US 11,530,210 B2Granted

Substituted heteroaromatic pyrazolo-pyridines and their use as GLUN2B receptor modulators

AssigneeJanssen Pharmaceutica NV

InventorsAfton Hiscox, Brice Stenne, Christa Chrovian, Christine Gelin, Andrew Samant, Michael A. Letavic, Curt Dvorak

Life of this patent

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Abstract

Substituted Pyrazolo-pyridines as GluN2B receptor ligands. Such compounds may be used in GluN2B receptor modulation and in pharmaceutical compositions and methods for the treatment of disease states, disorders, and conditions mediated by GluN2B receptor activity.

Claims129

Dependent claims

A compound having the structure of Formula (I):

or a pharmaceutically acceptable salt thereof,
wherein:
R1 is H, halo, or CH3;
Ar1 is selected from the group consisting of:
(a) phenyl substituted with one member selected from the group consisting of:
halo, C1-6alkyl, OC1-6alkyl, C1-6perhaloalkyl, and OC1-6perhaloalkyl;
(b) phenyl substituted with two or three members each independently selected from the group consisting of:
halo, C1-6alkyl, C1-6perhaloalkyl, OC1-6perhaloalkyl, and CO2H;
and
(c) thienyl substituted with a member selected from the group consisting of:
halo, C1-6alkyl, and C1-6perhaloalkyl;
and pyridine substituted with CF3;
and
R2 is selected from the group consisting of:
wherein
Ra is halo, C1-6alkyl or CN;
Rb is H or C1-2alkyl;
Rc is selected from the group consisting of:
H, C1-6alkyl, C1-6perhaloalkyl, CH2OH, OC1-6alkyl, OH, NH2, NH(CH3), N(CH3)2, NH(C═O)CH3, cyclopropyl, and phenyl;
X1 is NCH3, S or O;
X2 is O, NH or NCH3;
X3 is O or S;
X4 is NH or O;
X5 is NCH3 or O;
X6 is NCH3 or S;
and n is 2;
(b) phenyl;
phenyl substituted with one or two members independently selected from the group consisting of:
halo, OC1-6alkyl, C1-6perhaloalkyl, and CN;
and
wherein
Rd is H or OC1-6alkyl;
Re is a member selected from the group consisting of:
H, halo, C1-6alkyl,
C1-6perhaloalkyl, OC1-6alkyl, OC1-6perhaloalkyl, and CN;
and
Rf is H, C1-6alkyl or OC1-6alkyl.

34 more elements

A compound selected from the group consisting of:

