175870-40-3

Upstream product

• 87-69-4 L-Tartaric acid 
• 1374461-74-1 1-[3-(benzyloxy)propyl]-5-[(2R)-2-{[(1R)-1-phenylethyl]amino}propyl]indoline-7-carbonitrile 
• 1374461-73-0 1-[3-(benzyloxy)propyl]-5-[(2R)-2-([(1R)-1-phenylethyl]{2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]indoline-7-carbonitrile 
• 459868-64-5 1-[3-(benzyloxy)propyl]indoline 
• 1375180-30-5 1-[3-(benzyloxy)propyl]-5-formylindoline-7-carbonitrile 
• 459868-63-4 1-[3-(benzyloxy)propyl]indoline-5-carbaldehyde 
• 1375180-28-1 1-[3-(benzyloxy)propyl]-7-bromoindoline-5-carbaldehyde 
• 1374461-77-4 1-[3-(benzyloxy)propyl]-5-(2-nitroprop-1-en-1-yl)indoline-7-carbonitrile 
• 1096141-50-2 1-[3-(benzyloxy)propyl]-2,3-dihydro-5-(2-oxopropyl)-1H-indole-7-carbonitrile 
• 459868-77-0 2,3-dihydro-1-[3-(phenylmethoxy)propyl]-5-[(2R)-2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-indole-7-carbonitrile 
• 160969-00-6 1-(2-bromoethoxy)-2-(2,2,2-trifluoroethoxy)benzene 
• 26420-79-1 1-chloro-3-benzyloxypropane 
• 100-39-0 benzyl bromide 

Downstream Products

• 160970-54-7 silodosin 

Relevant academic research and scientific papers

METHOD FOR PREPARING SILODOSIN AND INTERMEDIATE THEREOF

Provided is a method for preparing silodosin. Also provided is a method for preparing an organic acid salt of a new intermediate 3-(7-cyano-5-((R)-2-((R)-1-phenylethylamino)propyl)-1-hydrogen-indolyl) propyl alcohol (ester or ether), and a new intermediate 3-(7-cyano-5-((R)-2-(((R)-1-phenethyl)(2-(2-(trifluoroethoxy)phenoxy) ethyl)amino)propyl)1-hydrogen-indolyl)propyl alcohol (ester or ether) and a salt thereof. The method has the following advantages: raw materials are cheap and easy to obtain, the operation is simple, the intermediate and product are easy to purify, the yield is high, and the method is applicable to industrial production.

A METHOD OF MANUFACTURING (-)-L-(3-HYDROXYPROPYL)-5-[(2R)-2-({2,2,2-TRIFLUOROETHOXY)- PHENOXYETHYL}AMINO)PROPYL]-2,3-DIHYDRO-LH-INDOLE-7-CARBOXAMIDE

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.