# US 10,765,662 B2 · Mono- or di-substituted indole derivatives as dengue viral replication inhibitors

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- Number: US 10,765,662 B2
- Document ID: US10765662B2
- Status: Granted
- Kind: B2
- Application number: 15/759,846
- Filed: 2016-09-15
- Published: 2018-09-13
- Granted: 2020-09-08
- Earliest claimed: 2015-09-16
- Assignees: Janssen Pharmaceuticals, Inc.; Katholieke Universiteit Leuven
- Applicants: Janssen Pharmaceuticals, Inc.; Katholieke Universiteit Leuven
- Inventors: Bart Rudolf Romanie Kesteleyn; Jean-François Bonfanti; Tim Hugo Maria Jonckers; Pierre Jean-Marie Bernard Raboisson; Dorothée Alice Marie-Eve Bardiot; Arnaud Didier M Marchand
- Web page: https://patentgrep.com/patent/US10765662B2

## CPC

- A61K 31/404: Indoles, e.g. pindolol
- A61P 31/14: for RNA viruses
- C07D 209/12: Radicals substituted by oxygen atoms
- Y02A 50/30: Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- Y02A: TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE

## 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

### Claim 1

A compound of formula (I)
or a stereo-isomeric form, a pharmaceutically acceptable salt, solvate or polymorph thereof consisting of a mono- or di-substituted indole group; wherein:
R1 is H, R2 is F, Cl or OCH3 and R3 is H;
R1 is H, R2 is F or Cl and R3 is CH3;
R1 is CH3, R2 is OCH3 and R3 is H;
R1 is F, R2 is F and R3 is H;
R1 is CH3, R2 is F and R3 is H;
R1 is CF3 or OCF3 and R2 is H and R3 is H;
R1 is OCF3, R2 is OCH3 and R3 is H; or
R1 is OCF3, R2 is H or R3 is CH3.

### Claim 2 (depends on 1)

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

### Claim 3 (depends on 1)

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

### Claim 4 (depends on 3)

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.

### Claim 5 (depends on 4)

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

### Claim 6 (depends on 2)

The compound of claim 2, which is:

### Claim 7 (depends on 2)

The compound of claim 2, which is:

### Claim 8 (depends on 2)

The compound of claim 2, which is:

### Claim 9 (depends on 2)

The compound of claim 2, which is:

### Claim 10 (depends on 2)

The compound of claim 2, which is:

### Claim 11 (depends on 2)

The compound of claim 2, which is:

### Claim 12 (depends on 2)

The compound of claim 2, which is:

### Claim 13 (depends on 2)

The compound of claim 2, which is:

### Claim 14 (depends on 2)

The compound of claim 2, which is:

### Claim 15 (depends on 2)

The compound of claim 2, which is:

### Claim 16 (depends on 2)

The compound of claim 2, which is:

### Claim 17 (depends on 2)

The compound of claim 2, which is: