abstract |
New ureido-and semicarbazide-derivs. of thiazole are of formula (I), and their salts with mineral and sulphonic acids or (when R5 is OH) their alkali(ne earth) salts. In (I), R1 is H or a mononuclear carbo- or heterocyclic residue with 3-10 ring atoms and >=1 S or N atom, opt. substd. by halogen, 1-3C haloalkyl, 1-6C alkyl and-or 1-3C alkoxy; R2 is H; or R1+R2 is -CH=CH-CH=CH-; Q is NH or NH-NH opt. substd. by 1-2C alkyl; R3 and R4 are H, aryl, or 1-3C alkyl opt. substd. by halogen, amino, 1-3C alkylamino, di-(1-3C alkyl) amino and/or is not >11C heterocyclic residue (e.g. N-benzylpiperazino); Y is -CHR3- or a single bond; and R5 is OH, 1-6C alkoxy, NH2, mono- or di(1-3C alkyl)amino, or a 5- or 6-membered heterocyclic amino residue with 1 or 2 N-atoms, the second of which is opt. substd. by alkyl, aryl or arlkyl. Their toxicity is considerably lower than that of amino-phenazone, and they are free from central, vegetative and cardiovascular side-effects. Specific (I) include methyl 3-(4-phenyl-2-thiazolyl-urdieo)-isovalerate. In an example, h is is prepd. by reacting 2-amino-4-phenylthiazole with 3-isocyanato-isovaleric acid methyl ester in the presence of pyridine. The prod. is isolated in the form of its hydrochloride. |