FR2374318A1 - 1-Benzhydryl:oxy-alkyl-4-phenylalkyl- or cinnamyl-piperazine derivs. - with dopaminergic, anticholinergic and antiparkinson activity (BE 14.6.78) - Google Patents

1-Benzhydryl:oxy-alkyl-4-phenylalkyl- or cinnamyl-piperazine derivs. - with dopaminergic, anticholinergic and antiparkinson activity (BE 14.6.78)

Info

Publication number
FR2374318A1
FR2374318A1 FR7737708A FR7737708A FR2374318A1 FR 2374318 A1 FR2374318 A1 FR 2374318A1 FR 7737708 A FR7737708 A FR 7737708A FR 7737708 A FR7737708 A FR 7737708A FR 2374318 A1 FR2374318 A1 FR 2374318A1
Authority
FR
France
Prior art keywords
piperazine
activity
alkyl
anticholinergic
dopaminergic
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
FR7737708A
Other languages
French (fr)
Other versions
FR2374318B1 (en
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.)
Gist Brocades NV
Original Assignee
Gist Brocades NV
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 claimed from GB52223/76A external-priority patent/GB1545094A/en
Application filed by Gist Brocades NV filed Critical Gist Brocades NV
Publication of FR2374318A1 publication Critical patent/FR2374318A1/en
Application granted granted Critical
Publication of FR2374318B1 publication Critical patent/FR2374318B1/fr
Granted 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
    • C07D295/16—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 acylated on ring nitrogen atoms
    • C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • 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

Landscapes

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

Abstract

New benzhydroloxyalkyl-piperazine derivs. are cpds. of formula (I) salts with acids and quaternary ammonium salts. In the formula R1-R9 are H, halogen 1-6C alkyl or 1-6 C alkoxy, n is 2 or 3, X is a group (CH2)m (m is 1,2 3 or 4) or -CH2CH=CH- in which the methylene gp. is linked to the piperazine nitrogen. (I) have activity similar to that of bromocriptine. With low toxicity, they have highly specific dopaminergic activity. They can be used for the treatment of Parkinson's disease and for combatting pathalogical states associated with hyperprolactinaemia (galactorrhoea, excessive puerperal milk flow, hypogonadism, infertility) and excessive secretion of growth hormone (acromegaly). (I) also have anticholinergic activity, which increass their effectiveness in the treatment of Parkinson's disease. Specific (I) include 1 - 2- bis(p-fluorophenyl)methoxy - ethyl -4-(3-phenyl-2-&propenyl)-piperazine. In an example this is prepd. by reacting 1-cinnamylpiperazine with bis(p-fluorophenyl)methyl 2-chloroethyl ether in methyl isobutyl ketone in the presence of K2CO3 and KI. the product is isolated in the form of its 1:2 maleate, m.pt. 192-4 degrees.
FR7737708A 1976-12-14 1977-12-14 1-Benzhydryl:oxy-alkyl-4-phenylalkyl- or cinnamyl-piperazine derivs. - with dopaminergic, anticholinergic and antiparkinson activity (BE 14.6.78) Granted FR2374318A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB52223/76A GB1545094A (en) 1976-12-14 1976-12-14 Piperazine derivatives
NL5222376 1976-12-14

Publications (2)

Publication Number Publication Date
FR2374318A1 true FR2374318A1 (en) 1978-07-13
FR2374318B1 FR2374318B1 (en) 1982-11-19

Family

ID=26267017

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7737708A Granted FR2374318A1 (en) 1976-12-14 1977-12-14 1-Benzhydryl:oxy-alkyl-4-phenylalkyl- or cinnamyl-piperazine derivs. - with dopaminergic, anticholinergic and antiparkinson activity (BE 14.6.78)

Country Status (1)

Country Link
FR (1) FR2374318A1 (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0099148A1 (en) * 1982-06-29 1984-01-25 Gist-Brocades N.V. Piperazine derivatives, processes for their preparation and pharmaceutical preparations containing them
EP0243905A1 (en) * 1986-04-28 1987-11-04 Richter Gedeon Vegyészeti Gyár R.T. 1-(omega-[bis-(phenyl)alkoxy]-alkyl)-4-(di-(phenyl)-methyl)piperazines, process for their preparation and medicines containing them
FR2601366A1 (en) * 1986-07-10 1988-01-15 Andre Buzas BENZHYDRYLOXYETHYL-PIPERAZINE DERIVATIVES, METHODS OF OBTAINING THEM AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB837986A (en) * 1956-07-10 1960-06-22 Henri Morren New piperazine derivatives and process for the preparation thereof

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB837986A (en) * 1956-07-10 1960-06-22 Henri Morren New piperazine derivatives and process for the preparation thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
NV1107/54 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0099148A1 (en) * 1982-06-29 1984-01-25 Gist-Brocades N.V. Piperazine derivatives, processes for their preparation and pharmaceutical preparations containing them
EP0243905A1 (en) * 1986-04-28 1987-11-04 Richter Gedeon Vegyészeti Gyár R.T. 1-(omega-[bis-(phenyl)alkoxy]-alkyl)-4-(di-(phenyl)-methyl)piperazines, process for their preparation and medicines containing them
FR2601366A1 (en) * 1986-07-10 1988-01-15 Andre Buzas BENZHYDRYLOXYETHYL-PIPERAZINE DERIVATIVES, METHODS OF OBTAINING THEM AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME
EP0254627A1 (en) * 1986-07-10 1988-01-27 Société anonyme: LES LABORATOIRES MERAM Derivatives of benzhydryloxyethylpiperazine, processes for their preparation and pharmaceutical compositions containing them
US4908365A (en) * 1986-07-10 1990-03-13 Andre Buzas Benzhydryloxyethylpiperazine derivatives, processes for their preparation and pharmaceutical compositions in which they are present

Also Published As

Publication number Publication date
FR2374318B1 (en) 1982-11-19

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