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Acethydrazide derivatives containing thieno[3.2-c]pyridine, preparation method and use thereof

A technology of acetyl hydrazide and pyridine, applied in the field of medicine, can solve problems such as weak alkalinity and difficult purification, and achieve the effect of inhibiting platelet aggregation

Inactive Publication Date: 2008-09-10
TIANJIN INSTITUTE OF PHARMA RESEARCH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Clopidogrel is superior to other drugs in improving the prognosis of ischemic events, with less ADR than ticlopyridine, and better safety than aspirin, but there are reports of TTP and hemolytic uremic syndrome (HUS)
[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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  • Acethydrazide derivatives containing thieno[3.2-c]pyridine, preparation method and use thereof
  • Acethydrazide derivatives containing thieno[3.2-c]pyridine, preparation method and use thereof
  • Acethydrazide derivatives containing thieno[3.2-c]pyridine, preparation method and use thereof

Examples

Experimental program
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Effect test

example 1

[0060] α,α-[(4-fluorophenyl)-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)]acetylhydrazide (compound 1)

[0061] In a reaction flask equipped with stirring, condenser and thermometer, add α,α-[(4-fluorophenyl)-(4,5,6,7-tetrahydrothieno[3,2-c]pyridine- 5-yl)] methyl acetate 19g, dehydrated ethanol 30ml, slowly heat under stirring, the reaction raw materials are dissolved, add 23.3g hydrazine hydrate (80%), continue heating to reflux, heat preservation reaction 6 hours (plate layer shows reaction completely). 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 13.11 g of white solid, yield 69%, HPLC: 98.11%, m.p.138.0°C~139.3°C, 1 H NMR (400MHz, DMSO-d6, δppm): 2.38-2.61 (br, 2H), 3.28-3.31 (t, 2H), 3.49-3.54 (t, 2H), 4.56 (s, 2H), 5.70 ...

Embodiment 2

[0063] α,α-[(4-chlorophenyl)-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)]-N'-(dimethylmethylene base) acetylhydrazide (compound 2)

[0064] In a reaction flask equipped with stirring, condenser and thermometer, add α,α-[(4-chlorophenyl)-(4,5,6,7-tetrahydrothieno[3,2-c]pyridine- 5-yl)] acetylhydrazide 4g, anhydrous methanol 40ml, start stirring, and heat to dissolve. Continue heating to 40°C, add 0.8g of acetone dropwise, and keep the reaction for 3 hours after the addition is complete. The reaction was stopped, cooled, and a light yellow solid was generated. Filter, wash with anhydrous methanol 3×2ml, and dry to obtain 3.8g of light yellow solid. HPLC: 99.3%, m.p.169.5-171.1°C, Rf=0.3 (developing solvent: petroleum ether (60-90°C):ethyl acetate=1:1). 1 HNMR (400MHz, DMSO-d6, δppm): 1.64(s, 3H), 1.86(s, 3H), 3.30-3.34(t, 2H), 3.58-3.62(t, 2H), 4.36(s, 2H), 5.61 (s, 1H), 7.13-7.77 (m, 6H), 9.99 (br s, 1H).

Embodiment 3

[0066] α,α-[(3-chlorophenyl)-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)]-N'-[(2-chlorobenzene base) methylene] acetylhydrazide (compound 3)

[0067] The compound is prepared according to the preparation process provided in Example 2, from α, α-[(3-chlorophenyl)-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl )] Acetylhydrazide and o-chlorobenzaldehyde reaction. HPLC: 99.7%, m.p.182.6-183.6°C, Rf=0.84 (developing solvent: petroleum ether (60-90°C):ethyl acetate=1:1). 1 H NMR (400MHz, DMSO-d6, δppm): 3.17-3.22(t, 2H), 3.40-3.51(t, 2H), 4.72(s, 2H), 5.46(s, 1H), 6.88-7.94(m, 10H), 8.46 (s, 1H), 11.99 (br s, 1H).

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Abstract

The invention discloses a thieno[3.2-c]pyridine containing acetyl hydrazine derivative or a salt chemically acceptable of the derivative; meanwhile, the invention also discloses a drug combination with the compounds as active-effective components and an application of the same as a medicine for treating platelet aggregation inhibitor, and particularly for preparing, preventing or curing diseases due to the platelet aggregation, such as coronary syndrome, myocardial infarction, myocardial ischemia and cardio-cerebrovascular 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] Thrombosis can lead to acute myocardial infarction, stroke, pulmonary embolism and other diseases of the heart, brain, and pulmonary circulation, 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, antiplatelet drugs have become the main drugs for the prevention and treatment of these diseases. Adenosine diphosphate (ADP) is an important agonist for the activation of platelets and the amplification of aggregation effects. By blocking the ADP receptors to inhibit the action of platelets, it has become an important way to prevent pathological thrombosis (coronary heart disease, cerebrovascular di...

Claims

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Application Information

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IPC IPC(8): C07D495/04A61K31/4365A61P7/02
Inventor 刘默刘登科刘颖徐为人张士俊成碟金丽媛汤立达刘昌孝
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH
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