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Crystal forms of orally-taken mitogen-activated protein kinase inhibitor and preparation method of crystal forms

A crystal form and solvent technology, applied in organic chemistry methods, organic chemistry, pharmaceutical formulations, etc., can solve problems affecting drug absorption and bioavailability, differences in clinical drug efficacy, solubility and stability, and achieve process purification effects Significant, convenient for long-term storage, and the effect of storage conditions is not harsh

Inactive Publication Date: 2016-05-11
CRYSTAL PHARMATECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Different crystal forms of solid chemical drugs can cause different solubility and stability, which will affect the absorption and bioavailability of drugs, and will lead to differences in clinical efficacy
However, there is currently no relevant report on the crystal form of the compound of formula (I), therefore, it is necessary to carry out a comprehensive and systematic polymorphic screening of the compound of formula (I) to select the most suitable crystal form for development.

Method used

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  • Crystal forms of orally-taken mitogen-activated protein kinase inhibitor and preparation method of crystal forms
  • Crystal forms of orally-taken mitogen-activated protein kinase inhibitor and preparation method of crystal forms
  • Crystal forms of orally-taken mitogen-activated protein kinase inhibitor and preparation method of crystal forms

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] The preparation method of formula (I) compound crystal form A:

[0070] Dissolve 10.2 mg of the compound of formula (I) in 1.8 mL of methanol, filter through a 0.45 μm nylon filter head, and place the clear solution in a 1.5 mL vial, and volatilize at room temperature to obtain solid crystal Form A.

[0071] The X-ray powder diffraction data of the crystal form obtained in this embodiment are shown in Table 1, and its XRPD figure is as follows figure 1 .

[0072] Table 1

[0073]

[0074]

Embodiment 2

[0076] The preparation method of formula (I) compound crystal form A:

[0077] Add 12.0 mg of the compound of formula (I) into 1.2 mL of tetrahydrofuran, stir at room temperature at a rate of 500 r / min for three days, and centrifuge to obtain a solid which is Form A.

[0078] The X-ray powder diffraction data of the crystal forms obtained in this example are shown in Table 2.

[0079] Table 2

[0080]

[0081]

Embodiment 3

[0083] The preparation method of formula (I) compound crystal form A:

[0084] Dissolve 17.0 mg of the compound of formula (I) in 0.1 mL of dimethylformamide, then slowly add 0.2 mL of water dropwise while stirring, continue stirring for two days, and centrifuge to obtain a solid that is Form A.

[0085] The X-ray powder diffraction data of the crystal forms obtained in this example are shown in Table 3.

[0086] table 3

[0087]

[0088]

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PUM

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Abstract

The invention relates to a crystal form for treating melanoma and ovarian cancer and a preparation method of the crystal form, in particular to crystal forms of an orally-taken mitogen-activated protein kinase inhibitor and a preparation method of the crystal forms. The crystal form A and the crystal form B are good in stability and significant in process purification effect, and the solubility and hygroscopicity of the crystal form A and the crystal form B meet medication requirements. The preparation method of the crystal forms is simple and low in cost and has important value in optimization and development of the medicine in the future.

Description

technical field [0001] The invention relates to the field of chemical medicine, in particular to 5-[(4-bromo-2-fluorophenyl)amino]-4-fluoro-N-(2-hydroxyethoxy)-1-methyl-1H-benzene Crystal form of imidazole-6-carboxamide and preparation method thereof. Background technique [0002] The new anti-cancer drug Binimetinib (MEK162) is an oral mitogen-activated protein kinase (mitogen-activated protein kinase) inhibitor developed by Array Biopharma. It is currently in Phase III clinical trials in the United States for NRAS gene mutant melanin Tumor, BRAF mutant melanoma, and recurrent low-grade plasma ovarian cancer. The chemical name of the drug is: 5-[(4-bromo-2-fluorophenyl)amino]-4-fluoro-N-(2-hydroxyethoxy)-1-methyl-1H-benzimidazole- 6-formamide, its structural formula is as shown in formula (I). [0003] [0004] Different crystal forms of solid chemical drugs can cause different solubility and stability, which will affect drug absorption and bioavailability, and lead t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/06A61K31/4184A61P35/00
CPCA61K31/4184C07D235/06C07B2200/13
Inventor 陈敏华张炎锋陆飞张晓宇
Owner CRYSTAL PHARMATECH CO LTD
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