SE7710367L - AZABYCLOHEXANES, ITS USE AND MANUFACTURE - Google Patents

AZABYCLOHEXANES, ITS USE AND MANUFACTURE

Info

Publication number
SE7710367L
SE7710367L SE7710367A SE7710367A SE7710367L SE 7710367 L SE7710367 L SE 7710367L SE 7710367 A SE7710367 A SE 7710367A SE 7710367 A SE7710367 A SE 7710367A SE 7710367 L SE7710367 L SE 7710367L
Authority
SE
Sweden
Prior art keywords
alkyl
formula
optically active
compounds
hydroxyl
Prior art date
Application number
SE7710367A
Other languages
Swedish (sv)
Other versions
SE435384B (en
Inventor
W J Fanshawe
J W Epstein
L S Crawley
C M Hofmann
S R Safir
Original Assignee
American Cyanamid Co
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
Priority claimed from US05/809,340 external-priority patent/US4118417A/en
Priority claimed from US05/809,339 external-priority patent/US4131611A/en
Priority claimed from US05/809,341 external-priority patent/US4118393A/en
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Publication of SE7710367L publication Critical patent/SE7710367L/en
Publication of SE435384B publication Critical patent/SE435384B/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C61/16—Unsaturated compounds
    • C07C61/40—Unsaturated compounds containing halogen
    • 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
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/36—Polyhydroxylic alcohols containing six-membered aromatic rings and other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C61/16—Unsaturated compounds
    • C07C61/28—Unsaturated compounds polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C62/30—Unsaturated compounds
    • C07C62/34—Unsaturated compounds containing ether groups, groups, groups, or groups
    • 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
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

Landscapes

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

Abstract

Optically active compounds of the formula: <IMAGE> are prepared by reduction of optically active corresponding compounds of the formula: <IMAGE> in which one R denotes an oxo or hydroxyl group, the other R denotes hydrogen or both Rs denote oxo groups or hydroxyl groups, with a hydride, at -70 to 125 DEG C and in an inert, aprotic solvent, or by resolution of the racemic compounds obtained from the reduction, using an optically active acid. In the formula I, the phenyl radical is unsubstituted or mono- or di-substituted by halogen, straight-chain C1-C6-alkyl, singly branched C1-C5-alkyl, C1-C6-alkoxy, trifluoromethyl, nitro, amino, acetamido and/or hydroxyl, X denotes hydrogen, straight-chain C1-C8-alkyl or a group CnH2nR1 where n = 1 to 3 and R1 = phenyl or p-fluorobenzoyl. The compounds are distinguished by an analgesic action; they can be used therapeutically as analgesics.
SE7710367A 1976-09-15 1977-09-15 ANALOGY PROCEDURE FOR PREPARATION OF 3-AZABICYCLO (3.1.0) ALKANES SE435384B (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US72340276A 1976-09-15 1976-09-15
US05/809,340 US4118417A (en) 1977-06-23 1977-06-23 Process for resolving cis-1-substituted phenyl-1,2-cyclopropanedicarboxylic acids
US05/809,339 US4131611A (en) 1975-07-31 1977-06-23 Azabicyclohexanes
US05/809,341 US4118393A (en) 1977-06-23 1977-06-23 Phenyl azabicyclohexanones

Publications (2)

Publication Number Publication Date
SE7710367L true SE7710367L (en) 1978-03-16
SE435384B SE435384B (en) 1984-09-24

Family

ID=27505564

Family Applications (2)

Application Number Title Priority Date Filing Date
SE7710367A SE435384B (en) 1976-09-15 1977-09-15 ANALOGY PROCEDURE FOR PREPARATION OF 3-AZABICYCLO (3.1.0) ALKANES
SE8203437A SE452610B (en) 1976-09-15 1982-06-03 SETTING DIVERSE RACEMIC CIS-1,2-CYCLOPROPANDICARBOXYLIC ACID DERIVATIVES

Family Applications After (1)

Application Number Title Priority Date Filing Date
SE8203437A SE452610B (en) 1976-09-15 1982-06-03 SETTING DIVERSE RACEMIC CIS-1,2-CYCLOPROPANDICARBOXYLIC ACID DERIVATIVES

Country Status (16)

