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Polycyclic carbamoyl pyridone analogue and preparation method and application thereof

A technology of polycyclic carbamoyl pyridone and cyclic carbamoyl pyridone, which is applied in the field of medicinal chemistry, can solve the problems of poor patient compliance, slow onset time and the like, achieves good functional group tolerance, the method is simple to operate, and the process Economical effect

Active Publication Date: 2021-04-20
CHONGQING MEDICAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Drugs such as oseltamivir, zanamivir, amantadine and rimantadine are currently widely used anti-influenza virus drugs in clinical practice. However, these drugs have a slow onset time and poor patient compliance

Method used

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  • Polycyclic carbamoyl pyridone analogue and preparation method and application thereof
  • Polycyclic carbamoyl pyridone analogue and preparation method and application thereof
  • Polycyclic carbamoyl pyridone analogue and preparation method and application thereof

Examples

Experimental program
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Embodiment 1

[0033] Add the compound of formula I, chloroacetaldehyde and 1,4-dioxane into a dry and clean reaction flask, stir and raise the temperature to 100°C for 5 hours, then add sodium bicarbonate to continue the reaction for 3 hours, and monitor the reaction by TLC. Cool to room temperature, add water / ethyl acetate to extract 3 times, combine the organic phases, add saturated brine to wash, collect the organic phases, dry over anhydrous sodium sulfate, filter, and concentrate under reduced pressure, the residue is purified to obtain the target product.

[0034] In an initial experiment, the inventors performed the cyclization of 2-amino-N-(2-hydroxyethyl)benzamide with chloroacetaldehyde to synthesize 3,4,11,11a-tetrahydro-[1,4]oxazine The reaction conditions of [3,4-b]quinazolin-6(1H)-one were explored, and the results are listed in Table 1. The first reaction condition tried was NaHCO 3 (1.2 equivalents) as a catalyst, in 1,4-dioxane as a solvent at 100 ° C for 8 hours. Reassur...

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Abstract

The invention provides a polycyclic carbamoyl pyridone analogue which is used as a polycyclic carbamoyl pyridone analogue and can be used as a medicine raw material or an intermediate for synthesizing a novel anti-influenza virus medicine. The polycyclic carbamoyl pyridone analogue is obtained by cyclization of the o-amino amide derivative and chloroacetaldehyde under the action of alkali without any other catalyst or additive, harsh reaction conditions are not needed, and the method is simple to operate and suitable for industrial production. The invention also discloses application of the polycyclic carbamoyl pyridone analogue in serving as an impurity reference substance of baloxavir dipivoxil analogue drugs.

Description

technical field [0001] The invention relates to a polycyclic carbamoyl pyridone, in particular to a polycyclic carbamoyl pyridone analogue and its preparation method and use, belonging to the technical field of medicinal chemistry. Background technique [0002] Influenza is an acute respiratory infectious disease caused by influenza virus. It has the characteristics of wide prevalence, strong infectivity, and high incidence. At present, vaccination and drug treatment are the main measures to deal with influenza virus infection. However, vaccination is difficult to effectively immunize high-risk groups such as the elderly and children, and at the same time cannot provide extensive and durable immune protection for the body; in addition, the continuous evolution of influenza virus strains and the emergence of new virus strains have greatly reduced the effectiveness of vaccines. sex. Therefore, drug treatment is still the best means of controlling the spread of influenza viru...

Claims

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Application Information

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IPC IPC(8): C07D498/04C07D498/14
Inventor 袁建勇王强胡雪原吴惠丽匡秋林
Owner CHONGQING MEDICAL UNIVERSITY
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