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Amantadine hydrochloride and resveratrol pharmaceutical co-crystal and preparation method thereof

A technology of amantadine hydrochloride and resveratrol, which is applied in the field of drug co-crystals, can solve the problems of toxic side effects and drug efficacy reduction, and achieve the effects of reducing toxic side effects, high yield, and mild reaction conditions

Inactive Publication Date: 2021-03-26
OCEAN UNIV OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Aiming at the problems in the prior art of amantadine hydrochloride caused by too high solubility of toxic side effects and reduced drug efficacy, the object of the present invention is to provide a drug co-crystal of amantadine hydrochloride and resveratrol and a preparation method thereof

Method used

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  • Amantadine hydrochloride and resveratrol pharmaceutical co-crystal and preparation method thereof
  • Amantadine hydrochloride and resveratrol pharmaceutical co-crystal and preparation method thereof
  • Amantadine hydrochloride and resveratrol pharmaceutical co-crystal and preparation method thereof

Examples

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Effect test

Embodiment 1

[0029] Embodiment 1: The preparation method of amantadine hydrochloride and resveratrol drug co-crystal is implemented according to the following steps:

[0030] Add amantadine hydrochloride (56.31 mg) and resveratrol (34.24 mg) in a molar ratio of 2:1 and mix them in a mortar, add 50 mL of isopropanol and quickly grind until dry, and continue grinding for 1 h to obtain a white powder , transfer the white powder to a round bottom flask, add 17 mL of acetonitrile and 1.7 mL of methanol (volume ratio: 10:1) mixed solvent to dissolve, stir for 4 h and then filter, leave the filtrate to evaporate for 3 days to obtain colorless columnar crystals.

[0031] In this example, the drug co-crystal of amantadine hydrochloride and resveratrol prepared by the solvent evaporation method is a colorless columnar crystal, and a single crystal sample with an appropriate size is selected for X-ray single crystal diffraction measurement. The STADIVARI diffractometer of STOE Company in Germany is u...

Embodiment 2

[0035] Embodiment 2: The preparation method of amantadine hydrochloride and resveratrol drug co-crystal is implemented according to the following steps:

[0036] The difference between this embodiment and Example 1 is that the volume ratio of acetonitrile and methanol in the system is 7:1, and other steps and parameters are the same as in Embodiment 1.

Embodiment 3

[0037] Embodiment 3: The preparation method of amantadine hydrochloride and resveratrol pharmaceutical co-crystal is implemented according to the following steps:

[0038] The difference between this embodiment and Example 1 is that the volume ratio of acetonitrile and methanol in the system is 13:1, and other steps and parameters are the same as in Embodiment 1.

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Abstract

The invention discloses an amantadine hydrochloride and resveratrol pharmaceutical co-crystal and a preparation method thereof, and relates to the technical field of pharmaceutical co-crystals. The pharmaceutical co-crystal is characterized in that two amantadine hydrochloride molecules and a resveratrol molecule form a basic structural unit, the chemical formula of the pharmaceutical co-crystal is [2C10H18ClN.C14H12O3], the pharmaceutical co-crystal belongs to a monoclinic system, and the space group is P21 / c. According to the pharmaceutical co-crystal prepared by adopting a solvent evaporation method and a cooling method, the dissolution rate of amantadine hydrochloride is properly reduced while the solubility of resveratrol is improved, so that the toxic and side effects caused by excessive dissolution of amantadine hydrochloride are favorably reduced; through bidirectional coupling optimization and advantage complementation of the two components in nature, the antiviral activity ofamantadine hydrochloride is significantly improved, and a new thought is provided for development of synergistic antiviral drugs; and the pharmaceutical co-crystal can keep the skeleton structure ofthe crystal unchanged after long-term placement at room temperature, and the preparation method is simple and easy to implement, low in cost and convenient for large-scale production.

Description

technical field [0001] The invention relates to the technical field of drug co-crystals, in particular to a drug co-crystal of amantadine hydrochloride and resveratrol and a preparation method thereof. Background technique [0002] In the long course of human history, viral diseases have always been one of the main killers of human health, killing hundreds of millions of people in the past few centuries. In order to defeat the virus, the rapid development of antiviral drugs has attracted much attention. As we all know, the creation of new drugs and the transformation of existing drugs are the eternal themes of drug research and development. However, the creation of new drugs has limitations such as long cycle time, high cost, and high failure rate; and viruses have the characteristics of rapid onset, wide infectivity, and high fatality rate, making it difficult for the traditional new drug research and development model to quickly respond to viral diseases in a short period...

Claims

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Application Information

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IPC IPC(8): C07C211/38C07C209/86C07C39/21C07C37/84A61P31/12
CPCA61P31/12C07B2200/13C07C39/21C07C211/38
Inventor 李延团牛圆圆王凌阳赵明钰吴智勇
Owner OCEAN UNIV OF CHINA
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