Silodosin

CAT#: H319611

CAS#: 160970-54-7

Description: Silodosin is an α1-adrenoceptor antagonist approved for the symptomatic treatment of benign prostatic hyperplasia. It acts as an α1-adrenoceptor antagonist with high uroselectivity (selectivity for the prostate). Since silodosin has high affinity for the α1A adrenergic receptor, it causes practically no orthostatic hypotension (in contrast to other α1 blockers). On the other side, the high selectivity seems to be the cause of silodosin's typical side effect of retrograde ejaculation.

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Synthetic Routes

Silodosin - Synthetic Route 1

Silodosin route01

Synthetic reference

Yamaguchi, Toshiaki; Tsuchiya, Ikuo; Kikuchi, Ken; Yanagi, Takashi. Process for preparation of silodosin. Assignee Kissei Pharmaceutical Co., Ltd., Japan. WO 2006046499. (2006).

Silodosin - Synthetic Route 2

Silodosin route02

Synthetic reference

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. First asymmetric synthesis of Silodosin through catalytic hydrogenation by using Ir-SIPHOX catalysts. Tetrahedron Letters. Volume 54. Issue 11. Pages 1449-1451. 2013.

Silodosin - Synthetic Route 3

Silodosin route03

Synthetic reference

Barve, Indrajeet J.; Chen, Li-Hsun; Wei, Patrick C. P.; Hung, Jui-Te; Sun, Chung-Ming. Enantioselective synthesis of (-)-(R) Silodosin by ultrasound-assisted diastereomeric crystallization. Tetrahedron. Volume 69. Issue 13. Pages 2834-2843. 2013.

Silodosin - Synthetic Route 4

Silodosin route04

Synthetic reference

Rajan, Srinivasan; Eswaraiah, Sajja; Mummadi, Venkatesh; Nicholas, Madhu Elevathingal. Process for preparation of indoline derivatives and their pharmaceutical compositions. Assignee MSN Laboratories Limited, India. WO 2012147107. (2012).

Silodosin - Synthetic Route 5

Silodosin route05

Synthetic reference

Jain, Rajesh; Rao, Jagadeeshwar R.; Rao, Siripragada Mahender. Novel process for the synthesis of indoline derivatives. Assignee Panacea Biotec Ltd., India. WO 2012131710. (2012).

Silodosin - Synthetic Route 6

Silodosin route06

Synthetic reference

Reddy, Reguri Buchi; Goud, Venkateshwar Thirumani; Nagabushanam, Nagamani; Ramasamy, Kamala; Devineni, Suresh; Shaik, Mahaboob Basha. An improved process for the preparation of silodosin. Assignee Orchid Chemicals and Pharmaceuticals Limited, India. WO 2012147019. (2012).

Silodosin - Synthetic Route 7

Silodosin route07

Synthetic reference

Gidwani, Ramesh Matioram; Kolhatkar, Mayur Vilas. Process for preparing an intermediate for silodosin. Assignee Ratiopharm GmbH, Germany. WO 2011124704. (2011).

Silodosin - Synthetic Route 8

Silodosin route08

Synthetic reference

Wang, Xiaomei; Wang, Zhefeng; Sui, Qiang; Liu, Qihao; Shi, Huilin. Preparation of optically active indoline compounds. Assignee Zhejiang Huahai Pharmaceutical Co., Ltd., Peop. Rep. China; Shanghai Institute of Pharmaceutical Industry. CN 101993406. (2011).

Silodosin - Synthetic Route 9

Silodosin route09

Synthetic reference

Joshi, Shreerang; Bhuta, Sachin; Talukdar, Sanjay; Sawant, Sudhir; Venkataraman, Deepak; Pise, Abhinay; Metkar, Shashikant; Chavan, Dattatraya; Luthra, Parven Kumar. Preparation of Silodosin and intermediates. Assignee Sandoz AG, India. WO 2011030356. (2011).

Silodosin - Synthetic Route 10

Silodosin route010

Synthetic reference

Vlasakova, Ruzena; Hajicek, Josef; Slavikova, Marketa. Process for preparing (-)-1-(3-hydroxypropyl)-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]-2,3-dihydro-1H-indole-7-carboxamide. Assignee Zentiva, K.S., Czech Rep. WO 2012062229. (2012).