348626-16-4

Basic information

• Product Name: tert-butyl 4-{4-[(5S)-5-({[(5-chloro-2-thienyl)carbonyl]amino}methyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl}piperazine-1-carboxylate
• Synonyms: tert-butyl 4-{4-[(5S)-5-({[(5-chloro-2-thienyl)carbonyl]amino}methyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl}piperazine-1-carboxylate
• CAS NO: 348626-16-4
• Molecular Weight: 539.028
• Mol File: 348626-16-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: tert-butyl 4-{4-[(5S)-5-({[(5-chloro-2-thienyl)carbonyl]amino}methyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl}piperazine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 4-{4-[(5S)-5-({[(5-chloro-2-thienyl)carbonyl]amino}methyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl}piperazine-1-carboxylate(348626-16-4)
• EPA Substance Registry System: tert-butyl 4-{4-[(5S)-5-({[(5-chloro-2-thienyl)carbonyl]amino}methyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl}piperazine-1-carboxylate(348626-16-4)

Safety Data

• Hazardous Substances Data: 348626-16-4(Hazardous Substances Data)

Upstream product

• 154590-36-0 tert-butyl 4-(4-(benzyloxycarbonyl)-2-fluorophenyl)piperazine-1-carboxylate 
• 154590-62-2 (R)-tert-butyl-4-(2-fluoro-4-(5-(hydroxymethyl)-2-oxooxazolidin-3-yl)phenyl)piperazine-1-carboxylate 
• 154590-35-9 tert-butyl 4-(4-amino-2-fluorophenyl)piperazine-1-carboxylate 
• 268209-15-0 tert-butyl 4-(4-((S)-5-(aminomethyl)-2-oxooxazolidin-3-yl)-2-fluorophenyl)piperazine-1-carboxylate 
• 24065-33-6 5-Chlorothiophene-2-carboxylic acid 

Relevant articles and documents

Discovery of the novel antithrombotic agent 5-chloro-N-({(5S)-2-oxo-3-[4- (3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide (BAY 59-7939): An oral, direct factor Xa inhibitor

Despite recent progress in antithrombotic therapy, there is still an unmet medical need for safe and orally available anticoagulants. The coagulation enzyme Factor Xa (FXa) is a particularly promising target, and recent efforts in this field have focused on the identification of small-molecule inhibitors with good oral bioavailability. We identified oxazolidinone derivatives as a new class of potent FXa inhibitors. Lead optimization led to the discovery of BAY 59-7939 (5), a highly potent and selective, direct FXa inhibitor with excellent in vivo antithrombotic activity. The X-ray crystal structure of 5 in complex with human FXa clarified the binding mode and the stringent requirements for high affinity. The interaction of the neutral ligand chlorothiophene in the S1 subsite allows for the combination of good oral bioavailability and high potency for nonbasic 5. Compound 5 is currently under clinical development for the prevention and treatment of thromboembolic diseases.