TW200938226A - Whitening agent and skin care agent - Google Patents
Whitening agent and skin care agent Download PDFInfo
- Publication number
- TW200938226A TW200938226A TW098104025A TW98104025A TW200938226A TW 200938226 A TW200938226 A TW 200938226A TW 098104025 A TW098104025 A TW 098104025A TW 98104025 A TW98104025 A TW 98104025A TW 200938226 A TW200938226 A TW 200938226A
- Authority
- TW
- Taiwan
- Prior art keywords
- compound
- acid
- whitening agent
- phase
- agent
- Prior art date
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- 230000002087 whitening effect Effects 0.000 title claims description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 50
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 26
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 2
- 230000000144 pharmacologic effect Effects 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 11
- 239000004615 ingredient Substances 0.000 abstract description 9
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 2
- 239000007854 depigmenting agent Substances 0.000 abstract 2
- 229920000877 Melamine resin Polymers 0.000 abstract 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 abstract 1
- 239000012071 phase Substances 0.000 description 31
- -1 pyrimidine compound Chemical class 0.000 description 29
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
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- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
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- YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2- Chemical compound [Na+].CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 description 1
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- 229940032094 squalane Drugs 0.000 description 1
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- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- SHWIJIJNPFXOFS-UHFFFAOYSA-N thiotaurine Chemical compound NCCS(O)(=O)=S SHWIJIJNPFXOFS-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229940093609 tricaprylin Drugs 0.000 description 1
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 1
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
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- 150000003700 vitamin C derivatives Chemical class 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000008170 walnut oil Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/16—Emollients or protectives, e.g. against radiation
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
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- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
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- Chemical & Material Sciences (AREA)
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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Toxicology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Immunology (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
200938226 六、發明說明： 本申請案主張2008年2月8日提出申請的日本專利申 請2008-29106號及2008年8月1日提出申請的日本專利 申請2008-199606號的優先權，並包含在本案中。 【發明所屬之技術領域】 本發明是關於美白劑及皮膚外用劑，尤其與其有效成 分。 【先前技術】 皮膚的黑斑、雀斑等的色素的沉積，是以激素的異常 或紫外線的刺激為誘因，在表皮色素細胞内黑色素產生的 宄進’黑色素在表皮沉積過剩而產生。 作為這種黑色素異常沉積的防止、改善之目的，一般 將美白劑調配於皮膚外用劑。目前，作為美白劑而調配於 皮膚外用劑的成分，有維生素c衍生物、麴酸、熊果素 (albutin，4-羥苯基-石-吡喃葡萄糖苷（gluc〇pyran〇一 side))或白藜蘆醇（rucinol，4_n_丁基間苯二酚 resorcinol))，鞣花酸（euagic acid)等，已知這些有抑 制黑色素生成之作用。 但是在其效果或安全性方面尚未得到可充分滿足者， 因而有開發新美白劑的需求。 一方面，在專利文獻1中，有記載具有鉀離子通道之 調節作用的吡唑嘧啶（pyraZ〇le pyrimidine)化合物。 又，專利文獻2至4有記載對稻熱病、稻胡麻葉枯病、 胡瓜白粉病等具有防除活性的σ比也嘴咬化合物。 320956 . 4 200938226 又，在專利文獻5有記載作為鎮痛劑有用的η比唑嘧啶 化合物。 但是，這些文獻中完全沒有記截有關黑色素生成抑制 作用或美白效果。 [專利文獻 1]W02006/100212 [專利文獻2]日本特開昭54-117029號公報 [專利文獻3]日本特開昭54-147921號公報 [專利文獻4 ]日本特開昭62-404號公報 [專利文獻5]日本特公昭42-19593號公報 【發明内容】 [發明所要解決的課題] 本發明是有鑑於前述先前技術的課題而實施者，其目 的為提供具有優越的黑色素生成抑制作用，而作為美白劑 有用的化合物，以及調配這些化合物的皮膚外用劑。 [要解決課題的手段] 為了要解決前述課題，本發明者等精心檢討的結果， 發現特定的嘧啶基11比唑化合物有優越的黑色素生成抑制作 用，並且細胞毒性也極低，而完成了本發明。 即，本發明之美白劑，其有效成分為下列一般式（1) 表示的嘧啶基吡唑化合物，或其藥理學上可容許之鹽。 5 320956 200938226
及R5各分別單獨為氳原子或匕 又，本發明提供一 及匕為氫原子者。美白劑’係在前述美白劑中，r2 又’本發明提供-種美白劑，係在 匕、L及Re為甲基者。 烷基 ❹ 前述美白劑中，、 黑色:生==供—種美白劑’其前述有效成分有抑制 又 〇 ’本發明提供-種皮膚外用劑，以及化妝料，該皮 胃外用劑係調配有前述任—項所記載的敍基対化合物 或其藥理學上可容許之鹽者。 [發明的效果] 本發明的美白劑具有優越的黑色素生成抑制作用，並 且其細胞毒性也極低，適於調配在作為美白劑之皮膚外用 劑中。 【實施方式】 本發明的美白劑，可以下列一般式（D表示。 • 6 320956 200938226
般式（1)中，R!、R3、L及Re各分別單獨為Cl_3烷基。 〇 本發明中’「Cl-3烷基」是指碳數1至3的直鏈狀、分 枝狀或環狀的餘和烴基。例如：甲基、乙基、η-丙基、異 丙基、環丙基等。理想的烷基可列舉如：甲基、乙基等， 尤其佳的是甲基。 匕及Rs各分別單獨為氳原子或（V3烷基。 本發明之美白劑的有效成分所合適的化合物例，可舉 如：Rl、匕、R4及R6為曱基的化合物。 又’本發明之美白劑的有效成分所合適的化合物例， Ο可舉如：匕及r5為氮原子的化合物。 —般式（1)的化合物，可以由公知的方法合成，也可以 購用市售品。以下，以代表性的合成例說明，但並不受其 限制。又，分子内有官能基，而這個官能基會妨礙反應或 有此疑慮時，以可用適當的保護基使反應有效率地進行者 為佳。保護基的利用，可遵照例如：Theodora W. Greene， Peter G. M. Wuts 之 Protective Groups in Organic Synthesis等而實施。 又’阻轉異構物（atropisomer)、幾何異構物或光學異 7 320956 200938226 構物等的異構物存在時，在選擇適當的原料、反應條件及 把行分離操作下，而得純粹的異構物或幾何異構物。在本 發明中，一般式（1)的化合物的純粹異構物，或其混合物也 包含在内。 一般式（1)的化合物’可用下列流程1所示的反應而 得。 流程1 :
在流程1中，聯胺化合物（2)與1，3-二羰基化合物（3a) 或1-磺醯基-3-羰基化合物（3b)的反應，可在例如甲醇等 適當的溶媒中，在鹽酸、乙酸等的酸觸媒存在下，視需要 而一邊加熱一邊進行。本反應例如可遵照：特開昭62-404 號公報（專利文獻 4)，Tetrahedron Lett.，45，4265(2004) 或 Gazzetta Chemica Italiana，93, 100(1963)等所記載 的方法實施。 作為上述流程1的起始原料之聯胺化合物（2)可取自 市售品，或可用公知的方法合成。 例如經由下列流程2所示的反應，以胺化合物（3)作為 起始原料而得目的之聯胺化合物（2)。本反應可遵照例如特 8 320956 200938226 開平8-208620號公報所記載的方法進行。 流程2 :
r3
H2S〇4/NaN02 - SnCI2/HCI
R3 ⑶ ⑵ Q 又，可由下列流程3所示的反應，由有脫離基Z(例如 鹵原子）的嘧啶化合物（4)而得目的之聯胺化合物（2)。本反 應可遵照例如 Chem. Pharm. Bull.，17(7)，1467(1969)， Chem. Pharm. Bull·，11(11)，1382(1963)，藥學雜誌’ 73, 635(1953)等所記載的方法而進行。
流程3 :
z
