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Preparation method of diosmin

A technology of diosmin and hesperidin, which is applied in the field of pharmaceutical preparation, can solve the problems of serious environmental pollution, complicated reaction, difficult product-related impurities, etc., and achieves the effects of serious environmental pollution, high product purity and great cost advantage.

Inactive Publication Date: 2014-12-31
成都华康生物工程有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Method ① The process line is long, the reaction is complicated, the related impurities are difficult to control, the yield is low, and it is difficult to realize industrial production
Adding solid alkali in method ② reduces the reaction speed, and at the same time causes product-related impurities to be difficult to control, which affects the product purity
Method ③ uses a large amount of iodine as the main auxiliary material. Due to the high price of iodine, the production cost of diosmin is high, and there is no cost advantage. Moreover, the iodine recovery operation in the later stage is dangerous and causes serious environmental pollution.

Method used

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  • Preparation method of diosmin

Examples

Experimental program
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Effect test

Embodiment 1

[0023] Add 200 milliliters of pyridine and 200 milliliters of dimethyl sulfoxide into the reflux reactor, add 100 grams of hesperidin after mixing, then add 0.3 grams of potassium iodide and 5 milliliters of sulfuric acid, heat and reflux for 6 hours, recover the organic solvent under reduced pressure, and concentrate to Thick paste, then add 500 ml of 50% (volume percentage) methanol solution containing 1.2 mol / L sodium hydroxide, heat to 50 ° C, stir to dissolve completely, filter with filter paper to remove insoluble impurities, and add hydrochloric acid to the filtrate to acidify The pH value was 5, and the crystallization was allowed to stand for 3 hours. The crystals were collected, washed with water and dried to obtain 87 g of diosmin.

Embodiment 2

[0025] Add 200 milliliters of pyridine and 200 milliliters of dimethyl sulfoxide into the reflux reaction kettle, add 100 grams of hesperidin after mixing, then add 0.5 grams of potassium iodide, 5 milliliters of sulfuric acid, heat and reflux for 5 hours, recover the solvent under reduced pressure, concentrate to thick paste, then add 500 ml of 50% methanol solution containing sodium hydroxide 1.2mol / L, heat to 50°C, stir to dissolve completely, filter with filter paper to remove insoluble impurities, add hydrochloric acid to the filtrate to acidify to pH 5, and let it stand After crystallization for 3 hours, the crystals were collected, washed with water and dried to obtain 88 g of diosmin.

Embodiment 3

[0027] Add 250 milliliters of pyridine and 250 milliliters of dimethyl sulfoxide in the reflux reactor, add 100 grams of hesperidin after mixing, then add 0.8 grams of potassium iodide, 5 milliliters of sulfuric acid, heat and reflux for 4 hours, recover the organic solvent under reduced pressure, and concentrate to Thick cream, then add 500 ml of 60% methanol solution containing sodium hydroxide 1.2mol / L, heat to 50°C, stir to dissolve completely, filter with filter paper to remove insoluble impurities, add hydrochloric acid to the filtrate to pH 6, static The crystallization was carried out for 3 hours, the crystals were collected, washed with water and dried to obtain 90 g of diosmin.

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Abstract

Relating to drug preparation, the invention discloses a preparation method of diosmin. The method comprises the steps of: (1) adding hesperidin into a mixed solvent of pyridine and dimethyl sulfoxide, then adding potassium iodide and sulfuric acid to carry out dehydrogenation reaction to obtain a reaction intermediate product; (2) adding a sodium hydroxide-containing methanol solution into the reaction intermediate product to react; and (3) then adding acid to adjust the pH value, and conducting standing crystallization, thus obtaining diosmin. Compared with existing preparation methods, the preparation method provided by the invention has the characteristics of low cost, simple process and high product purity, and is suitable for industrial mass production.

Description

technical field [0001] The invention relates to a medicine preparation, in particular to a preparation method of diosmin. Background technique [0002] Diosmin, English name Diosmin, also known as diosmin, molecular formula: C28H32O15, molecular weight: 608.54, Diosmin is a flavonoid drug, clinically used for chronic venous insufficiency, such as varicose veins, lower limbs Ulcers etc. The production of diosmin is mainly based on the natural extracted drug hesperidin through chemical synthesis. [0003] The synthetic method in the prior art generally has following several kinds: [0004] ①Hesperidin—hesperidin protected by acetyl group—oxidation reaction of bromine water—hydrolysis—diosmin. [0005] ②Hesperidin——solid base to remove water——iodine substitution reaction——morpholine deiodination reaction——diosmin. [0006] ③ Hesperidin - dehydration with high boiling point solvent (or dehydration with equipment) - iodine substitution reaction - alkali hydrolysis - diosmin. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/07C07H1/00
Inventor 夏时川
Owner 成都华康生物工程有限公司
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