CA2470111A1 - Production d'acides .alpha.-amines et d'acides .alpha.-amines n-sulfonyles chiralement purs - Google Patents
Production d'acides .alpha.-amines et d'acides .alpha.-amines n-sulfonyles chiralement purs Download PDFInfo
- Publication number
- CA2470111A1 CA2470111A1 CA002470111A CA2470111A CA2470111A1 CA 2470111 A1 CA2470111 A1 CA 2470111A1 CA 002470111 A CA002470111 A CA 002470111A CA 2470111 A CA2470111 A CA 2470111A CA 2470111 A1 CA2470111 A1 CA 2470111A1
- Authority
- CA
- Canada
- Prior art keywords
- substituted
- sulfonyl
- alpha
- amino acid
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D307/64—Sulfur atoms
-
- 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
- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hospice & Palliative Care (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Psychiatry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
L'invention concerne des procédés de production d'acides .alpha.-aminés et d'acides .alpha.-aminés N-sulfonylés chiralement purs. Un aldéhyde et un sel de cyanure sont mis en réaction avec une .alpha.-méthylbenzylamine afin d'obtenir un produit. Le produit est mis à réagir avec un acide fort, puis neutralisé et extrait. Le produit résultant est ensuite hydrogéné et hydrolysé afin d'obtenir un produit qui est dissout dans un acide fort pour donner un sel d'un acide .alpha.-aminé chiralement pur, duquel, après réaction, on tire l'acide .alpha.-aminé chiralement pur. Un autre procédé consiste à mélanger un hémihydrate d'éphédrine et de la N-sulfonyl .alpha.-éthylnorvaline dans de l'éthanol dans un rapport équimolaire, à chauffer le mélange afin de solubiliser les solides, à refroidir de façon à favoriser la formation d'un précipité, à laver avec un solvant organique afin d'obtenir un sel de diastéréoisomères, à recristalliser le sel dans un solvant organique et un acide fort aqueux, à séparer les couches, à laver l'extrait organique, à sécher et à concentrer afin d'obtenir un acide .alpha.-aminé N-sulfonylé chiralement pur.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/014,304 US6610734B2 (en) | 2000-12-13 | 2001-12-11 | Heterocyclic sulfonamide inhibitors of beta amyloid production |
US10/014,304 | 2001-12-11 | ||
US10/166,896 | 2002-06-11 | ||
US10/166,896 US6657070B2 (en) | 2000-12-13 | 2002-06-11 | Production of chirally pure α-amino acids and N-sulfonyl α-amino acids |
PCT/US2002/038117 WO2003050062A2 (fr) | 2001-12-11 | 2002-11-26 | Production d'acides $g(a)-amines et d'acides $g(a)-amines n-sulfonyles chiralement purs |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2470111A1 true CA2470111A1 (fr) | 2003-06-19 |
Family
ID=46204648
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002470111A Abandoned CA2470111A1 (fr) | 2001-12-11 | 2002-11-26 | Production d'acides .alpha.-amines et d'acides .alpha.-amines n-sulfonyles chiralement purs |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP1461332A4 (fr) |
JP (1) | JP4615861B2 (fr) |
AU (2) | AU2002351170B8 (fr) |
CA (1) | CA2470111A1 (fr) |
MX (1) | MXPA04005366A (fr) |
TW (1) | TWI260316B (fr) |
WO (1) | WO2003050062A2 (fr) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NZ526213A (en) | 2000-12-13 | 2005-05-27 | Wyeth Corp | Heterocyclic sulfonamide inhibitors of beta amyloid production |
US7300951B2 (en) | 2003-03-31 | 2007-11-27 | Wyeth | Fluoro- and trifluoroalkyl-containing heterocyclic sulfonamide inhibitors of beta amyloid production and derivatives thereof |
WO2005073198A1 (fr) | 2004-01-16 | 2005-08-11 | Wyeth | Inhibiteurs a base de sulfonamides heterocycliques de la production des beta-amyloides contenant un azole |
CA2649396A1 (fr) | 2006-04-21 | 2007-11-08 | Wyeth | Production d'intermediaires de type aminoalcools purs du point de vue chiral, leurs derives et leurs utilisations |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3802981A1 (de) * | 1988-02-02 | 1989-08-10 | Basf Ag | Verfahren zur reduktion reduzierbarer verbindungen |
US5264577A (en) * | 1992-04-22 | 1993-11-23 | Warner-Lambert Company | Cyclic amino acids and derivatives thereof |
DE69321845T2 (de) * | 1992-08-25 | 1999-04-29 | Monsanto Co | Hydroxyethylaminosulfonamide verwendbar als inhibitoren retroviraler proteasen |
US5968942A (en) * | 1992-08-25 | 1999-10-19 | G. D. Searle & Co. | α- and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors |
US6191306B1 (en) * | 1999-08-03 | 2001-02-20 | Eastman Chemical Company | Process for the preparation of cyclopropylglycine |
-
2002
- 2002-11-26 CA CA002470111A patent/CA2470111A1/fr not_active Abandoned
- 2002-11-26 MX MXPA04005366A patent/MXPA04005366A/es active IP Right Grant
- 2002-11-26 AU AU2002351170A patent/AU2002351170B8/en not_active Ceased
- 2002-11-26 JP JP2003551090A patent/JP4615861B2/ja not_active Expired - Fee Related
- 2002-11-26 WO PCT/US2002/038117 patent/WO2003050062A2/fr active Application Filing
- 2002-11-26 EP EP02786817A patent/EP1461332A4/fr not_active Withdrawn
- 2002-12-10 TW TW091135621A patent/TWI260316B/zh active
-
2009
- 2009-12-24 AU AU2009251195A patent/AU2009251195A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
TWI260316B (en) | 2006-08-21 |
TW200306292A (en) | 2003-11-16 |
JP2005511727A (ja) | 2005-04-28 |
WO2003050062A2 (fr) | 2003-06-19 |
EP1461332A4 (fr) | 2009-10-21 |
AU2009251195A1 (en) | 2010-01-21 |
JP4615861B2 (ja) | 2011-01-19 |
AU2002351170A1 (en) | 2003-06-23 |
AU2002351170B8 (en) | 2009-10-08 |
MXPA04005366A (es) | 2004-09-27 |
AU2002351170B2 (en) | 2009-09-24 |
WO2003050062A3 (fr) | 2003-11-20 |
EP1461332A2 (fr) | 2004-09-29 |
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Publication | Publication Date | Title |
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US6610734B2 (en) | Heterocyclic sulfonamide inhibitors of beta amyloid production | |
US7858658B2 (en) | Fluoro- and trifluoroalkyl-containing heterocyclic sulfonamide inhibitors of beta amyloid production and derivatives thereof | |
AU2002245123A1 (en) | Heterocyclic sulfonamide inhibitors of beta amyloid production | |
US6657070B2 (en) | Production of chirally pure α-amino acids and N-sulfonyl α-amino acids | |
BRPI0707741A2 (pt) | mÉtodos para preparar um amino Álcool, ou sal do mesmo, e um Álcool substituÍdo por sulfonamida | |
US7598422B2 (en) | Production of chirally pure amino alcohol intermediates, derivatives thereof, and uses thereof | |
AU2009251195A1 (en) | Production of chirally pure alpha-amino acids and n-sulfonyl alpha-amino acids | |
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AU2002359519A1 (en) | PROCESS FOR THE SYNTHESIS OF CHIRALLY PURE Beta-AMINO-ALCOHOLS | |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
FZDE | Dead |