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Method for separating and detecting 1, 2-propylene glycol enantiomer by gas chromatography

A technology of enantiomers and propylene glycol, applied in the field of analysis and detection, can solve the problems of inability to accurately quantify trace impurities, insufficient separation ability, poor chromatographic peak shape, etc., to solve the problem of drug quality control, ensure effectiveness and safety , the effect of less interference factors

Pending Publication Date: 2021-12-28
BEIJING SIHUAN PHARMA +3
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method still has defects such as poor chromatographic peak shape of derivative products, insufficient separation ability and chromatographic peak tailing.
[0006] The present invention provides a more rapid, efficient and environmentally friendly pre-column derivatization gas chromatographic separation for enantiomer impurities of (S)-1,2-propanediol (S)-1,2-propanediol The determination method effectively solves the technical defects of peak tailing in the chromatographic separation process of 1,2-propanediol and the inability to accurately quantify its trace impurities

Method used

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  • Method for separating and detecting 1, 2-propylene glycol enantiomer by gas chromatography
  • Method for separating and detecting 1, 2-propylene glycol enantiomer by gas chromatography
  • Method for separating and detecting 1, 2-propylene glycol enantiomer by gas chromatography

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Embodiment 1 detection method effectiveness verification

[0052] Sample preparation:

[0053] Weigh 200mg of (S)-1,2-propanediol, place it in a 20ml measuring bottle, dilute to volume with absolute ethanol, shake well, and use it as the test solution 1.

[0054] Weigh 50mg of (R)-1,2-propanediol, place it in a 10ml measuring bottle, dilute to the mark with absolute ethanol, shake well, measure 1ml and place it in a 10ml measuring bottle, use Dilute to volume with water and ethanol, shake well, and use as test solution 2.

[0055] Weigh 40 mg of (S)-1,2-propanediol, weigh it accurately, place it in a 10ml Nessler colorimetric tube or a 10ml centrifuge tube, add 200 μl of acetic anhydride and 10 μl of methanesulfonic acid, vortex and mix for 10 minutes, add Saturated sodium carbonate solution 3ml, after vortex mixing for 30 seconds, add 5ml of n-heptane for extraction, shake vigorously to make full contact, static layering, take the supernatant as the test solution 3. ...

Embodiment 2-5

[0064] Example 2-5 Derivatization reaction condition optimization

[0065] Take 40mg of (S)-1,2-propanediol, put it in a 10ml Nessler colorimetric tube or a 10ml centrifuge tube, add the derivatizing agent acetic anhydride and catalyst methanesulfonic acid respectively according to Table 1, vortex and mix for a certain period of time, Add 3ml of quenching agent (water, saturated sodium chloride solution or saturated sodium carbonate solution), vortex and mix for 30 seconds, add 5ml of n-heptane for extraction, shake vigorously to make full contact, static layering, take the supernatant as The test solution.

[0066] Get above-mentioned need testing solution, carry out gas chromatograph analysis according to the chromatographic condition of need testing solution 3 or 4 of embodiment 1. The results are shown in Table 1.

[0067] Table 1

[0068]

[0069]

Embodiment 6

[0070] Embodiment 6 detection method specific verification

[0071] Sample preparation:

[0072] 1. Take about 40mg each of (S)-1,2-propanediol and (R)-1,2-propanediol, put them in a 10ml Nessler colorimetric tube or a 10ml centrifuge tube, add 200μl of acetic anhydride and 10μl of methanesulfonic acid respectively , vortex and mix for 10 minutes, add 3ml of saturated sodium carbonate solution, vortex and mix for 30 seconds, add 5ml of n-heptane for extraction, static layering, take the supernatant, respectively as solution (1) and solution (2), according to The volume ratio is about 100:1. Measure the solution (1): solution (2) and mix them evenly. The resulting mixed solution is used as the resolution solution.

[0073] 2. Take solution (1) as (S)-1,2-propanediol derivative solution positioning solution; take solution (2) and dilute 100 times as (R)-1,2-propanediol derivative solution positioning solution.

[0074] 3. Take 10ml blank Nessler colorimetric tube or 10ml blank...

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Abstract

The invention provides a rapid, efficient and environment-friendly pre-column derivatization gas chromatography separation and determination method for enantiomer impurities of (S)-1, 2-propylene glycol of alcohol compounds (such as dapagliflozin synthesis raw materials), and effectively overcomes the technical defects of peak trailing in the chromatographic separation process of 1, 2-propylene glycol and incapability of accurately quantifying trace impurities in the 1, 2-propylene glycol.

Description

technical field [0001] The invention belongs to the technical field of analysis and detection, and in particular relates to a method for separating and detecting (S)-1,2-propanediol enantiomeric impurities in dapagliflozin synthesis raw materials. Background technique [0002] Darpagliflozin (Farxiga), not only can be used as a single drug or adjuvant therapy to improve blood sugar levels in patients with type 2 diabetes, but also has the additional benefits of losing weight and lowering blood pressure. In addition, it is the first to be approved for adjuvant treatment of type 1 diabetes The sodium-dependent glucose transporter (SGLT) inhibitor, jointly developed by AstraZeneca and Bristol-Myers Squibb, was approved by the European Medicines Agency (EMA) and the US Food and Drug Administration (FDA) in 2012 and 2014, respectively. The molecular formula of its main component Dapagliflozin is C 21 h 25 ClO 6 , its chemical name is: ((1S)-1,5-anhydro-1-C-[4-chloro-3-[(4-etho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G01N30/02G01N30/06
CPCG01N30/02G01N30/06G01N2030/067
Inventor 郑金敏韩冰雪王振军刘美霞邓声菊徐艳君王田园
Owner BEIJING SIHUAN PHARMA
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