Mono- or di-substituted indole derivatives as dengue viral replication inhibitors

Inventors: Bart Rudolf Romanie Kesteleyn (Berlare, BE); Jean-François Bonfanti (Ande, FR); Tim Hugo Maria Jonckers (Heist-op-den-Berg, BE); Pierre Jean-Marie Bernard Raboisson (Rosieres, BE); Dorothée Alice Marie-Eve Bardiot (Heverlee, BE); Arnaud Didier M Marchand (Bierbeek, BE)

Assignees: Janssen Pharmaceuticals, Inc.; Katholieke Universiteit Leuven

A61K31/404 A61P31/14 C07D209/12 Y02A50/385

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Quick Facts

Patent No.: US 10,786,484
App. No.: 15/759,844
Granted: Sep 29, 2020
Kind: B2

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Abstract

The present invention concerns mono- or di-substituted indole compounds, methods to prevent or treat dengue viral infections by using said compounds and also relates to said compounds for use as a medicine, more preferably for use as a medicine to treat or prevent dengue viral infections. The present invention furthermore relates to pharmaceutical compositions or combination preparations of the compounds, to the compositions or preparations for use as a medicine, more preferably for the prevention or treatment of dengue viral infections. The invention also relates to processes for preparation of the compounds.

Claims (26)

1. A compound of formula (I)

or a stereo-isomeric form, a pharmaceutically acceptable salt, solvate or polymorph thereof comprising a mono- or di-substituted indole group; wherein said formula (I) is selected from the group consisting of:

R 1 is H, R 2 is F or Cl and R 3 is H or CH 3 ;

R 1 is F, R 2 is F and R 3 is H;

R 1 is CH 3 , R 2 is OCH 3 and R 3 is H;

R 1 is CH 3 , R 2 is F and R 3 is H;

R 1 is CH 3 , R 2 is H and R 3 is F;

R 1 is Cl, R 2 is H and R 3 is CH 3 ;

R 1 is OCF 3 , R 2 is H or OCH 3 and R 3 is H; and

R 1 is OCF 3 , R 2 is H and R 3 is CH 3 .

2. The compound of claim 1 wherein said formula (I) is selected from the group:

3. A pharmaceutical composition comprising a compound of claim 1 and one or more pharmaceutically acceptable excipients, diluents or carriers.

4. A method of treating a dengue infection comprising administering an effective amount of the pharmaceutical composition of claim 3 to a patient in need thereof.

5. The method of claim 4 , wherein said method further comprises administering another antiviral agent to said patient.

6. The compound of claim 2 , which is:

7. The compound of claim 2 , which is:

8. The compound of claim 2 , which is:

9. The compound of claim 2 , which is:

10. The compound of claim 2 , which is:

11. The compound of claim 2 , which is:

12. The compound of claim 2 , which is:

13. The compound of claim 2 , which is:

14. The compound of claim 2 , which is:

15. The compound of claim 2 , which is:

16. The compound of claim 2 , which is:

17. The compound of claim 2 , which is:

Assignments (10)