IP Library › Granted Patent US 11,884,650
Granted Patent B2
US 11,884,650 · App. 17/743,615 · Granted Jan 30, 2024

Substituted heterocyclic compounds

Inventors: Steven H. Spergel (Warrington, PA); Ryan M. Moslin (Princeton, NJ); Michael Edward Mertzman (New Hope, PA)
Assignee: BRISTOL-MYERS SQUIBB COMPANY
C07D401/14C07D401/12
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Quick Facts
Patent No.
US 11,884,650
App. No.
17/743,615
Granted
Jan 30, 2024
Kind
B2
Abstract

There are disclosed compounds of the following formula I: or a stereoisomer or pharmaceutically acceptable salt thereof, wherein all substituents are as defined herein, which are useful in the modulation of IL-12, IL-23 and/or IFNα, by acting on Tyk-2 to cause signal transduction inhibition. The compounds of the invention may be useful for treating neurodegenerative diseases or disorders.

Claims (31)

1. A compound of formula I

or a stereoisomer or pharmaceutically acceptable salt thereof,

wherein

X is —N— or —CH—;

R 1 is —C(O)R 1a ;

R 1a is C 3-6 cycloalkyl;

R 2 is C 1-6 alkoxy;

R 3 is C 1-6 alkyl or C 3-6 cycloalkyl.

2. The compound according to claim 1 of the formula

or a stereoisomer or pharmaceutically acceptable salt thereof,

wherein

R 1 is —C(O)R 1a ;

R 1a is C 3-6 cycloalkyl;

R 2 is C 1-6 alkoxy;

R 3 is C 1-6 alkyl or C 3-6 cycloalkyl.

3. The compound according to claim 1 of the formula

or a stereoisomer or pharmaceutically acceptable salt thereof,

wherein

R 1 is —C(O)R 1a ;

R 1a is C 3-6 cycloalkyl;

R 2 is C 1-6 alkoxy;

R 3 is C 1-6 alkyl or C 3-6 cycloalkyl.

4. A compound or a pharmaceutically acceptable salt thereof, selected from

N-(4-((3-methoxy-4-(2-methyl-2H-1,2,3-triazol-4-yl)pyridin-2-yl)amino)-5-propionylpyridin-2-yl)cyclopropanecarboxamide,

N-(4-((3-methoxy-4-(2-cyclopropyl-2H-1,2,3-triazol-4-yl)pyridin-2-yl)amino)-5-propionylpyridin-2-yl)cyclopropanecarboxamide,

N-(4-((2-methoxy-3-(2-methyl-2H-1,2,3-triazol-4-yl)phenyl)amino)-5-propionylpyridin-2-yl)cyclopropanecarboxamide,

N-(4-((4-fluoro-2-methoxy-3-(2-methyl-2H-1,2,3-triazol-4-yl)phenyl)amino)-5-propionylpyridin-2-yl)cyclopropanecarboxamide,

N-(4-((3-fluoro-2-methoxy-3-(2-methyl-2H-1,2,3-triazol-4-yl)phenyl)amino)-5-propionylpyridin-2-yl)cyclopropanecarboxamide, and

N-(4-((3-methyl-2-methoxy-3-(2-methyl-2H-1,2,3-triazol-4-yl)phenyl)amino)-5-propionylpyridin-2-yl)cyclopropanecarboxamide.

5. A pharmaceutical composition comprising one or more compounds according to claim 1 and a pharmaceutically acceptable carrier or diluent.

6. A pharmaceutical composition comprising one or more compounds according to claim 4 and a pharmaceutically acceptable carrier or diluent.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 5, 2022
From: SPERGEL, STEVEN H.; MOSLIN, RYAN M.; MERTZMAN, MICHAEL EDWARD
To: BRISTOL-MYERS SQUIBB COMPANY
Reel/Frame 060397/0668 →
Continuity (3)
Provisional Application 63318508 · Mar 10, 2022
Provisional Application 63188498 · May 14, 2021
Related Publication 20220388987A1 · Dec 8, 2022