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Pyridine derivatives, preparation method thereof, and purpose thereof

A compound and pharmaceutical technology, applied in the field of medicine, can solve problems such as injury, side effects, and low cure rate

Active Publication Date: 2012-04-18
TIANJIN INSTITUTE OF PHARMA RESEARCH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chemotherapy is faster, but the cure rate is very low
At the same time, it is clinically found that many anticancer drugs have obvious damage and side effects on the normal body, such as mutagenesis and genotoxicity

Method used

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  • Pyridine derivatives, preparation method thereof, and purpose thereof
  • Pyridine derivatives, preparation method thereof, and purpose thereof
  • Pyridine derivatives, preparation method thereof, and purpose thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 2

[0059] Synthesis of Intermediate IV-1

[0060]

[0061] Add 12.2 g of intermediate III-1 to a reaction flask equipped with stirring, a condenser, and a thermometer, dissolve it with 40 mL of dichloromethane, and add 17.8 g of NBS while stirring. React under light at room temperature for 6 hours (the plate layer shows that the reaction is complete). with 3 x 30mL 35% Na 2 S 2 o 3 The reaction solution was washed with aqueous solution, and the dichloromethane layer was fully dried with anhydrous sodium sulfate, filtered, and the dichloromethane was evaporated under reduced pressure to obtain a light yellow oily product (HPLC: 96.2%). Rf = 0.36 [single site, developing solvent: v (dichloromethane): v (methanol) = 5: 1].

[0062] Referring to the method of Reference Example 2, intermediates IV-2 to IV-5 can be synthesized.

[0063] Table 3 List of Intermediates IV-2~IV-5

[0064]

Embodiment 1

[0066] Synthesis of (6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)(pyridin-2-yl)methanone oxime (Compound I-1)

[0067]

[0068] Add 10.0 g of intermediate IV-1 into a reaction flask equipped with stirring, a condenser, and a thermometer, dissolve it with 30 mL of anhydrous methanol, and add 6.5 g of anhydrous potassium carbonate while stirring. 7.0 g of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine was added to the reaction system in batches. After the addition was completed, the reaction was continued for 3.5h under reflux (the plate showed that the reaction was complete). Filter out the solid matter, evaporate anhydrous methanol to dryness, wash the reaction solution with 3×30mL water, extract with dichloromethane, fully dry with anhydrous sodium sulfate, filter, and evaporate dichloromethane under reduced pressure to obtain a black oil. Column separation [mobile phase: v (dichloromethane): v (methanol) = 5: 1], Rf = 0.45, gave a light yellow solid (HPLC: 99.3%).

[0069] Referr...

Embodiment 3

[0075] Formation of compound I-2 into taurate: Take 2.0 g of the white solid product of compound I-2 and dissolve it in 10 mL of anhydrous methanol. After heating to reflux, equimolar taurine was added, and the reaction was stirred under reflux for about 1.5h. After the reaction was completed, it was left to stand at room temperature for 24 h. Transparent crystals were precipitated, filtered and dried in vacuo.

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Abstract

The invention belongs to the technical field of medicines. The invention provides pyridine derivatives with a structure represented by a general formula I, and medical salts thereof. R1 and R2 are defined as in the claims. The invention also relates to a preparation method of the compounds. The invention also discloses medicine compositions with the compounds and the pharmaceutically acceptable salts thereof as active components, and an application thereof as anti-tumor medicines.

Description

technical field [0001] The invention belongs to the technical field of medicine, more specifically, relates to a class of compounds with antitumor properties, a preparation method thereof, a pharmaceutical composition containing them and the use as an antitumor drug. Background technique [0002] Cancer has become a major chronic disease that seriously endangers human health. According to statistics, there are 9 million people who suffer from cancer every year in the world, and 6 million patients die from cancer. Almost one cancer patient dies every second. The annual incidence of cancer in my country is about 1.2 million, the number of cancer deaths is as high as more than 900,000, and the number of patients waiting for treatment exceeds 1.5 million, and there is an increasing trend year by year. Therefore, cancer has become the second largest killer after cardiovascular disease. Clinically, tumors are treated in three major ways: surgery, radiotherapy, and chemotherapy. ...

Claims

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Application Information

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IPC IPC(8): C07D495/04A61K31/444A61P35/00A61P15/14A61P11/00A61P1/00
Inventor 刘登科刘颖刘冰妮穆帅祁浩飞牛端侯佳佳邹美香
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH
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