⑷ ⑵ 上述反應所用的其他化合物，也可適宜組合公知的方 法而合成。 一般式（1)的化合物，可視需要，以通常的方法轉換為 酸加成鹽。酸加成鹽的酸，可舉如：鹽酸、氳溴酸、硫酸、 磷酸等的無機酸，乙酸、丙酸、檸檬酸、乳酸、草酸、順 9 320956 200938226 丁稀二酸、反丁烯二酸、琥珀酸、酒石酸、甲基確酸等的 有機酸。 一般式（1)的化合物有優越的黑色素生成抑制作用， 又，其細胞毒性也非常低。因此，本化合物有用於做為美 白劑’可合適調配於皮膚外用劑，尤其適於以改善或預防 黑斑、雀斑、皮膚暗沉等為目的之皮膚外用劑。 將一般式（1)的化合物作為美白劑而調配於皮膚外用 劑時’在外用劑全量中之調配量，通常為0. 0002質量％以 上’而以0. 002質量％以上為佳。調配量過少時，效果不能 充分發揮。對上限並無特別規定，但通常在3〇質量％以下， 而在20質量％以下為為佳，在5%質量％以下為更佳。調配 量過多，有時也得不到與所增之量相應的顯著效果，有時 也會影響製劑的設計或使用性等。 本發明的皮膚外用劑，除了調配一般式（1)的化合物以 外’可用常法製造。 又，本發明的皮膚外用劑，除了 一般式（1)的化合物 外，在不損害本發明之效果的範圍内，可視需要而適宜調 ^般化妝品或醫藥品等的皮膚外用劑所使用的其他成 刀’例如：油分、濕潤劑、抗紫外線劑、抗氧化劑、金屬 離子螯合劑、界面活性劑、防腐劑、保濕劑、香料、水、 酉精、粉末、色料、生藥、其他各種藥效成分等。 還可適宜調配：維生素C、維生素c磷酸鎂、維生素c 2糖苷、戢果素、麴酸、白藜蘆醇、鞣花酸、胺曱環酸、 亞麻油酸等的其他美白劑。 320956 10 200938226 本發明的皮膚外用劑可以在化妝料、醫藥品、准藥品 (quasi-drug)的領域廣汎適用。其劑型只要可適用於皮 膚，並無特別限制，例如：溶液狀、乳化狀、固形狀、半 固形狀、粉末狀、粉末分散狀、水-油二層分離狀、水—油一 粉末三層分離狀、軟膏狀、凝膠狀、氣膠狀、泡狀（mousse)、 棒狀等，可適用任意劑型。又，其使用形態也可任意，例 如·化妝水、乳液、乳霜、面膜、精油、凍膠等的面部化 妝料，粉底、化妝底霜、遮瑕膏等的上妝用化妝品。 以下，舉具體例說明本發明，但本發明並不受其限制。 [實施例] 對一般式（1)的化合物，進行黑色素生成抑制試驗。 驗方法係如下述。 成抑制試驗 (1)細胞播種、試驗物質的添加
小鼠Β16黑色素瘤細胞以1〇〇, 000細胞/孔播種於6孔 板。第2天添加試驗物質溶液（溶媒：j)MS〇)。 (2)細皰増殖試驗 在添加試驗物質溶液的3天後，將培養基吸除，然後 添加含有ίο%阿爾瑪藍(Alamar Blue，溶液的emem培養<基 lmJ，在37°C下反應。30分鐘後，將1〇〇/W移到移到96 = 乂β發波長544nm、測定波長590nm測定螢光。將 該測定值作為細胞數的相對值，算出試驗物質添 月It試驗物質無添加組（對照組，僅添加溶媒）的細胞數 比年U細胞數）。％細胞數越高，表示細胞毒性越低。以％ 320956 11 200938226 性。婁在8〇/。以上4判斷為無毒性，未達應時判斷為有毒 (3)黑色素定量 200二1驗後的細胞以PBS洗淨3次’添加則囊 素量的：針：月二：定475冊的吸光度。以此值作為黑色 (只添加溶媒)的：色質添加組對試驗物質無添加組 ❹ 示黑色素生成抑制致果=率（％)。黑色素量比率越低，表 最終濃度中，將里色去兩。在判斷為無毒性的試驗物質 驗物質最終濃度;乍為抑成：_下的 …、色素生成的最小》農度（ppm)，而 >列標準評估黑色素生成之抑制效果。 ◎.抑制黑色素生成之最小濃度在^酬以下。 〇：抑制黑色素生成之最小濃度大於lppm並在 lOppm 以下。 ◎ X : lOppm以下而沒有抑制黑色素生成之效果（1〇ppm 以下時黑色素量比率不會在80%以下）。 在表1呈示本發明化合物的黑色素生成抑制試驗的結 果。 表1的化合物都可確認抑制黑色素生成的效果，以 lppm以下極低的濃度表示效果。 320956 12 200938226 〇 [表l] No. r2 Rs R4 Rs Re 抑制黑色素生成之效果 1 Me H Me Me H Me ◎ 2# Me H Me Me H Me ◎ 3 Me H Me Et H Et ◎ 4 Me H Me Me Me Me ◎ 5 Me Me Me Me H Me ◎ # : HC1鹽，Me :甲基，Et :乙基 對於本發明的雜環化合物，將現在臨床上於組成物中 之0.1至30質量％的濃度範圍實際使用的美白劑的熊果 素，及在黑色素瘤B16細胞上呈現顯著抑制黑色素生成之 效果的最小濃度做比較。