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Nucleoside prodrug and application thereof

A kind of use and pharmaceutical technology, applied in the field of medicine, can solve the problems of complex contact environment, etc., and achieve the effect of superior performance, good oral bioavailability, and high plasma drug exposure

Pending Publication Date: 2022-02-01
RISEN SUZHOU PHARMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the applicant found in the study that the prodrug of GS-441524 that can be used orally is rarely reported, and the oral drug that can be used to treat cats is even less
Compared with injection and other implementation methods, oral medicine has the advantages of convenient administration and pain relief, but because oral medicine is absorbed through the digestive tract, the environment it comes into contact with is more complicated

Method used

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  • Nucleoside prodrug and application thereof
  • Nucleoside prodrug and application thereof
  • Nucleoside prodrug and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0088] The present invention will be more readily understood by reference to the following examples, which are presented for illustration and should not be construed as limiting the scope of the invention in any way.

[0089] Unless otherwise defined or clearly dictated by context, all technical and scientific terms used in this application have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. It will be understood that any methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present invention. Unless otherwise stated, the materials and apparatus used in this application were all routinely obtained commercially.

preparation example

[0091] Synthesis of compound 1

[0092]

[0093] Compound 1-1 (4g, 13.7mmol, 1eq) was dispersed in acetone (80mL), and 2,2-dimethoxypropane (7.15g, 68.7mmol, 5eq) and p-toluenesulfonic acid hydrate (2.87g, 15.1 mmol, 1.1 eq). The mixture was stirred overnight at room temperature, then most of the solvent was spun off. The pH of the residue was adjusted to neutral with aqueous sodium bicarbonate, and the mixture was extracted with dichloromethane. The organic phase was dried and spin-dried, and the residue was subjected to silica gel column chromatography (MeOH / DCM=0%-7%) to obtain compound 1-2 (4.41 g, yield 95%).

[0094]Compound 1-2 (300mg, 0.9mmol, 1eq) was dispersed in dichloromethane (20mL), followed by adding isovaleric acid (101.7mg, 0.99mmol, 1.1eq), DMAP (5.5mg, 0.045mmol, 0.05eq) and DCC (224.2 mg, 1.09 mmol, 1.1 eq). The mixture was stirred overnight at room temperature, then filtered. After the filtrate was spin-dried, the residue was subjected to silica ge...

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PUM

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Abstract

The invention relates to a nucleoside prodrug capable of being orally taken for treating mammalian virus infection, and especially relates to a compound shown as a formula (I) or pharmaceutically acceptable salt or stereoisomer thereof, or a pharmaceutical composition thereof, and application of the compound or the composition in preparation of drugs for treating, inhibiting or preventing diseases caused by virus infection.

Description

technical field [0001] The invention relates to the field of medicine, in particular to the use of a nucleoside prodrug or a composition thereof in treating diseases caused by virus infection in humans, cats or other mammals. Background technique [0002] Among the acute infectious diseases, most of them are viral infectious diseases, which have the characteristics of high morbidity and high mortality. Viruses are a class of pathogenic microorganisms that are extremely small, lack independent metabolic capabilities, and exist in a parasitic manner. There are many kinds of viruses. At present, many viruses with high infectivity and pathogenicity to humans have been discovered. These viruses often cause outbreaks of local or even global infectious diseases and are extremely harmful to human society, such as influenza virus , respiratory syncytial virus (RSV), parainfluenza virus, atypical pneumonia (SARS) virus, Middle East respiratory syndrome (MERS) virus, Ebola virus, etc....

Claims

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Application Information

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IPC IPC(8): C07D487/04A61K31/53A61P31/12A61P31/14A61P31/16A61P31/20
CPCC07D487/04A61P31/12A61P31/14A61P31/16A61P31/20Y02A50/30
Inventor 吕佳声吉祥贺小林杜显超孔宪起陈大为
Owner RISEN SUZHOU PHARMA TECH CO LTD