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Preparation method of parecoxib sodium impurity compound

A parecoxib sodium and compound technology, applied in the field of drug synthesis, can solve the problems of long steps, low product yield, complicated preparation methods, etc., and achieve the effects of short route, high product purity, and high reaction yield

Pending Publication Date: 2020-12-04
LUNAN PHARMA GROUP CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] CN109734681A discloses the relevant situation of dimer (its chemical structural formula is shown in formula I) impurity compound, but, its preparation method is complicated, through bromination reaction, sulfonyl chloride reaction is in condensation reaction, and step is long; Also through low temperature and column Complicated operations such as chromatography
Product yield is low

Method used

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  • Preparation method of parecoxib sodium impurity compound
  • Preparation method of parecoxib sodium impurity compound
  • Preparation method of parecoxib sodium impurity compound

Examples

Experimental program
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Effect test

Embodiment 1

[0057] Sodium 4-(5-methyl-3-phenyloxazol-4-yl)benzenesulfonate (SM-1, 4.02g, 12.5mmol) and CuCl 2 (1.18g, 8.75mmol) was added into acetonitrile (50mL), and the temperature was controlled at 60-65°C to react for 3h. 正己烷 :V 乙酸乙酯 =3:1, 25mL) after recrystallization, the target product I was obtained, with a yield of 94.2% and a purity of 100%.

Embodiment 2

[0059] Sodium 4-(5-methyl-3-phenyloxazol-4-yl)benzenesulfonate (SM-1, 4.02g, 12.5mmol) and CuCl 2 (0.92g, 6.88mmol) was added to 1,4-dioxane (50mL), and the temperature was controlled at 75-80°C to react for 5h. / Butyl acetate system (V 正己烷 :V 乙酸丁酯 =3:1, 25mL) after recrystallization, the target product I was obtained, with a yield of 86.4% and a purity of 99.96%.

Embodiment 3

[0061] Sodium 4-(5-methyl-3-phenyloxazol-4-yl)benzenesulfonate (SM-1, 4.02g, 12.5mmol) and CuCl 2 (0.84g, 6.25mmol) was added to DME (50mL), and the temperature was controlled at 80-85°C for 6h. After the reaction solution was cooled to room temperature, it was filtered. 石油醚 :V 乙酸丁酯 =3:1, 25mL) after recrystallization, the target product I was obtained, with a yield of 82.4% and a purity of 99.97%.

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Abstract

The invention belongs to the technical field of drug synthesis, and discloses a preparation method of a parecoxib sodium impurity compound, which comprises the following steps: by using sodium 4-(5-methyl-3-phenyl-oxazol-4-yl)benzenesulfonate as a raw material, adding into a reaction solvent under the catalysis of a copper salt, controlling the temperature until the reaction is finished, cooling the reaction solution to room temperature, and filtering to obtain the parecoxib sodium impurity compound. The preparation method disclosed by the invention is novel, simple to operate, high in productpurity and also suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and in particular relates to a preparation method of parecoxib sodium impurity compound. Background technique [0002] The chemical name of parecoxib sodium is: N-[[4-(5-methyl-3-phenyl-oxazolyl)phenyl]sulfonyl]propionamide sodium salt, which is a specific COX-2 inhibitor , due to its good water solubility, is often used as an injection, mainly for the short-term treatment of postoperative pain, and can be used clinically for the treatment of moderate or severe postoperative acute pain. Its chemical structural formula is as follows: [0003] [0004] The preparation method of parecoxib sodium mainly uses 3,4-diphenyl-5-methylisoxazole as raw material, synthesizes valdecoxib through sulfonation and aminolysis reactions, and then undergoes propionylation and salt formation obtain the target product. However, in the process of synthesizing valdecoxib, after the sulfonation reaction,...

Claims

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Application Information

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IPC IPC(8): C07D261/08
CPCC07D261/08
Inventor 郭新亮杨培伦
Owner LUNAN PHARMA GROUP CORPORATION