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Preparation method of tamsulosin hydrochloride

A technology of tamsulosin hydrochloride and hydrochloride, applied in the field of preparation of tamsulosin hydrochloride, can solve the problems of high reaction cost, environmental pollution, optimization, etc., and achieves avoiding flammable gas, improving process safety, reducing The effect of process cost

Pending Publication Date: 2020-06-23
SUZHOU SUNCADIA BIOPHARM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Specifically, 5-acetonyl-2-methoxybenzenesulfonamide and (R)-1-phenylethylamine can obtain reduction products under the action of nickel or platinum catalysts, but hydrogen is used as hydrogen donor in this method And the reaction process needs to be heated. In addition, the use of heavy metals or precious metals in the reaction causes high reaction costs or environmental pollution. Although there are many patents later related to the preparation of tamsulosin hydrochloride, such as US7638649B, WO2004087623, WO2008152653, etc., all This step reaction has not been optimized. In view of the market demand of tamsulosin hydrochloride and the serious problems in the current process, reasonable process optimization is still required for this product

Method used

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  • Preparation method of tamsulosin hydrochloride
  • Preparation method of tamsulosin hydrochloride
  • Preparation method of tamsulosin hydrochloride

Examples

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Embodiment 1

[0043] Step 1, Synthesis of 5-[[(2R)-2-[(1R)-N-(1-methylbenzyl)]amino]propyl]-2-methoxysulfonamide hydrochloride

[0044] Put dichloromethane (2250mL, 15V) and (R)-1-phenylethylamine (150.0g, 1.0eq) into a 10L three-necked flask, start stirring, and add 5-acetonyl-2-methoxybenzenesulfonamide (316.2g, 1.05eq), slowly add acetic acid (74.3g, 1.0eq), warm up to 30-35°C, add sodium triacetoxyborohydride (314.8g, 1.2eq), stir for 16h, stop the reaction. Add dropwise 3mol / L dilute hydrochloric acid aqueous solution (958.0g), stir for 30min, add dropwise 30% sodium hydroxide aqueous solution (1096.0g), stir and separate layers, add saturated saline (1500.0g) to the organic phase, stir for 15min, pass diatom Soil (30.0g), separate the organic phase, add 33% hydrogen chloride ethanol solution (225.0g) dropwise, stir for 60 minutes, evaporate a large amount of solvent under reduced pressure, add acetonitrile (2250mL), stir for 30min, filter, and wash the wet product with acetonitrile ,...

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Abstract

The invention provides a preparation method of tamsulosin hydrochloride. Specifically, the preparation method comprises a step of reacting 5-acetonyl-2-methoxybenzenesulfonamide with (R)-1-phenylethylamine under the action of a reducing agent to obtain a compound as shown in a formula (IV) or pharmaceutically acceptable salt thereof, and further comprises a step of preparing tamsulosin hydrochloride from the compound as shown in the formula (IV) or pharmaceutically acceptable salt thereof. The preparation method provided by the invention is high in safety and strong in operability, avoids theuse of a heavy metal catalyst, and has an industrial actual use value.

Description

[0001] field of invention [0002] The disclosure relates to a preparation method of tamsulosin hydrochloride, which belongs to the field of pharmacy. Background technique [0003] Tamsulosin hydrochloride is a drug developed by Japan Yamanouchi Pharmaceutical Co., Ltd. for the treatment of dysuria caused by benign prostatic hyperplasia. The specific structure is as follows: [0004] [0005] Regarding the preparation method of tamsulosin hydrochloride, the method disclosed in the original research patent EP0380144B is as follows: [0006] [0007] Specifically, 5-acetonyl-2-methoxybenzenesulfonamide and (R)-1-phenylethylamine can obtain reduction products under the action of nickel or platinum catalysts, but hydrogen is used as hydrogen donor in this method And the reaction process needs to be heated. In addition, the use of heavy metals or precious metals in the reaction causes high reaction costs or environmental pollution. Although there are many patents later relat...

Claims

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Application Information

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IPC IPC(8): C07C303/40C07C311/37A61K31/18A61P13/08
CPCC07C303/40A61K31/18A61P13/08C07B2200/07C07C311/37
Inventor 张志鹏胡逸民李志亚潘昌明李凯
Owner SUZHOU SUNCADIA BIOPHARM CO LTD
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