Substituted imidazole derivatives and their preparation and use

Details Substituted imidazole derivatives and their preparation and use Substituted imidazole derivatives and their preparation and use

C - Chemistry, Metallurgy

07

D

260/314

C07D 233/54 (2006.01)

Patent

CA 1176259

ABSTRACT OF THE DISCLOSURE Novel substituted imidazole derivatives and the preparation thereof are provided herein. These imidazole derivatives have the general formula: Image or Image (I) wherein each of R1, R2 and R3, which can be the same or different, is hydrogen, chloro, bromo, fluoro, methyl, ethyl, methoxy, amino, hydroxy or nitro; R4 is hydrogen,or an alkyl radical of 1 to 7 carbon atoms; R5 is hydrogen, or a straight or branched alkyl group of 1 to 5 carbon atoms, or a phenyl group; and R6 is hydrogen, or an alkyl radical of 1 to 7 carbon atoms, or an unsubstituted benzyl, or a benzyl substituted by up to 3 sub- stituents selected from the same as R1, R2 and R3 recited above; X is -CH2, -CHOH-, or -CH=CH-; and n is an integer from 0 to 4, provided that R5 and R6 are simultaneously hydrogen only when n is 4 and X is -CH=CH-; when n is 0, X is -CH2- and R1, R2, R3 and R6 are all hydrogen and R is hydrogen or ethyl, then R5 is other than methyl or phenyl; when n is 0, X is CHOH, and R1, R2, R3 and R4 are all hydrogen, both of R5 and R6 are other than methyl; and when n is 2, X is CHOH, R1, R2, R3 and R4 are all hydrogen, and R6 is methyl, then R3 is other than 2-amino. It will be appreciated that when R6 is hydrogen the two aforesaid formulae are effectively the same. When R6 is substituted benzyl it preferably carries up to 3 substituents selected from the same readicals as R1, R2 and R3. The non-toxic pharmaceutically acceptable acid addition salts of these compounds are also provided herein. Such derivatives exhibit valuable pharmacological activity and are useful in the greatment of mammals, especially as antithrombotic agents. Furthermore, some of the compounds have proved to possess antihypertensive or .beta. -blocking activity. Antimicro- bial and antifungal properties have also been found. Abstract continued.

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