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 PDF

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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
Application number
CA002470111A
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English (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
Individual
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=***_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CA2470111(A1) "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
Application filed by Individual filed Critical Individual
Publication of CA2470111A1 publication Critical patent/CA2470111A1/fr
Abandoned legal-status Critical Current

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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

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  • 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.
CA002470111A 2001-12-11 2002-11-26 Production d'acides .alpha.-amines et d'acides .alpha.-amines n-sulfonyles chiralement purs Abandoned CA2470111A1 (fr)

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 US6657070B2 (en) 2000-12-13 2002-06-11 Production of chirally pure α-amino acids and N-sulfonyl α-amino acids
US10/166,896 2002-06-11
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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SI1341779T1 (sl) 2000-12-13 2006-12-31 Wyeth Corp Heterociklicni sulfonamidni inhibitorji produkcije beta amiloida
CL2004000647A1 (es) 2003-03-31 2005-02-04 Wyeth Corp Compuestos derivados de heterociclicos de sulfonamida que contienen fluoro y trifluoro alquilo; composicion farmaceutica; kit farmaceutico; procedimiento de preparacion; y su uso como inhibidores de beta amiloides para tratar alzheimer, angiopatia am
JP2007517905A (ja) 2004-01-16 2007-07-05 ワイス アゾールを含有するベータアミロイド産生のヘテロ環式スルホンアミド阻害剤
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)

* Cited by examiner, † Cited by third party
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
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 (da) * 1992-08-25 1999-07-05 Searle & Co Hydroxyethylaminosulfonamider til anvendelse som inhibitorer af retrovirale proteaser
US6191306B1 (en) * 1999-08-03 2001-02-20 Eastman Chemical Company Process for the preparation of cyclopropylglycine

Also Published As

Publication number Publication date
AU2002351170B8 (en) 2009-10-08
TWI260316B (en) 2006-08-21
MXPA04005366A (es) 2004-09-27
WO2003050062A3 (fr) 2003-11-20
AU2009251195A1 (en) 2010-01-21
EP1461332A2 (fr) 2004-09-29
WO2003050062A2 (fr) 2003-06-19
EP1461332A4 (fr) 2009-10-21
TW200306292A (en) 2003-11-16
AU2002351170B2 (en) 2009-09-24
JP2005511727A (ja) 2005-04-28
JP4615861B2 (ja) 2011-01-19
AU2002351170A1 (en) 2003-06-23

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Legal Events

Date Code Title Description
EEER Examination request
FZDE Dead