WO1981003493A1 - Derives de 4- (1-piperazinyle)-furo (3, 2-c) pyridine, leurs procedes de preparation et compositions pharmaceutiques les contenant - Google Patents

Derives de 4- (1-piperazinyle)-furo (3, 2-c) pyridine, leurs procedes de preparation et compositions pharmaceutiques les contenant Download PDF

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Publication number
WO1981003493A1
WO1981003493A1 PCT/EP1981/000060 EP8100060W WO8103493A1 WO 1981003493 A1 WO1981003493 A1 WO 1981003493A1 EP 8100060 W EP8100060 W EP 8100060W WO 8103493 A1 WO8103493 A1 WO 8103493A1
Authority
WO
WIPO (PCT)
Prior art keywords
furo
piperazinyl
formula
preparation
processes
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.)
Ceased
Application number
PCT/EP1981/000060
Other languages
German (de)
English (en)
French (fr)
Inventor
M Combourieu
N Busch
Y Bernet
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.)
Centre Europeen de Recherches Mauvernay CERM
Original Assignee
Centre Europeen de Recherches Mauvernay CERM
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 Centre Europeen de Recherches Mauvernay CERM filed Critical Centre Europeen de Recherches Mauvernay CERM
Priority to AU72273/81A priority Critical patent/AU7227381A/en
Priority to FI813293A priority patent/FI813293L/fi
Priority to DK498681A priority patent/DK498681A/da
Publication of WO1981003493A1 publication Critical patent/WO1981003493A1/de
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems

Definitions

  • the present invention relates to new 4- (1-piperazinyl) -furo [3,2-c] pyridine derivatives, to processes for their preparation and to pharmaceutical compositions containing same in the form of the free base or a pharmaceutically acceptable salt.
  • R represents hydrogen or a lower alkyl (1-6 C) group.
  • the compounds of formula I can be obtained by. condensation of piperazines with a 4-halo-furo [3,2-c] pyridine derivative (formula II).
  • the latter starting compound can, for example, be prepared starting from a 4-hydroxy-2-oxo-1,2-dihydro-pyridine derivative according to the following reaction steps:
  • the condensation of a compound II with piperazine is carried out using piperazine in excess, preferably by refluxing the mixture in a suitable solvent, such as ethylene glycol monomethyl ether.
  • a salt of the compounds of formula I is obtained by reaction of the free base with an organic or inorganic acid, such as HCl, HBr, H 3 PO 4 , acetic acid, maleic acid, fumaric acid, tartaric acid, etc.
  • organic or inorganic acid such as HCl, HBr, H 3 PO 4 , acetic acid, maleic acid, fumaric acid, tartaric acid, etc.
  • the compounds of the invention and the pharmaceutically acceptable salts thereof have potent psychopharmacological activities and particularly an anti-depressive activity.
  • the compounds of formula I, associated with the usual pharmaceutical carriers, can be administered enterally or parenterally, preferably in a daily dosage of from 0.1-50 mg / kg bodyweight, and more particularly from 1-10 mg / kg bodyweight.
  • the preferred daily dosage ranks for use in human is from about 50-100 mg.
  • psycopharmacological activity and especially the anti-depressive activity of compounds of formula I are illustrated by the following test results.
  • a - Antaqonism to reserpine ptosis in mice The product under study (or the vehicle alone - gum arabic and water 1/1 - for the control group) is administered by oesophageal Intubation to male mice of OF1 IFFA CREDO stock of mean weight 22 ⁇ 1 g, and then, 60 min. after treatment, all animals receive intraperitoneally 1 mg / kg -1 of reserpine base.
  • the compound I, in which R is CH 3 , and the reference compound quipazine are administered in a dose of 40 mg / kg and the compound I, in which R is hydrogen, in a dose of 10 mg / kg.
  • the compound obtained is converted into the maleattee salt; mp 295 ° C. (This salt further contained 1/4 H 2 O per mol.).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
PCT/EP1981/000060 1980-06-05 1981-05-29 Derives de 4- (1-piperazinyle)-furo (3, 2-c) pyridine, leurs procedes de preparation et compositions pharmaceutiques les contenant Ceased WO1981003493A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
AU72273/81A AU7227381A (en) 1980-06-05 1981-05-29 4-(1-piperazinyl)-furo(3,2-c) pyridine derivatives, processes for their preparation and pharmaceutical compositions containing same
FI813293A FI813293L (fi) 1980-06-05 1981-05-29 4-(1-piperazinyl)-furo/3,2-c/pyridinderivat foerfarande foer framstaellning av dem och dessa innehaollande farmaceutiska kompositioner
DK498681A DK498681A (da) 1980-06-05 1981-11-11 4-(1-piperazinyl)-furo (3,2-c) pyridinderivater fremgangsmaader til deres fremstilling og farmaceutiske midler indeholdende disse

