C≡C-(CH₂)₂O-Ph H H
1-2489 COC₄H₉ H H H Me 2 -C≡C-(CH₂)₂O-Ph H H
1-2490 COC₅H₁₁ H H H Me 2 -C≡C-(CH₂)₂O-Ph H H
1-2491 COC₆H₁₃ H H H Me 2 -C≡C-(CH₂)₂O-Ph H H
1-2492 COC₇H₁₅ H H H Me 2 -C≡C-(CH₂)₂O-Ph H H
1-2493 COC₈H₁₇ H H H Me 2 -C≡C-(CH₂)₂O-Ph H H
1-2494 COCH₃ H H H Me 2 -CO-(CH₂)₃-cHx H H
1-2495 COC₂H₅ H H H Me 2 -CO-(CH₂)₃-cHx H H
1-2496 COC₃H₇ H H H Me 2 -CO-(CH₂)₃-cHx H H
1-2497 COC₄H₉ H H H Me 2 -CO-(CH₂)₃-cHx H H
1-2498 COC₅H₁₁ H H H Me 2 -CO-(CH₂)₃-cHx H H
1-2499 COC₆H₁₃ H H H Me 2 -CO-(CH₂)₃-cHx H H
1-2500 COC₇H₁₅ H H H Me 2 -CO-(CH₂)₃-cHx H H
1-2501 COC₈H₁₇ H H H Me 2 -CO-(CH₂)₃-cHx H H
1-2502 COCH₃ H H H Me 2 -CO-(CH₂)₃-Ph H H
1-2503 COC₂H₅ H H H Me 2 -CO-(CH₂)₃-Ph H H
1-2504 COC₃H₇ H H H Me 2 -CO-(CH₂)₃-Ph H H
1-2505 COC₄H₉ H H H Me 2 -CO-(CH₂)₃-Ph H H
1-2506 COC₅H₁₁ H H H Me 2 -CO-(CH₂)₃-Ph H H
1-2507 COC₆H₁₃ H H H Me 2 -CO-(CH₂)₃-Ph H H
1-2508 COC₇H₁₅ H H H Me 2 -CO-(CH₂)₃-Ph H H
1-2509 COC₈H₁₇ H H H Me 2 -CO-(CH₂)₃-Ph H H
1-2510 COCH₃ H H H Me 2 -CO-(CH₂)₄-cHx H H
1-2511 COC₂H₅ H H H Me 2 -CO-(CH₂)₄-cHx H H
1-2512 COC₃H₇ H H H Me 2 -CO-(CH₂)₄-cHx H H
1-2513 COC₄H₉ H H H Me 2 -CO-(CH₂)₄-cHx H H
1-2514 COC₅H₁₁ H H H Me 2 -CO-(CH₂)₄-cHx H H
1-2515 COC₆H₁₃ H H H Me 2 -CO-(CH₂)₄-cHx H H
1-2516 COC₇H₁₅ H H H Me 2 -CO-(CH₂)₄-cHx H H
1-2517 COC₈H₁₇ H H H Me 2 -CO-(CH₂)₄-cHx H H
1-2518 COCH₃ H H H Me 2 -CO-(CH₂)₄-Ph H H
1-2519 COC₂H₅ H H H Me 2 -CO-(CH₂)₄-Ph H H
1-2520 COC₃H₇ H H H Me 2 -CO-(CH₂)₄-Ph H H
1-2521 COC₄H₉ H H H Me 2 -CO-(CH₂)₄-Ph H H
1-2522 COC₅H₁₁ H H H Me 2 -CO-(CH₂)₄-Ph H H
1-2523 COC₆H₁₃ H H H Me 2 -CO-(CH₂)₄-Ph H H
1-2524 COC₇H₁₅ H H H Me 2 -CO-(CH₂)₄-Ph H H
1-2525 COC₈H₁₇ H H H Me 2 -CO-(CH₂)₄-Ph H H
1-2526 COCH₃ H H H Me 2 -CO-(CH₂)₅-cHx H H
1-2527 COC₂H₅ H H H Me 2 -CO-(CH₂)₅-cHx H H
1-2528 COC₃H₇ H H H Me 2 -CO-(CH₂)₅-cHx H H
1-2529 COC₄H₉ H H H Me 2 -CO-(CH₂)₅-cHx H H
1-2530 COC₅H₁₁ H H H Me 2 -CO-(CH₂)₅-cHx H H
1-2531 COC₆H₁₃ H H H Me 2 -CO-(CH₂)₅-cHx H H
1-2532 COC₇H₁₅ H H H Me 2 -CO-(CH₂)₅-cHx H H
1-2533 COC₈H₁₇ H H H Me 2 -CO-(CH₂)₅-cHx H H
1-2534 COCH₃ H H H Me 2 -CO-(CH₂)₅-Ph H H
1-2535 COC₂H₅ H H H Me 2 -CO-(CH₂)₅-Ph H H
1-2536 COC₃H₇ H H H Me 2 -CO-(CH₂)₅-Ph H H
1-2537 COC₄H₉ H H H Me 2 -CO-(CH₂)₅-Ph H H
1-2538 COC₅H₁₁ H H H Me 2 -CO-(CH₂)₅-Ph H H
1-2539 COC₆H₁₃ H H H Me 2 -CO-(CH₂)₅-Ph H H
1-2540 COC₇H₁₅ H H H Me 2 -CO-(CH₂)₅-Ph H H
1-2541 COC₈H₁₇ H H H Me 2 -CO-(CH₂)₅-Ph H H
1-2542 COCH₃ H H H Me 2 -CH(OH)-(CH₂)₄-cHx H H
1-2543 COC₂H₅ H H H Me 2 -CH(OH)-(CH₂)₄-cHx H H
1-2544 COC₃H₇ H H H Me 2 -CH(OH)-(CH₂)₄-cHx H H
1-2545 COC₄H₉ H H H Me 2 -CH(OH)-(CH₂)₄-cHx H H
1-2546 COC₅H₁₁ H H H Me 2 -CH(OH)-(CH₂)₄-cHx H H
1-2547 COC₆H₁₃ H H H Me 2 -CH(OH)-(CH₂)₄-cHx H H
1-2548 COC₇H₁₅ H H H Me 2 -CH(OH)-(CH₂)₄-cHx H H
1-2549 COC₈H₁₇ H H H Me 2 -CH(OH)-(CH₂)₄-cHx H H
1-2550 COCH₃ H H H Me 2 -CH(OH)-(CH₂)₄-Ph H H
1-2551 COC₂H₅ H H H Me 2 -CH(OH)-(CH₂)₄-Ph H H
1-2552 COC₃H₇ H H H Me 2 -CH(OH)-(CH₂)₄-Ph H H
1-2553 COC₄H₉ H H H Me 2 -CH(OH)-(CH₂)₄-Ph H H
1-2554 COC₅H₁₁ H H H Me 2 -CH(OH)-(CH₂)₄-Ph H H
1-2555 COC₆H₁₃ H H H Me 2 -CH(OH)-(CH₂)₄-Ph H H
1-2556 COC₇H₁₅ H H H Me 2 -CH(OH)-(CH₂)₄-Ph H H
1-2557 COC₈H₁₇ H H H Me 2 -CH(OH)-(CH₂)₄-Ph H H
――――――――――――――――――――――――――――――――――――
表２
【００６３】
【化８】

【００６４】
【表２】
――――――――――――――――――――――――――――――――――――
Compd. R¹ R² R³ R_a ³ R⁴ n -X-Y-R⁵ R⁶ R⁷
――――――――――――――――――――――――――――――――――――
2-1 H H H H Me 1 -(CH₂)₅-cHx H H
2-2 H H H H Me 1 -(CH₂)₆-cHx H H
2-3 H H H H Me 1 -C≡C-(CH₂)₃-cHx H H
2-4 H H H H Me 1 -C≡C-(CH₂)₄-cHx H H
2-5 H H H H Me 1 -4-(cHx-CH₂O)Ph H H
2-6 H H H H Me 1 -(4-BzO-Ph) H H
2-7 H H H H Me 1 -C≡C-(CH₂)₂O-cHx H H
2-8 H H H H Me 1 -C≡C-(CH₂)₂O-Ph H H
2-9 H H H H Me 2 -(CH₂)₃-cHx H H
2-10 H H H H Me 2 -(CH₂)₃-Ph H H
2-11 H H H H Me 2 -(CH₂)₄-cHx H H
2-12 H H H H Me 2 -(CH₂)₄-Ph H H
2-13 H H H H Me 2 -(CH₂)₅-cPn H H
2-14 H H H H Me 2 -(CH₂)₅-cHx H H
2-15 H H H H Me 2 -(CH₂)₅-cHx Me H
2-16 H H H H Me 2 -(CH₂)₅-cHx H Me
2-17 H H H H Me 2 -(CH₂)₅-cHx F H
2-18 H H H H Me 2 -(CH₂)₅-cHx H F
2-19 H H Me Me Me 2 -(CH₂)₅-cHx H H
2-20 CO₂Me H H H Me 2 -(CH₂)₅-cHx H H
2-21 CO₂Et H H H Me 2 -(CH₂)₅-cHx H H
2-22 H H H H Me 2 -(CH₂)₅-(4-F-cHx) H H
2-23 H H H H Me 2 -(CH₂)₅-(4-Cl-cHx) H H
2-24 H H H H Me 2 -(CH₂)₅-(4-Br-cHx) H H
2-25 H H H H Me 2 -(CH₂)₅-(4-Me-cHx) H H
2-26 H H H H Me 2 -(CH₂)₅-(4-Et-cHx) H H
2-27 H H H H Me 2 -(CH₂)₅-(4-Pr-cHx) H H
2-28 H H H H Me 2 -(CH₂)₅-(4-iPr-cHx) H H
2-29 H H H H Me 2 -(CH₂)₅-(4-CF₃-cHx) H H
2-30 H H H H Me 2 -(CH₂)₅-(4-MeO-cHx) H H
2-31 H H H H Me 2 -(CH₂)₅-(4-EtO-cHx) H H
2-32 H H H H Me 2 -(CH₂)₅-(4-PrO-cHx) H H
2-33 H H H H Me 2 -(CH₂)₅-(4-iPrO-cHx) H H
2-34 H H H H Me 2 -(CH₂)₅-(3-MeS-cHx) H H
2-35 H H H H Me 2 -(CH₂)₅-(4-MeS-cHx) H H
2-36 H H H H Me 2 -(CH₂)₅-(2,4-diMe-cHx) H H
2-37 H H H H Me 2 -(CH₂)₅-(3,4-diMe-cHx) H H
2-38 H H H H Me 2 -(CH₂)₅-(3,5-diMe-cHx) H H
2-39 H H H H Me 2 -(CH₂)₅-Ph H H
2-40 H H H H Me 2 -(CH₂)₅-Ph Me H
2-41 H H H H Me 2 -(CH₂)₅-Ph H Me
2-42 H H H H Me 2 -(CH₂)₅-Ph F H
2-43 H H H H Me 2 -(CH₂)₅-Ph H F
2-44 H H Me Me Me 2 -(CH₂)₅-Ph H H
2-45 CO₂Me H H H Me 2 -(CH₂)₅-Ph H H
2-46 CO₂Et H H H Me 2 -(CH₂)₅-Ph H H
2-47 H H H H Me 2 -(CH₂)₅-(4-F-Ph) H H
2-48 H H H H Me 2 -(CH₂)₅-(4-Cl-Ph) H H
2-49 H H H H Me 2 -(CH₂)₅-(4-Br-Ph) H H
2-50 H H H H Me 2 -(CH₂)₅-(4-Me-Ph) H H
2-51 H H H H Me 2 -(CH₂)₅-(4-Et-Ph) H H
2-52 H H H H Me 2 -(CH₂)₅-(4-Pr-Ph) H H
2-53 H H H H Me 2 -(CH₂)₅-(4-iPr-Ph) H H
2-54 H H H H Me 2 -(CH₂)₅-(4-Bu-Ph) H H
2-55 H H H H Me 2 -(CH₂)₅-(4-CF₃-Ph) H H
2-56 H H H H Me 2 -(CH₂)₅-(4-MeO-Ph) H H
2-57 H H H H Me 2 -(CH₂)₅-(4-EtO-Ph) H H
2-58 H H H H Me 2 -(CH₂)₅-(4-PrO-Ph) H H
2-59 H H H H Me 2 -(CH₂)₅-(4-iPrO-Ph) H H
2-60 H H H H Me 2 -(CH₂)₅-(3-MeS-Ph) H H
2-61 H H H H Me 2 -(CH₂)₅-(4-MeS-Ph) H H
2-62 H H H H Me 2 -(CH₂)₅-(2,4-diMe-Ph) H H
2-63 H H H H Me 2 -(CH₂)₅-(3,4-diMe-Ph) H H
2-64 H H H H Me 2 -(CH₂)₅-(3,5-diMe-Ph) H H
2-65 H H H H Me 2 -(CH₂)₆-cPn H H
2-66 H H H H Me 2 -(CH₂)₆-cHx H H
2-67 H H H H Me 2 -(CH₂)₆-cHx Me H
2-68 H H H H Me 2 -(CH₂)₆-cHx H Me
2-69 H H H H Me 2 -(CH₂)₆-cHx F H
2-70 H H H H Me 2 -(CH₂)₆-cHx H F
2-71 H H Me Me Me 2 -(CH₂)₆-cHx H H
2-72 CO₂Me H H H Me 2 -(CH₂)₆-cHx H H
2-73 CO₂Et H H H Me 2 -(CH₂)₆-cHx H H
2-74 H H H H Me 2 -(CH₂)₆-(4-F-cHx) H H
2-75 H H H H Me 2 -(CH₂)₆-(4-Cl-cHx) H H
2-76 H H H H Me 2 -(CH₂)₆-(4-Br-cHx) H H
2-77 H H H H Me 2 -(CH₂)₆-(4-Me-cHx) H H
2-78 H H H H Me 2 -(CH₂)₆-(4-Et-cHx) H H
2-79 H H H H Me 2 -(CH₂)₆-(4-Pr-cHx) H H
2-80 H H H H Me 2 -(CH₂)₆-(4-iPr-cHx) H H
2-81 H H H H Me 2 -(CH₂)₆-(4-Bu-cHx) H H
2-82 H H H H Me 2 -(CH₂)₆-(4-CF₃-cHx) H H
2-83 H H H H Me 2 -(CH₂)₆-(4-MeO-cHx) H H
2-84 H H H H Me 2 -(CH₂)₆-(4-EtO-cHx) H H
2-85 H H H H Me 2 -(CH₂)₆-(4-PrO-cHx) H H
2-86 H H H H Me 2 -(CH₂)₆-(4-iPrO-cHx) H H
2-87 H H H H Me 2 -(CH₂)₆-(3-MeS-cHx) H H
2-88 H H H H Me 2 -(CH₂)₆-(4-MeS-cHx) H H
2-89 H H H H Me 2 -(CH₂)₆-(2,4-diMe-cHx) H H
2-90 H H H H Me 2 -(CH₂)₆-(3,4-diMe-cHx) H H
2-91 H H H H Me 2 -(CH₂)₆-(3,5-diMe-cHx) H H
2-92 H H H H Me 2 -(CH₂)₆-Ph H H
2-93 H H H H Me 2 -(CH₂)₆-Ph Me H
2-94 H H H H Me 2 -(CH₂)₆-Ph H Me
2-95 H H H H Me 2 -(CH₂)₆-Ph F H
2-96 H H H H Me 2 -(CH₂)₆-Ph H F
2-97 H H Me Me Me 2 -(CH₂)₆-Ph H H
2-98 CO₂Me H H H Me 2 -(CH₂)₆-Ph H H
2-99 CO₂Et H H H Me 2 -(CH₂)₆-Ph H H
2-100 H H H H Me 2 -(CH₂)₆-(4-F-Ph) H H
2-101 H H H H Me 2 -(CH₂)₆-(4-Cl-Ph) H H
2-102 H H H H Me 2 -(CH₂)₆-(4-Br-Ph) H H
2-103 H H H H Me 2 -(CH₂)₆-(4-Me-Ph) H H
2-104 H H H H Me 2 -(CH₂)₆-(4-Et-Ph) H H
2-105 H H H H Me 2 -(CH₂)₆-(4-Pr-Ph) H H
2-106 H H H H Me 2 -(CH₂)₆-(4-iPr-Ph) H H
2-107 H H H H Me 2 -(CH₂)₆-(4-Bu-Ph) H H
2-108 H H H H Me 2 -(CH₂)₆-(4-CF₃-Ph) H H
2-109 H H H H Me 2 -(CH₂)₆-(4-MeO-Ph) H H
2-110 H H H H Me 2 -(CH₂)₆-(4-EtO-Ph) H H
2-111 H H H H Me 2 -(CH₂)₆-(4-PrO-Ph) H H
2-112 H H H H Me 2 -(CH₂)₆-(4-iPrO-Ph) H H
2-113 H H H H Me 2 -(CH₂)₆-(3-MeS-Ph) H H
2-114 H H H H Me 2 -(CH₂)₆-(4-MeS-Ph) H H
2-115 H H H H Me 2 -(CH₂)₆-(2,4-diMe-Ph) H H
2-116 H H H H Me 2 -(CH₂)₆-(3,4-diMe-Ph) H H
2-117 H H H H Me 2 -(CH₂)₆-(3,5-diMe-Ph) H H
2-118 H H H H Me 2 -(CH₂)₇-cHx H H
2-119 H H H H Me 2 -(CH₂)₇-Ph H H
2-120 H H H H Me 2 -(CH₂)₈-cHx H H
2-121 H H H H Me 2 -(CH₂)₈-Ph H H
2-122 H H H H Me 2 -CH=CH-(CH₂)₃-cHx H H
2-123 H H Me Me Me 2 -CH=CH-(CH₂)₃-cHx H H
2-124 CO₂Me H H H Me 2 -CH=CH-(CH₂)₃-cHx H H
2-125 CO₂Et H H H Me 2 -CH=CH-(CH₂)₃-cHx H H
2-126 H H H H Me 2 -CH=CH-(CH₂)₃-Ph H H
2-127 H H Me Me Me 2 -CH=CH-(CH₂)₃-Ph H H
2-128 CO₂Me H H H Me 2 -CH=CH-(CH₂)₃-Ph H H
2-129 CO₂Et H H H Me 2 -CH=CH-(CH₂)₃-Ph H H
2-130 H H H H Me 2 -CH=CH-(CH₂)₄-cHx H H
2-131 H H H H Me 2 -CH=CH-(CH₂)₄-cHx H H
2-132 CO₂Me H H H Me 2 -CH=CH-(CH₂)₄-cHx H H
2-133 CO₂Et H H H Me 2 -CH=CH-(CH₂)₄-cHx H H
2-134 H H H H Me 2 -CH=CH-(CH₂)₄-Ph H H
2-135 H H H H Me 2 -CH=CH-(CH₂)₄-Ph H H
2-136 CO₂Me H H H Me 2 -CH=CH-(CH₂)₄-Ph H H
2-137 CO₂Et H H H Me 2 -CH=CH-(CH₂)₄-Ph H H
2-138 H H H H Me 2 -C=C-CH₂O-cHx H H
2-139 H H H H Me 2 -C=C-CH₂O-Ph H H
2-140 H H H H Me 2 -C=C-(CH₂)₂O-cHx H H
2-141 H H H H Me 2 -C=C-(CH₂)₂O-Ph H H
2-142 H H H H Me 2 -C≡C-CH₂-cHx H H
2-143 H H H H Me 2 -C≡C-CH₂-cHx H H
2-144 CO₂Me H H H Me 2 -C≡C-CH₂-cHx H H
2-145 CO₂Et H H H Me 2 -C≡C-CH₂-cHx H H
2-146 H H H H Me 2 -C≡C-CH₂-Ph H H
2-147 H H Me Me Me 2 -C≡C-CH₂-Ph H H
2-148 CO₂Me H H H Me 2 -C≡C-CH₂-Ph H H
2-149 CO₂Et H H H Me 2 -C≡C-CH₂-Ph H H
2-150 H H H H Me 2 -C≡C-(CH₂)₂-cHx H H
2-151 H H Me Me Me 2 -C≡C-(CH₂)₂-cHx H H
2-152 CO₂Me H H H Me 2 -C≡C-(CH₂)₂-cHx H H
2-153 CO₂Et H H H Me 2 -C≡C-(CH₂)₂-cHx H H
2-154 H H H H Me 2 -C≡C-(CH₂)₂-Ph H H
2-155 H H Me Me Me 2 -C≡C-(CH₂)₂-Ph H H
2-156 CO₂Me H H H Me 2 -C≡C-(CH₂)₂-Ph H H
2-157 CO₂Et H H H Me 2 -C≡C-(CH₂)₂-Ph H H
2-158 H H H H Me 2 -C≡C-(CH₂)₃-cPn H H
2-159 H H H H Me 2 -C≡C-(CH₂)₃-cHx H H
2-160 H H H H Me 2 -C≡C-(CH₂)₃-cHx Me H
2-161 H H H H Me 2 -C≡C-(CH₂)₃-cHx H Me
2-162 H H H H Me 2 -C≡C-(CH₂)₃-cHx F H
2-163 H H H H Me 2 -C≡C-(CH₂)₃-cHx H F
2-164 H H Me Me Me 2 -C≡C-(CH₂)₃-cHx H H
2-165 CO₂Me H H H Me 2 -C≡C-(CH₂)₃-cHx H H
2-166 CO₂Et H H H Me 2 -C≡C-(CH₂)₃-cHx H H
2-167 H H H H Me 2 -C≡C-(CH₂)₃-(4-F-cHx) H H
2-168 H H H H Me 2 -C≡C-(CH₂)₃-(4-Cl-cHx) H H
2-169 H H H H Me 2 -C≡C-(CH₂)₃-(4-Br-cHx) H H
2-170 H H H H Me 2 -C≡C-(CH₂)₃-(4-Me-cHx) H H
2-171 H H H H Me 2 -C≡C-(CH₂)₃-(4-Et-cHx) H H
2-172 H H H H Me 2 -C≡C-(CH₂)₃-(4-Pr-cHx) H H
2-173 H H H H Me 2 -C≡C-(CH₂)₃-(4-iPr-cHx) H H
2-174 H H H H Me 2 -C≡C-(CH₂)₃-(4-Bu-cHx) H H
2-175 H H H H Me 2 -C≡C-(CH₂)₃-(4-CF₃-cHx) H H
2-176 H H H H Me 2 -C≡C-(CH₂)₃-(4-MeO-cHx) H H
2-177 H H H H Me 2 -C≡C-(CH₂)₃-(4-EtO-cHx) H H
2-178 H H H H Me 2 -C≡C-(CH₂)₃-(4-PrO-cHx) H H
2-179 H H H H Me 2 -C≡C-(CH₂)₃-(4-iPrO-cHx) H H
2-180 H H H H Me 2 -C≡C-(CH₂)₃-(3-MeS-cHx) H H
2-181 H H H H Me 2 -C≡C-(CH₂)₃-(4-MeS-cHx) H H
2-182 H H H H Me 2 -C≡C-(CH₂)₃-(2,4-diMe-cHx) H H
2-183 H H H H Me 2 -C≡C-(CH₂)₃-(3,4-diMe-cHx) H H
2-184 H H H H Me 2 -C≡C-(CH₂)₃-(3,5-diMe-cHx) H H
2-185 H H H H Me 2 -C≡C-(CH₂)₃-Ph H H
2-186 H H H H Me 2 -C≡C-(CH₂)₃-Ph Me H
2-187 H H H H Me 2 -C≡C-(CH₂)₃-Ph H Me
2-188 H H H H Me 2 -C≡C-(CH₂)₃-Ph F H
2-189 H H H H Me 2 -C≡C-(CH₂)₃-Ph H F
2-190 H H Me Me Me 2 -C≡C-(CH₂)₃-Ph H H
2-191 CO₂Me H H H Me 2 -C≡C-(CH₂)₃-Ph H H
2-192 CO₂Et H H H Me 2 -C≡C-(CH₂)₃-Ph H H
2-193 H H H H Me 2 -C≡C-(CH₂)₃-(4-F-Ph) H H
2-194 H H H H Me 2 -C≡C-(CH₂)₃-(4-Cl-Ph) H H
2-195 H H H H Me 2 -C≡C-(CH₂)₃-(4-Br-Ph) H H
2-196 H H H H Me 2 -C≡C-(CH₂)₃-(4-Me-Ph) H H
2-197 H H H H Me 2 -C≡C-(CH₂)₃-(4-Et-Ph) H H
2-198 H H H H Me 2 -C≡C-(CH₂)₃-(4-Pr-Ph) H H
2-199 H H H H Me 2 -C≡C-(CH₂)₃-(4-iPr-Ph) H H
2-200 H H H H Me 2 -C≡C-(CH₂)₃-(4-Bu-Ph) H H
2-201 H H H H Me 2 -C≡C-(CH₂)₃-(4-CF₃-Ph) H H
2-202 H H H H Me 2 -C≡C-(CH₂)₃-(4-MeO-Ph) H H
2-203 H H H H Me 2 -C≡C-(CH₂)₃-(4-EtO-Ph) H H
2-204 H H H H Me 2 -C≡C-(CH₂)₃-(4-PrO-Ph) H H
2-205 H H H H Me 2 -C≡C-(CH₂)₃-(4-iPrO-Ph) H H
2-206 H H H H Me 2 -C≡C-(CH₂)₃-(3-MeS-Ph) H H
2-207 H H H H Me 2 -C≡C-(CH₂)₃-(4-MeS-Ph) H H
2-208 H H H H Me 2 -C≡C-(CH₂)₃-(2,4-diMe-Ph) H H
2-209 H H H H Me 2 -C≡C-(CH₂)₃-(3,4-diMe-Ph) H H
2-210 H H H H Me 2 -C≡C-(CH₂)₃-(3,5-diMe-Ph) H H
2-211 H H H H Me 2 -C≡C-(CH₂)₄-cPn H H
2-212 H H H H Me 2 -C≡C-(CH₂)₄-cHx H H
2-213 H H H H Me 2 -C≡C-(CH₂)₄-cHx Me H
2-214 H H H H Me 2 -C≡C-(CH₂)₄-cHx H Me
2-215 H H H H Me 2 -C≡C-(CH₂)₄-cHx F H
2-216 H H H H Me 2 -C≡C-(CH₂)₄-cHx H F
2-217 H H Me Me Me 2 -C≡C-(CH₂)₄-cHx H H
2-218 CO₂Me H H H Me 2 -C≡C-(CH₂)₄-cHx H H
2-219 CO₂Et H H H Me 2 -C≡C-(CH₂)₄-cHx H H
2-220 H H H H Me 2 -C≡C-(CH₂)₄-(4-F-cHx) H H
2-221 H H H H Me 2 -C≡C-(CH₂)₄-(4-Cl-cHx) H H
2-222 H H H H Me 2 -C≡C-(CH₂)₄-(4-Br-cHx) H H
2-223 H H H H Me 2 -C≡C-(CH₂)₄-(4-Me-cHx) H H
2-224 H H H H Me 2 -C≡C-(CH₂)₄-(4-Et-cHx) H H
2-225 H H H H Me 2 -C≡C-(CH₂)₄-(4-Pr-cHx) H H
2-226 H H H H Me 2 -C≡C-(CH₂)₄-(4-iPr-cHx) H H
2-227 H H H H Me 2 -C≡C-(CH₂)₄-(4-Bu-cHx) H H
2-228 H H H H Me 2 -C≡C-(CH₂)₄-(4-CF₃-cHx) H H
2-229 H H H H Me 2 -C≡C-(CH₂)₄-(4-MeO-cHx) H H
2-230 H H H H Me 2 -C≡C-(CH₂)₄-(4-EtO-cHx) H H
2-231 H H H H Me 2 -C≡C-(CH₂)₄-(4-PrO-cHx) H H
2-232 H H H H Me 2 -C≡C-(CH₂)₄-(4-iPrO-cHx) H H
2-233 H H H H Me 2 -C≡C-(CH₂)₄-(4-MeS-cHx) H H
2-234 H H H H Me 2 -C≡C-(CH₂)₄-(2,4-diMe-cHx) H H
2-235 H H H H Me 2 -C≡C-(CH₂)₄-(3,4-diMe-cHx) H H
2-236 H H H H Me 2 -C≡C-(CH₂)₄-(3,5-diMe-cHx) H H
2-237 H H H H Me 2 -C≡C-(CH₂)₄-Ph H H
2-238 H H H H Me 2 -C≡C-(CH₂)₄-Ph Me H
2-239 H H H H Me 2 -C≡C-(CH₂)₄-Ph H Me
2-240 H H H H Me 2 -C≡C-(CH₂)₄-Ph F H
2-241 H H H H Me 2 -C≡C-(CH₂)₄-Ph H F
2-242 H H Me Me Me 2 -C≡C-(CH₂)₄-Ph H H
2-243 CO₂Me H H H Me 2 -C≡C-(CH₂)₄-Ph H H
2-244 CO₂Et H H H Me 2 -C≡C-(CH₂)₄-Ph H H
2-245 H H H H Me 2 -C≡C-(CH₂)₄-(4-F-Ph) H H
2-246 H H H H Me 2 -C≡C-(CH₂)₄-(4-Cl-Ph) H H
2-247 H H H H Me 2 -C≡C-(CH₂)₄-(4-Br-Ph) H H
2-248 H H H H Me 2 -C≡C-(CH₂)₄-(4-Me-Ph) H H
2-249 H H H H Me 2 -C≡C-(CH₂)₄-(4-Et-Ph) H H
2-250 H H H H Me 2 -C≡C-(CH₂)₄-(4-Pr-Ph) H H
2-251 H H H H Me 2 -C≡C-(CH₂)₄-(4-iPr-Ph) H H
2-252 H H H H Me 2 -C≡C-(CH₂)₄-(4-Bu-Ph) H H
2-253 H H H H Me 2 -C≡C-(CH₂)₄-(4-CF₃-Ph) H H
2-254 H H H H Me 2 -C≡C-(CH₂)₄-(4-MeO-Ph) H H
2-255 H H H H Me 2 -C≡C-(CH₂)₄-(4-EtO-Ph) H H
2-256 H H H H Me 2 -C≡C-(CH₂)₄-(4-PrO-Ph) H H
2-257 H H H H Me 2 -C≡C-(CH₂)₄-(4-iPrO-Ph) H H
2-258 H H H H Me 2 -C≡C-(CH₂)₄-(3-MeS-Ph) H H
2-259 H H H H Me 2 -C≡C-(CH₂)₄-(4-MeS-Ph) H H
2-260 H H H H Me 2 -C≡C-(CH₂)₄-(2,4-diMe-Ph) H H
2-261 H H H H Me 2 -C≡C-(CH₂)₄-(3,4-diMe-Ph) H H
2-262 H H H H Me 2 -C≡C-(CH₂)₄-(3,5-diMe-Ph) H H
2-263 H H H H Me 2 -C≡C-(CH₂)₅-cHx H H
2-264 H H Me Me Me 2 -C≡C-(CH₂)₅-cHx H H
2-265 CO₂Me H H H Me 2 -C≡C-(CH₂)₅-cHx H H
2-266 CO₂Et H H H Me 2 -C≡C-(CH₂)₅-cHx H H
2-267 H H H H Me 2 -C≡C-(CH₂)₅-Ph H H
2-268 H H Me Me Me 2 -C≡C-(CH₂)₅-Ph H H
2-269 CO₂Me H H H Me 2 -C≡C-(CH₂)₅-Ph H H
2-270 CO₂Et H H H Me 2 -C≡C-(CH₂)₅-Ph H H
2-271 H H H H Me 2 -C≡C-(CH₂)₆-cHx H H
2-272 H H Me Me Me 2 -C≡C-(CH₂)₆-cHx H H
2-273 CO₂Me H H H Me 2 -C≡C-(CH₂)₆-cHx H H
2-274 CO₂Et H H H Me 2 -C≡C-(CH₂)₆-cHx H H
2-275 H H H H Me 2 -C≡C-(CH₂)₆-Ph H H
2-276 H H Me Me Me 2 -C≡C-(CH₂)₆-Ph H H
2-277 CO₂Me H H H Me 2 -C≡C-(CH₂)₆-Ph H H
2-278 CO₂Et H H H Me 2 -C≡C-(CH₂)₆-Ph H H
2-279 H H H H Me 2 -C≡C-CH₂O-cHx H H
2-280 H H Me Me Me 2 -C≡C-CH₂O-cHx H H
2-281 CO₂Me H H H Me 2 -C≡C-CH₂O-cHx H H
2-282 CO₂Et H H H Me 2 -C≡C-CH₂O-cHx H H
2-283 H H H H Me 2 -C≡C-CH₂O-Ph H H
2-284 H H Me Me Me 2 -C≡C-CH₂O-Ph H H
2-285 CO₂Me H H H Me 2 -C≡C-CH₂O-Ph H H
2-286 CO₂Et H H H Me 2 -C≡C-CH₂O-Ph H H
2-287 H H H H Me 2 -C≡C-(CH₂)₂O-cPn H H
2-288 H H H H Me 2 -C≡C-(CH₂)₂O-cHx H H
2-289 H H H H Me 2 -C≡C-(CH₂)₂O-cHx Me H
2-290 H H H H Me 2 -C≡C-(CH₂)₂O-cHx H Me
2-291 H H H H Me 2 -C≡C-(CH₂)₂O-cHx F H
2-292 H H H H Me 2 -C≡C-(CH₂)₂O-cHx H F
2-293 H H Me Me Me 2 -C≡C-(CH₂)₂-OCH₂-cHx H H
2-294 CO₂Me H H H Me 2 -C≡C-(CH₂)₂O-cHx H H
2-295 CO₂Et H H H Me 2 -C≡C-(CH₂)₂O-cHx H H
2-296 H H H H Me 2 -C≡C-(CH₂)₂O-(4-F-cHx) H H
2-297 H H H H Me 2 -C≡C-(CH₂)₂O-(4-Cl-cHx) H H
2-298 H H H H Me 2 -C≡C-(CH₂)₂O-(4-Br-cHx) H H
2-299 H H H H Me 2 -C≡C-(CH₂)₂O-(4-Me-cHx) H H
2-300 H H H H Me 2 -C≡C-(CH₂)₂O-(4-Et-cHx) H H
2-301 H H H H Me 2 -C≡C-(CH₂)₂O-(4-Pr-cHx) H H
2-302 H H H H Me 2 -C≡C-(CH₂)₂O-(4-iPr-cHx) H H
2-303 H H H H Me 2 -C≡C-(CH₂)₂O-(4-Bu-cHx) H H
2-304 H H H H Me 2 -C≡C-(CH₂)₂O-(4-CF₃-cHx) H H
2-305 H H H H Me 2 -C≡C-(CH₂)₂O-(4-MeO-cHx) H H
2-306 H H H H Me 2 -C≡C-(CH₂)₂O-(4-EtO-cHx) H H
2-307 H H H H Me 2 -C≡C-(CH₂)₂O-(4-PrO-cHx) H H
2-308 H H H H Me 2 -C≡C-(CH₂)₂O-(4-iPrO-cHx) H H
2-309 H H H H Me 2 -C≡C-(CH₂)₂O-(3-MeS-cHx) H H
2-310 H H H H Me 2 -C≡C-(CH₂)₂O-(4-MeS-cHx) H H
2-311 H H H H Me 2 -C≡C-(CH₂)₂O-(2,4-diMe-cHx) H H
2-312 H H H H Me 2 -C≡C-(CH₂)₂O-(3,4-diMe-cHx) H H
2-313 H H H H Me 2 -C≡C-(CH₂)₂O-(3,5-diMe-cHx) H H
2-314 H H H H Me 2 -C≡C-(CH₂)₂O-Ph H H
2-315 H H H H Me 2 -C≡C-(CH₂)₂O-Ph Me H
2-316 H H H H Me 2 -C≡C-(CH₂)₂O-Ph H Me
2-317 H H H H Me 2 -C≡C-(CH₂)₂O-Ph F H
2-318 H H H H Me 2 -C≡C-(CH₂)₂O-Ph H F
2-319 H H Me Me Me 2 -C≡C-(CH₂)₂-OCH₂-Ph H H
2-320 CO₂Me H H H Me 2 -C≡C-(CH₂)₂O-Ph H H
2-321 CO₂Et H H H Me 2 -C≡C-(CH₂)₂O-Ph H H
2-322 H H H H Me 2 -C≡C-(CH₂)₂O-(4-F-Ph) H H
2-323 H H H H Me 2 -C≡C-(CH₂)₂O-(4-Cl-Ph) H H
2-324 H H H H Me 2 -C≡C-(CH₂)₂O-(4-Br-Ph) H H
2-325 H H H H Me 2 -C≡C-(CH₂)₂O-(4-Me-Ph) H H
2-326 H H H H Me 2 -C≡C-(CH₂)₂O-(4-Et-Ph) H H
2-327 H H H H Me 2 -C≡C-(CH₂)₂O-(4-Pr-Ph) H H
2-328 H H H H Me 2 -C≡C-(CH₂)₂O-(4-iPr-Ph) H H
2-329 H H H H Me 2 -C≡C-(CH₂)₂O-(4-Bu-Ph) H H
2-330 H H H H Me 2 -C≡C-(CH₂)₂O-(4-CF₃-Ph) H H
2-331 H H H H Me 2 -C≡C-(CH₂)₂O-(4-MeO-Ph) H H
2-332 H H H H Me 2 -C≡C-(CH₂)₂O-(4-EtO-Ph) H H
2-333 H H H H Me 2 -C≡C-(CH₂)₂O-(4-PrO-Ph) H H
2-334 H H H H Me 2 -C≡C-(CH₂)₂O-(4-iPrO-Ph) H H
2-335 H H H H Me 2 -C≡C-(CH₂)₂O-(4-MeS-Ph) H H
2-336 H H H H Me 2 -C≡C-(CH₂)₂O-(2,4-diMe-Ph) H H
2-337 H H H H Me 2 -C≡C-(CH₂)₂O-(3,4-diMe-Ph) H H
2-338 H H H H Me 2 -C≡C-(CH₂)₂O-(3,5-diMe-Ph) H H
2-339 H H H H Me 2 -CO-(CH₂)₄-cHx H H
2-340 H H Me Me Me 2 -CO-(CH₂)₄-cHx H H
2-341 CO₂Me H H H Me 2 -CO-(CH₂)₄-cHx H H
2-342 CO₂Et H H H Me 2 -CO-(CH₂)₄-cHx H H
2-343 H H H H Me 2 -CO-(CH₂)₄-Ph H H
2-344 H H Me Me Me 2 -CO-(CH₂)₄-Ph H H
2-345 CO₂Me H H H Me 2 -CO-(CH₂)₄-Ph H H
2-346 CO₂Et H H H Me 2 -CO-(CH₂)₄-Ph H H
2-347 H H H H Me 2 -CO-(CH₂)₅-cHx H H
2-348 H H Me Me Me 2 -CO-(CH₂)₅-cHx H H
2-349 CO₂Me H H H Me 2 -CO-(CH₂)₅-cHx H H
2-350 CO₂Et H H H Me 2 -CO-(CH₂)₅-cHx H H
2-351 H H H H Me 2 -CO-(CH₂)₅-Ph H H
2-352 H H Me Me Me 2 -CO-(CH₂)₅-Ph H H
2-353 CO₂Me H H H Me 2 -CO-(CH₂)₅-Ph H H
2-354 CO₂Et H H H Me 2 -CO-(CH₂)₅-Ph H H
2-355 H H H H Me 2 -CH(OH)-(CH₂)₄-cHx H H
2-356 H H Me Me Me 2 -CH(OH)-(CH₂)₄-cHx H H
2-357 CO₂Me H H H Me 2 -CH(OH)-(CH₂)₄-cHx H H
2-358 CO₂Et H H H Me 2 -CH(OH)-(CH₂)₄-cHx H H
2-359 H H H H Me 2 -CH(OH)-(CH₂)₄-Ph H H
2-360 H H Me Me Me 2 -CH(OH)-(CH₂)₄-Ph H H
2-361 CO₂Me H H H Me 2 -CH(OH)-(CH₂)₄-Ph H H
2-362 CO₂Et H H H Me 2 -CH(OH)-(CH₂)₄-Ph H H
2-363 H H H H Me 2 -CH(OH)-(CH₂)₅-cHx H H
2-364 H H Me Me Me 2 -CH(OH)-(CH₂)₅-cHx H H
2-365 CO₂Me H H H Me 2 -CH(OH)-(CH₂)₅-cHx H H
2-366 CO₂Et H H H Me 2 -CH(OH)-(CH₂)₅-cHx H H
2-367 H H H H Me 2 -CH(OH)-(CH₂)₅-Ph H H
2-368 H H Me Me Me 2 -CH(OH)-(CH₂)₅-Ph H H
2-369 CO₂Me H H H Me 2 -CH(OH)-(CH₂)₅-Ph H H
2-370 CO₂Et H H H Me 2 -CH(OH)-(CH₂)₅-Ph H H
2-371 H H H H Me 2 -4-(cHx-CH₂O)Ph H H
2-372 H H Me Me Me 2 -4-(cHx-CH₂O)Ph H H
2-373 CO₂Me H H H Me 2 -4-(cHx-CH₂O)Ph H H
2-374 CO₂Et H H H Me 2 -4-(cHx-CH₂O)Ph H H
2-375 H H H H Me 2 -4-[cHx-(CH₂)₂O]Ph H H
2-376 H H H H Me 2 -4-[cHx-(CH₂)₃O]Ph H H
2-377 H H H H Me 2 -(4-BzO-Ph) H H
2-378 H H Me Me Me 2 -(4-BzO-Ph) H H
2-379 CO₂Me H H H Me 2 -(4-BzO-Ph) H H
2-380 CO₂Et H H H Me 2 -(4-BzO-Ph) H H
2-381 H H H H Me 2 -(4-BzO-2-F-Ph) H H
2-382 H H H H Me 2 -(4-BzO-3-F-Ph) H H
2-383 H H H H Me 2 -(4-BzO-2,3-diF-Ph) H H
2-384 H H H H Me 2 -(4-BzO-2-Cl-Ph) H H
2-385 H H H H Me 2 -(4-BzO-3-Cl-Ph) H H
2-386 H H H H Me 2 -(4-BzO-2,3-diCl-Ph) H H
2-387 H H H H Me 2 -(4-BzO-2-Me-Ph) H H
2-388 H H H H Me 2 -(4-BzO-3-Me-Ph) H H
2-389 H H H H Me 2 -(4-BzO-2,3-diMe-Ph) H H
2-390 H H H H Me 2 -4-[Ph-(CH₂)₂O]-Ph H H
2-391 H H H H Me 2 -4-[Ph-(CH₂)₃O]-Ph H H
2-392 H H H H Et 2 -(CH₂)₅-cHx H H
2-393 H H H H Et 2 -(CH₂)₆-cHx H H
2-394 H H H H Et 2 -C≡C-(CH₂)₃-cHx H H
2-395 H H H H Et 2 -C≡C-(CH₂)₄-cHx H H
2-396 H H H H Et 2 -4-(cHx-CH₂O)Ph H H
2-397 H H H H Et 2 -(4-BzO-Ph) H H
2-398 H H H H Et 2 -C≡C-(CH₂)₂O-cHx H H
2-399 H H H H Et 2 -C≡C-(CH₂)₂O-Ph H H
2-400 H H H H Pr 2 -(CH₂)₅-cHx H H
2-401 H H H H Pr 2 -(CH₂)₆-cHx H H
2-402 H H H H Pr 2 -C≡C-(CH₂)₃-cHx H H
2-403 H H H H Pr 2 -C≡C-(CH₂)₄-cHx H H
2-404 H H H H Pr 2 -4-(cHx-CH₂O)Ph H H
2-405 H H H H Pr 2 -(4-BzO-Ph) H H
2-406 H H H H Pr 2 -C≡C-(CH₂)₂O-cHx H H
2-407 H H H H Pr 2 -C≡C-(CH₂)₂O-Ph H H
2-408 H H H H Me 3 -(CH₂)₅-cHx H H
2-409 H H H H Me 3 -(CH₂)₆-cHx H H
2-410 H H H H Me 3 -C≡C-(CH₂)₃-cHx H H
2-411 H H H H Me 3 -C≡C-(CH₂)₄-cHx H H
2-412 H H H H Me 3 -4-(cHx-CH₂O)Ph H H
2-413 H H H H Me 3 -(4-BzO-Ph) H H
2-414 H H H H Me 3 -C≡C-(CH₂)₂O-cHx H H
2-415 H H H H Me 3 -C≡C-(CH₂)₂O-Ph H H
2-416 COCH₃ H H H Me 2 -(CH₂)₄-cHx H H
2-417 COC₂H₅ H H H Me 2 -(CH₂)₄-cHx H H
2-418 COC₃H₇ H H H Me 2 -(CH₂)₄-cHx H H
2-419 COC₄H₉ H H H Me 2 -(CH₂)₄-cHx H H
2-420 COC₅H₁₁ H H H Me 2 -(CH₂)₄-cHx H H
2-421 COC₆H₁₃ H H H Me 2 -(CH₂)₄-cHx H H
2-422 COC₇H₁₅ H H H Me 2 -(CH₂)₄-cHx H H
2-423 COC₈H₁₇ H H H Me 2 -(CH₂)₄-cHx H H
2-424 COCH₃ H H H Me 2 -(CH₂)₄-Ph H H
2-425 COC₂H₅ H H H Me 2 -(CH₂)₄-Ph H H
2-426 COC₃H₇ H H H Me 2 -(CH₂)₄-Ph H H
2-427 COC₄H₉ H H H Me 2 -(CH₂)₄-Ph H H
2-428 COC₅H₁₁ H H H Me 2 -(CH₂)₄-Ph H H
2-429 COC₆H₁₃ H H H Me 2 -(CH₂)₄-Ph H H
2-430 COC₇H₁₅ H H H Me 2 -(CH₂)₄-Ph H H
2-431 COC₈H₁₇ H H H Me 2 -(CH₂)₄-Ph H H
2-432 COCH₃ H H H Me 2 -(CH₂)₅-cHx H H
2-433 COC₂H₅ H H H Me 2 -(CH₂)₅-cHx H H
2-434 COC₃H₇ H H H Me 2 -(CH₂)₅-cHx H H
2-435 COC₄H₉ H H H Me 2 -(CH₂)₅-cHx H H
2-436 COC₅H₁₁ H H H Me 2 -(CH₂)₅-cHx H H
2-437 COC₆H₁₃ H H H Me 2 -(CH₂)₅-cHx H H
2-438 COC₇H₁₅ H H H Me 2 -(CH₂)₅-cHx H H
2-439 COC₈H₁₇ H H H Me 2 -(CH₂)₅-cHx H H
2-440 COCH₃ H H H Me 2 -(CH₂)₅-Ph H H
2-441 COC₂H₅ H H H Me 2 -(CH₂)₅-Ph H H
2-442 COC₃H₇ H H H Me 2 -(CH₂)₅-Ph H H
2-443 COC₄H₉ H H H Me 2 -(CH₂)₅-Ph H H
2-444 COC₅H₁₁ H H H Me 2 -(CH₂)₅-Ph H H
2-445 COC₆H₁₃ H H H Me 2 -(CH₂)₅-Ph H H
2-446 COC₇H₁₅ H H H Me 2 -(CH₂)₅-Ph H H
2-447 COC₈H₁₇ H H H Me 2 -(CH₂)₅-Ph H H
2-448 COCH₃ H H H Me 2 -C≡C-(CH₂)₃-cHx H H
2-449 COC₂H₅ H H H Me 2 -C≡C-(CH₂)₃-cHx H H
2-450 COC₃H₇ H H H Me 2 -C≡C-(CH₂)₃-cHx H H
2-451 COC₄H₉ H H H Me 2 -C≡C-(CH₂)₃-cHx H H
2-452 COC₅H₁₁ H H H Me 2 -C≡C-(CH₂)₃-cHx H H
2-453 COC₆H₁₃ H H H Me 2 -C≡C-(CH₂)₃-cHx H H
2-454 COC₇H₁₅ H H H Me 2 -C≡C-(CH₂)₃-cHx H H
2-455 COC₈H₁₇ H H H Me 2 -C≡C-(CH₂)₃-cHx H H
2-456 COCH₃ H H H Me 2 -C≡C-(CH₂)₃-Ph H H
2-457 COC₂H₅ H H H Me 2 -C≡C-(CH₂)₃-Ph H H
2-458 COC₃H₇ H H H Me 2 -C≡C-(CH₂)₃-Ph H H
2-459 COC₄H₉ H H H Me 2 -C≡C-(CH₂)₃-Ph H H
2-460 COC₅H₁₁ H H H Me 2 -C≡C-(CH₂)₃-Ph H H
2-461 COC₆H₁₃ H H H Me 2 -C≡C-(CH₂)₃-Ph H H
2-462 COC₇H₁₅ H H H Me 2 -C≡C-(CH₂)₃-Ph H H
2-463 COC₈H₁₇ H H H Me 2 -C≡C-(CH₂)₃-Ph H H
2-464 COCH₃ H H H Me 2 -C≡C-(CH₂)₄-cHx H H
2-465 COC₂H₅ H H H Me 2 -C≡C-(CH₂)₄-cHx H H
2-466 COC₃H₇ H H H Me 2 -C≡C-(CH₂)₄-cHx H H
2-467 COC₄H₉ H H H Me 2 -C≡C-(CH₂)₄-cHx H H
2-468 COC₅H₁₁ H H H Me 2 -C≡C-(CH₂)₄-cHx H H
2-469 COC₆H₁₃ H H H Me 2 -C≡C-(CH₂)₄-cHx H H
2-470 COC₇H₁₅ H H H Me 2 -C≡C-(CH₂)₄-cHx H H
2-471 COC₈H₁₇ H H H Me 2 -C≡C-(CH₂)₄-cHx H H
2-472 COCH₃ H H H Me 2 -C≡C-(CH₂)₄-Ph H H
2-473 COC₂H₅ H H H Me 2 -C≡C-(CH₂)₄-Ph H H
2-474 COC₃H₇ H H H Me 2 -C≡C-(CH₂)₄-Ph H H
2-475 COC₄H₉ H H H Me 2 -C≡C-(CH₂)₄-Ph H H
2-476 COC₅H₁₁ H H H Me 2 -C≡C-(CH₂)₄-Ph H H
2-477 COC₆H₁₃ H H H Me 2 -C≡C-(CH₂)₄-Ph H H
2-478 COC₇H₁₅ H H H Me 2 -C≡C-(CH₂)₄-Ph H H
2-479 COC₈H₁₇ H H H Me 2 -C≡C-(CH₂)₄-Ph H H
2-480 COCH₃ H H H Me 2 -C≡C-(CH₂)₂O-cHx H H
2-481 COC₂H₅ H H H Me 2 -C≡C-(CH₂)₂O-cHx H H
2-482 COC₃H₇ H H H Me 2 -C≡C-(CH₂)₂O-cHx H H
2-483 COC₄H₉ H H H Me 2 -C≡C-(CH₂)₂O-cHx H H
2-484 COC₅H₁₁ H H H Me 2 -C≡C-(CH₂)₂O-cHx H H
2-485 COC₆H₁₃ H H H Me 2 -C≡C-(CH₂)₂O-cHx H H
2-486 COC₇H₁₅ H H H Me 2 -C≡C-(CH₂)₂O-cHx H H
2-487 COC₈H₁₇ H H H Me 2 -C≡C-(CH₂)₂O-cHx H H
2-488 COCH₃ H H H Me 2 -C≡C-(CH₂)₂O-Ph H H
2-489 COC₂H₅ H H H Me 2 -C≡C-(CH₂)₂O-Ph H H
2-490 COC₃H₇ H H H Me 2 -C≡C-(CH₂)₂O-Ph H H
2-491 COC₄H₉ H H H Me 2 -C≡C-(CH₂)₂O-Ph H H
2-492 COC₅H₁₁ H H H Me 2 -C≡C-(CH₂)₂O-Ph H H
2-493 COC₆H₁₃ H H H Me 2 -C≡C-(CH₂)₂O-Ph H H
2-494 COC₇H₁₅ H H H Me 2 -C≡C-(CH₂)₂O-Ph H H
2-495 COC₈H₁₇ H H H Me 2 -C≡C-(CH₂)₂O-Ph H H
2-496 COCH₃ H H H Me 2 -CO-(CH₂)₄-cHx H H
2-497 COC₂H₅ H H H Me 2 -CO-(CH₂)₄-cHx H H
2-498 COC₃H₇ H H H Me 2 -CO-(CH₂)₄-cHx H H
2-499 COC₄H₉ H H H Me 2 -CO-(CH₂)₄-cHx H H
2-500 COC₅H₁₁ H H H Me 2 -CO-(CH₂)₄-cHx H H
2-501 COC₆H₁₃ H H H Me 2 -CO-(CH₂)₄-cHx H H
2-502 COC₇H₁₅ H H H Me 2 -CO-(CH₂)₄-cHx H H
2-503 COC₈H₁₇ H H H Me 2 -CO-(CH₂)₄-cHx H H
2-504 COCH₃ H H H Me 2 -CO-(CH₂)₄-Ph H H
2-505 COC₂H₅ H H H Me 2 -CO-(CH₂)₄-Ph H H
2-506 COC₃H₇ H H H Me 2 -CO-(CH₂)₄-Ph H H
2-507 COC₄H₉ H H H Me 2 -CO-(CH₂)₄-Ph H H
2-508 COC₅H₁₁ H H H Me 2 -CO-(CH₂)₄-Ph H H
2-509 COC₆H₁₃ H H H Me 2 -CO-(CH₂)₄-Ph H H
2-510 COC₇H₁₅ H H H Me 2 -CO-(CH₂)₄-Ph H H
2-511 COC₈H₁₇ H H H Me 2 -CO-(CH₂)₄-Ph H H
――――――――――――――――――――――――――――――――――――
上記表１[式（Ｉａ-1）及び（Ｉａ-２）]並びに表２[（Ｉｂ-１）及び（Ｉｂ-２）]において、
本発明の化合物（Ｉ）として好適には、
例示化合物番号：1-19, 1-23〜1-32, 1-36〜1-45, 1-49〜1-58, 1-62〜1-71, 1-75〜1-84, 1-88〜1-102, 1-106〜1-156, 1-160〜1-214, 1-218〜1-268, 1-272〜1-322, 1-325〜1-334, 1-338〜1-347, 1-351〜1-360, 1-364〜1-373, 1-377〜1-386, 1-390〜1-404, 1-408〜1-458, 1-462〜1-513, 1-517〜1-526, 1-530〜1-544, 1-548〜1-598, 1-602〜1-657, 1-670, 1-674〜1-683, 1-696, 1-700〜1-717, 1-721〜1-730, 1-734〜1-743, 1-747〜1-756, 1-760〜1-774, 1-778〜1-828, 1-832〜1-886, 1-890〜1-940, 1-944〜1-993, 1-997〜1-1006, 1-1010〜1-1019, 1-1045, 1-1049〜1-1058, 1-1062〜1-1076, 1-1080〜1-1130, 1-1134〜1-1185, 1-1189〜1-1198, 1-1202〜1-1208, 1-1212〜1-1216, 1-1220〜1-1270, 1-1274〜1-1331, 1-1335〜1-1344, 1-1348〜1-1357, 1-1361〜1-1370, 1-1374〜1-1387, 1-1391〜1-1400, 1-1404〜1-1418, 1-1422〜1-1472, 1-1476〜1-1527, 1-1531〜1-1540, 1-1544〜1-1558, 1-1562〜1-1612, 1-1616〜1-1673, 1-1677〜1-1686, 1-1690〜1-1699, 1-1703〜1-1712, 1-1716〜1-1729, 1-1733〜1-1744, 1-1748〜1-1767, 1-1772〜1-1793, 1-1797〜1-1818, 1-1824〜1-1846, 1-1850〜1-1869, 1-1872, 1-1876, 1-1880, 1-1884, 1-1888〜1-1892, 1-1896, 1-1900, 1-1908〜1-1913, 1-1917〜1-1939, 1-1943〜1-1966, 1-1970〜1-1991, 1-1995〜1-2013, 1-2017, 1- 2021, 1-2025, 1-2029, 1-2033, 1-2037〜1-2042, 1-2045〜1-2068, 1-2072〜1-2089, 1-2093, 1-2097, 1-2101, 1-2105, 1-2109, 1-2113, 1-2117, 1-2121, 1-2125, 1-2129, 1-2133, 1-2135, 1-2139〜1-2158, 1-2161〜1-2164, 1-2184〜1-2346, 1-2398〜1-2557,
2-9〜2-18, 2-22〜2-43, 2-47〜2-70, 2-74〜2-96, 2-100〜2-119, 2-142, 2-146, 2-150, 2-154, 2-158〜2-163, 2-167〜2-183, 2-185〜2-189, 2-193〜2-216, 2-220〜2-241, 2-245〜2-263, 2-267, 2-271, 2-275, 2-279, 2-283, 2-287〜2-292, 2-296〜2-318, 2-322〜2-338, 2-343, 2-347, 2-351, 2-371, 2-375〜2-377, 2-381〜2-407, 2-416〜2-511，
であり、更に好適には、
1-19, 1-32, 1-36〜1-45, 1-57, 1-62〜1-71, 1-84, 1-88, 1-97〜1-100, 1-152〜1-154, 1-160〜1-214, 1-218〜1-227, 1-264〜1-268, 1-272〜1-322, 1-334, 1-347, 1-360, 1-373, 1-386, 1-390〜1-402, 1-454〜1-458, 1-462〜1-513, 1-526, 1-530〜1-542, 1-594〜1-598, 1-602〜1-653, 1-743, 1-756, 1-760〜1-768, 1-770〜1-774, 1-778〜1-828, 1-832〜1-886, 1-890〜1-940, 1-944〜1-993, 1-1045, 1-1058, 1-1062〜1-1074, 1-1126〜1-1130, 1-1134〜1-1185, 1-1198, 1-1202〜1-1208, 1-1212, 1-1213, 1-1214, 1-1266〜1-1270, 1-1274〜1-1331, 1-1344, 1-1348〜1-1357, 1-1370, 1-1374〜1-1387, 1-1400, 1-1404〜1-1416, 1-1468〜1-1472, 1-1476〜1-1527, 1-1540, 1-1544〜1-1556, 1-1608〜1-1612, 1-1616〜1-1666, 1-1729, 1-1742, 1-1744, 1-1759〜1-1767, 1-1789〜1-1793, 1-1797〜1-1818, 1-1842〜1-1846, 1-1900, 1-1908〜1-1913, 1-1935〜1-1939, 1-1943〜1-1966, 1-1987〜1-1991, 1-2013, 1-2017, 1-2029, 1-2033, 1-2037〜1-2042, 1-2064〜1-2068, 1-2072〜1-2089, 1-2093, 1-2097, 1-2101, 1-2105, 1-2109, 1-2129, 1-2133, 1-2135, 1-2184〜1-2346, 1-2398〜1-2557,
2-11〜2-18, 2-39〜2-43, 2-47〜2-70, 2-185〜2-189, 2-193〜2-216, 2-287〜2-292, 2-338, 2-343, 2-347, 2-351, 2-416〜2-511，
であり、より好適には、
1-45, 1-71, 1-84, 1-88, 1-97〜1-100, 1-152〜1-154, 1-160〜1-206, 1-209〜1-212, 1-264〜1-266, 1-334, 1-373, 1-386, 1-390〜1-402, 1-454〜1-458, 1-462〜1-485, 1-509, 1-510, 1-513, 1-526, 1-530〜1-542, 1-594〜1-598, 1-602〜1-613, 1-649, 1-650, 1-743, 1-756, 1-760〜1-768, 1-770〜1-772, 1-824〜1-828, 1-832〜1-884, 1-936, 1-1045, 1-1058, 1-1062〜1-1074, 1-1126〜1-1130, 1-1134〜1-1145, 1-1148〜1-1151, 1-1162, 1-1163, 1-1179〜1-1182, 1-1185, 1-1198, 1-1202〜1-1208, 1-1212, 1-1213, 1-1214, 1-1266〜1-1270, 1-1274〜1-1285, 1-1288〜1-1291, 1-1319〜1-1322, 1-1329〜1-1331, 1-1344, 1-1348〜1-1357, 1-1370, 1-1387, 1-1400, 1-1404〜1-1416, 1-1468〜1-1472, 1-1476〜1-1487, 1-1490〜1-1493, 1-1504, 1-1505, 1-1521〜1-1524, 1-1527, 1-1540, 1-1544〜1-1556, 1-1608〜1-1612, 1-1616〜1-1627, 1-1663, 1-1664, 1-1729, 1-1742, 1-1744, 1-1761〜1-1766, 1-1789〜1-1791, 1-1815〜1-1818, 1-1900, 1-1909, 1-1962, 1-2064〜1-2066, 1-2089, 1-2093, 1-2097, 1-2105, 1-2133, 1-2216〜1-2288, 1-2290〜1-2346, 1-2398〜1-2557,
であり、更により好適な化合物は、
例示化合物番号式Iａ-１における1-71：リン酸モノ 2-アミノ-2-メチル-4-[5-(4-シクロヘキシルブチル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-84：リン酸モノ 2-アミノ-2-メチル-4-[5-(4-フェニルブチル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-98：リン酸モノ 2-アミノ-2-メチル-4-[5-(5-シクロヘキシルペンチル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-152：リン酸モノ 2-アミノ-2-メチル-4-[5-(5-フェニルペンチル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-210：リン酸モノ 2-アミノ-2-メチル-4-[5-(6-シクロヘキシルヘキシル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-264：リン酸モノ 2-アミノ-2-メチル-4-[5-(6-フェニルヘキシル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-373：リン酸モノ 2-アミノ-2-メチル-4-[5-(3-シクロヘキシルオキシプロピル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-386：リン酸モノ 2-アミノ-2-メチル-4-[5-(3-フェノキシプロピル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-400：リン酸モノ 2-アミノ-2-メチル-4-[5-(4-シクロヘキシルオキシブチル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-454：リン酸モノ 2-アミノ-2-メチル-4-[5-(4-フェノキシブチル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-509：リン酸モノ 2-アミノ-2-メチル-4-[5-(5-シクロヘキシルオキシペンチル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-510：リン酸モノ 2-アミノ-2-メチル-4-[5-(5-フェノキシペンチル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-513：リン酸モノ 2-アミノ-2-メチル-4-[5-(4-シクロヘキシルメトキシプロピル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-743：リン酸モノ 2-アミノ-2-メチル-4-[5-(4-シクロヘキシルブト-1-イニル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-756：リン酸モノ 2-アミノ-2-メチル-4-[5-(4-フェニルブト-1-イニル)チオフェン-2-イル]ブチルエステル、例示化合物番号式Iａ-１における1-770：リン酸モノ 2-アミノ-2-メチル-4-[5-(5-シクロヘキシルペント-1-イニル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-824：リン酸モノ 2-アミノ-2-メチル-4-[5-(5-フェニルペント-1-イニル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-882：リン酸モノ 2-アミノ-2-メチル-4-[5-(6-シクロヘキシルヘキシ-1-イニル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-936：リン酸モノ 2-アミノ-2-メチル-4-[5-(6-フェニルヘキシ-1-イニル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1045：リン酸モノ 2-アミノ-2-メチル-4-[5-(3-シクロヘキシルオキシプロピニル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1058：リン酸モノ 2-アミノ-2-メチル-4-[5-(3-フェノキシプロピニル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1072：リン酸モノ 2-アミノ-2-メチル-4-[5-(4-シクロヘキシルオキシブト-1-イニル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1126：リン酸モノ 2-アミノ-2-メチル-4-[5-(4-フェノキシブト-1-イニル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1181：リン酸モノ 2-アミノ-2-メチル-4-[5-(5-シクロヘキシルオキシペント-1-イニル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1182：リン酸モノ 2-アミノ-2-メチル-4-[5-(5-フェノキシペント-1-イニル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1185：リン酸モノ 2-アミノ-2-メチル-4-[5-(3-シクロヘキシルメトキシプロピニル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1329：リン酸モノ 2-アミノ-2-メチル-4-[5-(4-シクロヘキシルブタノイル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1330：リン酸モノ 2-アミノ-2-メチル-4-[5-(4-フェニルブタノイル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1331：リン酸モノ 2-アミノ-2-メチル-4-[5-(5-シクロヘキシルペンタノイル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1344：リン酸モノ 2-アミノ-2-メチル-4-[5-(5-フェニルペンタノイル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1357：リン酸モノ 2-アミノ-2-メチル-4-[5-(6-シクロヘキシルヘキサノイル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1370：リン酸モノ 2-アミノ-2-メチル-4-[5-(6-フェニルヘキサノイル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1387：リン酸モノ 2-アミノ-2-メチル-4-[5-(3-シクロヘキシルオキシプロパノイル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1400：リン酸モノ 2-アミノ-2-メチル-4-[5-(3-フェノキシプロパノイル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1414：リン酸モノ 2-アミノ-2-メチル-4-[5-(4-シクロヘキシルオキシブタノイル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1468：リン酸モノ 2-アミノ-2-メチル-4-[5-(4-フェノキシブタノイル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1523：リン酸モノ 2-アミノ-2-メチル-4-[5-(5-シクロヘキシルオキシペンタノイル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1524：リン酸モノ 2-アミノ-2-メチル-4-[5-(5-フェノキシペンタノイル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1527：リン酸モノ 2-アミノ-2-メチル-4-[5-(4-シクロヘキシルメトキシプロパノイル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1729：リン酸モノ 2-アミノ-2-メチル-4-[5-(4-シクロヘキシルメトキシフェニル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1742：リン酸モノ 2-アミノ-2-メチル-4-[5-(4-シクロヘキシルエトキシフェニル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1744：リン酸モノ 2-アミノ-2-メチル-4-[5-(4-ベンジルオキシフェニル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1761：リン酸モノ 2-アミノ-2-エチル-4-[5-(4-シクロヘキシルブチル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1764：リン酸モノ 2-アミノ-2-エチル-4-[5-(5-シクロヘキシルペンチル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1816：リン酸モノ 2-アミノ-2-エチル-4-[5-(6-シクロヘキシルヘキシル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1900：リン酸モノ 2-アミノ-2-エチル-4-[5-(4-シクロヘキシルブト-1-イニル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1909：リン酸モノ 2-アミノ-2-エチル-4-[5-(5-シクロヘキシルペント-1-イニル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1962：リン酸モノ 2-アミノ-2-エチル-4-[5-(6-シクロヘキシルヘキシ-1-イニル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2089：リン酸モノ 2-アミノ-2-エチル-4-[5-(4-シクロヘキシルブタノイル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2097：リン酸モノ 2-アミノ-2-エチル-4-[5-(5-シクロヘキシルペンタノイル)チオフェン-2-イル]ブチルエステル、
及び
例示化合物番号式Iａ-１における1-2105：リン酸モノ 2-アミノ-2-エチル-4-[5-(6-シクロヘキシルヘキサノイル)チオフェン-2-イル]ブチルエステル、
並びに
例示化合物番号式Iａ-１における1-463：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-フルオロフェノキシ)ブチル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-479：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-メトキシフェノキシ)ブチル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-594：リン酸モノ 2-アミノ-2-メチル-4-[5-(4-ベンジルオキシブチル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-760：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-フルオロフェニル)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-761：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-メチルフェニル)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-762：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-エチルフェニル)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-763：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-トリフルオロメチルフェニル)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-764：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-メトキシフェニル)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-765：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-エトキシフェニル)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-766：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-メチルチオフェニル)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-832：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3-フルオロフェニル)ペント-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-833：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(4-フルオロフェニル)ペント-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-834：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(4-クロロフェニル)ペント-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-836：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3-メチルフェニル)ペント-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-837：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(4-メチルフェニル)ペント-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-846：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3-トリフルオロメチルフェニル)ペント-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-847：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(4-トリフルオロフェニル)ペント-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-848：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3-メトキシフェニル)ペント-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-849：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(4-メトキシフェニル)ペント-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-860：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3-メチルチオフェニル)ペント-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-861：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(4-メチルフェニル)ペント-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-877：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3,4-ジメチルフェニル)ペント-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-878：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3,5-ジメチルフェニル)ペント-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1050：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(4-メチルシクロヘキシルオキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1062：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(4-フルオロフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1063：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(4-メチルフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1064：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(4-エチルフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1065：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(4-トリフルオロメチルフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1066：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(4-メトキシフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1067：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(4-エトキシフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1068：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(4-メチルチオフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1134：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(3-フルオロフェノキシ)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1135：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-フルオロフェノキシ)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1136：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-クロロフェノキシ)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1138：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(3-メチルフェノキシ)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1139：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-メチルフェノキシ)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1148：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(3-トリフルオロメチルフェノキシ)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1149：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-トリフルオロメチルフェノキシ)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1150：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(3-メトキシフェノキシ)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1151：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-メトキシフェノキシ)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1162：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(3-メチルチオフェノキシ)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1163：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-メチルチオフェノキシ)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1179：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(3,4-ジメチルフェノキシ)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1180：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(3,5-ジメチルフェノキシ)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1198：リン酸モノ 2-アミノ-2-メチル-4-[5-(3-フェニルメトキシプロピニル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1202：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(4-フルオロフェニル)メトキシプロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1203：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(4-メチルフェニル)メトキシプロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1204：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(4-エチルフェニル)メトキシプロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1205：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(4-トリフルオロメチルフェニル)メトキシプロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1206：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(4-メトキシフェニル)メトキシプロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1207：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(4-エトキシフェニル)メトキシプロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1208：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(4-メチルチオフェニル)メトキシプロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1212：リン酸モノ 2-アミノ-2-メチル-4-[5-(4-シクロヘキシルメトキシブト-1-イニル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1266：リン酸モノ 2-アミノ-2-メチル-4-[5-(4-フェニルメトキシブト-1-イニル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1274：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(3-フルオロフェニル)メトキシブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1275：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-フルオロフェニル)メトキシブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1276：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-クロロフェニル)メトキシブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1278：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(3-メチルフェニル)メトキシブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1279：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-メチルフェニル)メトキシブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1288：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(3-トリフルオロメチルフェニル)メトキシブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1289：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-トリフルオロメチルフェニル)メトキシブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1290：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(3-メトキシフェニル)メトキシブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1291：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-メトキシフェニル)メトキシブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1319：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(3,4-ジメチルフェニル)メトキシブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1320：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(3,5-ジメチルフェニル)メトキシブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1348：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(4-フルオロフェニル)ペンタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1349：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(4-メチルフェニル)ペンタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1350：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(4-エチルフェニル)ペンタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1351：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(4-トリフルオロメチルフェニル)ペンタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1352：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(4-メトキシフェニル)ペンタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1353：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(4-エトキシフェニル)ペンタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1354：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(4-メチルチオフェニル)ペンタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1476：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(3-フルオロフェノキシ)ブタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1477：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-フルオロフェノキシ)ブタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1478：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-クロロフェノキシ)ブタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1480：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(3-メチルフェノキシ)ブタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1481：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-メチルフェノキシ)ブタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1490：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(3-トリフルオロメチルフェノキシ)ブタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1491：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-トリフルオロメチルフェノキシ)ブタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1492：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(3-メトキシフェノキシ)ブタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1493：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-メトキシフェノキシ)ブタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1504：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(3-メチルチオフェノキシ)ブタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1505：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-メチルチオフェノキシ)ブタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1521：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(3,4-ジメチルフェノキシ)ブタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1522：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(3,5-ジメチルフェノキシ)ブタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2093：リン酸モノ 2-アミノ−エチル−4-[5-(4-フェニルブタノイル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2101：リン酸モノ 2-アミノ−エチル−4-[5-(5-フェニルペンタノイル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2109：リン酸モノ 2-アミノ−エチル−4-[5-(6-フェニルヘキサノイル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2257：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3,4-ジフルオロフェニル)ペント-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2258：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3,5-ジフルオロフェニル)ペント-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2259：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3-クロロフェニル)ペント-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2260：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3,4-ジクロロフェニル)ペント-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2261：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3,5-ジクロロフェニル)ペント-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2262：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3,4-ジトリフルオロメチルフェニル)ペント-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2263：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3,5-ジトリフルオロメチルフェニル)ペント-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2264：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3,4-ジメトキシフェニル)ペント-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2265：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3,5-ジメトキシフェニル)ペント-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2266：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3,4,5-トリメトキシフェニル)ペント-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2267：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3-アセチルフェニル)ペント-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2268：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(4-アセチルフェニル)ペント-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2269：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(3-フルオロフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2270：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(3,4-ジフルオロフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2271：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(3,5-ジフルオロフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2272：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(3-クロロフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2273：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(4-クロロフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2274：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(3,4-ジクロロフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2275：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(3,5-ジクロロフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2276：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(3-メチルフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2278：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(3,4-ジメチルフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2279：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(3,5-ジメチルフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2280：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(3-トリフルオロメチルフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2281：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(3,4-ジトリフルオロメチルフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2282：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(3,5-ジトリフルオロメチルフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2283：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(3-メトキシフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2284：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(3,4-ジメトキシフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2285：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(3,5-ジメトキシフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2286：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(3,4,5-トリメトキシフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2287：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(3-アセチルフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2288：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(4-アセチルフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2290：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(3,4-ジフルオロフェノキシ)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2291：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(3,5-ジフルオロフェノキシ)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2292：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(3-クロロフェノキシ)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2293：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(3,4-ジクロロフェノキシ)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2294：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(3,5-ジクロロフェノキシ)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2295：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(3,4-ジトリフルオロメチルフェノキシ)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2296：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(3,5-ジトリフルオロメチルフェノキシ)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2297：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(3,4-ジメトキシフェノキシ)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2298：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(3,5-ジメトキシフェノキシ)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2299：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(3,4,5-トリメトキシフェノキシ)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2300：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(3-アセチルフェノキシ)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2301：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-アセチルフェノキシ)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2328：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3-フルオロフェニル)ペンタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2329：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3，4-ジフルオロフェニル)ペンタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2330：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3，5-ジフルオロフェニル)ペンタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2331：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3-クロロフェニル)ペンタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2332：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(4-クロロフェニル)ペンタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2333：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3,4-ジクロロフェニル)ペンタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2334：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3,5-ジクロロフェニル)ペンタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2335：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3-メチルフェニル)ペンタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2336：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3,4-ジメチルフェニル)ペンタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2337：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3,5-ジメチルフェニル)ペンタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2338：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3-トリフルオロメチルフェニル)ペンタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2339：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3，4-ジトリフルオロメチルフェニル)ペンタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2340：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3,5-ジトリフルオロメチルフェニル)ペンタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2341：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3-メトキシフェニル)ペンタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2342：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3,4-ジメトキシフェニル)ペンタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2343：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3,5-ジメトキシフェニル)ペンタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2344：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3，4，5-トリメトキシフェニル)ペンタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2345：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(3-アセチルフェニル)ペンタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2346：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(4-アセチルフェニル)ペンタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Ia-２における1-71：3-アミノ-3-メチル-5-[5-(4-シクロヘキシルブチル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-84：3-アミノ-3-メチル-5-[5-(4-フェニルブチル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-98：3-アミノ-3-メチル-5-[5-(5-シクロヘキシルペンチル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-152：3-アミノ-3-メチル-5-[5-(5-フェニルペンチル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-210：3-アミノ-3-メチル-5-[5-(6-シクロヘキシルヘキシル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-264：3-アミノ-3-メチル-5-[5-(6-フェニルヘキシル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-373：3-アミノ-3-メチル-5-[5-(3-シクロヘキシルオキシプロピル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-386：3-アミノ-3-メチル-5-[5-(3-フェノキシプロピル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-400：3-アミノ-3-メチル-5-[5-(4-シクロヘキシルオキシブチル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-454：3-アミノ-3-メチル-5-[5-(4-フェノキシブチル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-509：3-アミノ-3-メチル-5-[5-(5-シクロヘキシルオキシペンチル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-510：3-アミノ-3-メチル-5-[5-(5-フェノキシペンチル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-513：3-アミノ-3-メチル-5-[5-(4-シクロヘキシルメトキシプロピル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1329：3-アミノ-3-メチル-5-[5-(4-シクロヘキシルブタノイル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1330：3-アミノ-3-メチル-5-[5-(4-フェニルブタノイル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1331：3-アミノ-3-メチル-5-[5-(5-シクロヘキシルペンタノイル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1344：3-アミノ-3-メチル-5-[5-(5-フェニルペンタノイル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1357：3-アミノ-3-メチル-5-[5-(6-シクロヘキシルヘキサノイル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1370：3-アミノ-3-メチル-5-[5-(6-フェニルヘキサノイル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1387：3-アミノ-3-メチル-5-[5-(3-シクロヘキシルオキシプロパノイル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1400：3-アミノ-3-メチル-5-[5-(3-フェノキシプロパノイル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1414：3-アミノ-3-メチル-5-[5-(4-シクロヘキシルオキシブタノイル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1468：3-アミノ-3-メチル-5-[5-(4-フェノキシブタノイル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1523：3-アミノ-3-メチル-5-[5-(5-シクロヘキシルオキシペンタノイル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1524：3-アミノ-3-メチル-5-[5-(5-フェノキシペンタノイル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1527：3-アミノ-3-メチル-5-[5-(4-シクロヘキシルメトキシプロパノイル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1729：3-アミノ-3-メチル-5-[5-(4-シクロヘキシルメトキシフェニル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1742：3-アミノ-3-メチル-5-[5-(4-シクロヘキシルエトキシフェニル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1744：3-アミノ-3-メチル-5-[5-(4-ベンジルオキシフェニル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1761：3-アミノ-3-エチル-5-[5-(4-シクロヘキシルブチル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1764：3-アミノ-3-エチル-5-[5-(5-シクロヘキシルペンチル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1816：3-アミノ-3-エチル-5-[5-(6-シクロヘキシルヘキシル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-2089：3-アミノ-3-エチル-5-[5-(4-シクロヘキシルブタノイル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-2097：3-アミノ-3-エチル-5-[5-(5-シクロヘキシルペンタノイル)チオフェン-2-イル]ペンチルホスホン酸、及び
例示化合物番号式Iａ-２における1-2105：3-アミノ-3-エチル-5-[5-(6-シクロヘキシルヘキサノイル)チオフェン-2-イル]ペンチルホスホン酸、
並びに
例示化合物番号式Iａ-２における1-463：3-アミノ-3-メチル-5-[5-[4-(4-フルオロフェノキシ)ブチル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-479：3-アミノ-3-メチル-5-[5-[4-(4-メトキシフェノキシ)ブチル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-594：3-アミノ-3-メチル-5-[5-(4-ベンジルオキシブチル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1348：3-アミノ-3-メチル-5-[5-[5-(4-フルオロフェニル)ペンタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1349：3-アミノ-3-メチル5-[5-[5-(4-メチルフェニル)ペンタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1350：3-アミノ-3-メチル-5-[5-[5-(4-エチルフェニル)ペンタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1351：3-アミノ-3-メチル-5-[5-[5-(4-トリフルオロメチルフェニル)ペンタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1352：3-アミノ-3-メチル-5-[5-[5-(4-メトキシフェニル)ペンタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1353：3-アミノ-3-メチル-5-[5-[5-(4-エトキシフェニル)ペンタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1354：3-アミノ-3-メチル-5-[5-[5-(4-メチルチオフェニル)ペンタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1476：3-アミノ-3-メチル-5-[5-[4-(3-フルオロフェノキシ)ブタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1477：3-アミノ-3-メチル-5-[5-[4-(4-フルオロフェノキシ)ブタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1478：3-アミノ-3-メチル-5-[5-[4-(4-クロロフェノキシ)ブタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1480：3-アミノ-3-メチル-5-[5-[4-(3-メチルフェノキシ)ブタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1481：3-アミノ-3-メチル-5-[5-[4-(4-メチルフェノキシ)ブタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1490：3-アミノ-3-メチル-5-[5-[4-(3-トリフルオロメチルフェノキシ)ブタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1491：3-アミノ-3-メチル-5-[5-[4-(4-トリフルオロメチルフェノキシ)ブタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1492：3-アミノ-3-メチル-5-[5-[4-(3-メトキシフェノキシ)ブタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1493：3-アミノ-3-メチル-5-[5-[4-(4-メトキシフェノキシ)ブタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1504：3-アミノ-3-メチル-5-[5-[4-(3-メチルチオフェノキシ)ブタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1505：3-アミノ-3-メチル-5-[5-[4-(4-メチルチオフェノキシ)ブタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1521：3-アミノ-3-メチル-5-[5-[4-(3,4-ジメチルフェノキシ)ブタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1522：3-アミノ-3-メチル-5-[5-[4-(3,5-ジメチルフェノキシ)ブタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-2093：3-アミノ−エチル−5-[5-(4-フェニルブタノイル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-2101：3-アミノ−エチル−5-[5-(5-フェニルペンタノイル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-2109：3-アミノ−エチル−5-[5-(6-フェニルヘキサノイル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-2328：3-アミノ-3-メチル-5-[5-[5-(3-フルオロフェニル)ペンタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-2329：3-アミノ-3-メチル-5-[5-[5-(3，4-ジフルオロフェニル)ペンタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-2330：3-アミノ-3-メチル-5-[5-[5-(3，5-ジフルオロフェニル)ペンタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-2331：3-アミノ-3-メチル-5-[5-[5-(3-クロロフェニル)ペンタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-2332：3-アミノ-3-メチル-5-[5-[5-(4-クロロフェニル)ペンタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-2333：3-アミノ-3-メチル-5-[5-[5-(3,4-ジクロロフェニル)ペンタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-2334：3-アミノ-3-メチル-5-[5-[5-(3,5-ジクロロフェニル)ペンタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-2335：3-アミノ-3-メチル-5-[5-[5-(3-メチルフェニル)ペンタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-2336：3-アミノ-3-メチル-5-[5-[5-(3,4-ジメチルフェニル)ペンタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-2337：3-アミノ-3-メチル-5-[5-[5-(3,5-ジメチルフェニル)ペンタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-2338：3-アミノ-3-メチル-5-[5-[5-(3-トリフルオロメチルフェニル)ペンタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-2339：3-アミノ-3-メチル-5-[5-[5-(3，4-ジトリフルオロメチルフェニル)ペンタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-2340：3-アミノ-3-メチル-5-[5-[5-(3,5-ジトリフルオロメチルフェニル)ペンタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-2341：3-アミノ-3-メチル-5-[5-[5-(3-メトキシフェニル)ペンタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-2342：3-アミノ-3-メチル-5-[5-[5-(3,4-ジメトキシフェニル)ペンタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-2343：3-アミノ-3-メチル-5-[5-[5-(3,5-ジメトキシフェニル)ペンタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-2344：3-アミノ-3-メチル-5-[5-[5-(3，4，5-トリメトキシフェニル)ペンタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-2345：3-アミノ-3-メチル-5-[5-[5-(3-アセチルフェニル)ペンタノイル]チオフェン-2-イル]ペンチルホスホン酸及び
例示化合物番号式Iａ-２における1-2346：3-アミノ-3-メチル-5-[5-[5-(4-アセチルフェニル)ペンタノイル]チオフェン-2-イル]ペンチルホスホン酸
であり、最も好適には、
例示化合物番号式Iａ-１における1-71：リン酸モノ 2-アミノ-2-メチル-4-[5-(4-シクロヘキシルブチル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-98：リン酸モノ 2-アミノ-2-メチル-4-[5-(5-シクロヘキシルペンチル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-152：リン酸モノ 2-アミノ-2-メチル-4-[5-(5-フェニルペンチル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-400：リン酸モノ 2-アミノ-2-メチル-4-[5-(4-シクロヘキシルオキシブチル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-463：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-フルオロフェノキシ)ブチル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-479：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-メトキシフェノキシ)ブチル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-594：リン酸モノ 2-アミノ-2-メチル-4-[5-(4-ベンジルオキシブチル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-743：リン酸モノ 2-アミノ-2-メチル-4-[5-(4-シクロヘキシルブト-1-イニル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-756：リン酸モノ 2-アミノ-2-メチル-4-[5-(4-フェニルブト-1-イニル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-770：リン酸モノ 2-アミノ-2-メチル-4-[5-(5-シクロヘキシルペント-1-イニル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-824：リン酸モノ 2-アミノ-2-メチル-4-[5-(5-フェニルペント-1-イニル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-833：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(4-フルオロフェニル)ペント-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-849：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(4-メトキシフェニル)ペント-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1050：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(4-メチルシクロヘキシルオキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1063：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(4-メチルフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1064：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(4-エチルフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1068：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(4-メチルチオフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1072：リン酸モノ 2-アミノ-2-メチル-4-[5-(4-シクロヘキシルオキシブト-1-イニル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1135：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-フルオロフェノキシ)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1139：リン酸モノ 2-アミノ-2-メチル-4-[5-[4-(4-メチルフェノキシ)ブト-1-イニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1185：リン酸モノ 2-アミノ-2-メチル-4-[5-(3-シクロヘキシルメトキシプロピニル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1266：リン酸モノ 2-アミノ-2-メチル-4-[5-(4-フェニルメトキシブト-1-イニル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1329：リン酸モノ 2-アミノ-2-メチル-4-[5-(4-シクロヘキシルブタノイル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1330：リン酸モノ 2-アミノ-2-メチル-4-[5-(4-フェニルブタノイル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1331：リン酸モノ 2-アミノ-2-メチル-4-[5-(5-シクロヘキシルペンタノイル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1344：リン酸モノ 2-アミノ-2-メチル-4-[5-(5-フェニルペンタノイル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1348：リン酸モノ 2-アミノ-2-メチル-4-[5-[5-(4-フルオロフェニル)ペンタノイル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1764：リン酸モノ 2-アミノ-2-エチル-4-[5-(5-シクロヘキシルペンチル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-1909：リン酸モノ 2-アミノ-2-エチル-4-[5-(5-シクロヘキシルペント-1-イニル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2097：リン酸モノ 2-アミノ-2-エチル-4-[5-(5-シクロヘキシルペンタノイル)チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2273：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(4-クロロフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2276：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(3-メチルフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2278：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(3,4-ジメチルフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2283：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(3-メトキシフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2284：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(3,4-ジメトキシフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2285：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(3,5-ジメトキシフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2287：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(3-アセチルフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-１における1-2288：リン酸モノ 2-アミノ-2-メチル-4-[5-[3-(4-アセチルフェノキシ)プロピニル]チオフェン-2-イル]ブチルエステル、
例示化合物番号式Iａ-２における1-71：3-アミノ-3-メチル-5-[5-(4-シクロヘキシルブチル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-98：3-アミノ-3-メチル-5-[5-(5-シクロヘキシルペンチル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-152：3-アミノ-3-メチル-5-[5-(5-フェニルペンチル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-400：3-アミノ-3-メチル-5-[5-(4-シクロヘキシルオキシブチル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-463：3-アミノ-3-メチル-5-[5-[4-(4-フルオロフェノキシ)ブチル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-479：3-アミノ-3-メチル-5-[5-[4-(4-メトキシフェノキシ)ブチル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-594：3-アミノ-3-メチル-5-[5-(4-ベンジルオキシブチル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1329：3-アミノ-3-メチル-5-[5-(4-シクロヘキシルブタノイル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1330：3-アミノ-3-メチル-5-[5-(4-フェニルブタノイル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1331：3-アミノ-3-メチル-5-[5-(5-シクロヘキシルペンタノイル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1344：3-アミノ-3-メチル-5-[5-(5-フェニルペンタノイル)チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1348：3-アミノ-3-メチル-5-[5-[5-(4-フルオロフェニル)ペンタノイル]チオフェン-2-イル]ペンチルホスホン酸、
例示化合物番号式Iａ-２における1-1764：3-アミノ-3-エチル-5-[5-(5-シクロヘキシルペンチル)チオフェン-2-イル]ペンチルホスホン酸
及び
例示化合物番号式Iａ-２における1-2097： 2-アミノ-2-エチル-4-[5-(5-シクロヘキシルペンタノイル)チオフェン-2-イル]ペンチルホスホン酸
である。
【００６５】
【発明の実施の形態】
本発明の化合物（Ｉ）は、以下に記載する方法に従って製造することができる。
【００６６】
Ａ法は、化合物（Ｉ）において、Ｚが酸素原子である化合物（Ｉ−１）を製造する方法である。
【００６７】
【化９】

