Process for preparation of bicalutamide

Details Process for preparation of bicalutamide Process for preparation of bicalutamide

C - Chemistry, Metallurgy

07

C

C07C 315/02 (2006.01) C07C 315/06 (2006.01) C07D 317/46 (2006.01)

Patent

CA 2582195

The present invention discloses a process for the synthesis of N-[4-Cyano-3- (trifluoromethyl) phenyl]-3-[(4-fluorophenyl) sulphonyl]-2-hydroxy-2-methyl propanamide (Form I). The invention discloses a reagent for oxidation of N-[4- Cyano-3-(trifluoromethyl) phenyl]-3-[(4-fluorophenyl) thio]-2-hydroxy-2-methyl propanamide to N-[4-Cyano-3-(trifluoromethyl) phenyl]-3-[(4-fluorophenyl) sulphonyl]-2-hydroxy-2-methyl propanamide. More particularly, the invention discloses a method of purification of N-[4-Cyano-3-(trifluoromethyl) phenyl]-3- [(4-fluorophenyl) sulphonyl]-2-hydroxy-2-methyl propanamide in a mixture of methylethyl ketone and hexane giving form (I). This form (I) is useful as an active pharmaceutical and has antiandrogenic activity.

L~invention concerne un procédé de synthèse de N-[4-cyano-3-(trifluorométhyl)phényl]-3-[(4-fluorophényl) sulphonyl]-2-hydroxy-2-méthylpropanamide (Formule I). L~invention concerne également un réactif pour l~oxydation de N-[4-cyano-3-(trifluorométhyl)phényl]-3-[(4-fluorophényl)thio]-2-hydroxy-2-méthylpropanamide en N-[4-cyano-3-(trifluorométhyl)phényl]-3-[(4-fluorophényl)sulphonyl]-2-hydroxy-2-méthylpropanamide. L~invention concerne plus particulièrement une méthode de purification de N-[4-cyano-3-(trifluorométhyl)phényl]-3-[(4-fluorophényl)sulphonyl]-2-hydroxy-2-méthylpropanamide dans un mélange de méthyléthylcétone et d~hexane donnant un composé de formule (I). Ce composé de formule (I) est utile en tant qu~actif pharmaceutique et présente une activité antiandrogénique.

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