IP Library › Granted Patent US 9,260,425
Granted Patent B2
US 9,260,425 · App. 13/571,595 · Granted Feb 16, 2016

Pyrazolo[3,4-c]pyridine compounds and methods of use

Inventors: Steven Do (San Jose, CA); Huiyong Hu (San Mateo, CA); Aleksandr Kolesnikov (San Francisco, CA); Wendy Lee (San Ramon, CA); Vickie H. Tsui (San Francisco, CA); Xiaojing Wang (Foster City, CA); Zhaoyang Wen (San Francisco, CA)
Assignee: Genetech, Inc.
C07D471/04C07D231/00
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Quick Facts
Patent No.
US 9,260,425
App. No.
13/571,595
Granted
Feb 16, 2016
Kind
B2
Abstract

Pyrazolo[3,4-c]pyridine compounds of Formula I, including stereoisomers, geometric isomers, tautomers, and pharmaceutically acceptable salts thereof, wherein R 1 and R 2 are as defined herein, are useful for inhibiting Pim kinase, and for treating disorders such as cancer mediated by Pim kinase. Methods of using compounds of Formula I for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.

Claims (412)

1. A compound selected from Formula I:

and stereoisomers, geometric isomers, tautomers, or pharmaceutically acceptable salts thereof, wherein:

R 1 is selected from C 2 -C 20 heterocyclyl, C 1 -C 20 heteroaryl, —(C 1 -C 20 heteroaryl)-(C 1 -C 20 heteroaryl), —(C 1 -C 20 heteroaryl)-(C 2 -C 20 heterocyclyl), —(C 1 -C 20 heteroaryl)-O—(C 2 -C 20 heterocyclyl), —(C 1 -C 20 heteroaryl)-O—(C 1 -C 12 alkylene)-(C 2 -C 20 heterocyclyl), —(C 1 -C 20 heteroaryl)-NR 3 —(C 2 -C 20 heterocyclyl), and —(C 1 -C 20 heteroaryl)-NR 3 —(C 1 -C 12 alkylene)-(C 2 -C 20 heterocyclyl);

R 2 is selected from C 2 -C 20 heterocyclyl, C 1 -C 20 heteroaryl, C 6 -C 20 aryl, —(C 6 -C 20 aryl)-(C 2 -C 20 heterocyclyl), —(C 1 -C 20 heteroaryl)-(C 1 -C 20 heteroaryl), —(C 1 -C 20 heteroaryl)-(C 2 -C 20 heterocyclyl), —(C 1 -C 20 heteroaryl)-(C 2 -C 20 heterocyclyl)-(C 2 -C 20 heterocyclyl), —(C 1 -C 20 heteroaryl)-NR 3 —(C 2 -C 20 heterocyclyl), —(C 1 -C 20 heteroaryl)-(C 1 -C 12 alkylene)-(C 2 -C 20 heterocyclyl), —(C 1 -C 20 heteroaryl)-NR 3 —(C 1 -C 12 alkylene)-(C 2 -C 20 heterocyclyl), and —(C 1 -C 20 heteroaryl)-NR 3 —(C 1 -C 12 alkylene)-(C 1 -C 20 heteroaryl);

R 3 is independently selected from H and C 1 -C 12 alkyl optionally substituted with F, Cl, CN, —CO 2 H, —COCH 3 , —CO 2 CH 3 , —CO 2 C(CH 3 ) 3 , —COCH(OH)CH 3 , —CONH 2 , —CONHCH 3 , —CON(CH 3 ) 2 , —NO 2 , —NH 2 , —NHCH 3 , —N(CH 3 ) 2 , —NHCOCH 3 , —N(CH 3 )COCH 3 , —NHS(O) 2 CH 3 , —NHCH 2 CH 2 NH 2 , —NHCH 2 CH 2 CH 2 NH 2 , —NHCH 2 CH 2 CH 2 CH 2 NH 2 , —N(CH 3 )C(CH 3 ) 2 CONH 2 , —N(CH 3 )CH 2 CH 2 S(O) 2 CH 3 , ═O, —OH, —OCH 3 , —OCH 2 CH 2 OCH 3 , —OCH 2 CH 2 NH 2 , —S(O) 2 N(CH 3 ) 2 , —SCH 3 , and —S(O) 2 CH 3 ;

where alkyl, alkylene, heterocyclyl, aryl, and heteroaryl are optionally substituted with one or more groups independently selected from F, Cl, Br, I, —CH 3 , —CH 2 CH 3 , —CH(CH 3 ) 2 , —CH 2 CH(CH 3 ) 2 , —CH 2 NH 2 , —CH 2 NHCH 3 , —CH 2 N(CH 3 ) 2 , —CH 2 CH 2 NH 2 , —CH 2 CHCH 2 NH 2 , —CH 2 CHCH 2 CH 2 NH 2 , —CH 2 CH(CH 3 )NH 2 , —CH 2 CONH 2 , —CH 2 OH, —CH 2 CH 2 OH, —C(CH 3 ) 2 OH, —CH(OH)CH(CH 3 ) 2 , —C(CH 3 ) 2 CH 2 OH, —CH 2 C(CH 3 ) 2 OH, —CH 2 CH 2 SO 2 CH 3 , —CN, —CF 3 , —CO 2 H, —COCH 3 , —CO 2 CH 3 , —CO 2 C(CH 3 ) 3 , —COCH(OH)CH 3 , —CONH 2 , —CONHCH 3 , —CON(CH 3 ) 2 , —C(CH 3 ) 2 CONH 2 , —NO 2 , —NH 2 , —NHCH 3 , —N(CH 3 ) 2 , —NHCOCH 3 , —N(CH 3 )COCH 3 , —NHS(O) 2 CH 3 , —NHCH 2 CH 2 NH 2 , —NHCH 2 CH 2 CH 2 NH 2 , —NHCH 2 CH 2 CH 2 CH 2 NH 2 , —N(CH 3 )C(CH 3 ) 2 CONH 2 , —N(CH 3 )CH 2 CH 2 S(O) 2 CH 3 , ═O, —OH, —OCH 3 , —OCH 2 CH 2 OCH 3 , —OCH 2 CH 2 NH 2 , —S(O) 2 N(CH 3 ) 2 , —SCH 3 , —CH 2 OCH 3 , —S(O) 2 CH 3 , cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, azetidinyl, azepanyl, oxetanyl, pyrrolidinyl, piperazinyl, piperidinyl, (piperidin-4-yl)ethyl), pyranyl, (piperidin-4-ylmethyl), morpholinomethyl, and morpholino.

