623906-29-6

Upstream product

• 53051-97-1 4H,5H,6H-cyclopenta[d][1,3]thiazol-2-amine 
• 75271-94-2 3-bromo-1,1-dimethoxypropan-2-one 
• 349481-42-1 ethyl 6,7-dihydro-5H-cyclopenta[d]imidazo[2,1-b][1,3]thiazole-2-carboxylate 
• 694-28-0 2-chlorocyclopentanone 
• 349481-43-2 6,7-dihydro-5H-cyclopenta[d]imidazo[2,1-b][1,3]thiazole-2-methanol 

Downstream Products

• 623906-28-5 4-nitrobenzyl (5R)-6-[(acetyloxy)(6,7-dihydro-5H-cyclopenta[d]imidazo[2,1-b][1,3]thiazol-2-yl)]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 

Relevant academic research and scientific papers

Process for preparing beta-lactamase inhibitors

The present invention relates to processes for preparing β-alkylidene penem derivatives that can be important as broad spectrum β-lactamase inhibitors and anti-bacterial agents.

Tricyclic 6-alkylidene-penem beta-lactamase inhibitors and beta-lactam antibiotic combination: a broad spectrum antibiotic

The present invention provides a β-lactam antibiotic such as cefepime and a compound of formula I, pharmaceutical compositions and the use thereof for the treatment of bacterial infection or disease in a patient in need thereof.

Tricyclic 6-alkylidene-penems as class-D beta-lactamases inhibitors

This invention relates to certain tricyclic 6-alkylidene penems which act as a inhibitor of class-D enzymes. β-Lactamases hydrolyze β-lactam antibiotics, and as such serve as the primary cause of bacterial resistance. The compounds of the present inventio

Structure-activity relationship of 6-methylidene penems bearing tricyclic heterocycles as broad-spectrum β-lactamase inhibitors: Crystallographic structures show unexpected binding of 1,4-thiazepine intermediates

The design and synthesis of a series of seven tricyclic 6-methylidene penems as novel class A and C serine β-lactamase inhibitors is described. These compounds proved to be very potent inhibitors of the TEM-1 and AmpC β-lactamases and less so against the class B metallo-β-lactamase CcrA. In combination with piperacillin, their in vitro activities enhanced susceptibility of all class C resistant strains from various bacteria. Crystallographic structures of a serine-bound reaction intermediate of 17 with the class A SHV-1 and class C GC1 enzymes have been established to resolutions of 2.0 and 1.4 A?, respectively, and refined to R-factors equal 0.163 and 0.145. In both β-lactamases, a seven-membered 1,4-thiazepine ring has formed. The stereogenic C7 atom in the ring has the R configuration in the SHV-1 intermediate and has both R and S configurations in the GC1 intermediate. Hydrophobic stacking interactions between the tricyclic C7 substituent and a tyrosine side chain, rather than electrostatic or hydrogen bonding by the C3 carboxylic acid group, dominate in both complexes. The formation of the 1,4- thiazepine ring structures is proposed based on a 7-endo-trig cyclization.

PROCESS FOR PREPARING 6-ALKYLIDENE PENEM DERIVATIVES

The present invention provides a process of making compounds of Formula (I), which are useful for the treatment of bacterial infection or disease.

HETEROTRICYCLYL 6-ALKYLIDENE-PENEMS AS ΒΕΤΑ-LACTAMASE INHIBITORS

The present invention provides a compound of formula I, pharmaceutical compositions and the use thereof for the treatment of bacterial infection or disease in a patient in need thereof.