Alpha-heterocyclyl-ureido-acetamido penicillin and cephalosporin cpds. - antibacterials for human and veterinary medicine active esp. against Pseudomonas

摘要

beta-Lactams of formula (I), their easily dissociated esters and pharmaceutically acceptable salts are new:- In the formula, Z = phenyl, RO-phenyl, cyclohexen-1-yl, cyclohexa-1,4-dienyl, or thienyl; R and R1 = H or alkyl-(O)n-CO; n = 0 or 1; R2 and R3 = H, halo, NO2, NH2 (opt. substd. by 1 or 2 alkyl or by acyl), or together are -CH=CH-CH=CH- opt. with one CH replaced by N, and/or one H replaced by R4 or 2 H's replaced by R4 and R5; R4 and R5 are each alkyl, alkoxy, dialkylamino or halo, or together they are -CH=CH-CH=CH- opt. with one CH replaced by N; W = H OH or alkyl; X = O or S; B = H or CH3O; A is C(CH3)2.- CHQ; CH2CE=CQ or CH2.C(CH2Y)=CQ; Q = COOH, tetrazol-5-yl, or if Y = R6 - pyridinium, it is COO-; E = halo or alkoxy; Y = H, OH, acetoxy, OCONH2, R6-pyridiniuim or -SHet; R6 = H or CONH2; Het = 3-methyl-1,2-4-thiazdiazol-5-yl, 5-methyl-1,34-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl (opt. substd. by 5-methyl), tetrazol-5yl (opt. substd. by 1-methyl), 1,2,3-triazol-4-yl, 4-methyloxazol-2-yl or 1-oxido-2-pyridino; all alkyl, acyl and alkoxy have 1-4C. Proviso is that if A=C(CH3)2.CH(COOH), then Z = o or m-RO-phenyl; p -(alkyl-(o)nCO)- phenyl, cyclohexen-1-yl or thienyl; and/or W = OH; and/or R2 and R3 = halo, NO2, NH2 (opt. substd. as above and/or B=CH3O. (I) are broad-spectrum antibiotics useful in human and veterinary medicine. They are active against e.g. Escherichia, Klebsiella and esp., Pseudomonas, including strains resistant to other beta-lactam antibiotics.