以化合物1、3及4作為代表例而 表示。 [表2] 試驗化合物 最小濃度（％) 熊果素 5x10—4 化合物1 1χ1(Γ6 化合物2 3x10—6 化合物3 3χ1(Γ6 如上述表2,本發明化合物以熊果素的約1/170至 1/500的濃度對於黑色素瘤B16細胞呈現抑制黑色素生成 之效果，而可理解相較於熊果素，以極低的濃度發揮效果。 13 320956 200938226 以下，呈示本發明的美白劑之雜環化合物的代表性合 成例。使用相對應的原料並遵照該等合成例進行反應，即 可得各種雜環化合物。 合成彳列1 〇密g定基呻匕唾彳匕合物的合成 在100m7的茄形燒瓶中放入聯胺化合物（原料A，9. 25 mmol)，1，3-二幾基化合物（原料B，9. 25mmol)，離子交換 水（3.0mO及乙酸（3.0mi)，回流1小時。反應終了後，添 加10% NaOH水溶液直到成為pHl 0以上後，以乙酸乙醋萃 取。將有機相以飽和食鹽水洗淨1次後，以無水硫酸鎮乾 燥，減壓下餾除溶媒後，以矽膠管柱層析法（己烷：乙酸乙 酉旨=10 : 1)精製，分別得到表3的密咬基11比β坐化合物。 [表3]
No. 構造 原料A 原料B • NMR 收率 1 (4, 6-二甲基 嘧啶-2-基） 聯胺 乙醯两_ 'H-NMRCCDCL·)： 2.34(3H,s), 2.53 (6H, s), 2.64(3H,s), 6.01 (lH,s), 6.88(lH,s) 58% 3 (4, 6-二甲基 嘴咬-2-基） 聯胺 3, 5-庚烧 二酮 ^-NMRCCDCh)： 1. 22-1. 30(6H，m), 2.53 (6H,s),2. 75(2H,q), 3.13(2H,q),6.10C1H, s), 6.88(1H, s) 79% 4 (4, 6-二曱基 哎咬-2-基） 聯胺 甲基_2, 4_ 戊烷二酮 'H-NMRCCDCh)： 1.97(3H,s), 2.29C3H, s), 2.52(6H,s), 2.65 (3H,s), 6.85C1H, s) 39% 14 320956 200938226 合成例 2 2-(3, 5-二甲基口比0坐-1-基）-4，6-二甲基口密g定鹽 酸鹽（化合物2)的合成 丨 在50ml茄形燒瓶中放入2-(3,5-二甲基吡唑-1-基） - -4, 6-二甲基°密σ定（化合物1 )(1. 00g，4· 94mmol)及甲醇 (4. 94mJ)，在室溫下滴入1. ON鹽酸（4. 94m/)。 滴完後，在室溫下攪拌1小時。反應終了後，減壓下 餾除溶媒，所得固體由乙醇與乙酸乙酯之混合溶媒再結 晶，藉此得到2-(3, 5-二甲基吡唑-1-基）-4, 6-二甲基嘧啶 ® 鹽酸鹽（化合物2)0. 93g(收率79%)。 6.15(lH，s)，7.15(lH，s), 7.20(lH，s)。 合成例 3 2_(3，5_二甲基口比g坐_1-基）-4，5, 6-三甲基。密咬 (化合物5)的合成 在lOOinl痴形燒瓶中放入1-肺基-3，5_二曱基°比〇坐硝 酸鹽（l.OOg，4.97mmol)，3-曱基-2,4-戊烷二酮（0.60忌， ❹ 5. 22mmol)，碳酸舒（1. 37g，9. 94mmol)及曱醇（6. 63mJ)， 在室溫下攪拌30分鐘後，回流6小時。反應終了後，濾去 固體後以乙酸乙酯萃取1次。將有機相以飽和食鹽水洗淨 1次後，再用無水硫酸鎂乾燥，減壓餾除溶媒後，以矽膠 管柱層析法（氯仿：己烷=1 : 1与氯仿）精製而得2-(3, 5-二 甲基吡唑-1-基）-4, 5, 6-三甲基嘧啶（化合物5)0. 10g(收量 9%)。 丽R(DMS0-d6) : 2.18(3H，s)，2.22(3H，s)，2.46(6H，s)， 2.49C3H, s), 6.06C1H, s) 15 320956 200938226 以下表示本發明的皮膚外用劑的配方例。在各配方例 中，可使用本發明化合物的1種或2種以上的化合物。下 述配方例的皮膚外用劑都經由本發明化合物的調配而發揮 美白效果。 配方例1 乳霜 (配方） 5.0 質量％ 4. 0 18. 0 3. 0 10. 0 0. 1 0. 2 0. 