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Method for preparing high-purity Fudosteine

A technology for fodosteine ​​and a purification method, which is applied in the field of purification for preparing high-purity fodosteine, can solve problems such as unmarked fodosteine ​​purity, and achieves a safe and controllable quality, mild conditions and high yield. Effect

Active Publication Date: 2011-09-14
SICHUAN KELUN PHARMA RES INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] In the above-mentioned documents, document (2) patent CN200910167947 reports that the purity of fudosteine ​​obtained is only more than 99%, and the rest of the documents do not indicate the purity of the obtained fudosteine

Method used

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  • Method for preparing high-purity Fudosteine
  • Method for preparing high-purity Fudosteine

Examples

Experimental program
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Effect test

Embodiment 1

[0042]Suspend 200g of L-cysteine ​​in 150ml of water, adjust the pH of the suspension to 9 with 2N sodium hydroxide solution, add 400ml of ethanol and 252g of 3-bromo-1-propanol to the suspension, stir overnight, and the reaction is complete Finally, adjust the pH to 5 with 10% hydrochloric acid solution, evaporate the solvent under reduced pressure, wash the residue repeatedly with 1500ml of acetone, and mash to obtain a powder; the obtained powder is subjected to ion exchange chromatography and treated with 15000ml of 2N ammonia water as the eluent, and the eluate is collected After concentrating under reduced pressure, the residue is fudosteine ​​crude product;

[0043] Take 100g of crude product of fudosteine ​​and add 50 times of water to dissolve at 90°C, add 0.03 times of the amount of water used for adsorption and decolorization of activated carbon, filter, add 5g of methanol, crystallize at -20°C, filter and dry to obtain 82g of pure product of fordosteine , the HPLC ...

Embodiment 2

[0045] Suspend 200g of L-cysteine ​​in a small amount of 150ml of water, adjust the pH of the suspension to 9 with 2N sodium hydroxide solution, add 400ml of ethanol and 252g of 3-bromo-1-propanol to the suspension, stir overnight, and react Adjust the pH to 5 with 10% hydrochloric acid solution, evaporate the solvent under reduced pressure, wash the residue repeatedly with 1500ml of acetone and crush to obtain powder; Concentrate under reduced pressure after liquid to obtain residue as crude product of fudosteine;

[0046] Take 100 g of the crude product of fudosteine ​​and add 500 times of water to dissolve at 20°C, add 0.01 times of the amount of water used for adsorption and decolorization of activated carbon, filter, add 5000ml of methanol, crystallize at 10°C, filter and dry to obtain 79g of pure fordosteine, The HPLC purity of fudosteine ​​obtained was 99.7%.

Embodiment 3

[0048] Suspend 200g of L-cysteine ​​in a small amount of 150ml of water, adjust the pH of the suspension to 9 with 2N sodium hydroxide solution, add 400ml of ethanol and 252g of 3-bromo-1-propanol to the suspension, stir overnight, and react Adjust the pH to 5 with 10% hydrochloric acid solution, evaporate the solvent under reduced pressure, wash the residue repeatedly with 1500ml of acetone and crush to obtain powder; Concentrate under reduced pressure after liquid to obtain residue as crude product of fudosteine;

[0049] Take 100 g of crude product of fudosteine ​​and add 300 times of water to dissolve at 50 ° C, add 0.04 times of the amount of water used for adsorption and decolorization of activated carbon, filter, add 900 g of methanol, crystallize at 0 ° C, filter and dry to obtain 93 g of pure product of fudosteine, The HPLC purity of fudosteine ​​obtained was 99.6%.

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Abstract

The invention discloses a method for preparing high-purity Fudosteine. The method comprises the following steps of: dissolving 100 weight parts of Fudosteine crude product with 40 to 600 weight volume parts of water at the temperature of between 100 and 10 DEG C; adding active carbon in an amount which is 0.005 to 0.05 times weight volume of the using amount of the water, and performing adsorption and decoloring; filtering; adding 4 to 6,000 weight volume parts of methanol, and crystallizing at the temperature of between -25 and 15 DEG C; and filtering and drying to obtain the pure Fudosteine product. The Fudosteine prepared by the method has the high performance liquid chromatography (HPLC) purity of over 99.5 percent and has the advantages of mild condition for purifying the Fudosteine, high yield, high purity, suitability for industrialized production and safe and controllable quality.

Description

technical field [0001] The present invention relates to a purification method of medicinal compounds, in particular to a purification method for preparing high-purity fudosteine. 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, which can effectively reduce the secretion of mucus in patients with chronic respiratory diseases, and has good antitussive and phlegm-reducing effects. The company and SS Pharmaceutical Co., Ltd. produced and launched the market. [0005] At present, the preparation and purification methods of fudosteine ​​have been disclosed as follows: [0006] 1. Prepared by reacting L-cysteine ​​with 3-halo-1-propanol. (1) Literature Biochemistry1991, 30, 4078-4081 and patent US5047428, the method is to react L-cysteine ​​with 3-bromo-1-propanol to obtain a crude product, which is obtained by wa...

Claims

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Application Information

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IPC IPC(8): C07C323/58C07C319/28
Inventor 黄耀宗杨琪
Owner SICHUAN KELUN PHARMA RES INST CO LTD
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