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Thienopyridone derivative, preparation method and uses thereof

A technology of pyridine and tetrahydrothiophene, applied in the field of medicine, can solve problems such as toxic and side effects, normal cell damage, and drug resistance

Inactive Publication Date: 2010-08-18
TIANJIN INSTITUTE OF PHARMA RESEARCH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are hundreds of anti-cancer drugs clinically, which can effectively prolong the life of cancer patients or improve the quality of life of cancer patients, but most of the drugs are cytotoxic drugs with low selectivity. At the same time, it also has serious damage to normal cells, causing strong toxic and side effects, and there is a problem of drug resistance
In addition, the existing chemical drugs are not ideal for the treatment of most solid tumors

Method used

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  • Thienopyridone derivative, preparation method and uses thereof
  • Thienopyridone derivative, preparation method and uses thereof
  • Thienopyridone derivative, preparation method and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] intermediate 1 preparation of

[0067]

[0068] 16.2 g of 4-phenylpiperazine was added to a reaction flask equipped with stirring, a condenser, and a thermometer, dissolved in 30 mL of dichloromethane, cooled to -30°C while stirring, and 41.5 g of anhydrous potassium carbonate was added. Dissolve 11.3 g of chloroacetyl chloride in 25 mL of dichloromethane and slowly add it dropwise to the reaction system. After the dropwise addition is complete, continue the reaction at -10°C for 2 h (the plate layer shows that the reaction is complete). The reaction solution was washed with 3×50 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 21.0 g of a colorless oily product (HPLC: 98.5%). Rf = 0.56 [single site, developer: v (petroleum ether): v (ethyl acetate) = 2: 1].

[0069] 1 H NMR (CDCl 3 , 400MHz) δ: 3.452~3.457(m, 2H), 3.460~3.465(m, 2...

Embodiment 2

[0071] intermediate 2 preparation of

[0072]

[0073] Add 17.6 g of p-methylphenylpiperazine to a reaction flask equipped with a stirring, condenser, and thermometer, dissolve it with 40 mL of chloroform, cool to -20°C while stirring, and add 30.4 g of triethylamine. Dissolve 20.2 g of bromoacetyl bromide in 30 mL of chloroform and slowly add it dropwise to the reaction system. After the dropwise addition is complete, continue the reaction at 0° C. for 4 h (the plate layer shows that the reaction is complete). The reaction solution was washed with 3×80 mL of water, and the chloroform layer was separated, fully dried with anhydrous sodium sulfate, filtered, and the chloroform was evaporated under reduced pressure to obtain 26.8 g of a colorless oily product (HPLC: 98.9%). Rf = 0.60 [single point, developer: v (petroleum ether): v (ethyl acetate) = 2: 1].

[0074] 1 H NMR (CDCl 3 , 400MHz) δ: 2.517~2.519(s, 3H), 3.453~3.458(m, 2H), 3.462~3.466(m, 2H), 3.631~3.636(m, 4H),...

Embodiment 3

[0076] intermediate 3 preparation of

[0077]

[0078] Referring to the method of Example 1, o-fluorophenylpiperazine was used instead of 4-phenylpiperazine, and reacted with chloroacetyl chloride to obtain a colorless oily product (HPLC: 99.6%). Rf = 0.58 [single site, developer: v (petroleum ether): v (ethyl acetate) = 2: 1].

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Abstract

The invention, belonging to the technical field of anti-malignant tumor medicines, provides a thienopyridone derivative having the structure shown as formula I and pharmaceutically acceptable salts thereof, wherein R1 and R2 are defined as specification. The invention further relates a preparation method of the compound, and simultaneously discloses pharmaceutical compositions with the compound or pharmaceutically acceptable salts thereof as effective active ingredient as well as uses of the pharmaceutical compositions as anti-malignant tumor medicines,.

Description

technical field [0001] The invention belongs to the technical field of medicine, more specifically, relates to a class of compounds with anti-malignant tumor effects and a preparation method thereof. Background technique [0002] Cancer is one of the most important killers of human health, and its death rate ranks first in my country and second in the world. According to the statistics of the World Health Organization, the number of cancer deaths in the world in 2007 reached 7.9 million (accounting for about 13% of all deaths), and lung cancer, gastric cancer, liver cancer, colon cancer and breast cancer are the main culprits of most cancer deaths every year. In recent years, the incidence of cancer has been increasing year by year due to the increasing risk of cancer risk factors such as urban air pollution, overweight or obesity, alcohol and tobacco abuse. In developing countries, as deaths from infectious diseases and child mortality decrease, more people live longer and...

Claims

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Application Information

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IPC IPC(8): C07D495/04A61K31/496A61P35/00
Inventor 刘登科刘颖刘冰妮刘默陈继方吴疆邹美香
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH
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