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Synthetic method of Rabeprazole Sulfone (2-[[[4-(3-methoxy propoxy)-3-methyl-2-pyridyl] methyl] sulfonyl]-1H-benzimidazole)

A technology of methoxypropoxyl and rabeprazole sulfone, which is applied in the field of medicine, can solve the problems of low product purity, long reaction time, and cumbersome experimental operations, and achieve simple synthesis steps, stable product quality, and high purity of prepared samples high effect

Active Publication Date: 2014-12-03
吉林修正药业新药开发有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The experimental operation of this method is more loaded down with trivial details, and reaction time is long, and the product purity obtained is lower

Method used

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  • Synthetic method of Rabeprazole Sulfone (2-[[[4-(3-methoxy propoxy)-3-methyl-2-pyridyl] methyl] sulfonyl]-1H-benzimidazole)
  • Synthetic method of Rabeprazole Sulfone (2-[[[4-(3-methoxy propoxy)-3-methyl-2-pyridyl] methyl] sulfonyl]-1H-benzimidazole)
  • Synthetic method of Rabeprazole Sulfone (2-[[[4-(3-methoxy propoxy)-3-methyl-2-pyridyl] methyl] sulfonyl]-1H-benzimidazole)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] 1. Weigh 1 part by weight of rabeprazole sulfide, add 1 part by weight of methylene chloride and heat to dissolve at 30-60°C, then add 1 part by weight of m-chloroperoxybenzoic acid, stir for 1-4 hours, and perform thin-layer chromatography Follow the reaction process, and concentrate under reduced pressure after the reaction is completed.

[0017] 2. Add 1 part by weight of methanol to the concentrated solution in step 1 to dissolve, then elute on a silica gel column, use a mixture of ethyl acetate:petroleum ether at 1:0.2 to 1:5 as the eluent, and combine the mixture containing the target substance eluent.

[0018] 3. Add the collected solution obtained in step 2 into a round bottom flask, concentrate under reduced pressure, then add 1 part by weight of methanol to dissolve the sample, and then add 1 part by weight of isopropyl ether to precipitate the sample. After filtering, the off-white compound rabeprazole sulfone is obtained,

Embodiment 2

[0020] 1. Weigh 1 part by weight of rabeprazole sulfide, add 3 parts by weight of dichloromethane and heat to dissolve at 30-60°C, then add 2 parts by weight of m-chloroperoxybenzoic acid, stir for 1-4 hours, thin layer Chromatography is used to track the reaction process, and after the reaction is completed, it is concentrated under reduced pressure;

[0021] 2. Add 3 parts by weight of methanol to the concentrated solution in step 1 to dissolve, then elute on a silica gel column, use a mixture of ethyl acetate:petroleum ether 1:0.2 to 1:5 as the eluent, and combine the mixture containing the target substance eluent.

[0022] 3. Add the collected liquid obtained in step 2 into a round bottom flask, concentrate under reduced pressure, then add 3 parts by weight of methanol to dissolve the sample, and then add 3 parts by weight of isopropyl ether to precipitate the sample. After filtration, the off-white compound rabeprazole sulfone is obtained.

Embodiment 3

[0024] 1. Weigh 1 part by weight of rabeprazole sulfide, add 5 parts by weight of dichloromethane and heat to dissolve at 30-60°C, then add 4 parts by weight of m-chloroperoxybenzoic acid, stir for 1-4 hours, trace by thin-layer chromatography The reaction process is concentrated under reduced pressure after completion of the reaction;

[0025] 2. Add 5 parts by weight of methanol to the concentrated solution in step 1 to dissolve, then elute on a silica gel column, use a mixture of ethyl acetate:petroleum ether at 1:0.2 to 1:5 as the eluent, and combine the mixture containing the target substance eluent.

[0026] 3. Add the collected liquid obtained in step 2 into a round bottom flask, concentrate under reduced pressure, then add 5 parts by weight of methanol to dissolve the sample, and then add 5 parts by weight of isopropyl ether to precipitate the sample. After filtration, the off-white compound rabeprazole sulfone is obtained.

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Abstract

Belonging to the medicine field, the invention more specifically relates to a synthetic method of an impurity Rabeprazole Sulfone (2-[[[4-(3-methoxy propoxy)-3-methyl-2-pyridyl] methyl] sulfonyl]-1H-benzimidazole) in a medicine Rabeprazole Sodium for treating alimentary peptic ulcer. Rabeprazole Sulfone with high purity is obtained through the method, and is used as a known impurity in quality analysis of Rabeprazole Sodium for clarifying position of impurity in a sample and investigating degree of separation between the impurity and the sample, so that the analysis method is more accurate. The method provided by the invention has the advantages of mild conditions, simple synthesis steps, stable product quality, simple experiment operations and high purity of the prepared sample.

Description

Technical field: [0001] The invention belongs to the field of medicine, in particular to the impurity rabeprazole sulfone (2-[[[4-(3-methoxypropoxy)-3-methyl- 2-pyridyl] methyl] sulfonyl] -1H-benzimidazole) synthetic method. Background technique: [0002] Proton pump inhibitors are effective drugs for the treatment of peptic ulcer disease. As a second-generation proton pump inhibitor, rabeprazole sodium can enhance gastric mucosal secretion and prostaglandin biosynthesis, protect esophageal mucosa, directly inhibit the final link of gastric acid secretion, and play an acid-suppressive role. At present, the general production process of rabeprazole sodium is to use thioether oxidation to synthesize rabeprazole sodium, a sulfoxide compound. During the oxidation process, excessive oxidation inevitably forms sulfone impurities, and rabeprazole sulfone is synthesized as rabeprazole sodium. The main by-product, its chemical name is 2-[[[4-(3-methoxypropoxy)-3-methyl-2-pyridyl]me...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/12
CPCC07D401/12
Inventor 曹翠阎君林子琦王化录白冰刘学峰展月
Owner 吉林修正药业新药开发有限公司