GB1416987A - Antibiotics - Google Patents

Abstract

1416987 Penicillin and cephalosporin compounds NATIONAL RESEARCH DEVELOPMENT CORP 26 Jan 1973 [9 Feb 1972] 55802/71 Heading C2C Novel penicillin and cephalosporin compounds substituted at the 3-position of the 2-azetidone ring by a hydrazono, hydrazino, acylhydrazono or acylhydrazino group are prepared by reducing a penicillin or cephalosporin compound substituted at the 3-position of the 2-azetidone ring by a diazo group to yield the hydrazono compound, which may then be acetylated, and obtaining the hydrazino and acylhydrazino compounds by reduction of the corresponding hydrazono or acylhydrazono compounds. Trichloro 7 - diazo - 3 - methylceph - 3 - em - 4- carboxylate is prepared by treating 7-amino-3- methylceph - 3 - em - 4 - carboxylate with isoamyl nitrite and formic acid and pouring the product into excess sodium bicarbonate solution. Benzyl 6-diazo-penicillinate is prepared by the sequential steps of treating penicillin G sodium salt with benzyl bromide to yield benzyl penicillin benzyl ester, which is reacted with dinitrogen tetroxide to form N-nitroso-penicillin G benzyl ester, which is then stirred with saturated sodium bicarbonate solution to yield the desired compound. Pharmaceutical compositions comprise the novel acylhydrazono or acylhydrazino compounds or non-toxic physiologically acceptable salts thereof together with a suitable diluent or carrier.