Triazine compound and application thereof in preparation of antiviral drugs

A compound and drug technology, applied in the field of triazine compounds and their use in the preparation of antiviral drugs, can solve the problems of difficulty in generating effective immunity, low immunization rate, shortening and the like, and achieve a reduction in single administration Dosage, increase blood concentration, and the effect of good therapeutic effect

Active Publication Date: 2022-05-17
YAOKANG ZHONGTUO (JIANGSU) PHARMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The vaccine itself has certain limitations: the immunization rate is low, it is difficult to produce effective herd immunity; it is difficult to produce effective immunity to high-risk groups, such as the elderly and immunocompromised groups; due to the lack of post-translational correction mechanism of viral RNA polymerase , so in the face of continuous mutation of the virus, it is necessary to continuously develop new vaccines, and at the same time, it is difficult to produce a sufficient number of new vaccines in a short period of time in the early stages of a rapid epidemic
Deuterium at certain sites not only cannot prolong the half-life, but may shorten it and degrade its pharmacokinetic properties; the effect of deuterium molecules on cell activity is even more unpredictable and inconclusive
On the other hand, the hydrogen at certain positions on the drug molecule is not easy to be deuterated due to steric hindrance and other reasons. Therefore, the deuterium of the drug is not arbitrary, and the effect of the deuterated site on the drug is unpredictable.

Method used

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  • Triazine compound and application thereof in preparation of antiviral drugs
  • Triazine compound and application thereof in preparation of antiviral drugs
  • Triazine compound and application thereof in preparation of antiviral drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Embodiment 1: the synthesis of compound 1-1

[0052]

[0053] Step 1: Synthesis of deuterated compound 4a

[0054]

[0055] (1) Compound 1 (18.6 g, 0.1 mol) was suspended in water (80 ml) and concentrated hydrochloric acid (25 ml, 0.3 mol), and NaNO 2 Aqueous solution (6.9 g, 0.1 mol) was added dropwise to the above solution, then stirred for 20 min, filtered, pre-cooled NaBF 4 (12. g, 0.1 mol) aqueous solution (40ml) was added to the above filtrate and stirred for 40min. Stop stirring, filter, wash the filter cake with cold ethanol and ether, collect the filter cake, and dry to obtain diazonium salt (11.5 g, 0.05 mol). Dissolve the diazonium salt in CHCl 3 (100 mL), KOAc (8.15 g, 0.78 mol) was added to the above solution, stirred at room temperature for 2 h, the reaction was complete, and the stirring was stopped. Add water (50 ml) to quench the reaction, extract with DCM (50 mL × 3), combine the organic phases, wash with saturated brine, anhydrous Na 2 S...

Embodiment 2

[0074] Embodiment 2: the synthesis of compound 1-2

[0075]

[0076] The synthesis method is as in Example 1-1, only the corresponding raw materials need to be replaced. 1 H NMR (400 MHz, DMSO- d 6 ,DC in D 2 O) δ 9.33 (1H, s), 8.43 (1H, s), 7.78 (1H, s), 7.65-7.49 (2H, m), 7.48 (1H, m), 5.37 (2H, s), 5.09 (2H , s), 4.19 (3H, s), 3.95 (1H, s). MS(ESI, m / z): 534 (M + +1).

Embodiment 3

[0077] Embodiment 3: the synthesis of compound 1-3

[0078]

[0079] The synthesis method is as in Example 1, only the corresponding raw materials need to be replaced. 1 H NMR (400 MHz, DMSO- d 6 , DClin D 2 O) δ 9.33 (1H, s), 8.43 (1H, s), 7.78 (1H, s), 7.63-7.48 (2H, m), 7.47(1H, m), 5.36 (2H, s), 5.09 (2H , s), 4.19 (3H, s), 3.95 (2H, s). MS (ESI, m / z): 533 (M + +1).

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PUM

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Abstract

The invention relates to a triazine compound with a structure represented by a formula A, or a stereoisomer, a prodrug, an active metabolite or a pharmaceutically acceptable salt, a solvate or a crystal form thereof, a pharmaceutical composition of the triazine compound, the stereoisomer, the prodrug, the active metabolite or the pharmaceutically acceptable salt, the solvate or the crystal form, and a use method of the triazine compound. In addition, the invention also relates to a method for preparing a 3C-like cysteine protease inhibitor or a medicine for treating and / or preventing virus infectious diseases. In particular, the present invention relates to the use for treating viral infectious diseases such as Middle East Syndrome Related Coronavirus (MERS-CoV), Severe Acute Respiratory Syndrome Related Coronavirus (SARS-CoV), Influenza A virus, Influenza B virus, Novel Coronavirus Pneumonia (COVID-19) and the like.

Description

technical field [0001] The present invention provides a triazine compound or its stereoisomer, prodrug, active metabolite or pharmaceutically acceptable salt, solvate or crystalline form, its preparation method, a pharmaceutical composition containing it, and the use of the combination The use of substances for the prevention or treatment of viral infectious diseases. Background technique [0002] Coronavirus (coronavirus) belongs to the genus Coronaviridae Coronaviridae in terms of systematic classification. Mature coronaviruses are corona-shaped or crown-shaped under the electron microscope, so they are named coronaviruses, which can easily cause central nervous system diseases, common colds, and lower respiratory tract infections. and diarrhea. In 2003, SARS-CoV-1 was the first coronavirus to spread in humans, causing more than 900 deaths (case fatality rate 10-15%), and more than 8,000 people were infected. In 2012, Middle East Respiratory Syndrome Coronavirus (MERS-Co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/14A61P31/12A61P31/14A61P31/16A61P31/18A61K31/53
CPCC07D403/14A61P31/12A61P31/14A61P31/16A61P31/18
Inventor 孟祥杰
Owner YAOKANG ZHONGTUO (JIANGSU) PHARMA TECH CO LTD
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