FR2429216A1 - CNS-active substd. alkyl-meta:tri:fluoro:methyl:thio:phenyl-piperazine - with psychotropic properties, useful in treatment of anxiety and depression - Google Patents

CNS-active substd. alkyl-meta:tri:fluoro:methyl:thio:phenyl-piperazine - with psychotropic properties, useful in treatment of anxiety and depression

Info

Publication number
FR2429216A1
FR2429216A1 FR7818352A FR7818352A FR2429216A1 FR 2429216 A1 FR2429216 A1 FR 2429216A1 FR 7818352 A FR7818352 A FR 7818352A FR 7818352 A FR7818352 A FR 7818352A FR 2429216 A1 FR2429216 A1 FR 2429216A1
Authority
FR
France
Prior art keywords
alkyl
substd
anxiety
cns
thio
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.)
Granted
Application number
FR7818352A
Other languages
French (fr)
Other versions
FR2429216B1 (en
Inventor
Henry Najer
Jean-Pierre Kaplan
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
Priority to FR7818352A priority Critical patent/FR2429216A1/en
Priority to FI791926A priority patent/FI791926A/en
Priority to DK251079A priority patent/DK251079A/en
Priority to IL57569A priority patent/IL57569A0/en
Priority to AU48112/79A priority patent/AU521110B2/en
Priority to PT69775A priority patent/PT69775A/en
Priority to NZ190758A priority patent/NZ190758A/en
Priority to LU81396A priority patent/LU81396A1/en
Priority to NO792020A priority patent/NO792020L/en
Priority to ES481632A priority patent/ES481632A1/en
Priority to IT23695/79A priority patent/IT1121588B/en
Priority to GR59368A priority patent/GR67646B/el
Priority to NL7904755A priority patent/NL7904755A/en
Priority to DE19792924681 priority patent/DE2924681A1/en
Priority to SE7905402A priority patent/SE7905402L/en
Priority to GB7921307A priority patent/GB2023594B/en
Publication of FR2429216A1 publication Critical patent/FR2429216A1/en
Application granted granted Critical
Publication of FR2429216B1 publication Critical patent/FR2429216B1/fr
Granted legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D211/74—Oxygen atoms
    • C07D211/76—Oxygen atoms attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/30—Oxygen or sulfur atoms
    • C07D233/32—One oxygen atom
    • C07D233/36—One oxygen atom with hydrocarbon radicals, substituted by nitrogen atoms, attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D235/26—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/18—Oxygen atoms
    • C07D263/20—Oxygen atoms attached in position 2
    • C07D263/22—Oxygen atoms attached in position 2 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to other ring 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
    • 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
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Phenylpiperazine derivs. of formula (I) and their pharmaceutically acceptable acid addn. salts are new: (where n is 1,2 or 3; R is 2-tetrahydrofuryl, -CH2-S-Z, -CH2-O-Z' or a gp. of formula (A) or (B); R1 and R2 are H or together complete a fused benzene ring; X is O,S, (alkyl)imino or CH2; m is 0 or 1; Z is H, alkyl or -CO-Z'; Z' is alkyl; all alkyl being 1-8C). Daily doses are 5-200 mg. LD50 is 250-1000 mg/kg p.o. and 75-230 mg/kg i.p.
FR7818352A 1978-06-20 1978-06-20 CNS-active substd. alkyl-meta:tri:fluoro:methyl:thio:phenyl-piperazine - with psychotropic properties, useful in treatment of anxiety and depression Granted FR2429216A1 (en)

Priority Applications (16)

Application Number Priority Date Filing Date Title
FR7818352A FR2429216A1 (en) 1978-06-20 1978-06-20 CNS-active substd. alkyl-meta:tri:fluoro:methyl:thio:phenyl-piperazine - with psychotropic properties, useful in treatment of anxiety and depression
DK251079A DK251079A (en) 1978-06-20 1979-06-15 METHOD OF PREPARATION OF PHENYLPIPERAZINE DERIVATIVES
IL57569A IL57569A0 (en) 1978-06-20 1979-06-15 Phenylpiperazine derivative,their preparation and pharmaceutical compositions containing them
AU48112/79A AU521110B2 (en) 1978-06-20 1979-06-15 Phenylpiperazine derivatives
FI791926A FI791926A (en) 1978-06-20 1979-06-15 PHENYLPIPERAZINE DERIVATIVES
ES481632A ES481632A1 (en) 1978-06-20 1979-06-18 1-substituted alkyl-4-(3- trifluoromethylthiophenyl)- piperazines
LU81396A LU81396A1 (en) 1978-06-20 1979-06-18 PHENYLPIPERAZINE DERIVATIVES
NO792020A NO792020L (en) 1978-06-20 1979-06-18 PROCEDURE FOR THE PREPARATION OF PHARMACOLOGICALLY ACTIVE PHENYL PIPERAZINES
PT69775A PT69775A (en) 1978-06-20 1979-06-18 PROCESS FOR THE PREPARATION OF PHENYLPIPERAZINE DERIVATIVES
IT23695/79A IT1121588B (en) 1978-06-20 1979-06-18 PHENYLPIPERAZINE DERIVATIVES
GR59368A GR67646B (en) 1978-06-20 1979-06-18
NZ190758A NZ190758A (en) 1978-06-20 1979-06-18 Phenylpiperazine derivatives and pharmaceutical compositions
DE19792924681 DE2924681A1 (en) 1978-06-20 1979-06-19 PHENYLPIPERAZINE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND MEDICINAL PRODUCTS CONTAINING THE SAME
SE7905402A SE7905402L (en) 1978-06-20 1979-06-19 PHENYL-PIPERAZINE DERIVATIVES
NL7904755A NL7904755A (en) 1978-06-20 1979-06-19 PHENYLPIPERAZINE DERIVATIVES, METHOD OF PREPARATION THEREOF, AND USE OF THIS DERIVATIVE IN A PHARMA-CEUTIC PRODUCT.
GB7921307A GB2023594B (en) 1978-06-20 1979-06-19 1-substituted alkyl -4 -piperazines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7818352A FR2429216A1 (en) 1978-06-20 1978-06-20 CNS-active substd. alkyl-meta:tri:fluoro:methyl:thio:phenyl-piperazine - with psychotropic properties, useful in treatment of anxiety and depression

Publications (2)

Publication Number Publication Date
FR2429216A1 true FR2429216A1 (en) 1980-01-18
FR2429216B1 FR2429216B1 (en) 1980-11-07

Family

ID=9209722

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7818352A Granted FR2429216A1 (en) 1978-06-20 1978-06-20 CNS-active substd. alkyl-meta:tri:fluoro:methyl:thio:phenyl-piperazine - with psychotropic properties, useful in treatment of anxiety and depression

Country Status (1)

Country Link
FR (1) FR2429216A1 (en)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1485847A (en) * 1963-03-29 1967-06-23 Miles Lab Manufacturing process of new quinazolinediones
US3362956A (en) * 1965-08-19 1968-01-09 Sterling Drug Inc 1-[(heterocyclyl)-lower-alkyl]-4-substituted-piperazines
FR6924M (en) * 1967-10-18 1969-05-05

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1485847A (en) * 1963-03-29 1967-06-23 Miles Lab Manufacturing process of new quinazolinediones
US3362956A (en) * 1965-08-19 1968-01-09 Sterling Drug Inc 1-[(heterocyclyl)-lower-alkyl]-4-substituted-piperazines
FR6924M (en) * 1967-10-18 1969-05-05

Also Published As

Publication number Publication date
FR2429216B1 (en) 1980-11-07

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