1-(Pyrimidin-2-ylmethyl)-6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridine;
1-[(5-Bromo-3-pyridyl)methyl]-6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridine;
5-[[6-[3-(Trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]pyridine-3-carbonitrile;
1-[(2-Methylpyrimidin-5-yl)methyl]-6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridine;
1-(Pyrazin-2-ylmethyl)-6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridine;
1-(Pyrimidin-4-ylmethyl)-6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridine;
2-[[6-[3-(Trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-1,3,4-oxadiazole;
2-[[6-[3-(Difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-oxazole;
2-[[6-(2,4-Difluoro-3-methyl-phenyl)pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-oxazole;
2-[[6-[3-(Difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-1,3,4-oxadiazole;
6-[3-(Difluoromethoxy)-4-fluoro-phenyl]-1-(1H-pyrazol-4-ylmethyl)pyrazolo[4,3-b]pyridine;
6-[3-(1,1-Difluoroethyl)phenyl]-1-(3-pyridylmethyl)pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethyl)-4-fluoro-phenyl]-1-[(5-methyl-4H-1,2,4-triazol-3-yl)methyl]pyrazolo[4,3-b]pyridine;
1-[(3-Methyl-1H-pyrazol-5-yl)methyl]-6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridine;
5-[[6-[3-(Difluoromethoxy)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-N-methyl-1,3,4-thiadiazol-2-amine;
5-[[6-[3-(difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-1,3,4-thiadiazol-2-amine;
5-[[6-[3-(Difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-1,3,4-thiadiazol-2-ol;
5-[[6-[3-(Difluoromethoxy)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-1,3,4-thiadiazol-2-amine;
N-(5-((6-(3-(Difluoromethoxy)-4-fluorophenyl)-1H-pyrazolo[4,3-b]pyridin-1-yl) methyl)-1,3,4-thiadiazol-2-yl)acetamide;
3-[[6-[3-(Trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-1,2,4-oxadiazole;
1-Benzyl-6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridine;
1-[(3-Fluorophenyl)methyl]-6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridine;
3-[[6-[3-(Trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]benzonitrile;
1-[(4-Methoxyphenyl)methyl]-6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridine;
6-[3-(Trifluoromethyl)phenyl]-1-[[4-(trifluoromethyl)phenyl]methyl]pyrazolo[4,3-b]pyridine;
3-[[6-[3-(Difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]benzonitrile;
6-[3-(Difluoromethyl)-4-fluoro-phenyl]-1-[(3,5-difluorophenyl)methyl]pyrazolo[4,3-b]pyridine;
3-[[6-[3-(Difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-fluoro-benzonitrile;
3-[[6-[3-(Difluoromethoxy)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]benzonitrile;
6-[3-(Difluoromethoxy)-4-fluoro-phenyl]-1-[(3,5-difluorophenyl)methyl]pyrazolo[4,3-b]pyridine;
3-[[6-[3-(Difluoromethoxy)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-fluoro-benzonitrile;
6-[3-(Difluoromethyl)-4-fluoro-phenyl]-1-[(5-methyl-2-thienyl)methyl]pyrazolo[4,3-b]pyridine;
6-(3-(Difluoromethyl)-4-fluorophenyl)-1-((5-fluorothiophen-2-yl)methyl)-1H-pyrazolo[4,3-b]pyridine;
5-((6-(3-(Difluoromethyl)-4-fluorophenyl)-1H-pyrazolo[4,3-b]pyridin-1-yl)methyl)thiophene-2-carbonitrile;
6-[3-(1,1-Difluoroethyl)phenyl]-1-(1H-pyrazol-4-ylmethyl)pyrazolo[4,3-b]pyridine;
1-[(1-Methylimidazol-4-yl)methyl]-6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridine;
1-[(2,5-Dimethylpyrazol-3-yl)methyl]-6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethyl)-4-fluoro-phenyl]-1-(1H-pyrazol-4-ylmethyl)pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethyl)-4-fluoro-phenyl]-1-[(1-methylpyrazol-3-yl)methyl]pyrazolo[4,3-b]pyridine;
6-[3-(1,1-Difluoroethyl)-4-fluoro-phenyl]-1-(1H-pyrazol-4-ylmethyl)pyrazolo[4,3-b]pyridine;
6-[4-Chloro-3-(difluoromethoxy)phenyl]-1-(1H-pyrazol-4-ylmethyl)pyrazolo[4,3-b]pyridine;
5-[[6-(4-Fluorophenyl)pyrazolo[4,3-b]pyridin-1-yl]methyl]-3-methyl-isoxazole;
3-[[6-(4-Fluorophenyl)pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-isoxazole;
3-[[6-[3-(Trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]isoxazole;
3-[[6-[3-(1,1-Difluoroethyl)phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-isoxazole;
4-[[6-[3-(Trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]oxazole;
5-Methyl-3-[[6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]isoxazole;
5-[[6-(4-Fluoro-3-methyl-phenyl)pyrazolo[4,3-b]pyridin-1-yl]methyl]-2-methyl-oxazole;
2-[[6-(4-Fluoro-3-methyl-phenyl)pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-oxazole;
5-[[6-[3-(Difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]isoxazole;
3-[[6-[3-(Difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]isoxazole;
5-[[6-[3-(Difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-3-methyl-isoxazole;
