Carboxyl derivatives of thienamycin

Claim 1

A compound having the structural formula: ##STR35## wherein X is oxygen, sulphur or NR' (R'=H or R); R is selected from the group consisting of hydrogen (X is not oxygen); alkyl having 1-10 carbon atoms; phenacyl and nuclear substituted phenacyl wherein the substituent is chloro, bromo, fluoro or alkyl having from 1-6 carbon atoms; alkoxyalkyl wherein the alkoxyl moiety has 1-6 carbon atoms and the alkyl moiety has 1-6 carbon atoms; alkanoyloxyalkyl having 2 to 12 carbon atoms; halo and perhaloalkyl wherein the halo is chloro, bromo, or fluoro and the alkyl chain has 1-6 carbon atoms; alkenyl having from 2-10 carbon atoms; alkoxycarbonyloxyalkyl having 3-14 carbon atoms; dialkylaminoacetoxyalkyl having 4-21 carbon atoms; alkanoylamidoalkyl having 2-13 carbon atoms; benzyl, benzhydryl, p-chlorobenzyl, o-nitrobenzyl, 3,5-dinitrobenzyl, p-methoxybenzyl, m-benzoylbenzyl, p-t-butylbenzyl, m-phenoxybenzyl, p-benzoylbenzyl, p-nitrobenzyl, 3,5-dichloro-4-hydroxybenzyl, p-methoxycarbonylbenzyl, p-methoxybenzhydryl, p-carboxybenzyl, the latter being either the free acid or the sodium salt, 2,4,6-trimethylbenzyl, p-pivaloyloxybenzyl, p-t-butoxycarbonyl benzyl, p-methylbenzyl, p-benzoyloxybenzyl, p-acetoxybenzyl, p-2-ethylhexanoylbenzoyl, p-ethoxycarbonylbenzyl, p-benzoylthiobenzyl, p-benzamidobenzyl, o-pivaloxyloxybenzyl, m-pivaloyloxybenzyl, p-isopropoxybenzyl, p-t-butoxybenzyl, 2,2-dimethyl-5-coumaranmethyl, p-trimethylsilylbenzyl, 3,5-bis-t-butoxy-4-hydroxybenzyl; 2-thienylmethyl, 2-furylmethyl, 3-t-butyl-5-isothiazolmethyl, 6-pivaloyloxy-3-pyridazinylethyl, 5-phenylthio-1-tetrazolylmethyl, phthalidyl; phenylethyl, 2-(p-methylphenyl)ethyl, (4-methoxy)phenozymethyl, phenoxymethyl, (4-chloro)phenoxymethyl, (4-nitro)phenoxymethyl, (4-benzyloxy)methyl, (4-methyl)phenoxymethyl, (4-benzyloxy)phenoxymethyl, (4-methyl)phenoxymethyl, (2-methoxy)phenoxymethyl, (1-phenoxy)ethyl, (4-amino)phenoxymethyl, (4-methoxy)phenylthiomethyl, (4-chloro)phenylthiomethyl, phenylthioethyl; (4-methyl)phenyl, (4-hydroxy)phenyl, (4-t-butyl)phenyl; p-nitrophenyl, 3,5-dinitrophenyl or p-carboxyphenyl, the latter having either the free acid or the sodium salt form, 3-phenyl-2-propenyl, benzyloxymethyl, (4-nitro)benzyloxymethyl, (4-chloro)benzyloxymethyl, methylthioethyl, ethylthioethyl, cyclohexylthiomethyl, decylthiobutyl, methylthiopropyl, isopropylthioethyl, methylthiobutyl, phenyl, 5-indanyl, acetylthiomethyl, acetoxymethyl, diethylamino, dimethylaminoethyl, 5-indanylmethyl, p-pivaloylbenzyl, benzyloxymethyl, acetylthioethyl, pivaloylthiomethyl and methylthiomethyl.