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US 4,068,080 AGranted
O-2-Isocephem-4-carboxylic acid derivatives as antibacterial agents
AssigneeBristol-Myers Company
InventorsMarcel Menard, Gary M. F. Lim, Terry T. Conway
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AssigneeBristol-Myers Company
InventorsMarcel Menard, Gary M. F. Lim, Terry T. Conway
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 Z is halo, hydroxyl, etherified hydroxyl or hydroxyl esterified with a carboxylic acid residue or a sulfonic acid residue and X is amino, azido or acylamino. Also included in the invention are compounds of formula I in which the carbonyl 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 ##STR162## wherein Z is etherified hydroxyl of the formula --OR.sub.3 in which R.sup.3 is benzyl or a 5- or 6-membered heterocyclic radical containing 1-4 atoms selected from N, O and S, said heterocyclic radical being optionally substituted by one or more substituents selected from halogen, amino, nitro, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 cycloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.4 alkenyl, trifluoromethyl, phenyl, benzyl, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylamino, di C.sub.1 -C.sub.4 alkylamino or alkoxyalkyl of up to 4 carbon atoms and R" is hydrogen or an easily cleavable ester carboxyl-protecting group selected from benzhydryl, benzyl, p-nitrobenzyl, p-methoxybenzyl, trichloroethyl, trimethylsilyl, phenacyl, acetonyl, (lower)alkyl, triphenylmethyl, methoxymethyl, indanyl, phthalidyl, pivaloyloxymethyl or acetoxymethyl, or a pharmaceutically acceptable salt thereof.
Dependencies are inferred from the claim text.