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New febuxostat crystal form and preparing method thereof

A febuxostat and crystal form technology, applied in bone diseases, organic chemistry, drug combination, etc., can solve problems such as the problem of not describing the crystal form

Inactive Publication Date: 2010-03-31
UTOPHARM SHANGHAI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] EP513379 reported the synthesis method of febuxostat, which mentioned recrystallization with ethanol to obtain the final product, but did not describe the problem of crystal form

Method used

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  • New febuxostat crystal form and preparing method thereof
  • New febuxostat crystal form and preparing method thereof
  • New febuxostat crystal form and preparing method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The preparation method of febuxostat crystal form X:

[0026] Add 1 g of febuxostat to 6 ml of methyl ethyl ketone, heat to reflux to dissolve, then cool to room temperature while stirring, and filter after stirring for 2 hours. Dry at 60°C. A 0.7 g sample of crystal form X was obtained, with a melting point of 201-204°C.

Embodiment 2

[0028] The preparation method of febuxostat crystal form X:

[0029] Add 5 g of febuxostat into 20 ml of methyl ethyl ketone, heat to reflux to dissolve, then cool to room temperature while stirring, and filter after stirring for 2 hours. Dry at 60°C. A 4.1 g sample of crystal form X was obtained, with a melting point of 201-204°C.

[0030] Form X powder X-ray diffraction 20 is: 4.08, 4.77, 5.73, 6.80, 7.17, 7.91, 8.27, 9.62, 9.99, 11.66, 12.70, 13.70, 14.30, 15.42, 15.90, 16.80, 17.51, 18.06, 18.42, 20.48 , 20.95, 23.27, 23.72, 24.78, 25.18, 25.82, 26.10, 26.64, 26.96, 27.90, 28.85, 29.70, 31.08, 34.18

Embodiment 3

[0032] The preparation method of febuxostat crystal form Y:

[0033] Add 2 g of febuxostat to 5 ml of acetone and reflux to dissolve, then add 10 ml of acetonitrile dropwise under stirring and reflux, cool to room temperature after the addition, stir for 1 hour, and filter. Dry at 60°C. Obtained febuxostat crystal form Y sample 1.4 g, melting point 202-204 ° C

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PUM

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Abstract

The invention discloses a new crystal form X, Y and Z of 2-(3-cyanogroup-4-isobutoxy) phenyl-4-methyl-5-thiazole formic acid (febuxostat for short) with the formula of I and a preparing method thereof, and is confirmed by a melting point and a powder X diffraction pattern. The febuxostat prepared with the method is stable in temperature, illumination and humidity and is favourable for storage fora long term; adopted solvent is safe and easy to remove, and the method has easy operation, is suitable for industrial production and is suitable for directly producing preparation.

Description

technical field [0001] The present invention relates to medicinal chemistry, in particular to the crystal form X, crystal Form Y, crystal form Z and preparation method thereof Background technique [0002] The common name of 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylic acid is febuxostat or febuxostat, which is mainly used for the treatment of hyperuricemia . [0003] EP513379 reports the synthesis method of febuxostat, in which it is mentioned that recrystallization with ethanol is used to obtain the final product, but the problem of the crystal form is not described. In Chinese patent CN1275126, it is recorded that febuxostat has five crystal forms A, B, C, D, G and an amorphous form, wherein crystal A is the relatively stable crystal form, crystal D is methanolate, and crystal G The crystals are hydrates. This patent uses a mixed solvent system of methanol / water or isopropanol / water for crystallization, and can perform crystal transformation according t...

Claims

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Application Information

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IPC IPC(8): C07D277/56A61P19/06
Inventor 罗军芝焦慧荣郤文斌王新光
Owner UTOPHARM SHANGHAI
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