【００６８】
上記式中、Ｒ¹、Ｒ²、Ｒ³、Ｒａ³、Ｒ⁴、Ｒ⁵、Ｒ⁶、Ｒ⁷、Ｘ、Ｙ及びｎは、前述したものと同意義を示す。Ｒ^10aは、低級アルキル基（特に、ｔ−ブチル基）又は低級アルコキシ基（特に、ｔ−ブトキシ基）を示し、Ｒ^4a、Ｒ^5a、Ｒ^6a、Ｒ^7a、Ｘ^a及びＹ^aは、各々、Ｒ^4a、Ｒ^5a、Ｒ^6a、Ｒ^7a、Ｘ^a及びＹ^aに含まれるアミノ、ヒドロキシ及び／又はカルボキシル基が、保護されてもよいアミノ、ヒドロキシ及び／又はカルボキシル基である他、それぞれ、Ｒ⁴、Ｒ⁵、Ｒ⁶、Ｒ⁷、Ｘ及びＹの基の定義におけるものと同意義を示し、Ｒ¹¹及びＲ¹²は、同一又は異なって、低級アルキル基（特に、エチルまたはイソプロピル基）を示す。
【００６９】
上記において、Ｒ^5a、Ｒ^6a、Ｒ^7a、Ｘ^a及びＹ^aの定義における「保護されてもよいアミノ基」の「保護基」は、有機合成化学の分野で使用されるアミノ基の保護基であれば特に限定はされないが、例えば、
前記「低級脂肪族アシル基」、クロロアセチル、トリフルオロアセチルのようなハロゲノ低級脂肪族アシル基、メトキシアセチルのような低級アルコキシで置換された低級脂肪族アシル基などの「低級脂肪族アシル類」；
ベンゾイル、１−インダンカルボニル、１−若しくは２−ナフトイルのような芳香族アシル基、４−クロロベンゾイル、４−フルオロベンゾイル、２，４，６−トリメチルベンゾイルのような前記置換基群ａから選択される基で１乃至３個置換された芳香族アシル基などの「芳香族アシル類」；
前記「低級アルコキシカルボニル基」、２，２，２−トリクロロエトキシカルボニル、２−トリメチルシリルエトキシカルボニルのようなハロゲンまたはトリ低級アルキルシリルで置換された低級アルコキシカルボニル基などの「低級アルコキシカルボニル基」；
ビニルオキシカルボニル、アリルオキシカルボニルのような「低級アルケニルオキシカルボニル基」；
ベンジルオキシカルボニルのようなアラルキルオキシカルボニル基、４−メトキシベンジルオキシカルボニル、３，４−ジメトキシベンジルオキシカルボニル、２−ニトロベンジルオキシカルボニルのような前記置換基群ａから選択される基で１乃至３個置換されたアラルキルオキシカルボニル基などの「アラルキルオキシカルボニル類」；
トリメチルシリル、トリエチルシリル、イソプロピルジメチルシリル、ｔ−ブチルジメチルシリルのようなトリ低級アルキルシリル基、ジフェニルメチルシリル、フェニルジイソプロピルシリルのようなアリールまたはアリールと低級アルキルとでトリ置換されたシリル基などの「シリル類」；
ベンジル、フェネチル、３−フェニルプロピル、α−ナフチルメチル、ジフェニルメチル、トリフェニルメチルのような１〜３個のアリール基で置換された低級アルキル基、４−メチルベンジル、２，４，６−トリメチルベンジル、４−メトキシベンジル、４−メトキシフェニルジフェニルメチル、２−ニトロベンジル、４−クロロベンジル、４−ブロモベンジル、４−シアノベンジル、４−シアノベンジルジフェニルメチル、ビス（２−ニトロフェニル）メチル、ピペロニルのような低級アルキル、低級アルコキシ、ニトロ、ハロまたはシアノでアリール環が置換された１乃至３個のアリール基で置換された低級アルキル基などの「アラルキル類」；又は
Ｎ，Ｎ−ジメチルアミノメチレン、ベンジリデン、４−メトキシベンジリデン、４−ニトロベンジリデン、サリシリデン、５−クロロサリシリデン、ジフェニルメチレン、（５−クロロ−２−ヒドロキシフェニル）フェニルメチレンのような「シッフ塩基を形成する置換されたメチレン基」であり得、好適には、低級アルコキシカルボニル基、アラルキルオキシカルボニル基又は置換基群ａから選択される基で１乃至３個置換されたアラルキルオキシカルボニル基であり、好適には、低級アルコキシカルボニル基又は低級アルケニルオキシカルボニル基であり、最も好適にはｔ-ブトキシカルボニル基又はアリルオキシカルボニル基である。
【００７０】
上記において、Ｒ^4a、Ｒ^5a、Ｒ^6a、Ｒ^7a、Ｘ^a及びＹ^aの定義における「保護されてもよいヒドロキシ基」の「保護基」は、有機合成化学の分野で使用されるヒドロキシ基の保護基であれば特に限定はされないが、例えば、
前記「低級脂肪族アシル類」；
前記「芳香族アシル類」；
テトラヒドロピラン−２−イル、３−ブロモテトラヒドロピラン−２−イル、４−メトキシテトラヒドロピラン−４−イル、テトラヒドロチオピラン−２−イル、４−メトキシテトラヒドロチオピラン−４−イルのような「テトラヒドロピラニル又はテトラヒドロチオピラニル類」；
テトラヒドロフラン−２−イル、テトラヒドロチオフラン−２−イルのような「テトラヒドロフラニル又はテトラヒドロチオフラニル類」；
前記「シリル類」；
メトキシメチル、１,１−ジメチル−１−メトキシメチル、エトキシメチルのような低級アルコキシメチル基、２−メトキシエトキシメチルのような低級アルコキシ化低級アルコキシメチル基、２，２，２−トリクロロエトキシメチル、ビス(２−クロロエトキシ) メチルのようなハロゲノ低級アルコキシメチル等の「低級アルコキシメチル類」；
１−エトキシエチル、１−( イソプロポキシ) エチルのような低級アルコキシ化エチル基、２，２，２−トリクロロエチルのようなハロゲン化エチル基等の「置換エチル類」；
前記「アラルキル類」；
前記「低級アルコキシカルボニル類」；
前記「低級アルケニルオキシカルボニル類」；又は
前記「アラルキルオキシカルボニル類」
であり得、好適には、低級脂肪族アシル基、芳香族アシル基、低級アルコキシカルボニル基又は（低級アルコキシ）メチル基であり、更に好適には、低級脂肪族アシル基又は（低級アルコキシ）メチル基であり、最も好適にはアセチル基又はメトキシメチル基である。
【００７１】
上記において、Ｒ^5a、Ｒ^6a、Ｒ^7a、Ｘ^a及びＹ^aの定義における「保護されてもよいカルボキシル基」の「保護基」は、有機合成化学の分野で使用されるカルボキシル基の保護基であれば特に限定はされないが、例えば、前記「低級アルキル基」；又は前記「アラルキル基」であり得、好適には低級アルキル基であり、最も好適には、メチル基である。
【００７２】
第Ａ−１工程は、一般式（I−１）を有する化合物を製造する工程であり、アルコール体（10）と化合物(II)とを反応させて亜リン酸エステル体とし、次いで、酸化剤と反応させ、所望により、式ＣＯ₂Ｒ^10aを有する基を含むアミノ基の保護基を除去し、ヒドロキシの保護基を除去し、カルボキシル基の保護基を除去し、リン酸基の保護基を除去し及び／又はアミノ基を低級脂肪族アシル化又は低級アルコキシカルボニル化（アシル化）することにより行われる。
【００７３】
所望の反応は、適宜順序を変えて行うことでき、保護基の除去は、適宜反応条件を選択して、選択的に除去することができる。
【００７４】
一級水酸基を有する化合物をリン酸エステル体に導くには、有機合成化学の分野で一般的に使用される方法に準じて行うことができる。例えば、実験化学講座２２（第４版：丸善）「有機合成IV」第３章「リン酸エステル」に記載の方法により、容易に導くことが可能である。実際には以下のような方法が好適である。
【００７５】
すなわち、アルコール体（10）と化合物（II）とを、不活性溶媒中、活性化剤存在下、反応させ亜リン酸エステル体を製造し、次いで、不活性溶媒中、酸化剤と反応させる方法である。
【００７６】
化合物（10）と化合物（II）との反応において使用される不活性溶媒は、例えば、ヘキサン、ヘプタンのような脂肪族炭化水素類；ベンゼン、トルエン、キシレンのような芳香族炭化水素類；塩化メチレン、クロロホルム、ジクロロメタン、１，２−ジクロロエタン、四塩化炭素のようなハロゲン化炭化水素類；ジエチルエーテル、ジイソプロピルエーテル、テトラヒドロフランのようなエーテル類或は上記溶媒の混合溶媒であり、好適には、ハロゲン化炭化水素類又はエーテル類（最も好適には、塩化メチレン又はテトラヒドロフラン）である。
【００７７】
使用される活性化剤は、例えば、１Ｈ−テトラゾール、５−メチル−１Ｈ−テトラゾール、５−フェニル−１Ｈ―テトラゾールのようなテトラゾール類、（好適には、１Ｈ−テトラゾール）である。
【００７８】
使用される化合物（II）は、好適には、ジアリル N,N-ジイソプロピルホスホロアミダイト、ジメチル N,N-ジイソプロピルホスホロアミダイト、ジエチル N,N-ジイソプロピルホスホロアミダイト、ジ−ｔ−ブチル N,N-ジイソプロピルホスホロアミダイト、ジベンジル N,N-ジイソプロピルホスホロアミダイト、ジメチル N,N-ジエチルホスホロアミダイト、ジ−ｔ−ブチル N,N-エチルホスホロアミダイト、ジベンジル N,N-ジエチルホスホロアミダイト、N.N-ジエチル−1,5−ジヒドロ−2,4,3−ベンゾジオキサホスフェピン−3−アミン、ビス（２−シアノエチル） N,N-ジイソプロピルホルホロアミダイト又はビス（９−フルオレニルメチル） N,N-ジイソプロピルホルホロアミダイトのようなホスホロアミダイト類であり、特に好適には、ジアリル N,N-ジイソプロピルホスホロアミダイトである。
【００７９】
反応温度は、原料化合物、溶媒の種類等によって異なるが、通常、−１０℃乃至６０℃（好適には０℃乃至３０℃）である。
【００８０】
反応時間は、原料化合物、溶媒、反応温度等により異なるが、通常、１０分間乃至２４時間（好適に３０分間乃至２時間）である。
【００８１】
上記反応で得られる亜リン酸エステル体は、反応の後処理及び単離をせずに、酸化剤と反応することができる。
【００８２】
酸化剤との反応において使用される不活性溶媒は、アルコール体（10）と化合物（II）との反応に使用されるものと同様のものである。
【００８３】
使用される酸化剤は、例えば、ｔ−ブチルヒドロペルオキシド、クメンヒドロペルオキシド、ｍ−クロロ過安息香酸、3,5−ジニトロ過安息香酸、０−カルボキシ過安息香酸、ジメチルオキソラン、過酢酸、過トリフルオロ酢酸、過フタル酸、過酸化水素水のような過酸化物であり、好適には、ｔ−ブチルヒドロペルオキシド又はｍ−クロロ過安息香酸である。
【００８４】
反応温度は、得られた亜リン酸エステル体、酸化剤、溶媒の種類等によって異なるが、通常、−７８℃乃至室温（好適には、―７８℃乃至０℃）である。
【００８５】
反応時間は、得られた亜リン酸エステル体、酸化剤、溶媒、反応温度等により異なるが、通常、５分間乃至２時間（好適には、５分間乃至３０分間）である。
【００８６】
アミノ、ヒドロキシ及びカルボキシル基の保護基の除去はその種類によって異なるが、一般に有機合成化学の技術において周知の方法、例えば、T.W.Green,（Protective Groups in Organic Synthesis）,John Wiley & Sons:J.F.W.McOmis,（Protective Groups in OrganicChemistry）,Plenum Pressに記載の方法により以下のように行うことができる。
【００８７】
アミノ基の保護基が、シリル類である場合には、通常、弗化テトラブチルアンモニウム、弗化水素酸、弗化水素酸−ピリジン、弗化カリウムのような弗素アニオンを生成する化合物で処理するか、又は、塩酸、臭化水素酸、硫酸、過塩素酸、リン酸のような無機酸又は酢酸、蟻酸、蓚酸、メタンスルホン酸、ｐ−トルエンスルホン酸、カンファースルホン酸、トリフルオロ酢酸、トリフルオロメタンスルホン酸のような有機酸（好適には、塩酸）で処理することにより除去できる。
【００８８】
尚、弗素アニオンにより除去する場合に、蟻酸、酢酸、プロピオン酸のような有機酸を加えることによって、反応が促進することがある。
【００８９】
上記反応に使用される溶媒は、好適には、ジエチルエーテル、ジイソプロピルエーテル、テトラヒドロフラン、ジオキサン、ジメトキシエタン、ジエチレングリコールジメチルエーテルのようなエ−テル類；アセトニトリル、イソブチロニトリルのようなニトリル類；酢酸のような有機酸；水；又は上記溶媒の混合溶媒であり、好適には、テトラヒドロフランである。
【００９０】
反応温度及び反応時間は、原料化合物、触媒、溶媒等により異なるが、通常、反応温度は、０℃乃至１００℃（好適には、１０℃乃至５０℃）であり、反応時間は、１０分間乃至２４時間（好適には、３０分間乃至６時間）である。
【００９１】
アミノ基の保護基が、アラルキル類又はアラルキルオキシカルボニル類である場合には、通常、不活性溶媒中、還元剤と接触させること（好適には、触媒下、常温にて水素を用いる接触還元）により除去する方法又は酸化剤を用いて除去する方法が好適である。
【００９２】
接触還元による除去に使用される溶媒は、本反応に不活性なものであれば特に限定はないが、例えば、ヘキサン、ヘプタン、リグロイン、石油エーテルのような脂肪族炭化水素類；トルエン、ベンゼン、キシレンのような芳香族炭化水素類；酢酸メチル、酢酸エチル、酢酸プロピル、酢酸ブチル、炭酸ジエチルのようなエステル類；ジエチルエーテル、ジイソプロピルエーテル、テトラヒドロフラン、ジオキサン、ジメトキシエタン、ジエチレングリコールジメチルエーテルのようなエーテル類；メタノール、エタノール、ｎ−プロパノール、イソプロパノール、ｎ−ブタノール、イソブタノール、ｔ−ブタノール、イソアミルアルコール、ジエチレングリコール、グリセリン、オクタノール、シクロヘキサノール、メチルセロソルブのようなアルコール類；酢酸のような有機酸類；水；又は上記溶媒と水との混合溶媒であり、好適には、アルコール類、エーテル類、有機酸類又は水（最も好適には、アルコール類又は有機酸類）である。
【００９３】
接触還元による除去に使用される触媒は、通常、接触還元反応に使用されるものであれば、特に限定はないが、好適には、パラジウム−炭素、ラネ−ニッケル、酸化白金、白金黒、ロジウム−酸化アルミニウム、トリフェニルホスフィン−塩化ロジウム、パラジウム−硫酸バリウムである。
【００９４】
水素の圧力は、特に限定はないが、通常１乃至１０気圧である。
【００９５】
反応温度及び反応時間は、原料化合物、触媒、溶媒等により異なるが、通常、反応温度は、０℃乃至１００℃であり、反応時間は、５分間乃至２４時間である。
【００９６】
酸化剤を用いる除去において使用される溶媒は、本反応に関与しないものであれば特に限定はないが、好適には、含水有機溶媒であり、このような有機溶媒は、例えば、クロロホルム、ジクロロメタン、１，２−ジクロロエタン、四塩化炭素のようなハロゲン化炭化水素類；アセトニトリルのようなニトリル類、ジエチルエーテル、ジイソプロピルエーテル、テトラヒドロフラン、ジオキサン、ジメトキシエタン、ジエチレングリコールジメチルエーテルのようなエ−テル類；アセトンのようなケトン類；ホルムアミド、ジメチルホルムアミド、ジメチルアセトアミド、ヘキサメチルリン酸トリアミドのようなアミド類；ジメチルスルホキシドのようなスルホキシド類；又はスルホランであり、好適には、ハロゲン化炭化水素類、エ−テル類又はスルホキシド類（最も好適には、ハロゲン化炭化水素類又はスルホキシド類）である。
【００９７】
使用される酸化剤は、酸化に使用される化合物であれば特に限定はないが、好適には、過硫酸カリウム、過硫酸ナトリウム、アンモニウムセリウムナイトレイト（ＣＡＮ）、２，３−ジクロロ−５，６−ジシアノ−ｐ−ベンゾキノン（ＤＤＱ）である。
【００９８】
反応温度及び反応時間は、原料化合物、触媒、溶媒等により異なるが、通常、反応温度は、０℃乃至１５０℃であり、反応時間は、１０分間乃至２４時間である。
【００９９】
また、アミノ基の保護基が、アラルキル類である場合には、不活性溶媒中、酸を用いて保護基を除去することもできる。
【０１００】
上記反応に使用される酸は、通常の反応において酸触媒として使用されるものであれば特に限定はないが、例えば、塩酸、臭化水素酸、硫酸、過塩素酸、リン酸のような無機酸；酢酸、蟻酸、蓚酸、メタンスルホン酸、ｐ−トルエンスルホン酸、カンファースルホン酸、トリフルオロ酢酸、トリフルオロメタンスルホン酸のような有機酸等のブレンステッド酸；塩化亜鉛、四塩化スズ、ボロントリクロリド、ボロントリフルオリド、ボロントリブロミドのようなルイス酸；又は酸性イオン交換樹脂であり、好適には、無機酸又は有機酸（最も好適には、塩酸、酢酸又はトリフルオロ酢酸）である。
【０１０１】
使用される不活性溶媒は、例えば、ヘキサン、ヘプタン、リグロイン、石油エーテルのような脂肪族炭化水素類；ベンゼン、トルエン、キシレンのような芳香族炭化水素類；クロロホルム、ジクロロメタン、１，２−ジクロロエタン、四塩化炭素のようなハロゲン化炭化水素類；酢酸メチル、酢酸エチル、酢酸プロピル、酢酸ブチル、炭酸ジエチルのようなエステル類；ジエチルエーテル、ジイソプロピルエーテル、テトラヒドロフラン、ジオキサン、ジメトキシエタン、ジエチレングリコールジメチルエーテルのようなエーテル類；メタノ−ル、エタノ−ル、ｎ−プロパノ−ル、イソプロパノ−ル、ｎ−ブタノ−ル、イソブタノ−ル、ｔ−ブタノ−ル、イソアミルアルコ−ル、ジエチレングリコール、グリセリン、オクタノール、シクロヘキサノール、メチルセロソルブのようなアルコ−ル類；ホルムアミド、ジメチルホルムアミド、ジメチルアセトアミド、ヘキサメチルリン酸トリアミドのようなアミド類；水；或は水又は上記溶媒の混合溶媒であり、好適には、エーテル類、アルコ−ル類又は水（最も好適には、ジオキサン、テトラヒドロフラン、エタノール又は水）である。
【０１０２】
反応温度は、原料化合物、使用される酸、溶媒等により異なるが、通常、−２０℃乃至沸点温度（好適には、０℃乃至１００℃）である。
【０１０３】
反応時間は、原料化合物、使用される酸、溶媒、反応温度等により異なるが、通常、１５分間乃至４８時間（好適には、３０分間乃至２０時間）である。
【０１０４】
アミノ基の保護基が、低級脂肪族アシル類、芳香族アシル類、低級アルコキシカルボニル類又はシッフ塩基を形成する置換されたメチレン基である場合には、不活性溶媒及び水の存在下に、酸又は塩基で加水分解することにより除去することができる。
【０１０５】
上記反応に使用される酸は、通常酸として使用されるもので反応を阻害しないものであれば特に限定はないが、例えば、臭化水素酸、塩酸、硫酸、過塩素酸、リン酸、硝酸のような無機酸であり、好適には塩酸である。
【０１０６】
上記反応に使用される塩基は、化合物の他の部分に影響を与えないものであれば特に限定はないが、好適には、炭酸リチウム、炭酸ナトリウム、炭酸カリウムのようなアルカリ金属炭酸塩類；水酸化リチウム、水酸化ナトリウム、水酸化カリウムのようなアルカリ金属水酸化物類；リチウムメトキシド、ナトリウムメトキシド、ナトリウムエトキシド、カリウム−ｔ−ブトキシドのような金属アルコキシド類；又はアンモニア水、濃アンモニア−メタノ−ルのようなアンモニア類であり、好適には、アルカリ金属水酸物である。
【０１０７】
上記反応に使用される溶媒は、通常の加水分解反応に使用されるものであれば特に限定はないが、例えば、メタノ−ル、エタノ−ル、ｎ−プロパノ−ル、イソプロパノ−ル、ｎ−ブタノ−ル、イソブタノ−ル、ｔ−ブタノ−ル、イソアミルアルコ−ル、ジエチレングリコール、グリセリン、オクタノール、シクロヘキサノール、メチルセロソルブのようなアルコ−ル類；ジエチルエーテル、ジイソプロピルエーテル、テトラヒドロフラン、ジオキサン、ジメトキシエタン、ジエチレングリコールジメチルエーテルのようなエ−テル類；水；又は水と上記有機溶媒との混合溶媒であり、好適にはエーテル類（最も好適にはジオキサン）である。
【０１０８】
反応温度及び反応時間は、原料化合物、溶媒及び使用される酸若しくは塩基等により異なり、特に限定はないが、副反応を抑制するために、通常、反応温度は、０℃乃至１５０℃であり、反応時間は、１時間乃至１０時間である。
【０１０９】
アミノ基の保護基が低級アルケニルオキシカルボニル類である場合には、アミノの保護基が前記の脂肪族アシル類、芳香族アシル類、アルコキシカルボニル類又はシッフ塩基を形成する置換されたメチレン基である場合の除去反応における塩基処理と同様に行われる。
【０１１０】
尚、アリルオキシカルボニル基の場合は、特に、不活性溶媒中、パラジウム、及びトリフェニルホスフィン若しくはニッケルテトラカルボニルを使用して、保護基を除去する方法が簡便で、副反応が少なく実施することができる。
【０１１１】
使用される不活性溶媒は、反応を阻害せず、原料化合物をある程度溶解するものであれば、特に限定はないが、好適には、メタノール、エタノール、イソプロパノールのようなアルコール類；ジエチルエーテル、ジイソプロピルエーテル、t-ブチルメチルエーテル、テトラヒドロフラン、ジオキサンのようなエーテル類；ベンゼン、トルエン、キシレンのような芳香族炭化水素類；ヘキサン、シクロヘキサンのような脂肪族炭化水素類；アセトニトリル、プロピオニトリルのようなニトリル類；又は酢酸エチル、酢酸プロピルのようなエステル類であり、さらに好適には、エーテル類（特に好適には、テトラヒドロフラン）又はニトリル類（特に好適には、アセトニトリル）である。
【０１１２】
反応温度及び反応時間は、原料化合物、触媒、溶媒等により異なるが、通常、反応温度は、０℃乃至１５０℃（好適には０℃乃至１００℃）であり、反応時間は、５分間乃至４８時間（好適には３０分間乃至２４時間）である。
【０１１３】
ヒドロキシ基の保護基が、シリル類である場合には、前記アミノの保護基がシリル類である場合と同様に処理して除去される。
【０１１４】
ヒドロキシ基の保護基が、アラルキル類又はアラルキルオキシカルボニル類である場合には、前記アミノ基の保護基がアラルキル類又はアラルキルオキシカルボニル類である場合と同様に処理して除去される。
【０１１５】
ヒドロキシ基の保護基が、低級アルコキシメチル類、テトラヒドロピラニル又はテトラヒドロチオピラニル類、テトラヒドロフラニル又はテトラヒドロチオフラニル類、又は置換されたエチル類である場合には、通常、不活性溶媒中、酸で処理することにより除去される。
【０１１６】
使用される酸としては、通常、ブレンステッド酸又はルイス酸として使用されるものであれば特に限定はなく、好適には、塩化水素；塩酸、硫酸、硝酸のような無機酸；酢酸、トリフルオロ酢酸、メタンスルホン酸、ｐ−トルエンスルホン酸のような有機酸：又は三弗化ホウ素のようなルイス酸であり、好適には、塩酸又は酢酸であり、また、ダウエックス５０Ｗのような強酸性の陽イオン交換樹脂も使用することができる。
【０１１７】
上記反応に使用される溶媒としては、本反応に不活性なものであれば特に限定はないが、例えば、ヘキサン、ヘプタン、リグロイン、石油エーテルのような脂肪族炭化水素類；ベンゼン、トルエン、キシレンのような芳香族炭化水素類；メチレンクロリド、クロロホルム、四塩化炭素、ジクロロエタン、クロロベンゼン、ジクロロベンゼンのようなハロゲン化炭化水素類；蟻酸エチル、酢酸エチル、酢酸プロピル、酢酸ブチル、炭酸ジエチルのようなエステル類；ジエチルエ−テル、ジイソプロピルエ−テル、テトラヒドロフラン、ジオキサン、ジメトキシエタン、ジエチレングリコールジメチルエーテルのようなエ−テル類；メタノ−ル、エタノ−ル、ｎ−プロパノ−ル、イソプロパノ−ル、ｎ−ブタノ−ル、イソブタノ−ル、ｔ−ブタノ−ル、イソアミルアルコ−ル、ジエチレングリコール、グリセリン、オクタノール、シクロヘキサノール、メチルセロソルブのようなアルコ−ル類；アセトン、メチルエチルケトン、メチルイソブチルケトン、イソホロン、シクロヘキサノンのようなケトン類；水；又は上記溶媒の混合溶媒であり、好適には、エ−テル類（最も好適には、テトラヒドロフラン）又はアルコール類（最も好適には、メタノール）である。
【０１１８】
反応温度及び反応時間は、原料化合物、使用される酸、溶媒等により異なるが、反応温度は、−１０℃乃至２００℃（好適には、０℃乃至１５０℃）であり、反応時間は、５分間乃至４８時間（好適には、３０分間乃至１０時間）である。
【０１１９】
ヒドロキシ基の保護基が、低級脂肪族アシル類、芳香族アシル類、低級アルコキシカルボニル基類又は低級アルケニルオキシカルボニル類である場合には、前記アミノの保護基が脂肪族アシル類、芳香族アシル類、アルコキシカルボニル類又はシッフ塩基を形成する置換されたメチレン基である場合の除去反応における塩基処理と同様に行われる。
【０１２０】
尚、ヒドロキシ基の保護基が、アリルオキシカルボニル基の場合は、特にパラジウム、及びトリフェニルホスフィン、又はビス（メチルジフェニルホスフィン）（１，５−シクロオクタジエン）イリジウム（Ｉ）・ヘキサフルオロホスフェートを使用して除去する方法が簡便で、副反応が少なく実施することができ、前記アミノ基の保護基がアリルオキシカルボニル基である場合と同様に処理して除去される。
【０１２１】
カルボキシル基の保護基が、低級アルキル基又はアラルキル基である場合は、ヒドロキシ基の保護基が前記の脂肪族アシル類、芳香族アシル類又はアルコキシカルボニル類である場合の除去反応の条件と同様にして、塩基と処理することにより達成される。
【０１２２】
カルボキシル基の保護基が、アラルキル基である場合には、前記アミノの保護基がアラルキル類又はアラルキルオキシカルボニル基である場合と同様に、接触還元により除去することもできる。
【０１２３】
リン酸基の保護基が、シアノ基、置換されてもよいシリル基、アリール基、ヘテロシクリル基、アリールチオ基、スルホニル基又はハロゲン原子により置換されても良い低級アルキル基である場合には、不活性溶媒中、水の存在下、酸で加水分解するか、あるいは、不活性溶媒中、ハロゲン化トリメチルシリル（例えば、ブロモトリメチルシリル又はヨードトリメチルシリル）と反応させることにより該保護基が除去される。
【０１２４】
上記加水分解に使用させる不活性溶媒は、例えば、メタノ−ル、エタノ−ルのようなアルコ−ル類；又はジエチルエーテル、ジイソプロピルエーテル、テトラヒドロフラン、ジオキサンのようなエーテル類であり、好適にはエーテル類であり、最も好適にはジオキサンである。
【０１２５】
上記反応で使用される酸は、例えば、塩酸、硫酸、リン酸、硝酸のような無機酸であり、好適には塩酸である。
【０１２６】
反応温度は、０℃乃至１５０℃（好適には２０℃乃至１００℃）であり、反応温度は、１時間乃至６０時間（好適には１時間乃至４８時間）である。
【０１２７】
上記のハロゲン化トリメチルシリルとの反応に使用される不活性溶媒は、例えば、ヘキサン、ヘプタンのような脂肪族炭化水素類；ベンゼン、トルエン、キシレンのような芳香族炭化水素類；塩化メチレン、クロロホルム、ジクロロメタン、１，２−ジクロロエタン、四塩化炭素のようなハロゲン化炭化水素類；アセトニトリルのようなニトリル類；ジエチルエーテル、ジイソプロピルエーテル、テトラヒドロフラン、ジオキサンのようなエーテル類；メタノ−ル、エタノ−ル、ｎ−プロパノ−ルのようなアルコ−ル類；或いは上記溶媒の混合溶媒であり、好適には、ハロゲン化炭化水素類又はニトリル類（より好適には、クロロホルム、ジクロロメタン又はアセトニトリル）である。
【０１２８】
反応温度は、原料化合物、使用される溶媒の種類等によって異なるが、通常、−７８℃乃至１００℃（好適には０℃乃至８０℃）である。
【０１２９】
反応時間は、原料化合物、使用される溶媒、反応温度等により異なるが、通常、１０分乃至２４時間（好適に１時間乃至６時間）である。
【０１３０】
リン酸基の保護基が低級アルケニル基である場合には、不活性溶媒中、アミン、蟻酸、蟻酸塩類、トリアルキルスズ化合物又は活性メチレン化合物の存在下、パラジウム化合物と反応させることにより、該保護基を除去することができる。
【０１３１】
上記反応に使用される不活性溶媒は、例えば、ヘキサン、ヘプタンのような脂肪族炭化水素類；トルエン、ベンゼン、キシレンのような芳香族炭化水素類；クロロホルム、ジクロロメタンのようなハロゲン化炭化水素類；アセトニトリルのようなニトリル類；酢酸メチル、酢酸エチル、酢酸プロピルのようなエステル類；ジエチルエーテル、ジイソプロピルエーテル、テトラヒドロフラン、ジオキサンのようなエ−テル類；メタノ−ル、エタノ−ル、ｎ−プロパノ−ル、イソプロパノ−ルのようなアルコ−ル類；酢酸のような有機酸類；水；又は上記溶媒と水との混合溶媒であり、好適には、ニトリル類又はエーテル類（特に好適には、アセトニトリル又はテトラヒドロフラン）である。
【０１３２】
上記反応で使用されるアミンは、例えば、トリエチルアミン、トリブチルアミン、ジイソプロピルエチルアミン、Ｎ−メチルモルホリン、１，４−ジアザビシクロ［２．２．２］オクタン（ＤＡＢＣＯ）のような第三級アミン類；ジエチルアミン、ジメチルアミン、ジイソプロピルアミン、ピロリジンのような第二級アミン類；又はエチルアミン、プロピルアミン、ブチルアミン、Ｎ，Ｎ−ジメチルアニリン、Ｎ，Ｎ−ジエチルアニリンのような第一級アミン類であり、好適には、ピロリジンである。
【０１３３】
上記反応で使用される蟻酸塩類は、好適には、蟻酸アンモニウム、蟻酸トリエチルアミン塩又は蟻酸ｎ−ブチルアミン塩である。
【０１３４】
上記反応に使用されるトリアルキルスズ化合物は、好適には、トリメチルスズ、トリエチルスズ又はトリブチルスズであり、特に好適には、トリブチルスズである。
【０１３５】
上記反応で使用される活性メチレン化合物は、例えば、マロン酸メチル、マロン酸エチルのようなマロン酸エステル類；シアノ酢酸メチルのようなシアノ酢酸エステル類；アセト酢酸メチル、アセト酢酸エチル、ベンゾイル酢酸エチルのようなβ−ケト酢酸エステル類；アセチルアセトン、ベンゾイルアセトン、ジベンゾイルメタン、１，３−シクロペンタジオン、１，３−シクロヘキサジオン、ジメドンのような１，３−ジケトン類；又は上記活性メチレン化合物のアルカリ金属塩であり、好適には、１，３−ジケトン類（特に、ジメドン）又はマロン酸エステル類のナトリウム塩（特に、ジエチルマロン酸ナトリウム塩）である。
【０１３６】
上記反応で使用されるパラジウム化合物は、例えば、テトラキス（トリフェニルホスフィン）パラジウム、ジクロロジ（トリフェニルホスフィン）パラジウムのようなＰｄ⁰化合物；又はジアセトキシパラジウム、ビス（ジベンジリデンアセトン）パラジウムのようなＰｄ^II化合物であり、好適には、テトラキス（トリフェニルホスフィン）パラジウムである。
【０１３７】
反応温度は、原料化合物、使用される溶媒の種類等によって異なるが、通常、０℃乃至１００℃（好適には２０℃乃至８０℃）である。
【０１３８】
反応時間は、原料化合物、使用される溶媒、反応温度等により異なるが、通常、１０分乃至４８時間（好適に３０分乃至２４時間）である。
【０１３９】
リン酸基の保護基が、アリールメチル基である場合は、前記アミノの保護基がアラルキル類又はアラルキルオキシカルボニル基である場合と同様に処理して除去される。
【０１４０】
リン酸基の保護基が、アリール基である場合は、前記アミノ基の保護基が、低級脂肪族アシル類、芳香族アシル類、低級アルコキシカルボニル類又はシッフ塩基を形成する置換されたメチレン基である場合と同様に処理して除去される。
【０１４１】
リン酸基の保護基が、アミド類である場合、前記アミノの保護基が脂肪族アシル類、芳香族アシル類、アルコキシカルボニル類又はシッフ塩基を形成する置換されたメチレン基である場合の除去反応における酸処理と同様に行われる。
【０１４２】
アミノ基をアシル化する方法は、化合物（10）を、不活性溶媒中、塩基の存在下又は非存在下、下記化合物
Ｒ^1a−Ｑ（III）
［式中、Ｒ^1aは、低級脂肪族アシル基又は低級アルコキシカルボニル基を示し、Ｑはハロゲン原子（好適には、塩素原子、臭素原子又は沃素原子）を示す。］と反応させることにより行なわれる。
【０１４３】
使用される不活性溶媒は、好適には、ジエチルエ−テル、ジイソプロピルエ−テル、テトラヒドロフラン、ジオキサン、ジメトキシエタン、ジエチレングリコールジメチルエーテルのようなエ−テル類；メタノ−ル、エタノ−ル、ｎ−プロパノ−ル、イソプロパノ−ル、ｎ−ブタノ−ル、イソブタノ−ル、ｔ−ブタノ−ル、イソアミルアルコ−ル、ジエチレングリコール、グリセリン、オクタノール、シクロヘキサノール、メチルセロソルブのようなアルコール類；酢酸エチル、酢酸プロピルのようなエステル類；アセトン、２−ブタノンのようなアルキルケトン類；ジクロロメタン、クロロホルム、四塩化炭素のようなハロゲン化炭化水素類；又は上記溶媒と水との混合溶媒であり、好適には、上記溶媒と水との混合溶媒（特に好適には、酢酸エチルと水との混合溶媒）である。
【０１４４】
使用される塩基は、例えば、炭酸カリウムのようなアルカリ金属炭酸塩類；炭酸水素ナトリウム、炭酸水素カリウムのようなアルカリ金属炭酸水素塩類；水酸化ナトリウム、水酸化カリウムのようなアルカリ金属水酸化物類；水酸化マグネシウム、水酸化カルシウムのようなアルカリ土類金属水酸化物；又はトリエチルアミン、トリブチルアミン、ジイソプロピルエチルアミン、Ｎ−メチルモルホリン、ピリジン、ピロリジンのような有機アミン類であり、好適には、アルカリ金属炭酸水素塩類（特に好適には、炭酸水素カリウム）である。
【０１４５】
反応温度は、原料化合物、使用される塩基、使用される溶媒の種類等によって異なるが、０℃乃至５０℃（好適には室温付近）である。
【０１４６】
反応時間は、原料化合物、使用される塩基、使用される溶媒、反応温度等により異なるが、３０分間乃至１０時間（好適には１時間乃至５時間）である。
【０１４７】
反応終了後、各反応の目的化合物（Ｉ-1）は常法に従って、反応混合物から採取される。例えば、反応混合物を適宜中和し、酸化剤が存在する場合は、適宜、還元剤で分解し、又は、不溶物が存在する場合には、適宜濾過により除去した後、水と酢酸エチルのような混和しない有機溶媒を加え、目的化合物を含む有機層を分離し、水等で洗浄後、無水硫酸マグネシウム、無水硫酸ナトリウム、無水炭酸水素ナトリウム等で乾燥後、溶剤を留去することによって得られる。得られた目的化合物は必要ならば、常法、例えば再結晶、再沈殿、クロマトグラフィー等の通常、有機化合物の分離精製に慣用されている方法を適宜組合せ、分離、精製することができる。
【０１４８】
Ｂ法は、化合物（I）において、Zがメチレンである化合物（Ｉ−２）を製造する方法である。
【０１４９】
【化１０】

【０１５０】
上記式中、Ｒ¹、Ｒ²、Ｒ³、Ｒａ³、Ｒ⁴、Ｒ^4a、Ｒ⁵、Ｒ^5a、Ｒ⁶、Ｒ^6a、Ｒ⁷、Ｒ^7a、Ｒ^10a、Ｘ、Ｘ^a、Ｙ、Ｙ^a及びｎは、前述したものと同意義を示す。
【０１５１】
第Ｂ−１工程は、一般式（10）を有する化合物を酸化して、一般式（ＩＶ）を有するアルデヒド体を製造する工程である。
【０１５２】
酸化反応は、一級アルコールからアルデヒドを生成する酸化反応であれば、特に限定はないが、例えば、塩化メチレン中、ピリジン及びクロム酸を用いて行われるCollins酸化；塩化メチレン中、塩化クロム酸ピリジニウム(PCC)を用いて行われるPCC酸化；塩化メチレン中、二クロム酸ピリジニウム(PDC)を用いて行われるPDC酸化；塩化メチレン中、親電子剤（例えば無水酢酸、無水トリフルオロ酢酸、塩化チオニル、塩化スルフリル、塩化オキザリル、ジシクロヘキシルカルボジイミド、ジフェニルケテン-p-トリルイミン、N,N-ジエチルアミノアセチレン、三酸化硫黄・ピリジン錯体など）及びジメチルスルホキシド(DMSO)を用いて行われる、Swern酸化のような、DMSO酸化；塩化メチレン若しくはベンゼン中、二酸化マンガンを用いて行われる二酸化マンガン酸化；又は塩化メチレン中、Dess-Martinペルヨージナンを用いて行われるDess-Martin酸化であり、好適には、塩化メチレン中で行われる、Dess-Martin酸化、PDC酸化又はSwern酸化である。
【０１５３】
反応温度は、原料化合物、溶剤、酸化剤の種類等によって異なるが、通常、−７８℃乃至１００℃であり、好適には、−７８℃乃至３０℃である。
【０１５４】
反応時間は、原料化合物、溶媒、酸化剤の種類、反応温度等によって異なるが、通常１０分間乃至２日間であり、好適には、３０分間乃至２４時間である。
【０１５５】
反応終了後、本反応の目的化合物であるアルデヒド体（IＶ）は常法に従って、反応混合物から採取される。例えば、酸化剤を亜硫酸水素ナトリウム水等で中和し、不溶物が存在する場合には濾過により除去後、そのまま濃縮すること或いは水と酢酸エチルのような混和しない有機溶媒を加え、目的化合物を含む有機層を分離し、無水硫酸ナトリウム、無水硫酸マグネシウム等で乾燥後、溶媒を留去することによって得られる。
【０１５６】
得られたアルデヒド体（IＶ）は、必要ならば、常法、例えば、再結晶、再沈殿、クロマトグラフィー等を利用して分離、精製することができる。
【０１５７】
第Ｂ−２工程は、不活性溶媒中、塩基の存在下、アルデヒド体（IＶ）を一般式（Ｖ）を有する化合物と反応させ、α,β-不飽和リン酸エステル体（ＶＩ）に導く工程である。
【０１５８】
上記反応に使用される不活性溶媒は、出発物質をある程度溶解するものであれば、特に限定はないが、好適には、ベンゼン、トルエン、キシレンのような芳香族炭化水素類；ジクロロメタン、クロロホルム、四塩化炭素のようなハロゲン化炭化水素類；ジエチルエーテル、ジイソプロピルエーテル、t-ブチルメチルエーテル、テトラヒドロフランのようなエーテル類；アセトニトリル、イソブチロニトリルのようなニトリル類；ホルムアミドのようなアミド類；又はジメチルスルホキシドのようなスルホキシド類であり、さらに好適には、芳香族炭化水素類又はエーテル類（特に好適には、ベンゼン又はテトラヒドロフラン）である。
【０１５９】
使用される塩基は、化合物（Ｖ）と反応させて、相当するカルバニオンを生成させるものであれば、特に限定はないが、好適には、炭酸ナトリウム、炭酸カリウムのようなアルカリ金属炭酸塩類；炭酸水素ナトリウム、炭酸水素カリウムのようなアルカリ金属炭酸水素塩類；水素化ナトリウム、水素化カリウムのようなアルカリ金属水素化物類；水酸化ナトリウム、水酸化カリウムのようなアルカリ金属水酸化物類；ナトリウムメトキシド、ナトリウムエトキシド、カリウムメトキシド、カリウムエトキシドのようなアルカリ金属アルコキシド類；N-メチルモルホリン、トリエチルアミンのような有機アミン類；又はブチルリチウム、リチウムジイソプロピルアミドのような有機金属塩基類であり、さらに好適には、アルカリ金属アルコキシド類、アルカリ金属水素化物類及び有機金属塩基類であり、特に好適には、水素化ナトリウムである。
【０１６０】
反応温度は、原料化合物、溶剤、ホスホニウム塩の種類、塩基の種類等によって異なるが、通常、−８０℃乃至１００℃であり、好適には、−２０℃乃至５０℃である。
【０１６１】
反応時間は、原料化合物、溶剤、ホスホニウム塩の種類、塩基の種類等によって異なるが、通常１０分間乃至２日間であり、好適には、１０分間乃至１２時間である。
【０１６２】
反応終了後、本反応の目的化合物である不飽和リン酸エステル化合物（ＶＩ）は常法に従って、反応混合物から採取される。例えば、反応液を希塩酸等で中和し、不溶物が存在する場合には濾過により除去後、そのまま濃縮すること或いは水と酢酸エチルのような混和しない有機溶媒を加え、目的化合物を含む有機層を分離し、無水硫酸ナトリウム、無水硫酸マグネシウム等で乾燥後、溶媒を留去することによって得られる。
【０１６３】
得られた不飽和リン酸エステル化合物（ＶＩ）は、必要ならば、常法、例えば、再結晶、再沈殿、クロマトグラフィー等を用いて、分離、精製することができる。
【０１６４】
第Ｂ−３工程は、一般式（Ｉ−２）を有する化合物を製造する工程であり、不飽和リン酸エステル化合物（ＶＩ）を不活性溶媒中、接触還元触媒の存在下、水素と反応させ、所望により、式ＣＯ₂Ｒ^10aを有する基を含むアミノ基の保護基を除去し、ヒドロキシの保護基を除去し、カルボキシル基の保護基を除去し、リン酸基の保護基を除去し及び／又はアミノ基をアシル化することにより行われる。
【０１６５】
不飽和リン酸エステル化合物（ＶＩ）を水素と反応させる反応で使用される不活性溶媒は、反応を阻害せず、出発物質をある程度溶解するものであれば、特に限定はないが、好適には、メタノール、エタノール、イソプロパノールのようなアルコール類；ジエチルエーテル、ジイソプロピルエーテル、t-ブチルメチルエーテル、テトラヒドロフラン、ジオキサンのようなエーテル類；ベンゼン、トルエン、キシレンのような芳香族炭化水素類；ヘキサン、シクロヘキサンのような脂肪族炭化水素類；又は酢酸エチル、酢酸プロピルのようなエステル類であり、さらに好適には、アルコール類（特に好適には、メタノール又はエタノール）である。
【０１６６】
使用される接触還元触媒は、好適には、パラジウム−炭素、水酸化パラジウム−炭素、パラジウム黒、酸化白金、白金黒、ロジウム−酸化アルミニウム、トリフェニルホスフィン−塩化ロジウム(Wilkinson錯体)、パラジウム−硫酸バリウム、ラネーニッケルであり、さらに好適には、パラジウム−炭素又はトリフェニルホスフィン−塩化ロジウム(Wilkinson錯体)である。
【０１６７】
水素の圧力は、特に限定はないが、通常１乃至１０気圧で行われる。
【０１６８】
反応温度は、原料化合物、溶剤、塩基の種類等によって異なるが、通常、０℃乃至１００℃（好適には、室温乃至６０℃）である。
【０１６９】
反応時間は、原料化合物、反応温度、溶剤、塩基の種類によって異なるが、通常、５分間乃至９６時間（好適には、1時間乃至４８時間）である。
【０１７０】
反応終了後、本反応の目的化合物（Ｉ―２）は常法に従って、反応混合物から採取される。例えば、反応混合物を適宜中和し、又、不溶物が存在する場合には濾過により除去した後、水と酢酸エチルのような混和しない有機溶媒を加え、目的化合物を含む有機層を分離し、水等で洗浄後、無水硫酸マグネシウム、無水硫酸ナトリウム、無水炭酸水素ナトリウム等で乾燥後、溶剤を留去することによって得られる。得られた目的化合物は必要ならば、常法、例えば再結晶、再沈殿、クロマトグラフィーを用いて、分離、精製することができる。
【０１７１】
所望により行われる、アミノ基の保護基を除去する反応、ヒドロキシの保護基を除去する反応、カルボキシル基の保護基を除去する反応、リン酸基の保護基を除去する反応及びアミノ基をアシル化する反応は、前述の第Ａ−１工程と同様に行うことができる。
【０１７２】
原料化合物（１０）は、公知化合物であるか又は公知方法に従って容易に製造される（例えば、ＷＯ０２／０６２６８号公報参照）。また、以下の方法によっても製造することができる。
【０１７３】
Ｃ法は、化合物（１０）を製造する方法である。
【０１７４】
【化１１】

【０１７５】
上記式中、Ｒ^4a、Ｒ^5a、Ｒ^6a、Ｒ^7a、Ｒ^10a、Ｘ^a、Ｙ^a及びｎは、前述したものと同意義を示し、Ｒ⁸は、ホルミル基、カルボキシル基又は低級アルコキシカルボニル基を示し、Ｒ⁹及びＲ^9aは、同一又は異なって、低級アルキル基を示し、Ｒ¹⁰は、低級脂肪族アシル基を示す。
【０１７６】
第Ｃ−１工程は、一般式（３）を有する化合物を製造する工程であり、一般式（２）を有する化合物を、不活性溶媒中、塩基の存在下又は非存在下（好適には存在下）、還元剤と反応させることにより行われる。尚、化合物（２）は、公知化合物であるか、又は公知方法に従って容易に製造される（例えば、ＷＯ０２／０６２６８号公報参照）。
【０１７７】
上記反応に使用される不活性溶媒は、例えば、ヘキサン、ヘプタン、リグロイン、石油エーテルのような脂肪族炭化水素類；ベンゼン、トルエン、キシレンのような芳香族炭化水素類；クロロホルム、ジクロロメタン、１，２−ジクロロエタン、四塩化炭素のようなハロゲン化炭化水素類；酢酸、酢酸メチル、酢酸エチル、酢酸プロピル、酢酸ブチル、炭酸ジエチルのようなエステル類；ジエチルエーテル、ジイソプロピルエーテル、テトラヒドロフラン、ジオキサン、ジメトキシエタン、ジエチレングリコールジメチルエーテルのようなエーテル類；メタノ−ル、エタノ−ル、ｎ−プロパノ−ル、イソプロパノ−ル、ｎ−ブタノ−ル、イソブタノ−ル、ｔ−ブタノ−ル、イソアミルアルコ−ル、ジエチレングリコール、グリセリン、オクタノール、シクロヘキサノール、メチルセロソルブのようなアルコ−ル類；ホルムアミド、ジメチルホルムアミド、ジメチルアセトアミド、ヘキサメチルリン酸トリアミドのようなアミド類；水；又は上記溶媒の混合溶媒であり、好適には、エーテル類（最も好適には、テトラヒドロフラン）である。
【０１７８】
上記反応に使用される塩基は、トリエチルアミン、トリブチルアミン、ジイソプロピルエチルアミン、Ｎ−メチルモルホリン、ピリジン、ピロリジンのような有機アミン類であり、好適には、トリエチルアミンである。
【０１７９】
上記反応に使用される還元剤は、例えば、水素化ホウ素ナトリウム、水素化ホウ素リチウム、水素化シアノホウ素ナトリウムのような水素化ホウ素アルカリ金属類；又は水素化ジイソブチルアルミニウム、水素化アルミニウムリチウム、水素化トリエトキシアルミニウムリチウムのような水素化アルミニウム化合物であり、好適には、水素化ホウ素アルカリ金属類（最も好適には、水素化ホウ素ナトリウム）である。
【０１８０】
反応温度は、原料化合物、使用される還元剤、溶媒の種類等によって異なるが、通常、−５０℃乃至１００℃（好適には０℃乃至５０℃）である。
【０１８１】
反応時間は、原料化合物、使用される還元剤、溶媒、反応温度等により異なるが、通常、１５分乃至１５０時間（好適には、１時間乃至１００時間）である。
【０１８２】
反応終了後、本反応の目的化合物（３）は常法に従って、反応混合物から採取される。例えば、反応混合物を適宜中和し、又、不溶物が存在する場合には濾過により除去した後、水と酢酸エチルのような混和しない有機溶媒を加え、目的化合物を含む有機層を分離し、水等で洗浄後、無水硫酸マグネシウム、無水硫酸ナトリウム、無水炭酸水素ナトリウム等で乾燥後、溶剤を留去することによって得られる。得られた目的化合物は必要ならば、常法、例えば再結晶、再沈殿、クロマトグラフィー等を用いて、分離、精製することができる。
【０１８３】
第Ｃ−２工程は、一般式（４）を有する化合物を製造する工程であり、不活性溶媒中、塩基の存在下、化合物（３）のヒドロキシ基を脱離基に変換した後、沃素化剤と反応させることにより行われる。
【０１８４】
ヒドロキシ基を脱離基に変換する試薬は、例えば、メタンスルホニルクロリド、Ｐ−トルエンスルホニルクロリドのようなスルホニルハライド；チオニルクロリド、チオニルブロミド、チオニルアイオダイドのようなチオニルハライド類；スルフリルクロリド、スルフリルブロミド、スルフリルアイオダイドのようなスルフリルハライド類；三塩化燐、三臭化燐、三沃化燐のような三ハロゲン化燐類；五塩化燐、五臭化燐、五沃化燐のような五ハロゲン化燐類；オキシ塩化燐、オキシ臭化燐、オキシ沃化燐のようなオキシハロゲン化燐類；のようなハロゲン化剤；又はメチルトリオキソレニウム（VII）のようなレニウム試薬であり、好適には、スルホニルハライド（特にＰ−トルエンスルホニルクロリド）である。
【０１８５】
ヒドロキシ基を脱離基に変換させる際に使用される塩基は、例えば、炭酸リチウム、炭酸ナトリウム、炭酸カリウムのようなアルカリ金属炭酸塩類；炭酸水素リチウム、炭酸水素ナトリウム、炭酸水素カリウムのようなアルカリ金属重炭酸塩類；水素化リチウム、水素化ナトリウム、水素化カリウムのようなアルカリ金属水素化物類；水酸化リチウム、水酸化ナトリウム、水酸化カリウムのようなアルカリ金属水酸化物類；リチウムメトキシド、ナトリウムメトキシド、ナトリウムエトキシド、カリウムｔ−ブトキシドのようなアルカリ金属アルコキシド類；又はトリエチルアミン、トリブチルアミン、ジイソプロピルエチルアミン、Ｎ−メチルモルホリン、ピリジン、４−（Ｎ，Ｎ−ジメチルアミノ）ピリジン、Ｎ，Ｎ−ジメチルアニリン、Ｎ，Ｎ−ジエチルアニリン、１，５−ジアザビシクロ［４．３．０］ノナ−５−エン、１，４−ジアザビシクロ［２．２．２］オクタン（ＤＡＢＣＯ）、１，８−ジアザビシクロ［５．４．０］−７−ウンデセン（ＤＢＵ）のような有機アミン類であり、好適には、有機アミン類（最も好適には、トリエチルアミン）である。
【０１８６】
ヒドロキシ基を脱離基に変換させる際に使用される不活性溶媒は、例えば、ヘキサン、ヘプタン、リグロイン、石油エーテルのような脂肪族炭化水素類；ベンゼン、トルエン、キシレンのような芳香族炭化水素類；クロロホルム、ジクロロメタン、１，２−ジクロロエタン、四塩化炭素のようなハロゲン化炭化水素類；ジエチルエーテル、ジイソプロピルエーテル、テトラヒドロフラン、ジオキサン、ジメトキシエタン、ジエチレングリコールジメチルエーテルのようなエーテル類；アセトン、２−ブタノンのようなケトン類；ホルムアミド、ジメチルホルムアミド、ジメチルアセトアミド、ヘキサメチルリン酸トリアミドのようなアミド類；ジメチルスルホキシドのようなスルホキシド類；又はスルホランであり、好適には、ハロゲン化炭化水素類（最も好適には、ジクロロメタン）である。
【０１８７】
ヒドロキシ基を脱離基に変換させる際の反応温度は、原料化合物、使用される試薬、溶媒の種類等によって異なるが、通常、−５０℃乃至２００℃（好適には、−１０℃乃至１５０℃）である。
【０１８８】
ヒドロキシ基を脱離基に変換させる際の反応時間は、原料化合物、使用される試薬、溶媒、反応温度等により異なるが、通常、１５分間乃至２４時間（好適には、３０分間乃至１２時間）である。
【０１８９】
上記反応に使用される沃素化剤は、例えば、五沃化燐、オキシ沃化燐、沃化ナトリウム、沃化カリウムであり、好適には、沃化ナトリウムである。
【０１９０】
脱離基を沃素化する際の反応温度は、原料化合物、使用される試薬、溶媒の種類等によって異なるが、通常、０℃乃至２００℃（好適には、１０℃乃至１５０℃）である。
【０１９１】
脱離基を沃素化する際の反応時間は、原料化合物、使用される試薬、溶媒、反応温度等により異なるが、通常、１５分間乃至２４時間（好適には３０分間乃至１２時間）である。
【０１９２】
反応終了後、本反応の目的化合物（４）は常法に従って、反応混合物から採取される。例えば、反応混合物を適宜中和し、又、不溶物が存在する場合には濾過により除去した後、水と酢酸エチルのような混和しない有機溶媒を加え、目的化合物を含む有機層を分離し、水等で洗浄後、無水硫酸マグネシウム、無水硫酸ナトリウム、無水炭酸水素ナトリウム等で乾燥後、溶剤を留去することによって得られる。得られた目的化合物は必要ならば、常法、例えば再結晶、再沈殿、クロマトグラフィー等を用いて、分離、精製することができる。
【０１９３】
第Ｃ−３工程は、一般式（６）を有する化合物を製造する工程であり、不活性溶媒中、化合物（４）を、塩基の存在下、一般式（５）を有する化合物と反応させることにより行われる。
【０１９４】
上記反応に使用される不活性溶媒は、例えば、ジエチルエーテル、ジイソプロピルエーテル、テトラヒドロフラン、ジオキサン、ジメトキシエタン、ジエチレングリコールジメチルエーテルのようなエーテル類；メタノ−ル、エタノ−ル、ｎ−プロパノ−ル、イソプロパノ−ル、ｎ−ブタノ−ル、イソブタノ−ル、ｔ−ブタノ−ル、イソアミルアルコ−ル、ジエチレングリコール、グリセリン、オクタノール、シクロヘキサノール、メチルセロソルブのようなアルコ−ル類；ホルムアミド、ジメチルホルムアミド、ジメチルアセトアミド、ヘキサメチルリン酸トリアミドのようなアミド類；水；又は上記溶媒の混合溶媒であり、好適には、アルコ−ル類又はアミド類（最も好適には、ジメチルホルムアミド）である。
【０１９５】
上記反応に使用される塩基は、例えば、前記第Ｃ−２工程のヒドロキシ基を脱離基に変換させる際に使用されるものと同様なものであり、好適には、アルカリ金属水素化物類又はアルカリ金属アルコキシド類（最も好適には、水素化ナトリウム）である。
【０１９６】
反応温度は、原料化合物、塩基、溶媒の種類等によって異なるが、通常、−７８℃乃至１００℃（好適には、０℃乃至５０℃）である。
【０１９７】
反応時間は、原料化合物、塩基、溶媒、反応温度等により異なるが、通常、１５分間乃至４８時間（好適には、３０分間乃至１２時間）である。
【０１９８】
反応終了後、本反応の目的化合物（６）は常法に従って、反応混合物から採取される。例えば、反応混合物を適宜中和し、又、不溶物が存在する場合には濾過により除去した後、水と酢酸エチルのような混和しない有機溶媒を加え、目的化合物を含む有機層を分離し、水等で洗浄後、無水硫酸マグネシウム、無水硫酸ナトリウム、無水炭酸水素ナトリウム等で乾燥後、溶剤を留去することによって得られる。得られた目的化合物は必要ならば、常法、例えば再結晶、再沈殿、クロマトグラフィー等を用いて、分離、精製することができる。
【０１９９】
第Ｃ−４工程は、一般式（７）を有する化合物を製造する工程であり、不活性溶媒中、水の存在下、化合物（６）を塩基と反応させ、１個の低級アルコキシカルボニル基を加水分解することにより行われる。
【０２００】
上記反応に使用される不活性溶媒は、本反応に不活性なものであれば特に限定はされないが、例えば、ヘキサン、ヘプタン、リグロイン、石油エーテルのような脂肪族炭化水素類；ベンゼン、トルエン、キシレンのような芳香族炭化水素類；ジエチルエーテル、ジイソプロピルエーテル、テトラヒドロフラン、ジオキサン、ジメトキシエタン、ジエチレングリコールジメチルエーテルのようなエーテル類；メタノ−ル、エタノ−ル、ｎ−プロパノ−ル、イソプロパノ−ル、ｎ−ブタノ−ル、イソブタノ−ル、ｔ−ブタノ−ル、イソアミルアルコ−ル、ジエチレングリコール、グリセリン、オクタノール、シクロヘキサノール、メチルセロソルブのようなアルコ−ル類；又は上記溶媒の混合溶媒であり、好適には、アルコ−ル類（最も好適には、エタノ−ル）である。
【０２０１】
上記反応に使用される塩基は、例えば、前記Ｃ−２工程のヒドロキシ基を脱離基に変換させる際に使用されるものと同様なものであり、好適には、アルカリ金属水酸化物類（最も好適には、水酸化カリウム）である。
【０２０２】
反応温度は、原料化合物、塩基、溶媒の種類等によって異なるが、通常、−２０℃乃至２００℃（好適には、０℃乃至５０℃）である。
【０２０３】
反応時間は、原料化合物、塩基、溶媒、反応温度等により異なるが、通常、３０分間乃至１２０時間（好適には、１時間乃至８０時間）である。
【０２０４】
反応終了後、本反応の目的化合物（７）は常法に従って、反応混合物から採取される。例えば、反応混合物を適宜中和し、又、不溶物が存在する場合には濾過により除去した後、水と酢酸エチルのような混和しない有機溶媒を加え、目的化合物を含む有機層を分離し、水等で洗浄後、無水硫酸マグネシウム、無水硫酸ナトリウム、無水炭酸水素ナトリウム等で乾燥後、溶剤を留去することによって得られる。得られた目的化合物は必要ならば、常法、例えば再結晶、再沈殿、クロマトグラフィーを用いて、分離、精製することができる。
【０２０５】
第Ｃ−５工程は、一般式（９）を有する化合物を製造する工程であり、化合物（７）のカルボキシル基をクルチウス転位反応に付し、カルバメートに変換する方法であり、化合物（７）を、不活性溶媒中、塩基の存在下、ジフェニルリン酸アジドのようなジアリールリン酸アジド誘導体と反応させた後、一般式（８）を有する化合物と反応させることにより行われる。
【０２０６】
上記反応に使用される不活性溶媒は、本反応に不活性なものであれば特に限定はされないが、例えば、ヘキサン、ヘプタン、リグロイン、石油エーテルのような脂肪族炭化水素類；ベンゼン、トルエン、キシレンのような芳香族炭化水素類；クロロホルム、ジクロロメタン、１，２−ジクロロエタン、四塩化炭素のようなハロゲン化炭化水素類；ジエチルエーテル、ジイソプロピルエーテル、テトラヒドロフラン、ジオキサン、ジメトキシエタン、ジエチレングリコールジメチルエーテルのようなエーテル類；又は上記溶媒の混合溶媒であり、好適には芳香族炭化水素類（最も好適には、ベンゼン）である。
【０２０７】
上記反応に使用される塩基は、例えば、前記第Ｃ−２工程のヒドロキシ基を脱離基に変換させる際に使用されるものと同様なものであり、好適には、有機アミン類（最も好適には、トリエチルアミン）である。
【０２０８】
化合物（７）をジアリールリン酸アジド誘導体と反応させる際の反応温度は、原料化合物、塩基、溶媒の種類等によって異なるが、通常、０℃乃至２００℃（好適には、２０℃乃至１５０℃）である。
【０２０９】
化合物（７）をジアリールリン酸アジド誘導体と反応させる際の反応時間は、原料化合物、塩基、溶媒、反応温度等により異なるが、通常、１５分間乃至２４時間（好適には３０分間乃至１２時間）である。
【０２１０】
化合物（７）をジアリールリン酸アジド誘導体と反応させた後、同一の反応溶液中で、化合物（８）を加えて反応させる。
【０２１１】
反応温度は、原料化合物、塩基、溶媒の種類等によって異なるが、通常、０℃乃至２００℃（好適には、２０℃乃至１５０℃）である。
【０２１２】
反応時間は、原料化合物、塩基、溶媒、反応温度等により異なるが、通常、１５分間乃至２４時間（好適には３０分間乃至１２時間）である。
【０２１３】
また、化合物（７）をジアリールリン酸アジド誘導体と反応させる際に、化合物（８）のうち、ジアリールリン酸アジド誘導体と直接反応しにくいものを一緒に反応させることにより、カルボキシル基を一気にカルバメートに変換することができる。
【０２１４】
反応終了後、本反応の目的化合物（９）は常法に従って、反応混合物から採取される。例えば、反応混合物を適宜中和し、又、不溶物が存在する場合には濾過により除去した後、水と酢酸エチルのような混和しない有機溶媒を加え、目的化合物を含む有機層を分離し、水等で洗浄後、無水硫酸マグネシウム、無水硫酸ナトリウム、無水炭酸水素ナトリウム等で乾燥後、溶剤を留去することによって得られる。得られた目的化合物は必要ならば、常法、例えば再結晶、再沈殿、クロマトグラフィー等を用いて、分離、精製することができる。
【０２１５】
第Ｃ−６工程は、一般式（10）を有する化合物を製造する工程であり、化合物（９）のエステル部分を還元し、所望により、式ＣＯ²Ｒ¹⁰を有する基を除去し、低級脂肪族アシル化又は低級アルコキシカルボニル化（アシル化）することにより行なわれる。
【０２１６】
化合物（９）のエステル部分を還元する反応は、前記Ｃ−１工程と同様に行われる。
【０２１７】
式ＣＯ₂Ｒ¹⁰を有する基を除去する反応及びアシル化は、前記Ａ−１工程と同様に行われる。
【０２１８】
本発明の一般式（Ｉ）を有するリン酸又はホスホン酸誘導体、その薬理上許容される塩又はその薬理上許容されるエステルは、毒性が低く優れた免疫抑制作用を有し、各種臓器移植又は皮膚移植での拒絶反応、全身性エリトマトーデス、慢性関節リウマチ、多発性筋炎、結合組織炎、骨格筋炎、骨関節炎、変形性関節症、皮膚筋炎、強皮症、ベーチェット病、Chron病、潰瘍性大腸炎、自己免疫性肝炎、再生不良性貧血、特発性血小板減少性紫斑病、自己免疫性溶血性貧血、多発性硬化症、自己免疫性水疱症、尋常性乾癬、血管炎症群、Wegener肉芽腫、ぶどう膜炎、シェーグレン症候群、特発性間質性肺炎、Goodpasture症候群、サルコイドーシス、アレルギー性肉芽腫性血管炎、気管支喘息、心筋炎、心筋症、大動脈炎症候群、心筋梗塞後症候群、原発性肺高血圧症、微小変化型ネフローゼ、膜性腎症、膜性増殖性腎炎、巣状糸球体硬化症、半月体形成性腎炎、重症筋無力症、炎症性ニューロパチー、アトピー性皮膚炎、慢性光線性皮膚炎、日光過敏症、蓐瘡、Ｓｙｄｅｎｈａｍ舞踏病，全身性硬化症、成人発症糖尿病、インスリン依存性糖尿病、若年性糖尿病、アテローム性動脈硬化症、糸球体腎炎、IgA腎症、尿細管間質性腎炎、原発性胆汁性肝硬変、原発性硬化性胆管炎、劇症肝炎、ウイルス性肝炎、GVHD、接触皮膚炎、敗血症等の自己免疫疾患又はその他免疫関連疾患、真菌、マイコプラズマ、ウィルス、原虫等の感染症、心不全、心肥大、不整脈、狭心症、心虚血、動脈塞栓、動脈瘤、静脈瘤、血行障害等の循環器系疾患、アルツハイマー病、痴呆、パーキンソン病、脳卒中、脳梗塞、脳虚血、鬱病、躁鬱病、統合失調症、ハンチントン舞踏病、癲癇、痙攣、多動症、脳炎、髄膜炎、食欲不振および過食等の中枢系疾患、リンパ腫、白血病、多尿、頻尿、糖尿病性網膜症等の各種疾患（特に好適には、各種臓器移植又は皮膚移植での拒絶反応、全身性エリトマトーデス、慢性関節リウマチ、多発性硬化症、アトピー性皮膚炎等の自己免疫疾患）の、温血動物用（特に、ヒト用）の予防剤若しくは治療剤（特に、治療薬）として有用である。
【０２１９】
本発明の一般式（Ｉ）を有する化合物、その薬理上許容される塩又はその薬理上許容されるエステルを、上記疾患の治療剤又は予防剤として使用する場合には、それ自体或は適宜の薬理学的に許容される、賦形剤、希釈剤等と混合し、例えば、錠剤、カプセル剤、顆粒剤、散剤若しくはシロップ剤等による経口的又は注射剤若しくは坐剤等による非経口的に投与することができる。
【０２２０】
これらの製剤は、賦形剤（例えば、乳糖、白糖、葡萄糖、マンニトール、ソルビトールのような糖誘導体；トウモロコシデンプン、バレイショデンプン、α澱粉、デキストリンのような澱粉誘導体；結晶セルロースのようなセルロース誘導体；アラビアゴム；デキストラン；プルランのような有機系賦形剤：及び、軽質無水珪酸、合成珪酸アルミニウム、珪酸カルシウム、メタ珪酸アルミン酸マグネシウムのような珪酸塩誘導体；リン酸水素カルシウムのようなリン酸塩；炭酸カルシウムのような炭酸塩；又は硫酸カルシウムのような硫酸塩等の無機系賦形剤である。）、滑沢剤（例えば、ステアリン酸、ステアリン酸カルシウム、ステアリン酸マグネシウムのようなステアリン酸金属塩；タルク；コロイドシリカ；ビーガム、ゲイ蝋のようなワックス類；硼酸；アジピン酸；硫酸ナトリウムのような硫酸塩；グリコール；フマル酸；安息香酸ナトリウム；ＤＬロイシン；脂肪酸ナトリウム塩；ラウリル硫酸ナトリウム、ラウリル硫酸マグネシウムのようなラウリル硫酸塩；無水珪酸、珪酸水和物のような珪酸類；又は上記澱粉誘導体である。）、結合剤（例えば、ヒドロキシプロピルセルロース、ヒドロキシプロピルメチルセルロース、ポリビニルピロリドン、マクロゴール、又は、前記賦形剤と同様の化合物である。）、崩壊剤（例えば、低置換度ヒドロキシプロピルセルロース、カルボキシルメチルセルロース、カルボキシルメチルセルロースカルシウム、内部架橋カルボキシルメチルセルロースナトリウムのようなセルロース誘導体；カルボキシルメチルスターチ、カルボキシルメチルスターチナトリウム又は架橋ポリビニルピロリドンのような化学修飾されたデンプン・セルロース類である。）、安定剤（例えば、メチルパラベン、プロピルパラベンのようなパラオキシ安息香酸エステル類；クロロブタノール、ベンジルアルコール、フェニルエチルアルコールのようなアルコール類；塩化ベンザルコニウム；フェノール、クレゾールのようなフェノール類；チメロサール；デヒドロ酢酸；又はソルビン酸である。）、矯味矯臭剤（例えば、通常使用される、甘味料、酸味料、香料等である。）、希釈剤等の添加剤を用いて周知の方法で製造される。
【０２２１】
その使用量は症状、年齢等により異なるが、経口投与の場合には、１回当り１日下限０．０５ｍｇ（好適には、５ｍｇ）、上限２００ｍｇ（好適には、４０ｍｇ）を、静脈内投与の場合には、１回当り１日下限０．０１ｍｇ（好適には、１ｍｇ）、上限１００ｍｇ（好適には、１０ｍｇ）を成人に対して、１日当り１乃至６回症状に応じて投与することが望ましい。
【０２２２】
【実施例】
以下に、実施例および試験例を示し、本発明を更に詳細に説明するが、本発明の範囲はこれらに限定されるものではない。
【０２２３】
（実施例１）
リン酸モノ−（2R）−アミノ−2−メチル−4−[5−（5−フェニルペンタノイル）チオフェン−2−イル]ブチルエステル
【０２２４】
【化１２】

【０２２５】
(ａ)
酢酸（2R）−アセチルアミノ−2−メチル−4−[5−（5−フェニルペント−1−イニル）チオフェン−2−イル]ブチルエステル
参考例2で合成した酢酸（2R）−アセチルアミノ−2−メチル−4−（5−ブロモチオフェン−2−イル）ブチルエステル4．00g（11．5mmol）をジメチルホルムアミド40mLに溶解させ、参考例4で合成した5−フェニルペント−1−イン4．97g（34．5mmol）、トリエチルアミン16.0mL（115mmol）、ヨウ化銅(Ｉ)437mg（2.30mmol）、ジクロロビス（トリフェニルホスフィン）パラジウ
ム806mg（1.15mmol）を加え、窒素雰囲気下80℃で2時間撹拌した。反応液を飽和塩化アンモニウム水溶液と混合し、酢酸エチルで抽出し、酢酸エチル層を水及び飽和食塩水で洗浄した。酢酸エチル層を無水硫酸ナトリウムで乾燥後、溶媒を減圧下留去した。残渣をシリカゲルクロマトグラフィー（溶出溶媒：ヘキサン／酢酸エチル＝1／1〜1／2）で精製し、さらに分取ＨＰLＣ（カラム：ＴＳＫｇｅｌＯＤＳ−80Ｔｓ 55×300mm、溶出溶媒：アセトニトリル／水＝1／1、流速50mL／miｎ）で精製して、標記化合物を無色油状態物として、3.27g（収率69％）得た。
核磁気共鳴スペクトル(400MHz, CDCl₃)， δ: 1.36(3H, s), 1.85-2.05(3H, m), 1.94(3H, s), 2.10(3H, s), 2.25-2.35(1H, m), 2.43(2H, t, J=7.0 Hz), 3.70-3.80(4H, m), 4.17(1H, d, J=11.2 Hz), 4.31(1H, d, J=11.2 Hz), 5.38(1H, bRs), 6.64(1H, d, J=3.6 Hz),6.94 (1H, d, J=3.6 Hz), 7.15-7.42(5H, m)。
マススペクトル(FAB)， m/z: 412 ((M + H)⁺) 。
【０２２６】
(ｂ)
（2R）−アミノ−2−メチル−4−[5−（5−フェニルペンタノイル）チオフェン−2−イル]ブタン−1−オール
実施例1(ａ)で得られた酢酸（2R）−アセチルアミノ−2−メチル−4−[5−（5−フェニルペント−1−イニル）チオフェン−2−イル]ブチルエステル3.27g（7．95mmol）をテトラヒドロフラン20mL、メタノール20mL及び水20mLに溶解させ、水酸化リチウム一水和物3.33g（79.5mmol）を加え、50℃で6時間攪拌した。反応液を水に注ぎ、塩化メチレンで抽出し、塩化メチレン層を無水硫酸ナトリウムで乾燥後、溶媒を減圧下留去した。得られた残渣をメタノール25mLに溶解させ、6規定硫酸25mLを加え100℃で2時間攪拌した。反応液に氷冷下20％水酸化ナトリウム水溶液を加えアルカリ性にした後、塩化メチレンで抽出し、塩化メチレン層を無水硫酸ナトリウムで乾燥後、溶媒を減圧下留去した。残渣をシリカゲルクロマトグラフィー（シリカゲル:ＣｈｒｏｍａｔｏｒｅｘＮＨ、100−200ｍｅｓｈ、溶出溶媒:塩化メチレン／メタノール＝1／0〜50／1）により精製して標記化合物を淡黄色固体として2.13g（収率76％）得た。
核磁気共鳴スペクトル(400MHz, CD₃OD)， δ: 1.09(3H, s), 1.62-1.86(6H, m), 2.64(2H, t, J=7.1 Hz), 2.84-2.98(4H, m), 3.34(1H, d, J=10.8 Hz), 3.38(1H, d, J=10.8 Hz), 6.93(1H, d, J=3.7 Hz), 7.10-7.28(5H, m), 7.68(1H, d, J=3.7 Hz)。
マススペクトル(FAB)， m/z: 346 ((M + H)⁺)。
【０２２７】
(ｃ)
（2R）−ｔ−ブトキシカルボニルアミノ−2−メチル−4−[5−（5−フェニルペンタノイル）チオフェン−2−イル]ブタン−1−オール
実施例１(ｂ)で得られた（2R）−アミノ−2−メチル−4−[5−（5−フェニルペンタノイル）チオフェン−2−イル]ブタン−1−オール724mg（2.09mmol）を塩化メチレン8mLに溶解し、1規定水酸化ナトリウム水溶液8m及びジ−ｔ−ブチルジカルボネート684mg（3.13mmol）を加え、室温で2時間撹拌した。反応液を塩化メチレンで希釈し、水を加えて分液した。塩化メチレン層を水及び飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥後、減圧下溶媒を留去した。残渣をシリカゲルクロマトグラフィー（展開溶媒:ヘキサン／酢酸エチル＝3／2）により精製して標記化合物を白色固体として890mg（収率95％）得た。
核磁気共鳴スペクトル(400MHz, CDCl₃)， δ: 1.21(3H, s), 1.43(9H, s), 1.66-1.83(4H, m), 1.97-2.06(1H, m), 2.13-2.21(1H, m), 2.61-2.68(2H, m), 2.78-2.98(4H, m), 3.64-3.72(2H, m), 3.96(1H, brs), 4.63(1H, brs), 6.84(1H, d, J=3.9Hz), 7.13-7.30(5H, m), 7.51(1H, d, J=3.9Hz)。
マススペクトル(FAB)， m/z: 446 ((M + H)⁺)。
【０２２８】
(ｄ)
リン酸ビス−アリル−モノ−（2R）−ｔ−ブトキシカルボニルアミノ−2−メチル−4−[5−（5−フェニルペンタノイル）チオフェン−2−イル]ブチルエステル
実施例1(ｃ)で得られた（2R）−ｔ−ブトキシカルボニルアミノ−2−メチル−4−[5−（5−フェニルペンタノイル）チオフェン−2−イル]ブタン−1−オール777mg（1.74mmol）を塩化メチレン8mLに溶解し、テトラゾール820mg（11.7mmol）を加えた。氷冷下、ジアリルジイソプロピルホスホロアミダイト922μL（3.49mmol）を加えた。氷冷下5分撹拌後室温に戻し2時間撹拌した。氷冷下メタノール1mLを加え、5−6M ｔ−ブチルハイドロパーオキサイド−デカン溶液1.05mL（5.22mmol）をゆっくり加えた。氷冷下10分撹拌後、飽和亜硫酸ナトリウム水溶液10mLを加え、塩化メチレンで希釈し分液した。塩化メチレン層を水、飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥後、減圧下溶媒を留去した。残渣をシリカゲルクロマトグラフィー（展開溶媒：ヘキサン／酢酸エチル＝3／2）により精製して標記化合物を無色油状物として420mg（収率46％）得た。
【０２２９】
核磁気共鳴スペクトル(400MHz, CDCl₃)， δ: 1.32(3H, s), 1.44(9H, s), 1.66-1.82(4H, m), 1.88-1.98(1H, m), 2.21-2.33(1H, m), 2.63-2.68(2H, m), 2.82-2.87(4H, m), 3.98-4.04(1H, m), 4.15-4.21(1H, m), 4.53-4.59(4H, m), 4.64(1H, bRrs), 5.24-5.41(4H, m), 5.59-6.00(2H, m), 6.83(1H, d, J=3.7Hz), 7.14-7.30(5H, m),7.51(1H, d, J=3.7Hz)。
マススペクトル(FAB)， m/z: 606 ((M + H)⁺)。
【０２３０】
(ｅ)
リン酸モノ−（2R）−アミノ−2−メチル−4−[5−（5−フェニルペンタノイル）チオフェン−2−イル]ブチルエステル
実施例1(ｄ)で得られたリン酸ビス−アリル−モノ−（2R）−ｔ−ブトキシカルボニルアミノ−2−メチル−4−[5−（5−フェニルペンタノイル）チオフェン−2−イル]ブチルエステル400mg（0.66mmol）をアセトニトリル5mLに溶解し、テトラキス（トリフェニルホスフィン）パラジウム37mg（0.03mmol）を加えた。氷冷下ピロリジン135μL（1.62mmol）を加えた。氷冷下30分撹拌後、室温に戻し、1時間30分撹拌した。溶媒を減圧下留去し、分取ＨＰLＣ（カラム：ＩｎｅｒｔｓｉｌＯＤＳ−3 20×250mm、溶出溶媒：アセトニトリル／0.1％酢酸アンモニウム水溶液＝1／1、流速：10mL／分）にて精製した。精製物をエタノール2mLに溶解し、氷冷下4規定塩酸ジオキサン溶液を2mL加えた。氷冷下30分撹拌後、室温に戻し、4時間撹拌した。溶媒を減圧下留去し、メタノール−水より再結晶し、標記化合物を淡黄色結晶として115mg（収率51％）得た。
核磁気共鳴スペクトル(400MHz, DMSO-d₆)， δ: 1.22(3H, s), 1.52-1.65(4H, m), 1.83-2.05(2H, m), 2.52-2.63(2H, m), 2.81-2.97(4H, m), 3.71-3.88(2H, m), 6.98(1H, d, J=3.7Hz), 7.14-7.28(5H, m),7.74(1H, d, J=3.7Hz)。
マススペクトル(FAB)， m/z: 426 ((M + H)⁺)。
【０２３１】
（実施例２）
リン酸モノ−（2R）−アミノ−2−メチル−4−[5−（4−シクロヘキシルオキシブト−1−イニル）チオフェン−2−イル]ブチルエステル
【０２３２】
【化１３】

【０２３３】
(a)
（2R）−アリルオキシカルボニルアミノ−2−メチル−4−[5−（4−シクロヘキシルオキシブト−1−イニル）チオフェン−2−イル]ブタン−1−オール
参考例6で合成した（2R）−アミノ−2−メチル−4−[5−（4−シクロヘキシルオキシブト−1−イニル）チオフェン−2−イル]ブタン−1−オールマレイン酸塩500mg（1.11mmol）に1規定水酸化ナトリウム水溶液10mLを加え、塩化メチレンで抽出した。塩化メチレン層を無水硫酸ナトリウムで乾燥後、減圧下溶媒を留去した。得られた残渣を酢酸エチル8mL及び水8mLに溶解し、炭酸水素カリウム141mg（1.33mmol）及びクロロギ酸アリル133μL（1.33mmol）を加え、室温で30分撹拌した。反応液を水にあけ、酢酸エチルで抽出し、酢酸エチル層を飽和食塩水で洗浄した。酢酸エチル層を無水硫酸ナトリウムで乾燥後、減圧下溶媒を留去した。残渣をシリカゲルクロマトグラフィー（展開溶媒：ヘキサン／酢酸エチル＝2／1〜3／2）により精製して標記化合物を無色油状物として465mg（100％）得た。
【０２３４】
核磁気共鳴スペクトル(400MHz, CDCl₃)， δ: 1.15-1.35(8H, m), 1.50-1.60(1H, m), 1.70-1.80(2H, m), 1.88-2.03(3H, m), 2.08-2.18(1H, m), 2.67(2H, t, J=7.2Hz), 2.72-2.90(2H, m), 3.27-3.34(1H, m),3.47(1H, brs), 3.62-3.75(4H, m), 4.53(2H, d, J=5.7Hz), 4.82(1H, brs), 5.22-5.35(2H, m), 5.86-5.97(1H, m), 6.63(1H, d, J=3.6Hz), 6.93(1H, d, J=3.6Hz)。
マススペクトル(FAB)， m/z: 420 ((M + H)⁺)。
【０２３５】
(b)
リン酸モノ−（2R）−アミノ−2−メチル−4−[5−（4−シクロヘキシルオキシブト−1−イニル）チオフェン−2−イル]ブチルエステル
実施例2(a)で得られた（2R）−アリルオキシカルボニルアミノ−2−メチル−4−[5−（4−シクロヘキシルオキシブト−1−イニル）チオフェン−2−イル]ブタン−1−オール465mg（1.11mmol）を塩化メチレン10mLに溶解し、テトラゾール465mg（6.64mmol）を加え、氷冷下、ジアリルジイソプロピルホスホロアミダイト1.17mL（4.43mmol）を加えた。室温で1時間撹拌後、氷冷下5−6M ｔ−ブチルハイドロパーオキサイド−デカン溶液0.66mL（3.32mmol）をゆっくり加えた。氷冷下5分撹拌後、10％チオ硫酸ナトリウム水溶液10mLを加え、塩化メチレンで抽出した。塩化メチレン層を水及び飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥後、減圧下溶媒を留去した。残渣をシリカゲルクロマトグラフィー（展開溶媒：ヘキサン／酢酸エチル＝3／1〜3／2）により精製した。得られた精製物248mg（0.43mmol）をアセトニトリル5mLに溶解し、テトラキス（トリフェニルホスフィン）パラジウム25mg（0.02mmol）を加え、さらに氷冷下ピロリジン179μL（2.14mmol）を加え、室温で2時間撹拌した。析出した沈殿をろ取し、アセトニトリル及び0．1％酢酸アンモニウム水溶液の混合物（1：1）10mLを加えて加熱し、放置した。得られた沈殿をろ取し、乾燥し、標記化合物を白色結晶として35mg（8％）得た。
【０２３６】
核磁気共鳴スペクトル(400MHz, CD₃COOD)， δ: 1.15-1.40(5H, m), 1.43(3H, s), 1.49-1.57(1H, m), 1.70-1.80(2H, m), 1.90-1.98(2H, m), 2.01-2.22(2H, m), 2.68(2H, t, J=6.6Hz), 2.84-3.00(2H, m), 3.37-3.46(1H, m), 3.71(2H, t, J=6.6Hz), 4.08-4.16(2H, m), 6.73(1H, d, J=3.7Hz), 6.96(1H, d, J=3.7Hz)。
マススペクトル(FAB)， m/z: 414 ((M + H)^-)。
【０２３７】
（実施例３）
（3R）−アミノ−3−メチル−5−[5−（5−フェニルペンチル）チオフェン−2−イル]ペンチルホスホン酸
【０２３８】
【化１４】

【０２３９】
(ａ)
（2R）−t−ブトキシカルボニルアミノ−2−メチル−4−[5−（5−フェニルペンチル）チオフェン−2−イル]−1−ブタナール
参考例８で得られた（2R）−アミノ−2−メチル−4−[5−（5−フェニルペンチル）チオフェン−2−イル]ブタン−1−オール1.26ｇ(3.97mmol)を塩化メチレン25mLに溶解させ、氷冷攪拌下、ジ−t−ブチルジカーボネート1.04g(4.76mmol)及びトリエチルアミン0.55mL(3.97mmol)を加え、室温にて１６時間攪拌した。反応終了後、反応液に水を加え酢酸エチルで抽出した。有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥後、減圧下溶媒を留去した。残渣をシリカゲルクロマトグラフィー（展開溶媒：ヘキサン／酢酸エチル＝１／１）により精製して、Ｎ−ｔ−ブトキシカルボニル体（N-Boc体）を1.12g(収率70%)得た。N-Boc体150mg（0.35mmol）を塩化メチレン7.5 mLに溶解させ、氷冷攪拌下、1,1,1−トリアセトキシ−1,1−ジヒドロ−1,2−ベンズイオドキソール−3(1H)−オン（Dess-Martin試薬）222mg(0.52mmol)を加え、室温にて１．５時間攪拌した。反応終了後、反応液にチオ硫酸ナトリウム水溶液を加え、室温にて３０分攪拌し、水を加えて酢酸エチルで抽出した。有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥後、減圧下溶媒を留去した。残渣をシリカゲルクロマトグラフィー（展開溶媒：ヘキサン／酢酸エチル＝５／１）により精製して標記化合物を無色シロップとして150mg(収率100%)得た。
【０２４０】
核磁気共鳴スペクトル(400MHz, CDCl₃)， δ: 9.33 (s, 1H), 7.42-7.23 (m, 2H), 7.22-7.17 (m, 3H), 6.54 (d, 1H, J = 3.66 Hz), 6.53 (d, 1H, J = 3.66 Hz), 5.25-5.11 ( brs, 1H), 2.73 (t, 2H, J = 7.70Hz), 2.41-2.26(m, 1H), 2.12-2.00(m, 1H), 2.71-1.58(m, 4H), 1.45 (s, 9H), 1.51-1.32 (m, 2H), 1.38 (s, 3H)。
赤外吸収スペクトル，νmax cm^-1 (CHCl3)：3443, 3413, 2981, 2934, 2858, 1708, 1495, 1453, 1369, 1253, 1164, 1074。
マススペクトル(FAB)， m/z: 430 ((M + H)^-)。
【０２４１】
(b)
（3R）−t−ブトキシカルボニルアミノ−3−メチル−5−[5−（5−フェニルペンチル）チオフェン−2−イル]−1−ペンテニルホスホン酸ジエチルエステルテトラエチルメチレンジホスホネート0.56mL(2.26mmol)をベンゼン15mLに溶解させ、氷冷攪拌下、60%水素化ナトリウム90mg(2.17mmol)を加えた。その後、室温にて３０分攪拌した後、実施例3(a)で得られた（2R）−t−ブトキシカルボニルアミノ−2−メチル−4−[5−（5−フェニルペンチル）チオフェン−2−イル]−1−ブタナール194mg(0.45mmol)を加え、室温にて２時間攪拌した。反応終了後、反応液に塩化アンモニウム水溶液を加え、有機層を酢酸エチルで抽出した。有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥後、減圧下溶媒を留去した。残渣をシリカゲルクロマトグラフィー（展開溶媒：ヘキサン／酢酸エチル＝１／１）により精製して標記化合物を無色シロップとして227mg(収率89％)得た。
【０２４２】
核磁気共鳴スペクトル（400MHz、CDCl3），δ： 7.29-7.26 (m, 2H), 7.19-7.16 (m, 3H), 6.76 (dd, 1H, J = 17.6, 22.7 Hz), 6.56-6.53(ｍ, 2H,), 5.70 (dd, 2H, J = 17.6, 17.8 Hz) 4.65-4.55 (br s, 1H), 4.18-4.02 (m, 4H), 2.80-2.67 (m, 4H), 2.61(t, 2H, J = 7.69 Hz), 2.23-2.21 (m, 1H), 2.08-1.90 (m, 1H), 1.73-1.55 (m, 4H), 1.43 (s, 9H), 1.34(t, 6H, J = 6.97 Hz), 1.26 (t, 3H, J = 6.97 Hz)。
赤外吸収スペクトル， ν_max cm^-1 (CDCl3)： 3443, 2982, 2933, 2858, 2244, 1718, 1495, 1454, 1368, 1245, 1166, 1057, 1029。
マススペクトル(FAB)， m/z: 564 ((M + H)^-)。
【０２４３】
(c)
（3R）−t−ブトキシカルボニルアミノ−3−メチル−5−[5−（5−フェニルペンチル）チオフェン−2−イル]ペンチルホスホン酸ジエチルエステル
実施例3(b)で得られた（3R）−t−ブトキシカルボニルアミノ−3−メチル−5−[5−（5−フェニルペンチル）チオフェン−2−イル]−1−ペンテニルホスホン酸ジエチルエステル100mg(0.18mmol)をエタノール4mLに溶解させ、室温攪拌下、クロロトリス（トリフェニルホスフィン）ロジウム82mgを加え、水素雰囲気下、70℃にて５時間攪拌した。反応終了後、減圧下溶媒を留去した。残渣をシリカゲルクロマトグラフィー（展開溶媒：ヘキサン／酢酸エチル＝１／３）により精製して、標記化合物を無色シロップとして62mg(収率62%)得た。
【０２４４】
核磁気共鳴スペクトル（400MHz、CDCl3），δ： 7.31-7.23 (m, 2H), 7.22-7.13 (m, 3H), 6.56 (d, 1H, J = 2.93 Hz), 6.53 (d, 1H, J = 2.93 Hz), 4.42-4.23 ( brs, 1H), 4.18-4.01 (m, 4H), 2.80-2.65 (m, 4H), 2.61(t, 2H，J = 7.70 Hz), 2.22-2.08(m, 2H), 1.91-1.53(m, 10H), 1.43 (s, 9H), 1.33 (t, 6H, J = 7.33 Hz), 1.21 (s, 3H)。
赤外吸収スペクトル，ν_max cm^-1 (CHCl3)： 3443, 2984, 2935, 1714, 1498, 1454, 1392, 1368, 1165, 1063, 1031, 967。
マススペクトル(FAB)， m/z: 566 ((M + H)^-)。
【０２４５】
(d)
（3R）−アミノ−3−メチル−5−[5−（5−フェニルペンチル）チオフェン−2−イル]ペンチルホスホン酸
実施例３(c)で得られた（3R）−t−ブトキシカルボニルアミノ−3−メチル−5−[5−（5−フェニルペンチル）チオフェン−2−イル]ペンチルホスホン酸ジエチルエステル63mg(0.11mmol)に４規定塩酸ジオキサン溶液3mLと水１mLを加え、80℃にて８時間攪拌した。反応終了後、減圧下溶媒を留去した。残渣をメタノール0.5mLに溶解し、水5mL加え、再結晶を行い、表記化合物28mg(収率62%)を得た。
【０２４６】
核磁気共鳴スペクトル（400MHz、CD3OD），δ： 7.25-7.18 (m, 2H), 7.18-7.19 (m, 3H), 6.64 (d, 1H, J = 3.30 Hz), 6.56 (d, 1H, J = 3.30 Hz), 2.83 (t, 2H, J = 8．79Hz), 2.74(t, 2H, J = 7.33 Hz), 2.59(t, 2H, J = 7.33 Hz), 2.05-1.85(m, 4H), 1.72-1.56 (m, 6H), 1.44-1.31 (m, 5H)。
赤外吸収スペクトル，ν_max cm^-1 (KBr)： 2930, 1632, 1552, 1496, 1453, 1389, 1180, 1048, 946, 800, 746, 698。
マススペクトル(FAB)， m/z: 408 ((M + H)^-)。
（実施例４）
（3R）−アミノ−3−メチル−5−[5−（5−フェニルペンタノイル）チオフェン−2−イル]ペンチルホスホン酸
【０２４７】
【化１５】

