IP Library Granted Patent US 9,580,430
Granted Patent B2
US 9,580,430 · App. 14/633,360 · Granted Feb 28, 2017

9H-pyrimido[4,5-B]indoles and related analogs as BET bromodomain inhibitors

Inventors: Shaomeng Wang (Saline, MI); Yujun Zhao (Ann Arbor, MI); Bing Zhou (Ann Arbor, MI); Angelo Aguilar (Ann Arbor, MI); Liu Liu (Ann Arbor, MI); Longchuan Bai (Ann Arbor, MI); Donna McEachern (Ann Arbor, MI); Duxin Sun (Ann Arbor, MI); Bo Wen (Ann Arbor, MI); Ruijuan Luo (Ann Arbor, MI); Ting Zhao (Ann Arbor, MI); Arul Chinnaiyan (Ann Arbor, MI); Irfan A. Asangani (Ann Arbor, MI); Jeanne Stuckey (Fenton, MI); Jennifer Lynn Meagher (Ann Arbor, MI); Xu Ran (Ann Arbor, MI); Yang Hu (Ann Arbor, MI)
Assignee: THE REGENTS OF THE UNIVERSITY OF MICHIGAN
C07D487/04A61K31/519C07D487/14C07D519/00
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Quick Facts
Patent No.
US 9,580,430
App. No.
14/633,360
Granted
Feb 28, 2017
Kind
B2
Abstract

The present disclosure provides substituted 9H-pyrimido[4,5-b]indoles and 5H-pyrido[4,3-b]indoles and related analogs represented by Formula I: and the pharmaceutically acceptable salts, hydrates, and solvates thereof, wherein R 1a , A, B 1 , B 2 , G, X 1 , Y 1 , Y 2 , and Y 3 are as defined as set forth in the specification. The present disclosure is also directed to the use of compounds of Formula I to treat a condition or disorder responsive to inhibition of BET bromodomains. Compounds of the present disclosure are especially useful for treating cancer.

Claims (358)

1. A compound having Formula I:

or a pharmaceutically acceptable salt, hydrate, or solvate thereof,

wherein:

B 1 is —N═ or —C(R 1b )—;

B 2 is —N═ or —C(R 1c )—;

Y 1 is —N═;

Y 2 is —C(R 2b )═;

Y 3 is —N═;

G is selected from the group consisting of halo, hydroxy, cyano, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, aralkyl, (heteroaryl)alkyl, —OS(═O) 2 CF 3 , and —Z—R 3 ;

R 1a is selected from the group consisting of hydrogen, hydroxy, alkyl, haloalkyl, alkoxy, alkylthio, amino, and halo;

R 1b is selected from the group consisting of hydrogen and halo;

R 1c is selected from the group consisting of hydrogen and fluoro;

R 2b is selected from the group consisting of hydrogen, amino, optionally substituted alkyl, hydroxyalkyl, alkoxyalkyl, heteroalkyl, (heterocyclo)alkyl, (amino)alkyl, optionally substituted cycloalkyl, optionally substituted heterocyclo, and carboxamido;

R 3 is selected from the group consisting of optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, and optionally substituted heterocyclo;

A is selected from the group consisting of

X 2 is selected from the group consisting of —O—, —S—, and —N(R 5c1 )—;

R 5c1 is selected from the group consisting of hydrogen and alkyl;

R 4a and R 4b are independently selected from the group consisting of hydrogen, halo, haloalkyl, and alkyl;

X 1 is —N(R 5a1 )—;

Z is selected from the group consisting of —C(═O)—, —O—, —S—, —SO 2 —, and —N(R 5b1 )—;

R 5a1 is hydrogen; and

R 5b1 is selected from the group consisting of hydrogen and alkyl, with the provisos that:

a) when G is halo, hydroxy, cyano, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, aralkyl, (heteroaryl)alkyl, or —OS(═O) 2 CF 3 then either B 1 or B 2 , or both, is —N═; or

b) when G is halo, hydroxy, cyano, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, aralkyl, (heteroaryl)alkyl, or —OS(═O) 2 CF 3 , then either R 1b or R 1c , or both, is fluoro.