3-[[6-[3-(Difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-isoxazole;
5-[[6-[3-(Difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-2-methyl-oxazole;
4-[[6-[3-(Difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-2-methyl-oxazole;
3-[[6-[3-(Difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-4-methyl-isoxazole;
4-[[6-[3-(Difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-3,5-dimethyl-isoxazole;
3-[[6-[3-(1,1-Difluoroethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-isoxazole;
3-[[6-[3-(Difluoromethoxy)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-isoxazole;
5-[[6-[3-(Difluoromethoxy)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-2-methyl-oxazole;
2-[[6-[3-(Difluoromethoxy)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-oxazole;
3-[[6-[4-Chloro-3-(difluoromethoxy)phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-isoxazole;
5-[[6-(2,4-Difluoro-3-methyl-phenyl)pyrazolo[4,3-b]pyridin-1-yl]methyl]-2-methyl-oxazole;
5-Methyl-3-[[6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]isothiazole;
2-[[6-[3-(Difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-thiazole;
2-[[6-[3-(Difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-4-methyl-thiazole;
4-[[6-[3-(Difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-2-methyl-thiazole;
2-[[6-(4-Fluoro-3-methyl-phenyl)pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-thiazole;
2-[[6-[3-(Difluoromethoxy)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-thiazole;
2-[[6-(2,4-Difluoro-3-methyl-phenyl)pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-thiazole;
1-[(1-Methyl-1,2,4-triazol-3-yl)methyl]-6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethoxy)-4-fluoro-phenyl]-1-[(1-methyltriazol-4-yl)methyl]pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethyl)-4-fluoro-phenyl]-1-[(1-methyl-1,2,4-triazol-3-yl)methyl]pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethyl)-4-fluoro-phenyl]-1-[(4-methyl-1,2,4-triazol-3-yl)methyl]pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethyl)-4-fluoro-phenyl]-1-[(4,5-dimethyl-1,2,4-triazol-3-yl)methyl]pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethyl)-4-fluoro-phenyl]-1-[(5-ethyl-4-methyl-1,2,4-triazol-3-yl)methyl]pyrazolo[4,3-b]pyridine;
2-[[6-(5-Chloro-2-thienyl)pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-1,3,4-oxadiazole;
2-Methyl-5-[[6-[5-(trifluoromethyl)-2-thienyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-1,3,4-oxadiazole;
2-[[6-[5-(Difluoromethyl)-2-thienyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-1,3,4-oxadiazole;
5-[[6-(4-Fluorophenyl)pyrazolo[4,3-b]pyridin-1-yl]methyl]-3-methyl-1,2,4-oxadiazole;
5-[[6-(3-Methoxyphenyl)pyrazolo[4,3-b]pyridin-1-yl]methyl]-3-methyl-1,2,4-oxadiazole;
2-[[6-[3-(1,1-Difluoroethyl)phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-1,3,4-oxadiazole;
2-[[6-[3-(1,1-Difluoroethyl)phenyl]-3-fluoro-pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-1,3,4-oxadiazole;
3-Methyl-5-[[6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-1,2,4-oxadiazole;
2-Methyl-5-[[6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-1,3,4-oxadiazole;
5-Methyl-3-[[6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-1,2,4-oxadiazole;
5-[[6-[3-(Trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-1,2,4-oxadiazole;
2-Methyl-5-[[6-[2-(trifluoromethyl)-4-pyridyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-1,3,4-oxadiazole;
2-[[6-(4-Fluoro-3-methyl-phenyl)pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-1,3,4-oxadiazole;
2-[[3-Fluoro-6-(4-fluoro-3-methyl-phenyl)pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-1,3,4-oxadiazole;
2-[[6-(4-Fluoro-3-methyl-phenyl)pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-(trifluoromethyl)-1,3,4-oxadiazole;
2-[[6-(3-Chloro-4-fluoro-phenyl)pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-1,3,4-oxadiazole;
2-[[6-(3-Chloro-4-fluoro-phenyl)-3-fluoro-pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-1,3,4-oxadiazole;
2-[[6-[3-(Difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-1,3,4-oxadiazole;
5-[[6-[3-(Difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-3-methyl-1,2,4-oxadiazole;
2-[[6-[3-(Difluoromethyl)-4-fluoro-phenyl]-3-fluoro-pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-1,3,4-oxadiazole;
3-[[6-[3-(Difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-1,2,4-oxadiazole;
3-[[6-[3-(Difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-4-methyl-1,2,5-oxadiazole;
2-Cyclopropyl-5-[[6-[3-(difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-1,3,4-oxadiazole;
2-[[6-[3-(Difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-isopropyl-1,3,4-oxadiazole;
