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Preparation methods of flurbiprofen axetil compound

A technology of flurbiprofen axetil and flurbiprofen, which is applied in the field of preparation of flurbiprofen axetil compounds, can solve the problems of complicated process and high cost, and achieve the effects of simple operation, low production cost and easy acquisition

Active Publication Date: 2014-03-26
GUANGDONG JIABO PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method is complex and expensive, and is only suitable for laboratory research.

Method used

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  • Preparation methods of flurbiprofen axetil compound
  • Preparation methods of flurbiprofen axetil compound
  • Preparation methods of flurbiprofen axetil compound

Examples

Experimental program
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preparation example Construction

[0031] The invention discloses a preparation method of flurbiprofen ester compounds, the method comprising the following steps:

[0032] 1) Put flurbiprofen and acid catalyst in a molar ratio of 1: (0.02~0.4) in a reactor containing an organic solvent, heat up to 20~150°C, and then drop esters, esters The addition amount of substance is 0.9~8 times of flurbiprofen molar weight, and constant temperature reaction is to the end, obtains reaction system; Among them, the ester substances are added slowly, the dropping time is controlled within 3~36h, and the constant temperature reaction is completed until the reaction system is obtained.

[0033] 2) Concentrate the reaction system by rotary evaporation under reduced pressure, which can remove the solvent in the reaction system, then add ethyl acetate and water with a volume ratio of 1: (0.5~2) to dissolve, and let stand The layers were separated to give an organic phase.

[0034] 3) Wash the organic phase until neutral. The spec...

Embodiment 1

[0053] Embodiment 1: the preparation of flurbiprofen axetil.

[0054] Put 1.23mol of flurbiprofen and 0.15mol of p-toluenesulfonic acid in a reactor containing 6.0L of acetonitrile, heat up to 65°C, then slowly add 2.25mol of 1,1-ethylene glycol diacetic acid dropwise Esters, constant temperature reaction to the end, to obtain a reaction system.

[0055] The reaction system was concentrated by rotary evaporation under reduced pressure to remove the solvent. The heating temperature of rotary evaporation under reduced pressure was 50°C and the vacuum degree was -0.1mPa, and then 3.0L of Ethyl acetate and 3.0L of water were dissolved, and the organic phase was obtained by standing and separating.

[0056] Wash 3 times with 3.0L of saturated sodium bicarbonate solution, then wash 2 times with 3.0L of water until neutral, dry with 30g of anhydrous sodium sulfate for 8h, then carry out rotary evaporation and concentration under reduced pressure to remove the solvent, and decompress...

Embodiment 2

[0062] Embodiment 2: the preparation of flurbiprofen methylene diacetate.

[0063] Put 0.13mol of flurbiprofen and 0.52mol of acid catalyst in a reactor containing 0.6L of acetonitrile, heat up to 88°C, then slowly add 0.49mol of methylene diacetate dropwise, and keep the temperature until the end of the reaction , to get the reaction system.

[0064] The reaction system was concentrated by rotary evaporation under reduced pressure to remove the solvent. The heating temperature of rotary evaporation under reduced pressure was 65°C and the vacuum degree was -0.086mPa, and then 0.3L of Ethyl acetate and 0.3 L of water were dissolved, and the organic phase was obtained by standing and separating.

[0065] Wash 3 times with 0.3L saturated sodium bicarbonate solution, then wash 2 times with 0.3L water until neutral, use 15g of calcium sulfate to dry for 5h, then carry out vacuum rotary evaporation and concentration treatment to remove solvent, and vacuum rotary evaporation The he...

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Abstract

The invention discloses preparation methods of a flurbiprofen axetil compound. The methods comprise the steps: firstly dropwise adding an ester compound into a mixture of flurbiprofen, an acid catalyst and an organic solvent to form a reaction system, or directly mixing flurbiprofen, an alcohol and the acid catalyst, after a reaction is finished, thus obtaining a reaction system, then carrying out spin steaming concentration treatment under reduced pressure, adding ethyl acetate and water to fully dissolve, standing and layering to obtain an organic phase, washing the organic phase, drying, purifying by passing through a silica gel column, and thus obtaining the flurbiprofen axetil compound. The preparation methods have the advantages of simple reaction operation, low requirements on production personnel and production equipment, small pollution degree and low production cost, are safe and effective, can avoid use of high-risk and high-toxic materials, and can be used for mass production.

Description

technical field [0001] The invention relates to the technical field of pharmaceutical synthesis, in particular to a preparation method of flurbiprofen ester compounds. Background technique [0002] The molecular formula of flurbiprofen is 2-(2-fluoro-4-biphenyl)propionic acid. It is a non-steroidal anti-inflammatory analgesic drug with good analgesic, anti-inflammatory and antipyretic effects. Its anti-inflammatory effect is 250 times that of aspirin. The analgesic effect is 50 times that of aspirin. Flurbiprofen plays an anti-inflammatory and analgesic role by inhibiting the activity of prostaglandin synthase cyclooxygenase. It is well tolerated, and long-term use neither promotes nor inhibits its own metabolism. Flurbiprofen introduces a fluorine atom into the molecular structure. Due to the unique properties caused by the fluorine atom, it has a strong effect among similar drugs and a small therapeutic dose, so it has strong anti-inflammatory, analgesic and antipyretic f...

Claims

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Application Information

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IPC IPC(8): C07C69/65C07C67/10
CPCC07C67/08C07C67/10C07C69/65
Inventor 徐礼锋刘红兵岳峰黄健鹏
Owner GUANGDONG JIABO PHARM CO LTD
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