PE20080109A1 - N-sulfonilacion selectiva de alcoholes sustituidos con 2-aminotrifluoralquilo - Google Patents
N-sulfonilacion selectiva de alcoholes sustituidos con 2-aminotrifluoralquiloInfo
- Publication number
- PE20080109A1 PE20080109A1 PE2007000169A PE2007000169A PE20080109A1 PE 20080109 A1 PE20080109 A1 PE 20080109A1 PE 2007000169 A PE2007000169 A PE 2007000169A PE 2007000169 A PE2007000169 A PE 2007000169A PE 20080109 A1 PE20080109 A1 PE 20080109A1
- Authority
- PE
- Peru
- Prior art keywords
- alkyl
- methylmorpholine
- substituted
- halogen
- trifluorometil
- Prior art date
Links
- 150000001298 alcohols Chemical group 0.000 title 1
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 abstract 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 abstract 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 abstract 1
- 150000001414 amino alcohols Chemical group 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 abstract 1
- 229940011051 isopropyl acetate Drugs 0.000 abstract 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 abstract 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/38—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/17—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
SE REFIERE A UN PROCESO PARA PREPARAR ALCOHOL SUSTITUIDO CON SULFONAMIDA-TRIFLUOROALQUILO DE FORMULA (I) O (II), DONDE R1 Y R2 SON CADA UNO H, ALQUILO C1-C6, CF3, ALQUENILO C2-C6, ENTRE OTROS; R3 ES H, ALQUILO C1-C6 SUSTITUIDO O NO; R4 ES ALQUILO (CF3)n, (CF3)n(ALQUILO SUSTITUIDO), (CF3)nALQUILFENILO, ENTRE OTROS; n ES 1-3; R5 ES H, HALOGENO, CF3; W, Y y Z SON CADA UNO C, CR6, N; X ES O, S, SO2, NR7; R6 ES H, HALOGENO, ALQUILO C1-C6 SUSTITUIDO O NO; R7 ES H, ALQUILO C1-C6, CICLOALQUILO C3-C8; R8, R9, R10, R11 Y R12 SON CADA UNO H, HALOGENO, ALQUILO C1-C6, ALCOXI C1-C6, NO2, ENTRE OTROS. DICHO PROCESO CONSISTE EN HACER REACCIONAR UN AMINO ALCOHOL SUSTITUIDO CON TRIFLUOROALQUILO TAL COMO (2S)-2-AMINO-4,4,4-TRIFULOR-3-(TRIFLUOROMETIL)BUTAN-1-OL, UN CLORURO DE SULFONILO Y UN SISTEMA DE BASE SOLVENTE SELECCCIONADO DE 4-METILMORFOLINA/ACETATO DE ISOPROPILO, TETRAHIDROFURANO/BASE DE HUNIG, 4-METILMORFOLINA/ACETONITRILO, 4-METILMORFOLINA/PROPIONITRILO, 4-METILMORFOLINA/TOLUENO. UN COMPUESTO PREPARADO MEDIANTE DICHO PROCESO ES: 4-CLORO-[N-(1S)-3,3,3-TRIFLUOR-1-(HIDROXIMETIL)-2-(TRIFLUOROMETIL)PROPIL]BENCENSULFONAMIDA. DICHOS COMPUESTOS SON INHIBIDORES DE LA PRODUCCION DE BETA AMILOIDES SIENDO UTILES EN EL TRATAMIENTO DE ALZHEIMER
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77430006P | 2006-02-17 | 2006-02-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PE20080109A1 true PE20080109A1 (es) | 2008-04-01 |
Family
ID=38124142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE2007000169A PE20080109A1 (es) | 2006-02-17 | 2007-02-15 | N-sulfonilacion selectiva de alcoholes sustituidos con 2-aminotrifluoralquilo |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US7838550B2 (es) |
| EP (1) | EP1984347A1 (es) |
| JP (1) | JP2009527476A (es) |
| KR (1) | KR20080094685A (es) |
| CN (1) | CN101384579A (es) |
| AR (1) | AR059517A1 (es) |
| AU (1) | AU2007217966A1 (es) |
| BR (1) | BRPI0707742A2 (es) |
| CA (1) | CA2637615A1 (es) |
| CR (1) | CR10158A (es) |
| EC (1) | ECSP088684A (es) |
| GT (1) | GT200800154A (es) |
| IL (1) | IL192929A0 (es) |
| NO (1) | NO20083488L (es) |
| PE (1) | PE20080109A1 (es) |
| RU (1) | RU2008131051A (es) |
| TW (1) | TW200732295A (es) |