5-[[6-[3-(Difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-N,N-dimethyl-1,3,4-oxadiazol-2-amine;
2-[[6-[3-(Difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-(trifluoromethyl)-1,3,4-oxadiazole;
2-[[6-[3-(Difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-phenyl-1,3,4-oxadiazole;
2-[[6-[3-(1,1-Difluoroethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-1,3,4-oxadiazole;
2-[[6-[3-(1,1-Difluoroethyl)-4-fluoro-phenyl]-3-fluoro-pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-1,3,4-oxadiazole;
2-[[6-[4-Chloro-3-(difluoromethyl)phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-1,3,4-oxadiazole;
2-[[6-[4-Chloro-3-(difluoromethyl)phenyl]-3-fluoro-pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-1,3,4-oxadiazole;
5-[[6-[3-Fluoro-5-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-3-methyl-1,2,4-oxadiazole;
5-[[6-[2-Fluoro-5-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-3-methyl-1,2,4-oxadiazole;
5-[[6-[4-Fluoro-3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-3-methyl-1,2,4-oxadiazole;
5-[[6-[2-Fluoro-3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-3-methyl-1,2,4-oxadiazole;
5-[[6-[3-(Difluoromethoxy)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-3-methyl-1,2,4-oxadiazole;
2-[[6-[3-(Difluoromethoxy)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-1,3,4-oxadiazole;
3-[[6-[3-(Difluoromethoxy)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-1,2,4-oxadiazole;
2-[[6-[3-(Difluoromethoxy)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-(trifluoromethyl)-1,3,4-oxadiazole;
2-[[6-[4-Chloro-3-(difluoromethoxy)phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-1,3,4-oxadiazole;
2-[[6-[4-Chloro-3-(difluoromethoxy)phenyl]-3-fluoro-pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-1,3,4-oxadiazole;
2-[[6-(2,4-Difluoro-3-methyl-phenyl)pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-1,3,4-oxadiazole;
2-[[6-(2,4-Difluoro-3-methyl-phenyl)pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-(trifluoromethyl)-1,3,4-oxadiazole;
4-[[6-[3-(Trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]thiadiazole;
2-[[6-[3-(Difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-1,3,4-thiadiazole;
2-[[6-[3-(Difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-1,3,4-thiadiazole;
2-[[6-[3-(Difluoromethyl)-4-fluoro-phenyl]-3-fluoro-pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-1,3,4-thiadiazole;
2-[[6-[3-(Difluoromethyl)-4-fluoro-phenyl]-3-methyl-pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-1,3,4-thiadiazole;
2-[[6-[3-(Difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-ethyl-1,3,4-thiadiazole;
5-((6-(3-(difluoromethyl)-4-fluorophenyl)-1H-pyrazolo[4,3-b]pyridin-1-yl)methyl)-N-methyl-1,3,4-thiadiazol-2-amine;
2-[[6-[3-(difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methoxy-1,3,4-thiadiazole;
N-(5-((6-(3-(Difluoromethyl)-4-fluorophenyl)-1H-pyrazolo[4,3-b]pyridin-1-yl)methyl)-1,3,4-thiadiazol-2-yl)acetamide;
2-(Difluoromethyl)-5-[[6-[3-(difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-1,3,4-thiadiazole;
2-Cyclopropyl-5-[[6-[3-(difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-1,3,4-thiadiazole;
2-[[6-[4-Chloro-3-(difluoromethyl)phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-1,3,4-thiadiazole;
2-[[6-(4-Fluoro-3-methyl-phenyl)pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-1,3,4-thiadiazole;
2-[[6-[3-(Difluoromethoxy)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-1,3,4-thiadiazole;
2-[[6-[3-(difluoromethoxy)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methoxy-1,3,4-thiadiazole;
2-[[6-[4-Chloro-3-(difluoromethoxy)phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-1,3,4-thiadiazole;
2-[[6-(2,4-Difluoro-3-methyl-phenyl)pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-1,3,4-thiadiazole;
6-(4-Methyl-2-thienyl)-1-(3-pyridylmethyl)pyrazolo[4,3-b]pyridine;
1-[(5-Methyl-3-pyridyl)methyl]-6-(4-methyl-2-thienyl)pyrazolo[4,3-b]pyridine;
6-(5-Methyl-2-thienyl)-1-(3-pyridylmethyl)pyrazolo[4,3-b]pyridine;
5-[[6-(5-Chloro-2-thienyl)pyrazolo[4,3-b]pyridin-1-yl]methyl]pyridine-3-carbonitrile;
6-(3-Chloro-2-thienyl)-1-(3-pyridylmethyl)pyrazolo[4,3-b]pyridine;
5-[[6-[5-(Difluoromethyl)-2-thienyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]pyridine-3-carbonitrile;
1-((6-Fluoropyridin-3-yl)methyl)-6-(5-(trifluoromethyl)thiophen-2-yl)-1H-pyrazolo[4,3-b]pyridine;
5-[[6-[5-(Trifluoromethyl)-2-thienyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]pyridine-3-carbonitrile;
1-[(6-Fluoro-3-pyridyl)methyl]-6-(m-tolyl)pyrazolo[4,3-b]pyridine;
1-[(5-Fluoro-3-pyridyl)methyl]-6-(m-tolyl)pyrazolo[4,3-b]pyridine;
3-Fluoro-1-[(5-fluoro-3-pyridyl)methyl]-6-(m-tolyl)pyrazolo[4,3-b]pyridine;
