GB1273836A - Thiazole derivatives - Google Patents

Abstract

1,273,836. Nitrothiazole derivatives. CIBAGEIGY A.G. 5 Dec., 1969 [13 Dec., 1968 (2); 3 Nov., 1969], No. 59614/69. Heading C2C. Novel compounds of Formula I in which R is a thiomorpholino radical which is substituted at at least one carbon atom, e.g. with alkyl or alkoxyalkyl groups, and/or is oxidized at the sulphur atom, are prepared by (a) reacting an amine of formula HR with a compound of Formula II in which X is an alkoxy or dialkylamino group, or (b) reacting 2-amino-5-nitrothiazole with a compound of formula R-CO-Cl in dimethylformamide, or (c) reacting 2-amino-5-nitrothiazole with an acetal of a formamide of formula HCOR, or (d) oxidizing 4-[N-(5-nitro-2-thiazolyl)-formidoyl]-thiomorpholine. Resulting unoxidized compounds can be converted into the S-monoxides or S,S-dioxides, and resulting S- monoxides into S,S-dioxides. Resulting free bases can be converted into acid addition salts. 4 - [N - (5 - nitro - 2 - thiazolyl) - formidoyl]- thiomorpholine is prepared by reacting 2-amino- 5-nitro-thiazole with 4-formylthiomorpholinedimethyl acetal. 4-Formylthiomorpholine-dimethyl acetal is prepared by reacting thiomorpholine with dimethylformamide-dimethyl acetal. 2,6-Cis-dimethyl-4- formyl-thiomorpholine-diethyl acetal is similarly prepared. Cis - 2,6 - dimethyl - thiomorpholine - 4 - carboxylic acid chloride is prepared by reacting phosgene with cis-2,6-dimethylthiomorpholine. Pharmaceutical compositions having amoebicidal, schistosomacidal and antibacterial activity, for enteral or parenteral administration, comprise a compound of Formula I, or a pharmaceutically acceptable acid addition salt thereof, together with a carrier.