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Rabeprazole sodium compound and novel preparation method thereof

A technology for rabeprazole sodium and compound is applied in the field of rabeprazole sodium compound and its new preparation method, which can solve the problems of long synthesis steps, unsuitable for industrialization, and difficult to control oxidation to sulfoxide and the like

Inactive Publication Date: 2010-08-18
HAINAN MEILAN SMITH KLINE PHARMA
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] In order to overcome the low yield and long synthetic steps in the production of rabeprazole sodium in the above-mentioned prior art, the weaker or easily controlled oxidant m-chloroperoxybenzoic acid and 30 % of hydrogen peroxide is difficult to control the disadvantage of oxidation to sulfoxide, which brings convenience to the purification; it also avoids the use of tert-butyl peroxyacid and vanadium pentoxide as catalyst oxidation in the literature reports, which leads to a relatively large amount of consumption and relatively high cost , not suitable for industrialization

Method used

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  • Rabeprazole sodium compound and novel preparation method thereof
  • Rabeprazole sodium compound and novel preparation method thereof
  • Rabeprazole sodium compound and novel preparation method thereof

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Embodiment 1

[0026] The synthesis of embodiment 1 rabeprazole sodium

[0027] (1) Synthesis of 2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylthio}-1H-benzimidazole

[0028] 300g (2mol) 2-mercaptobenzimidazole, 505g (2.2mol) 2-chloromethyl-3-methyl-4-[(3-methoxy)propoxy]-pyridine and 100g (2.4mol) Sodium hydroxide was added to 2500ml of ethanol, stirred and reacted at 50°C for 3 hours, then the ethanol was distilled off under reduced pressure, 5L of purified water was added, stirred, a solid was precipitated, filtered, and dried to obtain 632g of the product, with a yield of 92%.

[0029] (2) Synthesis of Rabeprazole

[0030] In a 5L reaction flask, add 343g (1mol) 2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylthio}-1H-benzimidazole, 2L The volume ratio is a mixed solvent of acetonitrile and dichloromethane of 1:1, then add 255g (1.1mol) trichloroisocyanuric acid and 95g (1.2mol) pyridine, stir at room temperature for 4 hours, then pour the reactant into 1L Stir in water, the...

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Abstract

The invention aims at providing a novel rabeprazole sodium compound and a novel preparation method thereof. A novel oxidizing agent of trichloroisocyanuric acid is adopted for controlling the oxidization from thioether into sulfoxide, and the oxidization from the thioether into the sulfoxide is perfectly controlled. Because the invention shortens the reaction steps, and few other impurities are introduced in the process of synthesizing chiral rabeprazole sodium, so the purification process is easier, the purity and the yield of obtained finally products are high, and the invention is applicable to large-scale industrial production.

Description

technical field [0001] The invention relates to a rabeprazole sodium compound and a new preparation method thereof, belonging to the technical field of medicine. Background technique [0002] Rabeprazole sodium, its chemical name is: 2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl}-1H-benzimidazole sodium , molecular formula: C 18 h 20 N 3 NaO 3 S, molecular weight: 381.43, structural formula: [0003] [0004] Rabeprazole sodium, a benzimidazole compound, is a second-generation proton pump inhibitor that specifically inhibits gastric parietal cell H + 、K + -ATPase system to block the final step of gastric acid secretion. The effect is dose-dependent, and can inhibit both basal and stimulated gastric acid secretion. This product is against choline and histamine H 2 No receptor antagonistic effect. [0005] The synthetic route of the rabeprazole sodium that literature has reported is as follows: [0006] Route 1: [0007] [0008] Route 2: [0...

Claims

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Application Information

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IPC IPC(8): C07D401/12
Inventor 郝志艳
Owner HAINAN MEILAN SMITH KLINE PHARMA
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