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 thereof

Info

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
Application number
GB277375A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dainippon Pharmaceutical Co Ltd
Original Assignee
Dainippon Pharmaceutical Co Ltd
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 JP1047074A external-priority patent/JPS5643463B2/ja
Priority claimed from JP2892674A external-priority patent/JPS5643464B2/ja
Priority claimed from JP2968374A external-priority patent/JPS5644071B2/ja
Application filed by Dainippon Pharmaceutical Co Ltd filed Critical Dainippon Pharmaceutical Co Ltd
Publication of GB1497083A publication Critical patent/GB1497083A/en
Expired legal-status Critical Current

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.
GB277375A 1974-01-23 1975-01-22 1-substituted-4-(1,2-diphenylethyl)-piperazine derivatives and their salts and the preparation thereof Expired GB1497083A (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (4)

* Cited by examiner, † Cited by third party
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