Application of dextro-chiral chloroquine phosphate in preparation of medicine for treating coronavirus

A kind of d-chloroquine phosphate, coronavirus technology, applied in the field of medicine

Pending Publication Date: 2021-09-07
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For chloroquine, there is no relevant report about chiral chloroquine in anti-coronavirus

Method used

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  • Application of dextro-chiral chloroquine phosphate in preparation of medicine for treating coronavirus
  • Application of dextro-chiral chloroquine phosphate in preparation of medicine for treating coronavirus
  • Application of dextro-chiral chloroquine phosphate in preparation of medicine for treating coronavirus

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] The preparation of embodiment 1 chiral chloroquine phosphate

[0016] (1) Preparation of S-(+)-chloroquine binaphthol phosphate

[0017] Take 8.3g of chloroquine racemate, add 9.7g of (S)-(+)-binaphthol phosphate, add 90g of isopropanol and 30g of acetone, heat to dissolve at 70°C, keep warm for 1h, stir and cool to room temperature, then cool down to 0~ Stand at 4°C for 18 hours, crystallize out, filter, drain, and save the filtrate as R-rich mother liquor. The filter cake is a light yellow solid. Dry at 60°C to obtain 11.8g. This solid is S-(+)-chloroquine binaphthol Phosphate salt.

[0018] (2) Recrystallization

[0019] Add 75g of isopropanol and 25g of acetone to 11.8g (17.7mmol) of the solid obtained in step (1), heat to dissolve at 70°C, stir slowly to room temperature, cool down to 0-4°C, and let stand for 6h to precipitate large crystals. Filtrate, drain to obtain a glossy loose solid, and dry at 60°C to obtain 8.6g.

[0020] (3) Preparation of S-(+)-chloro...

Embodiment 2

[0030] The preparation of embodiment 2 chiral chloroquine phosphate

[0031] (1) Preparation of R-(-)-chloroquine binaphthol phosphate

[0032] Take 4.6g of chloroquine racemate (CASNo.54-05-7), add 5.4g of (R)-(-)-binaphthol phosphate, add 50g of isopropanol and 16g of acetone, heat to dissolve at 60°C, keep warm for 1h, Stir and cool to room temperature, lower the temperature to 0-4°C, let stand for 12 hours, precipitate crystals, filter, and drain, the filtrate is stored as S-rich mother liquor, the filter cake is a light yellow solid, and 6.2g of solid is obtained by drying at 60°C. R-(-)-chloroquine binaphthol phosphate.

[0033] (2) Recrystallization

[0034] Add 6.2 g of the solid obtained in step (1) to 30 g of isopropanol and 9 g of acetone, heat to dissolve at 60 ° C, slowly stir to room temperature, cool to 0-4 ° C, let stand for 6 h, precipitate large crystals, filter, and drain It was a glossy and loose solid, and it was dried at 60°C to obtain 4.7 g of solid. ...

Embodiment 3

[0045] Embodiment 3 cell level evaluation D-, racemic chloroquine phosphate anti-new coronavirus (SARS-COV-2) effect

[0046] The experiment to evaluate the effect of drugs against the new coronavirus (SARS-COV-2) at the cellular level was conducted by the Guangzhou Institute of Respiratory Health. Among them, the cells used are VeroE6 cells, which are preserved by the virus room of the State Key Laboratory of Respiratory Diseases, Guangzhou Institute of Respiratory Health; the virus SARS-CoV-2, the titer is TCID 50 =10 -6 / 100μL, stored at -80°C by BSL-3 Laboratory of Guangzhou Customs Technology Center (Highly Pathogenic Pathogenic Microorganism Research Laboratory of State Key Laboratory of Respiratory Diseases). Use a viral titer of 100TCID 50 .

[0047] Right-handed chiral chloroquine chlorate is prepared by embodiment 1 step (1)

[0048] 2.1 Test drug antiviral experimental operation

[0049] (1) Test drug:

[0050] Table 1 Drug name, experimental concentration and...

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Abstract

The invention discloses application of dextro-chiral chloroquine phosphate in preparation of a medicine for treating coronavirus. The inventor of the invention finds that in an in-vitro cell experiment, the dextro-chiral chloroquine phosphate has a better anti-novel coronavirus effect than the currently applied chloroquine phosphate, and under the condition that the inhibition rate (78.33%) is the same, the drug concentration of the dextro-chiral chloroquine phosphate is 3.75 mu g / mL, and the drug concentration of racemic chloroquine is 6.25 mu g / mL. The invention provides a new way for treating coronavirus.

Description

technical field [0001] The invention belongs to the field of medicine, in particular to the application of right-handed chiral chloroquine phosphate in the preparation of drugs for treating coronavirus. Background technique [0002] Chloroquine phosphate is an old drug that has been used as early as the 1930s and 1940s, mainly for the treatment of malaria. Recent studies have shown that chloroquine has a certain inhibitory effect on the virus (2019-nCoV) that causes novel coronavirus pneumonia COVID-19. [0003] The side chain of chloroquine contains a chiral carbon, and all dosage forms of chloroquine in clinical use are racemates at present. Existing studies have shown that the chiral structure of some drugs is closely related to their biological activity. For example, the antipyretic and analgesic drug ibuprofen commonly used in daily life mainly works in the S configuration, and its R configuration is completely Not active. As for chloroquine, there is no relevant rep...

Claims

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Application Information

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IPC IPC(8): A61K31/4706A61P31/14
CPCA61K31/4706A61P31/14
Inventor 张逸伟廖能林东恩
Owner SOUTH CHINA UNIV OF TECH
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