Process for the preparation of tamsulosin

Details Process for the preparation of tamsulosin Process for the preparation of tamsulosin

C - Chemistry, Metallurgy

07

C

C07C 303/40 (2006.01) C07B 57/00 (2006.01) C07C 311/37 (2006.01)

Patent

CA 2607809

The invention includes an improved process for producing tamsulosin comprising reacting 5-(2-aminopropyl)-2-methoxybenzenesulfonamide with 2-(o- ethoxyphenoxy)ethyl bromide in an organic phosphite solvent to obtain tamsulosin. Optically pure (R)- 5-(2-aminopropyl)-2- methoxybenzenesulfonamide can be employed to produce optically pure (R)-tamsulosin product. The organic phosphite solvent utilized in the reaction can include tri-alkyl phosphites such as triethyl phosphite, trimethyl phosphite, and tributyl phosphite. Additionally, processes for producing tamsulosin having a low concentration of by-product contaminants, such as 5-((R)-2- {Bis-[2-(2- ethoxyphenoxy)ethyl]amino}-propyl)-2-methoxybenzenesulfonamide, and the use of such by-products to monitor the chemical purity of tamsulosin, are provided.

L'invention concerne un procédé amélioré de production de tamsulosine qui consiste à faire réagir du 5-(2-aminopropyl)-2-méthoxybenzènesulfonamide avec du 2-(o-éthoxyphénoxy)éthyl bromure dans un solvant phosphite organique afin d'obtenir de la tamsulosine. Du (R)-5-(2-aminopropyl)-2-méthoxybenzènesulfonamide optiquement pur peut être utilisé afin d'obtenir un produit (R)-tamsulosine optiquement pur. Le solvant phosphite organique utilisé dans la réaction peut comprendre des tri-alkyl phosphites de type triéthyl phosphite, triméthyl phosphite, et tributyl phosphite. L'invention concerne en outre des procédés de production de tamsulosine présentant une faible concentration en sous-produits contaminants, de type 5-((R)-2- {Bis-[2-(2-éthoxyphénoxy)éthyl]amino}-propyl)-2-méthoxybenzènesulfonamide, et l'utilisation de ces sous-produits pour contrôler la pureté chimique de la tamsulosine.

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