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Neuraminidase inhibitor containing hydrazide structure fragments and medical application thereof

An acetamido, pharmaceutical technology, applied in the field of medicinal chemistry, can solve problems such as central nervous system toxicity and side effects

Pending Publication Date: 2021-02-26
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Nowadays, there are two main anti-influenza drugs, M2 protein inhibitors and neuraminidase inhibitors. M2 protein inhibitors mainly include amantadine hydrochloride and rimantadine hydrochloride. After oral absorption, amantadine hydrochloride can penetrate blood Brain barrier, causing toxic and side effects in the central nervous system, and easy to develop drug resistance

Method used

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  • Neuraminidase inhibitor containing hydrazide structure fragments and medical application thereof
  • Neuraminidase inhibitor containing hydrazide structure fragments and medical application thereof
  • Neuraminidase inhibitor containing hydrazide structure fragments and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] ((3R, 4R, 5S)-4-acetamido-5-(1-(imidazole)-aminocarboxamido)-3-(1-ethylpropoxy)-1-cyclohexene-1 - Ethyl carboxylate (II)

[0039] Add 500 mg (1.60 mmol) of oseltamivir to a 100 mL round bottom flask, add 30 mL of dichloromethane to dissolve, add 260 mg (1.60 mmol) of carbonyldiimidazole in batches under ice-water bath, and stir. After the reaction, the organic phase was washed with saturated ammonium chloride solution and saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated to obtain 530 mg of crude product, which was further purified and put into the next reaction.

Embodiment 2

[0041] (3R,4R,5S)-4-Acetamido-5-(hydrazinecarboxamido)-3-(pentane-3-oxyl)cyclohex-1-ene-1-carboxylic acid ethyl ester (III)

[0042] Add compound 500mg (1.23mmol) (3R, 4R, 5S)-4-acetamido-5-(1-(imidazole)-aminoformamido)-3-(1-ethyl) in a 100mL round bottom flask Propoxy)-1-cyclohexene-1-carboxylate ethyl ester (II), add 1.92g of anhydrous sodium sulfate (13.52mmol), add 30mL of anhydrous chloroform, 132μL of hydrazine hydrate (2.71mmol), 255μL of three Ethylamine (1.85mmol) was reacted at room temperature for 0.5h, then heated to 35°C for 12h. After the reaction was completed, anhydrous sodium sulfate was removed by filtration, and chloroform was evaporated from the filtrate under reduced pressure to obtain a crude product, which was then slurried by adding 20 mL of acetonitrile to obtain 340 mg of a white solid with a yield of 80.0%.

Embodiment 3

[0044] (3R, 4R, 5S)-4-Acetamido-5-(2-methylenehydrazine-1-carboxamido)-3-(pentane-3-oxyl)cyclohex-1-ene-1- Ethyl carboxylate (IV-1)

[0045] Add compound 200mg (0.58mmol) (3R, 4R, 5S)-4-acetylamino-5-(hydrazine carboxamido)-3-(pentane-3-oxyl group) cyclohexyl-1 in 50mL round bottom flask -Ethyl-ene-1-carboxylate (III), sequentially add 10 mL of methanol, add 25.86 μL of formaldehyde (0.70 mmol), and stir at room temperature for 8 h. After the reaction, the methanol was distilled off under reduced pressure and purified by column chromatography to obtain 201 mg of a white solid with a yield of 90.0%.

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Abstract

The invention relates to the field of medicinal chemistry, and particularly relates to a neuraminidase inhibitor oseltamivir derivative containing hydrazide structure fragments as well as a preparation method and medical application of the neuraminidase inhibitor oseltamivir derivative. Specifically, the invention relates to application of the neuraminidase inhibitor oseltamivir derivative containing the hydrazide structure fragments in preparation of drugs for treating infectious diseases caused by viruses. The derivative and the pharmaceutically acceptable salt or isomer thereof are represented by a general formula (I) in the description, wherein R is described in the claims and the description.

Description

technical field [0001] The present invention relates to the field of medicinal chemistry, in particular to a class of neuraminidase inhibitor oseltamivir derivatives containing a hydrazide structural fragment, its preparation method and its medical use, and in particular to the neuron containing a hydrazide structural fragment. Application of the oseltamivir derivatives of the amino acid enzyme inhibitor in the preparation of drugs for treating infectious diseases caused by viruses. Background technique [0002] Influenza (abbreviated as influenza) is an acute respiratory infection caused by influenza virus. Among them, influenza A is highly transmissible and has a high morbidity and mortality rate, which is likely to cause a pandemic or a large outbreak. Today, influenza is still a disease that threatens human health. [0003] Nowadays, there are two main anti-influenza drugs, M2 protein inhibitors and neuraminidase inhibitors. M2 protein inhibitors mainly include amantadi...

Claims

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Application Information

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IPC IPC(8): C07C281/06C07D309/14C07D233/56C07C281/10C07C281/14C07C281/12A61K31/196A61K31/351A61P31/16
CPCC07C281/06C07D309/14C07D233/56C07C281/10C07C281/14C07C281/12A61P31/16C07C2601/16C07C2601/02
Inventor 田永寿赵红倩王矿磊
Owner SHENYANG PHARMA UNIVERSITY
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