Benzo[b]thiophenes, benzo[b]furans, thiochromans and...

C - Chemistry – Metallurgy – 07 – D

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C07D 405/00 (2006.01)

Patent

CA 1213591

A B S T R A C T Compounds of the formula Image I wherein n is 0 or an integer from 1 to 4; p is 0 or 1; q is 0, 1 or 2, R and R1 are independently hydrogen or halogen atoms, or lower alkyl, halolower alkyl, nitro or NR2R3 groups, wherein R2 and R3 are independently hydrogen atoms or lower alkyl groups; or R and R1 together in adjacent positions complete a fused saturated or unsaturated carbocyclic ring that may contain 5 to 7 carbon atoms; X is an oxygen or sulfur atom or a sulphinyl or sulphonyl group; Y is an imidazolyl or 1,2,4-triazolyl group, either of which may be substituted by a lower alkyl or aryl group, wherein said aryl group is a phenyl, halophenyl or lower alkyl phenyl group; Z is an alkyl, alkenyl, alkynyl, cycloalkyl or heterocyclic aromatic group, which may have at least one substituent selec- - 2 - ted from halogen atoms and lower alkyl, lower alkoxy, lower alkylidenedioxy, phenyl and N-(N'-lower alkanoylpiperazinyl) groups, provided that, when n is 0, Z is not 1-alkynyl; and, when n is 1 to 4, Z can also be an alkoxy, alkylthio, aryl, ary- loxy or arylthio group, or an aryl, aryloxy or arylthio group having substituents selected from halogen atoms and lower alkyl, lower alkoxy, lower alkylidenedioxy and N-(N'-lower alkanoyl- piperazinyl) groups; where the term "lower" indicates groups having 1 to 6 carbon atoms; and the broken line indicates a single or double bond, with the proviso that it is a double bond only when p is 0 and X is a sulfur atom; and the acid addition salts thereof; have antimicrobial, in particular antifungal, antibacterial and antiprotozoal activity. Compositions, especially pharma- ceutical compositions, containing them and processes for their preparation are also disclosed.

400570

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