2. The compound of claim 1 wherein R 1 is C 1 -C 20 heteroaryl.

3. The compound of claim 1 wherein R 1 is selected from the structures:

where the wavy line indicates the site of attachment.

4. The compound of claim 1 wherein R 2 is C 1 -C 20 heteroaryl.

5. The compound of claim 1 wherein R 2 is —(C 1 -C 20 heteroaryl)-(C 2 -C 20 heterocyclyl).

6. The compound of claim 1 wherein R 2 is selected from the structures:

where the wavy line indicates the site of attachment; and

R 4 is selected from F, Cl, Br, I, —CH 3 , —CH 2 CH 3 , —CH(CH 3 ) 2 , —CH 2 CH(CH 3 ) 2 , —CH 2 NH 2 , —CH 2 NHCH 3 , —CH 2 N(CH 3 ) 2 , —CH 2 CH 2 NH 2 , —CH 2 CHCH 2 NH 2 , —CH 2 CHCH 2 CH 2 NH 2 , —CH 2 CH(CH 3 )NH 2 , —CH 2 CONH 2 , —CH 2 OH, —CH 2 CH 2 OH, —C(CH 3 ) 2 OH, —CH(OH)CH(CH 3 ) 2 , —C(CH 3 ) 2 CH 2 OH, —CH 2 C(CH 3 ) 2 OH, —CH 2 CH 2 SO 2 CH 3 , —CN, —CF 3 , —CO 2 H, —COCH 3 , —CO 2 CH 3 , —CO 2 C(CH 3 ) 3 , —COCH(OH)CH 3 , —CONH 2 , —CONHCH 3 , —CON(CH 3 ) 2 , —C(CH 3 ) 2 CONH 2 , —NO 2 , —NH 2 , —NHCH 3 , —N(CH 3 ) 2 , —NHCOCH 3 , —N(CH 3 )COCH 3 , —NHS(O) 2 CH 3 , —NHCH 2 CH 2 NH 2 , —NHCH 2 CH 2 CH 2 NH 2 , —NHCH 2 CH 2 CH 2 CH 2 NH 2 , —N(CH 3 )C(CH 3 ) 2 CONH 2 , —N(CH 3 )CH 2 CH 2 S(O) 2 CH 3 , ═O, —OH, —OCH 3 , —OCH 2 CH 2 OCH 3 , —OCH 2 CH 2 NH 2 , —S(O) 2 N(CH 3 ) 2 , —SCH 3 , —CH 2 OCH 3 , —S(O) 2 CH 3 , cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, azetidinyl, azepanyl, oxetanyl, pyrrolidinyl, piperazinyl, piperidinyl, (piperidin-4-yl)ethyl), pyranyl, (piperidin-4-ylmethyl), morpholinomethyl, and morpholino; and

n is 0, 1, or 2.

7. The compound of claim 1 having the structure of Formula Ia:

where R 4 is selected from F, Cl, Br, I, —CH 3 , —CH 2 CH 3 , —CH(CH 3 ) 2 , —CH 2 CH(CH 3 ) 2 , —CH 2 NH 2 , —CH 2 NHCH 3 , —CH 2 N(CH 3 ) 2 , —CH 2 CH 2 NH 2 , —CH 2 CHCH 2 NH 2 , —CH 2 CHCH 2 CH 2 NH 2 , —CH 2 CH(CH 3 )NH 2 , —CH 2 CONH 2 , —CH 2 OH, —CH 2 CH 2 OH, —C(CH 3 ) 2 OH, —CH(OH)CH(CH 3 ) 2 , —C(CH 3 ) 2 CH 2 OH, —CH 2 C(CH 3 ) 2 OH, —CH 2 CH 2 SO 2 CH 3 , —CN, —CF 3 , —CO 2 H, —COCH 3 , —CO 2 CH 3 , —CO 2 C(CH 3 ) 3 , —COCH(OH)CH 3 , —CONH 2 , —CONHCH 3 , —CON(CH 3 ) 2 , —C(CH 3 ) 2 CONH 2 , —NO 2 , —NH 2 , —NHCH 3 , —N(CH 3 ) 2 , —NHCOCH 3 , —N(CH 3 )COCH 3 , —NHS(O) 2 CH 3 , —NHCH 2 CH 2 NH 2 , —NHCH 2 CH 2 CH 2 NH 2 , —NHCH 2 CH 2 CH 2 CH 2 NH 2 , —N(CH 3 )C(CH 3 ) 2 CONH 2 , —N(CH 3 )CH 2 CH 2 S(O) 2 CH 3 , ═O, —OH, —OCH 3 , —OCH 2 CH 2 OCH 3 , —OCH 2 CH 2 NH 2 , —S(O) 2 N(CH 3 ) 2 , —SCH 3 , —CH 2 OCH 3 , —S(O) 2 CH 3 , cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, azetidinyl, azepanyl, oxetanyl, pyrrolidinyl, piperazinyl, piperidinyl, (piperidin-4-yl)ethyl), pyranyl, (piperidin-4-ylmethyl), morpholinomethyl, and morpholino; and

n is 0, 1, or 2.