Country Link
JP (1) JPS5337656A (en)
AR (2) AR220684A1 (en)
AT (2) AT367036B (en)
AU (1) AU519620B2 (en)
BE (1) BE858683A (en)
CH (2) CH637929A5 (en)
DD (1) DD133943A5 (en)
DE (1) DE2740562A1 (en)
DK (3) DK146245C (en)
FR (1) FR2375212A1 (en)
GR (1) GR72713B (en)
HU (1) HU177531B (en)
NL (1) NL189041C (en)
PL (1) PL115869B1 (en)
SE (2) SE435384B (en)
YU (2) YU39499B (en)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4183857A (en) * 1978-07-06 1980-01-15 Shell Oil Company 3-Benzyl-3-azabicyclo(3.1.0)hexane-2,4-dione
IL65843A (en) * 1977-08-11 1986-12-31 American Cyanamid Co Pharmaceutical compositions for the treatment of depression containing 3-aza-bicyclo(3.1.0)hexane derivatives and certain novel compounds of this type
CA1117127A (en) * 1978-06-27 1982-01-26 Janet A. Day Derivatives of 3-azabicyclo(3.1.0)hexane and a process for their preparation
US4225499A (en) * 1978-07-06 1980-09-30 Shell Oil Company Process for preparing 3-azabicyclo(3.1.0)hexane-2-carbonitrile
JPS6332100A (en) * 1986-07-25 1988-02-10 東京電力株式会社 Shield excavator
JPH0658037B2 (en) * 1989-09-01 1994-08-03 日本鋼管株式会社 Shield excavator
US6372919B1 (en) 2001-01-11 2002-04-16 Dov Pharmaceutical, Inc. (+)-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane, compositions thereof, and uses as an anti-depressant agent
US6569887B2 (en) 2001-08-24 2003-05-27 Dov Pharmaceuticals Inc. (−)-1-(3,4-Dichlorophenyl)-3-azabicyclo[3.1.0]hexane, compositions thereof, and uses as a dopamine-reuptake
US20080081834A1 (en) 2002-07-31 2008-04-03 Lippa Arnold S Methods and compositions employing bicifadine for treating disability or functional impairment associated with acute pain, chronic pain, or neuropathic disorders
CN101410106A (en) * 2004-07-22 2009-04-15 惠氏公司 Methods of treating neurological disorders and conditions
JP2008507552A (en) * 2004-07-22 2008-03-13 ワイス Methods of treating nervous system disorders and conditions
US20070043100A1 (en) 2005-08-16 2007-02-22 Hagen Eric J Novel polymorphs of azabicyclohexane
KR101733180B1 (en) * 2005-07-27 2017-05-08 뉴로반스, 인크. Novel 1-aryl-3-azabicyclo[3.1.0]hexanes: preparation and use to treat neuropsychiatric disorders
US20080045725A1 (en) 2006-04-28 2008-02-21 Murry Jerry A Process For The Synthesis of (+) And (-)-1-(3,4-Dichlorophenyl)-3-Azabicyclo[3.1.0]Hexane
US8138377B2 (en) 2006-11-07 2012-03-20 Dov Pharmaceutical, Inc. Arylbicyclo[3.1.0]hexylamines and methods and compositions for their preparation and use
US9133159B2 (en) 2007-06-06 2015-09-15 Neurovance, Inc. 1-heteroaryl-3-azabicyclo[3.1.0]hexanes, methods for their preparation and their use as medicaments
US20140206740A1 (en) 2011-07-30 2014-07-24 Neurovance, Inc. Use Of (1R,5S)-(+)-(Napthalen-2-yl)-3-Azabicyclo[3.1.0]Hexane In The Treatment Of Conditions Affected By Monoamine Neurotransmitters

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1351754A (en) * 1970-07-02 1974-05-01 Allen & Hanburys Ltd Indenopyrrole derivatives

Also Published As

Publication number Publication date
DK438480A (en) 1980-10-16
NL189041C (en) 1992-12-16
FR2375212B1 (en) 1981-07-31
YU39499B (en) 1984-12-31
HU177531B (en) 1981-11-28
YU43523B (en) 1989-08-31
CH637931A5 (en) 1983-08-31
YU217477A (en) 1983-01-21
AR227507A1 (en) 1982-11-15
BE858683A (en) 1978-03-14
DD133943A5 (en) 1979-01-31
AU2844177A (en) 1979-03-08
DK438580A (en) 1980-10-16
PL115869B1 (en) 1981-05-30
DK146245B (en) 1983-08-08
AU519620B2 (en) 1981-12-17
DK407577A (en) 1978-03-16
SE8203437L (en) 1982-06-03
AT367036B (en) 1982-05-25
ATA661577A (en) 1981-10-15
DE2740562A1 (en) 1978-03-23
JPS5337656A (en) 1978-04-06
AT367037B (en) 1982-05-25
SE435384B (en) 1984-09-24
FR2375212A1 (en) 1978-07-21
CH637929A5 (en) 1983-08-31
SE452610B (en) 1987-12-07
NL7709691A (en) 1978-03-17
GR72713B (en) 1983-12-01
AR220684A1 (en) 1980-11-28
DE2740562C2 (en) 1989-05-03
JPS6129341B2 (en) 1986-07-05
ATA288280A (en) 1981-10-15
YU188582A (en) 1985-03-20
PL200831A1 (en) 1980-02-11
NL189041B (en) 1992-07-16
DK146245C (en) 1984-01-16

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