IP Library › Granted Patent US 10,206,907
Granted Patent B2
US 10,206,907 · App. 15/236,578 · Granted Feb 19, 2019

Compounds useful for the treatment of degenerative and inflammatory diseases

Inventors: Christel Jeanne Marie Menet (Mechelen, BE); Luc Juliaan Corina Van Rompaey (Mechelen, BE); Stephen Robert Fletcher (Herts, GB); Javier Blanc (Mechelen, BE); Nolwenn Jouannigot (Annecy le Vieux, FR); Alastair James Hodges (Essex, GB); Koen Kurt Smits (Boechout, BE)
Assignee: GALAPAGOS NV
A61K31/437A61K31/444A61K31/4545A61K31/4725A61K31/496A61K31/497A61K31/4995A61K31/501A61K31/506A61K31/5377A61K31/5386A61K31/541A61K31/551C07D471/04
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Quick Facts
Patent No.
US 10,206,907
App. No.
15/236,578
Granted
Feb 19, 2019
Kind
B2
Abstract

[1,2,4]triazolo[1,5-a]pyridine compounds are disclosed that have a formula represented by the following: The compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, diseases involving cartilage degradation, bone and/or joint degradation, for example osteoarthritis; and/or conditions involving inflammation or immune responses, such as Crohn's disease, rheumatoid arthritis, psoriasis, allergic airways disease (e.g. asthma, rhinitis), juvenile idiopathic arthritis, colitis, inflammatory bowel diseases, endotoxin-driven disease states (e.g. complications after bypass surgery or chronic endotoxin states contributing to e.g. chronic cardiac failure), diseases involving impairment of cartilage turnover (e.g. diseases involving the anabolic stimulation of chondrocytes), congenital cartilage malformations, diseases associated with hypersecretion of IL6 and transplantation rejection (e.g. organ transplant rejection) and proliferative diseases.

Claims (317)

1. A method for the treatment of Crohn's disease, comprising administering a therapeutically effective amount of a compound chosen from compounds of Formula III:

and pharmaceutically acceptable salts thereof, wherein

the group

is chosen from

n2 is chosen from 0, 1, 2, 3, and 4;

R 3b is chosen from —OPh, —O-(4-F-Ph), —CO—R 3c , and

R 3c is chosen from

Cy3 is chosen from

each R 5a is independently chosen from C 1 -C 4 alkyl, halo, CF 3 , and phenyl;

R 5b is chosen from H, aryl, 5-10 membered heteroaryl, C 3 -C 6 cycloalkyl, and 4-7 membered heterocycloalkyl;

R 5c is chosen from H and C 1 -C 4 alkyl;

m5 is chosen from 0, 1, and 2; and

n5 is chosen from 0, 1, and 2.

2. The method of claim 1 , wherein the compound is administered in the form of a pharmaceutical composition comprising at least one pharmaceutically acceptable carrier.

3. A method for the treatment of Crohn's disease, comprising administering a therapeutically effective amount of a compound chosen from compounds of the following formulae:

and pharmaceutically acceptable salts of any of the foregoing.

4. A method for the treatment of Crohn's disease, comprising administering a therapeutically effective amount of a compound chosen from compounds of the following formulae:

and pharmaceutically acceptable salts of any of the foregoing.

5. A method for the treatment of Crohn's disease, comprising administering a therapeutically effective amount of a compound chosen from compounds of the following formulae:

and pharmaceutically acceptable salts of any of the foregoing.

6. A method for the treatment of Crohn's disease, comprising administering a therapeutically effective amount of a compound chosen from

N-(5-(4-(4-methylpiperazin-1-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(3-(morpholinomethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(biphenyl-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-benzoylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-N-cyclopropylbenzamide,

N-(5-(4-(benzyloxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(N-cyclopropylsulfamoyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(3-(benzyloxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(benzyloxy)-3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(2-(benzyloxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(piperidine-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(morpholinomethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(pyrrolidine-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(thiophen-2-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)phenyl)benzamide,

N-(4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)phenyl)-4-(trifluoromethyl)benzamide,