8. The compound of claim 1 having the structure of Formula Ib:

where R 3 is selected from H, and C 1 -C 12 alkyl where alkyl is optionally substituted with F, Cl, CN, —CO 2 H, —COCH 3 , —CO 2 CH 3 , —CO 2 C(CH 3 ) 3 , —COCH(OH)CH 3 , —CONH 2 , —CONHCH 3 , —CON(CH 3 ) 2 , —NO 2 , —NH 2 , —NHCH 3 , —N(CH 3 ) 2 , —NHCOCH 3 , —N(CH 3 )COCH 3 , —NHS(O) 2 CH 3 , —NHCH 2 CH 2 NH 2 , —NHCH 2 CH 2 CH 2 NH 2 , —NHCH 2 CH 2 CH 2 CH 2 NH 2 , —N(CH 3 )C(CH 3 ) 2 CONH 2 , —N(CH 3 )CH 2 CH 2 S(O) 2 CH 3 , ═O, —OH, —OCH 3 , —OCH 2 CH 2 OCH 3 , —OCH 2 CH 2 NH 2 , —S(O) 2 N(CH 3 ) 2 , —SCH 3 , and —S(O) 2 CH 3 .

9. The compound of claim 1 having the structure of Formula Ic:

where R 4 is selected from F, Cl, Br, I, —CH 3 , —CH 2 CH 3 , —CH(CH 3 ) 2 , —CH 2 CH(CH 3 ) 2 , —CH 2 NH 2 , —CH 2 NHCH 3 , —CH 2 N(CH 3 ) 2 , —CH 2 CH 2 NH 2 , —CH 2 CHCH 2 NH 2 , —CH 2 CHCH 2 CH 2 NH 2 , —CH 2 CH(CH 3 )NH 2 , —CH 2 CONH 2 , —CH 2 OH, —CH 2 CH 2 OH, —C(CH 3 ) 2 OH, —CH(OH)CH(CH 3 ) 2 , —C(CH 3 ) 2 CH 2 OH, —CH 2 C(CH 3 ) 2 OH, —CH 2 CH 2 SO 2 CH 3 , —CN, —CF 3 , —CO 2 H, —COCH 3 , —CO 2 CH 3 , —CO 2 C(CH 3 ) 3 , —COCH(OH)CH 3 , —CONH 2 , —CONHCH 3 , —CON(CH 3 ) 2 , —C(CH 3 ) 2 CONH 2 , —NO 2 , —NH 2 , —NHCH 3 , —N(CH 3 ) 2 , —NHCOCH 3 , —N(CH 3 )COCH 3 , —NHS(O) 2 CH 3 , —NHCH 2 CH 2 NH 2 , —NHCH 2 CH 2 CH 2 NH 2 , —NHCH 2 CH 2 CH 2 CH 2 NH 2 , —N(CH 3 )C(CH 3 ) 2 CONH 2 , —N(CH 3 )CH 2 CH 2 S(O) 2 CH 3 , ═O, —OH, —OCH 3 , —OCH 2 CH 2 OCH 3 , —OCH 2 CH 2 NH 2 , —S(O) 2 N(CH 3 ) 2 , —SCH 3 , —CH 2 OCH 3 , —S(O) 2 CH 3 , cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, azetidinyl, azepanyl, oxetanyl, pyrrolidinyl, piperazinyl, piperidinyl, (piperidin-4-yl)ethyl), pyranyl, (piperidin-4-ylmethyl), morpholinomethyl, and morpholino; and

n is 0, 1, or 2.

10. The compound of claim 1 selected from

3-phenyl-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine;

3-(2-fluorophenyl)-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine;

(S)-1-(3-(3-(2-fluorophenyl)-1H-pyrazolo[3,4-c]pyridin-5-yl)pyridin-4-yl)piperidin-3-amine;

3-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)benzamide;

5-(pyridin-3-yl)-3-(3-(trifluoromethyl)phenyl)-1H-pyrazolo[3,4-c]pyridine;

1-(3-(3-(2-fluorophenyl)-1H-pyrazolo[3,4-c]pyridin-5-yl)pyridin-4-yl)piperidin-4-amine;

3-(2-fluorophenyl)-5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridine;

(S)-(1-(3-(3-(2-fluorophenyl)-1H-pyrazolo[3,4-c]pyridin-5-yl)pyridin-4-yl)pyrrolidin-3-yl)methanamine;

3-(6-fluoropyridin-2-yl)-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine;

6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2(1H)-one;

5-(1-methyl-1H-pyrazol-4-yl)-3-phenyl-1H-pyrazolo[3,4-c]pyridine;

3-(2-fluorophenyl)-5-(1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridine;

3-phenyl-5-(1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridine;

3-(2-fluorophenyl)-5-(pyrimidin-5-yl)-1H-pyrazolo[3,4-c]pyridine;

1-(3-(3-(2-fluorophenyl)-1H-pyrazolo[3,4-c]pyridin-5-yl)pyridin-4-yl)azepan-4-amine;

(S)-(1-(3-(3-(2-fluorophenyl)-1H-pyrazolo[3,4-c]pyridin-5-yl)pyridin-4-yl)piperidin-3-yl)methanamine;

(R)-1-(3-(3-(2-fluorophenyl)-1H-pyrazolo[3,4-c]pyridin-5-yl)pyridin-4-yl)piperidin-3-amine;

3-phenyl-5-(1H-1,2,4-triazol-1-yl)-1H-pyrazolo[3,4-c]pyridine;

N1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)ethane-1,2-diamine;

1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-4-amine;

5-(1H-imidazol-1-yl)-3-phenyl-1H-pyrazolo[3,4-c]pyridine;

