Thiooxime penicillin derivatives

Details Thiooxime penicillin derivatives Thiooxime penicillin derivatives

1977-11-09

1979-06-19

Rizzo, Nicholas S.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

424270, C07D27704

Patent

active

041586573

ABSTRACT:
Compounds of the formula ##STR1## wherein A is ##STR2## R is hydrogen, lower alkyl, benzyl, p-methoxybenzyl, p-nitrobenzyl, diphenylmethyl, tri(lower alkyl)silyl, lower alkoxymethyl, 2,2,2-trichloroethyl, ##STR3## or ##STR4## Y is halogen or lower alkoxy; R.sub.1 is lower alkyl, phenyl, or substituted phenyl; and X is hydrogen, lower alkanoyloxy, ##STR5## or certain heterothio groups; R.sub.4 is hydrogen or lower alkyl; R.sub.5 is lower alkyl; are disclosed. These compounds, particularly the free acids, possess the useful pharmacological property of inhibiting .beta.-lactamase enzymes as well as being useful as intermediates, particularly where R is a readily cleavable ester, in the preparation of antibacterially active 6.alpha.-methoxy penicillins and 7.alpha.-methoxy cephalosporins.

REFERENCES:
patent: 3624225 (1975-04-01), O'Callaghan et al.
patent: 3867538 (1975-02-01), Donovick
patent: 3907788 (1975-09-01), Nudelman
patent: 3952094 (1976-04-01), Cole et al.
Welch, J. Org. Chem., vol. 41, No. 12, pp. 2220-2222, (1976).

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