【０２４８】
(ａ)
（2R）−t−ブトキシカルボニルアミノ−2−メチル−4−[5−（5−フェニルペンタノイル）チオフェン−2−イル]−1−ブタナール
参考例１０で得られた（2R）−アミノ−2−メチル−4−[5−（5−フェニルペンタノイル）チオフェン−2−イル]ブタン−1−オール637mg (1.84mmol)を塩化メチレン(18mL)に溶解し、ジ−t−ブチルジカルボネート492mg (2.26mmol)およびトリエチルアミン5.61mL(6.80mmol)を加え、室温で２０時間攪拌した。減圧下濃縮し、反応液に水を加え、酢酸エチルで抽出し、酢酸エチル層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥した。ろ過後、減圧下溶媒を留去し、残渣をシリカゲルクロマトグラフィー(溶出溶媒：ヘキサン／酢酸エチル＝３／２)により精製して、N-Boc体［（2R）−t−ブトキシカルボニルアミノ−2−メチル−4−[5−（5−フェニルペンタノイル）チオフェン−2−イル]ブタン−1−オール］678mg(83%)を得た。
【０２４９】
得られたN-Boc体673mg(1.51mmol)を塩化メチレン(15mL)に溶解し、1,1,1−トリアセトキシ−1,1−ジヒドロ−1,2−ベンズイオドキソール−3(1H)−オン（Dess-Martin試薬）965mg(2.28mmol)を加え、窒素雰囲気下、室温で１時間攪拌した。減圧下濃縮し、反応液に１０％チオ硫酸ナトリウム水溶液を加え、過剰の試薬を分解した後、塩化メチレンで抽出し、塩化メチレン層を飽和重曹水および飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥した。ろ過後、減圧下溶媒を留去し、残渣をシリカゲルクロマトグラフィー(溶出溶媒：ヘキサン／酢酸エチル＝３／１)により精製して、標記化合物677mg(100%)を得た。
【０２５０】
核磁気共鳴スペクトル（400MHz、CDCl3），δ : 9.35 (s, 1H), 7.49 (d, 1H, J = 4.4 Hz), 7.29-7.25 (m, 3H), 7.18-7.15 (m, 2H), 6.80 (d, 1H, J = 4.4 Hz), 5.17 (br s, 1H), 2.87-2.79 (m, 1H), 2.84 (t, 2H, J = 6.8 Hz), 2.75-2.68 (m, 1H), 2.65 (t, 2H, J = 6.8 Hz), 2.40 (m, 1H), 2.15 (ddd, 1H, J = 5.9 Hz, 10.8 Hz, 14.3 Hz), 1.82-1.66 (m, 4H), 1.45 (s, 9H), 1.38 (s, 3H)。
マススペクトル（FAB⁺），m/z：444((M+H)⁺)。
【０２５１】
(b)
（3R）−t−ブトキシカルボニルアミノ−3−メチル−5−[5−（5−フェニルペンタノイル）チオフェン−2−イル]−1−ペンテニルホスホン酸ジエチルエステル
60%水素化ナトリウム70.1mg(1.75mmol)をテトラヒドロフラン(3mL)に懸濁し、氷冷下、テトラエチルメチレンジホスホネート0.43mL(1.73mmol)を５分間要して加え、その後室温にて１時間攪拌した。次いで、実施例4(a)得られた（2R）−t−ブトキシカルボニルアミノ−2−メチル−4−[5−（5−フェニルペンタノイル）チオフェン−2−イル]−1−ブタナール508mg(1.13mmol)をテトラヒドロフラン(7mL)に溶解した溶液を氷冷下、５分間要して加え、同温度にて１０分間攪拌した。反応液に酢酸0.10mL(1.75mmol)を加えて中和した後、減圧下濃縮し、反応液に水を加え、酢酸エチルで抽出し、酢酸エチル層を水および飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥した。ろ過した後、減圧下溶媒を留去し、残渣をシリカゲルクロマトグラフィー(溶出溶媒：酢酸エチル)により精製して、標記化合物614mg(94%)を得た。
【０２５２】
核磁気共鳴スペクトル（400MHz、CDCl3），δ : 7.50 (d, 1H, J = 3.9 Hz), 7.29-7.25 (m, 3H), 7.19-7.16 (m, 2H), 6.81 (d, 1H, J = 3.9 Hz), 6.76 (dd, 1H, J = 17.8 Hz, 22.5 Hz), 5.72 (dd, 1H, J = 17.8 Hz, 17.8 Hz), 4.58 (br s, 1H), 4.15-4.02 (m, 4H), 2.86-2.77 (m, 4H), 2.65 (t, 2H, J = 7.1 Hz), 2.33-2.24 (m, 1H), 2.06 (br s, 1H), 1.82-1.67 (m, 4H), 1.43 (s, 9H), 1.41 (s, 3H), 1.33 (t, 3H, J = 6.8 Hz)。
マススペクトル（FAB⁺），m/z：580((M+H)⁺)。
【０２５３】
(c)
（3R）−t−ブトキシカルボニルアミノ−3−メチル−5−[5−（5−フェニルペンタノイル）チオフェン−2−イル]ペンチルホスホン酸ジエチルエステル
10%パラジウム−炭素（50%含水）95.3mgをメタノール(1mL)に懸濁し、実施例4(b)で得られた（3R）−t−ブトキシカルボニルアミノ−3−メチル−5−[5−（5−フェニルペンタノイル）チオフェン−2−イル]−1−ペンテニルホスホン酸ジエチルエステル508mg(0.88mmol)をメタノール(8mL)に溶解した溶液を加え、水素雰囲気下、５０℃で４０時間攪拌した。反応液中のパラジウム−炭素をセライトろ過した後、ろ液を減圧下留去した。残渣をシリカゲルクロマトグラフィー(溶出溶媒：ヘキサン／酢酸エチル＝１／３〜酢酸エチル)により精製して、標記化合物408mg(収率80%)を得た。
【０２５４】
核磁気共鳴スペクトル（400MHz、CDCl3），δ : 7.51 (d, 1H, J = 3.6 Hz), 7.29-7.25 (m, 3H), 7.19-7.15 (m, 2H), 6.81 (d, 1H, J = 3.6 Hz), 4.37 (br s, 1H), 4.15-4.05 (m, 4H), 2.86-2.80 (m, 4H), 2.65 (t, 2H, J = 7.1 Hz), 2.30-2.12 (m, 2H), 1.94-1.86 (m, 1H), 1.82-1.66 (m, 7H), 1.43 (s, 9H), 1.33 (t, 3H, J = 6.8 Hz) 1.21 (s, 3H)。
マススペクトル（FAB⁺），m/z：580((M+H)⁺)。
【０２５５】
(d)
（3R）−アミノ−3−メチル−5−[5−（5−フェニルペンタノイル）チオフェン−2−イル]ペンチルホスホン酸
実施例４(c)で得られた（3R）−t−ブトキシカルボニルアミノ−3−メチル−5−[5−（5−フェニルペンタノイル）チオフェン−2−イル]ペンチルホスホン酸
ジエチルエステル130mg(0.22mmol)を塩化メチレン(2.2mL)に懸濁し、臭化トリメチルシラン0.30mL(0.22mmol)を加え、窒素雰囲気下、室温で４時間撹拌した。減圧下溶媒を留去した後、残渣に含水エタノールを加えて希釈し、これにアンモア水溶液および酢酸を加えてpH３として結晶を析出させた。析出結晶をろ取し、水およびエタノールで洗浄後、乾燥して、標記化合物82.1mg(収率85%)を得た。
【０２５６】
核磁気共鳴スペクトル（400MHz、CD₃CO₂D），δ ： 7.67 (d, 1H, J = 3.7 Hz), 7.26-7.22 (m, 2H), 7.18-7.12 (m, 3H), 6.97 (d, 1H, J = 3.7 Hz), 2.98 (t, 2H, J = 8.8 Hz), 2.93 (t, 2H, J = 7.3 Hz), 2.64 (t, 2H, J = 7.3 Hz), 2.23-2.07 (m, 4H), 2.06-1.93 (m, 2H), 1.80-1.65 (m, 4H), 1.46 (s, 3H)。
マススペクトル（FAB⁺），m/z：424((M+H)⁺)。
【０２５７】
（参考例１）
(4R)-メチル-4-[2-(チオフェン-2-イル)エチル]オキサゾリジン-2-オン
(a)
(2R)-t-ブトキシカルボニルアミノ-3-ヘキサノイルオキシ-2-メチル-1-プロパノール
2-t-ブトキシカルボニルアミノ-2-メチル-1,3-プロパンジオール20.0 g (97.4 mmol)をジイソプロピルエーテル200 ml中に懸濁し、ヘキサン酸ビニルエステル16.3 ml (0.10 mol)及びリパーゼ[Immobilized lipase from Pseudomonas sp. (TOYOBO; 0.67U/mg)] 0.8gを加え、室温で2時間激しく攪拌した。反応液を濾過後、濾液を減圧下留去した。得られた残渣をシリカゲルカラムクロマトグラフィー(溶出溶媒：ヘキサン／酢酸エチル＝10／1〜2／1)により精製して、標記化合物25.0 g (収率85 %)を無色油状物として得た。
【０２５８】
得られた標記化合物の光学純度は、分析用光学活性HPLCカラム（ChiralCel OF(ダイセル)、(0.46 cm x 25 cm)、溶出溶媒：ヘキサン／2-プロパノール＝70／30、流速：0.5 ml/min）で決定した。
【０２５９】
先に溶出されるもの（保持時間：8.2分）が2S体であり、後から溶出されるもの（保持時間：10.5分）が2R体であり、この反応における光学純度は85 %eeであることを確認した。
[α]^D ₂₅ -8.5 (c 1.86, CHCl₃)
核磁気共鳴スペクトル（400MHz、CDCl₃），δ: 4.86 (s, 1H), 4.25 (d, 1H, J = 11.2 Hz), 4.19 (d, 1H, J = 11.2 Hz), 3.86 (brs, 1H), 3.70-3.55 (m, 2H), 2.36 (t, 2H, J = 7.4 Hz), 1.68-1.58 (m, 2H), 1.44 (s, 9H), 1.40-1.30 (m, 4H), 1.25 (s, 3H), 0.90 (t, 3H, J = 7.0 Hz)。
赤外吸収スペクトル，ν_max cm^-1 (液状フィルム) : 3415, 3380, 2961, 2935, 2874, 1721, 1505, 1458, 1392, 1368, 1293, 1248, 1168, 1076。
マススペクトル（FAB），m/z：304((M+H)⁺)。
【０２６０】
(b)
(2R)-t-ブトキシカルボニルアミノ-3-ヘキサノイルオキシ-2-メチル-1-プロパナール
参考例1（a）で得られた(2R)-t-ブトキシカルボニルアミノ-3-ヘキサノイルオキシ-2-メチル-1-プロパノール30.7 g (0.10 mol)を塩化メチレン600 mlに溶解し、モレキュラーシーブ4Å 220 g及び塩化クロム酸ピリジニウム43.6 g (0.20 mol)を氷冷下加え、その後、室温で2時間攪拌した。反応液をエーテルで希釈後、濾過した。濾液を減圧下留去し、残渣をシリカゲルカラムクロマトグラフィー(溶出溶媒：ヘキサン／酢酸エチル＝10／1〜5／1)により精製して、標記化合物28.8 g (収率95 %)を無色油状物として得た。
核磁気共鳴スペクトル（400MHz、CDCl₃），δ: 9.45 (s, 1H), 5.26 (brs, 1H), 4.44 (d, 1H, J = 11.2 Hz), 4.32 (d, 1H, J = 11.2 Hz), 2.32 (t, 2H, J = 7.6 Hz), 1.70-1.55 (m, 2H), 1.45 (s, 9H), 1.38 (s, 3H), 1.40-1.25 (m, 4H), 0.90 (t, 3H, J = 7.0 Hz)。
赤外吸収スペクトル，ν_max cm^-1 (液状フィルム) : 3367, 2961, 2935, 2874, 1742, 1707, 1509, 1458, 1392, 1369, 1290, 1274, 1254, 1166, 1100, 1078。
マススペクトル（FAB），m/z：302((M+H)⁺)。
【０２６１】
（c）
(2R)-t-ブトキシカルボニルアミノ-1-ヘキサノイルオキシ-2-メチル-4-(チオフェン-2-イル)-3-ブテン
臭化 2-チエニルメチルトリフェニルホスホニウム塩67.1 g (0.15 mol)をテトラヒドロフラン750 mlに懸濁し、そこにt-ブトキシカリウム17.2 g (0.15 mol)を加え、室温で、窒素雰囲気下20分間撹拌した。反応液へ、テトラヒドロフラン250 mlに溶解した参考例1（b）で得られた(2R)-t-ブトキシカルボニルアミノ-3-ヘキサノイルオキシ-2-メチル-1-プロパナール23.0 g (76.4 mmol)を氷冷下、滴下し、滴下終了後、氷冷下で30分攪拌した。その後、反応液に水を加え、酢酸エチルで抽出し、酢酸エチル層を飽和食塩水で洗浄した。酢酸エチル層を無水硫酸ナトリウムで乾燥後、減圧下溶媒を留去した。残渣をシリカゲルカラムクロマトグラフィー(溶出溶媒：ヘキサン／酢酸エチル＝20／1)により精製して、標記化合物27.8 g (収率96 %)を無色油状物として得た。
核磁気共鳴スペクトル（400MHz、CDCl₃），δ: 7.32-7.26, 7.16-7.14 (m, 計1H), 7.04-7.01, 7.01-6.93 (m, 計2H), 6.63 (d, 0.5 H, J = 16.0 Hz), 6.60 (d, 0.5 H, J = 13.6 Hz), 6.10 (d, 0.5 H, J = 16.0 Hz), 5.58 (d, 0.5 H, J = 13.6 Hz), 4.94, 4.93 (brs, 計1H), 4.40-4.10 (m, 2H), 2.34 (t, 2H, J = 7.4 Hz), 1.70-1.55 (m, 2H), 1.57, 1.50, 1.44 (s, 計9H), 1.40-1.25 (m, 7H), 0.88 (t, 3H, J = 7.0 Hz)。
赤外吸収スペクトル，ν_max cm^-1 (液状フィルム) : 3370, 2961, 2933, 1725, 1495, 1456, 1391, 1367, 1247, 1167, 1109, 1100, 1072, 697。
マススペクトル（FAB），m/z：381(M⁺)。
【０２６２】
（d）
(4R)-メチル-4-[2-(チオフェン-2-イル)エテニル]オキサゾリジン-2-オン
参考例1（c）で得られた(2R)-t-ブトキシカルボニルアミノ-1-ヘキサノイルオキシ-2-メチル-4-(チオフェン-2-イル)-3-ブテン40.5 g (0.11 mol)をテトラヒドロフラン150 ml及びメタノール150 mlに溶解し、そこに1規定水酸化ナトリウム水溶液530 mlを氷冷下加え、氷冷下で30分及び室温で1時間攪拌した。反応液を減圧下濃縮後、水を加え、塩化メチレンで抽出し、塩化メチレン層を飽和食塩水で洗浄した。塩化メチレン層を無水硫酸ナトリウムで乾燥後、減圧下溶媒を留去し、粗生成物35.0 gを得た。この粗生成物をテトラヒドロフラン300 mlに溶解し、t-ブトキシカリウム17.8 g (0.16 mol)を氷冷下加え、氷冷下で10分及び室温で40分攪拌した。反応液に水を加え、酢酸エチルで抽出し、酢酸エチル層を飽和食塩水で洗浄した。酢酸エチル層を無水硫酸ナトリウムで乾燥後、減圧下溶媒を留去した。残渣をシリカゲルカラムクロマトグラフィー(溶出溶媒：ヘキサン／酢酸エチル＝3／1〜1／1)により精製して、標記化合物18.0 g (収率81 %)を白色固体として得た。
核磁気共鳴スペクトル（400MHz、CDCl₃），δ: 7.34 (d, 0.5H, J = 5.1 Hz), 7.19 (d, 0.5H, J=5.0Hz), 7.07-6.91 (m, 2H), 6.74 (d, 0.5H, J=16.0Hz), 6.59 (d, 0.5H, J=12.5), 6.17 (brs, 1H), 6.06 (d, 0.5H, J=16.0Hz), 5.65 (d, 0.5H, J=12.5Hz), 4.41 (d, 0.5H, J=8.6Hz), 4.31-4.16 (m, 1.5H), 1.60 (s, 1.5H), 1.55 (s, 1.5H)。
赤外吸収スペクトル，ν_max cm^-1 (KBr) : 3275, 3110, 2974, 1752, 1391, 1376, 1281, 1169, 1039, 960, 704。
マススペクトル（FAB），m/z：209(M⁺)。
【０２６３】
（e）
(4R)-メチル-4-[2-(チオフェン-2-イル)エチル]オキサゾリジン-2-オン
参考例1（d）で得られた(4R)-メチル-4-[2-(チオフェン-2-イル)エテニル]オキサゾリジン-2-オン18.0 g (86.0 mmol)をメタノール150 mlに溶解し、10%パラジウム−炭素4.5 gを加え、水素雰囲気下、10時間室温で攪拌した。反応液中のパラジウム−炭素を、シリカゲルを薄く敷いた桐山ロートを用いて濾過し、濾液を減圧下留去した。得られた固体をジエチルエーテルで洗浄後、乾燥して、標記化合物16.5 g (収率91 %)を白色固体として得た。
【０２６４】
得られた標記化合物の光学純度は、分析用光学活性HPLCカラム（ChiralCel OD-H(ダイセル)、(0.46 cm x 25 cm)、溶出溶媒：ヘキサン／2-プロパノール＝60／40、流速：0.5 ml／min）を用いて決定した。
【０２６５】
先に溶出されるもの（保持時間：16.8分）が2S体であり、後から溶出されるもの（保持時間：17.6分）が2R体であり、この反応における光学純度は85 %eeであることを確認した。
[α]^D ₂₅ +5.1 (c 2.4, CHCl₃)
核磁気共鳴スペクトル（400MHz、CDCl₃），δ: 7.15 (d, 1H, J = 5.2 Hz), 6.93 (dd, 1H, J = 5.2, 3.6 Hz), 6.81 (d, 1H, J = 3.6 Hz), 5.39 (brs, 1H), 4.19 (d, 1H, J = 8.4 Hz), 4.08 (d, 1H, J = 8.4 Hz), 3.00-2.84 (m, 2H), 2.08-1.92 (m, 2H), 1.42 (s, 3H)。
赤外吸収スペクトル，ν_max cm^-1 (KBr) : 3283, 1770, 1399, 1244, 1043, 941, 846, 775, 706, 691。
マススペクトル（EI），m/z：211(M⁺)。
【０２６６】
この光学純度85 %eeの(4R)-メチル-4-[2-(チオフェン-2-イル)エチル]オキサゾリジン-2-オン11 gに酢酸エチル25 mlとヘキサン5.0 mlを加えて、加熱溶解した後、室温で2時間放置した。析出した白色結晶を濾取し、乾燥を行い、光学純度99 %eeの標記化合物を4.0 g得た。
[α]^D ₂₅ +7.8 (c 2.0, CHCl₃)。
【０２６７】
（参考例２）
酢酸（2R）−アセチルアミノ−2−メチル−4−（5−ブロモチオフェン−2−イル）ブチルエステル
(a)
（2R）−アミノ−2−メチル−4−チオフェン−2−イルブタン−1−オール 1／2Ｄ−（−）−酒石酸塩
参考例1で得られた85%eeの（4R）−メチル−4−[2−（チオフェン−2−イル）エチル]オキサゾリジン−2−オン7.30g（34.6mmol）をテトラヒドロフラン35ml及びメタノール70mlに溶解し、氷冷下、5規定水酸化カリウム水溶液70mlを加え、80℃で2日間攪拌した。反応液に塩化メチレンを加え、水で洗浄した。塩化メチレン層を無水硫酸マグネシウムで乾燥し、溶媒を減圧下留去した。得られた残渣6.20gをエタノール60mlに溶解し、D-(-)-酒石酸5.19g（34.6 mmol）のエタノール50ml溶液を加え、析出した沈殿を濾取して、粗製の標記化合物7.56gを得た。得られた粗製の目的化合物7.54gをエタノール75ml及び水50mlを用いて再結晶を行い、標記化合物5.89g（98%ee）を得た。再度、得られた目的化合物5.88gをエタノール60ml及び水54mlを用いて再結晶を行い、標記化合物5.11g（収率57％、99.7%ee）を得た。
赤外吸収スペクトル,ν_max cm^-1 (KBr)：3400, 3218, 3126, 2937, 2596, 1599, 1530, 1400, 1124, 1077, 715。
元素分析値；（C₉H₁₅NOS・0.5C₄H₄O₆として％）
計算値：C,50.95; H,6.61; N,5.40; S,12.36
実測値：C,50.68; H,6.91; N,5.38; S,12.48
[α]_D ²⁴ -14 (c 1.00, H₂O)。
【０２６８】
(b)
酢酸（2R）−アセチルアミノ−2−メチル−4−（チオフェン−2−イル）ブチルエステル
参考例2(a)で得られた（2R）−アミノ−2−メチル−4−チオフェン−2−イルブタン−1−オール 1／2 D-(-)-酒石酸塩5.11g（19.6mmol）に、氷冷下、1規定水酸化ナトリウム水溶液30mlを加え、フリー体にした後、塩化メチレンで抽出した。塩化メチレン層を無水硫酸ナトリウムで乾燥後、減圧下溶媒を留去することにより、（2R）−アミノ−2−メチル−4−チオフェン−2−イルブタン−1−オール3.55g（収率98％）を得た。得られたフリー体1.51g（8.15 mmol）にピリジン30mlを加え、そこに、氷冷下、無水酢酸1.95ml（20.7 mmol）、4−（ジメチルアミノ）ピリジン200mg（1.64 mmol）を加えた。窒素雰囲気下、室温で、2時間半攪拌した。反応液を氷冷下、1規定塩酸150mlにあけ、酢酸エチルで抽出し、酢酸エチル層を1規定塩酸及び飽和食塩水で順次洗浄した。酢酸エチル層を無水硫酸ナトリウムで乾燥後、減圧下溶媒を留去した。残渣をシリカゲルクロマトグラフィー（溶出溶媒：ヘキサン／酢酸エチル＝3／1〜1／2）により精製し、標記化合物2.15g（収率98％）を得た。
核磁気共鳴スペクトル（400MHz, CDCl₃），δ： 1.37 (3H, s), 1.93 (3H, s), 1.94-2.10 (1H, m), 2.10 (3H,s), 2.24-2.38 (1H, m), 2.85 (2H, t, J=8.0 Hz), 4.18 (1H, d, J=11.6 Hz), 4.32 (1H, d, J=11.6 Hz), 5.39 (1H, brs), 6.81 (1H, dd, J=1.2, 3.6 Hz), 6.92 (1H, dd, J=3.6, 5.2 Hz), 7.12 (1H, dd, J=1.2, 5.2 Hz)。
赤外吸収スペクトル，ν_max cm^-1 (KBr): 3265, 3079, 2933, 2862, 1735, 1638, 1559, 1472, 1441, 1374, 1318, 1241, 1179, 1039, 701, 616。
【０２６９】
(c)
酢酸（2R）−アセチルアミノ−2−メチル−4−（5−ブロモチオフェン−2−イル）ブチルエステル
参考例2(b)で得られた酢酸（2R）−アセチルアミノ−2−メチル−4−（チオフェン−2−イル）ブチルエステル1.81g（6.70 mmol）をジメチルホルムアミド20mlに溶解させ、氷冷下、Ｎ-ブロモスクシンイミド1.27g（7.11 mmol）を加え、窒素雰囲気下、氷冷下で10分間及び室温で一昼夜攪拌した。反応液を水にあけ、酢酸エチルで抽出し、酢酸エチル層を飽和食塩水で洗浄した。酢酸エチル層を無水硫酸ナトリウムで乾燥後、溶媒を減圧下留去した。残渣をシリカゲルクロマトグラフィー（溶出溶媒：ヘキサン／酢酸エチル＝3／1〜1／2）により精製を行ない、標記化合物2.32g（収率99％）を得た。
核磁気共鳴スペクトル（400MHz, CDCl₃），δ： 1.35 (3H, s), 1.95 (3H, s), 1.95-2.08 (1H, m), 2.10 (3H,s), 2.24-2.37 (1H, m), 2.76 (2H, t, J=8.4 Hz), 4.15 (1H, d, J=11.2 Hz), 4.30 (1H, d, J=11.2 Hz), 5.39 (1H, brs), 6.57 (1H, d, J=3.6 Hz), 6.84 (1H, d, J=3.6 Hz)。
赤外吸収スペクトル，ν_max cm^-1 (液状フィルム) ： 3300, 3076, 2980, 2937, 1740, 1657, 1544, 1466, 1446, 1373, 1242, 1045, 794, 604。
【０２７０】
（参考例３）
5−（4−フルオロフェニル）ペント-1-イン
水素化ナトリウム2.11g（48.4mmol）を無水テトラヒドロフラン60ml中に懸濁させ、氷冷下、ジエチルホスホノ酢酸エチルエステル10.84g（48.4 mmol）を滴下し、10分間撹拌した。次いで4−フルオロベンズアルデヒド5.00g（40.3 mmol）を無水テトラヒドロフラン60mlに溶解した溶液を同温にて滴下した。反応液を同温度で3時間撹拌した後、氷水中150mlに注ぎ、酢酸エチルで抽出した。有機層を無水硫酸マグネシウムで乾燥後、溶媒を減圧留去し、残渣をフラッシュシリカゲルカラムクロマトグラフィー（溶出溶媒：ヘキサン／酢酸エチル＝10／1〜3／1）にて精製を行い、4−フルオロ桂皮酸エチルエステルを無色油状物として、6.69g（収率86％）得た。
【０２７１】
このエステル6.52g（33.6 mmol）を酢酸エチル100ml中に溶解し、5％ロジウム/アルミナ1.30gを加え、水素雰囲気下、室温にて8時間撹拌した。反応混合物をセライト濾過し、濾液を減圧濃縮し、残渣を無水テトラヒドロフラン30ml中に溶解した。この溶液を氷冷下、水素化アルミニウムリチウム1.26g（33.2 mmol）を無水テトラヒドロフラン60mlに懸濁させたものに滴下した。反応混合物を同温にて30分間撹拌後、飽和硫酸ナトリウム水溶液を加え、さらに室温で10分間撹拌した。混合物をセライト濾過し、濾液を酢酸エチルで抽出した。有機層を飽和食塩水で洗浄後、無水硫酸マグネシウムで乾燥した。溶媒を減圧留去し、残渣をフラッシュシリカゲルカラムクロマトグラフィー（溶出溶媒：ヘキサン／酢酸エチル＝5／1〜1／1）にて精製を行い、4−フルオロフェニルプロパン−1−オールを無色油状物として、4.86g（収率95％）得た。
【０２７２】
得られた4−フルオロフェニルプロパン−1−オール4.83g（31.3 mmol）を塩化メチレン50ml中に溶解し、氷冷下、トリエチルアミン6.55ml（47.0 mmol）及びメタンスルホニルクロリド2.91ml（37.6 mmol）を加え、窒素雰囲気下、同温度で30分間撹拌した。反応混合物を塩化メチレン50mlで希釈し、氷冷した10％塩酸及び飽和食塩水で順次洗浄後、硫酸マグネシウムで乾燥した。溶媒を減圧留去し、残渣をアセトン100ml中に溶解した。次いで沃化ナトリウム9.39g（62.6 mmol）を加え、窒素雰囲気下、50℃にて2時間撹拌した。反応混合物を酢酸エチル250mlで希釈後、10％チオ硫酸ナトリウム水溶液及び飽和食塩水で順次洗浄後、無水硫酸マグネシウムで乾燥した。溶媒を減圧留去し、残渣をフラッシュシリカゲルカラムクロマトグラフィー（溶出溶媒：ヘキサン／酢酸エチル＝5／1〜2／1）にて精製を行い、4−フルオロフェニル−1−ヨードプロパンを淡黄色油状物として、7.12g（収率86％）得た。
【０２７３】
ヘキサメチルホスホラミド20ml中にナトリウムアセチリド（18％キシレン懸濁液）50mlを加え、氷冷下、先に得られた4−フルオロフェニル−1−ヨードプロパン7.00g（26.5 mmol）を無水ジメチルホルムアミド20mlに溶解した溶液を加えた。反応混合物を室温にて、2時間撹拌した。氷冷下に氷水を注意深く注ぎ、混合物を酢酸エチルで抽出した。有機層を飽和食塩水で洗浄後、無水硫酸マグネシウムで乾燥した。溶媒を減圧留去し、残渣をフラッシュシリカゲルカラムクロマトグラフィー（溶出溶媒：ヘキサン）にて精製を行い、標記化合物を無色油状物として、2.67g（収率62％）得た。
核磁気共鳴スペクトル（400MHz, CDCl₃），δ： 1.82 (2H, m), 1.99 (1H, t, J=2.6 Hz), 2.19 (2H, m), 2.71 (2H, t, J=7.5 Hz), 6.97 (2H, m), 7.14 (2H, m)。
マススペクトル (EI) ，m/z: 162 (M⁺)。
【０２７４】
（参考例４）
5−フェニルペント−1−イン
参考例3と同様に、3−フェニル−1−ヨードプロパン及びナトリウムアセチリドを用いて、標記化合物を得た。
核磁気共鳴スペクトル（400MHz, CDCl₃），δ： 1.81-1.89 (2H, m), 1.99 (1H, t, J=2.8 Hz), 2.21 (2H, dt, J= 2.8, 7.6 Hz), 2.74 (2H, t, J=7.6 Hz), 7.16-7.23 (3H, m), 7.26-7.32 (2H, m)。
マススペクトル (EI)， m/z: 144 (M⁺)。
【０２７５】
（参考例５）
(2R)-アミノ-2-メチル-4-[5-(5-シクロヘキシルペント-1-イニル)チオフェン-2-イル]ブタン-1-オール
(a)
2-メチル-2-(2-チエニル)エチルマロン酸ジエチルエステル
水素化ナトリウム（55%）18.8 g （0.43mol）をジメチルホルムアミド（200 ml）中に懸濁させ、氷冷下、メチルマロン酸ジエチルエステル50.0 g （0.29mol）を30分間かけてゆっくりと加え、さらに30分撹拌した。次いで、2-(2-ヨードエチル)チオフェン75.2 g (0.32mol)をジメチルホルムアミド（200 ml）に溶かした溶液を窒素雰囲気下、15分かけて加え、さらに室温にて4時間撹拌した。反応混合物を氷冷した10%塩酸(500 ml)中に注ぎ、酢酸エチルで抽出した。有機層を飽和食塩水で洗浄後、無水硫酸マグネシウムで乾燥した。溶媒を減圧濃縮し、残渣をフラッシュシリカゲルカラムクロマトグラフィー（溶出溶媒：ヘキサン／酢酸エチル＝10／1〜5／1）にて精製を行い、標記化合物を無色油状物として、53.1 g (収率65%)得た。
赤外吸収スペクトル， ν_max cm^-1(CHCl₃)：2986, 1726, 1271, 1252。
マススペクトル（FAB），m/z：285 ((M+H)⁺)。
【０２７６】
(b)
2-メチル-2-(2-チエニル)エチルマロン酸モノ−エチルエステル
参考例5(a)で得られた2-メチル-2-(2-チエニル)エチルマロン酸ジエチルエステル52.7 g(0.19mol)をエタノール(240 ml)及び水(80 ml)中に溶解し、氷冷下、水酸化カリウム11.4 g(0.20mol)を加え、同温度で2時間撹拌した。さらに1時間ごとに水酸化カリウム5.7 g(0.1mol)を3回加え、計6時間撹拌した。水(300 ml)及び氷冷した10%塩酸(500 ml)を加え、酢酸エチルで抽出した。有機層を飽和食塩水で洗浄後、無水硫酸マグネシウムで乾燥した。溶媒を減圧濃縮し、残渣をフラッシュシリカゲルカラムクロマトグラフィー（溶出溶媒：ヘキサン／酢酸エチル＝2／1〜0／1）にて精製を行い、標記化合物を淡黄色油状物として、28.6 g (収率60%)得た。
【０２７７】
赤外吸収スペクトル， ν_max cm^-1(CHCl₃)：2987, 1732, 1712, 1251, 1109。
マススペクトル（FAB），m/z：257 ((M+H)⁺)。
【０２７８】
(c)
2-メトキシカルボニルアミノ-2-メチル-4-(2-チエニル)ブタン酸エチルエステル
参考例5(b)で得られた2-メチル-2-(2-チエニル)エチルマロン酸モノ−エチルエステル19.0 g (74.3mmol)をベンゼン(450 ml)中に溶解し、トリエチルアミン11.4 ml (81.7mmol)及びジフェニルリン酸アジド17.6 ml (81.7mmol)を加え、室温にて10分間撹拌後、さらに80℃にて1時間半撹拌した。次いでメタノール60.3 ml (1.49mol)を同温にて30分かけてゆっくりと滴下し、さらに同温度で8時間撹拌した。反応混合物を水(500 ml)中に注ぎ、酢酸エチルで抽出した。有機層を飽和食塩水で洗浄後、無水硫酸マグネシウムで乾燥した。溶媒を減圧濃縮し、残渣をフラッシュシリカゲルカラムクロマトグラフィー（溶出溶媒：ヘキサン／酢酸エチル＝8／1〜4／1）にて精製を行い、標記化合物を無色油状物として、14.7 g (収率69%)得た。
核磁気共鳴スペクトル (400MHz, CDCl₃)， δ：7.11 (1H, d, J = 5.1 Hz), 6.90 (1H, dd, J = 5.1, 3.5 Hz), 6.77 (1H, d, J = 3.5 Hz), 5.69 (1H, brs), 4.19 (2H, q. J = 7.3 Hz), 3.66 (3H, s), 2.84 (2H, dd, J = 10.5, 10.5 Hz), 2.64 (2H, m), 2.20 (2H, dd, J = 10.5, 8.4 Hz), 1.61 (3H, s), 1.28 (3H, t, J = 7.3 Hz)。
赤外吸収スペクトル，ν_maxcm^-1(CHCl₃)：3417, 2987, 1719, 1503, 1453, 1081。
マススペクトル（FAB），m/z：286 ((M＋H)⁺)。
【０２７９】
(d)
2-メトキシカルボニルアミノ-2-メチル-4-(2-チエニル)ブタン-1-オール
参考例5(c)で得られた2-メトキシカルボニルアミノ-2-メチル-4-(2-チエニル)ブタン酸エチルエステル14.7 g (51.6mmol)をエタノール(150 ml)及びテトラヒドロフラン(100 ml)中に溶解し、水素化ホウ素ナトリウム5.07 g (0.13mol)及び塩化リチウム5.68 g (0.13mol)を加え、窒素雰囲気下、室温で一晩撹拌した。翌朝、同様にして、水素化ホウ素ナトリウム5.07 g (0.13mol)及び塩化リチウム5.68 g (0.13mol)を加え、窒素雰囲気下、室温でさらに一晩撹拌した。これと同様の操作をさらに2日間行った。反応混合物を氷冷した10%塩酸(500 ml)中に注ぎ、酢酸エチルで抽出した。有機層を飽和食塩水で洗浄後、無水硫酸マグネシウムで乾燥した。溶媒を減圧濃縮し、残渣をフラッシュシリカゲルカラムクロマトグラフィー（溶出溶媒：ヘキサン／酢酸エチル＝2／1〜1／5）にて精製を行い、標記化合物を白色結晶として、11.7 g (収率93%)得た。
赤外吸収スペクトル，ν_maxcm^-1(KBr)：3406, 3244, 1687, 1562, 1264, 1089。
マススペクトル（FAB），m/z：244 ((M+H)⁺)。
元素分析値；(C₁₁H₁₇NO₃Sとして%)
計算値：C : 54.30, H : 7.04, N : 5.76, S: 13.18
実測値：C : 54.18, H : 6.98, N : 5.78, S: 13.34。
【０２８０】
(e)
2-メトキシカルボニルアミノ-2-メチル-4-(5-ブロモチオフェン-2-イル)ブタン-1-オール
参考例5(d)で得られた2-メトキシカルボニルアミノ-2-メチル-4-(2-チエニル)ブタン-1-オール11.7 g(48.0mmol)をジメチルホルムアミド(120 ml)中に溶解し、氷冷下、N-ブロモスクシンイミド10.8 g(60.8mmol)を加え、窒素雰囲気下、室温にて4時間撹拌した。反応混合物を氷冷した10%塩酸(300 ml)中に注ぎ、酢酸エチルで抽出した。有機層を飽和食塩水で洗浄後、無水硫酸マグネシウムで乾燥した。溶媒を減圧濃縮し、残渣をフラッシュシリカゲルカラムクロマトグラフィー（溶出溶媒：ヘキサン／酢酸エチル＝4／1〜1／3）にて精製を行い、標記化合物を淡黄色油状物として、12.4 g (収率80%)得た。
核磁気共鳴スペクトル (400MHz, CDCl₃)， δ： 6.84 (1H, d, J = 3.7 Hz), 6.57 (1H, d, J = 3.7 Hz), 4.80 (1H, brs), 3.68 (2H, m), 3.64 (3H, s), 2.80 (2H, m), 1.9-2.2 (2H, m), 1.24 (3H, s)。
赤外吸収スペクトル， ν_max cm^-1(CHCl₃)：3627, 3436, 2956, 1722, 1711, 1513, 1259, 1087, 1048。
マススペクトル（FAB），m/z：322 ((M+H)⁺)。
【０２８１】
(f)
4-[2-(5-ブロモチオフェン-2-イル)]エチル-4-メチルオキサゾリジン-2-オン参考例5(e)で得られた2-メトキシカルボニルアミノ-2-メチル-4-(5-ブロモチオフェン-2-イル)ブタン-1-オール12.4 g (38.6mmol)をジメチルホルムアミド(125 ml)中に溶解し、氷冷下、窒素雰囲気下にカリウム t-ブトキシド6.50 g (57.9mmol)を加え、さらに同温にて3時間撹拌した。反応混合物を氷冷した10%塩酸(300 ml)中に注ぎ、酢酸エチルで抽出した。有機層を飽和食塩水で洗浄後、無水硫酸マグネシウムで乾燥した。溶媒を減圧濃縮し、残渣をフラッシュシリカゲルカラムクロマトグラフィー（溶出溶媒：ヘキサン／酢酸エチル＝4／1〜1／2）にて精製を行い、標記化合物を白色結晶として、10.7 g (収率95%)得た。
【０２８２】
核磁気共鳴スペクトル (400MHz, CDCl₃)， δ：6.86 (1H, d, J = 3.7 Hz), 6.58 (1H, d, J = 3.7 Hz), 5.73 (1H, brs), 4.18 (1H, d, J = 8.6 Hz), 4.08 (1H, d, J = 8.6 Hz), 2.84 (2H, m), 1.94 (2H, m), 1.41 (3H, s)。
赤外吸収スペクトル， ν_max cm^-1(KBr)：3211, 1749, 1399, 1037, 798。
マススペクトル（FAB），m/z：290 ((M+H)⁺)。
元素分析値；(C₁₀H₁₂NO₂SBrとして%)
計算値：C : 41.39, H : 4.17, N : 4.83, S: 11.05, Br : 27.54
実測値：C : 41.36, H : 4.04, N : 4.82, S: 11.08, Br : 27.29。
【０２８３】
(g)
(4R)-[2-(5-ブロモチオフェン-2-イル)]エチル-4-メチルオキサゾリジン-2-オン及び(4S)-[2-(5-ブロモチオフェン-2-イル)]エチル-4-メチルオキサゾリジン-2-オン
参考例5(f)で得られた4-[2-(5-ブロモチオフェン-2-イル)]エチル-4-メチルオキサゾリジン-2-オンを分取用光学活性HPLCカラム(ChiralCel OD、ダイセル)を用いて光学分割を行った（カラム, ChiralCel OD (2 cmφ x 25 cm); 溶出溶媒：ヘキサン／2−プロパノール=70／30、流速： 5 ml/分）。先に溶出されるもの (保持時間：55 分)が4S体であり、後から溶出されるもの (保持時間：77 分)が4R体であった。尚、絶対配置についてはX線結晶構造解析により決定した。
(4S)体；[α]_D ²⁴ −4.2 (c 1.03, メタノール)
(4R)体；[α]_D ²⁴ +4.2 (c 1.00, メタノール)。
【０２８４】
(h)
(4R)-[2-[5-(5-シクロヘキシルペント-1-イニル)チオフェン-2-イル]]エチル-4-メチルオキサゾリジン-2-オン
参考例5(g)で得られた(4R)-[2-(5-ブロモチオフェン-2-イル)]エチル-4-メチルオキサゾリジン-2-オン450 mg (1.55mmol)をジメチルホルムアミド4.5 mlに溶解させ、5-シクロヘキシルペント-1-イン（50％キシレン溶液）1.40 g (4.65mmol)、トリエチルアミン2.16 ml (15.5mmol)、ヨウ化銅(Ｉ)30 mg (0.16mmol)及びジクロロビス（トリフェニルホスフィン）パラジウム109 mg (0.16mmol)を加え、窒素雰囲気下、80℃で2時間撹拌した。反応液を水にあけ、酢酸エチルで抽出し、酢酸エチル層を飽和食塩水で洗浄した。酢酸エチル層を無水硫酸ナトリウムで乾燥後、溶媒を減圧下留去した。残渣をシリカゲルクロマトグラフィー（溶出溶媒：ヘキサン／酢酸エチル＝4／1〜3／2）により精製して、標記化合物456 mg (収率82%)を得た。
核磁気共鳴スペクトル（400MHz, CDCl₃），δ: 6.92 (1H, d, J = 3.6 Hz), 6.63 (1H, d, J = 3.6 Hz), 5.45 (1H, brs), 4.18 (1H, d, J = 8.6 Hz), 4.07 (1H, d, J = 8.6 Hz), 2.78-2.90 (2H, m), 2.38 (2H, t, J = 7.2 Hz), 1.92-2.00 (2H, m), 1.55-1.75 (7H, m), 1.40 (3H, s), 1.10-1.35 (6H, m), 0.83-0.95 (2H, m)。
赤外吸収スペクトル，ν_maxcm^-1 (KBr) : 3450, 2926, 2852, 1758, 1382, 1046。
【０２８５】
(i)
(2R)-アミノ-2-メチル-4-[5-(5-シクロヘキシルペント-1-イニル)チオフェン-2-イル]ブタン-1-オール
参考例5(h)で得られた(4R)-[2-[5-(5-シクロヘキシルペント-1-イニル)チオフェン-2-イル]]エチル-4-メチルオキサゾリジン-2-オン456 mg (1.27mmol)をテトラヒドロフラン1 ml及びメタノール2 mlに溶解させ、氷冷下、5規定水酸化カリウム水溶液2 mlを加え、18時間加熱還流した。反応液に水を加え、塩化メチレンで抽出した。塩化メチレン層を無水硫酸ナトリウムで乾燥後、減圧下溶媒を留去した。残渣をシリカゲルクロマトグラフィー［溶出溶媒：（塩化メチレン／メタノール＝20／1）、（塩化メチレン／メタノール／アンモニア水＝10／1／0.1）］により精製して、標記化合物353 mg (収率83%)を得た。
核磁気共鳴スペクトル（400MHz, CDCl₃），δ: 6.92 (1H, d, J = 3.5 Hz), 6.62 (1H, d, J = 3.5 Hz), 3.37 (1H, d, J = 10.5 Hz), 3.32 (1H, d, J = 10.5 Hz), 2.75-2.90 (2H, m), 2.38 (2H, t, J = 7.1 Hz), 1.52-1.79 (9H, m), 1.12-1.33 (6H, m), 1.11 (3H, s), 0.81-0.96 (2H, m)。
赤外吸収スペクトル，ν_max cm^-1 (CHCl₃) : 2925, 2852, 1449, 1041。
マススペクトル（FAB），m/z：334 ((M+H)⁺)。
元素分析値；(C₂₀H₃₁NOS・0.3H₂Oとして%)
計算値：C : 70.87, H : 9.40, N : 4.13, S: 9.46
実測値：C : 70.83, H : 9.21, N : 4.22, S: 9.64
[α]_D ²⁴ ‐2.0 (c 0.60, メタノール)。
【０２８６】
（参考例６）
(2R)-アミノ-2-メチル-4-[5-(4-シクロヘキシルオキシブト-1-イニル)チオフェン-2-イル]ブタン-1-オールマレイン酸塩
4-[2-(5-ブロモチオフェン-2-イル)]エチル-4-メチルオキサゾリジン-2-オン及び4-シクロヘキシルオキシブト-1-インを出発原料として用い、参考例5(h)及び参考例5(i)と同様に反応して、次いでマレイン酸塩にして標記化合物(収率43%)を得た。
核磁気共鳴スペクトル（400MHz, CD₃OD），δ: 6.93 (1H, d, J = 3.6 Hz), 6.73 (1H, d, J = 3.6 Hz), 6.25 (2H, s), 3.57-3.67 (3H, m), 3.51 (1H, d, J = 11.6 Hz), 3.32-3.42 (1H, m), 2.78-2.95 (2H, m), 2.63 (2H, t, J = 6.7 Hz), 1.50-2.10 (7H, m), 1.17-1.37 (8H, m)。
赤外吸収スペクトル， ν_max cm^-1 (KBr) : 3394, 2932, 2858, 1583, 1506, 1386, 1367, 1194, 1104。
【０２８７】
（参考例７）
酢酸（２Ｒ）−アセチルアミノ−２−メチル−４−[５−（５−フェニルペント−１−イニル）チオフェン−２−イル]ブチルエステル
参考例２で合成した酢酸（2R）−アセチルアミノ−2−メチル−4−（5−ブロモチオフェン−2−イル）ブチルエステル1.60ｇ（4.59mmol）をジメチルホルムアミド16ｍｌに溶解させ、5-フェニルペント-1-イン1.99ｇ（13.8ミリモル）、トリエチルアミン6.40ｍｌ（45.9ミリモル）、ヨウ化銅（Ｉ）175ｍｇ（0.92ミリモル）及びジクロロビス（トリフェニルホスフィン）パラジウム322ｍｇ（0.46ミリモル）を加え、窒素雰囲気下80℃で2時間撹拌した。反応液を水にあけ、酢酸エチルで抽出し、酢酸エチル層を無水硫酸マグネシウムで乾燥後、溶媒を減圧下留去した。残渣をシリカゲルクロマトグラフィー（溶出溶媒：ヘキサン／酢酸エチル＝２／１〜２／３）により精製して、標記化合物1.41ｇ（収率75％）を得た。
核磁気共鳴スペクトル（400MHz, CDCl₃），δ：1.36 (3H, s), 1.85-2.05 (3H, m), 1.94 (3H, s), 2.10 (3H, s), 2.25-2.35 (1H, m), 2.43 (2H, t, J=7.0 Hz), 3.70-3.80 (4H, m), 4.17 (1H, d, J=11.2 Hz), 4.31 (1H, d, J=11.2 Hz), 5.38 (1H, brs), 6.64 (1H, d, J=3.6 Hz), 6.94 (1H, d, J=3.6 Hz), 7.15-7.42 (5H, m)。
赤外吸収スペクトル，ν_max cm^-1 (CHCl₃) ： 3443, 2946, 2862, 1737, 1681, 1511, 1374, 1251, 1042。
【０２８８】
（参考例８）
（2R）−アミノ−2−メチル−4−[5−（5−フェニルペンチル）チオフェン−2−イル]ブタン−1−オールシュウ酸塩
参考例７で得られた酢酸（2R）−アセチルアミノ−2−メチル−4−[5−（6−フェニルペント−1−イニル）チオフェン−2−イル]ブチル337ｍｇ（0.82ミリモル）をメタノール17mlに溶解させ、１０％パラジウム‐炭素170ｍｇを加え、水素雰囲気下、室温で16時間撹拌した。セライトで触媒を濾去後、濾液を減圧下留去し、酢酸（2R）−アセチルアミノ−2−メチル−4−[5−（5−フェニルペンチル）チオフェン−2−イル]ブチル318ｍｇ（収率93％）を得た。得られた酢酸ブチルエステル298ｍｇ（0.72ミリモル）をテトラヒドロフラン、メタノール及び水の混合液（１／１／１）６ｍｌ中に溶解し、水酸化リチウム・一水和物301ｍｇ（7.17mmol）を加え、50℃で６時間撹拌した。反応液を水にあけ、塩化メチレンで抽出し、塩化メチレン層を無水硫酸ナトリウムで乾燥後、溶媒を減圧下留去した。残渣243ｍｇをメタノールに溶解し、シュウ酸65ｍｇ（0.72 mmol）を加え、析出した結晶を濾取し、標記化合物を白色結晶として251ｍｇ（収率83％）得た。
核磁気共鳴スペクトル（400MHz, CD₃OD）， δ：1.31 (3H, s), 1.32-1.42 (2H, m), 1.58-1.70 (4H, m), 1.88-2.08 (2H, m), 2.59 (2H, t, J=7.6 Hz), 2.74 (2H, t, J=7.4 Hz), 2.75-2.91 (2H, m), 3.52 (1H, d, J=11.6 Hz), 3.61 (1H, d, J=11.6 Hz), 6.56 (1H, d, J=3.3 Hz), 6.63 (1H, d, J=3.3 Hz), 7.09-7.17 (3H, m), 7.19-7.27 (2H, m)。
赤外吸収スペクトル，ν_max cm^-1 (KBr)：3458, 3134, 2929, 2855, 2595, 1724, 1642, 1543, 1219, 710 cm^-1。
【０２８９】
（参考例９）
（2R）−アミノ−2−メチル−4−[5−（5−フェニルペント−1−イニル）チオフェン−2−イル]ブタン−1−オールシュウ酸塩
参考例７で得られた酢酸（2R）−アセチルアミノ−2−メチル−4−[5−（5−フェニルペント−1−イニル）チオフェン−2−イル]ブチルエステル1.40ｇ（3.40ｍｍｏｌ）をテトラヒドロフラン、メタノール及び水の混合液（１／１／１）14ｍｌ中に溶解し、水酸化リチウム・一水和物1.43ｇ（34.0ｍｍｏｌル）を加え、50℃で4時間撹拌した。反応液を水にあけ、塩化メチレンで抽出し、塩化メチレン層を無水硫／１／0.1）により精製して、（2R）−アミノ−2−メチル−4−[5−（5−フェニルペント−1−イニル）チオフェン−2−イル]ブタン−1−オール1.11ｇ（収率100％）を得た。得られたブタン−1−オール360ｍｇ（1.10ｍｍｏｌ）をメタノールに溶解し、シュウ酸99ｍｇ（1.10ｍｍｏｌ）を加え、析出した結晶をメタノールより再結晶を行ない、標記化合物を白色結晶として394ｍｇ（収率86％）得た。
核磁気共鳴スペクトル（400MHz, CD₃OD）， δ：1.31 (3H, s), 1.82-2.10 (4H, m), 2.40 (2H, t, J=7.0 Hz), 2.75 (2H, t, J=7.5 Hz), 2.80-2.95 (2H, m), 3.52 (1H, d, J=11.5 Hz), 3.61 (1H, d, J=11.5 Hz), 6.73 (1H, d, J=3.6 Hz), 6.94 (1H, d, J=3.6 Hz), 7.13-7.30 (5H, m)。
赤外吸収スペクトル，ν_max cm^-1 (KBr)：3383, 3106, 3026, 2980, 2942, 2622, 2514, 1721, 1609, 1539, 1198, 699。マススペクトル（FAB），m/z：328((M+H)⁺)（Free体）。
元素分析値；（C₂₀H₂₅NOS・C₂H₂O₄・0.2H₂Oとして％）
計算値：C,62.75; H,6.55; N,3.32; S,7.61
実測値：C,62.50; H,6.29; N,3.39; S,7.70。
[α]_D ²⁵ -0.9 (c 1.00, メタノール)。
【０２９０】
（参考例１０）
（2R）−アミノ−2−メチル−4−[5−（5−フェニルペンタノイル）チオフェン−2−イル]ブタン−1−オールシュウ酸塩
参考例９の第一工程で得られた（2R）−アミノ−2−メチル−4−[5−（5−フェニルペント−1−イニル）チオフェン−2−イル]ブタン−1−オールシュウ酸塩387ｍｇ（1.18ミリモル）をメタノール４ｍｌに溶解させ、6規定硫酸４ｍｌを加え、4時間加熱還流した。反応液を0℃に冷却後、１規定水酸化ナトリウム水溶液でアルカリ性（ｐＨ１４）にした後、塩化メチレンで抽出した。塩化メチレン層を無水硫酸ナトリウムで乾燥後、溶媒を減圧下留去し、残渣をシリカゲルクロマトグラフィー（Chromatorex NH(100-200 mesh)）（溶出溶媒：塩化メチレン／メタノール＝１／０〜50／１）により精製して、（2R）−アミノ−2−メチル−4−[5−（5−フェニルペンタノイル）チオフェン−2−イル]ブタン−1−オール336ｍｇ（収率82％）得た。これをメタノールに溶解し、シュウ酸88ｍｇ（0.97ｍｍｏｌ）を加え、得られた結晶をメタノールより再結晶を行ない、標記化合物を白色結晶として332ｍｇ（収率78％）得た。
核磁気共鳴スペクトル（400MHz, CD₃OD）， δ：1.19 (3H, s), 1.55-1.67 (4H, m), 1.80-1.98 (2H, m), 2.60 (2H, t, J=6.7 Hz), 2.83-2.96 (4H, m), 3.40 (1H, d, J=11.3 Hz), 3.47 (1H, d, J=11.3 Hz), 7.00 (1H, d, J=3.7 Hz), 7.13-7.22 (3H, m), 7.23-7.31 (2H, m), 7.80 (1H, d, J=3.7 Hz)。赤外吸収スペクトル，ν_max cm^-1 (KBr)：3126, 2942, 2657, 1915, 1718, 1649, 1609, 1547, 1445, 1205, 700
マススペクトル（FAB），m/z：346 ((M+H)⁺)（フリー体）。
元素分析値；（C₂₀H₂₇NO₂S・C₂H₂O₄・0.5H₂Oとして％）
計算値：C,59.44; H,6.80; N,3.15; S,7.21
実測値：C,59.62; H,6.53; N,3.31; S,7.43。
【０２９１】
（試験例1）
ラットHvGR（Host veRsus GRaft Reaction）に対する抑制活性の測定
（1） 2系統のラット［Lewis（雄、6週齢、日本チャールス・リバー株式会社）とWKAH/Hkm（雄、7週齢、日本エスエルシー株式会社）］を使用した。1群5匹のラット（宿主）を用いた。
（2） WKAH/HkmラットまたはLewisラットの脾臓から脾臓細胞を単離し、RPMI1640培地（ライフテクノロジー社製）で1x10⁸個/ml濃度に浮遊した。Lewisラットの両後肢足蹠皮内に、WKAH/HkmラットまたはLewisラットの脾臓細胞浮遊液0.1ml（脾臓細胞数として1x10⁷個）を注射した。
（3）試験化合物を5％ＳＢＥ−β−ＣＤ水溶液（ＳＢＥ：Sulfobutyl Ether）に溶解し、WKAH/Hkmラット脾臓細胞を注射されたLewisラットに、ラットの体重1kg当たり5mlの割合で、1日1回、脾臓細胞注射日から4日間連日で経口投与した。なお、同系群（Lewisラット脾臓細胞を注射されたLewisラット群）と対照群（WKAH/Hkmラット脾臓細胞を注射され、検体を投与されないLewisラット）には、検体の代わりに5％ＳＢＥ−β−ＣＤ水溶液を経口投与した。
（4）各個体の膝窩（popliteal）リンパ節重量から同系群の平均膝窩リンパ節重量を引き（「HvGRによる膝窩リンパ節重量」）、対照群の平均「HvGRによる膝窩リンパ節重量」に対する化合物投与群の各個体の「HvGRによる膝窩リンパ節重量」から抑制率を算出した。化合物の抑制活性は、化合物の投与量と抑制率から最小二乗法を用いて算出したID₅₀値（mg/kg）で表示した。
【０２９２】
【表３】

本試験の結果、本発明の化合物は優れた抑制活性を示した。
【０２９３】
【発明の効果】
本発明の一般式（Ｉ）を有するリン酸又はホスホン酸誘導体、その薬理上許容される塩又はその薬理上許容されるエステルは、毒性が低く優れた免疫抑制作用を有し、各種臓器移植又は皮膚移植での拒絶反応、全身性エリトマトーデス、慢性関節リウマチ、多発性筋炎、結合組織炎、骨格筋炎、骨関節炎、変形性関節症、皮膚筋炎、強皮症、ベーチェット病、Chron病、潰瘍性大腸炎、自己免疫性肝炎、再生不良性貧血、特発性血小板減少性紫斑病、自己免疫性溶血性貧血、多発性硬化症、自己免疫性水疱症、尋常性乾癬、血管炎症群、Wegener肉芽腫、ぶどう膜炎、シェーグレン症候群、特発性間質性肺炎、Goodpasture症候群、サルコイドーシス、アレルギー性肉芽腫性血管炎、気管支喘息、心筋炎、心筋症、大動脈炎症候群、心筋梗塞後症候群、原発性肺高血圧症、微小変化型ネフローゼ、膜性腎症、膜性増殖性腎炎、巣状糸球体硬化症、半月体形成性腎炎、重症筋無力症、炎症性ニューロパチー、アトピー性皮膚炎、慢性光線性皮膚炎、日光過敏症、蓐瘡、Ｓｙｄｅｎｈａｍ舞踏病，全身性硬化症、成人発症糖尿病、インスリン依存性糖尿病、若年性糖尿病、アテローム性動脈硬化症、糸球体腎炎、IgA腎症、尿細管間質性腎炎、原発性胆汁性肝硬変、原発性硬化性胆管炎、劇症肝炎、ウイルス性肝炎、GVHD、接触皮膚炎、敗血症等の自己免疫疾患又はその他免疫関連疾患、真菌、マイコプラズマ、ウィルス、原虫等の感染症、心不全、心肥大、不整脈、狭心症、心虚血、動脈塞栓、動脈瘤、静脈瘤、血行障害等の循環器系疾患、アルツハイマー病、痴呆、パーキンソン病、脳卒中、脳梗塞、脳虚血、鬱病、躁鬱病、統合失調症、ハンチントン舞踏病、癲癇、痙攣、多動症、脳炎、髄膜炎、食欲不振および過食等の中枢系疾患、リンパ腫、白血病、多尿、頻尿、糖尿病性網膜症等の各種疾患（特に好適には、各種臓器移植又は皮膚移植での拒絶反応、全身性エリトマトーデス、慢性関節リウマチ、多発性硬化症、アトピー性皮膚炎等の自己免疫疾患）の、温血動物用（特に、ヒト用）の予防剤若しくは治療剤（特に、治療薬）として有用である。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a phosphoric acid or phosphonic acid derivative having an excellent immunosuppressive action, a pharmacologically acceptable salt of phosphoric acid or phosphonic acid derivative, an ester of phosphoric acid or phosphonic acid derivative, or a pharmaceutical containing them as an active ingredient Relates to the composition.
[0002]
[Prior art]
Conventionally, in the treatment of immune-related diseases such as rheumatism and other autoimmune diseases, anti-inflammatory drugs such as steroids have been used for inflammatory reactions caused by abnormal immune reactions. However, these are symptomatic treatments and not fundamental treatments.
[0003]
Although it has been reported that abnormalities of the immune system are involved in the onset of diabetes and nephritis (see, for example, Non-Patent Document 1), [Kidney International, 51, 94 (1997); Journal of Immunology, 157, 4691 (1996)], no drug has been developed to improve the abnormality.
[0004]
On the other hand, the development of a method for suppressing an immune response is extremely important for preventing rejection in organs and cell transplants and for treating and preventing various autoimmune diseases. However, conventionally known immunosuppressive agents such as cyclosporin A (CsA) and tacrolimus (TRL) are known to be toxic to the kidney and liver, and in order to reduce such side effects, Although treatments such as using steroids have been widely used, the current situation is that they do not necessarily exhibit sufficient immunosuppressive effects without showing side effects.
[0005]
Against this background, attempts have been made to find compounds having low toxicity and excellent immunosuppressive action.
[0006]
Examples of the immunosuppressant include amino alcohol derivatives described in WO94 / 08943 (EP627406), WO96 / 06068, WO98 / 45249, and phosphate esters described in WO02 / 18395. Derivatives are known. However, none of the publications disclose the compound of the present invention.
[0007]
On the other hand, the compound of the present invention in which Z = O in the above general formula (I) is disclosed in WO 02/06268 as a compound in which the protective group of the hydroxy compound is a phosphate ester salt residue.
[0008]
[Patent Document 1]
WO94 / 08943 (EP627406) (page 371)
[Patent Document 2]
WO96 / 06068 (page 271)
[Patent Document 3]
WO98 / 45249 (page 81)
[Patent Document 4]
WO02 / 06268 (page 345)
[Non-Patent Document 1]
Kidney International, vol. 51, 94 (1997); Journal of Immunology, vol. 157, 4691 (1996)
[0009]
[Problems to be solved by the invention]
The compound of the present invention having the above general formula (I) has excellent immunosuppressive action with low toxicity, rejection in various organ transplants or skin transplants, systemic lupus erythematosus, rheumatoid arthritis, polymyositis, binding Histitis, skeletal myositis, osteoarthritis, osteoarthritis, dermatomyositis, scleroderma, Behcet's disease, Chron's disease, ulcerative colitis, autoimmune hepatitis, aplastic anemia, idiopathic thrombocytopenic purpura, Autoimmune hemolytic anemia, multiple sclerosis, autoimmune bullous disease, psoriasis vulgaris, vascular inflammation group, Wegener granulomas, uveitis, Sjogren's syndrome, idiopathic interstitial pneumonia, Goodpasture syndrome, sarcoidosis, allergy Granulomatous vasculitis, bronchial asthma, myocarditis, cardiomyopathy, aortitis syndrome, post-myocardial infarction syndrome, primary pulmonary hypertension, minimal change nephrosis, membranous nephropathy, membranoproliferative nephritis, focal thread Somatic sclerosis, crescent nephritis, myasthenia gravis, inflammatory neuropathy, atopic dermatitis, chronic actinic dermatitis, photosensitivity, pressure ulcer, Sydenham chorea, systemic sclerosis, adult-onset diabetes, Insulin-dependent diabetes, juvenile diabetes, atherosclerosis, glomerulonephritis, IgA nephropathy, tubulointerstitial nephritis, primary biliary cirrhosis, primary sclerosing cholangitis, fulminant hepatitis, viral hepatitis , GVHD, contact dermatitis, autoimmune diseases such as sepsis or other immune related diseases, infections such as fungi, mycoplasma, virus, protozoa, heart failure, cardiac hypertrophy, arrhythmia, angina, cardiac ischemia, arterial embolism, Cardiovascular diseases such as aneurysm, varicose vein, blood circulation disorder, Alzheimer's disease, dementia, Parkinson's disease, stroke, cerebral infarction, cerebral ischemia, depression, manic depression, schizophrenia, Huntington's chorea, epilepsy, Central diseases such as convulsions, hyperactivity, encephalitis, meningitis, anorexia and bulimia, various diseases such as lymphoma, leukemia, polyuria, frequent urination, diabetic retinopathy (especially rejection in various organ transplants or skin transplants) The present invention has been found out by finding it useful for reactions, autoimmune diseases such as systemic lupus erythematosus, rheumatoid arthritis, multiple sclerosis, and atopic dermatitis).
[0010]
Accordingly, the present invention relates to a phosphoric acid or phosphonic acid derivative, a pharmacologically acceptable salt of phosphoric acid or phosphonic acid derivative, or a pharmacologically acceptable ester of phosphoric acid or phosphonic acid derivative having low toxicity and excellent immunosuppressive action. Or providing a pharmaceutical composition containing them as active ingredients.
[0011]
[Means for Solving the Problems]
(1) The phosphoric acid or phosphonic acid derivative of the present invention has the following general formula (I).
[0012]
[Formula 4]

[0013]
In the above formula,
R¹And R²Are the same or different and each represents a hydrogen atom, a lower aliphatic acyl group or a lower alkoxycarbonyl group,
R^ThreeAnd Ra^ThreeAre the same or different and each represents a hydrogen atom or a protecting group for a phosphate group,
R^FourRepresents a hydrogen atom, a lower alkyl group or a hydroxy lower alkyl group,
n represents an integer of 1 to 6,
X is an ethylene group, vinylene group, ethynylene group, formula -D-CH₂A group having-(wherein D represents a carbonyl group, a group having the formula -CH (OH)-, an oxygen atom, a sulfur atom or a group having the formula -NH-), C₆-C_TenC substituted with 1 to 3 arylene groups or groups selected from substituent group a₆-C_TenRepresents an arylene group,
Y is a single bond, C₁-C_TenC substituted with 1 to 3 of alkylene group and a group selected from substituent groups a and b₁-C_TenAn alkylene group, C having an oxygen atom or a sulfur atom in the carbon chain or at the chain end₁-C_TenC having an oxygen atom or a sulfur atom in the carbon chain or at the chain end, substituted with 1 to 3 alkylene groups or groups selected from substituent groups a and b₁-C_TenIndicates an alkylene group
Z represents an oxygen atom or a methylene group,
R^FiveIs a hydrogen atom, C_Three-C_TenA cycloalkyl group, C₆-C_TenC substituted by 1 to 3 with a group selected from aryl group, sulfur atom, oxygen atom and / or 5- to 7-membered heterocyclic group containing 1 to 3 nitrogen atoms and substituent groups a and b_Three-C_TenC substituted with 1 to 3 of a cycloalkyl group and a group selected from substituent groups a and b₆-C_TenAn aryl group, or a 5- to 7-membered heterocyclic group containing 1 to 3 sulfur atoms, oxygen atoms and / or nitrogen atoms, substituted with 1 to 3 groups selected from substituent groups a and b;
R⁶And R⁷Are the same or different and each represents a hydrogen atom or a group selected from the substituent group a,
Substituent group a is a halogen atom, lower alkyl group, halogeno lower alkyl group, lower alkoxy group, lower alkylthio group, carboxyl group, lower alkoxycarbonyl group, hydroxy group, lower aliphatic acyl group, amino group, mono-lower alkyl A group consisting of an amino group, a di-lower alkylamino group, a lower aliphatic acylamino group, a cyano group and a nitro group;
Substituent group b is C_Three-C_TenA cycloalkyl group, C₆-C_TenC substituted with 1 to 3 aryl groups, 5 to 7-membered heterocyclic groups containing 1 to 3 sulfur atoms, oxygen atoms and / or nitrogen atoms, or a group selected from substituent group a_Three-C_TenC substituted with 1 to 3 cycloalkyl groups or groups selected from substituent group a₆-C_TenA group consisting of an aryl group and a 5- to 7-membered heterocyclic group containing 1 to 3 sulfur atoms, oxygen atoms and / or nitrogen atoms substituted with 1 to 3 groups selected from the substituent group a .
[0014]
However, R^FiveIs a hydrogen atom, Y is C 1-3 substituted with a group selected from substituent groups a and b₁-C_TenAn alkylene group, C having an oxygen atom or a sulfur atom in the carbon chain or at the chain end₁-C_TenC having an oxygen atom or a sulfur atom in the carbon chain or at the chain end, substituted with 1 to 3 alkylene groups or groups selected from substituent groups a and b₁-C_TenAn alkylene group is shown.
[0015]
The present invention is a compound having the formula (I), a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof.
(2) In (1), the compound having the formula (I) is represented by the formula (Ia)
[0016]
[Chemical formula 5]

[0017]
[Wherein R¹, R², R^Three, R^Four, R^Five, R⁶, R⁷, X, Y, Z and n have the same meaning as in (1). ], A pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof,
(3) In (1), the compound having the formula (I) is represented by the formula (Ib)
[0018]
[Chemical 6]

[0019]
(Wherein R¹, R², R^Three, R^Four, R^Five, R⁶, R⁷, X, Y, Z and n have the same meaning as in claim 1. ), A pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof,
(4) In any one item selected from (1) to (3),
R¹And R²Are the same or different, hydrogen atom, C₁-C_FourAliphatic acyl group or C₁-C_FourIn the compound which is a lower alkoxycarbonyl group or a pharmacologically acceptable salt thereof, (5) any one selected from (1) to (3),
R¹And R²Are the same or different and are a hydrogen atom or C₁-C₂Aliphatic acyl group or C₁-C₂A compound which is a lower alkoxycarbonyl group or a pharmacologically acceptable salt thereof,
(6) In any one item selected from (1) to (3),
R¹And R²Are the same or different and are a hydrogen atom, an acetyl group or a methoxycarbonyl group, or a pharmacologically acceptable salt thereof,
(7) In any one item selected from (1) to (3),
R¹And R²Is a hydrogen atom or a pharmacologically acceptable salt thereof,
(8) In any one item selected from (1) to (7),
R^ThreeAnd R^Threea or a pharmacologically acceptable salt thereof, wherein a is the same or different and is a hydrogen atom, a lower alkyl group, a lower alkenyl group or an aralkyl group,
(9) In any one item selected from (1) to (7),
R^ThreeAnd R^Threea or a pharmacologically acceptable salt thereof, wherein a is the same or different and is a hydrogen atom or a lower alkyl group,
(10) In any one item selected from (1) to (7),
R^ThreeAnd R^Threea is the same or different and is a hydrogen atom or C₁-C_FourA compound which is an alkyl group or a pharmacologically acceptable salt thereof,
(11) In any one item selected from (1) to (7),
R^ThreeAnd R^Threea or a pharmacologically acceptable salt thereof, wherein a is the same or different and is a hydrogen atom, a methyl group or an ethyl group,
(12) In any one item selected from (1) to (7),
R^ThreeAnd R^Threea compound in which a is a hydrogen atom or a pharmacologically acceptable salt thereof,
(13) In any one item selected from (1) to (12),
R^FourBut C₁-C_FourAlkyl group or hydroxy C₁-C_FourA compound which is an alkyl group or a pharmacologically acceptable salt thereof,
(14) In any one item selected from (1) to (12),
R^FourBut C₁-C₂Alkyl group or hydroxy C₁-C₂A compound which is an alkyl group or a pharmacologically acceptable salt thereof,
(15) In any one item selected from (1) to (12),
R^FourBut C₁-C₂A compound which is an alkyl group or a pharmacologically acceptable salt thereof,
(16) In any one item selected from (1) to (12),
R^FourIs a methyl group or a pharmacologically acceptable salt thereof,
(17) In any one item selected from (1) to (16),
a compound wherein n is 2 or 3, or a pharmacologically acceptable salt thereof,
(18) In any one item selected from (1) to (16),
a compound wherein n is 2, or a pharmacologically acceptable salt thereof,
(19) In any one item selected from (1) to (18),
X is an ethylene group, an ethynylene group, a formula -D-CH₂-In the formula, D represents a carbonyl group or a group having the formula -CH (OH)-. ], A phenylene group, a naphthylene group, or a compound which is a phenylene group or a naphthylene group substituted by 1 to 3 groups selected from the substituent group a or a pharmacologically acceptable salt thereof,
(20) In any one item selected from (1) to (18),
X is an ethylene group, an ethynylene group, a formula —CO—CH₂A compound or a pharmacologically acceptable salt thereof, which is a phenylene group substituted with 1 to 3 groups selected from the group consisting of-, a phenylene group, or a group selected from the group consisting of a halogen atom and a lower alkyl group;
(21) In any one item selected from (1) to (18),
X is an ethylene group, an ethynylene group or a formula —CO—CH₂A compound having a-or a pharmacologically acceptable salt thereof,
(22) In any one item selected from (1) to (21),
Y is C₁-C_TenC substituted with 1 to 3 alkylene groups or groups selected from substituent groups a and b₁-C_TenA compound which is an alkylene group or a pharmacologically acceptable salt thereof,
(23) In any one item selected from (1) to (21),
Y is C₁-C₆C substituted with 1 to 3 alkylene groups or hydroxy groups₁-C₆A compound which is an alkylene group or a pharmacologically acceptable salt thereof,
(24) In any one item selected from (1) to (21),
Y is C₁-C_FiveC substituted with 1 to 3 alkylene groups or hydroxy groups₁-C_FiveA compound which is an alkylene group or a pharmacologically acceptable salt thereof,
(25) In any one item selected from (1) to (21),
A compound or a pharmaceutically acceptable salt thereof, wherein Y is an ethylene group, trimethylene group, tetramethylene group or one hydroxy group, and is an ethylene group, trimethylene group or tetramethylene group;
(26) In any one item selected from (1) to (21),
A compound wherein Y is an ethylene group, a trimethylene group or a tetramethylene group, or a pharmacologically acceptable salt thereof,
(27) In any one item selected from (1) to (21),
A compound in which Y is an ethylene or trimethylene group or a pharmacologically acceptable salt thereof,
(28) In any one item selected from (1) to (21),
Y is C having an oxygen atom or a sulfur atom in the carbon chain or at the chain end.₁-C_TenC having an oxygen atom or a sulfur atom in the carbon chain or at the chain end, substituted with an alkylene group or one hydroxy group₁-C_TenA compound which is an alkylene group or a pharmacologically acceptable salt thereof,
(29) In any one item selected from (1) to (21),
Y is C having an oxygen atom or a sulfur atom in the carbon chain or at the chain end.₁-C_TenA compound which is an alkylene group or a pharmacologically acceptable salt thereof,
(30) In any one item selected from (1) to (21),
Y is C having an oxygen atom in the carbon chain or at the chain end₁-C_TenA compound which is an alkylene group or a pharmacologically acceptable salt thereof,
(31) In any one item selected from (1) to (21),
Y is C having an oxygen atom in the carbon chain or at the chain end₁-C₆A compound which is an alkylene group or a pharmacologically acceptable salt thereof,
(32) In any one item selected from (1) to (21),
Y represents the formula -O-CH₂-, -O- (CH₂)₂-, -O- (CH₂)_Three-, -CH₂-O-,-(CH₂)₂-O- or-(CH₂)_ThreeA compound which is a group having -O- or a pharmacologically acceptable salt thereof,
(33) In any one item selected from (1) to (21),
Y represents the formula —CH₂-O- or-(CH₂)₂A compound which is a group having -O- or a pharmacologically acceptable salt thereof,
(34) In any one item selected from (1) to (33),
R^FiveIs a hydrogen atom or a pharmacologically acceptable salt thereof,
(35) In any one item selected from (1) to (33),
R^FiveBut C_Three-C_TenA cycloalkyl group, C₆-C_TenC substituted with 1 to 3 aryl groups, 5 to 7-membered heterocyclic groups containing 1 to 3 sulfur atoms, oxygen atoms and / or nitrogen atoms, and groups selected from substituent groups a and b_Three-C_TenC substituted with 1 to 3 cycloalkyl groups or groups selected from substituent groups a and b₆-C_TenA compound which is an aryl group or a pharmacologically acceptable salt thereof,
(36) In any one item selected from (1) to (33),
R^FiveBut C_Three-C_TenA cycloalkyl group, C₆-C_TenC substituted with 1 to 3 aryl groups or a group selected from the group consisting of a halogen atom, a lower alkyl group, a halogeno lower alkyl group, a lower alkoxy group, a lower alkylthio group and a lower aliphatic acyl group_Three-C_TenA cycloalkyl group or C₆-C_TenA compound which is an aryl group or a pharmacologically acceptable salt thereof,
(37) In any one item selected from (1) to (33),
R^FiveBut C_Three-C_TenA cycloalkyl group, C₆-C_TenC substituted with 1 to 3 substituents by an aryl group or a group selected from the group consisting of a halogen atom, a lower alkyl group, a halogeno lower alkyl group, a lower alkoxy group and a lower aliphatic acyl group_Three-C_TenA cycloalkyl group or C₆-C_TenA compound which is an aryl group or a pharmacologically acceptable salt thereof,
(38) In any one item selected from (1) to (33),
R^FiveBut C_Five-C₆A compound which is a cycloalkyl group, a phenyl group or a naphthyl group or a pharmacologically acceptable salt thereof,
(39) In any one item selected from (1) to (33),
R^FiveIs a cyclohexyl group or a phenyl group or a pharmacologically acceptable salt thereof,
(40) In any one item selected from (1) to (39),
R⁶And R⁷Are the same or different and are a hydrogen atom, a halogen atom, a lower alkyl group, a halogeno lower alkyl group, a lower alkoxy group or a lower alkylthio group, or a pharmacologically acceptable salt thereof,
(41) In any one item selected from (1) to (39),
R⁶And R⁷Is a hydrogen atom or a pharmacologically acceptable salt thereof,
(42) In any one item selected from (1) to (41),
A compound in which Z is an oxygen atom or a pharmacologically acceptable salt thereof,
(43) In (1), any one compound selected from the following or a pharmacologically acceptable salt thereof:
Phosphoric acid mono 2-amino-2-methyl-4- [5- (4-cyclohexylbutyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- (5-cyclohexylpentyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- (5-phenylpentyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- (4-cyclohexyloxybutyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (4-fluorophenoxy) butyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (4-methoxyphenoxy) butyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- (4-benzyloxybutyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- (4-cyclohexylbut-1-ynyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- (4-phenylbut-1-ynyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- (5-cyclohexylpent-1-ynyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- (5-phenylpent-1-ynyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (4-fluorophenyl) pent-1-ynyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (4-methoxyphenyl) pent-1-ynyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (4-methylcyclohexyloxy) propynyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (4-methylphenoxy) propynyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (4-ethylphenoxy) propynyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (4-methylthiophenoxy) propynyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- (4-cyclohexyloxybut-1-ynyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (4-fluorophenoxy) but-1-ynyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (4-methylphenoxy) but-1-ynyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- (3-cyclohexylmethoxypropynyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- (4-phenylmethoxybut-1-ynyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- (4-cyclohexylbutanoyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- (4-phenylbutanoyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- (5-cyclohexylpentanoyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- (5-phenylpentanoyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (4-fluorophenyl) pentanoyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-ethyl-4- [5- (5-cyclohexylpentyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-ethyl-4- [5- (5-cyclohexylpent-1-ynyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-ethyl-4- [5- (5-cyclohexylpentanoyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (4-chlorophenoxy) propynyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (3-methylphenoxy) propynyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (3,4-dimethylphenoxy) propynyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (3-methoxyphenoxy) propynyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (3,4-dimethoxyphenoxy) propynyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (3,5-dimethoxyphenoxy) propynyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (3-acetylphenoxy) propynyl] thiophen-2-yl] butyl ester and
Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (4-acetylphenoxy) propynyl] thiophen-2-yl] butyl ester.
(44) In (1), any one compound selected from the following or a pharmacologically acceptable salt thereof:
3-amino-3-methyl-5- [5- (4-cyclohexylbutyl) thiophen-2-yl] pentylphosphonic acid,
3-amino-3-methyl-5- [5- (5-cyclohexylpentyl) thiophen-2-yl] pentylphosphonic acid,
3-Amino-3-methyl-5- [5- (5-phenylpentyl) thiophene-
2-yl] pentylphosphonic acid,
3-amino-3-methyl-5- [5- (4-cyclohexyloxybutyl) thiophen-2-yl] pentylphosphonic acid,
3-amino-3-methyl-5- [5- [4- (4-fluorophenoxy) butyl] thiophen-2-yl] pentylphosphonic acid,
3-amino-3-methyl-5- [5- [4- (4-methoxyphenoxy) butyl] thiophen-2-yl] pentylphosphonic acid,
3-amino-3-methyl-5- [5- (4-benzyloxybutyl) thiophen-2-yl] pentylphosphonic acid,
3-amino-3-methyl-5- [5- (4-cyclohexylbutanoyl) thiophen-2-yl] pentylphosphonic acid,
3-amino-3-methyl-5- [5- (4-phenylbutanoyl) thiophen-2-yl] pentylphosphonic acid,
3-amino-3-methyl-5- [5- (5-cyclohexylpentanoyl) thiophen-2-yl] pentylphosphonic acid,
3-amino-3-methyl-5- [5- (5-phenylpentanoyl) thiophen-2-yl] pentylphosphonic acid,
3-amino-3-methyl-5- [5- [5- (4-fluorophenyl) pentanoyl] thiophen-2-yl] pentylphosphonic acid,
3-amino-3-ethyl-5- [5- (5-cyclohexylpentyl) thiophen-2-yl] pentylphosphonic acid and
2-Amino-2-ethyl-4- [5- (5-cyclohexylpentanoyl) thiophen-2-yl] pentylphosphonic acid.
[0020]
In the above compound (I), (2) to (3); (4) to (7); (8) to (12); (13) to (16); (17) to (18); (19) Thru (21); (22) thru (33); (34) thru (39); (40) thru (41); and (42) Is also suitable.
[0021]
In the above formula (I), R^FiveAnd “C” in the definition of substituent group b.₆-C_TenAryl group "," C substituted with 1 to 3 groups selected from substituent group a₆-C_TenC ”substituted with 1 to 3 groups selected from the group“ aryl group ”and“ substituent groups a and b ”₆-C_TenThe aryl part of the “aryl group” can be, for example, phenyl, indenyl or naphthyl, preferably a phenyl or naphthyl group, and most preferably a phenyl group.
[0022]
“C” in the definition of X₆-C_TenArylene group "," C substituted with 1 to 3 groups selected from the substituent group a₆-C_TenArylene group "and" C substituted with 1 to 3 groups selected from substituent groups a and b "₆-C_TenThe arylene moiety of the “arylene group” can be, for example, phenylene, indenylene or naphthylene, preferably a phenylene or naphthylene group, and most preferably a phenylene group.
[0023]
“C” in the definition of Y₁-C_TenC ”substituted with 1 to 3 groups selected from the group“ alkylene group ”and“ substituent groups a and b ”₁-C_TenC of "alkylene group"₁-C_TenThe alkylene moiety is, for example, methylene, methylmethylene, ethylene, propylene, trimethylene, 1-methylethylene, tetramethylene, 1-methyltrimethylene, 2-methyltrimethylene, 3-methyltrimethylene, 1-methylpropylene, 1, 1-dimethylethylene, pentamethylene, 1-methyltetramethylene, 2-methyltetramethylene, 3-methyltetramethylene, 4-methyltetramethylene, 1,1-dimethyltrimethylene, 2,2-dimethyltrimethylene, 3, 3-dimethyltrimethylene, hexamethylene, 1-methylpentamethylene, 2-methylpentamethylene, 3-methylpentamethylene, 4-methylpentamethylene, 5-methylpentamethylene, 1,1-dimethyltetramethylene, 2,2 -Dimethyltetramethylene, 3 3-dimethyltetramethylene, 4,4-dimethyltetramethylene, heptamethylene, 1-methylhexamethylene, 2-methylhexamethylene, 5-methylhexamethylene, 3-ethylpentamethylene, octamethylene, 2-methylheptamethylene, 5-methylheptamethylene, 2-ethylhexamethylene, 2-ethyl-3-methylpentamethylene, 3-ethyl-2-methylpentamethylene, nonamethylene, 2-methyloctamethylene, 7-methyloctamethylene, 4-ethylhepta It may be a linear or branched alkylene group having 1 to 10 carbon atoms such as methylene, 3-ethyl-2-methylhexamethylene, 2-ethyl-1-methylhexamethylene, decamethylene, and preferably C₁-C₆An alkylene group, and more preferably C.₁-C_FiveAn alkylene group, even more preferably an ethylene, trimethylene or tetramethylene group, and most preferably an ethylene or trimethylene group.
[0024]
In the definition of Y, “C having an oxygen atom or a sulfur atom in the carbon chain or at the chain end”₁-C_TenC having an oxygen atom or a sulfur atom in the carbon chain or at the chain end, substituted with 1 to 3 alkylene groups "and" a group selected from substituent groups a and b "₁-C_TenC having "oxygen atom or sulfur atom in carbon chain or at chain end" of "alkylene group"₁-C_TenThe “alkylene” moiety is defined above as “C₁-C_TenA group having an oxygen atom or a sulfur atom in the chain end or chain of the "alkylene group", for example, the formula -O-CH₂-, -O- (CH₂)₂-, -O- (CH₂)_Three-, -O- (CH₂)_Four-, -O- (CH₂)_Five-, -O- (CH₂)₆-, -O- (CH₂)₇-, -O- (CH₂)₈-, -O- (CH₂)₉-, -O- (CH₂)_Ten-, -CH₂-O-CH₂-, -CH₂-O- (CH₂)₂-, -CH₂-O- (CH₂)_Three-, -CH₂-O- (CH₂)_Four-,-(CH₂)₂-O-CH₂-,-(CH₂)₂-O- (CH₂)₂-,-(CH₂)₂-O- (CH₂)_Three-,-(CH₂)₂-O- (CH₂)_Four-,-(CH₂)_Three-O-CH₂-,-(CH₂)_Three-O- (CH₂)₂-,-(CH₂)_Three-O- (CH₂)_Three-,-(CH₂)_Four-O-CH₂-,-(CH₂)_Four-O- (CH₂)₂-,-(CH₂)_Five-O-CH₂-, -CH₂-O-,-(CH₂)₂-O-,-(CH₂)_Three-O-,-(CH₂)_Four-O-,-(CH₂)_Five-O-,-(CH₂)₆-O-,-(CH₂)₇-O-,-(CH₂)₈-O-,-(CH₂)₉-O-,-(CH₂)_Ten-O-, -S-CH₂-, -S- (CH₂)₂-, -S- (CH₂)_Three-, -S- (CH₂)_Four-, -S- (CH₂)_Five-, -S- (CH₂)₆-, -S- (CH₂)₇-, -S- (CH₂)₈-, -S- (CH₂)₉-, -S- (CH₂)_Ten-, -CH₂-S-CH₂-, -CH₂-S- (CH₂)₂-, -CH₂-S- (CH₂)_Three-, -CH₂-S- (CH₂)_Four-,-(CH₂)₂-S-CH₂-,-(CH₂)₂-S- (CH₂)₂-,-(CH₂)₂-S- (CH₂)_Three-,-(CH₂)₂-S- (CH₂)_Four-,-(CH₂)_Three-S-CH₂-,-(CH₂)_Three-S- (CH₂)₂-,-(CH₂)_Three-S- (CH₂)_Three-,-(CH₂)_Four-S-CH₂-,-(CH₂)_Four-S- (CH₂)₂-,-(CH₂)_Five-S-CH₂-, -CH₂-S-,-(CH₂)₂-S-,-(CH₂)_Three-S-,-(CH₂)_Four-S-,-(CH₂)_Five-S-,-(CH₂)₆-S-,-(CH₂)₇-S-,-(CH₂)₈-S-,-(CH₂)₉-S- or-(CH₂)_TenA group having —S—, preferably C having an oxygen atom in the carbon chain or at the chain end.₁-C₆An alkylene group, more preferably of the formula —O—CH.₂-, -O- (CH₂)₂-, -O- (CH₂)_Three-, -CH₂-O-,-(CH₂)₂-O- or-(CH₂)_ThreeA group having —O—, most preferably the formula —CH₂-O- or-(CH₂)₂It is a group having —O—.
[0025]
R^FiveAnd “C” in the definition of substituent group b._Three-C_TenA cycloalkyl group ”,“ C substituted with 1 to 3 groups selected from the substituent group a._Three-C_TenC 1 -C 3 substituted with a group selected from the group “cycloalkyl group” and “substituent groups a and b”_Three-C_TenC of cycloalkyl group_Three-C_TenThe cycloalkyl moiety may be fused with other cyclic groups such as a benzene ring, and can be, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, norbornyl, adamantyl or indanyl, preferably , C_Five-C₆A cycloalkyl group, and most preferably a cyclohexyl group.
[0026]
R^FiveAnd “a 5- to 7-membered heterocyclic group containing 1 to 3 sulfur atoms, oxygen atoms and / or nitrogen atoms” in the definition of the substituent group b, and 1 to 3 substitutions with a group selected from the substituent group a Sulfur substituted with 1 to 3 sulfur atoms, oxygen atoms and / or 5- to 7-membered heterocyclic groups containing 1 to 3 nitrogen atoms and a group selected from substituent groups a and b 5-7 membered heterocyclic group containing 1 to 3 atoms, oxygen atom and / or nitrogen atom "5 to 7 membered heterocyclic group containing 1 to 3 sulfur atom, oxygen atom and / or nitrogen atom The moiety represents a 5- to 7-membered aromatic group containing 1 to 3 sulfur atom, oxygen atom and / or nitrogen atom, or a partially or fully reduced saturated heterocyclic group, for example, furyl, thienyl, pyrrolyl, azepinyl , Pyrazolyl, imidazolyl, oxazolyl, isoxa Ryl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, triazolyl, tetrazolyl, thiadiazolyl, pyranyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, tetrahydropyranyl, morpholinyl, thiomorpholinyl, pyrrolidinyl, pyrrolinyl, imidazolidinyl, pyrazolidinyl, piperidinyl, piperidinyl It may be oxazolidinyl, isoxazolidinyl, thiazolidinyl or pyrazolidinyl, preferably a 5- to 6-membered aromatic heterocyclic group containing 1 to 3 sulfur atoms, oxygen atoms and / or nitrogen atoms, and more preferably Is furyl, thienyl or pyrrolyl, even more preferably furyl or thienyl, and most preferably thienyl.
[0027]
The above “aromatic heterocyclic group” may be condensed with another cyclic group, and examples thereof include benzothienyl, isobenzofuranyl, chromenyl, xanthenyl, phenoxathiinyl, indolizinyl, It can be isoindolyl, indolyl, indazolyl, purinyl, quinolidinyl, isoquinolyl, quinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, carbazolyl, carbolinyl, acridinyl or isoindolinyl, preferably a benzothienyl group.
[0028]
The “halogen atom” in the definition of the substituent group a is a fluorine, chlorine, bromine or iodine atom, preferably a fluorine atom or a chlorine atom.
[0029]
R^FourAnd "lower alkyl group" in the definition of substituent group a is, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, t-butyl, pentyl, isopentyl, 2-methylbutyl, neopentyl, 1-ethyl Propyl, hexyl, isohexyl, 4-methylpentyl, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl, 3,3-dimethylbutyl, 2,2-dimethylbutyl, 1,1-dimethylbutyl, 1,2 -It may be a linear or branched alkyl group having 1 to 6 carbon atoms such as dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl group, and preferably Is C₁-C_FourAn alkyl group, and more preferably C.₁-C₂An alkyl group, and most preferably a methyl group.
[0030]
R^FourIn the definition of “hydroxy lower alkyl group”, a group in which the “lower alkyl group” is substituted with a hydroxy group, for example, hydroxymethyl, 2-hydroxyethyl, 3-hydroxypropyl, 4-hydroxybutyl, 5-hydroxy Pentyl, hydroxy C such as 6-hydroxyhexyl group₁-C₆It can be an alkyl group, preferably hydroxy C₁-C_FourAn alkyl group, more preferably a hydroxymethyl or 2-hydroxyethyl group, and most preferably a hydroxymethyl group.
[0031]
The “halogeno lower alkyl group” in the definition of the substituent group a represents a group in which a halogen atom is substituted on the “lower alkyl group”, and examples thereof include trifluoromethyl, trichloromethyl, difluoromethyl, dichloromethyl, dibromomethyl, fluoro Methyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 2-bromoethyl, 2-chloroethyl, 2-fluoroethyl, 2-iodoethyl, 3-chloropropyl, 4-fluorobutyl, Halogeno C such as 6-iodohexyl, 2,2-dibromoethyl group₁-C₆It can be an alkyl group, preferably halogeno C₁-C_FourAn alkyl group, more preferably trifluoromethyl, trichloromethyl, 2,2,2-trifluoroethyl or 2,2,2-trichloroethyl, and most preferably a trifluoromethyl group.
[0032]
The “lower alkoxy group” in the definition of the substituent group a represents a group in which the “lower alkyl group” is bonded to an oxygen atom. For example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t -Butoxy, pentoxy, isopentoxy, 2-methylbutoxy, 1-ethylpropoxy, 2-ethylpropoxy, neopentoxy, hexyloxy, 4-methylpentoxy, 3-methylpentoxy, 2-methylpentoxy, 3,3-dimethyl Straight chain having 1 to 6 carbon atoms such as butoxy, 2,2-dimethylbutoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,3-dimethylbutoxy group, or It may be a branched alkoxy group, preferably C₁-C_FourAn alkoxy group, more preferably C₁-C₂An alkoxy group, most preferably a methoxy group.
[0033]
The “lower alkylthio group” in the definition of the substituent group a represents a group in which the “lower alkyl group” is bonded to a sulfur atom. For example, methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, s-butylthio, t-butylthio, pentylthio, isopentylthio, 2-methylbutylthio, neopentylthio, hexylthio, 4-methylpentylthio, 3-methylpentylthio, 2-methylpentylthio, 3,3-dimethylbutylthio, 2, Straight chain having 1 to 6 carbon atoms such as 2-dimethylbutylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,3-dimethylbutylthio group Or a branched alkylthio group, preferably C₁-C_FourAn alkylthio group, more preferably C₁-C₂An alkylthio group, and most preferably a methylthio group.
[0034]
R¹, R²And “lower alkoxycarbonyl group” in the definition of substituent group a represents a group in which the “lower alkoxy group” is bonded to a carbonyl group, such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, Isobutoxycarbonyl, s-butoxycarbonyl, t-butoxycarbonyl, pentoxycarbonyl, isopentoxycarbonyl, 2-methylbutoxycarbonyl, neopentoxycarbonyl, hexyloxycarbonyl, 4-methylpentoxycarbonyl, 3-methylpentoxy Carbonyl, 2-methylpentoxycarbonyl, 3,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxy Carbonyl, 1,3-dimethyl-butoxycarbonyl, be straight-chain or branched-chain alkoxycarbonyl group having 1 to 6 carbon atoms such as 2,3-dimethyl-butoxycarbonyl group, preferably, C₁-C_FourAn alkoxycarbonyl group, more preferably C₁-C₂An alkoxycarbonyl group, most preferably a methoxycarbonyl group.
[0035]
R¹, R²And “lower aliphatic acyl group” in the definition of substituent group a represents a group in which a hydrogen atom or a saturated or unsaturated chain hydrocarbon group is bonded to a carbonyl group, such as formyl, acetyl, propionyl, butyryl, It may be a linear or branched lower aliphatic acyl group having 1 to 8 carbon atoms such as isobutyryl, valeryl, isovaleryl, pivaloyl, hexanoyl, heptanoyl, octanoyl, acryloyl, methacryloyl, crotonoyl group, preferably C₁-C_FourIt is a lower aliphatic acyl group, more preferably an acetyl or propionyl group, and most preferably an acetyl group.
[0036]
The “mono-lower alkylamino group” in the definition of the substituent group a represents a group in which the aforementioned “lower alkyl group” is bonded to one amino group, for example, methylamino, ethylamino, propylamino, isopropylamino, butyl Amino, isobutylamino, s-butylamino, t-butylamino, pentylamino, isopentylamino, 2-methylbutylamino, neopentylamino, 1-ethylpropylamino, hexylamino, isohexylamino, 4-methylpentylamino 3-methylpentylamino, 2-methylpentylamino, 1-methylpentylamino, 3,3-dimethylbutylamino, 2,2-dimethylbutylamino, 1,1-dimethylbutylamino, 1,2-dimethylbutylamino 1,3-dimethylbutylamino, 2,3-dimethyl Chiruamino, mono -C such as 2-ethyl-butylamino group₁-C₆It can be an alkylamino group, preferably mono-C₁-C_FourAn alkylamino group, more preferably mono-C₁-C₂An alkylamino group, and most preferably a methylamino group.
[0037]
“Di-lower alkylamino group” in the definition of substituent group a represents a group in which two “lower alkyl groups” are bonded to an amino group, and examples thereof include dimethylamino, diethylamino, N-ethyl-N-methylamino. Di-C such as dipropylamino, dibutylamino, dipentylamino, dihexylamino groups₁-C₆It can be an alkylamino group, preferably di-C₁-C_FourAn alkylamino group, more preferably di-C₁-C₂An alkylamino group, and most preferably a dimethylamino group.
[0038]
In the above formula, the “lower aliphatic acylamino group” in the definition of the substituent group a represents a group in which the “lower aliphatic acyl group” is bonded to an amino group, such as formylamino, acetylamino, propionylamino, butyrylamino. A straight or branched lower aliphatic acylamino group having 1 to 7 carbon atoms such as, isobutyrylamino, valerylamino, isovalerylamino, pivaloylamino, hexanoylamino, acryloylamino, methacryloylamino, crotonoylamino group Preferably, C₁-C_FourIt is an aliphatic acylamino group, more preferably an acetylamino or propionylamino group, and most preferably an acetylamino group.
[0039]
R^ThreeAnd Ra^ThreeThe “protecting group for phosphate group” in the definition of
Lower alkyl groups such as methyl, ethyl, isopropyl, butyl,
A lower alkyl group substituted with a cyano group such as 2-cyanoethyl and 2-cyano-1,1-dimethylethyl;
A lower alkyl group substituted with a lower alkyl such as 2- (methyldiphenylsilyl) ethyl, 2-trimethylsilylethyl or a silyl group tri-substituted with lower alkyl and aryl,
A lower alkyl group substituted with heterocyclyl such as 2- (2'-pyridyl) ethyl, 2- (4'-pyridyl) ethyl,
Lower alkyl group substituted by arylthio such as 2-phenylthioethyl, 2- (4'-nitrophenylthio) ethyl, 2- (4'-triphenylmethylphenylthio) ethyl
A lower alkyl group substituted with alkylsulfonyl, arylsulfonyl or arylalkylsulfonyl such as 2- (t-butylsulfonyl) ethyl, 2- (phenylsulfonyl) ethyl, 2- (benzylsulfonyl) ethyl;
2,2,2-trichloroethyl, 2,2,2-trichloroethyl-1,1-dimethylethyl, 2,2,2-tribromoethyl, 2,3-dibromopropyl, 2,2,2-trifluoro A halogeno lower alkyl group such as ethyl;
Substituted with 1 to 3 aryl groups such as benzyl, phenethyl, 3-phenylpropyl, α-naphthylmethyl, β-naphthylmethyl, diphenylmethyl, triphenylmethyl, α-naphthyldiphenylmethyl, 9-anthrylmethyl Lower alkyl groups such as o-nitrobenzyl, 4-nitrobenzyl, 2,4-dinitrobenzyl, 4-chlorobenzyl, 4-chloro-2-nitrobenzyl, 4-acyloxybenzyl, halo, or lower aliphatic A lower alkyl group substituted with an aryl group in which the aryl ring is substituted with an acyl, a lower alkyl group substituted with an aryl group having a substituent such as 2-nitrophenylethyl, a fluorenyl such as 9-fluorenylmethyl Aralkyls such as a lower alkyl group substituted by a group;
Lower alkenyl groups such as allyl and propenyl,
A lower alkenyl group substituted with cyano, such as 4-cyano-2-butenyl;
An aryl group such as phenyl;
2-methylphenyl, 2,6-dimethylphenyl, 2-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2-bromophenyl, 4-nitrophenyl, 3, Lower alkyl such as 5-dinitrophenyl, 4-chloro-2-nitrophenyl, 2-methoxy-5-nitrophenyl, lower alkyl trisubstituted with aryl groups, aryl groups substituted with lower alkoxy, nitro or halo ;
And
Amides such as anilide, 4-triphenylmethylanilide, [N- (2-trityloxy) ethyl] anilide, p- (N, N-dimethylamino) anilide, 3- (N, N-diethylaminomethyl) anilide
It is.
[0040]
The “phosphate protecting group” is preferably a lower alkyl group, a lower alkenyl group or a methyl group substituted with 1-3 phenyl or naphthyl, more preferably a methyl group, an ethyl group, An allyl group or a benzyl group, and most preferably a methyl group or an ethyl group.
[0041]
R^FiveIn the definition of “C 1- to 3-substituent substituted with a group selected from substituent groups a and b”_Three-C_TenSpecific examples of the “cycloalkyl group” include, for example, 2-fluorocyclopropyl, 2-chlorocyclopropyl, 2- or 3-fluorocyclopentyl, 2- or 3-chlorocyclopentyl, 2-, 3- or 4-fluorocyclohexyl. 2-, 3- or 4-chlorocyclohexyl, 2-, 3- or 4-bromocyclohexyl, 2-, 3- or 4-iodocyclohexyl, 2-methylcyclopropyl, 2-ethylcyclopropyl, 2- Or 3-methylcyclopentyl, 2- or 3-ethylcyclopentyl, 2-, 3- or 4-methylcyclohexyl, 2-, 3- or 4-ethylcyclohexyl, 2-trifluoromethylcyclopropyl, 2- or 3-tri Fluoromethylcyclobutyl, 2-youth 3-trifluoromethylcyclopentyl, 2-, 3- or 4-trifluoromethylcyclohexyl, 2-methoxycyclopropyl, 2- or 3-methoxycyclobutyl, 2- or 3-methoxycyclopentyl, 2-, 3- or 4 -Methoxycyclohexyl, 2-, 3- or 4-ethoxycyclohexyl, 2-, 3- or 4-propoxycyclohexyl, 2-, 3- or 4-isopropoxycyclohexyl, 2-, 3- or 4- (1-ethyl) Propoxy) cyclohexyl, 2-, 3- or 4- (2-ethylpropoxy) cyclohexyl, 2-carboxycyclopropyl, 2- or 3-carboxycyclopentyl, 2-, 3- or 4-carboxycyclohexyl, 2-methoxycarbonylcyclo Propyl, 2- or 3-methoxycarbonylcyclopentyl, 2-, 3- or 4-methoxycarbonylcyclohexyl, 2-hydroxycyclopropyl, 2- or 3-hydroxycyclopentyl, 2-, 3- or 4-hydroxycyclohexyl, 2- Formylcyclopropyl, 2- or 3-formylcyclopentyl, 2-, 3- or 4-formylcyclohexyl, 2-acetylcyclopropyl, 2- or 3-acetylcyclopentyl, 2-, 3- or 4-acetylcyclohexyl, 2- Aminocyclopropyl, 2- or 3-aminocyclopentyl, 2-, 3- or 4-aminocyclohexyl, 2-methylaminocyclopropyl, 2- or 3-methylaminocyclobutyl, 2- or 3-methyl Aminocyclopentyl, 2-, 3- or 4-methylaminocyclohexyl, 2-dimethylaminocyclopropyl, 2- or 3-dimethylaminocyclobutyl, 2- or 3-dimethylaminocyclopentyl, 2-, 3- or 4-dimethyl Aminocyclohexyl, 2-cyanocyclopropyl, 2- or 3-cyanocyclopentyl, 2-, 3- or 4-cyanocyclohexyl, 2- or 3-cyclohexylcyclopentyl, 2-, 3- or 4-cyclohexylcyclohexyl, 2-phenyl Cyclopropyl, 2- or 3-phenylcyclopentyl, 2-, 3- or 4-phenylcyclohexyl, 3,4-difluorocyclohexyl, 3,4-dichlorocyclohexyl, 2,3-dimethoxycyclohexyl 3,4-dimethoxy-cyclohexyl, 3,5-dimethoxyphenyl cyclohexyl, be a 3,4,5 cyclohexyl group, preferably, 1 to 3-substituted C_Three-C_TenA cycloalkyl group (the substituent is a group selected from the group consisting of a halogen atom, a lower alkyl group, a halogeno lower alkyl group, a lower alkoxy group, a lower alkylthio group and a lower aliphatic acyl group); Preferably 1 to 3 substituted C_Three-C_TenA cycloalkyl group (the substituent is a group selected from the group consisting of a halogen atom, a lower alkyl group, a halogeno lower alkyl group, a lower alkoxy group and a lower aliphatic acyl group), and more preferably. 1-substituted cyclohexyl group (the substituent is a group selected from the group consisting of a halogen atom, a lower alkyl group, a halogeno lower alkyl group, a lower alkoxy group and a lower aliphatic acyl group); Most preferably, it is a mono-substituted cyclohexyl group (the substituent is a group selected from the group consisting of a fluorine atom, a chlorine atom, methyl, trifluoromethyl, methoxy and acetyl groups).
[0042]
R^FiveIn the definition of “C 1- to 3-substituent substituted with a group selected from substituent groups a and b”₆-C_TenSpecific examples of the “aryl group” include, for example, 2-, 3- or 4-fluorophenyl, 2-, 3- or 4-chlorophenyl, 2-, 3- or 4-bromophenyl, 2-, 3- or 4- Iodophenyl, 2-, 3- or 4-methylphenyl, 2-, 3- or 4-ethylphenyl, 2-, 3- or 4-propylphenyl, 2-, 3- or 4-butylphenyl, 2- , 3- or 4-pentylphenyl, 2-, 3- or 4-trifluoromethylphenyl, 2-, 3- or 4-methoxyphenyl, 2-, 3- or 4-ethoxyphenyl, 2-, 3- or 4-propoxyphenyl, 2-, 3- or 4-isopropoxyphenyl, 2-, 3- or 4-butoxyphenyl, 2-, 3- or 4- (1- Tilpropoxy) phenyl, 2-, 3- or 4- (2-ethylpropoxy) phenyl, 2-, 3- or 4-methylthiophenyl, 2-, 3- or 4-ethylthiophenyl, 2-, 3- or 4-carboxyphenyl, 2-, 3- or 4-methoxycarbonylphenyl, 2-, 3- or 4-ethoxycarbonylphenyl, 2-, 3- or 4-hydroxyphenyl, 2-, 3- or 4-formylphenyl 2-, 3- or 4-acetylphenyl, 2-, 3- or 4-aminophenyl, 2-, 3- or 4-methylaminophenyl, 2-, 3- or 4-dimethylaminophenyl, 2-, 3- or 4-cyanophenyl, 2-, 3- or 4-cyclopentylphenyl, 2-, 3- or 4- Chlohexylphenyl, 2-, 3- or 4-biphenyl, 2,4-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 3,5 -Dichlorophenyl, 3,4-dibromophenyl, 2,3-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2,3-dimethoxyphenyl, 3,4-dimethoxyphenyl, 3,5-dimethoxy Phenyl, 3,4,5-trimethoxyphenyl, 3-fluoro-4-methoxyphenyl, 4-methyl-2-methoxyphenyl, 6-fluoro-4-methyl-2-methoxyphenyl, 5-fluoroindene-3- Yl, 5-fluoroinden-3-yl, 5-methylinden-3-yl, 5-methoxyi Nden-3-yl, 5-fluoroinden-2-yl, 5-chloroinden-2-yl, 5-methylinden-2-yl, 5-methoxyinden-2-yl, 5-hydroxyinden-3-yl 5-nitroinden-3-yl, 5-cyclohexylinden-3-yl, 5-phenylinden-3-yl, 5-phenoxyinden-3-yl, 5-benzyloxyinden-3-yl, 5-phenyl Thioinden-3-yl, 5-hydroxyinden-2-yl, 5-nitroinden-2-yl, 5-cyclohexylinden-2-yl, 5-phenylinden-2-yl, 5-fluoronaphthalene-2- Yl, 5-fluoronaphthalen-2-yl, 5-methylnaphthalen-2-yl, 5-methoxynaphthalen-2-yl, 5-fluoronaphthal Talen-1-yl, 5-fluoronaphthalen-1-yl, 5-methylnaphthalen-1-yl, 5-methoxynaphthalen-1-yl, 5-hydroxynaphthalen-2-yl, 5-nitronaphthalen-2-yl 5-cyclohexylnaphthalen-2-yl, 5-phenylnaphthalen-2-yl, 5-phenoxynaphthalen-2-yl, 5-benzyloxynaphthalen-2-yl, 5-phenylthionaphthalen-2-yl, 5- Hydroxynaphthalen-1-yl, 5-nitronaphthalen-1-yl, 5-cyclohexylnaphthalen-1-yl, 5-phenylnaphthalen-1-yl, preferably 1 to 3 substituted C₆-C_TenAn aryl group (the substituent is a group selected from the group consisting of a halogen atom, a lower alkyl group, a halogeno lower alkyl group, a lower alkoxy group, a lower alkylthio group, and a lower aliphatic acyl group), and more preferably. Includes 1 to 3 substituted C₆-C_TenAn aryl group (the substituent is a group selected from the group consisting of a halogen atom, a lower alkyl group, a halogeno lower alkyl group, a lower alkoxy group and a lower aliphatic acyl group), and more preferably, 1 to 3 substituted phenyl groups (the substituent is a group selected from the group consisting of a halogen atom, a lower alkyl group, a halogeno lower alkyl group, a lower alkoxy group, and a lower aliphatic acyl group). Even more preferably, one or two substituted phenyl groups (the substituent is a group selected from the group consisting of fluorine atom, chlorine atom, methyl, trifluoromethyl, methoxy and acetyl group, provided that The methoxy group is preferably a phenyl group having 1 to 3 substituents.), And most preferably 3-fluorophenyl, 4-fluorophenyl, 3 4-difluorophenyl, 3,5-difluorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 3-methylphenyl, 4-methylphenyl, 3,4-dimethylphenyl, 3 , 5-dimethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 3,4-ditrifluoromethylphenyl, 3,5-ditrifluoromethylphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3, 4-dimethoxyphenyl, 3,5-dimethoxyphenyl, 3,4,5-trimethoxyphenyl, 3-acetylphenyl or 4-acetylphenyl group.
[0043]
R^FiveSpecific examples of “5- to 7-membered heterocyclic group containing 1 to 3 sulfur atoms, oxygen atoms and / or nitrogen atoms, substituted by 1 to 3 groups selected from substituent groups a and b” in the definition of Examples are, for example, 3-, 4- or 5-methylfuran-2-yl, 2-, 4- or 5-methylfuran-3-yl, 3-, 4- or 5-fluorothiophen-2-yl, 2-, 4- or 5-fluorofuran-3-yl, 3-, 4- or 5-bromothiophen-2-yl, 2-, 4- or 5-bromofuran-3-yl, 3-, 4- or 5-methylthiophen-2-yl, 2-, 4- or 5-methylthiophen-3-yl, 3-, 4- or 5-ethylthiophen-2-yl, 2-, 4- or 5-ethylthiophene- 3-yl, 3-, 4-young Is 5-methoxythiophen-2-yl, 2-, 4- or 5-methoxythiophen-3-yl, 3- or 4-methylthiazol-5-yl, 3-, 4- or 5-fluorobenzothiophene- 2-yl, 3-, 4- or 5-bromobenzothiophen-2-yl, 3-, 4- or 5-methylbenzothiophen-2-yl, 3-, 4- or 5-methoxybenzothiophen-2-yl Yl, 2-, 4- or 5-fluorobenzothiophen-3-yl, 2-, 4- or 5-bromobenzothiophen-3-yl, 2-, 4- or 5-methylbenzothiophen-3-yl, 2-, 4- or 5-methoxybenzothiophen-3-yl, 4-, 5-, 6- or 7-methylbenzothiophen-2-yl, 3-, 4- Is 5-hydroxyfuran-2-yl, 2-, 4- or 5-hydroxyfuran-3-yl, 3-, 4- or 5-hydroxythiophen-2-yl, 3-, 4- or 5-nitrothiophene 2-yl, 3-, 4- or 5-phenylthiophen-2-yl, 2-, 4- or 5-hydroxythiophen-3-yl, 2-, 4- or 5-cyanothiophen-3-yl, 1-, 2- or 3-hydroxypyridin-4-yl, 1-, 2- or 3-cyanopyridin-4-yl, 1-, 2- or 3-phenylpyridin-4-yl group, preferably Is a 3-, 4- or 5-fluorothiophen-2-yl or 2-, 4- or 5-fluorofuran-3-yl group.
[0044]
“Pharmaceutically acceptable salt thereof” means that the compound having the general formula (I) of the present invention has a basic group such as an amino group, and is reacted with an acid. When it has an acidic group such as a group, it can be converted into a salt by reacting with a base, so that the salt is shown.
[0045]
Salts based on basic groups are, for example, hydrohalides, nitrates, perchlorates, sulfates such as hydrofluorates, hydrochlorides, hydrobromides, hydroiodides, Inorganic acid salts such as phosphates; lower alkane sulfonates such as methane sulfonate, trifluoromethane sulfonate and ethane sulfonate, aryl sulfonic acids such as benzene sulfonate and p-toluene sulfonate Organic salts such as salt, acetate, malate, fumarate, succinate, citrate, ascorbate, tartrate, oxalate, maleate; or glycine salt, lysine salt, arginine salt Amino acid salts such as ornithine, glutamate, aspartate, preferably organic acid salts (especially fumarate, oxalate or maleate) or halogenated Periodate (particularly hydrochloride) is.
[0046]
On the other hand, salts based on acidic groups include, for example, alkali metal salts such as sodium salt, potassium salt and lithium salt, alkaline earth metal salts such as calcium salt and magnesium salt, metal salts such as aluminum salt and iron salt Inorganic salts such as ammonium salts, t-octylamine salts, dibenzylamine salts, morpholine salts, glucosamine salts, phenylglycine alkyl ester salts, ethylenediamine salts, N-methylglucamine salts, guanidine salts, diethylamine salts, triethylamine salts , Dicyclohexylamine salt, N, N′-dibenzylethylenediamine salt, chloroprocaine salt, procaine salt, diethanolamine salt, N-benzylphenethylamine salt, piperazine salt, tetramethylammonium salt, tris (hydroxymethyl) aminomethane salt Organic Amine salts and the like; or glycine salts, lysine salts, arginine salts, ornithine salts, glutamate, be an amino acid salt such as aspartate, preferably a alkali metal salt (particularly sodium salt).
[0047]
The compound having the general formula (I) of the present invention, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof can absorb moisture by being left in the atmosphere or by recrystallization. Adsorbed water may be attached or a hydrate may be formed, and such a hydrate is also included in the salt of the present invention.
[0048]
Since the compound having the general formula (I), the pharmacologically acceptable salt thereof or the pharmacologically acceptable ester thereof of the present invention has an asymmetric carbon atom in the molecule, optical isomers exist. In the compounds of the present invention, the optical isomer and the mixture of optical isomers are all represented by a single formula, that is, the general formula (I). Accordingly, the present invention includes all optical isomers and mixtures of optical isomers in an arbitrary ratio.
[0049]
The compounds having the general formula (I) of the present invention are preferably of the formula —NR¹R²A compound having an absolute coordination of R with respect to an asymmetric carbon atom to which a group having R is bonded.
[0050]
The “ester” in the above is an ester, since the compound having the above general formula (I) can be converted into an ester, and as such an ester, “ester of hydroxy group” and “carboxyl group” An ester in which each ester residue is a “general protecting group in a reaction” or a “protecting group that can be cleaved by biological methods such as hydrolysis in vivo”.
[0051]
“General protecting group in reaction” refers to a protecting group that can be cleaved by a chemical method such as hydrogenolysis, hydrolysis, electrolysis, or photolysis.
[0052]
A “general protecting group in the reaction” such as “ester of hydroxy group” is, for example,
The “lower aliphatic acyl group”, a halogeno lower aliphatic acyl group such as chloroacetyl, dichloroacetyl, trichloroacetyl and trifluoroacetyl, a lower aliphatic acyl group substituted with lower alkoxy such as methoxyacetyl, etc. Aliphatic acyls ";
Aromatic acyl groups such as benzoyl, 1-indanecarbonyl, 2-indanecarbonyl, 1- or 2-naphthoyl, 4-chlorobenzoyl, 4-fluorobenzoyl, 2,4,6-trimethylbenzoyl, 4-toluoyl, 4 An aromatic acyl group substituted with 1 to 3 groups selected from the substituent group a such as anisoyl 4-nitrobenzoyl, 2-nitrobenzoyl, 2- (methoxycarbonyl) benzoyl, 4-phenylbenzoyl, etc. "Aromatic acyls";
“Tetrahydro, such as tetrahydropyran-2-yl, 3-bromotetrahydropyran-2-yl, 4-methoxytetrahydropyran-4-yl, tetrahydrothiopyran-2-yl, 4-methoxytetrahydrothiopyran-4-yl Pyranyl or tetrahydrothiopyranyls ";
“Tetrahydrofuranyl or tetrahydrothiofuranyls” such as tetrahydrofuran-2-yl, tetrahydrothiofuran-2-yl;
Tri-lower alkylsilyl groups such as trimethylsilyl, triethylsilyl, isopropyldimethylsilyl, t-butyldimethylsilyl, methyldiisopropylsilyl, methyldi-t-butylsilyl, triisopropylsilyl, diphenylmethylsilyl, diphenylbutylsilyl, diphenylisopropylsilyl, phenyl “Silyls” such as aryl such as diisopropylsilyl or silyl groups trisubstituted with aryl and lower alkyl;
Lower alkoxymethyl groups such as methoxymethyl, 1,1-dimethyl-1-methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, butoxymethyl, t-butoxymethyl, lower alkoxylation such as 2-methoxyethoxymethyl An “alkoxymethyl group” such as a lower alkoxymethyl group, a halogeno lower alkoxymethyl such as 2,2,2-trichloroethoxymethyl, bis (2-chloroethoxy) methyl;
“Substituted ethyls” such as 1-ethoxyethyl, lower alkoxylated ethyl groups such as 1- (isopropoxy) ethyl, and halogenated ethyl groups such as 2,2,2-trichloroethyl;
Substituted with 1 to 3 aryl groups such as benzyl, phenethyl, 3-phenylpropyl, α-naphthylmethyl, β-naphthylmethyl, diphenylmethyl, triphenylmethyl, α-naphthyldiphenylmethyl, 9-anthrylmethyl Lower alkyl group, 4-methylbenzyl, 2,4,6-trimethylbenzyl, 3,4,5-trimethylbenzyl, 4-methoxybenzyl, 4-methoxyphenyldiphenylmethyl, 2-nitrobenzyl, 4-nitrobenzyl, 4-chlorobenzyl, 4-bromobenzyl, 4-cyanobenzyl, 4-cyanobenzyldiphenylmethyl, bis (2-nitrophenyl) methyl, lower alkyl such as piperonyl, lower alkoxy, nitro, halo or cyano with an aryl ring Substituted with 1 to 3 substituted aryl groups "Aralkyl such" such as a lower alkyl group;
“Alkoxycarbonyls” such as the above-mentioned “lower alkoxycarbonyl group”, lower alkoxycarbonyl groups substituted with halogen or tri-lower alkylsilyl such as 2,2,2-trichloroethoxycarbonyl, 2-trimethylsilylethoxycarbonyl;
“Alkenyloxycarbonyls” such as vinyloxycarbonyl, allyloxycarbonyl; or
Selected from the above-mentioned substituent group a such as aralkyloxycarbonyl group such as benzyloxycarbonyl, 4-methoxybenzyloxycarbonyl, 3,4-dimethoxybenzyloxycarbonyl, 2-nitrobenzyloxycarbonyl, 4-nitrobenzyloxycarbonyl And “aralkyloxycarbonyls” such as an aralkyloxycarbonyl group substituted with 1 to 3 of the above groups.
[0053]
On the other hand, “protecting group that can be cleaved by biological methods such as hydrolysis in vivo” means a protective group that is cleaved by biological methods such as hydrolysis in the human body to produce a free acid or a salt thereof. Whether or not it is a derivative is administered to a laboratory animal such as a rat or mouse by intravenous injection, and then the body fluid of the animal is examined to determine the original compound or a pharmacologically acceptable salt thereof. Can be determined. A “protecting group that can be cleaved by biological methods such as hydrolysis in vivo” according to “esters of hydroxy groups”, for example,
Acyloxyalkyls such as ethylcarbonyloxymethyl, pivaloyloxymethyl, dimethylaminoacetyloxymethyl, 1-acetoxyethyl;
1- (methoxycarbonyloxy) ethyl, 1- (ethoxycarbonyloxy) ethyl, ethoxycarbonyloxymethyl, 1- (isopropoxycarbonyloxy) ethyl, 1- (t-butoxycarbonyloxy) ethyl, 1- (ethoxycarbonyloxy) ) 1- (alkoxycarbonyloxy) alkyls such as propyl, 1- (cyclohexyloxycarbonyloxy) ethyl;
Phthalidyl group;
“Carbonyloxyalkyls” such as oxodioxorenylmethyl groups such as 4-methyl-oxodioxorenylmethyl, 4-phenyl-oxodioxorenylmethyl, oxodioxorenylmethyl;
The “aliphatic acyls”;
The “aromatic acyls”;
“Half-ester salt residue of succinic acid”;
“Phosphate ester residue”;
“Ester forming residues such as amino acids”;
A carbamoyl group;
An aralkylidene group such as benzylidene; an alkoxyethylidene group such as methoxyethylidene, ethoxyethylidene; oxomethylene; a “protecting group for two hydroxy groups” such as thiooxomethylene; or
A “carbonyloxyalkyloxycarbonyl group” such as pivaloyloxymethyloxycarbonyl, preferably 1 to 3 groups selected from a lower aliphatic acyl group, an aromatic acyl group or a substituent group a; It is a substituted aromatic acyl group.
[0054]
The “hydroxy-protecting group” is particularly preferably an aliphatic acyl group or an aromatic acyl group.
[0055]
The “general protecting group in the reaction” in the “ester of carboxyl group” is preferably the aforementioned “lower alkyl group”; ethenyl, 1-propenyl, 2-propenyl, 1-methyl-2-propenyl, 1- Methyl-1-propenyl, 2-methyl-1-propenyl, 2-methyl-2-propenyl, 2-ethyl-2-propenyl, 1-butenyl, 2-butenyl, 1-methyl-2-butenyl, 1-methyl- 1-butenyl, 3-methyl-2-butenyl, 1-ethyl-2-butenyl, 3-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 1-ethyl-3-butenyl, 1- Pentenyl, 2-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl Lower alkenyl groups such as 4-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl; ethynyl, 2- Propynyl, 1-methyl-2-propynyl, 2-methyl-2-propynyl, 2-ethyl-2-propynyl, 2-butynyl, 1-methyl-2-butynyl, 2-methyl-2-butynyl, 1-ethyl- 2-butynyl, 3-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-ethyl-3-butynyl, 2-pentynyl, 1-methyl-2-pentynyl, 2-methyl-2- Pentynyl, 3-pentynyl, 1-methyl-3-pentynyl, 2-methyl-3-pentynyl, 4-pentynyl, 1-methyl-4-pentynyl, 2-methyl Lower alkynyl groups such as ru-4-pentynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl; said “halogeno lower alkyl”; 2-hydroxyethyl, 2,3-dihydroxypropyl, 3-hydroxy Hydroxy “lower alkyl” such as propyl, 3,4-dihydroxybutyl, 4-hydroxybutyl; “lower aliphatic acyl” such as acetylmethyl— “lower alkyl”; said “aralkyl”; A silyl group.
[0056]
The “protecting group that can be cleaved by biological methods such as hydrolysis in vivo” such as “ester of carboxyl group” is preferably methoxyethyl, 1-ethoxyethyl, 1-methyl-1-methoxy. Ethyl, 1- (isopropoxy) ethyl, 2-methoxyethyl, 2-ethoxyethyl, 1,1-dimethyl-1-methoxyethyl, ethoxymethyl, n-propoxymethyl, isopropoxymethyl, n-butoxymethyl, t- Lower alkoxy lower alkyl groups such as butoxymethyl, lower alkoxylated lower alkoxy lower alkyl groups such as 2-methoxyethoxymethyl, “aryl” oxy “lower alkyl groups” such as phenoxymethyl, 2,2,2-trichloro Halogenated lower alkoxides such as ethoxymethyl and bis (2-chloroethoxy) methyl “Alkoxyalkyl groups” such as lower alkyl groups; ““ lower alkoxy ”carbonyl“ lower alkyl groups ”” such as methoxycarbonylmethyl; “cyano“ lower alkyl groups ”” such as cyanomethyl and 2-cyanoethyl; methylthiomethyl, “Lower alkyl” thiomethyl groups such as ethylthiomethyl; ““ aryl ”thiomethyl groups” such as phenylthiomethyl and naphthylthiomethyl; “halogens” such as 2-methanesulfonylethyl and 2-trifluoromethanesulfonylethyl "Lower alkyl" sulfonyl "lower alkyl group" "optionally substituted with" "aryl" sulfonyl "lower alkyl group" such as 2-benzenesulfonylethyl and 2-toluenesulfonylethyl; Acyloxy) "lower alkyl group" "; previous Is or "amide forming residues of amino acids" such as phenylalanine; "phthalidyl group"; the "aryl group"; the "lower alkyl group"; carboxy "carboxyalkyl group" such as methyl.
[0057]
In the above “general protecting group in reaction” and “protecting group cleavable by biological methods such as hydrolysis in vivo” in the above “ester of carboxy group”, more preferably lower alkyl or aralkyl. It is a group.
[0058]
Specific examples of the compound having the general formula (I) of the present invention include the compounds described in Table 1 and Table 2 below, but the present invention is not limited to these compounds. . In the compounds represented by the same compound number, Z is O or —CH₂-Shows two compounds.
[0059]
Abbreviations in the table are as follows.
Bu: butyl group
iBu: Isobutyl group
Bz: benzyl group
Et: ethyl group
cHx: cyclohexyl group
Me: methyl group
Np (1): naphthalen-1-yl group
Np (2): Naphthalen-2-yl group
Ph: phenyl group
cPn: cyclopentyl group
Pr: Propyl group
iPr: Isopropyl group.
[0060]
Table 1
[0061]
[Chemical 7]

