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Synthesis method of tamsulosin hydrochloride

A technology of tamsulosin hydrochloride and a synthesis method, which is applied in the field of synthesis of tamsulosin hydrochloride, can solve the problems of complex synthesis process of tamsulosin hydrochloride, high cost, impure product and the like, and achieves good product purity and synthesis. Convenience and mild reaction conditions

Active Publication Date: 2014-01-08
天台宜生生化科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0018] The purpose of the present invention is to provide a kind of synthetic method of tamsulosin hydrochloride in order to overcome the shortcoming of complex synthesis process, high cost and impure product of tamsulosin hydrochloride in the prior art

Method used

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  • Synthesis method of tamsulosin hydrochloride
  • Synthesis method of tamsulosin hydrochloride
  • Synthesis method of tamsulosin hydrochloride

Examples

Experimental program
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Effect test

Embodiment 1

[0052] A kind of synthetic method of tamsulosin hydrochloride, described method is carried out according to the following steps:

[0053] (1) Condensation reaction: In a 1000ml reaction bottle, add RMBS (39.3g, 98%, the amount of substance is 0.245mol), EPEB 0.245mol, potassium hydroxide 0.3675mol and acetonitrile, wherein the amount of acetonitrile is the total amount of RMBS and EPEB 3 times the mass, heated up to 40°C, reacted for 15h, then lowered the temperature, filtered, the filtrate was distilled under reduced pressure to recover acetonitrile, and obtained condensate intermediate 53.2g, see Table 1, the purity of the condensate intermediate was 94.8%, and the yield was 93.5 % (Based on RMBS quality), the condensate intermediate is directly subjected to the next hydrogenation reaction without purification;

[0054] (2) Hydrogenation reaction: Take 50g of the condensate intermediate, add ethanol (150g) which is 3 times the mass of the condensate intermediate in a 1000ml ...

Embodiment 2

[0056] The basic operation steps of embodiment 2, embodiment 3, embodiment 4 and embodiment 5 are the same as embodiment 1, and the specific reaction conditions and results are shown in table 1.

[0057] Shown by table 1, synthetic method reaction condition of the present invention is gentle. During the reaction process, there are few by-products, the yield and purity of the intermediate product are high, and the obtained final product tamsulosin hydrochloride has good product purity and high yield.

[0058] Table 1 Concrete reaction conditions and results of embodiment 1 to embodiment 5

[0059]

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Abstract

The invention belongs to the technical field of chemical synthesis, and specifically relates to a synthesis method of tamsulosin hydrochloride. According to the synthesis method, benzene sulfonic amide shown as a formula (II) and bromine ether shown as a formula (III) are in a condensation reaction in an aprotic polar solvent in the presence of an acid-binding agent to generate a condensation compound intermediate shown as a formula (IV); the condensation compound intermediate is in organic solvent, in the presence of a catalyst, hydrogen is introduced into the organic solvent under certain pressure so as to hydrogenate the condensation compound intermediate, then, the R-tamsulosin free alkali shown as a formula (V) is obtained, and the R-tamsulosin free alkali further is subjected to a salt formation reaction with hydrochloric acid in an organic solvent C to produce the tamsulosin hydrochloride shown as a formula (I). In the reaction process for preparing the tamsulosin hydrochloride through the synthetic route provided by the invention, the phenomenon that bimolecular bromide and amine react with each other to generate a disubstituted by-product is avoided, and the obtained tamsulosin hydrochloride has high product purity and high yield; according to the synthesis method, the reaction conditions are moderate, and synthesis is convenient to finish.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a synthesis method of tamsulosin hydrochloride. Background technique [0002] Tamsulosin hydrochloride, the chemical name is (R)-5-[2-[[2-(2-ethoxyphenoxy)ethyl]-amino]propyl]-2-2methyl Oxybenzenesulfonamide hydrochloride, CAS: 106133-20-4, is the third-generation super-selective long-acting α1 inhibitor, which was successfully developed by Japan Yamanouchi Pharmaceutical Co., Ltd., and was approved by FDA in July 1992. The trade name is Harnal (Halle), and then jointly sold tamsulosin hydrochloride with Boehringer Ingelheim and Abbott, and was approved by the FDA in 1997 under the trade name Flomax. The drug can specifically inhibit the contraction of the smooth muscle of the prostate and quickly relieve the clinical symptoms of benign prostatic hyperplasia. [0003] [0004] The main methods of synthesizing tamsulosin in the prior art are: [0005] ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/37C07C303/40
Inventor 夏桂珍陈优郑建华贾建洪
Owner 天台宜生生化科技有限公司
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