AR067533A1 - Procesos e inetermediarios para la preparacion de compuestos de sulfonamida heterociclica - Google Patents
Procesos e inetermediarios para la preparacion de compuestos de sulfonamida heterociclicaInfo
- Publication number
- AR067533A1 AR067533A1 ARP080103019A ARP080103019A AR067533A1 AR 067533 A1 AR067533 A1 AR 067533A1 AR P080103019 A ARP080103019 A AR P080103019A AR P080103019 A ARP080103019 A AR P080103019A AR 067533 A1 AR067533 A1 AR 067533A1
- Authority
- AR
- Argentina
- Prior art keywords
- imide
- chiral oxazolidinone
- salt
- azide
- converting
- Prior art date
Links
- -1 SULFONAMIDE COMPOUNDS Chemical class 0.000 title abstract 3
- 229940124530 sulfonamide Drugs 0.000 title abstract 2
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 abstract 31
- 150000003949 imides Chemical class 0.000 abstract 30
- 150000003839 salts Chemical class 0.000 abstract 18
- 150000001540 azides Chemical class 0.000 abstract 12
- 150000001412 amines Chemical class 0.000 abstract 10
- 150000001414 amino alcohols Chemical class 0.000 abstract 8
- 229910052799 carbon Inorganic materials 0.000 abstract 6
- 125000004432 carbon atom Chemical group C* 0.000 abstract 6
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 abstract 6
- 125000001072 heteroaryl group Chemical group 0.000 abstract 4
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000003107 substituted aryl group Chemical group 0.000 abstract 2
- BVJHYSSQNCJGPA-QMMMGPOBSA-N (3s)-3-(3,5-difluorophenyl)-4,4,4-trifluorobutanoic acid Chemical compound OC(=O)C[C@H](C(F)(F)F)C1=CC(F)=CC(F)=C1 BVJHYSSQNCJGPA-QMMMGPOBSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 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
- C07C303/40—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 reactions not involving the formation of sulfonamide groups
-
- 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
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/083—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid anhydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/36—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by hydrogenation of carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
- C07C57/60—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings having unsaturation outside the rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/22—Oxygen atoms attached in position 2 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to other ring carbon 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
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Psychiatry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Reivindicacion 1: Un método para preparar un compuesto de sulfonamida de la estructura (1) en donde: R1 es arilo, arilo sustituido, heteroarilo, o heteroarilo sustituido: R2 y R3 son, independientemente, alquilo C1 a C6, alquilo C1, a C6 sustituido, arilo, arilo sustituido, heteroarilo, y heteroarilo sustituido; dicho método seleccionado del grupo integrado por: (a) un método que comprende: (i) hidrogenar enantioselectivamente R2C(=CHCOOH)R3 a R2CH(CH2COOH)R3 (ii) convertir R2CH(CH2COOH)R3 a una imida de una oxazolidinona quiral; (iii) sustituir el átomo de carbono o de dicha imida de dicha oxazolidinona quiral con una azida; (iv) convertir dicha imida de dicha oxazolidinona quiral que contiene dicha azida a una amina o sal de la misma; (v) reducir dicha amina o sal de la misma a un aminoalcohol o sal del mismo; y (vi) sulfonar dicho aminoalcohol o sal del mismo; (b) un método que comprende: (i) hidrogenar enantioselectivamente R2C(=CHCOOH)R3 a R2CH(CH2COOH)R3 (ii) convertir R2CH(CH2COOH)R3 a una imida de una oxazolidinona quiral; (iii) sustituir el átomo de carbono o de dicha imida de una oxazolidinona quiral con una azida; (iv) convertir dicha imida de una oxazolidinona quiral contiene una azida a una imida de una oxazolidinona quiral que contiene una amina o sal de la misma; (v) sulfonar dicha imida de una oxazolidinona quiral que contiene una amina o sal de la misma; y (vi) reducir dicha imida sulfonada de una oxazolidinona quiral que contiene una amina o sal de la misma; (c) un método que comprende (i) convertir R2C(=CHCOOH)R3 a una imida no saturada de una oxazolidinona quiral; (ii) hidrogenar diastereoselectivamente dicha imida no saturada de una oxazolidinona quiral a una imida de una oxazolidinona quiral; (iii) sustituir el átomo de carbono o de dicha imida de dicha oxazolidinona quiral con una azida; (iv) convertir dicha imida de dicha oxazolidinona quiral con dicha que azida a una amina o sal de la misma; (v) reducir dicha amina o sal de la misma a un aminoalcohol o sal del mismo; y (vi) sulfonar dicho aminoalcohol o sal del mismo; (d) un método que comprende: (i) hidrogenar enantioselectivamente R2C(=CHCOOH)R3 a R2CH(CH2COOH)R3; (ii) convertir R2CH(CH2COOH)R3 a una imida de una oxazolidinona quiral; (iii) sustituir el átomo de carbono o de dicha imida de dicha oxazolidinona quiral con una azida; (iv) convertir dicha imida de dicha oxazolidinona quiral que contiene