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 them

Info

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
Application number
GB9666/57A
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.)
Janssen Pharmaceutica NV
Original Assignee
Janssen Pharmaceutica NV
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
Application filed by Janssen Pharmaceutica NV filed Critical Janssen Pharmaceutica NV
Publication of GB809760A publication Critical patent/GB809760A/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
    • C07D295/16—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.
GB9666/57A 1956-04-20 1957-03-25 Improvements in or relating to pharmacologically active piperazine derivatives and processes for preparing them Expired GB809760A (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (19)

* Cited by examiner, † Cited by third party
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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