6-(4-Chlorophenyl)-1-[(5-fluoro-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-(4-Fluorophenyl)-1-(2-pyridylmethyl)pyrazolo[4,3-b]pyridine;
6-(4-Fluorophenyl)-1-[(5-methoxy-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
1-[[5-(Difluoromethoxy)-3-pyridyl]methyl]-6-(4-fluorophenyl)pyrazolo[4,3-b]pyridine;
6-(3-Fluorophenyl)-1-(2-pyridylmethyl)pyrazolo[4,3-b]pyridine;
6-(2-Fluorophenyl)-1-[(5-fluoro-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-(3-Methoxyphenyl)-1-(2-pyridylmethyl)pyrazolo[4,3-b]pyridine;
1-[(6-Fluoro-3-pyridyl)methyl]-6-(3-methoxyphenyl)pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethyl)phenyl]-1-(2-pyridylmethyl)pyrazolo[4,3-b]pyridine;
5-[[6-[3-(Difluoromethyl)phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]pyridine-3-carbonitrile;
1-[(5-Chloro-3-pyridyl)methyl]-6-[3-(difluoromethyl)phenyl]pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethoxy)phenyl]-1-[(5-fluoro-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-[3-(1,1-Difluoroethyl)phenyl]-1-[(5-methyl-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-[3-(1,1-Difluoroethyl)phenyl]-1-[(5-fluoro-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
1-(2-Pyridylmethyl)-6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridine;
1-(3-Pyridylmethyl)-6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridine;
1-(4-Pyridylmethyl)-6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridine;
1-[(6-Methyl-3-pyridyl)methyl]-6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridine;
1-[(2-Methyl-3-pyridyl)methyl]-6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridine;
1-[(5-Methyl-3-pyridyl)methyl]-6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridine;
1-[(4-Methyl-3-pyridyl)methyl]-6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridine;
1-[(6-Fluoro-3-pyridyl)methyl]-6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridine;
1-[(2-Fluoro-3-pyridyl)methyl]-6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridine;
1-[(5-Fluoro-3-pyridyl)methyl]-6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridine;
1-[(2-Methoxy-3-pyridyl)methyl]-6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridine;
1-[(5-Methoxy-3-pyridyl)methyl]-6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridine;
6-[3-(Trifluoromethyl)phenyl]-1-[[6-(trifluoromethyl)-3-pyridyl]methyl]pyrazolo[4,3-b]pyridine;
6-[3-(Trifluoromethyl)phenyl]-1-[[5-(trifluoromethyl)-3-pyridyl]methyl]pyrazolo[4,3-b]pyridine;
6-[3-(Trifluoromethyl)phenyl]-1-[[4-(trifluoromethyl)-3-pyridyl]methyl]pyrazolo[4,3-b]pyridine;
6-(4-Fluoro-3-methyl-phenyl)-1-(3-pyridylmethyl)pyrazolo[4,3-b]pyridine;
3-Fluoro-6-(4-fluoro-3-methyl-phenyl)-1-(3-pyridylmethyl)pyrazolo[4,3-b]pyridine;
6-(4-Fluoro-3-methyl-phenyl)-1-[(2-methyl-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-(4-Fluoro-3-methyl-phenyl)-1-[(5-methyl-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-(4-Fluoro-3-methyl-phenyl)-1-[(4-methyl-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-(4-Fluoro-3-methyl-phenyl)-1-[(6-fluoro-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-(4-Fluoro-3-methyl-phenyl)-1-[(5-fluoro-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-(3,5-Difluorophenyl)-1-[(4-methyl-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-(3,5-Difluorophenyl)-1-[(5-fluoro-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-(3,4-Difluorophenyl)-1-(2-pyridylmethyl)pyrazolo[4,3-b]pyridine;
6-(3,4-Difluorophenyl)-1-(3-pyridylmethyl)pyrazolo[4,3-b]pyridine;
6-(3,4-Difluorophenyl)-1-[(2-methyl-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-(3,4-Difluorophenyl)-1-[(5-methyl-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-(3,4-Difluorophenyl)-1-[(4-methyl-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-(3,4-Difluorophenyl)-1-[(6-fluoro-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-(3,4-Difluorophenyl)-1-[(5-fluoro-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-(3,4-Difluorophenyl)-1-[(5-methoxy-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
1-[[5-(Difluoromethoxy)-3-pyridyl]methyl]-6-(3,4-difluorophenyl)pyrazolo[4,3-b]pyridine;
6-(3-Chloro-4-fluoro-phenyl)-1-[(5-fluoro-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-(3-Chloro-4-fluoro-phenyl)-1-[(5-methoxy-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethyl)-4-fluoro-phenyl]-1-(2-pyridylmethyl)pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethyl)-4-fluoro-phenyl]-1-(3-pyridylmethyl)pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethyl)-4-fluoro-phenyl]-3-methyl-1-(3-pyridylmethyl)pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethyl)-4-fluoro-phenyl]-1-[(5-methyl-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-(3-(Difluoromethyl)-4-fluorophenyl)-1-((6-fluoropyridin-3-yl)methyl)-1H-pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethyl)-4-fluoro-phenyl]-1-[(5-fluoro-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
