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Novel crystal form of azilsartan and preparation method thereof

A technology of crystal form and crystal form, which is applied in the field of type B and its preparation, can solve the problems of solubility and low bioavailability of preparations, and achieve the effect of good stability

Inactive Publication Date: 2015-02-11
CP PHARMA QINGDAO CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In general, for oral solid water-insoluble drugs, the higher the melting point of the product crystal form, the better the stability, but the solubility of the corresponding product and the bioavailability of the preparation are relatively low

Method used

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  • Novel crystal form of azilsartan and preparation method thereof
  • Novel crystal form of azilsartan and preparation method thereof
  • Novel crystal form of azilsartan and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Preparation of Crystal Form B of Azilsartan

[0019] Add 5L of 0.04mol / L sodium hydroxide solution to a 10L three-necked flask, stir mechanically, add 450g of 1-[[2'-(2,5-dihydro-5-oxo-1,2,4oxadiazole-3 -yl)[1,1'-biphenyl]-4-yl]methyl]-2-ethoxy-1H-benzimidazole-7-carboxylic acid. (Temperature control throughout the process to T<20°C), stir to dissolve the solid, add 0.5 L of acetonitrile, stir to obtain a clear and transparent solution, add 1 mol / L hydrochloric acid, adjust the pH to 1-2, precipitate a large amount of solid, stir for 30 min, After suction filtration, the filter cake was rinsed with water until neutral, and the product was air-dried at 45°C to constant weight to obtain 423.7g of the target crystal form B product, with a yield of 94.2%.

Embodiment 2

[0021] Preparation of Crystal Form B of Azilsartan

[0022] Add 3L of 0.1mol / L sodium hydroxide solution to a 10L three-necked flask, stir mechanically, add 450g of 1-[[2'-(2,5-dihydro-5-oxo-1,2,4oxadiazole-3 -yl)[1,1'-biphenyl]-4-yl]methyl]-2-ethoxy-1H-benzimidazole-7-carboxylic acid. Stir to dissolve the solid, add 3L of acetonitrile, stir to obtain a clear and transparent solution, add 1mol / L hydrochloric acid, adjust the pH to 5-6, and precipitate a large amount of solid, stir for 30min, and filter with suction (the temperature is controlled to T<20°C during the whole process) , the filter cake was rinsed with water until neutral, and the product was air-dried at 45° C. to constant weight to obtain 393.5 g of the target product, with a yield of 87.4%.

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Abstract

The invention relates to a novel crystal form (called form B) of a latest-generation antihypertensive drug, namely, 1-[[2'-(2,5-dihydro-5-oxo-1,2,4oxadiazol-3-yl)[1,1'-biphenyl]-4-yl]methyl]-2-ethoxy-1H-benzimidazole-7-carboxylic acid (generic name: azilsartan), and a preparation method thereof. The azilsartan is found to have a polycrystalline state for the first time, and the novel crystal form is in a semi-stable state. As proved by research, a semi-stable-state product has high crystal form stability, can be preserved at the room temperature for six months, and is free from change in a powder-X diffraction pattern and constant in HPLC (High Performance Liquid Chromatography) purity. The novel crystal form which can be applied to further medicinal development is provided for the project development.

Description

technical field [0001] The present invention relates to a latest generation antihypertensive drug 1-[[2'-(2,5-dihydro-5-oxo-1,2,4 oxadiazol-3-yl)[1,1'- A new crystal form of biphenyl]-4-yl]methyl]-2-ethoxy-1H-benzimidazole-7-carboxylic acid (common name: Azilsartan), which is called Form B and its preparation method. Background technique [0002] The chemical name of azilsartan is 1-[[2'-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)[1,1'-biphenyl ]-4-yl]methyl]-2-ethoxy-1H-benzimidazole-7-carboxylic acid, the structural formula is shown in formula [I]. [0003] [0004] Azilsartan was developed by Japan's Takeda Pharmaceutical Co., Ltd. and launched in Japan in April 2012. It is an angiotensin Ⅱ receptor antagonist. It is the latest generation of sartan drugs for treating hypertension. It can be used alone or in combination with other blood pressure lowering drugs. It is regarded as the next generation product of candesartan cilexetil. Its prodrug is azilsartan medoxomil, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/10
CPCC07D413/10
Inventor 秦引林伍贤志
Owner CP PHARMA QINGDAO CO LTD
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