1415089-57-4

Basic information

• Product Name: 2-(difluoromethyl)-5-(isobutyramidomethyl)-N-(4-methyl-5-(4-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)nicotinamide phosphoric acid
• Synonyms: 2-(difluoromethyl)-5-(isobutyramidomethyl)-N-(4-methyl-5-(4-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)nicotinamide phosphoric acid
• CAS NO: 1415089-57-4
• Molecular Weight: 593.447
• Mol File: 1415089-57-4.mol

Chemical Properties

• CAS DataBase Reference: 2-(difluoromethyl)-5-(isobutyramidomethyl)-N-(4-methyl-5-(4-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)nicotinamide phosphoric acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(difluoromethyl)-5-(isobutyramidomethyl)-N-(4-methyl-5-(4-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)nicotinamide phosphoric acid(1415089-57-4)
• EPA Substance Registry System: 2-(difluoromethyl)-5-(isobutyramidomethyl)-N-(4-methyl-5-(4-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)nicotinamide phosphoric acid(1415089-57-4)

Safety Data

• Hazardous Substances Data: 1415089-57-4(Hazardous Substances Data)

Upstream product

• 1415090-10-6 ethyl 5-(((tert-butoxycarbonyl)amino)methyl)-2-(difluoromethyl)nicotinate 
• 1415089-74-5 4-methyl-5-(4-(trifluoromethyl)phenyl)-1H-imidazol-2-amine 
• 1415089-72-3 2-(difluoromethyl)-5-(isobutyramidomethyl)nicotinic acid 
• 1086400-66-9 (Z)-2-(ethoxymethylene)-4,4-difluoro-3-oxobutanoic acid ethyl ester 
• 352-24-9 ethyl 4,4-difluoro-3-oxobutyrate 
• 1415089-24-5 2-(difluoromethyl)-5-(isobutyramidomethyl)-N-(4-methyl-5-(4-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)nicotinamide 
• 1415089-73-4 2-methyl-3-(4-(trifluoromethyl)phenyl)imidazo[1,2-a]-pyrimidine 
• 1415089-71-2 ethyl 2-(difluoromethyl)-5-(isobutyramidomethyl)nicotinate 
• 1415089-65-4 ethyl 5-cyano-2-(difluoromethyl)nicotinate 
• 1346539-82-9 ethyl 5-bromo-2-(difluoromethyl)nicotinate 
• 1346535-38-3 ethyl 5-bromo-2-formylnicotinate 
• 95728-57-7 2-bromo-1-(4-trifluoromethylphenyl)propan-1-one 
• 711-33-1 4-trifluoromethyl propiophenone 
• 129477-21-0 ethyl 5-bromo-2-methyl-pyridine-3-carboxylate 

Relevant articles and documents

Discovery and Characterization of 2-Acylaminoimidazole Microsomal Prostaglandin e Synthase-1 Inhibitors

As part of a program aimed at the discovery of antinociceptive therapy for inflammatory conditions, a screening hit was found to inhibit microsomal prostaglandin E synthase-1 (mPGES-1) with an IC50 of 17.4 μM. Structural information was used to improve enzyme potency by over 1000-fold. Addition of an appropriate substituent alleviated time-dependent cytochrome P450 3A4 (CYP3A4) inhibition. Further structure-activity relationship (SAR) studies led to 8, which had desirable potency (IC50 = 12 nM in an ex vivo human whole blood (HWB) assay) and absorption, distribution, metabolism, and excretion (ADME) properties. Studies on the formulation of 8 identified 8·H3PO4 as suitable for clinical development. Omission of a lipophilic portion of the compound led to 26, a readily orally bioavailable inhibitor with potency in HWB comparable to celecoxib. Furthermore, 26 was selective for mPGES-1 inhibition versus other mechanisms in the prostanoid pathway. These factors led to the selection of 26 as a second clinical candidate.

Novel Imidazole Derivatives Useful for the Treatment of Arthritis

The present invention provides compounds of the formula below: where A, X and R1-R6 are as described herein, a pharmaceutical salt thereof, and a pharmaceutical composition containing this compound; methods of treating pain associated with osteoarthritis using one of the compounds or a pharmaceutically acceptable salt thereof, and processes for preparing the compounds.