Patent ID: 6037341
Filing Date: 2000-03-14
Classification: A61P,C07D,Y02P

Abstract:
A carbapenem compound represented by the following formula (I), or a salt thereof: ##STR67## wherein the ring A represents a 3- to 7-membered saturated or partially unsaturated heterocycle containing only nitrogen as heteroatoms and optionally having a ring substituent other than R.sup.6 and selected from the group consisting of a hydrogen atom, hydroxyl, mercapto, halogen, cyano, azido, alkyl, alkenyl, alkynyl, alkoxy, halogenoalkyl, guanidino, formimidoyl, acetimidoyl, carbamoyl, thiocarbamoyl, carbamoylalkyl, carbamido, alkanoyl, amino, alkylamino, dialkylamino, aminoalkyl, carboxy, alkoxycarbonyl, alkoxycarbonylalkyl, aminoalkylaminoalkyl, alkylcarbonyloxy, cycloalkyl, cycloalkenyl, phenyl, alkylthio, phenylthio, benzyl, benzoyl and halogenoaryl; R.sup.1 represents hydrogen or methyl; R.sup.2 and R.sup.5 are the same or different and each represents hydrogen or a protecting group of the hydroxyl group selected from the group consisting of trimethylsilyl, t-butyl dimethylsilyl, methoxymethyl, 2-methoxyethoxymethyl, tetrahydropyranyl, benzyl, p-methoxybenzyl, 2,4-dimethoxybenzyl, o-nitrobenzyl, p-nitrobenzyl, trityl, formyl, acetyl, t-butoxy-carbonyl, 2-iodoethoxycarbonyl, 2,2,2-trichloroethoxy-carbonyl, 2-propenyloxycarbonyl, 2-chloro-2-propenyloxycarbonyl, 3-methoxycarbonyl-2-propenyloxycarbonyl, 2-methyl-2-propenyloxycarbonyl, 2-butenyloxycarbonyl, cinnamyloxycarbonyl, benzyloxycarbonyl, p-methoxybenzyloxycarbonyl, o-nitrobenzyl-oxycarbonyl and p-nitrobenzyloxycarbonyl; R.sup.3 represents hydrogen or a protecting group of the carboxyl group selected from the group consisting of methyl, ethyl, isopropyl, t-butyl, 2-iodoethyl, 2,2,2-trichloroethyl, methoxymethyl, ethoxymethyl, isobutoxymethyl, butyrloxymethyl, pivaloyloxy-methyl, 1-methoxycarbonyloxyethyl, 1-ethoxycarbonyloxyethyl, benzyl, p-methoxybenzyl, o-nitrobenzyl, p-nitrobenzyl, benzhydryl and phthalidyl; R.sup.4 represents hydrogen, lower alkyl or a protecting group of the amino group selected from the group consisting of formyl, acetyl, chloroacetyl, dichloroacetyl, propionyl, phenylacetyl, phenoxyacetyl, thienylacetyl, benzyloxycarbonyl, t-butoxy carbonyl, p-nitrobenzyloxycarbonyl, 2,2,2-trichloroethyl, trityl, p-methoxybenzyl, p-nitrobenzyl, diphenylmethyl, pivaloyloxymethyl, trimethylsilyl, t-butyl dimethylsilyl, benzylidene, salicylidene, p-nitrobenzylidene, m-chlorobenzylidene, 3,5-di(t-butyl)-4-hydroxybenzylidene and 3,5-di(t-butyl)benzylidene; R.sup.6 represents: (1) hydrogen, (2) lower alkyl, optionally substituted by an optionally protected hydroxy, a carbamoyl, formimidoyl, acetimimidoyl or ##STR68## wherein R.sup.7 and R.sup.8 are the same or different and each represents hydrogen, lower alkyl, or a protecting group of the amino group, or (3) a protecting group of the amino group or a protecting group of the imino group; and m is 0 or 1, wherein the hydroxy is protected by the hydroxyl protecting group described above and the amino and imino group are protected by the amino protecting group described above.