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Method for preparing Meixianduoxin

A technology of metadoxine and pyroglutamic acid, applied in digestive system, organic chemistry, drug combination and other directions, can solve problems such as unfavorable industrialization, product purity only reaches 96%, long steps, etc. Novel process and cost-saving effect

Inactive Publication Date: 2007-12-26
YUANXING PHARM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The above-mentioned method for preparing metadoxine has the following defects: the method for preparing metadoxine provided by Italian patent IT1131855 has long steps and requires an ion-exchange chromatographic purification, which is not conducive to industrialization
However, the domestic solid-phase synthesis method needs to grind the solid powder of vitamin B6 base and pyroglutamic acid until exothermic and sticky, so that the solid will stick to the container, so this method is only suitable for small laboratory tests, not suitable for industry. production, and its product purity only reaches 96%, which cannot meet the pharmaceutical grade standard
In industrial scale production, it is difficult to evenly mix the two reactants that need to be ground until exothermic and sticky, and will stick to the container. If the amount of solvent added is small and the mixture cannot be fully mixed, it will be difficult to completely react

Method used

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  • Method for preparing Meixianduoxin
  • Method for preparing Meixianduoxin
  • Method for preparing Meixianduoxin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] 22.68g of L-pyroglutamic acid (0.176mol) and 29.70g of vitamin B6 base (0.176mol) were evenly mixed. During this process, there was no stickiness, and it was always in the form of dry powder. Put this mixed powder into a 150ml reaction bottle, then add 40ml of isopropanol under stirring, which contains 1.5ml of deionized water (the specific gravity of isopropanol is 0.7851), stir in a water bath at 35°C for 2 hours, and keep warm Stand at 35°C for 15 hours. Then filter, vacuum-dry the resulting white solid at 35°C for 4 hours, grind it finely, pass through an 80-mesh sieve, and then dry it in vacuum at 35°C for 5 hours to obtain 45.00g of white solid, the product is metadoxine, and the yield was 85.9%.

[0021] The reaction product obtained in this example is a white odorless crystalline powder with a slightly sour taste, easily soluble in water, slightly soluble in cold ethanol, insoluble in common organic solvents such as acetone, ether, chloroform, benzene, etc. Si...

Embodiment 2

[0042] Put 8.663g L-pyroglutamic acid (0.0671mol) and 11.353g vitamin B6 alkali (0.0671mol) into 100ml reaction bottle respectively, then add 30ml isopropanol under stirring, contain 1.0ml deionized water in isopropanol, Stir in a water bath at 38°C for 16 hours, then filter, vacuum-dry the resulting white solid at 40°C for 3 hours, grind it finely, pass through a 100-mesh sieve, and then dry it in vacuum at 40°C for 12 hours to obtain 16.19g of a white solid, the product It is metadoxine with a yield of 80.9%.

[0043] The reaction product of this embodiment is the specific confirmation of the metadoxine structure:

[0044] 1. The melting point of the reaction product: 98.0-100°C, consistent with the metadoxine in the literature;

[0045] 2. As shown in Figure 4, the infrared absorption spectrum (IR) figure shows that the characteristic absorption of the metadoxin ion to the salt is different from the characteristic absorption of the two starting reactants;

[0046] 3. As s...

Embodiment 3

[0056] Embodiment 3: preparation metadoxine

[0057] Mix 19.107g L-pyroglutamic acid (0.148mol) and 25.042g vitamin B6 base (0.148mol) evenly, put the mixed powder into a 100ml reaction bottle, then add 24.4ml isopropanol under stirring, Contain 0.5ml of deionized water, stir in a water bath at 30°C for 3 hours, keep at 30°C for 16 hours, then filter, dry the white solid at 45°C in vacuum for 4 hours, grind it finely, pass it through a 80-mesh sieve, and then filter it at 45°C After vacuum drying at ℃ for 2 hours, 36.11 g of white solid was obtained, and the product was metadoxine, with a yield of 81.8%.

[0058] The reaction product of this embodiment is the specific confirmation of the metadoxine structure:

[0059] 1. The melting point of the reaction product: 98.2-100.1°C, consistent with the metadoxine in the literature;

[0060] 2. As shown in Figure 6, the proton nuclear magnetic resonance spectrum ( 1 HNMR) detection (D 2 O, TMS, 300MHz)

[0061] δppm 1.787-1.899 ...

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Abstract

This invention relates to a method for preparing metadoxine. The method comprises: adding isopropanol to mixed solid powder of vitamin B6 alkali and pyroglutamic acid, reacting at 25-45 deg.C for 30 min-24 h, filtering, and drying the solid to obtain metadoxine. The mol. ratio of vitamin B6 alkali to pyroglutamic acid is 1:1. The weight ratio of pyroglutamic acid to isopropanol is 1 :( 1.0-4). The content of deionized water in isopropanol is 0-5%. The method has such advantages as no need for refinery, low solvent consumption, low cost, simple process, easy operation and high yield, and is suitable for industrialization. The obtained drug-grade metadoxine can be used to treat acute and chronic alcoholism and alcoholic liver disease.

Description

technical field [0001] The invention relates to a method for preparing medicine, in particular to a method for preparing metadoxine. Background technique [0002] The chemical name of metadoxine is the (1:1) salt of 5-keto-L-proline and 5-hydroxy-6-methyl-3,4-pyridinedimethanol, and its molecular formula is: C 8 h 11 NO 3 ·C 5 h 7 NO 3 , Molecular weight: 298.29. American Chemical Abstracts (CAS) registration number is 74536-44-0. Another name of metadoxine: vitamin B6 pyroglutamate, its structural formula is: [0003] [0004] Metadoxine is a metabolic balance drug used in the treatment of acute and chronic alcoholism, alcoholic liver disease. Metadoxin was first launched in Italy in 1985 under the trade name Metadoxil. In the drug instructions, the pharmacological effects of metadoxine are described as: Experimental studies have proved that metadoxine has a positive effect on alcoholic liver disease. Metadoxine can increase hepatic adenosine triphosphate (ATP...

Claims

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Application Information

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IPC IPC(8): C07D213/66C07D207/28A61K31/4425A61P43/00A61P1/16
Inventor 刘路郑意端张英辉廖冬宁谭凯李进旺
Owner YUANXING PHARM
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