GB1222486A - Alkyl-haloalkyl-2-nitroimidazoles - Google Patents

Abstract

1,222,486. 2-Nitroimidazoles. GRUPPO LEPETIT S.p.A. 20 Aug., 1969 [27 Aug., 1968], No. 41441/69. Heading C2C. Novel 2-nitroimidazoles of the general formula wherein R 1 and R 2 are each an alkyl or haloalkyl group having from 1 to 3 carbon atoms, one of them being an alkyl group and the other being a haloalkyl group, and salts thereof with organic and inorganic acids and alkyl halides are prepared by diazotization of a 2 aminoimidazole of the general formula with an equimolecular amount or slight excess of an alkali metal nitrite in concentrated fluoboric acid and reaction of the diazo compound so obtained with an excess (over the equimolecular amount) of an alkali metal nitrite in water in the presence of copper powder, followed optionally by salt formation. 2 - Amino - 5 - (2 - chloroethyl) - 1 - methylimidazole hydrochloride is prepared by treatment of 2-methylamine-butyrolactone hydrochloride with sodium amalgam in aqueous ethanol, followed by cyanamide, and reaction of the resulting 2-amino-5-(2-hydrozyethyl)-1- methylimidazole hydrochloride with thionyl chloride. 2 - Amino - 1 - (2 - chloroethyl) - 5 - methylimidazole hydrochloride is prepared by reaction of 2-bromo-propionaldehyde diethyl acetal with ethanolamine, treatment of the resulting 2 - (2 - hydroxyethylamino) - propionaldehyde diethyl acetal with cyanamide in the presence of hydrochloric acid and reaction of the resulting 2 - amino - 1 - (2 - hydroxyethyl) - 5 - methylimidazole hydrochloride (the picrate is also isolated) with thionyl chloride. 2-Amino-1-(2- chloroethyl) - 5 - ethylimidazole hydrochloride is prepared analogously. Pharmaceutical compositions having antimicrobial activity comprise, as active ingredient, one or more 2-nitroimidazoles of the first general formula above or salts thereof with organic or inorganic acids or alkyl halides, in admixture with a therapeutically acceptable diluent or carrier.