Derivate von Aminocephalosporansaeure und Verfahren zu ihrer Herstellung

摘要

1,131,645. Cephalosporins. BRISTOLMYERS CO. 2 Aug., 1966 [2 Aug., 1965], No. 34638/66. Headings C2A and C2C. Cephalosporins effective against Salmonella are 7-(41-purazanalkanoyl)-aminocephalosporanic acids, salts or derivatives of Formula I wherein R1 and R2 are each H or C 1-10 alkyl; A is H, OH, C 2-8 alkanoyloxy, benzoyloxy, quaternary ammonium (e.g. pyridinium, quinolinium, picolinium or lutidinium) or, when taken together with M, a monovalent C-O bond; and M is H, a pharmaceutically acceptable non-toxic cation, an anionic charge when A is a quaternary NH 4 radical or, when taken together with A, is a monovalent C-O bond. Typical compounds are 7-[α-(3-methoxy- 4 - purazan) - acetamido] - cephalosporanic acid, 3 - pyridiniummethyl-7-[α-(3-methoxy-4- furazan) - acetamido] - decephalosporanic acid inner salt and 3-hydroxymethyl-7-[α-(3-methoxy - 4 - furazan) - acetamido] - decephalosporanic acid. Salts are formed with metals such as Na, K, Ca and Al and with organic bases, e.g. triethylamine, procaine and dibenzylamine. Compounds of Formula I are prepared by acylating a compound of formula wherein A is as defined above, or a neutral salt thereof with an acid of formula or an acylating derivative thereof, wherein R1 and R2 have the above meanings. Where A is alkanoyloxy, the resulting compound may be treated with a tertiary amine to form the corresponding quaternary ammonium inner salt. 3-Hydroxy-4-furazanacetic acid is produced by treating hydroxylamine HCl with diethyl oxalacetate sodium at pH 8-8À5, followed by acidification and formation of the N,N1-dibenzylethylene diamine salt, from which the free acid is recovered. 3-Methoxy-4-furazanacetic acid is prepared by treating 3-hydroxy-4-furazanacetic acid with diazomethane in ether. A pharmaceutical composition for human or animal use comprises a cephalosporin of Formula I and a carrier. The cephalosporins may be used for treating mastitis in animals, as antibacterial agents and as nutritional supplements in animal feeds.