Method for producing chemical compounds

C - Chemistry – Metallurgy – 07 – D

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260/118.5

C07D 499/00 (2006.01)

Patent

CA 1265787

ABSTRACT OF THE DISCLOSURE Novel essentially pure crystalline 6 .beta. -halopenicillanic acid derivatives are provided herein. Such derivatives are of the formula I Image I in which X stands for chlorine, bromine or iodine. Novel pharmaceutically acceptable, non-toxic salts of the compounds of formula I, and novel pharmaceutically acceptable, easily hydrolyzable esters thereof, including salts of such esters are provided. Processes for the preparation of such compounds are also provided, which includes as essential steps preparing a mixture 6 .beta. - and 6 .alpha. -derivatives either by epimerizing the corresponding 6 .alpha. -derivative or by reducing the corresponding 6, 6-dihalo-derivative; and then separating the respective 6 .beta. -halo-derivative from said mixture. The 6 .beta. -halopenicillanic acids of formula I are potent inhibitors of .beta. -lactamases from a variety of gram-positive and gram-negative bacteria, making the 6 .beta. -halopenicillanic acids as well as their salts and easily hydrolyzable esters valuable in human and veterinary medicine.

352237

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