GB1497083A - 1-substituted-4-(1,2-diphenylethyl)-piperazine derivatives and their salts and the preparation thereof - Google Patents
1-substituted-4-(1,2-diphenylethyl)-piperazine derivatives and their salts and the preparation thereofInfo
- Publication number
- GB1497083A GB1497083A GB277375A GB277375A GB1497083A GB 1497083 A GB1497083 A GB 1497083A GB 277375 A GB277375 A GB 277375A GB 277375 A GB277375 A GB 277375A GB 1497083 A GB1497083 A GB 1497083A
- Authority
- GB
- United Kingdom
- Prior art keywords
- general formula
- group
- diphenylethyl
- salt
- reacting
- 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.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1497083 1 - (1,2 - Diphenylethyl) - piperazines DAINIPPON PHARMACEUTICAL CO Ltd 22 Jan 1975 [23 Jan 1974 12 March 1974 14 March 1974] 2773/75 Heading C2C Novel 1 - (1,2 - diphenylethyl) - piperazines of the general formula wherein X is a hydroxy, methoxy, methyl or trifluoromethyl group and R is a C 6-8 monocycloalkyl or 2-methoxyphenyl group, provided that, when X is a hydroxy group, R is a cyclohexyl group and, when X is a trifluoromethyl group, R is a 2-methoxyphenyl group, and pharmaceutically acceptable acid addition salts thereof are prepared (a) by reacting a 1,2-diphenylethylamine of the general formula wherein Z is a residue of a reactive ester of an alcohol, or an acid addition salt thereof with an amine of the general formula R-NH 2 , (b) by reacting a 1,2-diphenylethylamine of the general formula with an amine of the general formula or a salt thereof, (c) when X is a methoxy, methyl or trifluoromethyl group, by reacting a nitrile and a Grignard reagent of the respective general formulae wherein Z<SP>1</SP> is a halogen atom and X<SP>1</SP> is a methoxy, methyl or trifluoromethyl group; and (d) when X is a hydroxy group, by subjecting an ether of the general formula wherein Y is a C 1-7 alkyl or benzyl group, or a salt thereof to cleavage of the ether linkage, followed optionally by salification of the product. 1,2 - Diphenylethylamines of the second general formula above wherein X is other than a hydroxy group are prepared by reacting 3 - (2 - hydroxyethyl) - 2 - phenyloxazolidine with a Grignard reagent of the general formula in an inert solvent and halogenating the resulting amino-alcohol of the general formula Nitriles of the sixth general formula above are prepared by heating a salt of piperazine of the general formula with benzaldehyde and NaCN or KCN in water or an aqueous solvent. Ethers of the eighth general formula above (isolated as acid addition salts) are prepared analogously to process (b) above. Pharmaceutical compositions having analgesic, antitussive and antiinflammatory activity comprise, as active ingredient, at least one 1-(1,2- diphenylethyl)piperazine of the first general formula above or a pharmaceutically acceptable acid addition salt thereof, together with a pharmaceutically acceptable carrier and/or diluient therefor.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1047074A JPS5643463B2 (en) | 1974-01-23 | 1974-01-23 | |
JP2892674A JPS5643464B2 (en) | 1974-03-12 | 1974-03-12 | |
JP2968374A JPS5644071B2 (en) | 1974-03-14 | 1974-03-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1497083A true GB1497083A (en) | 1978-01-05 |
Family
ID=27278977
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB277375A Expired GB1497083A (en) | 1974-01-23 | 1975-01-22 | 1-substituted-4-(1,2-diphenylethyl)-piperazine derivatives and their salts and the preparation thereof |
Country Status (4)
Country | Link |
---|---|
CA (1) | CA1051433A (en) |
DE (1) | DE2502729A1 (en) |
FR (1) | FR2272672B1 (en) |
GB (1) | GB1497083A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2138016A (en) * | 1983-04-05 | 1984-10-17 | Bostik Ltd | Adhesive bonding |
EP0755680A2 (en) * | 1995-07-11 | 1997-01-29 | Pola Chemical Industries Inc | Use of piperazine compounds as narcotic antagonists |
-
1975
- 1975-01-21 CA CA218,369A patent/CA1051433A/en not_active Expired
- 1975-01-22 GB GB277375A patent/GB1497083A/en not_active Expired
- 1975-01-23 DE DE19752502729 patent/DE2502729A1/en not_active Ceased
- 1975-01-23 FR FR7502167A patent/FR2272672B1/fr not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2138016A (en) * | 1983-04-05 | 1984-10-17 | Bostik Ltd | Adhesive bonding |
EP0755680A2 (en) * | 1995-07-11 | 1997-01-29 | Pola Chemical Industries Inc | Use of piperazine compounds as narcotic antagonists |
EP0755680A3 (en) * | 1995-07-11 | 1998-01-14 | Pola Chemical Industries Inc | Use of piperazine compounds as narcotic antagonists |
US6100280A (en) * | 1995-07-11 | 2000-08-08 | Pola Chemical Industries, Inc. | Narcotic antagonist |
Also Published As
Publication number | Publication date |
---|---|
FR2272672B1 (en) | 1978-07-21 |
FR2272672A1 (en) | 1975-12-26 |
CA1051433A (en) | 1979-03-27 |
DE2502729A1 (en) | 1975-07-24 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PCNP | Patent ceased through non-payment of renewal fee |