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Preparation method of Fudosteine

A technology of fudosteine ​​and ethanol, which is applied in the field of preparation of antitussive and expectorant drug fudosteine, can solve the problems of product loss, cumbersome steps, and high product residue, and achieve the effect of improving quality and simplifying the process

Inactive Publication Date: 2016-09-28
WEIHAI DISU PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The biggest disadvantage of this method is that it is difficult to remove the inorganic salts in the final product, which easily leads to high residue
For example, US5047428 has reported that L-cysteine ​​and 3-bromo-1-propanol react to prepare fudosteine. The method has a long reaction time, and the reaction process can produce equimolar inorganic salts, and fudosteine ​​is soluble in water. , insoluble in organic solvents, it is not easy to remove inorganic salts from the product, resulting in high product residues, which is not conducive to industrial production; Chinese patent application 200910167947.0 reported the reaction of L-cysteine ​​and 3-chloro-1-propanol to prepare Fodos Fudosteine, using the solubility difference between fudosteine ​​and sodium chloride to purify fudosteine, but the experimental process requires hot filtration (≥95°C), the steps are cumbersome, the operation is complicated, and the product will be more lost

Method used

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  • Preparation method of Fudosteine
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Experimental program
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Effect test

Embodiment 1

[0020] At room temperature, dissolve 100g of L-cysteine ​​in a mixed solvent of a certain amount of water and ethanol (300g:750g), add 96g of allyl alcohol, then add 0.05ml of n-propylamine, and stir to dissolve. The temperature was raised to 40°C, and the reaction was stirred for 4.0h. After the reaction was completed, the temperature was lowered to 0° C., stirred and crystallized for 2 hours, and a white solid was obtained by suction filtration. Blast drying at 45°C to constant weight yielded 140.5 g of white solid powder with a content of 99.1%, and the residue was determined to be 0.01%. Yield 94.9%.

Embodiment 2

[0022] At room temperature, dissolve 100g of L-cysteine ​​in a mixed solvent of a certain amount of water and ethanol (300g:750g), add 96g of allyl alcohol, then add 0.05ml of isopropylamine, and stir to dissolve. The temperature was raised to 40°C, and the reaction was stirred for 4.0h. After the reaction was completed, the temperature was lowered to 0° C., stirred and crystallized for 2 hours, and a white solid was obtained by suction filtration. Air-dried at 45°C to constant weight to obtain 144.6 g of white solid powder, which was analyzed by HPLC with a content of 99.2% and a residue of 0.01%. The yield is 97.7%.

Embodiment 3

[0024] At room temperature, dissolve 100g of L-cysteine ​​in a mixed solvent of a certain amount of water and ethanol (300g:750g), add 96g of allyl alcohol, then add 0.05ml of triethylamine, and stir to dissolve. The temperature was raised to 40°C, and the reaction was stirred for 4.0h. After the reaction was completed, the temperature was lowered to 0° C., stirred and crystallized for 2 hours, and a white solid was obtained by suction filtration. Blast drying at 45°C to constant weight yielded 145.9 g of white solid powder with a content of 99.0%, and the residue was determined to be 0.01%. The yield is 98.6%.

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Abstract

The invention discloses a preparation method of Fudosteine, and relates to a preparation method suitable for industrially producing Fudosteine. Water and ethyl alcohol are adopted as reaction solvent, amine substances serves as the catalyst, cooling and crystallization are conducted after reaction, and the product is obtained in the form of sedimentation. The whole process is easy to control, repeatability is high, the yield of Fudosteine is stabilized at 95%, the residual amount is controlled within 0.05%, and the preparation method completely conforms to the medicinal standard and is quite suitable for industrial production.

Description

technical field [0001] The invention relates to the preparation of fudosteine, an antitussive and phlegm-reducing drug, and belongs to the technical field of medicine. Background technique [0002] Fudosteine ​​(chemical name: 3-hydroxypropylthioalanine) is a class of compounds with the basic skeleton of steine ​​developed by Japan SSP Pharmaceutical Co., Ltd. in 1988. It was first introduced in October 2001 Listed in Japan. Pharmacological experiments have proved that it has many functions such as inhibiting goblet cell hyperplasia, promoting serous tracheal secretion and inhibiting tracheal inflammation. Due to its strong efficacy, small side effects, wide indications and great market potential, fudosteine ​​is expected to become Alternative products of similar drugs. [0003] The synthetic method of this compound is mainly divided into two classes at present: [0004] One method is the reaction of L-cysteine ​​and allyl alcohol under the action of light, microwave, hea...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/58C07C319/18
CPCC07C319/18C07B2200/07C07C323/58
Inventor 李廷义蒋增强葛执信苗华明
Owner WEIHAI DISU PHARMA CO LTD
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