dicha azida a un aminoalcohol o sal del mismo; y (v) sulfonar dicho aminoalcohol o sal del mismo; (e) un método que comprende: (i) convertir R2C(=CHCOOH)R3 a una imida no saturada de una oxazolidinona quiral; (ii) hidrogenar diastereoselectivamente dicha imida no saturada de una oxazolidinona quiral a una imida de una oxazolidinona quiral; (iii) sustituir el átomo de carbono o de dicha imida de dicha oxazolidinona quiral con una azida; (iv) convertir dicha imida de dicha oxazolidinona quiral con dicha azida a un aminoalcohol o sal del mismo; y (v) sulfonar dicho aminoalcohol o sal del mismo; y (f) un método que comprende: (i) convertir R2C(=CHCOOH)R3 a una imida no saturada de una oxazolidinona quiral; (ii) hidrogenar diastereoselectivamente dicha imida no saturada de una oxazolidinona quiral a una imida de una oxazolidinona quiral; (iii) sustituir el átomo de carbono o de dicha imida de una oxazolidinona quiral con una azida; (iv) convertir dicha imida de una oxazolidinona quiral que contiene una azida a una imida de una oxazolidinona quiral que contiene una amina o sal de la misma; (v) sulfonar dicha imida de una oxazolidinona quiral que contiene una amina o sal de la misma; y (vi) reducir dicha imida de una oxazolidinona quiral que contiene una amina o sal de la misma. Reivindicacion 24: Un compuesto que está seleccionado del grupo integrado por (a) ácido (S)-3-(3,5-difluorfenil)-4,4,4-trifluorbutanoico, (b) (S)-4-bencil-3-((S)-3-(3,5.-difluorfenil)-4,4,4-trifluorbutanoil)oxazolidin-2-ona, (c) (S)-3-((2S,3R)-2-azido-3-(3,5-difluorfenil)-4,4,4-tritluorbutanoil)-4-benciloxazolidin-2-ona, (d) clorhidrato de (S)-3-((2S,3R)-2-amino-3-(3,5-difluorfenil)-4,4,4-trifluorbutanoil)-4-benciloxazolidin-2-ona, (e) clorhidrato de (2S,3R)-2-amino-3-(3,5-difluorfenil)-4,4,4-trifluorbutan-1-ol, y (f) N-((2S,3R)-1-((S)-4-bencil-2-oxo-oxazolidin-3-iI)-3-(3,5-difluorfenil)-4,4,4-trifluor-1-oxobutan-2-il)-5-clorotiofen-2-sulfonamida.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US95965507P | 2007-07-16 | 2007-07-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR067533A1 true AR067533A1 (es) | 2009-10-14 |
Family
ID=39790171
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP080103019A AR067533A1 (es) | 2007-07-16 | 2008-07-14 | Procesos e inetermediarios para la preparacion de compuestos de sulfonamida heterociclica |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20090023930A1 (es) |
| AR (1) | AR067533A1 (es) |
| CL (1) | CL2008002059A1 (es) |
| PA (1) | PA8789801A1 (es) |
| PE (1) | PE20090810A1 (es) |
| TW (1) | TW200914409A (es) |
| WO (1) | WO2009012203A1 (es) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006522126A (ja) * | 2003-03-31 | 2006-09-28 | ワイス | βアミロイド生産のフルオロ含有およびトリフルオロアルキル含有複素環スルホンアミド阻害物質およびその誘導体 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5461162A (en) * | 1994-07-27 | 1995-10-24 | Merck & Co., Inc. | Process of synthesizing n-acyl auxiliaries |
| US5594134A (en) * | 1995-03-31 | 1997-01-14 | Merck & Co., Inc. | Process of synthesizing N-acyl auxiliaries |
| IL124118A (en) * | 1998-04-16 | 2007-09-20 | Yissum Res Dev Co | Propylisopropyl acetic acid and propylisopropyl acetamide stereoisomers, method for their synthesis and pharmaceutical compositions containing them |
| AU2002245123B2 (en) * | 2000-12-13 | 2007-05-24 | Arqule, Inc. | Heterocyclic sulfonamide inhibitors of beta amyloid production |
| MXPA04012313A (es) * | 2002-06-11 | 2005-02-25 | Arqule Inc | Compuestos de fenilsulfonamida sustituida inhibidores de la produccion de beta-amiloide. |
| JP2006522126A (ja) * | 2003-03-31 | 2006-09-28 | ワイス | βアミロイド生産のフルオロ含有およびトリフルオロアルキル含有複素環スルホンアミド阻害物質およびその誘導体 |
| ATE443701T1 (de) * | 2004-01-16 | 2009-10-15 | Wyeth Corp | Heterocyclische, ein azol enthaltende sulfonamidinhibitoren der beta-amyloid-produktion |
| CN101415670A (zh) * | 2006-02-17 | 2009-04-22 | 惠氏公司 | 制备磺酰胺取代醇和其中间体的方法 |
| AU2007217966A1 (en) * | 2006-02-17 | 2007-08-30 | Wyeth | Selective N-sulfonylation of 2-amino trifluoroalkyl substituted alcohols |
| US7476762B2 (en) * | 2006-04-21 | 2009-01-13 | Wyeth | Methods for preparing sulfonamide compounds |
| US7550629B2 (en) * | 2006-04-21 | 2009-06-23 | Wyeth | Trifluoromethyl-containing phenylsulfonamide beta amyloid inhibitors |
-
2008
- 2008-07-14 TW TW097126641A patent/TW200914409A/zh unknown
- 2008-07-14 US US12/172,472 patent/US20090023930A1/en not_active Abandoned
- 2008-07-14 WO PCT/US2008/069938 patent/WO2009012203A1/en active Application Filing
- 2008-07-14 CL CL2008002059A patent/CL2008002059A1/es unknown
- 2008-07-14 PE PE2008001175A patent/PE20090810A1/es not_active Application Discontinuation
- 2008-07-14 PA PA20088789801A patent/PA8789801A1/es unknown
- 2008-07-14 AR ARP080103019A patent/AR067533A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CL2008002059A1 (es) | 2008-11-14 |
| PE20090810A1 (es) | 2009-07-20 |
| PA8789801A1 (es) | 2009-02-09 |
| TW200914409A (en) | 2009-04-01 |
| WO2009012203A1 (en) | 2009-01-22 |
| US20090023930A1 (en) | 2009-01-22 |
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