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Dexibuprofen purifying method

A refining method and organic solvent technology, applied in the field of refining ibuprofen, can solve the problems of high cost of sodium alcoholate, high impurity content, low yield, etc., and achieve simple and easy-to-control process steps, high product purity, and yield high rate effect

Inactive Publication Date: 2015-07-01
LUNAN BETTER PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But the cost of sodium alcoholate is high and easy to hydrolyze, so it is not suitable for large-scale production
And, above-mentioned each method yield is all lower
[0007] The impurity content of the currently commercially available dextroibuprofen raw materials is generally high, and the impurity ibuprofen ethyl ester is difficult to eliminate by traditional methods

Method used

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  • Dexibuprofen purifying method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Add 50 g of the crude product of Dexibuprofen into the reaction flask, add 500 mL of acetone and stir, heat at 30 ° C until the system is clear, add dropwise 10% sodium hydroxide solution to adjust the pH to 9.0, after the drop is complete, keep stirring for 20 minutes, Cool down to -10°C, stir and crystallize for 4 hours, and filter to obtain Dexibuprofen sodium salt. Dissolve the sodium salt in 400mL of pure water, add 200mL of n-hexane, add hydrochloric acid dropwise under stirring to adjust the pH to 1.1, extract, separate the liquids, extract the water phase with 200mL of n-hexane again, combine the organic phases, and wash two times with 200mL of pure water. Once, the organic phase was distilled under reduced pressure to obtain the pure product of Dexibuprofen, with a yield of 76%. After HPLC detection, the maximum single impurity is 0.07%, the total impurity is 0.5%, and the ee value is 99.5%.

Embodiment 2

[0046] Add 50 g of the crude product of Dexibuprofen into the reaction flask, add 250 mL of ethanol and stir, heat at 45 ° C until the system is clear, add dropwise 20% sodium hydroxide solution to adjust the pH to 9.5, after the drop is complete, keep stirring for 20 minutes, Cool down to 0°C, stir and crystallize for 2 hours, and filter to obtain Dexibuprofen sodium salt. Dissolve the sodium salt in 400mL of pure water, add 200mL of n-hexane, add concentrated hydrochloric acid dropwise under stirring to adjust the pH=1.5, extract, separate the liquids, extract the water phase with 200mL of n-hexane again, combine the organic phases, and wash with 200mL of pure water Twice, the organic phase was distilled under reduced pressure to obtain the pure product of Dexibuprofen with a yield of 81%. After HPLC detection, the maximum single impurity is 0.08%, the total impurity is 0.4%, and the ee value is 99.6%. · Ibuprofen ethyl ester impurity was detected.

Embodiment 3

[0048]Add 50g of the crude product of Dexibuprofen into the reaction flask, add 200mL of acetone and stir, heat at 50°C until the system is clear, add dropwise 25% sodium hydroxide solution to adjust the pH to 9.8, after dropping, keep stirring for 20 minutes, Cool down to 0°C, stir and crystallize for 2 hours, and filter to obtain Dexibuprofen sodium salt. Dissolve the sodium salt in 400mL of pure water, add 200mL of n-hexane, add concentrated hydrochloric acid dropwise under stirring to adjust the pH=3.1, extract, separate the liquids, extract the water phase with 200mL of n-hexane again, combine the organic phases, and wash with 200mL of pure water Twice, the organic phase was distilled under reduced pressure to obtain the pure product of Dexibuprofen, with a yield of 82%. After HPLC detection, the maximum single impurity is 0.05%, the total impurity is 0.21%, and the ee value is 99.9%.

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Abstract

The invention relates to a dexibuprofen purifying method. The method comprises the following steps: dissolving crude dexibuprofen in an organic solvent 1, adding a sodium hydroxide solution in a dropwise manner to adjust the pH value to 9-10, carrying out cooling crystallization to obtain dexibuprofen sodium; dissolving dexibuprofen sodium in purified water, adding an organic solvent 2, and adding hydrochloric acid in a dropwise manner under stirring in order to adjust the pH value to 1-2; and carrying out liquid separation, taking the obtained organic phase, and carrying out reduced pressure distillation on the organic phase to obtain a solid which is purified dexibuprofen. The product obtained through the method has high purity of above 99.7% and high yield of above 75%; the method can completely eliminate ibuprofen ester impurities, and allows the maximal content of single impurities to be smaller than 0.1% and the total content of the impurities to be smaller than 0.3%; and the method has the advantages of low cost, simplicity and easy control of process steps, and suitableness for large scale production.

Description

technical field [0001] The invention belongs to the technical field of medicine and chemical industry, and in particular relates to a refining method of Dexibuprofen. Background technique [0002] S(+)-ibuprofen [S(+)-ibuprofen] is the general name of S(+)-2-(4-isobutylphenyl)propionic acid, and its structural formula is: [0003] [0004] Molecular formula: C 13 h 18 o 2 Molecular weight: 206.28. [0005] Ibuprofen is a non-steroidal anti-inflammatory and analgesic drug. Compared with aspirin, it has stronger antipyretic, anti-inflammatory and analgesic effects, and has much fewer side effects. Since its listing in the late 1970s, ibuprofen has developed rapidly and has become one of the largest production and usage anti-inflammatory, antipyretic and analgesic drugs. D-ibuprofen is the optical isomer of ibuprofen S configuration. A large number of studies have shown that Dexibuprofen has the same curative effect as ibuprofen, but the dosage is small, and its safety...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C57/30C07C51/42C07C51/487
CPCC07C51/42C07B2200/07C07C51/487C07C57/30
Inventor 赵志全杨斌张德力王军
Owner LUNAN BETTER PHARMA
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