05 適量 適量 剩餘部分 硬脂酸 硬脂醇 肉苴蔻酸異丙酯 單硬酯酸甘油酯 丙二醇 本發明化合物 苛性鉀 亞硫酸氫鈉 防腐劑 香料 離子交換水 (製法） 於離子交換水中添加丙二醇及苛性_，並使之溶解， 加熱保持7G°C (水相）。將其他成分混合加熱融解並保持於 70°C (油相）。將油相缓緩加於水相，全部加完後暫保持該 溫度，使其起反應。之後，以均質混合機均勻乳化，在充 分攪拌中冷卻到30°C。 配方例2 乳霜 (配方） 16 320956 200938226 5.0 質量％ _ 硬脂酸 去水山梨醇單硬脂酸酯 2. 5 聚氧乙烯（20莫耳） -去水山梨醇單硬脂酸酯 1.5 熊果素 7.0 亞硫酸氫鈉 0.03 丙二醇 10.0 本發明化合物 0.05 ® 三辛酸甘油酯 10.0 鯊烯 5.0 對二甲胺苯曱酸辛酯 3.0 乙二胺四乙酸二鈉 0.01 對羥基苯甲酸乙酯 0.3 香料 適量 離子交換水 剩餘部分 〇 (製法） 將丙二醇及乙二胺四乙酸二鈉鹽添加於離子交換水而 溶解，保持在70°c (水相）。將其他成分混合加熱融解並保 持在70°C (油相），將油相缓緩加於水相在70°C進行預備乳 化，以均質混合機乳化均勻後，在充分攪拌中冷卻到30°C。 配方例3 乳霜 (配方） 固態石蠟 蜜蠟 5.0 質量％ 10. 0 17 320956 200938226 凡士林 15.0 液態石蠟 41.0 單硬脂酸甘油酯 2.0 POE(20)去水山梨醇單月桂酸酯 2. 0 肥皂粉末 硼砂 05 03 適量 剩餘部分 本發明化合物 亞硫酸氫納 對羥基苯甲酸乙酯 香料 離子交換水 (製法） 將肥皂粉末與硼砂加入離子交換水中，加熱溶解並保 持在70°C (水相）。將其他成分混合後加熱融解而保持在70 °C (油相）。將油相缓缓在攪拌下加於水相，進行反應。反 應終了後，以均質混合機乳化均勻，乳化後在充分攪拌下 冷卻至30°C。 西己方例4 乳液 (配方） 2.5 質量％ 1.5 5. 0 10. 0 2. 0 硬脂酸 録蠛醇 凡士林 液態石壤 POE(IO)單油酸酯 18 320956 3 200938226 聚乙二醇1500 三乙醇胺 羧乙烯聚合物 0.05 . 本發明化合物 0.01 亞硫酸氫鈉 0. 01 對羥基苯甲酸乙酯 0.3 香料 適量 離子交換水 剩餘部分 0 (製法） 將羧乙烯聚合物溶解於少量離子交換水（A相）。將聚 乙二醇1500與三乙醇胺加入剩下的離子交換水中，加熱溶 解保持在70°C (水相）。將其他成分混合後加熱融解而保持 在7 0 °C (油相）。將油相加入水相並進行預備乳化，添加A 相並以均質混合機乳化均勻，乳化後在充分攪拌中冷卻到 30〇C。 酉己方例5 乳液 ® (配方） 質量％ 微晶蠟 1.0 蜜蠟 2.0 羊毛脂 20.0 液態石蠟 10. 0 鯊烷 5.0 去水山梨醇倍半油酸酯 4.0 POE(20)去水山梨醇單油酸醋 1.0 19 320956 200938226 丙二醇 7.0 本發明化合物 1.0 亞硫酸氮納 0.01 對羥基苯曱酸乙酯 0. 3 香料 適量 離子交換水 剩餘部分 (製法） 將丙二醇加於離子交換水中，加熱而保持在70°C(水 相）。將其他成分混合後加熱融解而保持在7(TC (油相）。 加入於油相’ Ά質混合機乳 句勻。乳化後在充分授拌下冷卻至3〇乞。 凌塍 (配方） 95%乙醇 二丙二醇 Ρ〇Ε(50)油基醚 羧乙烯聚合物 苛性鈉 L-精胺酸 本發明化合物 2-羥基-4甲氧基二笨甲酮磺酸鈉 乙二胺四乙酸三鈉二水 對羥基苯甲酸乙酯 香料 10· 0質量％ 15.0 15 0 05 0.05〇. 2適量 320956 20 200938226 離子交換水 剩餘部分 (製法） 將羧乙烯聚合物均勻溶解於離子交換水中，另一方面 將本發明化合物、POEC50)油基醚溶解於95%乙醇中，而加 入於水相。繼而加入其他成分後，以苛性鈉、L-精胺酸中 和增稠。 配方例7 美容液 (配方） ❹（A相） 乙醇（95°/〇) 10.0 質量％ POEC20)辛基十二烷醇 1. 0 泛醇乙醚 0. 1 本發明化合物 2. 0 對羥基苯曱酸甲酯 0. 15 (B相） 氫氧化鉀 0. 1 (C相） 甘油 5. 0 二丙二醇 10. 0 亞硫酸氫鈉 0. 03 羧乙烯聚合物 0. 2 離子交換水 剩餘部分 (製法） 將A相、C相分別溶解均勻 ，將A相加於C相而可溶 〇 21 320956 200938226 化。繼而加入B相後裝入容器内。 配方例8 面膜 (配方） (A相） 二丙二醇 P〇E(60)硬蓖麻油 (B相） 本發明化合物 撖欖油 生育酚乙酸酯 對羥基苯甲酸乙酯 香料 (C相） 亞硫酸氯納 聚乙烯醇 (皂化度90，聚合度2, 〇〇〇) 乙醇 精製水 (製法） 5.0質量％ 0. 05 5. 0 0.2 0.2 0. 2 0. 03 13. 0 7. 0 剩餘部分
