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High-performance liquid-phase resolution method of rotigotine key intermediate

A high-performance liquid phase and high-performance liquid chromatography technology, applied in the field of drug analysis and detection, can solve the problems of inability to measure the content of enantiomer impurities and low accuracy of optical rotation, and achieve simple methods, ensure process control, and strong The effect of practicality

Inactive Publication Date: 2020-09-08
上海柏狮生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the similar properties of optical isomers, the current main detection methods for chiral enantiomers are optical rotation and high performance liquid chromatography. Due to the relatively low accuracy of optical rotation, the enantiomer impurities cannot be detected. content, so it is necessary to develop high performance liquid chromatography that can effectively separate chiral isomer impurities and accurately detect their content

Method used

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  • High-performance liquid-phase resolution method of rotigotine key intermediate
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  • High-performance liquid-phase resolution method of rotigotine key intermediate

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Experimental program
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Effect test

Embodiment 1

[0034] Instruments and conditions used: Agilent 1260 (Agilent Technologies, USA); Ultra SonicCleaner USK Type ultrasonic cleaner; XS105 electronic balance (Mettler-Toledo International Trade (Shanghai) Co., Ltd.)

[0035] Chromatographic column CHIRALPAK OD (250mmx4.6mm x5um) (Daicel (China) Investment Co., Ltd.)

[0036] The mobile phase flow rate is 1.2mL / min;

[0037] The temperature of the chromatographic column is 30°C;

[0038] The injection volume is 10uL;

[0039] The detection wavelength is 225nm;

[0040] In the mobile phase, calculated by volume percentage, n-hexane: ethanol: diethylamine: trifluoroacetic acid is 94%: 6%: 0.15%: 0.05%

[0041] Step 1: Prepare the S-configuration solution: Weigh 5.00 mg of the S-configuration rotigotine key intermediate into a 10mL volumetric flask, use the mobile phase as the diluent, dissolve, and dilute to volume with the diluent, mix well and shake well, Obtain the S configuration solution;

[0042] Step 2: Prepare the R-con...

Embodiment 2

[0047] Instruments and conditions used: Agilent 1260 (Agilent Technologies, USA); Ultra SonicCleaner USK Type ultrasonic cleaner; XS105 electronic balance (Mettler-Toledo International Trade (Shanghai) Co., Ltd.)

[0048] Chromatographic column CHIRALPAK OD (250mmx4.6mmx5um) (Daicel (China) Investment Co., Ltd.).

[0049] The mobile phase flow rate is 1.2mL / min;

[0050] The temperature of the chromatographic column is 30°C;

[0051] The injection volume is 10uL

[0052] The detection wavelength is 225nm;

[0053] In the mobile phase, calculated by volume percentage, n-hexane: ethanol: diethylamine: trifluoroacetic acid is 98%: 2%: 0.15%: 0.05%

[0054] Step 1: Prepare the S-configuration solution: Weigh 5.00 mg of the S-configuration rotigotine key intermediate into a 10mL volumetric flask, use the mobile phase as the diluent, dissolve, and dilute to volume with the diluent, mix well and shake well, Obtain the S configuration solution;

[0055] Step 2: Prepare the R-conf...

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Abstract

The invention relates to the technical field of drug analysis and detection, in particular to a high-performance liquid-phase resolution method of rotigotine key intermediate. According to the method,a high performance liquid chromatograph is adopted, a polysaccharide derivative normal phase coating type chiral chromatographic column is adopted, a mixed solution of n-hexane, ethanol, diethylamineand trifluoroacetic acid is adopted as a mobile phase, and the flow velocity of the mobile phase is 1.0-1.5 mL / min; the temperature of the chromatographic column is 30 + / -5 DEG C; the detection wavelength is 225nm; and the sample size is 5-15 [mu] L. According to the method disclosed by the invention, the R configuration and the S configuration of the rotigotine key intermediate can be effectively and thoroughly separated in a chromatogram; the content of a rotigotine optical isomer is accurately measured, the quality control problem of the rotigotine optical isomer is solved, process controlof the final product rotigotine optical isomer is ensured, and the method has great social significance in industrial production, and high practicability.

Description

technical field [0001] The invention relates to the technical field of drug analysis and detection, in particular to a high-efficiency liquid phase resolution method for a key intermediate of rotigotine. Background technique [0002] The chemical name of rotigotine (S)-5,6,7,8-tetrahydro-6-[propyl[2-(2-thiophene)ethyl]amino]-1-naphthol hydrochloride Salt, developed by Schwarz Biosciences in Germany, is used for the adjuvant treatment of early secondary Parkinson's disease and advanced Parkinson's disease. In May 2007, the U.S. FDA approved its marketing. Transdermal patch for Syndrome Syndrome. The chemical name of Rotigotine is ((S)-5,6,7,8-tetrahydro-6-(propyl(2-(2-thienyl)ethyl)amino)-1-naphthol ), the molecular formula is C 19 h 25 NOS, the drug is chiral, and the structural formula of rotigotine is as follows: [0003] [0004] According to the bibliographical reports of rotigotine, synthetic rotigotine is that compound 5-methoxytetralone and n-propylamine are s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G01N30/02G01N30/34
CPCG01N30/02G01N30/34G01N2030/027G01N2030/8877
Inventor 宋玉红王亚萍胡剑王红秀
Owner 上海柏狮生物科技有限公司