Pradaxa analogue with fluorine-containing group modified benzene ring as center and synthesis method thereof

A dabigatran etexilate and synthetic method technology, applied in organic chemistry, acaricides, etc., can solve the problems of high toxicity, increased risk in the preparation process, increased preparation cost of dabigatran etexilate analogues, etc., to achieve Effects of increased fat solubility and decreased drug metabolism rate

Inactive Publication Date: 2013-07-31
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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  • Pradaxa analogue with fluorine-containing group modified benzene ring as center and synthesis method thereof
  • Pradaxa analogue with fluorine-containing group modified benzene ring as center and synthesis method thereof
  • Pradaxa analogue with fluorine-containing group modified benzene ring as center and synthesis method thereof

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Embodiment 1

[0056] A kind of dabigatran etexilate analog centered on the phenyl ring modified by fluorine-containing group, with R in Fig. 3 1 for -F; R 2 for-C 2 h 5 For example, 3-[[[2-[[[4-[[[(hexyloxy)carbonyl]amino]iminomethyl]phenyl]amino]methyl]-1-ethyl-1H-benzene Ethyl imidazol-5-yl]carbonyl](4-fluorophenyl)amino]propionate.

[0057] 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] phenyl] amino] methyl] -1-ethyl-1H-benzimidazol-5-yl] carbonyl] (4-fluorophenyl) amino] the synthetic method of ethyl propionate, promptly with 4- Fluoroaniline is used as a raw material, and 3-[[[2-[[[4-[[[(hexyloxy)carbonyl]amino]iminomethyl]phenyl]amino]methyl]-1 is synthesized through 9 steps of reaction -ethyl-1H-benzimidazol-5-yl] carbonyl] (4-fluorophenyl) amino] ethyl propionate, each step of synthetic reaction is as follows:

[0058] (1) Synthesis of compound 1, n...

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Abstract

The invention discloses a pradaxa analogue with a fluorine-containing group modified benzene ring as a center and a synthesis method thereof. The pradaxa analogue centering on a fluorine-containing group modified benzene ring disclosed by the invention is finally synthesized through a series of reactions of a fluorine-containing group aniline compound serving as a starting material. The synthesis method of the pradaxa analogue has the advantages that operation is simple, used reagents are cheap and easily available, synthesis cost is relatively low, risks in the process of synthesis are reduced, the yield of each synthesis step is high, and synthesis time is hort.

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, which is converted into dabigatran with direct anticoagulant activity after being taken orally and absorbed by the gastrointestinal tract, and its structure is shown in Figure 1. [0003] The structural schematic diagram of dabigatran etexilate is shown in Figure 2. Dabigatran etexilate is the first new class of oral anticoagulant drugs listed 50 years after warfarin. Compared with warfarin, dabigatran etexilate Ester has the characteristics of oral admini...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/14A01P7/02
Inventor 任玉杰王庆伟陈海峰
Owner SHANGHAI INST OF TECH
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