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A preparing method for high-purity ilaprazole sodium

A high-purity technology of ilaprazole sodium, applied in the field of pharmaceutical preparation, can solve the problems of side reactions, difficult removal of sulfonyl peroxide, and inability to effectively remove impurities such as ilaprazole sodium salt, and achieves easy handling, The effect of simple and easy refining process and high product quality

Inactive Publication Date: 2016-10-26
LIVZON PHARM GRP INC +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] However, this route is prone to peroxidative side reactions in the middle of the oxidation process, resulting in the formation of peroxysulfonyl compounds that are difficult to remove
In the current technology, there is no preparation method that can effectively remove impurities and obtain high-purity ilaprazole sodium salt

Method used

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  • A preparing method for high-purity ilaprazole sodium
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  • A preparing method for high-purity ilaprazole sodium

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Example 1: 5-(1H-pyrrol-1-yl)-2-[[(4-methoxy-3-methyl)-2-pyridyl]-methyl]-sulfinyl-1H-benzene Preparation of imidazole potassium salt

[0025] Add methanol (110mL) and potassium hydroxide (3.1g) to a 250mL three-necked flask, stir to dissolve and clarify, then add 5-(1H-pyrrol-1-yl)-2-[[(4-methoxy-3- Methyl)-2-pyridyl]-methyl]-sulfinyl-1H-benzimidazole (20 g), and the mixture was stirred at 25° C. for 18 hours. The mixture was filtered, the filter cake was washed with methanol (20mL*2), and the collected solid was dried at 40°C for 4 hours to obtain 5-(1H-pyrrol-1-yl)-2-[[(4-methoxy-3 -Methyl)-2-pyridyl]-methyl]-sulfinyl-1H-benzimidazole potassium salt (20.0 g), yield: 90%.

Embodiment 2

[0026] Example 2: 5-(1H-pyrrol-1-yl)-2-[[(4-methoxy-3-methyl)-2-pyridyl]-methyl]-sulfinyl-1H-benzene Preparation of imidazole sodium salt

[0027] Add organic solvent A (110mL) and sodium hydroxide (2.2g) to a 250mL three-necked flask, stir to dissolve and clarify, then add 5-(1H-pyrrol-1-yl)-2-[[(4-methoxy- 3-methyl)-2-pyridyl]-methyl]-sulfinyl-1H-benzimidazole (20 g), and the mixture was stirred at a specific temperature for 18 hours. The mixture was filtered, the filter cake was washed with methanol (20mL*2), and the collected solid was dried at 40°C for 4 hours to obtain 5-(1H-pyrrol-1-yl)-2-[[(4-methoxy-3 -methyl)-2-pyridyl]-methyl]-sulfinyl-1H-benzimidazole sodium salt, specifically as shown in Table 1:

[0028] Table 1: Comparison of experimental results of organic solvent A and reaction temperature

[0029] serial number

[0030] As shown in the table above, the organic solvent A is preferably methanol or ethanol, and the reaction temperature is preferably...

Embodiment 3

[0031] Example 3: 5-(1H-pyrrol-1-yl)-2-[[(4-methoxy-3-methyl)-2-pyridyl]-methyl]-sulfinyl-1H-benzene Preparation of imidazole

[0032] Add ethanol (200mL) to a 500mL three-necked flask, 5-(1H-pyrrol-1-yl)-2-[[(4-methoxy-3-methyl)-2-pyridyl]-methyl] -Sulfinyl-1H-benzimidazole potassium salt (10g), add 10% acetic acid ethanol solution dropwise at 25°C to adjust the pH value to 9.0, let stand for 30 minutes and filter, filter cake with ethanol aqueous solution (50%, 30mL* 2) 5-(1H-pyrrol-1-yl)-2-[[(4-methoxy-3-methyl)-2-pyridyl]-methyl] after washing and drying at 30°C -Sulfinyl-1H-benzimidazole (7.4 g, white solid), yield: 82%, purity: 99.2%.

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Abstract

A preparing method for high-purity ilaprazole sodium is provided. The method includes 1) dissolving a 2-[(4-methoxy-3-methylpyridin-2-yl)methyl]sulfinyl-5-(1H-pyrrol-1-yl)-1H-benzimidazole crude product into an organic solvent, adding an inorganic alkali to form a salt, and filtering to obtain a 2-[(4-methoxy-3-methylpyridin-2-yl)methyl]sulfinyl-5-(1H-pyrrol-1-yl)-1H-benzimidazole salt (A), 2) dissolving the A into an organic solvent, adjusting pH with an acid until reaching alkalescence to prepare high-purity 2-[(4-methoxy-3-methylpyridin-2-yl)methyl]sulfinyl-5-(1H-pyrrol-1-yl)-1H-benzimidazole (B), and 3) reacting the prepared B with a sodium-containing compound in a water-containing solvent to prepare the ilaprazole sodium.

Description

technical field [0001] The invention relates to the field of medicine preparation, in particular to a method for refining ilaprazole sodium. Background technique [0002] 5-(1H-pyrrol-1-yl)-2-[[(4-methoxy-3-methyl)-2-pyridyl]-methyl]-sulfinic acid is described in Chinese patent CN94191913.7 The synthetic method of acyl-1H-benzimidazole, the synthetic method uses chloroform as a solvent, m-chloroperoxybenzoic acid as an oxidizing agent to oxidize 5-(1H-pyrrol-1-yl)-2-[[(4-methoxy -3-methyl)-2-pyridyl]-methyl]-mercapto-1H-benzimidazole to prepare 5-(1H-pyrrol-1-yl)-2-[[(4-methoxy-3- Methyl)-2-pyridyl]-methyl]-sulfinyl-1H-benzimidazole. The synthetic route is as follows: [0003] [0004] However, this route is prone to peroxidative side reactions in the middle of the oxidation process, resulting in the formation of peroxysulfonyl compounds that are difficult to remove. In the current technology, there is no preparation method that can effectively remove impurities and o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14
CPCC07D401/14
Inventor 冯杨肖鸿李桂铤李显焕王蕊
Owner LIVZON PHARM GRP INC
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