IP Library Granted Patent US 11,220,504
Granted Patent B2
US 11,220,504 · App. 16/382,727 · Granted Jan 11, 2022

Pyrrolo[3,2-d] pyrimidine derivatives for the treatment of viral infections and other diseases

Inventors: David Craig McGowan (Brussels, BE); Stefaan Julien Last (Lint, BE); Serge Maria Aloysius Pieters (Hulst, NL); Werner Embrechts (Beerse, BE); Tim Hugo Maria Jonckers (Heist-op-den-Berg, BE); Pierre Jean-Marie Bernard Raboisson (Wavre, BE)
Assignee: JANSSEN SCIENCES IRELAND UNLIMITED COMPANY
C07D487/04A61K31/407A61K31/519A61P31/12C07D519/00
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 11,220,504
App. No.
16/382,727
Granted
Jan 11, 2022
Kind
B2
Abstract

This invention concerns pyrrolo[3,2-d]pyrimidine derivatives, processes for their preparation, pharmaceutical compositions, and their use in treatment and/or therapy of diseases.

Claims (32)

1. A method of treating viral hepatitis in a subject in need thereof, the method comprising activating TLR7 and/or TLR8 in the subject by administering to the subject a therapeutically effective amount of a compound of formula (I):

or a pharmaceutically acceptable salt or solvate thereof;

wherein:

R 1 is selected from the group consisting of H, fluorine, and methyl;

R 2 is selected from the group consisting of H, halogen, and C 1-3 alkyl;

R 3 is C 1-6 alkyl optionally substituted by aryl wherein said aryl is optionally substituted by one or more substituents independently selected from the group consisting of aryloxy, halogen, aryl, alkylamino, dialkylamino, C 1-6 alkyl, —CO 2 H, —C(O)OC 1-6 alkyl, —CONH 2 ,—CN, and C 1-6 alkoxy;

or R 3 is C 1-6 alkyl optionally substituted by C 1-6 alkene, C 3-7 cycloalkyl or C 3-7 heterocycloalkyl;

or R 3 is C 1-6 alkyl optionally substituted by C 1-6 alkoxy, wherein said C 1-6 alkoxy is optionally substituted by aryl; and

R 4 is C 1-8 alkyl optionally substituted by one or more substituents independently selected from the group consisting of hydroxyl, C 1-6 alkoxy, C 1-6 alkyl, C 3-7 cycloalkyl, C 2-6 alkenyl, aryl, heteroaryl, and C 3-7 cycloalkyl, wherein said heteroaryl and said C 3-7 cycloalkyl are optionally further substituted by C 1-6 alkyl;

with the proviso that 2-amino, 4-(N-butylamino)-5-(alphamethylbenzyl)pyrrolo[3,2-d] pyrimidine is excluded.

2. The method of claim 1 wherein R 3 is methyl optionally substituted by aryl.

3. The method of claim 1 wherein each of R 3 and R 4 is independently 1-3 alkyl substituted by aryl.

4. The method of claim 1 wherein R 1 is fluorine and R 2 is hydrogen.

5. A method of treating viral hepatitis in a subject in need thereof, the method comprising activating TLR7 and/or TLR8 in the subject by administering to the subject a therapeutically effective amount of a pharmaceutical composition comprising a compound of claim 1 , or a pharmaceutically acceptable salt or solvate thereof, together with one or more pharmaceutically acceptable excipients, diluents or carriers.

6. A method of treating viral hepatitis in a subject in need thereof, the method comprising activating TLR7 and/or TLR8 in the subject by administering to the subject a therapeutically effective amount of a compound selected from the group consisting of:

or a pharmaceutically acceptable salt thereof.

7. 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):

or a pharmaceutically acceptable salt or solvate thereof;

wherein:

R 1 is selected from the group consisting of H, fluorine, and methyl;

R 2 is selected from the group consisting of H, halogen, and C 1-3 alkyl;

R 3 is C 1-6 alkyl optionally substituted by aryl wherein said aryl is optionally substituted by one or more substituents independently selected from the group consisting of aryloxy, halogen, aryl, alkylamino, dialkylamino, C 1-6 alkyl, —CO 2 H, —C(O)OC 1-6 alkyl, —CONH 2 ,—CN, and C 1-6 alkoxy;

or R 3 is C 1-6 alkyl optionally substituted by C 1-6 alkene, C 3-7 cycloalkyl or C 3-7 heterocycloalkyl;

or R 3 is C 1-6 alkyl optionally substituted by C 1-6 alkoxy, wherein said C 1-6 alkoxy is optionally substituted by aryl; and

R 4 is C 1-8 alkyl optionally substituted by one or more substituents independently selected from the group consisting of hydroxyl, C 1-6 alkoxy, C 1-6 alkyl, C 3-7 cycloalkyl, C 2-6 alkenyl, aryl, heteroaryl, and C 3-7 cycloalkyl, wherein said heteroaryl and said C 3-7 cycloalkyl are optionally further substituted by C 1-6 alkyl;

with the proviso that 2-amino, 4-(N-butylamino)-5-(alphamethylbenzyl)pyrrolo[3,2-d] pyrimidine is excluded.

8. A method of activating human TLR7 and/or TLR8 in a subject, comprising administering to the subject an effective amount of a compound selected from the group consisting of:

or a pharmaceutically acceptable salt thereof.

9. The method of claim 7 wherein R 3 is methyl optionally substituted by aryl.

10. The method of claim 7 wherein each of R 3 and R 4 is independently 1-3 alkyl substituted by aryl.

11. The method of claim 7 wherein R 1 is fluorine and R 2 is hydrogen.

12. A method of activating human TLR7 and/or TLR8 in a subject, comprising administering to the subject an effective amount of a pharmaceutical composition comprising the compound of claim 7 , or a pharmaceutically acceptable salt or solvate thereof, together with one or more pharmaceutically acceptable excipients, diluents or carriers.

Assignments (1)
CHANGE OF NAME Recorded Nov 19, 2021
From: JANSSEN SCIENCES IRELAND UC
To: JANSSEN SCIENCES IRELAND UNLIMITED COMPANY
Reel/Frame 058163/0290 →
Priority Claims (1)
EP 12187994 · Oct 10, 2012 · regional
Continuity (3)
Continuation 15333947 · Oct 25, 2016
Continuation 14434021
Related Publication 20190330217A1 · Oct 31, 2019