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A kind of preparation method of omeprazole metabolite

A technology of omeprazole and metabolites, which is applied in the field of drug synthesis, can solve the problem that metabolite research has not been reported, and achieves the effect of reasonable route design and strong operability

Active Publication Date: 2019-12-06
TLC NANJING PHARMA RANDD CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Omeprazole metabolite is a metabolite in the synthesis process of omeprazole. Through the synthesis and research of metabolites, relevant pharmacology and pharmacokinetic studies of omeprazole can be carried out. Meprazole's metabolic mechanism study provides test samples, but there is no report on the study of this metabolite

Method used

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  • A kind of preparation method of omeprazole metabolite
  • A kind of preparation method of omeprazole metabolite
  • A kind of preparation method of omeprazole metabolite

Examples

Experimental program
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Effect test

Embodiment 1

[0027] (1) Take 15g of 5,6-dimethylnicotinic acid methyl ester and dissolve it in 150mL of dichloromethane, add 31g of 75% m-chlorobenzoic acid in batches under ice bath, stir and react at room temperature for 3 hours, Thin-layer chromatography showed that the reaction was complete, and the organic phase was washed with saturated aqueous sodium bicarbonate to obtain 14.64 g of compound II as a yellow solid, with a yield of 89%;

[0028] (2) 6g of Compound II was added in batches to 30ml of 65% concentrated nitric acid in an ice bath, stirred and reacted at 90°C for 3 hours, thin-layer chromatography showed that the reaction was complete, the reaction solution was reduced to 0°C and water was added, and the product was dichloromethane Extraction, and the organic phase was dried with anhydrous sodium sulfate to obtain 5.6 g of compound III, with a yield of 75%;

[0029] (3) 4.5g of compound Compound III was dissolved in 45mL of methanol, 3.2g of sodium methoxide was added under ...

Embodiment 2

[0036] (1) Dissolve 15g of 5,6-dimethylnicotinic acid methyl ester in 150mL of methanol, add 26.8g of 75% m-chlorobenzoic acid in batches under ice bath, stir and react at room temperature for 3 hours, thin Layer chromatography showed that the reaction was complete, and the organic phase was washed with saturated aqueous sodium bicarbonate to obtain 14.64 g of compound II as a yellow solid, with a yield of 85%;

[0037] (2) 6g of Compound II was added in batches to 36ml of 65% concentrated nitric acid in an ice bath, stirred and reacted at 90°C for 3 hours, thin-layer chromatography showed that the reaction was complete, the reaction solution was lowered to 0°C and water was added, and the product was dichloromethane Extraction, the organic phase was dried with anhydrous sodium sulfate to obtain 5.6 g of compound III, with a yield of 74%;

[0038] (3) 4.5g of compound Compound III was dissolved in 45mL of methanol, 3.2g of sodium methoxide was added under ice-cooling, and reac...

Embodiment 3

[0045] (1) Dissolve 15g of 5,6-dimethylnicotinic acid methyl ester in 150mL of methanol, add 26.8g of 30% hydrogen peroxide in batches under ice bath, stir and react at room temperature for 3 hours, thin-layer chromatography shows that the reaction Completely, the organic phase was washed with a saturated aqueous sodium bicarbonate solution to obtain 14.64 g of compound II as a yellow solid, with a yield of 80%;

[0046] (2) 6g of Compound II was added in batches to 24ml of 65% concentrated nitric acid in an ice bath, stirred and reacted at 90°C for 3 hours, thin layer chromatography showed that the reaction was complete, the reaction solution was lowered to 0°C and water was added, and the product was dichloromethane Extraction, the organic phase was dried with anhydrous sodium sulfate to obtain 5.6 g of compound III, with a yield of 74%;

[0047] (3) 4.5g of compound Compound III was dissolved in 45mL of methanol, 3.2g of sodium methoxide was added under ice-cooling, and rea...

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Abstract

The invention discloses a preparation method of an omeprazole metabolite, and belongs to the field of pharmaceutical synthesis. A reaction route is reasonable in design; the operability is high. The preparation method comprises the following steps of reacting to synthesize a target compound with eight steps of firstly enabling 5,6-methyl dimethylnicotinate to be subjected to oxidation through nitrogen, nitrifying, carrying out nitro-substitution, rearranging, chloridizing, butting with 2-mercapto-5-methoxybenzimidazole, carrying out sulfur oxidation, and carrying out hydrolysis, and the like.The whole route of the preparation method is reasonable in design; the post treatment is simple; raw materials are cheap and are easily obtained, and a prepared and obtained target product has the purity which can be up to 99.7 percent or above, can be used for pharmacokinetic study, is used for providing a test sample for the study of a metabolic mechanism of omeprazole, and has important application value.

Description

technical field [0001] The invention belongs to the field of drug synthesis, in particular to a preparation method of omeprazole metabolites. Background technique [0002] Omeprazole, the chemical name is 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl]-1H-benzo Imidazole; researched and developed by ASRA Company of Sweden, it was launched in 1988 and approved for use in 65 countries by 1992; it is mainly used for duodenal ulcer and Zoller-Ellison syndrome, and can also be used for gastric ulcer and reflux Esophagitis; intravenous injection can be used for the treatment of acute bleeding of peptic ulcer. Combined with amoxicillin and clindamycin or metronidazole and clarithromycin to kill Helicobacter pylori. The quality, safety and efficacy of drugs should be scientifically evaluated before they go on the market, among which the impurities contained in drugs are the most critical issue, so controlling the content of impurities in drugs is the key to evalua...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/12
CPCC07D401/12
Inventor 宋化丰李志胡永铸崔希林
Owner TLC NANJING PHARMA RANDD CO LTD
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