1423218-40-9Relevant academic research and scientific papers
PROCESS FOR THE PREPARATION OF SILODOSIN
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, (2021/10/15)
The present invention relates to a new process of preparation of Silodosin, or a pharmaceutically acceptable salt thereof. Another aspect of the invention concerns compounds of formula II: or their pharmaceutically acceptable salts thereof, and their use for the preparation of Silodosin or a pharmaceutically acceptable salt thereof.
Convergent synthesis of (R)-silodosin via decarboxylative cross-coupling
Baran, Phil S.,Chen, Tie-Gen,Delbrayelle, Dominique,Echeverria, Pierre-Georges,Jentzer, Olivier,Mele, Lucas,Vantourout, Julien C.
, (2021/08/06)
A new approach to Silodosin capitalizing on a radical retrosynthetic strategy to dissect the molecule into two halves is reported. Using a reductive decarboxylative cross-coupling, a simple indoline can be coupled to a chiral pool-derived fragment to arrive at the target in only seven steps (LLS). This route avoids the use of resolution strategies or asymmetric hydrogenation that requires a subsequent Curtius rearrangement to install a key amino functionality.
METHOD OF PREPARING ADRENERGIC ANTAGONIST
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, (2016/10/10)
PROBLEM TO BE SOLVED: To provide a method of preparing a selective adrenergic antagonist for an α-1A-adrenergic receptor and a useful intermediate thereof. SOLUTION: This invention provides an advantageous production method of a novel intermediate particularly fitted for production on an industrial scale, regarding the production of a pharmaceutical compound represented by formula (I), silodosin: 1-(3-hydroxypropyl)-5-[(2R)-({2-[2-[2-(2,2,2-trifluoroethoxy) phenoxy]ethyl}amino) propyl]indoline-7-carboxamide, or salt thereof. COPYRIGHT: (C)2015,JPOandINPIT
Synthesis of Silodosin by Copper-Catalysed C-C Arylation
Calogero, Francesco,Allegrini, Pietro,Attolino, Emanuele,Passarella, Daniele
, p. 6011 - 6016 (2015/09/22)
The synthesis of silodosin, an antidysuria drug, has been accomplished starting from commercially available indoline. The synthetic strategy is based on CuI-catalysed C-C arylation, regioselective cyanation, and diastereoselective reductive amination. The enantiopure compound was obtained by selective crystallisation of a diasteroisomeric mixture.
Enantioselective synthesis of (-)-(R) Silodosin by ultrasound-assisted diastereomeric crystallization
Barve, Indrajeet J.,Chen, Li-Hsun,Wei, Patrick C.P.,Hung, Jui-Te,Sun, Chung-Ming
, p. 2834 - 2843 (2013/04/10)
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.
First asymmetric synthesis of Silodosin through catalytic hydrogenation by using Ir-SIPHOX catalysts
Yan, Pu-Cha,Zhang, Xian-Yi,Hu, Xiao-Wei,Zhang, Bin,Zhang, Xiang-Dong,Zhao, Michael,Che, Da-Qing,Li, Yuan-Qiang,Zhou, Qi-Lin
, p. 1449 - 1451 (2013/04/10)
An asymmetric synthesis of Silodosin was accomplished in high yield via catalytic hydrogenation of α,β-unsaturated carboxylic acid derivatives by using chiral catalyst Ir-SIPHOX, followed by Curtius rearrangement. Copyright
