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Impurities of R-lipoic acid or tromethamine salts thereof, preparation method for impurities and detection method for impurities

A technology of d-lipoic acid and impurity reference substances, applied in the field of medicinal chemistry and analysis, to achieve the effect of accurate and applicable analysis methods

Active Publication Date: 2017-10-03
JIANGSU AOSAIKANG PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the inventors conducted in-depth research and found that some impurities still belong to unknown impurities, which have not been separated and confirmed.

Method used

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  • Impurities of R-lipoic acid or tromethamine salts thereof, preparation method for impurities and detection method for impurities
  • Impurities of R-lipoic acid or tromethamine salts thereof, preparation method for impurities and detection method for impurities
  • Impurities of R-lipoic acid or tromethamine salts thereof, preparation method for impurities and detection method for impurities

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Example 1: Preparation of (R)-5-(1,2-dithiopentan-3-yl)pentanoic acid-2,2-dioxide (compound of formula I)

[0055] Dissolve 60g of D-lipoic acid tromethamine in 1000ml of purified water to prepare a 0.06g / ml solution, and irradiate the aqueous solution with 4500lx±500lx strong light for 15 days to obtain a primary preparation sample solution.

[0056] Chromatographic conditions for HPLC primary preparation:

[0057] Instrument: Innovative Tongheng preparative liquid phase LC6000, preparative column DAC100, diameter 10cm

[0058] Stationary phase: Octadecylsilane bonded silica gel, 1.5kg charge, 10μm

[0059] Mobile phase: A-0.15% phosphoric acid aqueous solution, B-acetonitrile

[0060] Detection wavelength: 215nm

[0061] Flow rate: 200ml / min

[0062] Column temperature: 25°C

[0063] Injection volume: 200ml

[0064] Elution method: Gradient elution

[0065]

[0066]Collect the substance corresponding to the target peak at a retention time of about 50-60min. ...

Embodiment 2

[0089] Example 2: Separation and detection of related substances of D-lipoic acid tromethamine according to the method included in USP

[0090] This embodiment investigates the separation effect of the main component and related substances in the D-lipoic acid trometamol sample by the method included in USP.

[0091] Preparation of each sample of D-lipoic acid tromethamine:

[0092] Sample 1 (undestroyed): Take about 15 mg of D-lipoic acid tromethamine, weigh it accurately, put it in a 10 ml measuring bottle, dissolve it with mobile phase and dilute to the mark, and shake well.

[0093] Sample 2 (oxidative damage): Take about 15 mg of D-lipoic acid tromethamine, accurately weigh it, put it in a 10 ml measuring bottle, add 1 ml of 3% hydrogen peroxide solution to dissolve, immediately dissolve and dilute to the mark with mobile phase, shake uniform.

[0094] Sample 3 (high temperature destruction): Take about 15mg of D-lipoic acid tromethamine, weigh it accurately, put it in ...

Embodiment 3

[0109] Embodiment 3: Separation and detection of D-lipoic acid tromethamine related substances according to the method of the present invention

[0110] This embodiment investigates the separation effect of the method of the present invention on the main component and related substances in the D-lipoic acid trometamol sample.

[0111] Preparation of each sample of D-lipoic acid tromethamine:

[0112] Sample 1 (undamaged): Take about 15 mg of D-lipoic acid tromethamine, accurately weigh it, put it in a 10ml measuring bottle, dissolve it with a diluent [0.05% phosphoric acid solution-acetonitrile (85:15)] and dilute to the mark , shake well.

[0113] Sample 2 (oxidative damage): Take about 15 mg of D-lipoic acid tromethamine, accurately weigh it, put it in a 10 ml measuring bottle, add 1 ml of 3% hydrogen peroxide solution to dissolve, and immediately add diluent [0.05% phosphoric acid solution-acetonitrile (85:15)] diluted to the mark and shaken well.

[0114] Sample 3A (hig...

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Abstract

The invention provides an impurity compound of R-lipoic acid or tromethamine salts thereof represented by a formula (I) shown in the description and a preparation method for the impurity compound. The preparation method comprises the steps of irradiating an aqueous solution of the R-lipoic acid or tromethamine salts thereof with strong light, and then, carrying out HPLC (High-Performance Liquid Chromatography) twice, thereby preparing the compound represented by the formula (I), wherein during primary preparation, a flowing phase is prepared from A: a 0.15% phosphoric acid aqueous solution and B: acetonitrile, and during secondary preparation, a flowing phase is prepared from A: a 0.1% trifluoroacetic acid aqueous solution and B: acetonitrile; and an elution mode is gradient elution. The invention further provides an HPLC detection method for related substances of the R-lipoic acid or tromethamine salts thereof, wherein a flowing phase is prepared from A: a 0.02% phosphoric acid solution and B: a 0.02% phosphoric acid solution-acetonitrile (40: 60), and an elution mode is gradient elution. The method is applied to quality research on raw materials and preparations of the R-lipoic acid or tromethamine salts thereof.

Description

technical field [0001] The invention relates to the field of medicinal chemistry and analysis, in particular to an impurity compound of D-lipoic acid or its tromethamine salt, a preparation method thereof, and an analysis and detection method for related substances of D-lipoic acid or its tromethamine salt. Background technique [0002] α-lipoic acid (α-Lipoic acid, structural formula is as follows), the chemical name is 1,2-dithiolane-3-pentanoic acid, the English name is l,2-Dithiolane-3-Pentanoic acid, which has excellent antioxidant effect , known as the universal antioxidant. Lipoic acid is widely used clinically, and can be used to treat diseases such as liver dysfunction, subacute necrotic encephalopathy, neurological diseases, radiation injuries, and heavy metal poisoning such as arsenic, cadmium, and mercury. [0003] [0004] With the in-depth study of the pharmacology and pharmacodynamics of α-lipoic acid, it is found that the two enantiomers of lipoic acid sh...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D339/04G01N30/02
CPCC07D339/04G01N30/02
Inventor 陈庆财陈祥峰范昌俊范丽芳陈伟刘文杰
Owner JIANGSU AOSAIKANG PHARMA CO LTD
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