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Crystal forms of clorsulon as well as preparation methods and applications of crystal forms

A cloxolone crystal form and cloxolone crystal technology are applied in the field of polymorph and the preparation of the crystal form, and can solve the problems of complicated preparation process, low crystal form purity, unfriendly environment and the like

Inactive Publication Date: 2018-04-03
ZHEJIANG HISUN PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Patent US4064239 discloses the melting points of two crystal forms of cloxolone prepared from the solvate of cloxolone ether (188-193°C and 205-207°C respectively), document 4-Amino-6 -(trichloroethenyl)-1,3-benzonedisulfonamide, a new potent fasciolicide.J.Med.Chem.,1977,20(9),pp1225–1227 published the solvate of cloxolone ether as raw material The melting points of the two crystalline products (194-203°C and 203-205°C, respectively), these cloxolone crystal forms have a wide melting range, and the crystal form purity is not high, it is speculated that they may be mixed crystals; and these cloxolone The preparation process of the Solon crystal form is cumbersome, and a second-class solvent is used, which consumes a lot of energy and is not environmentally friendly

Method used

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  • Crystal forms of clorsulon as well as preparation methods and applications of crystal forms
  • Crystal forms of clorsulon as well as preparation methods and applications of crystal forms
  • Crystal forms of clorsulon as well as preparation methods and applications of crystal forms

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0117] Add cloxolone 1g into water, wherein the weight volume ratio of cloxolone to water is 1:50; heat up to 90°C, and continue to stir for 60min to dissolve; add methyl isobutyl ketone, wherein, methyl isobutyl ketone The volume ratio of butyl ketone to water is 1:100; cool down to 25°C, crystallize; filter, vacuum dry at 45°C to obtain 0.5g crystals, HPLC=98.7%, X-ray powder diffraction pattern (XRD) , confirmed as Form A.

[0118] The X-ray powder diffraction, infrared, DSC and TGA spectra of this crystal form are detailed in Figure 1-4 , which is named Cloxolone Form A in the present invention.

Embodiment 2

[0120] Add cloxolone 1g into water, wherein the weight volume ratio of cloxolone to water is 1:50; heat up to 80°C, and continue to stir for 60min to dissolve; add methyl isobutyl ketone, wherein, methyl isobutyl ketone The volume ratio of butyl ketone to water is 1:100; cool down to 20°C, crystallize; filter, vacuum dry at 45°C to obtain 0.53g crystals, HPLC=98.6%, X-ray powder diffraction pattern (XRD) , confirmed as Form A.

Embodiment 3

[0122] Add cloxolone 1g into water, wherein the weight volume ratio of cloxolone to water is 1:50; heat up to 90°C, and continue to stir for 60min to dissolve; add methyl isobutyl ketone, wherein, methyl isobutyl ketone The volume ratio of butyl ketone to water is 1:100; cool down to 30°C, crystallize; filter, vacuum dry at 45°C to obtain 0.46g crystals, HPLC=98.8%, X-ray powder diffraction pattern (XRD) , confirmed as Form A.

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PUM

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Abstract

The invention relates to novel crystal forms A, B, C and D of clorsulon as well as preparation methods and applications of the crystal forms. The crystal forms have excellent properties in physical and chemical stability and processing adaptability.

Description

technical field [0001] The invention relates to the field of chemical pharmacy. More specifically, the present invention relates to polymorphic forms of cloxolone, methods for preparing the crystalline forms, pharmaceutical compositions containing them and their pharmaceutical use. technical background [0002] Cloxolone, alias cloxolone, cloxolone, molecular formula: C 8 h 8 Cl 3 N 3 o 4 S 2 , chemical name: 4-amino-6-(trichloroethenyl)-1,3-benzenedisulfonamide. [0003] Its structural formula is as follows: [0004] [0005] Cloxolone is a widely used veterinary anthelmintic, which is mainly used to treat parasitic diseases in the lungs of cattle and sheep, and has special effects against Fasciolicide (fasciola genus) diseases and insect pests; Cloxolone can Competitively inhibit 8-phosphoglyceride kinase and phosphoglyceride isomerase, block the oxidation of glucose into acetate and propionate, thereby blocking the main energy source of Fasciola hepatica, and p...

Claims

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Application Information

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IPC IPC(8): C07C303/44C07C311/39A61K31/63A61P33/00
CPCC07B2200/13C07C303/44C07C311/39
Inventor 李娜张亮陈连蔚苏笛
Owner ZHEJIANG HISUN PHARMA CO LTD
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