Alpha-(imidazolidinonyl carbonylamino) penicillins and cephalosporins - active against gram negative species and useful e.g. as feed additives

• Main Authors: PREISS,MICHAEL,DR, KOENIG,H.-B.,DR, METZGER,K.-G.,DR, SCHROECK,WILFRIED,DR
• Format: Patent
• Language: English; German
• Published: 12.08.1976
• Edition: 2
• Subjects: CHEMISTRY; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY

Antibiotics are of formula (I) and non-toxic salts and hydrates (where R = H or CH3O; Z = R1R2CN- or R1R2C(OH).NH-; R1 and R2 = H; opt. substd. alkyl or alkenyl; opt. substd. cycloalkyl, cycloalkenyl, cycloalkedienyl, aralkyl, aryl, or heterocyclyl; COOH; COOCH3; COOC2H5; CN; NO2; lower alkylcarbonyl; CONH2 or SO2NH2 (both opt. mono- or di-CH3 substd.); R1 and R2 can together complete and opt. unsatd. 3-7 membered, opt. substd. carbocyclic or heterocyclic ring; A = CH2CH2, CH2CH2CH2 or 1,2-phenylene; B = opt. substd. phenyl, cyclohexynl or cyclohexadienyl; X = S,O% SO; SO2 or CH2; Y = -C(CH3)2.CH(COOH)- or -CH2.C-(CH2T)=C(COOH)-; T = H, alkylcarbonyloxy, pyridinium, aminopyridinium, carbamoyloxy, N2, CN, OH, phenylthio (opt. substd.) or 5-6 membered heterocycylthio (opt. substd.). The cpds. exist as individual stereoisomers about C or mixts., and where Z = R1R2CN- as syn or anti isomers). (I) are antibacterials more active, and with a broader spectrum of activity against Gram negative species (esp. those which elaborate beta-lactamase), than known penicillins and cephalosporins. They can be used therapeutically, to preserve polymers, lubricants etc. and as feed additives to increase growth rate and improve feed utilisation.