Reactions of thiooxime cephalosporin and penicillin derivatives

Details Reactions of thiooxime cephalosporin and penicillin derivatives Reactions of thiooxime cephalosporin and penicillin derivatives

1978-06-19

1979-10-02

Rizzo, Nicholas S.

Organic compounds -- part of the class 532-570 series

Organic compounds

Chalcogen in the nitrogen containing substituent

424246, 424271, 2602452, C07D50118, C07D49942

Patent

active

041699467

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## Y is halogen or lower alkoxy; R.sub.1 is lower alkyl, phenyl, or substituted phenyl; and X is hydrogen, lower alkanoyloxy, ##STR4## 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 (1971-11-01), O'Calvaghan
patent: 3867538 (1975-02-01), Donovick
patent: 3907788 (1975-09-01), Nudelman
patent: 3952094 (1976-04-01), Cole et al.
patent: 4064344 (1977-12-01), Beattie et al.
patent: 4071682 (1978-01-01), Dolfini et al.
Welch, J. Org. Chem., vol. 41, No. 12, pp. 2220-2222 (1976).

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