[0062]
[Table 1]
――――――――――――――――――――――――――――――――――――
Compd. R¹    R²  R^Three  R_a ^Three  R^Four   n -X-Y-R^Five                       R⁶  R⁷
――――――――――――――――――――――――――――――――――――
1-1 H H H H Me 1-(CH₂)_Five-cHx H H
1-2 H H H H Me 1-(CH₂)₆-cHx H H
1-3 H H H H Me 1 -CH = CH- (CH₂)_Three-cHx H H
1-4 H H H H Me 1 -CH = CH- (CH₂)_Four-cHx H H
1-5 H H H H Me 1 -C≡C- (CH₂)_Three-cHx H H
1-6 H H H H Me 1 -C≡C- (CH₂)_Four-cHx H H
1-7 H H H H Me 1 -CO- (CH₂)_Four-cHx H H
1-8 H H H H Me 1 -CO- (CH₂)_Five-cHx H H
1-9 H H H H Me 1 -CH (OH)-(CH₂)_Four-cHx H H
1-10 H H H H Me 1 -CH (OH)-(CH₂)_Five-cHx H H
1-11 H H H H Me 1 -4- (cHx-CH₂O) Ph H H
1-12 H H H H Me 1-(4-BzO-Ph) H H
1-13 H H H H Me 1 -C≡C-CH₂O-cPn H H
1-14 H H H H Me 1 -C≡C- (CH₂)₂O-cPn H H
1-15 H H H H Me 1 -C≡C-CH₂O-cHx H H
1-16 H H H H Me 1 -C≡C- (CH₂)₂O-cHx H H
1-17 H H H H Me 1 -C≡C-CH₂O-Ph H H
1-18 H H H H Me 1 -C≡C- (CH₂)₂O-Ph H H
1-19 H H H H Me 2-(CH₂)₂-cHx H H
1-20 H H H H Me 2-(CH₂)₂-cHx H H
1-21 CO₂Me H H H Me 2-(CH₂)₂-cHx H H
1-22 CO₂Et H H H Me 2-(CH₂)₂-cHx H H
1-23 H H H H Me 2-(CH₂)₂-(4-F-cHx) H H
1-24 H H H H Me 2-(CH₂)₂-(4-Me-cHx) H H
1-25 H H H H Me 2-(CH₂)₂-(4-Et-cHx) H H
1-26 H H H H Me 2-(CH₂)₂-(4-CF_Three-cHx) H H
1-27 H H H H Me 2-(CH₂)₂-(4-MeO-cHx) H H
1-28 H H H H Me 2-(CH₂)₂-(4-EtO-cHx) H H
1-29 H H H H Me 2-(CH₂)₂-(4-MeS-cHx) H H
1-30 H H H H Me 2-(CH₂)₂-(4-cHx-cHx) H H
1-31 H H H H Me 2-(CH₂)₂-(4-Ph-cHx) H H
1-32 H H H H Me 2-(CH₂)₂-Ph H H
1-33 H H H H Me 2-(CH₂)₂-Ph H H
1-34 CO₂Me H H H Me 2-(CH₂)₂-Ph H H
1-35 CO₂Et H H H Me 2-(CH₂)₂-Ph H H
1-36 H H H H Me 2-(CH₂)₂-(4-F-Ph) H H
1-37 H H H H Me 2-(CH₂)₂-(4-Me-Ph) H H
1-38 H H H H Me 2-(CH₂)₂-(4-Et-Ph) H H
1-39 H H H H Me 2-(CH₂)₂-(4-CF_Three-Ph) H H
1-40 H H H H Me 2-(CH₂)₂-(4-MeO-Ph) H H
1-41 H H H H Me 2-(CH₂)₂-(4-EtO-Ph) H H
1-42 H H H H Me 2-(CH₂)₂-(4-MeS-Ph) H H
1-43 H H H H Me 2-(CH₂)₂-(4-cHx-Ph) H H
1-44 H H H H Me 2-(CH₂)₂-(4-Ph-Ph) H H
1-45 H H H H Me 2-(CH₂)_Three-cHx H H
1-46 H H Me Me Me 2-(CH₂)_Three-cHx H H
1-47 CO₂Me H H H Me 2-(CH₂)_Three-cHx H H
1-48 CO₂Et H H H Me 2-(CH₂)_Three-cHx H H
1-49 H H H H Me 2-(CH₂)_Three-(4-F-cHx) H H
1-50 H H H H Me 2-(CH₂)_Three-(4-Me-cHx) H H
1-51 H H H H Me 2-(CH₂)_Three-(4-Et-cHx) H H
1-52 H H H H Me 2-(CH₂)_Three-(4-CF_Three-cHx) H H
1-53 H H H H Me 2-(CH₂)_Three-(4-MeO-cHx) H H
1-54 H H H H Me 2-(CH₂)_Three-(4-EtO-cHx) H H
1-55 H H H H Me 2-(CH₂)_Three-(4-MeS-cHx) H H
1-56 H H H H Me 2-(CH₂)_Three-(4-cHx-cHx) H H
1-57 H H H H Me 2-(CH₂)_Three-(4-Ph-cHx) H H
1-58 H H H H Me 2-(CH₂)_Three-Ph H H
1-59 H H Me Me Me 2-(CH₂)_Three-Ph H H
1-60 CO₂Me H H H Me 2-(CH₂)_Three-Ph H H
1-61 CO₂Et H H H Me 2-(CH₂)_Three-Ph H H
1-62 H H H H Me 2-(CH₂)_Three-(4-F-Ph) H H
1-63 H H H H Me 2-(CH₂)_Three-(4-Me-Ph) H H
1-64 H H H H Me 2-(CH₂)_Three-(4-Et-Ph) H H
1-65 H H H H Me 2-(CH₂)_Three-(4-CF_Three-Ph) H H
1-66 H H H H Me 2-(CH₂)_Three-(4-MeO-Ph) H H
1-67 H H H H Me 2-(CH₂)_Three-(4-EtO-Ph) H H
1-68 H H H H Me 2-(CH₂)_Three-(4-MeS-Ph) H H
1-69 H H H H Me 2-(CH₂)_Three-(4-cHx-Ph) H H
1-70 H H H H Me 2-(CH₂)_Three-(4-Ph-Ph) H H
1-71 H H H H Me 2-(CH₂)_Four-cHx H H
1-72 H H H H Me 2-(CH₂)_Four-cHx H H
1-73 CO₂Me H H H Me 2-(CH₂)_Four-cHx H H
1-74 CO₂Et H H H Me 2-(CH₂)_Four-cHx H H
1-75 H H H H Me 2-(CH₂)_Four-(4-F-cHx) H H
1-76 H H H H Me 2-(CH₂)_Four-(4-Me-cHx) H H
1-77 H H H H Me 2-(CH₂)_Four-(4-Et-cHx) H H
1-78 H H H H Me 2-(CH₂)_Four-(4-CF_Three-cHx) H H
1-79 H H H H Me 2-(CH₂)_Four-(4-MeO-cHx) H H
1-80 H H H H Me 2-(CH₂)_Four-(4-EtO-cHx) H H
1-81 H H H H Me 2-(CH₂)_Four-(4-MeS-cHx) H H
1-82 H H H H Me 2-(CH₂)_Four-(4-cHx-cHx) H H
1-83 H H H H Me 2-(CH₂)_Four-(4-Ph-cHx) H H
1-84 H H H H Me 2-(CH₂)_Four-Ph H H
1-85 H H H H Me 2-(CH₂)_Four-Ph H H
1-86 CO₂Me H H H Me 2-(CH₂)_Four-Ph H H
1-87 CO₂Et H H H Me 2-(CH₂)_Four-Ph H H
1-88 H H H H Me 2-(CH₂)_Four-(4-F-Ph) H H
1-89 H H H H Me 2-(CH₂)_Four-(4-Me-Ph) H H
1-90 H H H H Me 2-(CH₂)_Four-(4-Et-Ph) H H
1-91 H H H H Me 2-(CH₂)_Four-(4-CF_Three-Ph) H H
1-92 H H H H Me 2-(CH₂)_Four-(4-MeO-Ph) H H
1-93 H H H H Me 2-(CH₂)_Four-(4-EtO-Ph) H H
1-94 H H H H Me 2-(CH₂)_Four-(4-MeS-Ph) H H
1-95 H H H H Me 2-(CH₂)_Four-(4-cHx-Ph) H H
1-96 H H H H Me 2-(CH₂)_Four-(4-Ph-Ph) H H
1-97 H H H H Me 2-(CH₂)_Five-cPn H H
1-98 H H H H Me 2-(CH₂)_Five-cHx H H
1-99 H H H H Me 2-(CH₂)_Five-cHx Me H
1-100 H H H H Me 2-(CH₂)_Five-cHx H Me
1-101 H H H H Me 2-(CH₂)_Five-cHx F H
1-102 H H H H Me 2-(CH₂)_Five-cHx H F
1-103 H H H H Me 2-(CH₂)_Five-cHx H H
1-104 CO₂Me H H H Me 2-(CH₂)_Five-cHx H H
1-105 CO₂Et H H H Me 2-(CH₂)_Five-cHx H H
1-106 H H H H Me 2-(CH₂)_Five-(3-F-cHx) H H
1-107 H H H H Me 2-(CH₂)_Five-(4-F-cHx) H H
1-108 H H H H Me 2-(CH₂)_Five-(4-Cl-cHx) H H
1-109 H H H H Me 2-(CH₂)_Five-(4-Br-cHx) H H
1-110 H H H H Me 2-(CH₂)_Five-(3-Me-cHx) H H
1-111 H H H H Me 2-(CH₂)_Five-(4-Me-cHx) H H
1-112 H H H H Me 2-(CH₂)_Five-(3-Et-cHx) H H
1-113 H H H H Me 2-(CH₂)_Five-(4-Et-cHx) H H
1-114 H H H H Me 2-(CH₂)_Five-(3-Pr-cHx) H H
1-115 H H H H Me 2-(CH₂)_Five-(4-Pr-cHx) H H
1-116 H H H H Me 2-(CH₂)_Five-(4-iPr-cHx) H H
1-117 H H H H Me 2-(CH₂)_Five-(3-Bu-cHx) H H
1-118 H H H H Me 2-(CH₂)_Five-(4-Bu-cHx) H H
1-119 H H H H Me 2-(CH₂)_Five-(3-CF_Three-cHx) H H
1-120 H H H H Me 2-(CH₂)_Five-(4-CF_Three-cHx) H H
1-121 H H H H Me 2-(CH₂)_Five-(3-MeO-cHx) H H
1-122 H H H H Me 2-(CH₂)_Five-(4-MeO-cHx) H H
1-123 H H H H Me 2-(CH₂)_Five-(3-EtO-cHx) H H
1-124 H H H H Me 2-(CH₂)_Five-(4-EtO-cHx) H H
1-125 H H H H Me 2-(CH₂)_Five-(3-PrO-cHx) H H
1-126 H H H H Me 2-(CH₂)_Five-(4-PrO-cHx) H H
1-127 H H H H Me 2-(CH₂)_Five-(3-iPrO-cHx) H H
1-128 H H H H Me 2-(CH₂)_Five-(4-iPrO-cHx) H H
1-129 H H H H Me 2-(CH₂)_Five-[3- (2-Et-PrO) -cHx] H H
1-130 H H H H Me 2-(CH₂)_Five-[4- (2-Et-PrO) -cHx] H H
1-131 H H H H Me 2-(CH₂)_Five-(3-iBuO-cHx) H H
1-132 H H H H Me 2-(CH₂)_Five-(4-iBuO-cHx) H H
1-133 H H H H Me 2-(CH₂)_Five-(3-MeS-cHx) H H
1-134 H H H H Me 2-(CH₂)_Five-(4-MeS-cHx) H H
1-135 H H H H Me 2-(CH₂)_Five-(3-EtS-cHx) H H
1-136 H H H H Me 2-(CH₂)_Five-(4-EtS-cHx) H H
1-137 H H H H Me 2-(CH₂)_Five-(3-PrS-cHx) H H
1-138 H H H H Me 2-(CH₂)_Five-(4-PrS-cHx) H H
1-139 H H H H Me 2-(CH₂)_Five-(3-iPrS-cHx) H H
1-140 H H H H Me 2-(CH₂)_Five-(4-iPrS-cHx) H H
1-141 H H H H Me 2-(CH₂)_Five-[3- (2-Et-PrS) -cHx] H H
1-142 H H H H Me 2-(CH₂)_Five-[4- (2-Et-PrS) -cHx] H H
1-143 H H H H Me 2-(CH₂)_Five-(3-iBuS-cHx) H H
1-144 H H H H Me 2-(CH₂)_Five-(4-iBuS-cHx) H H
1-145 H H H H Me 2-(CH₂)_Five-(3-cHx-cHx) H H
1-146 H H H H Me 2-(CH₂)_Five-(4-cHx-cHx) H H
1-147 H H H H Me 2-(CH₂)_Five-(3-Ph-cHx) H H
1-148 H H H H Me 2-(CH₂)_Five-(4-Ph-cHx) H H
1-149 H H H H Me 2-(CH₂)_Five-(2,4-diMe-cHx) H H
1-150 H H H H Me 2-(CH₂)_Five-(3,4-diMe-cHx) H H
1-151 H H H H Me 2-(CH₂)_Five-(3,5-diMe-cHx) H H
1-152 H H H H Me 2-(CH₂)_Five-Ph H H
1-153 H H H H Me 2-(CH₂)_Five-Ph Me H
1-154 H H H H Me 2-(CH₂)_Five-Ph H Me
1-155 H H H H Me 2-(CH₂)_Five-Ph F H
1-156 H H H H Me 2-(CH₂)_Five-Ph H F
1-157 H H H H Me 2-(CH₂)_Five-Ph H H
1-158 CO₂Me H H H Me 2-(CH₂)_Five-Ph H H
1-159 CO₂Et H H H Me 2-(CH₂)_Five-Ph H H
1-160 H H H H Me 2-(CH₂)_Five-(3-F-Ph) H H
1-161 H H H H Me 2-(CH₂)_Five-(4-F-Ph) H H
1-162 H H H H Me 2-(CH₂)_Five-(4-Cl-Ph) H H
1-163 H H H H Me 2-(CH₂)_Five-(4-Br-Ph) H H
1-164 H H H H Me 2-(CH₂)_Five-(3-Me-Ph) H H
1-165 H H H H Me 2-(CH₂)_Five-(4-Me-Ph) H H
1-166 H H H H Me 2-(CH₂)_Five-(3-Et-Ph) H H
1-167 H H H H Me 2-(CH₂)_Five-(4-Et-Ph) H H
1-168 H H H H Me 2-(CH₂)_Five-(3-Pr-Ph) H H
1-169 H H H H Me 2-(CH₂)_Five-(4-Pr-Ph) H H
1-170 H H H H Me 2-(CH₂)_Five-(3-iPr-Ph) H H
1-171 H H H H Me 2-(CH₂)_Five-(4-iPr-Ph) H H
1-172 H H H H Me 2-(CH₂)_Five-(3-Bu-Ph) H H
1-173 H H H H Me 2-(CH₂)_Five-(4-Bu-Ph) H H
1-174 H H H H Me 2-(CH₂)_Five-(3-CF_Three-Ph) H H
1-175 H H H H Me 2-(CH₂)_Five-(4-CF_Three-Ph) H H
1-176 H H H H Me 2-(CH₂)_Five-(3-MeO-Ph) H H
1-177 H H H H Me 2-(CH₂)_Five-(4-MeO-Ph) H H
1-178 H H H H Me 2-(CH₂)_Five-(3-EtO-Ph) H H
1-179 H H H H Me 2-(CH₂)_Five-(4-EtO-Ph) H H
1-180 H H H H Me 2-(CH₂)_Five-(3-PrO-Ph) H H
1-181 H H H H Me 2-(CH₂)_Five-(4-PrO-Ph) H H
1-182 H H H H Me 2-(CH₂)_Five-(3-iPrO-Ph) H H
1-183 H H H H Me 2-(CH₂)_Five-(4-iPrO-Ph) H H
1-184 H H H H Me 2-(CH₂)_Five-[3- (2-Et-PrO) -Ph] H H
1-185 H H H H Me 2-(CH₂)_Five-[4- (2-Et-PrO) -Ph] H H
1-186 H H H H Me 2-(CH₂)_Five-(3-iBuO-Ph) H H
1-187 H H H H Me 2-(CH₂)_Five-(4-iBuO-Ph) H H
1-188 H H H H Me 2-(CH₂)_Five-(3-MeS-Ph) H H
1-189 H H H H Me 2-(CH₂)_Five-(4-MeS-Ph) H H
1-190 H H H H Me 2-(CH₂)_Five-(3-EtS-Ph) H H
1-191 H H H H Me 2-(CH₂)_Five-(4-EtS-Ph) H H
1-192 H H H H Me 2-(CH₂)_Five-(3-PrS-Ph) H H
1-193 H H H H Me 2-(CH₂)_Five-(4-PrS-Ph) H H
1-194 H H H H Me 2-(CH₂)_Five-(3-iPrS-Ph) H H
1-195 H H H H Me 2-(CH₂)_Five-(4-iPrS-Ph) H H
1-196 H H H H Me 2-(CH₂)_Five-[3- (2-Et-PrS) -Ph] H H
1-197 H H H H Me 2-(CH₂)_Five-[4- (2-Et-PrS) -Ph] H H
1-198 H H H H Me 2-(CH₂)_Five-(3-iBuS-Ph) H H
1-199 H H H H Me 2-(CH₂)_Five-(4-iBuS-Ph) H H
1-200 H H H H Me 2-(CH₂)_Five-(3-cHx-Ph) H H
1-201 H H H H Me 2-(CH₂)_Five-(4-cHx-Ph) H H
1-202 H H H H Me 2-(CH₂)_Five-(3-Ph-Ph) H H
1-203 H H H H Me 2-(CH₂)_Five-(4-Ph-Ph) H H
1-204 H H H H Me 2-(CH₂)_Five-(2,4-diMe-Ph) H H
1-205 H H H H Me 2-(CH₂)_Five-(3,4-diMe-Ph) H H
1-206 H H H H Me 2-(CH₂)_Five-(3,5-diMe-Ph) H H
1-207 H H H H Me 2-(CH₂)_Five-Np (1) H H
1-208 H H H H Me 2-(CH₂)_Five-Np (2) H H
1-209 H H H H Me 2-(CH₂)₆-cPn H H
1-210 H H H H Me 2-(CH₂)₆-cHx H H
1-211 H H H H Me 2-(CH₂)₆-cHx Me H
1-212 H H H H Me 2-(CH₂)₆-cHx H Me
1-213 H H H H Me 2-(CH₂)₆-cHx F H
1-214 H H H H Me 2-(CH₂)₆-cHx H F
1-215 H H H H Me 2-(CH₂)₆-cHx H H
1-216 CO₂Me H H H Me 2-(CH₂)₆-cHx H H
1-217 CO₂Et H H H Me 2-(CH₂)₆-cHx H H
1-218 H H H H Me 2-(CH₂)₆-(3-F-cHx) H H
1-219 H H H H Me 2-(CH₂)₆-(4-F-cHx) H H
1-220 H H H H Me 2-(CH₂)₆-(4-Cl-cHx) H H
1-221 H H H H Me 2-(CH₂)₆-(4-Br-cHx) H H
1-222 H H H H Me 2-(CH₂)₆-(3-Me-cHx) H H
1-223 H H H H Me 2-(CH₂)₆-(4-Me-cHx) H H
1-224 H H H H Me 2-(CH₂)₆-(3-Et-cHx) H H
1-225 H H H H Me 2-(CH₂)₆-(4-Et-cHx) H H
1-226 H H H H Me 2-(CH₂)₆-(3-Pr-cHx) H H
1-227 H H H H Me 2-(CH₂)₆-(4-Pr-cHx) H H
1-228 H H H H Me 2-(CH₂)₆-(4-iPr-cHx) H H
1-229 H H H H Me 2-(CH₂)₆-(3-Bu-cHx) H H
1-230 H H H H Me 2-(CH₂)₆-(4-Bu-cHx) H H
1-231 H H H H Me 2-(CH₂)₆-(3-CF_Three-cHx) H H
1-232 H H H H Me 2-(CH₂)₆-(4-CF_Three-cHx) H H
1-233 H H H H Me 2-(CH₂)₆-(3-MeO-cHx) H H
1-234 H H H H Me 2-(CH₂)₆-(4-MeO-cHx) H H
1-235 H H H H Me 2-(CH₂)₆-(3-EtO-cHx) H H
1-236 H H H H Me 2-(CH₂)₆-(4-EtO-cHx) H H
1-237 H H H H Me 2-(CH₂)₆-(3-PrO-cHx) H H
1-238 H H H H Me 2-(CH₂)₆-(4-PrO-cHx) H H
1-239 H H H H Me 2-(CH₂)₆-(3-iPrO-cHx) H H
1-240 H H H H Me 2-(CH₂)₆-(4-iPrO-cHx) H H
1-241 H H H H Me 2-(CH₂)₆-[3- (2-Et-PrO) -cHx] H H
1-242 H H H H Me 2-(CH₂)₆-[4- (2-Et-PrO) -cHx] H H
1-243 H H H H Me 2-(CH₂)₆-(3-iBuO-cHx) H H
1-244 H H H H Me 2-(CH₂)₆-(4-iBuO-cHx) H H
1-245 H H H H Me 2-(CH₂)₆-(3-MeS-cHx) H H
1-246 H H H H Me 2-(CH₂)₆-(4-MeS-cHx) H H
1-247 H H H H Me 2-(CH₂)₆-(3-EtS-cHx) H H
1-248 H H H H Me 2-(CH₂)₆-(4-EtS-cHx) H H
1-249 H H H H Me 2-(CH₂)₆-(3-PrS-cHx) H H
1-250 H H H H Me 2-(CH₂)₆-(4-PrS-cHx) H H
1-251 H H H H Me 2-(CH₂)₆-(3-iPrS-cHx) H H
1-252 H H H H Me 2-(CH₂)₆-(4-iPrS-cHx) H H
1-253 H H H H Me 2-(CH₂)₆-[3- (2-Et-PrS) -cHx] H H
1-254 H H H H Me 2-(CH₂)₆-[4- (2-Et-PrS) -cHx] H H
1-255 H H H H Me 2-(CH₂)₆-(3-iBuS-cHx) H H
1-256 H H H H Me 2-(CH₂)₆-(4-iBuS-cHx) H H
1-257 H H H H Me 2-(CH₂)₆-(3-cHx-cHx) H H
1-258 H H H H Me 2-(CH₂)₆-(4-cHx-cHx) H H
1-259 H H H H Me 2-(CH₂)₆-(3-Ph-cHx) H H
1-260 H H H H Me 2-(CH₂)₆-(4-Ph-cHx) H H
1-261 H H H H Me 2-(CH₂)₆-(2,4-diMe-cHx) H H
1-262 H H H H Me 2-(CH₂)₆-(3,4-diMe-cHx) H H
1-263 H H H H Me 2-(CH₂)₆-(3,5-diMe-cHx) H H
1-264 H H H H Me 2-(CH₂)₆-Ph H H
1-265 H H H H Me 2-(CH₂)₆-Ph Me H
1-266 H H H H Me 2-(CH₂)₆-Ph H Me
1-267 H H H H Me 2-(CH₂)₆-Ph F H
1-268 H H H H Me 2-(CH₂)₆-Ph H F
1-269 H H Me Me Me 2-(CH₂)₆-Ph H H
1-270 CO₂Me H H H Me 2-(CH₂)₆-Ph H H
1-271 CO₂Et H H H Me 2-(CH₂)₆-Ph H H
1-272 H H H H Me 2-(CH₂)₆-(3-F-Ph) H H
1-273 H H H H Me 2-(CH₂)₆-(4-F-Ph) H H
1-274 H H H H Me 2-(CH₂)₆-(4-Cl-Ph) H H
1-275 H H H H Me 2-(CH₂)₆-(4-Br-Ph) H H
1-276 H H H H Me 2-(CH₂)₆-(3-Me-Ph) H H
1-277 H H H H Me 2-(CH₂)₆-(4-Me-Ph) H H
1-278 H H H H Me 2-(CH₂)₆-(3-Et-Ph) H H
1-279 H H H H Me 2-(CH₂)₆-(4-Et-Ph) H H
1-280 H H H H Me 2-(CH₂)₆-(3-Pr-Ph) H H
1-281 H H H H Me 2-(CH₂)₆-(4-Pr-Ph) H H
1-282 H H H H Me 2-(CH₂)₆-(3-iPr-Ph) H H
1-283 H H H H Me 2-(CH₂)₆-(4-iPr-Ph) H H
1-284 H H H H Me 2-(CH₂)₆-(3-Bu-Ph) H H
1-285 H H H H Me 2-(CH₂)₆-(4-Bu-Ph) H H
1-286 H H H H Me 2-(CH₂)₆-(3-CF_Three-Ph) H H
1-287 H H H H Me 2-(CH₂)₆-(4-CF_Three-Ph) H H
1-288 H H H H Me 2-(CH₂)₆-(3-MeO-Ph) H H
1-289 H H H H Me 2-(CH₂)₆-(4-MeO-Ph) H H
1-290 H H H H Me 2-(CH₂)₆-(3-EtO-Ph) H H
1-291 H H H H Me 2-(CH₂)₆-(4-EtO-Ph) H H
1-292 H H H H Me 2-(CH₂)₆-(3-PrO-Ph) H H
1-293 H H H H Me 2-(CH₂)₆-(4-PrO-Ph) H H
1-294 H H H H Me 2-(CH₂)₆-(3-iPrO-Ph) H H
1-295 H H H H Me 2-(CH₂)₆-(4-iPrO-Ph) H H
1-296 H H H H Me 2-(CH₂)₆-[3- (2-Et-PrO) -Ph] H H
1-297 H H H H Me 2-(CH₂)₆-[4- (2-Et-PrO) -Ph] H H
1-298 H H H H Me 2-(CH₂)₆-(3-iBuO-Ph) H H
1-299 H H H H Me 2-(CH₂)₆-(4-iBuO-Ph) H H
1-300 H H H H Me 2-(CH₂)₆-(3-MeS-Ph) H H
1-301 H H H H Me 2-(CH₂)₆-(4-MeS-Ph) H H
1-302 H H H H Me 2-(CH₂)₆-(3-EtS-Ph) H H
1-303 H H H H Me 2-(CH₂)₆-(4-EtS-Ph) H H
1-304 H H H H Me 2-(CH₂)₆-(3-PrS-Ph) H H
1-305 H H H H Me 2-(CH₂)₆-(4-PrS-Ph) H H
1-306 H H H H Me 2-(CH₂)₆-(3-iPrS-Ph) H H
1-307 H H H H Me 2-(CH₂)₆-(4-iPrS-Ph) H H
1-308 H H H H Me 2-(CH₂)₆-[3- (2-Et-PrS) -Ph] H H
1-309 H H H H Me 2-(CH₂)₆-[4- (2-Et-PrS) -Ph] H H
1-310 H H H H Me 2-(CH₂)₆-(3-iBuS-Ph) H H
1-311 H H H H Me 2-(CH₂)₆-(4-iBuS-Ph) H H
1-312 H H H H Me 2-(CH₂)₆-(3-cHx-Ph) H H
1-313 H H H H Me 2-(CH₂)₆-(4-cHx-Ph) H H
1-314 H H H H Me 2-(CH₂)₆-(3-Ph-Ph) H H
1-315 H H H H Me 2-(CH₂)₆-(4-Ph-Ph) H H
1-316 H H H H Me 2-(CH₂)₆-(2,4-diMe-Ph) H H
1-317 H H H H Me 2-(CH₂)₆-(3,4-diMe-Ph) H H
1-318 H H H H Me 2-(CH₂)₆-(3,5-diMe-Ph) H H
1-319 H H H H Me 2-(CH₂)₆-Np (1) H H
1-320 H H H H Me 2-(CH₂)₆-Np (2) H H
1-321 H H H H Me 2-(CH₂)₇-cHx H H
1-322 H H Me Me Me 2-(CH₂)₇-cHx H H
1-323 CO₂Me H H H Me 2-(CH₂)₇-cHx H H
1-324 CO₂Et H H H Me 2-(CH₂)₇-cHx H H
1-325 H H H H Me 2-(CH₂)₇-(4-F-cHx) H H
1-326 H H H H Me 2-(CH₂)₇-(4-Me-cHx) H H
1-327 H H H H Me 2-(CH₂)₇-(4-Et-cHx) H H
1-328 H H H H Me 2-(CH₂)₇-(4-CF_Three-cHx) H H
1-329 H H H H Me 2-(CH₂)₇-(4-MeO-cHx) H H
1-330 H H H H Me 2-(CH₂)₇-(4-EtO-cHx) H H
1-331 H H H H Me 2-(CH₂)₇-(4-MeS-cHx) H H
1-332 H H H H Me 2-(CH₂)₇-(4-cHx-cHx) H H
1-333 H H H H Me 2-(CH₂)₇-(4-Ph-cHx) H H
1-334 H H H H Me 2-(CH₂)₇-Ph H H
1-335 H H Me Me Me 2-(CH₂)₇-Ph H H
1-336 CO₂Me H H H Me 2-(CH₂)₇-Ph H H
1-337 CO₂Et H H H Me 2-(CH₂)₇-Ph H H
1-338 H H H H Me 2-(CH₂)₇-(4-F-Ph) H H
1-339 H H H H Me 2-(CH₂)₇-(4-Me-Ph) H H
1-340 H H H H Me 2-(CH₂)₇-(4-Et-Ph) H H
1-341 H H H H Me 2-(CH₂)₇-(4-CF_Three-Ph) H H
1-342 H H H H Me 2-(CH₂)₇-(4-MeO-Ph) H H
1-343 H H H H Me 2-(CH₂)₇-(4-EtO-Ph) H H
1-344 H H H H Me 2-(CH₂)₇-(4-MeS-Ph) H H
1-345 H H H H Me 2-(CH₂)₇-(4-cHx-Ph) H H
1-346 H H H H Me 2-(CH₂)₇-(4-Ph-Ph) H H
1-347 H H H H Me 2-(CH₂)₈-cHx H H
1-348 H H Me Me Me 2-(CH₂)₈-cHx H H
1-349 CO₂Me H H H Me 2-(CH₂)₈-cHx H H
1-350 CO₂Et H H H Me 2-(CH₂)₈-cHx H H
1-351 H H H H Me 2-(CH₂)₈-(4-F-cHx) H H
1-352 H H H H Me 2-(CH₂)₈-(4-Me-cHx) H H
1-353 H H H H Me 2-(CH₂)₈-(4-Et-cHx) H H
1-354 H H H H Me 2-(CH₂)₈-(4-CF_Three-cHx) H H
1-355 H H H H Me 2-(CH₂)₈-(4-MeO-cHx) H H
1-356 H H H H Me 2-(CH₂)₈-(4-EtO-cHx) H H
1-357 H H H H Me 2-(CH₂)₈-(4-MeS-cHx) H H
1-358 H H H H Me 2-(CH₂)₈-(4-cHx-cHx) H H
1-359 H H H H Me 2-(CH₂)₈-(4-Ph-cHx) H H
1-360 H H H H Me 2-(CH₂)₈-Ph H H
1-361 H H Me Me Me 2-(CH₂)₈-Ph H H
1-362 CO₂Me H H H Me 2-(CH₂)₈-Ph H H
1-363 CO₂Et H H H Me 2-(CH₂)₈-Ph H H
1-364 H H H H Me 2-(CH₂)₈-(4-F-Ph) H H
1-365 H H H H Me 2-(CH₂)₈-(4-Me-Ph) H H
1-366 H H H H Me 2-(CH₂)₈-(4-Et-Ph) H H
1-367 H H H H Me 2-(CH₂)₈-(4-CF_Three-Ph) H H
1-368 H H H H Me 2-(CH₂)₈-(4-MeO-Ph) H H
1-369 H H H H Me 2-(CH₂)₈-(4-EtO-Ph) H H
1-370 H H H H Me 2-(CH₂)₈-(4-MeS-Ph) H H
1-371 H H H H Me 2-(CH₂)₈-(4-cHx-Ph) H H
1-372 H H H H Me 2-(CH₂)₈-(4-Ph-Ph) H H
1-373 H H H H Me 2-(CH₂)_Three-O-cHx H H
1-374 H H Me Me Me 2-(CH₂)_Three-O-cHx H H
1-375 CO₂Me H H H Me 2-(CH₂)_Three-O-cHx H H
1-376 CO₂Et H H H Me 2-(CH₂)_Three-O-cHx H H
1-377 H H H H Me 2-(CH₂)_Three-O- (4-F-cHx) H H
1-378 H H H H Me 2-(CH₂)_Three-O- (4-Me-cHx) H H
1-379 H H H H Me 2-(CH₂)_Three-O- (4-Et-cHx) H H
1-380 H H H H Me 2-(CH₂)_Three-O- (4-CF_Three-cHx) H H
1-381 H H H H Me 2-(CH₂)_Three-O- (4-MeO-cHx) H H
1-382 H H H H Me 2-(CH₂)_Three-O- (4-EtO-cHx) H H
1-383 H H H H Me 2-(CH₂)_Three-O- (4-MeS-cHx) H H
1-384 H H H H Me 2-(CH₂)_Three-O- (4-cHx-cHx) H H
1-385 H H H H Me 2-(CH₂)_Three-O- (4-Ph-cHx) H H
1-386 H H H H Me 2-(CH₂)_Three-O-Ph H H
1-387 H H H H Me 2-(CH₂)_Three-O-Ph H H
1-388 CO₂Me H H H Me 2-(CH₂)_Three-O-Ph H H
1-389 CO₂Et H H H Me 2-(CH₂)_Three-O-Ph H H
1-390 H H H H Me 2-(CH₂)_Three-O- (4-F-Ph) H H
1-391 H H H H Me 2-(CH₂)_Three-O- (4-Me-Ph) H H
1-392 H H H H Me 2-(CH₂)_Three-O- (4-Et-Ph) H H
1-393 H H H H Me 2-(CH₂)_Three-O- (4-CF_Three-Ph) H H
1-394 H H H H Me 2-(CH₂)_Three-O- (4-MeO-Ph) H H
1-395 H H H H Me 2-(CH₂)_Three-O- (4-EtO-Ph) H H
1-396 H H H H Me 2-(CH₂)_Three-O- (4-MeS-Ph) H H
1-397 H H H H Me 2-(CH₂)_Three-O- (4-cHx-Ph) H H
1-398 H H H H Me 2-(CH₂)_Three-O- (4-Ph-Ph) H H
1-399 H H H H Me 2-(CH₂)_Four-O-cPn H H
1-400 H H H H Me 2-(CH₂)_Four-O-cHx H H
1-401 H H H H Me 2-(CH₂)_Four-O-cHx Me H
1-402 H H H H Me 2-(CH₂)_Four-O-cHx H Me
1-403 H H H H Me 2-(CH₂)_Four-O-cHx F H
1-404 H H H H Me 2-(CH₂)_Four-O-cHx H F
1-405 H H H H Me 2-(CH₂)_Four-O-cHx H H
1-406 CO₂Me H H H Me 2-(CH₂)_Four-O-cHx H H
1-407 CO₂Et H H H Me 2-(CH₂)_Four-O-cHx H H
1-408 H H H H Me 2-(CH₂)_Four-O- (3-F-cHx) H H
1-409 H H H H Me 2-(CH₂)_Four-O- (4-F-cHx) H H
1-410 H H H H Me 2-(CH₂)_Four-O- (4-Cl-cHx) H H
1-411 H H H H Me 2-(CH₂)_Four-O- (4-Br-cHx) H H
1-412 H H H H Me 2-(CH₂)_Four-O- (3-Me-cHx) H H
1-413 H H H H Me 2-(CH₂)_Four-O- (4-Me-cHx) H H
1-414 H H H H Me 2-(CH₂)_Four-O- (3-Et-cHx) H H
1-415 H H H H Me 2-(CH₂)_Four-O- (4-Et-cHx) H H
1-416 H H H H Me 2-(CH₂)_Four-O- (3-Pr-cHx) H H
1-417 H H H H Me 2-(CH₂)_Four-O- (4-Pr-cHx) H H
1-418 H H H H Me 2-(CH₂)_Four-O- (4-iPr-cHx) H H
1-419 H H H H Me 2-(CH₂)_Four-O- (3-Bu-cHx) H H
1-420 H H H H Me 2-(CH₂)_Four-O- (4-Bu-cHx) H H
1-421 H H H H Me 2-(CH₂)_Four-O- (3-CF_Three-cHx) H H
1-422 H H H H Me 2-(CH₂)_Four-O- (4-CF_Three-cHx) H H
1-423 H H H H Me 2-(CH₂)_Four-O- (3-MeO-cHx) H H
1-424 H H H H Me 2-(CH₂)_Four-O- (4-MeO-cHx) H H
1-425 H H H H Me 2-(CH₂)_Four-O- (3-EtO-cHx) H H
1-426 H H H H Me 2-(CH₂)_Four-O- (4-EtO-cHx) H H
1-427 H H H H Me 2-(CH₂)_Four-O- (3-PrO-cHx) H H
1-428 H H H H Me 2-(CH₂)_Four-O- (4-PrO-cHx) H H
1-429 H H H H Me 2-(CH₂)_Four-O- (3-iPrO-cHx) H H
1-430 H H H H Me 2-(CH₂)_Four-O- (4-iPrO-cHx) H H
1-431 H H H H Me 2-(CH₂)_Four-O- [3- (2-Et-PrO) -cHx] H H
1-432 H H H H Me 2-(CH₂)_Four-O- [4- (2-Et-PrO) -cHx] H H
1-433 H H H H Me 2-(CH₂)_Four-O- (3-iBuO-cHx) H H
1-434 H H H H Me 2-(CH₂)_Four-O- (4-iBuO-cHx) H H
1-435 H H H H Me 2-(CH₂)_Four-O- (3-MeS-cHx) H H
1-436 H H H H Me 2-(CH₂)_Four-O- (4-MeS-cHx) H H
1-437 H H H H Me 2-(CH₂)_Four-O- (3-EtS-cHx) H H
1-438 H H H H Me 2-(CH₂)_Four-O- (4-EtS-cHx) H H
1-439 H H H H Me 2-(CH₂)_Four-O- (3-PrS-cHx) H H
1-440 H H H H Me 2-(CH₂)_Four-O- (4-PrS-cHx) H H
1-441 H H H H Me 2-(CH₂)_Four-O- (3-iPrS-cHx) H H
1-442 H H H H Me 2-(CH₂)_Four-O- (4-iPrS-cHx) H H
1-443 H H H H Me 2-(CH₂)_Four-O- [3- (2-Et-PrS) -cHx] H H
1-444 H H H H Me 2-(CH₂)_Four-O- [4- (2-Et-PrS) -cHx] H H
1-445 H H H H Me 2-(CH₂)_Four-O- (3-iBuS-cHx) H H
1-446 H H H H Me 2-(CH₂)_Four-O- (4-iBuS-cHx) H H
1-447 H H H H Me 2-(CH₂)_Four-O- (3-cHx-cHx) H H
1-448 H H H H Me 2-(CH₂)_Four-O- (4-cHx-cHx) H H
1-449 H H H H Me 2-(CH₂)_Four-O- (3-Ph-cHx) H H
1-450 H H H H Me 2-(CH₂)_Four-O- (4-Ph-cHx) H H
1-451 H H H H Me 2-(CH₂)_Four-O- (2,4-diMe-cHx) H H
1-452 H H H H Me 2-(CH₂)_Four-O- (3,4-diMe-cHx) H H
1-453 H H H H Me 2-(CH₂)_Four-O- (3,5-diMe-cHx) H H
1-454 H H H H Me 2-(CH₂)_Four-O-Ph H H
1-455 H H H H Me 2-(CH₂)_Four-O-Ph Me H
1-456 H H H H Me 2-(CH₂)_Four-O-Ph H Me
1-457 H H H H Me 2-(CH₂)_Four-O-Ph F H
1-458 H H H H Me 2-(CH₂)_Four-O-Ph H F
1-459 H H Me Me 2-(CH₂)_Four-O-Ph H H
1-460 CO₂Me H H Me 2-(CH₂)_Four-O-Ph H H
1-461 CO₂Et H H Me 2-(CH₂)_Four-O-Ph H H
1-462 H H H H Me 2-(CH₂)_Four-O- (3-F-Ph) H H
1-463 H H H H Me 2-(CH₂)_Four-O- (4-F-Ph) H H
1-464 H H H H Me 2-(CH₂)_Four-O- (4-Cl-Ph) H H
1-465 H H H H Me 2-(CH₂)_Four-O- (4-Br-Ph) H H
1-466 H H H H Me 2-(CH₂)_Four-O- (3-Me-Ph) H H
1-467 H H H H Me 2-(CH₂)_Four-O- (4-Me-Ph) H H
1-468 H H H H Me 2-(CH₂)_Four-O- (3-Et-Ph) H H
1-469 H H H H Me 2-(CH₂)_Four-O- (4-Et-Ph) H H
1-470 H H H H Me 2-(CH₂)_Four-O- (3-Pr-Ph) H H
1-471 H H H H Me 2-(CH₂)_Four-O- (4-Pr-Ph) H H
1-472 H H H H Me 2-(CH₂)_Four-O- (3-iPr-Ph) H H
1-473 H H H H Me 2-(CH₂)_Four-O- (4-iPr-Ph) H H
1-474 H H H H Me 2-(CH₂)_Four-O- (3-Bu-Ph) H H
1-475 H H H H Me 2-(CH₂)_Four-O- (4-Bu-Ph) H H
1-476 H H H H Me 2-(CH₂)_Four-O- (3-CF_Three-Ph) H H
1-477 H H H H Me 2-(CH₂)_Four-O- (4-CF_Three-Ph) H H
1-478 H H H H Me 2-(CH₂)_Four-O- (3-MeO-Ph) H H
1-479 H H H H Me 2-(CH₂)_Four-O- (4-MeO-Ph) H H
1-480 H H H H Me 2-(CH₂)_Four-O- (3-EtO-Ph) H H
1-481 H H H H Me 2-(CH₂)_Four-O- (4-EtO-Ph) H H
1-482 H H H H Me 2-(CH₂)_Four-O- (3-PrO-Ph) H H
1-483 H H H H Me 2-(CH₂)_Four-O- (4-PrO-Ph) H H
1-484 H H H H Me 2-(CH₂)_Four-O- (3-iPrO-Ph) H H
1-485 H H H H Me 2-(CH₂)_Four-O- (4-iPrO-Ph) H H
1-486 H H H H Me 2-(CH₂)_Four-O- [3- (2-Et-PrO) -Ph] H H
1-487 H H H H Me 2-(CH₂)_Four-O- [4- (2-Et-PrO) -Ph] H H
1-488 H H H H Me 2-(CH₂)_Four-O- (3-iBuO-Ph) H H
1-489 H H H H Me 2-(CH₂)_Four-O- (4-iBuO-Ph) H H
1-490 H H H H Me 2-(CH₂)_Four-O- (3-MeS-Ph) H H
1-491 H H H H Me 2-(CH₂)_Four-O- (4-MeS-Ph) H H
1-492 H H H H Me 2-(CH₂)_Four-O- (3-EtS-Ph) H H
1-493 H H H H Me 2-(CH₂)_Four-O- (4-EtS-Ph) H H
1-494 H H H H Me 2-(CH₂)_Four-O- (3-PrS-Ph) H H
1-495 H H H H Me 2-(CH₂)_Four-O- (4-PrS-Ph) H H
1-496 H H H H Me 2-(CH₂)_Four-O- (3-iPrS-Ph) H H
1-497 H H H H Me 2-(CH₂)_Four-O- (4-iPrS-Ph) H H
1-498 H H H H Me 2-(CH₂)_Four-O- [3- (2-Et-PrS) -Ph] H H
1-499 H H H H Me 2-(CH₂)_Four-O- [4- (2-Et-PrS) -Ph] H H
1-500 H H H H Me 2-(CH₂)_Four-O- (3-iBuS-Ph) H H
1-501 H H H H Me 2-(CH₂)_Four-O- (4-iBuS-Ph) H H
1-502 H H H H Me 2-(CH₂)_Four-O- (3-cHx-Ph) H H
1-503 H H H H Me 2-(CH₂)_Four-O- (4-cHx-Ph) H H
1-504 H H H H Me 2-(CH₂)_Four-O- (3-Ph-Ph) H H
1-505 H H H H Me 2-(CH₂)_Four-O- (4-Ph-Ph) H H
1-506 H H H H Me 2-(CH₂)_Four-O- (2,4-diMe-Ph) H H
1-507 H H H H Me 2-(CH₂)_Four-O- (3,4-diMe-Ph) H H
1-508 H H H H Me 2-(CH₂)_Four-O- (3,5-diMe-Ph) H H
1-509 H H H H Me 2-(CH₂)_Five-O-cHx H H
1-510 H H H H Me 2-(CH₂)_Five-O-Ph H H
1-511 H H H H Me 2-(CH₂)₆-O-cHx H H
1-512 H H H H Me 2-(CH₂)₆-O-Ph H H
1-513 H H H H Me 2-(CH₂)_Three-OCH₂-cHx H H
1-514 H H Me Me Me 2-(CH₂)_Three-OCH₂-cHx H H
1-515 CO₂Me H H H Me 2-(CH₂)_Three-OCH₂-cHx H H
1-516 CO₂Et H H H Me 2-(CH₂)_Three-OCH₂-cHx H H
1-517 H H H H Me 2-(CH₂)_Three-OCH₂-(4-F-cHx) H H
1-518 H H H H Me 2-(CH₂)_Three-OCH₂-(4-Me-cHx) H H
1-519 H H H H Me 2-(CH₂)_Three-OCH₂-(4-Et-cHx) H H
1-520 H H H H Me 2-(CH₂)_Three-OCH₂-(4-CF_Three-cHx) H H
1-521 H H H H Me 2-(CH₂)_Three-OCH₂-(4-MeO-cHx) H H
1-522 H H H H Me 2-(CH₂)_Three-OCH₂-(4-EtO-cHx) H H
1-523 H H H H Me 2-(CH₂)_Three-OCH₂-(4-MeS-cHx) H H
1-524 H H H H Me 2-(CH₂)_Three-OCH₂-(4-cHx-cHx) H H
1-525 H H H H Me 2-(CH₂)_Three-OCH₂-(4-Ph-cHx) H H
1-526 H H H H Me 2-(CH₂)_Three-OCH₂-Ph H H
1-527 H H Me Me Me 2-(CH₂)_Three-OCH₂-Ph H H
1-528 CO₂Me H H H Me 2-(CH₂)_Three-OCH₂-Ph H H
1-529 CO₂Et H H H Me 2-(CH₂)_Three-OCH₂-Ph H H
1-530 H H H H Me 2-(CH₂)_Three-OCH₂-(4-F-Ph) H H
1-531 H H H H Me 2-(CH₂)_Three-OCH₂-(4-Me-Ph) H H
1-532 H H H H Me 2-(CH₂)_Three-OCH₂-(4-Et-Ph) H H
1-533 H H H H Me 2-(CH₂)_Three-OCH₂-(4-CF_Three-Ph) H H
1-534 H H H H Me 2-(CH₂)_Three-OCH₂-(4-MeO-Ph) H H
1-535 H H H H Me 2-(CH₂)_Three-OCH₂-(4-EtO-Ph) H H
1-536 H H H H Me 2-(CH₂)_Three-OCH₂-(4-MeS-Ph) H H
1-537 H H H H Me 2-(CH₂)_Three-OCH₂-(4-cHx-Ph) H H
1-538 H H H H Me 2-(CH₂)_Three-OCH₂-(4-Ph-Ph) H H
1-539 H H H H Me 2-(CH₂)_Four-OCH₂-cPn H H
1-540 H H H H Me 2-(CH₂)_Four-OCH₂-cHx H H
1-541 H H H H Me 2-(CH₂)_Four-OCH₂-cHx Me H
1-542 H H H H Me 2-(CH₂)_Four-OCH₂-cHx H Me
1-543 H H H H Me 2-(CH₂)_Four-OCH₂-cHx F H
1-544 H H H H Me 2-(CH₂)_Four-OCH₂-cHx H F
1-545 H H Me Me Me 2-(CH₂)_Four-OCH₂-cHx H H
1-546 CO₂Me H H H Me 2-(CH₂)_Four-OCH₂-cHx H H
1-547 CO₂Et H H H Me 2-(CH₂)_Four-OCH₂-cHx H H
1-548 H H H H Me 2-(CH₂)_Four-OCH₂-(3-F-cHx) H H
1-549 H H H H Me 2-(CH₂)_Four-OCH₂-(4-F-cHx) H H
1-550 H H H H Me 2-(CH₂)_Four-OCH₂-(4-Cl-cHx) H H
1-551 H H H H Me 2-(CH₂)_Four-OCH₂-(4-Br-cHx) H H
1-552 H H H H Me 2-(CH₂)_Four-OCH₂-(3-Me-cHx) H H
1-553 H H H H Me 2-(CH₂)_Four-OCH₂-(4-Me-cHx) H H
1-554 H H H H Me 2-(CH₂)_Four-OCH₂-(3-Et-cHx) H H
1-555 H H H H Me 2-(CH₂)_Four-OCH₂-(4-Et-cHx) H H
1-556 H H H H Me 2-(CH₂)_Four-OCH₂-(3-Pr-cHx) H H
1-557 H H H H Me 2-(CH₂)_Four-OCH₂-(4-Pr-cHx) H H
1-558 H H H H Me 2-(CH₂)_Four-OCH₂-(4-iPr-cHx) H H
1-559 H H H H Me 2-(CH₂)_Four-OCH₂-(3-Bu-cHx) H H
1-560 H H H H Me 2-(CH₂)_Four-OCH₂-(4-Bu-cHx) H H
1-561 H H H H Me 2-(CH₂)_Four-OCH₂-(3-CF_Three-cHx) H H
1-562 H H H H Me 2-(CH₂)_Four-OCH₂-(4-CF_Three-cHx) H H
1-563 H H H H Me 2-(CH₂)_Four-OCH₂-(3-MeO-cHx) H H
1-564 H H H H Me 2-(CH₂)_Four-OCH₂-(4-MeO-cHx) H H
1-565 H H H H Me 2-(CH₂)_Four-OCH₂-(3-EtO-cHx) H H
1-566 H H H H Me 2-(CH₂)_Four-OCH₂-(4-EtO-cHx) H H
1-567 H H H H Me 2-(CH₂)_Four-OCH₂-(3-PrO-cHx) H H
1-568 H H H H Me 2-(CH₂)_Four-OCH₂-(4-PrO-cHx) H H
1-569 H H H H Me 2-(CH₂)_Four-OCH₂-(3-iPrO-cHx) H H
1-570 H H H H Me 2-(CH₂)_Four-OCH₂-(4-iPrO-cHx) H H
1-571 H H H H Me 2-(CH₂)_Four-OCH₂-[3- (2-Et-PrO) -cHx] H H
1-572 H H H H Me 2-(CH₂)_Four-OCH₂-[4- (2-Et-PrO) -cHx] H H
1-573 H H H H Me 2-(CH₂)_Four-OCH₂-(3-iBuO-cHx) H H
1-574 H H H H Me 2-(CH₂)_Four-OCH₂-(4-iBuO-cHx) H H
1-575 H H H H Me 2-(CH₂)_Four-OCH₂-(3-MeS-cHx) H H
1-576 H H H H Me 2-(CH₂)_Four-OCH₂-(4-MeS-cHx) H H
1-577 H H H H Me 2-(CH₂)_Four-OCH₂-(3-EtS-cHx) H H
1-578 H H H H Me 2-(CH₂)_Four-OCH₂-(4-EtS-cHx) H H
1-579 H H H H Me 2-(CH₂)_Four-OCH₂-(3-PrS-cHx) H H
1-580 H H H H Me 2-(CH₂)_Four-OCH₂-(4-PrS-cHx) H H
1-581 H H H H Me 2-(CH₂)_Four-OCH₂-(3-iPrS-cHx) H H
1-582 H H H H Me 2-(CH₂)_Four-OCH₂-(4-iPrS-cHx) H H
1-583 H H H H Me 2-(CH₂)_Four-OCH₂-[3- (2-Et-PrS) -cHx] H H
1-584 H H H H Me 2-(CH₂)_Four-OCH₂-[4- (2-Et-PrS) -cHx] H H
1-585 H H H H Me 2-(CH₂)_Four-OCH₂-(3-iBuS-cHx) H H
1-586 H H H H Me 2-(CH₂)_Four-OCH₂-(4-iBuS-cHx) H H
1-587 H H H H Me 2-(CH₂)_Four-OCH₂-(3-cHx-cHx) H H
1-588 H H H H Me 2-(CH₂)_Four-OCH₂-(4-cHx-cHx) H H
1-589 H H H H Me 2-(CH₂)_Four-OCH₂-(3-Ph-cHx) H H
1-590 H H H H Me 2-(CH₂)_Four-OCH₂-(4-Ph-cHx) H H
1-591 H H H H Me 2-(CH₂)_Four-OCH₂-(2,4-diMe-cHx) H H
1-592 H H H H Me 2-(CH₂)_Four-OCH₂-(3,4-diMe-cHx) H H
1-593 H H H H Me 2-(CH₂)_Four-OCH₂-(3,5-diMe-cHx) H H
1-594 H H H H Me 2-(CH₂)_Four-OCH₂-Ph H H
1-595 H H H H Me 2-(CH₂)_Four-OCH₂-Ph Me H
1-596 H H H H Me 2-(CH₂)_Four-OCH₂-Ph H Me
1-597 H H H H Me 2-(CH₂)_Four-OCH₂-Ph F H
1-598 H H H H Me 2-(CH₂)_Four-OCH₂-Ph H F
1-599 H H Me Me Me 2-(CH₂)_Four-OCH₂-Ph H H
1-600 CO₂Me H H H Me 2-(CH₂)_Four-OCH₂-Ph H H
1-601 CO₂Et H H H Me 2-(CH₂)_Four-OCH₂-Ph H H
1-602 H H H H Me 2-(CH₂)_Four-OCH₂-(3-F-Ph) H H
1-603 H H H H Me 2-(CH₂)_Four-OCH₂-(4-F-Ph) H H
1-604 H H H H Me 2-(CH₂)_Four-OCH₂-(4-Cl-Ph) H H
1-605 H H H H Me 2-(CH₂)_Four-OCH₂-(4-Br-Ph) H H
1-606 H H H H Me 2-(CH₂)_Four-OCH₂-(3-Me-Ph) H H
1-607 H H H H Me 2-(CH₂)_Four-OCH₂-(4-Me-Ph) H H
1-608 H H H H Me 2-(CH₂)_Four-OCH₂-(3-Et-Ph) H H
1-609 H H H H Me 2-(CH₂)_Four-OCH₂-(4-Et-Ph) H H
1-610 H H H H Me 2-(CH₂)_Four-OCH₂-(3-Pr-Ph) H H
1-611 H H H H Me 2-(CH₂)_Four-OCH₂-(4-Pr-Ph) H H
1-612 H H H H Me 2-(CH₂)_Four-OCH₂-(3-iPr-Ph) H H
1-613 H H H H Me 2-(CH₂)_Four-OCH₂-(4-iPr-Ph) H H
1-614 H H H H Me 2-(CH₂)_Four-OCH₂-(3-Bu-Ph) H H
1-615 H H H H Me 2-(CH₂)_Four-OCH₂-(4-Bu-Ph) H H
1-616 H H H H Me 2-(CH₂)_Four-OCH₂-(3-CF_Three-Ph) H H
1-617 H H H H Me 2-(CH₂)_Four-OCH₂-(4-CF_Three-Ph) H H
1-618 H H H H Me 2-(CH₂)_Four-OCH₂-(3-MeO-Ph) H H
1-619 H H H H Me 2-(CH₂)_Four-OCH₂-(4-MeO-Ph) H H
1-620 H H H H Me 2-(CH₂)_Four-OCH₂-(3-EtO-Ph) H H
1-621 H H H H Me 2-(CH₂)_Four-OCH₂-(4-EtO-Ph) H H
1-622 H H H H Me 2-(CH₂)_Four-OCH₂-(3-PrO-Ph) H H
1-623 H H H H Me 2-(CH₂)_Four-OCH₂-(4-PrO-Ph) H H
1-624 H H H H Me 2-(CH₂)_Four-OCH₂-(3-iPrO-Ph) H H
1-625 H H H H Me 2-(CH₂)_Four-OCH₂-(4-iPrO-Ph) H H
1-626 H H H H Me 2-(CH₂)_Four-OCH₂-[3- (2-Et-PrO) -Ph] H H
1-627 H H H H Me 2-(CH₂)_Four-OCH₂-[4- (2-Et-PrO) -Ph] H H
1-628 H H H H Me 2-(CH₂)_Four-OCH₂-(3-iBuO-Ph) H H
1-629 H H H H Me 2-(CH₂)_Four-OCH₂-(4-iBuO-Ph) H H
1-630 H H H H Me 2-(CH₂)_Four-OCH₂-(3-MeS-Ph) H H
1-631 H H H H Me 2-(CH₂)_Four-OCH₂-(4-MeS-Ph) H H
1-632 H H H H Me 2-(CH₂)_Four-OCH₂-(3-EtS-Ph) H H
1-633 H H H H Me 2-(CH₂)_Four-OCH₂-(4-EtS-Ph) H H
1-634 H H H H Me 2-(CH₂)_Four-OCH₂-(3-PrS-Ph) H H
1-635 H H H H Me 2-(CH₂)_Four-OCH₂-(4-PrS-Ph) H H
1-636 H H H H Me 2-(CH₂)_Four-OCH₂-(3-iPrS-Ph) H H
1-637 H H H H Me 2-(CH₂)_Four-OCH₂-(4-iPrS-Ph) H H
1-638 H H H H Me 2-(CH₂)_Four-OCH₂-[3- (2-Et-PrS) -Ph] H H
1-639 H H H H Me 2-(CH₂)_Four-OCH₂-[4- (2-Et-PrS) -Ph] H H
1-640 H H H H Me 2-(CH₂)_Four-OCH₂-(3-iBuS-Ph) H H
1-641 H H H H Me 2-(CH₂)_Four-OCH₂-(4-iBuS-Ph) H H
1-642 H H H H Me 2-(CH₂)_Four-OCH₂-(3-cHx-Ph) H H
1-643 H H H H Me 2-(CH₂)_Four-OCH₂-(4-cHx-Ph) H H
1-644 H H H H Me 2-(CH₂)_Four-OCH₂-(3-Ph-Ph) H H
1-645 H H H H Me 2-(CH₂)_Four-OCH₂-(4-Ph-Ph) H H
1-646 H H H H Me 2-(CH₂)_Four-OCH₂-(2,4-diMe-Ph) H H
1-647 H H H H Me 2-(CH₂)_Four-OCH₂-(3,4-diMe-Ph) H H
1-648 H H H H Me 2-(CH₂)_Four-OCH₂-(3,5-diMe-Ph) H H
1-649 H H H H Me 2-(CH₂)_Five-OCH₂-cHx H H
1-650 H H H H Me 2-(CH₂)_Five-OCH₂-Ph H H
1-651 H H H H Me 2-(CH₂)₆-OCH₂-cHx H H
1-652 H H H H Me 2-(CH₂)₆-OCH₂-Ph H H
1-653 H H H H Me 2 -CH = CH-cHx H H
1-654 H H H H Me 2 -CH = CH-Ph H H
1-655 H H H H Me 2 -CH = CH- (CH₂)₂-cHx H H
1-656 H H H H Me 2 -CH = CH- (CH₂)₂-Ph H H
1-657 H H H H Me 2 -CH = CH- (CH₂)_Three-cHx H H
1-658 H H Me Me Me 2 -CH = CH- (CH₂)_Three-cHx H H
1-659 CO₂Me H H H Me 2 -CH = CH- (CH₂)_Three-cHx H H
1-660 CO₂Et H H H Me 2 -CH = CH- (CH₂)_Three-cHx H H
1-661 H H H H Me 2 -CH = CH- (CH₂)_Three-(4-F-cHx) H H
1-662 H H H H Me 2 -CH = CH- (CH₂)_Three-(4-Me-cHx) H H
1-663 H H H H Me 2 -CH = CH- (CH₂)_Three-(4-Et-cHx) H H
1-664 H H H H Me 2 -CH = CH- (CH₂)_Three-(4-CF_Three-cHx) H H
1-665 H H H H Me 2 -CH = CH- (CH₂)_Three-(4-MeO-cHx) H H
1-666 H H H H Me 2 -CH = CH- (CH₂)_Three-(4-EtO-cHx) H H
1-667 H H H H Me 2 -CH = CH- (CH₂)_Three-(4-MeS-cHx) H H
1-668 H H H H Me 2 -CH = CH- (CH₂)_Three-(4-cHx-cHx) H H
1-669 H H H H Me 2 -CH = CH- (CH₂)_Three-(4-Ph-cHx) H H
1-670 H H H H Me 2 -CH = CH- (CH₂)_Three-Ph H H
1-671 H H Me Me Me 2 -CH = CH- (CH₂)_Three-Ph H H
1-672 CO₂Me H H H Me 2 -CH = CH- (CH₂)_Three-Ph H H
1-673 CO₂Et H H H Me 2 -CH = CH- (CH₂)_Three-Ph H H
1-674 H H H H Me 2 -CH = CH- (CH₂)_Three-(4-F-Ph) H H
1-675 H H H H Me 2 -CH = CH- (CH₂)_Three-(4-Me-Ph) H H
1-676 H H H H Me 2 -CH = CH- (CH₂)_Three-(4-Et-Ph) H H
1-677 H H H H Me 2 -CH = CH- (CH₂)_Three-(4-CF_Three-Ph) H H
1-678 H H H H Me 2 -CH = CH- (CH₂)_Three-(4-MeO-Ph) H H
1-679 H H H H Me 2 -CH = CH- (CH₂)_Three-(4-EtO-Ph) H H
1-680 H H H H Me 2 -CH = CH- (CH₂)_Three-(4-MeS-Ph) H H
1-681 H H H H Me 2 -CH = CH- (CH₂)_Three-(4-cHx-Ph) H H
1-682 H H H H Me 2 -CH = CH- (CH₂)_Three-(4-Ph-Ph) H H
1-683 H H H H Me 2 -CH = CH- (CH₂)_Four-cHx H H
1-684 H H Me Me Me 2 -CH = CH- (CH₂)_Four-cHx H H
1-685 CO₂Me H H H Me 2 -CH = CH- (CH₂)_Four-cHx H H
1-686 CO₂Et H H H Me 2 -CH = CH- (CH₂)_Four-cHx H H
1-687 H H H H Me 2 -CH = CH- (CH₂)_Four-(4-F-cHx) H H
1-688 H H H H Me 2 -CH = CH- (CH₂)_Four-(4-Me-cHx) H H
1-689 H H H H Me 2 -CH = CH- (CH₂)_Four-(4-Et-cHx) H H
1-690 H H H H Me 2 -CH = CH- (CH₂)_Four-(4-CF_Three-cHx) H H
1-691 H H H H Me 2 -CH = CH- (CH₂)_Four-(4-MeO-cHx) H H
1-692 H H H H Me 2 -CH = CH- (CH₂)_Four-(4-EtO-cHx) H H
1-693 H H H H Me 2 -CH = CH- (CH₂)_Four-(4-MeS-cHx) H H
1-694 H H H H Me 2 -CH = CH- (CH₂)_Four-(4-cHx-cHx) H H
1-695 H H H H Me 2 -CH = CH- (CH₂)_Four-(4-Ph-cHx) H H
1-696 H H H H Me 2 -CH = CH- (CH₂)_Four-Ph H H
1-697 H H Me Me Me 2 -CH = CH- (CH₂)_Four-Ph H H
1-698 CO₂Me H H H Me 2 -CH = CH- (CH₂)_Four-Ph H H
1-699 CO₂Et H H H Me 2 -CH = CH- (CH₂)_Four-Ph H H
1-700 H H H H Me 2 -CH = CH- (CH₂)_Four-(4-F-Ph) H H
1-701 H H H H Me 2 -CH = CH- (CH₂)_Four-(4-Me-Ph) H H
1-702 H H H H Me 2 -CH = CH- (CH₂)_Four-(4-Et-Ph) H H
1-703 H H H H Me 2 -CH = CH- (CH₂)_Four-(4-CF_Three-Ph) H H
1-704 H H H H Me 2 -CH = CH- (CH₂)_Four-(4-MeO-Ph) H H
1-705 H H H H Me 2 -CH = CH- (CH₂)_Four-(4-EtO-Ph) H H
1-706 H H H H Me 2 -CH = CH- (CH₂)_Four-(4-MeS-Ph) H H
1-707 H H H H Me 2 -CH = CH- (CH₂)_Four-(4-cHx-Ph) H H
1-708 H H H H Me 2 -CH = CH- (CH₂)_Four-(4-Ph-Ph) H H
1-709 H H H H Me 2 -CH = CH- (CH₂)_Five-cHx H H
1-710 H H H H Me 2 -CH = CH- (CH₂)_Five-Ph H H
1-711 H H H H Me 2 -CH = CH- (CH₂)₆-cHx H H
1-712 H H H H Me 2 -CH = CH- (CH₂)₆-Ph H H
1-713 H H H H Me 2 -C = C-CH₂O-cHx H H
1-714 H H H H Me 2 -C = C-CH₂O-Ph H H
1-715 H H H H Me 2 -C = C- (CH₂)₂O-cHx H H
1-716 H H H H Me 2 -C = C- (CH₂)₂O-Ph H H
1-717 H H H H Me 2 -C≡C-cHx H H
1-718 H H Me Me Me 2 -C≡C-cHx H H
1-719 CO₂Me H H H Me 2 -C≡C-cHx H H
1-720 CO₂Et H H H Me 2 -C≡C-cHx H H
1-721 H H H H Me 2 -C≡C- (4-F-cHx) H H
1-722 H H H H Me 2 -C≡C- (4-Me-cHx) H H
1-723 H H H H Me 2 -C≡C- (4-Et-cHx) H H
1-724 H H H H Me 2 -C≡C- (4-CF_Three-cHx) H H
1-725 H H H H Me 2 -C≡C- (4-MeO-cHx) H H
1-726 H H H H Me 2 -C≡C- (4-EtO-cHx) H H
1-727 H H H H Me 2 -C≡C- (4-MeS-cHx) H H
1-728 H H H H Me 2 -C≡C- (4-cHx-cHx) H H
1-729 H H H H Me 2 -C≡C- (4-Ph-cHx) H H
1-730 H H H H Me 2 -C≡C-Ph H H
1-731 H H Me Me Me 2 -C≡C-Ph H H
1-732 CO₂Me H H H Me 2 -C≡C-Ph H H
1-733 CO₂Et H H H Me 2 -C≡C-Ph H H
1-734 H H H H Me 2 -C≡C- (4-F-Ph) H H
1-735 H H H H Me 2 -C≡C- (4-Me-Ph) H H
1-736 H H H H Me 2 -C≡C- (4-Pr-Ph) H H
1-737 H H H H Me 2 -C≡C- (4-Bu-Ph) H H
1-738 H H H H Me 2 -C≡C- (4-MeO-Ph) H H
1-739 H H H H Me 2 -C≡C- (4-EtO-Ph) H H
1-740 H H H H Me 2 -C≡C- (4-PrO-Ph) H H
1-741 H H H H Me 2 -C≡C- (4-cHx-Ph) H H
1-742 H H H H Me 2 -C≡C- (4-Ph-Ph) H H
1-743 H H H H Me 2 -C≡C- (CH₂)₂-cHx H H
1-744 H H Me Me Me 2 -C≡C- (CH₂)₂-cHx H H
1-745 CO₂Me H H H Me 2 -C≡C- (CH₂)₂-cHx H H
1-746 CO₂Et H H H Me 2 -C≡C- (CH₂)₂-cHx H H
1-747 H H H H Me 2 -C≡C- (CH₂)₂-(4-F-cHx) H H
1-748 H H H H Me 2 -C≡C- (CH₂)₂-(4-Me-cHx) H H
1-749 H H H H Me 2 -C≡C- (CH₂)₂-(4-Et-cHx) H H
1-750 H H H H Me 2 -C≡C- (CH₂)₂-(4-CF_Three-cHx) H H
1-751 H H H H Me 2 -C≡C- (CH₂)₂-(4-MeO-cHx) H H
1-752 H H H H Me 2 -C≡C- (CH₂)₂-(4-EtO-cHx) H H
1-753 H H H H Me 2 -C≡C- (CH₂)₂-(4-MeS-cHx) H H
1-754 H H H H Me 2 -C≡C- (CH₂)₂-(4-cHx-cHx) H H
1-755 H H H H Me 2 -C≡C- (CH₂)₂-(4-Ph-cHx) H H
1-756 H H H H Me 2 -C≡C- (CH₂)₂-Ph H H
1-757 H H Me Me Me 2 -C≡C- (CH₂)₂-Ph H H
1-758 CO₂Me H H H Me 2 -C≡C- (CH₂)₂-Ph H H
1-759 CO₂Et H H H Me 2 -C≡C- (CH₂)₂-Ph H H
1-760 H H H H Me 2 -C≡C- (CH₂)₂-(4-F-Ph) H H
1-761 H H H H Me 2 -C≡C- (CH₂)₂-(4-Me-Ph) H H
1-762 H H H H Me 2 -C≡C- (CH₂)₂-(4-Et-Ph) H H
1-763 H H H H Me 2 -C≡C- (CH₂)₂-(4-CF_Three-Ph) H H
1-764 H H H H Me 2 -C≡C- (CH₂)₂-(4-MeO-Ph) H H
1-765 H H H H Me 2 -C≡C- (CH₂)₂-(4-EtO-Ph) H H
1-766 H H H H Me 2 -C≡C- (CH₂)₂-(4-MeS-Ph) H H
1-767 H H H H Me 2 -C≡C- (CH₂)₂-(4-cHx-Ph) H H
1-768 H H H H Me 2 -C≡C- (CH₂)₂-(4-Ph-Ph) H H
1-769 H H H H Me 2 -C≡C- (CH₂)_Three-cPn H H
1-770 H H H H Me 2 -C≡C- (CH₂)_Three-cHx H H
1-771 H H H H Me 2 -C≡C- (CH₂)_Three-cHx Me H
1-772 H H H H Me 2 -C≡C- (CH₂)_Three-cHx H Me
1-773 H H H H Me 2 -C≡C- (CH₂)_Three-cHx F H
1-774 H H H H Me 2 -C≡C- (CH₂)_Three-cHx H F
1-775 H H Me Me Me 2 -C≡C- (CH₂)_Three-cHx H H
1-776 CO₂Me H H H Me 2 -C≡C- (CH₂)_Three-cHx H H
1-777 CO₂Et H H H Me 2 -C≡C- (CH₂)_Three-cHx H H
1-778 H H H H Me 2 -C≡C- (CH₂)_Three-(3-F-cHx) H H
1-779 H H H H Me 2 -C≡C- (CH₂)_Three-(4-F-cHx) H H
1-780 H H H H Me 2 -C≡C- (CH₂)_Three-(4-Cl-cHx) H H
1-781 H H H H Me 2 -C≡C- (CH₂)_Three-(4-Br-cHx) H H
1-782 H H H H Me 2 -C≡C- (CH₂)_Three-(3-Me-cHx) H H
1-783 H H H H Me 2 -C≡C- (CH₂)_Three-(4-Me-cHx) H H
1-784 H H H H Me 2 -C≡C- (CH₂)_Three-(3-Et-cHx) H H
1-785 H H H H Me 2 -C≡C- (CH₂)_Three-(4-Et-cHx) H H
1-786 H H H H Me 2 -C≡C- (CH₂)_Three-(3-Pr-cHx) H H
1-787 H H H H Me 2 -C≡C- (CH₂)_Three-(4-Pr-cHx) H H
1-788 H H H H Me 2 -C≡C- (CH₂)_Three-(4-iPr-cHx) H H
1-789 H H H H Me 2 -C≡C- (CH₂)_Three-(3-Bu-cHx) H H
1-790 H H H H Me 2 -C≡C- (CH₂)_Three-(4-Bu-cHx) H H
1-791 H H H H Me 2 -C≡C- (CH₂)_Three-(3-CF_Three-cHx) H H
1-792 H H H H Me 2 -C≡C- (CH₂)_Three-(4-CF_Three-cHx) H H
1-793 H H H H Me 2 -C≡C- (CH₂)_Three-(3-MeO-cHx) H H
1-794 H H H H Me 2 -C≡C- (CH₂)_Three-(4-MeO-cHx) H H
1-795 H H H H Me 2 -C≡C- (CH₂)_Three-(3-EtO-cHx) H H
1-796 H H H H Me 2 -C≡C- (CH₂)_Three-(4-EtO-cHx) H H
1-797 H H H H Me 2 -C≡C- (CH₂)_Three-(3-PrO-cHx) H H
1-798 H H H H Me 2 -C≡C- (CH₂)_Three-(4-PrO-cHx) H H
1-799 H H H H Me 2 -C≡C- (CH₂)_Three-(3-iPrO-cHx) H H
1-800 H H H H Me 2 -C≡C- (CH₂)_Three-(4-iPrO-cHx) H H
1-801 H H H H Me 2 -C≡C- (CH₂)_Three-[3- (2-Et-PrO) -cHx] H H
1-802 H H H H Me 2 -C≡C- (CH₂)_Three-[4- (2-Et-PrO) -cHx] H H
1-803 H H H H Me 2 -C≡C- (CH₂)_Three-(3-iBuO-cHx) H H
1-804 H H H H Me 2 -C≡C- (CH₂)_Three-(4-iBuO-cHx) H H
1-805 H H H H Me 2 -C≡C- (CH₂)_Three-(3-MeS-cHx) H H
1-806 H H H H Me 2 -C≡C- (CH₂)_Three-(4-MeS-cHx) H H
1-807 H H H H Me 2 -C≡C- (CH₂)_Three-(3-EtS-cHx) H H
1-808 H H H H Me 2 -C≡C- (CH₂)_Three-(4-EtS-cHx) H H
1-809 H H H H Me 2 -C≡C- (CH₂)_Three-(3-PrS-cHx) H H
1-810 H H H H Me 2 -C≡C- (CH₂)_Three-(4-PrS-cHx) H H
1-811 H H H H Me 2 -C≡C- (CH₂)_Three-(3-iPrS-cHx) H H
1-812 H H H H Me 2 -C≡C- (CH₂)_Three-(4-iPrS-cHx) H H
1-813 H H H H Me 2 -C≡C- (CH₂)_Three-[3- (2-Et-PrS) -cHx] H H
1-814 H H H H Me 2 -C≡C- (CH₂)_Three-[4- (2-Et-PrS) -cHx] H H
1-815 H H H H Me 2 -C≡C- (CH₂)_Three-(3-iBuS-cHx) H H
1-816 H H H H Me 2 -C≡C- (CH₂)_Three-(4-iBuS-cHx) H H
1-817 H H H H Me 2 -C≡C- (CH₂)_Three-(3-cHx-cHx) H H
1-818 H H H H Me 2 -C≡C- (CH₂)_Three-(4-cHx-cHx) H H
1-819 H H H H Me 2 -C≡C- (CH₂)_Three-(3-Ph-cHx) H H
1-820 H H H H Me 2 -C≡C- (CH₂)_Three-(4-Ph-cHx) H H
1-821 H H H H Me 2 -C≡C- (CH₂)_Three-(2,4-diMe-cHx) H H
1-822 H H H H Me 2 -C≡C- (CH₂)_Three-(3,4-diMe-cHx) H H
1-823 H H H H Me 2 -C≡C- (CH₂)_Three-(3,5-diMe-cHx) H H
1-824 H H H H Me 2 -C≡C- (CH₂)_Three-Ph H H
1-825 H H H H Me 2 -C≡C- (CH₂)_Three-Ph Me H
1-826 H H H H Me 2 -C≡C- (CH₂)_Three-Ph H Me
1-827 H H H H Me 2 -C≡C- (CH₂)_Three-Ph F H
1-828 H H H H Me 2 -C≡C- (CH₂)_Three-Ph H F
1-829 H H Me Me Me 2 -C≡C- (CH₂)_Three-Ph H H
1-830 CO₂Me H H H Me 2 -C≡C- (CH₂)_Three-Ph H H
1-831 CO₂Et H H H Me 2 -C≡C- (CH₂)_Three-Ph H H
1-832 H H H H Me 2 -C≡C- (CH₂)_Three-(3-F-Ph) H H
1-833 H H H H Me 2 -C≡C- (CH₂)_Three-(4-F-Ph) H H
1-834 H H H H Me 2 -C≡C- (CH₂)_Three-(4-Cl-Ph) H H
1-835 H H H H Me 2 -C≡C- (CH₂)_Three-(4-Br-Ph) H H
1-836 H H H H Me 2 -C≡C- (CH₂)_Three-(3-Me-Ph) H H
1-837 H H H H Me 2 -C≡C- (CH₂)_Three-(4-Me-Ph) H H
1-838 H H H H Me 2 -C≡C- (CH₂)_Three-(3-Et-Ph) H H
1-839 H H H H Me 2 -C≡C- (CH₂)_Three-(4-Et-Ph) H H
1-840 H H H H Me 2 -C≡C- (CH₂)_Three-(3-Pr-Ph) H H
1-841 H H H H Me 2 -C≡C- (CH₂)_Three-(4-Pr-Ph) H H
1-842 H H H H Me 2 -C≡C- (CH₂)_Three-(3-iPr-Ph) H H
1-843 H H H H Me 2 -C≡C- (CH₂)_Three-(4-iPr-Ph) H H
1-844 H H H H Me 2 -C≡C- (CH₂)_Three-(3-Bu-Ph) H H
1-845 H H H H Me 2 -C≡C- (CH₂)_Three-(4-Bu-Ph) H H
1-846 H H H H Me 2 -C≡C- (CH₂)_Three-(3-CF_Three-Ph) H H
1-847 H H H H Me 2 -C≡C- (CH₂)_Three-(4-CF_Three-Ph) H H
1-848 H H H H Me 2 -C≡C- (CH₂)_Three-(3-MeO-Ph) H H
1-849 H H H H Me 2 -C≡C- (CH₂)_Three-(4-MeO-Ph) H H
1-850 H H H H Me 2 -C≡C- (CH₂)_Three-(3-EtO-Ph) H H
1-851 H H H H Me 2 -C≡C- (CH₂)_Three-(4-EtO-Ph) H H
1-852 H H H H Me 2 -C≡C- (CH₂)_Three-(3-PrO-Ph) H H
1-853 H H H H Me 2 -C≡C- (CH₂)_Three-(4-PrO-Ph) H H
1-854 H H H H Me 2 -C≡C- (CH₂)_Three-(3-iPrO-Ph) H H
1-855 H H H H Me 2 -C≡C- (CH₂)_Three-(4-iPrO-Ph) H H
1-856 H H H H Me 2 -C≡C- (CH₂)_Three-[3- (2-Et-PrO) -Ph] H H
1-857 H H H H Me 2 -C≡C- (CH₂)_Three-[4- (2-Et-PrO) -Ph] H H
1-858 H H H H Me 2 -C≡C- (CH₂)_Three-(3-iBuO-Ph) H H
1-859 H H H H Me 2 -C≡C- (CH₂)_Three-(4-iBuO-Ph) H H
1-860 H H H H Me 2 -C≡C- (CH₂)_Three-(3-MeS-Ph) H H
1-861 H H H H Me 2 -C≡C- (CH₂)_Three-(4-MeS-Ph) H H
1-862 H H H H Me 2 -C≡C- (CH₂)_Three-(3-EtS-Ph) H H
1-863 H H H H Me 2 -C≡C- (CH₂)_Three-(4-EtS-Ph) H H
1-864 H H H H Me 2 -C≡C- (CH₂)_Three-(3-PrS-Ph) H H
1-865 H H H H Me 2 -C≡C- (CH₂)_Three-(4-PrS-Ph) H H
1-866 H H H H Me 2 -C≡C- (CH₂)_Three-(3-iPrS-Ph) H H
1-867 H H H H Me 2 -C≡C- (CH₂)_Three-(4-iPrS-Ph) H H
1-868 H H H H Me 2 -C≡C- (CH₂)_Three-[3- (2-Et-PrS) -Ph] H H
1-869 H H H H Me 2 -C≡C- (CH₂)_Three-[4- (2-Et-PrS) -Ph] H H
1-870 H H H H Me 2 -C≡C- (CH₂)_Three-(3-iBuS-Ph) H H
1-871 H H H H Me 2 -C≡C- (CH₂)_Three-(4-iBuS-Ph) H H
1-872 H H H H Me 2 -C≡C- (CH₂)_Three-(3-cHx-Ph) H H
1-873 H H H H Me 2 -C≡C- (CH₂)_Three-(4-cHx-Ph) H H
1-874 H H H H Me 2 -C≡C- (CH₂)_Three-(3-Ph-Ph) H H
1-875 H H H H Me 2 -C≡C- (CH₂)_Three-(4-Ph-Ph) H H
1-876 H H H H Me 2 -C≡C- (CH₂)_Three-(2,4-diMe-Ph) H H
1-877 H H H H Me 2 -C≡C- (CH₂)_Three-(3,4-diMe-Ph) H H
1-878 H H H H Me 2 -C≡C- (CH₂)_Three-(3,5-diMe-Ph) H H
1-879 H H H H Me 2 -C≡C- (CH₂)_Three-Np (1) H H
1-880 H H H H Me 2 -C≡C- (CH₂)_Three-Np (2) H H
1-881 H H H H Me 2 -C≡C- (CH₂)_Four-cPn H H
1-882 H H H H Me 2 -C≡C- (CH₂)_Four-cHx H H
1-883 H H H H Me 2 -C≡C- (CH₂)_Four-cHx Me H
1-884 H H H H Me 2 -C≡C- (CH₂)_Four-cHx H Me
1-885 H H H H Me 2 -C≡C- (CH₂)_Four-cHx F H
1-886 H H H H Me 2 -C≡C- (CH₂)_Four-cHx H F
1-887 H H Me Me Me 2 -C≡C- (CH₂)_Four-cHx H H
1-888 CO₂Me H H H Me 2 -C≡C- (CH₂)_Four-cHx H H
1-889 CO₂Et H H H Me 2 -C≡C- (CH₂)_Four-cHx H H
1-890 H H H H Me 2 -C≡C- (CH₂)_Four-(3-F-cHx) H H
1-891 H H H H Me 2 -C≡C- (CH₂)_Four-(4-F-cHx) H H
1-892 H H H H Me 2 -C≡C- (CH₂)_Four-(4-Cl-cHx) H H
1-893 H H H H Me 2 -C≡C- (CH₂)_Four-(4-Br-cHx) H H
1-894 H H H H Me 2 -C≡C- (CH₂)_Four-(3-Me-cHx) H H
1-895 H H H H Me 2 -C≡C- (CH₂)_Four-(4-Me-cHx) H H
1-896 H H H H Me 2 -C≡C- (CH₂)_Four-(3-Et-cHx) H H
1-897 H H H H Me 2 -C≡C- (CH₂)_Four-(4-Et-cHx) H H
1-898 H H H H Me 2 -C≡C- (CH₂)_Four-(3-Pr-cHx) H H
1-899 H H H H Me 2 -C≡C- (CH₂)_Four-(4-Pr-cHx) H H
1-900 H H H H Me 2 -C≡C- (CH₂)_Four-(4-iPr-cHx) H H
1-901 H H H H Me 2 -C≡C- (CH₂)_Four-(3-Bu-cHx) H H
1-902 H H H H Me 2 -C≡C- (CH₂)_Four-(4-Bu-cHx) H H
1-903 H H H H Me 2 -C≡C- (CH₂)_Four-(3-CF_Three-cHx) H H
1-904 H H H H Me 2 -C≡C- (CH₂)_Four-(4-CF_Three-cHx) H H
1-905 H H H H Me 2 -C≡C- (CH₂)_Four-(3-MeO-cHx) H H
1-906 H H H H Me 2 -C≡C- (CH₂)_Four-(4-MeO-cHx) H H
1-907 H H H H Me 2 -C≡C- (CH₂)_Four-(3-EtO-cHx) H H
1-908 H H H H Me 2 -C≡C- (CH₂)_Four-(4-EtO-cHx) H H
1-909 H H H H Me 2 -C≡C- (CH₂)_Four-(3-PrO-cHx) H H
1-910 H H H H Me 2 -C≡C- (CH₂)_Four-(4-PrO-cHx) H H
1-911 H H H H Me 2 -C≡C- (CH₂)_Four-(3-iPrO-cHx) H H
1-912 H H H H Me 2 -C≡C- (CH₂)_Four-(4-iPrO-cHx) H H
1-913 H H H H Me 2 -C≡C- (CH₂)_Four-[3- (2-Et-PrO) -cHx] H H
1-914 H H H H Me 2 -C≡C- (CH₂)_Four-[4- (2-Et-PrO) -cHx] H H
1-915 H H H H Me 2 -C≡C- (CH₂)_Four-(3-iBuO-cHx) H H
1-916 H H H H Me 2 -C≡C- (CH₂)_Four-(4-iBuO-cHx) H H
1-917 H H H H Me 2 -C≡C- (CH₂)_Four-(3-MeS-cHx) H H
1-918 H H H H Me 2 -C≡C- (CH₂)_Four-(4-MeS-cHx) H H
1-919 H H H H Me 2 -C≡C- (CH₂)_Four-(3-EtS-cHx) H H
1-920 H H H H Me 2 -C≡C- (CH₂)_Four-(4-EtS-cHx) H H
1-921 H H H H Me 2 -C≡C- (CH₂)_Four-(3-PrS-cHx) H H
1-922 H H H H Me 2 -C≡C- (CH₂)_Four-(4-PrS-cHx) H H
1-923 H H H H Me 2 -C≡C- (CH₂)_Four-(3-iPrS-cHx) H H
1-924 H H H H Me 2 -C≡C- (CH₂)_Four-(4-iPrS-cHx) H H
1-925 H H H H Me 2 -C≡C- (CH₂)_Four-[3- (2-Et-PrS) -cHx] H H
1-926 H H H H Me 2 -C≡C- (CH₂)_Four-[4- (2-Et-PrS) -cHx] H H
1-927 H H H H Me 2 -C≡C- (CH₂)_Four-(3-iBuS-cHx) H H
1-928 H H H H Me 2 -C≡C- (CH₂)_Four-(4-iBuS-cHx) H H
1-929 H H H H Me 2 -C≡C- (CH₂)_Four-(3-cHx-cHx) H H
1-930 H H H H Me 2 -C≡C- (CH₂)_Four-(4-cHx-cHx) H H
1-931 H H H H Me 2 -C≡C- (CH₂)_Four-(3-Ph-cHx) H H
1-932 H H H H Me 2 -C≡C- (CH₂)_Four-(4-Ph-cHx) H H
1-933 H H H H Me 2 -C≡C- (CH₂)_Four-(2,4-diMe-cHx) H H
1-934 H H H H Me 2 -C≡C- (CH₂)_Four-(3,4-diMe-cHx) H H
1-935 H H H H Me 2 -C≡C- (CH₂)_Four-(3,5-diMe-cHx) H H
1-936 H H H H Me 2 -C≡C- (CH₂)_Four-Ph H H
1-937 H H H H Me 2 -C≡C- (CH₂)_Four-Ph Me H
1-938 H H H H Me 2 -C≡C- (CH₂)_Four-Ph H Me
1-939 H H H H Me 2 -C≡C- (CH₂)_Four-Ph F H
1-940 H H H H Me 2 -C≡C- (CH₂)_Four-Ph H F
1-941 H H Me Me Me 2 -C≡C- (CH₂)_Four-Ph H H
1-942 CO₂Me H H H Me 2 -C≡C- (CH₂)_Four-Ph H H
1-943 CO₂Et H H H Me 2 -C≡C- (CH₂)_Four-Ph H H
1-944 H H H H Me 2 -C≡C- (CH₂)_Four-(3-F-Ph) H H
1-945 H H H H Me 2 -C≡C- (CH₂)_Four-(4-F-Ph) H H
1-946 H H H H Me 2 -C≡C- (CH₂)_Four-(4-Cl-Ph) H H
1-947 H H H H Me 2 -C≡C- (CH₂)_Four-(4-Br-Ph) H H
1-948 H H H H Me 2 -C≡C- (CH₂)_Four-(3-Me-Ph) H H
1-949 H H H H Me 2 -C≡C- (CH₂)_Four-(4-Me-Ph) H H
1-950 H H H H Me 2 -C≡C- (CH₂)_Four-(3-Et-Ph) H H
1-951 H H H H Me 2 -C≡C- (CH₂)_Four-(4-Et-Ph) H H
1-952 H H H H Me 2 -C≡C- (CH₂)_Four-(3-Pr-Ph) H H
1-953 H H H H Me 2 -C≡C- (CH₂)_Four-(4-Pr-Ph) H H
1-954 H H H H Me 2 -C≡C- (CH₂)_Four-(3-iPr-Ph) H H
1-955 H H H H Me 2 -C≡C- (CH₂)_Four-(4-iPr-Ph) H H
1-956 H H H H Me 2 -C≡C- (CH₂)_Four-(3-Bu-Ph) H H
1-957 H H H H Me 2 -C≡C- (CH₂)_Four-(4-Bu-Ph) H H
1-958 H H H H Me 2 -C≡C- (CH₂)_Four-(3-CF_Three-Ph) H H
1-959 H H H H Me 2 -C≡C- (CH₂)_Four-(4-CF_Three-Ph) H H
1-960 H H H H Me 2 -C≡C- (CH₂)_Four-(3-MeO-Ph) H H
1-961 H H H H Me 2 -C≡C- (CH₂)_Four-(4-MeO-Ph) H H
1-962 H H H H Me 2 -C≡C- (CH₂)_Four-(3-EtO-Ph) H H
1-963 H H H H Me 2 -C≡C- (CH₂)_Four-(4-EtO-Ph) H H
1-964 H H H H Me 2 -C≡C- (CH₂)_Four-(3-PrO-Ph) H H
1-965 H H H H Me 2 -C≡C- (CH₂)_Four-(4-PrO-Ph) H H
1-966 H H H H Me 2 -C≡C- (CH₂)_Four-(3-iPrO-Ph) H H
1-967 H H H H Me 2 -C≡C- (CH₂)_Four-(4-iPrO-Ph) H H
1-968 H H H H Me 2 -C≡C- (CH₂)_Four-[3- (2-Et-PrO) -Ph] H H
1-969 H H H H Me 2 -C≡C- (CH₂)_Four-[4- (2-Et-PrO) -Ph] H H
1-970 H H H H Me 2 -C≡C- (CH₂)_Four-(3-iBuO-Ph) H H
1-971 H H H H Me 2 -C≡C- (CH₂)_Four-(4-iBuO-Ph) H H
1-972 H H H H Me 2 -C≡C- (CH₂)_Four-(3-MeS-Ph) H H
1-973 H H H H Me 2 -C≡C- (CH₂)_Four-(4-MeS-Ph) H H
1-974 H H H H Me 2 -C≡C- (CH₂)_Four-(3-EtS-Ph) H H
1-975 H H H H Me 2 -C≡C- (CH₂)_Four-(4-EtS-Ph) H H
1-976 H H H H Me 2 -C≡C- (CH₂)_Four-(3-PrS-Ph) H H
1-977 H H H H Me 2 -C≡C- (CH₂)_Four-(4-PrS-Ph) H H
1-978 H H H H Me 2 -C≡C- (CH₂)_Four-(3-iPrS-Ph) H H
1-979 H H H H Me 2 -C≡C- (CH₂)_Four-(4-iPrS-Ph) H H
1-980 H H H H Me 2 -C≡C- (CH₂)_Four-[3- (2-Et-PrS) -Ph] H H
1-981 H H H H Me 2 -C≡C- (CH₂)_Four-[4- (2-Et-PrS) -Ph] H H
1-982 H H H H Me 2 -C≡C- (CH₂)_Four-(3-iBuS-Ph) H H
1-983 H H H H Me 2 -C≡C- (CH₂)_Four-(4-iBuS-Ph) H H
1-984 H H H H Me 2 -C≡C- (CH₂)_Four-(3-cHx-Ph) H H
1-985 H H H H Me 2 -C≡C- (CH₂)_Four-(4-cHx-Ph) H H
1-986 H H H H Me 2 -C≡C- (CH₂)_Four-(3-Ph-Ph) H H
1-987 H H H H Me 2 -C≡C- (CH₂)_Four-(4-Ph-Ph) H H
1-988 H H H H Me 2 -C≡C- (CH₂)_Four-(2,4-diMe-Ph) H H
1-989 H H H H Me 2 -C≡C- (CH₂)_Four-(3,4-diMe-Ph) H H
1-990 H H H H Me 2 -C≡C- (CH₂)_Four-(3,5-diMe-Ph) H H
1-991 H H H H Me 2 -C≡C- (CH₂)_Four-Np (1) H H
1-992 H H H H Me 2 -C≡C- (CH₂)_Four-Np (2) H H
1-993 H H H H Me 2 -C≡C- (CH₂)_Five-cHx H H
1-994 H H Me Me Me 2 -C≡C- (CH₂)_Five-cHx H H
1-995 CO₂Me H H H Me 2 -C≡C- (CH₂)_Five-cHx H H
1-996 CO₂Et H H H Me 2 -C≡C- (CH₂)_Five-cHx H H
1-997 H H H H Me 2 -C≡C- (CH₂)_Five-(4-F-cHx) H H
1-998 H H H H Me 2 -C≡C- (CH₂)_Five-(4-Me-cHx) H H
1-999 H H H H Me 2 -C≡C- (CH₂)_Five-(4-Et-cHx) H H
1-1000 H H H H Me 2 -C≡C- (CH₂)_Five-(4-CF_Three-cHx) H H
1-1001 H H H H Me 2 -C≡C- (CH₂)_Five-(4-MeO-cHx) H H
1-1002 H H H H Me 2 -C≡C- (CH₂)_Five-(4-EtO-cHx) H H
1-1003 H H H H Me 2 -C≡C- (CH₂)_Five-(4-MeS-cHx) H H
1-1004 H H H H Me 2 -C≡C- (CH₂)_Five-(4-cHx-cHx) H H
1-1005 H H H H Me 2 -C≡C- (CH₂)_Five-(4-Ph-cHx) H H
1-1006 H H H H Me 2 -C≡C- (CH₂)_Five-Ph H H
1-1007 H H Me Me Me 2 -C≡C- (CH₂)_Five-Ph H H
1-1008 CO₂Me H H H Me 2 -C≡C- (CH₂)_Five-Ph H H
1-1009 CO₂Et H H H Me 2 -C≡C- (CH₂)_Five-Ph H H
1-1010 H H H H Me 2 -C≡C- (CH₂)_Five-(4-F-Ph) H H
1-1011 H H H H Me 2 -C≡C- (CH₂)_Five-(4-Me-Ph) H H
1-1012 H H H H Me 2 -C≡C- (CH₂)_Five-(4-Et-Ph) H H
1-1013 H H H H Me 2 -C≡C- (CH₂)_Five-(4-CF_Three-Ph) H H
1-1014 H H H H Me 2 -C≡C- (CH₂)_Five-(4-MeO-Ph) H H
1-1015 H H H H Me 2 -C≡C- (CH₂)_Five-(4-EtO-Ph) H H
1-1016 H H H H Me 2 -C≡C- (CH₂)_Five-(4-MeS-Ph) H H
1-1017 H H H H Me 2 -C≡C- (CH₂)_Five-(4-cHx-Ph) H H
1-1018 H H H H Me 2 -C≡C- (CH₂)_Five-(4-Ph-Ph) H H
1-1019 H H H H Me 2 -C≡C- (CH₂)₆-cHx H H
1-1020 H H Me Me Me 2 -C≡C- (CH₂)₆-cHx H H
1-1021 CO₂Me H H H Me 2 -C≡C- (CH₂)₆-cHx H H
1-1022 CO₂Et H H H Me 2 -C≡C- (CH₂)₆-cHx H H
1-1023 H H H H Me 2 -C≡C- (CH₂)₆-(4-F-cHx) H H
1-1024 H H H H Me 2 -C≡C- (CH₂)₆-(4-Me-cHx) H H
1-1025 H H H H Me 2 -C≡C- (CH₂)₆-(4-Et-cHx) H H
1-1026 H H H H Me 2 -C≡C- (CH₂)₆-(4-CF_Three-cHx) H H
1-1027 H H H H Me 2 -C≡C- (CH₂)₆-(4-MeO-cHx) H H
1-1028 H H H H Me 2 -C≡C- (CH₂)₆-(4-EtO-cHx) H H
1-1029 H H H H Me 2 -C≡C- (CH₂)₆-(4-MeS-cHx) H H
1-1030 H H H H Me 2 -C≡C- (CH₂)₆-(4-cHx-cHx) H H
1-1031 H H H H Me 2 -C≡C- (CH₂)₆-(4-Ph-cHx) H H
1-1032 H H H H Me 2 -C≡C- (CH₂)₆-Ph H H
1-1033 H H Me Me 2 -C≡C- (CH₂)₆-Ph H H
1-1034 CO₂Me H H Me 2 -C≡C- (CH₂)₆-Ph H H
1-1035 CO₂Et H H Me 2 -C≡C- (CH₂)₆-Ph H H
1-1036 H H H H Me 2 -C≡C- (CH₂)₆-(4-F-Ph) H H
1-1037 H H H H Me 2 -C≡C- (CH₂)₆-(4-Me-Ph) H H
1-1038 H H H H Me 2 -C≡C- (CH₂)₆-(4-Et-Ph) H H
1-1039 H H H H Me 2 -C≡C- (CH₂)₆-(4-CF_Three-Ph) H H
1-1040 H H H H Me 2 -C≡C- (CH₂)₆-(4-MeO-Ph) H H
1-1041 H H H H Me 2 -C≡C- (CH₂)₆-(4-EtO-Ph) H H
1-1042 H H H H Me 2 -C≡C- (CH₂)₆-(4-MeS-Ph) H H
1-1043 H H H H Me 2 -C≡C- (CH₂)₆-(4-cHx-Ph) H H
1-1044 H H H H Me 2 -C≡C- (CH₂)₆-(4-Ph-Ph) H H
1-1045 H H H H Me 2 -C≡C-CH₂-O-cHx H H
1-1046 H H Me Me Me 2 -C≡C-CH₂-O-cHx H H
1-1047 CO₂Me H H H Me 2 -C≡C-CH₂-O-cHx H H
1-1048 CO₂Et H H H Me 2 -C≡C-CH₂-O-cHx H H
1-1049 H H H H Me 2 -C≡C-CH₂-O- (4-F-cHx) H H
1-1050 H H H H Me 2 -C≡C-CH₂-O- (4-Me-cHx) H H
1-1051 H H H H Me 2 -C≡C-CH₂-O- (4-Et-cHx) H H
1-1052 H H H H Me 2 -C≡C-CH₂-O- (4-CF_Three-cHx) H H
1-1053 H H H H Me 2 -C≡C-CH₂-O- (4-MeO-cHx) H H
1-1054 H H H H Me 2 -C≡C-CH₂-O- (4-EtO-cHx) H H
1-1055 H H H H Me 2 -C≡C-CH₂-O- (4-MeS-cHx) H H
1-1056 H H H H Me 2 -C≡C-CH₂-O- (4-cHx-cHx) H H
1-1057 H H H H Me 2 -C≡C-CH₂-O- (4-Ph-cHx) H H
1-1058 H H H H Me 2 -C≡C-CH₂-O-Ph H H
1-1059 H H Me Me Me 2 -C≡C-CH₂-O-Ph H H
1-1060 CO₂Me H H H Me 2 -C≡C-CH₂-O-Ph H H
1-1061 CO₂Et H H H Me 2 -C≡C-CH₂-O-Ph H H
1-1062 H H H H Me 2 -C≡C-CH₂-O- (4-F-Ph) H H
1-1063 H H H H Me 2 -C≡C-CH₂-O- (4-Me-Ph) H H
1-1064 H H H H Me 2 -C≡C-CH₂-O- (4-Et-Ph) H H
1-1065 H H H H Me 2 -C≡C-CH₂-O- (4-CF_Three-Ph) H H
1-1066 H H H H Me 2 -C≡C-CH₂-O- (4-MeO-Ph) H H
1-1067 H H H H Me 2 -C≡C-CH₂-O- (4-EtO-Ph) H H
1-1068 H H H H Me 2 -C≡C-CH₂-O- (4-MeS-Ph) H H
1-1069 H H H H Me 2 -C≡C-CH₂-O- (4-cHx-Ph) H H
1-1070 H H H H Me 2 -C≡C-CH₂-O- (4-Ph-Ph) H H
1-1071 H H H H Me 2 -C≡C- (CH₂)₂O-cPn H H
1-1072 H H H H Me 2 -C≡C- (CH₂)₂O-cHx H H
1-1073 H H H H Me 2 -C≡C- (CH₂)₂O-cHx Me H
1-1074 H H H H Me 2 -C≡C- (CH₂)₂O-cHx H Me
1-1075 H H H H Me 2 -C≡C- (CH₂)₂O-cHx F H
1-1076 H H H H Me 2 -C≡C- (CH₂)₂O-cHx H F
1-1077 H H Me Me Me 2 -C≡C- (CH₂)₂O-cHx H H
1-1078 CO₂Me H H H Me 2 -C≡C- (CH₂)₂O-cHx H H
1-1079 CO₂Et H H H Me 2 -C≡C- (CH₂)₂O-cHx H H
1-1080 H H H H Me 2 -C≡C- (CH₂)₂O- (3-F-cHx) H H
1-1081 H H H H Me 2 -C≡C- (CH₂)₂O- (4-F-cHx) H H
1-1082 H H H H Me 2 -C≡C- (CH₂)₂O- (4-Cl-cHx) H H
1-1083 H H H H Me 2 -C≡C- (CH₂)₂O- (4-Br-cHx) H H
1-1084 H H H H Me 2 -C≡C- (CH₂)₂O- (3-Me-cHx) H H
1-1085 H H H H Me 2 -C≡C- (CH₂)₂O- (4-Me-cHx) H H
1-1086 H H H H Me 2 -C≡C- (CH₂)₂O- (3-Et-cHx) H H
1-1087 H H H H Me 2 -C≡C- (CH₂)₂O- (4-Et-cHx) H H
1-1088 H H H H Me 2 -C≡C- (CH₂)₂O- (3-Pr-cHx) H H
1-1089 H H H H Me 2 -C≡C- (CH₂)₂O- (4-Pr-cHx) H H
1-1090 H H H H Me 2 -C≡C- (CH₂)₂O- (4-iPr-cHx) H H
1-1091 H H H H Me 2 -C≡C- (CH₂)₂O- (3-Bu-cHx) H H
1-1092 H H H H Me 2 -C≡C- (CH₂)₂O- (4-Bu-cHx) H H
1-1093 H H H H Me 2 -C≡C- (CH₂)₂O- (3-CF_Three-cHx) H H
1-1094 H H H H Me 2 -C≡C- (CH₂)₂O- (4-CF_Three-cHx) H H
1-1095 H H H H Me 2 -C≡C- (CH₂)₂O- (3-MeO-cHx) H H
1-1096 H H H H Me 2 -C≡C- (CH₂)₂O- (4-MeO-cHx) H H
1-1097 H H H H Me 2 -C≡C- (CH₂)₂O- (3-EtO-cHx) H H
1-1098 H H H H Me 2 -C≡C- (CH₂)₂O- (4-EtO-cHx) H H
1-1099 H H H H Me 2 -C≡C- (CH₂)₂O- (3-PrO-cHx) H H
1-1100 H H H H Me 2 -C≡C- (CH₂)₂O- (4-PrO-cHx) H H
1-1101 H H H H Me 2 -C≡C- (CH₂)₂O- (3-iPrO-cHx) H H
1-1102 H H H H Me 2 -C≡C- (CH₂)₂O- (4-iPrO-cHx) H H
1-1103 H H H H Me 2 -C≡C- (CH₂)₂O- [3- (2-Et-PrO) -cHx] H H
1-1104 H H H H Me 2 -C≡C- (CH₂)₂O- [4- (2-Et-PrO) -cHx] H H
1-1105 H H H H Me 2 -C≡C- (CH₂)₂O- (3-iBuO-cHx) H H
1-1106 H H H H Me 2 -C≡C- (CH₂)₂O- (4-iBuO-cHx) H H
1-1107 H H H H Me 2 -C≡C- (CH₂)₂O- (3-MeS-cHx) H H
1-1108 H H H H Me 2 -C≡C- (CH₂)₂O- (4-MeS-cHx) H H
1-1109 H H H H Me 2 -C≡C- (CH₂)₂O- (3-EtS-cHx) H H
1-1110 H H H H Me 2 -C≡C- (CH₂)₂O- (4-EtS-cHx) H H
1-1111 H H H H Me 2 -C≡C- (CH₂)₂O- (3-PrS-cHx) H H
1-1112 H H H H Me 2 -C≡C- (CH₂)₂O- (4-PrS-cHx) H H
1-1113 H H H H Me 2 -C≡C- (CH₂)₂O- (3-iPrS-cHx) H H
1-1114 H H H H Me 2 -C≡C- (CH₂)₂O- (4-iPrS-cHx) H H
1-1115 H H H H Me 2 -C≡C- (CH₂)₂O- [3- (2-Et-PrS) -cHx] H H
1-1116 H H H H Me 2 -C≡C- (CH₂)₂O- [4- (2-Et-PrS) -cHx] H H
1-1117 H H H H Me 2 -C≡C- (CH₂)₂O- (3-iBuS-cHx) H H
1-1118 H H H H Me 2 -C≡C- (CH₂)₂O- (4-iBuS-cHx) H H
1-1119 H H H H Me 2 -C≡C- (CH₂)₂O- (3-cHx-cHx) H H
1-1120 H H H H Me 2 -C≡C- (CH₂)₂O- (4-cHx-cHx) H H
1-1121 H H H H Me 2 -C≡C- (CH₂)₂O- (3-Ph-cHx) H H
1-1122 H H H H Me 2 -C≡C- (CH₂)₂O- (4-Ph-cHx) H H
1-1123 H H H H Me 2 -C≡C- (CH₂)₂O- (2,4-diMe-cHx) H H
1-1124 H H H H Me 2 -C≡C- (CH₂)₂O- (3,4-diMe-cHx) H H
1-1125 H H H H Me 2 -C≡C- (CH₂)₂O- (3,5-diMe-cHx) H H
1-1126 H H H H Me 2 -C≡C- (CH₂)₂O-Ph H H
1-1127 H H H H Me 2 -C≡C- (CH₂)₂O-Ph Me H
1-1128 H H H H Me 2 -C≡C- (CH₂)₂O-Ph H Me
1-1129 H H H H Me 2 -C≡C- (CH₂)₂O-Ph F H
1-1130 H H H H Me 2 -C≡C- (CH₂)₂O-Ph H F
1-1131 H H Me Me Me 2 -C≡C- (CH₂)₂O-Ph H H
1-1132 CO₂Me H H H Me 2 -C≡C- (CH₂)₂O-Ph H H
1-1133 CO₂Et H H H Me 2 -C≡C- (CH₂)₂O-Ph H H
1-1134 H H H H Me 2 -C≡C- (CH₂)₂O- (3-F-Ph) H H
1-1135 H H H H Me 2 -C≡C- (CH₂)₂O- (4-F-Ph) H H
1-1136 H H H H Me 2 -C≡C- (CH₂)₂O- (4-Cl-Ph) H H
1-1137 H H H H Me 2 -C≡C- (CH₂)₂O- (4-Br-Ph) H H
1-1138 H H H H Me 2 -C≡C- (CH₂)₂O- (3-Me-Ph) H H
1-1139 H H H H Me 2 -C≡C- (CH₂)₂O- (4-Me-Ph) H H
1-1140 H H H H Me 2 -C≡C- (CH₂)₂O- (3-Et-Ph) H H
1-1141 H H H H Me 2 -C≡C- (CH₂)₂O- (4-Et-Ph) H H
1-1142 H H H H Me 2 -C≡C- (CH₂)₂O- (3-Pr-Ph) H H
1-1143 H H H H Me 2 -C≡C- (CH₂)₂O- (4-Pr-Ph) H H
1-1144 H H H H Me 2 -C≡C- (CH₂)₂O- (3-iPr-Ph) H H
1-1145 H H H H Me 2 -C≡C- (CH₂)₂O- (4-iPr-Ph) H H
1-1146 H H H H Me 2 -C≡C- (CH₂)₂O- (3-Bu-Ph) H H
1-1147 H H H H Me 2 -C≡C- (CH₂)₂O- (4-Bu-Ph) H H
1-1148 H H H H Me 2 -C≡C- (CH₂)₂O- (3-CF_Three-Ph) H H
1-1149 H H H H Me 2 -C≡C- (CH₂)₂O- (4-CF_Three-Ph) H H
1-1150 H H H H Me 2 -C≡C- (CH₂)₂O- (3-MeO-Ph) H H
1-1151 H H H H Me 2 -C≡C- (CH₂)₂O- (4-MeO-Ph) H H
1-1152 H H H H Me 2 -C≡C- (CH₂)₂O- (3-EtO-Ph) H H
1-1153 H H H H Me 2 -C≡C- (CH₂)₂O- (4-EtO-Ph) H H
1-1154 H H H H Me 2 -C≡C- (CH₂)₂O- (3-PrO-Ph) H H
1-1155 H H H H Me 2 -C≡C- (CH₂)₂O- (4-PrO-Ph) H H
1-1156 H H H H Me 2 -C≡C- (CH₂)₂O- (3-iPrO-Ph) H H
1-1157 H H H H Me 2 -C≡C- (CH₂)₂O- (4-iPrO-Ph) H H
1-1158 H H H H Me 2 -C≡C- (CH₂)₂O- [3- (2-Et-PrO) -Ph] H H
1-1159 H H H H Me 2 -C≡C- (CH₂)₂O- [4- (2-Et-PrO) -Ph] H H
1-1160 H H H H Me 2 -C≡C- (CH₂)₂O- (3-iBuO-Ph) H H
1-1161 H H H H Me 2 -C≡C- (CH₂)₂O- (4-iBuO-Ph) H H
1-1162 H H H H Me 2 -C≡C- (CH₂)₂O- (3-MeS-Ph) H H
1-1163 H H H H Me 2 -C≡C- (CH₂)₂O- (4-MeS-Ph) H H
1-1164 H H H H Me 2 -C≡C- (CH₂)₂O- (3-EtS-Ph) H H
1-1165 H H H H Me 2 -C≡C- (CH₂)₂O- (4-EtS-Ph) H H
1-1166 H H H H Me 2 -C≡C- (CH₂)₂O- (3-PrS-Ph) H H
1-1167 H H H H Me 2 -C≡C- (CH₂)₂O- (4-PrS-Ph) H H
1-1168 H H H H Me 2 -C≡C- (CH₂)₂O- (3-iPrS-Ph) H H
1-1169 H H H H Me 2 -C≡C- (CH₂)₂O- (4-iPrS-Ph) H H
1-1170 H H H H Me 2 -C≡C- (CH₂)₂O- [3- (2-Et-PrS) -Ph] H H
1-1171 H H H H Me 2 -C≡C- (CH₂)₂O- [4- (2-Et-PrS) -Ph] H H
1-1172 H H H H Me 2 -C≡C- (CH₂)₂O- (3-iBuS-Ph) H H
1-1173 H H H H Me 2 -C≡C- (CH₂)₂O- (4-iBuS-Ph) H H
1-1174 H H H H Me 2 -C≡C- (CH₂)₂O- (3-cHx-Ph) H H
1-1175 H H H H Me 2 -C≡C- (CH₂)₂O- (4-cHx-Ph) H H
1-1176 H H H H Me 2 -C≡C- (CH₂)₂O- (3-Ph-Ph) H H
1-1177 H H H H Me 2 -C≡C- (CH₂)₂O- (4-Ph-Ph) H H
1-1178 H H H H Me 2 -C≡C- (CH₂)₂O- (2,4-diMe-Ph) H H
1-1179 H H H H Me 2 -C≡C- (CH₂)₂O- (3,4-diMe-Ph) H H
1-1180 H H H H Me 2 -C≡C- (CH₂)₂O- (3,5-diMe-Ph) H H
1-1181 H H H H Me 2 -C≡C- (CH₂)_ThreeO-cHx H H
1-1182 H H H H Me 2 -C≡C- (CH₂)_ThreeO-Ph H H
1-1183 H H H H Me 2 -C≡C- (CH₂)_FourO-cHx H H
1-1184 H H H H Me 2 -C≡C- (CH₂)_FourO-Ph H H
1-1185 H H H H Me 2 -C≡C-CH₂-OCH₂-cHx H H
1-1186 H H Me Me Me 2 -C≡C-CH₂-OCH₂-cHx H H
1-1187 CO₂Me H H H Me 2 -C≡C-CH₂-OCH₂-cHx H H
1-1188 CO₂Et H H H Me 2 -C≡C-CH₂-OCH₂-cHx H H
1-1189 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-F-cHx) H H
1-1190 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-Me-cHx) H H
1-1191 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-Et-cHx) H H
1-1192 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-CF_Three-cHx) H H
1-1193 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-MeO-cHx) H H
1-1194 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-EtO-cHx) H H
1-1195 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-MeS-cHx) H H
1-1196 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-cHx-cHx) H H
1-1197 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-Ph-cHx) H H
1-1198 H H H H Me 2 -C≡C-CH₂-OCH₂-Ph H H
1-1199 H H Me Me Me 2 -C≡C-CH₂-OCH₂-Ph H H
1-1200 CO₂Me H H H Me 2 -C≡C-CH₂-OCH₂-Ph H H
1-1201 CO₂Et H H H Me 2 -C≡C-CH₂-OCH₂-Ph H H
1-1202 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-F-Ph) H H
1-1203 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-Me-Ph) H H
1-1204 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-Et-Ph) H H
1-1205 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-CF_Three-Ph) H H
1-1206 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-MeO-Ph) H H
1-1207 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-EtO-Ph) H H
1-1208 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-MeS-Ph) H H
1-1209 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-cHx-Ph) H H
1-1210 H H H H Me 2 -C≡C-CH₂-OCH₂-(4-Ph-Ph) H H
1-1211 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-cPn H H
1-1212 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-cHx H H
1-1213 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-cHx Me H
1-1214 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-cHx H Me
1-1215 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-cHx F H
1-1216 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-cHx H F
1-1217 H H Me Me Me 2 --C≡C- (CH₂)₂-OCH₂-CH₂-cHx H H
1-1218 CO₂Me H H H Me 2 -C≡C- (CH₂)₂-OCH₂-cHx H H
1-1219 CO₂Et H H H Me 2 -C≡C- (CH₂)₂-OCH₂-cHx H H
1-1220 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-F-cHx) H H
1-1221 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-F-cHx) H H
1-1222 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-Cl-cHx) H H
1-1223 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-Br-cHx) H H
1-1224 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-Me-cHx) H H
1-1225 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-Me-cHx) H H
1-1226 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-Et-cHx) H H
1-1227 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-Et-cHx) H H
1-1228 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-Pr-cHx) H H
1-1229 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-Pr-cHx) H H
1-1230 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-iPr-cHx) H H
1-1231 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-Bu-cHx) H H
1-1232 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-Bu-cHx) H H
1-1233 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-CF_Three-cHx) H H
1-1234 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-CF_Three-cHx) H H
1-1235 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-MeO-cHx) H H
1-1236 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-MeO-cHx) H H
1-1237 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-EtO-cHx) H H
1-1238 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-EtO-cHx) H H
1-1239 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-PrO-cHx) H H
1-1240 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-PrO-cHx) H H
1-1241 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-iPrO-cHx) H H
1-1242 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-iPrO-cHx) H H
1-1243 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-[3- (2-Et-PrO) cHx] H H
1-1244 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-[4- (2-Et-PrO) cHx] H H
1-1245 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-iBuO-cHx) H H
1-1246 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-iBuO-cHx) H H
1-1247 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-MeS-cHx) H H
1-1248 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-MeS-cHx) H H
1-1249 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-EtS-cHx) H H
1-1250 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-EtS-cHx) H H
1-1251 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-PrS-cHx) H H
1-1252 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-PrS-cHx) H H
1-1253 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-iPrS-cHx) H H
1-1254 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-iPrS-cHx) H H
1-1255 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-[3- (2-Et-PrS) cHx] H H
1-1256 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-[4- (2-Et-PrS) cHx] H H
1-1257 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-iBuS-cHx) H H
1-1258 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-iBuS-cHx) H H
1-1259 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-cHx-cHx) H H
1-1260 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-cHx-cHx) H H
1-1261 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-Ph-cHx) H H
1-1262 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-Ph-cHx) H H
1-1263 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(2,4-diMe-cHx) H H
1-1264 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3,4-diMe-cHx) H H
1-1265 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3,5-diMe-cHx) H H
1-1266 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-Ph H H
1-1267 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-Ph Me H
1-1268 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-Ph H Me
1-1269 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-Ph F H
1-1270 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-Ph H F
1-1271 H H Me Me Me 2 -C≡C- (CH₂)₂-OCH₂-CH₂-Ph H H
1-1272 CO₂Me H H H Me 2 -C≡C- (CH₂)₂-OCH₂-Ph H H
1-1273 CO₂Et H H H Me 2 -C≡C- (CH₂)₂-OCH₂-Ph H H
1-1274 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-F-Ph) H H
1-1275 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-F-Ph) H H
1-1276 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-Cl-Ph) H H
1-1277 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-Br-Ph) H H
1-1278 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-Me-Ph) H H
1-1279 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-Me-Ph) H H
1-1280 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-Et-Ph) H H
1-1281 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-Et-Ph) H H
1-1282 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-Pr-Ph) H H
1-1283 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-Pr-Ph) H H
1-1284 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-iPr-Ph) H H
1-1285 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-iPr-Ph) H H
1-1286 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-Bu-Ph) H H
1-1287 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-Bu-Ph) H H
1-1288 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-CF_Three-Ph) H H
1-1289 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-CF_Three-Ph) H H
1-1290 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-MeO-Ph) H H
1-1291 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-MeO-Ph) H H
1-1292 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-EtO-Ph) H H
1-1293 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-EtO-Ph) H H
1-1294 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-PrO-Ph) H H
1-1295 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-PrO-Ph) H H
1-1296 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-iPrO-Ph) H H
1-1297 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-iPrO-Ph) H H
1-1298 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-[3- (2-Et-PrO) Ph] H H
1-1299 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-[4- (2-Et-PrO) Ph] H H
1-1300 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-iBuO-Ph) H H
1-1301 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-iBuO-Ph) H H
1-1302 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-MeS-Ph) H H
1-1303 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-MeS-Ph) H H
1-1304 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-EtS-Ph) H H
1-1305 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-EtS-Ph) H H
1-1306 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-PrS-Ph) H H
1-1307 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-PrS-Ph) H H
1-1308 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-iPrS-Ph) H H
1-1309 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-iPrS-Ph) H H
1-1310 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-[3- (2-Et-PrS) Ph] H H
1-1311 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-[4- (2-Et-PrS) Ph] H H
1-1312 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-iBuS-Ph) H H
1-1313 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-iBuS-Ph) H H
1-1314 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-cHx-Ph) H H
1-1315 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-cHx-Ph) H H
1-1316 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3-Ph-Ph) H H
1-1317 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(4-Ph-Ph) H H
1-1318 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(2,4-diMe-Ph) H H
1-1319 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3,4-diMe-Ph) H H
1-1320 H H H H Me 2 -C≡C- (CH₂)₂-OCH₂-(3,5-diMe-Ph) H H
1-1321 H H H H Me 2 -C≡C- (CH₂)_Three-OCH₂-cHx H H
1-1322 H H H H Me 2 -C≡C- (CH₂)_Three-OCH₂-Ph H H
1-1323 H H H H Me 2 -C≡C- (CH₂)_Four-OCH₂-cHx H H
1-1324 H H H H Me 2 -C≡C- (CH₂)_Four-OCH₂-Ph H H
1-1325 H H H H Me 2 -CO-CH₂-(4-cHx-Ph) H H
1-1326 H H H H Me 2 -CO-CH₂-(4-Ph-Ph) H H
1-1327 H H H H Me 2 -CO- (CH₂)₂-cHx H H
1-1328 H H H H Me 2 -CO- (CH₂)₂-Ph H H
1-1329 H H H H Me 2 -CO- (CH₂)_Three-cHx H H
1-1330 H H H H Me 2 -CO- (CH₂)_Three-Ph H H
1-1331 H H H H Me 2 -CO- (CH₂)_Four-cHx H H
1-1332 H H Me Me Me 2 -CO- (CH₂)_Four-cHx H H
1-1333 CO₂Me H H H Me 2 -CO- (CH₂)_Four-cHx H H
1-1334 CO₂Et H H H Me 2 -CO- (CH₂)_Four-cHx H H
1-1335 H H H H Me 2 -CO- (CH₂)_Four-(4-F-cHx) H H
1-1336 H H H H Me 2 -CO- (CH₂)_Four-(4-Me-cHx) H H
1-1337 H H H H Me 2 -CO- (CH₂)_Four-(4-Et-cHx) H H
1-1338 H H H H Me 2 -CO- (CH₂)_Four-(4-CF_Three-cHx) H H
1-1339 H H H H Me 2 -CO- (CH₂)_Four-(4-MeO-cHx) H H
1-1340 H H H H Me 2 -CO- (CH₂)_Four-(4-EtO-cHx) H H
1-1341 H H H H Me 2 -CO- (CH₂)_Four-(4-MeS-cHx) H H
1-1342 H H H H Me 2 -CO- (CH₂)_Four-(4-cHx-cHx) H H
1-1343 H H H H Me 2 -CO- (CH₂)_Four-(4-Ph-cHx) H H
1-1344 H H H H Me 2 -CO- (CH₂)_Four-Ph H H
1-1345 H H Me Me Me 2 -CO- (CH₂)_Four-Ph H H
1-1346 CO₂Me H H H Me 2 -CO- (CH₂)_Four-Ph H H
1-1347 CO₂Et H H H Me 2 -CO- (CH₂)_Four-Ph H H
1-1348 H H H H Me 2 -CO- (CH₂)_Four-(4-F-Ph) H H
1-1349 H H H H Me 2 -CO- (CH₂)_Four-(4-Me-Ph) H H
1-1350 H H H H Me 2 -CO- (CH₂)_Four-(4-Et-Ph) H H
1-1351 H H H H Me 2 -CO- (CH₂)_Four-(4-CF_Three-Ph) H H
1-1352 H H H H Me 2 -CO- (CH₂)_Four-(4-MeO-Ph) H H
1-1353 H H H H Me 2 -CO- (CH₂)_Four-(4-EtO-Ph) H H
1-1354 H H H H Me 2 -CO- (CH₂)_Four-(4-MeS-Ph) H H
1-1355 H H H H Me 2 -CO- (CH₂)_Four-(4-cHx-Ph) H H
1-1356 H H H H Me 2 -CO- (CH₂)_Four-(4-Ph-Ph) H H
1-1357 H H H H Me 2 -CO- (CH₂)_Five-cHx H H
1-1358 H H Me Me Me 2 -CO- (CH₂)_Five-cHx H H
1-1359 CO₂Me H H H Me 2 -CO- (CH₂)_Five-cHx H H
1-1360 CO₂Et H H H Me 2 -CO- (CH₂)_Five-cHx H H
1-1361 H H H H Me 2 -CO- (CH₂)_Five-(4-F-cHx) H H
1-1362 H H H H Me 2 -CO- (CH₂)_Five-(4-Me-cHx) H H
1-1363 H H H H Me 2 -CO- (CH₂)_Five-(4-Et-cHx) H H
1-1364 H H H H Me 2 -CO- (CH₂)_Five-(4-CF_Three-cHx) H H
1-1365 H H H H Me 2 -CO- (CH₂)_Five-(4-MeO-cHx) H H
1-1366 H H H H Me 2 -CO- (CH₂)_Five-(4-EtO-cHx) H H
1-1367 H H H H Me 2 -CO- (CH₂)_Five-(4-MeS-cHx) H H
1-1368 H H H H Me 2 -CO- (CH₂)_Five-(4-cHx-cHx) H H
1-1369 H H H H Me 2 -CO- (CH₂)_Five-(4-Ph-cHx) H H
1-1370 H H H H Me 2 -CO- (CH₂)_Five-Ph H H
1-1371 H H Me Me Me 2 -CO- (CH₂)_Five-Ph H H
1-1372 CO₂Me H H H Me 2 -CO- (CH₂)_Five-Ph H H
1-1373 CO₂Et H H H Me 2 -CO- (CH₂)_Five-Ph H H
1-1374 H H H H Me 2 -CO- (CH₂)_Five-(4-F-Ph) H H
1-1375 H H H H Me 2 -CO- (CH₂)_Five-(4-Me-Ph) H H
1-1376 H H H H Me 2 -CO- (CH₂)_Five-(4-Et-Ph) H H
1-1377 H H H H Me 2 -CO- (CH₂)_Five-(4-CF_Three-Ph) H H
1-1378 H H H H Me 2 -CO- (CH₂)_Five-(4-MeO-Ph) H H
1-1379 H H H H Me 2 -CO- (CH₂)_Five-(4-EtO-Ph) H H
1-1380 H H H H Me 2 -CO- (CH₂)_Five-(4-MeS-Ph) H H
1-1381 H H H H Me 2 -CO- (CH₂)_Five-(4-cHx-Ph) H H
1-1382 H H H H Me 2 -CO- (CH₂)_Five-(4-Ph-Ph) H H
1-1383 H H H H Me 2 -CO- (CH₂)₆-cHx H H
1-1384 H H H H Me 2 -CO- (CH₂)₆-Ph H H
1-1385 H H H H Me 2 -CO- (CH₂)₇-cHx H H
1-1386 H H H H Me 2 -CO- (CH₂)₇-Ph H H
1-1387 H H H H Me 2 -CO- (CH₂)₂-O-cHx H H
1-1388 H H Me Me Me 2 -CO- (CH₂)₂-O-cHx H H
1-1389 CO₂Me H H H Me 2 -CO- (CH₂)₂-O-cHx H H
1-1390 CO₂Et H H H Me 2 -CO- (CH₂)₂-O-cHx H H
1-1391 H H H H Me 2 -CO- (CH₂)₂-O- (4-F-cHx) H H
1-1392 H H H H Me 2 -CO- (CH₂)₂-O- (4-Me-cHx) H H
1-1393 H H H H Me 2 -CO- (CH₂)₂-O- (4-Et-cHx) H H
1-1394 H H H H Me 2 -CO- (CH₂)₂-O- (4-CF_Three-cHx) H H
1-1395 H H H H Me 2 -CO- (CH₂)₂-O- (4-MeO-cHx) H H
1-1396 H H H H Me 2 -CO- (CH₂)₂-O- (4-EtO-cHx) H H
1-1397 H H H H Me 2 -CO- (CH₂)₂-O- (4-MeS-cHx) H H
1-1398 H H H H Me 2 -CO- (CH₂)₂-O- (4-cHx-cHx) H H
1-1399 H H H H Me 2 -CO- (CH₂)₂-O- (4-Ph-cHx) H H
1-1400 H H H H Me 2 -CO- (CH₂)₂-O-Ph H H
1-1401 H H Me Me Me 2 -CO- (CH₂)₂-O-Ph H H
1-1402 CO₂Me H H H Me 2 -CO- (CH₂)₂-O-Ph H H
1-1403 CO₂Et H H H Me 2 -CO- (CH₂)₂-O-Ph H H
1-1404 H H H H Me 2 -CO- (CH₂)₂-O- (4-F-Ph) H H
1-1405 H H H H Me 2 -CO- (CH₂)₂-O- (4-Me-Ph) H H
1-1406 H H H H Me 2 -CO- (CH₂)₂-O- (4-Et-Ph) H H
1-1407 H H H H Me 2 -CO- (CH₂)₂-O- (4-CF_Three-Ph) H H
1-1408 H H H H Me 2 -CO- (CH₂)₂-O- (4-MeO-Ph) H H
1-1409 H H H H Me 2 -CO- (CH₂)₂-O- (4-EtO-Ph) H H
1-1410 H H H H Me 2 -CO- (CH₂)₂-O- (4-MeS-Ph) H H
1-1411 H H H H Me 2 -CO- (CH₂)₂-O- (4-cHx-Ph) H H
1-1412 H H H H Me 2 -CO- (CH₂)₂-O- (4-Ph-Ph) H H
1-1413 H H H H Me 2 -CO- (CH₂)_Three-O-cPn H H
1-1414 H H H H Me 2 -CO- (CH₂)_Three-O-cHx H H
1-1415 H H H H Me 2 -CO- (CH₂)_Three-O-cHx Me H
1-1416 H H H H Me 2 -CO- (CH₂)_Three-O-cHx H Me
1-1417 H H H H Me 2 -CO- (CH₂)_Three-O-cHx F H
1-1418 H H H H Me 2 -CO- (CH₂)_Three-O-cHx H F
1-1419 H H Me Me Me 2 -CO- (CH₂)_Three-O-cHx H H
1-1420 CO₂Me H H H Me 2 -CO- (CH₂)_Three-O-cHx H H
1-1421 CO₂Et H H H Me 2 -CO- (CH₂)_Three-O-cHx H H
1-1422 H H H H Me 2 -CO- (CH₂)_Three-O- (3-F-cHx) H H
1-1423 H H H H Me 2 -CO- (CH₂)_Three-O- (4-F-cHx) H H
1-1424 H H H H Me 2 -CO- (CH₂)_Three-O- (4-Cl-cHx) H H
1-1425 H H H H Me 2 -CO- (CH₂)_Three-O- (4-Br-cHx) H H
1-1426 H H H H Me 2 -CO- (CH₂)_Three-O- (3-Me-cHx) H H
1-1427 H H H H Me 2 -CO- (CH₂)_Three-O- (4-Me-cHx) H H
1-1428 H H H H Me 2 -CO- (CH₂)_Three-O- (3-Et-cHx) H H
1-1429 H H H H Me 2 -CO- (CH₂)_Three-O- (4-Et-cHx) H H
1-1430 H H H H Me 2 -CO- (CH₂)_Three-O- (3-Pr-cHx) H H
1-1431 H H H H Me 2 -CO- (CH₂)_Three-O- (4-Pr-cHx) H H
1-1432 H H H H Me 2 -CO- (CH₂)_Three-O- (4-iPr-cHx) H H
1-1433 H H H H Me 2 -CO- (CH₂)_Three-O- (3-Bu-cHx) H H
1-1434 H H H H Me 2 -CO- (CH₂)_Three-O- (4-Bu-cHx) H H
1-1435 H H H H Me 2 -CO- (CH₂)_Three-O- (3-CF_Three-cHx) H H
1-1436 H H H H Me 2 -CO- (CH₂)_Three-O- (4-CF_Three-cHx) H H
1-1437 H H H H Me 2 -CO- (CH₂)_Three-O- (3-MeO-cHx) H H
1-1438 H H H H Me 2 -CO- (CH₂)_Three-O- (4-MeO-cHx) H H
1-1439 H H H H Me 2 -CO- (CH₂)_Three-O- (3-EtO-cHx) H H
1-1440 H H H H Me 2 -CO- (CH₂)_Three-O- (4-EtO-cHx) H H
1-1441 H H H H Me 2 -CO- (CH₂)_Three-O- (3-PrO-cHx) H H
1-1442 H H H H Me 2 -CO- (CH₂)_Three-O- (4-PrO-cHx) H H
1-1443 H H H H Me 2 -CO- (CH₂)_Three-O- (3-iPrO-cHx) H H
1-1444 H H H H Me 2 -CO- (CH₂)_Three-O- (4-iPrO-cHx) H H
1-1445 H H H H Me 2 -CO- (CH₂)_Three-O- [3- (2-Et-PrO) cHx] H H
1-1446 H H H H Me 2 -CO- (CH₂)_Three-O- [4- (2-Et-PrO) cHx] H H
1-1447 H H H H Me 2 -CO- (CH₂)_Three-O- (3-iBuO-cHx) H H
1-1448 H H H H Me 2 -CO- (CH₂)_Three-O- (4-iBuO-cHx) H H
1-1449 H H H H Me 2 -CO- (CH₂)_Three-O- (3-MeS-cHx) H H
1-1450 H H H H Me 2 -CO- (CH₂)_Three-O- (4-MeS-cHx) H H
1-1451 H H H H Me 2 -CO- (CH₂)_Three-O- (3-EtS-cHx) H H
1-1452 H H H H Me 2 -CO- (CH₂)_Three-O- (4-EtS-cHx) H H
1-1453 H H H H Me 2 -CO- (CH₂)_Three-O- (3-PrS-cHx) H H
1-1454 H H H H Me 2 -CO- (CH₂)_Three-O- (4-PrS-cHx) H H
1-1455 H H H H Me 2 -CO- (CH₂)_Three-O- (3-iPrS-cHx) H H
1-1456 H H H H Me 2 -CO- (CH₂)_Three-O- (4-iPrS-cHx) H H
1-1457 H H H H Me 2 -CO- (CH₂)_Three-O- [3- (2-Et-PrS) cHx] H H
1-1458 H H H H Me 2 -CO- (CH₂)_Three-O- [4- (2-Et-PrS) cHx] H H
1-1459 H H H H Me 2 -CO- (CH₂)_Three-O- (3-iBuS-cHx) H H
1-1460 H H H H Me 2 -CO- (CH₂)_Three-O- (4-iBuS-cHx) H H
1-1461 H H H H Me 2 -CO- (CH₂)_Three-O- (3-cHx-cHx) H H
1-1462 H H H H Me 2 -CO- (CH₂)_Three-O- (4-cHx-cHx) H H
1-1463 H H H H Me 2 -CO- (CH₂)_Three-O- (3-Ph-cHx) H H
1-1464 H H H H Me 2 -CO- (CH₂)_Three-O- (4-Ph-cHx) H H
1-1465 H H H H Me 2 -CO- (CH₂)_Three-O- (2,4-diMe-cHx) H H
1-1466 H H H H Me 2 -CO- (CH₂)_Three-O- (3,4-diMe-cHx) H H
1-1467 H H H H Me 2 -CO- (CH₂)_Three-O- (3,5-diMe-cHx) H H
1-1468 H H H H Me 2 -CO- (CH₂)_Three-O-Ph H H
1-1469 H H H H Me 2 -CO- (CH₂)_Three-O-Ph Me H
1-1470 H H H H Me 2 -CO- (CH₂)_Three-O-Ph H Me
1-1471 H H H H Me 2 -CO- (CH₂)_Three-O-Ph F H
1-1472 H H H H Me 2 -CO- (CH₂)_Three-O-Ph H F
1-1473 H H Me Me Me 2 -CO- (CH₂)_Three-O-Ph H H
1-1474 CO₂Me H H H Me 2 -CO- (CH₂)_Three-O-Ph H H
1-1475 CO₂Et H H H Me 2 -CO- (CH₂)_Three-O-Ph H H
1-1476 H H H H Me 2 -CO- (CH₂)_Three-O- (3-F-Ph) H H
1-1477 H H H H Me 2 -CO- (CH₂)_Three-O- (4-F-Ph) H H
1-1478 H H H H Me 2 -CO- (CH₂)_Three-O- (4-Cl-Ph) H H
1-1479 H H H H Me 2 -CO- (CH₂)_Three-O- (4-Br-Ph) H H
1-1480 H H H H Me 2 -CO- (CH₂)_Three-O- (3-Me-Ph) H H
1-1481 H H H H Me 2 -CO- (CH₂)_Three-O- (4-Me-Ph) H H
1-1482 H H H H Me 2 -CO- (CH₂)_Three-O- (3-Et-Ph) H H
1-1483 H H H H Me 2 -CO- (CH₂)_Three-O- (4-Et-Ph) H H
1-1484 H H H H Me 2 -CO- (CH₂)_Three-O- (3-Pr-Ph) H H
1-1485 H H H H Me 2 -CO- (CH₂)_Three-O- (4-Pr-Ph) H H
1-1486 H H H H Me 2 -CO- (CH₂)_Three-O- (3-iPr-Ph) H H
1-1487 H H H H Me 2 -CO- (CH₂)_Three-O- (4-iPr-Ph) H H
1-1488 H H H H Me 2 -CO- (CH₂)_Three-O- (3-Bu-Ph) H H
1-1489 H H H H Me 2 -CO- (CH₂)_Three-O- (4-Bu-Ph) H H
1-1490 H H H H Me 2 -CO- (CH₂)_Three-O- (3-CF_Three-Ph) H H
1-1491 H H H H Me 2 -CO- (CH₂)_Three-O- (4-CF_Three-Ph) H H
1-1492 H H H H Me 2 -CO- (CH₂)_Three-O- (3-MeO-Ph) H H
1-1493 H H H H Me 2 -CO- (CH₂)_Three-O- (4-MeO-Ph) H H
1-1494 H H H H Me 2 -CO- (CH₂)_Three-O- (3-EtO-Ph) H H
1-1495 H H H H Me 2 -CO- (CH₂)_Three-O- (4-EtO-Ph) H H
1-1496 H H H H Me 2 -CO- (CH₂)_Three-O- (3-PrO-Ph) H H
1-1497 H H H H Me 2 -CO- (CH₂)_Three-O- (4-PrO-Ph) H H
1-1498 H H H H Me 2 -CO- (CH₂)_Three-O- (3-iPrO-Ph) H H
1-1499 H H H H Me 2 -CO- (CH₂)_Three-O- (4-iPrO-Ph) H H
1-1500 H H H H Me 2 -CO- (CH₂)_Three-O- [3- (2-Et-PrO) -Ph] H H
1-1501 H H H H Me 2 -CO- (CH₂)_Three-O- [4- (2-Et-PrO) -Ph] H H
1-1502 H H H H Me 2 -CO- (CH₂)_Three-O- (3-iBuO-Ph) H H
1-1503 H H H H Me 2 -CO- (CH₂)_Three-O- (4-iBuO-Ph) H H
1-1504 H H H H Me 2 -CO- (CH₂)_Three-O- (3-MeS-Ph) H H
1-1505 H H H H Me 2 -CO- (CH₂)_Three-O- (4-MeS-Ph) H H
1-1506 H H H H Me 2 -CO- (CH₂)_Three-O- (3-EtS-Ph) H H
1-1507 H H H H Me 2 -CO- (CH₂)_Three-O- (4-EtS-Ph) H H
1-1508 H H H H Me 2 -CO- (CH₂)_Three-O- (3-PrS-Ph) H H
1-1509 H H H H Me 2 -CO- (CH₂)_Three-O- (4-PrS-Ph) H H
1-1510 H H H H Me 2 -CO- (CH₂)_Three-O- (3-iPrS-Ph) H H
1-1511 H H H H Me 2 -CO- (CH₂)_Three-O- (4-iPrS-Ph) H H
1-1512 H H H H Me 2 -CO- (CH₂)_Three-O- [3- (2-Et-PrS) -Ph] H H
1-1513 H H H H Me 2 -CO- (CH₂)_Three-O- [4- (2-Et-PrS) -Ph] H H
1-1514 H H H H Me 2 -CO- (CH₂)_Three-O- (3-iBuS-Ph) H H
1-1515 H H H H Me 2 -CO- (CH₂)_Three-O- (4-iBuS-Ph) H H
1-1516 H H H H Me 2 -CO- (CH₂)_Three-O- (3-cHx-Ph) H H
1-1517 H H H H Me 2 -CO- (CH₂)_Three-O- (4-cHx-Ph) H H
1-1518 H H H H Me 2 -CO- (CH₂)_Three-O- (3-Ph-Ph) H H
1-1519 H H H H Me 2 -CO- (CH₂)_Three-O- (4-Ph-Ph) H H
1-1520 H H H H Me 2 -CO- (CH₂)_Three-O- (2,4-diMe-Ph) H H
1-1521 H H H H Me 2 -CO- (CH₂)_Three-O- (3,4-diMe-Ph) H H
1-1522 H H H H Me 2 -CO- (CH₂)_Three-O- (3,5-diMe-Ph) H H
1-1523 H H H H Me 2 -CO- (CH₂)_Four-O-cHx H H
1-1524 H H H H Me 2 -CO- (CH₂)_Four-O-Ph H H
1-1525 H H H H Me 2 -CO- (CH₂)_Five-O-cHx H H
1-1526 H H H H Me 2 -CO- (CH₂)_Five-O-Ph H H
1-1527 H H H H Me 2 -CO- (CH₂)₂-OCH₂-cHx H H
1-1528 H H Me Me Me 2 -CO- (CH₂)₂-OCH₂-cHx H H
1-1529 CO₂Me H H H Me 2 -CO- (CH₂)₂-OCH₂-cHx H H
1-1530 CO₂Et H H H Me 2 -CO- (CH₂)₂-OCH₂-cHx H H
1-1531 H H H H Me 2 -CO- (CH₂)₂-OCH₂-(4-F-cHx) H H
1-1532 H H H H Me 2 -CO- (CH₂)₂-OCH₂-(4-Me-cHx) H H
1-1533 H H H H Me 2 -CO- (CH₂)₂-OCH₂-(4-Et-cHx) H H
1-1534 H H H H Me 2 -CO- (CH₂)₂-OCH₂-(4-CF_Three-cHx) H H
1-1535 H H H H Me 2 -CO- (CH₂)₂-OCH₂-(4-MeO-cHx) H H
1-1536 H H H H Me 2 -CO- (CH₂)₂-OCH₂-(4-EtO-cHx) H H
1-1537 H H H H Me 2 -CO- (CH₂)₂-OCH₂-(4-MeS-cHx) H H
1-1538 H H H H Me 2 -CO- (CH₂)₂-OCH₂-(4-cHx-cHx) H H
1-1539 H H H H Me 2 -CO- (CH₂)₂-OCH₂-(4-Ph-cHx) H H
1-1540 H H H H Me 2 -CO- (CH₂)₂-OCH₂-Ph H H
1-1541 H H Me Me Me 2 -CO- (CH₂)₂-OCH₂-Ph H H
1-1542 CO₂Me H H H Me 2 -CO- (CH₂)₂-OCH₂-Ph H H
1-1543 CO₂Et H H H Me 2 -CO- (CH₂)₂-OCH₂-Ph H H
1-1544 H H H H Me 2 -CO- (CH₂)₂-OCH₂-(4-F-Ph) H H
1-1545 H H H H Me 2 -CO- (CH₂)₂-OCH₂-(4-Me-Ph) H H
1-1546 H H H H Me 2 -CO- (CH₂)₂-OCH₂-(4-Et-Ph) H H
1-1547 H H H H Me 2 -CO- (CH₂)₂-OCH₂-(4-CF_Three-Ph) H H
1-1548 H H H H Me 2 -CO- (CH₂)₂-OCH₂-(4-MeO-Ph) H H
1-1549 H H H H Me 2 -CO- (CH₂)₂-OCH₂-(4-EtO-Ph) H H
1-1550 H H H H Me 2 -CO- (CH₂)₂-OCH₂-(4-MeS-Ph) H H
1-1551 H H H H Me 2 -CO- (CH₂)₂-OCH₂-(4-cHx-Ph) H H
1-1552 H H H H Me 2 -CO- (CH₂)₂-OCH₂-(4-Ph-Ph) H H
1-1553 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-CH₂-cPn H H
1-1554 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-cHx H H
1-1555 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-cHx Me H
1-1556 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-cHx H Me
1-1557 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-cHx F H
1-1558 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-cHx H F
1-1559 H H Me Me Me 2 -CO- (CH₂)_Three-OCH₂-cHx H H
1-1560 COMe H H H Me 2 -CO- (CH₂)_Three-OCH₂-cHx H H
1-1561 CO₂Et H H H Me 2 -CO- (CH₂)_Three-OCH₂-cHx H H
1-1562 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-F-cHx) H H
1-1563 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-F-cHx) H H
1-1564 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-Cl-cHx) H H
1-1565 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-Br-cHx) H H
1-1566 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-Me-cHx) H H
1-1567 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-Me-cHx) H H
1-1568 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-Et-cHx) H H
1-1569 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-Et-cHx) H H
1-1570 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-Pr-cHx) H H
1-1571 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-Pr-cHx) H H
1-1572 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-iPr-cHx) H H
1-1573 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-Bu-cHx) H H
1-1574 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-Bu-cHx) H H
1-1575 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-CF_Three-cHx) H H
1-1576 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-CF_Three-cHx) H H
1-1577 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-MeO-cHx) H H
1-1578 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-MeO-cHx) H H
1-1579 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-EtO-cHx) H H
1-1580 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-EtO-cHx) H H
1-1581 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-PrO-cHx) H H
1-1582 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-PrO-cHx) H H
1-1583 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-iPrO-cHx) H H
1-1584 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-iPrO-cHx) H H
1-1585 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-[3- (2-Et-PrO) cHx] H H
1-1586 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-[4- (2-Et-PrO) cHx] H H
1-1587 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-iBuO-cHx) H H
1-1588 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-iBuO-cHx) H H
1-1589 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-MeS-cHx) H H
1-1590 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-MeS-cHx) H H
1-1591 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-EtS-cHx) H H
1-1592 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-EtS-cHx) H H
1-1593 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-PrS-cHx) H H
1-1594 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-PrS-cHx) H H
1-1595 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-iPrS-cHx) H H
1-1596 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-iPrS-cHx) H H
1-1597 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-[3- (2-Et-PrS) cHx] H H
1-1598 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-[4- (2-Et-PrS) cHx] H H
1-1599 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-iBuS-cHx) H H
1-1600 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-iBuS-cHx) H H
1-1601 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-cHx-cHx) H H
1-1602 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-cHx-cHx) H H
1-1603 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-Ph-cHx) H H
1-1604 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-Ph-cHx) H H
1-1605 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(2,4-diMe-cHx) H H
1-1606 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3,4-diMe-cHx) H H
1-1607 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3,5-diMe-cHx) H H
1-1608 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-Ph H H
1-1609 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-Ph Me H
1-1610 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-Ph H Me
1-1611 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-Ph F H
1-1612 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-Ph H F
1-1613 H H Me Me Me 2 -CO- (CH₂)_Three-OCH₂-Ph H H
1-1614 CO₂Me H H H Me 2 -CO- (CH₂)_Three-OCH₂-Ph H H
1-1615 CO₂Me H H H Me 2 -CO- (CH₂)_Three-OCH₂-Ph H H
1-1616 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-F-Ph) H H
1-1617 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-F-Ph) H H
1-1618 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-Cl-Ph) H H
1-1619 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-Br-Ph) H H
1-1620 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-Me-Ph) H H
1-1621 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-Me-Ph) H H
1-1622 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-Et-Ph) H H
1-1623 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-Et-Ph) H H
1-1624 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-Pr-Ph) H H
1-1625 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-Pr-Ph) H H
1-1626 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-iPr-Ph) H H
1-1627 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-iPr-Ph) H H
1-1628 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-Bu-Ph) H H
1-1629 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-Bu-Ph) H H
1-1630 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-CF_Three-Ph) H H
1-1631 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-CF_Three-Ph) H H
1-1632 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-MeO-Ph) H H
1-1633 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-MeO-Ph) H H
1-1634 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-EtO-Ph) H H
1-1635 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-EtO-Ph) H H
1-1636 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-PrO-Ph) H H
1-1637 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-PrO-Ph) H H
1-1638 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-iPrO-Ph) H H
1-1639 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-iPrO-Ph) H H
1-1640 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-[3- (2-Et-PrO) Ph] H H
1-1641 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-[4- (2-Et-PrO) Ph] H H
1-1642 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-iBuO-Ph) H H
1-1643 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-iBuO-Ph) H H
1-1644 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-MeS-Ph) H H
1-1645 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-MeS-Ph) H H
1-1646 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-EtS-Ph) H H
1-1647 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-EtS-Ph) H H
1-1648 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-PrS-Ph) H H
1-1649 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-PrS-Ph) H H
1-1650 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-iPrS-Ph) H H
1-1651 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-iPrS-Ph) H H
1-1652 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-[3- (2-Et-PrS) Ph] H H
1-1653 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-[4- (2-Et-PrS) Ph] H H
1-1654 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-iBuS-Ph) H H
1-1655 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-iBuS-Ph) H H
1-1656 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-cHx-Ph) H H
1-1657 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-cHx-Ph) H H
1-1658 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3-Ph-Ph) H H
1-1659 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(4-Ph-Ph) H H
1-1660 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(2,4-diMe-Ph) H H
1-1661 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3,4-diMe-Ph) H H
1-1662 H H H H Me 2 -CO- (CH₂)_Three-OCH₂-(3,5-diMe-Ph) H H
1-1663 H H H H Me 2 -CO- (CH₂)_Four-OCH₂-cHx H H
1-1664 H H H H Me 2 -CO- (CH₂)_Four-OCH₂-Ph H H
1-1665 H H H H Me 2 -CO- (CH₂)_Five-OCH₂-cHx H H
1-1666 H H H H Me 2 -CO- (CH₂)_Five-OCH₂-Ph H H
1-1667 H H H H Me 2 -CH (OH) -CH₂-cHx H H
1-1668 H H H H Me 2 -CH (OH) -CH₂-Ph H H
1-1669 H H H H Me 2 -CH (OH)-(CH₂)₂-cHx H H
1-1670 H H H H Me 2 -CH (OH)-(CH₂)₂-Ph H H
1-1671 H H H H Me 2 -CH (OH)-(CH₂)_Three-cHx H H
1-1672 H H H H Me 2 -CH (OH)-(CH₂)_Three-Ph H H
1-1673 H H H H Me 2 -CH (OH)-(CH₂)_Four-cHx H H
1-1674 H H Me Me Me 2 -CH (OH)-(CH₂)_Four-cHx H H
1-1675 CO₂Me H H H Me 2 -CH (OH)-(CH₂)_Four-cHx H H
1-1676 CO₂Et H H H Me 2 -CH (OH)-(CH₂)_Four-cHx H H
1-1677 H H H H Me 2 -CH (OH)-(CH₂)_Four-(4-F-cHx) H H
1-1678 H H H H Me 2 -CH (OH)-(CH₂)_Four-(4-Me-cHx) H H
1-1679 H H H H Me 2 -CH (OH)-(CH₂)_Four-(4-Et-cHx) H H
1-1680 H H H H Me 2 -CH (OH)-(CH₂)_Four-(4-CF_Three-cHx) H H
1-1681 H H H H Me 2 -CH (OH)-(CH₂)_Four-(4-MeO-cHx) H H
1-1682 H H H H Me 2 -CH (OH)-(CH₂)_Four-(4-EtO-cHx) H H
1-1683 H H H H Me 2 -CH (OH)-(CH₂)_Four-(4-MeS-cHx) H H
1-1684 H H H H Me 2 -CH (OH)-(CH₂)_Four-(4-cHx-cHx) H H
1-1685 H H H H Me 2 -CH (OH)-(CH₂)_Four-(4-Ph-cHx) H H
1-1686 H H H H Me 2 -CH (OH)-(CH₂)_Four-Ph H H
1-1687 H H Me Me Me 2 -CH (OH)-(CH₂)_Four-Ph H H
1-1688 CO₂Me H H H Me 2 -CH (OH)-(CH₂)_Four-Ph H H
1-1689 CO₂Et H H H Me 2 -CH (OH)-(CH₂)_Four-Ph H H
1-1690 H H H H Me 2 -CH (OH)-(CH₂)_Four-(4-F-Ph) H H
1-1691 H H H H Me 2 -CH (OH)-(CH₂)_Four-(4-Me-Ph) H H
1-1692 H H H H Me 2 -CH (OH)-(CH₂)_Four-(4-Et-Ph) H H
1-1693 H H H H Me 2 -CH (OH)-(CH₂)_Four-(4-CF_Three-Ph) H H
1-1694 H H H H Me 2 -CH (OH)-(CH₂)_Four-(4-MeO-Ph) H H
1-1695 H H H H Me 2 -CH (OH)-(CH₂)_Four-(4-EtO-Ph) H H
1-1696 H H H H Me 2 -CH (OH)-(CH₂)_Four-(4-MeS-Ph) H H
1-1697 H H H H Me 2 -CH (OH)-(CH₂)_Four-(4-cHx-Ph) H H
1-1698 H H H H Me 2 -CH (OH)-(CH₂)_Four-(4-Ph-Ph) H H
1-1699 H H H H Me 2 -CH (OH)-(CH₂)_Five-cHx H H
1-1700 H H Me Me Me 2 -CH (OH)-(CH₂)_Five-cHx H H
1-1701 CO₂Me H H H Me 2 -CH (OH)-(CH₂)_Five-cHx H H
1-1702 CO₂Et H H H Me 2 -CH (OH)-(CH₂)_Five-cHx H H
1-1703 H H H H Me 2 -CH (OH)-(CH₂)_Five-(4-F-cHx) H H
1-1704 H H H H Me 2 -CH (OH)-(CH₂)_Five-(4-Me-cHx) H H
1-1705 H H H H Me 2 -CH (OH)-(CH₂)_Five-(4-Et-cHx) H H
1-1706 H H H H Me 2 -CH (OH)-(CH₂)_Five-(4-CF_Three-cHx) H H
1-1707 H H H H Me 2 -CH (OH)-(CH₂)_Five-(4-MeO-cHx) H H
1-1708 H H H H Me 2 -CH (OH)-(CH₂)_Five-(4-EtO-cHx) H H
1-1709 H H H H Me 2 -CH (OH)-(CH₂)_Five-(4-MeS-cHx) H H
1-1710 H H H H Me 2 -CH (OH)-(CH₂)_Five-(4-cHx-cHx) H H
1-1711 H H H H Me 2 -CH (OH)-(CH₂)_Five-(4-Ph-cHx) H H
1-1712 H H H H Me 2 -CH (OH)-(CH₂)_Five-Ph H H
1-1713 H H Me Me Me 2 -CH (OH)-(CH₂)_Five-Ph H H
1-1714 CO₂Me H H H Me 2 -CH (OH)-(CH₂)_Five-Ph H H
1-1715 CO₂Et H H H Me 2 -CH (OH)-(CH₂)_Five-Ph H H
1-1716 H H H H Me 2 -CH (OH)-(CH₂)_Five-(4-F-Ph) H H
1-1717 H H H H Me 2 -CH (OH)-(CH₂)_Five-(4-Me-Ph) H H
1-1718 H H H H Me 2 -CH (OH)-(CH₂)_Five-(4-Et-Ph) H H
1-1719 H H H H Me 2 -CH (OH)-(CH₂)_Five-(4-CF_Three-Ph) H H
1-1720 H H H H Me 2 -CH (OH)-(CH₂)_Five-(4-MeO-Ph) H H
1-1721 H H H H Me 2 -CH (OH)-(CH₂)_Five-(4-EtO-Ph) H H
1-1722 H H H H Me 2 -CH (OH)-(CH₂)_Five-(4-MeS-Ph) H H
1-1723 H H H H Me 2 -CH (OH)-(CH₂)_Five-(4-cHx-Ph) H H
1-1724 H H H H Me 2 -CH (OH)-(CH₂)_Five-(4-Ph-Ph) H H
1-1725 H H H H Me 2 -CH (OH)-(CH₂)₆-cHx H H
1-1726 H H H H Me 2 -CH (OH)-(CH₂)₆-Ph H H
1-1727 H H H H Me 2 -CH (OH)-(CH₂)₇-cHx H H
1-1728 H H H H Me 2 -CH (OH)-(CH₂)₇-Ph H H
1-1729 H H H H Me 2 -4- (cHx-CH₂O) Ph H H
1-1730 H H Me Me Me 2 -4- (cHx-CH₂O) Ph H H
1-1731 CO₂Me H H H Me 2 -4- (cHx-CH₂O) Ph H H
1-1732 CO₂Et H H H Me 2 -4- (cHx-CH₂O) Ph H H
1-1733 H H H H Me 2 -4- (cHx-CH₂O) -2-F-Ph H H
1-1734 H H H H Me 2 -4- (cHx-CH₂O) -3-F-Ph H H
1-1735 H H H H Me 2 -4- (cHx-CH₂O) -2,3-diF-Ph H H
1-1736 H H H H Me 2 -4- (cHx-CH₂O) -2-Cl-Ph H H
1-1737 H H H H Me 2 -4- (cHx-CH₂O) -3-Cl-Ph H H
1-1738 H H H H Me 2 -4- (cHx-CH₂O) -2,3-diCl-Ph H H
1-1739 H H H H Me 2 -4- (cHx-CH₂O) -2-Me-Ph H H
1-1740 H H H H Me 2 -4- (cHx-CH₂O) -3-Me-Ph H H
1-1741 H H H H Me 2 -4- (cHx-CH₂O) -2,3-diMe-Ph H H
1-1742 H H H H Me 2 -4- [cHx- (CH₂)₂O] Ph H H
1-1743 H H H H Me 2 -4- [cHx- (CH₂)_ThreeO] Ph H H
1-1744 H H H H Me 2-(4-BzO-Ph) H H
1-1745 H H Me Me Me 2-(4-BzO-Ph) H H
1-1746 CO₂Me H H H Me 2-(4-BzO-Ph) H H
1-1747 CO₂Et H H H Me 2-(4-BzO-Ph) H H
1-1748 H H H H Me 2-(4-BzO-2-F-Ph) H H
1-1749 H H H H Me 2-(4-BzO-3-F-Ph) H H
1-1750 H H H H Me 2-(4-BzO-2,3-diF-Ph) H H
1-1751 H H H H Me 2-(4-BzO-2-Cl-Ph) H H
1-1752 H H H H Me 2-(4-BzO-3-Cl-Ph) H H
1-1753 H H H H Me 2-(4-BzO-2,3-diCl-Ph) H H
1-1754 H H H H Me 2-(4-BzO-2-Me-Ph) H H
1-1755 H H H H Me 2-(4-BzO-3-Me-Ph) H H
1-1756 H H H H Me 2-(4-BzO-2,3-diMe-Ph) H H
1-1757 H H H H Me 2 -4- [Ph- (CH₂)₂O] -Ph H H
1-1758 H H H H Me 2 -4- [Ph- (CH₂)_ThreeO] -Ph H H
1-1759 H H H H Et 2-(CH₂)_Three-cHx H H
1-1760 H H H H Et 2-(CH₂)_Three-Ph H H
1-1761 H H H H Et 2-(CH₂)_Four-cHx H H
1-1762 H H H H Et 2-(CH₂)_Four-Ph H H
1-1763 H H H H Et 2-(CH₂)_Five-cPn H H
1-1764 H H H H Et 2-(CH₂)_Five-cHx H H
1-1765 H H H H Et 2-(CH₂)_Five-cHx Me H
1-1766 H H H H Et 2-(CH₂)_Five-cHx H Me
1-1767 H H H H Et 2-(CH₂)_Five-cHx F H
1-1768 H H H H Et 2-(CH₂)_Five-cHx H F
1-1769 H H Me Me Et 2-(CH₂)_Five-cHx H H
1-1770 CO₂Me H H H Et 2-(CH₂)_Five-cHx H H
1-1771 CO₂Et H H H Et 2-(CH₂)_Five-cHx H H
1-1772 H H H H Et 2-(CH₂)_Five-(4-F-cHx) H H
1-1773 H H H H Et 2-(CH₂)_Five-(4-Cl-cHx) H H
1-1774 H H H H Et 2-(CH₂)_Five-(4-Br-cHx) H H
1-1775 H H H H Et 2-(CH₂)_Five-(4-Me-cHx) H H
1-1776 H H H H Et 2-(CH₂)_Five-(4-Et-cHx) H H
1-1777 H H H H Et 2-(CH₂)_Five-(4-Pr-cHx) H H
1-1778 H H H H Et 2-(CH₂)_Five-(4-iPr-cHx) H H
1-1779 H H H H Et 2-(CH₂)_Five-(4-CF_Three-cHx) H H
1-1780 H H H H Et 2-(CH₂)_Five-(4-MeO-cHx) H H
1-1781 H H H H Et 2-(CH₂)_Five-(4-EtO-cHx) H H
1-1782 H H H H Et 2-(CH₂)_Five-(4-PrO-cHx) H H
1-1783 H H H H Et 2-(CH₂)_Five-(4-iPrO-cHx) H H
1-1784 H H H H Et 2-(CH₂)_Five-(3-MeS-cHx) H H
1-1785 H H H H Et 2-(CH₂)_Five-(4-MeS-cHx) H H
1-1786 H H H H Et 2-(CH₂)_Five-(2,4-diMe-cHx) H H
1-1787 H H H H Et 2-(CH₂)_Five-(3,4-diMe-cHx) H H
1-1788 H H H H Et 2-(CH₂)_Five-(3,5-diMe-cHx) H H
1-1789 H H H H Et 2-(CH₂)_Five-Ph H H
1-1790 H H H H Et 2-(CH₂)_Five-Ph Me H
1-1791 H H H H Et 2-(CH₂)_Five-Ph H Me
1-1792 H H H H Et 2-(CH₂)_Five-Ph F H
1-1793 H H H H Et 2-(CH₂)_Five-Ph H F
1-1794 H H Me Me Et 2-(CH₂)_Five-Ph H H
1-1795 CO₂Me H H H Et 2-(CH₂)_Five-Ph H H
1-1796 CO₂Et H H H Et 2-(CH₂)_Five-Ph H H
1-1797 H H H H Et 2-(CH₂)_Five-(4-F-Ph) H H
1-1798 H H H H Et 2-(CH₂)_Five-(4-Cl-Ph) H H
1-1799 H H H H Et 2-(CH₂)_Five-(4-Br-Ph) H H
1-1800 H H H H Et 2-(CH₂)_Five-(4-Me-Ph) H H
1-1801 H H H H Et 2-(CH₂)_Five-(4-Et-Ph) H H
1-1802 H H H H Et 2-(CH₂)_Five-(4-Pr-Ph) H H
1-1803 H H H H Et 2-(CH₂)_Five-(4-iPr-Ph) H H
1-1804 H H H H Et 2-(CH₂)_Five-(4-Bu-Ph) H H
1-1805 H H H H Et 2-(CH₂)_Five-(4-CF_Three-Ph) H H
1-1806 H H H H Et 2-(CH₂)_Five-(4-MeO-Ph) H H
1-1807 H H H H Et 2-(CH₂)_Five-(4-EtO-Ph) H H
1-1808 H H H H Et 2-(CH₂)_Five-(4-PrO-Ph) H H
1-1809 H H H H Et 2-(CH₂)_Five-(4-iPrO-Ph) H H
1-1810 H H H H Et 2-(CH₂)_Five-(3-MeS-Ph) H H
1-1811 H H H H Et 2-(CH₂)_Five-(4-MeS-Ph) H H
1-1812 H H H H Et 2-(CH₂)_Five-(2,4-diMe-Ph) H H
1-1813 H H H H Et 2-(CH₂)_Five-(3,4-diMe-Ph) H H
1-1814 H H H H Et 2-(CH₂)_Five-(3,5-diMe-Ph) H H
1-1815 H H H H Et 2-(CH₂)₆-cPn H H
1-1816 H H H H Et 2-(CH₂)₆-cHx H H
1-1817 H H H H Et 2-(CH₂)₆-cHx Me H
1-1818 H H H H Et 2-(CH₂)₆-cHx H Me
1-1819 H H H H Et 2-(CH₂)₆-cHx F H
1-1820 H H H H Et 2-(CH₂)₆-cHx H F
1-1821 H H Me Me Et 2-(CH₂)₆-cHx H H
1-1822 CO₂Me H H H Et 2-(CH₂)₆-cHx H H
1-1823 CO₂Et H H H Et 2-(CH₂)₆-cHx H H
1-1824 H H H H Et 2-(CH₂)₆-(4-F-cHx) H H
1-1825 H H H H Et 2-(CH₂)₆-(4-Cl-cHx) H H
1-1826 H H H H Et 2-(CH₂)₆-(4-Br-cHx) H H
1-1827 H H H H Et 2-(CH₂)₆-(4-Me-cHx) H H
1-1828 H H H H Et 2-(CH₂)₆-(4-Et-cHx) H H
1-1829 H H H H Et 2-(CH₂)₆-(4-Pr-cHx) H H
1-1830 H H H H Et 2-(CH₂)₆-(4-iPr-cHx) H H
1-1831 H H H H Et 2-(CH₂)₆-(4-Bu-cHx) H H
1-1832 H H H H Et 2-(CH₂)₆-(4-CF_Three-cHx) H H
1-1833 H H H H Et 2-(CH₂)₆-(4-MeO-cHx) H H
1-1834 H H H H Et 2-(CH₂)₆-(4-EtO-cHx) H H
1-1835 H H H H Et 2-(CH₂)₆-(4-PrO-cHx) H H
1-1836 H H H H Et 2-(CH₂)₆-(4-iPrO-cHx) H H
1-1837 H H H H Et 2-(CH₂)₆-(3-MeS-cHx) H H
1-1838 H H H H Et 2-(CH₂)₆-(4-MeS-cHx) H H
1-1839 H H H H Et 2-(CH₂)₆-(2,4-diMe-cHx) H H
1-1840 H H H H Et 2-(CH₂)₆-(3,4-diMe-cHx) H H
1-1841 H H H H Et 2-(CH₂)₆-(3,5-diMe-cHx) H H
1-1842 H H H H Et 2-(CH₂)₆-Ph H H
1-1843 H H H H Et 2-(CH₂)₆-Ph Me H
1-1844 H H H H Et 2-(CH₂)₆-Ph H Me
1-1845 H H H H Et 2-(CH₂)₆-Ph F H
1-1846 H H H H Et 2-(CH₂)₆-Ph H F
1-1847 H H Me Me Et 2-(CH₂)₆-Ph H H
1-1848 CO₂Me H H H Et 2-(CH₂)₆-Ph H H
1-1849 CO₂Et H H H Et 2-(CH₂)₆-Ph H H
1-1850 H H H H Et 2-(CH₂)₆-(4-F-Ph) H H
1-1851 H H H H Et 2-(CH₂)₆-(4-Cl-Ph) H H
1-1852 H H H H Et 2-(CH₂)₆-(4-Br-Ph) H H
1-1853 H H H H Et 2-(CH₂)₆-(4-Me-Ph) H H
1-1854 H H H H Et 2-(CH₂)₆-(4-Et-Ph) H H
1-1855 H H H H Et 2-(CH₂)₆-(4-Pr-Ph) H H
1-1856 H H H H Et 2-(CH₂)₆-(4-iPr-Ph) H H
1-1857 H H H H Et 2-(CH₂)₆-(4-Bu-Ph) H H
1-1858 H H H H Et 2-(CH₂)₆-(4-CF_Three-Ph) H H
1-1859 H H H H Et 2-(CH₂)₆-(4-MeO-Ph) H H
1-1860 H H H H Et 2-(CH₂)₆-(4-EtO-Ph) H H
1-1861 H H H H Et 2-(CH₂)₆-(4-PrO-Ph) H H
1-1862 H H H H Et 2-(CH₂)₆-(4-iPrO-Ph) H H
1-1863 H H H H Et 2-(CH₂)₆-(3-MeS-Ph) H H
1-1864 H H H H Et 2-(CH₂)₆-(4-MeS-Ph) H H
1-1865 H H H H Et 2-(CH₂)₆-(2,4-diMe-Ph) H H
1-1866 H H H H Et 2-(CH₂)₆-(3,4-diMe-Ph) H H
1-1867 H H H H Et 2-(CH₂)₆-(3,5-diMe-Ph) H H
1-1868 H H H H Et 2-(CH₂)₇-cHx H H
1-1869 H H H H Et 2-(CH₂)₇-Ph H H
1-1870 H H H H Et 2 -CH = CH-cHx H H
1-1871 H H H H Et 2 -CH = CH-Ph H H
1-1872 H H H H Et 2 -CH = CH- (CH₂)_Three-cHx H H
1-1873 H H Me Me Et 2 -CH = CH- (CH₂)_Three-cHx H H
1-1874 CO₂Me H H H Et 2 -CH = CH- (CH₂)_Three-cHx H H
1-1875 CO₂Et H H H Et 2 -CH = CH- (CH₂)_Three-cHx H H
1-1876 H H H H Et 2 -CH = CH- (CH₂)_Three-Ph H H
1-1877 H H Me Me Et 2 -CH = CH- (CH₂)_Three-Ph H H
1-1878 CO₂Me H H H Et 2 -CH = CH- (CH₂)_Three-Ph H H
1-1879 CO₂Et H H H Et 2 -CH = CH- (CH₂)_Three-Ph H H
1-1880 H H H H Et 2 -CH = CH- (CH₂)_Four-cHx H H
1-1881 H H Me Me Et 2 -CH = CH- (CH₂)_Four-cHx H H
1-1882 CO₂Me H H H Et 2 -CH = CH- (CH₂)_Four-cHx H H
1-1883 CO₂Et H H H Et 2 -CH = CH- (CH₂)_Four-cHx H H
1-1884 H H H H Et 2 -CH = CH- (CH₂)_Four-Ph H H
1-1885 H H Me Me Et 2 -CH = CH- (CH₂)_Four-Ph H H
1-1886 CO₂Me H H H Et 2 -CH = CH- (CH₂)_Four-Ph H H
1-1887 CO₂Et H H H Et 2 -CH = CH- (CH₂)_Four-Ph H H
1-1888 H H H H Et 2 -CH = CH-CH₂O-cHx H H
1-1889 H H H H Et 2 -CH = CH-CH₂O-Ph H H
1-1890 H H H H Et 2 -CH = CH- (CH₂)₂O-cHx H H
1-1891 H H H H Et 2 -CH = CH- (CH₂)₂O-Ph H H
1-1892 H H H H Et 2 -C≡C-CH₂-cHx H H
1-1893 H H Me Me Et 2 -C≡C-CH₂-cHx H H
1-1894 CO₂Me H H H Et 2 -C≡C-CH₂-cHx H H
1-1895 CO₂Et H H H Et 2 -C≡C-CH₂-cHx H H
1-1896 H H H H Et 2 -C≡C-CH₂-Ph H H
1-1897 H H Me Me Et 2 -C≡C-CH₂-Ph H H
1-1898 CO₂Me H H H Et 2 -C≡C-CH₂-Ph H H
1-1899 CO₂Et H H H Et 2 -C≡C-CH₂-Ph H H
1-1900 H H H H Et 2 -C≡C- (CH₂)₂-cHx H H
1-1901 H H Me Me Et 2 -C≡C- (CH₂)₂-cHx H H
1-1902 CO₂Me H H H Et 2 -C≡C- (CH₂)₂-cHx H H
1-1903 CO₂Et H H H Et 2 -C≡C- (CH₂)₂-cHx H H
1-1904 H H H H Et 2 -C≡C- (CH₂)₂-Ph H H
1-1905 H H Me Me Et 2 -C≡C- (CH₂)₂-Ph H H
1-1906 CO₂Me H H H Et 2 -C≡C- (CH₂)₂-Ph H H
1-1907 CO₂Et H H H Et 2 -C≡C- (CH₂)₂-Ph H H
1-1908 H H H H Et 2 -C≡C- (CH₂)_Three-cPn H H
1-1909 H H H H Et 2 -C≡C- (CH₂)_Three-cHx H H
1-1910 H H H H Et 2 -C≡C- (CH₂)_Three-cHx Me H
1-1911 H H H H Et 2 -C≡C- (CH₂)_Three-cHx H Me
1-1912 H H H H Et 2 -C≡C- (CH₂)_Three-cHx F H
1-1913 H H H H Et 2 -C≡C- (CH₂)_Three-cHx H F
1-1914 H H Me Me Et 2 -C≡C- (CH₂)_Three-cHx H H
1-1915 CO₂Me H H H Et 2 -C≡C- (CH₂)_Three-cHx H H
1-1916 CO₂Et H H H Et 2 -C≡C- (CH₂)_Three-cHx H H
1-1917 H H H H Et 2 -C≡C- (CH₂)_Three-(4-F-cHx) H H
1-1918 H H H H Et 2 -C≡C- (CH₂)_Three-(4-Cl-cHx) H H
1-1919 H H H H Et 2 -C≡C- (CH₂)_Three-(4-Br-cHx) H H
1-1920 H H H H Et 2 -C≡C- (CH₂)_Three-(4-Me-cHx) H H
1-1921 H H H H Et 2 -C≡C- (CH₂)_Three-(4-Et-cHx) H H
1-1922 H H H H Et 2 -C≡C- (CH₂)_Three-(4-Pr-cHx) H H
1-1923 H H H H Et 2 -C≡C- (CH₂)_Three-(4-iPr-cHx) H H
1-1924 H H H H Et 2 -C≡C- (CH₂)_Three-(4-Bu-cHx) H H
1-1925 H H H H Et 2 -C≡C- (CH₂)_Three-(4-CF_Three-cHx) H H
1-1926 H H H H Et 2 -C≡C- (CH₂)_Three-(4-MeO-cHx) H H
1-1927 H H H H Et 2 -C≡C- (CH₂)_Three-(4-EtO-cHx) H H
1-1928 H H H H Et 2 -C≡C- (CH₂)_Three-(4-PrO-cHx) H H
1-1929 H H H H Et 2 -C≡C- (CH₂)_Three-(4-iPrO-cHx) H H
1-1930 H H H H Et 2 -C≡C- (CH₂)_Three-(3-MeS-cHx) H H
1-1931 H H H H Et 2 -C≡C- (CH₂)_Three-(4-MeS-cHx) H H
1-1932 H H H H Et 2 -C≡C- (CH₂)_Three-(2,4-diMe-cHx) H H
1-1933 H H H H Et 2 -C≡C- (CH₂)_Three-(3,4-diMe-cHx) H H
1-1934 H H H H Et 2 -C≡C- (CH₂)_Three-(3,5-diMe-cHx) H H
1-1935 H H H H Et 2 -C≡C- (CH₂)_Three-Ph H H
1-1936 H H H H Et 2 -C≡C- (CH₂)_Three-Ph Me H
1-1937 H H H H Et 2 -C≡C- (CH₂)_Three-Ph H Me
1-1938 H H H H Et 2 -C≡C- (CH₂)_Three-Ph F H
1-1939 H H H H Et 2 -C≡C- (CH₂)_Three-Ph H F
1-1940 H H Me Me Et 2 -C≡C- (CH₂)_Three-Ph H H
1-1941 CO₂Me H H H Et 2 -C≡C- (CH₂)_Three-Ph H H
1-1942 CO₂Et H H H Et 2 -C≡C- (CH₂)_Three-Ph H H
1-1943 H H H H Et 2 -C≡C- (CH₂)_Three-(4-F-Ph) H H
1-1944 H H H H Et 2 -C≡C- (CH₂)_Three-(4-Cl-Ph) H H
1-1945 H H H H Et 2 -C≡C- (CH₂)_Three-(4-Br-Ph) H H
1-1946 H H H H Et 2 -C≡C- (CH₂)_Three-(4-Me-Ph) H H
1-1947 H H H H Et 2 -C≡C- (CH₂)_Three-(4-Et-Ph) H H
1-1948 H H H H Et 2 -C≡C- (CH₂)_Three-(4-Pr-Ph) H H
1-1949 H H H H Et 2 -C≡C- (CH₂)_Three-(4-iPr-Ph) H H
1-1950 H H H H Et 2 -C≡C- (CH₂)_Three-(4-Bu-Ph) H H
1-1951 H H H H Et 2 -C≡C- (CH₂)_Three-(4-CF_Three-Ph) H H
1-1952 H H H H Et 2 -C≡C- (CH₂)_Three-(4-MeO-Ph) H H
1-1953 H H H H Et 2 -C≡C- (CH₂)_Three-(4-EtO-Ph) H H
1-1954 H H H H Et 2 -C≡C- (CH₂)_Three-(4-PrO-Ph) H H
1-1955 H H H H Et 2 -C≡C- (CH₂)_Three-(4-iPrO-Ph) H H
1-1956 H H H H Et 2 -C≡C- (CH₂)_Three-(3-MeS-Ph) H H
1-1957 H H H H Et 2 -C≡C- (CH₂)_Three-(4-MeS-Ph) H H
1-1958 H H H H Et 2 -C≡C- (CH₂)_Three-(2,4-diMe-Ph) H H
1-1959 H H H H Et 2 -C≡C- (CH₂)_Three-(3,4-diMe-Ph) H H
1-1960 H H H H Et 2 -C≡C- (CH₂)_Three-(3,5-diMe-Ph) H H
1-1961 H H H H Et 2 -C≡C- (CH₂)_Four-cPn H H
1-1962 H H H H Et 2 -C≡C- (CH₂)_Four-cHx H H
1-1963 H H H H Et 2 -C≡C- (CH₂)_Four-cHx Me H
1-1964 H H H H Et 2 -C≡C- (CH₂)_Four-cHx H Me
1-1965 H H H H Et 2 -C≡C- (CH₂)_Four-cHx F H
1-1966 H H H H Et 2 -C≡C- (CH₂)_Four-cHx H F
1-1967 H H Me Me Et 2 -C≡C- (CH₂)_Four-cHx H H
1-1968 CO₂Me H H H Et 2 -C≡C- (CH₂)_Four-cHx H H
1-1969 CO₂Et H H H Et 2 -C≡C- (CH₂)_Four-cHx H H
1-1970 H H H H Et 2 -C≡C- (CH₂)_Four-(4-F-cHx) H H
1-1971 H H H H Et 2 -C≡C- (CH₂)_Four-(4-Cl-cHx) H H
1-1972 H H H H Et 2 -C≡C- (CH₂)_Four-(4-Br-cHx) H H
1-1973 H H H H Et 2 -C≡C- (CH₂)_Four-(4-Me-cHx) H H
1-1974 H H H H Et 2 -C≡C- (CH₂)_Four-(4-Et-cHx) H H
1-1975 H H H H Et 2 -C≡C- (CH₂)_Four-(4-Pr-cHx) H H
1-1976 H H H H Et 2 -C≡C- (CH₂)_Four-(4-iPr-cHx) H H
1-1977 H H H H Et 2 -C≡C- (CH₂)_Four-(4-Bu-cHx) H H
1-1978 H H H H Et 2 -C≡C- (CH₂)_Four-(4-CF_Three-cHx) H H
1-1979 H H H H Et 2 -C≡C- (CH₂)_Four-(4-MeO-cHx) H H
1-1980 H H H H Et 2 -C≡C- (CH₂)_Four-(4-EtO-cHx) H H
1-1981 H H H H Et 2 -C≡C- (CH₂)_Four-(4-PrO-cHx) H H
1-1982 H H H H Et 2 -C≡C- (CH₂)_Four-(4-iPrO-cHx) H H
1-1983 H H H H Et 2 -C≡C- (CH₂)_Four-(4-MeS-cHx) H H
1-1984 H H H H Et 2 -C≡C- (CH₂)_Four-(2,4-diMe-cHx) H H
1-1985 H H H H Et 2 -C≡C- (CH₂)_Four-(3,4-diMe-cHx) H H
1-1986 H H H H Et 2 -C≡C- (CH₂)_Four-(3,5-diMe-cHx) H H
1-1987 H H H H Et 2 -C≡C- (CH₂)_Four-Ph H H
1-1988 H H H H Et 2 -C≡C- (CH₂)_Four-Ph Me H
1-1989 H H H H Et 2 -C≡C- (CH₂)_Four-Ph H Me
1-1990 H H H H Et 2 -C≡C- (CH₂)_Four-Ph F H
1-1991 H H H H Et 2 -C≡C- (CH₂)_Four-Ph H F
1-1992 H H Me Me Et 2 -C≡C- (CH₂)_Four-Ph H H
1-1993 CO₂Me H H H Et 2 -C≡C- (CH₂)_Four-Ph H H
1-1994 CO₂Et H H H Et 2 -C≡C- (CH₂)_Four-Ph H H
1-1995 H H H H Et 2 -C≡C- (CH₂)_Four-(4-F-Ph) H H
1-1996 H H H H Et 2 -C≡C- (CH₂)_Four-(4-Cl-Ph) H H
1-1997 H H H H Et 2 -C≡C- (CH₂)_Four-(4-Br-Ph) H H
1-1998 H H H H Et 2 -C≡C- (CH₂)_Four-(4-Me-Ph) H H
1-1999 H H H H Et 2 -C≡C- (CH₂)_Four-(4-Et-Ph) H H
1-2000 H H H H Et 2 -C≡C- (CH₂)_Four-(4-Pr-Ph) H H
1-2001 H H H H Et 2 -C≡C- (CH₂)_Four-(4-iPr-Ph) H H
1-2002 H H H H Et 2 -C≡C- (CH₂)_Four-(4-Bu-Ph) H H
1-2003 H H H H Et 2 -C≡C- (CH₂)_Four-(4-CF_Three-Ph) H H
1-2004 H H H H Et 2 -C≡C- (CH₂)_Four-(4-MeO-Ph) H H
1-2005 H H H H Et 2 -C≡C- (CH₂)_Four-(4-EtO-Ph) H H
1-2006 H H H H Et 2 -C≡C- (CH₂)_Four-(4-PrO-Ph) H H
1-2007 H H H H Et 2 -C≡C- (CH₂)_Four-(4-iPrO-Ph) H H
1-2008 H H H H Et 2 -C≡C- (CH₂)_Four-(3-MeS-Ph) H H
1-2009 H H H H Et 2 -C≡C- (CH₂)_Four-(4-MeS-Ph) H H
1-2010 H H H H Et 2 -C≡C- (CH₂)_Four-(2,4-diMe-Ph) H H
1-2011 H H H H Et 2 -C≡C- (CH₂)_Four-(3,4-diMe-Ph) H H
1-2012 H H H H Et 2 -C≡C- (CH₂)_Four-(3,5-diMe-Ph) H H
1-2013 H H H H Et 2 -C≡C- (CH₂)_Five-cHx H H
1-2014 H H Me Me Et 2 -C≡C- (CH₂)_Five-cHx H H
1-2015 CO₂Me H H H Et 2 -C≡C- (CH₂)_Five-cHx H H
1-2016 CO₂Et H H H Et 2 -C≡C- (CH₂)_Five-cHx H H
1-2017 H H H H Et 2 -C≡C- (CH₂)_Five-Ph H H
1-2018 H H Me Me Et 2 -C≡C- (CH₂)_Five-Ph H H
1-2019 CO₂Me H H H Et 2 -C≡C- (CH₂)_Five-Ph H H
1-2020 CO₂Et H H H Et 2 -C≡C- (CH₂)_Five-Ph H H
1-2021 H H H H Et 2 -C≡C- (CH₂)₆-cHx H H
1-2022 H H Me Me Et 2 -C≡C- (CH₂)₆-cHx H H
1-2023 CO₂Me H H H Et 2 -C≡C- (CH₂)₆-cHx H H
1-2024 CO₂Et H H H Et 2 -C≡C- (CH₂)₆-cHx H H
1-2025 H H H H Et 2 -C≡C- (CH₂)₆-Ph H H
1-2026 H H Me Me Et 2 -C≡C- (CH₂)₆-Ph H H
1-2027 CO₂Me H H H Et 2 -C≡C- (CH₂)₆-Ph H H
1-2028 CO₂Et H H H Et 2 -C≡C- (CH₂)₆-Ph H H
1-2029 H H H H Et 2 -C≡C-CH₂O-cHx H H
1-2030 H H Me Me Et 2 -C≡C-CH₂O-cHx H H
1-2031 CO₂Me H H H Et 2 -C≡C-CH₂O-cHx H H
1-2032 CO₂Et H H H Et 2 -C≡C-CH₂O-cHx H H
1-2033 H H H H Et 2 -C≡C-CH₂O-Ph H H
1-2034 H H Me Me Et 2 -C≡C-CH₂O-Ph H H
1-2035 CO₂Me H H H Et 2 -C≡C-CH₂O-Ph H H
1-2036 CO₂Et H H H Et 2 -C≡C-CH₂O-Ph H H
1-2037 H H H H Et 2 -C≡C- (CH₂)₂O-cPn H H
1-2038 H H H H Et 2 -C≡C- (CH₂)₂O-cHx H H
1-2039 H H H H Et 2 -C≡C- (CH₂)₂O-cHx Me H
1-2040 H H H H Et 2 -C≡C- (CH₂)₂O-cHx H Me
1-2041 H H H H Et 2 -C≡C- (CH₂)₂O-cHx F H
1-2042 H H H H Et 2 -C≡C- (CH₂)₂O-cHx H F
1-2043 H H Me Me Et 2 -C≡C- (CH₂)₂O-cHx H H
1-2044 CO₂Me H H H Et 2 -C≡C- (CH₂)₂O-cHx H H
1-2045 CO₂Et H H H Et 2 -C≡C- (CH₂)₂O-cHx H H
1-2046 H H H H Et 2 -C≡C- (CH₂)₂O- (4-F-cHx) H H
1-2047 H H H H Et 2 -C≡C- (CH₂)₂O- (4-Cl-cHx) H H
1-2048 H H H H Et 2 -C≡C- (CH₂)₂O- (4-Br-cHx) H H
1-2049 H H H H Et 2 -C≡C- (CH₂)₂O- (4-Me-cHx) H H
1-2050 H H H H Et 2 -C≡C- (CH₂)₂O- (4-Et-cHx) H H
1-2051 H H H H Et 2 -C≡C- (CH₂)₂O- (4-Pr-cHx) H H
1-2052 H H H H Et 2 -C≡C- (CH₂)₂O- (4-iPr-cHx) H H
1-2053 H H H H Et 2 -C≡C- (CH₂)₂O- (4-Bu-cHx) H H
1-2054 H H H H Et 2 -C≡C- (CH₂)₂O- (4-CF_Three-cHx) H H
1-2055 H H H H Et 2 -C≡C- (CH₂)₂O- (4-MeO-cHx) H H
1-2056 H H H H Et 2 -C≡C- (CH₂)₂O- (4-EtO-cHx) H H
1-2057 H H H H Et 2 -C≡C- (CH₂)₂O- (4-PrO-cHx) H H
1-2058 H H H H Et 2 -C≡C- (CH₂)₂O- (4-iPrO-cHx) H H
1-2059 H H H H Et 2 -C≡C- (CH₂)₂O- (3-MeS-cHx) H H
1-2060 H H H H Et 2 -C≡C- (CH₂)₂O- (4-MeS-cHx) H H
1-2061 H H H H Et 2 -C≡C- (CH₂)₂O- (2,4-diMe-cHx) H H
1-2062 H H H H Et 2 -C≡C- (CH₂)₂O- (3,4-diMe-cHx) H H
1-2063 H H H H Et 2 -C≡C- (CH₂)₂O- (3,5-diMe-cHx) H H
1-2064 H H H H Et 2 -C≡C- (CH₂)₂O-Ph H H
1-2065 H H H H Et 2 -C≡C- (CH₂)₂O-Ph Me H
1-2066 H H H H Et 2 -C≡C- (CH₂)₂O-Ph H Me
1-2067 H H H H Et 2 -C≡C- (CH₂)₂O-Ph F H
1-2068 H H H H Et 2 -C≡C- (CH₂)₂O-Ph H F
1-2069 H H Me Me Et 2 -C≡C- (CH₂)₂-OCH₂-Ph H H
1-2070 CO₂Me H H H Et 2 -C≡C- (CH₂)₂O-Ph H H
1-2071 CO₂Et H H H Et 2 -C≡C- (CH₂)₂O-Ph H H
1-2072 H H H H Et 2 -C≡C- (CH₂)₂O- (4-F-Ph) H H
1-2073 H H H H Et 2 -C≡C- (CH₂)₂O- (4-Cl-Ph) H H
1-2074 H H H H Et 2 -C≡C- (CH₂)₂O- (4-Br-Ph) H H
1-2075 H H H H Et 2 -C≡C- (CH₂)₂O- (4-Me-Ph) H H
1-2076 H H H H Et 2 -C≡C- (CH₂)₂O- (4-Et-Ph) H H
1-2077 H H H H Et 2 -C≡C- (CH₂)₂O- (4-Pr-Ph) H H
1-2078 H H H H Et 2 -C≡C- (CH₂)₂O- (4-iPr-Ph) H H
1-2079 H H H H Et 2 -C≡C- (CH₂)₂O- (4-Bu-Ph) H H
1-2080 H H H H Et 2 -C≡C- (CH₂)₂O- (4-CF_Three-Ph) H H
1-2081 H H H H Et 2 -C≡C- (CH₂)₂O- (4-MeO-Ph) H H
1-2082 H H H H Et 2 -C≡C- (CH₂)₂O- (4-EtO-Ph) H H
1-2083 H H H H Et 2 -C≡C- (CH₂)₂O- (4-PrO-Ph) H H
1-2084 H H H H Et 2 -C≡C- (CH₂)₂O- (4-iPrO-Ph) H H
1-2085 H H H H Et 2 -C≡C- (CH₂)₂O- (4-MeS-Ph) H H
1-2086 H H H H Et 2 -C≡C- (CH₂)₂O- (2,4-diMe-Ph) H H
1-2087 H H H H Et 2 -C≡C- (CH₂)₂O- (3,4-diMe-Ph) H H
1-2088 H H H H Et 2 -C≡C- (CH₂)₂O- (3,5-diMe-Ph) H H
1-2089 H H H H Et 2 -CO- (CH₂)_Three-cHx H H
1-2090 H H Me Me Et 2 -CO- (CH₂)_Three-cHx H H
1-2091 CO₂Me H H H Et 2 -CO- (CH₂)_Three-cHx H H
1-2092 CO₂Et H H H Et 2 -CO- (CH₂)_Three-cHx H H
1-2093 H H H H Et 2 -CO- (CH₂)_Three-Ph H H
1-2094 H H Me Me Et 2 -CO- (CH₂)_Three-Ph H H
1-2095 CO₂Me H H H Et 2 -CO- (CH₂)_Three-Ph H H
1-2096 CO₂Et H H H Et 2 -CO- (CH₂)_Three-Ph H H
1-2097 H H H H Et 2 -CO- (CH₂)_Four-cHx H H
1-2098 H H Me Me Et 2 -CO- (CH₂)_Four-cHx H H
1-2099 CO₂Me H H H Et 2 -CO- (CH₂)_Four-cHx H H
1-2100 CO₂Et H H H Et 2 -CO- (CH₂)_Four-cHx H H
1-2101 H H H H Et 2 -CO- (CH₂)_Four-Ph H H
1-2102 H H Me Me Et 2 -CO- (CH₂)_Four-Ph H H
1-2103 CO₂Me H H H Et 2 -CO- (CH₂)_Four-Ph H H
1-2104 CO₂Et H H H Et 2 -CO- (CH₂)_Four-Ph H H
1-2105 H H H H Et 2 -CO- (CH₂)_Five-cHx H H
1-2106 H H Me Me Et 2 -CO- (CH₂)_Five-cHx H H
1-2107 CO₂Me H H H Et 2 -CO- (CH₂)_Five-cHx H H
1-2108 CO₂Et H H H Et 2 -CO- (CH₂)_Five-cHx H H
1-2109 H H H H Et 2 -CO- (CH₂)_Five-Ph H H
1-2110 H H Me Me Et 2 -CO- (CH₂)_Five-Ph H H
1-2111 CO₂Me H H H Et 2 -CO- (CH₂)_Five-Ph H H
1-2112 CO₂Et H H H Et 2 -CO- (CH₂)_Five-Ph H H
1-2113 H H H H Et 2 -CH (OH)-(CH₂)_Four-cHx H H
1-2114 H H Me Me Et 2 -CH (OH)-(CH₂)_Four-cHx H H
1-2115 CO₂Me H H H Et 2 -CH (OH)-(CH₂)_Four-cHx H H
1-2116 CO₂Et H H H Et 2 -CH (OH)-(CH₂)_Four-cHx H H
1-2117 H H H H Et 2 -CH (OH)-(CH₂)_Four-Ph H H
1-2118 H H Me Me Et 2 -CH (OH)-(CH₂)_Four-Ph H H
1-2119 CO₂Me H H H Et 2 -CH (OH)-(CH₂)_Four-Ph H H
1-2120 CO₂Et H H H Et 2 -CH (OH)-(CH₂)_Four-Ph H H
1-2121 H H H H Et 2 -CH (OH)-(CH₂)_Five-cHx H H
1-2122 H H Me Me Et 2 -CH (OH)-(CH₂)_Five-cHx H H
1-2123 CO₂Me H H H Et 2 -CH (OH)-(CH₂)_Five-cHx H H
1-2124 CO₂Et H H H Et 2 -CH (OH)-(CH₂)_Five-cHx H H
1-2125 H H H H Et 2 -CH (OH)-(CH₂)_Five-Ph H H
1-2126 H H Me Me Et 2 -CH (OH)-(CH₂)_Five-Ph H H
1-2127 CO₂Me H H H Et 2 -CH (OH)-(CH₂)_Five-Ph H H
1-2128 CO₂Et H H H Et 2 -CH (OH)-(CH₂)_Five-Ph H H
1-2129 H H H H Et 2 -4- (cHx-CH₂O) Ph H H
1-2130 H H Me Me Et 2 -4- (cHx-CH₂O) Ph H H
1-2131 CO₂Me H H H Et 2 -4- (cHx-CH₂O) Ph H H
1-2132 CO₂Et H H H Et 2 -4- (cHx-CH₂O) Ph H H
1-2133 H H H H Et 2 -4- [cHx- (CH₂)₂O] Ph H H
1-2134 H H H H Et 2 -4- [cHx- (CH₂)_ThreeO] Ph H H
1-2135 H H H H Et 2-(4-BzO-Ph) H H
1-2136 H H Me Me Et 2-(4-BzO-Ph) H H
1-2137 CO₂Me H H H Et 2-(4-BzO-Ph) H H
1-2138 CO₂Et H H H Et 2-(4-BzO-Ph) H H
1-2139 H H H H Et 2-(4-BzO-2-F-Ph) H H
1-2140 H H H H Et 2-(4-BzO-3-F-Ph) H H
1-2141 H H H H Et 2-(4-BzO-2,3-diF-Ph) H H
1-2142 H H H H Et 2-(4-BzO-2-Cl-Ph) H H
1-2143 H H H H Et 2-(4-BzO-3-Cl-Ph) H H
1-2144 H H H H Et 2-(4-BzO-2,3-diCl-Ph) H H
1-2145 H H H H Et 2-(4-BzO-2-Me-Ph) H H
1-2146 H H H H Et 2-(4-BzO-3-Me-Ph) H H
1-2147 H H H H Et 2-(4-BzO-2,3-diMe-Ph) H H
1-2148 H H H H Et 2 -4- [Ph- (CH₂)₂O] -Ph H H
1-2149 H H H H Et 2 -4- [Ph- (CH₂)_ThreeO] -Ph H H
1-2150 H H H H Pr 2-(CH₂)_Five-cHx H H
1-2151 H H H H Pr 2-(CH₂)_Five-Ph H H
1-2152 H H H H Pr 2-(CH₂)₆-cHx H H
1-2153 H H H H Pr 2-(CH₂)₆-Ph H H
1-2154 H H H H Pr 2 -C≡C-CH₂-cHx H H
1-2155 H H H H Pr 2 -C≡C- (CH₂)_Three-cHx H H
1-2156 H H H H Pr 2 -C≡C- (CH₂)_Three-Ph H H
1-2157 H H H H Pr 2 -C≡C- (CH₂)_Four-cHx H H
1-2158 H H H H Pr 2 -C≡C- (CH₂)_Four-Ph H H
1-2159 CO₂Me H H H Pr 2 -C≡C-CH₂O-Ph H H
1-2160 CO₂Et H H H Pr 2 -C≡C-CH₂O-Ph H H
1-2161 H H H H Pr 2 -C≡C- (CH₂)₂O-cHx H H
1-2162 H H H H Pr 2 -C≡C- (CH₂)₂O-Ph H H
1-2163 H H H H Pr 2 -4- (cHx-CH₂O) Ph H H
1-2164 H H H H Pr 2-(4-BzO-Ph) H H
1-2165 H H H H Me 3-(CH₂)_Five-cHx H H
1-2166 H H H H Me 3-(CH₂)₆-cHx H H
1-2167 H H H H Me 3 -CH = CH- (CH₂)_Three-cHx H H
1-2168 H H H H Me 3 -CH = CH- (CH₂)_Four-cHx H H
1-2169 H H H H Me 3 -C≡C- (CH₂)_Three-cHx H H
1-2170 H H H H Me 3 -C≡C- (CH₂)_Four-cHx H H
1-2171 H H H H Me 3 -CO- (CH₂)_Four-cHx H H
1-2172 H H H H Me 3 -CO- (CH₂)_Five-cHx H H
1-2173 H H H H Me 3 -CO- (CH₂)_Four-Ph H H
1-2174 H H H H Me 3 -CO- (CH₂)_Five-Ph H H
1-2175 H H H H Me 3 -CH (OH)-(CH₂)_Four-cHx H H
1-2176 H H H H Me 3 -CH (OH)-(CH₂)_Five-cHx H H
1-2177 H H H H Me 3 -4- (cHx-CH₂O) Ph H H
1-2178 H H H H Me 3-(4-BzO-Ph) H H
1-2179 H H H H Me 3 -C≡C-CH₂O-cPn H H
1-2180 H H H H Me 3 -C≡C- (CH₂)₂O-cPn H H
1-2181 H H H H Me 3 -C≡C-CH₂O-cHx H H
1-2182 H H H H Me 3 -C≡C- (CH₂)₂O-cHx H H
1-2183 H H H H Me 3 -C≡C-CH₂O-Ph H H
1-2184 H H H H Me 3 -C≡C- (CH₂)₂O-Ph H H
1-2185 H H H H Me 2-(CH₂)_Four-(3-F-Ph) H H
1-2186 H H H H Me 2-(CH₂)_Four-(3,4-diF-Ph) H H
1-2187 H H H H Me 2-(CH₂)_Four-(3,5-diF-Ph) H H
1-2188 H H H H Me 2-(CH₂)_Four-(3-Cl-Ph) H H
1-2189 H H H H Me 2-(CH₂)_Four-(4-Cl-Ph) H H
1-2190 H H H H Me 2-(CH₂)_Four-(3,4-diCl-Ph) H H
1-2191 H H H H Me 2-(CH₂)_Four-(3,5-diCl-Ph) H H
1-2192 H H H H Me 2-(CH₂)_Four-(3-Me-Ph) H H
1-2193 H H H H Me 2-(CH₂)_Four-(3,4-diMe-Ph) H H
1-2194 H H H H Me 2-(CH₂)_Four-(3,5-diMe-Ph) H H
1-2195 H H H H Me 2-(CH₂)_Four-(3-CF_Three-Ph) H H
1-2196 H H H H Me 2-(CH₂)_Four-(3,4-diCF_Three-Ph) H H
1-2197 H H H H Me 2-(CH₂)_Four-(3,5-diCF_Three-Ph) H H
1-2198 H H H H Me 2-(CH₂)_Four-(3-MeO-Ph) H H
1-2199 H H H H Me 2-(CH₂)_Four-(3,4-diMeO-Ph) H H
1-2200 H H H H Me 2-(CH₂)_Four-(3,5-diMeO-Ph) H H
1-2201 H H H H Me 2-(CH₂)_Four-(3,4,5-triMeO-Ph) H H
1-2202 H H H H Me 2-(CH₂)_Four-(3-Ac-Ph) H H
1-2203 H H H H Me 2-(CH₂)_Four-(4-Ac-Ph) H H
1-2204 H H H H Me 2-(CH₂)_Five-(3,4-diF-Ph) H H
1-2205 H H H H Me 2-(CH₂)_Five-(3,5-diF-Ph) H H
1-2206 H H H H Me 2-(CH₂)_Five-(3-Cl-Ph) H H
1-2207 H H H H Me 2-(CH₂)_Five-(3,4-diCl-Ph) H H
1-2208 H H H H Me 2-(CH₂)_Five-(3,5-diCl-Ph) H H
1-2209 H H H H Me 2-(CH₂)_Five-(3,4-diCF_Three-Ph) H H
1-2210 H H H H Me 2-(CH₂)_Five-(3,5-diCF_Three-Ph) H H
1-2211 H H H H Me 2-(CH₂)_Five-(3,4-diMeO-Ph) H H
1-2212 H H H H Me 2-(CH₂)_Five-(3,5-diMeO-Ph) H H
1-2213 H H H H Me 2-(CH₂)_Five-(3,4,5-triMeO-Ph) H H
1-2214 H H H H Me 2-(CH₂)_Five-(3-Ac-Ph) H H
1-2215 H H H H Me 2-(CH₂)_Five-(4-Ac-Ph) H H
1-2216 H H H H Me 2-(CH₂)_Three-O- (3-F-Ph) H H
1-2217 H H H H Me 2-(CH₂)_Three-O- (3,4-diF-Ph) H H
1-2218 H H H H Me 2-(CH₂)_Three-O- (3,5-diF-Ph) H H
1-2219 H H H H Me 2-(CH₂)_Three-O- (3-Me-Ph) H H
1-2220 H H H H Me 2-(CH₂)_Three-O- (3,4-diMe-Ph) H H
1-2221 H H H H Me 2-(CH₂)_Three-O- (3,5-diMe-Ph) H H
1-2222 H H H H Me 2-(CH₂)_Three-O- (3-CF_Three-Ph) H H
1-2223 H H H H Me 2-(CH₂)_Three-O- (3,4-diCF_Three-Ph) H H
1-2224 H H H H Me 2-(CH₂)_Three-O- (3,5-diCF_Three-Ph) H H
1-2225 H H H H Me 2-(CH₂)_Three-O- (3-MeO-Ph) H H
1-2226 H H H H Me 2-(CH₂)_Three-O- (3,4-diMeO-Ph) H H
1-2227 H H H H Me 2-(CH₂)_Three-O- (3,5-diMeO-Ph) H H
1-2228 H H H H Me 2-(CH₂)_Three-O- (3,4,5-triMeO-Ph) H H
1-2229 H H H H Me 2-(CH₂)_Three-O- (3-Ac-Ph) H H
1-2230 H H H H Me 2-(CH₂)_Three-O- (4-Ac-Ph) H H
1-2231 H H H H Me 2-(CH₂)_Four-O- (3,4-diF-Ph) H H
1-2232 H H H H Me 2-(CH₂)_Four-O- (3,5-diF-Ph) H H
1-2233 H H H H Me 2-(CH₂)_Four-O- (3,4-diMeO-Ph) H H
1-2234 H H H H Me 2-(CH₂)_Four-O- (3,5-diMeO-Ph) H H
1-2235 H H H H Me 2-(CH₂)_Four-O- (3,4,5-triMeO-Ph) H H
1-2236 H H H H Me 2-(CH₂)_Four-O- (3-Ac-Ph) H H
1-2237 H H H H Me 2-(CH₂)_Four-O- (4-Ac-Ph) H H
1-2238 H H H H Me 2 -C≡C- (CH₂)₂-(3-F-Ph) H H
1-2239 H H H H Me 2 -C≡C- (CH₂)₂-(3,4-diF-Ph) H H
1-2240 H H H H Me 2 -C≡C- (CH₂)₂-(3,5-diF-Ph) H H
1-2241 H H H H Me 2 -C≡C- (CH₂)₂-(3-Cl-Ph) H H
1-2242 H H H H Me 2 -C≡C- (CH₂)₂-(4-Cl-Ph) H H
1-2243 H H H H Me 2 -C≡C- (CH₂)₂-(3,4-diCl-Ph) H H
1-2244 H H H H Me 2 -C≡C- (CH₂)₂-(3,5-diCl-Ph) H H
1-2245 H H H H Me 2 -C≡C- (CH₂)₂-(3-Me-Ph) H H
1-2246 H H H H Me 2 -C≡C- (CH₂)₂-(3,4-diMe-Ph) H H
1-2247 H H H H Me 2 -C≡C- (CH₂)₂-(3,5-diMe-Ph) H H
1-2248 H H H H Me 2 -C≡C- (CH₂)₂-(3-CF_Three-Ph) H H
1-2249 H H H H Me 2 -C≡C- (CH₂)₂-(3,4-diCF_Three-Ph) H H
1-2250 H H H H Me 2 -C≡C- (CH₂)₂-(3,5-diCF_Three-Ph) H H
1-2251 H H H H Me 2 -C≡C- (CH₂)₂-(3-MeO-Ph) H H
1-2252 H H H H Me 2 -C≡C- (CH₂)₂-(3,4-diMeO-Ph) H H
1-2253 H H H H Me 2 -C≡C- (CH₂)₂-(3,5-diMeO-Ph) H H
1-2254 H H H H Me 2 -C≡C- (CH₂)₂-(3,4,5-triMeO-Ph) H H
1-2255 H H H H Me 2 -C≡C- (CH₂)₂-(3-Ac-Ph) H H
1-2256 H H H H Me 2 -C≡C- (CH₂)₂-(4-Ac-Ph) H H
1-2257 H H H H Me 2 -C≡C- (CH₂)_Three-(3,4-diF-Ph) H H
1-2258 H H H H Me 2 -C≡C- (CH₂)_Three-(3,5-diF-Ph) H H
1-2259 H H H H Me 2 -C≡C- (CH₂)_Three-(3-Cl-Ph) H H
1-2260 H H H H Me 2 -C≡C- (CH₂)_Three-(3,4-diCl-Ph) H H
1-2261 H H H H Me 2 -C≡C- (CH₂)_Three-(3,5-diCl-Ph) H H
1-2262 H H H H Me 2 -C≡C- (CH₂)_Three-(3,4-diCF_Three-Ph) H H
1-2263 H H H H Me 2 -C≡C- (CH₂)_Three-(3,5-diCF_Three-Ph) H H
1-2264 H H H H Me 2 -C≡C- (CH₂)_Three-(3,4-diMeO-Ph) H H
1-2265 H H H H Me 2 -C≡C- (CH₂)_Three-(3,5-diMeO-Ph) H H
1-2266 H H H H Me 2 -C≡C- (CH₂)_Three-(3,4,5-triMeO-Ph) H H
1-2267 H H H H Me 2 -C≡C- (CH₂)_Three-(3-Ac-Ph) H H
1-2268 H H H H Me 2 -C≡C- (CH₂)_Three-(4-Ac-Ph) H H
1-2269 H H H H Me 2 -C≡C-CH₂-O- (3-F-Ph) H H
1-2270 H H H H Me 2 -C≡C-CH₂-O- (3,4-diF-Ph) H H
1-2271 H H H H Me 2 -C≡C-CH₂-O- (3,5-diF-Ph) H H
1-2272 H H H H Me 2 -C≡C-CH₂-O- (3-Cl-Ph) H H
1-2273 H H H H Me 2 -C≡C-CH₂-O- (4-Cl-Ph) H H
1-2274 H H H H Me 2 -C≡C-CH₂-O- (3,4-diCl-Ph) H H
1-2275 H H H H Me 2 -C≡C-CH₂-O- (3,5-diCl-Ph) H H
1-2276 H H H H Me 2 -C≡C-CH₂-O- (3-Me-Ph) H H
1-2277 H H H H Me 2 -C≡C-CH₂-O- (2,4-diMe-Ph) H H
1-2278 H H H H Me 2 -C≡C-CH₂-O- (3,4-diMe-Ph) H H
1-2279 H H H H Me 2 -C≡C-CH₂-O- (3,5-diMe-Ph) H H
1-2280 H H H H Me 2 -C≡C-CH₂-O- (3-CF_Three-Ph) H H
1-2281 H H H H Me 2 -C≡C-CH₂-O- (3,4-diCF_Three-Ph) H H
1-2282 H H H H Me 2 -C≡C-CH₂-O- (3,5-diCF_Three-Ph) H H
1-2283 H H H H Me 2 -C≡C-CH₂-O- (3-MeO-Ph) H H
1-2284 H H H H Me 2 -C≡C-CH₂-O- (3,4-diMeO-Ph) H H
1-2285 H H H H Me 2 -C≡C-CH₂-O- (3,5-diMeO-Ph) H H
1-2286 H H H H Me 2 -C≡C-CH₂-O- (3,4,5-triMeO-Ph) H H
1-2287 H H H H Me 2 -C≡C-CH₂-O- (3-Ac-Ph) H H
1-2288 H H H H Me 2 -C≡C-CH₂-O- (4-Ac-Ph) H H
1-2289 H H H H Me 2 -C≡C-CH₂-O- (4-CO₂H-Ph) H H
1-2290 H H H H Me 2 -C≡C- (CH₂)₂-O- (3,4-diF-Ph) H H
1-2291 H H H H Me 2 -C≡C- (CH₂)₂-O- (3,5-diF-Ph) H H
1-2292 H H H H Me 2 -C≡C- (CH₂)₂-O- (3-Cl-Ph) H H
1-2293 H H H H Me 2 -C≡C- (CH₂)₂-O- (3,4-diCl-Ph) H H
1-2294 H H H H Me 2 -C≡C- (CH₂)₂-O- (3,5-diCl-Ph) H H
1-2295 H H H H Me 2 -C≡C- (CH₂)₂-O- (3,4-diCF_Three-Ph) H H
1-2296 H H H H Me 2 -C≡C- (CH₂)₂-O- (3,5-diCF_Three-Ph) H H
1-2297 H H H H Me 2 -C≡C- (CH₂)₂-O- (3,4-diMeO-Ph) H H
1-2298 H H H H Me 2 -C≡C- (CH₂)₂-O- (3,5-diMeO-Ph) H H
1-2299 H H H H Me 2 -C≡C- (CH₂)₂-O- (3,4,5-triMeO-Ph) H H
1-2300 H H H H Me 2 -C≡C- (CH₂)₂-O- (3-Ac-Ph) H H
1-2301 H H H H Me 2 -C≡C- (CH₂)₂-O- (4-Ac-Ph) H H
1-2302 H H H H Me 2 -CO- (CH₂)_Three-(3-F-Ph) H H
1-2303 H H H H Me 2 -CO- (CH₂)_Three-(4-F-Ph) H H
1-2304 H H H H Me 2 -CO- (CH₂)_Three-(3,4-diF-Ph) H H
1-2305 H H H H Me 2 -CO- (CH₂)_Three-(3,5-diF-Ph) H H
1-2306 H H H H Me 2 -CO- (CH₂)_Three-(3-Cl-Ph) H H
1-2307 H H H H Me 2 -CO- (CH₂)_Three-(4-Cl-Ph) H H
1-2308 H H H H Me 2 -CO- (CH₂)_Three-(3,4-diCl-Ph) H H
1-2309 H H H H Me 2 -CO- (CH₂)_Three-(3,5-diCl-Ph) H H
1-2310 H H H H Me 2 -CO- (CH₂)_Three-(3-Me-Ph) H H
1-2311 H H H H Me 2 -CO- (CH₂)_Three-(4-Me-Ph) H H
1-2312 H H H H Me 2 -CO- (CH₂)_Three-(3,4-diMe-Ph) H H
1-2313 H H H H Me 2 -CO- (CH₂)_Three-(3,5-diMe-Ph) H H
1-2314 H H H H Me 2 -CO- (CH₂)_Three-(3-Et-Ph) H H
1-2315 H H H H Me 2 -CO- (CH₂)_Three-(4-Et-Ph) H H
1-2316 H H H H Me 2 -CO- (CH₂)_Three-(3-CF_Three-Ph) H H
1-2317 H H H H Me 2 -CO- (CH₂)_Three-(4-CF_Three-Ph) H H
1-2318 H H H H Me 2 -CO- (CH₂)_Three-(3,4-diCF_Three-Ph) H H
1-2319 H H H H Me 2 -CO- (CH₂)_Three-(3,5-diCF_Three-Ph) H H
1-2320 H H H H Me 2 -CO- (CH₂)_Three-(3-MeO-Ph) H H
1-2321 H H H H Me 2 -CO- (CH₂)_Three-(4-MeO-Ph) H H
1-2322 H H H H Me 2 -CO- (CH₂)_Three-(3,4-diMeO-Ph) H H
1-2323 H H H H Me 2 -CO- (CH₂)_Three-(3,5-diMeO-Ph) H H
1-2324 H H H H Me 2 -CO- (CH₂)_Three-(3,4,5-triMeO-Ph) H H
1-2325 H H H H Me 2 -CO- (CH₂)_Three-(4-MeS-Ph) H H
1-2326 H H H H Me 2 -CO- (CH₂)_Three-(3-Ac-Ph) H H
1-2327 H H H H Me 2 -CO- (CH₂)_Three-(4-Ac-Ph) H H
1-2328 H H H H Me 2 -CO- (CH₂)_Four-(3-F-Ph) H H
1-2329 H H H H Me 2 -CO- (CH₂)_Four-(3,4-diF-Ph) H H
1-2330 H H H H Me 2 -CO- (CH₂)_Four-(3,5-diF-Ph) H H
1-2331 H H H H Me 2 -CO- (CH₂)_Four-(3-Cl-Ph) H H
1-2332 H H H H Me 2 -CO- (CH₂)_Four-(4-Cl-Ph) H H
1-2333 H H H H Me 2 -CO- (CH₂)_Four-(3,4-diCl-Ph) H H
1-2334 H H H H Me 2 -CO- (CH₂)_Four-(3,5-diCl-Ph) H H
1-2335 H H H H Me 2 -CO- (CH₂)_Four-(3-Me-Ph) H H
1-2336 H H H H Me 2 -CO- (CH₂)_Four-(3,4-diMe-Ph) H H
1-2337 H H H H Me 2 -CO- (CH₂)_Four-(3,5-diMe-Ph) H H
1-2338 H H H H Me 2 -CO- (CH₂)_Four-(3-CF_Three-Ph) H H
1-2339 H H H H Me 2 -CO- (CH₂)_Four-(3,4-diCF_Three-Ph) H H
1-2340 H H H H Me 2 -CO- (CH₂)_Four-(3,5-diCF_Three-Ph) H H
1-2341 H H H H Me 2 -CO- (CH₂)_Four-(3-MeO-Ph) H H
1-2342 H H H H Me 2 -CO- (CH₂)_Four-(3,4-diMeO-Ph) H H
1-2343 H H H H Me 2 -CO- (CH₂)_Four-(3,5-diMeO-Ph) H H
1-2344 H H H H Me 2 -CO- (CH₂)_Four-(3,4,5-triMeO-Ph) H H
1-2345 H H H H Me 2 -CO- (CH₂)_Four-(3-Ac-Ph) H H
1-2346 H H H H Me 2 -CO- (CH₂)_Four-(4-Ac-Ph) H H
1-2347 H H H H Me 2 -CH (OH)-(CH₂)_Three-(3-F-Ph) H H
1-2348 H H H H Me 2 -CH (OH)-(CH₂)_Three-(4-F-Ph) H H
1-2349 H H H H Me 2 -CH (OH)-(CH₂)_Three-(3,4-diF-Ph) H H
1-2350 H H H H Me 2 -CH (OH)-(CH₂)_Three-(3,5-diF-Ph) H H
1-2351 H H H H Me 2 -CH (OH)-(CH₂)_Three-(3-Cl-Ph) H H
1-2352 H H H H Me 2 -CH (OH)-(CH₂)_Three-(4-Cl-Ph) H H
1-2353 H H H H Me 2 -CH (OH)-(CH₂)_Three-(3,4-diCl-Ph) H H
1-2354 H H H H Me 2 -CH (OH)-(CH₂)_Three-(3,5-diCl-Ph) H H
1-2355 H H H H Me 2 -CH (OH)-(CH₂)_Three-(3-Me-Ph) H H
1-2356 H H H H Me 2 -CH (OH)-(CH₂)_Three-(4-Me-Ph) H H
1-2357 H H H H Me 2 -CH (OH)-(CH₂)_Three-(3,4-diMe-Ph) H H
1-2358 H H H H Me 2 -CH (OH)-(CH₂)_Three-(3,5-diMe-Ph) H H
1-2359 H H H H Me 2 -CH (OH)-(CH₂)_Three-(3-Et-Ph) H H
1-2360 H H H H Me 2 -CH (OH)-(CH₂)_Three-(4-Et-Ph) H H
1-2361 H H H H Me 2 -CH (OH)-(CH₂)_Three-(3-CF_Three-Ph) H H
1-2362 H H H H Me 2 -CH (OH)-(CH₂)_Three-(4-CF_Three-Ph) H H
1-2363 H H H H Me 2 -CH (OH)-(CH₂)_Three-(3,4-diCF_Three-Ph) H H
1-2364 H H H H Me 2 -CH (OH)-(CH₂)_Three-(3,5-diCF_Three-Ph) H H
1-2365 H H H H Me 2 -CH (OH)-(CH₂)_Three-(3-MeO-Ph) H H
1-2366 H H H H Me 2 -CH (OH)-(CH₂)_Three-(4-MeO-Ph) H H
1-2367 H H H H Me 2 -CH (OH)-(CH₂)_Three-(3,4-diMeO-Ph) H H
1-2368 H H H H Me 2 -CH (OH)-(CH₂)_Three-(3,5-diMeO-Ph) H H
1-2369 H H H H Me 2 -CH (OH)-(CH₂)_Three-(3,4,5-triMeO-Ph) H H
1-2370 H H H H Me 2 -CH (OH)-(CH₂)_Three-(4-MeS-Ph) H H
1-2371 H H H H Me 2 -CH (OH)-(CH₂)_Three-(3-Ac-Ph) H H
1-2372 H H H H Me 2 -CH (OH)-(CH₂)_Three-(4-Ac-Ph) H H
1-2373 H H H H Me 2 -CH (OH)-(CH₂)_Four-(3-F-Ph) H H
1-2374 H H H H Me 2 -CH (OH)-(CH₂)_Four-(3,4-diF-Ph) H H
1-2375 H H H H Me 2 -CH (OH)-(CH₂)_Four-(3,5-diF-Ph) H H
1-2376 H H H H Me 2 -CH (OH)-(CH₂)_Four-(3-Cl-Ph) H H
1-2377 H H H H Me 2 -CH (OH)-(CH₂)_Four-(4-Cl-Ph) H H
1-2378 H H H H Me 2 -CH (OH)-(CH₂)_Four-(3,4-diCl-Ph) H H
1-2379 H H H H Me 2 -CH (OH)-(CH₂)_Four-(3,5-diCl-Ph) H H
1-2380 H H H H Me 2 -CH (OH)-(CH₂)_Four-(3-Me-Ph) H H
1-2381 H H H H Me 2 -CH (OH)-(CH₂)_Four-(3,4-diMe-Ph) H H
1-2382 H H H H Me 2 -CH (OH)-(CH₂)_Four-(3,5-diMe-Ph) H H
1-2383 H H H H Me 2 -CH (OH)-(CH₂)_Four-(3-CF_Three-Ph) H H
1-2384 H H H H Me 2 -CH (OH)-(CH₂)_Four-(3,4-diCF_Three-Ph) H H
1-2385 H H H H Me 2 -CH (OH)-(CH₂)_Four-(3,5-diCF_Three-Ph) H H
1-2386 H H H H Me 2 -CH (OH)-(CH₂)_Four-(3-MeO-Ph) H H
1-2387 H H H H Me 2 -CH (OH)-(CH₂)_Four-(3,4-diMeO-Ph) H H
1-2388 H H H H Me 2 -CH (OH)-(CH₂)_Four-(3,5-diMeO-Ph) H H
1-2389 H H H H Me 2 -CH (OH)-(CH₂)_Four-(3,4,5-triMeO-Ph) H H
1-2390 H H H H Me 2 -CH (OH)-(CH₂)_Four-(3-Ac-Ph) H H
1-2391 H H H H Me 2 -CH (OH)-(CH₂)_Four-(4-Ac-Ph) H H
1-2392 H H H H Me 2 -O- (CH₂)_Three-cHx H H
1-2393 H H H H Me 2 -O- (CH₂)_Four-cHx H H
1-2394 H H H H Me 2 -O- (CH₂)_Five-cHx H H
1-2395 H H H H Me 2 -O- (CH₂)_Three-Ph H H
1-2396 H H H H Me 2 -O- (CH₂)_Four-Ph H H
1-2397 H H H H Me 2 -O- (CH₂)_Five-Ph H H
1-2398 COCH_Three H H H Me 2-(CH₂)_Four-cHx H H
1-2399 COC₂H_Five H H H Me 2-(CH₂)_Four-cHx H H
1-2400 COC_ThreeH₇ H H H Me 2-(CH₂)_Four-cHx H H
1-2401 COC_FourH₉ H H H Me 2-(CH₂)_Four-cHx H H
1-2402 COC_FiveH₁₁ H H H Me 2-(CH₂)_Four-cHx H H
1-2403 COC₆H₁₃ H H H Me 2-(CH₂)_Four-cHx H H
1-2404 COC₇H₁₅ H H H Me 2-(CH₂)_Four-cHx H H
1-2405 COC₈H₁₇ H H H Me 2-(CH₂)_Four-cHx H H
1-2406 COCH_Three  H H H Me 2-(CH₂)_Four-Ph H H
1-2407 COC₂H_Five H H H Me 2-(CH₂)_Four-Ph H H
1-2408 COC_ThreeH₇ H H H Me 2-(CH₂)_Four-Ph H H
1-2409 COC_FourH₉ H H H Me 2-(CH₂)_Four-Ph H H
1-2410 COC_FiveH₁₁ H H H Me 2-(CH₂)_Four-Ph H H
1-2411 COC₆H₁₃ H H H Me 2-(CH₂)_Four-Ph H H
1-2412 COC₇H₁₅ H H H Me 2-(CH₂)_Four-Ph H H
1-2413 COC₈H₁₇ H H H Me 2-(CH₂)_Four-Ph H H
1-2414 COCH_Three  H H H Me 2-(CH₂)_Five-cHx H H
1-2415 COC₂H_Five H H H Me 2-(CH₂)_Five-cHx H H
1-2416 COC_ThreeH₇ H H H Me 2-(CH₂)_Five-cHx H H
1-2417 COC_FourH₉ H H H Me 2-(CH₂)_Five-cHx H H
1-2418 COC_FiveH₁₁ H H H Me 2-(CH₂)_Five-cHx H H
1-2419 COC₆H₁₃ H H H Me 2-(CH₂)_Five-cHx H H
1-2420 COC₇H₁₅ H H H Me 2-(CH₂)_Five-cHx H H
1-2421 COC₈H₁₇ H H H Me 2-(CH₂)_Five-cHx H H
1-2422 COCH_Three  H H H Me 2-(CH₂)_Five-Ph H H
1-2423 COC₂H_Five H H H Me 2-(CH₂)_Five-Ph H H
1-2424 COC_ThreeH₇ H H H Me 2-(CH₂)_Five-Ph H H
1-2425 COC_FourH₉ H H H Me 2-(CH₂)_Five-Ph H H
1-2426 COC_FiveH₁₁ H H H Me 2-(CH₂)_Five-Ph H H
1-2427 COC₆H₁₃ H H H Me 2-(CH₂)_Five-Ph H H
1-2428 COC₇H₁₅ H H H Me 2-(CH₂)_Five-Ph H H
1-2429 COC₈H₁₇ H H H Me 2-(CH₂)_Five-Ph H H
1-2430 COCH_Three  H H H Me 2 -C≡C- (CH₂)₂-cHx H H
1-2431 COC₂H_Five H H H Me 2 -C≡C- (CH₂)₂-cHx H H
1-2432 COC_ThreeH₇ H H H Me 2 -C≡C- (CH₂)₂-cHx H H
1-2433 COC_FourH₉ H H H Me 2 -C≡C- (CH₂)₂-cHx H H
1-2434 COC_FiveH₁₁ H H H Me 2 -C≡C- (CH₂)₂-cHx H H
1-2435 COC₆H₁₃ H H H Me 2 -C≡C- (CH₂)₂-cHx H H
1-2436 COC₇H₁₅ H H H Me 2 -C≡C- (CH₂)₂-cHx H H
1-2437 COC₈H₁₇ H H H Me 2 -C≡C- (CH₂)₂-cHx H H
1-2438 COCH_Three  H H H Me 2 -C≡C- (CH₂)₂-Ph H H
1-2439 COC₂H_Five H H H Me 2 -C≡C- (CH₂)₂-Ph H H
1-2440 COC_ThreeH₇ H H H Me 2 -C≡C- (CH₂)₂-Ph H H
1-2441 COC_FourH₉ H H H Me 2 -C≡C- (CH₂)₂-Ph H H
1-2442 COC_FiveH₁₁ H H H Me 2 -C≡C- (CH₂)₂-Ph H H
1-2443 COC₆H₁₃ H H H Me 2 -C≡C- (CH₂)₂-Ph H H
1-2444 COC₇H₁₅ H H H Me 2 -C≡C- (CH₂)₂-Ph H H
1-2445 COC₈H₁₇ H H H Me 2 -C≡C- (CH₂)₂-Ph H H
1-2446 COCH_Three  H H H Me 2 -C≡C- (CH₂)_Three-cHx H H
1-2447 COC₂H_Five H H H Me 2 -C≡C- (CH₂)_Three-cHx H H
1-2448 COC_ThreeH₇ H H H Me 2 -C≡C- (CH₂)_Three-cHx H H
1-2449 COC_FourH₉ H H H Me 2 -C≡C- (CH₂)_Three-cHx H H
1-2450 COC_FiveH₁₁ H H H Me 2 -C≡C- (CH₂)_Three-cHx H H
1-2451 COC₆H₁₃ H H H Me 2 -C≡C- (CH₂)_Three-cHx H H
1-2452 COC₇H₁₅ H H H Me 2 -C≡C- (CH₂)_Three-cHx H H
1-2453 COC₈H₁₇ H H H Me 2 -C≡C- (CH₂)_Three-cHx H H
1-2454 COCH_Three  H H H Me 2 -C≡C- (CH₂)_Three-Ph H H
1-2455 COC₂H_Five H H H Me 2 -C≡C- (CH₂)_Three-Ph H H
1-2456 COC_ThreeH₇ H H H Me 2 -C≡C- (CH₂)_Three-Ph H H
1-2457 COC_FourH₉ H H H Me 2 -C≡C- (CH₂)_Three-Ph H H
1-2458 COC_FiveH₁₁ H H H Me 2 -C≡C- (CH₂)_Three-Ph H H
1-2459 COC₆H₁₃ H H H Me 2 -C≡C- (CH₂)_Three-Ph H H
1-2460 COC₇H₁₅ H H H Me 2 -C≡C- (CH₂)_Three-Ph H H
1-2461 COC₈H₁₇ H H H Me 2 -C≡C- (CH₂)_Three-Ph H H
1-2462 COCH_Three  H H H Me 2 -C≡C- (CH₂)_Four-cHx H H
1-2463 COC₂H_Five H H H Me 2 -C≡C- (CH₂)_Four-cHx H H
1-2464 COC_ThreeH₇ H H H Me 2 -C≡C- (CH₂)_Four-cHx H H
1-2465 COC_FourH₉ H H H Me 2 -C≡C- (CH₂)_Four-cHx H H
1-2466 COC_FiveH₁₁ H H H Me 2 -C≡C- (CH₂)_Four-cHx H H
1-2467 COC₆H₁₃ H H H Me 2 -C≡C- (CH₂)_Four-cHx H H
1-2468 COC₇H₁₅ H H H Me 2 -C≡C- (CH₂)_Four-cHx H H
1-2469 COC₈H₁₇ H H H Me 2 -C≡C- (CH₂)_Four-cHx H H
1-2470 COCH_Three  H H H Me 2 -C≡C- (CH₂)_Four-Ph H H
1-2471 COC₂H_Five H H H Me 2 -C≡C- (CH₂)_Four-Ph H H
1-2472 COC_ThreeH₇ H H H Me 2 -C≡C- (CH₂)_Four-Ph H H
1-2473 COC_FourH₉ H H H Me 2 -C≡C- (CH₂)_Four-Ph H H
1-2474 COC_FiveH₁₁ H H H Me 2 -C≡C- (CH₂)_Four-Ph H H
1-2475 COC₆H₁₃ H H H Me 2 -C≡C- (CH₂)_Four-Ph H H
1-2476 COC₇H₁₅ H H H Me 2 -C≡C- (CH₂)_Four-Ph H H
1-2477 COC₈H₁₇ H H H Me 2 -C≡C- (CH₂)_Four-Ph H H
1-2478 COCH_Three  H H H Me 2 -C≡C- (CH₂)₂O-cHx H H
1-2479 COC₂H_Five H H H Me 2 -C≡C- (CH₂)₂O-cHx H H
1-2480 COC_ThreeH₇ H H H Me 2 -C≡C- (CH₂)₂O-cHx H H
1-2481 COC_FourH₉ H H H Me 2 -C≡C- (CH₂)₂O-cHx H H
1-2482 COC_FiveH₁₁ H H H Me 2 -C≡C- (CH₂)₂O-cHx H H
1-2483 COC₆H₁₃ H H H Me 2 -C≡C- (CH₂)₂O-cHx H H
1-2484 COC₇H₁₅ H H H Me 2 -C≡C- (CH₂)₂O-cHx H H
1-2485 COC₈H₁₇ H H H Me 2 -C≡C- (CH₂)₂O-cHx H H
1-2486 COCH_Three  H H H Me 2 -C≡C- (CH₂)₂O-Ph H H
1-2487 COC₂H_Five H H H Me 2 -C≡C- (CH₂)₂O-Ph H H
1-2488 COC_ThreeH₇ H H H Me 2 -C≡C- (CH₂)₂O-Ph H H
1-2489 COC_FourH₉ H H H Me 2 -C≡C- (CH₂)₂O-Ph H H
1-2490 COC_FiveH₁₁ H H H Me 2 -C≡C- (CH₂)₂O-Ph H H
1-2491 COC₆H₁₃ H H H Me 2 -C≡C- (CH₂)₂O-Ph H H
1-2492 COC₇H₁₅ H H H Me 2 -C≡C- (CH₂)₂O-Ph H H
1-2493 COC₈H₁₇ H H H Me 2 -C≡C- (CH₂)₂O-Ph H H
1-2494 COCH_Three  H H H Me 2 -CO- (CH₂)_Three-cHx H H
1-2495 COC₂H_Five H H H Me 2 -CO- (CH₂)_Three-cHx H H
1-2496 COC_ThreeH₇ H H H Me 2 -CO- (CH₂)_Three-cHx H H
1-2497 COC_FourH₉ H H H Me 2 -CO- (CH₂)_Three-cHx H H
1-2498 COC_FiveH₁₁ H H H Me 2 -CO- (CH₂)_Three-cHx H H
1-2499 COC₆H₁₃ H H H Me 2 -CO- (CH₂)_Three-cHx H H
1-2500 COC₇H₁₅ H H H Me 2 -CO- (CH₂)_Three-cHx H H
1-2501 COC₈H₁₇ H H H Me 2 -CO- (CH₂)_Three-cHx H H
1-2502 COCH_Three  H H H Me 2 -CO- (CH₂)_Three-Ph H H
1-2503 COC₂H_Five H H H Me 2 -CO- (CH₂)_Three-Ph H H
1-2504 COC_ThreeH₇ H H H Me 2 -CO- (CH₂)_Three-Ph H H
1-2505 COC_FourH₉ H H H Me 2 -CO- (CH₂)_Three-Ph H H
1-2506 COC_FiveH₁₁ H H H Me 2 -CO- (CH₂)_Three-Ph H H
1-2507 COC₆H₁₃ H H H Me 2 -CO- (CH₂)_Three-Ph H H
1-2508 COC₇H₁₅ H H H Me 2 -CO- (CH₂)_Three-Ph H H
1-2509 COC₈H₁₇ H H H Me 2 -CO- (CH₂)_Three-Ph H H
1-2510 COCH_Three  H H H Me 2 -CO- (CH₂)_Four-cHx H H
1-2511 COC₂H_Five H H H Me 2 -CO- (CH₂)_Four-cHx H H
1-2512 COC_ThreeH₇ H H H Me 2 -CO- (CH₂)_Four-cHx H H
1-2513 COC_FourH₉ H H H Me 2 -CO- (CH₂)_Four-cHx H H
1-2514 COC_FiveH₁₁ H H H Me 2 -CO- (CH₂)_Four-cHx H H
1-2515 COC₆H₁₃ H H H Me 2 -CO- (CH₂)_Four-cHx H H
1-2516 COC₇H₁₅ H H H Me 2 -CO- (CH₂)_Four-cHx H H
1-2517 COC₈H₁₇ H H H Me 2 -CO- (CH₂)_Four-cHx H H
1-2518 COCH_Three  H H H Me 2 -CO- (CH₂)_Four-Ph H H
1-2519 COC₂H_Five H H H Me 2 -CO- (CH₂)_Four-Ph H H
1-2520 COC_ThreeH₇ H H H Me 2 -CO- (CH₂)_Four-Ph H H
1-2521 COC_FourH₉ H H H Me 2 -CO- (CH₂)_Four-Ph H H
1-2522 COC_FiveH₁₁ H H H Me 2 -CO- (CH₂)_Four-Ph H H
1-2523 COC₆H₁₃ H H H Me 2 -CO- (CH₂)_Four-Ph H H
1-2524 COC₇H₁₅ H H H Me 2 -CO- (CH₂)_Four-Ph H H
1-2525 COC₈H₁₇ H H H Me 2 -CO- (CH₂)_Four-Ph H H
1-2526 COCH_Three  H H H Me 2 -CO- (CH₂)_Five-cHx H H
1-2527 COC₂H_Five H H H Me 2 -CO- (CH₂)_Five-cHx H H
1-2528 COC_ThreeH₇ H H H Me 2 -CO- (CH₂)_Five-cHx H H
1-2529 COC_FourH₉ H H H Me 2 -CO- (CH₂)_Five-cHx H H
1-2530 COC_FiveH₁₁ H H H Me 2 -CO- (CH₂)_Five-cHx H H
1-2531 COC₆H₁₃ H H H Me 2 -CO- (CH₂)_Five-cHx H H
1-2532 COC₇H₁₅ H H H Me 2 -CO- (CH₂)_Five-cHx H H
1-2533 COC₈H₁₇ H H H Me 2 -CO- (CH₂)_Five-cHx H H
1-2534 COCH_Three  H H H Me 2 -CO- (CH₂)_Five-Ph H H
1-2535 COC₂H_Five H H H Me 2 -CO- (CH₂)_Five-Ph H H
1-2536 COC_ThreeH₇ H H H Me 2 -CO- (CH₂)_Five-Ph H H
1-2537 COC_FourH₉ H H H Me 2 -CO- (CH₂)_Five-Ph H H
1-2538 COC_FiveH₁₁ H H H Me 2 -CO- (CH₂)_Five-Ph H H
1-2539 COC₆H₁₃ H H H Me 2 -CO- (CH₂)_Five-Ph H H
1-2540 COC₇H₁₅ H H H Me 2 -CO- (CH₂)_Five-Ph H H
1-2541 COC₈H₁₇ H H H Me 2 -CO- (CH₂)_Five-Ph H H
1-2542 COCH_Three  H H H Me 2 -CH (OH)-(CH₂)_Four-cHx H H
1-2543 COC₂H_Five H H H Me 2 -CH (OH)-(CH₂)_Four-cHx H H
1-2544 COC_ThreeH₇ H H H Me 2 -CH (OH)-(CH₂)_Four-cHx H H
1-2545 COC_FourH₉ H H H Me 2 -CH (OH)-(CH₂)_Four-cHx H H
1-2546 COC_FiveH₁₁ H H H Me 2 -CH (OH)-(CH₂)_Four-cHx H H
1-2547 COC₆H₁₃ H H H Me 2 -CH (OH)-(CH₂)_Four-cHx H H
1-2548 COC₇H₁₅ H H H Me 2 -CH (OH)-(CH₂)_Four-cHx H H
1-2549 COC₈H₁₇ H H H Me 2 -CH (OH)-(CH₂)_Four-cHx H H
1-2550 COCH_Three  H H H Me 2 -CH (OH)-(CH₂)_Four-Ph H H
1-2551 COC₂H_Five H H H Me 2 -CH (OH)-(CH₂)_Four-Ph H H
1-2552 COC_ThreeH₇ H H H Me 2 -CH (OH)-(CH₂)_Four-Ph H H
1-2553 COC_FourH₉ H H H Me 2 -CH (OH)-(CH₂)_Four-Ph H H
1-2554 COC_FiveH₁₁ H H H Me 2 -CH (OH)-(CH₂)_Four-Ph H H
1-2555 COC₆H₁₃ H H H Me 2 -CH (OH)-(CH₂)_Four-Ph H H
1-2556 COC₇H₁₅ H H H Me 2 -CH (OH)-(CH₂)_Four-Ph H H
1-2557 COC₈H₁₇ H H H Me 2 -CH (OH)-(CH₂)_Four-Ph H H
――――――――――――――――――――――――――――――――――――
Table 2
[0063]
[Chemical 8]

