188816-92-4

Upstream product

• 399-06-4 4,4,4-trifluoro-1-(pyridin-4-yl)butane-1,3-dione 
• 17852-52-7 4-hydrazinobenzene-1-sulfonamide hydrochloride 
• 357651-51-5 C₉H₆F₃NO₂ 
• 1122-54-9 methyl (4-pyridyl) ketone 

Downstream Products

• 1085525-56-9 1-methyl-4-[2-(4-sulfamoylphenyl)-5-(trifluoromethyl)-2H-pyrazol-3-yl]pyridinium iodide 
• 627094-65-9 1-(4-aminosulfonylphenyl)-5-(piperidin-4-yl)-3-trifluoromethyl-1H-pyrazole 

Relevant academic research and scientific papers

Synthesis of new 4-[2-(4-methyl(amino)sulfonylphenyl)-5-trifluoromethyl-2H-pyrazol-3-yl]-1,2,3,6-tetrahydropyridines: A search for novel nitric oxide donor anti-inflammatory agents

A group of 4-[2-(4-methyl(amino)sulfonylphenyl)-5-trifluoromethyl-2H-pyrazol-3-yl]-1,2,3,6-tetrahydropyridines (11-14) possessing a variety of substituents (Me, CO2Et, H, N = O) attached to the 1,2,3,6-tetrahydropyridyl N1-nitrogen atom were synthesized and evaluated as anti-inflammatory agents. Structure-activity relationship data showed that the N-methyl-1,2,3,6-tetrahydropyridyl moiety is a suitable bioisosteric replacement for the tolyl moiety in celecoxib. The most potent compound 4-[5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-3-trifluoromethylpyrazol-1-yl]benzenesulfonamide (11b; ED50 = 61.2 mg/kg po) exhibited an anti-inflammatory activity between that of the reference drugs celecoxib (ED50 = 10.8 mg/kg po) and aspirin (ED50 = 128.7 mg/kg po). The synthesis of model hybrid nitric oxide donor N-diazen-1-ium-1,2-diolate derivatives of 4-[2-(4-methyl(amino)sulfonylphenyl)-5-trifluoromethyl-2H-pyrazol-3-yl]-1,2,3,6-tetrahydropyridines (5) requires further investigation since the reaction of 1,2,3,6-tetrahydropyridines with nitric oxide furnished the undesired N-nitroso-1,2,3,6-tetrahydrohydropyridyl product rather than the desired N-diazen-1-ium-1,2-diolate-1,2,3,6-tetrahydropyridyl product.

Substituted pyrazolyl benzenesulfonamides for the treatment of inflammation

A class of pyrazolyl benzenesulfonamide compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula II: STR1 or a pharmaceutically-acceptable salt thereof.

Substituted pyrazolyl benzenesulfonamides for use in veterinary therapies

A method of using pyrazolyl benzenesulfonamide compounds in treating inflammation and inflammation-related disorders in companion animals is disclosed.

Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: Identification of 4-[5-(4-methylphenyl)- 3(trifluoromethyl)-1h-pyrazol-1-yl]benzenesulfonamide (sc-58635, celecoxib)

A series of sulfonamide-containing 1,5-diarylpyrazole derivatives were prepared and evaluated for their ability to block cyclooxygenase-2 (COX-2) in vitro and in vivo. Extensive structure-activity relationship (SAR) work was carried out within this series, and a number of potent and selective inhibitors of COX-2 were identified. Since an early structural lead (1f, SC- 236) exhibited an unacceptably long plasma half-life, a number of pyrazole analogs containing potential metabolic sites were evaluated further in vivo in an effort to identify compounds with acceptable pharmacokinetic profiles. This work led to the identification of 1i (4-[5-(4-methylphenyl)-3- (trifluoromethyl)-1H-pyrazol-1-y1]benzenesulfonamide, SC-58635, celecoxib), which is currently in phase III clinical trials for the treatment of rheumatoid arthritis and osteoarthritis.

Substituted pyrazolyl benzenesulfonamide for the treatment of inflammation

A class of pyrazolyl benzenesulfonamide compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula I: STR1

SUBSTITUTED PYRAZOLYL BENZENESULFONAMIDES

A class of pyrazolyl benzenesulfonamide compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula I: or a pharmaceutically-acceptable salt thereof