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR8012553A FR2483923A1 (fr) 1980-06-05 1980-06-05 6-methyl-4-(1-piperazinyl)-furo (3,2-c) pyridine, son procede d'obtention et son application en therapeutique
FR8012553 1980-06-05

Publications (1)

Publication Number Publication Date
WO1981003493A1 true WO1981003493A1 (fr) 1981-12-10

Family

ID=9242757

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1981/000060 Ceased WO1981003493A1 (fr) 1980-06-05 1981-05-29 Derives de 4- (1-piperazinyle)-furo (3, 2-c) pyridine, leurs procedes de preparation et compositions pharmaceutiques les contenant

Country Status (9)

Country Link
EP (1) EP0041891A1 (cg-RX-API-DMAC7.html)
JP (1) JPS57500876A (cg-RX-API-DMAC7.html)
DK (1) DK498681A (cg-RX-API-DMAC7.html)
ES (1) ES8203380A1 (cg-RX-API-DMAC7.html)
FR (1) FR2483923A1 (cg-RX-API-DMAC7.html)
GR (1) GR75664B (cg-RX-API-DMAC7.html)
PT (1) PT73123B (cg-RX-API-DMAC7.html)
WO (1) WO1981003493A1 (cg-RX-API-DMAC7.html)
ZA (1) ZA813678B (cg-RX-API-DMAC7.html)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4831031A (en) * 1988-01-22 1989-05-16 Pfizer Inc. Aryl piperazinyl-(C2 or C4) alkylene heterocyclic compounds having neuroleptic activity

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4559749B2 (ja) * 2004-02-16 2010-10-13 あすか製薬株式会社 ピペラジニルピリジン誘導体
JP4596792B2 (ja) * 2004-02-24 2010-12-15 あすか製薬株式会社 ５−ｈｔ１ａ作動作用と５−ｈｔ３拮抗作用を併有する薬剤

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Bulletin de la Societe Chimique de France, no. 5, May 1971 (Paris, FR) E. Bisagni: "Furannes et pyrroles disubstitués en 2,3 X. Synthèse de furo [3,2-c] pyridines à partir du formyl-2 carbéthoxy-3 furanne", pages 1727-30 *
Chimie Therapeutique, volume VIII, no. 5, issued September - October 1973, (Chantenay-Malabry, FR) E. Bisagni: "Aza-indoles-II. Nouveaux dérivés aza-5 indoliques et leurs propriétés pharmacologiques", pages 559-566 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4831031A (en) * 1988-01-22 1989-05-16 Pfizer Inc. Aryl piperazinyl-(C2 or C4) alkylene heterocyclic compounds having neuroleptic activity

Also Published As

Publication number Publication date
PT73123B (en) 1982-07-15
ES502824A0 (es) 1982-04-01
ES8203380A1 (es) 1982-04-01
GR75664B (cg-RX-API-DMAC7.html) 1984-08-02
EP0041891A1 (fr) 1981-12-16
JPS57500876A (cg-RX-API-DMAC7.html) 1982-05-20
ZA813678B (en) 1982-06-30
DK498681A (da) 1981-12-10
FR2483923A1 (fr) 1981-12-11
FR2483923B1 (cg-RX-API-DMAC7.html) 1983-05-27
PT73123A (en) 1981-07-01

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