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Title:
METHOD FOR SYNTHESIZING SILODOSIN AND INTERMEDIATE THEREOF
Document Type and Number:
WIPO Patent Application WO/2018/205919
Kind Code:
A1
Abstract:
The invention provides a method for synthesizing silodosin and an intermediate thereof, the steps being: deacetylation of a chlorinated substance 2 with hydrochloric acid/acetic acid to obtain indoline 3; then carrying out an SN2 substitution reaction to obtain an imide 4; subsequently carrying out an N alkylation reaction to obtain a benzoate 5; then reducing carbonyl to obtain indoline 6; then carrying out a Vilsmeier reaction to obtain an aldehyde 7; then carrying out oximation and dehydration to obtain a nitrile 8; and by means of an amine 9 obtained by a reaction with a hydrazine hydrate, carrying out resolution with L-tartaric acid to obtain a key silodosin intermediate 10. Condensation is carried out under alkaline conditions to obtain 11, which is salified and crystallized with L-malic acid to form a salt 12, and then hydrolyzed with alkaline hydrogen peroxide to obtain silodosin 1. In the present invention, L-malic acid is used for salification and crystallization, with impurities which are difficult to remove, such as dimers, being effectively removed, the reaction conversion rate being higher, the industrial production cost being effectively reduced, the use of dangerous reagents being avoided, the production steps being simplified and the safety of synthesis being improved.

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Inventors:
ZHU GUORONG (CN)
WANG ZHEN (CN)
YANG HUILIN (CN)
HUANG RONGMING (CN)
TU YONGJUN (CN)
Application Number:
PCT/CN2018/085967
Publication Date:
November 15, 2018
Filing Date:
May 08, 2018
Export Citation:
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Assignee:
ZHEJIANG TIANYU PHARMACEUTICAL CO LTD (CN)
International Classes:
C07D209/08
Domestic Patent References:
WO2015126076A12015-08-27
WO2012131710A22012-10-04
WO2017051324A12017-03-30
Foreign References:
KR20150066777A2015-06-17
CN106045895A2016-10-26
JP2016003183A2016-01-12
CN107056675A2017-08-18
US5387603A1995-02-07
CN102690223A2012-09-26
Other References:
See also references of EP 3450426A4
Attorney, Agent or Firm:
BOSS & YOUNG PATENT AND TRADEMARK LAW OFFICE (CN)
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