2. A compound having Formula II:

or a pharmaceutically acceptable salt, hydrate, or solvate thereof, wherein:

R 1 is selected from the group consisting of hydrogen, hydroxy, alkyl, haloalkyl, alkoxy, alkylthio, amino, and halo;

R 2 is selected from the group consisting of hydrogen, amino, alkyl, hydroxyalkyl, alkoxyalkyl, (heterocyclo)alkyl, (amino)alkyl, optionally substituted cycloalkyl, optionally substituted heterocyclo, and carboxamido;

R 3 is selected from the group consisting of optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, and optionally substituted heterocyclo;

A is selected from the group consisting of:

R 4a and R 4b are independently selected from the group consisting of hydrogen and alkyl;

X 2 is selected from the group consisting of —O—, —S—, and —N(R 5c1 )—; and

R 5c1 is selected from the group consisting of hydrogen and alkyl;

X 1 is —N(R 5a1 )—;

Y 1 is —N═;

Z is selected from the group consisting of —O—, —S—, —SO 2 —, and —N(R 5b1 )—;

R 5a1 is hydrogen; and

R 5b1 is selected from the group consisting of hydrogen and alkyl.

3. The compound of claim 2 , or a pharmaceutically acceptable salt, hydrate, or solvate thereof, wherein:

R 2 is selected from the group consisting of hydrogen, alkyl, hydroxyalkyl, (heterocyclo)alkyl, alkoxyalkyl, (amino)alkyl, optionally substituted cycloalkyl, optionally substituted heterocyclo, and carboxamido; and

R 3 is selected from the group consisting of optionally substituted aryl, optionally substituted heteroaryl, and optionally substituted heterocyclo.

4. The compound of claim 2 having Formula IV:

or a pharmaceutically acceptable salt, hydrate, or solvate thereof.

5. The compound of claim 2 , or a pharmaceutically acceptable salt, hydrate, or solvate thereof, wherein Z is —NH—.

6. The compound of claim 2 , or a pharmaceutically acceptable salt, hydrate, or solvate thereof, wherein R 2 is alkyl.

7. The compound of claim 2 , or a pharmaceutically acceptable salt, hydrate, or solvate thereof, wherein R 3 is optionally substituted 5-membered heteroaryl selected from the group consisting of:

R 5a , R 5b , R 5c are each independently selected from the group consisting of hydrogen, halo, cyano, alkylcarbonyl, alkoxycarbonyl, haloalkyl, optionally substituted alkyl, hydroxyalkyl, alkoxyalkyl, alkenyl, aralkyl, optionally substituted cycloalkyl, optionally substituted heterocyclo, optionally substituted aryl, optionally substituted heteroaryl, and carboxamido;

X 3 is selected from the group consisting of —O—, —S—, and —N(R 5d )—;

R 5d is selected from the group consisting of hydrogen, optionally substituted alkyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, (amino)alkyl, aralkyl, (heterocyclo)alkyl, optionally substituted cycloalkyl, optionally substituted heterocyclo, optionally substituted aryl, optionally substituted heteroaryl, carboxamido, (carboxamido)alkyl, and —C(═O)R 5e ; and

R 5e is selected from the group consisting of alkyl and alkoxy.

8. The compound of claim 2 , or a pharmaceutically acceptable salt, hydrate, or solvate thereof, having Formula IX:

9. The compound of claim 8 , or a pharmaceutically acceptable salt, hydrate, or solvate thereof, wherein R 5a , R 5c , and R 5d are independently selected from the group consisting of hydrogen, C 1-6 alkyl, and C 3-6 cycloalkyl.

10. The compound of claim 9 , or a pharmaceutically acceptable salt, hydrate, or solvate thereof, wherein: R 1 is —OCH 3 , R 2 is selected from the group consisting of —CH 3 and —CH 2 OCH 3 ; and Z is —N(H)—.

