209960-58-7

Usage

Uses

Used in Pharmaceutical Research and Development:
2-(3-CYANO-4-FLUORO-PHENYL)-5-TRIFLUORO-METHYL-2H-PYRAZOLE-3-CARBOXYLIC ACID is used as a chemical entity in pharmaceutical research for its potential biological activity. 2-(3-CYANO-4-FLUORO-PHENYL)-5-TRIFLUORO-METHYL-2H-PYRAZOLE-3-CARBOXYLIC ACID's specific properties and uses are under investigation to determine its efficacy and safety in various therapeutic applications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2-(3-CYANO-4-FLUORO-PHENYL)-5-TRIFLUORO-METHYL-2H-PYRAZOLE-3-CARBOXYLIC ACID serves as a starting material or a building block for the synthesis of new drug candidates. Its unique structural elements, including the pyrazole core and the substituents, may offer novel mechanisms of action or selectivity towards specific biological targets.
Used in Drug Discovery:
2-(3-CYANO-4-FLUORO-PHENYL)-5-TRIFLUORO-METHYL-2H-PYRAZOLE-3-CARBOXYLIC ACID is utilized in drug discovery processes to identify new lead compounds with potential therapeutic benefits. Its chemical structure may be optimized through medicinal chemistry techniques to enhance its pharmacokinetic and pharmacodynamic profiles for specific indications.
Note: Since the provided materials do not specify the exact applications or industries for 2-(3-CYANO-4-FLUORO-PHENYL)-5-TRIFLUORO-METHYL-2H-PYRAZOLE-3-CARBOXYLIC ACID, the uses listed are general and based on the compound's potential in pharmaceutical and chemical research contexts. Further investigation would be required to determine specific applications and industries.

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

• 754193-45-8 2-(3-cyano-4-fluoro-phenyl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl chloride 
• 503615-25-6 1-(4-{2-[1-(3-amino-1,2-benzisoxazol-5-yl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]-2-oxoethyl}-3-fluorophenyl)-2(1H)-pyridinone trifluoroacetate 
• 503614-66-2 2-fluoro-5-[5-{[2-fluoro-4-(2-oxo-1(2H)-pyridinyl)phenyl]acetyl}-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzonitrile 
• 1117747-30-4 methyl 3-[1-(3-cyano-4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]-2-[2-fluoro-4-(2-oxo-1(2H)-pyridinyl)phenyl]-3-oxopropanoate 
• 540510-46-1 [1-(4-{[2-(3-amino-benzo[d]isoxazol-5-yl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl]-amino}-3-fluoro-phenyl)-1H-imidazol-2-ylmethyl]-methyl-carbamic acid benzyl ester 
• 540510-45-0 benzyl {1-[4-({[1-(3-cyano-4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]carbonyl}amino)-3-fluorophenyl]-1H-imidazol-2-yl}methyl(methyl)carbamate 
• 540510-50-7 N-[4-[(2-t-butyldimethylsilyloxymethyl)-1H-imidazol-1-yl]-2-fluorophenyl]-1-(3-amino-1,2-benzisoxazol-5-yl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide 
• 1026874-23-6 2-(3-cyano-4-fluoro-phenyl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid [4-(3-tert-butylsulfamoyl-pyridin-4-yl)-2-fluoro-phenyl]-amide 
• 540510-49-4 N-[4-[(2-tert-butyldimethylsilyloxymethyl)-1H-imidazol-1-yl]-2-fluorophenyl]-1-(3-cyano-4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide 
• 754193-52-7 1-(3'-cyano-4'-fluorophenyl)-3-trifluoromethyl-N-[2-fluoro-4-[(2'-pyrrolidin-1-ylmethyl)imidazol-1-yl]phenyl]-1H-pyrazole-5-carboxyamide 
• 218298-94-3 1-(3'-aminobenzisoxazol-5'-yl)-3-trifluoromethyl-5-[2-fluoro-4-(N-pyrrolidinocarbonyl)phenyl-aminocarbonyl]pyrazole 

Relevant academic research and scientific papers

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.

Process for the preparation of 1,3,5-trisubstituted pyrazoles via [3+2] cycloaddition

A process for the preparation of 1,3,5-trisubstituted pyrazole compounds, which are useful intermediates in the synthesis of factor Xa inhibitors.

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).

Synthesis of 1,3,5-trisubstituted pyrazoles

A novel process for making 1,3,5-trisubstituted pyrazoles of the type shown below from appropriate phenyl hydrazines is described. These compounds are useful as factor Xa inhibitors.