NEW ANTIMICROBIALLY ACTIVE COMPOUNDS

摘要

1320712 Nitroimidazole derivatives SCHERING AG 8 July 1970 [10 July 1969] 33178/70 Heading C2C Novel compounds of Formula I in which X represents a hydrocarbon group containing up to 5 carbon atoms, a 2-hydroxyethyl group, a 2-benzoyloxy-ethyl group or an acyloxyethyl group in which the acyl part contains up to 5 carbon atoms, Y and Z each represents a hydrogen atom or Y and Z together represent -O-CH 2 -, -CH 2 -O-, -SO-CH 2 -, -SO 2 -CH 2 -, -CH 2 -SO, -CH 2 -SO 2 -, -CH 2 -, -O-, -S-, -SO-, -SO 2 -, -S-CH 2 -, -CH 2 -S-, -CH 2 -CH 2 -, or -CHA-, A representing a -CH 3 , -C 2 H 5 or -C 6 H 5 group, R 1 and R 2 each represents a hydrogen atom, an alkyl group containing up to 5 carbon atoms, a halogen atom, a hydroxyl group, an acyloxy group containing up to 5 carbon atoms or an alkoxy group containing up to 5 carbon atoms, and R 3 represents a hydrogen atom, a hydrocarbon group containing up to 5 carbon atoms, a halogen atom, a hydroxyl group, an etherified hydroxyl group which, if it is an hydroxyl group etherified by an aliphatic unsubstituted hydrocarbon group, does not contain more than 5 carbon atoms, a hydroxyl group esterified by a carboxylic or sulphonic acid containing up to 10 carbon atoms, a free or N-substituted amino group or a free or N-substituted aminoalkoxy group, and their physiologically tolerable acid addition and quaternary ammonium salts, are prepared by (a) reacting an aldehyde of Formula II or a functional derivative thereof, in an acidic medium, with a compound of Formula III or an acid addition salt thereof, or (b) nitrating a compound of Formula IV or (c) oxidizing a compound of Formula I in which Y and Z together represent a thio group or a group containing a thio group, to form the corresponding sulphoxides and sulphones, and, if desired, converting a resulting compound into a physiologically tolerable acid addition or quaternary ammonium salt, or converting an acid addition salt into the free compound. The compounds I may be also converted into different compounds I. Starting materials and intermediates. The preparation of certain of the compounds of Formulae II (and their derivatives), III and IV is disclosed and also the preparation of: 5- nitro - 1 - ethyl - 2 - hydroxymethyl - imidazole, 5 - nitro - 2 - hydroxymethyl - 1 - (21- benzoyloxyethyl) - imidazole, 5 - (21 - hydroxyethoxy) - 1 - indanone, 6 - (21 - hydroxyethoxy) - 1 - tetralone, 5- (21 - p - toluenesulphonyloxy - ethoxy) - 1 - indanone, 6 - (21- p - toluenesulphonyloxy - ethoxy)- 1 - tetralone, and 41 - (211- p - toluenesulphonyloxy-ethoxy)-acetophenone. Pharmaceutical compositions having antibacterial, antiprotozoal and antifungal activity, for oral, parenteral or topical administration, comprise one of the above novel compounds together with a suitable carrier.