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High-purity troxerutin and preparation method thereof

A high-purity, rutin technology, applied in the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., can solve the problems of large yield loss, high cost, complicated process, etc., to meet quality requirements and production cycle. The effect of shortening and simplifying the separation process

Active Publication Date: 2017-05-10
HEFEI LIFEON PHARMA
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Problems solved by technology

And the purity of the target product obtained by the above method——7,3',4'-trihydroxyethyl rutin is not more than 91%
Obviously, the higher the purity of trihydroxyethyl rutin in the target product, the more difficult the preparation technology and the greater the loss of yield
Although the method of chromatographic separation or macroporous resin adsorption separation (such as: CN 104177461A) can obtain trihydroxyethyl rutin with a purity of 98% or even 99.0%, due to the characteristics of the method itself, it can only be used to prepare standard substances. difficult to apply to industrial production
[0010] In order to limit the amount of generation of tetrahydroxyethyl rutin isomers in the etherification process, Hebei United University (CN103113437A) discloses a preparation method of troxerutin, but from the analysis of the final product of its embodiment 1 to embodiment 3 From the results (purity of trihydroxyethyl rutin: 91-92%; tetrahydroxyethyl rutin: 6-7%; dihydroxyethyl rutin: 2-3%), the method has no effect on tetrahydroxyethyl rutin. Ding's inhibitory effect is still poor
For the same purpose, Li Si, Liang Xutong, etc. invented a new method (preparation method of trihydroxyethyl rutin, CN104177461A) that is different from the above-mentioned patent method, but the method of intermediate conversion and subsequent operations (such as ion exchange Resin desalination, macroporous resin adsorption, etc.) process is too loaded down with trivial details, cycle is long, cost is high, lacks economical practicality, so the raw material cost of preparing more than 98.0% trihydroxyethyl rutin by this method is as high as 2000~5000 yuan per kilogram , while the current market price of domestic medicinal troxerutin is lower or even far lower than 2,000 yuan per kilogram. From the perspective of production, it obviously lacks production value, so it is difficult to carry out industrial production

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  • High-purity troxerutin and preparation method thereof
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[0027] The preparation method of high-purity troxerutin includes step S1—the first stage etherification step: carry out etherification reaction of rutin and ethylene oxide under the conditions of a mixed solvent system of alcohol and water and an alkaline catalyst, and keep the reaction liquid The peak area percentage of tetrahydroxyethyl rutin in the medium is below 1.5% (detected by high-performance liquid chromatography), and the front-stage etherification reaction is stopped; wherein, rutin, the ethylene oxide, alcohol The mass ratio of water, alkaline catalyst is 1:0.1~0.4:1.5~6.5:0.5~8.0:0.008~0.012, and the reaction temperature of etherification reaction is 60~80°C.

[0028] Wherein, the reaction liquid refers to the reaction liquid during the etherification reaction. The etherification reaction can be carried out according to the conventional etherification reaction operation. Specifically, the etherification reaction is: mix a mixed solvent of alcohol and water with a...

Embodiment 1

[0052] The preparation method of the high-purity troxerutin provided by the present embodiment comprises the following steps:

[0053] S1: The etherification reaction is: mix isopropanol, anhydrous salt water and potassium hydroxide, pass argon into it for 10 minutes, then heat to 60-63°C, add refined rutin with a liquid phase purity of 96.10%, and then pass through Ethylene oxide, and control the reaction pH to 8.0 to 8.3, and the reaction temperature is 60 to 65°C to continue the etherification reaction until the peak area ratio of tetrahydroxyethyl rutin in the reaction liquid is detected by high performance liquid chromatography to be 0.55 % stop ventilation reaction; wherein, the mass ratio of rutin, ethylene oxide, isopropanol, anhydrous salt water, potassium hydroxide is 1:0.32:1.5:2.0:0.008;

[0054] S2: Adjust the pH of the substance (reaction solution) to 8.0-8.5, and the temperature to 70-75°C, add manganese acetate to the reaction solution, stir for 13 minutes, and...

Embodiment 2

[0061] The preparation method of the high-purity troxerutin provided by the present embodiment comprises the following steps:

[0062] S1: Mix ethanol, ultrapure water and sodium hydroxide, pass nitrogen into it for 12 minutes, then heat to 65°C, add refined rutin with a liquid phase purity of 97%, and then pass in ethylene oxide to control the concentration of the reaction solution. The pH is 8.7-9.0, the reaction temperature is 75-80°C, and the etherification reaction is continued until the reaction liquid is clarified. In the early stage, samples are taken every 1.2 hours for PHLC detection, and the peak area of ​​tetrahydroxyethyl rutin in the reaction liquid is 0.8 % stop the ventilation reaction; wherein, the mass ratio of rutin, ethylene oxide, ethanol, ultrapure water, sodium hydroxide is 1:0.32:2.5:2.5:0.012;

[0063] S2: Adjust the pH of the reaction solution to 9.2 to 9.5 and the temperature to 86 to 90°C. Add a proportioned amount of chromium acetate solution dropw...

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Abstract

The invention provides high-purity troxerutin and a preparation method thereof, and relates to the technical field of medicinal chemistry and organic synthetic chemistry. The preparation method comprises a front etherification step, a complexation step, a post etherification step and a post-treatment step. The preparation method of the high-purity troxerutin is relatively low in cost, the high-purity troxerutin can be prepared and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to the technical fields of medicinal chemistry and organic synthetic chemistry, in particular to a high-purity troxerutin and a preparation method thereof. Background technique [0002] Troxerutin (Troxerutin) is also known as Weinaolutong, trihydroxyethyl rutin. The chemical name is 7,3',4'-trihydroxyethyl rutin (referred to as trihydroxyethyl rutin). Molecular formula C 33 h 42 o 19 ; Molecular weight; 742.69; CAS NO:7085-55-4; Chemical structural formula is as follows: [0003] [0004] Troxerutin is an anticoagulant and thrombolytic drug, usually administered orally or by injection in clinical practice. The new national pharmacopoeia (2015 edition) stipulates that the troxerutin raw material contains 7,3’,4’-trihydroxyethylrutin (C 33 h 42 o 19 ) shall not be lower than 80% (oral grade) and 88.0% (injection grade). As an injection-grade raw material drug, the sum of the peak areas of the isomers 1, 2, and 4-hydroxy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/07C07H1/00
Inventor 李孝常范冰冰汪泉李冰蒋运运高美华季俊虬
Owner HEFEI LIFEON PHARMA
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