885692-72-8

Basic information

• Product Name: 4-cyano-1H-imidazole-2-carboxylic acid {2-cyclohex-1-enyl-4-[1-(R)-(+)-(2,3-dihydroxypropionyl)piperidin-4-yl]phenyl}amide
• Synonyms: 4-cyano-1H-imidazole-2-carboxylic acid {2-cyclohex-1-enyl-4-[1-(R)-(+)-(2,3-dihydroxypropionyl)piperidin-4-yl]phenyl}amide
• CAS NO: 885692-72-8
• Molecular Weight: 463.536
• Mol File: 885692-72-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4-cyano-1H-imidazole-2-carboxylic acid {2-cyclohex-1-enyl-4-[1-(R)-(+)-(2,3-dihydroxypropionyl)piperidin-4-yl]phenyl}amide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-cyano-1H-imidazole-2-carboxylic acid {2-cyclohex-1-enyl-4-[1-(R)-(+)-(2,3-dihydroxypropionyl)piperidin-4-yl]phenyl}amide(885692-72-8)
• EPA Substance Registry System: 4-cyano-1H-imidazole-2-carboxylic acid {2-cyclohex-1-enyl-4-[1-(R)-(+)-(2,3-dihydroxypropionyl)piperidin-4-yl]phenyl}amide(885692-72-8)

Safety Data

• Hazardous Substances Data: 885692-72-8(Hazardous Substances Data)

Upstream product

• 214360-73-3 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline 
• 138647-49-1 4-Trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 
• 885693-41-4 4-cyano-1H-imidazole-2-carboxylic acid {2-cyclohex-1-enyl-4-[1-(R)-(+)-(2,2-dimethyl[1,3]dioxolane-4-carbonyl)piperidin-4-yl]phenyl}amide 
• 885693-02-7 (4-{[4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carbon-yl]-amino}-3-cyclohex-1-enyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 885693-01-6 4-(4-amino-3-cyclohex-1-enyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 885693-00-5 4-(4-amino-3-bromophenyl)piperidine-1-carboxylic acid tert-butyl ester 
• 170011-57-1 tert-butyl 4-(4-aminophenyl)piperidin-1-carboxylate 
• 873454-43-4 4-(4-aminophenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Optimization of a potent class of arylamide colony-stimulating factor-1 receptor inhibitors leading to anti-inflammatory clinical candidate 4-cyano-N -[2-(1-cyclohexen-1-yl)-4-[1-[(dimethylamino)acetyl]-4-piperidinyl]phenyl]-1 H -imidazole-2-carboxamide (JNJ-28312141)

A class of potent inhibitors of colony-stimulating factor-1 receptor (CSF-1R or FMS), as exemplified by 8 and 21, was optimized to improve pharmacokinetic and pharmacodynamic properties and potential toxicological liabilities. Early stage absorption, distribution, metabolism, and excretion assays were employed to ensure the incorporation of druglike properties resulting in the selection of several compounds with good activity in a pharmacodynamic screening assay in mice. Further investigation, utilizing the type II collagen-induced arthritis model in mice, culminated in the selection of anti-inflammatory development candidate JNJ-28312141 (23, FMS IC50 = 0.69 nM, cell assay IC50 = 2.6 nM). Compound 23 also demonstrated efficacy in rat adjuvant and streptococcal cell wall-induced models of arthritis and has entered phase I clinical trials.