[0064]
[Table 2]
――――――――――――――――――――――――――――――――――――
Compd. R¹    R²  R^Three  R_a ^Three  R^Four   n -X-Y-R^Five                     R⁶  R⁷
――――――――――――――――――――――――――――――――――――
2-1 H H H H Me 1-(CH₂)_Five-cHx H H
2-2 H H H H Me 1-(CH₂)₆-cHx H H
2-3 H H H H Me 1 -C≡C- (CH₂)_Three-cHx H H
2-4 H H H H Me 1 -C≡C- (CH₂)_Four-cHx H H
2-5 H H H H Me 1 -4- (cHx-CH₂O) Ph H H
2-6 H H H H Me 1-(4-BzO-Ph) H H
2-7 H H H H Me 1 -C≡C- (CH₂)₂O-cHx H H
2-8 H H H H Me 1 -C≡C- (CH₂)₂O-Ph H H
2-9 H H H H Me 2-(CH₂)_Three-cHx H H
2-10 H H H H Me 2-(CH₂)_Three-Ph H H
2-11 H H H H Me 2-(CH₂)_Four-cHx H H
2-12 H H H H Me 2-(CH₂)_Four-Ph H H
2-13 H H H H Me 2-(CH₂)_Five-cPn H H
2-14 H H H H Me 2-(CH₂)_Five-cHx H H
2-15 H H H H Me 2-(CH₂)_Five-cHx Me H
2-16 H H H H Me 2-(CH₂)_Five-cHx H Me
2-17 H H H H Me 2-(CH₂)_Five-cHx F H
2-18 H H H H Me 2-(CH₂)_Five-cHx H F
2-19 H H Me Me Me 2-(CH₂)_Five-cHx H H
2-20 CO₂Me H H H Me 2-(CH₂)_Five-cHx H H
2-21 CO₂Et H H H Me 2-(CH₂)_Five-cHx H H
2-22 H H H H Me 2-(CH₂)_Five-(4-F-cHx) H H
2-23 H H H H Me 2-(CH₂)_Five-(4-Cl-cHx) H H
2-24 H H H H Me 2-(CH₂)_Five-(4-Br-cHx) H H
2-25 H H H H Me 2-(CH₂)_Five-(4-Me-cHx) H H
2-26 H H H H Me 2-(CH₂)_Five-(4-Et-cHx) H H
2-27 H H H H Me 2-(CH₂)_Five-(4-Pr-cHx) H H
2-28 H H H H Me 2-(CH₂)_Five-(4-iPr-cHx) H H
2-29 H H H H Me 2-(CH₂)_Five-(4-CF_Three-cHx) H H
2-30 H H H H Me 2-(CH₂)_Five-(4-MeO-cHx) H H
2-31 H H H H Me 2-(CH₂)_Five-(4-EtO-cHx) H H
2-32 H H H H Me 2-(CH₂)_Five-(4-PrO-cHx) H H
2-33 H H H H Me 2-(CH₂)_Five-(4-iPrO-cHx) H H
2-34 H H H H Me 2-(CH₂)_Five-(3-MeS-cHx) H H
2-35 H H H H Me 2-(CH₂)_Five-(4-MeS-cHx) H H
2-36 H H H H Me 2-(CH₂)_Five-(2,4-diMe-cHx) H H
2-37 H H H H Me 2-(CH₂)_Five-(3,4-diMe-cHx) H H
2-38 H H H H Me 2-(CH₂)_Five-(3,5-diMe-cHx) H H
2-39 H H H H Me 2-(CH₂)_Five-Ph H H
2-40 H H H H Me 2-(CH₂)_Five-Ph Me H
2-41 H H H H Me 2-(CH₂)_Five-Ph H Me
2-42 H H H H Me 2-(CH₂)_Five-Ph F H
2-43 H H H H Me 2-(CH₂)_Five-Ph H F
2-44 H H Me Me Me 2-(CH₂)_Five-Ph H H
2-45 CO₂Me H H H Me 2-(CH₂)_Five-Ph H H
2-46 CO₂Et H H H Me 2-(CH₂)_Five-Ph H H
2-47 H H H H Me 2-(CH₂)_Five-(4-F-Ph) H H
2-48 H H H H Me 2-(CH₂)_Five-(4-Cl-Ph) H H
2-49 H H H H Me 2-(CH₂)_Five-(4-Br-Ph) H H
2-50 H H H H Me 2-(CH₂)_Five-(4-Me-Ph) H H
2-51 H H H H Me 2-(CH₂)_Five-(4-Et-Ph) H H
2-52 H H H H Me 2-(CH₂)_Five-(4-Pr-Ph) H H
2-53 H H H H Me 2-(CH₂)_Five-(4-iPr-Ph) H H
2-54 H H H H Me 2-(CH₂)_Five-(4-Bu-Ph) H H
2-55 H H H H Me 2-(CH₂)_Five-(4-CF_Three-Ph) H H
2-56 H H H H Me 2-(CH₂)_Five-(4-MeO-Ph) H H
2-57 H H H H Me 2-(CH₂)_Five-(4-EtO-Ph) H H
2-58 H H H H Me 2-(CH₂)_Five-(4-PrO-Ph) H H
2-59 H H H H Me 2-(CH₂)_Five-(4-iPrO-Ph) H H
2-60 H H H H Me 2-(CH₂)_Five-(3-MeS-Ph) H H
2-61 H H H H Me 2-(CH₂)_Five-(4-MeS-Ph) H H
2-62 H H H H Me 2-(CH₂)_Five-(2,4-diMe-Ph) H H
2-63 H H H H Me 2-(CH₂)_Five-(3,4-diMe-Ph) H H
2-64 H H H H Me 2-(CH₂)_Five-(3,5-diMe-Ph) H H
2-65 H H H H Me 2-(CH₂)₆-cPn H H
2-66 H H H H Me 2-(CH₂)₆-cHx H H
2-67 H H H H Me 2-(CH₂)₆-cHx Me H
2-68 H H H H Me 2-(CH₂)₆-cHx H Me
2-69 H H H H Me 2-(CH₂)₆-cHx F H
2-70 H H H H Me 2-(CH₂)₆-cHx H F
2-71 H H Me Me Me 2-(CH₂)₆-cHx H H
2-72 CO₂Me H H H Me 2-(CH₂)₆-cHx H H
2-73 CO₂Et H H H Me 2-(CH₂)₆-cHx H H
2-74 H H H H Me 2-(CH₂)₆-(4-F-cHx) H H
2-75 H H H H Me 2-(CH₂)₆-(4-Cl-cHx) H H
2-76 H H H H Me 2-(CH₂)₆-(4-Br-cHx) H H
2-77 H H H H Me 2-(CH₂)₆-(4-Me-cHx) H H
2-78 H H H H Me 2-(CH₂)₆-(4-Et-cHx) H H
2-79 H H H H Me 2-(CH₂)₆-(4-Pr-cHx) H H
2-80 H H H H Me 2-(CH₂)₆-(4-iPr-cHx) H H
2-81 H H H H Me 2-(CH₂)₆-(4-Bu-cHx) H H
2-82 H H H H Me 2-(CH₂)₆-(4-CF_Three-cHx) H H
2-83 H H H H Me 2-(CH₂)₆-(4-MeO-cHx) H H
2-84 H H H H Me 2-(CH₂)₆-(4-EtO-cHx) H H
2-85 H H H H Me 2-(CH₂)₆-(4-PrO-cHx) H H
2-86 H H H H Me 2-(CH₂)₆-(4-iPrO-cHx) H H
2-87 H H H H Me 2-(CH₂)₆-(3-MeS-cHx) H H
2-88 H H H H Me 2-(CH₂)₆-(4-MeS-cHx) H H
2-89 H H H H Me 2-(CH₂)₆-(2,4-diMe-cHx) H H
2-90 H H H H Me 2-(CH₂)₆-(3,4-diMe-cHx) H H
2-91 H H H H Me 2-(CH₂)₆-(3,5-diMe-cHx) H H
2-92 H H H H Me 2-(CH₂)₆-Ph H H
2-93 H H H H Me 2-(CH₂)₆-Ph Me H
2-94 H H H H Me 2-(CH₂)₆-Ph H Me
2-95 H H H H Me 2-(CH₂)₆-Ph F H
2-96 H H H H Me 2-(CH₂)₆-Ph H F
2-97 H H Me Me Me 2-(CH₂)₆-Ph H H
2-98 CO₂Me H H H Me 2-(CH₂)₆-Ph H H
2-99 CO₂Et H H H Me 2-(CH₂)₆-Ph H H
2-100 H H H H Me 2-(CH₂)₆-(4-F-Ph) H H
2-101 H H H H Me 2-(CH₂)₆-(4-Cl-Ph) H H
2-102 H H H H Me 2-(CH₂)₆-(4-Br-Ph) H H
2-103 H H H H Me 2-(CH₂)₆-(4-Me-Ph) H H
2-104 H H H H Me 2-(CH₂)₆-(4-Et-Ph) H H
2-105 H H H H Me 2-(CH₂)₆-(4-Pr-Ph) H H
2-106 H H H H Me 2-(CH₂)₆-(4-iPr-Ph) H H
2-107 H H H H Me 2-(CH₂)₆-(4-Bu-Ph) H H
2-108 H H H H Me 2-(CH₂)₆-(4-CF_Three-Ph) H H
2-109 H H H H Me 2-(CH₂)₆-(4-MeO-Ph) H H
2-110 H H H H Me 2-(CH₂)₆-(4-EtO-Ph) H H
2-111 H H H H Me 2-(CH₂)₆-(4-PrO-Ph) H H
2-112 H H H H Me 2-(CH₂)₆-(4-iPrO-Ph) H H
2-113 H H H H Me 2-(CH₂)₆-(3-MeS-Ph) H H
2-114 H H H H Me 2-(CH₂)₆-(4-MeS-Ph) H H
2-115 H H H H Me 2-(CH₂)₆-(2,4-diMe-Ph) H H
2-116 H H H H Me 2-(CH₂)₆-(3,4-diMe-Ph) H H
2-117 H H H H Me 2-(CH₂)₆-(3,5-diMe-Ph) H H
2-118 H H H H Me 2-(CH₂)₇-cHx H H
2-119 H H H H Me 2-(CH₂)₇-Ph H H
2-120 H H H H Me 2-(CH₂)₈-cHx H H
2-121 H H H H Me 2-(CH₂)₈-Ph H H
2-122 H H H H Me 2 -CH = CH- (CH₂)_Three-cHx H H
2-123 H H Me Me Me 2 -CH = CH- (CH₂)_Three-cHx H H
2-124 CO₂Me H H H Me 2 -CH = CH- (CH₂)_Three-cHx H H
2-125 CO₂Et H H H Me 2 -CH = CH- (CH₂)_Three-cHx H H
2-126 H H H H Me 2 -CH = CH- (CH₂)_Three-Ph H H
2-127 H H Me Me Me 2 -CH = CH- (CH₂)_Three-Ph H H
2-128 CO₂Me H H H Me 2 -CH = CH- (CH₂)_Three-Ph H H
2-129 CO₂Et H H H Me 2 -CH = CH- (CH₂)_Three-Ph H H
2-130 H H H H Me 2 -CH = CH- (CH₂)_Four-cHx H H
2-131 H H H H Me 2 -CH = CH- (CH₂)_Four-cHx H H
2-132 CO₂Me H H H Me 2 -CH = CH- (CH₂)_Four-cHx H H
2-133 CO₂Et H H H Me 2 -CH = CH- (CH₂)_Four-cHx H H
2-134 H H H H Me 2 -CH = CH- (CH₂)_Four-Ph H H
2-135 H H H H Me 2 -CH = CH- (CH₂)_Four-Ph H H
2-136 CO₂Me H H H Me 2 -CH = CH- (CH₂)_Four-Ph H H
2-137 CO₂Et H H H Me 2 -CH = CH- (CH₂)_Four-Ph H H
2-138 H H H H Me 2 -C = C-CH₂O-cHx H H
2-139 H H H H Me 2 -C = C-CH₂O-Ph H H
2-140 H H H H Me 2 -C = C- (CH₂)₂O-cHx H H
2-141 H H H H Me 2 -C = C- (CH₂)₂O-Ph H H
2-142 H H H H Me 2 -C≡C-CH₂-cHx H H
2-143 H H H H Me 2 -C≡C-CH₂-cHx H H
2-144 CO₂Me H H H Me 2 -C≡C-CH₂-cHx H H
2-145 CO₂Et H H H Me 2 -C≡C-CH₂-cHx H H
2-146 H H H H Me 2 -C≡C-CH₂-Ph H H
2-147 H H Me Me Me 2 -C≡C-CH₂-Ph H H
2-148 CO₂Me H H H Me 2 -C≡C-CH₂-Ph H H
2-149 CO₂Et H H H Me 2 -C≡C-CH₂-Ph H H
2-150 H H H H Me 2 -C≡C- (CH₂)₂-cHx H H
2-151 H H Me Me Me 2 -C≡C- (CH₂)₂-cHx H H
2-152 CO₂Me H H H Me 2 -C≡C- (CH₂)₂-cHx H H
2-153 CO₂Et H H H Me 2 -C≡C- (CH₂)₂-cHx H H
2-154 H H H H Me 2 -C≡C- (CH₂)₂-Ph H H
2-155 H H Me Me Me 2 -C≡C- (CH₂)₂-Ph H H
2-156 CO₂Me H H H Me 2 -C≡C- (CH₂)₂-Ph H H
2-157 CO₂Et H H H Me 2 -C≡C- (CH₂)₂-Ph H H
2-158 H H H H Me 2 -C≡C- (CH₂)_Three-cPn H H
2-159 H H H H Me 2 -C≡C- (CH₂)_Three-cHx H H
2-160 H H H H Me 2 -C≡C- (CH₂)_Three-cHx Me H
2-161 H H H H Me 2 -C≡C- (CH₂)_Three-cHx H Me
2-162 H H H H Me 2 -C≡C- (CH₂)_Three-cHx F H
2-163 H H H H Me 2 -C≡C- (CH₂)_Three-cHx H F
2-164 H H Me Me Me 2 -C≡C- (CH₂)_Three-cHx H H
2-165 CO₂Me H H H Me 2 -C≡C- (CH₂)_Three-cHx H H
2-166 CO₂Et H H H Me 2 -C≡C- (CH₂)_Three-cHx H H
2-167 H H H H Me 2 -C≡C- (CH₂)_Three-(4-F-cHx) H H
2-168 H H H H Me 2 -C≡C- (CH₂)_Three-(4-Cl-cHx) H H
2-169 H H H H Me 2 -C≡C- (CH₂)_Three-(4-Br-cHx) H H
2-170 H H H H Me 2 -C≡C- (CH₂)_Three-(4-Me-cHx) H H
2-171 H H H H Me 2 -C≡C- (CH₂)_Three-(4-Et-cHx) H H
2-172 H H H H Me 2 -C≡C- (CH₂)_Three-(4-Pr-cHx) H H
2-173 H H H H Me 2 -C≡C- (CH₂)_Three-(4-iPr-cHx) H H
2-174 H H H H Me 2 -C≡C- (CH₂)_Three-(4-Bu-cHx) H H
2-175 H H H H Me 2 -C≡C- (CH₂)_Three-(4-CF_Three-cHx) H H
2-176 H H H H Me 2 -C≡C- (CH₂)_Three-(4-MeO-cHx) H H
2-177 H H H H Me 2 -C≡C- (CH₂)_Three-(4-EtO-cHx) H H
2-178 H H H H Me 2 -C≡C- (CH₂)_Three-(4-PrO-cHx) H H
2-179 H H H H Me 2 -C≡C- (CH₂)_Three-(4-iPrO-cHx) H H
2-180 H H H H Me 2 -C≡C- (CH₂)_Three-(3-MeS-cHx) H H
2-181 H H H H Me 2 -C≡C- (CH₂)_Three-(4-MeS-cHx) H H
2-182 H H H H Me 2 -C≡C- (CH₂)_Three-(2,4-diMe-cHx) H H
2-183 H H H H Me 2 -C≡C- (CH₂)_Three-(3,4-diMe-cHx) H H
2-184 H H H H Me 2 -C≡C- (CH₂)_Three-(3,5-diMe-cHx) H H
2-185 H H H H Me 2 -C≡C- (CH₂)_Three-Ph H H
2-186 H H H H Me 2 -C≡C- (CH₂)_Three-Ph Me H
2-187 H H H H Me 2 -C≡C- (CH₂)_Three-Ph H Me
2-188 H H H H Me 2 -C≡C- (CH₂)_Three-Ph F H
2-189 H H H H Me 2 -C≡C- (CH₂)_Three-Ph H F
2-190 H H Me Me Me 2 -C≡C- (CH₂)_Three-Ph H H
2-191 CO₂Me H H H Me 2 -C≡C- (CH₂)_Three-Ph H H
2-192 CO₂Et H H H Me 2 -C≡C- (CH₂)_Three-Ph H H
2-193 H H H H Me 2 -C≡C- (CH₂)_Three-(4-F-Ph) H H
2-194 H H H H Me 2 -C≡C- (CH₂)_Three-(4-Cl-Ph) H H
2-195 H H H H Me 2 -C≡C- (CH₂)_Three-(4-Br-Ph) H H
2-196 H H H H Me 2 -C≡C- (CH₂)_Three-(4-Me-Ph) H H
2-197 H H H H Me 2 -C≡C- (CH₂)_Three-(4-Et-Ph) H H
2-198 H H H H Me 2 -C≡C- (CH₂)_Three-(4-Pr-Ph) H H
2-199 H H H H Me 2 -C≡C- (CH₂)_Three-(4-iPr-Ph) H H
2-200 H H H H Me 2 -C≡C- (CH₂)_Three-(4-Bu-Ph) H H
2-201 H H H H Me 2 -C≡C- (CH₂)_Three-(4-CF_Three-Ph) H H
2-202 H H H H Me 2 -C≡C- (CH₂)_Three-(4-MeO-Ph) H H
2-203 H H H H Me 2 -C≡C- (CH₂)_Three-(4-EtO-Ph) H H
2-204 H H H H Me 2 -C≡C- (CH₂)_Three-(4-PrO-Ph) H H
2-205 H H H H Me 2 -C≡C- (CH₂)_Three-(4-iPrO-Ph) H H
2-206 H H H H Me 2 -C≡C- (CH₂)_Three-(3-MeS-Ph) H H
2-207 H H H H Me 2 -C≡C- (CH₂)_Three-(4-MeS-Ph) H H
2-208 H H H H Me 2 -C≡C- (CH₂)_Three-(2,4-diMe-Ph) H H
2-209 H H H H Me 2 -C≡C- (CH₂)_Three-(3,4-diMe-Ph) H H
2-210 H H H H Me 2 -C≡C- (CH₂)_Three-(3,5-diMe-Ph) H H
2-211 H H H H Me 2 -C≡C- (CH₂)_Four-cPn H H
2-212 H H H H Me 2 -C≡C- (CH₂)_Four-cHx H H
2-213 H H H H Me 2 -C≡C- (CH₂)_Four-cHx Me H
2-214 H H H H Me 2 -C≡C- (CH₂)_Four-cHx H Me
2-215 H H H H Me 2 -C≡C- (CH₂)_Four-cHx F H
2-216 H H H H Me 2 -C≡C- (CH₂)_Four-cHx H F
2-217 H H Me Me Me 2 -C≡C- (CH₂)_Four-cHx H H
2-218 CO₂Me H H H Me 2 -C≡C- (CH₂)_Four-cHx H H
2-219 CO₂Et H H H Me 2 -C≡C- (CH₂)_Four-cHx H H
2-220 H H H H Me 2 -C≡C- (CH₂)_Four-(4-F-cHx) H H
2-221 H H H H Me 2 -C≡C- (CH₂)_Four-(4-Cl-cHx) H H
2-222 H H H H Me 2 -C≡C- (CH₂)_Four-(4-Br-cHx) H H
2-223 H H H H Me 2 -C≡C- (CH₂)_Four-(4-Me-cHx) H H
2-224 H H H H Me 2 -C≡C- (CH₂)_Four-(4-Et-cHx) H H
2-225 H H H H Me 2 -C≡C- (CH₂)_Four-(4-Pr-cHx) H H
2-226 H H H H Me 2 -C≡C- (CH₂)_Four-(4-iPr-cHx) H H
2-227 H H H H Me 2 -C≡C- (CH₂)_Four-(4-Bu-cHx) H H
2-228 H H H H Me 2 -C≡C- (CH₂)_Four-(4-CF_Three-cHx) H H
2-229 H H H H Me 2 -C≡C- (CH₂)_Four-(4-MeO-cHx) H H
2-230 H H H H Me 2 -C≡C- (CH₂)_Four-(4-EtO-cHx) H H
2-231 H H H H Me 2 -C≡C- (CH₂)_Four-(4-PrO-cHx) H H
2-232 H H H H Me 2 -C≡C- (CH₂)_Four-(4-iPrO-cHx) H H
2-233 H H H H Me 2 -C≡C- (CH₂)_Four-(4-MeS-cHx) H H
2-234 H H H H Me 2 -C≡C- (CH₂)_Four-(2,4-diMe-cHx) H H
2-235 H H H H Me 2 -C≡C- (CH₂)_Four-(3,4-diMe-cHx) H H
2-236 H H H H Me 2 -C≡C- (CH₂)_Four-(3,5-diMe-cHx) H H
2-237 H H H H Me 2 -C≡C- (CH₂)_Four-Ph H H
2-238 H H H H Me 2 -C≡C- (CH₂)_Four-Ph Me H
2-239 H H H H Me 2 -C≡C- (CH₂)_Four-Ph H Me
2-240 H H H H Me 2 -C≡C- (CH₂)_Four-Ph F H
2-241 H H H H Me 2 -C≡C- (CH₂)_Four-Ph H F
2-242 H H Me Me Me 2 -C≡C- (CH₂)_Four-Ph H H
2-243 CO₂Me H H H Me 2 -C≡C- (CH₂)_Four-Ph H H
2-244 CO₂Et H H H Me 2 -C≡C- (CH₂)_Four-Ph H H
2-245 H H H H Me 2 -C≡C- (CH₂)_Four-(4-F-Ph) H H
2-246 H H H H Me 2 -C≡C- (CH₂)_Four-(4-Cl-Ph) H H
2-247 H H H H Me 2 -C≡C- (CH₂)_Four-(4-Br-Ph) H H
2-248 H H H H Me 2 -C≡C- (CH₂)_Four-(4-Me-Ph) H H
2-249 H H H H Me 2 -C≡C- (CH₂)_Four-(4-Et-Ph) H H
2-250 H H H H Me 2 -C≡C- (CH₂)_Four-(4-Pr-Ph) H H
2-251 H H H H Me 2 -C≡C- (CH₂)_Four-(4-iPr-Ph) H H
2-252 H H H H Me 2 -C≡C- (CH₂)_Four-(4-Bu-Ph) H H
2-253 H H H H Me 2 -C≡C- (CH₂)_Four-(4-CF_Three-Ph) H H
2-254 H H H H Me 2 -C≡C- (CH₂)_Four-(4-MeO-Ph) H H
2-255 H H H H Me 2 -C≡C- (CH₂)_Four-(4-EtO-Ph) H H
2-256 H H H H Me 2 -C≡C- (CH₂)_Four-(4-PrO-Ph) H H
2-257 H H H H Me 2 -C≡C- (CH₂)_Four-(4-iPrO-Ph) H H
2-258 H H H H Me 2 -C≡C- (CH₂)_Four-(3-MeS-Ph) H H
2-259 H H H H Me 2 -C≡C- (CH₂)_Four-(4-MeS-Ph) H H
2-260 H H H H Me 2 -C≡C- (CH₂)_Four-(2,4-diMe-Ph) H H
2-261 H H H H Me 2 -C≡C- (CH₂)_Four-(3,4-diMe-Ph) H H
2-262 H H H H Me 2 -C≡C- (CH₂)_Four-(3,5-diMe-Ph) H H
2-263 H H H H Me 2 -C≡C- (CH₂)_Five-cHx H H
2-264 H H Me Me Me 2 -C≡C- (CH₂)_Five-cHx H H
2-265 CO₂Me H H H Me 2 -C≡C- (CH₂)_Five-cHx H H
2-266 CO₂Et H H H Me 2 -C≡C- (CH₂)_Five-cHx H H
2-267 H H H H Me 2 -C≡C- (CH₂)_Five-Ph H H
2-268 H H Me Me Me 2 -C≡C- (CH₂)_Five-Ph H H
2-269 CO₂Me H H H Me 2 -C≡C- (CH₂)_Five-Ph H H
2-270 CO₂Et H H H Me 2 -C≡C- (CH₂)_Five-Ph H H
2-271 H H H H Me 2 -C≡C- (CH₂)₆-cHx H H
2-272 H H Me Me Me 2 -C≡C- (CH₂)₆-cHx H H
2-273 CO₂Me H H H Me 2 -C≡C- (CH₂)₆-cHx H H
2-274 CO₂Et H H H Me 2 -C≡C- (CH₂)₆-cHx H H
2-275 H H H H Me 2 -C≡C- (CH₂)₆-Ph H H
2-276 H H Me Me Me 2 -C≡C- (CH₂)₆-Ph H H
2-277 CO₂Me H H H Me 2 -C≡C- (CH₂)₆-Ph H H
2-278 CO₂Et H H H Me 2 -C≡C- (CH₂)₆-Ph H H
2-279 H H H H Me 2 -C≡C-CH₂O-cHx H H
2-280 H H Me Me Me 2 -C≡C-CH₂O-cHx H H
2-281 CO₂Me H H H Me 2 -C≡C-CH₂O-cHx H H
2-282 CO₂Et H H H Me 2 -C≡C-CH₂O-cHx H H
2-283 H H H H Me 2 -C≡C-CH₂O-Ph H H
2-284 H H Me Me Me 2 -C≡C-CH₂O-Ph H H
2-285 CO₂Me H H H Me 2 -C≡C-CH₂O-Ph H H
2-286 CO₂Et H H H Me 2 -C≡C-CH₂O-Ph H H
2-287 H H H H Me 2 -C≡C- (CH₂)₂O-cPn H H
2-288 H H H H Me 2 -C≡C- (CH₂)₂O-cHx H H
2-289 H H H H Me 2 -C≡C- (CH₂)₂O-cHx Me H
2-290 H H H H Me 2 -C≡C- (CH₂)₂O-cHx H Me
2-291 H H H H Me 2 -C≡C- (CH₂)₂O-cHx F H
2-292 H H H H Me 2 -C≡C- (CH₂)₂O-cHx H F
2-293 H H Me Me Me 2 -C≡C- (CH₂)₂-OCH₂-cHx H H
2-294 CO₂Me H H H Me 2 -C≡C- (CH₂)₂O-cHx H H
2-295 CO₂Et H H H Me 2 -C≡C- (CH₂)₂O-cHx H H
2-296 H H H H Me 2 -C≡C- (CH₂)₂O- (4-F-cHx) H H
2-297 H H H H Me 2 -C≡C- (CH₂)₂O- (4-Cl-cHx) H H
2-298 H H H H Me 2 -C≡C- (CH₂)₂O- (4-Br-cHx) H H
2-299 H H H H Me 2 -C≡C- (CH₂)₂O- (4-Me-cHx) H H
2-300 H H H H Me 2 -C≡C- (CH₂)₂O- (4-Et-cHx) H H
2-301 H H H H Me 2 -C≡C- (CH₂)₂O- (4-Pr-cHx) H H
2-302 H H H H Me 2 -C≡C- (CH₂)₂O- (4-iPr-cHx) H H
2-303 H H H H Me 2 -C≡C- (CH₂)₂O- (4-Bu-cHx) H H
2-304 H H H H Me 2 -C≡C- (CH₂)₂O- (4-CF_Three-cHx) H H
2-305 H H H H Me 2 -C≡C- (CH₂)₂O- (4-MeO-cHx) H H
2-306 H H H H Me 2 -C≡C- (CH₂)₂O- (4-EtO-cHx) H H
2-307 H H H H Me 2 -C≡C- (CH₂)₂O- (4-PrO-cHx) H H
2-308 H H H H Me 2 -C≡C- (CH₂)₂O- (4-iPrO-cHx) H H
2-309 H H H H Me 2 -C≡C- (CH₂)₂O- (3-MeS-cHx) H H
2-310 H H H H Me 2 -C≡C- (CH₂)₂O- (4-MeS-cHx) H H
2-311 H H H H Me 2 -C≡C- (CH₂)₂O- (2,4-diMe-cHx) H H
2-312 H H H H Me 2 -C≡C- (CH₂)₂O- (3,4-diMe-cHx) H H
2-313 H H H H Me 2 -C≡C- (CH₂)₂O- (3,5-diMe-cHx) H H
2-314 H H H H Me 2 -C≡C- (CH₂)₂O-Ph H H
2-315 H H H H Me 2 -C≡C- (CH₂)₂O-Ph Me H
2-316 H H H H Me 2 -C≡C- (CH₂)₂O-Ph H Me
2-317 H H H H Me 2 -C≡C- (CH₂)₂O-Ph F H
2-318 H H H H Me 2 -C≡C- (CH₂)₂O-Ph H F
2-319 H H Me Me Me 2 -C≡C- (CH₂)₂-OCH₂-Ph H H
2-320 CO₂Me H H H Me 2 -C≡C- (CH₂)₂O-Ph H H
2-321 CO₂Et H H H Me 2 -C≡C- (CH₂)₂O-Ph H H
2-322 H H H H Me 2 -C≡C- (CH₂)₂O- (4-F-Ph) H H
2-323 H H H H Me 2 -C≡C- (CH₂)₂O- (4-Cl-Ph) H H
2-324 H H H H Me 2 -C≡C- (CH₂)₂O- (4-Br-Ph) H H
2-325 H H H H Me 2 -C≡C- (CH₂)₂O- (4-Me-Ph) H H
2-326 H H H H Me 2 -C≡C- (CH₂)₂O- (4-Et-Ph) H H
2-327 H H H H Me 2 -C≡C- (CH₂)₂O- (4-Pr-Ph) H H
2-328 H H H H Me 2 -C≡C- (CH₂)₂O- (4-iPr-Ph) H H
2-329 H H H H Me 2 -C≡C- (CH₂)₂O- (4-Bu-Ph) H H
2-330 H H H H Me 2 -C≡C- (CH₂)₂O- (4-CF_Three-Ph) H H
2-331 H H H H Me 2 -C≡C- (CH₂)₂O- (4-MeO-Ph) H H
2-332 H H H H Me 2 -C≡C- (CH₂)₂O- (4-EtO-Ph) H H
2-333 H H H H Me 2 -C≡C- (CH₂)₂O- (4-PrO-Ph) H H
2-334 H H H H Me 2 -C≡C- (CH₂)₂O- (4-iPrO-Ph) H H
2-335 H H H H Me 2 -C≡C- (CH₂)₂O- (4-MeS-Ph) H H
2-336 H H H H Me 2 -C≡C- (CH₂)₂O- (2,4-diMe-Ph) H H
2-337 H H H H Me 2 -C≡C- (CH₂)₂O- (3,4-diMe-Ph) H H
2-338 H H H H Me 2 -C≡C- (CH₂)₂O- (3,5-diMe-Ph) H H
2-339 H H H H Me 2 -CO- (CH₂)_Four-cHx H H
2-340 H H Me Me Me 2 -CO- (CH₂)_Four-cHx H H
2-341 CO₂Me H H H Me 2 -CO- (CH₂)_Four-cHx H H
2-342 CO₂Et H H H Me 2 -CO- (CH₂)_Four-cHx H H
2-343 H H H H Me 2 -CO- (CH₂)_Four-Ph H H
2-344 H H Me Me Me 2 -CO- (CH₂)_Four-Ph H H
2-345 CO₂Me H H H Me 2 -CO- (CH₂)_Four-Ph H H
2-346 CO₂Et H H H Me 2 -CO- (CH₂)_Four-Ph H H
2-347 H H H H Me 2 -CO- (CH₂)_Five-cHx H H
2-348 H H Me Me Me 2 -CO- (CH₂)_Five-cHx H H
2-349 CO₂Me H H H Me 2 -CO- (CH₂)_Five-cHx H H
2-350 CO₂Et H H H Me 2 -CO- (CH₂)_Five-cHx H H
2-351 H H H H Me 2 -CO- (CH₂)_Five-Ph H H
2-352 H H Me Me Me 2 -CO- (CH₂)_Five-Ph H H
2-353 CO₂Me H H H Me 2 -CO- (CH₂)_Five-Ph H H
2-354 CO₂Et H H H Me 2 -CO- (CH₂)_Five-Ph H H
2-355 H H H H Me 2 -CH (OH)-(CH₂)_Four-cHx H H
2-356 H H Me Me Me 2 -CH (OH)-(CH₂)_Four-cHx H H
2-357 CO₂Me H H H Me 2 -CH (OH)-(CH₂)_Four-cHx H H
2-358 CO₂Et H H H Me 2 -CH (OH)-(CH₂)_Four-cHx H H
2-359 H H H H Me 2 -CH (OH)-(CH₂)_Four-Ph H H
2-360 H H Me Me Me 2 -CH (OH)-(CH₂)_Four-Ph H H
2-361 CO₂Me H H H Me 2 -CH (OH)-(CH₂)_Four-Ph H H
2-362 CO₂Et H H H Me 2 -CH (OH)-(CH₂)_Four-Ph H H
2-363 H H H H Me 2 -CH (OH)-(CH₂)_Five-cHx H H
2-364 H H Me Me Me 2 -CH (OH)-(CH₂)_Five-cHx H H
2-365 CO₂Me H H H Me 2 -CH (OH)-(CH₂)_Five-cHx H H
2-366 CO₂Et H H H Me 2 -CH (OH)-(CH₂)_Five-cHx H H
2-367 H H H H Me 2 -CH (OH)-(CH₂)_Five-Ph H H
2-368 H H Me Me Me 2 -CH (OH)-(CH₂)_Five-Ph H H
2-369 CO₂Me H H H Me 2 -CH (OH)-(CH₂)_Five-Ph H H
2-370 CO₂Et H H H Me 2 -CH (OH)-(CH₂)_Five-Ph H H
2-371 H H H H Me 2 -4- (cHx-CH₂O) Ph H H
2-372 H H Me Me Me 2 -4- (cHx-CH₂O) Ph H H
2-373 CO₂Me H H H Me 2 -4- (cHx-CH₂O) Ph H H
2-374 CO₂Et H H H Me 2 -4- (cHx-CH₂O) Ph H H
2-375 H H H H Me 2 -4- [cHx- (CH₂)₂O] Ph H H
2-376 H H H H Me 2 -4- [cHx- (CH₂)_ThreeO] Ph H H
2-377 H H H H Me 2-(4-BzO-Ph) H H
2-378 H H Me Me Me 2-(4-BzO-Ph) H H
2-379 CO₂Me H H H Me 2-(4-BzO-Ph) H H
2-380 CO₂Et H H H Me 2-(4-BzO-Ph) H H
2-381 H H H H Me 2-(4-BzO-2-F-Ph) H H
2-382 H H H H Me 2-(4-BzO-3-F-Ph) H H
2-383 H H H H Me 2-(4-BzO-2,3-diF-Ph) H H
2-384 H H H H Me 2-(4-BzO-2-Cl-Ph) H H
2-385 H H H H Me 2-(4-BzO-3-Cl-Ph) H H
2-386 H H H H Me 2-(4-BzO-2,3-diCl-Ph) H H
2-387 H H H H Me 2-(4-BzO-2-Me-Ph) H H
2-388 H H H H Me 2-(4-BzO-3-Me-Ph) H H
2-389 H H H H Me 2-(4-BzO-2,3-diMe-Ph) H H
2-390 H H H H Me 2 -4- [Ph- (CH₂)₂O] -Ph H H
2-391 H H H H Me 2 -4- [Ph- (CH₂)_ThreeO] -Ph H H
2-392 H H H H Et 2-(CH₂)_Five-cHx H H
2-393 H H H H Et 2-(CH₂)₆-cHx H H
2-394 H H H H Et 2 -C≡C- (CH₂)_Three-cHx H H
2-395 H H H H Et 2 -C≡C- (CH₂)_Four-cHx H H
2-396 H H H H Et 2 -4- (cHx-CH₂O) Ph H H
2-397 H H H H Et 2-(4-BzO-Ph) H H
2-398 H H H H Et 2 -C≡C- (CH₂)₂O-cHx H H
2-399 H H H H Et 2 -C≡C- (CH₂)₂O-Ph H H
2-400 H H H H Pr 2-(CH₂)_Five-cHx H H
2-401 H H H H Pr 2-(CH₂)₆-cHx H H
2-402 H H H H Pr 2 -C≡C- (CH₂)_Three-cHx H H
2-403 H H H H Pr 2 -C≡C- (CH₂)_Four-cHx H H
2-404 H H H H Pr 2 -4- (cHx-CH₂O) Ph H H
2-405 H H H H Pr 2-(4-BzO-Ph) H H
2-406 H H H H Pr 2 -C≡C- (CH₂)₂O-cHx H H
2-407 H H H H Pr 2 -C≡C- (CH₂)₂O-Ph H H
2-408 H H H H Me 3-(CH₂)_Five-cHx H H
2-409 H H H H Me 3-(CH₂)₆-cHx H H
2-410 H H H H Me 3 -C≡C- (CH₂)_Three-cHx H H
2-411 H H H H Me 3 -C≡C- (CH₂)_Four-cHx H H
2-412 H H H H Me 3 -4- (cHx-CH₂O) Ph H H
2-413 H H H H Me 3-(4-BzO-Ph) H H
2-414 H H H H Me 3 -C≡C- (CH₂)₂O-cHx H H
2-415 H H H H Me 3 -C≡C- (CH₂)₂O-Ph H H
2-416 COCH_Three  H H H Me 2-(CH₂)_Four-cHx H H
2-417 COC₂H_Five H H H Me 2-(CH₂)_Four-cHx H H
2-418 COC_ThreeH₇ H H H Me 2-(CH₂)_Four-cHx H H
2-419 COC_FourH₉ H H H Me 2-(CH₂)_Four-cHx H H
2-420 COC_FiveH₁₁ H H H Me 2-(CH₂)_Four-cHx H H
2-421 COC₆H₁₃ H H H Me 2-(CH₂)_Four-cHx H H
2-422 COC₇H₁₅ H H H Me 2-(CH₂)_Four-cHx H H
2-423 COC₈H₁₇ H H H Me 2-(CH₂)_Four-cHx H H
2-424 COCH_Three  H H H Me 2-(CH₂)_Four-Ph H H
2-425 COC₂H_Five H H H Me 2-(CH₂)_Four-Ph H H
2-426 COC_ThreeH₇ H H H Me 2-(CH₂)_Four-Ph H H
2-427 COC_FourH₉ H H H Me 2-(CH₂)_Four-Ph H H
2-428 COC_FiveH₁₁ H H H Me 2-(CH₂)_Four-Ph H H
2-429 COC₆H₁₃ H H H Me 2-(CH₂)_Four-Ph H H
2-430 COC₇H₁₅ H H H Me 2-(CH₂)_Four-Ph H H
2-431 COC₈H₁₇ H H H Me 2-(CH₂)_Four-Ph H H
2-432 COCH_Three  H H H Me 2-(CH₂)_Five-cHx H H
2-433 COC₂H_Five H H H Me 2-(CH₂)_Five-cHx H H
2-434 COC_ThreeH₇ H H H Me 2-(CH₂)_Five-cHx H H
2-435 COC_FourH₉ H H H Me 2-(CH₂)_Five-cHx H H
2-436 COC_FiveH₁₁ H H H Me 2-(CH₂)_Five-cHx H H
2-437 COC₆H₁₃ H H H Me 2-(CH₂)_Five-cHx H H
2-438 COC₇H₁₅ H H H Me 2-(CH₂)_Five-cHx H H
2-439 COC₈H₁₇ H H H Me 2-(CH₂)_Five-cHx H H
2-440 COCH_Three  H H H Me 2-(CH₂)_Five-Ph H H
2-441 COC₂H_Five H H H Me 2-(CH₂)_Five-Ph H H
2-442 COC_ThreeH₇ H H H Me 2-(CH₂)_Five-Ph H H
2-443 COC_FourH₉ H H H Me 2-(CH₂)_Five-Ph H H
2-444 COC_FiveH₁₁ H H H Me 2-(CH₂)_Five-Ph H H
2-445 COC₆H₁₃ H H H Me 2-(CH₂)_Five-Ph H H
2-446 COC₇H₁₅ H H H Me 2-(CH₂)_Five-Ph H H
2-447 COC₈H₁₇ H H H Me 2-(CH₂)_Five-Ph H H
2-448 COCH_Three  H H H Me 2 -C≡C- (CH₂)_Three-cHx H H
2-449 COC₂H_Five H H H Me 2 -C≡C- (CH₂)_Three-cHx H H
2-450 COC_ThreeH₇ H H H Me 2 -C≡C- (CH₂)_Three-cHx H H
2-451 COC_FourH₉ H H H Me 2 -C≡C- (CH₂)_Three-cHx H H
2-452 COC_FiveH₁₁ H H H Me 2 -C≡C- (CH₂)_Three-cHx H H
2-453 COC₆H₁₃ H H H Me 2 -C≡C- (CH₂)_Three-cHx H H
2-454 COC₇H₁₅ H H H Me 2 -C≡C- (CH₂)_Three-cHx H H
2-455 COC₈H₁₇ H H H Me 2 -C≡C- (CH₂)_Three-cHx H H
2-456 COCH_Three  H H H Me 2 -C≡C- (CH₂)_Three-Ph H H
2-457 COC₂H_Five H H H Me 2 -C≡C- (CH₂)_Three-Ph H H
2-458 COC_ThreeH₇ H H H Me 2 -C≡C- (CH₂)_Three-Ph H H
2-459 COC_FourH₉ H H H Me 2 -C≡C- (CH₂)_Three-Ph H H
2-460 COC_FiveH₁₁ H H H Me 2 -C≡C- (CH₂)_Three-Ph H H
2-461 COC₆H₁₃ H H H Me 2 -C≡C- (CH₂)_Three-Ph H H
2-462 COC₇H₁₅ H H H Me 2 -C≡C- (CH₂)_Three-Ph H H
2-463 COC₈H₁₇ H H H Me 2 -C≡C- (CH₂)_Three-Ph H H
2-464 COCH_Three  H H H Me 2 -C≡C- (CH₂)_Four-cHx H H
2-465 COC₂H_Five H H H Me 2 -C≡C- (CH₂)_Four-cHx H H
2-466 COC_ThreeH₇ H H H Me 2 -C≡C- (CH₂)_Four-cHx H H
2-467 COC_FourH₉ H H H Me 2 -C≡C- (CH₂)_Four-cHx H H
2-468 COC_FiveH₁₁ H H H Me 2 -C≡C- (CH₂)_Four-cHx H H
2-469 COC₆H₁₃ H H H Me 2 -C≡C- (CH₂)_Four-cHx H H
2-470 COC₇H₁₅ H H H Me 2 -C≡C- (CH₂)_Four-cHx H H
2-471 COC₈H₁₇ H H H Me 2 -C≡C- (CH₂)_Four-cHx H H
2-472 COCH_Three  H H H Me 2 -C≡C- (CH₂)_Four-Ph H H
2-473 COC₂H_Five H H H Me 2 -C≡C- (CH₂)_Four-Ph H H
2-474 COC_ThreeH₇ H H H Me 2 -C≡C- (CH₂)_Four-Ph H H
2-475 COC_FourH₉ H H H Me 2 -C≡C- (CH₂)_Four-Ph H H
2-476 COC_FiveH₁₁ H H H Me 2 -C≡C- (CH₂)_Four-Ph H H
2-477 COC₆H₁₃ H H H Me 2 -C≡C- (CH₂)_Four-Ph H H
2-478 COC₇H₁₅ H H H Me 2 -C≡C- (CH₂)_Four-Ph H H
2-479 COC₈H₁₇ H H H Me 2 -C≡C- (CH₂)_Four-Ph H H
2-480 COCH_Three  H H H Me 2 -C≡C- (CH₂)₂O-cHx H H
2-481 COC₂H_Five H H H Me 2 -C≡C- (CH₂)₂O-cHx H H
2-482 COC_ThreeH₇ H H H Me 2 -C≡C- (CH₂)₂O-cHx H H
2-483 COC_FourH₉ H H H Me 2 -C≡C- (CH₂)₂O-cHx H H
2-484 COC_FiveH₁₁ H H H Me 2 -C≡C- (CH₂)₂O-cHx H H
2-485 COC₆H₁₃ H H H Me 2 -C≡C- (CH₂)₂O-cHx H H
2-486 COC₇H₁₅ H H H Me 2 -C≡C- (CH₂)₂O-cHx H H
2-487 COC₈H₁₇ H H H Me 2 -C≡C- (CH₂)₂O-cHx H H
2-488 COCH_Three  H H H Me 2 -C≡C- (CH₂)₂O-Ph H H
2-489 COC₂H_Five H H H Me 2 -C≡C- (CH₂)₂O-Ph H H
2-490 COC_ThreeH₇ H H H Me 2 -C≡C- (CH₂)₂O-Ph H H
2-491 COC_FourH₉ H H H Me 2 -C≡C- (CH₂)₂O-Ph H H
2-492 COC_FiveH₁₁ H H H Me 2 -C≡C- (CH₂)₂O-Ph H H
2-493 COC₆H₁₃ H H H Me 2 -C≡C- (CH₂)₂O-Ph H H
2-494 COC₇H₁₅ H H H Me 2 -C≡C- (CH₂)₂O-Ph H H
2-495 COC₈H₁₇ H H H Me 2 -C≡C- (CH₂)₂O-Ph H H
2-496 COCH_Three  H H H Me 2 -CO- (CH₂)_Four-cHx H H
2-497 COC₂H_Five H H H Me 2 -CO- (CH₂)_Four-cHx H H
2-498 COC_ThreeH₇ H H H Me 2 -CO- (CH₂)_Four-cHx H H
2-499 COC_FourH₉ H H H Me 2 -CO- (CH₂)_Four-cHx H H
2-500 COC_FiveH₁₁ H H H Me 2 -CO- (CH₂)_Four-cHx H H
2-501 COC₆H₁₃ H H H Me 2 -CO- (CH₂)_Four-cHx H H
2-502 COC₇H₁₅ H H H Me 2 -CO- (CH₂)_Four-cHx H H
2-503 COC₈H₁₇ H H H Me 2 -CO- (CH₂)_Four-cHx H H
2-504 COCH_Three  H H H Me 2 -CO- (CH₂)_Four-Ph H H
2-505 COC₂H_Five H H H Me 2 -CO- (CH₂)_Four-Ph H H
2-506 COC_ThreeH₇ H H H Me 2 -CO- (CH₂)_Four-Ph H H
2-507 COC_FourH₉ H H H Me 2 -CO- (CH₂)_Four-Ph H H
2-508 COC_FiveH₁₁ H H H Me 2 -CO- (CH₂)_Four-Ph H H
2-509 COC₆H₁₃ H H H Me 2 -CO- (CH₂)_Four-Ph H H
2-510 COC₇H₁₅ H H H Me 2 -CO- (CH₂)_Four-Ph H H
2-511 COC₈H₁₇ H H H Me 2 -CO- (CH₂)_Four-Ph H H
――――――――――――――――――――――――――――――――――――
In Table 1 above [Formulas (Ia-1) and (Ia-2)] and Table 2 [(Ib-1) and (Ib-2)],
The compound (I) of the present invention is preferably
Illustrative compound numbers: 1-19, 1-23 to 1-32, 1-36 to 1-45, 1-49 to 1-58, 1-62 to 1-71, 1-75 to 1-84, 1- 88-1-102, 1-106-1-156, 1-160-1-214, 1-218-1-268, 1-272-1-322, 1-325-1-334, 1-338- 1-347, 1-351 ~ 1-360, 1-364 ~ 1-373, 1-377 ~ 1-386, 1-390 ~ 1-404, 1-408 ~ 1-458, 1-462 ~ 1- 513, 1-517 to 1-526, 1-530 to 1-544, 1-548 to 1-598, 1-602 to 1-657, 1-670, 1-674 to 1-683, 1-696, 1-700 to 1-717, 1-721 to 1-730, 1-734 to 1-743, 1-747 to 1-756, 1-760 to 1-774, 1-778 to 1-828, 1- 832 to 1-886, 1-890 to 1-940, 1-944 to 1-993, 1-997 to 1-1006, 1-1010 to 1-1019, 1-1045, 1-1049 to 1-1058, 1-1062 to 1-1076, 1-1080 to 1-1130, 1-1134 to 1-1185, 1-1189 to 1-1198, 1-1202 to 1-1208, 1-1212 to 1-1216, 1- 1220-1-1270, 1-1274-1-1331, 1-1335-1-1344, 1-1348-1-1357, 1-1361-1-1370, 1-1374-1-1387, 1-1391- 1-1400, 1-1404 to 1-1418, 1-1422 to 1-1472, 1-1476 to 1-1527, 1-1531 to 1-1540, 1-1544 to 1-1558, 1-1562 to 1- 1612, 1-1616 to 1-1673, 1-1677 to 1-1686, 1-1690 to 1-1699, 1-1703 to 1-1712, 1-1716 to 1-1729, 1-1733 to 1-1744, 1-17 48 ~ 1-1767, 1-1772 ~ 1-1793, 1-1797 ~ 1-1818, 1-1824 ~ 1-1846, 1-1850 ~ 1-1869, 1-1872, 1-1876, 1-1880, 1-1884, 1-1888 to 1-1892, 1-1896, 1-1900, 1-1908 to 1-1913, 1-1917 to 1-1939, 1-1943 to 1-1966, 1-1970 to 1- 1991, 1-1995 to 1-2013, 1-2017, 1-2021, 1-2025, 1-2029, 1-2033, 1-2037 to 1-2042, 1-2045 to 1-2068, 1-2072 to 1-2089, 1-2093, 1-2097, 1-2101, 1-2105, 1-2109, 1-2113, 1-2117, 1-2121, 1-2125, 1-2129, 1-2133, 1- 2135, 1-2139-1-2158, 1-2161-1-2164, 1-2184-1-2346, 1-2398-1-2557,
2-9 to 2-18, 2-22 to 2-43, 2-47 to 2-70, 2-74 to 2-96, 2-100 to 2-119, 2-142, 2-146, 2- 150, 2-154, 2-158 to 2-163, 2-167 to 2-183, 2-185 to 2-189, 2-193 to 2-216, 2-220 to 2-241, 2-245 to 2-263, 2-267, 2-271, 2-275, 2-279, 2-283, 2-287 to 2-292, 2-296 to 2-318, 2-322 to 2-338, 2- 343, 2-347, 2-351, 2-371, 2-375 to 2-377, 2-381 to 2-407, 2-416 to 2-511,
And more preferably
1-19, 1-32, 1-36 to 1-45, 1-57, 1-62 to 1-71, 1-84, 1-88, 1-97 to 1-100, 1-152 to 1- 154, 1-160 to 1-214, 1-218 to 1-227, 1-264 to 1-268, 1-272 to 1-322, 1-334, 1-347, 1-360, 1-373, 1-386, 1-390 ~ 1-402, 1-454 ~ 1-458, 1-462 ~ 1-513, 1-526, 1-530 ~ 1-542, 1-594 ~ 1-598, 1- 602 to 1-653, 1-743, 1-756, 1-760 to 1-768, 1-770 to 1-774, 1-778 to 1-828, 1-832 to 1-886, 1-890 to 1-940, 1-944 to 1-993, 1-1045, 1-1058, 1-1062 to 1-1074, 1-1126 to 1-1130, 1-1134 to 1-1185, 1-1198, 1- 1202-1-1208, 1-1212, 1-1213, 1-1214, 1-1266-1-1270, 1-1274-1-1331, 1-1344, 1-1348-1-1357, 1-1370, 1-1374-1-1387, 1-1400, 1-1404-1-1416, 1-1468-1-1472, 1-1476-1-1527, 1-1540, 1-1544-1-1556, 1- 1608 to 1-1612, 1-1616 to 1-1666, 1-1729, 1-1742, 1-1744, 1-1759 to 1-1767, 1-1789 to 1-1793, 1-1797 to 1-1818, 1-1842〜1-1846, 1-1900, 1-1908〜1-1913, 1-1935〜1-1939, 1-1943〜1-1966, 1-1987〜1-1991, 1-2013, 1- 2017, 1-2029, 1-2033, 1-2037〜1-2042, 1-2064〜1-2068, 1-2072〜1-2089, 1-2093, 1-2097, 1-2101, 1-2105, 1-2109, 1-2129, 1- 2133, 1-2135, 1-2184〜1-2346, 1-2398〜1-2557,
2-11 to 2-18, 2-39 to 2-43, 2-47 to 2-70, 2-185 to 2-189, 2-193 to 2-216, 2-287 to 2-292, 2- 338, 2-343, 2-347, 2-351, 2-416 to 2-511,
And more preferably
1-45, 1-71, 1-84, 1-88, 1-97 to 1-100, 1-152 to 1-154, 1-160 to 1-206, 1-209 to 1-212, 1- 264 ~ 1-266, 1-334, 1-373, 1-386, 1-390 ~ 1-402, 1-454 ~ 1-458, 1-462 ~ 1-485, 1-509, 1-510, 1-513, 1-526, 1-530 to 1-542, 1-594 to 1-598, 1-602 to 1-613, 1-649, 1-650, 1-743, 1-756, 1- 760 to 1-768, 1-770 to 1-772, 1-824 to 1-828, 1-832 to 1-884, 1-936, 1-1045, 1-1058, 1-1062 to 1-1074, 1-1126-1-1130, 1-1134-1-1145, 1-1148-1-1151, 1-1162, 1-1163, 1-1179-1-1182, 1-1185, 1-1198, 1- 1202-1-1208, 1-1212, 1-1213, 1-1214, 1-1266-1-1270, 1-1274-1-1285, 1-1288-1-1291, 1-1319-1-1322, 1-1329-1-1331, 1-1344, 1-1348-1-1357, 1-1370, 1-1387, 1-1400, 1-1404-1-1416, 1-1468-1-1472, 1- 1476-1-1487, 1-1490-1-1493, 1-1504, 1-1505, 1-1521-1-1524, 1-1527, 1-1540, 1-1544-1-1556, 1-1608- 1-1612, 1-1616 to 1-1627, 1-1663, 1-1664, 1-1729, 1-1742, 1-1744, 1-1761 to 1-1766, 1-1789 to 1-1791, 1- 1815 ~ 1-1818, 1-1900, 1-1909, 1-1962, 1-2064 ~ 1-2066, 1-2089, 1-2093, 1-2097, 1-2105, 1-2133, 1-2216 ~ 1-2288, 1-2 290 ~ 1-2346, 1-2398 ~ 1-2557,
And even more preferred compounds are
Illustrative compound number 1-71 in formula Ia-1: mono 2-amino-2-methyl-4- [5- (4-cyclohexylbutyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-84 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- (4-phenylbutyl) thiophen-2-yl] butyl ester,
Illustrative compound number 1-98 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- (5-cyclohexylpentyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-152 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- (5-phenylpentyl) thiophen-2-yl] butyl ester
Exemplified Compound No. 1-210 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- (6-cyclohexylhexyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-264 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- (6-phenylhexyl) thiophen-2-yl] butyl ester,
Exemplified Compound No. 1-373 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- (3-cyclohexyloxypropyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-386 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- (3-phenoxypropyl) thiophen-2-yl] butyl ester
Illustrative compound number 1-400 in formula Ia-1: mono 2-amino-2-methyl-4- [5- (4-cyclohexyloxybutyl) thiophen-2-yl] butyl ester phosphate
Exemplified Compound No. 1-454 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- (4-phenoxybutyl) thiophen-2-yl] butyl ester
Illustrative compound number 1-509 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- (5-cyclohexyloxypentyl) thiophen-2-yl] butyl ester
Illustrative compound number 1-510 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- (5-phenoxypentyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-513 in formula Ia-1: mono 2-amino-2-methyl-4- [5- (4-cyclohexylmethoxypropyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-743 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- (4-cyclohexylbut-1-ynyl) thiophen-2-yl] butyl ester
Illustrative compound number 1-756 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- (4-phenylbut-1-ynyl) thiophen-2-yl] butyl ester phosphate, illustrative compound number Formula 1-770 in Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- (5-cyclohexylpent-1-ynyl) thiophen-2-yl] butyl ester
Exemplified Compound No. 1-824 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- (5-phenylpent-1-ynyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-882 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- (6-cyclohexylhex-1-ynyl) thiophen-2-yl] butyl ester
Exemplified Compound No. 1-936 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- (6-phenylhex-1-ynyl) thiophen-2-yl] butyl ester phosphate
Exemplified Compound No. 1-1045 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- (3-cyclohexyloxypropynyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number: 1-1058 in Formula Ia-1: mono 2-amino-2-methyl-4- [5- (3-phenoxypropynyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number: 1-1072 in formula Ia-1: mono 2-amino-2-methyl-4- [5- (4-cyclohexyloxybut-1-ynyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-1126 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- (4-phenoxybut-1-ynyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-1181 in formula Ia-1: mono 2-amino-2-methyl-4- [5- (5-cyclohexyloxypent-1-ynyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-1182 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- (5-phenoxypent-1-ynyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-1185 in formula Ia-1: Mono 2-amino-2-methyl-4- [5- (3-cyclohexylmethoxypropynyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-1329 in formula Ia-1: Mono 2-amino-2-methyl-4- [5- (4-cyclohexylbutanoyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-1330 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- (4-phenylbutanoyl) thiophen-2-yl] butyl ester,
Illustrative compound number 1-1331 in formula Ia-1: Mono 2-amino-2-methyl-4- [5- (5-cyclohexylpentanoyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-1344 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- (5-phenylpentanoyl) thiophen-2-yl] butyl ester
Exemplified Compound No. 1-1357 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- (6-cyclohexylhexanoyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-1370 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- (6-phenylhexanoyl) thiophen-2-yl] butyl ester
Exemplified Compound No. 1-1387 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- (3-cyclohexyloxypropanoyl) thiophen-2-yl] butyl ester,
Exemplified Compound No. 1-1400 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- (3-phenoxypropanoyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-1414 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- (4-cyclohexyloxybutanoyl) thiophen-2-yl] butyl ester
Exemplified Compound No. 1-1468 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- (4-phenoxybutanoyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-1523 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- (5-cyclohexyloxypentanoyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-1524 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- (5-phenoxypentanoyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-1527 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- (4-cyclohexylmethoxypropanoyl) thiophen-2-yl] butyl ester of phosphoric acid,
Illustrative compound number 1-1729 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- (4-cyclohexylmethoxyphenyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-1742 in formula Ia-1: Mono 2-amino-2-methyl-4- [5- (4-cyclohexylethoxyphenyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-1744 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- (4-benzyloxyphenyl) thiophen-2-yl] butyl ester
Exemplified Compound No. 1-1761 in Formula Ia-1: Mono 2-amino-2-ethyl-4- [5- (4-cyclohexylbutyl) thiophen-2-yl] butyl ester phosphate
Exemplified Compound No. 1-1764 in Formula Ia-1: Mono 2-amino-2-ethyl-4- [5- (5-cyclohexylpentyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-1816 in Formula Ia-1: Mono 2-amino-2-ethyl-4- [5- (6-cyclohexylhexyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-1900 in formula Ia-1: mono-2-amino-2-ethyl-4- [5- (4-cyclohexylbut-1-ynyl) thiophen-2-yl] butyl ester phosphate
Exemplified Compound No. 1-1909 in Formula Ia-1: Phosphoric acid mono 2-amino-2-ethyl-4- [5- (5-cyclohexylpent-1-ynyl) thiophen-2-yl] butyl ester,
Illustrative compound number 1-1962 in Formula Ia-1: mono 2-amino-2-ethyl-4- [5- (6-cyclohexylhex-1-ynyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-2089 in Formula Ia-1: Mono 2-amino-2-ethyl-4- [5- (4-cyclohexylbutanoyl) thiophen-2-yl] butyl ester phosphate
Exemplified Compound No. 1-2097 in Formula Ia-1: Mono 2-amino-2-ethyl-4- [5- (5-cyclohexylpentanoyl) thiophen-2-yl] butyl ester phosphate
as well as
Illustrative compound number 1-2105 in Formula Ia-1: Mono 2-amino-2-ethyl-4- [5- (6-cyclohexylhexanoyl) thiophen-2-yl] butyl ester phosphate
And
Exemplified Compound No. 1-463 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (4-fluorophenoxy) butyl] thiophen-2-yl] butyl ester
Illustrative compound number 1-479 in formula Ia-1: mono 2-amino-2-methyl-4- [5- [4- (4-methoxyphenoxy) butyl] thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-594 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- (4-benzyloxybutyl) thiophen-2-yl] butyl ester
Illustrative compound number 1-760 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (4-fluorophenyl) but-1-ynyl] thiophen-2-yl] butyl ester,
Illustrative compound number 1-761 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (4-methylphenyl) but-1-ynyl] thiophen-2-yl] butyl ester,
Illustrative compound number 1-762 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (4-ethylphenyl) but-1-ynyl] thiophen-2-yl] butyl ester,
Exemplified Compound No. 1-763 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (4-trifluoromethylphenyl) but-1-ynyl] thiophen-2-yl ] Butyl ester,
Exemplified Compound No. 1-764 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [4- (4-methoxyphenyl) but-1-ynyl] thiophen-2-yl] butyl phosphate ester,
Illustrative compound number 1-765 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (4-ethoxyphenyl) but-1-ynyl] thiophen-2-yl] butyl ester,
Illustrative compound number 1-766 in formula Ia-1: mono 2-amino-2-methyl-4- [5- [4- (4-methylthiophenyl) but-1-ynyl] thiophen-2-yl] butyl phosphate ester,
Illustrative compound number 1-832 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (3-fluorophenyl) pent-1-ynyl] thiophen-2-yl] butyl ester,
Illustrative compound number 1-833 in formula Ia-1: mono 2-amino-2-methyl-4- [5- [5- (4-fluorophenyl) pent-1-ynyl] thiophen-2-yl] butyl phosphate ester,
Illustrative compound number 1-834 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (4-chlorophenyl) pent-1-ynyl] thiophen-2-yl] butyl ester ,
Illustrative compound number: 1-836 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (3-methylphenyl) pent-1-ynyl] thiophen-2-yl] butyl ester,
Exemplified Compound No. 1-837 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (4-methylphenyl) pent-1-ynyl] thiophen-2-yl] butyl ester,
Illustrative compound number 1-846 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (3-trifluoromethylphenyl) pent-1-ynyl] thiophen-2-yl ] Butyl ester,
Illustrative Compound Number 1-847 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (4-trifluorophenyl) pent-1-ynyl] thiophen-2-yl] Butyl ester,
Illustrative compound number 1-848 in formula Ia-1: mono 2-amino-2-methyl-4- [5- [5- (3-methoxyphenyl) pent-1-ynyl] thiophen-2-yl] butyl phosphate ester,
Illustrative compound number 1-849 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (4-methoxyphenyl) pent-1-ynyl] thiophen-2-yl] butyl ester,
Illustrative compound number 1-860 in formula Ia-1: Mono 2-amino-2-methyl-4- [5- [5- (3-methylthiophenyl) pent-1-ynyl] thiophen-2-yl] butyl phosphate ester,
Illustrative compound number 1-861 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (4-methylphenyl) pent-1-ynyl] thiophen-2-yl] butyl ester,
Illustrative compound number 1-877 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [5- (3,4-dimethylphenyl) pent-1-ynyl] thiophen-2-yl phosphate ] Butyl ester,
Illustrative compound number 1-878 in formula Ia-1: mono 2-amino-2-methyl-4- [5- [5- (3,5-dimethylphenyl) pent-1-ynyl] thiophen-2-yl phosphate ] Butyl ester,
Illustrative compound number 1-1050 in formula Ia-1: mono 2-amino-2-methyl-4- [5- [3- (4-methylcyclohexyloxy) propynyl] thiophen-2-yl] butyl ester phosphate
Exemplified Compound No. 1-1062 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [3- (4-fluorophenoxy) propynyl] thiophen-2-yl] butyl ester phosphate
Illustrative compound number: 1-1063 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (4-methylphenoxy) propynyl] thiophen-2-yl] butyl ester
Exemplified Compound No. 1-1064 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (4-ethylphenoxy) propynyl] thiophen-2-yl] butyl ester,
Exemplified Compound No. 1-1065 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (4-trifluoromethylphenoxy) propynyl] thiophen-2-yl] butyl ester,
Exemplified Compound No. 1-1066 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (4-methoxyphenoxy) propynyl] thiophen-2-yl] butyl ester,
Exemplified Compound No. 1-1067 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (4-ethoxyphenoxy) propynyl] thiophen-2-yl] butyl ester,
Illustrative compound number 1-1068 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (4-methylthiophenoxy) propynyl] thiophen-2-yl] butyl ester,
Illustrative Compound Number 1-1134 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [4- (3-fluorophenoxy) but-1-ynyl] thiophen-2-yl] butyl phosphate ester,
Illustrative Compound Number 1-1135 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [4- (4-fluorophenoxy) but-1-ynyl] thiophen-2-yl] butyl phosphate ester,
Illustrative Compound Number 1-1136 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [4- (4-chlorophenoxy) but-1-ynyl] thiophen-2-yl] butyl phosphate ester,
Illustrative compound number 1-1138 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (3-methylphenoxy) but-1-ynyl] thiophen-2-yl] butyl ester,
Illustrative Compound Number 1-1139 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [4- (4-methylphenoxy) but-1-ynyl] thiophen-2-yl] butyl phosphate ester,
Exemplified Compound No. 1-1148 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (3-trifluoromethylphenoxy) but-1-ynyl] thiophen-2-yl ] Butyl ester,
Illustrative compound number 1-1149 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (4-trifluoromethylphenoxy) but-1-ynyl] thiophen-2-yl ] Butyl ester,
Illustrative Compound Number 1-1150 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [4- (3-methoxyphenoxy) but-1-ynyl] thiophen-2-yl] butyl phosphate ester,
Illustrative Compound Number 1-1151 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [4- (4-methoxyphenoxy) but-1-ynyl] thiophen-2-yl] butyl phosphate ester,
Illustrative compound number 1-1162 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [4- (3-methylthiophenoxy) but-1-ynyl] thiophen-2-yl] butyl phosphate ester,
Illustrative compound number 1-1163 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (4-methylthiophenoxy) but-1-ynyl] thiophen-2-yl] butyl ester,
Illustrative Compound Number 1-1179 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [4- (3,4-dimethylphenoxy) but-1-ynyl] thiophen-2-yl phosphate ] Butyl ester,
Illustrative compound number 1-1180 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (3,5-dimethylphenoxy) but-1-ynyl] thiophen-2-yl ] Butyl ester,
Illustrative compound number 1-1198 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- (3-phenylmethoxypropynyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-1202 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [3- (4-fluorophenyl) methoxypropynyl] thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-1203 in formula Ia-1: mono 2-amino-2-methyl-4- [5- [3- (4-methylphenyl) methoxypropynyl] thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-1204 in formula Ia-1: mono 2-amino-2-methyl-4- [5- [3- (4-ethylphenyl) methoxypropynyl] thiophen-2-yl] butyl ester phosphate
Illustrative Compound Number 1-1205 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [3- (4-trifluoromethylphenyl) methoxypropynyl] thiophen-2-yl] butyl ester phosphate ,
Illustrative compound number 1-1206 in formula Ia-1: mono 2-amino-2-methyl-4- [5- [3- (4-methoxyphenyl) methoxypropynyl] thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-1207 in formula Ia-1: mono 2-amino-2-methyl-4- [5- [3- (4-ethoxyphenyl) methoxypropynyl] thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-1208 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (4-methylthiophenyl) methoxypropynyl] thiophen-2-yl] butyl ester,
Illustrative compound number 1-1212 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- (4-cyclohexylmethoxybut-1-ynyl) thiophen-2-yl] butyl ester,
Illustrative compound number 1-1266 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- (4-phenylmethoxybut-1-ynyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-1274 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [4- (3-fluorophenyl) methoxybut-1-ynyl] thiophen-2-yl] butyl phosphate ester,
Illustrative compound number 1-1275 in formula Ia-1: Mono 2-amino-2-methyl-4- [5- [4- (4-fluorophenyl) methoxybut-1-ynyl] thiophen-2-yl] butyl phosphate ester,
Illustrative compound number 1-1276 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (4-chlorophenyl) methoxybut-1-ynyl] thiophen-2-yl] butyl ester ,
Illustrative Compound Number 1-1278 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [4- (3-methylphenyl) methoxybut-1-ynyl] thiophen-2-yl] butyl phosphate ester,
Illustrative compound number 1-1279 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (4-methylphenyl) methoxybut-1-ynyl] thiophen-2-yl] butyl ester,
Illustrative Compound Number 1-1288 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (3-trifluoromethylphenyl) methoxybut-1-ynyl] thiophen-2-yl ] Butyl ester,
Illustrative compound number 1-1289 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (4-trifluoromethylphenyl) methoxybut-1-ynyl] thiophen-2-yl ] Butyl ester,
Exemplified Compound No. 1-1290 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [4- (3-methoxyphenyl) methoxybut-1-ynyl] thiophen-2-yl] butyl phosphate ester,
Illustrative compound number 1-1291 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (4-methoxyphenyl) methoxybut-1-ynyl] thiophen-2-yl] butyl ester,
Illustrative compound number 1-1319 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (3,4-dimethylphenyl) methoxybut-1-ynyl] thiophen-2-yl ] Butyl ester,
Exemplified Compound No. 1-1320 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (3,5-dimethylphenyl) methoxybut-1-ynyl] thiophen-2-yl ] Butyl ester,
Illustrative compound number 1-1348 in formula Ia-1: mono 2-amino-2-methyl-4- [5- [5- (4-fluorophenyl) pentanoyl] thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-1349 in formula Ia-1: mono 2-amino-2-methyl-4- [5- [5- (4-methylphenyl) pentanoyl] thiophen-2-yl] butyl ester phosphate
Exemplified Compound No. 1-1350 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (4-ethylphenyl) pentanoyl] thiophen-2-yl] butyl ester
Exemplified Compound No. 1-1351 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (4-trifluoromethylphenyl) pentanoyl] thiophen-2-yl] butyl ester
Illustrative compound number 1-1352 in formula Ia-1: mono-2-amino-2-methyl-4- [5- [5- (4-methoxyphenyl) pentanoyl] thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-1353 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (4-ethoxyphenyl) pentanoyl] thiophen-2-yl] butyl ester,
Illustrative compound number 1-1354 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [5- (4-methylthiophenyl) pentanoyl] thiophen-2-yl] butyl ester of phosphoric acid,
Illustrative compound number 1-1476 in formula Ia-1: mono 2-amino-2-methyl-4- [5- [4- (3-fluorophenoxy) butanoyl] thiophen-2-yl] butyl ester of phosphoric acid,
Illustrative compound number 1-1477 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (4-fluorophenoxy) butanoyl] thiophen-2-yl] butyl ester,
Illustrative compound number 1-1478 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (4-chlorophenoxy) butanoyl] thiophen-2-yl] butyl ester,
Exemplified Compound No. 1-1480 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (3-methylphenoxy) butanoyl] thiophen-2-yl] butyl ester,
Exemplified Compound No. 1-1481 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (4-methylphenoxy) butanoyl] thiophen-2-yl] butyl ester
Exemplified Compound No. 1-1490 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [4- (3-trifluoromethylphenoxy) butanoyl] thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-1491 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [4- (4-trifluoromethylphenoxy) butanoyl] thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-1492 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [4- (3-methoxyphenoxy) butanoyl] thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-1493 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (4-methoxyphenoxy) butanoyl] thiophen-2-yl] butyl ester,
Illustrative compound number 1-1504 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (3-methylthiophenoxy) butanoyl] thiophen-2-yl] butyl ester
Illustrative compound number 1-1505 in formula Ia-1: mono 2-amino-2-methyl-4- [5- [4- (4-methylthiophenoxy) butanoyl] thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-1521 in formula Ia-1: mono 2-amino-2-methyl-4- [5- [4- (3,4-dimethylphenoxy) butanoyl] thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-1522 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [4- (3,5-dimethylphenoxy) butanoyl] thiophen-2-yl] butyl ester phosphate
Exemplified Compound No. 1-2093 in Formula Ia-1: Phosphoric acid mono 2-amino-ethyl-4- [5- (4-phenylbutanoyl) thiophen-2-yl] butyl ester,
Illustrative compound number 1-2101 in Formula Ia-1: Phosphoric acid mono 2-amino-ethyl-4- [5- (5-phenylpentanoyl) thiophen-2-yl] butyl ester
Illustrative compound number 1-2109 in Formula Ia-1: Mono 2-amino-ethyl-4- [5- (6-phenylhexanoyl) thiophen-2-yl] butyl ester phosphate
Exemplified Compound No. 1-2257 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [5- (3,4-difluorophenyl) pent-1-ynyl] thiophen-2-yl phosphate ] Butyl ester,
Exemplified compound number 1-2258 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (3,5-difluorophenyl) pent-1-ynyl] thiophen-2-yl ] Butyl ester,
Illustrative compound number 1-2259 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (3-chlorophenyl) pent-1-ynyl] thiophen-2-yl] butyl ester ,
Exemplified Compound No. 1-2260 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (3,4-dichlorophenyl) pent-1-ynyl] thiophen-2-yl] Butyl ester,
Illustrative compound number 1-2261 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (3,5-dichlorophenyl) pent-1-ynyl] thiophen-2-yl] Butyl ester,
Illustrative compound number 1-2262 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (3,4-ditrifluoromethylphenyl) pent-1-ynyl] thiophene-2 -Il] butyl ester,
Illustrative Compound Number 1-2263 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (3,5-ditrifluoromethylphenyl) pent-1-ynyl] thiophene-2 -Il] butyl ester,
Exemplified Compound No. 1-2264 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [5- (3,4-dimethoxyphenyl) pent-1-ynyl] thiophen-2-yl phosphate ] Butyl ester,
Illustrative compound number 1-2265 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (3,5-dimethoxyphenyl) pent-1-ynyl] thiophen-2-yl ] Butyl ester,
Exemplified Compound No. 1-2266 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (3,4,5-trimethoxyphenyl) pent-1-ynyl] thiophene- 2-yl] butyl ester,
Illustrative compound number 1-2267 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (3-acetylphenyl) pent-1-ynyl] thiophen-2-yl] butyl ester,
Illustrative compound number: 1-2268 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (4-acetylphenyl) pent-1-ynyl] thiophen-2-yl] butyl ester,
Exemplified Compound No. 1-2269 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (3-fluorophenoxy) propynyl] thiophen-2-yl] butyl ester,
Exemplified Compound No. 1-2270 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [3- (3,4-difluorophenoxy) propynyl] thiophen-2-yl] butyl ester phosphate
Exemplified Compound No. 1-2271 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (3,5-difluorophenoxy) propynyl] thiophen-2-yl] butyl ester,
Exemplified Compound No. 1-2272 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [3- (3-chlorophenoxy) propynyl] thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-2273 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (4-chlorophenoxy) propynyl] thiophen-2-yl] butyl ester,
Exemplified Compound No. 1-2274 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [3- (3,4-dichlorophenoxy) propynyl] thiophen-2-yl] butyl ester phosphate
Exemplified Compound No. 1-2275 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [3- (3,5-dichlorophenoxy) propynyl] thiophen-2-yl] butyl ester phosphate
Exemplified Compound No. 1-2276 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (3-methylphenoxy) propynyl] thiophen-2-yl] butyl ester,
Exemplified Compound No. 1-2278 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [3- (3,4-dimethylphenoxy) propynyl] thiophen-2-yl] butyl ester phosphate
Exemplified Compound No. 1-2279 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (3,5-dimethylphenoxy) propynyl] thiophen-2-yl] butyl ester,
Exemplified Compound No. 1-2280 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (3-trifluoromethylphenoxy) propynyl] thiophen-2-yl] butyl ester,
Illustrative Compound Number 1-2281 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (3,4-ditrifluoromethylphenoxy) propynyl] thiophen-2-yl] butyl ester,
Illustrative Compound Number 1-2282 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (3,5-ditrifluoromethylphenoxy) propynyl] thiophen-2-yl] butyl ester,
Illustrative compound number 1-2283 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (3-methoxyphenoxy) propynyl] thiophen-2-yl] butyl ester,
Exemplified Compound No. 1-2284 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [3- (3,4-dimethoxyphenoxy) propynyl] thiophen-2-yl] butyl ester phosphate
Exemplified Compound No. 1-2285 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (3,5-dimethoxyphenoxy) propynyl] thiophen-2-yl] butyl ester
Exemplified Compound No. 1-2286 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [3- (3,4,5-trimethoxyphenoxy) propynyl] thiophen-2-yl] phosphate Butyl ester,
Exemplified Compound No. 1-2287 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (3-acetylphenoxy) propynyl] thiophen-2-yl] butyl ester,
Illustrative compound number 1-2288 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (4-acetylphenoxy) propynyl] thiophen-2-yl] butyl ester,
Exemplified Compound No. 1-2290 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [4- (3,4-difluorophenoxy) but-1-ynyl] thiophen-2-yl phosphate ] Butyl ester,
Exemplified Compound No. 1-2291 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (3,5-difluorophenoxy) but-1-ynyl] thiophen-2-yl ] Butyl ester,
Illustrative Compound Number 1-2292 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [4- (3-chlorophenoxy) but-1-ynyl] thiophen-2-yl] butyl phosphate ester,
Illustrative compound number 1-2293 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (3,4-dichlorophenoxy) but-1-ynyl] thiophen-2-yl ] Butyl ester,
Exemplified compound number 1-2294 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (3,5-dichlorophenoxy) but-1-ynyl] thiophen-2-yl ] Butyl ester,
Illustrative compound number 1-2295 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (3,4-ditrifluoromethylphenoxy) but-1-ynyl] thiophene-2 -Il] butyl ester,
Illustrative compound number 1-2296 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (3,5-ditrifluoromethylphenoxy) but-1-ynyl] thiophene-2 -Il] butyl ester,
Illustrative compound number 1-2297 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (3,4-dimethoxyphenoxy) but-1-ynyl] thiophen-2-yl ] Butyl ester,
Exemplified Compound No. 1-2298 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (3,5-dimethoxyphenoxy) but-1-ynyl] thiophen-2-yl ] Butyl ester,
Exemplified compound number 1-2299 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (3,4,5-trimethoxyphenoxy) but-1-ynyl] thiophene- 2-yl] butyl ester,
Illustrative compound number: 1-2300 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (3-acetylphenoxy) but-1-ynyl] thiophen-2-yl] butyl ester,
Exemplified Compound No. 1-2301 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [4- (4-acetylphenoxy) but-1-ynyl] thiophen-2-yl] butyl phosphate ester,
Illustrative compound number 1-2328 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (3-fluorophenyl) pentanoyl] thiophen-2-yl] butyl ester,
Illustrative compound number 1-2329 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (3,4-difluorophenyl) pentanoyl] thiophen-2-yl] butyl ester
Illustrative compound number 1-2330 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (3,5-difluorophenyl) pentanoyl] thiophen-2-yl] butyl ester
Exemplified Compound No. 1-2331 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [5- (3-chlorophenyl) pentanoyl] thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-2332 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (4-chlorophenyl) pentanoyl] thiophen-2-yl] butyl ester,
Exemplified Compound No. 1-2333 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (3,4-dichlorophenyl) pentanoyl] thiophen-2-yl] butyl ester,
Illustrative compound number 1-2334 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (3,5-dichlorophenyl) pentanoyl] thiophen-2-yl] butyl ester,
Illustrative compound number 1-2335 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (3-methylphenyl) pentanoyl] thiophen-2-yl] butyl ester
Illustrative compound number 1-2336 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (3,4-dimethylphenyl) pentanoyl] thiophen-2-yl] butyl ester,
Illustrative compound number 1-2337 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (3,5-dimethylphenyl) pentanoyl] thiophen-2-yl] butyl ester,
Illustrative compound number 1-2338 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (3-trifluoromethylphenyl) pentanoyl] thiophen-2-yl] butyl ester,
Illustrative compound number: 1-2339 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (3,4-ditrifluoromethylphenyl) pentanoyl] thiophen-2-yl] butyl ester,
Exemplified Compound No. 1-2340 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (3,5-ditrifluoromethylphenyl) pentanoyl] thiophen-2-yl] butyl ester,
Exemplified Compound No. 1-2341 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (3-methoxyphenyl) pentanoyl] thiophen-2-yl] butyl ester,
Exemplified Compound No. 1-2342 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [5- (3,4-dimethoxyphenyl) pentanoyl] thiophen-2-yl] butyl ester phosphate
Exemplified Compound No. 1-2343 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (3,5-dimethoxyphenyl) pentanoyl] thiophen-2-yl] butyl ester,
Illustrative compound number 1-2344 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (3,4,5-trimethoxyphenyl) pentanoyl] thiophen-2-yl] Butyl ester,
Illustrative compound number 1-2345 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (3-acetylphenyl) pentanoyl] thiophen-2-yl] butyl ester
Exemplified Compound No. 1-2346 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (4-acetylphenyl) pentanoyl] thiophen-2-yl] butyl ester,
Illustrative compound number 1-71 in formula Ia-2: 3-amino-3-methyl-5- [5- (4-cyclohexylbutyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-84 in formula Ia-2: 3-amino-3-methyl-5- [5- (4-phenylbutyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-98 in formula Ia-2: 3-amino-3-methyl-5- [5- (5-cyclohexylpentyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-152 in Formula Ia-2: 3-amino-3-methyl-5- [5- (5-phenylpentyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-210 in formula Ia-2: 3-amino-3-methyl-5- [5- (6-cyclohexylhexyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-264 in formula Ia-2: 3-amino-3-methyl-5- [5- (6-phenylhexyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-373 in Formula Ia-2: 3-amino-3-methyl-5- [5- (3-cyclohexyloxypropyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-386 in formula Ia-2: 3-amino-3-methyl-5- [5- (3-phenoxypropyl) thiophen-2-yl] pentylphosphonic acid,
Exemplified compound number 1-400 in formula Ia-2: 3-amino-3-methyl-5- [5- (4-cyclohexyloxybutyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-454 in formula Ia-2: 3-amino-3-methyl-5- [5- (4-phenoxybutyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-509 in formula Ia-2: 3-amino-3-methyl-5- [5- (5-cyclohexyloxypentyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-510 in formula Ia-2: 3-amino-3-methyl-5- [5- (5-phenoxypentyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-513 in formula Ia-2: 3-amino-3-methyl-5- [5- (4-cyclohexylmethoxypropyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1329 in formula Ia-2: 3-amino-3-methyl-5- [5- (4-cyclohexylbutanoyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1330 in formula Ia-2: 3-amino-3-methyl-5- [5- (4-phenylbutanoyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1331 in formula Ia-2: 3-amino-3-methyl-5- [5- (5-cyclohexylpentanoyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1344 in formula Ia-2: 3-amino-3-methyl-5- [5- (5-phenylpentanoyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1357 in Formula Ia-2: 3-amino-3-methyl-5- [5- (6-cyclohexylhexanoyl) thiophen-2-yl] pentylphosphonic acid,
Exemplified Compound No. 1-1370 in Formula Ia-2: 3-amino-3-methyl-5- [5- (6-phenylhexanoyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1387 in formula Ia-2: 3-amino-3-methyl-5- [5- (3-cyclohexyloxypropanoyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1400 in Formula Ia-2: 3-amino-3-methyl-5- [5- (3-phenoxypropanoyl) thiophen-2-yl] pentylphosphonic acid,
Exemplified Compound No. 1-1414 in Formula Ia-2: 3-amino-3-methyl-5- [5- (4-cyclohexyloxybutanoyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1468 in formula Ia-2: 3-amino-3-methyl-5- [5- (4-phenoxybutanoyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1523 in formula Ia-2: 3-amino-3-methyl-5- [5- (5-cyclohexyloxypentanoyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1524 in formula Ia-2: 3-amino-3-methyl-5- [5- (5-phenoxypentanoyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1527 in formula Ia-2: 3-amino-3-methyl-5- [5- (4-cyclohexylmethoxypropanoyl) thiophen-2-yl] pentylphosphonic acid,
Exemplified Compound No. 1-1729 in Formula Ia-2: 3-amino-3-methyl-5- [5- (4-cyclohexylmethoxyphenyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative Compound Number 1-1742 in Formula Ia-2: 3-amino-3-methyl-5- [5- (4-cyclohexylethoxyphenyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1744 in formula Ia-2: 3-amino-3-methyl-5- [5- (4-benzyloxyphenyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number: 1-1761 in Formula Ia-2: 3-amino-3-ethyl-5- [5- (4-cyclohexylbutyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1764 in Formula Ia-2: 3-amino-3-ethyl-5- [5- (5-cyclohexylpentyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1816 in Formula Ia-2: 3-amino-3-ethyl-5- [5- (6-cyclohexylhexyl) thiophen-2-yl] pentylphosphonic acid,
Exemplified Compound No. 1-2089 in Formula Ia-2: 3-amino-3-ethyl-5- [5- (4-cyclohexylbutanoyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-2097 in Formula Ia-2: 3-amino-3-ethyl-5- [5- (5-cyclohexylpentanoyl) thiophen-2-yl] pentylphosphonic acid, and
Illustrative compound number 1-2105 in formula Ia-2: 3-amino-3-ethyl-5- [5- (6-cyclohexylhexanoyl) thiophen-2-yl] pentylphosphonic acid,
And
Exemplified Compound No. 1-463 in Formula Ia-2: 3-amino-3-methyl-5- [5- [4- (4-fluorophenoxy) butyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-479 in Formula Ia-2: 3-amino-3-methyl-5- [5- [4- (4-methoxyphenoxy) butyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-594 in Formula Ia-2: 3-amino-3-methyl-5- [5- (4-benzyloxybutyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1348 in formula Ia-2: 3-amino-3-methyl-5- [5- [5- (4-fluorophenyl) pentanoyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1349 in formula Ia-2: 3-amino-3-methyl 5- [5- [5- (4-methylphenyl) pentanoyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1350 in formula Ia-2: 3-amino-3-methyl-5- [5- [5- (4-ethylphenyl) pentanoyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1351 in formula Ia-2: 3-amino-3-methyl-5- [5- [5- (4-trifluoromethylphenyl) pentanoyl] thiophen-2-yl] pentylphosphonic acid,
Exemplified Compound No. 1-1352 in Formula Ia-2: 3-amino-3-methyl-5- [5- [5- (4-methoxyphenyl) pentanoyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1353 in formula Ia-2: 3-amino-3-methyl-5- [5- [5- (4-ethoxyphenyl) pentanoyl] thiophen-2-yl] pentylphosphonic acid,
Exemplified Compound No. 1-1354 in Formula Ia-2: 3-amino-3-methyl-5- [5- [5- (4-methylthiophenyl) pentanoyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1476 in formula Ia-2: 3-amino-3-methyl-5- [5- [4- (3-fluorophenoxy) butanoyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1477 in formula Ia-2: 3-amino-3-methyl-5- [5- [4- (4-fluorophenoxy) butanoyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1478 in formula Ia-2: 3-amino-3-methyl-5- [5- [4- (4-chlorophenoxy) butanoyl] thiophen-2-yl] pentylphosphonic acid,
Exemplified Compound No. 1-1480 in Formula Ia-2: 3-amino-3-methyl-5- [5- [4- (3-methylphenoxy) butanoyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1481 in formula Ia-2: 3-amino-3-methyl-5- [5- [4- (4-methylphenoxy) butanoyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1490 in formula Ia-2: 3-amino-3-methyl-5- [5- [4- (3-trifluoromethylphenoxy) butanoyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1491 in formula Ia-2: 3-amino-3-methyl-5- [5- [4- (4-trifluoromethylphenoxy) butanoyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1492 in Formula Ia-2: 3-amino-3-methyl-5- [5- [4- (3-methoxyphenoxy) butanoyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1493 in Formula Ia-2: 3-amino-3-methyl-5- [5- [4- (4-methoxyphenoxy) butanoyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1504 in Formula Ia-2: 3-amino-3-methyl-5- [5- [4- (3-methylthiophenoxy) butanoyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1505 in formula Ia-2: 3-amino-3-methyl-5- [5- [4- (4-methylthiophenoxy) butanoyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1521 in formula Ia-2: 3-amino-3-methyl-5- [5- [4- (3,4-dimethylphenoxy) butanoyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1522 in Formula Ia-2: 3-amino-3-methyl-5- [5- [4- (3,5-dimethylphenoxy) butanoyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-2093 in Formula Ia-2: 3-amino-ethyl-5- [5- (4-phenylbutanoyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-2101 in Formula Ia-2: 3-amino-ethyl-5- [5- (5-phenylpentanoyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-2109 in Formula Ia-2: 3-amino-ethyl-5- [5- (6-phenylhexanoyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-2328 in Formula Ia-2: 3-amino-3-methyl-5- [5- [5- (3-fluorophenyl) pentanoyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-2329 in formula Ia-2: 3-amino-3-methyl-5- [5- [5- (3,4-difluorophenyl) pentanoyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-2330 in formula Ia-2: 3-amino-3-methyl-5- [5- [5- (3,5-difluorophenyl) pentanoyl] thiophen-2-yl] pentylphosphonic acid,
Exemplified Compound No. 1-2331 in Formula Ia-2: 3-amino-3-methyl-5- [5- [5- (3-chlorophenyl) pentanoyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-2332 in formula Ia-2: 3-amino-3-methyl-5- [5- [5- (4-chlorophenyl) pentanoyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-2333 in Formula Ia-2: 3-amino-3-methyl-5- [5- [5- (3,4-dichlorophenyl) pentanoyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-2334 in formula Ia-2: 3-amino-3-methyl-5- [5- [5- (3,5-dichlorophenyl) pentanoyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-2335 in formula Ia-2: 3-amino-3-methyl-5- [5- [5- (3-methylphenyl) pentanoyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-2336 in formula Ia-2: 3-amino-3-methyl-5- [5- [5- (3,4-dimethylphenyl) pentanoyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-2337 in formula Ia-2: 3-amino-3-methyl-5- [5- [5- (3,5-dimethylphenyl) pentanoyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-2338 in formula Ia-2: 3-amino-3-methyl-5- [5- [5- (3-trifluoromethylphenyl) pentanoyl] thiophen-2-yl] pentylphosphonic acid,
Exemplified Compound No. 1-2339 in Formula Ia-2: 3-amino-3-methyl-5- [5- [5- (3,4-ditrifluoromethylphenyl) pentanoyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-2340 in formula Ia-2: 3-amino-3-methyl-5- [5- [5- (3,5-ditrifluoromethylphenyl) pentanoyl] thiophen-2-yl] pentylphosphonic acid,
Exemplified Compound No. 1-2341 in Formula Ia-2: 3-amino-3-methyl-5- [5- [5- (3-methoxyphenyl) pentanoyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-2342 in Formula Ia-2: 3-amino-3-methyl-5- [5- [5- (3,4-dimethoxyphenyl) pentanoyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-2343 in formula Ia-2: 3-amino-3-methyl-5- [5- [5- (3,5-dimethoxyphenyl) pentanoyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-2344 in Formula Ia-2: 3-amino-3-methyl-5- [5- [5- (3,4,5-trimethoxyphenyl) pentanoyl] thiophen-2-yl] pentylphosphonic acid ,
Exemplified Compound No. 1-2345 in Formula Ia-2: 3-amino-3-methyl-5- [5- [5- (3-acetylphenyl) pentanoyl] thiophen-2-yl] pentylphosphonic acid and
Illustrative compound number 1-2346 in Formula Ia-2: 3-amino-3-methyl-5- [5- [5- (4-acetylphenyl) pentanoyl] thiophen-2-yl] pentylphosphonic acid
And most preferably
Illustrative compound number 1-71 in formula Ia-1: mono 2-amino-2-methyl-4- [5- (4-cyclohexylbutyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-98 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- (5-cyclohexylpentyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-152 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- (5-phenylpentyl) thiophen-2-yl] butyl ester
Illustrative compound number 1-400 in formula Ia-1: mono 2-amino-2-methyl-4- [5- (4-cyclohexyloxybutyl) thiophen-2-yl] butyl ester phosphate
Exemplified Compound No. 1-463 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (4-fluorophenoxy) butyl] thiophen-2-yl] butyl ester
Illustrative compound number 1-479 in formula Ia-1: mono 2-amino-2-methyl-4- [5- [4- (4-methoxyphenoxy) butyl] thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-594 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- (4-benzyloxybutyl) thiophen-2-yl] butyl ester
Illustrative compound number 1-743 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- (4-cyclohexylbut-1-ynyl) thiophen-2-yl] butyl ester
Illustrative compound number 1-756 in formula Ia-1: mono 2-amino-2-methyl-4- [5- (4-phenylbut-1-ynyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-770 in formula Ia-1: mono 2-amino-2-methyl-4- [5- (5-cyclohexylpent-1-ynyl) thiophen-2-yl] butyl ester phosphate
Exemplified Compound No. 1-824 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- (5-phenylpent-1-ynyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-833 in formula Ia-1: mono 2-amino-2-methyl-4- [5- [5- (4-fluorophenyl) pent-1-ynyl] thiophen-2-yl] butyl phosphate ester,
Illustrative compound number 1-849 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (4-methoxyphenyl) pent-1-ynyl] thiophen-2-yl] butyl ester,
Illustrative compound number 1-1050 in formula Ia-1: mono 2-amino-2-methyl-4- [5- [3- (4-methylcyclohexyloxy) propynyl] thiophen-2-yl] butyl ester phosphate
Illustrative compound number: 1-1063 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (4-methylphenoxy) propynyl] thiophen-2-yl] butyl ester
Exemplified Compound No. 1-1064 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (4-ethylphenoxy) propynyl] thiophen-2-yl] butyl ester,
Illustrative compound number 1-1068 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (4-methylthiophenoxy) propynyl] thiophen-2-yl] butyl ester,
Illustrative compound number: 1-1072 in formula Ia-1: mono 2-amino-2-methyl-4- [5- (4-cyclohexyloxybut-1-ynyl) thiophen-2-yl] butyl ester phosphate
Illustrative Compound Number 1-1135 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [4- (4-fluorophenoxy) but-1-ynyl] thiophen-2-yl] butyl phosphate ester,
Illustrative Compound Number 1-1139 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [4- (4-methylphenoxy) but-1-ynyl] thiophen-2-yl] butyl phosphate ester,
Illustrative compound number 1-1185 in formula Ia-1: Mono 2-amino-2-methyl-4- [5- (3-cyclohexylmethoxypropynyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-1266 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- (4-phenylmethoxybut-1-ynyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-1329 in formula Ia-1: Mono 2-amino-2-methyl-4- [5- (4-cyclohexylbutanoyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-1330 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- (4-phenylbutanoyl) thiophen-2-yl] butyl ester,
Illustrative compound number 1-1331 in formula Ia-1: Mono 2-amino-2-methyl-4- [5- (5-cyclohexylpentanoyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-1344 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- (5-phenylpentanoyl) thiophen-2-yl] butyl ester
Illustrative compound number 1-1348 in formula Ia-1: mono 2-amino-2-methyl-4- [5- [5- (4-fluorophenyl) pentanoyl] thiophen-2-yl] butyl ester phosphate
Exemplified Compound No. 1-1764 in Formula Ia-1: Mono 2-amino-2-ethyl-4- [5- (5-cyclohexylpentyl) thiophen-2-yl] butyl ester phosphate
Exemplified Compound No. 1-1909 in Formula Ia-1: Phosphoric acid mono 2-amino-2-ethyl-4- [5- (5-cyclohexylpent-1-ynyl) thiophen-2-yl] butyl ester,
Exemplified Compound No. 1-2097 in Formula Ia-1: Mono 2-amino-2-ethyl-4- [5- (5-cyclohexylpentanoyl) thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-2273 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (4-chlorophenoxy) propynyl] thiophen-2-yl] butyl ester,
Exemplified Compound No. 1-2276 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (3-methylphenoxy) propynyl] thiophen-2-yl] butyl ester,
Exemplified Compound No. 1-2278 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [3- (3,4-dimethylphenoxy) propynyl] thiophen-2-yl] butyl ester phosphate
Illustrative compound number 1-2283 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (3-methoxyphenoxy) propynyl] thiophen-2-yl] butyl ester,
Exemplified Compound No. 1-2284 in Formula Ia-1: Mono 2-amino-2-methyl-4- [5- [3- (3,4-dimethoxyphenoxy) propynyl] thiophen-2-yl] butyl ester phosphate
Exemplified Compound No. 1-2285 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (3,5-dimethoxyphenoxy) propynyl] thiophen-2-yl] butyl ester
Exemplified Compound No. 1-2287 in Formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (3-acetylphenoxy) propynyl] thiophen-2-yl] butyl ester,
Illustrative compound number 1-2288 in formula Ia-1: Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (4-acetylphenoxy) propynyl] thiophen-2-yl] butyl ester,
Illustrative compound number 1-71 in formula Ia-2: 3-amino-3-methyl-5- [5- (4-cyclohexylbutyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-98 in formula Ia-2: 3-amino-3-methyl-5- [5- (5-cyclohexylpentyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-152 in Formula Ia-2: 3-amino-3-methyl-5- [5- (5-phenylpentyl) thiophen-2-yl] pentylphosphonic acid,
Exemplified compound number 1-400 in formula Ia-2: 3-amino-3-methyl-5- [5- (4-cyclohexyloxybutyl) thiophen-2-yl] pentylphosphonic acid,
Exemplified Compound No. 1-463 in Formula Ia-2: 3-amino-3-methyl-5- [5- [4- (4-fluorophenoxy) butyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-479 in Formula Ia-2: 3-amino-3-methyl-5- [5- [4- (4-methoxyphenoxy) butyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-594 in Formula Ia-2: 3-amino-3-methyl-5- [5- (4-benzyloxybutyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1329 in formula Ia-2: 3-amino-3-methyl-5- [5- (4-cyclohexylbutanoyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1330 in formula Ia-2: 3-amino-3-methyl-5- [5- (4-phenylbutanoyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1331 in formula Ia-2: 3-amino-3-methyl-5- [5- (5-cyclohexylpentanoyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1344 in formula Ia-2: 3-amino-3-methyl-5- [5- (5-phenylpentanoyl) thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number 1-1348 in formula Ia-2: 3-amino-3-methyl-5- [5- [5- (4-fluorophenyl) pentanoyl] thiophen-2-yl] pentylphosphonic acid,
Illustrative compound number: 1-1764 in formula Ia-2: 3-amino-3-ethyl-5- [5- (5-cyclohexylpentyl) thiophen-2-yl] pentylphosphonic acid
as well as
Illustrative compound number: 1-2097 in formula Ia-2: 2-amino-2-ethyl-4- [5- (5-cyclohexylpentanoyl) thiophen-2-yl] pentylphosphonic acid
It is.
[0065]
DETAILED DESCRIPTION OF THE INVENTION
Compound (I) of the present invention can be produced according to the method described below.
[0066]
Method A is a method for producing compound (I-1) in which Z is an oxygen atom in compound (I).
[0067]
[Chemical 9]

