GB1382536A - Piperazine derivatives - Google Patents

Piperazine derivatives

Info

Publication number
GB1382536A
GB1382536A GB1985073A GB1985073A GB1382536A GB 1382536 A GB1382536 A GB 1382536A GB 1985073 A GB1985073 A GB 1985073A GB 1985073 A GB1985073 A GB 1985073A GB 1382536 A GB1382536 A GB 1382536A
Authority
GB
United Kingdom
Prior art keywords
formula
compound
reaction
reacting
piperazine
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
GB1985073A
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.)
Synthelabo SA
Original Assignee
Synthelabo SA
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 Synthelabo SA filed Critical Synthelabo SA
Publication of GB1382536A publication Critical patent/GB1382536A/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
    • C07D295/08—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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/20—Hypnotics; Sedatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • 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
    • C07D295/084—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 attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—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 attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • 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
    • C07D295/14—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/15—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Anesthesiology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

1382536 Piperazine derivatives SYNTHELABO 26 April 1973 [3 May 1972] 19850/73 Heading C2C The invention comprises piperazine derivatives of the formula in which A is -(CH 2 ) n -COOR where n is an integer from 1 to 6 and R is a straight or branched alkyl radical of 1 to 6 carbon atoms, or A is -CH 2 -(CH 2 ) n -R 1 in which n is as above and R 1 is CN or COOH, and their pharmaceutically acceptable acid addition salts and, where R 1 is COOH, their pharmaceutically acceptable salts with bases. The piperazine derivatives may be prepared by (a) reacting N-(m-trifluoromethylthiophenyl)-piperazine with a halogeno compound of the formula A-X in which X is chlorine, bromine or iodine and A is as above. The reaction may be carried out by heating the two starting materials together in an inert organic solvent in the presence of an acceptor for the hydrohalic acid liberated; (b) reacting a compound of formula with a compound of formula in which one of Y and Z is CH 2 -CH 2 -X and the other is hydrogen and A and X are as above. The reaction may be carried out in an inert organic solvent in the presence of an acceptor for the hydrohalic acid liberated; (c) and in which A is -CH 2 CH 2 CN or -CH 2 -CH 2 COOR reacting together N - (m - trifluoromethylthiophenyl)-piperazine and an acrylic compound of formula CH 2 =CH-T in which T is CN or COOR. The reaction may be carried out with or without a solvent and preferably in the presence of a condensation catalyst such as benzyltrimethylammonium hydroxide. A still further method of making the compounds in which A is CH 2 -(CH 2 ) n -CN comprises reacting a compound of formula with a metallic cyanide. The compound of formula above wherein X is chlorine, bromine or iodine and n is an integer of from 1 to 6 is also claimed per se and may be prepared by the reaction of a halogenation agent with an alcohol of the formula
GB1985073A 1972-05-03 1973-04-26 Piperazine derivatives Expired GB1382536A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7215642A FR2186237B1 (en) 1972-05-03 1972-05-03

Publications (1)

Publication Number Publication Date
GB1382536A true GB1382536A (en) 1975-02-05

Family

ID=9097886

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1985073A Expired GB1382536A (en) 1972-05-03 1973-04-26 Piperazine derivatives

Country Status (10)

Country Link
JP (1) JPS526996B2 (en)
BE (1) BE798872A (en)
DE (1) DE2322070A1 (en)
DK (1) DK138423B (en)
ES (1) ES414340A1 (en)
FR (1) FR2186237B1 (en)
GB (1) GB1382536A (en)
IE (1) IE37581B1 (en)
NL (1) NL149800B (en)
SE (1) SE388198B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8598348B2 (en) 2009-02-17 2013-12-03 H. Lundbeck A/S Purification of 1-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS57137766A (en) * 1981-02-17 1982-08-25 Toyota Motor Corp Lubricating structure of differential device

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8598348B2 (en) 2009-02-17 2013-12-03 H. Lundbeck A/S Purification of 1-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine

Also Published As

Publication number Publication date
FR2186237A1 (en) 1974-01-11
NL7306171A (en) 1973-11-06
JPS526996B2 (en) 1977-02-26
IE37581L (en) 1973-11-03
IE37581B1 (en) 1977-08-31
SE388198B (en) 1976-09-27
JPS4947381A (en) 1974-05-08
DK138423B (en) 1978-09-04
DK138423C (en) 1979-02-12
DE2322070A1 (en) 1973-11-15
FR2186237B1 (en) 1975-10-31
NL149800B (en) 1976-06-15
ES414340A1 (en) 1976-05-16
BE798872A (en) 1973-10-29

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee