PROCESS FOR THE PREPARATION OF R-(-)-TAMSULOSIN HYDROCHLORIDE AND NOVEL INTERMEDIATES

New process for industrial preparation of R-(-)-tamsulosine HCl of formula (I). In this process (R,S)-5-[2-(N-benzyl-amino)-propyl]-2-methoxy-benzenesulphonamide of formula (I), acid addition salts and enantiomers thereof and R-5-[2-[N-(2-ethoxy-phenoxy)-ethyl]-N­benzyl]-amino]-propyl-2-methoxy-benz...

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Main Authors FOGASSY ELEMER DR, TOERLEY JOZSEF, DEMETER ADAM, GIZUR TIBOR DR, EGRI GABRIELLA DR, BALINT JOZSEF DR
Format Patent
LanguageEnglish
Published 29.01.2007
Edition7
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Summary:New process for industrial preparation of R-(-)-tamsulosine HCl of formula (I). In this process (R,S)-5-[2-(N-benzyl-amino)-propyl]-2-methoxy-benzenesulphonamide of formula (I), acid addition salts and enantiomers thereof and R-5-[2-[N-(2-ethoxy-phenoxy)-ethyl]-N­benzyl]-amino]-propyl-2-methoxy-benzenesulphonamide of formula (III) are new intermediates. R-(-)-tamsulosine HCl of formula (I) is prepared by reacting the secondary benzylamine of formula (II) with an alkylating agent to R-5-[2-[N-(2-ethoxy-phenoxy)-ethyl]-N-benzyl]­amino]-propyl-2-methoxy-benzenesulphonamide of formula (III), the benzyl protecting group is removed and then HCl salt is formed. The optically active compound of formula (II) is prepared by reductive condensation of (4-methoxy-3-sulphamoyl-phenyl)-acetone and benzylamine and the obtained racemic compound is optically resolved by chiral acid.
Bibliography:Application Number: HUP0202963