| WO (1) | WO2007098030A1 (es) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK1465861T3 (da) | 2001-12-20 | 2009-08-31 | Bristol Myers Squibb Co | Alpha-(N-sulfonamid)acetamidderivater som beta-amyloidhæmmere |
| NZ542468A (en) * | 2003-03-31 | 2009-01-31 | Wyeth Corp | Fluoro- and trifluoroalkyl-containing heterocyclic sulfonamide inhibitors of beta amyloid production and derivatives thereof |
| US7550629B2 (en) * | 2006-04-21 | 2009-06-23 | Wyeth | Trifluoromethyl-containing phenylsulfonamide beta amyloid inhibitors |
| US7476762B2 (en) * | 2006-04-21 | 2009-01-13 | Wyeth | Methods for preparing sulfonamide compounds |
| PE20090824A1 (es) * | 2007-07-16 | 2009-07-24 | Wyeth Corp | Proceso para la preparacion de trifluoralquil-fenil sulfonamidas y de sulfonamidas heterociclicas |
| PA8789801A1 (es) * | 2007-07-16 | 2009-02-09 | Wyeth Corp | Procesos e intermadiarios para la preparacion de compuestos de silfonamida heterocíclica |
| PE20090445A1 (es) * | 2007-07-16 | 2009-05-18 | Wyeth Corp | Inhibidores de produccion de beta amiloide |
| US8084477B2 (en) | 2007-10-31 | 2011-12-27 | Bristol-Myers Squibb Company | Alpha-(N-sulfonamido)acetamide compound as an inhibitor of beta amyloid peptide production |
| US8093276B2 (en) * | 2007-10-31 | 2012-01-10 | Bristol-Myers Squibb Company | Alpha-(N-sulfonamido)acetamide compound as an inhibitor of beta amyloid peptide production |
| JP2011523633A (ja) * | 2008-05-08 | 2011-08-18 | ブリストル−マイヤーズ スクイブ カンパニー | ２−アリールグリシンアミド誘導体 |
| US8044077B2 (en) | 2009-03-19 | 2011-10-25 | Bristol-Myers Squibb Company | Alpha-(N-sulfonamido)acetamide compounds incorporating deuterium as inhibitors of beta amyloid peptide production |
| US20110071199A1 (en) * | 2009-03-20 | 2011-03-24 | Bristol-Myers Squibb Company | Thiophenyl Sulfonamides for the Treatment of Alzheimer's Disease |
| US7977362B2 (en) * | 2009-03-20 | 2011-07-12 | Bristol-Myers Squibb Company | Alpha-(N-benzenesulfonamido)cycloalkyl derivatives |
| US8252821B2 (en) * | 2009-04-14 | 2012-08-28 | Bristol-Myers Squibb Company | Bioavailable capsule compositions of amorphous alpha-(N-sulfonamido)acetamide compound |
| TW201043269A (en) * | 2009-04-14 | 2010-12-16 | Bristol Myers Squibb Co | Bioavailable compositions of amorphous alpha-(N-sulfonamido)acetamide compound |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5795890A (en) | 1995-09-27 | 1998-08-18 | Ono Pharmaceutical Co., Ltd. | Sulfonamide derivatives |
| JPH09241262A (ja) | 1996-03-08 | 1997-09-16 | Kao Corp | ３−オキサ−２，７−ジアザビシクロ〔３．３．０〕オクタン誘導体 |
| US5962231A (en) | 1997-09-30 | 1999-10-05 | Incyte Pharmaceuticals, Inc. | Human glutathione-S-transferase |
| CA2309332C (en) | 1997-11-12 | 2002-12-03 | Bayer Aktiengesellschaft | 2-phenyl substituted imidazotriazinones as phosphodiesterase inhibitors |
| JPH11343279A (ja) | 1998-03-16 | 1999-12-14 | Shionogi & Co Ltd | スルホンアミド誘導体およびそれらを含有するＴＮＦ―α産生抑制剤 |
| GB9805520D0 (en) | 1998-03-17 | 1998-05-13 | Zeneca Ltd | Chemical compounds |
| DE19827640A1 (de) | 1998-06-20 | 1999-12-23 | Bayer Ag | 7-Alkyl- und Cycloalkyl-substituierte Imidazotriazinone |
| WO2001047928A2 (de) | 1999-12-24 | 2001-07-05 | Bayer Aktiengesellschaft | Imidazo 1,3,5 triazinone und ihre verwendung |
| EP1261609B1 (de) | 1999-12-24 | 2004-11-03 | Bayer HealthCare AG | Triazolotriazinone und ihre verwendung |
| BR0116063A (pt) | 2000-12-13 | 2004-08-03 | Wyeth Corp | Inibidores de sulfonamida heterocìclica da produção de beta amilóide e seus usos |
| US6657070B2 (en) | 2000-12-13 | 2003-12-02 | Wyeth | Production of chirally pure α-amino acids and N-sulfonyl α-amino acids |