N-(5-(4-(2-phenylacetamido)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(morpholine-4-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-N-(pyridin-4-yl)benzamide,

N-cyclohexyl-4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)benzamide,

N-(5-(4-(4-tert-butylpiperidine-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(1,4-diazepane-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-N-(3-fluorobenzyl)benzamide,

4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-N-methyl-N-phenylbenzamide,

4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-N-(4-methoxybenzyl)-N-methylbenzamide,

4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-N-(1-methylpiperidin-4-yl)benzamide,

N-(5-(4-(4-fluorophenylsulfonamido)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)phenyl)-2-fluorobenzamide,

N-(4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)phenyl)pyrazine-2-carboxamide,

N-(5-(4-(pyridin-3-ylmethoxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(pyridin-2-ylmethoxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(3-(trifluoromethoxy)benzyloxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(cyclobutylmethoxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(cyclopentyloxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(cyclohexylmethoxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide, 4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-N-(pyridin-3-ylmethyl)benzamide, 4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-N-phenylbenzamide,

N-(5-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)pyridin-2-yl)benzamide,

N-(4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)phenyl)cyclohexanecarboxamide,

N-(5-(4-phenoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-((1-methyl-1H-pyrazol-3-yl)methylmethyl-1H-pyrazol-3-yl)methoxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-((3,5-dimethylisoxazol-4-yl)methoxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-((1,3-dimethyl-1H-pyrazol-5-yl)methyldimethyl-1H-pyrazol-5-yl)methoxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(2-(3,5-dimethyl-1H-pyrazol-4-yl)ethyldimethyl-1H-pyrazol-4-yl)ethoxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-((5-methylisoxazol-3-yl)methoxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)phenyl)-3-methoxybenzamide,

N-(5-(4-(2-fluorophenylsulfonamido)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)phenyl)picolinamide,

N-benzyl-4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)benzamide,

N-(5-(4-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(cyclopropanesulfonamido)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-N-(2-phenoxyethyl)benzamide,

N-(5-(4-((1,5-dimethyl-1H-pyrazol-3-yl)methyldimethyl-1H-pyrazol-3-yl)methoxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-((2,5-dimethyloxazol-4-yl)methoxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(pyridine-3-sulfonamido)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(1,3-dimethyl-1H-pyrazole-4-sulfonamido)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(pyridin-3-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(1H-pyrazol-4-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)phenyl)-1-methyl-3-propyl-1H-pyrazole-5-carboxamide,

N-(4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)phenyl)cyclobutanecarboxamide,

N-(5-(4-(4-methylpiperazine-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(benzylamino)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(4-(ethoxymethyl)piperidine-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(4-benzoylpiperidine-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(4-benzyl-1,4-diazepane-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(2-phenylethylsulfonamido)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(phenylmethylsulfonamido)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-((6-(trifluoromethyl)pyridin-3-yl)methoxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(phenylsulfonamido)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-N-(2-(pyrrolidin-1-yl)ethyl)benzamide,

4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-N-(3-morpholinopropyl)benzamide,

N-(5-(4-(4-propylphenylsulfonamido)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(4-(4-chlorophenyl)piperidine-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-N-phenethylbenzamide,

N-(5-(4-(2-(3-fluorophenyl)ethylsulfonamido)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(2-fluoro-4-(piperidine-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-butyl-4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-N-(3-morpholinopropyl)benzamide,

N-(5-(4-((2-(4-(trifluoromethyl)phenyl)thiazol-4-yl)methoxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(4-acetamidobenzyloxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(6-(2-(tetrahydro-2H-pyran-4-yl)ethylamino)pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(4-(2-morpholinoethyl)piperidine-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-N-methyl-N-phenethylbenzamide,

4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-N-(4-(trifluoromethyl)phenethyl)benzamide,

N-(5-(4-(2-(1H-pyrazol-1-yl)ethyl1H-pyrazol-1-yl)ethoxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-((1,2,4-oxadiazol-3-yl)methoxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-3-fluoro-N-(2-phenoxyethyl)benzamide,

N-(5-(4-(4-morpholinopiperidine-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-N-(2-methyl-1-morpholinopropan-2-yl)benzamide,

