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Synthetic method of omeprazole sulfone

A technology of omeprazole sulfonyl compound and synthesis method, which is applied in the field of medicine, can solve the problems of low yield of preparation method, cumbersome experimental operation, and low product yield, and achieve high yield of sample preparation, simple experimental operation, The effect of high purity

Inactive Publication Date: 2017-06-20
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

Said method preparation method yield is low
This method experimental operation is more loaded down with trivial details, and reaction time is long, and the product yield obtained is low

Method used

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  • Synthetic method of omeprazole sulfone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] 1. Weigh 1g of omeprazole sulfide, add 10ml of dichloromethane and heat to dissolve at 40°C, add 1g of m-chloroperoxybenzoic acid, stir for 3h, and then concentrate under reduced pressure;

[0022] 2. Add 20ml of methanol to the concentrated solution in step 1 to dissolve, then elute on a silica gel column, use ethyl acetate and petroleum ether (1:1) (v / v) as the eluent, and combine the elutions containing the target substance liquid.

[0023] 3. Add the collected liquid obtained in step 2 into a round bottom flask, concentrate under reduced pressure, then dissolve the sample with 10ml of methanol, and then use 20ml of isopropyl ether to precipitate the sample. After filtration, an off-white compound was obtained with a yield of 82% and a purity of 99.3%.

[0024] Result confirmation data: mp: 118~120℃; ESI-MS(m / Z)[M+H + ]: 361.45;

[0025] IR (KBr, cm -1 ): 3436, 3055, 2995, 2904, 2805, 1626, 1590, 1510, 1468, 1410, 1205; UV (nm): 306.1, 299.63, 273.0.

[0026] 1...

Embodiment 2

[0028] 1. Weigh 1g of omeprazole sulfide, add 5ml of dichloromethane and heat to dissolve at 50°C, add 0.5g of m-chloroperoxybenzoic acid, stir for 5h, and then concentrate under reduced pressure;

[0029] 2. Add 10ml of methanol to the concentrated solution in step 1 to dissolve, then elute on a silica gel column, use ethyl acetate and petroleum ether (1:0.2) (v / v) as the eluent, and combine the elutions containing the target substance liquid.

[0030] 3. Add the collected liquid obtained in step 2 into a round bottom flask, concentrate under reduced pressure, then dissolve the sample with 5ml of methanol, and then use 15ml of isopropyl ether to precipitate the sample. After filtration, the off-white compound was obtained with a yield of 79% and a purity of 99.2%.

[0031] Result confirmation data: mp: 118~120℃; ESI-MS(m / Z)[M+H + ]: 362.12;

[0032] IR (KBr, cm -1 ): 3441, 3056, 2993, 2909, 2803, 1628, 1591, 1512, 1471, 1408, 1201; UV (nm): 306.3, 299.56, 273.2.

[0033]...

Embodiment 3

[0035] 1. Weigh 1g of omeprazole sulfide, add 20ml of dichloromethane and heat to dissolve at 65°C, add 2g of m-chloroperoxybenzoic acid, stir for 2h, and then concentrate under reduced pressure;

[0036] 2. Add 15ml of methanol to the concentrated solution in step 1 to dissolve, then elute on a silica gel column, use ethyl acetate and petroleum ether (1:4.5) (v / v) as the eluent, and combine the elutions containing the target substance liquid.

[0037] 3. Add the collected solution obtained in step 2 into a round bottom flask, concentrate under reduced pressure, then dissolve the sample with 20ml of methanol, and then use 30ml of isopropyl ether to precipitate the sample. After filtration, an off-white compound was obtained with a yield of 84% and a purity of 99.5%.

[0038] Result confirmation data: mp: 118~120℃; ESI-MS(m / Z)[M+H + ]: 361.71;

[0039] IR (KBr, cm -1 ): 3430, 3052, 2990, 2901, 2804, 1627, 1592, 1513, 1469, 1413, 1203; UV (nm): 305.8, 299.11, 272.8.

[0040...

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Abstract

The synthetic method of omeprazole sulfonylate comprises: (1) adding dichloromethane to omeprazole sulfide and dissolving under heating, then adding m-chloroperoxybenzoic acid, concentrating under reduced pressure after reaction; (2) adding methylene chloride to step Add methanol to the concentrated solution of (1) to dissolve, then elute on a silica gel column, and elute with ethyl acetate and petroleum ether; (3) concentrate the eluent obtained in step (2) under reduced pressure to obtain an oily substance, and then Dissolve the sample with methanol, add isopropyl ether to precipitate the sample, and after filtration, the off-white product of the present invention is obtained with a yield of 78%. The positive effect of the present invention is: the omeprazole sulfonylate with higher yield and higher purity is obtained. It is used as a known impurity in the quality analysis of omeprazole, the position of the impurity in the sample is clarified, the separation between the impurity and the sample is investigated, and the analysis method is more accurate. The method has mild conditions, simple steps, stable quality, high sample yield and high purity.

Description

[0001] Technical field: [0002] The invention belongs to the field of medicine, in particular to impurity omeprazole sulfonylate (5-methoxy-2-[(4-methoxy-3,5-dimethyl The synthetic method of base pyridin-2-yl)methylsulfonyl]-1H-benzimidazole). [0003] Background technique: [0004] Omeprazole is the first-generation benzimidazole gastric acid proton pump inhibitor developed by Astra Zeneca in Sweden. It is a common drug for the treatment of peptic ulcer and reflux gastritis and other diseases. The last step of gastric acid secretion is proton in gastric parietal cells The pump drives intracellular H + K + In exchange, PPIs block the last channel of gastric acid secretion and inhibit gastric acid secretion, thereby treating peptic ulcers. During the process of production and storage, some side reactions and impurities will occur, which directly or indirectly affect the quality of the drug. Therefore, it is very important to fully and accurately grasp the information of impu...

Claims

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Application Information

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IPC IPC(8): C07D401/12
CPCC07D401/12
Inventor 曹翠阎君白冰徐建李桂峰常红刘学峰于施
Owner 吉林修正药业新药开发有限公司
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