| JP4250529B2 (ja) | 2001-12-11 | 2009-04-08 | ワイス | キラル的に純粋なβ−アミノアルコールの合成方法 |
| TW200307539A (en) | 2002-02-01 | 2003-12-16 | Bristol Myers Squibb Co | Cycloalkyl inhibitors of potassium channel function |
| JP2005526765A (ja) | 2002-03-11 | 2005-09-08 | シエーリング アクチエンゲゼルシャフト | Ｃｄｋ−阻害性２−ヘテロアリール−ピリミジン類、それらの生成及び医薬としての使用 |
| US7288547B2 (en) | 2002-03-11 | 2007-10-30 | Schering Ag | CDK-inhibitory 2-heteroaryl-pyrimidines, their production and use as pharmaceutical agents |
| TW200403058A (en) | 2002-04-19 | 2004-03-01 | Bristol Myers Squibb Co | Heterocyclo inhibitors of potassium channel function |
| JP4530849B2 (ja) | 2002-06-11 | 2010-08-25 | ワイス・エルエルシー | βアミロイド産生の置換フェニルスルホンアミド阻害剤 |
| WO2004078731A1 (en) | 2003-03-06 | 2004-09-16 | 'chemical Diversity Research Institute', Ltd. | Quinoline-carboxylic acids and the derivatives thereof, a focused library |
| NZ542468A (en) | 2003-03-31 | 2009-01-31 | Wyeth Corp | Fluoro- and trifluoroalkyl-containing heterocyclic sulfonamide inhibitors of beta amyloid production and derivatives thereof |
| ES2330451T3 (es) | 2004-01-16 | 2009-12-10 | Wyeth | Inhibidores a base de sulfonamidas heterociclicas de la produccion de beta-amiloides que contienen un azol. |
| PE20080169A1 (es) * | 2006-02-17 | 2008-04-11 | Wyeth Corp | Metodo para preparar alcoholes sustituidos con sulfonamidas y sus compuestos intermedios |
-
2007
- 2007-02-15 CA CA002637615A patent/CA2637615A1/en not_active Abandoned
- 2007-02-15 US US11/706,938 patent/US7838550B2/en not_active Expired - Fee Related
- 2007-02-15 TW TW096105702A patent/TW200732295A/zh unknown
- 2007-02-15 AU AU2007217966A patent/AU2007217966A1/en not_active Abandoned
- 2007-02-15 RU RU2008131051/04A patent/RU2008131051A/ru not_active Application Discontinuation
- 2007-02-15 JP JP2008555375A patent/JP2009527476A/ja not_active Withdrawn
- 2007-02-15 EP EP07750893A patent/EP1984347A1/en not_active Withdrawn
- 2007-02-15 AR ARP070100655A patent/AR059517A1/es unknown
- 2007-02-15 KR KR1020087019732A patent/KR20080094685A/ko not_active Withdrawn
- 2007-02-15 WO PCT/US2007/004091 patent/WO2007098030A1/en not_active Ceased
- 2007-02-15 BR BRPI0707742-4A patent/BRPI0707742A2/pt not_active IP Right Cessation
- 2007-02-15 PE PE2007000169A patent/PE20080109A1/es not_active Application Discontinuation
- 2007-02-15 CN CNA2007800054762A patent/CN101384579A/zh active Pending
-
2008
- 2008-07-17 CR CR10158A patent/CR10158A/es not_active Application Discontinuation
- 2008-07-21 IL IL192929A patent/IL192929A0/en unknown
- 2008-08-12 NO NO20083488A patent/NO20083488L/no not_active Application Discontinuation
- 2008-08-12 GT GT200800154A patent/GT200800154A/es unknown
- 2008-08-15 EC EC2008008684A patent/ECSP088684A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL192929A0 (en) | 2009-02-11 |
| TW200732295A (en) | 2007-09-01 |
| US20070197800A1 (en) | 2007-08-23 |
| AR059517A1 (es) | 2008-04-09 |
| RU2008131051A (ru) | 2010-03-27 |
| US7838550B2 (en) | 2010-11-23 |
| AU2007217966A1 (en) | 2007-08-30 |
| NO20083488L (no) | 2008-09-05 |
| CR10158A (es) | 2008-10-29 |
| ECSP088684A (es) | 2008-09-29 |
| GT200800154A (es) | 2008-10-21 |
| WO2007098030A1 (en) | 2007-08-30 |
| KR20080094685A (ko) | 2008-10-23 |
| JP2009527476A (ja) | 2009-07-30 |
| CN101384579A (zh) | 2009-03-11 |
| CA2637615A1 (en) | 2007-08-30 |
| BRPI0707742A2 (pt) | 2011-05-10 |
| WO2007098030A8 (en) | 2007-10-25 |
| EP1984347A1 (en) | 2008-10-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FX | Voluntary withdrawal |