5-[[6-[3-(Difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]pyridine-3-carbonitrile;
6-[3-(Difluoromethyl)-4-fluoro-phenyl]-1-[(6-methoxy-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethyl)-4-fluoro-phenyl]-1-[(6-methoxy-2-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethyl)-4-fluoro-phenyl]-1-[(2-methoxy-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethyl)-4-fluoro-phenyl]-1-[(5-methoxy-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
1-[(5-Chloro-3-pyridyl)methyl]-6-[3-(difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethyl)-4-fluoro-phenyl]-1-[[5-(difluoromethyl)-3-pyridyl]methyl]pyrazolo[4,3-b]pyridine;
1-[[5-(Difluoromethoxy)-3-pyridyl]methyl]-6-[3-(difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethyl)-4-fluoro-phenyl]-1-[[5-(trifluoromethyl)-3-pyridyl]methyl]pyrazolo[4,3-b]pyridine;
5-[[6-[3-(Difluoromethyl)-2-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]pyridine-3-carbonitrile;
1-[(5-Chloro-3-pyridyl)methyl]-6-[3-(difluoromethyl)-2-fluoro-phenyl]pyrazolo[4,3-b]pyridine;
6-(3,4-Dichlorophenyl)-1-[(6-fluoro-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-(3,4-Dichlorophenyl)-1-[(5-methoxy-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-[3-(1,1-Difluoroethyl)-4-fluoro-phenyl]-1-(3-pyridylmethyl)pyrazolo[4,3-b]pyridine;
6-[3-(1,1-Difluoroethyl)-4-fluoro-phenyl]-1-[(5-methyl-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-[3-(1,1-Difluoroethyl)-4-fluoro-phenyl]-1-[(5-fluoro-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
5-[[6-[3-(1,1-Difluoroethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]pyridine-3-carbonitrile;
6-[3-(1,1-Difluoroethyl)-4-fluoro-phenyl]-1-[(5-methoxy-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
1-[(5-Chloro-3-pyridyl)methyl]-6-[3-(1,1-difluoroethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethoxy)-4-fluoro-phenyl]-1-(2-pyridylmethyl)pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethoxy)-4-fluoro-phenyl]-1-(3-pyridylmethyl)pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethoxy)-4-fluoro-phenyl]-1-[(5-methyl-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethoxy)-4-fluoro-phenyl]-1-[(5-fluoro-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
5-[[6-[3-(Difluoromethoxy)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]pyridine-3-carbonitrile;
6-[3-(Difluoromethoxy)-4-fluoro-phenyl]-1-[(6-methoxy-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethoxy)-4-fluoro-phenyl]-1-[(6-methoxy-2-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethoxy)-4-fluoro-phenyl]-1-[(2-methoxy-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethoxy)-4-fluoro-phenyl]-1-[(5-methoxy-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
1-[(5-Chloro-3-pyridyl)methyl]-6-[3-(difluoromethoxy)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridine;
6-[4-Chloro-3-(Difluoromethyl)phenyl]-1-[(5-methoxy-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
1-[(5-Fluoro-3-pyridyl)methyl]-6-[4-fluoro-3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridine;
6-[4-Fluoro-3-(trifluoromethyl)phenyl]-1-[(5-methoxy-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-(3-Bromo-4-fluorophenyl)-1-((6-fluoropyridin-3-yl)methyl)-1H-pyrazolo[4,3-b]pyridine;
5-[[6-[4-Chloro-3-(1,1-difluoroethyl)phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]pyridine-3-carbonitrile;
6-[4-Chloro-3-(1,1-difluoroethyl)phenyl]-1-[(5-chloro-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-[4-Chloro-3-(difluoromethoxy)phenyl]-1-(3-pyridylmethyl)pyrazolo[4,3-b]pyridine;
6-[4-Chloro-3-(difluoromethoxy)phenyl]-1-[(5-methyl-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-[4-Chloro-3-(difluoromethoxy)phenyl]-1-[(5-fluoro-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
5-[[6-[4-Chloro-3-(difluoromethoxy)phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]pyridine-3-carbonitrile;
6-[4-Chloro-3-(difluoromethoxy)phenyl]-1-[(5-methoxy-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-[4-Chloro-3-(difluoromethoxy)phenyl]-1-[(5-chloro-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-(2,4-Difluoro-3-methyl-phenyl)-1-(2-pyridylmethyl)pyrazolo[4,3-b]pyridine;
6-(2,4-Difluoro-3-methyl-phenyl)-1-(3-pyridylmethyl)pyrazolo[4,3-b]pyridine;
6-(2,4-Difluoro-3-methyl-phenyl)-1-[(5-methyl-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-(2,4-Difluoro-3-methyl-phenyl)-1-[(4-methyl-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-(2,4-Difluoro-3-methyl-phenyl)-1-[(6-fluoro-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
