IP Library › Granted Patent US 11,124,500
Granted Patent B2
US 11,124,500 · App. 16/902,806 · Granted Sep 21, 2021

Disubstituted pyrazole compounds

Inventors: David Andrew Coates (New Palestine, IN); Timothy Barrett Durham (Indianapolis, IN); Richard Duane Johnston (Greenfield, IN); Steven Marc Massey (Indianapolis, IN); Patrick Gianpietro Spinazze (Avon, IN); Douglas Richard Stack (Fishers, IN); James Lee Toth (Knightstown, IN)
Assignee: Eli Lilly and Company
C07D403/14A61P1/16A61P3/10A61P9/04A61P13/12
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Quick Facts
Patent No.
US 11,124,500
App. No.
16/902,806
Granted
Sep 21, 2021
Kind
B2
Abstract

The present invention provides a compound of Formula I or a pharmaceutically acceptable salt thereof, and the use of compounds of Formula I for treating metabolic conditions, such as type 2 diabetes mellitus, heart failure, diabetic kidney disease, and non-alcoholic steatohepatitis.

Claims (32)

1. A compound of the formula:

wherein

X is N, or C substituted with CN;

R 1 is selected from: H,

R 2 and R 3 are both H, or one is H and the other is OH;

R 4 , R 5 , R 6 , R 7 and R 9 are independently H or CH 3 ;

R 8 is H, CH 3 , CH 2 CH 2 OH, C(═O)CH 2 NH 2 , or C(═O)CH 3 ; and

R 10 is OH or NH 2 ;

or a pharmaceutically acceptable salt thereof.

2. The compound according to claim 1 , wherein R 1 is selected from:

or a pharmaceutically acceptable salt thereof.

3. The compound according to claim 1 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

4. The compound according to claim 1 , wherein X is N, or a pharmaceutically acceptable salt thereof.

5. The compound according to claim 1 , wherein X is C substituted with CN, or a pharmaceutically acceptable salt thereof.

6. The compound according to claim 1 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

7. The compound, or pharmaceutically acceptable salt thereof, according to claim 6 , which is a succinate salt.

8. A method of treating type 2 diabetes mellitus in a patient, comprising administering to a patient in need of such treatment an effective amount of a compound of claim 1 , or a pharmaceutically acceptable salt thereof.

9. A method of treating heart failure in a patient, comprising administering to a patient in need of such treatment an effective amount of a compound of claim 1 , or a pharmaceutically acceptable salt thereof.

10. A method of treating diabetic kidney disease in a patient, comprising administering to a patient in need of such treatment an effective amount of a compound of claim 1 , or a pharmaceutically acceptable salt thereof.

11. A method of treating non-alcoholic steatohepatitis in a patient, comprising administering to a patient in need of such treatment an effective amount of a compound of claim 1 , or a pharmaceutically acceptable salt thereof.

12. A method of treating type 2 diabetes mellitus in a patient, comprising administering to a patient in need of such treatment an effective amount of a compound of claim 6 ,

or a pharmaceutically acceptable salt thereof.

13. A method of treating heart failure in a patient, comprising administering to a patient in need of such treatment an effective amount of a compound of claim 6 ,

or a pharmaceutically acceptable salt thereof.

14. A method of treating diabetic kidney disease in a patient, comprising administering to a patient in need of such treatment an effective amount of a compound of claim 6 ,

or a pharmaceutically acceptable salt thereof.

15. A method of treating non-alcoholic steatohepatitis in a patient, comprising administering to a patient in need of such treatment an effective amount of a compound of claim 6 ,

or a pharmaceutically acceptable salt thereof.

16. A pharmaceutical composition, comprising a compound, or a pharmaceutically acceptable salt thereof, according to claim 1 with one or more pharmaceutically acceptable carriers, diluents, or excipients.

17. A process for preparing a pharmaceutical composition, comprising admixing a compound, or a pharmaceutically acceptable salt thereof, according to claim 1 with one or more pharmaceutically acceptable carriers, diluents, or excipients.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 16, 2020
From: COATES, DAVID ANDREW; DURHAM, TIMOTHY ANDREW; JOHNSTON, RICHARD DUANE; MASSEY, STEVEN MARC; SPINAZZE, PATRICK GIANPIETRO; STACK, DOUGLAS RICHARD; TOTH, JAMES LEE
To: ELI LILLY AND COMPANY
Reel/Frame 052952/0791 →
Continuity (3)
Provisional Application 62975887 · Feb 13, 2020
Provisional Application 62862382 · Jun 17, 2019
Related Publication 20200392118A1 · Dec 17, 2020