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Method for preparing tiopronin

A technology of tiopronin and sodium disulfide, applied in the field of medicine, can solve problems such as low yield of tiopronin, unfavorable treatment of three wastes, and increased reaction steps

Active Publication Date: 2013-01-30
SUZHOU ERYE PHARMA CO LTD
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  • Abstract
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Problems solved by technology

The sodium disulfide used in methods (2) and (3) is cheap, but the subsequent disulfide bond reduction requires the use of a large amount of zinc powder, which produces a large amount of industrial waste, which is not conducive to the treatment of three wastes; and the disulfide is first formed and then reduced to obtain the final product, increased reaction steps, resulting in low yield of tiopronin

Method used

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  • Method for preparing tiopronin
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  • Method for preparing tiopronin

Examples

Experimental program
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Embodiment Construction

[0034] 1. Preparation of α-chloropropionyl chloride

[0035] Add 108.6 g (1 mol) of α-chloropropionic acid and 178.4 g (1.5 mol) of thionyl chloride into a 100 mL round-bottomed flask, reflux for 5 h, collect the distillate with bp 109~111°C to obtain 120.1 g of colorless liquid , the yield is 94.5%.

[0036] 2. Preparation of α-chloropropionylglycine

[0037] Add 37.4 g (0.5 mol) of glycine, 53.0 g (0.5 mol) of anhydrous sodium carbonate and 500ml of water into a 1000 mL four-necked flask, and stir to dissolve. Cool in an ice-salt bath, and add α-chloropropane dropwise under vigorous stirring Acyl chloride 63.3 g (0.5 mol), continue to stir for 3 h after addition, acidify with hydrochloric acid to pH = 1, extract with ethyl acetate, dry over anhydrous sodium sulfate, filter, concentrate the filtrate until crystals precipitate, place, filter The precipitated crystals were dried to obtain 56.1 g of small colorless needle-like crystals, with a yield of 68%, mp 104~105°C.

[0...

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Abstract

The invention provides a method for preparing tiopronin. The method comprises the following steps of: (1) making alpha-chloropropionic acid react with thionyl chloride to obtain alpha-chloropropionylchloride; (2) making alpha-chloropropionylchloride react with glycine to obtain alpha-chloroglycine; and (3) making alpha-chloroglycine react further to obtain the tiopronin. The method has the advantages of small quantity of steps, low pollution and high yield.

Description

[0001] technical field [0002] The invention relates to a preparation method of cetiopronin, which belongs to the technical field of medicine. [0003] Background technique [0004] The chemical name of Tiopronin (Tiopronin, (1)) is N-(α-mercaptopropionyl) glycine, which was developed by Santen Pharmaceutical Co., Ltd. in Japan. It was first listed in Japan in 1964 as a metabolic antidote. Tiopronin is a glycine derivative containing free sulfhydryl groups, which can reduce the mitochondrial ATPase activity of liver cells, improve the function of liver cells, and is suitable for long-term treatment of chronic diseases without toxic side effects. Clinically, it is often used as a hepatoprotective drug for the treatment of acute and chronic hepatitis, early cirrhosis, fatty liver, alcoholic liver injury and other diseases. [0005] [0006] In the mid-1990s, domestic production was approved, and it is currently widely used clinically. In the prior art, the synthesis met...

Claims

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Application Information

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IPC IPC(8): C07C323/60C07C319/02
Inventor 张健陈学文朱炜颜彦
Owner SUZHOU ERYE PHARMA CO LTD
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