N-(5-(4-(4-(benzyl(methyl)amino)piperidine-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-N-(3,4-dimethoxyphenethyl)-N-methylbenzamide,

4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-N-(2-(1-phenyl-1H-pyrazol-4-yl)ethyl)benzamide,

N-(5-(4-(3-phenoxypropanamido)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(3-phenylpropanamido)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(4-(pyridin-3-yloxy)piperidine-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide

4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-3-fluoro-N-phenethylbenzamide,

N-(5-(4-(4-(3-chlorophenyl)piperazine-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-N-(3-phenylpropyl)benzamide,

N-(5-(4-(2-(4-fluorophenoxy)ethoxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(2-(3-fluorophenylamino)-2-oxoethoxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(2-oxo-2-(piperidin-1-yl)ethoxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(2-(methyl(phenyl)amino)-2-oxoethoxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

(S)—N-(1-benzylpyrrolidin-3-yl)-4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)benzamide,

(R)—N-(1-benzylpyrrolidin-3-yl)-4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)benzamide,

N-(5-(4-(2-phenoxyethylsulfonamido)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-N-(2-(pyridin-3-yl)ethyl)benzamide,

N-(5-(4-(1H-pyrazol-1-yl)benzyloxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(4-((4-methylpiperazin-1-yl)methyl)benzyloxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(2-(pyridin-3-yl)ethoxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(4-(1H-benzo[d]imidazol-2-yl)piperidine-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-morpholinophenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(4-(2-methoxyphenyl)piperidine-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(4-(4-chlorophenyl)-4-hydroxypiperidine-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(4-(o-tolyloxymethyl)piperidine-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(3,5-dimethylpiperidine-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-N-isopropyl-N-(4-(piperidin-1-yl)benzyl)benzamide,

4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-N-propyl-N-((tetrahydrofuran-2-yl)methyl)benzamide,

N-(5-(4-(4-fluoropiperidine-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(4-(1H-indol-2-yl)piperidine-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(piperidin-1-ylmethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

1-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)benzyl)piperidine-4-carboxamide,

N-(5-(4-((4-acetylpiperazin-1-yl)methyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-((4-(pyridin-2-yl)piperazin-1-yl)methyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-((4-(pyrimidin-2-yl)piperazin-1-yl)methyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(2-methylpiperidine-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(3-methylpiperidine-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(4-methylpiperidine-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(4-phenethylpiperidine-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(4-(trifluoromethyl)piperidine-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(4-(6-fluorobenzo[d]isoxazol-3-yl)piperidine-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-benzyl-4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-N-(2-(dimethylamino)ethyl)benzamide,

4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-N-(4-fluorobenzyl)-N-(1-methoxypropan-2-yl)benzamide,

N-(5-(4-(4-(1H-benzo[d][1,2,3]triazol-1-yl)piperidine-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-N-(4-fluorobenzyl)-N-((tetrahydrofuran-2-yl)methyl)benzamide,

N-(5-(4-(imino(4-(2-(2-methyl-1H-imidazol-1-yl)ethyl)piperidin-1-yl)methyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-((methyl(2-(pyridin-2-yl)ethyl)amino)methyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(4-benzyl-4-hydroxypiperidine-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(benzyl(methyl)amino)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-((1H-tetrazol-5-yl)methyl1H-tetrazol-5-yl)methoxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-((methyl(4-(pyridin-2-yl)benzyl)amino)methyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-((((1,5-dimethyl-1H-pyrazol-3-yl)methyl)(methyl)amino)methyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-((methyl(4-(pyrimidin-5-yl)benzyl)amino)methyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide

N-(5-(4-(methyl(pyridin-3-ylmethyl)amino)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(benzyloxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)acetamide,

N-(5-(4-(3-(trifluoromethyl)piperidine-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-((6-morpholinopyridin-3-yl)methoxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-((6-(1H-pyrazol-4-yl)pyridin-3-yl)methyl1H-pyrazol-4-yl)pyridin-3-yl)methoxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-((6-(4-methylpiperazin-1-yl)pyridin-3-yl)methoxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(4,4-difluoropipendine-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(3-phenylpipendine-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-((6-(pyrrolidin-1-yl)pyridin-3-yl)methoxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(3,3-dimethylpipendine-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-((6-cyanopyridin-3-yl)methoxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

