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Stellate spike protein-targeted anti-respiratory tract infection virus bifunctional compounds and preparation method and application of salts of stellate spike protein -targeted anti-respiratory tract infection virus bifunctional compounds

A technology of compounds and hydrates, applied in antiviral agents, respiratory diseases, chemical instruments and methods, etc., can solve problems such as failure, difficulty in targeting drugs, and no curative effect of antiviral drugs, and achieve good pathogen specificity and high Clinical Safety Effects

Active Publication Date: 2021-03-19
SHENZHEN CELL INSPIRE PHARM DEV CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, wild animals carry nearly 500,000 viruses that may infect humans, and it is impossible to develop specific targeted drugs for each virus
The explosiveness of the virus epidemic and the high variability of the virus make it difficult for simple targeted drugs to respond to the needs of epidemic prevention and control in a timely manner, because it is easy to fail due to the rapid mutation of RNA viruses
In addition to the long development cycle, the main problems with simple targeted antiviral drugs are:
[0004] (1) Drug resistance due to rapid mutation of the virus,
[0005] (2) Critically ill patients in the late stage of infection are life-threatening due to inflammatory storm or vascular embolism, and specific antiviral drugs are often ineffective at this time

Method used

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  • Stellate spike protein-targeted anti-respiratory tract infection virus bifunctional compounds and preparation method and application of salts of stellate spike protein -targeted anti-respiratory tract infection virus bifunctional compounds
  • Stellate spike protein-targeted anti-respiratory tract infection virus bifunctional compounds and preparation method and application of salts of stellate spike protein -targeted anti-respiratory tract infection virus bifunctional compounds
  • Stellate spike protein-targeted anti-respiratory tract infection virus bifunctional compounds and preparation method and application of salts of stellate spike protein -targeted anti-respiratory tract infection virus bifunctional compounds

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Experimental program
Comparison scheme
Effect test

preparation example Construction

[0098] According to some embodiments of the present invention, the present invention provides a method for preparing the star-shaped bifunctional compound targeting spinin-containing virus causing lung infection, comprising the following steps:

[0099]

[0100] The synthetic route of the star-shaped bifunctional compound targeting spinin-containing virus causing lung infection is shown above. Phenolic raw materials containing carboxylic acid groups (R 1 -COOH) was added to dichloromethane (DMF, pyridine, tetrahydrofuran, etc. can be used instead), dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP) were added at the same time, and stirred at room temperature for 0.5h. Sugars with or without protective groups, aromatic rings with hydroxyl groups, aliphatic chains with hydroxyl groups (R 2 -OH), stirred at room temperature or under heating for 8h. Extract with ethyl acetate or dichloromethane, take the organic layer, spin dry the organic solvent, and obtain t...

Embodiment 1

[0102] The synthesis of embodiment 1 compound 1

[0103] 3,4,5-Tribenzyloxybenzoic acid (2.2 mmol), dicyclohexylcarbodiimide (DCC, 2.2 mmol) and 4-dimethylaminopyridine (DMAP, 0.2 mmol), added to dichloromethane , while stirring at room temperature for 0.5h. Then 1,4-benzenediol (1 mmol) was added and stirred at room temperature for 8 h. Then use ethyl acetate to extract, take the organic layer, spin dry the organic solvent, and obtain the intermediate after separation and purification by column chromatography. The intermediate and palladium carbon (60 mg) were added to methanol, the air was drained and filled with hydrogen, stirred at room temperature for 2 h, the palladium carbon was removed by filtration, and the organic layer was spin-dried. Compound 1 was obtained by column chromatography with a total yield of 62.4%. The synthesis process of compound 1 is as follows: figure 1 shown.

Embodiment 2

[0104] The synthesis of embodiment 2 compound 2

[0105] 3,4,5-Tribenzyloxybenzoic acid (3.3 mmol), dicyclohexylcarbodiimide (DCC, 3.3 mmol) and 4-dimethylaminopyridine (DMAP, 0.3 mmol), added to dichloromethane , while stirring at room temperature for 0.5h. Then 2-(6-(benzyloxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)acetamide (1 mmol) was added and stirred at room temperature for 8 h. Then use ethyl acetate to extract, take the organic layer, spin dry the organic solvent, and obtain the intermediate after separation and purification by column chromatography. The intermediate and palladium carbon (100 mg) were added to methanol, the air was drained and filled with hydrogen, stirred at room temperature for 2 h, the palladium carbon was removed by filtration, and the organic layer was spin-dried. Compound 2 was obtained by column chromatography with a total yield of 53.5%. The synthesis process of compound 2 is as follows figure 2 shown.

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Abstract

The invention relates to the field of medicine design and medicinal chemistry, in particular to stellate spike protein-targeted anti-respiratory tract infection virus bifunctional compounds and a preparation method and application of salts of the stellate spike protein -targeted anti-respiratory tract infection virus bifunctional compounds. The novel stellate spike protein-targeted anti-respiratory tract infection virus bifunctional compounds have a significant anti-Corona Virus Disease-19 spike protein targeting and a certain broad spectrum. Molecules and salts thereof have at least one R(X)<n> basic unit that binds to a spike protein-containing virus or viruses containing spike proteins on the surfaces at a positive binding site, such as the RBD domain or allosteric site, so that coronavirus or other viruses expressing spike protein on the surface is prevented from invading host cells and preventing the occurrence of viral infections. The molecules and salts thereof interact with vitamin K dependent protein in a human body to inhibit expression of vitamin K so as to inhibit blood coagulation in the human body, so that vascular embolism caused by corona virus is treated, and a curative effect on pneumonia caused by severe virus infection is achieved.

Description

technical field [0001] The present invention relates to the fields of drug design and medicinal chemistry, and more specifically, relates to a preparation method and application of a class of bifunctional compounds targeting star-shaped spine protein against respiratory virus infection and salts thereof. Background technique [0002] New Coronary Pneumonia (COVID-19) has become a global health challenge. Since it is a newly discovered virus, no specific drugs or vaccines have been approved for treatment. Currently, much effort is focused on screening older drugs for inhibitors of key enzymes in the viral life cycle. Although special channels are given for new use of old drugs, the results of clinical trials published so far remain to be seen. [0003] The main idea of ​​the current mainstream antiviral drug research is: to obtain target molecules (mainly proteins) related to virus replication, design or screen their inhibitors, and clarify the mode of action of receptors an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H13/08C07D311/64C07C69/88A61K31/7028A61K31/352A61K31/235A61P31/14A61P9/00A61P11/00A61P35/00A61P19/02A61P29/00A61P13/00A61P1/12
CPCC07H13/08C07D311/64C07C69/88A61P31/14A61P9/00A61P11/00A61P35/00A61P19/02A61P29/00A61P13/00A61P1/12C07D311/22C07D311/36
Inventor 徐峻郝梦娇张毓婷陈浩
Owner SHENZHEN CELL INSPIRE PHARM DEV CO LTD
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