3-(1-imidazolylalkyl) indoles

Details 3-(1-imidazolylalkyl) indoles 3-(1-imidazolylalkyl) indoles

C - Chemistry, Metallurgy

07

D

260/262, 260/280

C07D 403/00 (2006.01) C07D 209/14 (2006.01) C07D 521/00 (2006.01)

Patent

CA 1120479

ABSTRACT 3-1-(Imidazolylalkyl)indoles of the formula: Image wherein R1 is hydrogen or C1 -C4 lower alkyl, R2 is hydrogen, C1 -C6 alkyl, C3 -C6 cycloalkyl or a phenyl group optionally substituted with C1 -C4 lower alkyl, C1 -C4 lower alkoxy, fluorine, chlorine or bromine; R3 is hydrogen, C1 - C4 lower alkyl, C1 -C4 alkoxy, hydroxy, trifluoromethyl, di (C1 -C4 lower alkyl)amino, fluorine, chiorine or bromine, x is a group: -(CH2) n-, -CH2- Image -CH2- Image or -CH2- Image wherein n is an integer of from 1 to 3; Y is CO2R4, CONHR5, CON(C1 -C4 lower'alkyl)2, CN, 5- tetrarolyl, CONHCOR6, CONHCN or CONHSO2R6, or, when x is -(CH2)n- and n is 2 or 3, Y is NH2, NHCOR6, NHCO2(C1 -C4 lower alkyl), NHCONHR5, NHSO2R6, OH or a group: - 2 - Image or Image R4 is hydrogen or C1 - C4 lower alkyl; R5 is hydrogen, C1 - C4 lower alkyl, C3 -C6 cycloalkyl, phenyl, thiazolyl, pyridyl, pyrzinyl, pyrimidinyl, or pyridazinyl, R6 is C1 -C4 lower alkyl, C3 -C6 cycloalkyl, pyridyl or a phenyl group optionally substituted with C1 -C4 lower alkyl, C1 -C4 lower alkoxy, fluorine, chlorine or bromine, and the pharmaceutically acceptable acid addition salts thereof and bioprecursore therefor are able to selectively inhibit the action of the thromboxane syn- thetase enzyme without significantly inhibiting the action of the prostacycline synthetase or cyclooxygenase enzymes and are this useful in the treatment of ischaemic heart disease, stroke, transient ischaemic attack, thrombosis, migraine and the vasoular complications of diabetes.

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