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Synthesis method of fudosteine

A synthetic method and mixed solution technology, applied in sulfide preparation, organic chemistry, etc., can solve the problems of low product purity and low yield, and achieve the effect of high product yield and mild reaction conditions

Active Publication Date: 2015-02-04
YICHANG HEC CHANGJIANG PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For example, Chinese patent ZL200510059733.3 adopts thermal initiation to prepare fudosteine ​​(purity≤95%, yield≤85%); the document "Fudosteine ​​Synthesis Technology" adopts potassium persulfate and sodium sulfite to initiate preparation of fudosteine, It has the problem of inorganic residue ≥ 0.05%
In addition, in the document "Study on the Synthesis of the Expectorant Drug Fudosteine", ultraviolet light is used to initiate, but the yield is low and the product purity is not high.

Method used

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  • Synthesis method of fudosteine
  • Synthesis method of fudosteine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Take 20g of L-cysteine, put it into a 1000mL four-necked bottle, add 140g of purified water, add dropwise 35mL of glacial acetic acid, mix and dissolve at 40°C, and add dropwise 15g of allyl alcohol. React under 365nm ultraviolet light for 8 hours, add 800mL of 95% ethanol dropwise, cool to 20°C, keep warm for 2h, filter, wash the filter cake with 50mL of 95% ethanol, dry to obtain 29.1g of crude fudosteine, and then use 450mL of 15% The ethanol was heated to 40°C, stirred and dissolved, cooled to 20°C after 2 hours, filtered, the filter cake was washed with 50mL of 95% ethanol, and dried to obtain 28.2g of fudosteine, with a yield of 94%, a purity of 99.83% by HPLC, and a maximum purity of 0.06 %.

Embodiment 2

[0018] Take 20g of L-cysteine, put it into a 1000mL four-necked bottle, add 140g of purified water, add dropwise 55mL of glacial acetic acid, mix and dissolve at 40°C, and add dropwise 20g of allyl alcohol. React under 210nm ultraviolet light irradiation for 6h, add 700mL85% ethanol dropwise, cool down to 20°C, keep warm for 2h, filter, wash the filter cake with 50mL85% ethanol, dry to obtain 28.8g crude fudosteine, and then use 550mL25% The ethanol was heated to 40°C, stirred and dissolved, cooled to 20°C after 2 hours, filtered, the filter cake was washed with 50mL of 85% ethanol, and dried to obtain 27.6g of fudosteine, with a yield of 92%, a purity of 99.75% by HPLC, and a maximum purity of 0.04 %.

Embodiment 3

[0020] Take 20g of L-cysteine, put it into a 1000mL four-necked bottle, add 140g of purified water, add dropwise 30mL of glacial acetic acid, mix and dissolve at 40°C, and add dropwise 17g of allyl alcohol. React under 280nm ultraviolet light irradiation for 6h, add dropwise 900mL of absolute ethanol, cool to 20°C, keep warm for 2h, filter, wash the filter cake with 50mL of absolute ethanol, dry to obtain 29.3g of crude product fudosteine, and then use 550mL of 25% ethanol was heated to 40°C, stirred and dissolved, cooled to 20°C after 2 hours, filtered, the filter cake was washed with 50mL of absolute ethanol, and dried to obtain 28.5g of fudosteine, the yield was 95%, and the purity by HPLC was 99.59%. Simplex 0.07%.

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Abstract

The invention discloses a synthesis method of fudosteine. The synthesis method comprises the following steps: in a glacial acetic acid-water system serving as a solvent, initiating a free radical reaction between L-cysteine and allyl alcohol which serve as starting raw materials at 40 DEG C by ultraviolet light; then, dropwise adding a certain amount of ethanol solution, cooling to 20 DEG C, and filtering to obtain a crude product of fudosteine; recrystallizing the crude product of fudosteine with 5-100% ethanol; filtering for the second time and drying to finally obtain high-purity fudosteine. The synthesis method of fudosteine is mild in synthesis condition and high in product yield which is higher than or equal to 92%; HPLC purity is higher than or equal to 99% and the maximum net contamination is less than or equal to 0.1%. The synthesis method of fudosteine can meet the demands of the market on fudosteine bulk drug.

Description

technical field [0001] The invention relates to the field of chemistry, in particular to a method for synthesizing fodostan, which belongs to the technical field of drug synthesis. Background technique [0002] Fudosteine, the chemical name is 3-hydroxypropylthioalanine, and its chemical structure is as follows: [0003] [0004] Fudosteine ​​is an expectorant with a new mechanism of action. It can inhibit the excessive formation of mucus-secreting goblet cells in the trachea and the production of highly viscous fucoidin. It has good antitussive and phlegm-reducing effects. Efficacy, it was first approved in Japan in October 2001 to be produced and marketed by Mitsubishi Pharmaceutical Co., Ltd. and SS Pharmaceutical Co., Ltd. But for now, it still has a great market demand. [0005] There are mainly two methods for synthesizing fudosteine. One is to condense L-cysteine ​​and halogenated propanol under alkaline conditions. The fudosteine ​​obtained by this method is imp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/58C07C319/18
Inventor 严凯肖艳唐金龙何安李晓曦
Owner YICHANG HEC CHANGJIANG PHARMA CO LTD
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