4-aryl-1-phenylalkyl-1,2,3,6-tetrahydropyridines having...

C - Chemistry – Metallurgy – 07 – D

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C07D 211/70 (2006.01) A61K 31/44 (2006.01) C07C 17/263 (2006.01) C07C 25/18 (2006.01) C07C 29/32 (2006.01) C07C 33/24 (2006.01) C07C 33/46 (2006.01) C07D 211/52 (2006.01) C07D 401/04 (2006.01)

Patent

CA 2225746

The present invention relates to the compounds of formula Image wherein Y is -CH- or -N-; R1 is hydrogen, a halogen or a CF3, (C3-C4)alkyl or (C1-C4)alkoxy group; R2 is hydrogen, a halogen, a hydroxyl or a CF3, (C3-C4)alkyl or (C1-C4)alkoxy group; R3 and R4 are each hydrogen or a (C1-C3)alkyl; and X is (a) a (C3- C6)alkyl, a (C3-C6)alkoxy, a (C3-C7)carboxyalkyl, a (C1-C4)- alkoxycarbonyl(C3-C6)alkyl, a (C3-C7)carboxyalkoxy or a (C1- C4)alkoxycarbonyl(C3-C6)alkoxy; (b) a radical selected from a (C3-C7)cycloalkyl, (C3-C7)cycloalkoxy, (C3-C7)cycloalkylmethyl, (C3-C7)cycloalkylamino and cyclohexenyl, it being possible for said radical to be substituted by a halogen, hydroxyl, (C1- C4)alkoxy, carboxyl, (C1-C4)alkoxycarbonyl, amino or mono- or di-(C1-C4)alkylamino; or (c) a group selected from a phenyl, phenoxy, phenylamino, N-(C1-C3)alkylphenylamino, phenylmethyl, phenylethyl, phenylcarbonyl, phenylthio, phenylsulfonyl, phenylsulfinyl and styryl, it being possible for said group to be monosubstituted or polysubstituted on the phenyl group by a halogen, CF3, (C1-C4)alkyl, (C1-C4)alkoxy, cyano, amino, mono- or di-(C1-C4)alkylamino, (C1-C4)acylamino, carboxyl, (C1-C4)- alkoxycarbonyl, aminocarbonyl, mono- or di-(C1-C4)-alkyl- aminocarbonyl, amino(C1-C4)alkyl, hydroxy(C1-C4)alkyl or halo- geno(C1-C4)alkyl, as well as the salts and solvates thereof and the quaternary ammonium salts thereof; to a process for their preparation and to pharmaceutical compositions containing them. These compounds have a neurotrophic and neuroprotective activity.

La présente invention concerne les composés de formule (I), dans laquelle Y représente -CH- ou -N-; R1 représente l'hydrogène, un halogène, un groupe CF3, (C3-C4)alkyle ou (C1-C4)alcoxyle; R2 représente l'hydrogène, un halogène, un hydroxyle, un groupe CF3, (C3-C4)alkyle ou (C1-C4)alcoxyle; R3 et R4 représentent chacun l'hydrogène ou un (C1-C3)alkyle; X représente (a) un (C3-C6)alkyle; un (C3-C6)alcoxyle; un (C3-C7)carboxyalkyle; un (C1-C4)alcoxycarbonyl(C3-C6)alkyle; un (C3-C7)carboxyalcoxyle; ou un (C1-C4)alcoxycarbonyl(C3-C6)alcoxyle; (b) un radical choisi parmi un (C3-C7)cycloalkyle, (C3-C7)cycloalkyloxy, (C3-C7)cycloalkylméthyle, (C3-C7)cycloalkylamino et cyclohexényle, ledit radical pouvant être substitué par un halogène, hydroxy, (C1-C4)alcoxy, carboxy, (C1-C4)alcoxycarbonyle, amino, mono- ou di-(C1-C4)alkylamino; ou (c) un groupe choisi parmi un phényle, phénoxy, phénylamino, N-(C1-C3)alkyl-phénylamino, phénylméthyle, phényléthyle, phénylcarbonyle, phénylthio, phénylsulfonyle, phénylsulfinyle ou styryle, ledit groupe pouvant être mono- ou polysubstitué sur le groupe phényle par un halogène, CF3, (C1-C4)alkyle, (C1-C4)alcoxy, cyano, amino, mono- ou di-(C1-C4)alkylamino, (C1-C4)acylamino, carboxy, (C1-C4)alcoxycarbonyle, aminocarbonyle, mono- ou di-(C1-C4)alkylaminocarbonyle, amino(C1-C4)alkyle, hydroxy(C1-C4)alkyle ou halogéno(C1-C4)alkyle; ainsi que leurs sels et solvates et leurs sels d'ammonium quaternaires, un procédé pour leur préparation et des compositions pharmaceutiques les contenant. Ces composés ont une activité neurotrophique et neuroprotectrice.

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