6-(2,4-Difluoro-3-methyl-phenyl)-1-[(5-fluoro-3-pyridyl)methyl]pyrazolo[4,3-b]pyridine;
1-(2-Pyridylmethyl)-6-(3,4,5-trifluorophenyl)pyrazolo[4,3-b]pyridine;
1-[(5-Fluoro-3-pyridyl)methyl]-6-(3,4,5-trifluorophenyl)pyrazolo[4,3-b]pyridine;
1-[(5-Methoxy-3-pyridyl)methyl]-6-(3,4,5-trifluorophenyl)pyrazolo[4,3-b]pyridine;
1-[[5-(Difluoromethoxy)-3-pyridyl]methyl]-6-(3,4,5-trifluorophenyl)pyrazolo[4,3-b]pyridine;
1-(Pyridazin-4-ylmethyl)-6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridine;
6-(m-Tolyl)-1-(pyridazin-3-ylmethyl)pyrazolo[4,3-b]pyridine;
6-(3-Fluorophenyl)-1-(pyridazin-3-ylmethyl)pyrazolo[4,3-b]pyridine;
6-[3-(1,1-Difluoroethyl)phenyl]-1-(pyridazin-3-ylmethyl)pyrazolo[4,3-b]pyridine;
1-(Pyridazin-3-ylmethyl)-6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridine;
6-(4-Fluoro-3-methyl-phenyl)-1-(pyridazin-3-ylmethyl)pyrazolo[4,3-b]pyridine;
6-[3-(1,1-Difluoroethyl)-4-fluoro-phenyl]-1-(pyridazin-3-ylmethyl)pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethyl)-4-fluoro-phenyl]-1-(pyridazin-3-ylmethyl)pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethyl)-4-fluoro-phenyl]-1-[(6-methylpyridazin-3-yl)methyl]pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethoxy)-4-fluoro-phenyl]-1-(pyridazin-3-ylmethyl)pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethoxy)-4-fluoro-phenyl]-1-[(6-methylpyridazin-3-yl)methyl]pyrazolo[4,3-b]pyridine;
6-[4-Chloro-3-(difluoromethoxy)phenyl]-1-(pyridazin-3-ylmethyl)pyrazolo[4,3-b]pyridine;
6-(3,4-Difluorophenyl)-1-(pyridazin-3-ylmethyl)pyrazolo[4,3-b]pyridine;
6-(4-Chloro-3-methyl-phenyl)-1-(pyridazin-3-ylmethyl)pyrazolo[4,3-b]pyridine;
1-(Pyridazin-3-ylmethyl)-6-(3,4,5-trifluorophenyl)pyrazolo[4,3-b]pyridine;
6-(2,4-Difluoro-3-methyl-phenyl)-1-(pyridazin-3-ylmethyl)pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethyl)-4-fluoro-phenyl]-1-(pyrimidin-4-ylmethyl)pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethoxy)-4-fluoro-phenyl]-1-(pyrimidin-4-ylmethyl)pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethyl)-4-fluoro-phenyl]-1-(pyrazin-2-ylmethyl)pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethoxy)-4-fluoro-phenyl]-1-(pyrazin-2-ylmethyl)pyrazolo[4,3-b]pyridine;
6-[3-(1,1-Difluoroethyl)phenyl]-1-(pyrimidin-5-ylmethyl)pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethyl)-4-fluoro-phenyl]-1-(pyrimidin-5-ylmethyl)pyrazolo[4,3-b]pyridine;
1-(Pyrimidin-5-ylmethyl)-6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridine;
6-[3-(1,1-Difluoroethyl)-4-fluoro-phenyl]-1-(pyrimidin-5-ylmethyl)pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethoxy)-4-fluoro-phenyl]-1-(pyrimidin-5-ylmethyl)pyrazolo[4,3-b]pyridine;
6-[4-Chloro-3-(difluoromethoxy)phenyl]-1-(pyrimidin-5-ylmethyl)pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethyl)-4-fluoro-phenyl]-1-[(6-methylpyrimidin-4-yl)methyl]pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethoxy)-4-fluoro-phenyl]-1-[(6-methylpyrimidin-4-yl)methyl]pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethyl)-4-fluoro-phenyl]-1-[(2-methylpyrimidin-4-yl)methyl]pyrazolo[4,3-b]pyridine;
1-[(2-Methylpyrimidin-4-yl)methyl]-6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethoxy)-4-fluoro-phenyl]-1-[(2-methylpyrimidin-4-yl)methyl]pyrazolo[4,3-b]pyridine;
6-(3,4-Difluorophenyl)-1-[(2-methylpyrimidin-5-yl)methyl]pyrazolo[4,3-b]pyridine;
6-(4-Chloro-3-methyl-phenyl)-1-[(2-methylpyrimidin-5-yl)methyl]pyrazolo[4,3-b]pyridine;
1-[(5-Methylpyrimidin-2-yl)methyl]-6-[3-(trifluoromethyl)phenyl]pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethyl)-4-fluoro-phenyl]-1-[(6-methoxypyrimidin-4-yl)methyl]pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethoxy)-4-fluoro-phenyl]-1-[(6-methoxypyrimidin-4-yl)methyl]pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethyl)-4-fluoro-phenyl]-1-[(2-methoxypyrimidin-4-yl)methyl]pyrazolo[4,3-b]pyridine;
6-[3-(Difluoromethoxy)-4-fluoro-phenyl]-1-[(2-methoxypyrimidin-4-yl)methyl]pyrazolo[4,3-b]pyridine;
(5-((6-(3-(Difluoromethyl)-4-fluorophenyl)-1H-pyrazolo[4,3-b]pyridin-1-yl)methyl)-1,3,4-oxadiazol-2-yl)methanol;
2-Fluoro-5-(1-((5-methyl-1,3,4-oxadiazol-2-yl)methyl)-1H-pyrazolo[4,3-b]pyridin-6-yl)benzoic acid;
6-(3-(Difluoromethyl)-4-fluorophenyl)-1-((6-(fluoro-18F)pyridin-3-yl)methyl)-1H-pyrazolo[4,3-b]pyridine;
2-[[3-Bromo-6-[3-(difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-1,3,4-oxadiazole;
2-[[6-[3-(Difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-1,3,4-oxadiazole;
2-[[3-Deuterio-6-[3-(difluoromethyl)-4-fluoro-phenyl]pyrazolo[4,3-b]pyridin-1-yl]methyl]-5-methyl-1,3,4-oxadiazole;
and pharmaceutically acceptable salts, thereof.