1-cyano-N-(4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)phenyl)cyclopropanecarboxamide,

N-(5-(4-((6-(1-methyl-1H-pyrazol-4-yl)pyridin-3-yl)methylmethyl-1H-pyrazol-4-yl)pyridin-3-yl)methoxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(cyanomethyl)-4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-N-phenethylbenzamide,

N-(5-(4-(pyridin-3-ylmethylamino)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-((6-(1H-tetrazol-5-yl)pyridin-3-yl)methyl1H-tetrazol-5-yl)pyridin-3-yl)methoxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(1-(pyridin-2-yl)ethoxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

Methyl 6-((4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)phenylcyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)phenoxy)methyl)nicotinate,

5-((4-(2-(cyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)phenylcyclopropanecarboxamido)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)phenoxy)methyl)picolinamide,

N-(5-(1-(pyridin-2-ylmethyl)-1H-1,2,3-triazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(pyridin-2-ylmethylsulfonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(pyridin-3-ylmethylsulfonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

Cyclopropanecarboxylic acid {5-[4-(1-hydroxy-pyridin-3-ylmethoxy)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-(6-methyl-pyridin-3-ylmethoxy)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide

Cyclopropanecarboxylic acid {5-[4-(6-chloro-pyridin-3-ylmethoxy)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide

Cyclopropanecarboxylic acid {5-[4-(1-methyl-1H-[1,2,4]triazol-3-ylmethoxy)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid (5-{4-[2-(3,5-dimethyl-isoxazol-4-yl)-ethoxy]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

Cyclopropanecarboxylic acid {5-[4-(acetyl-pyridin-3-ylmethyl-amino)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

4-[2-(Cyclopropanecarbonyl-amino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-N-(6-methoxy-pyridin-3-yl)-benzamide,

4-[2-(Cyclopropanecarbonyl-amino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-N-(6-morpholin-4-yl-pyridin-3-yl)-benzamide,

4-[2-(Cyclopropanecarbonyl-amino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-N-[6-(4-methyl-piperazin-1-yl)-pyridin-3-yl]-benzamide,

4-[2-(Cyclopropanecarbonyl-amino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-N-pyridin-3-yl-benzamide,

Cyclopropanecarboxylic acid {5-[4-(acetyl-pyridin-2-ylmethyl-amino)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-(4-hydroxy-piperidine-1-carbonyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-(4-cyano-piperidine-1-carbonyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-(2-pyridin-2-yl-ethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid (5-{4-[(4-chloro-2-fluoro-phenylamino)-methyl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

Cyclopropanecarboxylic acid {5-[4-(3,3-dimethyl-morpholin-4-ylmethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-((2R,6S)-2,6-dimethyl-morpholin-4-ylmethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-(2,6-dimethyl-morpholine-4-carbonyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-(3,3-dimethyl-morpholine-4-carbonyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-((1S,4S)-2-oxa-5-aza-bicyclo[2.2.1]heptane-5-carbonyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

4-[2-(Cyclopropanecarbonyl-amino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-N-(5-cyclopropyl-2-methyl-2H-pyrazol-3-yl)-benzamide,

Cyclopropanecarboxylic acid (5-{4-[4-(morpholine-4-carbonyl)-piperidine-1-carbonyl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

Cyclopropanecarboxylic acid {5-[4-(4-acetyl-piperazine-1-carbonyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

4-[2-(Cyclopropanecarbonyl-amino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-N-pyridazin-3-yl-benzamide,

Cyclopropanecarboxylic acid {5-[4-(pyridazin-3-ylaminomethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-(pyridin-3-ylaminomethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid (5-{4-[(4-cyanomethyl-phenylamino)-methyl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

Cyclopropanecarboxylic acid (5-{4-[(2-cyanomethyl-phenylamino)-methyl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