1-(6-(3-(2-fluorophenyl)-1H-pyrazolo[3,4-c]pyridin-5-yl)pyrazin-2-yl)piperidin-4-amine;

(S)-3-(2-fluorophenyl)-5-(4-(piperidin-3-yloxy)pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine;

(R)-1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

3-phenyl-5-(pyrimidin-5-yl)-1H-pyrazolo[3,4-c]pyridine;

(S)-1-(6-(3-(2-fluorophenyl)-1H-pyrazolo[3,4-c]pyridin-5-yl)pyrazin-2-yl)pyrrolidin-3-amine;

(S)-1-(6-(3-(2-fluorophenyl)-1H-pyrazolo[3,4-c]pyridin-5-yl)pyrazin-2-yl)piperidin-3-amine;

(R)-1-(6-(3-(2-fluorophenyl)-1H-pyrazolo[3,4-c]pyridin-5-yl)pyrazin-2-yl)piperidin-3-amine;

(R)-1-(6-(3-(2-fluorophenyl)-1H-pyrazolo[3,4-c]pyridin-5-yl)pyrazin-2-yl)pyrrolidin-3-amine;

3-(2-fluorophenyl)-5-(4-(piperidin-4-ylmethoxy)pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine;

3-(1H-pyrazol-4-yl)-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine;

1-(5-(3-(2-fluorophenyl)-1H-pyrazolo[3,4-c]pyridin-5-yl)pyridin-3-yl)piperidin-4-amine;

1-(5-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-3-yl)piperidin-4-amine;

N1-(4-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)ethane-1,2-diamine;

1-(4-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-4-amine;

(S)-1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

3-(6-(piperazin-1-yl)pyridin-2-yl)-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine;

3,5-bis(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridine;

(R)-(1-(5-(3-(2-fluorophenyl)-1H-pyrazolo[3,4-c]pyridin-5-yl)pyridin-3-yl)pyrrolidin-3-yl)methanamine;

(1-(5-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-3-yl)piperidin-4-yl)methanamine;

1-(5-(3-(2-fluorophenyl)-1H-pyrazolo[3,4-c]pyridin-5-yl)pyridin-3-yl)azepan-4-amine;

(1-(5-(3-(2-fluorophenyl)-1H-pyrazolo[3,4-c]pyridin-5-yl)pyridin-3-yl)piperidin-4-yl)methanamine;

(R)-(1-(5-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-3-yl)pyrrolidin-3-yl)methanamine;

1-(5-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-3-yl)azepan-4-amine;

N-(piperidin-4-yl)-5-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-3-amine;

5-(3-(2-fluorophenyl)-1H-pyrazolo[3,4-c]pyridin-5-yl)-N-(piperidin-4-yl)pyridin-3-amine;

3-(2-fluoro-5-methoxyphenyl)-5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridine;

(S)-1-(6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

1-(6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-4-amine;

3-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine;

3,5-di(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine;

(R)-1-(6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

2-(4-(3-(6-fluoropyridin-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)-1H-pyrazol-1-yl)acetamide;

(S)-1-(6-(3-(2-fluorophenyl)-1H-pyrazolo[3,4-c]pyridin-5-yl)pyrazin-2-yl)azepan-4-amine;

(S)-1-(5-(3-(2-fluorophenyl)-1H-pyrazolo[3,4-c]pyridin-5-yl)pyridin-3-yl)piperidin-3-amine;

3-(6-(piperazin-1-yl)pyridin-2-yl)-5-(tetrahydro-2H-pyran-3-yl)-1H-pyrazolo[3,4-c]pyridine;

(1-(6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-4-yl)methanamine;

6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)-N-(piperidin-4-ylmethyl)pyridin-2-amine;

5-(1-methyl-1H-pyrazol-4-yl)-3-(6-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

5-(furan-3-yl)-3-phenyl-1H-pyrazolo[3,4-c]pyridine;

3-(1-(piperidin-4-ylmethyl)-1H-pyrazol-4-yl)-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine;

3-(6-(1,4-diazepan-1-yl)pyridin-2-yl)-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine;

1-(6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)azepan-4-amine;

(R)-1-(6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)pyrrolidin-3-amine;

(S)-1-(5-(3-(2-fluorophenyl)-1H-pyrazolo[3,4-c]pyridin-5-yl)pyridin-3-yl)pyrrolidin-3-amine;

(R)-1-(5-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

(R)-1-(5-(3-(2-fluorophenyl)-1H-pyrazolo[3,4-c]pyridin-5-yl)pyridin-3-yl)pyrrolidin-3-amine;

3-(1H-pyrazol-3-yl)-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine;

5-(pyridin-3-yl)-3-(pyridin-4-yl)-1H-pyrazolo[3,4-c]pyridine;

3-(2-fluorophenyl)-5-(4-(piperidin-4-yloxy)pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine;

(S)-1-(5-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)azepan-4-amine;

5-(4-(azetidin-3-yloxy)pyridin-3-yl)-3-(2-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine;

(R)-3-(2-fluorophenyl)-5-(4-(piperidin-3-ylmethoxy)pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine;

6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)-N-(piperidin-4-yl)pyridin-2-amine;

(S)-3-(2-fluorophenyl)-5-(4-(piperidin-3-ylmethoxy)pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine;

(S)-1-(5-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)pyrrolidin-3-amine;

(R)-1-(5-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)pyrrolidin-3-amine;

3-(pyridin-2-yl)-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine;

3-(2-fluoro-5-methylphenyl)-5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridine;

(S)-1-(6-(5-(5-fluoropyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

3-(3-(2-fluorophenyl)-1H-pyrazolo[3,4-c]pyridin-5-yl)-N-(piperidin-4-ylmethyl)pyridin-4-amine;

