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Febuxostat 2-methylimidazole salt and preparation method thereof and pharmaceutical composition containing febuxostat 2-methylimidazole salt

A technology of methylimidazolium salt and febuxostat, which is applied in the field of medicine and chemical industry, can solve the problems of difficult crystal form control and low solubility of febuxostat, and achieve the effects of good crystal form stability, high solubility and simple operation

Inactive Publication Date: 2017-05-31
广州奈米微晶生物科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The first object of the present invention is to provide a pharmaceutically acceptable febuxostat 2-methylimidazolium salt and its crystal form for the technical problems of low solubility of febuxostat and difficult crystal form control.

Method used

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  • Febuxostat 2-methylimidazole salt and preparation method thereof and pharmaceutical composition containing febuxostat 2-methylimidazole salt
  • Febuxostat 2-methylimidazole salt and preparation method thereof and pharmaceutical composition containing febuxostat 2-methylimidazole salt
  • Febuxostat 2-methylimidazole salt and preparation method thereof and pharmaceutical composition containing febuxostat 2-methylimidazole salt

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preparation example Construction

[0044] The preparation method of febuxostat 2-methylimidazole salt of the present invention is relatively convenient.

[0045] (1) Dissolving febuxostat and 2-methylimidazole in an organic solvent respectively, and obtaining a corresponding solution;

[0046] In step (1), preferably, the molar ratio of the raw material febuxostat and 2-methylimidazole is (3:1) to (1:1); more preferably, the mol ratio of febuxostat and 2-methylimidazole is The molar ratio is (2.2:1)~(1.8:1);

[0047] Meanwhile, in step (1), preferably, the volume-to-mass ratio of the organic solvent to febuxostat or 2-methylimidazole is (5-50): 1; more preferably, the organic solvent to febuxostat or 2 - The volume-to-mass ratio of methylimidazole is (8-20): 1;

[0048] Meanwhile, the organic solvent is one of C1-C4 low-carbon alcohols, ethers, esters, ketones or nitriles, or a mixed organic solvent of several;

[0049] Preferably, the alcohol solvents are methanol, ethanol, propanol, isopropanol, butanol; e...

Embodiment 1

[0058] Dissolve 10.0 g of febuxostat in 100 mL of methanol; take 1.1 g of 2-methylimidazole and dissolve it in 10 mL of methanol, mix and stir the obtained two solutions, concentrate, cool to 10 °C for crystallization, and filter to obtain colorless crystals 3.3 gram;

[0059] of the crystal 1 H NMR showed: δ: 8.22(s, 2H), 8.17(d, 2H), 7.33(d, 2H), 7.18(s, 2H), 3.98(d, 4H), 2.64(s, 6H), 2.44( s, 3H), 2.08 (hept, 2H), 1.01 (d, 12H);

[0060] The powder XRD pattern of the crystal is as follows figure 2 shown, by figure 2 It can be seen that the obtained crystal has obvious diffraction peaks at 2θ angles of 8.82°, 9.13°, 14.38°, 15.88°, 19.53°, 24.90°, 25.61°, 27.70°, 32.00°, and 34.80°;

[0061] DSC of crystals as image 3 shown; by image 3 The melting point of this salt was found to be 169±2°C.

[0062] Infrared spectra of crystals such as Figure 4 shown, by Figure 4 The infrared spectrum diagram shows that the febuxostat 2-methylimidazole crystal of the present i...

Embodiment 2

[0065] Dissolve 6.3 g of febuxostat in 40 mL of acetonitrile, dissolve 1.2 g of 2-methylimidazole in 5 mL of acetonitrile, mix and stir the two solutions, concentrate, cool to 5 °C for crystallization, and filter to obtain colorless crystals 4.0 g.

[0066] The NMR, powder XRD diffraction and infrared spectrum tests of the crystal obtained in Example 2 are consistent with the results in Example 1, and its melting point is 169.3°C.

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Abstract

The invention discloses a febuxostat 2-methylimidazole salt and a preparation method thereof and a pharmaceutical composition containing the febuxostat 2-methylimidazole salt. The molar ratio of components of the salt is 2:1; and the space group of the crystal form is a triclinic system. The salt has characteristic peaks at diffraction angles 2theta of 8.87+ / -0.2 degrees, 9.08+ / -0.2 degrees, 14.44+ / -0.2 degrees, 15.88+ / -0.2 degrees, 19.48+ / -0.2 degrees, 24.94+ / -0.2 degrees, 25.60+ / -0.2 degrees, 27.67+ / -0.2 degrees and 34.87+ / -0.2 degrees in a powder X-ray diffraction pattern employing Cu-Kalpha as a radiation source. The febuxostat 2-methylimidazole salt is high in solubility, high in crystallinity, convenient in preparation method and good in reproducibility.

Description

technical field [0001] The invention belongs to the technical field of medicine and chemical industry, and more particularly relates to febuxostat 2-methylimidazolium salt, a preparation method thereof and a pharmaceutical composition comprising the same. Background technique [0002] Febuxostat (also known as: Febuxostat, the structure is shown below) is a selective inhibitor of non-purine xanthine oxidoreductase (XOR), developed by Japan's Teijin Co., Ltd. and approved for listing in EMEA in April 2008 , FDA approved for listing in February 2009. The drug can effectively inhibit the activity of XOR, and can reduce the conversion of purine to uric acid, so as to reduce the level of uric acid in the body and achieve the purpose of treating gout. [0003] [0004] Compared with allopurinol, the inhibitory effect of febuxostat on XOR is not affected by the redox state of the enzyme, and has a significant inhibitory effect on both oxidized and reduced XOR; at the same time,...

Claims

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Application Information

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IPC IPC(8): C07D277/56C07D233/58A61K31/426A61K31/4164A61P19/06
CPCC07D277/56C07B2200/13C07D233/58
Inventor 张雷张宪瑞李晶关溯
Owner 广州奈米微晶生物科技有限公司
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