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Two crystal forms of azilsartan and preparation method thereof

A crystal form and X-ray technology, applied in the field of medicinal chemistry, can solve the problems of significant antihypertensive effect, and achieve the effects of long-term preservation, good fluidity, and low production cost

Inactive Publication Date: 2013-09-25
HEFEI IND PHARMA INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In summary, there are not many crystal forms of azilsartan reported in the literature, but the drug has a significant antihypertensive effect and has a broad market prospect, so further research on its crystal forms is very necessary

Method used

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  • Two crystal forms of azilsartan and preparation method thereof
  • Two crystal forms of azilsartan and preparation method thereof
  • Two crystal forms of azilsartan and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Preparation of Azilsartan Form B:

[0021] Add 3g of azilsartan into a 50ml eggplant-shaped bottle, add 3ml of DMF and 18ml of acetone, stir electromagnetically, heat to 65°C to completely dissolve, stop heating and stirring, cool to room temperature for about 30 minutes, and place at room temperature for 2 hours, then Place at 0-5°C for 5 hours. After suction filtration, the filter cake was washed with a small amount of acetone, and vacuum-dried at 35° C. for 12 hours to obtain 2.3 g of white crystals.

[0022] X-ray powder diffraction pattern see figure 1 , see the DSC analysis chart figure 2 .

Embodiment 2

[0024] Preparation of Azilsartan Form C:

[0025] Add 3g of azilsartan into a 25ml eggplant-shaped bottle, add 3ml of DMF, stir electromagnetically and heat to 85°C to dissolve, add isopropanol dropwise to saturation (12ml), stop heating and stirring, and cool to room temperature for 30 minutes. During the cooling process, a small amount of solid precipitated out, and after standing at room temperature for 2 hours, it was left overnight at 0-5°C. After suction filtration, the filter cake was washed with a small amount of isopropanol, and vacuum-dried at 35° C. for 12 hours to obtain 2.5 g of white crystals.

[0026] X-ray powder diffraction pattern see image 3 , see the DSC analysis chart Figure 4 .

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Abstract

The invention belongs to the technical field of medicinal chemistry, and particularly relates to two crystal forms of azilsartan and a preparation method thereof. For the crystal form B of the azilsartan, in a X-ray powder diffraction pattern, 2theta has characteristic peaks near 7.46 degrees, 8.43 degrees, 9.38 degrees, 10.96 degrees, 18.90 degrees, 21.06 degrees, 21.98 degrees, 22.71 degrees, 23.11 degrees and 24.89 degrees. For the crystal form C, in the X-ray powder diffraction pattern, 2theta has characteristic peaks near 9.52 degrees, 11.64 degrees, 13.51 degrees, 20.85 degrees, 21.83 degrees, 22.40 degrees, 23.44 degrees, 25.17 degrees, 26.17 degrees and 29.06 degrees. The crystal form B and crystal form C of the azilsartan have better stability and fluidity and are beneficial to long-time storage.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and specifically relates to two crystal forms of azilsartan and a preparation method thereof. Background technique [0002] Azilsartan, chemical name 2-ethoxy-1-[[2'-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)biphenyl -4-yl] methyl] benzimidazole-7-carboxylic acid, structural formula (I) is as follows: [0003] [0004] The drug is a selective angiotensin II receptor antagonist developed by Takeda Corporation of Japan, which was approved for marketing in Japan in January 2012 for the treatment of hypertension. In addition, as its prodrug, Azilsartan medoxomil (TAK-491) was also approved by the US FDA on February 25, 2011. Azilsartan medoxomil is hydrolyzed into azilsartan medoxomil in the gastrointestinal tract after oral administration. Thomson Reuters predicts that the annual sales of azilsartan medoxomil will reach 703.3 million in 2014. Dollar. These all show that the drug has...

Claims

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Application Information

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IPC IPC(8): C07D413/10
Inventor 徐云根周海平刘伟何广卫
Owner HEFEI IND PHARMA INST
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