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Pyridine-containing nitric oxide donor compound, its preparation method and use

A compound and pharmaceutical technology, applied in the field of medicine, can solve the problems of low cure rate, toxic and side effects, damage to anticancer drugs, etc.

Active Publication Date: 2017-11-10
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 to the normal body.

Method used

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  • Pyridine-containing nitric oxide donor compound, its preparation method and use
  • Pyridine-containing nitric oxide donor compound, its preparation method and use
  • Pyridine-containing nitric oxide donor compound, its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] 3-(Cyclopropylcarbamoyl)-2-((4-(1-oxo-2-nitrate)ethyl)-3-methylpiperazin-1-yl)pyridine (Compound Ⅰ-1)

[0063]

[0064] Add intermediate III-1 (3.2g, 0.01mol) to the reaction flask equipped with stirring, condenser and thermometer, dissolve in anhydrous acetonitrile (20m1), and add anhydrous acetonitrile solution of silver nitrate (2.0g, 0.012mol) (10m1), refluxed for 5h under stirring in the dark, TLC showed that the reaction was complete and cooled to room temperature, and the solvent was evaporated to dryness under reduced pressure. Dichloromethane (20ml) was added to the residue, stirred for 10min, filtered, and the filtrate was evaporated to dryness under reduced pressure. Add absolute ethanol (30ml), decolorize with activated carbon, evaporate to dryness under reduced pressure, and dry under reduced pressure at room temperature overnight to obtain light yellow transparent oil I-1 (3.1g, yield 90%), purity 98.9% (HPLC method). HRMS (m / z): 364.1615.

[0065] Co...

Embodiment 2

[0069] Compound Ⅰ-3 into hydrochloride: take 2.0 g of compound Ⅰ-3 light yellow oily product and dissolve it in 10 mL of anhydrous ether. Cool in an ice-water bath to 0°C, add dropwise 25% diethyl ether solution of hydrochloric acid until the pH is 2, and continue stirring for about 1 h in an ice-water bath. Filter to obtain a white solid.

Embodiment 3

[0071] Compound Ⅰ-4 into gluconate: take 2.0 g of compound Ⅰ-4 yellow oily product and dissolve it in 10 mL of absolute ethanol. After heating to reflux, equimolar gluconic acid was added, and the reaction was stirred under reflux for about 2h. After the reaction was completed, it was left to stand at room temperature for 24 h. Filter to obtain light yellow solid.

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PUM

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Abstract

The invention discloses a pyridine-containing nitric oxide donor derivative having a structure shown as a formula I, and a pharmaceutically-acceptable salt thereof. In the formula I, n=1, 2 or 3; R1 is alkyl or a naphthenic base having 1-4 carbon atoms; R2 and R3 are hydrogen and alkyl having 1-4 carbon atoms simultaneously or separately; and R4 is hydrogen or alkyl having 1-4 carbon atoms. The invention further discloses a preparation method of the derivative, and discloses a medicinal composition taking the derivative or the pharmaceutically-acceptable salt thereof as an active effective component, and an application of the medicinal composition as an antitumor medicament, particularly application of the medicinal composition to preparation of medicaments for treating the breast cancer, the lung cancer and the stomach cancer.

Description

technical field [0001] The invention belongs to the technical field of medicine, and more specifically, relates to a class of compounds with antitumor effects, a preparation method thereof, a pharmaceutical composition containing them and the use as an antitumor drug. Background technique [0002] In the nitric oxide (NO) molecule, there are 5 electrons in the outer layer of the N atom, and 6 electrons in the outer layer of the O atom. After forming a covalent bond, there is still an unpaired electron in the molecular orbital. The chemical property is unstable and the half-life is Short and highly fat-soluble, it is easy to diffuse through the cell membrane and diffuse into adjacent tissues. With its active chemical properties, it will quickly interact with the target substance and produce biological effects. NO is connected with certain drugs, which can not only enhance the efficacy of drugs, increase new adaptations, but also significantly reduce adverse reactions. [000...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04C07D213/82A61K31/496A61P35/00
CPCC07D213/82C07D401/04
Inventor 李兴伟张远崔莹黄淑云罗振福
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH
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