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Synthesis method of meloxicam

A meloxicam and synthesis method technology, applied in the field of drug synthesis, can solve the problems of high toxicity of xylene, long reaction time, and large amount of solvent, and achieve the effects of less solvent amount, short reaction time, and less environmental pollution

Active Publication Date: 2012-11-14
QINGDAO AGRI UNIV +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The amount of solvent used in this route is relatively large, the reaction time is relatively long, and the solvent xylene is also highly toxic, and the dichloroethane used for recrystallization is a highly toxic substance.

Method used

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  • Synthesis method of meloxicam
  • Synthesis method of meloxicam

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Add 283g (1mol) 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-ethyl carboxylate-1,1-dioxide and 126g (1.1mol) 2-amino -5-Methylthiazole, then add 600mL dimethyl sulfoxide, stir, heat up to 189 degrees, distill off ethanol at the same time during the reaction, add 450mL ethanol to the reaction solution after 3 hours of reaction, cool to room temperature and filter to obtain Crude product, the crude product was recrystallized from tetrahydrofuran to obtain 323g of meloxicam, with a yield of 92% and a content of 99.4%.

Embodiment 2

[0022] Add 283g (1mol) 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-ethyl carboxylate-1,1-dioxide and 137g (1.2mol) 2-amino -5-Methylthiazole, then add 1000mL dimethyl sulfoxide, stir, heat up to 189 degrees, distill off ethanol at the same time during the reaction, react for 3 hours, add 1.6L ethanol to the reaction solution after the reaction is completed, cool to After filtering at room temperature, the crude product was obtained. The crude product was recrystallized from tetrahydrofuran to obtain 316 g of meloxicam, with a yield of 90% and a content of 99.6%.

Embodiment 3

[0024] Add 283g (1mol) 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-ethyl carboxylate-1,1-dioxide and 148g (1.3mol) 2-amino -5-Methylthiazole, then add 1000mL dimethyl sulfoxide, stir, heat up to 140°C, distill off ethanol at the same time during the reaction, add 1L ethanol to the reaction solution after 12 hours of reaction, cool to room temperature and filter to obtain Crude product, the crude product was recrystallized from tetrahydrofuran to obtain 306g of meloxicam, with a yield of 87% and a content of 99.3%.

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Abstract

The invention relates to a synthesis method of meloxicam, belonging to the field of medicine synthesis. The method comprises the following steps of: adding 4-hydroxyl-2-methyl-2H-1,2-benzothiazine-3-ethyl formate-1,1-dioxide and 2-amino-5-methylthiazole into dimethyl sulfoxide; reacting at a certain temperature while steaming out ethanol; after the reaction, adding a certain amount of ethanol into the reaction liquid; cooling and filtering to obtain a crude product of meloxicam; and recrystallizing the crude product to obtain a high-purity purified product of meloxicam.

Description

technical field [0001] The invention relates to a synthesis method of meloxicam, which belongs to the field of drug synthesis. Background technique [0002] The English name of meloxicam is Meloxicam, and its chemical name is 4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide -1,1-dioxide, the molecular formula is C14H15O4S2, the molecular weight is 351.42, and its structural formula is as follows: [0003] [0004] Meloxicam is a new type of non-steroidal anti-inflammatory analgesics (NSAIDs), which is a thiazide derivative with strong analgesic and anti-inflammatory effects. It was developed by Boehringer Ingelheim in Germany. Its greatest feature is the selective inhibition of type II cyclooxygenase (COX-2), which is mainly used for the treatment of rheumatoid arthritis and osteoarthritis, and can also be used for antipyretic and analgesic. Compared with the traditional non-steroidal anti-inflammatory drugs currently used, it has strong an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/12
Inventor 郝智慧林扬贾德强姚德勇沈巍张瑞丽王艳玲
Owner QINGDAO AGRI UNIV
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