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Process for synthesizing lornoxicam intermediate against inflammation and pain

An anti-inflammatory analgesic, lornoxicam technology, applied in the field of compound synthesis, can solve the problems of low total yield, long reaction route, high raw material price, etc., and achieve the goal of reducing the discharge of three wastes, reducing risks, and low consumption Effect

Inactive Publication Date: 2005-11-23
JIANGSU POLYTECHNIC UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] The purpose of the present invention is to overcome the low total yield that exists in existing synthetic technology; The reaction route is longer; Raw material price is high (30,000 yuan / kg) and serious pollution etc. problems, a kind of brand-new synthetic method is provided:

Method used

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  • Process for synthesizing lornoxicam intermediate against inflammation and pain
  • Process for synthesizing lornoxicam intermediate against inflammation and pain
  • Process for synthesizing lornoxicam intermediate against inflammation and pain

Examples

Experimental program
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Effect test

Embodiment 1

[0016] (1). Synthesis of methyl 5-chloro-3-sulfonamidoacetate thiophene-2-carboxylate:

[0017] Add 10.3g of methyl 5-chloro-3-chlorosulfonylthiophene-2-carboxylate and 30g of methanol into a 250ml four-necked flask. At the same time, 54.5g of 8% sodium carbonate aqueous solution and 18g of 26% glycine methyl ester hydrochloride aqueous solution were added dropwise, and after the addition was completed, they were incubated at 15°C for 10 hours. Then, it was filtered and dried to obtain 12 g of methyl 5-chloro-3-sulfonamidoacetate thiophene-2-carboxylate, with a melting point of 117-118.5° C. and a yield of 95.8%.

[0018] (2). Synthesis of 6-chloro-4-hydroxyl-2H-thieno[2,3-e]-1,2-thiazine-3-carboxylic acid methyl ester-1,1-dioxide:

[0019] 12.5 g of methyl 6-chloro-3-sulfonamidoacetate thiophene-2-carboxylate and 74 g of 8% sodium methoxide in methanol were reacted at 65° C. for 8 hours. Cool to room temperature, then filter to obtain 6.7g 6-chloro-4-hydroxyl-2H-thieno[2,3-...

Embodiment 2

[0023] (1). Synthesis of methyl 5-chloro-3-sulfonamidoacetate thiophene-2-carboxylate:

[0024] Add 10.3g of methyl 5-chloro-3-chlorosulfonylthiophene-2-carboxylate and 30g of methanol water into a 250ml four-necked flask. At the same time, 69g of 6% sodium carbonate aqueous solution and 47g of 10% glycine methyl ester hydrochloride aqueous solution were added dropwise, and after the addition was completed, they were incubated at 15°C for 20 hours. Then, it was filtered and dried to obtain 11.8 g of methyl 5-chloro-3-sulfonamidoacetate, thiophene-2-carboxylate, with a yield of 94.2%.

[0025] (2). Synthesis of 6-chloro-4-hydroxyl-2H-thieno[2,3-e]-1,2-thiazine-3-carboxylic acid methyl ester-1,1-dioxide:

[0026] 12.5 g of methyl 6-chloro-3-sulfonamidoacetate thiophene-2-carboxylate and 40 g of 16% sodium methoxide in methanol were reacted at 71° C. for 4 hours. Cool to room temperature, then filter to obtain 7g 6-chloro-4-hydroxyl-2H-thieno[2,3-e]-1,2-thiazine-3-carboxylic ac...

Embodiment 3

[0030] (1). Synthesis of methyl 5-chloro-3-sulfonamidoacetate thiophene-2-carboxylate:

[0031] Add 10.3g of methyl 5-chloro-3-chlorosulfonylthiophene-2-carboxylate and 30g of methanol into a 250ml four-necked flask. At the same time, 125g of 3% sodium carbonate aqueous solution and 80g of 6% glycine methyl ester hydrochloride aqueous solution were added dropwise, and after the addition was completed, the mixture was kept at 15° C. for 10 hours. Then it was filtered and dried to obtain 11.2 g of methyl 5-chloro-3-sulfonamidoacetate thiophene-2-carboxylate with a yield of 89.4%.

[0032] (2). Synthesis of 6-chloro-4-hydroxyl-2H-thieno[2,3-e]-1,2-thiazine-3-carboxylic acid methyl ester-1,1-dioxide:

[0033] 12.5 g of methyl 6-chloro-3-sulfonamidoacetate thiophene-2-carboxylate and 120 g of 6% sodium methoxide in methanol were reacted at 40° C. for 15 hours. Cool to room temperature, then filter to obtain 6.3g of 6-chloro-4-hydroxyl-2H-thieno[2,3-e]-1,2-thiazine-3-carboxylic ac...

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Abstract

Disclosed is a process for synthesizing lornoxicam intermediate against inflammation and pain, which comprises using 5-chloro-3-thiophene sulfonyl chloride-2-carboxylate as raw material, charging 2-10% of sodium carbonate aqueous solution and 5-30% of glycine methylester hydrochloride simultaneously into water and methanol phases, thermal insulating 6-26 hours at 10-60 deg. C, then filtering and drying to obtain 6-chloro-3-sulfamoyl amido methyl acetate thiophene-2 methyl formate, reacting it with 5-27% of sodium methylate methanol solution 1-15 hours at 30-75 deg. C, filtering to obtain 6-chloro-4-hydroxyl-2H-thione[2,3-e]-1 and 2-thiazine-3-methyl formate-1,1-dioxide, then reacting the filtered substance with dimethyl sulfate in 1-10% aqueous solution of sodium-hydroxide.

Description

technical field [0001] The present invention relates to a compound synthesis method, specifically a 6-chloro-4-hydroxyl-2-methyl-2H-thieno[2,3-e]-1,2-thiazine-3-carboxylic acid methyl ester- A synthesis method of 1,1-dioxide, which is used to synthesize the anti-inflammatory and analgesic drug lornoxicam. Background technique [0002] The anti-inflammatory analgesic drug Lornoxicam Lomoxicam is a selective cyclooxygenase inhibitor non-steroidal anti-inflammatory analgesic drug developed by Norway Nycomed Company. It was first launched in Denmark in October 1997 and has been sold in more than 30 countries worldwide It has been listed in the country and included in the analgesic ladder program formulated by the World Health Organization. In 2002, domestic import sales were approved. This product has powerful anti-inflammatory and analgesic effects; it can be taken orally or injected, and is mainly used for the treatment of mild to moderate pain caused by rheumatoid arthritis...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/04
Inventor 吴卫忠裘兆蓉朱红星朱国彪
Owner JIANGSU POLYTECHNIC UNIVERSITY
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