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Thiofuran-pyridine [3, 2-c] contained acethydrazide derivative and preparation method and application thereof

A technology of acetyl hydrazide and 2-c, applied in the field of medicine, can solve the problems of many adverse reactions and large individual differences, etc.

Active Publication Date: 2012-07-04
TIANJIN INSTITUTE OF PHARMA RESEARCH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Ticlopidine, which is currently used clinically, is the first thienopyridine ADP receptor antagonist. Compared with the traditional antiplatelet drug aspirin, it has a slight advantage, but has many adverse reactions (ADR). Ticlopidine for aspirin ineffective or intolerant patients
Clopidogrel is the second thienopyridine drug developed by Sanofi in France. Compared with ticlopyridine, it only has one more carboxymethyl group in the side chain, and its antithrombotic effect is stronger, and its ADR is smaller than that of ticlopyridine. , but there are large individual differences and hemolytic uremic syndrome, etc.

Method used

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  • Thiofuran-pyridine [3, 2-c] contained acethydrazide derivative and preparation method and application thereof
  • Thiofuran-pyridine [3, 2-c] contained acethydrazide derivative and preparation method and application thereof
  • Thiofuran-pyridine [3, 2-c] contained acethydrazide derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 2

[0056] α,α-[(4-chlorophenyl)-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)]acetylhydrazide

[0057]

[0058] According to the preparation process provided in Reference Example 1, the compound was prepared from α,α-[(4-chlorophenyl)-(4,5,6,7-tetrahydrothieno[3,2-c]pyridine-5- base)] methyl acetate and hydrazine hydrate reaction. HPLC: 99.0%, Rf=0.84 [single point, developing solvent: v (petroleum ether 60-90° C.): v (ethyl acetate) = 1:1]. 1 H NMR (DMSO-d 6 , 400MHz) δ: 2.25-2.46(br, 2H), 3.03-3.15(t, 2H), 3.36-3.41(t, 2H), 4.41(s, 2H), 5.54(s, 1H), 6.79-7.85( m, 6H), 10.07 (br, 1H).

Embodiment 3

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

[0061]

[0062] According to the preparation process provided in Reference Example 1, the compound was prepared from α,α-[(3-chlorophenyl)-(4,5,6,7-tetrahydrothieno[3,2-c]pyridine-5- base)] methyl acetate and hydrazine hydrate reaction. HPLC: 98.2%, Rf=0.80 [single point, developer: v (petroleum ether 60-90°C): v (ethyl acetate) = 1:1].

[0063] Reference Example 4:

[0064] α,α-[(2,4-dichlorophenyl)-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)]acetohydrazide

[0065]

Embodiment 1

[0068] α,α-[(4-fluorophenyl)-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)]-N'-(2-methoxycarbonyl Tetrahydrothienide-3-yl) acetylhydrazide (Compound 1)

[0069]

[0070] 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)] acetylhydrazide 4g, anhydrous methanol 40mL, start stirring, and heat to dissolve. Continue heating to 40°C, add 2-methoxycarbonyltetrahydrothiophene-3-one, after the addition is complete, keep the reaction for 3 hours (the plate layer shows that the reaction is complete). The reaction was stopped, cooled, and a light yellow solid was generated. Filter, wash with anhydrous methanol 3×2 mL, and dry to obtain 3.8 g of light yellow solid. HPLC: 99.3%, m.p.169.5-171.1°C, Rf=0.63 [single point, developing solvent: v (petroleum ether 60-90°C):v (ethyl acetate)=1:1]. 1 H NMR (DMSO-d 6 , 400MHz) δ: 2.64-2.72(m, 3H), 2.86-2.99(t, 2H), 3.30-3.34(t, 2H), 3.58(s, 3H), 3....

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Abstract

The invention discloses a thiofuran-pyridine [3, 2-c] contained acethydrazide derivative or pharmaceutically acceptable salts and a preparation method thereof, and also discloses a medical composition using the compound as an active effective component and application in the aspect of being used as medicaments for resisting platelet aggregation, particularly in the aspects of preparing medicaments for preventing or treating cardiovascular and cerebrovascular diseases, such as acute coronary syndrome, myocardial infarction, myocardial ischemia and the like caused by platelet aggregation.

Description

technical field [0001] The present invention belongs to the technical field of medicine, more specifically, relates to a compound with anti-platelet aggregation effect, its preparation method, composition and application. 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 cause 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 ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/04A61K31/4365A61P7/02A61P9/10A61P9/00
Inventor 刘颖刘登科刘默刘冰妮黄长江陈继方周云松白玫汤立达
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH
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