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Compound crystal, preparation method and application

A compound and crystal technology, applied in the field of chemistry and medicine, can solve problems such as not providing crystal structure data

Active Publication Date: 2021-04-09
BEIJING INSTITUTE OF PETROCHEMICAL TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A new crystal form is reported in CN 107759529 A patent, but no crystal structure data is provided

Method used

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  • Compound crystal, preparation method and application
  • Compound crystal, preparation method and application
  • Compound crystal, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] After mixing Favipiravir and p-aminobenzoic acid uniformly at a molar ratio of 1:1, take about 2 g of solid, add about 0.5 ml of ethyl acetate, and grind manually in a mortar for 30 minutes. The samples were dried in a forced air oven at 30°C. The resulting product is analyzed by XRD and is a co-crystal of Favipiravir-p-aminobenzoic acid.

Embodiment 2

[0033] After mixing Favipiravir and p-aminobenzoic acid uniformly at a molar ratio of 1:1, take about 2g of solid, add 10ml of methyl tert-butyl ether, and suspend and stir with magnetic stirring at room temperature for 72h-96h. After the sample was filtered, the obtained solid was dried in a blast drying oven at 60°C. Gained solid shows through XRD analysis, is the eutectic of favipiravir-p-aminobenzoic acid.

Embodiment 3

[0035] Take 0.6g of p-aminobenzoic acid, add 50ml of ethyl acetate, dissolve after heating. Then add 0.456g of Favipiravir and stir for 2h. After the solid was filtered, it was air-dried at 40°C. XRD analysis showed that it was a co-crystal of favipiravir-para-aminobenzoic acid.

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Abstract

The invention discloses a compound crystal, and a preparation method and application thereof, belonging to the technical field of chemical medicines. The compound crystal is a eutectic crystal of favipiravir and p-aminobenzoic acid, the unit cell of the eutectic crystal belongs to a monoclinic system and a P21 / c space group, and the unit cell parameters are as follows: alpha = gamma = 90 degrees and beta = 92.578 (3) degrees. The equivalent solubility of the favipiravir in the compound crystal provided by the invention is reduced by about 50%, so that the dissolution rate of the favipiravir is favorably reduced, the onset time of the favipiravir is prolonged, and the toxic and side effects of the favipiravir are reduced.

Description

technical field [0001] The invention belongs to the technical field of chemistry and medicine, and in particular relates to a compound crystal, a preparation method and an application. Background technique [0002] The chemical structural formulas of 6-fluoro-3-hydroxypyrazine-2-carboxamide (favipiravir, cas259793-96-9, Chinese name Favipiravir) and 4-aminobenzoic acid are shown in Formula 1 and Formula 2. [0003] [0004] 6-Fluoro-3-hydroxypyrazine-2-carboxamide is a pyrazine analog drug developed by Toyama Chemical Co., Ltd. in Japan, which was originally approved for the treatment of drug-resistant influenza. 6-fluoro-3-hydroxypyrazine-2-carboxamide can not only inhibit the replication of influenza A and type B, but also has great hope in the treatment of avian influenza. There are currently studies using Favipiravir for the treatment of other deadly viral infections, such as Ebola virus, Lassa virus and new coronavirus (COVID-19). [0005] In WO12043700A1 and WO120...

Claims

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Application Information

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IPC IPC(8): C07D241/24C07C229/60C07C227/42A61K31/4965A61P31/16
CPCC07D241/24C07C229/60A61P31/16C07B2200/13
Inventor 何运良张阗王学重周浩宇
Owner BEIJING INSTITUTE OF PETROCHEMICAL TECHNOLOGY
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