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Preparation method of hydroxychloroquine sulfate

A technology of hydroxychloroquine sulfate and hydroxychloroquine, applied in the direction of organic chemistry, etc., can solve the problems of increased impurity content and quantity, unfavorable industrial production, long preparation process time, etc., achieve short reaction time, beneficial to industrial production, and good reproducibility Effect

Pending Publication Date: 2020-07-17
REYOUNG PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0015] However, the entire preparation process in this method takes too long, consumes high energy, and reduces the income per unit time, and the long-term reaction will lead to an increase in the content and quantity of impurities, which is not conducive to industrial production.

Method used

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  • Preparation method of hydroxychloroquine sulfate
  • Preparation method of hydroxychloroquine sulfate
  • Preparation method of hydroxychloroquine sulfate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] The preparation of hydroxychloroquine sulfate:

[0045] (1)

[0046]

[0047] In reaction flask, drop into 4,7-dichloroquinoline (198.0g, 1.0mol), anhydrous KF (116.2g, 2.0mol), hexadecyltrimethylammonium bromide (10.9g, 0.03mol) and acetonitrile (693 mL), nitrogen replacement. The temperature was raised to 80° C., and the reaction was carried out for 2 hours. TLC monitoring showed that the reaction was complete. Add 5-(N-ethyl-N-2-hydroxyethylamine)-2-pentylamine (217.9g, 1.25mol), keep warm and continue to react for 3h. After the reaction is completed, cool down to 30°C, filter with suction, and depressurize the filtrate concentrate. Add 400 mL of purified water to the concentrate, adjust the pH to 10 with 5% sodium hydroxide, precipitate a solid, and filter with suction to obtain crude hydroxychloroquine. Add n-heptane (800mL) to the crude product, heat to reflux, make a slurry, cool to 0°C, heat and crystallize for 2h, filter, and dry at 60°C for 4h to obtain h...

Embodiment 2

[0051] Preparation of hydroxychloroquine:

[0052] The only difference between Example 2 and Example 1 is that the solvent acetonitrile is replaced by the solvent DMF. Hydroxychloroquine (280.1 g) was prepared with a yield of 83.4%, a purity of 99.7%, and a maximum purity of 0.07%.

Embodiment 3

[0054] Preparation of hydroxychloroquine:

[0055] The only difference between Example 3 and Example 2 is that the reaction temperature is 110°C. Hydroxychloroquine (273.8g) was prepared with a yield of 81.5%, a purity of 99.7%, and a maximum of 0.09%.

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Abstract

The invention relates to a preparation method of hydroxychloroquine sulfate, and belongs to the technical field of medicine synthesis. According to the preparation method of hydroxychloroquine sulfate, 7-chloro-4-fluoroquinoline and 5-(N-ethyl-N-2-hydroxyethyl amine)-2-pentylamine are subjected to a reaction to prepare hydroxychloroquine, and then hydroxychloroquine and sulfuric acid are salifiedto prepare hydroxychloroquine sulfate. The 7-chloro-4-fluoroquinoline is prepared from 4,7-dichloroquinoline through a halogen exchange reaction. The preparation method of hydroxychloroquine sulfate has the advantages of low reaction temperature, short reaction time, fewer byproducts, simple technique and favorable reproducibility, and is beneficial to industrial production.

Description

technical field [0001] The invention relates to a preparation method of hydroxychloroquine sulfate, which belongs to the technical field of drug synthesis. Background technique [0002] The information disclosed in this background section is only intended to increase the understanding of the general background of the present invention, and is not necessarily taken as an acknowledgment or any form of suggestion that the information constitutes the prior art already known to those skilled in the art. [0003] Hydroxychloroquine sulfate (CAS number: 747-36-4, structure shown in the following formula) is an antimalarial drug, which also has anti-inflammatory, immune regulation and anticoagulant effects. Currently, hydroxychloroquine is mainly used clinically to treat rheumatoid Arthritis, juvenile chronic arthritis, discoid lupus erythematosus, and systemic lupus erythematosus. [0004] [0005] The inventors have found that the current synthetic routes for hydroxychloroquin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/46
CPCC07D215/46
Inventor 苗得足高峰陈雪亮孙兆柱李卫聂爱华
Owner REYOUNG PHARMA
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