IP Library Granted Patent US 9,944,598
Granted Patent B2
US 9,944,598 · App. 15/515,574 · Granted Apr 17, 2018

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
C07D209/14A61K31/404
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Quick Facts
Patent No.
US 9,944,598
App. No.
15/515,574
Granted
Apr 17, 2018
Kind
B2
Abstract

The present invention concerns mono- or di-substituted indole derivatives (I) which are useful to prevent or treat dengue viral infections 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 (31)

1. A compound of formula (I)

wherein:

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

when R 1 is F or CH 3 , R 2 is OCH 3 then R 3 is H;

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

when R 1 is H, and R 2 is OCH 3 then R 3 is H;

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

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

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

or a stereo-isomeric form, a pharmaceutically acceptable salt, solvate or polymorph thereof.

2. A compound of claim 1 selected from the group consisting of:

or a stereo-isomeric form, a pharmaceutically acceptable salt, solvate or polymorph thereof.

3. A pharmaceutical composition comprising a compound of formula (I) or a stereo- isomeric form, a pharmaceutically acceptable salt, solvate or polymorph thereof; according to claim 1 and one or more pharmaceutically acceptable excipients, diluents or carriers.

4. A method of treating a dengue viral infection, comprising administering to a mammal a therapeutically effective amount of at least one compound or a stereo- isomeric form, a pharmaceutically acceptable salt, solvate or polymorph thereof as claimed in claim 1 .

5. A method of inhibiting the replication of dengue virus in a biological sample or patient, comprising administering to said biological sample or patient a therapeutically effective amount of at least one compound or a stereo- isomeric form, a pharmaceutically acceptable salt, solvate or polymorph thereof as claimed in claim 1 .

6. The method as claimed in claim 5 further comprising co-administering an additional therapeutic agent.

7. The method as claimed in claim 6 wherein said additional therapeutic agent is at least one selected from the group consisting of an antiviral agent and a dengue vaccine.

8. A pharmaceutical composition comprising a compound or a stereo- isomeric form, a pharmaceutically acceptable salt, solvate or polymorph thereof according to claim 2 and one or more pharmaceutically acceptable excipients, diluents or carriers.

9. A method of treating a dengue viral infection, comprising administering to a mammal a therapeutically effective amount of at least one compound or a stereo- isomeric form, a pharmaceutically acceptable salt, solvate or polymorph thereof as claimed in claim 2 .

10. The compound of claim 2 which is

or a stereo-isomeric form, a pharmaceutically acceptable salt, solvate or polymorph thereof.

11. The compound of claim 10 , which is

12. The method of claim 4 wherein said compound is

or a stereo- isomeric form, a pharmaceutically acceptable salt, solvate or polymorph thereof.

13. The method of claim 12 , wherein said compound is

14. The method of claim 5 , wherein said compound is

or a stereo- isomeric form, a pharmaceutically acceptable salt, solvate or polymorph thereof.

15. The method of claim 14 , wherein said compound is

16. The pharmaceutical composition of claim 8 , wherein said compound is

or a stereo- isomeric form, a pharmaceutically acceptable salt, solvate or polymorph thereof.

17. The pharmaceutical composition of claim 16 , wherein said compound is

Assignments (6)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 17, 2017
From: KESTELEYN, BART RUDOLF ROMANIE; JONCKERS, TIM HUGO MARIA; RABOISSON, PIERRE JEAN-MARIE BERNARD
To: JANSSEN INFECTIOUS DISEASES BVBA
Reel/Frame 042032/0635 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 17, 2017
From: BONFANTI, JEAN-FRANÇOIS
To: JANSSEN-CILAG
Reel/Frame 042033/0799 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 17, 2017
From: BARDIOT, DOROTHÉE ALICE MARIE-EVE; MARCHAND, ARNAUD DIDIER M
To: CISTIM LEUVEN VZW
Reel/Frame 042033/0805 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 17, 2017
From: JANSSEN INFECTIOUS DISEASES BVBA
To: JANSSEN PHARMACEUTICALS, INC.
Reel/Frame 042033/0831 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 17, 2017
From: JANSSEN-CILAG
To: JANSSEN PHARMACEUTICALS, INC.
Reel/Frame 042033/0833 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 17, 2017
From: CISTIM LEUVEN VZW
To: KATHOLIEKE UNIVERSITEIT LEUVEN
Reel/Frame 042033/0883 →
Priority Claims (2)
EP 14187374 · Oct 1, 2014 · regional
EP 15159164 · Mar 16, 2015 · regional
Continuity (1)
Related Publication 20170298017A1 · Oct 19, 2017