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Hydroxychloroquine sulfate crystal form A and preparation method thereof

A technology of hydroxychloroquine sulfate crystal and hydroxychloroquine sulfate, which is applied in the field of hydroxychloroquine sulfate crystal form A and its preparation, can solve the problems of poor stability of hydroxychloroquine sulfate, and achieve the effects of easy industrial production, good stability, and stable and reliable quality

Inactive Publication Date: 2018-11-02
SHANGHAI ZHONGXI SUNVE PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The problem to be solved by the present invention is to provide a kind of hydroxychloroquine sulfate crystal form A and preparation method thereof for the poor stability problem of hydroxychloroquine sulfate in the prior art

Method used

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  • Hydroxychloroquine sulfate crystal form A and preparation method thereof
  • Hydroxychloroquine sulfate crystal form A and preparation method thereof
  • Hydroxychloroquine sulfate crystal form A and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0039] The synthesis of embodiment 1 hydroxychloroquine

[0040] Add 100g of 4,7-dichloroquinoline and 130g of 5-(N-ethyl-N-2-hydroxyethylamine)-2-pentylamine into the reactor, pass through argon protection, raise the temperature to 70°C to make 4 , Dissolve 7-dichloroquinoline, heat up to 115°C for 10 minutes, heat up to 137°C for 10 hours, cool down (below 80°C) after the reaction is complete, and adjust pH>12 with sodium hydroxide solution (mass concentration: 6%), Extracted with dichloromethane, washed with water until neutral, and distilled off the dichloromethane under reduced pressure to obtain 157 g of crude hydroxychloroquine with a yield of 92.5%. Add 200g of acetone and 250g of methyl acetate to the crude product of hydroxychloroquine, heat to dissolve at 65°C, slowly cool down to 10°C over 4 hours, filter, and wash the filter cake with a mixed solution of acetone and methyl acetate to obtain a wet product of hydroxychloroquine. Dry at 60°C for 4 hours to obtain dr...

Embodiment 2-19

[0041] The preparation of embodiment 2-19 hydroxychloroquine sulfate crystal form A

[0042] Dissolve the hydroxychloroquine obtained in Example 1 in an organic solvent, add dropwise an aqueous solution of sulfuric acid with a mass fraction of 40-60% until cloudy, after the dropwise addition, heat up to 35°C-55°C, keep warm for crystallization, and then lower the temperature by 15°C Then keep it warm for 1h, filter, and dry at 50°C to obtain hydroxychloroquine sulfate crystal form A.

[0043] Wherein, the hydroxychloroquine sulfate crystal form A prepared in Example 2 has the following properties: figure 1 The X-ray powder diffraction spectrum shown has characteristic peaks at 2θ=16.9°, 17.1°, 17.5°, 19.9°, 21.3°, 23.5°, 23.9°, and 26.7°; its DSC spectrum is as figure 2 As shown, there is an endothermic peak at 246 °C.

[0044] The concrete condition of table 1 embodiment 2-19

[0045]

[0046]

[0047]

[0048] In the above table, the heat preservation in the heat ...

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Abstract

The invention discloses a hydroxychloroquine sulfate crystal form A and a preparation method thereof and uses means of XRPD, DSC and IR for representation. The hydroxychloroquine sulfate crystal formA provided by the invention improves the chemical stability of hydroxychloroquine sulfate, is simple in preparation method and easy in industrialized production and can provide a study foundation to development of more hydroxychloroquine sulfate dosage forms at the same time. In the preparation method provided by the invention, a sulfuric acid aqueous solution with the mass percentage being 40-60percent is used, the safety and the operability are improved, and the heat release risk generated by using concentrated sulfuric acid is effectively lowered.

Description

technical field [0001] The invention relates to hydroxychloroquine sulfate crystal form A and a preparation method thereof. Background technique [0002] Hydroxychloroquine Sulfate (Hydroxychloroquine Sulfate), its chemical name is 2-[[4-[(7-chloro-4-quinolyl)amino]pentyl]ethylamino]-ethanol sulfate, CAS number is 747-36- 40. Hydroxychloroquine sulfate was successfully developed by Winthrop Company. It was first listed in the United States in 1956 and has been listed in France, Denmark, Japan, Germany, Finland and other countries and regions. U.S. FDA approved hydroxychloroquine sulfate tablets on May 29, 1998 for the treatment of lupus erythematosus and rheumatoid arthritis. Hydroxychloroquine sulfate is more and more widely used in the rheumatic field because of its unique mechanism of action and better safety. After the 1990s, the clinical treatment of more than 90% of rheumatic diseases all selects hydroxychloroquine sulfate. Its structure is as follows: [0003] ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/46
CPCC07B2200/13C07D215/46
Inventor 李晓东颜国明卫金强祝鹏程余坤矫丁云晖俞伟丁雁
Owner SHANGHAI ZHONGXI SUNVE PHARMA
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