[0068]
In the above formula, R¹, R², R^Three, Ra^Three, R^Four, R^Five, R⁶, R⁷, X, Y and n have the same meaning as described above. R^10aRepresents a lower alkyl group (particularly a t-butyl group) or a lower alkoxy group (particularly a t-butoxy group);^4a, R^5a, R^6a, R^7a, X^aAnd Y^aAre respectively R^4a, R^5a, R^6a, R^7a, X^aAnd Y^aIn addition to the amino, hydroxy and / or carboxyl group which may be protected, the amino, hydroxy and / or carboxyl group contained in R, respectively, R^Four, R^Five, R⁶, R⁷, X and Y have the same meaning as in the definition of the group, and R¹¹And R¹²Are the same or different and each represents a lower alkyl group (particularly an ethyl or isopropyl group).
[0069]
In the above, R^5a, R^6a, R^7a, X^aAnd Y^aThe “protecting group” of the “amino group that may be protected” in the definition of is not particularly limited as long as it is a protecting group of an amino group used in the field of organic synthetic chemistry.
“Lower aliphatic acyl groups” such as the above “lower aliphatic acyl groups”, halogeno lower aliphatic acyl groups such as chloroacetyl and trifluoroacetyl, and lower aliphatic acyl groups substituted with lower alkoxy such as methoxyacetyl ;
Selected from the above substituent group a such as benzoyl, 1-indanecarbonyl, aromatic acyl group such as 1- or 2-naphthoyl, 4-chlorobenzoyl, 4-fluorobenzoyl, 2,4,6-trimethylbenzoyl “Aromatic acyls”, such as aromatic acyl groups substituted with 1 to 3 of
A “lower alkoxycarbonyl group” such as the above “lower alkoxycarbonyl group”, a lower alkoxycarbonyl group substituted with a halogen or tri-lower alkylsilyl such as 2,2,2-trichloroethoxycarbonyl, 2-trimethylsilylethoxycarbonyl;
A “lower alkenyloxycarbonyl group” such as vinyloxycarbonyl, allyloxycarbonyl;
1 to 3 groups selected from the substituent group a such as aralkyloxycarbonyl group such as benzyloxycarbonyl, 4-methoxybenzyloxycarbonyl, 3,4-dimethoxybenzyloxycarbonyl, 2-nitrobenzyloxycarbonyl “Aralkyloxycarbonyls” such as individually substituted aralkyloxycarbonyl groups;
Tri-lower silyl groups such as trimethylsilyl, triethylsilyl, isopropyldimethylsilyl, t-butyldimethylsilyl, aryl such as diphenylmethylsilyl, phenyldiisopropylsilyl, or silyl groups trisubstituted with aryl and lower alkyl, etc. Silyls ";
Lower alkyl group substituted with 1 to 3 aryl groups such as benzyl, phenethyl, 3-phenylpropyl, α-naphthylmethyl, diphenylmethyl, triphenylmethyl, 4-methylbenzyl, 2,4,6-trimethyl Benzyl, 4-methoxybenzyl, 4-methoxyphenyldiphenylmethyl, 2-nitrobenzyl, 4-chlorobenzyl, 4-bromobenzyl, 4-cyanobenzyl, 4-cyanobenzyldiphenylmethyl, bis (2-nitrophenyl) methyl, “Aralkyls” such as lower alkyl groups substituted with 1 to 3 aryl groups substituted on the aryl ring with lower alkyl, lower alkoxy, nitro, halo or cyano, such as piperonyl; or
“Schiff bases such as N, N-dimethylaminomethylene, benzylidene, 4-methoxybenzylidene, 4-nitrobenzylidene, salicylidene, 5-chlorosalicylidene, diphenylmethylene, (5-chloro-2-hydroxyphenyl) phenylmethylene Preferably a aralkyloxycarbonyl group substituted with 1 to 3 lower alkoxycarbonyl group, aralkyloxycarbonyl group or a group selected from substituent group a. , Preferably a lower alkoxycarbonyl group or a lower alkenyloxycarbonyl group, and most preferably a t-butoxycarbonyl group or an allyloxycarbonyl group.
[0070]
In the above, R^4a, R^5a, R^6a, R^7a, X^aAnd Y^aThe “protecting group” of the “optionally protected hydroxy group” in the definition of is not particularly limited as long as it is a protecting group of a hydroxy group used in the field of synthetic organic chemistry.
The aforementioned “lower aliphatic acyls”;
The “aromatic acyls”;
“Tetrahydro, such as tetrahydropyran-2-yl, 3-bromotetrahydropyran-2-yl, 4-methoxytetrahydropyran-4-yl, tetrahydrothiopyran-2-yl, 4-methoxytetrahydrothiopyran-4-yl Pyranyl or tetrahydrothiopyranyls ";
“Tetrahydrofuranyl or tetrahydrothiofuranyls” such as tetrahydrofuran-2-yl, tetrahydrothiofuran-2-yl;
The “silyls”;
Methoxymethyl, 1,1-dimethyl-1-methoxymethyl, lower alkoxymethyl groups such as ethoxymethyl, lower alkoxylated lower alkoxymethyl groups such as 2-methoxyethoxymethyl, 2,2,2-trichloroethoxymethyl, “Lower alkoxymethyls” such as halogeno lower alkoxymethyl such as bis (2-chloroethoxy) methyl;
“Substituted ethyls” such as 1-ethoxyethyl, lower alkoxylated ethyl groups such as 1- (isopropoxy) ethyl, and halogenated ethyl groups such as 2,2,2-trichloroethyl;
The aforementioned “aralkyls”;
The aforementioned “lower alkoxycarbonyls”;
The aforementioned “lower alkenyloxycarbonyls”; or
The above “aralkyloxycarbonyls”
Preferably a lower aliphatic acyl group, an aromatic acyl group, a lower alkoxycarbonyl group or a (lower alkoxy) methyl group, more preferably a lower aliphatic acyl group or a (lower alkoxy) methyl group And most preferably an acetyl group or a methoxymethyl group.
[0071]
In the above, R^5a, R^6a, R^7a, X^aAnd Y^aThe “protecting group” of the “optionally protected carboxyl group” in the definition of is not particularly limited as long as it is a protecting group for a carboxyl group used in the field of organic synthetic chemistry. Or the above-mentioned “aralkyl group”, preferably a lower alkyl group, and most preferably a methyl group.
[0072]
Step A-1 is a step of producing a compound having the general formula (I-1), and reacting the alcohol form (10) with the compound (II) to form a phosphite form, and then oxidizing agent And optionally, the formula CO₂R^10aThe amino protecting group is removed, the hydroxy protecting group is removed, the carboxyl protecting group is removed, the phosphate protecting group is removed, and / or the amino group is converted into a lower aliphatic acyl group. Or by lower alkoxycarbonylation (acylation).
[0073]
The desired reaction can be carried out by changing the order as appropriate, and the protecting group can be removed selectively by appropriately selecting the reaction conditions.
[0074]
In order to introduce a compound having a primary hydroxyl group into a phosphate ester, it can be carried out according to a method generally used in the field of synthetic organic chemistry. For example, it can be easily derived by the method described in Experimental Chemistry Course 22 (4th edition: Maruzen) “Organic Synthesis IV”, Chapter 3, “Phosphate Esters”. In practice, the following method is suitable.
[0075]
That is, a method in which an alcohol form (10) and compound (II) are reacted in an inert solvent in the presence of an activator to produce a phosphite ester form, and then reacted with an oxidizing agent in an inert solvent It is.
[0076]
Inert solvents used in the reaction of compound (10) with compound (II) are, for example, aliphatic hydrocarbons such as hexane and heptane; aromatic hydrocarbons such as benzene, toluene and xylene; Halogenated hydrocarbons such as methylene, chloroform, dichloromethane, 1,2-dichloroethane, carbon tetrachloride; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, or a mixed solvent of the above solvents. Halogenated hydrocarbons or ethers (most preferably methylene chloride or tetrahydrofuran).
[0077]
The activators used are, for example, tetrazoles such as 1H-tetrazole, 5-methyl-1H-tetrazole, 5-phenyl-1H-tetrazole (preferably 1H-tetrazole).
[0078]
The compound (II) used is preferably diallyl N, N-diisopropyl phosphoramidite, dimethyl N, N-diisopropyl phosphoramidite, diethyl N, N-diisopropyl phosphoramidite, di-t-butyl N, N-diisopropyl phosphoramidite, dibenzyl N, N-diisopropyl phosphoramidite, dimethyl N, N-diethyl phosphoramidite, di-t-butyl N, N-ethyl phosphoramidite, dibenzyl N, N-diethyl phosphoramidite NN-diethyl-1,5-dihydro-2,4,3-benzodioxaphosphin-3-amine, bis (2-cyanoethyl) N, N-diisopropylformamidite or bis (9-fluorenyl) Methyl) phosphoramidites such as N, N-diisopropylformolamidite, particularly preferably diallyl N, N-dii Propyl phosphoramidite.
[0079]
The reaction temperature varies depending on the raw material compound, the type of the solvent and the like, but is usually −10 ° C. to 60 ° C. (preferably 0 ° C. to 30 ° C.).
[0080]
While the reaction time varies depending on the raw material compound, the solvent, the reaction temperature, etc., it is generally 10 minutes to 24 hours (preferably 30 minutes to 2 hours).
[0081]
The phosphite ester obtained by the above reaction can react with an oxidizing agent without post-treatment and isolation of the reaction.
[0082]
The inert solvent used in the reaction with the oxidizing agent is the same as that used in the reaction between the alcohol form (10) and compound (II).
[0083]
The oxidizing agents used are, for example, t-butyl hydroperoxide, cumene hydroperoxide, m-chloroperbenzoic acid, 3,5-dinitroperbenzoic acid, 0-carboxyperbenzoic acid, dimethyloxolane, peracetic acid, peracetic acid. Peroxides such as trifluoroacetic acid, perphthalic acid, and hydrogen peroxide are preferable, and t-butyl hydroperoxide or m-chloroperbenzoic acid is preferable.
[0084]
The reaction temperature varies depending on the obtained phosphite ester, oxidizing agent, type of solvent, and the like, but is usually -78 ° C to room temperature (preferably -78 ° C to 0 ° C).
[0085]
The reaction time varies depending on the obtained phosphite ester, oxidant, solvent, reaction temperature and the like, but is usually 5 minutes to 2 hours (preferably 5 minutes to 30 minutes).
[0086]
The removal of amino, hydroxy and carboxyl protecting groups varies depending on the type, but is generally well known in the art of synthetic organic chemistry, such as TWGreen, (Protective Groups in Organic Synthesis), John Wiley & Sons: JFWMcOmis, (Protective Groups in Organic Chemistry), which can be carried out by the method described in Plenum Press as follows.
[0087]
When the amino protecting group is a silyl compound, it is usually treated with a compound that generates a fluorine anion such as tetrabutylammonium fluoride, hydrofluoric acid, hydrofluoric acid-pyridine, or potassium fluoride. Or inorganic acid or acetic acid such as hydrochloric acid, hydrobromic acid, sulfuric acid, perchloric acid, phosphoric acid, formic acid, oxalic acid, methanesulfonic acid, p-toluenesulfonic acid, camphorsulfonic acid, trifluoroacetic acid, trifluoro It can be removed by treatment with an organic acid such as romethanesulfonic acid (preferably hydrochloric acid).
[0088]
In addition, when removing with a fluorine anion, reaction may be accelerated | stimulated by adding organic acids, such as formic acid, an acetic acid, and propionic acid.
[0089]
The solvent used in the above reaction is preferably an ether such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, diethylene glycol dimethyl ether; a nitrile such as acetonitrile or isobutyronitrile; Such an organic acid; water; or a mixed solvent of the above solvents, and preferably tetrahydrofuran.
[0090]
Although the reaction temperature and reaction time vary depending on the raw material compound, catalyst, solvent, etc., the reaction temperature is usually 0 ° C. to 100 ° C. (preferably 10 ° C. to 50 ° C.), and the reaction time is 10 minutes to 24 hours (preferably 30 minutes to 6 hours).
[0091]
When the amino-protecting group is aralkyl or aralkyloxycarbonyl, it is usually brought into contact with a reducing agent in an inert solvent (preferably catalytic reduction using hydrogen at room temperature under a catalyst). A method of removing by using an oxidizing agent or a method of removing using an oxidizing agent is suitable.
[0092]
The solvent used for the removal by catalytic reduction is not particularly limited as long as it is inert to this reaction. For example, aliphatic hydrocarbons such as hexane, heptane, ligroin, petroleum ether; toluene, benzene, Aromatic hydrocarbons such as xylene; esters such as methyl acetate, ethyl acetate, propyl acetate, butyl acetate, diethyl carbonate; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, diethylene glycol dimethyl ether Methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, t-butanol, isoamyl alcohol, diethylene glycol, glycerin, octanol, cyclohexanol, methyl cellosolve, etc. Alcohols; organic acids such as acetic acid; water; or a mixed solvent of the above solvent and water, preferably alcohols, ethers, organic acids or water (most preferably alcohols or organic acids) It is.
[0093]
The catalyst used for the removal by catalytic reduction is not particularly limited as long as it is usually used for the catalytic reduction reaction, but preferably palladium-carbon, Raney-nickel, platinum oxide, platinum black, rhodium. -Aluminum oxide, triphenylphosphine-rhodium chloride, palladium-barium sulfate.
[0094]
The pressure of hydrogen is not particularly limited, but is usually 1 to 10 atmospheres.
[0095]
Although the reaction temperature and reaction time vary depending on the raw material compound, catalyst, solvent, etc., the reaction temperature is usually 0 ° C. to 100 ° C., and the reaction time is 5 minutes to 24 hours.
[0096]
The solvent used in the removal using an oxidizing agent is not particularly limited as long as it does not participate in this reaction, but is preferably a water-containing organic solvent. Examples of such an organic solvent include chloroform, dichloromethane, Halogenated hydrocarbons such as 1,2-dichloroethane and carbon tetrachloride; nitriles such as acetonitrile, ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, diethylene glycol dimethyl ether; Ketones such as formamide, dimethylformamide, dimethylacetamide, amides such as hexamethylphosphoric triamide; sulfoxides such as dimethyl sulfoxide; or sulfolane, preferably halogenated hydrocarbons, ethers Kind The (most preferably, halogenated hydrocarbons or sulfoxides) sulfoxides is.
[0097]
The oxidizing agent used is not particularly limited as long as it is a compound used for oxidation, but preferably potassium persulfate, sodium persulfate, ammonium cerium nitrate (CAN), 2,3-dichloro-5, 6-dicyano-p-benzoquinone (DDQ).
[0098]
Although the reaction temperature and reaction time vary depending on the raw material compound, catalyst, solvent, etc., the reaction temperature is usually 0 ° C. to 150 ° C., and the reaction time is 10 minutes to 24 hours.
[0099]
Further, when the amino-protecting group is an aralkyl, the protecting group can be removed using an acid in an inert solvent.
[0100]
The acid used in the above reaction is not particularly limited as long as it is used as an acid catalyst in a normal reaction. For example, inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, perchloric acid, and phosphoric acid are used. Acids; Bronsted acids such as acetic acid, formic acid, oxalic acid, methanesulfonic acid, p-toluenesulfonic acid, camphorsulfonic acid, trifluoroacetic acid, trifluoromethanesulfonic acid, etc .; zinc chloride, tin tetrachloride, borontri Lewis acids such as chloride, boron trifluoride, boron tribromide; or acidic ion exchange resins, preferably inorganic or organic acids (most preferably hydrochloric acid, acetic acid or trifluoroacetic acid).
[0101]
Inert solvents used are, for example, hexane, heptane, ligroin, aliphatic hydrocarbons such as petroleum ether; aromatic hydrocarbons such as benzene, toluene, xylene; chloroform, dichloromethane, 1,2-dichloroethane. Halogenated hydrocarbons such as carbon tetrachloride; esters such as methyl acetate, ethyl acetate, propyl acetate, butyl acetate, and diethyl carbonate; such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, and diethylene glycol dimethyl ether Ethers such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, t-butanol, isoamyl alcohol, diethylene glycol, glycerin, octanol, cyclohexane Alcohols such as sanol and methyl cellosolve; amides such as formamide, dimethylformamide, dimethylacetamide and hexamethylphosphoric triamide; water; or water or a mixed solvent of the above solvents, preferably ether , Alcohols or water (most preferably dioxane, tetrahydrofuran, ethanol or water).
[0102]
The reaction temperature varies depending on the raw material compound, the acid used, the solvent, and the like, but is usually −20 ° C. to boiling point temperature (preferably 0 ° C. to 100 ° C.).
[0103]
The reaction time varies depending on the raw material compound, the acid used, the solvent, the reaction temperature and the like, but is usually 15 minutes to 48 hours (preferably 30 minutes to 20 hours).
[0104]
When the amino-protecting group is a lower aliphatic acyl, aromatic acyl, lower alkoxycarbonyl or substituted methylene group forming a Schiff base, an acid is present in the presence of an inert solvent and water. Alternatively, it can be removed by hydrolysis with a base.
[0105]
The acid used in the above reaction is not particularly limited as long as it is usually used as an acid and does not inhibit the reaction. For example, hydrobromic acid, hydrochloric acid, sulfuric acid, perchloric acid, phosphoric acid, nitric acid And is preferably hydrochloric acid.
[0106]
The base used in the above reaction is not particularly limited as long as it does not affect other parts of the compound, but preferably alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate; water Alkali metal hydroxides such as lithium oxide, sodium hydroxide and potassium hydroxide; metal alkoxides such as lithium methoxide, sodium methoxide, sodium ethoxide and potassium tert-butoxide; or aqueous ammonia and concentrated ammonia -Ammonia such as methanol, preferably alkali metal hydroxides.
[0107]
The solvent used in the above reaction is not particularly limited as long as it is used in a usual hydrolysis reaction. For example, methanol, ethanol, n-propanol, isopropanol, n- Alcohols such as butanol, isobutanol, t-butanol, isoamyl alcohol, diethylene glycol, glycerin, octanol, cyclohexanol, methyl cellosolve; diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane Ethers such as diethylene glycol dimethyl ether; water; or a mixed solvent of water and the above organic solvent, preferably ethers (most preferably dioxane).
[0108]
The reaction temperature and reaction time vary depending on the raw material compound, the solvent, the acid or base used, and are not particularly limited. However, in order to suppress side reactions, the reaction temperature is usually 0 ° C. to 150 ° C., The reaction time is 1 to 10 hours.
[0109]
When the amino protecting group is a lower alkenyloxycarbonyl, the amino protecting group is a substituted methylene group forming the above-mentioned aliphatic acyl, aromatic acyl, alkoxycarbonyl or Schiff base. In the same manner as the base treatment in the removal reaction.
[0110]
In the case of an allyloxycarbonyl group, in particular, a method of removing a protective group using palladium and triphenylphosphine or nickel tetracarbonyl in an inert solvent is simple and may be carried out with few side reactions. it can.
[0111]
The inert solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the raw material compound to some extent, but preferably alcohols such as methanol, ethanol, isopropanol; diethyl ether, diisopropyl Ethers such as ether, t-butyl methyl ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene and xylene; aliphatic hydrocarbons such as hexane and cyclohexane; acetonitrile and propionitrile Nitriles; or esters such as ethyl acetate and propyl acetate, and more preferably ethers (particularly preferably tetrahydrofuran) or nitriles (particularly preferably acetonitrile).
[0112]
Although the reaction temperature and reaction time vary depending on the raw material compound, catalyst, solvent, etc., the reaction temperature is usually 0 ° C. to 150 ° C. (preferably 0 ° C. to 100 ° C.), and the reaction time is 5 minutes to 48. Time (preferably 30 minutes to 24 hours).
[0113]
When the hydroxy protecting group is a silyl group, it is removed by treatment in the same manner as in the case where the amino protecting group is a silyl group.
[0114]
When the protective group for hydroxy group is aralkyl or aralkyloxycarbonyl, it is removed by treatment in the same manner as in the case where the protective group for amino group is aralkyl or aralkyloxycarbonyl.
[0115]
When the protecting group of the hydroxy group is lower alkoxymethyl, tetrahydropyranyl or tetrahydrothiopyranyl, tetrahydrofuranyl or tetrahydrothiofuranyl, or substituted ethyls, usually in an inert solvent, It is removed by treatment with acid.
[0116]
The acid to be used is not particularly limited as long as it is usually used as a Bronsted acid or Lewis acid, and is preferably hydrogen chloride; inorganic acid such as hydrochloric acid, sulfuric acid, nitric acid; acetic acid, trifluoro Organic acids such as acetic acid, methanesulfonic acid, p-toluenesulfonic acid: or Lewis acids such as boron trifluoride, preferably hydrochloric acid or acetic acid, and strongly acidic such as Dowex 50W The cation exchange resin can also be used.
[0117]
The solvent used in the above reaction is not particularly limited as long as it is inert to this reaction. For example, aliphatic hydrocarbons such as hexane, heptane, ligroin, petroleum ether; benzene, toluene, xylene Aromatic hydrocarbons such as; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene; such as ethyl formate, ethyl acetate, propyl acetate, butyl acetate, diethyl carbonate Esters; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, diethylene glycol dimethyl ether; methanol, ethanol, n-propanol, isopropanol, n-butanol -L, isobutanol, t-butanol , Isoamyl alcohol, diethylene glycol, glycerin, octanol, cyclohexanol, alcohols such as methyl cellosolve; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, cyclohexanone; water; or a mixture of the above solvents Solvents, preferably ethers (most preferably tetrahydrofuran) or alcohols (most preferably methanol).
[0118]
The reaction temperature and reaction time vary depending on the raw material compound, the acid used, the solvent, and the like, but the reaction temperature is −10 ° C. to 200 ° C. (preferably 0 ° C. to 150 ° C.), and the reaction time is 5 Minutes to 48 hours (preferably 30 minutes to 10 hours).
[0119]
When the protecting group for hydroxy group is lower aliphatic acyl, aromatic acyl, lower alkoxycarbonyl group or lower alkenyloxycarbonyl, the amino protecting group is aliphatic acyl, aromatic acyl In the same manner as the base treatment in the removal reaction in the case of a substituted methylene group forming an alkoxycarbonyl or a Schiff base.
[0120]
In the case where the protective group for the hydroxy group is an allyloxycarbonyl group, palladium, triphenylphosphine, or bis (methyldiphenylphosphine) (1,5-cyclooctadiene) iridium (I) .hexafluorophosphate is particularly preferable. The removal method is simple and can be carried out with few side reactions, and is removed by treatment in the same manner as in the case where the protective group for the amino group is an allyloxycarbonyl group.
[0121]
When the protecting group for the carboxyl group is a lower alkyl group or an aralkyl group, the conditions for the removal reaction when the protecting group for the hydroxy group is an aliphatic acyl, aromatic acyl or alkoxycarbonyl are as described above. This can be achieved by treatment with a base.
[0122]
When the protecting group for the carboxyl group is an aralkyl group, it can be removed by catalytic reduction as in the case where the amino protecting group is an aralkyl or an aralkyloxycarbonyl group.
[0123]
Inactive when the protecting group of the phosphate group is a cyano group, an optionally substituted silyl group, an aryl group, a heterocyclyl group, an arylthio group, a sulfonyl group, or a lower alkyl group that may be substituted with a halogen atom The protecting group is removed by hydrolysis with acid in the presence of water in a solvent or by reaction with a trimethylsilyl halide (eg, bromotrimethylsilyl or iodotrimethylsilyl) in an inert solvent.
[0124]
The inert solvent used for the hydrolysis is, for example, an alcohol such as methanol or ethanol; or an ether such as diethyl ether, diisopropyl ether, tetrahydrofuran or dioxane, preferably an ether. Most preferred is dioxane.
[0125]
The acid used in the above reaction is, for example, an inorganic acid such as hydrochloric acid, sulfuric acid, phosphoric acid, or nitric acid, and preferably hydrochloric acid.
[0126]
The reaction temperature is 0 ° C. to 150 ° C. (preferably 20 ° C. to 100 ° C.), and the reaction temperature is 1 hour to 60 hours (preferably 1 hour to 48 hours).
[0127]
Examples of the inert solvent used in the reaction with the above-mentioned trimethylsilyl halide include aliphatic hydrocarbons such as hexane and heptane; aromatic hydrocarbons such as benzene, toluene and xylene; methylene chloride, chloroform, Halogenated hydrocarbons such as dichloromethane, 1,2-dichloroethane, carbon tetrachloride; nitriles such as acetonitrile; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane; methanol, ethanol, Alcohols such as n-propanol; or a mixed solvent of the above-mentioned solvents, preferably halogenated hydrocarbons or nitriles (more preferably, chloroform, dichloromethane or acetonitrile).
[0128]
The reaction temperature varies depending on the raw material compound, the type of solvent used and the like, but is usually -78 ° C to 100 ° C (preferably 0 ° C to 80 ° C).
[0129]
The reaction time varies depending on the raw material compound, the solvent used, the reaction temperature and the like, but is usually 10 minutes to 24 hours (preferably 1 hour to 6 hours).
[0130]
When the protective group for the phosphate group is a lower alkenyl group, the protective group is reacted with a palladium compound in an inert solvent in the presence of an amine, formic acid, formates, a trialkyltin compound or an active methylene compound. The group can be removed.
[0131]
Examples of the inert solvent used in the above reaction include aliphatic hydrocarbons such as hexane and heptane; aromatic hydrocarbons such as toluene, benzene and xylene; halogenated hydrocarbons such as chloroform and dichloromethane. Nitriles such as acetonitrile; esters such as methyl acetate, ethyl acetate, propyl acetate; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane; methanol, ethanol, n-propanol Alcohols such as alcohol and isopropanol; organic acids such as acetic acid; water; or a mixed solvent of the above solvent and water, preferably nitriles or ethers (particularly preferably Acetonitrile or tetrahydrofuran).
[0132]
Examples of the amine used in the above reaction include tertiary amines such as triethylamine, tributylamine, diisopropylethylamine, N-methylmorpholine, 1,4-diazabicyclo [2.2.2] octane (DABCO); Secondary amines such as dimethylamine, diisopropylamine and pyrrolidine; or primary amines such as ethylamine, propylamine, butylamine, N, N-dimethylaniline and N, N-diethylaniline Is pyrrolidine.
[0133]
The formate used in the above reaction is preferably ammonium formate, triethylamine formate or n-butylamine formate.
[0134]
The trialkyltin compound used in the above reaction is preferably trimethyltin, triethyltin or tributyltin, and particularly preferably tributyltin.
[0135]
The active methylene compounds used in the above reaction are, for example, malonic acid esters such as methyl malonate and ethyl malonate; cyanoacetic acid esters such as methyl cyanoacetate; methyl acetoacetate, ethyl acetoacetate, ethyl benzoylacetate Β-ketoacetic acid esters such as: 1,3-diketones such as acetylacetone, benzoylacetone, dibenzoylmethane, 1,3-cyclopentadione, 1,3-cyclohexadione, dimedone; or the active methylene An alkali metal salt of the compound, preferably 1,3-diketones (particularly dimedone) or sodium salt of malonic ester (particularly diethylmalonic acid sodium salt).
[0136]
Examples of the palladium compound used in the above reaction include Pd such as tetrakis (triphenylphosphine) palladium and dichlorodi (triphenylphosphine) palladium.⁰Compound; or Pd such as diacetoxypalladium, bis (dibenzylideneacetone) palladium^IIA compound, preferably tetrakis (triphenylphosphine) palladium.
[0137]
The reaction temperature varies depending on the raw material compound, the type of solvent used and the like, but is usually 0 ° C. to 100 ° C. (preferably 20 ° C. to 80 ° C.).
[0138]
The reaction time varies depending on the raw material compound, the solvent used, the reaction temperature and the like, but is usually 10 minutes to 48 hours (preferably 30 minutes to 24 hours).
[0139]
When the protecting group of the phosphate group is an arylmethyl group, it is removed by treatment in the same manner as in the case where the amino protecting group is an aralkyl or aralkyloxycarbonyl group.
[0140]
When the protecting group of the phosphate group is an aryl group, the protecting group of the amino group is a substituted methylene group that forms a lower aliphatic acyl, aromatic acyl, lower alkoxycarbonyl, or Schiff base. It is processed and removed in the same way as in some cases.
[0141]
When the protecting group of the phosphate group is an amide, the removal reaction when the amino protecting group is a substituted methylene group forming an aliphatic acyl, aromatic acyl, alkoxycarbonyl or Schiff base It is carried out in the same manner as in the acid treatment.
[0142]
The method for acylating an amino group is carried out by subjecting compound (10) to the following compound in an inert solvent in the presence or absence of a base:
R^1a-Q (III)
[Wherein R^1aRepresents a lower aliphatic acyl group or a lower alkoxycarbonyl group, and Q represents a halogen atom (preferably a chlorine atom, a bromine atom or an iodine atom). ] Is made to react.
[0143]
The inert solvent used is preferably an ether such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, diethylene glycol dimethyl ether; methanol, ethanol, n-propanol Alcohols such as ethyl acetate, propyl acetate, isopropanol, n-butanol, isobutanol, t-butanol, isoamyl alcohol, diethylene glycol, glycerin, octanol, cyclohexanol, methyl cellosolve; Such esters; alkyl ketones such as acetone and 2-butanone; halogenated hydrocarbons such as dichloromethane, chloroform and carbon tetrachloride; or a mixed solvent of the above solvent and water, preferably the above Mixed solvent of solvent and water (particularly preferably, A mixed solvent) of ethyl and water.
[0144]
Examples of the base used include alkali metal carbonates such as potassium carbonate; alkali metal hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide. Alkaline earth metal hydroxides such as magnesium hydroxide and calcium hydroxide; or organic amines such as triethylamine, tributylamine, diisopropylethylamine, N-methylmorpholine, pyridine and pyrrolidine, preferably alkali Metal hydrogen carbonates (particularly preferably, potassium hydrogen carbonate).
[0145]
The reaction temperature is 0 ° C. to 50 ° C. (preferably near room temperature), although it varies depending on the raw material compound, the base used, the type of solvent used and the like.
[0146]
The reaction time varies depending on the raw material compound, the base used, the solvent used, the reaction temperature and the like, but is 30 minutes to 10 hours (preferably 1 hour to 5 hours).
[0147]
After completion of the reaction, the target compound (I-1) of each reaction is collected from the reaction mixture according to a conventional method. For example, the reaction mixture is appropriately neutralized, and if an oxidizing agent is present, it is appropriately decomposed with a reducing agent, or if an insoluble matter is present, it is appropriately removed by filtration, and then water and ethyl acetate. It is obtained by adding an immiscible organic solvent, separating the organic layer containing the target compound, washing with water, etc., drying over anhydrous magnesium sulfate, anhydrous sodium sulfate, anhydrous sodium bicarbonate, etc., and then distilling off the solvent. . If necessary, the obtained target compound can be separated and purified by appropriately combining conventional methods such as recrystallization, reprecipitation, chromatography, etc., which are usually used for separation and purification of organic compounds.
[0148]
Method B is a method for producing compound (I-2) in which Z is methylene in compound (I).
[0149]
[Chemical Formula 10]

