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Heterocycle non-nucleosides compound and preparation method thereof, medicament composition and purpose as antivirus antivirus inhibitor

A technology of nucleosides and compounds, applied in antiviral agents, organic chemistry, pharmaceutical formulations, etc., can solve problems such as cytotoxicity

Active Publication Date: 2012-12-19
TAIZHOU HAIHE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Among the currently approved antiviral drugs, the vast majority are nucleoside compounds, and they have been found to have the following disadvantages during clinical application: 1) Cytotoxicity; 2) The emergence of drug-resistant virus mutants produced by long-term drug use requires Therefore, the development of non-nucleoside antiviral drugs has become an attractive direction

Method used

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  • Heterocycle non-nucleosides compound and preparation method thereof, medicament composition and purpose as antivirus antivirus inhibitor
  • Heterocycle non-nucleosides compound and preparation method thereof, medicament composition and purpose as antivirus antivirus inhibitor
  • Heterocycle non-nucleosides compound and preparation method thereof, medicament composition and purpose as antivirus antivirus inhibitor

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0100]

[0101] Compound 1.1 (3.3mmol), compound 2.1 (3mmol), N-ethyl-N'-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC) (3.3mmol), N,N- Dimethylpyridine (DMAP) (0.3mmol) and molecular sieves were mixed, cooled in an ice bath (0°C), and then DMF (5mL) and pyridine (4.5mmol) were added in turn, followed by TLC to determine the degree of completion of the reaction. It was diluted with water (25 mL), extracted with EtOAc (25 mL), concentrated to remove the solvent, and separated by column chromatography petroleum ether / ethyl acetate (volume ratio 5:1) to obtain compound 3.1. After that, compound 3.1 (0.6mmol) was mixed with ammonium acetate (NH 4 OAc) (15mmol) and sodium acetate (NaOAc) (30mmol) were mixed, heated to 130°C, followed by TLC to determine the degree of completion of the reaction, then cooled to room temperature, diluted with water (50mL), extracted with ethyl acetate (50mL), concentrated The solvent was removed, and the compound 4i.1 was obtained by pet...

preparation Embodiment 2

[0105]

[0106] Compound 3.1 (0.6mmol) was mixed with Lawesson's reagent (0.9mmol), then THF (5mL) was added, heated to reflux, TLC was followed to determine the degree of completion of the reaction, then cooled to room temperature, the reaction solution was concentrated to remove the solvent, and petroleum ether / ethyl acetate (volume ratio 3:1) column chromatography to obtain compound 4ii.1.

[0107]Using the same method as Preparation Example 1, but adopting the different substituted carboxylic acids (compound 1) listed in the following table to replace pyridine-2-carboxylic acid, different compound 2 to replace compound 2.1, different compound 3 can be synthesized; then, Using the same method as Preparation Example 2, the following target compounds were synthesized:

[0108] The following compounds were synthesized in the same way:

[0109]

[0110]

[0111]

[0112]

[0113]

preparation Embodiment 3

[0115]

[0116] Compound 3.1 (0.6mmol) and POCl 3 (3mL) mixed, heated to 80 ° C, TLC to track the degree of completion of the determination of the reaction, then pour the reaction solution into 0 ° C saturated sodium bicarbonate (NaHCO 3 ) solution (50mL), remove POCl 3 , and then extracted with ethyl acetate (50 mL), concentrated to remove the solvent, and separated by petroleum ether / ethyl acetate (volume ratio 4:1) column chromatography to obtain compound 4iii.1.

[0117] Using the same method as in Preparation Example 1, but using different substituted carboxylic acids (compound 1) listed in the table below to replace pyridine-2-carboxylic acid, different compounds 3 can be synthesized; then, using the same method as in Preparation Example 3 method, the following target compounds were synthesized:

[0118]

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Abstract

The invention relates a kind of antiviral agents, more concretely, relates to a kind of heterocyclic non-nucleoside compounds with the following structures, their preparation and pharmaceutical compositions including the compounds. The said compounds can be used as antiviral agents and as medicaments for treating diseases such as hepatitis B, influenza, herpes, HIV and so on.

Description

technical field [0001] The present invention relates to a class of antiviral inhibitors, in particular to a class of heterocyclic non-nucleoside compounds and their preparation methods, and pharmaceutical compositions containing the compounds, which can be used as antiviral inhibitors for use in For the treatment of hepatitis B, influenza, herpes, AIDS and other diseases. Background technique [0002] Human pathogenic virus is a kind of nucleic acid particle with extremely simple structure. Most of them lack enzyme system and can only rely on host cells to replicate their nucleic acid and protein, and then assemble into virus particles to proliferate. Virus infection can cause various diseases and seriously endanger human health and life. According to incomplete statistics, about 60% of epidemic infectious diseases are caused by virus infection. So far, more than 3,000 viruses have been discovered in the world, and new viruses are still being discovered. At the World Cong...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/04C07D417/14C07D263/32C07D277/32A61K31/427A61P31/12
CPCC07D263/32C07D277/24C07D277/56C07D513/04C07D263/34C07D417/04A61P31/12A61P31/16A61P31/18A61P31/22A61K31/427C07D277/32
Inventor 南发俊左建平陈海军王桂凤顾民朱峰华唐炜
Owner TAIZHOU HAIHE PHARM CO LTD
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