5-(5-fluoropyridin-3-yl)-3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

(R)-3-(2-fluorophenyl)-5-(4-(pyrrolidin-3-ylmethoxy)pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine;

(R)-1-(6-(5-(5-fluoropyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

(S)-3-(2-fluorophenyl)-5-(4-(pyrrolidin-3-ylmethoxy)pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine;

3-(6-(piperazin-1-yl)pyridin-2-yl)-5-(tetrahydrofuran-3-yl)-1H-pyrazolo[3,4-c]pyridine;

5-(1H-imidazol-5-yl)-3-phenyl-1H-pyrazolo[3,4-c]pyridine;

3-phenyl-5-(pyrazin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

3-(1-(piperidin-4-yl)-1H-pyrazol-3-yl)-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine;

3-(6-((1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-yl)pyridin-2-yl)-5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridine;

N-(2-(1H-imidazol-4-yl)ethyl)-6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-amine;

3-(2-fluorophenyl)-5-(1H-imidazol-5-yl)-1H-pyrazolo[3,4-c]pyridine;

3-(2-fluorophenyl)-5-(pyrazin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

3-(2-fluorophenyl)-5-(4-(2-(piperidin-4-yl)ethoxy)pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine;

1-(6-(3-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)pyrazin-2-yl)piperidin-4-amine;

(R)-1-(3-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)phenyl)piperidin-3-amine;

1-methyl-4-(3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)piperazin-2-one;

1-(3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)urea;

1-(6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)azepan-3-amine;

(S)-1-(6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)azepan-4-amine;

4-amino-1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidine-4-carboxamide;

1-(6-(3-(2,6-difluorophenyl)-1H-pyrazolo[3,4-c]pyridin-5-yl)pyrazin-2-yl)piperidin-4-amine;

1-(6-(3-phenyl-1H-pyrazolo[3,4-c]pyridin-5-yl)pyrazin-2-yl)piperidin-4-amine;

3-(1-methyl-1H-pyrazol-3-yl)-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine;

1-(6-(3-(1-methyl-1H-pyrazol-3-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)pyrazin-2-yl)piperidin-4-amine;

5-(1-methyl-1H-pyrazol-4-yl)-3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

4-amino-N-methyl-1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidine-4-carboxamide;

(R)-2-(1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-yl)ethanamine;

3-(3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)pyridin-2-amine;

3-(piperazin-1-yl)-5-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)benzo nitrile;

1-(3-chloro-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-4-amine;

(S)-2-(1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-yl)ethanamine;

1-(3-methyl-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-4-amine;

(R)-1-(6-(3-(2-fluorophenyl)-1H-pyrazolo[3,4-c]pyridin-5-yl)pyrazin-2-yl)azepan-4-amine;

(R)-1-(6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)azepan-4-amine;

5-(1-methyl-1H-pyrazol-4-yl)-3-(6-(piperidin-4-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

(S)-1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)azepan-4-amine;

(R)-1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)azepan-4-amine;

2-methyl-1-(4-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)-1H-pyrazol-1-yl)propan-2-ol;

5-(pyridin-3-yl)-3-(pyrrolidin-1-yl)-1H-pyrazolo[3,4-c]pyridine;

1-methyl-3-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)imidazolidin-2-one;

3-(5-chloro-6-(4-methylpiperazin-1-yl)pyridin-2-yl)-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine;

3,5-di(pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

3-(5-methyl-6-(4-methylpiperazin-1-yl)pyridin-2-yl)-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine;

1-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyrrolidin-2-one;

1-methyl-4-(3-phenyl-1H-pyrazolo[3,4-c]pyridin-5-yl)-1H-pyrrol-2(5H)-one;

1-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)piperidin-2-one;

3-(6-(piperidin-1-yl)pyridin-2-yl)-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine;

1-(6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-ol;

1-methyl-4-(3-phenyl-1H-pyrazolo[3,4-c]pyridin-5-yl)pyrrolidin-2-one;

(R)-5-(1-methyl-1H-pyrazol-4-yl)-3-(6-(piperidin-3-yloxy)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

(S)-1-(3-chloro-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

(R)-1-(3-chloro-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

4-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)morpholine;

(S)-1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)pyrrolidin-3-amine;

(S)-(1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)pyrrolidin-3-yl)methanamine;

(R)-(1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)pyrrolidin-3-yl)methanamine;

(R)-1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-ol;

1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-4-ol;

3-(6-(4,4′-bipiperidin-1-yl)pyridin-2-yl)-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine;

3-(6-fluoro-5-methylpyridin-2-yl)-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine;

3-(5-methylpyridin-2-yl)-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine;

(R)-1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)pyrrolidin-3-amine;

(S)-1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-ol;

(1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-4-yl)methanamine;

4-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperazin-2-one;

N1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)propane-1,3-diamine;

3-(3,4-dihydro-2H-pyran-5-yl)-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine;

2-(4-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperazin-1-yl)ethanol;

N1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)butane-1,4-diamine;

3-(4,5-dihydrofuran-3-yl)-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine;

(R)-1-(6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

1-(6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)-3-(trifluoromethyl)pyrrolidin-3-amine;

(R)-1-(3-bromo-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)pyrrolidin-3-amine;

1-(3-methyl-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-4-ol;

(S)-1-(3-bromo-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

(R)-1-(3-bromo-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

(R)-1-(3-bromo-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-ol;

1-(3-bromo-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-4-ol;

(R)-1-(3-bromo-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)pyrrolidin-3-ol;

1-(6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-4-ol;

2-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)-2,8-diazaspiro[4.5]decan-1-one;

1-(piperidin-4-ylmethyl)-3-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)imidazolidin-2-one;

