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Thiophenopyridine substituted acetyl hyarazine derivative

A technology of pyridine and tetrahydrothiophene, applied in the field of medicine, can solve problems such as weak alkalinity and difficult purification

Inactive Publication Date: 2005-10-19
TIANJIN INSTITUTE OF PHARMA RESEARCH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At the same time, because clopidogrel is an oily substance with a very weak alkalinity, it needs to be mixed with a strong acid to form a salt, but it is unstable in the presence of moisture, so that the free base is precipitated, and there are certain difficulties in purification
Due to its strong acidity, it is subject to certain restrictions in preparation

Method used

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  • Thiophenopyridine substituted acetyl hyarazine derivative
  • Thiophenopyridine substituted acetyl hyarazine derivative
  • Thiophenopyridine substituted acetyl hyarazine derivative

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0079] (S)-α,α-[(2-chlorophenyl)-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)]acetylhydrazide (compound 1) (hereinafter referred to as hydrazide)

[0080] In the reaction bottle equipped with stirring, condenser and thermometer, add 38g of clopidogrel and 30ml of absolute ethanol, heat slowly under stirring to dissolve the reaction raw materials, add 45.6g of hydrazine hydrate (80%), and continue heating to reflux , insulation reaction for 4 hours (the plate layer shows that the reaction is complete). Then the solvent was evaporated under reduced pressure, and after evaporation, 50ml of distilled water and 30ml of dichloromethane were added to the residue, fully stirred, and the organic layer was separated. Sodium is fully dry. Dichloromethane was evaporated under reduced pressure to obtain 23.4 g of white solid. (HPLC: 97.16%), m.p.139.0°C-139.3°C.

Embodiment 2

[0082] (S)-α,α-[(2-chlorophenyl)-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)]-N'-[( E)-(Styryl)methylidene]acetylhydrazide (Compound 2)

[0083] Add 4 g of hydrazide and 40 ml of anhydrous methanol into a reaction flask equipped with stirring, a condenser, and a thermometer, start stirring, and heat to dissolve. Continue heating to 40°C, add 1.8g cinnamic aldehyde dropwise, after the addition is complete, keep the reaction for 3 hours. The reaction was stopped and cooled to produce a yellow solid. Filter, wash with anhydrous methanol 3×2ml, and dry to obtain 4.4g of yellow solid. (HPLC: 97.92%), m.p.173.3°C~174.2°C, Rf=0.65 (developing solvent: petroleum ether (60°C~90°C):ethyl acetate=1:1)

Embodiment 3

[0085] (S)-α,α-[(2-chlorophenyl)-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)]-N'-[( E)-(4-methoxyphenyl)methylidene]acetylhydrazide (compound 3)

[0086] The compound is obtained by the reaction of hydrazide and p-methoxybenzaldehyde according to the preparation process provided in Example 2.

[0087] HPLC: 95.92%, m.p.193.3-194.6°C, Rf=0.54 (developing solvent: petroleum ether (60-90°C):ethyl acetate=1:1).

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Abstract

The present invention discloses thiopheno pyridine substituted acetyl hyarazine derivative compound as shown in expression I and its pharmaceutically acceptable salt, medicine composition with the compound as effective component, and their application as platelet aggregation resisting medicine, especially as medicine for preventing and treating platelet aggregation caused coronary artery syndromes, myocardial infarction, myocardial ischemia and other cardiac and cerebral vascular diseases.

Description

technical field [0001] The invention belongs to the technical field of medicine, more specifically, relates to a compound with anti-platelet aggregation effect and a preparation method thereof. Background technique [0002] As the population aging problem becomes more and more serious, cardiovascular and cerebrovascular diseases have become the "number one killer" that seriously affects people's health and life. For this reason, countries around the world have invested a lot of manpower and material resources in the diagnosis and treatment of this type of disease, making it a continuous research and development hotspot. Thrombosis can lead to acute myocardial infarction, stroke, pulmonary embolism and other heart, brain, and pulmonary circulation diseases, threatening human health and life, and is also a common complication in surgery and a factor of reocclusion after interventional angioplasty. Since platelet aggregation plays an important role in thrombus formation, antip...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/4355A61K31/4365A61P7/02A61P9/10C07D493/04C07D495/04
Inventor 刘登科王平保赵专友蒋庆峰闫芳芳黄汉忠席文恭徐旭刘默黄长江任戎
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH
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