Cyclopropanecarboxylic acid (5-{4-[(2-fluoro-phenylamino)-methyl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

4-{4-[2-(Cyclopropanecarbonyl-amino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-benzylamino}-benzamide,

3-{4-[2-(Cyclopropanecarbonyl-amino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-benzylamino}-benzamide,

Cyclopropanecarboxylic acid {5-[4-(pyrimidin-2-ylaminomethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid (5-{4-[(1S,4S)-1-(2-oxa-5-aza-bicyclo[2.2.1]hept-5-yl)methyl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

Cyclopropanecarboxylic acid {5-[4-(2-phenyl-morpholin-4-ylmethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-(4-cyano-piperidin-1-ylmethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-(4-fluoro-piperidin-1-ylmethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-(4,4-difluoro-piperidin-1-ylmethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid [5-(4-{[6-(4-methyl-piperazin-1-yl)-pyridin-3-ylamino]-methyl}-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-amide,

Cyclopropanecarboxylic acid (5-{4-[(6-methoxy-pyridin-3-ylamino)-methyl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

Cyclopropanecarboxylic acid (5-{4-[(6-morpholin-4-yl-pyridin-3-ylamino)-methyl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

Cyclopropanecarboxylic acid [5-(4-phenoxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-amide,

Cyclopropanecarboxylic acid {5-[4-(6-cyano-pyridin-3-yl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-(4-trifluoromethyl-piperidin-1-ylmethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid (5-{4-[4-(2,2,2-trifluoro-ethyl)-piperazin-1-ylmethyl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

Cyclopropanecarboxylic acid {5-[4-(4-hydroxy-piperidin-1-ylmethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid (5-{4-[4-(1-hydroxy-1-methyl-ethyl)-piperidin-1-ylmethyl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

Cyclopropanecarboxylic acid {5-[4-(pyridin-2-ylaminomethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid (5-{4-[(2,4-difluoro-3-methoxy-phenylamino)-methyl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

Cyclopropanecarboxylic acid (5-{4-[(2,6-difluoro-phenylamino)-methyl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

Cyclopropanecarboxylic acid {5-[4-(4-diethylamino-piperidin-1-ylmethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid (5-{4-[(2-fluoro-5-trifluoromethyl-phenylamino)-methyl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

3-{4-[2-(Cyclopropanecarbonyl-amino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-benzylamino}-4-methyl-benzamide,

Cyclopropanecarboxylic acid {5-[4-(4-hydroxymethyl-piperidin-1-ylmethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

3-{4-[2-(Cyclopropanecarbonyl-amino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-benzyloxy}-benzamide,

Cyclopropanecarboxylic acid {5-[4-(3-diethylamino-pyrrolidin-1-ylmethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-((1R,4R)-5-ethyl-2,5-diaza-bicyclo[2.2.1]hept-2-ylmethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-(3-oxo-morpholin-4-ylmethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

3-{4-[2-(Cyclopropanecarbonyl-amino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-benzylamino}-4-methoxy-benzamide,

Cyclopropanecarboxylic acid (5-{4-[(2-fluoro-6-methyl-pyridin-3-ylamino)-methyl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

Cyclopropanecarboxylic acid (5-{4-[(3,5-difluoro-pyridin-2-ylamino)-methyl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

Cyclopropanecarboxylic acid (5-{4-[(4-cyano-2-fluoro-phenylamino)-methyl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

Cyclopropanecarboxylic acid (5-{4-[(2-fluoro-4-methyl-phenylamino)-methyl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide

Cyclopropanecarboxylic acid [5-(4-pyrrolidin-1-ylmethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-amide,

Cyclopropanecarboxylic acid [5-(4-phenylaminomethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-amide,

Cyclopropanecarboxylic acid (5-{4-[3-(acetyl-methyl-amino)-pyrrolidin-1-ylmethyl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

Cyclopropanecarboxylic acid {5-[4-(3-dimethylamino-pyrrolidin-1-ylmethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-(3,3-difluoro-pyrrolidin-1-ylmethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid (5-{4-[3-(4-cyano-phenoxymethyl)-azetidin-1-ylmethyl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

