GB889223A - Phenylpiperazinylalkyl esters and amides - Google Patents

Phenylpiperazinylalkyl esters and amides

Info

Publication number
GB889223A
GB889223A GB26208/59A GB2620859A GB889223A GB 889223 A GB889223 A GB 889223A GB 26208/59 A GB26208/59 A GB 26208/59A GB 2620859 A GB2620859 A GB 2620859A GB 889223 A GB889223 A GB 889223A
Authority
GB
United Kingdom
Prior art keywords
reacting
phenyl
piperazine
cnh2n
radical
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
GB26208/59A
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.)
Bayer Corp
Original Assignee
Miles Laboratories Inc
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 Miles Laboratories Inc filed Critical Miles Laboratories Inc
Publication of GB889223A publication Critical patent/GB889223A/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
    • C07D295/04—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
    • C07D295/12—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 or doubly bound nitrogen atoms
    • C07D295/125—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 or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—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 or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

Abstract

The invention comprises compounds of the general formula <FORM:0889223/IV (b)/1> wherein R represents a hydrogen or chlorine atom or a methoxy radical, CnH2n represents a straight or branched alkylene chain in which n is 2, 3, 4 or 5, A represents an oxygen atom or an -NH- group, and Ar represents a phenyl, 4 - methoxyphenyl, 3,4 - dimethoxyphenyl, 3,4 - methylenedioxyphenyl or 3,4,5-trimethoxyphenyl radical) and their non-toxic water-soluble acid addition salts having therapeutically acceptable anions, and pharmaceutical compositions containing these compounds (see Group VI). The esters may be made by reacting a 1-phenyl-piperazine with a haloalkanol (or a carboxylic ester thereof with subsequent hydrolysis) or with a lower alkylene oxide, and esterifying the resulting 1-phenyl-4-(o -hydroxyalkyl)-piperazine with a benzoyl chloride ArCOCl, or (when R=CH3O) reacting p-anisidine with ethylene oxide and thionyl chloride to form N,N-bis-(2-chloroethyl)-p-anisidine, reacting this with an aminoalkanol H2N-(CnH2n)-OH and esterifying the product as before. The amides may be made by reacting a 1-phenylpiperazine with a haloalkyl or alkenyl cyanide, hydrogenating the resulting 1-phenyl-4-(o -cyanoalkyl)-piperazine and reacting the resulting amine with a benzoyl chloride ArCOCl.ALSO:Pharmaceutical compositions, having sedative activity, comprise about 25-300 mg. of a compound of the general formula <FORM:0889223/VI/1> (wherein R represents a hydrogen or chlorine atom or a methoxy radical, CnH2n represents a straight or branched alkylene chain in which n is 2, 3, 4 or 5, A represents an oxygen atom or an -NH- group, and Ar represents a phenyl, 4-methoxyphenyl, 3,4-dimethoxyphenyl, 3,4-methylenedioxyphenyl or 3,4,5 - trimethoxyphenyl radical), or a non-toxic water-soluble acid addition salt thereof, with a pharmaceutical carrier in unit dosage form (e.g. tablets, powders, capsules, suspensions or injection solutions). Specified salts are hydrohalides, sulphates and maleates.
GB26208/59A 1958-08-01 1959-07-30 Phenylpiperazinylalkyl esters and amides Expired GB889223A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US889223XA 1958-08-01 1958-08-01

Publications (1)

Publication Number Publication Date
GB889223A true GB889223A (en) 1962-02-14

Family

ID=22214289

Family Applications (1)

Application Number Title Priority Date Filing Date
GB26208/59A Expired GB889223A (en) 1958-08-01 1959-07-30 Phenylpiperazinylalkyl esters and amides

Country Status (1)

Country Link
GB (1) GB889223A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3953449A (en) 1973-05-09 1976-04-27 Synthelabo 2-(4-M-CF3 or -SCF3 phenylpiperazino)-ethyl benzoates
EP0104614A1 (en) * 1982-09-24 1984-04-04 Chugai Seiyaku Kabushiki Kaisha Phenylpiperazine derivatives and process for producing the same
EP0895993A1 (en) * 1997-08-08 1999-02-10 Bayer Ag Process for the preparation of N-aryl-N'aklyl-piperazines

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3953449A (en) 1973-05-09 1976-04-27 Synthelabo 2-(4-M-CF3 or -SCF3 phenylpiperazino)-ethyl benzoates
EP0104614A1 (en) * 1982-09-24 1984-04-04 Chugai Seiyaku Kabushiki Kaisha Phenylpiperazine derivatives and process for producing the same
EP0895993A1 (en) * 1997-08-08 1999-02-10 Bayer Ag Process for the preparation of N-aryl-N'aklyl-piperazines
US5922874A (en) * 1997-08-08 1999-07-13 Bayer Atkiengesellschaft Process for preparing N-aryl-N'-alkyl-piperazines

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