Indoline compound and process for producing the same

Details Indoline compound and process for producing the same Indoline compound and process for producing the same

C - Chemistry, Metallurgy

07

D

C07D 209/42 (2006.01)

Patent

CA 2583660

A process for industrially producing silodosin, which is a therapeutic agent for urination disorders accompanying prostatic hypertrophy. The process for silodosin production is characterized by mixing 3-{7-cyano-5-[(2R)-2-({2~[2- (2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]-2,3~dihydro-1H-indol-1- yl}propyl benzoate with oxalic acid to yield an oxalate, subsequently hydrolyzing the oxalate to yield 1-(3-hydroxypropyl)-5-[(2R)-2-({2-[2-(2,2,2- trifluoro~ethoxy)phenoxy]ethyl}amino)propyl]-2,3-dihydro-1H-indole-7- carbonitrile, and hydrolyzing it. Also provided is an intermediate for use in the production.

La présente invention a pour objet un procédé de synthèse industrielle de la silodosine, un agent thérapeutique destiné à lutter contre les troubles urinaires accompagnant l'hypertrophie de la prostate. Ledit procédé est caractérisé en ce qu~il inclut une étape de mélange de benzoate de 3-{7-cyano-5-[(2R)-2-({2­[2-(2,2,2-trifluoroéthoxy)phénoxy]éthyl}amino)propyl]-2,3­-dihydro-1H-indol-1-yl}propyle et d~acide oxalique pour obtenir un oxalate, une étape d'hydrolyse dudit oxalate pour obtenir le 1-(3-hydroxypropyl)-5-[(2R)-2-({2-[2-(2,2,2-trifluoro­éthoxy)phénoxy]éthyl}amino)propyl]-2,3-dihydro-1H-indole-7-carbonitrile, et une étape d~hydrolyse de ce dernier composé. La présente invention a également pour objet un intermédiaire de ce procédé de synthèse.

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