SE7710367L - AZABYCLOHEXANES, ITS USE AND MANUFACTURE - Google Patents
AZABYCLOHEXANES, ITS USE AND MANUFACTUREInfo
- 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
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- -1 nitro, amino, acetamido Chemical group 0.000 abstract 2
- 125000004043 oxo group Chemical group O=* 0.000 abstract 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 abstract 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 229940035676 analgesics Drugs 0.000 abstract 1
- 239000000730 antalgic agent Substances 0.000 abstract 1
- 239000000010 aprotic solvent Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 150000004678 hydrides Chemical class 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (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.
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 |
US05/809,340 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 |
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)
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 |
CN101014337A (en) * | 2004-07-22 | 2007-08-08 | 惠氏公司 | Methods of treating nervous system disorders and conditions |
CA2574310A1 (en) * | 2004-07-22 | 2006-02-02 | Wyeth | Method for treating nervous system disorders and conditions |
US20070043100A1 (en) | 2005-08-16 | 2007-02-22 | Hagen Eric J | Novel polymorphs of azabicyclohexane |
BRPI0613943B1 (en) * | 2005-07-27 | 2021-06-22 | Otsuka America Pharmaceutical, Inc | COMPOUND, PHARMACEUTICAL COMPOSITION INCLUDING IT, USES OF A COMPOUND AND A PHARMACEUTICAL COMPOSITION, AS WELL AS NEUROBIOLOGICALLY ACTIVE COMPOSITION |
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)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1351754A (en) * | 1970-07-02 | 1974-05-01 | Allen & Hanburys Ltd | Indenopyrrole derivatives |
-
1977
- 1977-08-16 GR GR54169A patent/GR72713B/el unknown
- 1977-08-26 AR AR268968A patent/AR220684A1/en active
- 1977-09-01 AU AU28441/77A patent/AU519620B2/en not_active Ceased
- 1977-09-02 NL NLAANVRAGE7709691,A patent/NL189041C/en not_active IP Right Cessation
- 1977-09-08 DE DE19772740562 patent/DE2740562A1/en active Granted
- 1977-09-13 CH CH1118977A patent/CH637929A5/en not_active IP Right Cessation
- 1977-09-13 YU YU2174/77A patent/YU39499B/en unknown
- 1977-09-14 DK DK407577A patent/DK146245C/en not_active IP Right Cessation
- 1977-09-14 AT AT0661577A patent/AT367036B/en not_active IP Right Cessation
- 1977-09-14 FR FR7727755A patent/FR2375212A1/en active Granted
- 1977-09-14 HU HU77AE508A patent/HU177531B/en unknown
- 1977-09-14 BE BE180894A patent/BE858683A/en not_active IP Right Cessation
- 1977-09-14 PL PL1977200831A patent/PL115869B1/en unknown
- 1977-09-15 SE SE7710367A patent/SE435384B/en not_active IP Right Cessation
- 1977-09-15 DD DD77201039A patent/DD133943A5/en unknown
- 1977-09-16 JP JP11064777A patent/JPS5337656A/en active Granted
-
1978
- 1978-09-19 AR AR273764A patent/AR227507A1/en active
-
1980
- 1980-05-30 AT AT0288280A patent/AT367037B/en not_active IP Right Cessation
- 1980-10-16 DK DK438480A patent/DK438480A/en not_active Application Discontinuation
- 1980-10-16 DK DK438580A patent/DK438580A/en not_active Application Discontinuation
-
1982
- 1982-04-05 CH CH209382A patent/CH637931A5/en not_active IP Right Cessation
- 1982-06-03 SE SE8203437A patent/SE452610B/en not_active IP Right Cessation
- 1982-08-23 YU YU1885/82A patent/YU43523B/en unknown
Also Published As
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Legal Events
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