SE8203437L - AZABICYCLOHEXANES, ITS USE AND PREPARATION - Google Patents

AZABICYCLOHEXANES, ITS USE AND PREPARATION

Info

Publication number
SE8203437L
SE8203437L SE8203437A SE8203437A SE8203437L SE 8203437 L SE8203437 L SE 8203437L SE 8203437 A SE8203437 A SE 8203437A SE 8203437 A SE8203437 A SE 8203437A SE 8203437 L SE8203437 L SE 8203437L
Authority
SE
Sweden
Prior art keywords
formula
alkyl
optically active
compounds
hydroxyl
Prior art date
Application number
SE8203437A
Other languages
Swedish (sv)
Other versions
SE452610B (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 US05/809,341 external-priority patent/US4118393A/en
Priority claimed from US05/809,339 external-priority patent/US4131611A/en
Priority claimed from US05/809,340 external-priority patent/US4118417A/en
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Publication of SE8203437L publication Critical patent/SE8203437L/en
Publication of SE452610B publication Critical patent/SE452610B/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)
  • Medicinal Chemistry (AREA)
  • Pain & Pain Management (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biomedical Technology (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: are prepared by reduction of optically active corresponding compounds of the formula: 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.

Claims (1)

PATENTKRAV satt att aterlosa en farening med formeln COOH COOH van i R betecknar \rate eller alkyl med 1 - 6 kolatomer och fenylgruppen är osubstituerad, mono- eller di-substituerad med vats, halogen, alkyl med 1 - 6 kolatomer, alkoxi medCLAIMS set forth to atherosate a compound of the formula COOH COOH van in R 1. - 6 kolatomer, trifluormetyl, nitro, amino, acetamido oiler hydroxi till deras (+) och (-)-isomerer, kdnnetecknat darav, att nifinnda forening far reagera med antingen (+) eller (-)-m-(1-nafty1)-etylamin, i ett organiskt losningsmedel for framstallning av en fast substans, att namnda fasta substans samlas, uPPslammas i vatten, installes pa basisk reaktion, extraheras med eter och surgares.1-6 carbon atoms, trifluoromethyl, nitro, amino, acetamido or hydroxy to their (+) and (-) - isomers, characterized in that the compound found may react with either (+) or (-) - m- (1- naphthyl) -ethylamine, in an organic solvent for the preparation of a solid, that said solid is collected, slurried in water, installed on a basic reaction, extracted with ether and acidified.
SE8203437A 1976-09-15 1982-06-03 SETTING DIVERSE RACEMIC CIS-1,2-CYCLOPROPANDICARBOXYLIC ACID DERIVATIVES SE452610B (en)

Applications Claiming Priority (4)

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

Publications (2)

Publication Number Publication Date
SE8203437L true SE8203437L (en) 1982-06-03
SE452610B SE452610B (en) 1987-12-07

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 Before (1)

