Chemical Properties
White to pale yellow crystalline powder
Originator
Somalgen,Bago,Argentina,1972
Uses
Anti-inflammatory; analgesic.
Definition
ChEBI: 2-[3-(trifluoromethyl)anilino]-3-pyridinecarboxylic acid (3-oxo-1H-isobenzofuran-1-yl) ester is a member of benzofurans.
Manufacturing Process
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.
Brand name
Somalgen (Laboratorio Bago, S.A., Argentina).
Therapeutic Function
Antiinflammatory, Analgesic
Biological Activity
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.
