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Anti-hepatitis B virus compound as well as preparation method and application thereof

A compound and anti-hepatitis B technology, applied in antiviral agents, preparation of sugar derivatives, chemical instruments and methods, etc., can solve problems such as drug resistance and unclear drug targets, and achieve low price, high efficacy, and easy synthetic effect

Active Publication Date: 2021-06-18
南京颐媛生物医学研究院有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These drugs for the treatment of hepatitis B virus still face many problems, such as drug resistance and unclear drug targets, and it is still necessary to research and develop new drugs against hepatitis B virus with high efficacy, low toxicity and low price

Method used

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  • Anti-hepatitis B virus compound as well as preparation method and application thereof
  • Anti-hepatitis B virus compound as well as preparation method and application thereof
  • Anti-hepatitis B virus compound as well as preparation method and application thereof

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preparation example Construction

[0043] The invention additionally provides a preparation method of the anti-hepatitis B virus compound. The preparation method includes six steps, and each step can be completed through different embodiments to finally synthesize the compound 4-thiouridine isobutyrate having anti-hepatitis B virus activity. The preparation method of the anti-hepatitis B virus compound comprises the following steps:

[0044] Step 1: the preparation method of compound 3

[0045] .

Embodiment 1

[0047] 25 g of uracil 1, 26.4 g of (2R,3S,4S,5S)-5-(acetoxymethyl)tetrahydrofuran-2,3,4-triacetate triester 2, 48 g of N,O- Bis(trimethylsilyl)acetamide was dissolved in 380 mL of acetonitrile, and reacted under the protection of argon, the oil bath was heated to 90°C and heated to reflux for 2 h, 26 g of trimethylsilyl trifluoromethanesulfonate was added, and continued Heated to reflux for 16h. After the reaction solution was naturally cooled to room temperature, 200 mL of saturated sodium bicarbonate solution and 500 mL of ethyl acetate were added, filtered, the filtrate was separated into the water phase, and the organic phase was washed twice with water and once with saturated saline, and then washed with anhydrous sodium sulfate After drying and filtering, the organic phase was concentrated under reduced pressure to obtain compound 3.

Embodiment 2

[0049] 20g of uracil, 14.09g of (2R,3S,4S,5S)-5-(acetoxymethyl)tetrahydrofuran-2,3,4-triacetate triester, 38.3g of N,O-bis( Dissolve trimethylsilyl)acetamide in 350 mL of acetonitrile, react under the protection of argon, heat the oil bath to 90°C and heat to reflux for 2h, add 20.7g of trimethylsilyl trifluoromethanesulfonate, continue to heat and reflux 16h. The reaction solution was naturally cooled to room temperature, added 150 mL saturated sodium bicarbonate solution and 450 mL ethyl acetate, filtered, the filtrate was separated into the water phase, the organic phase was washed twice with water, once with saturated brine, and dried over anhydrous sodium sulfate , after filtration, the organic phase was concentrated under reduced pressure to obtain compound 3.

[0050] Further, the compound 3 obtained in Example 1 and Example 2 are both yellow oils, and the crude compound 3 obtained in Example 1 and Example 2 does not need to be purified, and can directly participate in...

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Abstract

The invention provides an anti-hepatitis B virus compound and a preparation method and application thereof, the compound is 4-thiouridine isobutyrate, the molecular formula is C13H18N2O6S, and the structural formula is shown in the specification. The compound provided by the invention can effectively inhibit the activity of hepatitis B virus, can be used as a substitute drug for lamivudine and telbivudine, solves the problem of drug resistance of lamivudine and the like in the aspect of resisting hepatitis B virus, is high in drug effect, low in toxicity and low in price, and provides a direction for development of drugs for treating hepatitis B. In addition, the invention discloses a preparation method of the compound 4-thiouridine isobutyrate, and the preparation method is mild in condition, easy to synthesize and suitable for industrial production.

Description

technical field [0001] The invention relates to an anti-hepatitis B virus compound and its preparation method and application, belonging to the technical field of medicinal chemistry. Background technique [0002] Hepatitis B virus (HBV) infection is one of the major diseases that affect human health. About 1 million patients die from HBV every year, accounting for the top 10 causes of death in the world. [0003] Currently, there are three main types of drugs for the treatment of chronic viral hepatitis. The first type is nucleoside (acid) drugs, such as lamivudine, adefovir, entecavir, telbivudine, tenofovir, etc.; The first category is interferon drugs, such as: interferon α and pegylated interferon α; the third category is traditional Chinese medicine, such as schisandra, matrine, oleanolic acid and its derivatives, plant polysaccharides, etc. These drugs for the treatment of HBV still face many problems, such as drug resistance and unclear drug targets, and it is still...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/067C07H1/00A61P31/20A61K31/7072
CPCA61P31/20C07H1/00C07H19/067
Inventor 鲍甫义张智马丁来周明陆晓冬李润峰史训龙冯力佟有恩刘冬平
Owner 南京颐媛生物医学研究院有限公司
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