11. The compound of claim 2 , or a pharmaceutically acceptable salt, hydrate, or solvate thereof, having Formula XVIII:

12. The compound of claim 11 , or a pharmaceutically acceptable salt, hydrate, or solvate thereof, wherein R 5f is selected from the group consisting of C 1-6 alkyl and C 3-6 cycloalkyl.

13. The compound of claim 12 , or a pharmaceutically acceptable salt, hydrate, or solvate thereof, wherein: R 1 is —OCH 3 ; R 2 is selected from the group consisting of —CH 3 and —CH 2 OCH 3 ; and Z is —N(H)—.

14. The compound of claim 4 , or a pharmaceutically acceptable salt, hydrate, or solvate thereof, selected from the group consisting of:

N-(3-cyclopropyl- 1 -methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-cyclopropyl-1-ethyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine; and

N-(3-cyclopropyl- 1 -methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-(methoxymethyl)-9H-pyrimido[4,5-b]indol-4-amine.

15. The compound of claim 1 , or a pharmaceutically acceptable salt, hydrate, or solvate thereof, selected from the group consisting of:

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(3-methyl-1-phenyl-1H-pyrazol-5-yl)-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(3-phenyl-1H-pyrazol-4-yl)-9H-pyrimido[4,5-b]indol-4-amine;

4-(4-((4-Isopropyl-5-methyl-4H-1,2,4-triazol-3-yl)thio)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-7-yl)-3,5-dimethylisoxazole;

7-(3,5-dimethylisoxazol-4-yl)-N-(1-isopropyl-5-methyl-3-phenyl-1H-pyrazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(5-methyl-4-phenyl-1H-pyrazol-3-yl)-9H-pyrimido[4,5-b]indol-4-amine;

N-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)-2-(oxazol-2-yl)-4-phenylthiazol-5-amine;

N-(1-(3-chlorophenyl)-3-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(1,3-dimethyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(1-isopropyl-3-methyl-1H-pyrazol-5-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(1-methyl-1H-pyrazolo[3,4-b]pyridin-3-yl)-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(1-methyl-1H-pyrazolo[4,3-c]pyridin-3-yl)-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(1-methyl-1H-indazol-3-yl)-9H-pyrimido[4,5-b]indol-4-amine;

N-(5-chloro-1-methyl-1H-indazol-3-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(pyrazolo[1,5-a]pyridin-3-yl)-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(pyrazolo[1,5-a]pyrimidin-3-yl)-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N-(1-methyl-1H-indazol-3-yl)-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-2-isopropyl-6-methoxy-N-(1-methyl-1H-indazol-3-yl)-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N-(6-methoxy-1-methyl-1H-indazol-3-yl)-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N-(1-methyl-1H-indazol-3-yl)-2-(tetrahydro-2H-pyran-4-yl)-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(1-isopropyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

4-(4-((2-chlorophenyl)thio)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-7-yl)-3,5-dimethylisoxazole;

4-(4-((3-chlorophenyl)thio)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-7-yl)-3,5-dimethylisoxazole;

4-(4-((2-isopropylphenyl)thio)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-7-yl)-3,5-dimethylisoxazole;

4-(4-((1H-indol-3-yl)thio)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-7-yl)-3,5-dimethylisoxazole;

4-(4-((3-(tert-butyl)phenyl)thio)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-7-yl)-3,5-dimethylisoxazole;

(R)—N-(chroman-4-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(1-isopropyl-1H-1,2,4-triazol-5-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-(tert-butyl)-1,5-dimethyl-1H-pyrazol-4-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(5-(tert-butyl)-1,3-dimethyl-1H-pyrazol-4-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(4-isopropyl-1H-pyrazol-5-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

4-(tert-butyl)-N-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)thiazol-5-amine;

N-(1,3-dimethyl-1H-pyrazol-4-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(1,3,5-trimethyl-1H-pyrazol-4-yl)-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(1-isopropyl-3,5-dimethyl-1H-pyrazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(1-isopropyl-4-methyl-1H-pyrazol-5-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

