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Imidazopyridine derivatives as respiratory syncytial virus antiviral agents

A technology of imidazopyridine and derivatives, applied in the field of treating respiratory syncytial virus infection, can solve the problems of needing parenteral administration, limited therapeutic effect, high cost, etc., and achieves excellent bioavailability, high selectivity, and low cardiotoxicity. Effect

Pending Publication Date: 2022-02-08
ANDIKANG (WUXI) BIOLOGICAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

RSV-IG palivizumab (polyclonal and monoclonal antibody immunostimulant) is intended for prophylactic use, both are expensive and require parenteral administration
Ribavirin also has limited therapeutic activity and mutagenic toxicity

Method used

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  • Imidazopyridine derivatives as respiratory syncytial virus antiviral agents
  • Imidazopyridine derivatives as respiratory syncytial virus antiviral agents
  • Imidazopyridine derivatives as respiratory syncytial virus antiviral agents

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] 3-({5-Chloro-1-[3-(methylsulfonyl)propyl]-1H-indol-2-yl}methyl)-1-methyl-1,3-dihydro-2H- imidazo[4,5-c]pyridin-2-one

[0052] The synthetic route is as follows:

[0053]

[0054] Preparation of 3-(methylsulfonyl)propyl-4-toluenesulfonate

[0055] N 2For protection, 50g of 3-(methylthio)propyl-1-ol was dissolved in 300ml of DCM, 94.5g of methanesulfonyl chloride was added, the reaction solution was cooled to 0°C, and then 2.48g of N,N,N',N'- Tetramethyl-1,6-hexanediamine and 57.23 g of triethylamine were stirred and reacted for 3 hr, and the reaction was complete as detected by TLC. The reaction was quenched by adding 120ml of purified water at 10-15°C. Extract, wash with 3N hydrochloric acid solution, and save the DCM layer for later use.

[0056] 376.3g of potassium peroxymonosulfate was dissolved in 1500ml of water, dropped into the DCM organic layer of the previous step, stirred at room temperature, and the reaction was complete as detected by TLC. The organ...

Embodiment 2

[0072] 3-({5-Chloro-1-[3-(methylsulfonyl)propyl]-1H-indol-2-yl}methyl-d 2 )-1-(2,2,2-trifluoroethyl)-1,3-dihydro-2H-imidazo[4,5-c]pyridin-2-one

[0073] The synthetic route is as follows:

[0074]

[0075] Preparation of Intermediate 5

[0076] Add 10g (64.88mmol) 4-methoxy-3-nitropyridine, 16.07g (162.21mmol) 2,2,2-trifluoroethylamine, 40ml absolute ethanol into the reactor, 16.77g (129.76mmol ) DIPEA / 10ml of absolute ethanol was added dropwise to the reaction liquid, stirred, and the temperature was raised to 78°C after the addition, and reacted for 5hr. Cooled to room temperature, added DCM for extraction, the organic layer was washed twice with water, and concentrated under reduced pressure to obtain 9.6g of solid.

[0077] Add 9 g (40.7 mmol) of the solid from the previous step to the reactor, add 180 ml of 95% ethanol, 9.1 g (162.79 mmol) of reduced iron powder, 7.62 g (142.44 mmol) of ammonium chloride / 80 ml of water, and adjust the pH to 5 with 1N HCl -6, reflux ...

Embodiment 3

[0087] 3-({5-chloro-1-[3-(methylsulfonyl)propyl]-1H-indol-2-yl}methyl)-1-(methyl-d 3 )-1,3-dihydro-2H-imidazo[4,5-c]pyridin-2-one

[0088] The synthetic route is as follows:

[0089]

[0090] Preparation of Intermediate 8

[0091] 5g (32.44mmol) 4-methoxy-3-nitropyridine, 5.49g (81.1mmol) methylamine-d 3 Hydrochloride and 20ml of absolute ethanol were added to the pressure reactor, 18.89g (145.99mmol) DIPEA / 5ml of absolute ethanol was added dropwise to the reaction solution, stirred, the temperature was raised to 78°C after the addition, and the reaction was carried out for 5hr. Cooled to room temperature, DCM was added for extraction, the DCM layer was washed twice with water, and concentrated under reduced pressure to obtain 3.2 g of solid.

[0092] Add 3 g (19.59 mmol) of the solid from the previous step into the reactor, add 60 ml of 95% ethanol, 4.37 g (68.56 mmol) of reduced iron powder, 3.69 g (68.56 mmol) of ammonium chloride / 20 ml of water, and adjust the pH to 5 ...

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PUM

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Abstract

The present invention provides a substituted imidazopyridine derivative, a prodrug, an oxide, a salt, a metal complex or a stereochemical isomer having the structure of Formula I and a pharmaceutical composition containing the same, and a method of using the composition for the treatment of RSV viral infections. The compound provided by the invention has the advantages of high metabolic stability, high solubility, high oral absorbability, good bioavailability, fast detoxification, good antiviral activity, high therapeutic index, low cardiotoxicity and the like.

Description

technical field [0001] The present invention provides a substituted imidazopyridine derivative, prodrug, oxide, salt, metal complex or stereochemical isomer and a pharmaceutical composition containing it, and using the composition for the treatment of respiratory syndrome method of viral infection. [0002] technical background [0003] Human RSV or Respiratory Syncytial Virus is a large RNA virus, which together with bovine RSV virus is a member of the family Pneumoviridae, genus Orthopneumovirus. Respiratory syncytial virus (RSV), a paramyxovirus genus of the Paramyxoviridae family, is a single-stranded RNA virus responsible for many epidemic human and animal diseases. Almost all children will develop RSV infection by their second birthday. RSV is a leading cause of lower respiratory tract infections in infancy and childhood, and 0.5% to 2% of those infected require hospitalization. In old age, susceptibility rises again, and RSV has been implicated in large outbreaks of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04A61K31/437A61P31/14A61P31/16A61P11/00A61P11/14A61P11/10A61P29/00
CPCC07D471/04A61P31/14A61P31/16A61P11/00A61P11/14A61P11/10A61P29/00
Inventor 朱孝云蒋维平
Owner ANDIKANG (WUXI) BIOLOGICAL TECH CO LTD
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