872018-43-4

Basic information

• Product Name: (S)-2-(4-cyano-3-fluorophenyl)-2-oxoethyl 2-(tertbutoxycarbonylamino)-3-phenylpropanoate
• Synonyms: (S)-2-(4-cyano-3-fluorophenyl)-2-oxoethyl 2-(tertbutoxycarbonylamino)-3-phenylpropanoate
• CAS NO: 872018-43-4
• Molecular Weight: 426.444
• Mol File: 872018-43-4.mol

Chemical Properties

• CAS DataBase Reference: (S)-2-(4-cyano-3-fluorophenyl)-2-oxoethyl 2-(tertbutoxycarbonylamino)-3-phenylpropanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-(4-cyano-3-fluorophenyl)-2-oxoethyl 2-(tertbutoxycarbonylamino)-3-phenylpropanoate(872018-43-4)
• EPA Substance Registry System: (S)-2-(4-cyano-3-fluorophenyl)-2-oxoethyl 2-(tertbutoxycarbonylamino)-3-phenylpropanoate(872018-43-4)

Safety Data

• Hazardous Substances Data: 872018-43-4(Hazardous Substances Data)

Upstream product

• 153556-42-4 4-bromo-3-fluorobenzoic acid 
• 177787-22-3 4-cyano-3-fluoro-benzoyl chloride 
• 176508-81-9 4-cyano-3-fluorobenzoic acid 
• 366790-50-3 4-(2-bromoacetyl)-2-fluorobenzonitrile 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 

Downstream Products

• 872017-92-0 (S)-tert-butyl 1-(4-(4-cyano-3-fluorophenyl)-1H-imidazol-2-yl)-2-phenylethylcarbamate 

Relevant articles and documents

Phenylimidazoles as potent and selective inhibitors of coagulation factor XIa with in vivo antithrombotic activity

Novel inhibitors of FXIa containing an (S)-2-phenyl-1-(4-phenyl-1H-imidazol-2-yl)ethanamine core have been optimized to provide compound 16b, a potent, reversible inhibitor of FXIa (Ki = 0.3 nM) having in vivo antithrombotic efficacy in the rabbit AV-shunt thrombosis model (ID50 = 0.6 mg/kg + 1 mg kg-1 h-1). Initial analog selection was informed by molecular modeling using compounds 11a and 11h overlaid onto the X-ray crystal structure of tetrahydroquinoline 3 complexed to FXIa. Further optimization was achieved by specific modifications derived from careful analysis of the X-ray crystal structure of the FXIa/11h complex. Compound 16b was well tolerated and enabled extensive pharmacologic evaluation of the FXIa mechanism up to the ID90 for thrombus inhibition.

ARYLPROPIONAMIDE, ARYLACRYLAMIDE, ARYLPROPYNAMIDE, OR ARYLMETHYLUREA ANALOGS AS FACTOR XIA INHIBITORS

The present invention provides compounds of Formula (I): Formula (I) or a stereoisomer, tautomer, pharmaceutically acceptable salt or solvate form thereof, wherein the variables A, L1, M and R11 are as defined herein. The compounds of Formula (I) are selective inhibitors of serine protease enzymes of the coagulation cascade and/or contact activation system; for example thrombin, factor Xa, factor XIa, factor IXa, factor VIIa and/or plasma kallikrein. In particular, it relates to compounds that are selective factor XIa inhibitors. This invention also relates to pharmaceutical compositions comprising these compounds and methods of treating thromboembolic and/or inflammatory disorders using the same.