2-methyl-1-(6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-ylamino)propan-2-ol;

(R)-1-(4-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyrimidin-2-yl)piperidin-3-amine;

1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperazin-2-one;

2-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)isonicotinamide;

1-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)-3-(pyrrolidin-3-ylmethyl)imidazolidin-2-one;

(S)-3-amino-1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)pyrrolidin-2-one;

(S)-1-(3-methyl-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)pyrrolidin-3-ol;

(R)-1-(3-methyl-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)pyrrolidin-3-ol;

(S)-1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)-3-vinylpyridin-2-yl)piperidin-3-amine;

(S)-1-(3-(prop-1-en-2-yl)-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

(R)-1-(3-methyl-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-ol;

(R)-1-(3-methyl-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

(R)-1-(3-methyl-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)azepan-4-amine;

(S)-1-(3-bromo-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)azepan-4-amine;

(R)-1-(3-bromo-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)azepan-4-amine;

(S)-1-(3-methyl-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)azepan-4-amine;

(S)-1-(3-methyl-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

(R)-1-(3-methyl-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)pyrrolidin-3-amine;

(S)-1-(3-methyl-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)pyrrolidin-3-amine;

(S)-1-(3-bromo-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)pyrrolidin-3-ol;

(1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-yl)methanamine;

3-(3-(piperazin-1-yl)pyrrolidin-1-yl)-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine;

(3S,5R)-5-fluoro-1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

4-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)-1,4-diazepan-2-one;

5-(3-phenyl-1H-pyrazolo[3,4-c]pyridin-5-yl)thiazole;

(1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-2-yl)methanamine;

3-(4-aminopiperidine-1-carbonyl)-1-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyrrolidin-2-one;

N-(2-aminoethyl)-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)picolinamide;

(S)-1-(3-ethyl-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

(S)-1-(3-isopropyl-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

N-(azetidin-3-yl)-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)picolinamide;

1-methyl-4-(3-phenyl-1H-pyrazolo[3,4-c]pyridin-5-yl)piperazin-2-one;

1-methyl-4-(3-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)piperazin-2-one;

5-(1-methyl-1H-pyrazol-4-yl)-3-(pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

2-(1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)pyrrolidin-3-yl)ethanamine;

(S)-3-amino-1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-3-yl)pyrrolidin-2-one;

4-(3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)piperazin-2-one;

(4-aminopiperidin-1-yl) (6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)methanone;

N-(piperidin-4-yl)-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)picolinamide;

5-(3-(pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)thiazole;

4-(3-(2-fluorophenyl)-1H-pyrazolo[3,4-c]pyridin-5-yl)-1-methylpiperazin-2-one;

(S)-1-(3-ethynyl-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

(S)-3-methyl-1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

(S)-1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-3-yl)pyrrolidine-2-carboxamide;

(S)-4-(3-(6-(3-aminopiperidin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)piperazin-2-one;

1-(3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)piperazin-2-one;

(R)-3-methyl-1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

5-(3-(2-fluorophenyl)-1H-pyrazolo[3,4-c]pyridin-5-yl)thiazole;

(S)-1-(6-(5-(thiazol-5-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

(R)-1-(6-(5-(thiazol-5-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

1-methyl-4-(3-(pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)piperazin-2-one;

2-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)-5-(trifluoromethyl)pyridine 1-oxide;

3-methyl-1-(3-phenyl-1H-pyrazolo[3,4-c]pyridin-5-yl)imidazolidine-2,4-dione;

5-(1-ethyl-1H-pyrazol-4-yl)-3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

2-(4-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)-1,4-diazepan-1-yl)ethanol;

5-(3-(6-(piperidin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)thiazole;

5-(3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)thiazole;

5-(1-methyl-1H-pyrazol-4-yl)-3-(2-(piperidin-1-yl)pyrimidin-4-yl)-1H-pyrazolo[3,4-c]pyridine;

5-(1-methyl-1H-pyrazol-4-yl)-3-(2-(piperazin-1-yl)pyrimidin-4-yl)-1H-pyrazolo[3,4-c]pyridine;

(S)-1-(3-butyl-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

5-(1H-imidazol-1-yl)-3-(6-(piperidin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

(R)-1-(4-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyrimidin-2-yl)piperidin-3-amine;

(S)-1-(4-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyrimidin-2-yl)piperidin-3-amine;

1-methyl-4-(3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)pyridin-2(1H)-one;

5-(6-methylpyridin-3-yl)-3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

5-(1H-imidazol-1-yl)-3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

(R)-1-(6-(5-(1H-imidazol-1-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

(R)-3-(3-(6-(3-aminopiperidin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)oxazolidin-2-one;

3-methyl-1-(3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)imidazolidine-2,4-dione;

5-(1-ethyl-1H-pyrazol-4-yl)-3-(6-(4-methylpiperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

3-(3-(6-(piperidin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)oxazolidin-2-one;

(S)-3-(3-(6-(3-aminopiperidin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)oxazolidin-2-one;

3-(6-(piperazin-1-yl)pyridin-2-yl)-5-(1-propyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridine;

(S)-1-(3-bromo-6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

(S)-1-(6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)-N-methylpiperidin-3-amine;

5-(6-fluoropyridin-3-yl)-3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

1-(3-amino-2,2-dimethylpropyl)-5-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2(1H)-one;

(S)-1-(6-(5-(1H-imidazol-1-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

5-(1-isobutyl-1H-pyrazol-4-yl)-3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

5-(1-(2-methoxyethyl)-1H-pyrazol-4-yl)-3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

3-methyl-1-(6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-ol;

5-(5-methylpyridin-3-yl)-3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

(3S,5R)-1-(6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)-5-fluoropiperidin-3-amine;

(S)-1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)-3-(trifluoromethyl)pyridin-2-yl)piperidin-3-amine;