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

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
AU2005266997A1 (en) * 2004-07-22 2006-02-02 Wyeth Method for treating nervous system disorders and conditions
RU2007102292A (en) * 2004-07-22 2008-08-27 Вайет (Us) METHOD FOR TREATING DISORDERS AND DISEASES OF THE NERVOUS SYSTEM
US20070043100A1 (en) 2005-08-16 2007-02-22 Hagen Eric J Novel polymorphs of azabicyclohexane
AU2006275870B2 (en) 2005-07-27 2013-01-10 Otsuka America Pharmaceutical, Inc. 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
CH637929A5 (en) 1983-08-31
YU217477A (en) 1983-01-21
JPS6129341B2 (en) 1986-07-05
DK407577A (en) 1978-03-16
JPS5337656A (en) 1978-04-06
GR72713B (en) 1983-12-01
FR2375212A1 (en) 1978-07-21
SE435384B (en) 1984-09-24
DE2740562A1 (en) 1978-03-23
PL115869B1 (en) 1981-05-30
SE7710367L (en) 1978-03-16
AT367036B (en) 1982-05-25
AU2844177A (en) 1979-03-08
DD133943A5 (en) 1979-01-31
ATA288280A (en) 1981-10-15
SE452610B (en) 1987-12-07
AT367037B (en) 1982-05-25
HU177531B (en) 1981-11-28
ATA661577A (en) 1981-10-15
NL189041B (en) 1992-07-16
YU43523B (en) 1989-08-31
YU188582A (en) 1985-03-20
YU39499B (en) 1984-12-31
NL189041C (en) 1992-12-16
AR227507A1 (en) 1982-11-15
AU519620B2 (en) 1981-12-17
DK146245C (en) 1984-01-16
BE858683A (en) 1978-03-14
PL200831A1 (en) 1980-02-11
FR2375212B1 (en) 1981-07-31
DK146245B (en) 1983-08-08
AR220684A1 (en) 1980-11-28
CH637931A5 (en) 1983-08-31
DE2740562C2 (en) 1989-05-03
NL7709691A (en) 1978-03-17
DK438580A (en) 1980-10-16
DK438480A (en) 1980-10-16

Similar Documents

Publication Publication Date Title
SE8203437L (en) AZABICYCLOHEXANES, ITS USE AND PREPARATION
SU578883A3 (en) Method of preparing pyrazoloisoquinolines or salts thereof
FR2405245A1 (en) BENZYL-PYRROLYL-METHYL CARBOXYLATE INSECTICIDES AND ACARICIDES
KR870007166A (en) Method for preparing phenyl naphthyridine
ES428295A1 (en) Procedure for the obtaining of sulphonated canfene derivatives. (Machine-translation by Google Translate, not legally binding)
JPS5559127A (en) Novel intermediate compound for producing prostanoids and its manufacture
SE7510787L (en) NEW NITROGENIC, POLYCYCLIC ASSOCIATIONS, SALTS THEREOF AND THEIR OPTICAL ANTIPODS, JUST LIKE THEIR PREPARATION
ES8206535A1 (en) Improvement in the method for producing 7-aminocephem compounds.
GB1472699A (en) Unsaturated phosphorus-containing carboxylic acid derivatives
JPS5368741A (en) Preparation of substd. diphenylamine derivative
CH608785A5 (en) Process for producing new N-acylglutamines
JPS5533440A (en) Optically active benzyl(2-hydroxymethylcyclohexyl) amine, its preparation, and its optical resolution
ES447615A1 (en) Derivatives of 7-aminocephalosporanic acid
ES421284A1 (en) Procedure for the preparation of derivatives of pirrocolinacetic acids. (Machine-translation by Google Translate, not legally binding)
JPS537640A (en) Synthesis of diphenylamine derivatives
ES445336A1 (en) Oxoindanylpropionic acids and process for the preparation thereof
JPS5758651A (en) Preparation of diamino acid derivative
ES486377A1 (en) Process for the preparation of 5-mercapto-1,2,3-triazoles
ES421341A1 (en) Di-hydroxygenzenesulphonic acid salts
GB1472368A (en) Process for the preparation of 4-hydroxy-3-methoxy-phenylace tonitrile
JPS5540661A (en) Preparation of 2,2,4-trimethyl-1,2-dihydroquinoline
JPS5679651A (en) Preparation of benzaldehyde derivative
JPS5620544A (en) Preparation of ethylene glycol monoethyl ether acetate
SU790614A1 (en) ETHYL ETHER 6- / 2-CHLORO-PHENOXY / -SORBIC ACID, MANIFESTING HERBICIDAL ACTIVITY AND METHOD FOR ITS OBTAINING
ES8206522A1 (en) Process for the Preparation of Apovincaminic Acid Esters

Legal Events

Date Code Title Description
NUG Patent has lapsed

Ref document number: 8203437-2

Effective date: 19930406

Format of ref document f/p: F