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Fluorine-containing benzimidazole compounds and preparation method and application thereof

A technology of benzimidazole and compound, applied in the field of compound synthesis, can solve the problems of long time required, long preparation process, low yield and the like

Inactive Publication Date: 2018-10-12
上海泰坦科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Benzimidazole compounds are very good for anticoagulant therapy, but there are some problems in the prior art that the preparation process is complicated, the preparation process is long, the time required is long, and the yield is not high. For the development of anticoagulant drugs, on the one hand It is to optimize the preparation process of existing anticoagulant drugs, and on the other hand, it is more expected to develop more other drugs with anticoagulant effects to meet clinical and experimental needs

Method used

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  • Fluorine-containing benzimidazole compounds and preparation method and application thereof
  • Fluorine-containing benzimidazole compounds and preparation method and application thereof
  • Fluorine-containing benzimidazole compounds and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0089] In this example, the target compound A was prepared by the following preparation method: Its preparation method is as follows:

[0090] (1) Add ethyl acrylate dropwise to the N,N-dimethylformamide organic solvent of p-fluoroaniline at room temperature, the molar ratio of p-fluoroaniline to ethyl acrylate is 1:1.1, and add An appropriate amount of diethylamine was reacted at room temperature for 3 hours to obtain compound 1, and the reaction formula was as follows:

[0091]

[0092] (2) 3-nitro-4-chloro-benzoic acid and hydroxylamine aqueous solution were reacted for 2 hours at a temperature of 40° C., wherein the molar ratio of 3-nitro-4-chloro-benzoic acid to hydroxylamine was 1:1.2 to obtain 3-nitro-4-hydroxylamino-benzoic acid compound, the reaction formula is as follows:

[0093]

[0094] (3) 3-nitro-4-hydroxyamino-benzoic acid compound and thionyl chloride were reacted in dichloromethane solvent at 70°C for 8 hours at a molar ratio of 1:1.1 under the actio...

Embodiment 2

[0112] In this example, the target compound B was prepared by the following preparation method: Its preparation method is as follows:

[0113] (1) Add ethyl acrylate dropwise to the N,N-dimethylformamide organic solvent of 3-fluoromethylaniline at room temperature, the molar ratio of 3-fluoromethylaniline to ethyl acrylate is 1 : 1.2, and add an appropriate amount of diethylamine to the reaction, react at room temperature for 5 hours, obtain compound 3, and the reaction formula is as follows:

[0114]

[0115] (2) 3-nitro-4-chloro-benzoic acid and hydroxylamine aqueous solution were reacted for 1 hour at a temperature of 50° C., wherein the molar ratio of 3-nitro-4-chloro-benzoic acid to hydroxylamine was 1:1.3 to obtain 3-nitro-4-hydroxylamino-benzoic acid compound, the reaction formula is as follows:

[0116]

[0117] (3) 3-nitro-4-hydroxyamino-benzoic acid compound and thionyl chloride react at 60°C in dichloromethane solvent under the action of catalyst benzyltrie...

Embodiment 3

[0135] In this example, the target compound C was prepared by the following preparation method: Its preparation method is as follows:

[0136] (1) Add ethyl acrylate dropwise to the N,N-dimethylformamide organic solvent of the aniline compound shown in formula II at room temperature, the molar ratio of the aniline compound shown in formula II to ethyl acrylate is 1:1.3 , and add an appropriate amount of diethylamine to the reaction, and react at room temperature for 8 hours to obtain compound 4, the reaction formula is as follows:

[0137]

[0138] (2) 3-nitro-4-chloro-benzoic acid and hydroxylamine aqueous solution were reacted for 2 hours at a temperature of 40° C., wherein the molar ratio of 3-nitro-4-chloro-benzoic acid to hydroxylamine was 1:1.2 to obtain 3-nitro-4-hydroxylamino-benzoic acid compound, the reaction formula is as follows:

[0139]

[0140] (3) 3-nitro-4-hydroxyamino-benzoic acid compound and thionyl chloride were reacted in dichloromethane solvent ...

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Abstract

The invention provides fluorine-containing benzimidazole compounds and a preparation method and application thereof. The fluorine-containing benzimidazole compounds have a structure represented in a formula I; the fluorine-containing benzimidazole compounds have a simple structure, good anticoagulant activity, and can prolong the time of blood coagulation, the preparation method of the fluorine-containing benzimidazole compounds is simple and efficient, and industrial production can be achieved easily.

Description

technical field [0001] The invention belongs to the technical field of compound synthesis, and relates to a fluorine-containing benzimidazole compound and a preparation method and application thereof. Background technique [0002] Benzimidazole compounds are widely used in medicinal chemistry and organic synthesis. Dabigatran and dabigatran etexilate are typical benzimidazole compounds and are very important anticoagulant drugs. [0003] CN 107686476 A discloses a preparation process of dabigatran etexilate mesylate, its structure is It is a non-peptide thrombin inhibitor with good anticoagulant effect. [0004] CN 103804354 A discloses a preparation method of dabigatran etexilate, prepared dabigatran etexilate has the following structure It is used to prevent and treat acute venous thrombosis and has good anticoagulant function. [0005] CN 103420980 A discloses a dabigatran derivative, which has the following structure where R 1 Represents H, or C1-C3 alkyl; R 2 s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/14C07D401/12A61P7/02
CPCA61P7/02C07D235/14C07D401/12
Inventor 谢应波张庆张华徐肖冰罗桂云张维燕
Owner 上海泰坦科技股份有限公司
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