75722-77-9

Upstream product

• 421-83-0 trifluoromethane sulfonyl chloride 
• 51056-28-1 benzhydryl 6α-hydroxypenicillinate 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 15058-64-7 6-α-hydroxypenicillanic acid 
• 551-16-6 6-Aminopenicillanic Acid 

Downstream Products

• 75722-86-0 (2S,5R,6R)-6-Acetylsulfanyl-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 75722-91-7 (2S,5R,6R)-6-Ethoxythiocarbonylsulfanyl-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 75722-90-6 (2S,5R,6R)-6-Diethylthiocarbamoylsulfanyl-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 76517-36-7 6-β-iodopenicillanic acid benzhydryl ester 
• 683751-10-2 (2S,5R,6R)-3,3-Dimethyl-4,4,7-trioxo-6-(2,2,2-trichloro-ethoxycarbonylsulfanyl)-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 683751-09-9 (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2,2,2-trichloro-ethoxycarbonylsulfanyl)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 683751-12-4 (2S,5R,6S)-6-Mercapto-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 683751-05-5 (2S,5R,6R)-6-Mercapto-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 75722-82-6 benzhydryl 6-beta-chloropenicillanate 
• 75527-85-4 benzhydryl 6β-bromopenicillanate 

Relevant academic research and scientific papers

Penicillin-derived inhibitors that simultaneously target both metallo- and serine-β-lactamases

The synthesis and β-lactamase inhibitory activity of four 6-(mercaptomethyl)penicillinates and the four corresponding 6-(hydroxymethyl) penicillinates are described. These penicillins include both C6 stereoisomers as well as the sulfide and sulfone oxidation states of the penam thiazolidine sulfur. All compounds were evaluated as inhibitors of representative metallo- and serine-β-lactamases enzymes. Selected (mercaptomethyl)penicillinates are shown to inactivate both metallo- and serine-β-lactamases and to display synergism with piperacillin against β-lactamase producing strains.

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.