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Preparation method of 4-(5, 5-dihydroxymethyl-2-oxopyrrolidinyl)-3-guanidino methylene benzoic acid

A technology of guanidinomethylene benzoic acid and oxypyrrolidinyl, which is applied in the field of synthesis of benzoic acid derivative drugs, can solve the problems of low yield of benzoic acid derivatives, unfavorable industrial production, low drug resistance of viruses, etc. Achieve the effects of short time period, high purity and high yield

Pending Publication Date: 2022-06-28
BEIJING THTD PHARMA TECH JOINT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In the related art, among the drugs with the above-mentioned functions, benzoic acid derivatives have attracted attention due to their low cost and low drug resistance of viruses, but when preparing such benzoic acid derivatives, the yield of the obtained benzoic acid derivatives The rate is low, only 50-55%, which is not conducive to industrial production

Method used

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  • Preparation method of 4-(5, 5-dihydroxymethyl-2-oxopyrrolidinyl)-3-guanidino methylene benzoic acid
  • Preparation method of 4-(5, 5-dihydroxymethyl-2-oxopyrrolidinyl)-3-guanidino methylene benzoic acid
  • Preparation method of 4-(5, 5-dihydroxymethyl-2-oxopyrrolidinyl)-3-guanidino methylene benzoic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] Formula (II) compound synthesis:

[0083] Weigh 1.14g (2.8mmol) of the compound of formula (I) and dissolve it in 20mL of 95% ethanol solution (ethanol / water (v / v)=95:5), then add 0.25mL of concentrated hydrochloric acid (HCl is 2.8mmol), After 0.40 g (9.5 mmol) of cyanamide, a cloudy mixed solution (pH 4.0) was obtained. The mixture was heated to reflux at a heating temperature of 78° C. until the solution became clear, and then stirred and heated to reflux for 1 h. The reaction solution was cooled to room temperature in a water bath at 20°C, and then concentrated hydrochloric acid was added to adjust the pH value to 1. Then 20 mL of water was added dropwise to the reaction solution. During the dropwise addition, crystals were continuously precipitated and crystallized at room temperature for 1 h; the temperature of the reaction solution was cooled to 3° C. in an ice-water bath, and then kept at 3° C. for crystallization for 1 h. Subsequent filtration obtained the fi...

Embodiment 2

[0087] The difference between this example and Example 1 is that when synthesizing the compound of formula (II), the amount of cyanamide added is 0.29g (7.0mmol).

[0088] When refluxing for 1 h, the reaction solution was taken for liquid chromatography detection, and the results showed that no compound of formula (I) was detected.

[0089] The reaction solution was treated according to the same process as in Example 1 to obtain a white solid (0.96 g, 79% yield) with a purity of 98.8%: MS (m / z) 435 (M+1).

[0090] The obtained compound of formula (II) was all used to prepare the compound of formula (III), and the preparation process was the same as in Example 1 to obtain a white solid (0.48g, 66% yield) with a purity of 99.1%: MS (m / z) 335 (M+1).

Embodiment 3

[0092] The difference between this example and Example 1 is that when synthesizing the compound of formula (II), the amount of cyanamide added is 0.35 g (8.4 mmol).

[0093] The reaction solution was treated according to the same process as in Example 1 to obtain a white solid (1.01 g, 83% yield) with a purity of 99.0%: MS (m / z) 435 (M+1).

[0094] The obtained compound of formula (II) was used to prepare the compound of formula (III), and the preparation process was the same as in Example 1 to obtain a white solid (0.59g, 77% yield) with a purity of 99.8%: MS (m / z) 335 (M+1).

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Abstract

The invention relates to the technical field of synthesis of benzoic acid derivative drugs, particularly discloses a preparation method of 4-(5, 5-dihydroxymethyl-2-oxopyrrolidinyl)-3-guanidino methylene benzoic acid, and solves the problems of low yield and low purity of a target product. The synthesis method comprises the following steps: S1, mixing a compound shown as a formula (I) with cyanamide, and heating and refluxing under an acidic condition to obtain a compound shown as a formula (II); wherein the molar ratio of the compound shown in the formula (I) to cyanamide is 1: (2.5-4.5); and S2, hydrolyzing the compound in the formula (II) to obtain a compound in a formula (III). The compound shown in the formula (III) prepared by the preparation method is high in yield and high in purity.

Description

technical field [0001] This application relates to the technical field of synthesis of benzoic acid derivative drugs, more specifically, it relates to 4-(5,5-dimethylol-2-oxopyrrolidinyl)-3-guanidinomethylenebenzoic acid method of preparation. Background technique [0002] Influenza (Influenza, referred to as influenza) is an acute respiratory infection caused by influenza virus, and it is also a highly contagious and fast-spreading disease. Usually manifested as high fever, headache, fatigue and other symptoms, its complications include: bacterial pneumonia, ear infection, dehydration and so on. Influenza is a serious infectious disease with a high prevalence in the population. [0003] In recent years, studies on influenza virus at home and abroad have clarified the mechanism of influenza virus replication in vivo and its pathogenicity, and discovered some targets that can be used as anti-influenza virus drugs. Among these targets, neuraminidase (Neuraminidase, NA) is a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/26
CPCC07D207/26
Inventor 杨红瑾王红平祝国清吕素冉
Owner BEIJING THTD PHARMA TECH JOINT CO LTD
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