A kind of substituted naphthalene ring compound, pharmaceutical composition and application thereof

A compound and composition technology, applied in the field of medicine, to achieve the effect of improving applicability, good pharmacokinetic parameter characteristics, and increasing drug concentration

Active Publication Date: 2021-04-30
SHENZHEN TARGETRX INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because the drugs work on every cell in the body, these drugs have many side effects

Method used

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  • A kind of substituted naphthalene ring compound, pharmaceutical composition and application thereof
  • A kind of substituted naphthalene ring compound, pharmaceutical composition and application thereof
  • A kind of substituted naphthalene ring compound, pharmaceutical composition and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Example 1 Preparation of N-(6-(3-tert-butyl-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-d3- Methoxyphenyl)naphthalen-2-yl)methanesulfonamide (Compound D-1)

[0056]

[0057] Concrete synthetic steps are as follows:

[0058]

[0059] Step 1. Synthesis of N-(2-cyanophenyl)pyridineamide (Compound 3).

[0060] Add pyridine-2-carboxylic acid (1.23g, 10mmol), 2-cyanoaniline (1.42g, 12mmol), 2-(7-benzotriazole oxide)-N, N, N', N'-tetramethyluronium hexafluorophosphate (HATU, 7.6g, 20mmol) and N,N-diisopropylethylamine (DIPEA, 5.17g, 40mmol), were dissolved in 50mL DMF, stirred at room temperature to react 4- After 6 hours, after the reaction was detected by TLC, ethyl acetate was added for dilution, washed successively with 5% aqueous citric acid solution, water, sodium bicarbonate solution and saturated brine, concentrated, and recrystallized by adding a small amount of isopropanol to obtain 1.23 g of the product. Rate: 55.15%.

[0061] Step 2. Synthesis of 6-hy...

Embodiment 2

[0076] The compounds of the above examples were evaluated for biological activity.

[0077] In order to verify the effect of the compounds described herein on HCV, the inventors used the HCV Replicon System (HCV Replicon System) as an evaluation model. Since it was first reported by Science in 1999, the HCV replicon system has become one of the most important tools for studying HCV RNA replication, pathogenicity and virus persistence. -NCR minimal region, and the HCV replicon system has been successfully used as a model for the evaluation of antiviral drugs. The inventors of the present invention conducted verification according to the methods described in Science, 1999, 285(5424), 110-3, and J. Virol, 2003, 77(5), 3007-19.

[0078] (1) Detect compound anti-HCV 1a and 1b genotype replicon activity

[0079] HCV-1a and HCV-1b stably transfected replicon cells were used to detect the inhibitory activity of compounds on HCV genotype 1a and 1b replicon. In this experiment, Dasab...

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Abstract

Provided are a substituted naphthalene ring compound, a pharmaceutical composition, and applications thereof. The naphthalene ring compound is a compound represented by formula (I), or its polymorph, pharmaceutically acceptable salt, prodrug, stereo Isomers, isotopic variations, hydrates or solvates. The naphthalene ring compound can be used as a hepatitis C virus inhibitor, has better hepatitis C virus protein NS5B inhibitory activity, and better pharmacodynamics/pharmacokinetic performance, so it is more suitable for preparing and treating hepatitis C virus infection medicine. Formula (I).

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a hepatitis C virus inhibitor, a pharmaceutical composition and applications thereof. Background technique [0002] HCV (Hepatitis C Virus, Hepatitis C Virus) is an RNA virus belonging to the Hepacivirus genus in the Flaviviridae family. Encapsulated HCV virions contain a positive-sense RNA genome that encodes all known virus-specific proteins in a single uninterrupted open reading frame. The open reading frame comprises approximately 9500 nucleotides and encodes a single large polyprotein of approximately 3000 amino acids. Polyproteins include core protein, envelope proteins E1 and E2, membrane-bound protein P7, and nonstructural proteins NS2, NS3, NS4A, NS4B, NS5A, and NS5B. [0003] In recent years, the incidence of hepatitis C has been increasing year by year. From 2006 to 2010, there were 70681 cases, 92378 cases, 108446 cases, 131849 cases and 163174 cases re...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/22A61K31/513A61P31/12
CPCA61K31/513C07D239/22
Inventor 王义汉赵九洋
Owner SHENZHEN TARGETRX INC
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