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Method for ammonolyzing and synthesizing meloxicam under catalysis of Lewis acid

A meloxicam and acid-catalyzed technology, applied in the direction of organic chemistry, can solve the problems of long reaction time, poor product color, poor refining effect, etc., and achieve the effect of short reaction time and easy purification

Inactive Publication Date: 2010-11-24
SHANDONG FANGMING PHARMACEUTICAL CO LTD
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Problems solved by technology

[0006] The main problem of this process is that in the step c process, the ammonolysis reaction temperature is generally at 110°C to 140°C, and the reaction time is 24 to 28 hours. At high temperature, partial decomposition and carbonization occur, the yield is low, usually about 60%, the product color is poor, and the refining effect is not good

Method used

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Examples

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Effect test

Embodiment Construction

[0010] In a 1000ml reaction flask, add 44g of ethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide, 2-amino-5-methylthiazole 24g, 4g of silica gel, 90ml of DMF, 400ml of xylene, heated to reflux, kept at reflux for the first 3 hours, then distilled off most of the xylene and DMF under reduced pressure for the next 3 hours, cooled to room temperature, stirred for 7 hours, and filtered to obtain the crude product.

[0011] The crude product was refluxed with tetrahydrofuran and activated carbon for 15 minutes, filtered, cooled to room temperature, shaken, rinsed with tetrahydrofuran, dried at 60°C, and measured to obtain 46.5 g of the product, with a yield of 85%. The purity of the product reached 99% by HPLC. The appearance: Light yellowish green, the product quality conforms to the 2005 edition of "Chinese Pharmacopoeia".

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Abstract

The invention relates to a method for ammonolyzing and synthesizing meloxicam under the catalysis of Lewis acid. Under the catalysis of silicate Lewis acid, the meloxicam is synthesized from 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylic acid ethyl ester 1,1-dioxide and 2-amino-5methylthiazol. Compared with the direct ammonolysis method, the method has the advantages that: (1) the reaction time is about 4 to 6 hours which is shortened by four times and ammonolysis is complete; and (2) the ammonolysis yield is high which is more than or equal to 85 percent; decomposers and carbides are avoided; the product is easy to purify; the method for synthesizing the meloxicam is suitable for mass production; the product purity reaches 99 percent through HPLC detection; the product is light yellow green; and the product quality meets Chinese pharmacopoeia 2005.

Description

Technical field [0001] The invention relates to a new synthesis method of meloxicam. It belongs to the technical field of organic synthesis. Background technique [0002] Meloxicam is an enoleic acid non-steroidal pain drug that can selectively inhibit cyclooxygenase-2 (cox-2), so it has less toxic side effects on the gastrointestinal tract and is mainly used for the treatment of arthritis and rheumatoid arthritis, the main synthetic methods of the current plant are: [0003] a, sodium saccharin and chloroacetate condensation; [0004] b. The condensate undergoes ring expansion under the condition of an organic base, and at the same time methylates to obtain 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylic acid ethyl ester 1,1-dioxide thing; [0005] c, 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylic acid ethyl ester 1,1-dioxide and 2-amino-5 methylthiazole in mixed organic phase (DMF and xylene), ammonolysis was carried out, and the reaction was completed, coo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/12
Inventor 刘存领范兴山王飞龙崔改英
Owner SHANDONG FANGMING PHARMACEUTICAL CO LTD
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