GB809760A - Improvements in or relating to pharmacologically active piperazine derivatives and processes for preparing them - Google Patents
Improvements in or relating to pharmacologically active piperazine derivatives and processes for preparing themInfo
- Publication number
- GB809760A GB809760A GB9666/57A GB966657A GB809760A GB 809760 A GB809760 A GB 809760A GB 9666/57 A GB9666/57 A GB 9666/57A GB 966657 A GB966657 A GB 966657A GB 809760 A GB809760 A GB 809760A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chlorobenzhydryl
- piperazine
- methoxy
- reacting
- isopropyl
- 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
- C07D295/16—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 acylated on ring nitrogen atoms
- C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises piperazine derivatives of the general formula (I): <FORM:0809760/IV (b)/1> (wherein Y is an hydrogen atom or an unsubstituted or halogen, alkyl or alkoxy substituted aralkyl or aralkenyl group, X is -CH2-or -CO-, and R1, R2 and R3 are hydrogen or halogen atoms or alkoxy or alkyl groups containing not more than five carbon atoms) and their preparation by reacting piperazine with halides of the formul : <FORM:0809760/IV (b)/2> and Hal-Y in any desired order, in the presence of an hydrogen halide binding agent which may, if desired, be an excess of the basic component, or, when X is -CH2, by reducing the corresponding compound in which X is -CO- by means of lithium aluminium hydride. In examples: 1 - (4 - tert. - butylcinnamoyl) - 4 - (4-chlorobenzhydryl)-piperazine is prepared by reacting 4 - (tert. - butyl) - cinnamoyl chloride with 1 - (4 - chlorobenzhydryl) - piperazine in benzene; 1 - (4 - methylcinnamyl) - 4 - (4 - chlorobenzhydryl)-piperazine is prepared by reducing 1 - (4 - methylcinnamoyl) - 4 - (4 - chlorobenzhydryl) - piperazin with lithium aluminium hydride in ether, and converted to the hydrochloride; 1-cinnamyl-4-(4-chlorobenzhydryl)-piperazine is obtained by reacting 4-chlorobenzhydryl chloride with 1-cinnamyl-piperazine in toluene, if desired, in the presence of potassium carbonate, and converted to the hydrochloride. The physical and pharmacological data relating to other compounds of the general formula (I) in which Y is an hydrogen atom or a benzyl, cinnamoyl, benzhydryl or p-methyl-, p-isopropyl-, p-methoxy-, p-methoxy-p1-chloro-, p-methyl-p1-chloro- or p-isopropyl-p1-chlorobenzhydryl radical and one or more of R1, R2 and R3 are methoxy or isopropyl radicals are also given.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL809760X | 1956-04-20 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB809760A true GB809760A (en) | 1959-03-04 |
Family
ID=19836801
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB9666/57A Expired GB809760A (en) | 1956-04-20 | 1957-03-25 | Improvements in or relating to pharmacologically active piperazine derivatives and processes for preparing them |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB809760A (en) |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3422195A (en) * | 1963-09-27 | 1969-01-14 | A C F Amsterdam Chemie Farmaci | Antihistaminic and motion sickness preventing compositions |
US3625965A (en) * | 1966-12-28 | 1971-12-07 | Kyorin Seiyaku Kk | 1-CINNAMYL-4-LOWER ALKYLCARBONYL-or 4-PHENYLCARBONYL PIPERIZINES |
EP0000333A2 (en) * | 1977-06-18 | 1979-01-24 | BASF Aktiengesellschaft | Cyclic amine derivatives and fungicides containing them |
FR2474031A1 (en) * | 1980-01-21 | 1981-07-24 | Delalande Sa | N-tri:methoxy-cinnamoyl-N'-aralkyl-piperazine derivs. - useful for treating cardiac deficiencies |
FR2497512A2 (en) * | 1981-01-07 | 1982-07-09 | Delalande Sa | N-tri:methoxy-cinnamoyl-N'-aralkyl-piperazine derivs. - useful for treating cardiac deficiencies |
EP0187639A1 (en) * | 1985-01-11 | 1986-07-16 | Kanebo, Ltd. | Novel piperazine derivatives, processes for production thereof, and pharmaceutical compositions comprising said compounds as active ingredient |
EP0209843A2 (en) * | 1985-07-16 | 1987-01-28 | Kanebo, Ltd. | Benzylpiperazine compound, preparation thereof, pharmaceutical composition, and use |