[0150]
In the above formula, R¹, R², R^Three, Ra^Three, R^Four, R^4a, R^Five, R^5a, R⁶, R^6a, R⁷, R^7a, R^10a, X, X^a, Y, Y^aAnd n have the same meaning as described above.
[0151]
Step B-1 is a step of producing an aldehyde compound having the general formula (IV) by oxidizing the compound having the general formula (10).
[0152]
The oxidation reaction is not particularly limited as long as it is an oxidation reaction that generates an aldehyde from a primary alcohol. For example, Collins oxidation performed in methylene chloride using pyridine and chromic acid; in methylene chloride, pyridinium chromate ( PCC oxidation performed using PCC); PDC oxidation performed using pyridinium dichromate (PDC) in methylene chloride; electrophiles (eg acetic anhydride, trifluoroacetic anhydride, thionyl chloride, chloride) in methylene chloride DMSO oxidation, such as Swern oxidation, using sulfuryl, oxalyl chloride, dicyclohexylcarbodiimide, diphenylketene-p-tolylimine, N, N-diethylaminoacetylene, sulfur trioxide / pyridine complex ; Mann dioxide, which is performed using manganese dioxide in methylene chloride or benzene. Phosphorylation; or in methylene chloride, a Dess-Martin oxidation which is conducted using the Dess-Martin periodinane, preferably carried out in methylene chloride, Dess-Martin oxidation, PDC oxidation or Swern oxidation.
[0153]
The reaction temperature varies depending on the raw material compound, the solvent, the type of oxidizing agent, and the like, but is usually −78 ° C. to 100 ° C., and preferably −78 ° C. to 30 ° C.
[0154]
The reaction time varies depending on the raw material compound, the solvent, the type of oxidizing agent, the reaction temperature, etc., but is usually 10 minutes to 2 days, preferably 30 minutes to 24 hours.
[0155]
After completion of the reaction, the aldehyde (IV) which is the target compound of this reaction is collected from the reaction mixture according to a conventional method. For example, the oxidizing agent is neutralized with sodium hydrogen sulfite water or the like, and insoluble matters are removed by filtration and then concentrated as it is, or an immiscible organic solvent such as water and ethyl acetate is added to add the target compound. The organic layer is separated and dried over anhydrous sodium sulfate, anhydrous magnesium sulfate or the like, and then the solvent is distilled off.
[0156]
The obtained aldehyde form (IV) can be separated and purified using a conventional method, for example, recrystallization, reprecipitation, chromatography or the like, if necessary.
[0157]
In Step B-2, the aldehyde form (IV) is reacted with the compound having the general formula (V) in the presence of a base in an inert solvent to lead to an α, β-unsaturated phosphate ester form (VI). It is a process.
[0158]
The inert solvent used in the above reaction is not particularly limited as long as it dissolves the starting material to some extent, but preferably, aromatic hydrocarbons such as benzene, toluene, xylene; dichloromethane, chloroform, Halogenated hydrocarbons such as carbon tetrachloride; ethers such as diethyl ether, diisopropyl ether, t-butyl methyl ether, tetrahydrofuran; nitriles such as acetonitrile and isobutyronitrile; amides such as formamide; Or sulfoxides such as dimethyl sulfoxide, more preferably aromatic hydrocarbons or ethers (particularly preferably benzene or tetrahydrofuran).
[0159]
The base to be used is not particularly limited as long as it reacts with compound (V) to produce the corresponding carbanion. Preferably, alkali metal carbonates such as sodium carbonate and potassium carbonate; Alkali metal hydrogencarbonates such as sodium hydride and potassium hydrogencarbonate; alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; sodium methoxy Alkali metal alkoxides such as sodium ethoxide, sodium ethoxide, potassium methoxide, potassium ethoxide; organic amines such as N-methylmorpholine and triethylamine; or organometallic bases such as butyllithium and lithium diisopropylamide More preferably, alkali metal alkoxy Class, an alkali metal hydrides and organometallic bases, particularly preferably a sodium hydride.
[0160]
The reaction temperature varies depending on the raw material compound, the solvent, the type of phosphonium salt, the type of base, and the like, but is usually −80 ° C. to 100 ° C., and preferably −20 ° C. to 50 ° C.
[0161]
While the reaction time varies depending on the raw material compound, the solvent, the type of phosphonium salt, the type of base, etc., it is usually 10 minutes to 2 days, preferably 10 minutes to 12 hours.
[0162]
After completion of the reaction, the unsaturated phosphate ester compound (VI) which is the target compound of this reaction is collected from the reaction mixture according to a conventional method. For example, neutralize the reaction solution with dilute hydrochloric acid, etc., and remove any insoluble matter by filtration, then concentrate as it is or add an immiscible organic solvent such as water and ethyl acetate, and add an organic layer containing the target compound. Is separated and dried over anhydrous sodium sulfate, anhydrous magnesium sulfate and the like, and then the solvent is distilled off.
[0163]
The obtained unsaturated phosphate ester compound (VI) can be separated and purified using a conventional method, for example, recrystallization, reprecipitation, chromatography or the like, if necessary.
[0164]
Step B-3 is a step of producing a compound having the general formula (I-2). The unsaturated phosphate ester compound (VI) is reacted with hydrogen in an inert solvent in the presence of a catalytic reduction catalyst. If desired, the formula CO₂R^10aRemoving a protecting group of an amino group including a group having an amino group, removing a protecting group of a hydroxy, removing a protecting group of a carboxyl group, removing a protecting group of a phosphate group and / or acylating an amino group Is done.
[0165]
The inert solvent used in the reaction of reacting the unsaturated phosphate ester compound (VI) with hydrogen is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent. , Alcohols such as methanol, ethanol and isopropanol; ethers such as diethyl ether, diisopropyl ether, t-butyl methyl ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene and xylene; hexane and cyclohexane Or esters such as ethyl acetate and propyl acetate, and more preferably alcohols (particularly preferably methanol or ethanol).
[0166]
The catalytic reduction catalyst used is preferably palladium-carbon, palladium hydroxide-carbon, palladium black, platinum oxide, platinum black, rhodium-aluminum oxide, triphenylphosphine-rhodium chloride (Wilkinson complex), palladium-sulfuric acid. Barium and Raney nickel are preferable, and palladium-carbon or triphenylphosphine-rhodium chloride (Wilkinson complex) is more preferable.
[0167]
The pressure of hydrogen is not particularly limited, but is usually 1 to 10 atm.
[0168]
The reaction temperature varies depending on the raw material compound, the solvent, the type of base and the like, but is usually 0 ° C. to 100 ° C. (preferably room temperature to 60 ° C.).
[0169]
While the reaction time varies depending on the raw material compound, reaction temperature, solvent and base type, it is generally 5 minutes to 96 hours (preferably 1 hour to 48 hours).
[0170]
After completion of the reaction, the target compound (I-2) of this reaction is collected from the reaction mixture according to a conventional method. For example, neutralize the reaction mixture as appropriate, or remove insoluble matter by filtration, add water and an immiscible organic solvent such as ethyl acetate, and separate the organic layer containing the target compound, After washing with water and the like, it is obtained by drying with anhydrous magnesium sulfate, anhydrous sodium sulfate, anhydrous sodium hydrogencarbonate and the like and then distilling off the solvent. If necessary, the obtained target compound can be separated and purified by a conventional method such as recrystallization, reprecipitation, or chromatography.
[0171]
Reaction to remove amino protecting group, reaction to remove hydroxy protecting group, reaction to remove carboxyl protecting group, reaction to remove protecting group of phosphoric acid group and acylation of amino group as desired The reaction to be carried out can be carried out in the same manner as in the aforementioned step A-1.
[0172]
The starting compound (10) is a known compound or is easily produced according to a known method (see, for example, WO 02/06268). Moreover, it can manufacture also with the following method.
[0173]
Method C is a method for producing compound (10).
[0174]
Embedded image

[0175]
In the above formula, R^4a, R^5a, R^6a, R^7a, R^10a, X^a, Y^aAnd n are as defined above, and R⁸Represents a formyl group, a carboxyl group or a lower alkoxycarbonyl group, R⁹And R^9aAre the same or different and each represents a lower alkyl group, R^TenRepresents a lower aliphatic acyl group.
[0176]
Step C-1 is a step of producing a compound having the general formula (3), and the compound having the general formula (2) is present in an inert solvent in the presence or absence of a base (preferably present). Bottom), by reacting with a reducing agent. The compound (2) is a known compound or can be easily produced according to a known method (see, for example, WO02 / 06268).
[0177]
Examples of the inert solvent used in the above reaction include aliphatic hydrocarbons such as hexane, heptane, ligroin, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, and xylene; chloroform, dichloromethane, 1, Halogenated hydrocarbons such as 2-dichloroethane and carbon tetrachloride; esters such as acetic acid, methyl acetate, ethyl acetate, propyl acetate, butyl acetate and diethyl carbonate; diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane and dimethoxyethane Ethers such as diethylene glycol dimethyl ether; methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, t-butanol, isoamyl alcohol, diethylene glycol, Glycerin, octa Alcohol, cyclohexanol, methyl cellosolve, etc .; formamide, dimethylformamide, dimethylacetamide, amides such as hexamethylphosphoric triamide; water; or a mixed solvent of the above solvents, preferably Ethers (most preferably tetrahydrofuran).
[0178]
The base used in the above reaction is an organic amine such as triethylamine, tributylamine, diisopropylethylamine, N-methylmorpholine, pyridine, pyrrolidine, and preferably triethylamine.
[0179]
The reducing agent used in the above reaction is, for example, alkali metal borohydrides such as sodium borohydride, lithium borohydride, sodium cyanoborohydride; or diisobutylaluminum hydride, lithium aluminum hydride, hydrogenated Aluminum hydride compounds such as lithium triethoxyaluminum, preferably alkali metal borohydrides (most preferably sodium borohydride).
[0180]
The reaction temperature varies depending on the raw material compound, the reducing agent used, the type of solvent, and the like, but is usually −50 ° C. to 100 ° C. (preferably 0 ° C. to 50 ° C.).
[0181]
The reaction time varies depending on the raw material compound, the reducing agent used, the solvent, the reaction temperature and the like, but is usually 15 minutes to 150 hours (preferably 1 hour to 100 hours).
[0182]
After completion of the reaction, the target compound (3) of this reaction is collected from the reaction mixture according to a conventional method. For example, neutralize the reaction mixture as appropriate, or remove insoluble matter by filtration, add water and an immiscible organic solvent such as ethyl acetate, and separate the organic layer containing the target compound, After washing with water and the like, it is obtained by drying with anhydrous magnesium sulfate, anhydrous sodium sulfate, anhydrous sodium hydrogencarbonate and the like and then distilling off the solvent. If necessary, the obtained target compound can be separated and purified by a conventional method such as recrystallization, reprecipitation, chromatography and the like.
[0183]
Step C-2 is a step of producing a compound having the general formula (4). After converting the hydroxy group of the compound (3) to a leaving group in an inert solvent in the presence of a base, iodination is performed. By reacting with the agent.
[0184]
Examples of the reagent for converting a hydroxy group into a leaving group include sulfonyl halides such as methanesulfonyl chloride and P-toluenesulfonyl chloride; thionyl halides such as thionyl chloride, thionyl bromide and thionyl iodide; Sulfuryl halides such as sulfuryl iodide; phosphorus trihalides such as phosphorus trichloride, phosphorus tribromide and phosphorus triiodide; five such as phosphorus pentachloride, phosphorus pentabromide and phosphorus pentaiodide Phosphorus halides; halogenating agents such as phosphorus oxychloride, phosphorus oxybromide, phosphorus oxyiodide; or rhenium reagents such as methyltrioxorhenium (VII); Preferred is a sulfonyl halide (particularly P-toluenesulfonyl chloride).
[0185]
Examples of the base used for converting the hydroxy group into the leaving group include alkali metal carbonates such as lithium carbonate, sodium carbonate and potassium carbonate; alkalis such as lithium hydrogen carbonate, sodium hydrogen carbonate and potassium hydrogen carbonate. Metal bicarbonates; alkali metal hydrides such as lithium hydride, sodium hydride, potassium hydride; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide; lithium methoxide, Alkali metal alkoxides such as sodium methoxide, sodium ethoxide, potassium t-butoxide; or triethylamine, tributylamine, diisopropylethylamine, N-methylmorpholine, pyridine, 4- (N, N-dimethylamino) pyridine, N, N-dimethylaniline N, N-diethylaniline, 1,5-diazabicyclo [4.3.0] non-5-ene, 1,4-diazabicyclo [2.2.2] octane (DABCO), 1,8-diazabicyclo [5. 4.0] -7-undecene (DBU), preferably organic amines (most preferably triethylamine).
[0186]
Examples of the inert solvent used for converting the hydroxy group into the leaving group include aliphatic hydrocarbons such as hexane, heptane, ligroin and petroleum ether; aromatic hydrocarbons such as benzene, toluene and xylene. Halogenated hydrocarbons such as chloroform, dichloromethane, 1,2-dichloroethane, carbon tetrachloride; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, diethylene glycol dimethyl ether; acetone, 2-butanone Ketones such as: formamide, dimethylformamide, dimethylacetamide, amides such as hexamethylphosphoric triamide; sulfoxides such as dimethyl sulfoxide; or sulfolane, preferably halogenated carbon Hydrogen compounds (most preferably, dichloromethane) it is.
[0187]
The reaction temperature for converting a hydroxy group to a leaving group varies depending on the raw material compound, the reagent used, the type of solvent, etc., but is usually −50 ° C. to 200 ° C. (preferably −10 ° C. to 150 ° C. ).
[0188]
The reaction time for converting the hydroxy group to the leaving group varies depending on the raw material compound, the reagent used, the solvent, the reaction temperature, etc., but is usually 15 minutes to 24 hours (preferably 30 minutes to 12 hours). It is.
[0189]
The iodinating agent used in the above reaction is, for example, phosphorus pentaiodide, phosphorus oxyiodide, sodium iodide, or potassium iodide, and preferably sodium iodide.
[0190]
The reaction temperature for iodination of the leaving group varies depending on the raw material compound, the reagent used, the type of solvent, etc., but is usually 0 ° C. to 200 ° C. (preferably 10 ° C. to 150 ° C.).
[0191]
The reaction time for iodination of the leaving group varies depending on the raw material compound, the reagent used, the solvent, the reaction temperature, etc., but is usually 15 minutes to 24 hours (preferably 30 minutes to 12 hours).
[0192]
After completion of the reaction, the target compound (4) of this reaction is collected from the reaction mixture according to a conventional method. For example, neutralize the reaction mixture as appropriate, or remove insoluble matter by filtration, add water and an immiscible organic solvent such as ethyl acetate, and separate the organic layer containing the target compound, After washing with water and the like, it is obtained by drying with anhydrous magnesium sulfate, anhydrous sodium sulfate, anhydrous sodium hydrogencarbonate and the like and then distilling off the solvent. If necessary, the obtained target compound can be separated and purified by a conventional method such as recrystallization, reprecipitation, chromatography and the like.
[0193]
Step C-3 is a step of producing a compound having the general formula (6), and reacting the compound (4) with a compound having the general formula (5) in the presence of a base in an inert solvent. Is done.
[0194]
Examples of the inert solvent used in the above reaction include ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, and diethylene glycol dimethyl ether; methanol, ethanol, n-propanol, and isopropanol. Alcohols such as benzene, n-butanol, isobutanol, t-butanol, isoamyl alcohol, diethylene glycol, glycerin, octanol, cyclohexanol, methyl cellosolve; Amides such as hexamethylphosphoric triamide; water; or a mixed solvent of the above solvents, preferably alcohols or amides (most preferably dimethylformamide).
[0195]
The base used in the above reaction is, for example, the same as that used when converting the hydroxy group in Step C-2 to a leaving group, preferably alkali metal hydrides or Alkali metal alkoxides (most preferably sodium hydride).
[0196]
The reaction temperature varies depending on the raw material compound, base, type of solvent, etc., but is usually −78 ° C. to 100 ° C. (preferably 0 ° C. to 50 ° C.).
[0197]
The reaction time varies depending on the raw material compound, base, solvent, reaction temperature and the like, but is usually 15 minutes to 48 hours (preferably 30 minutes to 12 hours).
[0198]
After completion of the reaction, the target compound (6) of this reaction is collected from the reaction mixture according to a conventional method. For example, neutralize the reaction mixture as appropriate, or remove insoluble matter by filtration, add water and an immiscible organic solvent such as ethyl acetate, and separate the organic layer containing the target compound, After washing with water and the like, it is obtained by drying with anhydrous magnesium sulfate, anhydrous sodium sulfate, anhydrous sodium hydrogencarbonate and the like and then distilling off the solvent. If necessary, the obtained target compound can be separated and purified by a conventional method such as recrystallization, reprecipitation, chromatography and the like.
[0199]
Step C-4 is a step of producing a compound having the general formula (7). The compound (6) is reacted with a base in the presence of water in an inert solvent to form one lower alkoxycarbonyl group. This is done by hydrolysis.
[0200]
The inert solvent used in the above reaction is not particularly limited as long as it is inert to this reaction. For example, aliphatic hydrocarbons such as hexane, heptane, ligroin, petroleum ether; benzene, toluene, Aromatic hydrocarbons such as xylene; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, diethylene glycol dimethyl ether; methanol, ethanol, n-propanol, isopropanol, n Alcohols such as butanol, isobutanol, t-butanol, isoamyl alcohol, diethylene glycol, glycerin, octanol, cyclohexanol, methyl cellosolve; or a mixed solvent of the above solvents, preferably Are alcohols (most preferably Ethanol - is a le).
[0201]
The base used in the above reaction is, for example, the same as that used when converting the hydroxy group in Step C-2 to a leaving group, and preferably alkali metal hydroxides ( Most preferred is potassium hydroxide).
[0202]
The reaction temperature varies depending on the raw material compound, the base, the type of the solvent, and the like, but is usually −20 ° C. to 200 ° C. (preferably 0 ° C. to 50 ° C.).
[0203]
The reaction time varies depending on the raw material compound, base, solvent, reaction temperature and the like, but is usually 30 minutes to 120 hours (preferably 1 hour to 80 hours).
[0204]
After completion of the reaction, the target compound (7) of this reaction is collected from the reaction mixture according to a conventional method. For example, neutralize the reaction mixture as appropriate, or remove insoluble matter by filtration, add water and an immiscible organic solvent such as ethyl acetate, and separate the organic layer containing the target compound, After washing with water and the like, it is obtained by drying with anhydrous magnesium sulfate, anhydrous sodium sulfate, anhydrous sodium hydrogencarbonate and the like and then distilling off the solvent. If necessary, the obtained target compound can be separated and purified by a conventional method such as recrystallization, reprecipitation, or chromatography.
[0205]
Step C-5 is a step of producing a compound having the general formula (9), which is a method of subjecting the carboxyl group of the compound (7) to a Curtius rearrangement reaction to convert it to a carbamate, and converting the compound (7) The reaction is carried out by reacting with a diaryl phosphate azide derivative such as diphenyl phosphate azide in the presence of a base in an inert solvent and then with a compound having the general formula (8).
[0206]
The inert solvent used in the above reaction is not particularly limited as long as it is inert to this reaction. For example, aliphatic hydrocarbons such as hexane, heptane, ligroin, petroleum ether; benzene, toluene, Aromatic hydrocarbons such as xylene; Halogenated hydrocarbons such as chloroform, dichloromethane, 1,2-dichloroethane, carbon tetrachloride; Diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, diethylene glycol dimethyl ether, etc. Ethers; or a mixed solvent of the above-mentioned solvents, and preferably aromatic hydrocarbons (most preferably benzene).
[0207]
The base used in the above reaction is, for example, the same one used when converting the hydroxy group in Step C-2 to a leaving group, and preferably an organic amine (most preferred). Is triethylamine).
[0208]
The reaction temperature for reacting compound (7) with a diarylphosphoric acid azide derivative varies depending on the raw material compound, base, type of solvent, etc., but is usually 0 ° C. to 200 ° C. (preferably 20 ° C. to 150 ° C.). It is.
[0209]
The reaction time for reacting compound (7) with a diarylphosphoric acid azide derivative varies depending on the raw material compound, base, solvent, reaction temperature, etc., but is usually 15 minutes to 24 hours (preferably 30 minutes to 12 hours). It is.
[0210]
After reacting compound (7) with a diarylphosphoric acid azide derivative, compound (8) is added and reacted in the same reaction solution.
[0211]
The reaction temperature varies depending on the kind of the raw material compound, base, solvent, etc., but is usually 0 ° C. to 200 ° C. (preferably 20 ° C. to 150 ° C.).
[0212]
The reaction time varies depending on the raw material compound, base, solvent, reaction temperature and the like, but is usually 15 minutes to 24 hours (preferably 30 minutes to 12 hours).
[0213]
In addition, when reacting the compound (7) with a diarylphosphoric acid azide derivative, by reacting the compound (8) which is difficult to react directly with the diarylphosphoric acid azide derivative together, the carboxyl group is converted to a carbamate all at once. Can be converted.
[0214]
After completion of the reaction, the target compound (9) of this reaction is collected from the reaction mixture according to a conventional method. For example, neutralize the reaction mixture as appropriate, or remove insoluble matter by filtration, add water and an immiscible organic solvent such as ethyl acetate, and separate the organic layer containing the target compound, After washing with water and the like, it is obtained by drying with anhydrous magnesium sulfate, anhydrous sodium sulfate, anhydrous sodium hydrogencarbonate and the like and then distilling off the solvent. If necessary, the obtained target compound can be separated and purified by a conventional method such as recrystallization, reprecipitation, chromatography and the like.
[0215]
Step C-6 is a step of producing a compound having the general formula (10), and reducing the ester moiety of the compound (9)²R^TenThis is carried out by removing the group having a lower aliphatic acylation or lower alkoxycarbonylation (acylation).
[0216]
The reaction for reducing the ester moiety of compound (9) is carried out in the same manner as in step C-1.
[0217]
Formula CO₂R^TenThe reaction for removing the group having acyl and acylation are carried out in the same manner as in the step A-1.
[0218]
The phosphoric acid or phosphonic acid derivative having the general formula (I) of the present invention, its pharmacologically acceptable salt or its pharmacologically acceptable ester has an excellent immunosuppressive action with low toxicity and can be used for various organ transplantation or Skin graft rejection, systemic lupus erythematosus, rheumatoid arthritis, polymyositis, connective tissue inflammation, skeletal myositis, osteoarthritis, osteoarthritis, dermatomyositis, scleroderma, Behcet's disease, Chron's disease, ulcerative colon Inflammation, autoimmune hepatitis, aplastic anemia, idiopathic thrombocytopenic purpura, autoimmune hemolytic anemia, multiple sclerosis, autoimmune bullosa, psoriasis vulgaris, vascular inflammation group, Wegener granulomas, Uveitis, Sjogren's syndrome, idiopathic interstitial pneumonia, Goodpasture syndrome, sarcoidosis, allergic granulomatous vasculitis, bronchial asthma, myocarditis, cardiomyopathy, aortitis syndrome, post-myocardial infarction syndrome, Pulmonary hypertension, minimal change nephrosis, membranous nephropathy, membranoproliferative nephritis, focal glomerulosclerosis, crescent nephritis, myasthenia gravis, inflammatory neuropathy, atopic dermatitis, chronic Photodermatitis, photosensitivity, pressure ulcer, Sydenham chorea, systemic sclerosis, adult-onset diabetes, insulin-dependent diabetes, juvenile diabetes, atherosclerosis, glomerulonephritis, IgA nephropathy, tubule Interstitial nephritis, primary biliary cirrhosis, primary sclerosing cholangitis, fulminant hepatitis, viral hepatitis, GVHD, contact dermatitis, autoimmune diseases such as sepsis or other immune related diseases, fungi, mycoplasma, virus, Infectious diseases such as protozoa, heart failure, cardiac hypertrophy, arrhythmia, angina pectoris, cardiac ischemia, arterial embolism, aneurysm, varicose vein, circulatory disorders such as blood circulation disorder, Alzheimer's disease, dementia, Parkinson's disease, stroke, cerebral infarction , Cerebral ischemia, depression, manic depression, schizophrenia, Huntington's chorea, epilepsy, convulsions, hyperactivity, encephalitis, meningitis, anorexia and binge eating, central diseases such as lymphoma, leukemia, polyuria, frequent urination, Of various diseases such as diabetic retinopathy (particularly preferably, rejection in various organ transplantation or skin transplantation, systemic lupus erythematosus, rheumatoid arthritis, multiple sclerosis, atopic dermatitis, etc.) It is useful as a prophylactic or therapeutic agent (especially therapeutic agent) for warm-blooded animals (especially for humans).
[0219]
When the compound having the general formula (I) of the present invention, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof is used as a therapeutic or prophylactic agent for the above-mentioned diseases, it is suitable for itself or appropriately. Mix with pharmacologically acceptable excipients, diluents, etc., for example, orally by tablets, capsules, granules, powders or syrups, or parenterally by injections or suppositories can do.
[0220]
These formulations include excipients (eg sugar derivatives such as lactose, sucrose, sucrose, mannitol, sorbitol; starch derivatives such as corn starch, potato starch, alpha starch, dextrin; cellulose derivatives such as crystalline cellulose; Gum arabic; dextran; organic excipients such as pullulan; and silicate derivatives such as light anhydrous silicic acid, synthetic aluminum silicate, calcium silicate, magnesium magnesium aluminosilicate; phosphates such as calcium hydrogen phosphate Carbonates such as calcium carbonate; or inorganic excipients such as sulfates such as calcium sulfate.), Lubricants (eg, stearic acid, calcium stearate, metal stearate such as magnesium stearate); Salt; talc; colloidal silica; like veegum, gay wax Wax; boric acid; adipic acid; sulfate such as sodium sulfate; glycol; fumaric acid; sodium benzoate; DL leucine; fatty acid sodium salt; lauryl sulfate such as sodium lauryl sulfate and magnesium lauryl sulfate; silicic anhydride, silicic acid Silicates such as hydrates; or the above-mentioned starch derivatives), binders (for example, hydroxypropylcellulose, hydroxypropylmethylcellulose, polyvinylpyrrolidone, macrogol, or the same compounds as the excipients. ), Disintegrants (eg, cellulose derivatives such as low substituted hydroxypropylcellulose, carboxymethylcellulose, carboxymethylcellulose calcium, sodium carboxymethylcellulose; carboxymethyl starch, carboxy Chemically modified starch and celluloses such as sodium silmethyl starch or cross-linked polyvinyl pyrrolidone), stabilizers (for example, para-oxybenzoates such as methylparaben, propylparaben; chlorobutanol, benzyl alcohol, phenylethyl) Alcohols such as alcohol; benzalkonium chloride; phenols such as phenol and cresol; thimerosal; dehydroacetic acid; or sorbic acid), flavoring agents (eg, commonly used sweeteners, acidulants , Fragrances, etc.), and manufactured by a well-known method using additives such as diluents.
[0221]
The amount used varies depending on the symptoms, age, etc. In the case of oral administration, the lower limit of 0.05 mg (preferably 5 mg) and the upper limit of 200 mg (preferably 40 mg) per day are administered intravenously. In this case, a daily lower limit of 0.01 mg (preferably 1 mg) and an upper limit of 100 mg (preferably 10 mg) should be administered to adults 1 to 6 times daily according to symptoms. Is desirable.
[0222]
【Example】
Hereinafter, the present invention will be described in more detail with reference to examples and test examples, but the scope of the present invention is not limited thereto.
[0223]
Example 1
Phosphoric acid mono- (2R) -amino-2-methyl-4- [5- (5-phenylpentanoyl) thiophen-2-yl] butyl ester
[0224]
Embedded image