Cyclopropanecarboxylic acid {5-[4-(2-oxo-2-piperidin-1-yl-ethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid (5-{4-[2-(1,1-dioxo-thiomorpholin-4-yl)-2-oxo-ethyl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

Cyclobutanecarboxylic acid 4-[2-(cyclopropanecarbonyl-amino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-benzylamide,

Cyclopropanecarboxylic acid {5-[4-(3-dimethylamino-piperidine-1-carbonyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-(3-hydroxy-piperidine-1-carbonyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-(3,3-difluoro-pyrrolidine-1-carbonyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid 4-[2-(cyclopropanecarbonyl-amino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-benzylamide,

4-[2-(Cyclopropanecarbonyl-amino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-N-(1,1-dioxo-tetrahydrothiophen-3-yl)-N-methyl-benzamide,

1-{4-[2-(Cyclopropanecarbonyl-amino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-benzoyl}-piperidine-4-carboxylic acid amide

1-{4-[2-(Cyclopropanecarbonyl-amino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-benzoyl}-piperidine-2-carboxylic acid amide,

Cyclopropanecarboxylic acid {5-[4-(3-hydroxymethyl-piperidine-1-carbonyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-(3-oxo-piperazine-1-carbonyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid (5-{4-[3-(4-cyano-phenoxy)-azetidin-1-ylmethyl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

(1-{4-[2-(Cyclopropanecarbonyl-amino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-benzyl}-azetidin-3-yl)-carbamic acid tert-butyl ester,

Cyclopropanecarboxylic acid {5-[4-(3-fluoro-piperidin-1-ylmethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-(4-methoxy-piperidin-1-ylmethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-(4-ethoxy-piperidin-1-ylmethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid (5-{4-[3-(acetyl-methyl-amino)-azetidin-1-ylmethyl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

Cyclopropanecarboxylic acid (5-{4-[3-(4-cyano-benzyloxy)-azetidin-1-yl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

Cyclopropanecarboxylic acid {5-[4-(3-diethylamino-pyrrolidine-1-carbonyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-(4-hydroxy-4-phenyl-piperidine-1-carbonyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-(3-acetylamino-azetidine-1-carbonyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-(3-cyano-azetidin-1-yl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-(3-dimethylamino-pyrrolidine-1-carbonyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid (5-{4-[3-(piperidine-1-carbonyl)-piperidine-1-carbonyl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

Cyclopropanecarboxylic acid {5-[4-(3-dimethylamino-azetidin-1-ylmethyl)-phenyl][1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid (5-{4-[4-(pyridin-3-yloxymethyl)-piperidine-1-carbonyl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

Cyclopropanecarboxylic acid {5-[4-(4-methoxy-piperidine-1-carbonyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-(4-ethoxy-piperidine-1-carbonyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

1-{4-[2-(Cyclopropanecarbonyl-amino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-benzoyl}-piperidine-3-carboxylic acid diethylamide,

Cyclopropanecarboxylic acid {5-[4-(3-acetylamino-piperidine-1-carbonyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid (5-{4-[acetyl-(6-cyano-pyridin-3-ylmethyl)-amino]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

Cyclopropanecarboxylic acid {5-[4-(3-dimethylaminomethyl-azetidin-1-ylmethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

1-{4-[2-(Cyclopropanecarbonyl-amino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-benzyl}-azetidine-3-carboxylic acid dimethylamide,

Cyclopropanecarboxylic acid {5-[4-(3-morpholin-4-yl-azetidin-1-ylmethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-(4-cyanomethyl-phenoxymethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-(isoxazol-3-ylaminomethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-(3-cyano-azetidin-1-ylmethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid (5-{4-[(1,1-dioxo-tetrahydro-thiophen-3-ylamino)-methyl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

Cyclopropanecarboxylic acid {5-[4-((S)-3-hydroxy-pyrrolidin-1-ylmethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

2-{4-[2-(Cyclopropanecarbonyl-amino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-benzylamino}-benzamide,

