209960-58-7

Basic information

• Product Name: 2-(3-CYANO-4-FLUORO-PHENYL)-5-TRIFLUORO-METHYL-2H-PYRAZOLE-3-CARBOXYLIC ACID
• Synonyms: 2-(3-CYANO-4-FLUORO-PHENYL)-5-TRIFLUORO-METHYL-2H-PYRAZOLE-3-CARBOXYLIC ACID
• CAS NO: 209960-58-7
• Molecular Formula: C₁₂H₅F₄N₃O₂
• Molecular Weight: 299.1806128
• Mol File: 209960-58-7.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(3-CYANO-4-FLUORO-PHENYL)-5-TRIFLUORO-METHYL-2H-PYRAZOLE-3-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3-CYANO-4-FLUORO-PHENYL)-5-TRIFLUORO-METHYL-2H-PYRAZOLE-3-CARBOXYLIC ACID(209960-58-7)
• EPA Substance Registry System: 2-(3-CYANO-4-FLUORO-PHENYL)-5-TRIFLUORO-METHYL-2H-PYRAZOLE-3-CARBOXYLIC ACID(209960-58-7)

Safety Data

• Hazardous Substances Data: 209960-58-7(Hazardous Substances Data)

Usage

General Description

2-(3-CYANO-4-FLUORO-PHENYL)-5-TRIFLUORO-METHYL-2H-PYRAZOLE-3-CARBOXYLIC ACID is a chemical compound with the molecular formula C14H7F4N3O2. It is a pyrazole derivative with a carboxylic acid group, as well as cyanide, fluorine, and trifluoromethyl substituents. 2-(3-CYANO-4-FLUORO-PHENYL)-5-TRIFLUORO-METHYL-2H-PYRAZOLE-3-CARBOXYLIC ACID has potential applications in pharmaceutical research and development, as it may possess biological activity. Its specific properties and potential uses would need to be further investigated through laboratory and clinical research.

Upstream product

• 326-90-9 4,4,4-trifluoro-1-(2-furanyl)-1,3-butanedione 
• 53312-81-5 3-cyano-4-fluoroaniline 
• 335275-96-2 ethyl 1-(4-fluoro-3-cyano)phenyl-3-trifluoromethylpyrazole-5-carboxylate 
• 17417-09-3 2-fluoro-5-nitrobenzonitrile 

Downstream Products

• 913176-68-8 5-[6-(4-bromo-phenyl)-7-oxo-3-trifluoromethyl-6,7-dihydro-pyrazolo[4,3-d]pyrimidin-1-yl]-2-fluoro-benzonitrile 
• 913176-82-6 5-{4-amino-5-[(4-bromo-phenyl)-acetyl]-3-trifluoromethyl-pyrazol-1-yl}-2-fluoro-benzonitrile 
• 913176-67-7 4-amino-2-(3-cyano-4-fluoro-phenyl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid (4-bromo-phenyl)-amide 
• 913176-83-7 5-[6-(4-bromo-phenyl)-7-oxo-3-trifluoromethyl-4,7-dihydro-pyrazolo[4,3-b]pyridin-1-yl]-2-fluoro-benzonitrile 
• 913176-85-9 5-[6-(4-bromo-phenyl)-7-oxo-3-trifluoromethyl-4,7-dihydro-pyrazolo[4,3-c]pyridazin-1-yl]-2-fluoro-benzonitrile 
• 913176-66-6 2-(3-cyano-4-fluoro-phenyl)-4-nitro-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid (4-bromo-phenyl)-amide 
• 913176-69-9 5-[6-(4-bromo-phenyl)-5-methyl-7-oxo-3-trifluoromethyl-6,7-dihydro-pyrazolo[4,3-d]pyrimidin-1-yl]-2-fluoro-benzonitrile 
• 913176-73-5 5-[6-(4-bromo-phenyl)-5,7-dioxo-3-trifluoromethyl-4,5,6,7-tetrahydro-pyrazolo[4,3-d]pyrimidin-1-yl]-2-fluoro-benzonitrile 
• 913176-81-5 5-{5-[(4-bromo-phenyl)-cyano-acetyl]-4-nitro-3-trifluoromethyl-pyrazol-1-yl}-2-fluoro-benzonitrile 
• 913176-84-8 5-[5-amino-6-(4-bromo-phenyl)-7-oxo-3-trifluoromethyl-4,7-dihydro-pyrazolo[4,3-b]pyridin-1-yl]-2-fluoro-benzonitrile 
• 913176-80-4 2-(4-bromo-phenyl)-3-[2-(3-cyano-4-fluoro-phenyl)-4-nitro-5-trifluoromethyl-2H-pyrazol-3-yl]-3-oxo-propionic acid methyl ester 
• 280120-78-7 2-fluoro-5-[6-(2'-formyl-biphenyl-4-yl)-7-oxo-3-trifluoromethyl-6,7-dihydro-pyrazolo[4,3-d]pyrimidin-1-yl]-benzonitrile 
• 280120-79-8 2-fluoro-5-[6-(2'-hydroxymethyl-biphenyl-4-yl)-7-oxo-3-trifluoromethyl-6,7-dihydro-pyrazolo[4,3-d]pyrimidin-1-yl]-benzonitrile 

Relevant articles and documents

HUMAN PLASMA KALLIKREIN INHIBITORS

Disclosed are compounds of formula (I), as described herein, and pharmaceutically acceptable salts thereof. The compounds are inhibitors of plasma kallikrein. Also provided are pharmaceutical compositions comprising at least one compound of the invention, and methods involving use of the compounds and compositions of the invention in the treatment and prevention of diseases and conditions characterized by unwanted plasma kallikrein activity.

Discovery of 1-(3′-aminobenzisoxazol-5′-yl)-3-trifluoromethyl- N-[2-fluoro-4-[(2′-dimethylaminomethyl)imidazol-1-yl]phenyl] -1H-pyrazole-5-carboxyamide hydrochloride (razaxaban), a highly potent, selective, and orally bioavailable factor Xa inhibitor

Modification of a series of pyrazole factor Xa inhibitors to incorporate an aminobenzisoxazole as the P1 ligand resulted in compounds with improved selectivity for factor Xa relative to trypsin and plasma kallikrein. Further optimization of the P4 moiety led to compounds with enhanced permeability and reduced protein binding. The SAR and pharmacokinetic profile of this series of compounds is described herein. These efforts culminated in 1-(3′-aminobenzisoxazol-5′-yl)-3-trifluoromethyl-N-[2-fluoro-4- [(2′-dimethylaminomethyl)imidazol-1-yl]phenyl]-1H-pyrazole-5-carboxyamide (11d), a potent, selective, and orally bioavailable inhibitor of factor Xa. On the basis of its excellent in vitro potency and selectivity profile, high free fraction in human plasma, good oral bioavailability, and in vivo efficacy in antithrombotic models, the HCl salt of this compound was selected for clinical development as razaxaban (DPC 906, BMS-561389).