[0225]
(a)
Acetic acid (2R) -acetylamino-2-methyl-4- [5- (5-phenylpent-1-ynyl) thiophen-2-yl] butyl ester
4.00 g (11.5 mmol) of acetic acid (2R) -acetylamino-2-methyl-4- (5-bromothiophen-2-yl) butyl ester synthesized in Reference Example 2 was dissolved in 40 mL of dimethylformamide. 4.97 g (34.5 mmol) of 5-phenylpent-1-yne synthesized in Step 4, 16.0 mL (115 mmol) of triethylamine, 437 mg (2.30 mmol) of copper (I) iodide, dichlorobis (triphenylphosphine) paradiu
806 mg (1.15 mmol) was added, and the mixture was stirred at 80 ° C. for 2 hours under a nitrogen atmosphere. The reaction solution was mixed with saturated aqueous ammonium chloride solution and extracted with ethyl acetate, and the ethyl acetate layer was washed with water and saturated brine. The ethyl acetate layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: hexane / ethyl acetate = 1/1 to 1/2), and further preparative HPLC (column: TSKgel ODS-80Ts 55 × 300 mm, elution solvent: acetonitrile / water = 1/1). And purified at a flow rate of 50 mL / min) to give 3.27 g (69% yield) of the title compound as a colorless oil.
Nuclear magnetic resonance spectrum (400MHz, CDCl_Three), Δ: 1.36 (3H, s), 1.85-2.05 (3H, m), 1.94 (3H, s), 2.10 (3H, s), 2.25-2.35 (1H, m), 2.43 (2H, t, J = 7.0 Hz), 3.70-3.80 (4H, m), 4.17 (1H, d, J = 11.2 Hz), 4.31 (1H, d, J = 11.2 Hz), 5.38 (1H, bRs), 6.64 (1H, d , J = 3.6 Hz), 6.94 (1H, d, J = 3.6 Hz), 7.15-7.42 (5H, m).
Mass spectrum (FAB), m / z: 412 ((M + H)⁺)
[0226]
(b)
(2R) -Amino-2-methyl-4- [5- (5-phenylpentanoyl) thiophen-2-yl] butan-1-ol
3.27 g of acetic acid (2R) -acetylamino-2-methyl-4- [5- (5-phenylpent-1-ynyl) thiophen-2-yl] butyl ester obtained in Example 1 (a) (7. 95 mmol) was dissolved in 20 mL of tetrahydrofuran, 20 mL of methanol and 20 mL of water, 3.33 g (79.5 mmol) of lithium hydroxide monohydrate was added, and the mixture was stirred at 50 ° C. for 6 hours. The reaction mixture was poured into water and extracted with methylene chloride. The methylene chloride layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was dissolved in 25 mL of methanol, 25 mL of 6N sulfuric acid was added, and the mixture was stirred at 100 ° C. for 2 hours. The reaction solution was made alkaline by adding 20% aqueous sodium hydroxide solution under ice-cooling, extracted with methylene chloride, the methylene chloride layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (silica gel: Chromatorex NH, 100-200 mesh, elution solvent: methylene chloride / methanol = 1 / 0-50 / 1) to give 2.13 g (76% yield) of the title compound as a pale yellow solid. Obtained.
Nuclear magnetic resonance spectrum (400MHz, CD_ThreeOD), δ: 1.09 (3H, s), 1.62-1.86 (6H, m), 2.64 (2H, t, J = 7.1 Hz), 2.84-2.98 (4H, m), 3.34 (1H, d, J = 10.8 Hz), 3.38 (1H, d, J = 10.8 Hz), 6.93 (1H, d, J = 3.7 Hz), 7.10-7.28 (5H, m), 7.68 (1H, d, J = 3.7 Hz).
Mass spectrum (FAB), m / z: 346 ((M + H)⁺).
[0227]
(c)
(2R) -t-Butoxycarbonylamino-2-methyl-4- [5- (5-phenylpentanoyl) thiophen-2-yl] butan-1-ol
724 mg (2.09 mmol) of (2R) -amino-2-methyl-4- [5- (5-phenylpentanoyl) thiophen-2-yl] butan-1-ol obtained in Example 1 (b) was salified. Dissolved in 8 mL of methylene, 8 m of 1N aqueous sodium hydroxide solution and 684 mg (3.13 mmol) of di-t-butyl dicarbonate were added, and the mixture was stirred at room temperature for 2 hours. The reaction solution was diluted with methylene chloride, and water was added for liquid separation. The methylene chloride layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (developing solvent: hexane / ethyl acetate = 3/2) to obtain 890 mg (yield 95%) of the title compound as a white solid.
Nuclear magnetic resonance spectrum (400MHz, CDCl_Three), Δ: 1.21 (3H, s), 1.43 (9H, s), 1.66-1.83 (4H, m), 1.97-2.06 (1H, m), 2.13-2.21 (1H, m), 2.61-2.68 (2H , m), 2.78-2.98 (4H, m), 3.64-3.72 (2H, m), 3.96 (1H, brs), 4.63 (1H, brs), 6.84 (1H, d, J = 3.9Hz), 7.13- 7.30 (5H, m), 7.51 (1H, d, J = 3.9Hz).
Mass spectrum (FAB), m / z: 446 ((M + H)⁺).
[0228]
(d)
Bis-allyl-mono- (2R) -t-butoxycarbonylamino-2-methyl-4- [5- (5-phenylpentanoyl) thiophen-2-yl] butyl ester
(2R) -t-Butoxycarbonylamino-2-methyl-4- [5- (5-phenylpentanoyl) thiophen-2-yl] butan-1-ol 777 mg (1.74) obtained in Example 1 (c) mmol) was dissolved in 8 mL of methylene chloride, and 820 mg (11.7 mmol) of tetrazole was added. Under ice-cooling, 922 μL (3.49 mmol) of diallyldiisopropyl phosphoramidite was added. The mixture was stirred for 5 minutes under ice cooling, then returned to room temperature and stirred for 2 hours. 1 mL of methanol was added under ice-cooling, and 1.05 mL (5.22 mmol) of 5-6M t-butyl hydroperoxide-decane solution was slowly added. After stirring for 10 minutes under ice cooling, 10 mL of a saturated aqueous sodium sulfite solution was added, and the mixture was diluted with methylene chloride and separated. The methylene chloride layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (developing solvent: hexane / ethyl acetate = 3/2) to obtain 420 mg (yield 46%) of the title compound as a colorless oil.
[0229]
Nuclear magnetic resonance spectrum (400MHz, CDCl_Three), Δ: 1.32 (3H, s), 1.44 (9H, s), 1.66-1.82 (4H, m), 1.88-1.98 (1H, m), 2.21-2.33 (1H, m), 2.63-2.68 (2H , m), 2.82-2.87 (4H, m), 3.98-4.04 (1H, m), 4.15-4.21 (1H, m), 4.53-4.59 (4H, m), 4.64 (1H, bRrs), 5.24-5.41 (4H, m), 5.59-6.00 (2H, m), 6.83 (1H, d, J = 3.7Hz), 7.14-7.30 (5H, m), 7.51 (1H, d, J = 3.7Hz).
Mass spectrum (FAB), m / z: 606 ((M + H)⁺).
[0230]
(e)
Phosphoric acid mono- (2R) -amino-2-methyl-4- [5- (5-phenylpentanoyl) thiophen-2-yl] butyl ester
Bis-allyl-mono- (2R) -t-butoxycarbonylamino-2-methyl-4- [5- (5-phenylpentanoyl) thiophen-2-yl] phosphate obtained in Example 1 (d) 400 mg (0.66 mmol) of butyl ester was dissolved in 5 mL of acetonitrile, and 37 mg (0.03 mmol) of tetrakis (triphenylphosphine) palladium was added. Under ice-cooling, pyrrolidine 135 μL (1.62 mmol) was added. After stirring for 30 minutes under ice cooling, the mixture was returned to room temperature and stirred for 1 hour and 30 minutes. The solvent was distilled off under reduced pressure and purified by preparative HPLC (column: Inertsil ODS-3 20 × 250 mm, elution solvent: acetonitrile / 0.1% aqueous ammonium acetate solution = 1/1, flow rate: 10 mL / min). The purified product was dissolved in 2 mL of ethanol, and 2 mL of 4N hydrochloric acid dioxane solution was added under ice cooling. The mixture was stirred for 30 minutes under ice cooling, then returned to room temperature and stirred for 4 hours. The solvent was distilled off under reduced pressure and recrystallized from methanol-water to obtain 115 mg (yield 51%) of the title compound as pale yellow crystals.
Nuclear magnetic resonance spectrum (400MHz, DMSO-d₆), Δ: 1.22 (3H, s), 1.52-1.65 (4H, m), 1.83-2.05 (2H, m), 2.52-2.63 (2H, m), 2.81-2.97 (4H, m), 3.71-3.88 (2H, m), 6.98 (1H, d, J = 3.7Hz), 7.14-7.28 (5H, m), 7.74 (1H, d, J = 3.7Hz).
Mass spectrum (FAB), m / z: 426 ((M + H)⁺).
[0231]
(Example 2)
Phosphoric acid mono- (2R) -amino-2-methyl-4- [5- (4-cyclohexyloxybut-1-ynyl) thiophen-2-yl] butyl ester
[0232]
Embedded image

[0233]
(a)
(2R) -Allyloxycarbonylamino-2-methyl-4- [5- (4-cyclohexyloxybut-1-ynyl) thiophen-2-yl] butan-1-ol
500 mg (1.11 mmol) (2R) -amino-2-methyl-4- [5- (4-cyclohexyloxybut-1-ynyl) thiophen-2-yl] butan-1-ol maleate synthesized in Reference Example 6 10 mL of 1N aqueous sodium hydroxide solution was added to) and extracted with methylene chloride. The methylene chloride layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was dissolved in 8 mL of ethyl acetate and 8 mL of water, 141 mg (1.33 mmol) of potassium hydrogen carbonate and 133 μL (1.33 mmol) of allyl chloroformate were added, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into water and extracted with ethyl acetate, and the ethyl acetate layer was washed with saturated brine. The ethyl acetate layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel chromatography (developing solvent: hexane / ethyl acetate = 2/1 to 3/2) to obtain 465 mg (100%) of the title compound as a colorless oil.
[0234]
Nuclear magnetic resonance spectrum (400MHz, CDCl_Three), Δ: 1.15-1.35 (8H, m), 1.50-1.60 (1H, m), 1.70-1.80 (2H, m), 1.88-2.03 (3H, m), 2.08-2.18 (1H, m), 2.67 (2H, t, J = 7.2Hz), 2.72-2.90 (2H, m), 3.27-3.34 (1H, m), 3.47 (1H, brs), 3.62-3.75 (4H, m), 4.53 (2H, d , J = 5.7Hz), 4.82 (1H, brs), 5.22-5.35 (2H, m), 5.86-5.97 (1H, m), 6.63 (1H, d, J = 3.6Hz), 6.93 (1H, d, J = 3.6Hz).
Mass spectrum (FAB), m / z: 420 ((M + H)⁺).
[0235]
(b)
Phosphoric acid mono- (2R) -amino-2-methyl-4- [5- (4-cyclohexyloxybut-1-ynyl) thiophen-2-yl] butyl ester
(2R) -allyloxycarbonylamino-2-methyl-4- [5- (4-cyclohexyloxybut-1-ynyl) thiophen-2-yl] butan-1-ol obtained in Example 2 (a) 465 mg (1.11 mmol) was dissolved in 10 mL of methylene chloride, 465 mg (6.64 mmol) of tetrazole was added, and 1.17 mL (4.43 mmol) of diallyl diisopropyl phosphoramidite was added under ice cooling. After stirring at room temperature for 1 hour, 0.66 mL (3.32 mmol) of 5-6 M t-butyl hydroperoxide-decane solution was slowly added under ice cooling. After stirring for 5 minutes under ice cooling, 10 mL of a 10% aqueous sodium thiosulfate solution was added, and the mixture was extracted with methylene chloride. The methylene chloride layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (developing solvent: hexane / ethyl acetate = 3/1 to 3/2). Dissolve 248 mg (0.43 mmol) of the purified product in 5 mL of acetonitrile, add 25 mg (0.02 mmol) of tetrakis (triphenylphosphine) palladium, add 179 μL (2.14 mmol) of pyrrolidine under ice cooling, and stir at room temperature for 2 hours. did. The deposited precipitate was collected by filtration, added with 10 mL of a mixture of acetonitrile and 0.1% ammonium acetate aqueous solution (1: 1), heated and allowed to stand. The resulting precipitate was collected by filtration and dried to give 35 mg (8%) of the title compound as white crystals.
[0236]
Nuclear magnetic resonance spectrum (400MHz, CD_ThreeCOOD), δ: 1.15-1.40 (5H, m), 1.43 (3H, s), 1.49-1.57 (1H, m), 1.70-1.80 (2H, m), 1.90-1.98 (2H, m), 2.01- 2.22 (2H, m), 2.68 (2H, t, J = 6.6Hz), 2.84-3.00 (2H, m), 3.37-3.46 (1H, m), 3.71 (2H, t, J = 6.6Hz), 4.08 -4.16 (2H, m), 6.73 (1H, d, J = 3.7Hz), 6.96 (1H, d, J = 3.7Hz).
Mass spectrum (FAB), m / z: 414 ((M + H)^-).
[0237]
(Example 3)
(3R) -Amino-3-methyl-5- [5- (5-phenylpentyl) thiophen-2-yl] pentylphosphonic acid
[0238]
Embedded image

[0239]
(a)
(2R) -t-Butoxycarbonylamino-2-methyl-4- [5- (5-phenylpentyl) thiophen-2-yl] -1-butanal
1.26 g (3.97 mmol) of (2R) -amino-2-methyl-4- [5- (5-phenylpentyl) thiophen-2-yl] butan-1-ol obtained in Reference Example 8 was added to 25 mL of methylene chloride. The mixture was dissolved, and 1.04 g (4.76 mmol) of di-t-butyl dicarbonate and 0.55 mL (3.97 mmol) of triethylamine were added with stirring under ice cooling, followed by stirring at room temperature for 16 hours. After completion of the reaction, water was added to the reaction solution and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (developing solvent: hexane / ethyl acetate = 1/1) to obtain 1.12 g (yield 70%) of Nt-butoxycarbonyl form (N-Boc form). 150 mg (0.35 mmol) of N-Boc compound was dissolved in 7.5 mL of methylene chloride, and 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3 (1H ) -One (Dess-Martin reagent) 222 mg (0.52 mmol) was added, and the mixture was stirred at room temperature for 1.5 hours. After completion of the reaction, an aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was stirred at room temperature for 30 minutes. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (developing solvent: hexane / ethyl acetate = 5/1) to obtain 150 mg (yield 100%) of the title compound as a colorless syrup.
[0240]
Nuclear magnetic resonance spectrum (400MHz, CDCl_Three), Δ: 9.33 (s, 1H), 7.42-7.23 (m, 2H), 7.22-7.17 (m, 3H), 6.54 (d, 1H, J = 3.66 Hz), 6.53 (d, 1H, J = 3.66 Hz), 5.25-5.11 (brs, 1H), 2.73 (t, 2H, J = 7.70Hz), 2.41-2.26 (m, 1H), 2.12-2.00 (m, 1H), 2.71-1.58 (m, 4H) , 1.45 (s, 9H), 1.51-1.32 (m, 2H), 1.38 (s, 3H).
Infrared absorption spectrum, νmax cm^-1 (CHCl3): 3443, 3413, 2981, 2934, 2858, 1708, 1495, 1453, 1369, 1253, 1164, 1074.
Mass spectrum (FAB), m / z: 430 ((M + H)^-).
[0241]
(b)
0.53 mL (2.26 mmol) of (3R) -t-butoxycarbonylamino-3-methyl-5- [5- (5-phenylpentyl) thiophen-2-yl] -1-pentenylphosphonic acid diethyl ester tetraethyl methylene diphosphonate It was dissolved in 15 mL of benzene, and 90 mg (2.17 mmol) of 60% sodium hydride was added with stirring under ice cooling. Then, after stirring at room temperature for 30 minutes, (2R) -t-butoxycarbonylamino-2-methyl-4- [5- (5-phenylpentyl) thiophene-2- obtained in Example 3 (a) was obtained. Yl] -1-butanal (194 mg, 0.45 mmol) was added, and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, an aqueous ammonium chloride solution was added to the reaction solution, and the organic layer was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (developing solvent: hexane / ethyl acetate = 1/1) to obtain 227 mg (yield 89%) of the title compound as a colorless syrup.
[0242]
Nuclear magnetic resonance spectrum (400MHz, CDCl3), δ: 7.29-7.26 (m, 2H), 7.19-7.16 (m, 3H), 6.76 (dd, 1H, J = 17.6, 22.7 Hz), 6.56-6.53 (m, 2H,), 5.70 (dd, 2H, J = 17.6, 17.8 Hz) 4.65-4.55 (br s, 1H), 4.18-4.02 (m, 4H), 2.80-2.67 (m, 4H), 2.61 (t, 2H , J = 7.69 Hz), 2.23-2.21 (m, 1H), 2.08-1.90 (m, 1H), 1.73-1.55 (m, 4H), 1.43 (s, 9H), 1.34 (t, 6H, J = 6.97 Hz), 1.26 (t, 3H, J = 6.97 Hz).
Infrared absorption spectrum, ν_max cm^-1 (CDCl3): 3443, 2982, 2933, 2858, 2244, 1718, 1495, 1454, 1368, 1245, 1166, 1057, 1029.
Mass spectrum (FAB), m / z: 564 ((M + H)^-).
[0243]
(c)
(3R) -t-Butoxycarbonylamino-3-methyl-5- [5- (5-phenylpentyl) thiophen-2-yl] pentylphosphonic acid diethyl ester
100 mg of (3R) -t-butoxycarbonylamino-3-methyl-5- [5- (5-phenylpentyl) thiophen-2-yl] -1-pentenylphosphonic acid diethyl ester obtained in Example 3 (b) (0.18 mmol) was dissolved in 4 mL of ethanol, 82 mg of chlorotris (triphenylphosphine) rhodium was added with stirring at room temperature, and the mixture was stirred at 70 ° C. for 5 hours in a hydrogen atmosphere. After completion of the reaction, the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (developing solvent: hexane / ethyl acetate = 1/3) to obtain 62 mg (yield 62%) of the title compound as a colorless syrup.
[0244]
Nuclear magnetic resonance spectrum (400MHz, CDCl3), δ: 7.31-7.23 (m, 2H), 7.22-7.13 (m, 3H), 6.56 (d, 1H, J = 2.93 Hz), 6.53 (d, 1H, J = 2.93 Hz), 4.42-4.23 (brs, 1H), 4.18-4.01 (m, 4H), 2.80-2.65 (m, 4H), 2.61 (t, 2H, J = 7.70 Hz), 2.22-2.08 (m, 2H ), 1.91-1.53 (m, 10H), 1.43 (s, 9H), 1.33 (t, 6H, J = 7.33 Hz), 1.21 (s, 3H).
Infrared absorption spectrum, ν_max cm^-1 (CHCl3): 3443, 2984, 2935, 1714, 1498, 1454, 1392, 1368, 1165, 1063, 1031, 967.
Mass spectrum (FAB), m / z: 566 ((M + H)^-).
[0245]
(d)
(3R) -Amino-3-methyl-5- [5- (5-phenylpentyl) thiophen-2-yl] pentylphosphonic acid
63 mg (0.11 mmol) of (3R) -t-butoxycarbonylamino-3-methyl-5- [5- (5-phenylpentyl) thiophen-2-yl] pentylphosphonic acid diethyl ester obtained in Example 3 (c) 4 mL of 4N dioxane hydrochloride solution and 1 mL of water were added to the solution, and the mixture was stirred at 80 ° C. for 8 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. The residue was dissolved in 0.5 mL of methanol, 5 mL of water was added, and recrystallization was performed to obtain 28 mg (yield 62%) of the title compound.
[0246]
Nuclear magnetic resonance spectrum (400MHz, CD3OD), δ: 7.25-7.18 (m, 2H), 7.18-7.19 (m, 3H), 6.64 (d, 1H, J = 3.30 Hz), 6.56 (d, 1H, J = 3.30 Hz), 2.83 (t, 2H, J = 8.79 Hz), 2.74 (t, 2H, J = 7.33 Hz), 2.59 (t, 2H, J = 7.33 Hz), 2.05-1.85 (m, 4H), 1.72-1.56 (m, 6H), 1.44-1.31 (m, 5H).
Infrared absorption spectrum, ν_max cm^-1 (KBr): 2930, 1632, 1552, 1496, 1453, 1389, 1180, 1048, 946, 800, 746, 698.
Mass spectrum (FAB), m / z: 408 ((M + H)^-).
Example 4
(3R) -Amino-3-methyl-5- [5- (5-phenylpentanoyl) thiophen-2-yl] pentylphosphonic acid
[0247]
Embedded image

[0248]
(a)
(2R) -t-Butoxycarbonylamino-2-methyl-4- [5- (5-phenylpentanoyl) thiophen-2-yl] -1-butanal
637 mg (1.84 mmol) of (2R) -amino-2-methyl-4- [5- (5-phenylpentanoyl) thiophen-2-yl] butan-1-ol obtained in Reference Example 10 was added to methylene chloride (18 mL). ), 492 mg (2.26 mmol) of di-t-butyl dicarbonate and 5.61 mL (6.80 mmol) of triethylamine were added, and the mixture was stirred at room temperature for 20 hours. After concentration under reduced pressure, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography (eluent: hexane / ethyl acetate = 3/2) to give N-Boc form [(2R) -t-butoxycarbonylamino-2. 678 mg (83%) of -methyl-4- [5- (5-phenylpentanoyl) thiophen-2-yl] butan-1-ol] were obtained.
[0249]
673 mg (1.51 mmol) of the obtained N-Boc compound was dissolved in methylene chloride (15 mL), and 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3 (1H) -965 mg (2.28 mmol) of ON (Dess-Martin reagent) was added, and it stirred at room temperature for 1 hour under nitrogen atmosphere. Concentrate under reduced pressure, add 10% aqueous sodium thiosulfate solution to the reaction mixture to decompose excess reagent, extract with methylene chloride, wash the methylene chloride layer with saturated aqueous sodium bicarbonate and saturated brine, and wash with anhydrous sodium sulfate. Dried. After filtration, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent: hexane / ethyl acetate = 3/1) to obtain 677 mg (100%) of the title compound.
[0250]
Nuclear magnetic resonance spectrum (400MHz, CDCl3), δ: 9.35 (s, 1H), 7.49 (d, 1H, J = 4.4 Hz), 7.29-7.25 (m, 3H), 7.18-7.15 (m, 2H), 6.80 (d, 1H, J = 4.4 Hz), 5.17 (br s, 1H), 2.87-2.79 (m, 1H), 2.84 (t, 2H, J = 6.8 Hz), 2.75-2.68 (m, 1H), 2.65 (t, 2H, J = 6.8 Hz), 2.40 (m, 1H), 2.15 (ddd, 1H, J = 5.9 Hz, 10.8 Hz, 14.3 Hz), 1.82-1.66 (m, 4H), 1.45 (s, 9H ), 1.38 (s, 3H).
Mass spectrum (FAB⁺), M / z: 444 ((M + H)⁺).
[0251]
(b)
(3R) -t-Butoxycarbonylamino-3-methyl-5- [5- (5-phenylpentanoyl) thiophen-2-yl] -1-pentenylphosphonic acid diethyl ester
Suspension of 60% sodium hydride (70.1 mg, 1.75 mmol) in tetrahydrofuran (3 mL) was added to ice-cooled tetraethyl methylene diphosphonate (0.43 mL, 1.73 mmol) over 5 minutes, and the mixture was stirred at room temperature for 1 hour. . Next, 508 mg (1.13) of (2R) -t-butoxycarbonylamino-2-methyl-4- [5- (5-phenylpentanoyl) thiophen-2-yl] -1-butanal obtained in Example 4 (a) was obtained. mmol) in tetrahydrofuran (7 mL) was added over 5 minutes under ice cooling, and the mixture was stirred at the same temperature for 10 minutes. The reaction mixture was neutralized by adding 0.10 mL (1.75 mmol) of acetic acid and concentrated under reduced pressure. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated brine, and anhydrous. Dried over magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent: ethyl acetate) to obtain 614 mg (94%) of the title compound.
[0252]
Nuclear magnetic resonance spectrum (400MHz, CDCl3), δ: 7.50 (d, 1H, J = 3.9 Hz), 7.29-7.25 (m, 3H), 7.19-7.16 (m, 2H), 6.81 (d, 1H, J = 3.9 Hz), 6.76 (dd, 1H, J = 17.8 Hz, 22.5 Hz), 5.72 (dd, 1H, J = 17.8 Hz, 17.8 Hz), 4.58 (br s, 1H), 4.15-4.02 (m, 4H) , 2.86-2.77 (m, 4H), 2.65 (t, 2H, J = 7.1 Hz), 2.33-2.24 (m, 1H), 2.06 (br s, 1H), 1.82-1.67 (m, 4H), 1.43 ( s, 9H), 1.41 (s, 3H), 1.33 (t, 3H, J = 6.8 Hz).
Mass spectrum (FAB⁺), M / z: 580 ((M + H)⁺).
[0253]
(c)
(3R) -t-Butoxycarbonylamino-3-methyl-5- [5- (5-phenylpentanoyl) thiophen-2-yl] pentylphosphonic acid diethyl ester
95.3 mg of 10% palladium-carbon (containing 50% water) was suspended in methanol (1 mL), and (3R) -t-butoxycarbonylamino-3-methyl-5- [5-] obtained in Example 4 (b) was suspended. A solution of 508 mg (0.88 mmol) of (5-phenylpentanoyl) thiophen-2-yl] -1-pentenylphosphonic acid diethyl ester in methanol (8 mL) was added, and the mixture was stirred at 50 ° C. for 40 hours in a hydrogen atmosphere. After palladium-carbon in the reaction solution was filtered through Celite, the filtrate was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: hexane / ethyl acetate = 1 / 3-ethyl acetate) to give 408 mg (yield 80%) of the title compound.
[0254]
Nuclear magnetic resonance spectrum (400MHz, CDCl3), δ: 7.51 (d, 1H, J = 3.6 Hz), 7.29-7.25 (m, 3H), 7.19-7.15 (m, 2H), 6.81 (d, 1H, J = 3.6 Hz), 4.37 (br s, 1H), 4.15-4.05 (m, 4H), 2.86-2.80 (m, 4H), 2.65 (t, 2H, J = 7.1 Hz), 2.30-2.12 (m, 2H) , 1.94-1.86 (m, 1H), 1.82-1.66 (m, 7H), 1.43 (s, 9H), 1.33 (t, 3H, J = 6.8 Hz) 1.21 (s, 3H).
Mass spectrum (FAB⁺), M / z: 580 ((M + H)⁺).
[0255]
(d)
(3R) -Amino-3-methyl-5- [5- (5-phenylpentanoyl) thiophen-2-yl] pentylphosphonic acid
(3R) -t-Butoxycarbonylamino-3-methyl-5- [5- (5-phenylpentanoyl) thiophen-2-yl] pentylphosphonic acid obtained in Example 4 (c)
130 mg (0.22 mmol) of diethyl ester was suspended in methylene chloride (2.2 mL), 0.30 mL (0.22 mmol) of trimethylsilane bromide was added, and the mixture was stirred at room temperature for 4 hours under a nitrogen atmosphere. After distilling off the solvent under reduced pressure, the residue was diluted with aqueous ethanol, and an aqueous ammonia solution and acetic acid were added thereto to adjust the pH to 3 to precipitate crystals. The precipitated crystals were collected by filtration, washed with water and ethanol, and dried to give the title compound (82.1 mg, yield 85%).
[0256]
Nuclear magnetic resonance spectrum (400MHz, CD_ThreeCO₂D), δ: 7.67 (d, 1H, J = 3.7 Hz), 7.26-7.22 (m, 2H), 7.18-7.12 (m, 3H), 6.97 (d, 1H, J = 3.7 Hz), 2.98 (t , 2H, J = 8.8 Hz), 2.93 (t, 2H, J = 7.3 Hz), 2.64 (t, 2H, J = 7.3 Hz), 2.23-2.07 (m, 4H), 2.06-1.93 (m, 2H) , 1.80-1.65 (m, 4H), 1.46 (s, 3H).
Mass spectrum (FAB⁺), M / z: 424 ((M + H)⁺).
[0257]
(Reference Example 1)
(4R) -Methyl-4- [2- (thiophen-2-yl) ethyl] oxazolidine-2-one
(a)
(2R) -t-Butoxycarbonylamino-3-hexanoyloxy-2-methyl-1-propanol
20.0 g (97.4 mmol) of 2-t-butoxycarbonylamino-2-methyl-1,3-propanediol was suspended in 200 ml of diisopropyl ether, 16.3 ml (0.10 mol) of hexanoic acid vinyl ester and lipase [Immobilized lipase from Pseudomonas sp. (TOYOBO; 0.67 U / mg)] 0.8 g was added, and the mixture was vigorously stirred at room temperature for 2 hours. The reaction solution was filtered, and the filtrate was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: hexane / ethyl acetate = 10/1 to 2/1) to give 25.0 g (yield 85%) of the title compound as a colorless oil.
[0258]
The optical purity of the obtained title compound was determined by analytical optically active HPLC column (ChiralCel OF (Daicel), (0.46 cm × 25 cm), elution solvent: hexane / 2-propanol = 70/30, flow rate: 0.5 ml / min. ).
[0259]
The first elution (retention time: 8.2 minutes) is 2S, and the later elution (retention time: 10.5 minutes) is 2R. The optical purity in this reaction is 85% ee. It was confirmed.
[α]^D _{twenty five} -8.5 (c 1.86, CHCl_Three)
Nuclear magnetic resonance spectrum (400MHz, CDCl_Three), Δ: 4.86 (s, 1H), 4.25 (d, 1H, J = 11.2 Hz), 4.19 (d, 1H, J = 11.2 Hz), 3.86 (brs, 1H), 3.70-3.55 (m, 2H) , 2.36 (t, 2H, J = 7.4 Hz), 1.68-1.58 (m, 2H), 1.44 (s, 9H), 1.40-1.30 (m, 4H), 1.25 (s, 3H), 0.90 (t, 3H , J = 7.0 Hz).
Infrared absorption spectrum, ν_max cm^-1 (Liquid film): 3415, 3380, 2961, 2935, 2874, 1721, 1505, 1458, 1392, 1368, 1293, 1248, 1168, 1076.
Mass spectrum (FAB), m / z: 304 ((M + H)⁺).
[0260]
(b)
(2R) -t-Butoxycarbonylamino-3-hexanoyloxy-2-methyl-1-propanal
30.7 g (0.10 mol) of (2R) -t-butoxycarbonylamino-3-hexanoyloxy-2-methyl-1-propanol obtained in Reference Example 1 (a) was dissolved in 600 ml of methylene chloride, and molecular sieves were obtained. 220 g of 4 kg and 43.6 g (0.20 mol) of pyridinium chromate were added under ice cooling, and then the mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with ether and filtered. The filtrate was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane / ethyl acetate = 10/1 to 5/1) to give 28.8 g (yield 95%) of the title compound as a colorless oil. Got as.
Nuclear magnetic resonance spectrum (400MHz, CDCl_Three), Δ: 9.45 (s, 1H), 5.26 (brs, 1H), 4.44 (d, 1H, J = 11.2 Hz), 4.32 (d, 1H, J = 11.2 Hz), 2.32 (t, 2H, J = 7.6 Hz), 1.70-1.55 (m, 2H), 1.45 (s, 9H), 1.38 (s, 3H), 1.40-1.25 (m, 4H), 0.90 (t, 3H, J = 7.0 Hz).
Infrared absorption spectrum, ν_max cm^-1 (Liquid film): 3367, 2961, 2935, 2874, 1742, 1707, 1509, 1458, 1392, 1369, 1290, 1274, 1254, 1166, 1100, 1078.
Mass spectrum (FAB), m / z: 302 ((M + H)⁺).
[0261]
(C)
(2R) -t-Butoxycarbonylamino-1-hexanoyloxy-2-methyl-4- (thiophen-2-yl) -3-butene
67.1 g (0.15 mol) of 2-thienylmethyltriphenylphosphonium bromide was suspended in 750 ml of tetrahydrofuran, to which 17.2 g (0.15 mol) of potassium t-butoxy was added, and the mixture was stirred at room temperature for 20 minutes in a nitrogen atmosphere. 23.0 g (76.4 mmol) of (2R) -t-butoxycarbonylamino-3-hexanoyloxy-2-methyl-1-propanal obtained in Reference Example 1 (b) dissolved in 250 ml of tetrahydrofuran into the reaction solution Was added dropwise under ice-cooling, and stirred for 30 minutes under ice-cooling after completion of the dropwise addition. Thereafter, water was added to the reaction solution, followed by extraction with ethyl acetate, and the ethyl acetate layer was washed with saturated brine. The ethyl acetate layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane / ethyl acetate = 20/1) to give 27.8 g (yield 96%) of the title compound as a colorless oil.
Nuclear magnetic resonance spectrum (400MHz, CDCl_Three), Δ: 7.32-7.26, 7.16-7.14 (m, total 1H), 7.04-7.01, 7.01-6.93 (m, total 2H), 6.63 (d, 0.5 H, J = 16.0 Hz), 6.60 (d, 0.5 H, J = 13.6 Hz), 6.10 (d, 0.5 H, J = 16.0 Hz), 5.58 (d, 0.5 H, J = 13.6 Hz), 4.94, 4.93 (brs, 1H total), 4.40-4.10 (m, 2H), 2.34 (t, 2H, J = 7.4 Hz), 1.70-1.55 (m, 2H), 1.57, 1.50, 1.44 (s, total 9H), 1.40-1.25 (m, 7H), 0.88 (t, 3H , J = 7.0 Hz).
Infrared absorption spectrum, ν_max cm^-1 (Liquid film): 3370, 2961, 2933, 1725, 1495, 1456, 1391, 1367, 1247, 1167, 1109, 1100, 1072, 697.
Mass spectrum (FAB), m / z: 381 (M⁺).
[0262]
(D)
(4R) -Methyl-4- [2- (thiophen-2-yl) ethenyl] oxazolidine-2-one
40.5 g (0.11 mol) of (2R) -t-butoxycarbonylamino-1-hexanoyloxy-2-methyl-4- (thiophen-2-yl) -3-butene obtained in Reference Example 1 (c) Dissolved in 150 ml of tetrahydrofuran and 150 ml of methanol, 530 ml of 1N aqueous sodium hydroxide solution was added thereto under ice cooling, and the mixture was stirred for 30 minutes under ice cooling and 1 hour at room temperature. The reaction mixture was concentrated under reduced pressure, water was added, the mixture was extracted with methylene chloride, and the methylene chloride layer was washed with saturated brine. The methylene chloride layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 35.0 g of a crude product. This crude product was dissolved in 300 ml of tetrahydrofuran, 17.8 g (0.16 mol) of potassium t-butoxy was added under ice cooling, and the mixture was stirred for 10 minutes under ice cooling and for 40 minutes at room temperature. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine. The ethyl acetate layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane / ethyl acetate = 3/1 to 1/1) to give the title compound (18.0 g, yield 81%) as a white solid.
Nuclear magnetic resonance spectrum (400MHz, CDCl_Three), Δ: 7.34 (d, 0.5H, J = 5.1 Hz), 7.19 (d, 0.5H, J = 5.0Hz), 7.07-6.91 (m, 2H), 6.74 (d, 0.5H, J = 16.0Hz) ), 6.59 (d, 0.5H, J = 12.5), 6.17 (brs, 1H), 6.06 (d, 0.5H, J = 16.0Hz), 5.65 (d, 0.5H, J = 12.5Hz), 4.41 (d , 0.5H, J = 8.6Hz), 4.31-4.16 (m, 1.5H), 1.60 (s, 1.5H), 1.55 (s, 1.5H).
Infrared absorption spectrum, ν_max cm^-1 (KBr): 3275, 3110, 2974, 1752, 1391, 1376, 1281, 1169, 1039, 960, 704.
Mass spectrum (FAB), m / z: 209 (M⁺).
[0263]
(E)
(4R) -Methyl-4- [2- (thiophen-2-yl) ethyl] oxazolidine-2-one
18.0 g (86.0 mmol) of (4R) -methyl-4- [2- (thiophen-2-yl) ethenyl] oxazolidine-2-one obtained in Reference Example 1 (d) was dissolved in 150 ml of methanol, and 10 % Palladium-carbon (4.5 g) was added, and the mixture was stirred at room temperature for 10 hours under a hydrogen atmosphere. The palladium-carbon in the reaction solution was filtered using a Kiriyama funnel with a thin silica gel, and the filtrate was distilled off under reduced pressure. The obtained solid was washed with diethyl ether and dried to give 16.5 g (yield 91%) of the title compound as a white solid.
[0264]
The optical purity of the obtained title compound was determined by analytical optically active HPLC column (ChiralCel OD-H (Daicel), (0.46 cm × 25 cm), elution solvent: hexane / 2-propanol = 60/40, flow rate: 0.5 ml. / Min).
[0265]
The first elution (retention time: 16.8 minutes) is 2S, and the later elution (retention time: 17.6 minutes) is 2R. The optical purity in this reaction is 85% ee. It was confirmed.
[α]^D _{twenty five} +5.1 (c 2.4, CHCl_Three)
Nuclear magnetic resonance spectrum (400MHz, CDCl_Three), Δ: 7.15 (d, 1H, J = 5.2 Hz), 6.93 (dd, 1H, J = 5.2, 3.6 Hz), 6.81 (d, 1H, J = 3.6 Hz), 5.39 (brs, 1H), 4.19 (d, 1H, J = 8.4 Hz), 4.08 (d, 1H, J = 8.4 Hz), 3.00-2.84 (m, 2H), 2.08-1.92 (m, 2H), 1.42 (s, 3H).
Infrared absorption spectrum, ν_max cm^-1 (KBr): 3283, 1770, 1399, 1244, 1043, 941, 846, 775, 706, 691.
Mass spectrum (EI), m / z: 211 (M⁺).
[0266]
25 ml of ethyl acetate and 5.0 ml of hexane were added to 11 g of (4R) -methyl-4- [2- (thiophen-2-yl) ethyl] oxazolidine-2-one having an optical purity of 85% ee and dissolved by heating. Then, it was left at room temperature for 2 hours. The precipitated white crystals were collected by filtration and dried to obtain 4.0 g of the title compound having an optical purity of 99% ee.
[α]^D _{twenty five} +7.8 (c 2.0, CHCl_Three).
[0267]
(Reference Example 2)
Acetic acid (2R) -acetylamino-2-methyl-4- (5-bromothiophen-2-yl) butyl ester
(a)
(2R) -Amino-2-methyl-4-thiophen-2-ylbutan-1-ol 1 / 2D-(-)-tartrate
Dissolve 85% ee (4R) -methyl-4- [2- (thiophen-2-yl) ethyl] oxazolidin-2-one 7.30 g (34.6 mmol) obtained in Reference Example 1 in 35 ml of tetrahydrofuran and 70 ml of methanol. Under ice-cooling, 70 ml of 5N aqueous potassium hydroxide solution was added, and the mixture was stirred at 80 ° C. for 2 days. Methylene chloride was added to the reaction solution and washed with water. The methylene chloride layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. 6.20 g of the resulting residue was dissolved in 60 ml of ethanol, a solution of 5.19 g (34.6 mmol) of D-(-)-tartaric acid in 50 ml of ethanol was added, and the deposited precipitate was collected by filtration to obtain 7.56 g of the crude title compound. It was. The obtained crude target compound (7.54 g) was recrystallized using 75 ml of ethanol and 50 ml of water to obtain 5.89 g (98% ee) of the title compound. Again, 5.88 g of the obtained target compound was recrystallized using 60 ml of ethanol and 54 ml of water to obtain 5.11 g of the title compound (57% yield, 99.7% ee).
Infrared absorption spectrum, ν_max cm^-1 (KBr): 3400, 3218, 3126, 2937, 2596, 1599, 1530, 1400, 1124, 1077, 715.
Elemental analysis value; (C₉H₁₅NOS ・ 0.5C_FourH_FourO₆As%)
Calculated values: C, 50.95; H, 6.61; N, 5.40; S, 12.36
Found: C, 50.68; H, 6.91; N, 5.38; S, 12.48
[α]_D ^{twenty four} -14 (c 1.00, H₂O).
[0268]
(b)
Acetic acid (2R) -acetylamino-2-methyl-4- (thiophen-2-yl) butyl ester
To 5.11 g (19.6 mmol) of (2R) -amino-2-methyl-4-thiophen-2-ylbutan-1-ol 1/2 D-(−)-tartrate obtained in Reference Example 2 (a), Under ice-cooling, 30 ml of 1N aqueous sodium hydroxide solution was added to make it free, and then extracted with methylene chloride. The methylene chloride layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to give 3.52 g of (2R) -amino-2-methyl-4-thiophen-2-ylbutan-1-ol (98% yield). Got. 30 ml of pyridine was added to 1.51 g (8.15 mmol) of the obtained free form, and 1.95 ml (20.7 mmol) of acetic anhydride and 200 mg (1.64 mmol) of 4- (dimethylamino) pyridine were added thereto under ice cooling. The mixture was stirred at room temperature for 2 and a half hours under a nitrogen atmosphere. The reaction solution was poured into 150 ml of 1N hydrochloric acid under ice cooling, extracted with ethyl acetate, and the ethyl acetate layer was washed successively with 1N hydrochloric acid and saturated brine. The ethyl acetate layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel chromatography (eluent: hexane / ethyl acetate = 3/1 to 1/2) to obtain 2.15 g (yield 98%) of the title compound.
Nuclear magnetic resonance spectrum (400MHz, CDCl_Three), Δ: 1.37 (3H, s), 1.93 (3H, s), 1.94-2.10 (1H, m), 2.10 (3H, s), 2.24-2.38 (1H, m), 2.85 (2H, t, J = 8.0 Hz), 4.18 (1H, d, J = 11.6 Hz), 4.32 (1H, d, J = 11.6 Hz), 5.39 (1H, brs), 6.81 (1H, dd, J = 1.2, 3.6 Hz), 6.92 (1H, dd, J = 3.6, 5.2 Hz), 7.12 (1H, dd, J = 1.2, 5.2 Hz).
Infrared absorption spectrum, ν_max cm^-1 (KBr): 3265, 3079, 2933, 2862, 1735, 1638, 1559, 1472, 1441, 1374, 1318, 1241, 1179, 1039, 701, 616.
[0269]
(c)
Acetic acid (2R) -acetylamino-2-methyl-4- (5-bromothiophen-2-yl) butyl ester
Acetic acid (2R) -acetylamino-2-methyl-4- (thiophen-2-yl) butyl ester 1.81 g (6.70 mmol) obtained in Reference Example 2 (b) was dissolved in 20 ml of dimethylformamide, and cooled with ice. , 1.27 g (7.11 mmol) of N-bromosuccinimide was added, and the mixture was stirred for 10 minutes under ice-cooling in a nitrogen atmosphere and at room temperature overnight. The reaction mixture was poured into water and extracted with ethyl acetate, and the ethyl acetate layer was washed with saturated brine. The ethyl acetate layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: hexane / ethyl acetate = 3/1 to 1/2) to obtain 2.32 g (yield 99%) of the title compound.
Nuclear magnetic resonance spectrum (400MHz, CDCl_Three), Δ: 1.35 (3H, s), 1.95 (3H, s), 1.95-2.08 (1H, m), 2.10 (3H, s), 2.24-2.37 (1H, m), 2.76 (2H, t, J = 8.4 Hz), 4.15 (1H, d, J = 11.2 Hz), 4.30 (1H, d, J = 11.2 Hz), 5.39 (1H, brs), 6.57 (1H, d, J = 3.6 Hz), 6.84 ( 1H, d, J = 3.6 Hz).
Infrared absorption spectrum, ν_max cm^-1 (Liquid film): 3300, 3076, 2980, 2937, 1740, 1657, 1544, 1466, 1446, 1373, 1242, 1045, 794, 604.
[0270]
(Reference Example 3)
5- (4-Fluorophenyl) pent-1-yne
2.11 g (48.4 mmol) of sodium hydride was suspended in 60 ml of anhydrous tetrahydrofuran, and 10.84 g (48.4 mmol) of diethylphosphonoacetic acid ethyl ester was added dropwise under ice cooling, followed by stirring for 10 minutes. Subsequently, a solution prepared by dissolving 5.00 g (40.3 mmol) of 4-fluorobenzaldehyde in 60 ml of anhydrous tetrahydrofuran was added dropwise at the same temperature. The reaction solution was stirred at the same temperature for 3 hours, poured into 150 ml of ice water, and extracted with ethyl acetate. The organic layer is dried over anhydrous magnesium sulfate, the solvent is distilled off under reduced pressure, and the residue is purified by flash silica gel column chromatography (elution solvent: hexane / ethyl acetate = 10/1 to 3/1) to give 4-fluoro 6.69 g (yield 86%) of cinnamic acid ethyl ester was obtained as a colorless oil.
[0271]
6.52 g (33.6 mmol) of this ester was dissolved in 100 ml of ethyl acetate, 1.30 g of 5% rhodium / alumina was added, and the mixture was stirred at room temperature for 8 hours in a hydrogen atmosphere. The reaction mixture was filtered through Celite, the filtrate was concentrated under reduced pressure, and the residue was dissolved in 30 ml of anhydrous tetrahydrofuran. Under ice cooling, this solution was added dropwise to a suspension of 1.26 g (33.2 mmol) of lithium aluminum hydride in 60 ml of anhydrous tetrahydrofuran. The reaction mixture was stirred at the same temperature for 30 min, saturated aqueous sodium sulfate solution was added, and the mixture was further stirred at room temperature for 10 min. The mixture was filtered through celite, and the filtrate was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by flash silica gel column chromatography (eluent: hexane / ethyl acetate = 5/1 to 1/1) to give 4-fluorophenylpropan-1-ol as a colorless oil As a result, 4.86 g (yield 95%) was obtained.
[0272]
4.83 g (31.3 mmol) of 4-fluorophenylpropan-1-ol obtained was dissolved in 50 ml of methylene chloride, and 6.55 ml (47.0 mmol) of triethylamine and 2.91 ml (37.6 mmol) of methanesulfonyl chloride were added under ice cooling. The mixture was stirred at the same temperature for 30 minutes under a nitrogen atmosphere. The reaction mixture was diluted with 50 ml of methylene chloride, washed successively with ice-cooled 10% hydrochloric acid and saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue was dissolved in 100 ml of acetone. Next, 9.39 g (62.6 mmol) of sodium iodide was added, and the mixture was stirred at 50 ° C. for 2 hours under a nitrogen atmosphere. The reaction mixture was diluted with 250 ml of ethyl acetate, washed successively with 10% aqueous sodium thiosulfate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by flash silica gel column chromatography (elution solvent: hexane / ethyl acetate = 5/1 to 2/1) to give 4-fluorophenyl-1-iodopropane as a pale yellow oil As a product, 7.12 g (yield 86%) was obtained.
[0273]
50 ml of sodium acetylide (18% xylene suspension) is added to 20 ml of hexamethylphosphoramide, and 7.00 g (26.5 mmol) of 4-fluorophenyl-1-iodopropane obtained above is added to 20 ml of anhydrous dimethylformamide under ice-cooling. The solution dissolved in was added. The reaction mixture was stirred at room temperature for 2 hours. Ice water was carefully poured under ice cooling, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by flash silica gel column chromatography (elution solvent: hexane) to obtain 2.67 g (yield 62%) of the title compound as a colorless oil.
Nuclear magnetic resonance spectrum (400MHz, CDCl_Three), Δ: 1.82 (2H, m), 1.99 (1H, t, J = 2.6 Hz), 2.19 (2H, m), 2.71 (2H, t, J = 7.5 Hz), 6.97 (2H, m), 7.14 (2H, m).
Mass spectrum (EI), m / z: 162 (M⁺).
[0274]
(Reference Example 4)
5-Phenylpent-1-yne
In the same manner as in Reference Example 3, the title compound was obtained using 3-phenyl-1-iodopropane and sodium acetylide.
Nuclear magnetic resonance spectrum (400MHz, CDCl_Three), Δ: 1.81-1.89 (2H, m), 1.99 (1H, t, J = 2.8 Hz), 2.21 (2H, dt, J = 2.8, 7.6 Hz), 2.74 (2H, t, J = 7.6 Hz) , 7.16-7.23 (3H, m), 7.26-7.32 (2H, m).
Mass spectrum (EI), m / z: 144 (M⁺).
[0275]
(Reference Example 5)
(2R) -Amino-2-methyl-4- [5- (5-cyclohexylpent-1-ynyl) thiophen-2-yl] butan-1-ol
(a)
2-Methyl-2- (2-thienyl) ethylmalonic acid diethyl ester
18.8 g (0.43 mol) of sodium hydride (55%) was suspended in dimethylformamide (200 ml), and 50.0 g (0.29 mol) of methylmalonic acid diethyl ester was slowly added over 30 minutes under ice cooling. The mixture was further stirred for 30 minutes. Next, a solution of 75.2 g (0.32 mol) of 2- (2-iodoethyl) thiophene in dimethylformamide (200 ml) was added over 15 minutes under a nitrogen atmosphere, and the mixture was further stirred at room temperature for 4 hours. The reaction mixture was poured into ice-cooled 10% hydrochloric acid (500 ml) and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure, and the residue was purified by flash silica gel column chromatography (eluent: hexane / ethyl acetate = 10/1 to 5/1) to give 53.1 g of the title compound as a colorless oil (yield 65 %)Obtained.
Infrared absorption spectrum, ν_max cm^-1(CHCl_Three): 2986, 1726, 1271, 1252.
Mass spectrum (FAB), m / z: 285 ((M + H)⁺).
[0276]
(b)
2-Methyl-2- (2-thienyl) ethylmalonic acid mono-ethyl ester
Dissolve 52.7 g (0.19 mol) of 2-methyl-2- (2-thienyl) ethylmalonic acid diethyl ester obtained in Reference Example 5 (a) in ethanol (240 ml) and water (80 ml) and add ice. Under cooling, 11.4 g (0.20 mol) of potassium hydroxide was added and stirred at the same temperature for 2 hours. Further, 5.7 g (0.1 mol) of potassium hydroxide was added three times every hour, and the mixture was stirred for a total of 6 hours. Water (300 ml) and ice-cooled 10% hydrochloric acid (500 ml) were added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure, and the residue was purified by flash silica gel column chromatography (eluent: hexane / ethyl acetate = 2 / 1-0 / 1) to give 28.6 g (yield) of the title compound as a pale yellow oil. 60%).
[0277]
Infrared absorption spectrum, ν_max cm^-1(CHCl_Three): 2987, 1732, 1712, 1251, 1109.
Mass spectrum (FAB), m / z: 257 ((M + H)⁺).
[0278]
(c)
2-Methoxycarbonylamino-2-methyl-4- (2-thienyl) butanoic acid ethyl ester
19.0 g (74.3 mmol) of 2-methyl-2- (2-thienyl) ethylmalonic acid mono-ethyl ester obtained in Reference Example 5 (b) was dissolved in benzene (450 ml), and 11.4 ml (81.7 ml) of triethylamine was dissolved. mmol) and 17.6 ml (81.7 mmol) of diphenylphosphoric acid azide were added, stirred at room temperature for 10 minutes, and further stirred at 80 ° C. for 1 hour and a half. Next, 60.3 ml (1.49 mol) of methanol was slowly added dropwise at the same temperature over 30 minutes, and further stirred at the same temperature for 8 hours. The reaction mixture was poured into water (500 ml) and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure, and the residue was purified by flash silica gel column chromatography (eluent: hexane / ethyl acetate = 8/1 to 4/1) to give the title compound as a colorless oil, 14.7 g (yield 69 %)Obtained.
Nuclear magnetic resonance spectrum (400MHz, CDCl_Three), Δ: 7.11 (1H, d, J = 5.1 Hz), 6.90 (1H, dd, J = 5.1, 3.5 Hz), 6.77 (1H, d, J = 3.5 Hz), 5.69 (1H, brs), 4.19 (2H, q. J = 7.3 Hz), 3.66 (3H, s), 2.84 (2H, dd, J = 10.5, 10.5 Hz), 2.64 (2H, m), 2.20 (2H, dd, J = 10.5, 8.4 Hz), 1.61 (3H, s), 1.28 (3H, t, J = 7.3 Hz).
Infrared absorption spectrum, ν_maxcm^-1(CHCl_Three): 3417, 2987, 1719, 1503, 1453, 1081.
Mass spectrum (FAB), m / z: 286 ((M + H)⁺).
[0279]
(d)
2-Methoxycarbonylamino-2-methyl-4- (2-thienyl) butan-1-ol
14.7 g (51.6 mmol) of 2-methoxycarbonylamino-2-methyl-4- (2-thienyl) butanoic acid ethyl ester obtained in Reference Example 5 (c) in ethanol (150 ml) and tetrahydrofuran (100 ml) Then, sodium borohydride (5.07 g, 0.13 mol) and lithium chloride (5.68 g, 0.13 mol) were added, and the mixture was stirred overnight at room temperature under a nitrogen atmosphere. The next morning, 5.07 g (0.13 mol) of sodium borohydride and 5.68 g (0.13 mol) of lithium chloride were added in the same manner, and the mixture was further stirred overnight at room temperature under a nitrogen atmosphere. This same operation was performed for another 2 days. The reaction mixture was poured into ice-cooled 10% hydrochloric acid (500 ml) and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure, and the residue was purified by flash silica gel column chromatography (eluent: hexane / ethyl acetate = 2/1 to 1/5) to give 11.7 g (yield 93%) of the title compound as white crystals. )Obtained.
Infrared absorption spectrum, ν_maxcm^-1(KBr): 3406, 3244, 1687, 1562, 1264, 1089.
Mass spectrum (FAB), m / z: 244 ((M + H)⁺).
Elemental analysis value; (C₁₁H₁₇NO_Three% As S)
Calculated values: C: 54.30, H: 7.04, N: 5.76, S: 13.18
Found: C: 54.18, H: 6.98, N: 5.78, S: 13.34.
[0280]
(e)
2-Methoxycarbonylamino-2-methyl-4- (5-bromothiophen-2-yl) butan-1-ol
11.7 g (48.0 mmol) of 2-methoxycarbonylamino-2-methyl-4- (2-thienyl) butan-1-ol obtained in Reference Example 5 (d) was dissolved in dimethylformamide (120 ml), Under ice cooling, 10.8 g (60.8 mmol) of N-bromosuccinimide was added, and the mixture was stirred at room temperature for 4 hours under a nitrogen atmosphere. The reaction mixture was poured into ice-cooled 10% hydrochloric acid (300 ml) and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure, and the residue was purified by flash silica gel column chromatography (eluent: hexane / ethyl acetate = 4/1 to 1/3) to give the title compound as a pale yellow oil, 12.4 g (yield 80%).
Nuclear magnetic resonance spectrum (400MHz, CDCl_Three), Δ: 6.84 (1H, d, J = 3.7 Hz), 6.57 (1H, d, J = 3.7 Hz), 4.80 (1H, brs), 3.68 (2H, m), 3.64 (3H, s), 2.80 (2H, m), 1.9-2.2 (2H, m), 1.24 (3H, s).
Infrared absorption spectrum, ν_max cm^-1(CHCl_Three): 3627, 3436, 2956, 1722, 1711, 1513, 1259, 1087, 1048.
Mass spectrum (FAB), m / z: 322 ((M + H)⁺).
[0281]
(f)
2- [2- (5-Bromothiophen-2-yl)] ethyl-4-methyloxazolidin-2-one 2-methoxycarbonylamino-2-methyl-4- (5) obtained in Reference Example 5 (e) -Bromothiophen-2-yl) butan-1-ol 12.4 g (38.6 mmol) was dissolved in dimethylformamide (125 ml), and 6.50 g (57.9 mmol) of potassium t-butoxide was added under ice-cooling and nitrogen atmosphere. In addition, the mixture was further stirred at the same temperature for 3 hours. The reaction mixture was poured into ice-cooled 10% hydrochloric acid (300 ml) and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure, and the residue was purified by flash silica gel column chromatography (eluent: hexane / ethyl acetate = 4/1 to 1/2) to give 10.7 g (yield 95%) of the title compound as white crystals. )Obtained.
[0282]
Nuclear magnetic resonance spectrum (400MHz, CDCl_Three), Δ: 6.86 (1H, d, J = 3.7 Hz), 6.58 (1H, d, J = 3.7 Hz), 5.73 (1H, brs), 4.18 (1H, d, J = 8.6 Hz), 4.08 (1H , d, J = 8.6 Hz), 2.84 (2H, m), 1.94 (2H, m), 1.41 (3H, s).
Infrared absorption spectrum, ν_max cm^-1(KBr): 3211, 1749, 1399, 1037, 798.
Mass spectrum (FAB), m / z: 290 ((M + H)⁺).
Elemental analysis value; (C_TenH₁₂NO₂(% As SBr)
Calculated values: C: 41.39, H: 4.17, N: 4.83, S: 11.05, Br: 27.54
Found: C: 41.36, H: 4.04, N: 4.82, S: 11.08, Br: 27.29.
[0283]
(g)
(4R)-[2- (5-Bromothiophen-2-yl)] ethyl-4-methyloxazolidin-2-one and (4S)-[2- (5-Bromothiophen-2-yl)] ethyl-4 -Methyloxazolidine-2-one
Preparative optically active HPLC column (ChiralCel OD, Daicel) 4- [2- (5-bromothiophen-2-yl)] ethyl-4-methyloxazolidine-2-one obtained in Reference Example 5 (f) (Column, ChiralCel OD (2 cmφ × 25 cm); elution solvent: hexane / 2-propanol = 70/30, flow rate: 5 ml / min). What was eluted first (retention time: 55 minutes) was 4S, and what was eluted later (retention time: 77 minutes) was 4R. The absolute configuration was determined by X-ray crystal structure analysis.
(4S) body; [α]_D ^{twenty four} −4.2 (c 1.03, methanol)
(4R) body; [α]_D ^{twenty four} +4.2 (c 1.00, methanol).
[0284]
(h)
(4R)-[2- [5- (5-Cyclohexylpent-1-ynyl) thiophen-2-yl]] ethyl-4-methyloxazolidine-2-one
450 mg (1.55 mmol) of (4R)-[2- (5-bromothiophen-2-yl)] ethyl-4-methyloxazolidin-2-one obtained in Reference Example 5 (g) was added to 4.5 ml of dimethylformamide. Dissolve, 1.40 g (4.65 mmol) of 5-cyclohexylpent-1-yne (50% xylene solution), 2.16 ml (15.5 mmol) of triethylamine, 30 mg (0.16 mmol) of copper (I) iodide and dichlorobis (triphenylphosphine) ) Palladium 109 mg (0.16 mmol) was added, and the mixture was stirred at 80 ° C. for 2 hours under a nitrogen atmosphere. The reaction mixture was poured into water and extracted with ethyl acetate, and the ethyl acetate layer was washed with saturated brine. The ethyl acetate layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (eluent: hexane / ethyl acetate = 4 / 1-3 / 2) to give 456 mg (yield 82%) of the title compound.
Nuclear magnetic resonance spectrum (400MHz, CDCl_Three), Δ: 6.92 (1H, d, J = 3.6 Hz), 6.63 (1H, d, J = 3.6 Hz), 5.45 (1H, brs), 4.18 (1H, d, J = 8.6 Hz), 4.07 (1H , d, J = 8.6 Hz), 2.78-2.90 (2H, m), 2.38 (2H, t, J = 7.2 Hz), 1.92-2.00 (2H, m), 1.55-1.75 (7H, m), 1.40 ( 3H, s), 1.10-1.35 (6H, m), 0.83-0.95 (2H, m).
Infrared absorption spectrum, ν_maxcm^-1 (KBr): 3450, 2926, 2852, 1758, 1382, 1046.
[0285]
(i)
(2R) -Amino-2-methyl-4- [5- (5-cyclohexylpent-1-ynyl) thiophen-2-yl] butan-1-ol
(4R)-[2- [5- [5-cyclohexylpent-1-ynyl) thiophen-2-yl]] ethyl-4-methyloxazolidine-2-one 456 mg obtained in Reference Example 5 (h) ( 1.27 mmol) was dissolved in 1 ml of tetrahydrofuran and 2 ml of methanol, 2 ml of 5N aqueous potassium hydroxide solution was added under ice cooling, and the mixture was heated to reflux for 18 hours. Water was added to the reaction mixture, and the mixture was extracted with methylene chloride. The methylene chloride layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography [elution solvent: (methylene chloride / methanol = 20/1), (methylene chloride / methanol / aqueous ammonia = 10/1 / 0.1)] to give 353 mg (yield 83%) of the title compound. )
Nuclear magnetic resonance spectrum (400MHz, CDCl_Three), Δ: 6.92 (1H, d, J = 3.5 Hz), 6.62 (1H, d, J = 3.5 Hz), 3.37 (1H, d, J = 10.5 Hz), 3.32 (1H, d, J = 10.5 Hz) ), 2.75-2.90 (2H, m), 2.38 (2H, t, J = 7.1 Hz), 1.52-1.79 (9H, m), 1.12-1.33 (6H, m), 1.11 (3H, s), 0.81- 0.96 (2H, m).
Infrared absorption spectrum, ν_max cm^-1 (CHCl_Three): 2925, 2852, 1449, 1041.
Mass spectrum (FAB), m / z: 334 ((M + H)⁺).
Elemental analysis value; (C₂₀H₃₁NOS ・ 0.3H₂O as%)
Calculated values: C: 70.87, H: 9.40, N: 4.13, S: 9.46
Actual value: C: 70.83, H: 9.21, N: 4.22, S: 9.64
[α]_D ^{twenty four} -2.0 (c 0.60, methanol).
[0286]
(Reference Example 6)
(2R) -Amino-2-methyl-4- [5- (4-cyclohexyloxybut-1-ynyl) thiophen-2-yl] butan-1-ol maleate
4- [2- (5-Bromothiophen-2-yl)] ethyl-4-methyloxazolidine-2-one and 4-cyclohexyloxybut-1-yne were used as starting materials, and Reference Example 5 (h) and Reference Reaction was carried out in the same manner as in Example 5 (i), and then converted to the maleate to give the title compound (yield 43%).
Nuclear magnetic resonance spectrum (400MHz, CD_ThreeOD), δ: 6.93 (1H, d, J = 3.6 Hz), 6.73 (1H, d, J = 3.6 Hz), 6.25 (2H, s), 3.57-3.67 (3H, m), 3.51 (1H, d , J = 11.6 Hz), 3.32-3.42 (1H, m), 2.78-2.95 (2H, m), 2.63 (2H, t, J = 6.7 Hz), 1.50-2.10 (7H, m), 1.17-1.37 ( 8H, m).
Infrared absorption spectrum, ν_max cm^-1 (KBr): 3394, 2932, 2858, 1583, 1506, 1386, 1367, 1194, 1104.
[0287]
(Reference Example 7)
Acetic acid (2R) -acetylamino-2-methyl-4- [5- (5-phenylpent-1-ynyl) thiophen-2-yl] butyl ester
1.60 g (4.59 mmol) of acetic acid (2R) -acetylamino-2-methyl-4- (5-bromothiophen-2-yl) butyl ester synthesized in Reference Example 2 was dissolved in 16 ml of dimethylformamide, and 5-phenylpento Add 1.99 g (13.8 mmol) of -1-yne, 6.40 ml (45.9 mmol) of triethylamine, 175 mg (0.92 mmol) of copper (I) iodide and 322 mg (0.46 mmol) of dichlorobis (triphenylphosphine) palladium, and add 80 under nitrogen atmosphere. Stir for 2 hours at ° C. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (eluent: hexane / ethyl acetate = 2/1 to 2/3) to obtain 1.41 g (yield 75%) of the title compound.
Nuclear magnetic resonance spectrum (400MHz, CDCl_Three), Δ: 1.36 (3H, s), 1.85-2.05 (3H, m), 1.94 (3H, s), 2.10 (3H, s), 2.25-2.35 (1H, m), 2.43 (2H, t, J = 7.0 Hz), 3.70-3.80 (4H, m), 4.17 (1H, d, J = 11.2 Hz), 4.31 (1H, d, J = 11.2 Hz), 5.38 (1H, brs), 6.64 (1H, d , J = 3.6 Hz), 6.94 (1H, d, J = 3.6 Hz), 7.15-7.42 (5H, m).
Infrared absorption spectrum, ν_max cm^-1 (CHCl_Three): 3443, 2946, 2862, 1737, 1681, 1511, 1374, 1251, 1042.
[0288]
(Reference Example 8)
(2R) -Amino-2-methyl-4- [5- (5-phenylpentyl) thiophen-2-yl] butan-1-ol oxalate
Acetic acid (2R) -acetylamino-2-methyl-4- [5- (6-phenylpent-1-ynyl) thiophen-2-yl] butyl 337 mg (0.82 mmol) obtained in Reference Example 7 was added to 17 ml of methanol. After dissolution, 170% of 10% palladium-carbon was added, and the mixture was stirred at room temperature for 16 hours under a hydrogen atmosphere. The catalyst was removed by filtration through Celite, and the filtrate was evaporated under reduced pressure. Acetic acid (2R) -acetylamino-2-methyl-4- [5- (5-phenylpentyl) thiophen-2-yl] butyl (318 mg, yield) 93%). 298 mg (0.72 mmol) of the obtained butyl acetate ester was dissolved in 6 ml of a mixed solution of tetrahydrofuran, methanol and water (1/1/1), and 301 mg (7.17 mmol) of lithium hydroxide monohydrate was added. Stir at 6 ° C. for 6 hours. The reaction mixture was poured into water and extracted with methylene chloride. The methylene chloride layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. 243 mg of the residue was dissolved in methanol, 65 mg (0.72 mmol) of oxalic acid was added, and the precipitated crystals were collected by filtration to obtain 251 mg (yield 83%) of the title compound as white crystals.
Nuclear magnetic resonance spectrum (400MHz, CD_ThreeOD), δ: 1.31 (3H, s), 1.32-1.42 (2H, m), 1.58-1.70 (4H, m), 1.88-2.08 (2H, m), 2.59 (2H, t, J = 7.6 Hz) , 2.74 (2H, t, J = 7.4 Hz), 2.75-2.91 (2H, m), 3.52 (1H, d, J = 11.6 Hz), 3.61 (1H, d, J = 11.6 Hz), 6.56 (1H, d, J = 3.3 Hz), 6.63 (1H, d, J = 3.3 Hz), 7.09-7.17 (3H, m), 7.19-7.27 (2H, m).
Infrared absorption spectrum, ν_max cm^-1 (KBr): 3458, 3134, 2929, 2855, 2595, 1724, 1642, 1543, 1219, 710 cm^-1.
[0289]
(Reference Example 9)
(2R) -Amino-2-methyl-4- [5- (5-phenylpent-1-ynyl) thiophen-2-yl] butan-1-ol oxalate
Acetic acid (2R) -acetylamino-2-methyl-4- [5- (5-phenylpent-1-ynyl) thiophen-2-yl] butyl ester 1.40 g (3.40 mmol) obtained in Reference Example 7 was added to tetrahydrofuran. Then, the mixture was dissolved in 14 ml of a mixed solution of methanol and water (1/1/1), 1.43 g (34.0 mmol) of lithium hydroxide monohydrate was added, and the mixture was stirred at 50 ° C. for 4 hours. The reaction solution was poured into water, extracted with methylene chloride, the methylene chloride layer was purified by anhydrous sulfur / 1 / 0.1), and (2R) -amino-2-methyl-4- [5- (5-phenylpent- 1-Inyl) thiophen-2-yl] butan-1-ol (1.11 g, yield 100%) was obtained. 360 mg (1.10 mmol) of the resulting butan-1-ol was dissolved in methanol, 99 mg (1.10 mmol) of oxalic acid was added, and the precipitated crystals were recrystallized from methanol to give 394 mg (yield) of the title compound as white crystals. 86%).
Nuclear magnetic resonance spectrum (400MHz, CD_ThreeOD), δ: 1.31 (3H, s), 1.82-2.10 (4H, m), 2.40 (2H, t, J = 7.0 Hz), 2.75 (2H, t, J = 7.5 Hz), 2.80-2.95 (2H , m), 3.52 (1H, d, J = 11.5 Hz), 3.61 (1H, d, J = 11.5 Hz), 6.73 (1H, d, J = 3.6 Hz), 6.94 (1H, d, J = 3.6 Hz) ), 7.13-7.30 (5H, m).
Infrared absorption spectrum, ν_max cm^-1 (KBr): 3383, 3106, 3026, 2980, 2942, 2622, 2514, 1721, 1609, 1539, 1198, 699. Mass spectrum (FAB), m / z: 328 ((M + H)⁺) (Free body).
Elemental analysis value; (C₂₀H_{twenty five}NOS ・ C₂H₂O_Four・ 0.2H₂O as%)
Calculated value: C, 62.75; H, 6.55; N, 3.32; S, 7.61
Found: C, 62.50; H, 6.29; N, 3.39; S, 7.70.
[α]_D ^{twenty five} -0.9 (c 1.00, methanol).
[0290]
(Reference Example 10)
(2R) -Amino-2-methyl-4- [5- (5-phenylpentanoyl) thiophen-2-yl] butan-1-ol oxalate
(2R) -Amino-2-methyl-4- [5- (5-phenylpent-1-ynyl) thiophen-2-yl] butan-1-ol oxalate obtained in the first step of Reference Example 9 387 mg (1.18 mmol) was dissolved in 4 ml of methanol, 4 ml of 6N sulfuric acid was added, and the mixture was heated to reflux for 4 hours. The reaction mixture was cooled to 0 ° C., made alkaline (pH 14) with 1N aqueous sodium hydroxide solution, and extracted with methylene chloride. The methylene chloride layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the residue was chromatographed on silica gel (Chromatorex NH (100-200 mesh)) (elution solvent: methylene chloride / methanol = 1 / 0-50 / 1). ) To give 336 mg (82% yield) of (2R) -amino-2-methyl-4- [5- (5-phenylpentanoyl) thiophen-2-yl] butan-1-ol. This was dissolved in methanol, oxalic acid 88 mg (0.97 mmol) was added, and the obtained crystals were recrystallized from methanol to obtain 332 mg (yield 78%) of the title compound as white crystals.
Nuclear magnetic resonance spectrum (400MHz, CD_ThreeOD), δ: 1.19 (3H, s), 1.55-1.67 (4H, m), 1.80-1.98 (2H, m), 2.60 (2H, t, J = 6.7 Hz), 2.83-2.96 (4H, m) , 3.40 (1H, d, J = 11.3 Hz), 3.47 (1H, d, J = 11.3 Hz), 7.00 (1H, d, J = 3.7 Hz), 7.13-7.22 (3H, m), 7.23-7.31 ( 2H, m), 7.80 (1H, d, J = 3.7 Hz). Infrared absorption spectrum, ν_max cm^-1 (KBr): 3126, 2942, 2657, 1915, 1718, 1649, 1609, 1547, 1445, 1205, 700
Mass spectrum (FAB), m / z: 346 ((M + H)⁺) (Free body).
Elemental analysis value; (C₂₀H₂₇NO₂S ・ C₂H₂O_Four・ 0.5H₂O as%)
Calculated value: C, 59.44; H, 6.80; N, 3.15; S, 7.21
Found: C, 59.62; H, 6.53; N, 3.31; S, 7.43.
[0291]
(Test Example 1)
Measurement of inhibitory activity against rat HvGR (Host veRsus GRaft Reaction)
(1) Two strains of rats [Lewis (male, 6 weeks old, Charles River Japan) and WKAH / Hkm (male, 7 weeks old, SLC Japan)] were used. One group of 5 rats (host) was used.
(2) Isolate spleen cells from spleens of WKAH / Hkm rats or Lewis rats and use 1x10 RPMI1640 medium (Life Technology)⁸Floating to a concentration of pcs / ml. In Lewis rat both hind limbs, 0.1 ml of spleen cell suspension of WKAH / Hkm rat or Lewis rat (1x10 spleen cells)⁷Injection).
(3) A test compound is dissolved in 5% SBE-β-CD aqueous solution (SBE: Sulfobutyl Ether) and injected into WKAH / Hkm rat spleen cells at a rate of 5 ml per 1 kg body weight of the rat per day. It was orally administered once every day for 4 days from the day of spleen cell injection. The syngeneic group (Lewis rat group injected with Lewis rat spleen cells) and the control group (WKAH / Hkm rat spleen cell injected and Lewis rats not administered with the sample) had 5% SBE-β instead of the sample. -An aqueous CD solution was administered orally.
(4) Subtract the average popliteal lymph node weight of the syngeneic group from the popliteal lymph node weight of each individual ("popliteal lymph node weight by HvGR"), and the average "popliteal lymph node weight by HvGR" in the control group The inhibition rate was calculated from “popliteal lymph node weight by HvGR” of each individual in the compound administration group. The inhibitory activity of a compound is an ID calculated using the least squares method from the dose and inhibition rate of the compound.₅₀It was expressed as a value (mg / kg).
[0292]
[Table 3]

As a result of this test, the compound of the present invention showed excellent inhibitory activity.
[0293]
【The invention's effect】
The phosphoric acid or phosphonic acid derivative having the general formula (I) of the present invention, its pharmacologically acceptable salt or its pharmacologically acceptable ester has an excellent immunosuppressive action with low toxicity and can be used for various organ transplantation or Skin graft rejection, systemic lupus erythematosus, rheumatoid arthritis, polymyositis, connective tissue inflammation, skeletal myositis, osteoarthritis, osteoarthritis, dermatomyositis, scleroderma, Behcet's disease, Chron's disease, ulcerative colon Inflammation, autoimmune hepatitis, aplastic anemia, idiopathic thrombocytopenic purpura, autoimmune hemolytic anemia, multiple sclerosis, autoimmune bullosa, psoriasis vulgaris, vascular inflammation group, Wegener granulomas, Uveitis, Sjogren's syndrome, idiopathic interstitial pneumonia, Goodpasture syndrome, sarcoidosis, allergic granulomatous vasculitis, bronchial asthma, myocarditis, cardiomyopathy, aortitis syndrome, post-myocardial infarction syndrome, Pulmonary hypertension, minimal change nephrosis, membranous nephropathy, membranoproliferative nephritis, focal glomerulosclerosis, crescent nephritis, myasthenia gravis, inflammatory neuropathy, atopic dermatitis, chronic Photodermatitis, photosensitivity, pressure ulcer, Sydenham chorea, systemic sclerosis, adult-onset diabetes, insulin-dependent diabetes, juvenile diabetes, atherosclerosis, glomerulonephritis, IgA nephropathy, tubule Interstitial nephritis, primary biliary cirrhosis, primary sclerosing cholangitis, fulminant hepatitis, viral hepatitis, GVHD, contact dermatitis, autoimmune diseases such as sepsis or other immune related diseases, fungi, mycoplasma, virus, Infectious diseases such as protozoa, heart failure, cardiac hypertrophy, arrhythmia, angina pectoris, cardiac ischemia, arterial embolism, aneurysm, varicose vein, circulatory disorders such as blood circulation disorder, Alzheimer's disease, dementia, Parkinson's disease, stroke, cerebral infarction , Cerebral ischemia, depression, manic depression, schizophrenia, Huntington's chorea, epilepsy, convulsions, hyperactivity, encephalitis, meningitis, anorexia and binge eating, central diseases such as lymphoma, leukemia, polyuria, frequent urination, Of various diseases such as diabetic retinopathy (particularly preferably, rejection in various organ transplantation or skin transplantation, systemic lupus erythematosus, rheumatoid arthritis, multiple sclerosis, atopic dermatitis, etc.) It is useful as a prophylactic or therapeutic agent (especially therapeutic agent) for warm-blooded animals (especially for humans).

Claims

Formula (I)

[Where:
R ¹ and R ² are the same or different and each represents a hydrogen atom, a lower aliphatic acyl group or a lower alkoxycarbonyl group,
R ³ and Ra ³ are the same or different and each represents a hydrogen atom or a protecting group for a phosphate group;
R ⁴ represents a hydrogen atom, a lower alkyl group or a hydroxy lower alkyl group,
n represents an integer of 1 to 6,
X is an ethylene group, vinylene group, ethynylene group, a group having the formula —D—CH ₂ — (wherein D is a carbonyl group, a group having the formula —CH (OH) —, an oxygen atom, a sulfur atom, or a formula a group having a -NH-.), shows a C ₆ -C ₁₀ arylene group or 1 to 3 groups selected from substituent group a substituted C ₆ -C ₁₀ arylene group,
Y represents a single bond, C ₁ -C ₁₀ alkylene group, and 1 to 3 substituted with a group selected from Substituent group a and b the C ₁ -C ₁₀ alkylene group, an oxygen atom in the carbon chain or the chain ends Or a C ₁ -C ₁₀ alkylene group having a sulfur atom, or C ₁ having an oxygen atom or a sulfur atom in the carbon chain or at the chain end, substituted with 1 to 3 groups selected from the substituent groups a and b Z indicates -C ₁₀ alkylene group, an oxygen atom or a methylene group,
R ⁵ represents a hydrogen atom, a C ₃ -C ₁₀ cycloalkyl group, a C ₆ -C ₁₀ aryl group, a sulfur atom, an oxygen atom and / or a 5- to 7-membered heterocyclic group containing 1 to 3 nitrogen atoms, a substituent C ₃ -C ₁₀ cycloalkyl group substituted with 1 to 3 groups selected from groups a and b, C ₆ -C ₁₀ substituted with groups selected from substituent groups a and b An aryl group, or a 5- to 7-membered heterocyclic group containing 1 to 3 sulfur atoms, oxygen atoms and / or nitrogen atoms, substituted with 1 to 3 groups selected from substituent groups a and b;
R ⁶ and R ⁷ are the same or different and each represents a hydrogen atom or a group selected from the substituent group a,
Substituent group a is a halogen atom, lower alkyl group, halogeno lower alkyl group, lower alkoxy group, lower alkylthio group, carboxyl group, lower alkoxycarbonyl group, hydroxy group, lower aliphatic acyl group, amino group, mono-lower alkyl A group consisting of an amino group, a di-lower alkylamino group, a lower aliphatic acylamino group, a cyano group and a nitro group;
Substituent group b is, C ₃ -C ₁₀ cycloalkyl group, C ₆ -C ₁₀ aryl group, a sulfur atom, an oxygen atom and / or nitrogen atoms from 1 to 3 containing 5 to 7-membered heterocyclic group, the substituent group a C ₃ -C ₁₀ cycloalkyl group substituted with 1 to 3 groups selected from a, a C ₆ -C ₁₀ aryl group substituted with 1 to 3 groups selected from substituent group a, and a substituent A group consisting of a 5- to 7-membered heterocyclic group containing 1 to 3 sulfur atoms, oxygen atoms and / or nitrogen atoms substituted with 1 to 3 groups selected from the group a.
However, when R ⁵ is a hydrogen atom, Y represents a C ₁ -C ₁₀ alkylene group substituted with 1 to 3 groups selected from the substituent groups a and b, an oxygen atom in the carbon chain or at the chain end. Or a C ₁ -C ₁₀ alkylene group having a sulfur atom, or C ₁ having an oxygen atom or a sulfur atom in the carbon chain or at the chain end, substituted with 1 to 3 groups selected from the substituent groups a and b —C _{10 represents an} alkylene group. ]
Or a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof.

2. The compound according to claim 1, wherein the compound having formula (I) is of formula (Ia)

Or a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof.

The compound having formula (I) according to claim 1, wherein the compound having formula (Ib)

In any one selected from Claim 1 thru | or 3,
A compound or a pharmacologically acceptable salt thereof, wherein R ¹ and R ² are the same or different and each is a hydrogen atom, a C ₁ -C ₄ aliphatic acyl group or a C ₁ -C ₄ alkoxycarbonyl group.

In any one selected from Claim 1 thru | or 3,
Salts R ¹ and R ² are the same or different, are permissible hydrogen atom or a C ₁ -C ₂ aliphatic acyl group or a C ₁ -C ₂ alkoxycarbonyl group compound or a pharmacologically.

In any one selected from Claim 1 thru | or 3,
Salts R ¹ and R ² are the same or different, hydrogen atom, it is a compound or a pharmacologically acceptable an acetyl group or a methoxycarbonyl group.

In any one selected from Claim 1 thru | or 3,
A compound or a pharmacologically acceptable salt thereof, wherein R ¹ and R ² are hydrogen atoms.

In any one selected from Claim 1 thru | or 7,
Salts R ³ and R ³ a are the same or different, a hydrogen atom, a lower alkyl group, lower alkenyl group or acceptable compound or a pharmacologically an aralkyl group.

In any one selected from Claim 1 thru | or 7,
R ³ and R ³ a are the same or different, a hydrogen atom or a lower alkyl group, compound or a pharmacologically acceptable salt thereof.

In any one selected from Claim 1 thru | or 7,
A compound or a pharmacologically acceptable salt thereof, wherein R ³ and R ³ a are the same or different and each is a hydrogen atom or a C ₁ -C ₄ alkyl group.

In any one selected from Claim 1 thru | or 7,
A compound or a pharmacologically acceptable salt thereof, wherein R ³ and R ³ a are the same or different and each is a hydrogen atom, a methyl group or an ethyl group.

In any one selected from Claim 1 thru | or 7,
A compound or a pharmacologically acceptable salt thereof, wherein R ³ and R ³ a are hydrogen atoms.

In any one selected from Claim 1 thru | or 12,
A compound or a pharmaceutically acceptable salt thereof, wherein R ⁴ is a C ₁ -C ₄ alkyl group or a hydroxy C ₁ -C ₄ alkyl group.

In any one selected from Claim 1 thru | or 12,
A compound or a pharmacologically acceptable salt thereof, wherein R ⁴ is a C ₁ -C ₂ alkyl group or a hydroxy C ₁ -C ₂ alkyl group.

In any one selected from Claim 1 thru | or 12,
A compound or a pharmacologically acceptable salt thereof, wherein R ⁴ is a C ₁ -C ₂ alkyl group.

In any one selected from Claim 1 thru | or 12,
A compound or a pharmacologically acceptable salt thereof, wherein R ⁴ is a methyl group.

In any one selected from Claim 1 thru | or 16,
A compound wherein n is 2 or 3, or a pharmacologically acceptable salt thereof.

In any one selected from Claim 1 thru | or 16,
A compound wherein n is 2, or a pharmacologically acceptable salt thereof.

19. Any one selected from claims 1 to 18,
X is an ethylene group, an ethynylene group or a group having the formula —D—CH ₂ — [wherein D represents a carbonyl group or a group having the formula —CH (OH) —. ], A phenylene group, a naphthylene group, or a compound which is a phenylene group or a naphthylene group substituted by 1 to 3 groups selected from the substituent group a or a pharmacologically acceptable salt thereof.

19. Any one selected from claims 1 to 18,
X is an ethylene group, an ethynylene group, a group having the formula —CO—CH ₂ —, a phenylene group, or a phenylene group substituted with 1 to 3 groups selected from the group consisting of a halogen atom and a lower alkyl group. Compound or pharmacologically acceptable salt thereof.

In any one of claims 1 to 18,
A compound or a pharmacologically acceptable salt thereof, wherein X is an ethylene group, an ethynylene group or a group having the formula —CO—CH ₂ —.

In any one selected from Claim 1 thru | or 21,
Salts Y is acceptable C ₁ -C ₁₀ alkylene group or a C ₁ -C ₁₀ alkylene group compounds 1 to 3 substituted with a group selected from Substituent group a and b, or a pharmacologically.

In any one of claims 1 to 21,
Y is C ₁ -C ₆ compounds or a pharmacologically acceptable salt thereof is an alkylene group or 1 to 3 substituted C ₁ -C ₆ alkylene group with a hydroxy group.

In any one of claims 1 to 21,
Y is C ₁ -C ₅ compound or a pharmacologically acceptable salt thereof is an alkylene group or a hydroxy 1 to 3 substituted C ₁ -C ₅ alkylene group in group.

In any one of claims 1 to 21,
A compound or a pharmacologically acceptable salt thereof, wherein Y is an ethylene group, trimethylene group, tetramethylene group, or an ethylene group, trimethylene group or tetramethylene group substituted with one hydroxy group.

In any one of claims 1 to 21,
A compound or a pharmacologically acceptable salt thereof, wherein Y is an ethylene group, trimethylene group or tetramethylene group.

In any one of claims 1 to 21,
A compound or a pharmacologically acceptable salt thereof, wherein Y is an ethylene or trimethylene group.

In any one of claims 1 to 21,
Y has an oxygen atom or sulfur atom in the carbon chain or at the chain end, substituted with a C ₁ -C ₁₀ alkylene group having an oxygen atom or sulfur atom at the carbon chain or at the chain end, or one hydroxy group C ₁ -C ₁₀ compound or pharmacologically acceptable salt thereof is an alkylene group.

In any one of claims 1 to 21,
Y is, C ₁ -C ₁₀ compound or pharmacologically acceptable salt thereof is an alkylene group having an oxygen atom or a sulfur atom in the carbon chain or the chain ends.

In any one of claims 1 to 21,
Y is, C ₁ -C ₁₀ compound or pharmacologically acceptable salt thereof is an alkylene group having an oxygen atom in the carbon chain or the chain ends.

In any one of claims 1 to 21,
A compound or a pharmacologically acceptable salt thereof, wherein Y is a C ₁ -C ₆ alkylene group having an oxygen atom in the carbon chain or at the chain end.

In any one of claims 1 to 21,
Y is the formula _{-O-CH 2 -, - O-} (CH 2) 2 -, - O- (CH 2) 3 -, - CH 2 -O -, - (CH 2) 2 -O- or - ( CH ₂₎ group, compound or pharmacologically acceptable salt thereof having ₃ -O-.

In any one of claims 1 to 21,
A compound or a pharmacologically acceptable salt thereof, wherein Y is a group having the formula —CH ₂ —O— or — (CH ₂ ) ₂ —O—.

34. Any one of claims 1 to 33 selected from
R ⁵ is The compound or pharmacologically acceptable salt thereof is a hydrogen atom.

34. Any one of claims 1 to 33 selected from
R ⁵ is a C ₃ -C ₁₀ cycloalkyl group, a C ₆ -C ₁₀ aryl group, a sulfur atom, an oxygen atom and / or a 5- to 7-membered heterocyclic group containing 1 to 3 nitrogen atoms, a substituent group a and a C ₃ -C ₁₀ cycloalkyl group substituted with 1 to 3 groups selected from b or a C ₆ -C ₁₀ aryl group substituted with 1 to 3 groups selected from substituent groups a and b A compound or a pharmacologically acceptable salt thereof.

34. Any one of claims 1 to 33 selected from
R ⁵ is a C ₃ -C ₁₀ cycloalkyl group, a C ₆ -C ₁₀ aryl group, or a group consisting of a halogen atom, a lower alkyl group, a halogeno lower alkyl group, a lower alkoxy group, a lower alkylthio group, and a lower aliphatic acyl group. Or a pharmacologically acceptable salt thereof, which is a C ₃ -C ₁₀ cycloalkyl group or a C ₆ -C ₁₀ aryl group substituted with 1 to 3 groups selected from:

34. Any one of claims 1 to 33 selected from
R ⁵ is selected from the group consisting of C ₃ -C ₁₀ cycloalkyl group, C ₆ -C ₁₀ aryl group, or halogen atom, lower alkyl group, halogeno lower alkyl group, lower alkoxy group and lower aliphatic acyl group. Or a pharmacologically acceptable salt thereof, which is a C ₃ -C ₁₀ cycloalkyl group or C ₆ -C ₁₀ aryl group substituted with 1 to 3 groups.

34. Any one of claims 1 to 33 selected from
A compound or a pharmacologically acceptable salt thereof, wherein R ⁵ is a C ₅ -C ₆ cycloalkyl group, a phenyl group or a naphthyl group.

34. Any one of claims 1 to 33 selected from
A compound or a pharmacologically acceptable salt thereof, wherein R ⁵ is a cyclohexyl group or a phenyl group.

40. Any one selected from claims 1 to 39,
A compound or a pharmacologically acceptable salt thereof, wherein R ⁶ and R ⁷ are the same or different and each is a hydrogen atom, a halogen atom, a lower alkyl group, a halogeno lower alkyl group, a lower alkoxy group or a lower alkylthio group.

40. Any one of claims 1 to 39, selected from
A compound or a pharmacologically acceptable salt thereof, wherein R ⁶ and R ⁷ are hydrogen atoms.

In any one selected from Claims 1 thru | or 41,
A compound or a pharmacologically acceptable salt thereof, wherein Z is an oxygen atom.

In Claim 1, any one compound or its pharmacologically acceptable salt selected from the following:
Phosphoric acid mono 2-amino-2-methyl-4- [5- (4-cyclohexylbutyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- (5-cyclohexylpentyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- (5-phenylpentyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- (4-cyclohexyloxybutyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (4-fluorophenoxy) butyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (4-methoxyphenoxy) butyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- (4-benzyloxybutyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- (4-cyclohexylbut-1-ynyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- (4-phenylbut-1-ynyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- (5-cyclohexylpent-1-ynyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- (5-phenylpent-1-ynyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (4-fluorophenyl) pent-1-ynyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (4-methoxyphenyl) pent-1-ynyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (4-methylcyclohexyloxy) propynyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (4-methylphenoxy) propynyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (4-ethylphenoxy) propynyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (4-methylthiophenoxy) propynyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- (4-cyclohexyloxybut-1-ynyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (4-fluorophenoxy) but-1-ynyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [4- (4-methylphenoxy) but-1-ynyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- (3-cyclohexylmethoxypropynyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- (4-phenylmethoxybut-1-ynyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- (4-cyclohexylbutanoyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- (4-phenylbutanoyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- (5-cyclohexylpentanoyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- (5-phenylpentanoyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [5- (4-fluorophenyl) pentanoyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-ethyl-4- [5- (5-cyclohexylpentyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-ethyl-4- [5- (5-cyclohexylpent-1-ynyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-ethyl-4- [5- (5-cyclohexylpentanoyl) thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (4-chlorophenoxy) propynyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (3-methylphenoxy) propynyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (3,4-dimethylphenoxy) propynyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (3-methoxyphenoxy) propynyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (3,4-dimethoxyphenoxy) propynyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (3,5-dimethoxyphenoxy) propynyl] thiophen-2-yl] butyl ester,
Phosphoric acid mono 2-amino-2-methyl-4- [5- [3- (3-acetylphenoxy) propynyl] thiophen-2-yl] butyl ester and phosphoric acid mono 2-amino-2-methyl-4- [ 5- [3- (4-Acetylphenoxy) propynyl] thiophen-2-yl] butyl ester.

In Claim 1, any one compound or its pharmacologically acceptable salt selected from the following:
3-amino-3-methyl-5- [5- (4-cyclohexylbutyl) thiophen-2-yl] pentylphosphonic acid,
3-amino-3-methyl-5- [5- (5-cyclohexylpentyl) thiophen-2-yl] pentylphosphonic acid,
3-amino-3-methyl-5- [5- (5-phenylpentyl) thiophen-2-yl] pentylphosphonic acid,
3-amino-3-methyl-5- [5- (4-cyclohexyloxybutyl) thiophen-2-yl] pentylphosphonic acid,
3-amino-3-methyl-5- [5- [4- (4-fluorophenoxy) butyl] thiophen-2-yl] pentylphosphonic acid,
3-amino-3-methyl-5- [5- [4- (4-methoxyphenoxy) butyl] thiophen-2-yl] pentylphosphonic acid,
3-amino-3-methyl-5- [5- (4-benzyloxybutyl) thiophen-2-yl] pentylphosphonic acid,
3-amino-3-methyl-5- [5- (4-cyclohexylbutanoyl) thiophen-2-yl] pentylphosphonic acid,
3-amino-3-methyl-5- [5- (4-phenylbutanoyl) thiophen-2-yl] pentylphosphonic acid,
3-amino-3-methyl-5- [5- (5-cyclohexylpentanoyl) thiophen-2-yl] pentylphosphonic acid,
3-amino-3-methyl-5- [5- (5-phenylpentanoyl) thiophen-2-yl] pentylphosphonic acid,
3-amino-3-methyl-5- [5- [5- (4-fluorophenyl) pentanoyl] thiophen-2-yl] pentylphosphonic acid,
3-amino-3-ethyl-5- [5- (5-cyclohexylpentyl) thiophen-2-yl] pentylphosphonic acid and
2-Amino-2-ethyl-4- [5- (5-cyclohexylpentanoyl) thiophen-2-yl] pentylphosphonic acid.