O-2-isocephem-4-carboxylic acid derivatives as antibacterial agents
AssigneeBristol-Myers Company
InventorsDonald E. Horning, Leeson R. Morris, James L. Douglas
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AssigneeBristol-Myers Company
InventorsDonald E. Horning, Leeson R. Morris, James L. Douglas
Estimating the term…
There is described the stereoselective total synthesis of novel .DELTA..sup.2,3 -1,4-morpholine-2-carboxylic acids possessing a fused .beta.-lactam ring in the 1,6-position and carrying a substituent cis to carbon 5 in the 7-position of the fused ring system represented by the general formula ##STR1## wherein X is amino, azido or acylamido and Z represents optionally substituted C.sub.1 -C.sub.6 alkyl, aryl, aralkyl or heterocyclic. Also included in the invention are compounds of formula I in which the carboxyl group at the 2-position is protected as by an easily cleavable ester group and salts of both the free acids and carboxyl-protected compounds of formula I. The compounds of formula I are potent antibacterial agents or are of use as intermediates in the preparation of such antibacterial agents.
A compound having the formula ##STR192## wherein R.sup." is hydrogen or an easily cleavable ester carboxyl-protecting group selected from the group consisting of benzhydryl, p-nitrobenzyl, p-methoxybenzyl, trichloroethyl, trimethylsilyl, phenacyl, acetonyl, (lower)alkyl, triphenylmethyl, methoxymethyl, indanyl, phthalidyl, pivaloyloxymethyl and acetoxymethyl and Z represents C.sub.1 -C.sub.6 alkyl optionally substituted by one or more hydroxy, halo, amino, nitro, di(C.sub.1 -C.sub.4 alkyl)amino, carboxy, sulfo or cyano substituent, or a pharmaceutically acceptable salt thereof
Dependencies are inferred from the claim text.