Anirolac

Originator

Anirolac,Syntex Inc.

Uses

Antiinflammatory; analgesic.

Uses

Anirolac is a nonsteroidal anti-inflammatory drug with analgesic properties. Study suggests that pain relief due to Anirolac is equivalent to that of Naproxen (N377520).

Manufacturing Process

A solution of 1.1 equivalent of N,N-dimethyl-p-methoxybenzamide and 1 equivalent of phosphorous oxychloride in 2 ml of 1,2-dichloroethane is refluxed for 30 minutes. To this solution is added a solution of 1 equivalent of isopropyl 1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate in 2 ml of 1,2- dichloroethane. The reaction mixture is refluxed under an argon atmosphere for 8 hours, treated with equivalent of sodium acetate and refluxed for a further 5 hours. The resultant mixture is then evaporated to dryness and the residue is chromatographed on 12 g of silica gel, eluting with hexane: ethyl acetate (3:1), monitoring the course of the reaction by TLC. Isopropyl 5-pmethoxybenzoyl- 1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate was obtained as an oil. UV, IR, NMR spectrum confirmed the structure of obtained compound.
A solution of 1 equivalent of isopropyl 5-p-methoxybenzoyl-1,2-dihydro-3Hpyrrolo[ 1,2-a]pyrrole-1-carboxylate in 10 ml of methanol is treated with a solution of 1 equivalent of potassium carbonate in 5 ml of water. The reaction mixture is refluxed under nitrogen atmosphere for 30 minutes, cooled, and evaporated to dryness. The residue is taken up in 10 ml of 10% aqueous hydrochloric acid and 50 ml of water and the resultant mixture extracted with ethyl acetate (2x50 ml). The combined extracts are dried over magnesium sulfate and evaporated to dryness under reduced pressure. Crystallization of the residue from ethyl acetate-hexane affords 5-p-methoxybenzoyl-1,2- dihydro-3H-pyrrolo[1, 2-a]pyrrole-1-carboxylic acid (anirolac); MP: 187°- 187.5°C.

Therapeutic Function

Antiinflammatory, Analgesic

Raw materials

Preparation Products