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Azilsartan crystal and preparation method thereof

A technology of crystal and unit cell volume, which is applied in the field of medicine and achieves the effects of satisfying large-scale production, high crystal purity and yield, and simple preparation method

Inactive Publication Date: 2015-01-07
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There is no report on the crystal structure of Azilsartan

Method used

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  • Azilsartan crystal and preparation method thereof
  • Azilsartan crystal and preparation method thereof
  • Azilsartan crystal and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] The preparation method of Azilsartan crystal is as follows:

[0014] In a 100mL beaker, add 50mg of azilsartan, add 50mL of anhydrous methanol, heat until there is reflux on the cup wall, stop heating after the azilsartan is completely dissolved, add anhydrous methanol to the system to 50mL, cover with plastic wrap Seal the beaker, leave a small hole to slowly volatilize the solvent, place the flask in a stable environment, and let it stand at 20°C to slowly volatilize the solvent. After 2 days, a colorless block crystal grows, and the crystal After the growth is complete, filter, wash with anhydrous methanol, and dry to obtain 44.6 mg of a crystal sample with a purity of 99.68% and a melting point of 208-210°C.

[0015] The proton nuclear magnetic resonance spectrum data of product are as follows:

[0016] H-NMR (400MHz, DMSO-d6): δ1.47 (3H, t, J = 7.0), 4.67 (2H, q, J = 7.0), 5.77 (2H, s), 7.07-7.70 (11H, m) .

[0017] Wherein, the chemical shift δ=1.47(3H) and 4.7...

Embodiment 2

[0026] Azilsartan crystal culture method comparative examples are as follows:

[0027] In a 100mL beaker, add 50mg of azilsartan, add 50mL of ethyl acetate, heat until there is reflux on the wall of the beaker, stop heating after the azilsartan is completely dissolved, add ethyl acetate to the system to 50mL, cover with plastic wrap Seal the beaker, leave small holes to slowly volatilize the solvent, place the flask in a stable environment, and let it stand at 20°C to slowly volatilize the solvent. After 2 days, a white crystalline solid precipitates out, and the crystal growth is complete. Afterwards, filter, wash with ethyl acetate, and dry to obtain 43.7mg of crystal samples with a purity of 99.54% and a melting point of 208-211°C, but regular crystals that can be tested by X-ray single crystal diffraction were not obtained.

Embodiment 3

[0029] Azilsartan crystal culture method comparative examples are as follows:

[0030] In a 100mL beaker, add 50mg of azilsartan, add 50mL of absolute ethanol, heat until there is reflux on the wall of the beaker, stop heating after the azilsartan is completely dissolved, add absolute ethanol to the system to 50mL, cover with plastic wrap Seal the beaker, leave small holes to slowly volatilize the solvent, place the flask in a stable environment, and let it stand at 20°C to slowly volatilize the solvent. After 2 days, a white crystalline solid precipitates out, and the crystal growth is complete. Afterwards, filter, wash with absolute ethanol, and dry to obtain 43.9 mg of a crystal sample with a purity of 99.61% and a melting point of 208-209° C., but regular crystals that can be tested by X-ray single crystal diffraction were not obtained.

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Abstract

The invention belongs to the field of medicine, and particularly relates to an azilsartan crystal and a preparation method thereof. The crystal is a monoclinic system, the space group is P2(1) / c, and the cell parameters are as follows: a=9.718(2)A, b=11.319(3)A, c=20.074(5)A, alpha=0 degrees, beta=90.383(5) degrees and gamma=90 degrees; the cell volume is 2208.0(8)A<3>; the dihedral angle between the benzimidazole ring and adjacent benzene ring is 68.42 degrees; the dihedral angle between two connected benzene rings is 59.84 degrees; and the dihedral angle between 5-oxo-1,2,4-oxadiazole ring and connected benzene ring is 71.83 degrees. The preparation method comprises the following steps: mixing azilsartan and absolute methanol, dissolving by heating under reflux, and slowly crystallizing in a stable environment at 10-30 DEG C to obtain the azilsartan crystal. The preparation method is simple, has the advantage of single crystal form, and has obvious effect on purifying azilsartan.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to an azilsartan crystal and a preparation method thereof. Background technique [0002] Azilsartan (Azilsartan, chemical name: 1-[[2'-(4,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)[1,1-link Phenyl]-4-base]methyl]-2-ethoxyl-1H-benzimidazole-7-carboxylic acid), is a new generation of angiotensin II receptor antagonist developed by Takeda Corporation in Japan, used for the treatment of hypertension. The drug was approved for marketing in Japan in January 2012, under the trade name: Azilva. Azilsartan is a new generation of selective AT1 subtype angiotensin Ⅱ receptor blockers (ARBs) antihypertensive drugs, compared with angiotensin converting enzyme inhibitors (ACEI) antihypertensive drugs, it has a stable With the advantages of lowering blood pressure and not causing dry cough, the market prospect is very broad. The structure of this compound is as follows: [0003] [0004] Pol...

Claims

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Application Information

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IPC IPC(8): C07D413/10
CPCC07D413/10
Inventor 李正义刘蓉刘大伟钱纪生陈亮孙小强
Owner CHANGZHOU UNIV
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