3-(4-chlorophenyl)-N-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)-5-methylisoxazol-4-amine;

3-(3-chlorophenyl)-N-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)-5-methylisoxazol-4-amine;

4-(3-chlorophenyl)-N-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)-2-(oxazol-2-yl)thiazol-5amine;

4-(4-chlorophenyl)-N-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)-2-(oxazol-2-yl)thiazol-5-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(1H-indol-3-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)-2-isopropyl-4-phenylthiazol-5-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(5-methyl-2-phenyl-1H-pyrrol-3-yl)-9H-pyrimido[4,5-b]indol-4-amine;

N-(2-(3-chlorophenyl)-5-methyl-1H-pyrrol-3-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

4-((7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)amino)-N,2-dimethyl-5-phenyl-1H-pyrrole-3-carboxamide;

(4-((7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)amino)-2-methyl-5-phenyl-1H-pyrrol-3-yl)(morpholino)methanone;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N-(5-methoxy-[1,1′-biphenyl]-2-yl)-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(4′-chloro-5-methoxy-[1,1′-biphenyl]-2-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(4-((dimethylamino)methyl)-5-methoxy-[1,1′-biphenyl]-2-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(7-phenyl-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-9H-pyrimido[4,5-b]indol-4-amine;

N-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)-4-methyl-7-phenyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N-(6-methoxy-4-phenylpyridin-3-yl)-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N-(4-methoxy-2-(pyridin-2-yl)phenyl)-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N-(4-methoxy-2-(pyridin-4-yl)phenyl)-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N-(4-methoxy-2-(oxazol-2-yl)phenyl)-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(4-ethoxynaphthalen-1-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(1H-indazol-3-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(6-fluoro-1-methyl-1H-indazol-3-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N-(5-methoxy-1-methyl-1H-indazol-3-yl)-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(1H-indol-3-yl)-2-isopropyl-6-methoxy-9H-pyrimido[4,5-b]indol-4-amine;

N-(1-(tert-butyl)-3-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-2-isopropyl-N-(1-isopropyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)-6-methoxy-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(3-isopropyl-1-methyl-1H-pyrazol-5-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

2-(5-((7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)amino)-3-methyl-1H-pyrazol-1-yl)ethan-1-ol;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(3-methyl-1-(pyridin-4-yl)-1H-pyrazol-5-yl)-9H-pyrimido[4,5-b]indol-4-amine;

N-(1,3-dimethyl-1H-pyrazol-5-yl)-7-(3,5-dimethyl-4H-1,2,4-triazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethyl-4H-1,2,4-triazol-4-yl)-6-methoxy-2-methyl-N-(1-methyl-1H-indazol-3-yl)-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethyl-4H-1,2,4-triazol-4-yl)-6-methoxy-2-methyl-N-(pyrazolo[1,5-a]pyridin-3-yl)-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethyl-1H-pyrazol-4-yl)-N-(1,3-dimethyl-1H-pyrazol-5-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-2-isopropyl-N-(1-isopropyl-3-methyl-1H-pyrazol-5-yl)-6-methoxy-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(1-isopropyl-3-methyl-1H-pyrazol-5-yl)-6-methoxy-2-(tetrahydro-2H-pyran-4-yl)-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(1-isopropyl-3-methyl-1H-pyrazol-5-yl)-6-methoxy-9H-pyrimido[4,5-b]indol-4-amine;

N-(1,4-dimethyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(1,4-dimethyl-1H-pyrazol-3-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(4-isopropyl-1-methyl-1H-pyrazol-3-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(4-isopropyl-1-methyl-1H-pyrazol-5-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(1,3,4-trimethyl-1H-pyrazol-5-yl)-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(1-isopropyl-3,4-dimethyl-1H-pyrazol-5-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(1,3-diisopropyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5b]-indol-4-yl)-4-isopropyl-2-methylthiazol-5-amine;

