5-nitroimidazole derivatives

摘要

The invention comprises as novel compounds the C1- 8 hydrocarbon esters, the salts, the acid chlorides and the acid bromides of 1 - (C1- 5 alkyl) - 5 - nitroimidazole - 2 - carboxyli acids, and the preparation thereof (1) by reacting a 1 - (C1- 5 alkyl) - 2 - hydroxymethyl-5 -nitroimidazole with an oxidizing agent in an alkaline medium to produce an alkali metal salt of 1 - (C1- 5 alkyl) - 5 - nitroimidazole - 2 -carboxylic acid, (2) by reacting a salt of 1-(C1- 5 alkyl) - 5 - nitroimidazole - 2 - carboxylic acid with a chlorinating or brominating agent to produce the corresponding acid chloride or bromide, or with an esterifying agent in a solvent medium to produce a C1- 8 hydrocarbon ester of the acid, (3) by reacting a 1-(C1- 5 alkyl)-5-nitroimidazole-2-carboxylic acid ester with a chlorinating or brominating agent to produce the corresponding acid chloride or acid bromide, or (4) by reacting a 1-(C1- 5 alkyl)-5-nitroimidazole -2-carbonyl chloride or bromide with an alcohol in the presence of an acid binding agent to produce the corresponding C1- 8 hydrocarbonyl ester. The salts of the invention may also be prepared from the C1- 8 hydrocarbonyl esters. The 1 - (C1- 5 alkyl) - 2 - hydroxymethyl - 5-nitroimidazoles are prepared by nitrating 2-hydroxymethyl-imidazole, if desired after first protecting the hydroxy group by esterification or etherification, the protective group being removed after the nitration reaction, and alkylating the 2-hydroxymethyl-5-nitroimidazole thus prepared. 2-Acetoxymethyl-imidazole is prepared by reacting 2 hydroxymethyl-imidazole with acetic anhydride and liberating the base from the 2-acetoxy-methyl-imidazole acetic acid salt formed. Imidazole-2-carboxaldehyde is obtained as a by-product when 2-acetoxymethyl-imidazole is reacted with nitric acid. Ethyl 1 - methyl - 5 - nitroimidazole - 2-carboxylate has anti-histomonal activity and may be formulated for veterinary use as aqueous solutions or be admixed with feedstuff.