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Peramivir impurity F as well as preparation method and application thereof

A technology of impurities and acidic solvents, applied in the field of medicinal chemistry, can solve the problems related to reports of no impurities and achieve the effect of ensuring drug safety

Inactive Publication Date: 2021-04-30
天津应天成科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] During the impurity research of peramivir, the impurity F of peramivir was found, and there was no relevant report about this impurity in other literatures

Method used

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  • Peramivir impurity F as well as preparation method and application thereof
  • Peramivir impurity F as well as preparation method and application thereof
  • Peramivir impurity F as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Add 5 g of peramivir to 150 mL of 6 mol / L hydrochloric acid, raise the temperature to 50-60°C and stir for 4 hours, stop stirring to obtain a reaction solution; concentrate under reduced pressure at 50-60°C until there is no fraction. (yield 78.1%, HPLC purity: 95.75%, see figure 1 ; [M+H]+ peak 287.39, see figure 2 ; 1 H-NMR see image 3 ).

[0036] figure 1 The specific situation of the HPLC collection of illustrative plates is as follows table 2:

[0037] Table 2

[0038] name Peak time (min) Peak area Area percentage Peak height Peak Height Percentage Impurity F 4.673 9960110 95.75 1045616 96.14 unknown 5.920 211079 2.03 22324 2.05 unknown 16.850 93319 0.90 8358 0.77 unknown 18.517 137713 1.32 11287 1.04

[0039] image 3 1 H-NMR analysis is as follows:

[0040] 1 H-NMR (500MHz,D 2 O)δ(ppm) 0.75~0.79(s,6H,-CH3), 1.12~1.58(m,4H,-CH), 1.60~1.58(m,1H,-CH), 1.89~1.93(m,2H, -CH2), 2.51~2.55(m,1H...

Embodiment 2

[0042] Add 5 g of peramivir to 150 mL of 4 mol / L hydrochloric acid, raise the temperature to 50-60°C and stir for 4 hours, stop stirring to obtain a reaction solution; concentrate under reduced pressure at 50-60°C until there is no fraction. (Yield 70.1%, HPLC purity: 95.8%).

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Abstract

The invention provides a peramivir impurity F. The structural formula of the peramivir impurity F is shown as a formula (I). The preparation method of the peramivir impurity F comprises the following steps that A, peramivir reacts under the condition of an acid solvent, the weight-volume ratio of peramivir to the acid solvent is 1: 10-1: 100, and the unit is Kg: L; wherein the reaction temperature is 20-100 DEG C, the reaction time is 2-10 hours, and a reaction solution is obtained; and B,the reaction solution is concentrated under reduced pressure to obtain the peramivir impurity F; through research on peramivir impurities, a brand-new peramivir impurity F is obtained, the peramivir impurity F is hydrochloride, after mass spectrometric determination and hydrogen chloride deduction of the peramivir impurity F, a [M+1] peak 287.39 exists in MS, the corresponding molecular weight is 286.39, the purity reaches 95.0% or above, the peramivir impurity F can be used as a reference substance for impurity research for peramivir content determination, and the medication safety of peramivir can be effectively guaranteed.

Description

technical field [0001] The present invention relates to but not limited to the field of medicinal chemistry, in particular to a peramivir impurity F and its preparation method and application. Background technique [0002] Peramivir, chemical name: (1S,2S,3S,4R)-3-[(S)-1-Acetamido-2-ethylbutyl]-4-guanidino-2-hydroxycyclopentane -1-Carboxylic acid; a neuraminidase inhibitor targeting the surface glycoprotein neuraminidase of influenza virus, the first neuraminidase inhibitor approved as a single intravenous injection . Peramivir is suitable for patients aged 18 years and above with acute uncomplicated influenza and only two days of flu symptoms. The existing clinical trial data proves that it is effective against influenza A and influenza B. [0003] According to the internationally recognized drug registration, it must meet the requirements of the International Conference on Harmonization of Human Drug Registration (ICH) and the European Pharmacopoeia, which requires stric...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C279/16C07C277/08G01N1/28
CPCC07C279/16C07C277/08G01N1/28C07B2200/07C07C2601/08G01N2001/2893
Inventor 王志国杨虎斌李学东苏明明张帝
Owner 天津应天成科技有限公司
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