IP Library Granted Patent US 11,053,256
Granted Patent B2
US 11,053,256 · App. 16/312,687 · Granted Jul 6, 2021

Dihydropyranopyrimidines for the treatment of viral infections

Inventors: Tim Hugo Maria Jonckers (Heist-op-den-Berg, BE); Pierre Jean-Marie Bernard Raboisson (Wavre, BE); Jérôme Émile Georges Guillemont (Andé, FR); David Craig McGowan (Brussels, BE); Werner Constant Johan Embrechts (Beerse, BE); Ludwig Paul Cooymans (Beerse, BE); Laurent Calmus (Braine l'Alleud, BE)
Assignee: Janssen Sciences Ireland Unlimited Company
C07D491/052
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Quick Facts
Patent No.
US 11,053,256
App. No.
16/312,687
Granted
Jul 6, 2021
Kind
B2
Abstract

This invention relates to dihydropyranopynmidine derivatives, processes for their preparation, pharmaceutical compositions, and their use in treating viral infections.

Claims (19)

1. A method of treating viral hepatitis in which the activation of TLR7 and/or TLR8 is involved in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of a compound of formula (I), (II) or (III) having the structure

or a pharmaceutically acceptable salt, tautomer, stereo-isomeric form, or solvate thereof, wherein

R 1 is C 1-6 alkyl substituted by one or more substituents independently selected from hydroxyl or C 1-3 alkoxy;

R 2 is selected from hydrogen, fluorine, C 1-3 alkyl, cyclopropyl, —CF 3 , C 1-3 alkoxy or nitrile.

2. A method of treating viral hepatitis in which the activation of TLR7 and/or TLR8 is involved in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of a compound having a structure selected from the group consisting of:

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

3. The method of claim 1 , wherein the activation of TLR8 is involved in the subject in need thereof.

4. The method of claim 1 , wherein R 1 is C 1-6 alkyl substituted by hydroxyl.

5. The method of claim 1 , wherein R 1 is C 6 alkyl substituted by hydroxyl.

6. The method of claim 1 , wherein R 1 is:

7. The method of claim 1 , wherein R 1 is:

8. The method of claim 1 , wherein R 2 is hydrogen.

9. The method of claim 2 , wherein the activation of TLR8 is involved in the subject in need thereof.

10. A method of activating human TLR7 and/or TLR8 in a subject, comprising administering to the subject an effective amount of a compound of formula (I), (II) or (III) having the structure

or a pharmaceutically acceptable salt, tautomer, stereo-isomeric form, or solvate thereof, wherein

R 1 is C 1-6 alkyl substituted by one or more substituents independently selected from hydroxyl or C 1-3 alkoxy;

R 2 is selected from hydrogen, fluorine, C 1-3 alkyl, cyclopropyl, —CF 3 , C 1-3 alkoxy or nitrile.

11. The method of claim 10 , wherein the compound has a structure selected from the group consisting of:

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

Assignments (7)
CHANGE OF NAME Recorded May 19, 2021
From: JANSSEN SCIENCES IRELAND UC
To: JANSSEN SCIENCES IRELAND UNLIMITED COMPANY
Reel/Frame 056290/0562 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 16, 2019
From: JONCKERS, TIM HUGO MARIA; RABOISSON, PIERRE JEAN-MARIE BERNARD; MC GOWAN, DAVID CRAIG; EMBRECHTS, WERNER CONSTANT JOHAN; COOYMANS, LUDWIG PAUL
To: JANSSEN PHARMACEUTICA NV
Reel/Frame 048031/0261 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 16, 2019
From: GUILLEMONT, JEROME EMILE GEORGES
To: JANSSEN-CILAG
Reel/Frame 048031/0725 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 16, 2019
From: CALMUS, LAURENT
To: NOVALIX SAS
Reel/Frame 048031/0963 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 16, 2019
From: JANSSEN PHARMACEUTICA NV
To: JANSSEN SCIENCES IRELAND UC
Reel/Frame 048032/0295 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 16, 2019
From: JANSSEN-CILAG
To: JANSSEN SCIENCES IRELAND UC
Reel/Frame 048032/0423 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 16, 2019
From: NOVALIX SAS
To: JANSSEN SCIENCES IRELAND UC
Reel/Frame 048032/0675 →
Priority Claims (1)
EP 16177401 · Jul 1, 2016 · regional
Continuity (1)
Related Publication 20190322678A1 · Oct 24, 2019