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Hydroxychloroquine derivative and its synthetic method

A technology of hydroxychloroquine and its synthetic method, which is applied in the field of 2-[[4-[amino]pentyl]ethylamino]-ethylsulfate and hydroxychloroquine derivatives II, and can solve the problems of less public information, etc.

Active Publication Date: 2012-10-17
WUHAN WUYAO SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There is very little public information on compound II, and its medicinal value is mainly reported. As an impurity of hydroxychloroquine sulfate, especially its synthesis method, there is no report

Method used

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  • Hydroxychloroquine derivative and its synthetic method
  • Hydroxychloroquine derivative and its synthetic method
  • Hydroxychloroquine derivative and its synthetic method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The synthetic method 1 of embodiment 1 compound II

[0027] In a three-necked reaction flask, add 20g of hydroxychloroquine sulfate, 40mL of concentrated sulfuric acid, and 200mL of dichloromethane, stir, heat to reflux, and react for 10 hours. After the reaction is complete, the reaction solution is poured into 500mL of water, and adjusted to neutrality with Extracted with dichloromethane, the organic phase was spin-dried, 100mL ethyl acetate was added to the residue, stirred at room temperature for 12h, a large amount of solid was precipitated, filtered by suction, and dried to obtain 17.4g of off-white solid, which was compound II, with a yield of 70.2%, HPLC The peak area normalized method content is 99.5%.

Embodiment 2

[0028] The influence of embodiment 2 different solvents on the preparation yield, quality of compound II

[0029] According to the synthetic method 1 of compound II, the selected solvents are respectively: dichloromethane, chloroform, toluene, DMF, completed 4 experiments, obtained 4 samples, and its yield and quality data are shown in the following table:

[0030] sample

[0031] Conclusion: Dichloromethane is used as the reaction solvent, and the yield and quality are relatively the best.

Embodiment 3

[0032] The influence of embodiment 3 different solid precipitation reagents on the preparation yield, quality of compound II

[0033] According to the synthetic method 1 of compound II, the selected solid precipitation solvents are respectively: ethyl acetate, acetone, petroleum ether, n-hexane, 4 experiments are completed, and 4 samples are obtained. The yield and quality data are shown in the following table:

[0034] sample

[0035] 2

[0036] Conclusion: Ethyl acetate is used as a reagent for solid precipitation, and the yield and quality are relatively the best.

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Abstract

The invention discloses a hydroxychloroquine derivative II, which is 2-[[4-[7-chloro-4-quinolyl)amino]pentyl]ethylamino]-ethyl sulfate, and its synthetic method; the hydroxychloroquine derivative II is a sulphoacid esterification product of hydroxychloroquine, which is one of main impurities of the hydroxychloroquine medicine and its preparation; the compound II can be used for analyzing and detecting the purity of hydroxychloroquine and its salt, and can be used for controlling the quality of the hydroxychloroquine and its salt; The invention discloses the synthetic method of the compound II, and an application of the prepared impurities comparison product used in the quality control of hydroxychloroquine and its preparation.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a hydroxychloroquine derivative II, i.e. 2-[[4-[(7-chloro-4-quinolyl)amino]pentyl]ethylamino]-ethyl sulfate , and its synthesis method, and use. Background technique [0002] Hydroxychloroquine sulfate is an antimalarial drug that can be used in the treatment of systemic lupus erythematosus, and it is also a unique antirheumatic drug. In addition, hydroxychloroquine also has photoprotective and cholesterol-lowering effects. Some recent trials have shown that hydroxychloroquine can reduce some adverse reactions of glucocorticoids. Hydroxychloroquine has good safety and reliable curative effect, and is being more and more widely used in clinical practice. [0003] The chemical name of hydroxychloroquine derivative II is: 2-[[4-[(7-chloro-4-quinolyl) amino] pentyl] ethylamino]-ethyl sulfate structure is as follows: [0004] [0005] Derivative II [0006] Durin...

Claims

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Application Information

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IPC IPC(8): C07D215/46G01N30/88
Inventor 杨波陈彦郭亚兵张静张晓
Owner WUHAN WUYAO SCI & TECH
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