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Peramivir impurity M as well as preparation method and application thereof
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A technology of impurities and sodium hydroxide, which is applied in the preparation of urea derivatives, chemical instruments and methods, and the preparation of test samples, etc., can solve the problems of no impurity-related reports and achieve the effect of ensuring drug safety
Pending Publication Date: 2021-01-26
天津应天成科技有限公司
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[0006] During the impurity research of peramivir, the impurity M of peramivir was found, and there was no relevant report about this impurity in other literatures
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Embodiment 1
[0032] Add 5 g of peramivir to 150 mL of 1 mol / L sodiumhydroxide solution, raise the temperature to 70°C and stir for 4 hours, stop stirring to obtain a reaction solution; add 250 mL of 1 mol / L hydrochloric acid to adjust the pH to about 3-4, a large amount of solids are precipitated, pump Filter to obtain peramivir impurity M. (Yield 78.1%, HPLC purity: 99.856%, see figure 1 ; [M+H]+ peak 330.47, see figure 2 ; HNMR See image 3 ).
[0034] figure 1 The specific situation of the HPLC collection of illustrative plates is as table 2:
[0035] Table 2
[0036] name Peak time (min) area content(%) Peak width (...
Embodiment 2
[0038] Add 5 g of peramivir to 150 mL of 2 mol / L sodiumhydroxide solution, raise the temperature to 80°C and stir for 6 hours, stop stirring to obtain a reaction solution; add 400 mL of 1 mol / L hydrochloric acid to adjust the pH to about 3-4, a large amount of solids are precipitated, pump Filter to obtain peramivir impurity M. (Yield 70.1%, HPLC purity: 94.8%).
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Abstract
The invention provides a peramivirimpurity M. The structural formula of the peramivirimpurity M is shown as a formula (I). The preparation method of the peramivirimpurity M comprises the followingsteps: A, reacting peramivir in an alkaline solution, and conducting stirring at the reaction temperature of 10-100 DEG C for 2-10 hours to obtain a reaction solution; and B, adjusting the pH value ofthe reaction solution to 3-4 by using an acid, separating out solids, and carrying out suction filtration to obtain the peramivir impurity M. By researching the peramivir impurity, the brand-new peramivir impurity M is obtained, the corresponding molecular weight of the peramivir impurity M is 329.40 and the purity of the peramivir impurity M reaches 95.0% or above through mass spectrometric determination, and the peramivir impurity M can be used as a reference substance for impurity research for peramivir content determination and can effectively guarantee the medication safety of peramivir.
Description
technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a peramivir impurity M 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 glycoproteinneuraminidase 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 strict control of im...
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