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Preparation method of Silodosin

A silodosin and two-substituted technology, applied in the field of silodosin preparation, can solve the problems affecting the industrialization process, poor selectivity, difficult sources, etc., and achieve the effects of promoting economic and technological development, controlling costs, and simplifying the process

Inactive Publication Date: 2015-04-08
南京联智医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method solves the shortcomings of poor condensation reaction selectivity and low yield in the aforementioned method, but due to the source of raw material 2-[2-(2,2,2-trifluoroethoxy)phenoxy]acetaldehyde (X) Relatively difficult, affecting the industrialization process of the process

Method used

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  • Preparation method of Silodosin
  • Preparation method of Silodosin
  • Preparation method of Silodosin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Add 1-(3-hydroxypropyl)-7-cyano-5-(2-oxopropyl)indoline (II) (2.58g, 10mmol), 2-[2- (2,2,2-Trifluoroethoxy)phenoxy]ethylamine (III) (2.58g, 11mmol) and 35mL of 1,2-dichloroethane, added triacetoxyboron under nitrogen atmosphere at room temperature Sodium hydride (3.0 g, 14 mmol) and acetic acid (0.9 g, 15 mmol) were heated to 45-50° C., stirred for 20 hours, and the reaction was detected by TLC. Add 1N sodium hydroxide to quench the reaction, extract twice with 1,2-dichloroethane, combine the organic phases, dry over anhydrous sodium sulfate, and remove the solvent under reduced pressure to obtain 2,3-dihydro-1-(3- Hydroxypropyl)-7-cyano-5-[2-[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethylamino]propyl]-1H-indole (IV) 4.1 g, yield 86.0%.

Embodiment 2

[0031] Add 1-(3-hydroxypropyl)-7-formamido-5-(2-oxopropyl)indoline (II) (2.76g, 10mmol), 2-[2 -(2,2,2-Trifluoroethoxy)phenoxy]ethylamine (III) (2.58g, 11mmol) and 1,2-dichloroethane 50mL, triacetoxy Sodium borohydride (3.0 g, 14 mmol) and acetic acid (0.9 g, 15 mmol) were heated to 50-55° C., stirred for 24 hours, and the reaction was detected by TLC. Add 1N sodium hydroxide to quench the reaction, extract twice with 1,2-dichloroethane, combine the organic phases, dry over anhydrous sodium sulfate, and remove the solvent under reduced pressure to obtain 2,3-dihydro-1-(3- Hydroxypropyl)-7-formamido-5-[2-[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethylamino]propyl]-1H-ind Indole (IV) 4.0g, yield 80.8%.

Embodiment 3

[0033] Add 2,3-dihydro-1-(3-hydroxypropyl)-7-formamido-5-[2-[2-[2-(2,2,2-trifluoroethoxy Base) phenoxy] ethylamino] propyl] -1H-indole (IV) (2.5g, 5mmol) and methanol 40mL, add S-(+)-mandelic acid (0.8g, 5mmol) under stirring, and Place in an ultrasonic generator and vibrate for 30 minutes, filter the insoluble matter, wash the filter cake with 10 mL of a mixture of ether and methanol, dry the white solid obtained, dissolve it in 40 mL of ethyl acetate and 40 mL of 10% sodium hydroxide, and stir at room temperature for 1 hour , standing for liquid separation, the organic phase was dried with anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 0.88 g of white solid silodosin (I), with a yield of 35.2%.

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Abstract

The invention discloses a preparation method of Silodosin (I). The preparation method comprises the steps of: subjecting 1, 7-disubstituted-5-(2-oxopropyl) indoline (II) and 2-[2-(2, 2, 2-trifluoroethoxy)phenoxy]ethylamine (III) to an amination reduction reaction to obtain 2, 3-dihydro-1, 7-disubstituted-5-[2-[2-[2-(2, 2, 2-trifluoroethoxy)phenoxy]ethylamine]propyl]-1H-indole (IV), and subjecting the intermediate (IV) to splitting and conversion of the 1, 7- functional group, thus obtaining the Silodosin (I). The preparation method has high chemical selectivity, can effectively control the cost, and can improve the quality of the product, thus promoting the economic and technological development of the bulk drug.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis method design and preparation of raw materials and intermediates, and in particular relates to a preparation method of silodosin. Background technique [0002] Silodosin (Silodosin, also known as Silodosin) is an alpha drug developed by Japan's Kissei Pharmaceutical Company. 1 - Receptor antagonists, useful in the treatment of symptoms associated with benign prostatic hyperplasia or hypertrophy. Japan's Jusheng Pharmaceutical Co., Ltd. and Daiichi Sankyo Pharmaceutical Co., Ltd. jointly applied for it, and it was first approved for marketing in Japan in May 2006. The trade name used is Urief. Subsequently, Jusheng and Daiichi Sankyo also authorized silodosin to Watson Pharmaceutical Company of the United States, which was approved by the US Food and Drug Administration (FDA) in August 2008 and launched in the United States. The silodosin capsule preparation imported by Japan's Daiichi ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/08
Inventor 许学农
Owner 南京联智医药科技有限公司
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