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WO2008155619A3 - Preparation of optically-active cyclic amino acids - Google Patents

Preparation of optically-active cyclic amino acids Download PDF

Info

Publication number
WO2008155619A3
WO2008155619A3 PCT/IB2008/001556 IB2008001556W WO2008155619A3 WO 2008155619 A3 WO2008155619 A3 WO 2008155619A3 IB 2008001556 W IB2008001556 W IB 2008001556W WO 2008155619 A3 WO2008155619 A3 WO 2008155619A3
Authority
WO
WIPO (PCT)
Prior art keywords
optically
preparation
amino acids
cyclic amino
formula
Prior art date
Application number
PCT/IB2008/001556
Other languages
French (fr)
Other versions
WO2008155619A2 (en
Inventor
Bruce Allen Pearlman
Original Assignee
Pfizer
Bruce Allen Pearlman
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
Application filed by Pfizer, Bruce Allen Pearlman filed Critical Pfizer
Publication of WO2008155619A2 publication Critical patent/WO2008155619A2/en
Publication of WO2008155619A3 publication Critical patent/WO2008155619A3/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C255/46—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of non-condensed rings
    • 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
    • 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
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • A61P25/20—Hypnotics; Sedatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/30—Preparation of optical isomers
    • C07C227/32—Preparation of optical isomers by stereospecific synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/28—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and containing rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/96—Spiro-condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Anesthesiology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Methods and materials for preparing an optically active compound of Formula (1), or a pharmaceutically acceptable salt thereof, or an opposite enantiomer of the compound of Formula (1) or pharmaceutically acceptable salt thereof, are disclosed. The method includes reducing a cyano moiety of a compound of Formula (5), or an opposite enantiomer thereof, or a salt of the compound of Formula (5) or opposite enantiomer thereof, to an amino moiety, wherein R1, R2, and R5 are defined in the specification.
PCT/IB2008/001556 2007-06-21 2008-06-09 Preparation of optically-active cyclic amino acids WO2008155619A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US94558407P 2007-06-21 2007-06-21
US60/945,584 2007-06-21

Publications (2)

Publication Number Publication Date
WO2008155619A2 WO2008155619A2 (en) 2008-12-24
WO2008155619A3 true WO2008155619A3 (en) 2009-08-13

Family

ID=40101023

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2008/001556 WO2008155619A2 (en) 2007-06-21 2008-06-09 Preparation of optically-active cyclic amino acids

Country Status (4)

Country Link
JP (1) JP2009108024A (en)
AR (1) AR069268A1 (en)
TW (1) TW200906770A (en)
WO (1) WO2008155619A2 (en)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999021824A1 (en) * 1997-10-27 1999-05-06 Warner-Lambert Company Cyclic amino acids and derivatives thereof useful as pharmaceutical agents
WO1999031075A1 (en) * 1997-12-16 1999-06-24 Warner-Lambert Company 1-substituted-1-aminomethyl-cycloalkane derivatives (=gabapentin analogues), their preparation and their use in the treatment of neurological disorders
WO2001042191A1 (en) * 1999-12-08 2001-06-14 Warner-Lambert Company Branched chain amino acid-dependent aminotransferase inhibitors and their use in the treatment of diabetic retinopathy

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999021824A1 (en) * 1997-10-27 1999-05-06 Warner-Lambert Company Cyclic amino acids and derivatives thereof useful as pharmaceutical agents
WO1999031075A1 (en) * 1997-12-16 1999-06-24 Warner-Lambert Company 1-substituted-1-aminomethyl-cycloalkane derivatives (=gabapentin analogues), their preparation and their use in the treatment of neurological disorders
WO2001042191A1 (en) * 1999-12-08 2001-06-14 Warner-Lambert Company Branched chain amino acid-dependent aminotransferase inhibitors and their use in the treatment of diabetic retinopathy

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
GARETH GRIFFITHS ET AL: "Novel Syntheses of Gabapentin via Addition of Hydrocyanic Acid to Cyclohexylidenemalonate or Cyano(cyclohexylidene)acetate", HELVETICA CHIMICA ACTA, VERLAG HELVETICA CHIMICA ACTA. BASEL, CH, vol. 74, no. 2, 1 January 1991 (1991-01-01), pages 309 - 314, XP002100736, ISSN: 0018-019X *

Also Published As

Publication number Publication date
TW200906770A (en) 2009-02-16
AR069268A1 (en) 2010-01-13
JP2009108024A (en) 2009-05-21
WO2008155619A2 (en) 2008-12-24

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