RU99115082A - DIPHENYLALKYL-TETRAHYDROPYRIDINES, METHOD FOR THEIR RECEPTION AND PHARMACEUTICAL COMPOSITIONS THEM CONTAINING - Google Patents

Claims (10)

1. The compound of formula I

in which Y represents-CH- or -N-;
R ₁ is halogen, a CF ₃ , (C ₁ -C ₄ ) alkyl or a (C ₁ -C ₄ ) alkoxy group;
R ₂ and R ₃ are each hydrogen or (C ₁ -C ₃ ) alkyl;
n is 0 or 1;
Ph ₁ and Ph ₂ denote, each independently, an unsubstituted, monosubstituted or polysubstituted phenyl group,
as well as its salts and solvates and its quaternary ammonium salts. 2. The compound according to claim 1, wherein Y is CH, and R ₁ is CF ₃ , or Y is N, and R ₁ is Cl. 3. The compound according to claim 1 or 2, in which R ₂ and R ₃ are both hydrogen atoms. 4. The compound according to claim 1 of formula I '

in which R ′ ₁ is CF ₃ , and Y ′ is CH, or R ′ ₁ is C1, and Y ′ is N, and n, Ph ₁ and Ph ₂ are as defined for compounds I in claim 1, and its salts and solvates and its quaternary ammonium salts. 5. The compound according to any one of paragraphs. 1-4, in which Ph ₁ and Ph ₂ denote each phenyl group, a phenyl group substituted in position 2, 3 or 4 by a fluorine atom, chlorine or methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, second butyl, tert-butyl, trifluoromethyl, cyano, methoxy, methylthio, methylsulfonyl, ethoxy, ethylthio, ethylsulfonyl, (C ₁ -C ₃ ) alkoxycarbonyl or di (C ₁ -C ₃ ) alkylaminocarbonyl group; phenyl group, disubstituted in positions 2, 4; 3, 4; 3, 5 or 2, 6 atoms of chlorine, fluorine or methyl, ethyl, trifluoromethyl, cyano or methoxy; or a phenyl group, trisubstituted in positions 3, 4, 5; 2, 4, 5 or 2, 4, 6 by a chlorine, fluorine or methyl atom, ethyl, trifluoromethyl, cyano or methoxy. 6. The compound according to claim 5, in which Ph ₁ and Ph _{2 are the} same. 7. The compound according to claim 1, selected among
1- (2,2-diphenylethyl) -4- (3-trifluoromethylphenyl) -1,2,3,6-tetrahydropyridine,
1- [2,2- (4,4'-dichlorodiphenyl) ethyl] -4- (3-trifluoromethylphenyl) -1,2,3,6-tetrahydropyridine,
1- [2,2- (3,3'-bistrifluoromethyldiphenyl) ethyl] -4- (3-trifluoromethylphenyl) -1,2,3,6-tetrahydropyridine,
1- [2,2- (4,4'-dimethoxydiphenyl) ethyl] -4- (3-trifluoromethylphenyl) -1,2,3,6-tetrahydropyridine,
1- [2- (4-fluorophenyl) -2-phenylethyl] -4- (3-trifluoromethylphenyl) -1,2,3,6-tetrahydropyridine,
1- (3,3-diphenyl-propyl) -4- (3-triforpermethylphenyl) -1,2,3,6-tetrahydropyridine,
1- [2,2- (4,4'-dichlorodiphenyl) ethyl] -4- (6-chloropyrid-2-yl) -1,2,3,6-tetrahydropyridine and their salts, solvates or quaternary ammonium salts. 8. The method of producing compounds of the formula I according to claim 1, their salts or solvates and their quaternary ammonium salts, characterized in that:
(a) aryl-1,2,3,6-tetrahydropyridine of the formula II,

in which Y and R _1, such as those defined for compounds I in claim 1, are reacted with an acid of formula III,

in which p, R ₂ , R ₃ , Ph ₁ and Ph ₂ are as defined for compounds (I) in § 1, or one of its functional derivatives;
(b) the intermediate carbonyl compound of formula IV is reduced.

and (c) isolate the compound of formula (1) thus obtained and, in some cases, convert it to one of its salts or one of its solvates, or to one of its quaternary ammonium salts.  9. Pharmaceutical composition containing as an active start a compound according to any one of paragraphs. 1-7.  10. Pharmaceutical composition containing as active principles the compound according to any one of paragraphs. 1-7 and the compound indicated for the symptomatic treatment of senile dementia such as Alzheimer's disease (DAT), or their pharmaceutically acceptable salts.