A co-crystal of coenzyme QH and nicotinamide and its preparation method and application

A technology of nicotinamide and coenzyme, which is applied in ether preparation, organic chemical methods, organic chemistry, etc., can solve problems such as oxidation and co-crystallization preparation methods, and achieve improved chemical stability, excellent chemical stability, and good reproducibility Effect

Active Publication Date: 2022-02-15
COCRYSTAL PHARMA TECH SHANGHAI CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] CN103635452A has prepared a stable crystal form of coenzyme QH, but it will still be oxidized if placed in the air for a long time
However, these two ligands are not suitable for large-scale use in food, and the preparation method of the co-crystal is complicated, requiring stirring in a solvent for more than 3 days

Method used

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  • A co-crystal of coenzyme QH and nicotinamide and its preparation method and application
  • A co-crystal of coenzyme QH and nicotinamide and its preparation method and application
  • A co-crystal of coenzyme QH and nicotinamide and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] Add 10 grams of oxidized coenzyme Q10 and 6 grams of L-ascorbic acid to 100 grams of 95% ethanol, stir at 78°C for reduction reaction, cool to 0°C after 20 hours, keep stirring at this temperature for 1 hour, and filter under reduced pressure . The filter cake was rinsed three times with 95% ethanol, and dried under reduced pressure to obtain a white eutectic. All operations were performed under nitrogen protection except drying under reduced pressure. The weight ratio of coenzyme QH / oxidized coenzyme Q10 in the obtained sample was 99.2 / 0.8.

[0075] This powder is detected by differential scanning calorimetry (DSC), the result Figure 13 shown. Depend on Figure 13 It can be seen that QH has a characteristic endothermic peak at about 49 °C.

Embodiment 2

[0077] Add 0.4 g of nicotinamide and 1 g of the coenzyme QH obtained in Example 1 to 10 ml of isopropanol / isopropyl acetate = 1 / 1 solvent, stir and dissolve at 40°C, and recrystallize to obtain a white precipitate , filtered the precipitate through a Buchner funnel, and dried the solid in a vacuum oven at room temperature for 12 hours to obtain a co-crystal of coenzyme QH and nicotinamide.

[0078] The contents of coenzyme QH and nicotinamide in the co-crystal of coenzyme QH and nicotinamide were measured respectively by high performance liquid chromatography, and it was found that the content of coenzyme QH was about 86.1%, and the content of nicotinamide was about 12.6%. In this co-crystal, the stoichiometric ratio of coenzyme QH to nicotinamide is about 1:1.

[0079] This co-crystal was characterized by solid state methods such as X-ray powder diffraction (XRPD), differential scanning calorimetry (DSC) and infrared (IR) spectroscopy. The results are as follows Figure 1-F...

Embodiment 3

[0084] Add 0.122 g of nicotinamide and 0.87 g of the coenzyme QH obtained in Example 1 into 2 ml of ethanol, stir and dissolve at 60°C, recrystallize to obtain a white solid, and dry the solid in a vacuum oven at room temperature for 12 hours. A co-crystal of coenzyme QH and nicotinamide was obtained.

[0085] The contents of coenzyme QH and nicotinamide in the co-crystal of coenzyme QH and nicotinamide were measured respectively by high performance liquid chromatography, and it was found that the content of coenzyme QH was about 84.0%, and the content of nicotinamide was about 11.8%. In this co-crystal, the stoichiometric ratio of coenzyme QH to nicotinamide is about 1:1.

[0086] This is characterized by solid state methods such as X-ray powder diffraction (XRPD), differential scanning calorimetry (DSC) and infrared (IR) spectroscopy. The results are basically consistent with the co-crystal detection results of coenzyme QH and nicotinamide in Example 2.

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Abstract

The invention relates to a co-crystal of coenzyme QH and nicotinamide, a preparation method and application thereof. Compared with the existing coenzyme QH, the co-crystal has a higher melting point and has better stability. The preparation method of the coenzyme QH co-crystal is simple, easy to control and good in reproducibility. The invention greatly improves the convenience of using the coenzyme QH, saves the cost in storage, transportation and use, and broadens the application range of the coenzyme QH.

Description

technical field [0001] The invention relates to the technical field of coenzyme Q10, in particular to a co-crystal of coenzyme QH and nicotinamide and a preparation method thereof. Compared with the existing coenzyme QH, the co-crystal has a higher melting point and has better stability. The preparation method of the coenzyme QH co-crystal is simple, easy to control and good in reproducibility. The invention greatly improves the convenience of using the coenzyme QH, saves the cost in storage, transportation and use, and broadens the application range of the coenzyme QH. Background technique [0002] Coenzyme Q10 is the only coenzyme Q substance in the human body, and it is a fat-soluble compound that exists widely in organisms. It is a coenzyme that is not tightly bound to proteins in the respiratory chain, and it plays an important role in proton translocation and electron transfer in the human respiratory chain. As an activator of cell metabolism and cellular respiratio...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C43/23C07C41/40C07C41/46C07D213/82
CPCC07C43/23C07D213/82C07B2200/13
Inventor 梅雪锋张奇鲍俊杰陆鹂烨
Owner COCRYSTAL PHARMA TECH SHANGHAI CO LTD
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