GB1368256A - 1- trifluoromethyl-phenyl- 4-cyclic-amidoalkyl- piperazines useful as amorectic agents - Google Patents

1- trifluoromethyl-phenyl- 4-cyclic-amidoalkyl- piperazines useful as amorectic agents

Info

Publication number
GB1368256A
GB1368256A GB2053672A GB2053672A GB1368256A GB 1368256 A GB1368256 A GB 1368256A GB 2053672 A GB2053672 A GB 2053672A GB 2053672 A GB2053672 A GB 2053672A GB 1368256 A GB1368256 A GB 1368256A
Authority
GB
United Kingdom
Prior art keywords
compound
formula
reacting
hal
product
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
GB2053672A
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.)
Pfizer Ltd
Original Assignee
Pfizer Ltd
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
Priority to BE788280D priority Critical patent/BE788280A/en
Application filed by Pfizer Ltd filed Critical Pfizer Ltd
Priority to GB2053672A priority patent/GB1368256A/en
Priority to AU45940/72A priority patent/AU4594072A/en
Priority to NL7211694A priority patent/NL7211694A/xx
Priority to IE117372A priority patent/IE37697B1/en
Priority to DE19722242382 priority patent/DE2242382A1/en
Priority to AT1089573A priority patent/AT320655B/en
Priority to AT752072A priority patent/AT321307B/en
Priority to FR7231080A priority patent/FR2154449A1/fr
Priority to CH1293572A priority patent/CH554899A/en
Priority to CH356874A priority patent/CH551430A/en
Priority to AR24388272A priority patent/AR200387A1/en
Priority to JP8802072A priority patent/JPS4885584A/ja
Priority to ES406374A priority patent/ES406374A1/en
Publication of GB1368256A publication Critical patent/GB1368256A/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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

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

Abstract

1368256 1-Trifluoromethylphenyl 4-(cyclic amido-alkyl)-piperazines PFIZER Ltd 4 Sept 1972 [4 Sept 1971 3 May 1972] 41322/71 and 20536/72 Heading C2C Novel compounds of the Formula (I) where R denotes a succinimido, glutarimido, 2,4 - dioxo - 1 (or 3) - imidazolidinyl or 2,4- dioxo - 1 (or 3) - hexahydropyrimidinyl group, the last two groups being optionally substituted on the imino N atom with a CH 3 or C 2 H 5 group; X denotes H, F, Cl or Br; and n is 2 or 3, and their non-toxic acid addition salts, are obtained (1) by reacting a 1-aryl piperazine (II) with an alkyl halide hal-(CH 2 ) n R, where hal is a halogen atom, e.g. Cl or Br, or a tosylalate tosyl(OH 2 ) n -R by heating in a dry inert organic solvent in the presence of a base; (2) by reacting a compound of the Formula (III) with a lower alkyl isocyanate or #-isocyanatopropionate to form a compound (IV) where R<SP>1</SP> is lower alkyl and m is 1 or 2, and then heating this product to effect ring closure, e.g. using an oil bath at 200‹ C. for several hours, (3) by reacting an amine of Formula (III) with a hal-CH 2 COOR<SP>2</SP> or hal-CH 2 CH 2 COOR<SP>2</SP>, in which the lower alkyl group R<SP>2</SP> is preferably methyl or ethyl, to yield a product of Formula (V) which is then reacted with methyl or ethyl isocyanate to yield (VI) (4) by reacting an amine (III) with succinic anhydride or glutaric anhydride at elevated temperature with or without solvent to form a product (VII) in which p is 2 or 3; (5) by appropriate nuclear aromatic halogenation of compounds (I) in which X is H; (6) by nitrosating a compound (I) in which X is H, reducing the nitroso group to amino, diazotizing followed by Sandmeyer reaction with CuCl or CuBr to form the Cl- or Br-substituted product; (7) by reducing a compound of Formula (I) in which X is NO 2 to an -NH 2 followed by diazotization and Sandmeyer reaction as a (6); (8) by reacting an aniline derivative (XII) with a compound [Y(CH 2 ) 3 ] 2 N-(CH 2 ) n R in which Y is OH or halogen. An intermediate, 1-(2-aminoethyl)-4-(4-bromo- 3 - trifluoromethylphenyl)piperazine is obtained by brominating 1 - (2 - aminomethyl) - 4 - (3- trifluoromethylphenyl)piperazine. A pharmaceutical composition for reducing appetite comprises a compound of Formula (I) above with a non-toxic carrier or diluent in forms suitable for oral or parenteral administration.
GB2053672A 1971-09-04 1972-05-03 1- trifluoromethyl-phenyl- 4-cyclic-amidoalkyl- piperazines useful as amorectic agents Expired GB1368256A (en)