、相、β相、C相分別溶解均勻，將b相加入於a相 而可溶化。繼而將其加入於C相後裝入容器内。 ___ (配方） 滑石 43. 1 質量％ 22 •320956 200938226 高嶺土 絲雲母 鋅華 二氧化鈦 黃色氧化鐵 黑色氧化鐵 鯊烷 異硬脂酸 Ρ0Ε去水山梨醇單油酸酯 辛酸異鯨蠟酯 本發明化合物 防腐劑 香料 (製法） 15. 0 10. 0 7. 0 3. 8
4. 適量 適量 將滑石至黑色氧化鐵的粉末成分以混合機充分混合， 〇在此加人m辛酸㈣_的油性成分、本發明化人 物、防腐劑、香料而充分揉捏後，裝人容器内成型。σ Ig>方例__底料d霜刮） (配方） (粉體部） 二氧化鈦 絲雲母 高嶺土 黃色氧化鐵 10· 3質量％ 5.4 3. 00. 8 320956 23 200938226 紅色氣化鐵（benga 1 a) 0.2 11. 5 4. 5 4. 〇 0. 5 50. 〇 4. 5 3. 0 適量 適量 黑色氧化鐵 (油相） 十甲基環五矽氧烷 液態石蟻 聚氧乙烯變性二甲基聚矽氧烷 本發明化合物 (水相） 精製水 1，3-丁二醇 去水山梨醇倍半油酸酯 防腐劑 香料 (製法） -將水相加熱授拌後’加入充分混合粉碎的粉體部後以 均質混合機處理。再加入加熱混合的油相以均質混合機處 理後，在攪拌下加入香料冷卻至室溫。 芕例.11化妝水 0.05質量％ 1.0 0. 01
(1) 本發明化合物 (2) 天門冬胺酸 (3) 生育酚乙酸酯 (4) 甘油 (5) 1，3-丁二醇 (6) 乙醇 320956 200938226 (7) POE(60)硬化蓖麻油 0.5 (8) 對羥基苯甲酸曱酯 0.2 (9) 檸檬酸 0.05 (10) 檸檬酸鈉 0.1 (11) 香料 0.05 (12) 精製水 剩餘部分 (製法）
溶解（2)、（4)、（5)、（9)及（10)於（12)成為精製水溶 液。另外將（1)、（3)、（7)、（8)、及（11)溶解於（6)，將其 加於前述的精製水溶液而可溶化，過濾而得化妝水。 配方例12 化妝水 A :醇相 乙醇 5. 0 質量％ POE油基醚 2. 0 2-乙基己基-P-二甲基胺基苯曱酸酯 0. 18 0. 05 9. 5 0. 5 0. 5 5. 0 0· 3 本發明化合物 香料 B :水相 1,3-丁二醇 2-0-乙基維生素C 吡咯烷酮羧酸鈉 乳清萃取液 於驗醯胺 甘油 5.0 25 320956 200938226 羥丙基-yS-環糊精 乙二胺羥乙基三乙酸三鈉 離胺酸 胺曱環酸 精製水 (製法） 1.01.0 0. 051. 0 剩餘部分 將A的醇相加於B的水相，使可溶化而得化妝水。 配方例13 乳霜（美白） 鹽酸反-4-(反胺曱基環己烷羰基）胺 甲基環己烷羧酸 4-甲氧基柳酸鉀 3-0-乙基維生素C 亞麻油酸 硫辛酸納 本發明化合物 輔腾 QlO(CoQlO) 凡士林 二甲基聚矽氧烷 乙醇 山 |醇（behenyl alcohol) 鲨肝醇（batyl alcohol) 甘油 1. 0質量％ 03 1，3-丁二醇 聚乙二醇20000 26 320956
0. 200938226 荷荷爸油 鯊烷 植物留醇羥基硬脂酸酯 (phytosteryl hydroxystearate) 季戊四醇四2-乙基己酸酯 聚氧乙烯硬化蓖麻油 氫氧化鉀 焦亞硫酸鈉 六偏磷酸鈉 甘草次酸硬脂酯 泛醇乙醚 熊果素 胺曱環酸 生育酚乙酸酯 玻尿酸鈉 . 對羥基苯甲酸酯 乙二胺四乙酸三鈉 ί-t-丁基-4’ -甲氧基二苯甲醯基甲烷 二對曱氧基桂皮酸酯單甘油2-乙基己酸酯0. 黃色氧化鐵 黃原膠（xanthan gum) 羧乙烯聚合物 精製水 配方例14 雙層型乳霜（防曬） 適量 0. 1 0. 2 剩餘部分 27 320956 200938226 2.0質量％ 胺曱環酸 4-曱氧基柳酸鉀 本發明化合物 0.03 二曱基聚矽氧烷 25.0 十曱基環五矽氧烷 25.0 三曱基矽氧基矽酸酯 5.0 聚氧乙烯·曱基聚矽氧烷共聚物 2.0 二丙二醇 5.0
