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Method for detecting enantiomer content in (s,s)-2,8-diazabicyclo[4,3,0]nonane

A technology of diazabicyclo and enantiomer, which is applied in the field of drug detection, can solve the problems of poor repeatability, precision and accuracy, inaccurate quantitative determination of isomer content, low recovery rate, etc., to achieve guaranteed Production quality, complete derivatization reaction, fast response effect

Active Publication Date: 2021-06-08
SHANDONG QIDU PHARMA
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Problems solved by technology

[0007] At present, Chinese patent CN104133019A discloses a method for detecting the enantiomers of diazabicyclononane, using o-fluoronitrobenzene for pre-column derivatization detection of (S,S)-2,8-diazabicyclo[ 4,3,0] nonane enantiomers, however, its repeatability, precision and accuracy are relatively poor
[0008] Literature (Oriental Journal of Chemistry.31(2015) 2207-2212) reported that (S,S)-2,8-diazabicyclo[4,3,0]nonane was derivatized with NBD-Cl and determined by HPLC isomer method, but the recovery rate of this method is low, and the isomer content cannot be determined accurately and quantitatively

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  • Method for detecting enantiomer content in (s,s)-2,8-diazabicyclo[4,3,0]nonane
  • Method for detecting enantiomer content in (s,s)-2,8-diazabicyclo[4,3,0]nonane
  • Method for detecting enantiomer content in (s,s)-2,8-diazabicyclo[4,3,0]nonane

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Experimental program
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Effect test

Embodiment 1

[0054] Detection method:

[0055] 1. Chromatographic conditions:

[0056] Chromatographic column: CHIRALPAK AD-H chiral column, 250×4.6mm, particle size 5μm; detection wavelength 246nm; mobile phase: n-hexane-absolute ethanol (volume ratio 55:45); column temperature: 30°C; flow rate: 1.0 ml / min; running time: 25min; injection volume: 10μl;

[0057] 2. Solution preparation

[0058] 2.1 Preparation of (R,R)-2,8-diazabicyclo[4,3,0]nonane derivative solution:

[0059]Accurately weigh 50mg of (R,R)-2,8-diazabicyclo[4,3,0]nonane, put it into a reaction bottle, add 20ml of solvent and a derivatization reagent of 1.2 times the amount of the substance, 20-30 °C and stirred for 0.5 hours to obtain the corresponding derivative solution;

[0060] Precisely measure 0.15ml of (R,R)-2,8-diazabicyclo[4,3,0]nonane derivative solution, put it in a 25ml volumetric flask, add ethanol to dilute to the mark, shake well, and you get it;

[0061] 2.2 Preparation of system suitability solution: ...

Embodiment 2

[0073] System suitability for the determination of enantiomer content in (S,S)-2,8-diazabicyclo[4,3,0]nonane using 1-dimethylaminonaphthalene-5-sulfonyl chloride as derivatization reagent experiment:

[0074] 1. Derivatization reaction of (S,S)-2,8-diazabicyclo[4,3,0]nonane

[0075] Weigh 1.0g of (S,S)-2,8-diazabicyclo[4,3,0]nonane into a reaction flask, add 20ml of dichloromethane and 2.14g (1.2 times the amount of the substance) of 1- Dimethylaminonaphthalene-5-sulfonyl chloride, stirred at 20-30°C for 0.5 hours to obtain a derivative solution;

[0076] Precisely measure 0.15ml of (S,S)-2,8-diazabicyclo[4,3,0]nonane derivative solution, put it in a 25ml volumetric flask, add absolute ethanol to dilute to the mark, and use it as the test sample solution;

[0077] 2. Derivatization reaction of (R,R)-2,8-diazabicyclo[4,3,0]nonane

[0078] Weigh 50mg of (R,R)-2,8-diazabicyclo[4,3,0]nonane into a reaction flask, add 20ml of dichloromethane and 1.34g of 1-dimethylaminonaphthal...

Embodiment 3

[0088] Derivatization Reagent Using 1-Dimethylaminonaphthalene-5-sulfonyl Chloride as a Derivatization Reagent for Enantiomer Content Accuracy in (S,S)-2,8-diazabicyclo[4,3,0]nonane .

[0089] Accuracy is obtained by adding quantitative limit, index 80%, 100%, and 120% of three isomers with different concentrations to the tested product. By adding a known amount of isomers, measure the content of the isomers in the added sample, and then deduct the original isomer content in the sample, the ratio (recovery rate) between the measured result and the actual amount added is expressed in percentage ( %) expression, the recovery rate is required to be between 90% and 108%, to prove that the method has good accuracy.

[0090] The test results are shown in Table 3.

[0091] Table 3 Recovery test results

[0092]

[0093] Conclusion: Under the 4 concentrations, the recoveries of isomers are between 96.30% and 100.11%, and the average recovery is 98.13%, which meets the requiremen...

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Abstract

The invention belongs to the technical field of drug detection, and in particular relates to a method for detecting the content of enantiomers in (S,S)-2,8-diazabicyclo[4,3,0]nonane. The present invention uses 1-dimethylaminonaphthalene-5-sulfonyl chloride as a derivatization reagent to derivatize (S,S)-2,8-diazabicyclo[4,3,0]nonane, and then uses HPLC to perform derivatization Detection, the enantiomer content was calculated by the area normalization method. The invention detects the content of enantiomers in (S,S)‑2,8‑diazabicyclo[4,3,0]nonane, and has low cost, rapid reaction, simple operation, complete derivatization reaction, and relatively low cost. The derivation method reported in other literature has higher accuracy, which is important for controlling the quality of (S,S)-2,8-diazabicyclo[4,3,0]nonane and ensuring the production quality of moxifloxacin hydrochloride significance.

Description

technical field [0001] The invention belongs to the technical field of drug detection, and in particular relates to a method for detecting the content of enantiomers in (S,S)-2,8-diazabicyclo[4,3,0]nonane. Background technique [0002] Moxifloxacin hydrochloride (Moxifloxacin hydrochloride) belongs to the fourth-generation fluoroquinolone chemically synthesized antibiotic drug, which was launched by Bayer Company of Germany in 1999. Since it was launched on the market, it has been widely used clinically due to its broad antibacterial spectrum, strong antibacterial power, good curative effect, small side effects, and no cross-resistance with other antibacterial drugs. As a new type of quinolones, the azabicyclic structure on the c-7 side chain strengthens the antibacterial effect on Gram-positive bacteria. [0003] In the production process of moxifloxacin hydrochloride, (S,S)-2,8-diazabicyclo[4,3,0]nonane is widely used as its side chain azabicyclo intermediate, so its qual...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): G01N30/02G01N30/06
CPCG01N30/02G01N30/06G01N2030/067
Inventor 李宗涛张涛崔良峰任传杰黄翠苹周广涛康乐刘海萍王朋翟民郑亮
Owner SHANDONG QIDU PHARMA
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