EP0244319A2 (en) * | 1986-04-28 | 1987-11-04 | TERUMO KABUSHIKI KAISHA trading as TERUMO CORPORATION | Amide derivatives and antiallergic agents containing the same |
EP0157420A3 (en) * | 1984-04-04 | 1987-11-19 | Terumo Kabushiki Kaisha Trading As Terumo Corporation | Amide derivatives and 5-lipoxygenase inhibitors containing the same as an active ingredient |
EP0551617A2 (en) * | 1991-12-13 | 1993-07-21 | Ube Industries, Ltd. | Cinnamyl piperazine derivatives method of manufacturing the same and agricultural/horticultural fungicides containing cinnamyl piperazine derivatives |
CN101235020B (en) * | 2008-03-05 | 2012-09-05 | 南京医科大学 | Substituted cinnamamide derivatives and application of the same as nerve protecting agent |
CN102942538A (en) * | 2012-11-07 | 2013-02-27 | 南京医科大学 | Substituted benzhydryl piperazine derivative and preparation method and application thereof |
-
1957
- 1957-03-25 GB GB9666/57A patent/GB809760A/en not_active Expired
Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3422195A (en) * | 1963-09-27 | 1969-01-14 | A C F Amsterdam Chemie Farmaci | Antihistaminic and motion sickness preventing compositions |
US3625965A (en) * | 1966-12-28 | 1971-12-07 | Kyorin Seiyaku Kk | 1-CINNAMYL-4-LOWER ALKYLCARBONYL-or 4-PHENYLCARBONYL PIPERIZINES |
EP0000333A2 (en) * | 1977-06-18 | 1979-01-24 | BASF Aktiengesellschaft | Cyclic amine derivatives and fungicides containing them |
EP0000333A3 (en) * | 1977-06-18 | 1979-07-25 | Basf Aktiengesellschaft | Cyclic amine derivatives and fungicides containing them |
FR2474031A1 (en) * | 1980-01-21 | 1981-07-24 | Delalande Sa | N-tri:methoxy-cinnamoyl-N'-aralkyl-piperazine derivs. - useful for treating cardiac deficiencies |
FR2497512A2 (en) * | 1981-01-07 | 1982-07-09 | Delalande Sa | N-tri:methoxy-cinnamoyl-N'-aralkyl-piperazine derivs. - useful for treating cardiac deficiencies |
EP0399569A1 (en) * | 1984-04-04 | 1990-11-28 | TERUMO KABUSHIKI KAISHA trading as TERUMO CORPORATION | Amide derivatives and 5-lipoxygenase inhibitors containing the same as an active ingredient |
EP0157420A3 (en) * | 1984-04-04 | 1987-11-19 | Terumo Kabushiki Kaisha Trading As Terumo Corporation | Amide derivatives and 5-lipoxygenase inhibitors containing the same as an active ingredient |
EP0187639A1 (en) * | 1985-01-11 | 1986-07-16 | Kanebo, Ltd. | Novel piperazine derivatives, processes for production thereof, and pharmaceutical compositions comprising said compounds as active ingredient |
EP0209843A2 (en) * | 1985-07-16 | 1987-01-28 | Kanebo, Ltd. | Benzylpiperazine compound, preparation thereof, pharmaceutical composition, and use |
EP0209843A3 (en) * | 1985-07-16 | 1988-04-20 | Kanebo, Ltd. | Benzylpiperazine compound, preparation thereof, pharmaceutical composition, and use |
EP0244319A2 (en) * | 1986-04-28 | 1987-11-04 | TERUMO KABUSHIKI KAISHA trading as TERUMO CORPORATION | Amide derivatives and antiallergic agents containing the same |
EP0244319A3 (en) * | 1986-04-28 | 1990-04-25 | TERUMO KABUSHIKI KAISHA trading as TERUMO CORPORATION | Amide derivatives and antiallergic agents containing the same |
US4859673A (en) * | 1986-04-28 | 1989-08-22 | Terumo Kabushiki Kaisha | Amide derivatives and antiallergic agents containing the same |
EP0551617A2 (en) * | 1991-12-13 | 1993-07-21 | Ube Industries, Ltd. | Cinnamyl piperazine derivatives method of manufacturing the same and agricultural/horticultural fungicides containing cinnamyl piperazine derivatives |
EP0551617A3 (en) * | 1991-12-13 | 1993-11-03 | Ube Industries | Cinnamyl piperazine derivatives method of manufacturing the same and agricultural/horticultural fungicides containing cinnamyl piperazine derivatives |
CN101235020B (en) * | 2008-03-05 | 2012-09-05 | 南京医科大学 | Substituted cinnamamide derivatives and application of the same as nerve protecting agent |
CN102942538A (en) * | 2012-11-07 | 2013-02-27 | 南京医科大学 | Substituted benzhydryl piperazine derivative and preparation method and application thereof |
CN102942538B (en) * | 2012-11-07 | 2014-11-05 | 南京医科大学 | Substituted benzhydryl piperazine derivative and preparation method and application thereof |
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