棕櫚酸糊精敷蓋微粒子鋅華（60nm) 15. 0 甘草次酸二鉀 0.02 麵胱甘肽（glutathione) 1.0 硫代牛磺酸 0.05 苦參萃取物（苦參Sophora 1.0 flavescens 萃取物） 對羥基苯曱酸酯 適量
苯氧基乙醇 適量 乙二胺四乙酸三鈉 適量 對曱氧基桂皮酸2-乙基己酯 7. 5 二曱基二硬脂基銨鋰皂石 0.5 (dimethyldistearylaramonium hectorite) 球狀聚丙烯酸烷酯粉末 5.0 丁基乙基丙二醇 0.5 剩餘部分 適量 精製水 香料 28 320956 200938226 配方例15 凝膠（美白） 4-甲氧基柳酸鉀 白藜蘆醇 二氫硫辛酸 野芝麻 (Lamium album var. barbatum) 二曱基聚矽氧烷 甘油 1，3_丁二醇 聚乙二醇1500 聚乙二醇20000 辛酸録壤酉旨 檸檬酸 檸檬酸鈉 六偏礦^酸納 本發明化合物 甘草次酸二舒 微生素C葡萄糖苷 生育酚乙酸酯 黄答萃取物 虎耳草（Saxifraga stolonifera) 萃取物 乙二胺四乙酸三鈉 黃原膠
質量％
0 29 320956 200938226 0. 05 1.5 適量 適量 剩餘部分 丙烯酸•甲基丙烯酸烷酯 共聚物（pemulen TR-2) 洋菜粉末 苯氧基乙醇 二丁基羥甲苯 精製水 配方例16 面膜（保濕） 反式4-胺甲基環己烷羧酸甲醯胺鹽酸鹽10. 0質量％ 二氫硫辛醯胺 營實 乙醇 1，3-丁二酵 聚乙二醇4000 撖欖油 澳洲胡桃油 植物留醇羥基硬脂酸酯 乳酸 乳酸鈉 L-維生素C硫酸醋二納 本發明化合物 α -生育酚2-L-維生素C磷酸二酯鉀 維生素Ε乙酸酉旨 魚膠原蛋白 軟骨素硫酸鈉 1. 10 05 05 ❹ ❹ 30 320956 200938226 (Chondroitin sodiuim sulfate) 羧曱基纖維素鈉 聚乙烯醇 對羥基苯甲酸酯 精製水 香料 配方例17 化粧水（保濕） 胺甲環酸 4-曱氧基柳酸鉀 硫辛酸 金縷梅（Hamamelis japonica) 氧化矽敷蓋氧化鋅 次牛磺酸 苦參萃取物 桃仁萃取物 山毛櫸的芽萃取物 A醇 本發明化合物 乙醇 甘油 1，3-丁二醇 聚氧乙烯聚氧丙烯癸基十四基醚 六偏鱗酸納 三甲基甘胺酸 0. 2 12. 0 適量 適量 適量 1.0
10. 0 01
質量％ 31 .320956 200938226 聚天門冬酸鈉 α -生育酚2-L-維生素C鱗酸二酯鉀 硫代牛磺酸 綠茶萃取物 西洋薄荷萃取物 鳶尾根萃取物 (Iris Florentina Root Extract) 乙二胺四乙酸三鈉 羧乙烯聚合物 氫氧化鉀 苯氧基乙醇 精製水 香料 【圖式簡單說明】 無。 【主要元件符號說明】 無。
0. 05 0. 02 適量 剩餘部分 適量
32 320956
Claims (1)
- 化合物或其藥理學切料的鹽作為有效成分， ❹ Ο 200938226 七、申清專利範圍.:. 1·種美白劑’其特徵為以—般式⑴表示㈣咬基吼峻(1) (式中，Rl、R3、匕及R6各分別單獨為Ch烷基，R2 及r5各分別單獨為氫原子或Ci3絲）。 .:申明專利乾圍第}項的美白劑，其中，R2及匕為氫原 子0 3.如申請專利範㈣1項或第2項的美白劑，其中，Ri、 I、R4及R6為甲基。 4·:申請專利範圍第i項至第3項中任一項的美白劑，盆 中’前述有效成分騎似色素生成者。 ，、 5·:種皮膚外配有申請專·时丨項至第* 項中任一項的°密°定基対化合物或其藥理學上可料 的鹽者。 干工」谷訐 6.—種化妝料’係調配有申請專利範圍第丨項至 ^項的t定基㈣化合物或其藥理學上可容許的鹽 320956 33 200938226 四、指定代表圖：本案無圖式。 k (一)本案指定代表圖為：第（ ）圖。 (二)本代表圖之元件符號簡單說明： 五、本案若有化學式時，請揭示最能顯示發明特徵的化學式：3 320956
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