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Dabigatran etexilate analog centered by fluorine-containing-group-modified benzene ring and synthesis method thereof

A dabigatran etexilate and synthetic method technology, applied in the direction of organic chemistry, etc., can solve the problems of increasing the preparation cost of dabigatran etexilate analogues, high toxicity, and increased risk in the preparation process

Inactive Publication Date: 2014-04-02
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] The second purpose of the present invention is to solve the problem of using volatile and toxic fluoride in the preparation process of fluorine-containing dabigatran etexilate analogues in the prior art Gases such as HCl, NH3 thereby increased the preparation cost of dabigatran etexilate analogue, and technical problems such as the danger increase of preparation process provide a kind of safe and reliable, synthetic process is simple, synthetic A relatively low-cost synthetic method of dabigatran etexilate analogues centered on a fluorine-containing group-modified benzene ring

Method used

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  • Dabigatran etexilate analog centered by fluorine-containing-group-modified benzene ring and synthesis method thereof
  • Dabigatran etexilate analog centered by fluorine-containing-group-modified benzene ring and synthesis method thereof
  • Dabigatran etexilate analog centered by fluorine-containing-group-modified benzene ring and synthesis method thereof

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Embodiment 1

[0059] A dabigatran etexilate analog centered on a fluorine-containing group-modified benzene ring, namely image 3 Ar in -5-methyl-pyridine; R 1 for -F; R 2 for -CH 3 , namely 3-[[[2-[[[4-[[[(hexyloxy)carbonyl]amino]iminomethyl]-2-fluoro-phenyl]amino]methyl]-1-methyl- 1 H -Benzimidazol-5-yl]carbonyl]-(5-methyl-pyridin-2-yl)-amino]propionic acid ethyl ester.

[0060] The above-mentioned dabigatran etexilate analogue centered on a fluorine-containing group-modified benzene ring, that is, 3-[[[2-[[[4-[[[(hexyloxy)carbonyl]amino]imino Methyl]2-fluoro-phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](5-methyl-pyridin-2-yl)amino]propionic acid ethyl Method for the synthesis of esters. That is, 2-amino-5-methylpyridine is used as a raw material, and 3-[[[2-[[[4-[[[(hexyloxy)carbonyl]amino]iminomethyl]2 -Fluoro-phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](5-methyl-pyridin-2-yl)amino]propionic acid ethyl ester, per step The synthesis reaction is as f...

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Abstract

The invention discloses a dabigatran etexilate analog centered by fluorine-containing-group-modified benzene ring and a synthesis method thereof. A fluorine-containing-group p-aminophenyl cyanide compound used as an initial raw material is subjected to a series of reactions to finally synthesize the dabigatran etexilate analog centered by fluorine-containing-group-modified benzene ring. The synthesis method is simple to operate, and has the advantages of cheap and accessible reagents, lower synthesis cost, lower risks in the synthesis process, higher yield for each synthesis step, short synthesis time and the like.

Description

technical field [0001] The invention relates to a dabigatran etexilate analog centered on a fluorine-containing group-modified benzene ring and a synthesis method thereof, belonging to the field of chemical synthesis. Background technique [0002] The direct thrombin inhibitor dabigatran etexilate (dabigatrau etexilate, trade name Pradaxa) was developed by Boehringer Ingelheim, Germany, and was first launched in Germany and the UK in April 2008. It is a new type, non-peptide, competitive , a reversible thrombin inhibitor, after being taken orally and absorbed by the gastrointestinal tract, it will be converted into dabigatran with direct anticoagulant activity in the body, and its structural diagram is shown in figure 1 shown. [0003] The structural representation of dabigatran etexilate is as follows: figure 2 As shown, dabigatran etexilate is the first new category of oral anticoagulant drugs listed on the market in 50 years after warfarin. Medication monitoring, less...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12
CPCC07D401/12
Inventor 任玉杰李美霖王庆伟
Owner SHANGHAI INST OF TECH
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