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Ethylene-glycol-alcoholized 3-pyridinol-4-ketone compound and preparation method and application thereof

A ketone compound, hydroxypyridine technology, applied in organic chemistry, drug combination, antidote, etc., can solve the problem of high drug price

Inactive Publication Date: 2015-11-04
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are no iron-removing drugs or generic drugs with similar functions on the market in my country, which also leads to high drug prices

Method used

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  • Ethylene-glycol-alcoholized 3-pyridinol-4-ketone compound and preparation method and application thereof
  • Ethylene-glycol-alcoholized 3-pyridinol-4-ketone compound and preparation method and application thereof
  • Ethylene-glycol-alcoholized 3-pyridinol-4-ketone compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0056] Example 1, the synthesis of 3-benzyloxy-2-methyl-4H-pyran-4-one

[0057]

[0058] Dissolve 122.3g NaOH in 278mL water, then add it into 1160mL ethanol solution containing 390g malt powder, mix well, add 422g benzyl chloride under stirring, heat and stir at 60°C for 3.5h after mixing well. After the reaction system is cooled, remove solid impurities by suction filtration, wash the filter residue with ethanol, spin dry after combining the washing liquid and the filtrate, dissolve the remaining substance with dichloromethane, then wash with 5wt% NaOH solution, and finally wash with water, and the organic layer After drying with anhydrous sodium sulfate and spin-drying the solvent, a light yellow oily liquid can be obtained. After cooling, recrystallize with ether to obtain the target product with a yield of 82%.

[0059] MS(ESI,m / z):[M+H] + calcd for C 13 h 13 o 3 217.09; found 217.10. 1 H NMR (CDCl 3 ):δ2.08(s,3H),5.16(s,2H),6.37(d,J=5.64Hz,1H),7.41-7.30(m,5H),7....

example 2

[0060] Example 2, the synthesis of 3-benzyloxy-2-ethyl-4H-pyran-4-one

[0061] Dissolve 122.3g NaOH in 278mL water, then add it into 1160mL ethanol solution containing 390g malt powder, mix well, add 422g benzyl chloride under stirring, heat and stir at 60°C for 3.5h after fully mixing; the reaction system is cooled Finally, remove solid impurities by suction filtration, wash the filter residue with ethanol, spin dry after combining the washing liquid and the filtrate, dissolve the remaining substance with dichloromethane, then wash with 5wt% NaOH solution, and finally wash with water, and wash the organic layer with anhydrous After drying with sodium sulfate, the solvent was spin-dried to obtain a light yellow oily liquid, which was recrystallized with ether after cooling to obtain the target product with a yield of 81%.

[0062]

example 3

[0063] Example 3, the synthesis of 3-benzyloxy-6-hydroxymethyl-4H-pyran-4-one

[0064]

[0065] Keeping the reaction conditions of Example 1 unchanged, malt powder was replaced by an equivalent amount of kojic acid to obtain 3-benzyloxy-6-hydroxymethyl-4H-pyran-4-one with a yield of 70%.

[0066] MS(ESI,m / z):[M+H] + calcd for C 13 h 13 o 4 233.08; found 233.17. 1 H NMR (DMSO-d 6 )δ: 4.30(s,2H), 4.95(s,2H), 5.71(br s,1H), 6.33(s,1H), 7.34-7.44(m,5H), 8.19(s,1H). 13 C NMR (DMSO-d 6 )δ: 173.17, 168.04, 146.58, 141.14, 136.12, 128.41(2C), 128.16, 128.11(2C), 111.12, 70.51, 59.28.

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Abstract

The invention discloses an ethylene-glycol-alcoholized 3-pyridinol-4-ketone compound and a preparation method and application thereof. The ethylene-glycol-alcoholized 3-pyridinol-4-ketone compound comprises ethylene-glycol-alcoholized 3-pyridinol-4-ketone derivatives and salt of the ethylene-glycol-alcoholized 3-pyridinol-4-ketone derivatives. The structural formula of the ethylene-glycol-alcoholized 3-pyridinol-4-ketone derivatives can be seen in the specification. The ethylene-glycol-alcoholized 3-pyridinol-4-ketone derivatives are designed in an optimized mode, ethylene-glycol-alcoholized groups are introduced, the biological activity of chelation iron ions of the ethylene-glycol-alcoholized 3-pyridinol-4-ketone derivatives is improved, toxic effects are reduced, the high oral activity is achieved, and the iron discharge capacity of the ethylene-glycol-alcoholized 3-pyridinol-4-ketone derivatives is remarkable. Experiments prove that the metabolism effect of the ethylene-glycol-alcoholized 3-pyridinol-4-ketone compound for the iron overload disease is obviously better than that of 3-hydroxy-1,2-dimenthyl-4-(1H)-pyridone, and the ethylene-glycol-alcoholized 3-pyridinol-4-ketone compound can be used for preparing medicine for preventing the iron overload disease.

Description

1. Technical field [0001] The present invention relates to an ethylene glycolated 3-hydroxypyridin-4-one compound and its preparation method and application. The compound can treat toxic symptoms caused by excessive accumulation of iron in the body, such as thalassemia and other diseases that depend on long-term massive blood transfusion Diseases, as well as damage caused by excessive accumulation of iron ions in local tissues have special medicinal value. 2. Background technology [0002] Since the first PEGylated drug was developed in the 1970s, modified PEGylated proteins and small molecule drugs have greatly improved the cure of some chronic diseases, such as hepatitis C, leukemia, some Immunodeficiency disorders, rheumatoid arthritis, and Crohn's disease. The most important pegylation drugs include Pegademase bovine, Pegaspargase, Pegfilgrastim, Pegvisomant, and Certolizumab pegol), some PEGylated drugs are under rapid development, such as PEG-uricase and PEGylated he...

Claims

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Application Information

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IPC IPC(8): C07D213/69A61P39/04
CPCC07D213/69
Inventor 张兴元李军配罗伯特·海德文森索·阿巴特
Owner UNIV OF SCI & TECH OF CHINA