Method for separating and detecting enantiomer of ezetimibe key intermediate

An enantiomer and ezetimibe technology, which is applied in the field of drug analysis, can solve problems such as the analysis and detection method of key intermediates of ezetimibe, and achieve safety and effectiveness, high sensitivity, and method accurate effect

Active Publication Date: 2015-07-08
CHANGZHOU YABANG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] At present, there is no report on the analysis and detection methods of

Method used

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  • Method for separating and detecting enantiomer of ezetimibe key intermediate
  • Method for separating and detecting enantiomer of ezetimibe key intermediate
  • Method for separating and detecting enantiomer of ezetimibe key intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1: Preparation of Derivatized Product of Ezetimibe Key Intermediate A

[0037] At room temperature, add 0.1mL of isopropanol and 10mg of ezetimibe key intermediate A to a 1.5ml EP tube, shake, then add 35μl of 1mol / L sulfuric acid solution, place on a shaker for 2h, then add Dilute the sample with 0.5ml of isopropanol and transfer it to the filter, filter, wash the EP tube and filter with a small amount of isopropanol, take the filter cake, evaporate the solvent at room temperature, and obtain the derivative of the key intermediate A of ezetimibe chemical products.

Embodiment 2

[0038] Example 2: Preparation of Enantiomeric Derivatized Products of Ezetimibe Key Intermediate A

[0039] At room temperature, add 0.1 mL of isopropanol and 10 mg of the enantiomer of ezetimibe key intermediate A to a 1.5 ml EP tube, shake, then add 35 μl of 1 mol / L sulfuric acid solution, place on a shaker Shake it up for 2 hours, then add 0.5ml of isopropanol to dilute the sample and transfer it to the filter, filter, wash the EP tube and filter with a small amount of isopropanol, take the filter cake, and evaporate the solvent at room temperature to obtain ezetimibe Derivatization products of enantiomers of key intermediate A.

Embodiment 3

[0041] Instruments and Conditions:

[0042] High performance liquid chromatography: Agilent, 1260Bin Pump, 1260VWD detector, 1260TCC column thermostat, 1260ALS autosampler, ChemStation workstation;

[0043] Column: IC (150mm×4.6mm×5μm);

[0044] Mobile phase: water: acetonitrile: tetrahydrofuran = 65: 31.6: 3.4;

[0045] Flow rate: 1.0ml / min;

[0046] Detection wavelength: 230nm;

[0047] Column temperature: 30°C;

[0048] Injection volume: 20 μl.

[0049] Experimental procedure: take the derivatized products in Examples 2 and 3 in equal amounts, mix them, dissolve and dilute them with acetonitrile-water mixed solvent (acetonitrile:water=40:60) to a concentration of about 1 mg / ml each, and measure them precisely Inject 20 μl into the liquid chromatograph, record the chromatogram, and see the results in figure 1 .

[0050] figure 1 The one with a retention time of 22.152 min is the derivatization product of the key intermediate A of ezetimibe, and the one with a reten...

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Abstract

The invention discloses a method for separating and detecting an ezetimibe key intermediate A and an enantiomer thereof by using pre-column derivatization high performance liquid chromatography. The method comprises the following steps: carrying out reaction for removing trimethylsilyl protecting groups on the ezetimibe key intermediate A and the enantiomer thereof in an organic alcohol solution by using an acidic solution of a certain concentration, and after reacting for certain time, performing simple after-treatment, thereby obtaining a derivatization product without protecting groups. The ezetimibe key intermediate A and the enantiomer thereof subjected to derivatization can be separated and detected by adopting the high performance liquid chromatography by taking chiral packing as a stationary phase.

Description

technical field [0001] The invention relates to a method for separating and detecting enantiomers of key intermediates of ezetimibe, belonging to the field of drug analysis. Background technique [0002] Ezetimibe is a selective intestinal cholesterol absorption inhibitor developed and marketed by Schering-Plough Pharmaceuticals. It was launched in the United States in 2002 under the trade name Zetia. In July 2011, CFDA approved this variety to be launched in China, and the trade name is Ezetrol. [0003] Ezetimibe is the first marketed selective intestinal cholesterol absorption inhibitor. Its mechanism of action is to attach to the brush border of small intestinal villi and effectively inhibit the absorption of cholesterol and phytosterols, thereby reducing the cholesterol in the small intestine to the liver. The transport in the liver reduces the storage of cholesterol in the liver and thus reduces the plasma cholesterol level. It does not increase bile secretion, nor d...

Claims

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Application Information

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IPC IPC(8): G01N30/02
Inventor 陈再新蒋晓琴朱峰王勇军夏正君吉小龙王彬王璠
Owner CHANGZHOU YABANG PHARMA
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