6-Alpha-halopenicillanic acid 1,1-dioxides

Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal

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424270, 424271, 2602391, C07D49900

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active

044204264

ABSTRACT:
A process for the preparation of penicillanic acid 1,1-dioxide and esters thereof readily hydrolyzable in vivo, which comprises oxidation of a 6-halopenicillanic acid, or an ester thereof readily hydrolyzable in vivo, to the corresponding 6-halopenicillanic acid 1,1-dioxide or ester thereof, followed by dehalogenation (e.g. by hydrogenolysis). Certain of the 6-halopenicillanic acid 1,1-dioxides and esters thereof readily hydrolyzable in vivo are novel intermediates. Penicillanic acid 1,1-dioxide, and esters thereof readily hydrolyzable in vivo are known compounds which are beta-lactamase inhibitors and which enhance the effectiveness of certain beta-lactam antibiotics (e.g. the penicillins) in the treatment of bacterial infections in mammals, particularly humans.

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Busson et al., "Recent Advances in the Chemistry of Beta-Lactam Antibiotics", J. Elks, ed., Burlington House, London, 1977, Chapter 32, pp. 304-313.
Clayton, Journal of the Chemical Society (London), Part C, 2123 (1969).
Cartwright et al., Nature, 278, 360 (1979).

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