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Anti-viral compound intermediate 1-acyl-pyrazole-3-carboxylic acid and preparation method thereof

A technology of antiviral drugs and compounds, applied in organic chemistry and other fields, can solve problems such as disease rebound and drug resistance, and achieve the effect of accelerating metabolism, mild operating conditions, and good blocking effect

Inactive Publication Date: 2010-10-13
扬州康伊尔医药科技有限公司
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AI Technical Summary

Problems solved by technology

[0002] Nucleoside compounds as antiviral drugs generally use purine, guanine, pyrimidine and their analogs as bases. As antiviral drugs, they often have good antiviral effects in the initial stage of use, but with the use of The increase of time will produce different degrees of drug resistance, or the disease will rebound after stopping the drug

Method used

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  • Anti-viral compound intermediate 1-acyl-pyrazole-3-carboxylic acid and preparation method thereof
  • Anti-viral compound intermediate 1-acyl-pyrazole-3-carboxylic acid and preparation method thereof
  • Anti-viral compound intermediate 1-acyl-pyrazole-3-carboxylic acid and preparation method thereof

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Embodiment Construction

[0026] One, such as figure 1 Compound I can be prepared by a two-step reaction:

[0027] Step 1: Dissolve tert-butyl pyrazole-3-carboxylate (IV) in a solvent, add a nitrogen-containing organic base, an acylating agent and a catalyst N,N-lutidine, at a temperature from 0°C to the boiling point of the solvent Under these conditions, 1-N-acylation reaction occurs to generate 1-acylated derivative (V). Wherein the molar ratio of tert-butyl pyrazole-3-carboxylate and acylating reagent is 1:1~1.5, and the molar ratio of tert-butyl pyrazole-3-carboxylate and nitrogen-containing organic base is 1:1.2 ~2.

[0028] Step 2: The 1-acylated derivative (V) prepared in step 1 can be directly used in the next step of deprotection: under the condition of 0 ° C to the boiling point of the solvent, the 1-acylated derivative (V) and acid A deprotection reaction occurs to generate 1-acyl-pyrazole-3-carboxylic acid (I); then the pH of the reaction solution is adjusted to 2-4, the organic phase i...

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Abstract

The invention relates to anti-viral compound intermediate 1-acyl-pyrazole-3-carboxylic acid and a preparation method thereof, which belong to the field of organic synthesis. Firstly, pyrazole-3-carboxylic acid tert-butyl reacts with acylation reagent and nitrogen-containing organic alkali to generate 1-acylated derivative; and then the tert-butyl group of the 1-acylated derivative is removed under the action of acid to obtain the 1-acyl-pyrazole-3-carboxylic acid. Same as other nucleosides, the product has the capability of specifically binding NDA and RNA, has better decoration, can block the activity of RNA polymerase, plays a very good role in blocking virus replication, simultaneously has good anti-drug resistance and is beneficial to long-termed use.

Description

technical field [0001] The invention relates to a chemical synthesis method of a compound, in particular to a preparation method of an intermediate having an antiviral compound, and belongs to the field of organic synthesis. Background technique [0002] Nucleoside compounds as antiviral drugs generally use purine, guanine, pyrimidine and their analogs as bases. As antiviral drugs, they often have good antiviral effects in the initial stage of use, but with the use of The increase of time will produce different degrees of drug resistance, or the disease will rebound after stopping the drug. Contents of the invention [0003] The object of the present invention is to provide an intermediate compound, 1-acyl-pyrazole-3-carboxylic acid, which can be synthesized as an antiviral drug or pesticide and has good resistance to drug resistance. [0004] The molecular structural formula of 1-acyl-pyrazole-3-carboxylic acid of the present invention is: [0005] [0006] In the fo...

Claims

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Application Information

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IPC IPC(8): C07D231/14
Inventor 范尔康孙智华居小平王竝王涛王广录
Owner 扬州康伊尔医药科技有限公司
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