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

A technology of coronavirus, chloroquine phosphate, 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 L-chiral chloroquine phosphate in preparation of medicine for treating coronavirus
  • Application of L-chiral chloroquine phosphate in preparation of medicine for treating coronavirus
  • Application of L-chiral chloroquine phosphate in preparation of medicine for treating coronavirus

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] The preparation of embodiment 1 chiral chloroquine phosphate

[0017] (1) Preparation of S-(+)-chloroquine binaphthol phosphate

[0018] 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.

[0019] (2) Recrystallization

[0020] 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.

[0021] (3) Preparation of S-(+)-chloro...

Embodiment 2

[0031] The preparation of embodiment 2 chiral chloroquine phosphate

[0032] (1) Preparation of R-(-)-chloroquine binaphthol phosphate

[0033] Take 4.6g of chloroquine racemate (CAS No.54-05-7), add 5.4g of (R)-(-)-binaphthol phosphate, add 50g of isopropanol and 16g of acetone, heat to dissolve at 60°C, and keep warm for 1h , stirred and cooled to room temperature, cooled to 0-4°C, stood still for 12 hours, precipitated crystals, filtered, drained, the filtrate was stored as S-rich mother liquor, the filter cake was a light yellow solid, and 6.2g of solid was obtained by drying at 60°C. It is R-(-)-chloroquine binaphthol phosphate.

[0034] (2) Recrystallization

[0035] 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...

Embodiment 3

[0046] Embodiment 3 cell level evaluation L-, D-, racemic chloroquine phosphate anti-new coronavirus (SARS-COV-2) effect

[0047] 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 .

[0048] Left-handed chiral chloroquine phosphate is prepared by embodiment 2 step (1), and right-handed chiral chloroquine chlorate is prepared by embodiment 1 step (1).

[0049] 2.1 Test drug antiviral experimental operat...

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Abstract

The invention discloses an application of L-chiral chloroquine phosphate in preparation of a medicine for treating coronavirus. Based on the fact that in an in-vitro cell experiment, L-chiral chloroquine phosphate has a remarkable inhibition effect on cytopathy caused by infection of Vero E6 cells by novel coronavirus SARS-CoV-2, the IC50 value is 1.45 mu g / mL, the inhibition concentration is remarkably lower than that of D-chloroquine phosphate and racemate chloroquine phosphate. The important significance is realized on the prevention, control and treatment of novel coronavirus infection.

Description

technical field [0001] The invention belongs to the field of medicine, in particular to the application of left-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. However, based on the current clinical application effects, Zhong Nanshan, an academician of the Chinese Academy of Engineering, pointed out that chloroquine phosphate is not enough to be called a special drug for the treatment of new coronary pneumonia, but it has therapeutic effects and has few side effects, so it is worth exploring and studying. [0003] The side chain of chloroquine contains a chiral carbon, and all dosage forms of chloroquine in clinical use are racemate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/4706A61P31/14A61P11/00C07D215/46
CPCA61K31/4706C07D215/46A61P31/14A61P11/00C07B2200/07
Inventor 张逸伟廖能林东恩
Owner SOUTH CHINA UNIV OF TECH
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