6-(1-carbamoyl-1-hydroxymethyl)penicillanic acid derivatives

Claim 1

A compound having the formula ##STR25## wherein n is 0, 1 or 2; R is hydrogen, a radical group forming an ester hydrolyzable under physiological conditions, or an acyloxymethyl or 1-(acyloxy)ethyl radical derived from a conventional beta-lactam antibiotic; and R 1 and R 2 are taken separately and are each independently hydrogen, (C 1 -C 7 )alkyl, phenyl, (C 7 -C 12 )phenylalkyl, (C 3 -C 7 )cycloalkyl, naphthyl, or ##STR26## where m is 1 or 2 and p is 1, 2 or 3; or one of said groups substituted on aliphatic, aromatic or heterocyclic carbon with (C 1 -C 4 )alkyl, phenyl, hydroxy, hydroxymethyl, 2-hydroxyethyl, (C 1 -C 4 )alkoxy, (C 2 -C 5 )alkanoyloxy, carbamoyloxy, formamido, (C 2 -C 5 )alkanecarboxamido, (C 1 -C 4 )alkanesulfonamido, ##STR27## on heterocyclic nitrogen with (C 1 -C 4 )alkyl, phenyl, (C 7 -C 9 )phenylalkyl, pyridyl, 2-hydroxyethyl, formyl, (C 2 -C 5 )alkanoyl; or ##STR28## R 1 and R 2 are taken together with the nitrogen to which they are attached to form a pyrrolidine, piperidine, perhydroazepine, morpholine, piperazine, homopiperazine, indoline, isoindoline, 1,2,3,4-tetrahydroquinoline, 1,2,3,4-tetrahydroisoquinoline or ##STR29## ring system; or one of said ring systems substituted on aliphatic, aromatic or heterocyclic carbon with (C 1 -C 4 )alkyl, phenyl, hydroxy, hydroxymethyl, 2-hydroxyethyl, (C 1 -C 4 )alkoxy, (C 2 -C 5 )alkanoyloxy, carbamoyloxy, formamido, (C 2 -C 5 )alkanecarboxamido, (C 1 -C 4 )alkanesulfonamido, ##STR30## on heterocyclic nitrogen with (C 1 -C 4 )alkyl, phenyl, (C 7 -C 9 )phenylalkyl, pyridyl, 2-hydroxyethyl, formyl, (C 2 -C 5 )alkanoyl; or ##STR31## R 3 and R 4 are taken separately and are each hydrogen, (C 1 -C 4 )alkyl or phenyl; or R 3 and R 4 are taken together with the nitrogen to which they are attached to form a pyrrolidine, piperidine, morpholine, or 4-[(C 1 -C 3 )alkyl or phenyl]piperazine ring; with the provisos that in said group --NR 1 R 2 (a) there is no tetrahedral carbon atom which is simultaneously bonded to two of the same or different atoms selected from the group consisting of nitrogen, oxygen or sulfur and (b) when both of R 1 and R 2 are other than hydrogen, then the carbons of R 1 and R 2 which are adjacent to the nitrogen branch point are substituted with a total of at least two hydrogens; a pharmaceutically acceptable cationic salt when the compound contains a carboxylic acid group; or a pharmaceutically acceptable acid addition salt when the compound contains a basic nitrogen atom.