Dabigatran etexilate analogue with fluorine-containing group modified pyridine ring as center and synthesis method of analogue

A dabigatran etexilate and synthetic method technology, applied in the direction of drug combination, blood disease, extracellular fluid disease, etc., can solve the problems of increasing the risk of the preparation process, low oral bioavailability, high incidence of bleeding, etc., to achieve Reduce the difficulty and risk, shorten the synthesis time, and reduce the drug metabolism rate

Inactive Publication Date: 2013-08-14
SHANGHAI INST OF TECH
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Problems solved by technology

[0004] But dabigatran etexilate still has the following defects as direct coagulant at present: the oral bioavailability of dabigatran etexilate is low
[0006] At present, dabigatran etexilate has low bioavailability, bleeding will occur during anticoagulant therapy, especially when used in high doses, the incidence of bleeding is higher and other technical problems
And in its preparation process, the key steps also need to u...

Method used

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  • Dabigatran etexilate analogue with fluorine-containing group modified pyridine ring as center and synthesis method of analogue
  • Dabigatran etexilate analogue with fluorine-containing group modified pyridine ring as center and synthesis method of analogue
  • Dabigatran etexilate analogue with fluorine-containing group modified pyridine ring as center and synthesis method of analogue

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Embodiment 1

[0056] A dabigatran etexilate analog centered on a pyridine ring modified by a fluorine-containing group, with image 3 R in 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- Benzimidazol-5-yl]carbonyl](5-fluoropyridin-2-yl)amino]propanoic acid ethyl ester.

[0057] The above-mentioned a kind of dabigatran etexilate analog centered on a pyridine ring modified by a fluorine-containing group is 3-[[[2-[[[4-[[[(hexyloxy)carbonyl]amino]imino Methyl] phenyl] amino] methyl] -1-ethyl-1H-benzimidazol-5-yl] carbonyl] (5-fluoropyridin-2-yl) amino] the synthetic method of ethyl propionate, namely Using 5-fluoropyridin-2-ylamino as raw material, the final product is a fluorine-modified dabigatran etexilate analog through 9-step reaction synthesis, namely 3-[[[2-[[[4-[[[ (Hexyloxy)carbonyl]amino]iminomethyl]phenyl]amino]methyl]-1-ethyl-1H-benzimidazol-5-yl]carbonyl](5-fluoropyridin-2-yl) Amino] ethyl propionat...

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Abstract

The invention discloses a dabigatran etexilate analogue with fluorine-containing group modified pyridine ring as a center and a synthesis method of the analogue. According to the synthesis method, with a fluorine-containing group aminopyridine compound as a starting material, a series of reactions are carried out to prepare he fluorine-containing group modified dabigatran etexilate analogue. The synthesis method of the analogue has the advantages that the operation is simple, used reagents are low in cost and easily available, synthesis cost is relatively low, rick in the synthetic process is low, yield of each synthesis step is high, and synthesis time is short.

Description

technical field [0001] The invention relates to a dabigatran etexilate analog centered on a pyridine ring modified by a fluorine-containing group 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...

Claims

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Application Information

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IPC IPC(8): C07D401/12A61P7/02
Inventor 任玉杰陈海峰王庆伟
Owner SHANGHAI INST OF TECH
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