US 12,110,290 B2Granted

Triazolopyridinyl compounds as kinase inhibitors

AssigneeBristol-Myers Squibb Company

InventorsGuanglin Luo, Jie Chen, Carolyn Diane Dzierba, David B. Frennesson, Junqing Guo, Amy C. Hart, Xirui Hu, Michael E. Mertzman, Matthew Reiser Patton, Jianliang Shi, Steven H. Spergel, Brian Lee Venables, Yong-Jin Wu, Zili Xiao, Michael G. Yang

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Abstract

Compounds having formula (I), and enantiomers, and diastereomers, stereoisomers, pharmaceutically-acceptable salts thereof, are useful as kinase modulators, including RIPK1 modulation. All the variables are as defined herein.

Claims14

Dependent claims

A compound having formula (I), or salt thereof,

wherein
R1 is H, C1-3 alkyl, C1-3 alkoxy, C1-3 haloalkyl, C1-3 haloalkoxy, C1-3 deuteroalkyl, C1-3 deuteroalkoxy, halo, or cyclopropyl;
R2 is H, or halo;
R3 is H, halo, C1-3 alkyl or C1-3 deuteroalkyl;
R4 is H or F;
R5a and R5b are each H;
one of R6a and R6b is H and the other is F;
R7a and R7b are each, independently, H, deuterium, OH, F, C1-2 alkyl, or C1-2 haloalkyl;
R8 is H, F, Cl, C1-3 alkyl, C1-3 alkoxy, C1-3 deuteroalkyl, or C1-3 deuteroalkoxy;
R9 is H or CH3;
ring Z is phenyl;
Y is F, Cl, C1-3 alkyl, C1-3 alkoxy, CN, C1-3 haloalkyl, C1-3 haloalkoxy, C1-3 deuteroalkyl, C1-3 deuteroalkoxy, C(O)OCH3, or C═CH;
and
n is 0, 1, 2, or 3.

11 more elements

A compound, or salt thereof, wherein the compound is selected from

3-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-6-chloro-N-(3-(4-chlorophenyl)-2-fluoro-3-hydroxypropyl)-2-fluorobenzamide;
3-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-6-chloro-2-fluoro-N-((2S,3S)-2-fluoro-3-(4-fluorophenyl)-3-hydroxybutyl)benzamide;
3-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-6-chloro-2-fluoro-N-((2R,3R)-2-fluoro-3-(4-fluorophenyl)-3-hydroxybutyl)benzamide;
3-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-6-chloro-2-fluoro-N-((2S,3R)-2-fluoro-3-(4-fluorophenyl)-3-hydroxybutyl)benzamide;
3-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-6-chloro-2-fluoro-N-((2R,3S)-2-fluoro-3-(4-fluorophenyl)-3-hydroxybutyl)benzamide;
3-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-fluoro-N-((2S,3S)-2-fluoro-3-(4-fluorophenyl)-3-hydroxybutyl)-6-(methyl-d3)benzamide;
3-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-fluoro-N-((2R,3R)-2-fluoro-3-(4-fluorophenyl)-3-hydroxybutyl)-6-(methyl-d3)benzamide;
3-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-fluoro-N-((2S,3R)-2-fluoro-3-(4-fluorophenyl)-3-hydroxybutyl)-6-(methyl-d3)benzamide;
3-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-2-fluoro-N-((2R,3S)-2-fluoro-3-(4-fluorophenyl)-3-hydroxybutyl)-6-(methyl-d3)benzamide;
3-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-6-chloro-2-fluoro-N-((2S,3S)-2-fluoro-3-(4-fluorophenyl)-3-hydroxypropyl)benzamide;
3-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-6-chloro-2-fluoro-N-((2R,3R)-2-fluoro-3-(4-fluorophenyl)-3-hydroxypropyl)benzamide;
3-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-6-chloro-2-fluoro-N-((2R,3S)-2-fluoro-3-(4-fluorophenyl)-3-hydroxypropyl)benzamide;
3-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-6-chloro-2-fluoro-N-((2S,3R)-2-fluoro-3-(4-fluorophenyl)-3-hydroxypropyl)benzamide;
3-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-((2R,3S)-3-(4-chlorophenyl)-2-fluoro-3-hydroxypropyl)-2-fluoro-6-methylbenzamide;
3-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-((2S,3R)-3-(4-chlorophenyl)-2-fluoro-3-hydroxypropyl)-2-fluoro-6-methylbenzamide;
3-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-((2S,3S)-3-(4-chlorophenyl)-2-fluoro-3-hydroxypropyl)-2-fluoro-6-methylbenzamide;
and
3-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-((2R,3R)-3-(4-chlorophenyl)-2-fluoro-3-hydroxypropyl)-2-fluoro-6-methylbenzamide.

15 more elements

Dependencies are inferred from the claim text.

Facts

Application: 18/347,703Filed 6 Jul 2023 · continuation
Priority: 19 Oct 2020
Published: US 2024/0109888 A14 Apr 2024
Granted: 8 Oct 2024
Term ends: Not estimatedThe source records don’t support an estimate.

Classification7 codes

C07D 471/04
In which the condensed system contains two hetero rings: ortho-condensed systems
A61P 9/04
Drugs for disorders of the cardiovascular system: inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
A61P 17/06
Drugs for dermatological disorders: antipsoriatics
A61P 25/28
Drugs for disorders of the nervous system: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents,…

Family

Application63/093,463Us provisional application · filed 19 Oct 2020
Application17/503,516Parent of this continuation · filed 18 Oct 2021
US 2024/0109888 A1Pre-grant publication · published 4 Apr 2024
US 11,767,322 B2Parent of this continuation
US 2022/0119388 A1Published application
US 12,110,290 B2This patent

From the US filing history. Foreign family members aren’t listed.

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