Pyrrolopyrimidine compounds used as TLR7 agonist

Patent metadata

Field	Value
Publication number	US-9962388-B2
Application number	US-201515503977-A
Country	US
Kind code	B2
Filing date	Aug 14, 2015
Priority date	Aug 15, 2014
Publication date	May 8, 2018
Grant date	May 8, 2018

Abstract

The present invention relates to a pyrrolopyrimidine compound as TLR7 agonist, and particularly relates to a compound of formula (I) or a pharmaceutically acceptable salt thereof, a preparation process thereof, a pharmaceutical composition containing such compounds and use thereof for manufacturing a medicament against viral infection.

First claim

The invention claimed is:

1. A compound of formula (I) or a pharmaceutically acceptable salt thereof

wherein
L 1 is —O—;
L 2 is —CH 2 —;
R 1 is selected from the group consisting of hydrogen and C 1-10 alkyl, wherein the above C 1-10 alkyl is optionally substituted by one or more R 4 ;
R 2 is selected from the group consisting of hydrogen, cyano, COOH, and CONH 2 ;
B is selected from the group consisting of aryl and heteroaryl;
L 3 is selected from the group consisting of C 0-6 alkylene and imino, wherein the above C 0-6 alkylene and imino are optionally substituted by one or more R 4 ;
R 3 is selected from the group consisting of hydrogen, amino, C 1-10 alkyl, C 3-10 cyclohydrocarbyl, and 3-10 membered heterocyclohydrocarbyl, wherein the above amino, C 1-10 alkyl, C 3-10 cyclohydrocarbyl, and 3-10 membered heterocyclohydrocarbyl are optionally substituted by one or more R 4 ; or
R 3 and L 3 together with the adjacent atom at the ring B form a saturated or unsaturated 5-8 membered ring, the 5-8 membered ring is optionally substituted by one or more R 4 ;
n is 0, 1, 2, 3, 4 or 5;
R 4 is selected from the group consisting of halogen, —R, —OR, and ═O; and
R is independently selected from the group consisting of H and C 1-8 alkyl.

2. The compound according to claim 1 , characterized in that, R 1 is selected from the group consisting of hydrogen and C 1-6 alkyl, wherein the above C 1-6 alkyl is optionally substituted by one or more R 4 .

3. The compound according to claim 2 , characterized in that, R 1 is selected from the group consisting of C 1-6 alkyl, wherein the above C 1-6 alkyl is optionally substituted by one or more R 4 .

4. The compound according to claim 1 , characterized in that, R 2 is selected from the group consisting of hydrogen, cyano and —CONH 2 .

5. The compound according to claim 1 , characterized in that, B is selected from the group consisting of phenyl and pyridyl.

6. The compound according to claim 1 , characterized in that, L 3 is selected from the group consisting of C 0-6 alkylene, wherein the above C 0-6 alkylene is optionally substituted by one or more R 4 .

7. The compound according to claim 1 , characterized in that, R 3 is selected from the group consisting of hydrogen, amino, C 1-6 alkyl and 3-8 membered heterocyclohydrocarbyl, wherein the above amino, C 1-6 alkyl and 3-8 membered heterocyclohydrocarbyl are optionally substituted by one or more R 4 ; or R 3 and L 3 together with the adjacent atom at the ring B form a saturated or unsaturated 5-8 membered ring, the 5-8 membered ring is optionally substituted by one or more R 4 .

8. The compound according to claim 1 . selected from:

or the pharmaceutically acceptable salt thereof.

9. A pharmaceutical composition, comprising the compound according to claim 1 or the pharmaceutically acceptable salt thereof in a therapeutically effective amount and one or more pharmaceutically acceptable carriers or excipients.

10. A method for treating viral infection, comprising administering the compound according to claim 1 or the pharmaceutically acceptable salt thereof to a subject in need thereof.

Assignees

• Chia Tai Tianqing Pharmaceutical Group Co Ltd

Inventors

• Ding Zhaozhong
• Wu Hao
• Sun Fei
• Wu Lifang
• Yang Ling

Classifications

• A61P31/12

  Antivirals · CPC title

• A61P31/20

  for DNA viruses · CPC title

• C07D265/28

  1,4-Oxazines; Hydrogenated 1,4-oxazines · CPC title

• C07D487/04 Primary

  Ortho-condensed systems · CPC title

• A61K31/519 Primary

  ortho- or peri-condensed with heterocyclic rings · CPC title