Antibacterial alpha-ureido penicillin derivs. - prepd. by reaction of a 1-amino-cycloalkane-carboxamido-penicillanic acid cpd. with e.g. a 4-hydroxy-5-pyrimidinyl isocyanate

摘要

New ureido-substd. penicillin derivs. are cpds. of formula (Ia) and their tautomers of formula (Ib) and, when E is H, their pharmacologically tolerable salts with organic and inorganic bases: n is 1 or 2; R is H, Me, Et, (substd.)cyclopropyl, -NH-Z-X (where Z is opt. branched 1-6C alkylene or 3-6C cycloalkylene; X is CN, OH, SH, -CO-N(R3)(R4), -CO-R3, -COOR4, -N(R3)(R4), -NH-COR3, -NH-CO-N(R3)(R4), -NH-CS-N(R3)(R4), -NH-SO2-R3, -OR3, -O-COR3, -SR3, -SOR3 or -SO2R3, (where R3 is 1-4C alkyl or phenyl; R4 is H or 1-4C alkyl, or N(R3)(R4) is 3- to 6-membered heteromonocyclic ring), -NH-(CH2)m-C6H2-(R5)(R6)(R7) (m is 0 or 1; R5, R6, R7 are H, halogen, Me, Et, i-Pr, NH2, NHMe, NMe2, NEt2, NEt2, morpholino, OH, OMe, OEt, NO2, acetamido, -SO2-Me, acetyl, -O-CO-Me, -COOMe, -COOH, -CONH2, -CO-NHMe, -CO-NMe2, CN, -SMe, -SOMe, -SO2-NH2 or CF3, at least one of R5-R7 being other than H), -NH-(CH2)m-Het, where Het is a heterocyclyl gp., and E is H or a protecting gp. which is readily cleaved off in vitro or in vivo. (I) are antibacterials useful in the prophylaxis and treatment of local and systemic infections in human and veterinary medicine. They can also be used as preservatives for inorganic and organic materials (including foodstuffs).