666174-91-0

Upstream product

• 88957-58-8 sodium (2S,5R)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo-[3.2.0]-heptane-2-carboxylate-4,4-dioxide 
• 100-39-0 benzyl bromide 
• 76646-91-8 6,6-dibromopenicillanic acid-1,1-dioxide 
• 50-00-0 formaldehyd 
• 76454-54-1 benzyl (2S,5R)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo [3.2.0]-heptane-2-carboxylate-4,4-dioxide 

Downstream Products

• 666174-87-4 [(1R)-1-(benzoyl)oxy]ethyl (2S,5R,6R)-3,3-dimethyl-6-(hydroxymethyl)-7-oxo-4-thia-1-azabicyclo-[3.2.0]heptane-2-carboxylate-4,4-dioxide 

Relevant academic research and scientific papers

Process enabling and the scale-up of 6β-hydroxymethylsulbactam and its esters

The optimization of the synthesis of 6β-hydroxymethylsulbactam is described. The primary challenge in this synthesis is the installation of the 6β-hydroxymethyl group with the proper stereochemistry. Engineering challenges associated with the addition of gaseous formaldehyde to a Grignard reagent at low temperature and a number of approaches to achieving the appropriate β-stereochemistry are presented.

BETA-LACTAMASE INHIBITOR PRODRUG

Prodrugs of 6-β-hydroxymethylpenicillanic acid sulfone having the structure wherein R is H or methyl, each X is methylene, and Y is 0, or wherein R is H, each X is 0 and Y is methylene, and solvates thereof are disclosed. Also disclosed are pharmaceutical compositions comprising a prodrug of the present invention, or a solvate thereof, an optional beta-lactam antibiotic and at least one pharmaceutically acceptable carrier. Further disclosed is a method for increasing the therapeutic effectiveness of a beta-lactam antibiotic in 20 a mammal by administering an effective amount of a beta-lactam antibiotic and an effectiveness-increasing amount of a prodrug of the present invention, or a solvate thereof. Additionally disclosed is a method for treating a bacterial infection in a mammal by administering a therapeutically effective amount of a pharmaceutical composition of the present invention to a mammal in need thereof.

BETA-LACTAMASE INHIBITOR PRODRUG

Prodrugs of 6-?-hydroxymethylpenicillanic acid sulfone having the structure wherein R is H or methyl, and solvates thereof, are disclosed. Also disclosed are pharmaceutical compositions comprising a prodrug of the present invention, or a solvate thereof, an optional beta-lactam antibiotic and at least one pharmaceutically acceptable carrier. Further disclosed is a method for increasing the therapeutic effectiveness of a beta-lactam antibiotic in a mammal by administering an effective amount of a betalactam antibiotic and an effectiveness-increasing amount of a prodrug of the present invention, or a solvate thereof. Additionally disclosed is a method for treating a bacterial infection in a mammal by administering a therapeutically effective amount of a pharmaceutical composition of the present invention to a mammal in need thereof.