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Thienopyridine ester derivative containing nitrile group, its preparation method and its purpose

A kind of pyridine, nitrile technology, applied in the field of medicine, can solve the problem of patients with heavy bleeding

Active Publication Date: 2011-11-16
TIANJIN INSTITUTE OF PHARMA RESEARCH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The results of its clinical controlled trial with clopidogrel showed that prasugrel was more effective in reducing deaths from non-fatal heart disease and stroke, but caused patients to bleed more

Method used

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  • Thienopyridine ester derivative containing nitrile group, its preparation method and its purpose
  • Thienopyridine ester derivative containing nitrile group, its preparation method and its purpose
  • Thienopyridine ester derivative containing nitrile group, its preparation method and its purpose

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] intermediate 1 preparation of

[0033]

[0034] Add 19.2 g of 5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one into a reaction flask equipped with stirring, condenser and thermometer, and dissolve it with 70 mL of acetonitrile , cooled to -10°C with stirring, and 41.5 g of anhydrous potassium carbonate was added. 19.6 g of 2-cyanobenzyl bromide was added to the reaction system in batches, and after the addition, the temperature was raised to 45° C. to continue the reaction for 4 h (the plate showed that the reaction was complete). Filter, evaporate the filtrate to dryness of acetonitrile, add 50mL of dichloromethane, wash the reaction solution with 3×50mL of water, separate the dichloromethane layer, fully dry it with anhydrous sodium sulfate, filter, and evaporate the dichloromethane under reduced pressure to obtain Yellow oily product 22.6 g (HPLC: 97.2%). Rf = 0.47 [single site, developer: v (petroleum ether): v (ethyl acetate) = 1:2]. MS, m / Z: 270.0 (M).

Embodiment 2

[0036] intermediate 2 preparation of

[0037]

[0038]Add 5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one 19.2g in the reaction flask equipped with stirring, condenser and thermometer, and dissolve This was dispersed, cooled to 0° C. with stirring, and 30.4 g of triethylamine was added. 15.2 g of 3-cyanobenzyl chloride was added to the reaction system in batches, and after the addition, the temperature was raised to reflux to continue the reaction for 5 h (the plate showed that the reaction was complete). The reaction solution was washed with 3×80 mL of water, and the dichloromethane layer was separated, fully dried with anhydrous sodium sulfate, filtered, and the dichloromethane was evaporated under reduced pressure to obtain 20.8 g of a light yellow solid product (HPLC: 96.4%). Rf = 0.45 [single site, developer: v (petroleum ether): v (ethyl acetate) = 1:2]. MS, m / Z: 270.0 (M).

Embodiment 3

[0040] intermediate 3 preparation of

[0041]

[0042] Add 19.2 g of 5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one into a reaction flask equipped with stirring, condenser and thermometer, and disperse it with 65mL of toluene , cooled to 10°C with stirring, and 23.7 g of pyridine was added. 19.6 g of 4-cyanobenzyl bromide was added to the reaction system in batches, and after the addition, the temperature was raised to 95° C. to continue the reaction for 2.5 h (the plate showed that the reaction was complete). The reaction solution was washed with 3×50 mL of water, the toluene layer was separated, fully dried with anhydrous sodium sulfate, filtered, and the toluene was evaporated under reduced pressure to obtain 21.4 g of a yellow oily product (HPLC: 94.2%). Rf = 0.41 [single point, developer: v (petroleum ether): v (ethyl acetate) = 1:2]. MS, m / Z: 270.0 (M).

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Abstract

The invention belongs to the medical technology field of anti-platelet aggregation effect, and provides a thienopyridine ester derivative containing nitrile group and its pharmaceutically acceptable salt possessing a structure shown in a general formula I, wherein R is a nitrile group. The invention also relates to a preparation method of the above compound, simultaneously, the present invention also discloses the medical composition using the compound or its pharmaceutically acceptable salt as an effective activity ingredient, and the applications as medicines for anti-platelet aggregation.

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. Although thrombolytic therapy, interventional therapy and even surgical treatment carried out in recent years have made remarkable progress in the treatment of acute myocardial infarction and cerebral infarction, the success rate of patient rescue has been greatly improved, and the quality of life has also been significantly improved, but cardiovascular and cerebrovascular After all, the disability rate is as high as 30%. Therefore, the development of drugs for the preven...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04A61K31/4365A61P7/02A61P9/10A61P9/00
CPCA61K31/4365C07D495/04A61K9/0019A61K9/1652A61K9/19A61K9/2054A61K9/2059A61K47/10A61K47/26A61P7/02A61P9/00A61P9/10
Inventor 刘登科刘颖岳南陈芙蓉谭初兵周云松刘鹏赵益桂只德广刘默刘冰妮黄长江汤立达
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH
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