66898-62-2

White to pale yellow crystalline powder

Somalgen,Bago,Argentina,1972

Anti-inflammatory; analgesic.

ChEBI: 2-[3-(trifluoromethyl)anilino]-3-pyridinecarboxylic acid (3-oxo-1H-isobenzofuran-1-yl) ester is a member of benzofurans.

49 ml of triethylamine were added to a suspension of 2-(3'- trifluoromethylanilino)nicotinic acid (70.6 g in 250 ml of dimethylformamide). After stirring for 30 minutes 53.3 g of 3-bromophthalide were added. The reaction mixture was maintained at 25°C to 30°C during 4 hours. Ethyl acetate (750 ml) was poured into the reaction mixture. This solution was filtered and extracted with water (4 x 250 ml), discarding the water layer.
The organic layer was dried with anhydrous magnesium sulfate and then filtered. The solution was concentrated under vacuum at 30°C to 35°C until reduced to half of its original volume and then cooled to 5°C to allow the crystallization of the compound. Thus, the cake was filtered, washed with cool ethyl acetate, and dried under vacuum. Yield: 74% (76.7 g) of phthalidyl ester of 2-(3'-trifluoromethylanilino)-pyridin-3-carboxylic acid, melting point: 165°C to 167°C.

Somalgen (Laboratorio Bago, S.A., Argentina).

Antiinflammatory, Analgesic

Calcium-activated chloride channel (hCLCA1/mCLCA3) blocker; reduces mucin synthesis and release in cell culture and animal models. Possesses anti-inflammatory actions via inhibition of cyclooxygenases and inhibits Cl - /HCO 3 - exchanger activity. Increases survival in a cystic fibrosis mouse model of distal intestinal obstructive syndrome.