Antidepressant 2-(4,5-dihydro-1h-imidazolyl)-dihydro-1h-...

Details Antidepressant 2-(4,5-dihydro-1h-imidazolyl)-dihydro-1h-... Antidepressant 2-(4,5-dihydro-1h-imidazolyl)-dihydro-1h-...

C - Chemistry, Metallurgy

07

D

167/226, 167/237

C07D 401/04 (2006.01) A61K 31/415 (2006.01) C07D 403/02 (2006.01) C07D 403/04 (2006.01) C07D 403/06 (2006.01)

Patent

CA 1291759

ABSTRACT OF THE DISCLOSURE 2-(4,5-Dihydro-1H-imidazol-2-yl)-2,3-dihydro-1H- indoles, 2-(4,5-dihydro-1H-imidazol-2-yl)-1,2,3,4-tetra- hydroquinolines and 2-(4,5-dihydro-1H-imidazol-2-yl)-1H- indoles of the formulae below, useful as antidepressant agents, are prepared by reacting a respective lower-alkyl 2,3-dihydro- 1H-indole-2-carboxylate, 1,2,3,g-tetrahydroquinoline-2- carboxylate or 1H-indole-2-carboxylate derivative with ethylenediamine or an N-lower-alkylethylenediamine in the presence of a Lewis-type acid: (I) Image (II) (III) (where, in the compounds of formula I: R' is hydrogen, halogen or benzyl; R" is hydrogen or lower-alkyl; R1 is hydrogen, lower-alkyl, lower-alkenyl, lower-alkoxy- lower-alkyl, phenyl or phenyl-lower-alkyl; R2 is hydrogen, lower-alkyl, lower-alkenyl, lower-alkoxy- lower-alkyl, lower-alkylmercapto-lower-alkyl or di-lower- alkylamino-lower-alkyl; R3 is hydrogen, lower-alkyl or methylene; and n is 0 or the integer 1; in the compounds of formula II: R" is hydrogen or lower-alkyl; R' 1 is hydrogen or lower-alkyl; R' 3 is hydrogen or lower-alkyl; and R4 is hydrogen or phenyl; and in the compounds of formula III. R' is hydrogen, halogen or benzyl; R" is hydrogen or lower -alkyl; R" 1 is lower-alkyl; R" 3 is hydrogen or lower-alkoxy; and n is 0 or the integer 1).

498165

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