IE37581B1 - New piperazine derivatives - Google Patents

New piperazine derivatives

Info

Publication number
IE37581B1
IE37581B1 IE673/73A IE67373A IE37581B1 IE 37581 B1 IE37581 B1 IE 37581B1 IE 673/73 A IE673/73 A IE 673/73A IE 67373 A IE67373 A IE 67373A IE 37581 B1 IE37581 B1 IE 37581B1
Authority
IE
Ireland
Prior art keywords
formula
compound
reaction
reacting
piperazine
Prior art date
Application number
IE673/73A
Other versions
IE37581L (en
Original Assignee
Synthelabo
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 filed Critical Synthelabo
Publication of IE37581L publication Critical patent/IE37581L/en
Publication of IE37581B1 publication Critical patent/IE37581B1/en

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 [GB1382536A]
IE673/73A 1972-05-03 1973-04-30 New piperazine derivatives IE37581B1 (en)

Applications Claiming Priority (1)

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

Publications (2)

Publication Number Publication Date
IE37581L IE37581L (en) 1973-11-03
IE37581B1 true IE37581B1 (en) 1977-08-31

Family

ID=9097886

Family Applications (1)

Application Number Title Priority Date Filing Date
IE673/73A IE37581B1 (en) 1972-05-03 1973-04-30 New 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)

Families Citing this family (2)

* 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
TW201033181A (en) 2009-02-17 2010-09-16 Lundbeck & Co As H Purification of 1-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine

Also Published As

Publication number Publication date
SE388198B (en) 1976-09-27
DK138423B (en) 1978-09-04
DK138423C (en) 1979-02-12
NL7306171A (en) 1973-11-06
FR2186237B1 (en) 1975-10-31
GB1382536A (en) 1975-02-05
DE2322070A1 (en) 1973-11-15
FR2186237A1 (en) 1974-01-11
JPS4947381A (en) 1974-05-08
BE798872A (en) 1973-10-29
ES414340A1 (en) 1976-05-16
NL149800B (en) 1976-06-15
IE37581L (en) 1973-11-03
JPS526996B2 (en) 1977-02-26

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