GB935384A — Tetracycline derivatives and preparation thereof

USPTO Abstract

Relates to aryl azo tetracycline compounds of the formula <FORM:0935384/IV(a)/1> or <FORM:0935384/IV(a)/2> and the N4-benzyl betaines thereof, wherein A is hydrogen or methyl, B and Q are each hydrogen or hydroxyl but when Q is hydroxyl A is methyl, D is hydrogen or dimethylamino, X is halogen and Ar is the organic residue of an aromatic diazonium salt having 6 to 12 carbon atoms, and also relates to the corresponding 7- or 9-amino-tetracycline compounds which may be obtained by reduction of the corresponding aryl diazo compound or nitro compound. These amino compounds may be converted to a diazonium salt and the diazonium group replaced by a desired substituent such as a cyano, fluoro, chloro, bromo, iodo, amino, cyanato, thiocyanato, nitro, arsenoxy mercapto, azido or alkylmercapto group. The Specification describes the preparation of many tetracycline derivatives of which the following are typical:- 7-phenylazotetracycline, 7-amino-tetracycline, 7-amino-6-deoxy-tetracycline, 7-chloro-6-deoxy-6-demethyl-tetracycline, 7-iodo-6-deoxy-tetracycline, 9-fluoro-6-deoxy-tetracycline, 7-cyano-6-deoxy-4-desdimethylaminotetracyline and 9-amino-tetracycline-7-fluoro- 6-deoxy-5-hydroxytetracycline. The tetracycline derivatives may be used in pharmaceutical compositions. Specification 885,760 is referred to.