Antibacterial alpha-ureido-acyl penicillin and cephalosporin - prepd. e.g. by reaction of the alpha-acylamino-beta-lactam with a heterocyclic isocyanate

摘要

Alpha-ureido-acylamino-beta-lactam derivs. are cpds. of formula (I) and, when E is H, their salts with (in)organic bases (where A is (4-hydroxy)phenyl, 2- or 3-thienyl, 2- or 3-furyl, cyclohexyl, 1-cyclo-hexenyl, 2,4-cyclohexadien-1-yl, or phenyl substd. in the 3- and 4-positions by Cl, OH and/or OMe; R is a bicyclic heterocyclic ring of formula (Ia) in which Y is a divalent residue forming a 5- or 6-membered saturated or unsaturated heterocyclic ring with 1-4 identical or different heteroatoms, and R' is H, halo, 1-4C hydrocarbyl, phenyl, OH, 1-4C alkoxy, SH, 1-4C alkylthio, NH2, 1-6C mono- or dialkylamino, (1-3C alkoxy)-carbonyl, or a saturated N-contg. 5- or 6-membered heteromonocyclic ring opt. contg. an additional O,N or S heteroatom; and X is a group of formula (Ib) or (Ic) in which D is H, acetoxy, carbamoyloxy or -S-Het (Het= 3-methyl-1,2,4-thiadiazol-5-yl, 2-methyl-1,3,4-oxadiazol-5-yl, 1,3,4-thiadiazol-2-yl, 2-methyl-1,3,4-thiadiazol-5-yl, tetrazol-5-yl, 1-methyl-tetrazol-5-yl or 1,2,3-triazol-4-yl and E is H or a group which is readily cleaved off in vitro or in vivo). (I) are antibiotics with a broad spectrum of activity against Gram-positive and Gram-negative bacteria, and can be used in human and veterinary medicine for the prophylaxis and treatment of local and systemic infections.