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Preparation method of troxerutin

A technology of trishydroxyethylrutin and monohydroxyethylrutin is applied in the field of preparation of trishydroxyethylrutin, can solve the problems of difficult removal, no product supply, undisclosed preparation method, etc., and achieves low cost, Production cost saving, good practicability

Inactive Publication Date: 2014-12-03
JINAN XINLITE TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Another important reason is that rutin from natural sources and its impurities are very similar in structure, which makes the purification of rutin difficult, and it is difficult to obtain high-purity rutin by conventional methods. A purification method of rutin is disclosed in patent CN200810007927.2. Only gram-level rutin with a purity of 98% was obtained by complex countercurrent chromatography. In fact, the preparation of troxerutin currently uses commercially available rutin with lower purity as raw materials. The impurities contained in these raw materials It will also participate in the hydroxyethylation reaction, and its properties are very similar to trihydroxyethyl rutin in the final product, which is difficult to remove
In fact, the preparation of high-purity trihydroxyethyl rutin is very difficult, except for preparative chromatography [Li Jun et al., Preparation of Troxerutin Reference Substance by Liquid Chromatographic Separation, Impurities in Chinese Pharmaceutical Industry, 2004, 35 (5) , 285-7] In addition to obtaining 99% of the trihydroxyethyl rutin reference substance, the use of conventional methods to prepare more than 98% of the trihydroxyethyl rutin monomer has not been reported, even if it is sold on the market and claims to contain 99% product, but its preparation method has not been disclosed, and there is no product supply, and the chromatographic purity of the trihydroxyethyl rutin reference substance prepared by multiple solvent recrystallizations using the prior art is only 96-97%

Method used

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  • Preparation method of troxerutin
  • Preparation method of troxerutin
  • Preparation method of troxerutin

Examples

Experimental program
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Embodiment 1

[0065] 1. 328 grams, 0.86 moles of borax (Na 2 B 4 o 7 10H 2 O) Add 2500ml of deionized water, stir to dissolve, then add 605 grams, 0.82 moles of rutin, stir at 40-45°C until dissolved, filter to obtain a clear aqueous solution of rutin-borax complex. The solution was kept at 40-45°C. Under the stirring state, 88 grams, 2 moles of ethylene oxide were gradually passed into the reaction solution. The reaction time was about 6 hours. The reaction was detected by HPLC until it was completely reacted. The pH of the reaction solution was adjusted to 2.0 with 5N hydrochloric acid. , placed at 3-5°C for 12 hours, and suction filtered to obtain a solid filter cake containing 504 grams of 7-monohydroxyethyl rutin, with a yield of 95%.

[0066] 2. Take 1,460 grams of 7-monohydroxyethyl rutin aqueous solid obtained in 1, add 4,750 ml of deionized water, heat to 60°C under stirring, dissolve it completely, filter, place the filtrate at 3-5°C overnight, and suction filter to obtain the ...

Embodiment 2

[0071] 1. 164 grams, 0.43 moles of borax (Na 2 B 4 o 7 10H 2 O); 12 grams, 0.3 moles of sodium hydroxide (NaOH) was added to 2000ml of deionized water, stirred and dissolved, then added 605 grams, 0.82 moles of rutin, heated to and kept at 40-45 ° C, under stirring, the 88 Gradually, 2 moles of ethylene oxide were introduced into the reaction solution step by step. The reaction time was about 12 hours. The reaction was detected by HPLC until it was completely reacted. A solid filter cake was obtained, containing 510 grams of 7-monohydroxyethyl rutin, with a yield of 96%. .

[0072] 2. Take 510 grams of 7-monohydroxyethyl rutin obtained in 1 (total weight 1450, water content 940 grams), add 2000 ml of deionized water, heat to 40 °C under stirring, add a saturated aqueous solution of sodium bicarbonate dropwise until the solids are completely Dissolve, filter, and adjust the pH of the filtrate to 4.0 with 0.1 mole hydrochloric acid, place it overnight at 3-5°C, filter with ...

Embodiment 3

[0077] 1. 328 grams, 0.86 moles of borax (Na 2 B 4 o 7 10H 2 O) Add 2000ml of deionized water, stir to dissolve, then add 605g, 0.82 mole of rutin, stir at 40-45°C until dissolved, filter to obtain a clear aqueous solution of rutin-borax complex. The solution is kept at 40-45°C. Under the stirring state, 88 grams, 2 moles of ethylene oxide are gradually passed into the reaction solution. The reaction time is about 6 hours. The reaction is completely detected by HPLC. The reaction solution is directly pretreated by conventional methods. Good D101 macroporous resin for separation and purification, the amount of resin used is 25 kg, after the sample is loaded, rinse with deionized water until the pH of the effluent is near neutral, first rinse with 2000ml of 10% ethanol, then rinse with 10000ml of 60% ethanol, and then rinse with Rinse completely with 90% ethanol, collect the effluent of 60% ethanol, concentrate in vacuum until there is no alcohol smell, add water to 12000ml, ...

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Abstract

The present invention relates to a preparation method of trihydroxyethyl rutoside. In the method, rutin is firstly prepared into 7-monohydroxyethyl rutoside in a content of greater than or equal to 98% by weight, and then 7-monohydroxyethyl rutoside is hydroxyethylated continuously to obtain troxerutin having the impurity of non hydroxyethylated rutoside derivatives less than 2%. The content of 7,3',4'-trihydroxyethyl rutoside in the troxerutin is above 80% by weight. The product is further refined, and the 7,3',4'-trihydroxyethyl rutoside in a content of greater than or equal to 98% by weight could be obtained.

Description

technical field [0001] The invention relates to a preparation method of a medicinal compound, in particular to a preparation method of trihydroxyethyl rutin. Background technique [0002] Troxerutin (Troxerutin) is also known as: Weinaolutong, the chemical name of its main component is 7,3',4'-trihydroxyethyl rutin (referred to as trihydroxyethyl rutin), molecular formula C 33 h 42 o 19 , CAS NO.7085-55-4, molecular weight: 742.69, structural formula as follows: [0003] [0004] Troxerutin is an anticoagulant and thrombolytic drug, and its preparation usually uses rutin and ethylene oxide as raw materials, methanol and water as the medium, and synthesizes troxerutin in the presence of an alkali catalyst. Currently there are ready-made troxerutin raw materials for sale in the market, and its content includes different content specifications of 60%, 80%, and 88%. [0005] Trihydroxyethyl rutin in troxerutin is its active ingredient, and the higher the content, the bett...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/07C07H1/00
CPCC07H1/00C07H17/07Y02P20/582C07H1/06
Inventor 李思梁旭彤李大鹏
Owner JINAN XINLITE TECH
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