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Pyridone derivative, and preparation method and application thereof

A kind of technology of pyridone and derivatives, applied in the field of medicine

Active Publication Date: 2017-05-10
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Based on the pharmacophore model and active conformation of 2-pyridone hepatitis B virus inhibitors, the present invention adopts molecular hybridization and electronic isosteric drug design strategies to design and synthesize a series of pyridone compounds. Such compounds are not available in the prior art. No related reports

Method used

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  • Pyridone derivative, and preparation method and application thereof
  • Pyridone derivative, and preparation method and application thereof
  • Pyridone derivative, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Embodiment 1. Preparation of compound 2

[0056] Take a 1L single-necked bottle, dissolve 5-nitropyridin-2-ol (5g, 35.7mmol) in 500mL of water, slowly add N-bromosuccinimide (3g, 35.7mmol), and stir at 25°C for 3 hours Thin-layer chromatography detected that the reaction was complete, suction filtered, washed with water (100 mL), washed with petroleum ether (50 mL), dried, and weighed to obtain 7.09 g of a light yellow solid with a yield of 90%.

[0057]

[0058] Compound 2 spectral data: 1 H-NMR (400MHz, CD 3 OD) δppm: 8.68(d, 2H, J=2.8Hz), 8.66(d, 2H, J=2.8Hz).

Embodiment 2

[0059] Embodiment 2. Preparation of compound 3a

[0060] Take a 100mL anaerobic reaction flask, dissolve compound 2 (2g, 9.13mmol) and p-methoxyphenylboronic acid (1.53g, 10.05mmol) in water (15mL) and a mixed solution of 1,4 dioxane (45mL) In , add potassium carbonate (3.79g, 27.4mmol), replace the nitrogen, quickly add tetrakis triphenylphosphine palladium (0.63g, 0.55mmol); replace the nitrogen again, reflux reaction at 100°C. After the reaction, part of 1,4-dioxane was rotary evaporated, water (60mL) was added, extracted with ethyl acetate (25mL x 3), the organic phases were combined, washed with saturated brine (50mL x 3), dried over anhydrous sodium sulfate, Concentrate and wash with methanol to obtain 1.2 g of yellow solid 3a with a yield of 53% and a melting point of 212-215°C.

[0061]

[0062] Spectral data of compound 1: 1 H-NMR (400MHz, DMSO) δppm: 12.80(s, 1H), 8.62(d, J=3.1Hz, 1H), 8.15(d, J=3.0Hz, 1H), 7.72(d, J=8.8Hz, 2H), 6.99(d, J=8.8Hz, 2H), 3.80(s, 3H...

Embodiment 3

[0063] Embodiment 3. Preparation of compound 4a

[0064] Compound 3a (300 mg, 1.22 mmol) was dissolved in 12 mL of methanol, 10% palladium on carbon (65 mg, 10%) was added to replace the hydrogen, and stirred overnight at 25°C. After the reaction was completed, methanol (20 mL) was added, filtered with diatomaceous earth, washed with methanol (15 mL x 2), and the filtrate was collected and concentrated to obtain 220 mg of tan solid compound 4a with a yield of 83%.

[0065]

[0066] Spectral analysis data of compound 4a: ESI-MS: 217.5[M+H] + ,433.6[2M+H] + .

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Abstract

The invention discloses a pyridone derivative, and a preparation method and an application thereof. The compound has a structure as shown in a formula I or a formula II in the specification. The invention also relates to a preparation method for the compound with the structure as shown in the formula I or the formula II in the specification, and a pharmaceutical composition and the application of the above-mentioned compound in preparation of anti-HBV drugs.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to pyridone derivatives, a preparation method and pharmaceutical use thereof. Background technique [0002] Viral hepatitis type B (viral hepatitis type B), referred to as hepatitis B (Hepatitis B), is a major infectious disease caused by hepatitis B virus (HBV), long-term development can lead to acute and chronic viral hepatitis, severe hepatitis, liver cirrhosis and primary hepatocellular carcinoma (hepatocellular carcinoma, HCC). According to the report of the World Health Organization (WHO), nearly 2 billion people in the world have been infected with HBV, of which about 240 million people are chronic HBV infected people, and an average of about 780,000 people die each year from acute and chronic hepatitis and related complications caused by HBV infection. disease. The drugs currently used to prevent and treat chronic hepatitis B (CHB) mainly include vaccines, int...

Claims

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Application Information

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IPC IPC(8): C07D213/64C07D213/73C07D213/75C07D405/04C07D213/61A61K31/4418A61K31/443A61P31/20
CPCC07D213/61C07D213/64C07D213/73C07D213/75C07D405/04
Inventor 刘新泳贾海永展鹏俞霁
Owner SHANDONG UNIV
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