NOVEL IMIDAZOLE COMPOUNDS

摘要

1373346 Imidazoles BEECHAM GROUP Ltd 6 Dec 1971 [9 Dec 1970] 58385/70 Heading C2C Novel imidazoles of the general formula and tautomers thereof, wherein R 1 is a carbocyclic or heterocyclic aromatic group optionally substituted by one or two halogen atoms, optionally substituted hydroxyl, amino, thiol, sulphonic or carboxylic groups, or cyano, nitro, acyl, alkyl, aryl or haloalkyl groups; R 2 is an amino or hydroxyl group or an alkoxy, aryloxy or aralkoxy group optionally substituted by a halogen atom or optionally substituted hydroxyl or amino groups; R 4 is a hydrogen atom or a methyl group; R 5 is a methyl or #-haloethyl group and R 6 is a hydrogen atom or a hydrocarbon group optionally substituted by a halogen atom or an optionally substituted hydroxyl or tertiary amino group; and acid addition salts, solvates and solvated acid addition salts thereof are prepared by reaction of the corresponding diazonium salt of the general formula wherein R1 4 is a negative charge or a methyl group (an external anion being present) with an amine of the general formula HNR 5 R 6 ; followed optionally by modification or replacement of substituents R 1 and R 2 to form other substituents R 1 and R 2 by means known per se and/or by salification and/or solvation of the product. Diazonium salts of the second general formula above are prepared by diazotization of the corresponding amine with nitrous acid. 5-Amino-4-carbethoxy-2-phenylimidazole (hydrochloride) is prepared by reaction of α-iminobenzylbenzyl thioetherhydrocyloride with ethyl aminocyanoacetate. Pharmaceutical compositions having bactericidal, antifungal and anti-tumour activity comprise, as active ingredient, an imidazole of the first general formula above or an acid addition salt, solvate or solvated acid addition salt thereof, together with at least one pharmaceutically acceptable carrier, diluent or excipient.