4-(1-(3-bromo-6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)azetidin-3-yl)-1,1-dioxothiomorpholine;

2-methyl-1-(4-(3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)-1H-pyrazol-1-yl)propan-2-ol;

5-(1-isopropyl-1H-pyrazol-4-yl)-3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

5-(1-cyclobutyl-1H-pyrazol-4-yl)-3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

5-(1-(2-fluoroethyl)-1H-pyrazol-4-yl)-3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

1-(3-bromo-6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-4-amine;

(S)-1-(3-bromo-6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-ol;

(R)-1-(3-bromo-6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-ol;

5-(1-ethyl-1H-pyrazol-4-yl)-3-(6-((3aR,6aS)-hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

(S)-5-(1-ethyl-1H-pyrazol-4-yl)-3-(6-(3-methylpiperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

(R)-5-(1-ethyl-1H-pyrazol-4-yl)-3-(6-(3-methylpiperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

4-(3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)morpholine;

3-(5-bromo-6-(4-methylpiperazin-1-yl)pyridin-2-yl)-5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridine;

(S)-1-(3-bromo-6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

3-(5-bromo-6-(piperazin-1-yl)pyridin-2-yl)-5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridine;

4-(1-(3-bromo-6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)azetidin-3-yl)piperazin-2-one;

3-(5-bromo-6-(3,3-dimethyl-4-(2-(methylsulfonyl)ethyl)piperazin-1-yl)pyridin-2-yl)-5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridine;

(R)-1-(3-bromo-6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

4-(1-(3-bromo-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)azetidin-3-yl)piperazin-2-one;

3-(6-(1,4-diazepan-1-yl)pyridin-2-yl)-5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridine;

(S)-1-(6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)-1,4-diazepan-6-ol;

(R)-1-(6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)-1,4-diazepan-6-ol;

(S)-1-(6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)-3-vinylpyridin-2-yl)piperidin-3-amine;

4-(1-(3-methyl-6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)azetidin-3-yl)-1,1-dioxo thiomorpholine;

(S)-1-(6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)-3-(prop-1-en-2-yl)pyridin-2-yl)piperidin-3-amine;

3-(3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)oxazolidin-2-one;

5-(1-(oxetan-3-ylmethyl)-1H-pyrazol-4-yl)-3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

1-(3-methyl-6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-4-amine;

(R)-1-(3-methyl-6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-ol;

4-(3-methyl-6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)morpholine;

4-(6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)morpholine;

3-(6-(4-fluoropiperidin-4-yl)pyridin-2-yl)-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine;

4-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-4-ol;

(S)-3-methyl-1-(6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-ol;

(R)-3-methyl-1-(6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-ol;

4-(1-(3-methyl-6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)azetidin-3-yl)piperazin-2-one;

4-(1-(3-methyl-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)azetidin-3-yl)piperazin-2-one;

(S)-1-(6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)-3-(prop-1-en-2-yl)pyridin-2-yl)piperidin-3-amine;

3-(6-(3,3-dimethyl-4-(2-(methylsulfonyl)ethyl)piperazin-1-yl)-5-methylpyridin-2-yl)-5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridine;

(S)-1-(3-ethyl-6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

(S)-1-(6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)-3-methylpyridin-2-yl)piperidin-3-amine;

(S)-1-(6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)-3-vinylpyridin-2-yl)piperidin-3-amine;

5-(1-ethyl-1H-pyrazol-4-yl)-3-(5-methyl-6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

(S)-1-(3-methyl-6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

(S)-1-(3-isopropyl-6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

4-fluoro-1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-ol;

5-(5-methoxypyridin-3-yl)-3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

N-methyl-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-amine;

5-(5-ethylpyridin-3-yl)-3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

5-(1-methyl-1H-pyrazol-4-yl)-3-(2-(piperidin-4-yl)pyrimidin-4-yl)-1H-pyrazolo[3,4-c]pyridine;

5-(1-methyl-1H-pyrazol-4-yl)-3-(5-methyl-6-(4-methylpiperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

(S)-1-(3-methyl-6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-ol;

(S)-1-(6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-ol;

(R)-1-(6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)-3-methylpyridin-2-yl)piperidin-3-amine;

3-(6-((3S,5R)-3,5-dimethylpiperazin-1-yl)pyridin-2-yl)-5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridine;

(S)-1-(6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

3-(6-(3,3-dimethylpiperazin-1-yl)pyridin-2-yl)-5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridine;

3-(6-(6,6-difluoro-1,4-diazepan-1-yl)pyridin-2-yl)-5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridine;

5-(1-tert-butyl-1H-pyrazol-4-yl)-3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

4-(3-bromo-6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)morpholine;

4-(6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)morpholine;

(R)-1-(6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-ol;

cis-4-fluoro-1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

trans-4-fluoro-1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

(3S,5R)-1-(3-bromo-6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)-5-fluoropiperidin-3-amine;

(3R,5R)-1-(3-bromo-6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)-5-fluoropiperidin-3-amine;

(3S,5R)-1-(3-bromo-6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)-5-fluoropiperidin-3-amine;

3-(6-(1,4-diazepan-1-yl)-4-methylpyridin-2-yl)-5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridine;

(R)-1-(6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)-3-methylpiperidin-3-ol;

N1-(6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)cyclohexane-1,3-diamine;

trans-1-(6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)-4-fluoropiperidin-3-amine;

(4-(6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperazin-2-yl)methanol;

(S)-1-(6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridine-2-yl)-3-methylpiperidin-3-ol;

cis-1-(6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)-4-fluoropiperidin-3-amine;

(S)-1-(5-chloro-6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

3-(6-(piperazin-1-yl)pyridin-2-yl)-5-(5-(trifluoromethyl)pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine;

