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Nitrogen-containing heterocyclic thienopyridine compounds and preparation method and application thereof

A compound, pyridine technology, applied in the field of medicine, can solve problems such as poor selectivity, low specificity, multi-drug resistance of tumors, etc.

Inactive 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

Traditional chemotherapeutic drugs have obvious clinical therapeutic effects, but their disadvantages are: low specificity and poor selectivity, leading to obvious toxic and side effects, and prone to serious tumor multi-drug resistance, which limits clinical application. Looking for safe and effective anti-tumor drugs Drugs have always been the pursuit of the pharmaceutical industry

Method used

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  • Nitrogen-containing heterocyclic thienopyridine compounds and preparation method and application thereof
  • Nitrogen-containing heterocyclic thienopyridine compounds and preparation method and application thereof
  • Nitrogen-containing heterocyclic thienopyridine compounds and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] 5-(pyridin-2-yl-methyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (Compound I-A-1)

[0069]

[0070] Add 13.9 g of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine into a reaction flask equipped with stirring, condenser and thermometer, dissolve it with 50 mL of acetonitrile, and cool it to -10 °C, 41.5 g of anhydrous potassium carbonate was added. 17.2 g of 2-bromomethylpyridine was added to the reaction system in batches, and after the addition, the temperature was raised to 45° C. to continue the reaction for 3 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 White solid product 15.7g (HPLC: 97.9%), yield 68.4%. Rf = 0.55 [single site, developer: v (petroleum ether): v (ethyl acetat...

Embodiment 2

[0072] 5-(quinolin-2-yl-methyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (Compound I-A-2)

[0073]

[0074] Add 13.9 g of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine into a reaction flask equipped with stirring, condenser and thermometer, dissolve it with 80 mL of dichloromethane, and cool it to At 0°C, 30.4 g of triethylamine was added. 17.8 g of 2-(chloromethyl)quinoline was added to the reaction system in batches, and after the addition, the temperature was raised to reflux to continue the reaction for 4 hours (the plate showed that the reaction was complete). Wash the reaction solution with 3×80mL water, separate the dichloromethane layer, fully dry it with anhydrous sodium sulfate, filter, and evaporate the dichloromethane under reduced pressure to obtain 19.9g of white solid product (HPLC: 98.4%), the yield 70.9%. Rf = 0.53 [single site, developer: v (petroleum ether): v (ethyl acetate) = 2: 1]. 1 H NMR (CDCl3, 400MHz) δ: 2.918(s, 4H), 3.684(s, 2H), 4.055(s, 2H), 6.689~...

Embodiment 3

[0076] Intermediate II-B- 1 preparation of

[0077]

[0078] Add 19.2g 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 65mL of toluene , cooled to 10°C with stirring, and 23.7 g of pyridine was added. 17.2 g of 2-bromomethylpyridine 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 h (the plate showed that the reaction was complete). The reaction solution was washed with 3×70 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 a light yellow waxy product (HPLC: 97.4%). Rf=0.51 [single point, developer: v (petroleum ether): v (ethyl acetate) = 1:2]. 1 H NMR (DMSO-d6, 400MHz) δ: 3.072~3.101(t, 2H), 3.578~3.607(t, 2H), 4.248(s, 2H), 4.284~4.301(t, 1H), 4.617(s, 2H) ), 6.577(s, 1H),...

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Abstract

The invention belongs to the technical field of drugs for resisting malignant tumor and provides nitrogen-containing heterocyclic thienopyridine compounds with the structure shown as a general formula I and salts thereof, wherein R1 is hydrogen, and C1-C4 are alkanoyloxy substituted by alkyl; and R2 is nitrogen-containing six-membered heterocycle, i.e. benzoazo six-membered heterocycle. The invention further relates to a method for preparing the compounds, and also discloses drug compositions taking the compounds or the salts thereof as the active effective components and application thereof as drugs for resisting malignant tumor.

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] Tumor is a common disease that threatens human life. According to statistics, the total number of cancer deaths in the world reaches 7 million people every year. In my country, more than 1 million people die from cancer every year, and gradually increase. It has become the first cause of death in urban population. Traditional chemotherapeutic drugs have obvious clinical therapeutic effects, but their disadvantages are: low specificity and poor selectivity, leading to obvious toxic and side effects, and prone to serious tumor multi-drug resistance, which limits clinical application. Looking for safe and effective anti-tumor drugs Drugs have always been the pursuit of the pharmaceutical industry. Contents of the invention [0003] One object of the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/04A61K31/4709A61K31/444A61P35/00A61P35/02
Inventor 刘登科刘颖刘默刘冰妮周云松祁浩飞侯佳佳王平保
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH
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