Priority Applications (14)

Application Number Priority Date Filing Date Title
BE788280D BE788280A (en) 1971-09-04 NEWS 1- (3-TRIFLUORO-METHYL-PHENYL) -4 - ((CYCLIC AMIDO) - ALKYL) PIPERAZINES AND PHARMACEUTICAL COMPOSITION CONTAINING THEM
GB2053672A GB1368256A (en) 1971-09-04 1972-05-03 1- trifluoromethyl-phenyl- 4-cyclic-amidoalkyl- piperazines useful as amorectic agents
AU45940/72A AU4594072A (en) 1971-09-04 1972-08-24 Trifluoromethylphenyl piperazine derivatives as anorectic agents
NL7211694A NL7211694A (en) 1971-09-04 1972-08-28
IE117372A IE37697B1 (en) 1971-09-04 1972-08-29 1-(trifluoromethyl-phenyl)-4-(cyclic-amido-alkyl)piperazines useful as anorectic agents
DE19722242382 DE2242382A1 (en) 1971-09-04 1972-08-29 NEW PIPERAZINE COMPOUNDS
AT752072A AT321307B (en) 1971-09-04 1972-09-01 Process for the preparation of new piperazine derivatives and their salts
AT1089573A AT320655B (en) 1971-09-04 1972-09-01 Process for the preparation of new piperazine derivatives and their salts
FR7231080A FR2154449A1 (en) 1971-09-04 1972-09-01
CH1293572A CH554899A (en) 1971-09-04 1972-09-01 PROCESS FOR THE PREPARATION OF 1- (3-TRIFLUOROMETHYLPHENYL) -4 ((CYCLIC AMIDO) -ALKYL) -PIPERAZINES.
CH356874A CH551430A (en) 1971-09-04 1972-09-01 PROCESS FOR THE PREPARATION OF 1- (3-TRIFLUOROMETHYLPHENYL) 4 - ((CYCLIC AMIDO) -ALKYL) -PIPERAZINES.
AR24388272A AR200387A1 (en) 1971-09-04 1972-09-01 PROCEDURE FOR PREPARING TRIFLUOROMETHYLPHENYLPIPERAZINE DERIVATIVES
JP8802072A JPS4885584A (en) 1971-09-04 1972-09-04
ES406374A ES406374A1 (en) 1971-09-04 1972-09-04 1- trifluoromethyl-phenyl- 4-cyclic-amidoalkyl- piperazines useful as amorectic agents

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB4132271 1971-09-04
GB2053672A GB1368256A (en) 1971-09-04 1972-05-03 1- trifluoromethyl-phenyl- 4-cyclic-amidoalkyl- piperazines useful as amorectic agents

Publications (1)

Publication Number Publication Date
GB1368256A true GB1368256A (en) 1974-09-25

Family

ID=26254732

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2053672A Expired GB1368256A (en) 1971-09-04 1972-05-03 1- trifluoromethyl-phenyl- 4-cyclic-amidoalkyl- piperazines useful as amorectic agents

Country Status (12)