295 more elements

Dependencies are inferred from the claim text.

Facts

Application: 16/899,829Filed 12 Jun 2020 · us provisional application
Priority: PK 349/20203 Jun 2020
Published: US 2021/0017169 A121 Jan 2021
Granted: 20 Dec 2022
Term ends: Not estimatedThe source records don’t support an estimate.

Classification4 codes

A61P 25/00
Drugs for disorders of the nervous system
C07D 471/04
In which the condensed system contains two hetero rings: ortho-condensed systems
A61P
Therapeutic uses of medicines
C07D
Heterocyclic compounds

Family

Application62/861,665Us provisional application · filed 14 Jun 2019
US 2021/0017169 A1Pre-grant publication · published 21 Jan 2021
US 11,530,210 B2This patent

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

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Abstract

Facts

Application

16/899,829Filed 12 Jun 2020 · us provisional application

Priority

PK 349/20203 Jun 2020

Published

US 2021/0017169 A121 Jan 2021

Granted

20 Dec 2022

Term ends

Not estimatedThe source records don’t support an estimate.

Classification4 codes

A61P 25/00
Drugs for disorders of the nervous system
C07D 471/04
In which the condensed system contains two hetero rings: ortho-condensed systems
A61P
Therapeutic uses of medicines
C07D
Heterocyclic compounds