N-(phenoxyalkyl)imidazoles as selective inhibitors of the...

C - Chemistry – Metallurgy – 07 – D

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C07D 233/56 (2006.01) C07D 403/12 (2006.01) C07D 521/00 (2006.01)

Patent

CA 1108137

ABSTRACT N-(Phenoxyalkyl)imidazole of the formula: Image wherein R is NO2, CN, SO2NH2, C1-C4 alkanoyl, CO2R , CH2CO2R , OCH2CO2R , CONHR3, CH2CONHR3, OCH2CONHR3, CON(R4)2, CH2CON(R4)2, OCH2CON(R4)2, NHR5, CH2NHR5, tetrazolyl, CH2-tetrazolyl and OCH2-tetrazolyl; R1 is H, C1-C4 alkyl, C1-C4 alkoxy or halogen; R2 is H or C1-C4 alkyl; R3 is H, C1-C4 alkyl, C1-C4 alkanoyl, C1-C4 alkylsulphonyl, CN, benzoyl or benzenesulphonyl, the phenyl ring in said benzoyl or benzenesulphonyl groups being optionally substituted with one or more C1-C4 alkyl, C1-C4 alkoxy or CF3 groups or halogen atoms; each R4 is C1-C4 alkyl or two groups R4 together with the nitrogen atom to which they are attachet form a pyrrolidino, piperidino or morpholino group; R5 is H, C1-C4 alkanoyl, C1-C4 alkoxycarbonyl, carbamoyl, C1-C4 alkylcarbamoyl; and n is 2 or 3; and the pharmaceutically acceptable acid addition salts there- of and bioprecursors therefor, are able to selectively inhibit the action of the thromboxane synthetase enzyme without significantly inhibiting the action of the prostacycline synthetase or cyclooxygenase enzymes and are thus useful in the trestment of ischaemic heart disease, stroke, transient ischaemic attack, thrombosis, migraine and the vascular complications of diabetes.

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