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Thiophene pyridine derivative as well as preparation method and application thereof

A compound and technology of general formula, applied in the field of thiophenepyridine derivatives and their preparation, can solve the problems of cardiovascular events, increased mortality, serious aftermath, etc.

Inactive Publication Date: 2017-10-31
HC SYNTHETIC PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

After the occurrence of clopidogrel resistance, the consequences are very serious, with a significant increase in cardiovascular events and mortality

Method used

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  • Thiophene pyridine derivative as well as preparation method and application thereof
  • Thiophene pyridine derivative as well as preparation method and application thereof
  • Thiophene pyridine derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0110] Embodiment 1: the preparation method of compound 1, its synthetic route is as follows:

[0111]

[0112] The levorotatory form of Intermediate 1 (10 mmol) was dissolved in 20 mL of anhydrous dichloromethane, and added dropwise to the anhydrous dichloromethane in which Intermediate 2 (11 mmol) and triethylamine (15 mmol) were dissolved at about 0 °C. After completion, the temperature was controlled at about 0°C and stirring was continued for 2 hours. The reaction solution was poured into 60 mL of ice water, extracted with ethyl acetate (100 mL × 3), the organic phases were combined, the organic phases were washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, concentrated and evaporated to dryness, and the target was obtained by flash column chromatography The product compound 1.

Embodiment 2

[0113] Embodiment 2: The preparation method of compound 2 is as follows:

[0114] It was prepared according to the method of Example 1, except that the intermediate 1 levorotate was replaced with the intermediate 1 dextrorotor.

Embodiment 3

[0115] Embodiment 3: The preparation method of compound 3 is as follows:

[0116] Prepared according to the method of Example 1, except that the intermediate 1 levorotate is replaced by the intermediate 1 racemate.

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Abstract

The invention belongs to the technical field of medicinal chemistry and in particular discloses a thiophene pyridine derivative as well as a preparation method and application thereof. According to the invention, structure of a thiophene pyridine compound is transformed, and a series of thiophene pyridine derivative new compounds are synthesized by mainly carrying out the step of producing esters with aspirin and aspirin derivatives; the compounds enter into a body and then are rapidly metabolized into effective metabolites, and metabolism of an enzyme CYP2C19 is successfully avoided, and the compounds can be directly metabolized into active compounds and play therapeutic effect, so that the problem of resistance of the thiophene pyridine compound is solved, antithrombotic activity of the compounds is effectively improved, and hemorrhage risk is not obviously influenced; and meanwhile, the compounds have more ideal liver and kidney protective effect and also have potential therapeutic significance on other cardiovascular diseases.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, in particular to a thiophenepyridine derivative and a preparation method and application thereof. Background technique [0002] Thrombotic disease is a variety of diseases caused by the stenosis and occlusion of the vascular lumen caused by thrombus and leading to ischemia and infarction of major organs. Factors leading to thrombosis include platelet adhesion and aggregation on the surface of damaged vessel walls, blood stasis, activation of coagulation factors to promote thrombin formation and low fibrinolytic activity. Drugs used clinically for the treatment of thrombosis can be divided into three categories: antiplatelet drugs, anticoagulants and thrombolytic drugs. Antiplatelet drugs have both therapeutic and preventive effects, and are the main category of antithrombotic drugs. Antiplatelet drugs refer to drugs that can inhibit the adhesion, aggregation and release functions of...

Claims

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Application Information

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IPC IPC(8): C07D495/04A61K31/4365A61P7/02A61P9/10
CPCC07D495/04
Inventor 张起愿刘晓鹏
Owner HC SYNTHETIC PHARMA CO LTD
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