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2-sulfomethylpyrazole pyrimidinone compound as well as preparation method, pharmaceutical composition and application thereof

一种硫甲基吡唑嘧啶酮、化合物的技术，应用在化学合成和药物领域，能够解决交叉耐药、口服剂量加大、水溶性和透膜性差等问题

Active Publication Date: 2019-11-22
YUNNAN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The technical problem to be solved by this invention is to overcome the relatively poor water solubility and membrane permeability of existing non-nucleoside HIV-1 reverse transcriptase inhibitors (NNRTIs) in the prior art, thereby causing its bioavailability Low and increased oral doses further cause problems such as toxic side effects and cross-drug resistance, thus providing a 2-thiomethylpyrazopyrimidinone compound different from the prior art, its preparation method, pharmaceutical composition and application

Method used

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  • 2-sulfomethylpyrazole pyrimidinone compound as well as preparation method, pharmaceutical composition and application thereof
  • 2-sulfomethylpyrazole pyrimidinone compound as well as preparation method, pharmaceutical composition and application thereof
  • 2-sulfomethylpyrazole pyrimidinone compound as well as preparation method, pharmaceutical composition and application thereof

Examples

Experimental program
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preparation Embodiment 1

[0164] Preparation Example 1: Preparation of Target Compound I

[0165] The synthetic route of target compound 1-1 is shown in the following formula:

[0166]

[0167] Step (1): Preparation of ethyl 2,4-dioxo-4-phenylbutyrate (intermediate 2-1)

[0168] Take 40mL of ethanol in a 200mL round bottom flask, add sodium (2g, 0.083mol) in batches under stirring at room temperature, after cooling to room temperature, add acetophenone (5g, 0.042mol), and then add diethyl oxalate (7.4g, 0.046mol), reacted at room temperature for 8h, added 1mol / L hydrochloric acid to adjust the pH to 8, evaporated ethanol to dryness, added 10mL water, extracted 3 times with 20mL ethyl acetate, combined the organic phases, washed with saturated brine, and anhydrous Na2SO4 dried. Filtration and concentration yielded 9.3 g of intermediate 2-1, which can be directly used in the next reaction without purification.

[0169] Step (2): Preparation of ethyl 5-phenyl-1H-pyrazole-3-carboxylate (intermediate ...

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Abstract

The invention discloses a 2-sulfomethylpyrazole pyrimidinone compound as well as a preparation method, a pharmaceutical composition and applications of the 2-sulfomethylpyrazole pyrimidinone compound.The structure of the 2-sulfomethylpyrazole pyrimidinone compound is as shown in a formula I, which is described in the specification. The 2-sulfomethylpyrazole pyrimidinone compound disclosed by theinvention can be used as an HIV-1 inhibitor and is used for preparing a medicine for treating and / or preventing immunodeficiency viruses.

Description

technical field [0001] The present invention relates to the technical fields of chemical synthesis and medicine, in particular to a 2-thiomethylpyrazolopyrimidinone compound, its preparation method, pharmaceutical composition and application. Background technique [0002] Acquired immunodeficiency syndrome (AIDS), also known as AIDS, is a disease caused by human immunodeficiency virus (Human immunodeficiency virus, HIV) infection. Reverse transcriptase (Reverse transcriptase, RT), as a key enzyme that catalyzes the conversion of viral RNA to DNA, is a key target for the design of anti-AIDS drugs. [0003] Non-nucleoside reverse transcriptase inhibitors (non-nucleoside reverse transcriptase inhibitors, NNRTIs) have many advantages such as high efficiency, low toxicity, and good selectivity, and are an important part of the current highly effective antiretroviral therapy (cART) for the treatment of AIDS. Although the emergence of cART has greatly reduced the mortality rate of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/12A61K31/506A61P31/18
CPCC07D403/12A61K31/513A61P31/18C07D405/14C07D403/14
Inventor 何严萍张洪彬郑永唐武玉萌唐成润芮若梅王江远杨柳萌
Owner YUNNAN UNIV