IP Library Granted Patent US 10,077,240
Granted Patent B2
US 10,077,240 · App. 15/598,734 · Granted Sep 18, 2018

Compositions and methods for modulating farnesoid X receptors

Inventors: Donatella Chianelli (San Diego, CA); Valentina Molteni (San Diego, CA); John Nelson (San Diego, CA); Jason Thomas Roland (San Diego, CA); Paul Vincent Rucker (Carlsbad, CA); David Charles Tully (Danville, CA)
Assignee: Novartis AG
C07D231/54A61K31/416A61K31/4162A61K31/4439A61K31/4745C07D471/04C07D471/06C07D491/052
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Quick Facts
Patent No.
US 10,077,240
App. No.
15/598,734
Granted
Sep 18, 2018
Kind
B2
Abstract

The present invention relates to compounds of Formula I, a stereoisomer, enantiomer, a pharmaceutically acceptable salt or an amino acid conjugate thereof; wherein variables are as defined herein; and their pharmaceutical compositions, which are useful as modulators of the activity of Farnesoid X receptors (FXR).

Claims (22)

1. A compound selected from the group consisting of:

4-fluoro-3-(2-(8-fluoro-N-(2-fluorobenzyl)-1-methyl-1,4-dihydrochromeno[4,3-c]pyrazole-3-carboxamido)acetamido)benzoic acid L-arginine salt;

4-fluoro-3-(2-(8-fluoro-N-(2-fluorobenzyl)-1-methyl-1,4-dihydrochromeno[4,3-c]pyrazole-3-carboxamido)acetamido)benzoic acid sodium salt;

4-fluoro-3-(2-(8-fluoro-N-(3-fluorobenzyl)-1-methyl-1,4-dihydrochromeno[4,3-c]pyrazole-3-carboxamido)acetamido)benzoic acid L-arginine salt;

4-fluoro-3-(2-(8-fluoro-N-(3-fluorobenzyl)-1-methyl-1,4-dihydrochromeno[4,3-c]pyrazole-3-carboxamido)acetamido)benzoic acid L-lysine salt;

4-((N-benzyl-8-chloro-1-methyl-1,4-dihydrochromeno[4,3-c]pyrazole-3-carboxamido)methyl)benzoic acid TRIS salt;

4-((N-benzyl-8-chloro-1-methyl-1,4-dihydrochromeno[4,3-c]pyrazole-3-carboxamido)methyl)benzoic acid meglumine monohydrate; and

4-((N-benzyl-8-chloro-1-methyl-1,4-dihydrochromeno[4,3-c]pyrazole-3-carboxamido)methyl)benzoic acid meglumine salt.

2. A pharmaceutical composition comprising a therapeutically effective amount of a compound of claim 1 or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

3. A combination comprising a therapeutically effective amount of a compound of claim 1 or a pharmaceutically acceptable salt thereof, and a second therapeutic agent.

4. A method for treating a condition mediated by farnesoid X receptors (FXR) in a subject suffering therefrom, comprising administering to the subject a therapeutically effective amount of a compound of claim 1 or a pharmaceutically acceptable salt thereof, and optionally in combination with a second therapeutic agent.

5. The method of claim 4 , wherein said condition mediated by FXR is a liver disease or a gastrointestinal disease.

6. The method of claim 5 , wherein said condition mediated by FXR is a liver disease selected from intrahepatic cholestasis, estrogen-induced cholestasis, drug-induced cholestasis, cholestasis of pregnancy, parenteral nutrition-associated cholestasis, progressive familial cholestasis (PFIC), Alagille syndrome, primary biliary cirrhosis (PBC), primary sclerosing cholangitis, ductopenic liver transplant rejection, liver transplant associated graft versus host disease, cystic fibrosis liver disease, non-alcoholic fatty liver disease (NAFLD), non-alcoholic steatohepatitis (NASH), alcoholic liver disease, and parenteral nutrition-associated liver disease.

7. The method of claim 6 , wherein said condition mediated by FXR is non-alcoholic fatty liver disease (NAFLD) or non-alcoholic steatohepatitis (NASH).

8. The method of claim 5 , wherein said condition mediated by FXR is a gastrointestinal disease selected from primary bile acid diarrhea, secondary bile acid diarrhea, bile reflux gastritis, and inflammatory bowel disease.

9. The method of claim 4 , wherein said compound is 4-fluoro-3-(2-(8-fluoro-N-(2-fluorobenzyl)-1-methyl-1,4-dihydrochromeno[4,3-c]pyrazole-3-carboxamido)acetamido)benzoic acid L-arginine salt.

10. The method of claim 4 , wherein said compound is 4-fluoro-3-(2-(8-fluoro-N-(2-fluorobenzyl)-1-methyl-1,4-dihydrochromeno[4,3-c]pyrazole-3-carboxamido)acetamido)benzoic acid sodium salt.

11. The method of claim 4 , wherein said compound is 4-fluoro-3-(2-(8-fluoro-N-(3-fluorobenzyl)-1-methyl-1,4-dihydrochromeno[4,3-c]pyrazole-3-carboxamido)acetamido)benzoic acid L-arginine salt.

12. The method of claim 4 , wherein said compound is 4-fluoro-3-(2-(8-fluoro-N-(3-fluorobenzyl)-1-methyl-1,4-dihydrochromeno[4,3-c]pyrazole-3-carboxamido)acetamido)benzoic acid L-lysine salt.

13. The method of claim 4 , wherein said compound is 4-((N-benzyl-8-chloro-1-methyl-1,4-dihydrochromeno[4,3-c]pyrazole-3-carboxamido)methyl)benzoic acid TRIS salt.

14. The method of claim 4 , wherein said compound is 4-((N-benzyl-8-chloro-1-methyl-1,4-dihydrochromeno[4,3-c]pyrazole-3-carboxamido)methyl)benzoic acid meglumine monohydrate.

15. The method of claim 4 , wherein said compound is 4-((N-benzyl-8-chloro-1-methyl-1,4-dihydrochromeno[4,3-c]pyrazole-3-carboxamido)methyl)benzoic acid meglumine salt.

Assignments (5)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 15, 2018
From: CHIANELLI, DONATELLA; LIU, XIAODONG; MOLTENI, VALENTINA; NELSON, JOHN; ROLAND, JASON THOMAS; RUCKER, PAUL VINCENT; TULLY, DAVID C.
To: NOVARTIS INSTITUTE FOR FUNCTIONAL GENOMICS, INC., DBA THE GENOMICS INSTITUTE OF THE NOVARTIS RESEARCH FOUNDATION
Reel/Frame 046102/0838 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 15, 2018
From: NOVARTIS INSTITUTE FOR FUNCTIONAL GENOMICS, INC., DBA THE GENOMICS INSTITUTE OF THE NOVARTIS RESEARCH FOUNDATION
To: IRM LLC
Reel/Frame 046103/0065 →
MERGER Recorded Jun 15, 2018
From: IRM LLC
To: NOVARTIS INTERNATIONAL PHARMACEUTICAL LTD.
Reel/Frame 046103/0441 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 15, 2018
From: NOVARTIS INTERNATIONAL PHARMACEUTICAL LTD.
To: NOVARTIS INTERNATIONAL PHARMACEUTICAL AG
Reel/Frame 046103/0644 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 15, 2018
From: NOVARTIS INTERNATIONAL PHARMACEUTICAL AG
To: NOVARTIS AG
Reel/Frame 046103/0976 →
Continuity (3)
Continuation 15034280
Provisional Application 61900013 · Nov 5, 2013
Related Publication 20170275256A1 · Sep 28, 2017