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Separation detection method of apremilast and apremilast enantiomer

An enantiomer and detection method technology, applied in the field of separation and detection of apremilast and its enantiomers, can solve the problems of unpredictable separation effect, failure to meet the minimum resolution requirements, etc., and achieve accuracy High, specific effects

Active Publication Date: 2015-07-22
SUZHOU YABAO PHARMA R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are no specific examples, and the separation effect that can be achieved cannot be predicted. We separated Apremilast and its enantiomers according to the method described in the patent, and found that the separation degree of the two was only 1.26, which did not reach Minimum resolution requirement of 1.5
[0006] Therefore, there is currently no effective method reported in the literature that can accurately and sensitively separate and detect apremilast and its enantiomers

Method used

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  • Separation detection method of apremilast and apremilast enantiomer
  • Separation detection method of apremilast and apremilast enantiomer
  • Separation detection method of apremilast and apremilast enantiomer

Examples

Experimental program
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Effect test

Embodiment 1

[0042] Example 1 Patent 201410765717.5 method

[0043] Instruments and Conditions

[0044] High performance liquid chromatography: Agilent 1260

[0045] Chromatographic column: AD-H (ChiralPak 250*4.6mm, 5μm)

[0046] Mobile phase: n-hexane-isopropanol-diethylamine-trifluoroacetic acid=80:20:0.2:0.5

[0047] Flow rate: 1.0mL / min

[0048] Detection wavelength: 240nm

[0049] Column temperature: 40°C

[0050] Injection volume: 10μL

[0051] Take an appropriate amount of Apremilast racemate (batch number: 20140708, self-made by Yabao Pharmaceutical Group Co., Ltd.), add a certain amount of absolute ethanol, dissolve it by ultrasonic waves, and prepare a drug containing 0.1 mg of racemate per 1 mL. solution. Carry out high performance liquid chromatography analysis by above-mentioned condition, record chromatogram, the result sees attached figure 1 . according to figure 1 It can be seen from the results that the separation degree of the two is 1....

Embodiment 2

[0053] Instruments and Conditions

[0054] High performance liquid chromatography: Agilent 1260

[0055] Chromatographic column: AD-H (ChiralPak 250*4.6mm, 5μm)

[0056] Mobile phase: n-hexane-absolute ethanol-diethylamine=50:50:0.1

[0057] Flow rate: 1.0mL / min

[0058] Detection wavelength: 240nm

[0059] Column temperature: 25°C

[0060] Injection volume: 10μL

[0061] Experimental procedure

[0062] Take apremilast R-isomer (batch number: 20140719, ee: 99.12%, made by Yabao Pharmaceutical Group Co., Ltd.), racemate (batch number: 20140708, made by Yabao Pharmaceutical Group Co., Ltd.) and Apremilast samples (batch number: 20140829, ee: 98.64%, self-produced by Yabao Pharmaceutical Group Co., Ltd.) are each appropriate amount, respectively, add a certain amount of absolute ethanol, dissolve it by ultrasonic, and make it contain about Premilast R-isomer 0.2mg positioning solution, racemate 0.1mg solution and apremilast 0.5mg sample solution. Carry out high performanc...

Embodiment 3

[0064] Instruments and Conditions

[0065] High performance liquid chromatography: Agilent 1260

[0066] Chromatographic column: AD-H (ChiralPak 250*4.6mm, 5μm)

[0067] Mobile phase: n-hexane-absolute ethanol-diethylamine=50:50:0.1

[0068] Flow rate: 1.0mL / min

[0069] Detection wavelength: 240nm

[0070] Column temperature: 20°C

[0071] Injection volume: 10μL

[0072] Experimental procedure

[0073] Take an appropriate amount of apremilast racemate, add a certain amount of absolute ethanol, dissolve it by ultrasonication, and make a solution containing about 0.1 mg of racemate per 1 mL. Carry out high performance liquid chromatography analysis by above-mentioned condition, record chromatogram, the result sees attached Figure 6 . Depend on Figure 5 It can be known that Apremilil and its enantiomers can be completely separated under this condition, the peak elution time of Apremilil is 31.760min, and the peak elution time of its enantiomers is 27.573min (relative ...

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Abstract

The invention discloses a high-efficient liquid phase chromatograph separation detection method of apremilast and apremilast enantiomer. A chromatographic condition is to adopt a direct-chain starch chiral column, and an n-hexane-low alcohol solution is adopted as a flow phase to carry out the separation determination for apremilast and apremilast enantiomer. By adopting the high-efficient liquid phase chromatograph separation detection method of the apremilast and apremilast enantiomer, the apremilast enantiomer can be effectively separated and determined, the specificity is high, the accuracy is high, and the method can be used for effectively controlling the quality of apremilast active ingredients.

Description

technical field [0001] The invention relates to the field of pharmaceutical analytical chemistry, in particular to a separation and detection method for apremilast and its enantiomers. Background technique [0002] Apremilast is a phosphodiesterase inhibitor. It is the first small-molecule drug approved by the FDA on March 21, 2014 for the treatment of arthritis caused by psoriasis. The original research company is Celgene. The chemical structural formula is as follows: [0003] [0004] Separation of enantiomers containing chiral carbon atoms has always been a difficult point in quality control during the synthesis and preparation of chiral drugs. Apremilast is a chiral drug. In order to ensure the safety of the drug, it is necessary to detect the content of enantiomer impurities in the drug in the quality standard. Enantiomers cannot be separated by conventional high-performance liquid chromatography and must be separated using a suitable chiral column. [0005] Chin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G01N30/88G01N30/06
Inventor 王羽姚勇敢李敏刘保杰
Owner SUZHOU YABAO PHARMA R&D CO LTD
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