5-(1-ethyl-1H-pyrazol-4-yl)-3-(6-(3-(trifluoromethyl)piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

5-(1-ethyl-1H-pyrazol-4-yl)-3-(4-(trifluoromethyl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

5-(5-(methylsulfonyl)pyridin-3-yl)-3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

(R)-1-(6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)azepan-4-amine;

1-(4-(6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperazin-1-yl)ethanone;

2-(4-(3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)-1H-pyrazol-1-yl)acetonitrile;

5-(1-ethyl-1H-pyrazol-4-yl)-3-(4-methoxypyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

(S)-1-(3-ethyl-6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

(S)-1-(6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)-3-isopropylpyridin-2-yl)piperidin-3-amine;

5-(1-ethyl-1H-pyrazol-4-yl)-3-(6-(piperazin-1-yl)pyrazin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

5-(1-ethyl-1H-pyrazol-4-yl)-3-(6-(4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

(S)-1-(6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)azepan-4-amine;

(R)-1-(6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)-N-methylpiperidin-3-amine;

1-(5-(3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)pyridin-3-yl)ethanol;

3-(4-cyclopropylpyridin-2-yl)-5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridine;

(S)-1-(3-cyclopropyl-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

(S)-1-(3-cyclopropyl-6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

5-(1-cyclopropyl-1H-pyrazol-4-yl)-3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

3-(6-(piperazin-1-yl)pyridin-2-yl)-5-(1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridine;

3-(6-(1,4-diazepan-1-yl)pyridin-2-yl)-5-(1-(2-fluoroethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridine;

2-(1,4-diazepan-1-yl)-6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)isonicotinonitrile;

5-(1-ethyl-1H-pyrazol-4-yl)-3-(6-(5-(trifluoromethyl)-1,4-diazepan-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

5-(1-ethyl-1H-pyrazol-4-yl)-3-(4-methylpyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

5-(1-ethyl-1H-pyrazol-4-yl)-3-(4-ethylpyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

1-(6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)azepan-3-ol;

(3S,5R)-5-fluoro-1-(6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

2-(4-(3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)-1H-pyrazol-1-yl)ethanol;

5-(1-(cyclopropylmethyl)-1H-pyrazol-4-yl)-3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

(2-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-4-yl)methanol;

1-(6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)-1,4-diazepane-6-carbonitrile;

5-(1-ethyl-1H-pyrazol-4-yl)-3-(4-(prop-1-en-2-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

(S)-1-(6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)azepan-3-ol;

(R)-1-(6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)azepan-3-ol;

(S)-5-(1-(2-fluoroethyl)-1H-pyrazol-4-yl)-3-(6-(3-methylpiperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

5-(1-ethyl-1H-pyrazol-4-yl)-3-(6-(6-fluoro-1,4-diazepan-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

5-(6-methylpyrazin-2-yl)-3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

(S)-1-(3-cyclopropyl-6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

5-(1-ethyl-1H-pyrazol-4-yl)-3-(4-isopropylpyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

5-(1-ethyl-1H-pyrazol-4-yl)-3-(pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

(3S,5R)-5-fluoro-1-(3-methyl-6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

(3S,5R)-1-(6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)-3-methylpyridin-2-yl)-5-fluoropiperidin-3-amine;

(1-(6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)-1,4-diazepan-6-yl)methanol;

(1-(6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)-1,4-diazepan-6-yl)methanol;

N-(6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)azepan-3-amine;

1-(6-(5-(1-(2-fluoroethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)azepan-3-amine;

3-ethyl-5-(3-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)pyrimidin-4(3H)-one;

5-(1-(2-fluoroethyl)-1H-pyrazol-4-yl)-3-(6-(3-methylpiperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

(3R,5R)-5-fluoro-1-(6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine;

1-(6-(5-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)azepan-3-amine;

(S)-1-(6-(5-(1-(2-fluoroethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)azepan-3-amine;

(R)-1-(6-(5-(1-(2-fluoroethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)azepan-3-amine; and

(R)-5-(1-(2-fluoroethyl)-1H-pyrazol-4-yl)-3-(6-(3-methylpiperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[3,4-c]pyridine.

11. A pharmaceutical composition comprised of a compound of claim 1 and a pharmaceutically acceptable carrier, glidant, diluent, or excipient.

12. The pharmaceutical composition according to claim 11 , further comprising a second chemotherapeutic agent.

13. A kit for treating a condition mediated by Pim kinase, comprising:

a) a first pharmaceutical composition comprising a compound of claim 1 ; and

b) instructions for use.

14. The compound of claim 1 selected from

3-(6-(1,4-diazepan-1-yl)pyridin-2-yl)-5-(6-methylpyrazin-2-yl)-1H-pyrazolo[3,4-c]pyridine;

3-(2,5-difluorophenyl)-5-(1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridine;

4-(3-(2-fluorophenyl)-1H-pyrazolo[3,4-c]pyridin-5-yl)-1H-pyrazol-3-amine;

3-(2-fluorophenyl)-5-(3-(trifluoromethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridine;

3-(2-fluorophenyl)-5-(5-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridine; and

2-(5-(1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)-3-fluoroaniline.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 2, 2013
From: GENENTECH, INC.
To: F. HOFFMANN-LA ROCHE AG
Reel/Frame 030726/0792 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 20, 2012
From: DO, STEVEN; HU, HUIYONG; KOLESNIKOV, ALEKSANDR; LEE, WENDY; TSUI, VICKIE H.; WANG, XIAOJING; WEN, ZHAOYANG
To: GENENTECH, INC.
Reel/Frame 028995/0906 →
Continuity (2)
Provisional Application 61522857 · Aug 12, 2011
Related Publication 20130039906A1 · Feb 14, 2013