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Resolution method of naproxen enantiomer

A technology of enantiomers and naproxen, which is applied in the field of medicine, can solve the problems of complicated post-treatment of mobile phase addition method and expensive chiral stationary phase method, and achieve simple and easy resolution method, rapid and effective separation, The effect of high sensitivity

Pending Publication Date: 2019-09-06
斯诺科(杭州)生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In view of this, the object of the present invention is to provide a kind of simple and easy naproxen enantiomer resolution method, solve the problems such as mobile phase addition method post-processing complexity and chiral stationary phase method are relatively expensive, simultaneously after resolution Handling is simple and easy

Method used

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  • Resolution method of naproxen enantiomer
  • Resolution method of naproxen enantiomer
  • Resolution method of naproxen enantiomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] (1) Add (-)-(1S,4S)-borneol (1.87g, 12mmol), naproxen (2.30g, 10mmol) and p-toluenesulfonic acid (0.1g, 0.5mmol) into a round bottom flask in sequence , Its molar ratio is 1.2:1:0.05, dissolved in 30mL of toluene, heated to reflux with stirring, and thin layer chromatography to detect the progress of the reaction. After the reaction is over, the toluene is distilled off, 200-300 mesh silica gel column chromatography is performed with petroleum ether and ethyl acetate as eluents, the effluent is detected by thin layer chromatography, and the effluent is dried by rotary evaporation to obtain pure naproxen bornyl ester. 2.21g.

[0028] (2) Take 10 mg of naproxen bornyl ester obtained in step (1), dissolve it in methanol, transfer it to a 25ml volumetric flask, and dilute to volume with methanol to obtain the test solution; divide the test solution into the following liquid phase Chromatographic conditions for high performance liquid chromatography analysis;

[0029] Use the f...

Embodiment 2

[0031] Example 2: Resolution of Naproxen

[0032] (1) Add (-)-(1S,4S)-borneol (1.87g, 12mmol), naproxen (2.30g, 10mmol) and p-toluenesulfonic acid (0.1g, 0.5mmol) into a round bottom flask in sequence , Its molar ratio is 1.2:1:0.05, dissolved in 30mL of toluene, heated to reflux with stirring, and thin layer chromatography to detect the progress of the reaction. After the reaction is over, the toluene is distilled off, 200-300 mesh silica gel column chromatography is performed with petroleum ether and ethyl acetate as eluents, the effluent is detected by thin layer chromatography, and the effluent is dried by rotary evaporation to obtain pure naproxen bornyl ester. 2.21g.

[0033] (2) Take 10 mg of naproxen bornyl ester obtained in step (1), dissolve it in methanol, transfer it to a 25ml volumetric flask, and dilute to volume with methanol to obtain the test solution; divide the test solution into the following liquid phase Chromatographic conditions for high performance liquid ...

Embodiment 3

[0036] Example 3: Resolution of Naproxen

[0037] (1) Add (-)-(1S,4S)-borneol (1.87g, 12mmol), naproxen (2.30g, 10mmol) and p-toluenesulfonic acid (0.1g, 0.5mmol) into a round bottom flask in sequence , Its molar ratio is 1.2:1:0.05, dissolved in 30mL toluene, heated to reflux with stirring, and thin layer chromatography to detect the progress of the reaction. After the reaction is over, toluene is distilled off, 200-300 mesh silica gel column chromatography is performed with petroleum ether and ethyl acetate as eluents, the effluent is detected by thin layer chromatography, and the effluent is dried by rotary evaporation to obtain pure naproxen bornyl ester. 2.21g.

[0038] (2) Take 10 mg of naproxen bornyl ester obtained in step (1), dissolve it in methanol, transfer it to a 25ml volumetric flask, and dilute to volume with methanol to obtain the test solution; divide the test solution into the following liquid phase Chromatographic conditions for high performance liquid chromat...

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Abstract

The invention belongs to the technical field of medicines, and particularly discloses a resolution method of a naproxen enantiomer. The method mainly comprises the following steps that naproxen is mixed with (-)-(1S,4S)-borneol and p-toluenesulfonic acid for an esterification reaction, through separation and purification, naproxen borneol ester is obtained, then the naproxen borneol ester is dissolved in methyl alcohol and subjected to resolution through a high performance liquid chromatography method, and a naproxen borneol ester diastereoisomer is obtained. According to the resolution method, the cheap (-)-(1S,4S)-borneol is adopted as a chiral reagent for pre-column derivatization, an achiral chromatographic column is selected as a chromatographic column, the method is simple and easy to implement, a flowing phase is simple, and a chiral additive is not needed; after-treatment is simple, the economical and practical purpose is achieved, the sensitivity is high, and the naproxen enantiomer can be quickly and effectively separated.

Description

Technical field [0001] The present invention relates to the technical field of medicine, in particular to a method for the resolution of enantiomers of naproxen. Background technique [0002] Non-steroidal anti-inflammatory drugs are currently the most widely used drugs in the world with high anti-inflammatory, antipyretic and analgesic effects. Most non-steroidal anti-inflammatory drugs are chiral. Studies have found that such drug enantiomers may have significantly different pharmacological activities or adverse reactions in the organism. Naproxen [naproxen, chemical name 2-(6-methoxy-2-naphthyl)propionic acid], is a 2-arylpropionic acid non-steroidal anti-inflammatory drug. It has antipyretic, anti-inflammatory and analgesic effects. It is mainly used to treat rheumatic spondylitis, rheumatoid arthritis and postpartum and postoperative pain relief. Naproxen exists in a pair of optically active enantiomers, the (S)-enantiomer is 28 times more effective than the (R)-enantiomer...

Claims

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Application Information

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IPC IPC(8): C07C51/42C07C51/493C07C67/08C07C67/56C07C59/64C07C69/734
CPCC07B2200/07C07C51/42C07C51/493C07C67/08C07C67/56C07C2602/42C07C59/64C07C69/734
Inventor 陈朗钱丹娟
Owner 斯诺科(杭州)生物科技有限公司