Cyclopropanecarboxylic acid {5-[4-((R)-3-hydroxy-pyrrolidin-1-ylmethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

4-Methyl-piperazine-1-carboxylic acid 4-[2-(cyclopropanecarbonyl-amino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-benzylamide,

Morpholine-4-carboxylic acid 4-[2-(cyclopropanecarbonyl-amino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-benzylamide,

(1-{4-[2-(Cyclopropanecarbonyl-amino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-benzyl}-piperidin-4-yl)-carbamic acid tert-butyl ester,

Cyclopropanecarboxylic acid {5-[4-(3-oxo-piperazin-1-ylmethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid [5-(4-cyclopropylaminomethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-amide

Cyclopropanecarboxylic acid {5-[4-(3-hydroxy-piperidin-1-ylmethyl)-phenyl][1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-(3,3-dimethyl-azetidin-1-ylmethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-(3,3-difluoro-azetidin-1-ylmethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-(pyridin-3-ylcarbamoylmethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid (5-{4-[2-(3,3-difluoro-azetidin-1-yl)-2-oxo-ethyl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

Cyclopropanecarboxylic acid {5-[4-(2-azetidin-1-yl-2-oxo-ethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid (5-{4-[2-oxo-2-(4-trifluoromethyl-piperidin-1-yl)-ethyl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

Cyclopropanecarboxylic acid (5-{4-[2-(3,5-dimethyl-piperidin-1-yl)-2-oxo-ethyl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

Cyclopropanecarboxylic acid (5-{4-[2-(3-methoxy-azetidin-1-yl)-2-oxo-ethyl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

Cyclopropanecarboxylic acid (5-{4-[2-(3-acetylamino-azetidin-1-yl)-2-oxo-ethyl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

Cyclopropanecarboxylic acid (5-{4-[2-(4-acetylamino-piperidin-1-yl)-2-oxo-ethyl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

1-(2-{4-[2-(Cyclopropanecarbonyl-amino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-phenyl}-acetyl)-azetidine-3-carboxylic acid dimethylamide,

Cyclopropanecarboxylic acid (5-{4-[3-(4-cyano-benzyloxy)-azetidine-1-carbonyl]-phenyl}-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide,

Cyclopropanecarboxylic acid {5-[4-(3-morpholin-4-yl-azetidine-1-carbonyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-(3-dimethylamino-azetidine-1-carbonyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-(3-cyano-azetidine-1-carbonyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide,

Cyclopropanecarboxylic acid {5-[4-(3-dimethylaminomethyl-azetidine-1-carbonyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide, and

4-[2-(Cyclopropanecarbonyl-amino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-N-(1H-1,2,4-triazol-3-yl)-benzamide, and

pharmaceutically acceptable salts of any of the foregoing.

Assignments (6)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 16, 2024
From: GALAPAGOS NV
To: ALFASIGMA S.P.A.
Reel/Frame 067126/0592 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 18, 2017
From: FLETCHER, STEPHEN ROBERT
To: GALAPAGOS SASU
Reel/Frame 041008/0415 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 18, 2017
From: GALAPAGOS SASU
To: GALAPAGOS NV
Reel/Frame 041008/0692 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 18, 2017
From: HODGES, ALASTAIR JAMES
To: BIOFOCUS DPI LTD.
Reel/Frame 041009/0005 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 18, 2017
From: BIOFOCUS DPI LTD.
To: GALAPAGOS NV
Reel/Frame 041009/0097 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 17, 2017
From: MENET, CHRISTEL JEANNE MARIE; BLANC, JAVIER; JOUANNIGOT, NOLWENN; VAN ROMPAEY, LUC JULIAAN CORINA; SMITS, KOEN KURT
To: GALAPAGOS NV
Reel/Frame 040989/0595 →
Continuity (5)
Division 14507396 · Oct 6, 2014
Division 13055936
Provisional Application 61135920 · Jul 25, 2008
Provisional Application 61220685 · Jun 26, 2009
Related Publication 20170035738A1 · Feb 9, 2017
Cited By (4)
US 12,234,235 US 12,329,758 US 12,502,394 US 12,558,360