MXPA04005366A - PRODUCTION OF CHIRALLY PURE alpha-AMINO ACIDS ADN N-SULFONYL alpha-AMINO ACIDS. - Google Patents
PRODUCTION OF CHIRALLY PURE alpha-AMINO ACIDS ADN N-SULFONYL alpha-AMINO ACIDS.Info
- Publication number
- MXPA04005366A MXPA04005366A MXPA04005366A MXPA04005366A MXPA04005366A MX PA04005366 A MXPA04005366 A MX PA04005366A MX PA04005366 A MXPA04005366 A MX PA04005366A MX PA04005366 A MXPA04005366 A MX PA04005366A MX PA04005366 A MXPA04005366 A MX PA04005366A
- Authority
- MX
- Mexico
- Prior art keywords
- alpha
- amino acids
- chirally pure
- salt
- sulfonyl
- Prior art date
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
Methods for production of chirally pure alpha-amino acids and N-sulfonyl alpha-amino acids are described. An aldehyde and a cyanide salt are reacted with an alpha-methylbenzylamine to afford a product. The product reacts with a strong acid, is neutralized, and is extracted. The resulting product is subsequently hydrogenated and hydrolyzed to provide a product which is dissolved in a strong acid to provide a salt of a chirally pure alpha-amino acid, which is reacted to provide the chirally pure alpha-amino acid. Another method involves mixing ephedrine hemihydrate and an N-sulfonyl alpha-ethylnorvaline in ethanol at a molar ratio of 1:1; heating the mixture to dissolve the solids; cooling to allow formation of a precipitate; washing with an organic solvent to give diastereomeric salt; recrystallizing the salt; dissolving the recrystallized salt in an organic solvent and strong aqueous acid, separating the layers; washing the organic extract; drying and concentrating to provide chirally pure N-sulfonyl alpha-amino acid.
Applications Claiming Priority (3)
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 |
US10/166,896 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 (en) | 2001-12-11 | 2002-11-26 | PRODUCTION OF CHIRALLY PURE α-AMINO ACIDS ADN N-SULFONYL α-AMINO ACIDS |
Publications (1)
Publication Number | Publication Date |
---|---|
MXPA04005366A true MXPA04005366A (en) | 2004-09-27 |
Family
ID=46204648
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
MXPA04005366A MXPA04005366A (en) | 2001-12-11 | 2002-11-26 | PRODUCTION OF CHIRALLY PURE alpha-AMINO ACIDS ADN N-SULFONYL alpha-AMINO ACIDS. |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP1461332A4 (en) |
JP (1) | JP4615861B2 (en) |
AU (2) | AU2002351170B8 (en) |
CA (1) | CA2470111A1 (en) |
MX (1) | MXPA04005366A (en) |
TW (1) | TWI260316B (en) |
WO (1) | WO2003050062A2 (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SI1341779T1 (en) | 2000-12-13 | 2006-12-31 | Wyeth Corp | Heterocyclic sulfonamide inhibitors of beta amyloid production |
CL2004000647A1 (en) | 2003-03-31 | 2005-02-04 | Wyeth Corp | COMPOUNDS DERIVED FROM SULFONAMIDE HETEROCICLES CONTAINING FLUORO AND TRIFLUORO RENT; PHARMACEUTICAL COMPOSITION; PHARMACEUTICAL KIT; PREPARATION PROCEDURE; AND ITS USE AS BETA AMILOID INHIBITORS TO TREAT ALZHEIMER, ANGIOPATIA AM |
JP2007517905A (en) | 2004-01-16 | 2007-07-05 | ワイス | Beta-amyloidogenic heterocyclic sulfonamide inhibitors containing azoles |
AU2007243490A1 (en) | 2006-04-21 | 2007-11-08 | Wyeth | Production of chirally pure amino alcohol intermediates, derivatives thereof, and uses thereof |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3802981A1 (en) * | 1988-02-02 | 1989-08-10 | Basf Ag | METHOD FOR REDUCING REDUCABLE CONNECTIONS |
US5264577A (en) * | 1992-04-22 | 1993-11-23 | Warner-Lambert Company | Cyclic amino acids and derivatives thereof |
US5968942A (en) * | 1992-08-25 | 1999-10-19 | G. D. Searle & Co. | α- and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors |
DK0656887T3 (en) * | 1992-08-25 | 1999-07-05 | Searle & Co | Hydroxyethylaminosulfonamides for use as inhibitors of retroviral proteases |
US6191306B1 (en) * | 1999-08-03 | 2001-02-20 | Eastman Chemical Company | Process for the preparation of cyclopropylglycine |
-
2002
- 2002-11-26 JP JP2003551090A patent/JP4615861B2/en not_active Expired - Fee Related
- 2002-11-26 EP EP02786817A patent/EP1461332A4/en not_active Withdrawn
- 2002-11-26 CA CA002470111A patent/CA2470111A1/en not_active Abandoned
- 2002-11-26 MX MXPA04005366A patent/MXPA04005366A/en active IP Right Grant
- 2002-11-26 WO PCT/US2002/038117 patent/WO2003050062A2/en active Application Filing
- 2002-11-26 AU AU2002351170A patent/AU2002351170B8/en not_active Ceased
- 2002-12-10 TW TW091135621A patent/TWI260316B/en active
-
2009
- 2009-12-24 AU AU2009251195A patent/AU2009251195A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
AU2002351170B8 (en) | 2009-10-08 |
TWI260316B (en) | 2006-08-21 |
WO2003050062A3 (en) | 2003-11-20 |
AU2009251195A1 (en) | 2010-01-21 |
CA2470111A1 (en) | 2003-06-19 |
EP1461332A2 (en) | 2004-09-29 |
WO2003050062A2 (en) | 2003-06-19 |
EP1461332A4 (en) | 2009-10-21 |
TW200306292A (en) | 2003-11-16 |
AU2002351170B2 (en) | 2009-09-24 |
JP2005511727A (en) | 2005-04-28 |
JP4615861B2 (en) | 2011-01-19 |
AU2002351170A1 (en) | 2003-06-23 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
FG | Grant or registration |