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Polycyclic compound and pharmaceutical composition and application thereof

A technology for polycyclic compounds and compounds, used in organic chemistry, pharmaceutical formulations, bulk chemical production, etc.

Pending Publication Date: 2021-11-02
SHIJIAZHUANG DISCOVERY MEDICINE TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the overall incidence of adverse reactions is comparable to that of oseltamivir and placebo, which are 25% and 30% respectively, which is generally higher.
And, about 10% of the resistance

Method used

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  • Polycyclic compound and pharmaceutical composition and application thereof
  • Polycyclic compound and pharmaceutical composition and application thereof
  • Polycyclic compound and pharmaceutical composition and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087]

[0088] Synthesis of compound 1b:

[0089] Add 5g of compound 1a, 65mg of p-toluenesulfonic acid, 2.7g of ethylene glycol, and 50ml of benzene into the reaction flask, and heat the system to reflux with a water separator for 24 hours. The system was concentrated to dryness, dichloromethane and water were added, the organic phase was separated, concentrated to dryness and separated by a silica gel column to obtain 3.94g of compound 1b with a yield of 72%, ESI-MS (+): m / z 506.19 [M +H];

[0090] Synthesis of compound 1c:

[0091] Add 3.8g of compound 1b, 30ml of methanol and 0.45g of 10% palladium carbon into the reaction flask, and hydrogenate at room temperature and pressure for 24 hours. After the reaction, the system was filtered with diatomaceous earth; the system was concentrated to dryness under reduced pressure, and purified by silica gel column to obtain 1.9 g of compound 1c, with a yield of 90%, ESI-MS (+): m / z 282.12 [M+H];

Embodiment 2

[0093]

[0094] Synthesis of compound 2b:

[0095]Add 5g of compound 1a, 65mg of p-toluenesulfonic acid, 4.5g of 2-hydroxy-2-methylpropionic acid, and 50ml of benzene into the reaction flask, and heat the system to reflux for 24 hours with a water separator. The system was concentrated to dryness, dichloromethane and water were added, the organic phase was separated, concentrated to dryness and separated by a silica gel column to obtain 4.03g of compound 2b with a yield of 68%, ESI-MS (+): m / z548.22[ M+H];

[0096] Synthesis of compound 2c:

[0097] Add 3.8g of compound 2b, 30ml of methanol and 0.41g of 10% palladium carbon into the reaction flask, and hydrogenate at room temperature and pressure for 24 hours. After the reaction, the system was filtered with diatomaceous earth; the system was concentrated to dryness under reduced pressure, and purified by silica gel column to obtain 2.04g of compound 2c, with a yield of 91%, ESI-MS (+): m / z 324.10 [M+H];

Embodiment 3

[0099]

[0100] Synthesis of compound 3b:

[0101] Add 5g of compound 1a, 65mg of p-toluenesulfonic acid, 3.86g of 2-amino-2-methylpropanol, and 50ml of benzene into the reaction flask, and heat the system to reflux for 24 hours with a water separator. The system was concentrated to dryness, dichloromethane and water were added, the organic phase was separated, concentrated to dryness and separated by a silica gel column to obtain 4.33g of compound 3b, yield 75%, ESI-MS (+): m / z 533.21 [M +H];

[0102] Synthesis of compound 3c:

[0103] Add 3.8g of compound 3b, 30ml of methanol and 0.42g of 10% palladium carbon into the reaction bottle, and hydrogenate at room temperature and pressure for 24 hours. After the reaction, the system was filtered with diatomaceous earth; the system was concentrated to dryness under reduced pressure, and purified by silica gel column to obtain 1.94g of compound 3c, with a yield of 88%, ESI-MS (+): m / z 309.13 [M+H];

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Abstract

The invention discloses a polycyclic compound and a pharmaceutical composition and application thereof. The substituted polycyclic compound is shown as a formula (I). The compound has low toxicity to normal cells, can play a significant anti-influenza virus role in vivo, has high drug safety, and can be developed into anti-influenza virus drugs.

Description

technical field [0001] The present invention relates to but not limited to the technical field of medicinal chemistry, and in particular relates to a polycyclic compound and its pharmaceutical composition and use. Background technique [0002] Influenza virus (Influenza Virus) is divided into three types: Influenza A Virus (IAV), Influenza B Virus (IBV), and Influenza C Virus (ICV). Among them, the surface antigen of influenza A virus is prone to mutation, which is called drift (Drift), to avoid the recognition of the human immune system, and the result of this drift is the cause of influenza outbreaks. Human influenza outbreaks are mainly caused by influenza A virus and influenza B virus infection. Influenza C virus mainly infects humans and other mammals such as pigs and cattle, and usually only causes a small-scale epidemic. [0003] Baloxavir marboxil, commonly known as baloxavir dipivoxil, sold under the brand name Xofluza TM , the first single-dose oral antiviral dru...

Claims

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Application Information

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IPC IPC(8): C07D498/22A61P31/16A61K31/5386
CPCC07D498/22A61P31/16Y02P20/55
Inventor 张哲峰李海德王伟付海舰
Owner SHIJIAZHUANG DISCOVERY MEDICINE TECH CO LTD
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