666174-87-4Relevant academic research and scientific papers
Process enabling and the scale-up of 6β-hydroxymethylsulbactam and its esters
Norris, Timothy,Ripin, David H. Brown,Ahlijanian, Paul,Andresen, Brian M.,Barrila, Mark T.,Colon-Cruz, Roberto,Couturier, Michel,Hawkins, Joel M.,Loubkina, Ioulia V.,Rutherford, Jennifer,Stickley, Kurt,Wei, Lulin,Vollinga, Roel,De Pater, Robert,Maas, Peter,De Lange, Ben,Callant, Dominique,Konings, Jeroen,Andrien, Jean,Versleijen, Jos,Hulshof, Jos,Daia, Elena,Johnson, Natalka,Sung, David W. L.
, p. 432 - 439 (2005)
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.
A new efficient stereoselective debromination reaction with trialkylgermanium hydrides useful in the design of short synthetic routes to β-lactamase inhibitor prodrugs
Norris, Timothy,Dowdeswell, Christian,Johnson, Natalka,Daia, Dan
, p. 792 - 799 (2005)
Prodrugs derived from the β-lactamase inhibitor 6-β- hydroxymethylsulbactam can be synthesized efficiently in a three-step process by making use of the highly stereoselective radical denomination utilizing tri-n-butylgermanium hydride. This reagent is cap
BETA-LACTAMASE INHIBITOR PRODRUG
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Page 30-31, (2010/02/06)
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.
