IP Library Granted Patent US 9,663,499
Granted Patent B2
US 9,663,499 · App. 14/895,813 · Granted May 30, 2017

Small molecule inhibitors of fibrosis

Inventors: Luke Lairson (La Jolla, CA); Michael Bollong (San Diego, CA); Peter G. Schultz (La Jolla, CA); Arnab K. Chatterjee (San Diego, CA); Baiyuan Yang (San Diego, CA); Puneet Kumar (Woodbridge, CA); Kaveri Urkalan (San Diego, CA)
Assignees: The California Institute for Biomedical Research; The Scripps Research Institute
C07D405/14A61K31/496A61K31/497A61K31/498A61K31/501A61K31/506A61K31/5377C07D417/14
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Quick Facts
Patent No.
US 9,663,499
App. No.
14/895,813
Granted
May 30, 2017
Kind
B2
Abstract

Described herein are compounds and compositions for the treatment of a fibrotic disease.

Claims (37)

1. A method to treat fibrosis, a disorder characterized by fibrosis, or a disease characterized by fibrosis, the method comprising administering a composition comprising a therapeutically effective amount of a compound of Formula (I), a pharmaceutically acceptable salt, solvate, N-oxide, stereoisomer, or isomer thereof:

wherein:

A 1 is phenyl;

A 2 is phenyl, or pyridine;

B is

C is

D is

E is

heteroaryl, cycloalkyl, heterocyclyl, or alkyl;

each R 1 , R 2 , R 3 , and R 4 is independently selected from H and alkyl;

R 7 is alkyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, or -alkylene(NR 13 R 14 );

each R 8 is independently selected from alkyl, halo, nitrile, alkoxy, haloalkyl and —SO 2 R 13 ;

each R 13 and R 14 is independently selected from H and alkyl;

Y 1 and Y 2 are O;

n is 1;

m is 1;

p is 1, 2, 3, or 4;

s is 0, 1, or 2;

t is 0, 1, or 2;

u is 0, 1, 2, or 3; and

v is 0, 1, or 2.

2. The method of claim 1 , wherein A 1 is phenyl and s is 0 or 1.

3. The method of claim 2 , wherein A 2 is phenyl and t is 0.

4. The method of claim 3 , wherein C is

and R 7 is alkyl.

5. The method of claim 4 , wherein E is

and u is 0, 1, or 2.

6. The method of claim 5 , wherein D is

7. The method of claim 6 , wherein D is

8. The method of claim 7 , wherein v is 0.

9. The method of claim 8 , wherein p is 1.

10. The method of claim 9 , wherein R 1 , R 2 , R 3 , and R 4 are hydrogen.

11. The method of claim 1 , wherein the compound is selected from:

12. The method of claim 1 , wherein the fibrosis is liver fibrosis, idiopathic pulmonary fibrosis, kidney fibrosis, or cardiac fibrosis.

13. The method of claim 1 , wherein the fibrosis is idiopathic pulmonary fibrosis.

14. The method of claim 1 , wherein the disease characterized by fibrosis or the disorder characterized by fibrosis is a chronic autoimmune disease.

15. The method of claim 14 , wherein the chronic autoimmune disease is scleroderma.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 22, 2016
From: LAIRSON, LUKE; SCHULTZ, PETER G.; CHATTERJEE, ARNAB K.; YANG, BAIYUAN; KUMAR, PUNEET; URKALAN, KAVERI
To: THE CALIFORNIA INSTITUTE FOR BIOMEDICAL RESEARCH
Reel/Frame 037791/0411 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 22, 2016
From: LAIRSON, LUKE; BOLLONG, MICHAEL; SCHULTZ, PETER G.
To: THE SCRIPPS RESEARCH INSTITUTE
Reel/Frame 037880/0470 →
Continuity (2)
Provisional Application 61832768 · Jun 7, 2013
Related Publication 20160130258A1 · May 12, 2016