161024-53-9

Upstream product

• 160969-03-9 1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene 
• 175837-01-1 1-acetyl-5-(2-aminopropyl)-2,3-dihydro-1H-indole-7-carbonitrile 

Downstream Products

• 160969-20-0 tert-butyl [(2R)-1-(7-cyanoindolin-5-yl)propan-2-yl]-{2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}carbamate 
• 1423218-40-9 tert-butyl (2R)-(1-(1-(3-benzyloxypropyl)-7-cyanoindolin-5-yl)propane-2-yl)-N-(2-(2-(2,2,2-trifluoroethoxy)phenoxy)ethyl)carbamate 
• 1427271-99-5 (R)-tert-butyl(1-(7-cyano-1-(3-hydroxypropyl)indolin-5-yl)propan-2-yl)(2-(2-(2,2,2-trifluoroethoxy)phenoxy)ethyl)carbamate 
• 885340-13-6 1-(3-hydroxypropyl)-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]-2,3-dihydro-1H-indole-7-carbonitrile 
• 1427272-02-3 (R)-tert-butyl(1-(1-allyl-7-cyanoindolin-5-yl)propan-2-yl)(2-(2-(2,2,2-trifluoroethoxy)phenoxy)ethyl)carbamate 
• 160970-54-7 silodosin 
• 160969-12-0 (R)-tert-butyl(1-(1-acetyl-7-cyanoindolin-5-yl)propan-2-yl)(2-(2-(2,2,2-trifluoroethoxy)phenoxy)ethyl)carbamate 

Relevant academic research and scientific papers

Enantioselective synthesis of (-)-(R) Silodosin by ultrasound-assisted diastereomeric crystallization

Enantioselective synthesis of clinically approved drug - Silodosin for the treatment of benign prostatic hyperplasia from the commercially available compounds 1-acetyl-5-(2-aminopropyl) indoline-7-carbonitrile A and 2-(2-(2,2,2-trifluoroethoxy)phenoxy)ethyl methanesulfonate C is explored. Key step in the synthesis is chiral resolution of intermediate 1, which was achieved by a simple diastereomeric crystallization using (S)-(+)-mandelic acid assisted by ultrasonication. The present synthetic strategy has lesser number of steps and is vastly improved the overall yield in this short route towards target compound - Silodosin.

1,5,7-trisubstituted indoline compounds and salts thereof

Indoline compounds represented by the formula: STR1 wherein R represents a saturated or unsaturated aliphatic acyl group which may have one or more halogen atoms, a hydroxy group, a lower alkoxy group, a carboxy group, a lower alkoxycarbonyl group, a cycloalkyl group or an aryl group as substituents; a hydroxyalkyl group; an aliphatic acyloxyalkyl group; a lower alkyl group having a lower alkoxy group, a carboxy group, a lower alkoxycarbonyl group, an aryl substituted lower alkoxycarbonyl group, a carbamoyl group, a mono- or dialkyl substituted carbamoyl group or a cyano group as substituents; an aromatic acyl group which may have one or more halogen atoms as substituents; a furoyl group or a pyridylcarbonyl group; R1 represents a lower alkyl group which may have one or more halogen atoms or an aryl group as substituents; and pharmaceutically acceptable salts thereof, exhibit a selective suppressive action on urethral contractions, and thus are useful as therapeutic agents for the treatment of dysuria with less hypotension including postural hypotension.