Country Link
JP (1) JPS4885584A (en)
AR (1) AR200387A1 (en)
AT (2) AT320655B (en)
AU (1) AU4594072A (en)
BE (1) BE788280A (en)
CH (2) CH551430A (en)
DE (1) DE2242382A1 (en)
ES (1) ES406374A1 (en)
FR (1) FR2154449A1 (en)
GB (1) GB1368256A (en)
IE (1) IE37697B1 (en)
NL (1) NL7211694A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0015615A1 (en) * 1979-03-01 1980-09-17 Duphar International Research B.V Phenyl piperazine derivatives, their preparation and antiagressive medicines containing them
EP0048043A1 (en) * 1980-09-12 1982-03-24 Duphar International Research B.V Phenyl piperazine derivatives having analgetic activity
EP0048045A1 (en) * 1980-09-12 1982-03-24 Duphar International Research B.V Phenyl piperazine derivatives having antiagressive activity
US4452798A (en) * 1982-06-22 1984-06-05 Warner-Lambert Company 1-Substituted phenyl-4-alkyl hydantoin piperazine compounds as antihypertensive agents
US6090809A (en) * 1997-11-13 2000-07-18 Ranbaxy Laboratories Limited 1-(4-arylpiperazin-1-yl)-ω-[n-(α..omega.-dicarboximido)]-alkanes useful as uro-selective α1 -adrenoceptor blockers

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2263211A1 (en) * 1972-12-23 1974-07-04 Boehringer Sohn Ingelheim NEW ARYLPIPERAZINE AND PROCESS FOR THEIR PRODUCTION
DE2727469A1 (en) * 1977-06-18 1978-12-21 Hoechst Ag NEW HEXAHYDROPYRIMIDINE, METHOD FOR THE PRODUCTION THEREOF AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS
JPS5976059A (en) * 1982-10-21 1984-04-28 Sumitomo Chem Co Ltd Cyclic imide derivative and its acid addition salt
AU1979799A (en) * 1998-07-21 2000-02-14 Ranbaxy Laboratories Limited Arylpiperazine derivatives useful as uro-selective alpha-1-adrenoceptor blockers
WO2000005205A1 (en) * 1998-07-21 2000-02-03 Ranbaxy Laboratories Limited Arylpiperazine derivatives useful as uroselective alpha1-adrenoceptor blockers
AU2002253429A1 (en) * 2002-04-08 2003-10-20 Ranbaxy Laboratories Limited ALPHA, OMEGA-DICARBOXIMIDE DERIVATIVES AS USEFUL URO-SELECTIVE Alpha1Alpha ADRENOCEPTOR BLOCKERS

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0015615A1 (en) * 1979-03-01 1980-09-17 Duphar International Research B.V Phenyl piperazine derivatives, their preparation and antiagressive medicines containing them
EP0048043A1 (en) * 1980-09-12 1982-03-24 Duphar International Research B.V Phenyl piperazine derivatives having analgetic activity
EP0048045A1 (en) * 1980-09-12 1982-03-24 Duphar International Research B.V Phenyl piperazine derivatives having antiagressive activity
US4452798A (en) * 1982-06-22 1984-06-05 Warner-Lambert Company 1-Substituted phenyl-4-alkyl hydantoin piperazine compounds as antihypertensive agents
US6090809A (en) * 1997-11-13 2000-07-18 Ranbaxy Laboratories Limited 1-(4-arylpiperazin-1-yl)-ω-[n-(α..omega.-dicarboximido)]-alkanes useful as uro-selective α1 -adrenoceptor blockers

Also Published As

Publication number Publication date
AU4594072A (en) 1974-02-28
NL7211694A (en) 1973-03-06
DE2242382A1 (en) 1973-03-15
AT320655B (en) 1975-02-25
JPS4885584A (en) 1973-11-13
IE37697B1 (en) 1977-09-28
ES406374A1 (en) 1975-07-16
AT321307B (en) 1975-03-25
IE37697L (en) 1973-03-04
CH554899A (en) 1974-10-15
AR200387A1 (en) 1974-11-08
FR2154449A1 (en) 1973-05-11
BE788280A (en) 1973-02-28
CH551430A (en) 1974-07-15

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Legal Events

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