IP Library › Granted Patent US 9,415,037
Granted Patent B2
US 9,415,037 · App. 14/507,396 · Granted Aug 16, 2016

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
A61K31/437A61K31/4545A61K31/4725A61K31/496A61K31/497A61K31/501A61K31/506A61K31/5377A61K31/541A61K31/551C07D471/04
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Quick Facts
Patent No.
US 9,415,037
App. No.
14/507,396
Granted
Aug 16, 2016
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 (319)

1. A method for the treatment of ulcerative colitis, said method comprising administering a therapeutically effective amount of a compound according to Formula III:

wherein the group

is selected from:

n2 is n1, and n1 is 0, 1, 2, 3 or 4;

R 3b is

—OPh, and O-(4-F-Ph), or

CO—R 3c ; and R 3c is:

or

R 3b is

Cy3 is selected from:

each R 5a is independently C 1 -C 4 alkyl, halo, CF 3 or Phenyl;

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

R 5c is H, or C 1 -C 4 alkyl;

m5 is 0, 1, or 2;

n5 is 0, 1, or 2,

or a pharmaceutically acceptable salt thereof.

2. The method of claim 1 wherein said compound is prepared and administered as a pharmaceutical composition comprising a pharmaceutically acceptable carrier and a pharmaceutically effective amount of said compound or a pharmaceutically acceptable salt thereof.

3. A method for the treatment of ulcerative colitis, said method comprising administering a therapeutically effective amount of a compound according to formulae Va, Vb, Vc, or Vd:

4. A method for the treatment of ulcerative colitis, said method comprising administering a therapeutically effective amount of a compound according to formulae VIc, or VId:

5. A method for the treatment of ulcerative colitis, said method comprising administering a therapeutically effective amount of a compound according to formulae VIIa, VIIb, VIIc, VIId, VIIe or VIIf:

6. A method for the treatment of ulcerative colitis, said method comprising administering a therapeutically effective amount of a compound selected 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-acetoylpiperazin-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-difluoropiperidine-1-carbonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide,

N-(5-(4-(3-phenylpiperidine-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-dimethylpiperidine-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-(1,1-dioxo-thiomorpholin-4-ylmethyl)-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.

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 May 6, 2016
From: MENET, CHRISTEL JEANNE MARIE; BLANC, JAVIER; JOUANNIGOT, NOLWENN; VAN ROMPAEY, LUC JULIAAN CORINA; SMITS, KOEN KURT
To: GALAPAGOS NV
Reel/Frame 038484/0606 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 6, 2016
From: FLETCHER, STEPHEN ROBERT
To: GALAPAGOS SASU
Reel/Frame 038484/0811 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 6, 2016
From: GALAPAGOS SASU
To: GALAPAGOS NV
Reel/Frame 038484/0921 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 6, 2016
From: HODGES, ALASTAIR JAMES
To: BIOFOCUS DPI
Reel/Frame 038485/0056 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 6, 2016
From: BIOFOCUS DPI LTD.
To: GALAPAGOS NV
Reel/Frame 038485/0152 →
Continuity (4)
Division 13055936
Provisional Application 61135920 · Jul 25, 2008
Provisional Application 61220685 · Jun 26, 2009
Related Publication 20150150856A1 · Jun 4, 2015