1374461-77-4Relevant academic research and scientific papers
A METHOD OF MANUFACTURING (-)-L-(3-HYDROXYPROPYL)-5-[(2R)-2-({2,2,2-TRIFLUOROETHOXY)- PHENOXYETHYL}AMINO)PROPYL]-2,3-DIHYDRO-LH-INDOLE-7-CARBOXAMIDE
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, (2012/05/31)
A method of manufacturing optically pure or optically enriched silodosin of formula I and of its pharmaceutically acceptable salts, in which a secondary amine of general formula II, wherein Bn denotes a phenylmethyl group, substituted or unsubstituted in the benzene ring, e.g. benzyl or 4-methoxybenzyl, or the benzhydryl or trityl group, (a) is N-alkylated with an alkylating agent of general formula III, wherein X denotes a good leaving group, such as a halogen or an alkane sulfonyloxyl group RS020 or an arene SLilfonyloxyl group ArS020, R means an alkyl group with 1 to 4 carbon atoms and Ar is a substituted or unsubstituted phenyl group; (b) the obtained tertiary amine of general formula IV, wherein Bn is as defined above, is hydrogenolyzed with hydrogen on a metal catalyst; (c) and the resulting nitrile of formula V, wherein Bn is as defined above, is hydrolyzed by treatment with alkaline agents; and optionally, (d) additional O-debenzylation of the amide-ether of general formula VI, wherein Bn is as defined above, with dealkylating agents is carried out; and, if desired, the obtained silodosin is transformed to the respective salts by treatment with pharmaceutically acceptable acids.
