75722-76-8

Upstream product

• 15058-64-7 6-α-hydroxypenicillanic acid 
• 824-94-2 p-methoxybenzyl chloride 
• 623-12-1 4-chloromethoxybenzene 

Downstream Products

• 75722-78-0 4-methoxybenzyl 6α-trifloxypenicillanate 
• 75722-79-1 4-methoxybenzyl 6β-iodopenicillanate 
• 74772-32-0 6β-iodopenicillanic acid 

Relevant academic research and scientific papers

6-beta-Halopenicillanic acid 1,1-dioxides as beta-lactamase inhibitors

6-beta-Halopenicillanic acid 1,1-dioxides, physiologically acceptable salts thereof and esters thereof readily hydrolyzable; pharmaceutical compositions containing a 6-beta-halopenicillanic acid 1,1-dioxide, a physiologically acceptable salt thereof or an ester thereof readily hydrolyzable; and a method for enhancing the effectiveness of a beta-lactam antibiotic, using a 6-beta-halopenicillanic acid 1,1-dioxide, a physiologically acceptable salt thereof or an ester thereof readily hydrolyzable.

6-Alpha-halopenicillanic acid 1,1-dioxides

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.

6-Perhaloalkylsulfonyloxy-penicillanic acids and derivatives thereof

6-Alpha and 6-beta-substituted penicillanic acid derivatives of the formula: STR1 wherein R is H or a conventional penicillin carboxy protecting group or an ester forming residue readily hydrolyzable in vivo and R1 is a perhaloalkyl group of from 1 to 4 carbon atoms wherein the halogen atoms are fluoro or chloro, undergo SN2 nucleophilic displacement with halide or azide ions with inversion of configuration at C-6 to yield the corresponding 6-beta or 6-alpha-halo- or azido-substituted product.