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Method for synthesizing and purifying Fasudil hydrochloride

A technology of fasudil hydrochloride and purification method, which is applied in the field of synthesis and purification of fasudil hydrochloride, can solve problems such as difficult removal, achieve the effects of reducing the generation of impurities, solving the problem of excessive residual impurities, and simple operation

Inactive Publication Date: 2011-04-20
JIANGSU WANBANG BIOPHARMLS +1
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  • Abstract
  • Description
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Problems solved by technology

[0003] However, the existing Fasudil hydrochloride finished products all contain three types of impurities: 1, the dimer of 5-isoquinolinesulfonyl chloride and homopiperazine; 2, the difficult-to-remove raw material homopiperazine; 3, during the reaction Pigment of the product

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  • Method for synthesizing and purifying Fasudil hydrochloride
  • Method for synthesizing and purifying Fasudil hydrochloride
  • Method for synthesizing and purifying Fasudil hydrochloride

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Embodiment Construction

[0031] A method for synthesizing and purifying fasudil hydrochloride, using 5-isoquinolinesulfonic acid as a starting material, and obtaining a high-purity product through steps including chlorination, synthesis with homopiperazine, and acid-base treatment, is characterized in that it includes Follow the steps below:

[0032] The first step: in 5-isoquinolinesulfonic acid, first add catalyst N, N-dimethylformamide (DMF), then add thionyl chloride, wherein, the quality of 5-isoquinolinesulfonic acid and catalyst The ratio is 10:1, stirring, heating at 80°C for reflux reaction for 1 hour, cooling to 60°C, recovering thionyl chloride by distillation under reduced pressure, and further removing residual thionyl chloride by dichloromethane beating to obtain 5- Isoquinolinesulfonyl chloride hydrochloride (A);

[0033] Step 2: In dichloromethane, first add 5-isoquinolinesulfonyl chloride hydrochloride (A), then add water, slowly add sodium bicarbonate while stirring, and adjust the ...

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Abstract

The invention relates to a method for synthesizing and purifying Fasudil hydrochloride, comprising the following steps of: adding N,N-dimethylformamide and thionyl dichloride to 5-isoquinoline sulfonic acid to obtain a 5-isoquinoline sulfonyl chloride hydrochloride; adding the 5-isoquinoline sulfonyl chloride hydrochloride, water and sodium bicarbonate to dichloroethene to obtain a 5-isoquinoline sulfonyl chloride solution; dripping the 5-isoquinoline sulfonyl chloride solution to homopiperazine at zero DEG C to obtain a hexahydro-1-(5-sulfonyl isoquinoline)-1(H)-1,4-benzodiazepine solution; removing impurities in three steps; adjusting the pH value to be 4.5-5.5 with an acidizing fluid, extracting, and discarding an organic phase dissolved with a dipolymer impurity; adjusting the pH value to be 9.5-10.5 with alkali, extracting and discarding a water phase dissolved with homopiperazine impurities and a majority of pigments; removing the residue pigment by passing through silica gel; and finally, washing, drying, filtering, then dripping a hydrochloric acid-ethanol solution at 0 DEG C, and crystallizing while stirring to prepare the Fasudil hydrochloride. The invention has the advantages that the three kinds of impurities are effectively removed through the three-step purification process, and the purity of a product reaches more than 99.9%.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing and purifying fasudil hydrochloride. Background technique [0002] Fasudil hydrochloride is a new type of drug with a wide range of pharmacological effects. Its molecular structure is 5-isoquinoline sulfonamide derivatives, which are RHO kinase inhibitors. By increasing the activity of myosin light chain phosphatase, it expands Blood vessels, reduce the tension of endothelial cells, improve the microcirculation of brain tissue, prevent and aggravate blood stealing in the brain, and at the same time antagonize inflammatory factors, protect nerves against apoptosis, and promote nerve regeneration. [0003] However, the existing Fasudil hydrochloride finished products all contain three types of impurities: 1, the dimer of 5-isoquinolinesulfonyl chloride and homopiperazine; 2, the difficult-to-remove raw material homopiperazine; 3, during the reaction The c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12
Inventor 辛海强乔德水林彬李孝成高雪芹
Owner JIANGSU WANBANG BIOPHARMLS
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