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Preparation method of tamsulosin hydrochloride with high optical purity

A technology of tamsulosin hydrochloride and optical purity, applied in the fields of medical technology and chemistry, can solve the problems of time-consuming and laborious separation of enantiomers, low yield and high cost, and achieves the solution of rework treatment, good reproducibility, low cost effect

Active Publication Date: 2015-09-23
CHENGDU LIKAI CHIRAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] The existing reporting methods all have the problem of how to obtain high optical purity, and they all inevitably need to go through a lengthy, time-consuming and laborious process of separating enantiomers
are faced with low yields and high costs
However, none of the reported methods mentioned how to deal with any abnormal situation such as the products produced by the reaction failing to meet the required optical purity. Without a backup rework solution, it is likely to bring huge risks of high investment.

Method used

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  • Preparation method of tamsulosin hydrochloride with high optical purity

Examples

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Effect test

Embodiment 1

[0036] Preparation of (R)-5-(2-(2-(2-ethoxyphenoxy)ethylamino)propyl)-2-methoxysulfonamide hydrochloride with high optical purity

[0037] Add 10 g of the crude product of (R)-5-(2-(2-(2-ethoxyphenoxy)ethylamino)propyl)-2-methoxysulfonamide hydrochloride successively to the reaction flask (Its chemical purity is 90%, e.e. value=51.3%, that is, (R)-5-(2-(2-(2-ethoxyphenoxy)ethylamino)propyl)-2-methoxy The basic sulfonamide hydrochloride content is 68.09%, (S)-5-(2-(2-(2-ethoxyphenoxy)ethylamino)propyl)-2-methoxy basic sulfonamide hydrochloride Salt content is 21.92%), ethanol 60 mL, water 30 mL, the mixture is stirred and heated to 50-60 o C dissolves and clarifies; then naturally cools down to room temperature, a small amount of white solid precipitates, and cools to 15°C in an ice-water bath o Below C, and stirred for 30 minutes; filtered, washed with 67% (volume percentage) ethanol / water, and the filter cake was discarded; the filtrate was collected, concentrated to ...

Embodiment 2

[0039] Preparation of (R)-5-(2-(2-(2-ethoxyphenoxy)ethylamino)propyl)-2-methoxysulfonamide hydrochloride with high optical purity

[0040] Add 10 g of the crude product of (R)-5-(2-(2-(2-ethoxyphenoxy)ethylamino)propyl)-2-methoxysulfonamide hydrochloride successively to the reaction flask (Chemical purity 95%, e.e. value=72.9%, that is, (R)-5-(2-(2-(2-ethoxyphenoxy)ethylamino)propyl)-2-methoxysulfonyl The content of amide hydrochloride is 82.13%, and the content of (S)-5-(2-(2-(2-ethoxyphenoxy)ethylamino)propyl)-2-methoxysulfonamide hydrochloride 12.87%), isopropanol 50 mL, water 50 mL, the mixture was stirred and heated to 50-60 o C dissolves and clarifies. Then the temperature was naturally cooled to room temperature, and a small amount of white solid was precipitated. Cool down to 15 in an ice bath o C below, and stirred for 30 minutes. Filter, wash with 50% isopropanol / water, and discard the filter cake. Collect the filtrate, concentrate to dryness under reduce...

Embodiment 3

[0042] Preparation of (R)-5-(2-(2-(2-ethoxyphenoxy)ethylamino)propyl)-2-methoxysulfonamide hydrochloride with high optical purity

[0043] Add 10 g of the crude product of (R)-5-(2-(2-(2-ethoxyphenoxy)ethylamino)propyl)-2-methoxysulfonamide hydrochloride successively to the reaction flask (e.e. value = 86.7%, which is the content of (R)-5-(2-(2-(2-ethoxyphenoxy)ethylamino)propyl)-2-methoxysulfonamide hydrochloride 93.35%, (S)-5-(2-(2-(2-ethoxyphenoxy)ethylamino)propyl)-2-methoxysulfonamide hydrochloride content is 6.65%), Its chemical purity is 99.6%, methanol 30 mL, water 60 mL, the mixture is stirred and heated to 50-60 o C dissolves and clarifies. Then the temperature was naturally cooled to room temperature, and a small amount of white solid was precipitated. Cool down to 15 in an ice bath o C below, and stirred for 30 minutes. Filter, wash with 33% methanol / water, and discard the filter cake. The filtrate was collected, concentrated to dryness under reduced pressure...

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Abstract

The invention discloses a preparation method of tamsulosin hydrochloride with high optical purity, and belongs to a medicine technology and a chemical field. A recrystallization method is adopted, crude products of (R)-5-(2-(2-(2-ethoxyphenoxy) ethyl amino) propyl)-2-methoxyl phenyl sulfonamide hydrochloride are refined, so that pure products of the (R)-5-(2-(2-(2-ethoxyphenoxy) ethyl amino) propyl)-2-methoxyl group sulfonamide hydrochloride of which the e.e. value is larger than 99.8% is obtained; a crystallizing solvent adopted by the recrystallization method is a mixed solvent consisting of an organic solvent and water, the organic solvent is selected from one of methanol, ethyl alcohol, acetone, acetonitrile and isopropyl alcohol, and the recrystallization temperature is under 15 DEG C. The preparation method disclosed by the invention is simple to operate, short in period, low in cost and good in repeatability, and can solve the inevitable problem of rework for treatment in the industrial production.

Description

technical field [0001] The invention relates to the fields of medical technology and chemistry, in particular to a preparation method of tamsulosin hydrochloride with high optical purity. Background technique [0002] Tamsulosin Hydrochloride (Tamsulosin Hydrochloride), chemical name: (R)-5-(2-(2-(2-ethoxyphenoxy)ethyl)amino)propyl)-2-methoxy Benzenesulfonamide hydrochloride is a new type of long-acting α-1 adrenoceptor antagonist. The drug has the characteristics of good selectivity, fast curative effect and few side effects, and is widely used clinically for the treatment of benign prostatic hyperplasia. [0003] Tamsulosin Hydrochloride (CAS: 106463-17-6, English name: Tamsulosin Hydrochloride) is a chiral compound, and its medicinal active ingredient is the R-configuration enantiomer (I). In order to ensure the selectivity and efficacy of clinical medication, the pharmacopoeias of various countries have higher requirements for the optical purity of tamsulosin hydrochlo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/37C07C303/44
Inventor 袁伟成左健周鸣强徐小英张晓梅
Owner CHENGDU LIKAI CHIRAL TECH
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