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WO2003050062A3 - PRODUCTION OF CHIRALLY PURE α-AMINO ACIDS ADN N-SULFONYL α-AMINO ACIDS - Google Patents

PRODUCTION OF CHIRALLY PURE α-AMINO ACIDS ADN N-SULFONYL α-AMINO ACIDS Download PDF

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Publication number
WO2003050062A3
WO2003050062A3 PCT/US2002/038117 US0238117W WO03050062A3 WO 2003050062 A3 WO2003050062 A3 WO 2003050062A3 US 0238117 W US0238117 W US 0238117W WO 03050062 A3 WO03050062 A3 WO 03050062A3
Authority
WO
WIPO (PCT)
Prior art keywords
amino acids
sulfonyl
chirally pure
salt
product
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.)
Ceased
Application number
PCT/US2002/038117
Other languages
French (fr)
Other versions
WO2003050062A2 (en
Inventor
Lynn Resnick
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wyeth LLC
Original Assignee
Wyeth LLC
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=46204648&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO2003050062(A3) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority claimed from US10/014,304 external-priority patent/US6610734B2/en
Priority claimed from US10/166,896 external-priority patent/US6657070B2/en
Priority to MXPA04005366A priority Critical patent/MXPA04005366A/en
Priority to CA002470111A priority patent/CA2470111A1/en
Priority to EP02786817A priority patent/EP1461332A4/en
Priority to IL16220602A priority patent/IL162206A0/en
Application filed by Wyeth LLC filed Critical Wyeth LLC
Priority to JP2003551090A priority patent/JP4615861B2/en
Priority to AU2002351170A priority patent/AU2002351170B8/en
Publication of WO2003050062A2 publication Critical patent/WO2003050062A2/en
Publication of WO2003050062A3 publication Critical patent/WO2003050062A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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 α-amino acids and N-sulfonyl α-amino acids are described. An aldehyde and a cyanide salt are reacted with an α-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 α-amino acid, which is reacted to provide the chirally pure α-amino acid. Another method involves mixing ephedrine hemihydrate and an N-sulfonyl α-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 α-amino acid.
PCT/US2002/038117 2001-12-11 2002-11-26 PRODUCTION OF CHIRALLY PURE α-AMINO ACIDS ADN N-SULFONYL α-AMINO ACIDS Ceased WO2003050062A2 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
AU2002351170A AU2002351170B8 (en) 2001-12-11 2002-11-26 Production of chirally pure alpha-amino acids and N-sulfonyl alpha-amino acids
JP2003551090A JP4615861B2 (en) 2001-12-11 2002-11-26 Production of chirally pure α-amino acids and N-sulfonyl α-amino acids
MXPA04005366A MXPA04005366A (en) 2001-12-11 2002-11-26 PRODUCTION OF CHIRALLY PURE alpha-AMINO ACIDS ADN N-SULFONYL alpha-AMINO ACIDS.
CA002470111A CA2470111A1 (en) 2001-12-11 2002-11-26 Production of chirally pure .alpha.-amino acids and n-sulfonyl .alpha.-amino acids
EP02786817A EP1461332A4 (en) 2001-12-11 2002-11-26 Production of chirally pure alpha-amino acids and n-sulfonyl alpha-amino acids
IL16220602A IL162206A0 (en) 2001-12-11 2002-11-26 Production of chirally pure-aminoacid and n-sulfo nyl amino acids

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US10/014,304 2001-12-11
US10/014,304 US6610734B2 (en) 2000-12-13 2001-12-11 Heterocyclic sulfonamide inhibitors of beta amyloid production
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

Publications (2)

Publication Number Publication Date
WO2003050062A2 WO2003050062A2 (en) 2003-06-19
WO2003050062A3 true WO2003050062A3 (en) 2003-11-20

Family

ID=46204648

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2002/038117 Ceased WO2003050062A2 (en) 2001-12-11 2002-11-26 PRODUCTION OF CHIRALLY PURE α-AMINO ACIDS ADN N-SULFONYL α-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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HUP0303857A3 (en) 2000-12-13 2007-07-30 Wyeth Corp Heterocyclic sulifonamide inhibitors of beta amyloid production
CA2517155A1 (en) 2003-03-31 2004-10-28 Wyeth Fluoro-and trifluoroalkyl-containing heterocyclic sulfonamide inhibitors of beta amyloid production and derivatives thereof
WO2005073198A1 (en) 2004-01-16 2005-08-11 Wyeth Heterocyclic sulfonamide inhibitors of beta amyloid production containing an azole
JP2009534385A (en) 2006-04-21 2009-09-24 ワイス Preparation of chirally pure amino alcohol intermediates, their derivatives, and their use

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6248775B1 (en) * 1992-08-25 2001-06-19 G. D. Searle & Co. α- and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors

Family Cites Families (4)

* Cited by examiner, † Cited by third party
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
CA2140929C (en) * 1992-08-25 2006-09-12 Michael L. Vazquez Hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
US6191306B1 (en) * 1999-08-03 2001-02-20 Eastman Chemical Company Process for the preparation of cyclopropylglycine

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6248775B1 (en) * 1992-08-25 2001-06-19 G. D. Searle & Co. α- and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP1461332A4 *

Also Published As

Publication number Publication date
AU2002351170B8 (en) 2009-10-08
JP2005511727A (en) 2005-04-28
AU2002351170B2 (en) 2009-09-24
TW200306292A (en) 2003-11-16
EP1461332A2 (en) 2004-09-29
WO2003050062A2 (en) 2003-06-19
AU2009251195A1 (en) 2010-01-21
AU2002351170A1 (en) 2003-06-23
EP1461332A4 (en) 2009-10-21
JP4615861B2 (en) 2011-01-19
CA2470111A1 (en) 2003-06-19
MXPA04005366A (en) 2004-09-27
TWI260316B (en) 2006-08-21

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