N-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5b]-indol-4-yl)-4-methylthiazol-2-amine;

N-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5b]-indol-4-yl)-5-methylthiazol-2-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(1-isopropyl-5-methyl-1H-imidazol-2-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(1-isopropyl-4-methyl-1H-imidazol-2-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(1-isopropyl-1H-imidazol-5-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)-5-isopropyl-3-methylisoxazol-4-amine;

N-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)-3-isopropyl-5-methylisoxazol-4-amine;

N-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)-4-isopropyl-2-methyloxazol-5-amine;

4-(4-((3-chlorophenyl)sulfonyl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-7-yl)-3,5-dimethylisoxazole;

4-(4-((4-isopropyl-4H-1,2,4-triazol-3-yl)sulfonyl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-7-yl)-3,5-dimethylisoxazole;

4-(4-(3-chlorophenoxy)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-7-yl)-3,5-dimethylisoxazole;

4-(6-methoxy-2-methyl-4-(pyridin-3-yloxy)-9H-pyrimido[4,5-b]indol-7-yl)-3,5-dimethylisoxazole;

N-(3-chlorophenyl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)-5-methyl-3-phenylisoxazol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(imidazo[1,2-a]pyridin-3-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N-(4-methoxynaphthalen-1-yl)-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-([1,2,4]triazolo[4,3-a]pyridin-3-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(1H-pyrrolo[2,3-b]pyridin-3-yl)-9H-pyrimido[4,5-b]indol-4-amine;

N-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)thieno[2,3-b]pyridin-3-amine;

4-(6-methoxy-2-methyl-4-(quinolin-4-yloxy)-9H-pyrimido[4,5-b]indol-7-yl)-3,5-dimethylisoxazole;

4-(4-((5-bromopyridin-3-yl)oxy)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-7-yl)-3,5-dimethylisoxazole;

N-(5-chloropyridin-3-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-chloro-4-fluorophenyl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(5-methylpyridin-3-yl)-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(4-methylpyridin-3-yl)-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(4-methylpyridin-2-yl)-9H-pyrimido[4,5-b]indol-4-amine; and

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(6-methylpyridin-2-yl)-9H-pyrimido[4,5-b]indol-4-amine.

16. The compound of claim 1 , or a pharmaceutically acceptable salt, hydrate, or solvate thereof, selected from the group consisting of:

N-cyclohexyl-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-cyclopentyl-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(1,5-dimethyl-1H-pyrazol-3-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(1-ethyl-3-methyl-1H-pyrazol-5-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(1-(tert-butyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(1-cyclopentyl-3-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(1-cyclobutyl-3-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-tert-butyl-1-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(2-methyl-2,4,5,6-tetrahydrocyclopenta-[c]pyrazol-3-yl)-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(1-methyl-1H-pyrazolo[4,3-b]pyridin-3-yl)-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(1-methyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(2-methyl-4,5,6,7-tetrahydro-2H-indazol-3-yl)-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-(tert-butyl)-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(5-fluoro-1-methyl-1H-indazol-3-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(7-fluoro-1-methyl-1H-indazol-3-yl)-6-methoxy-2-methyl-9H -pyrimido[4,5-b]indol-4-amine;

2-(3-((7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)amino)-1H-indazol-1-yl)ethanol;

7-(3,5-dimethylisoxazol-4-yl)-N-(4-fluoro-1-methyl-1H-indazol-3-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

3-(tert-butyl)-N-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)isothiazol-5-amine;

N-(5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(1-cyclopentyl-4-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-cyclobutyl-1-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(2-isopropyl-2,4,5,6-tetrahydrocyclopenta[c]pyrazol-3-yl)-6-methoxy-2-methyl-9H pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(2-isopropyl-4,5,6,7-tetrahydro-2H-indazol-3-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-3-yl)-9H-pyrimido[4,5-b]indol-4-amine;

N-(4-cyclopropyl-1,3-dimethyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(2-ethyl-2,4,5,6-tetrahydrocyclopenta[c]pyrazol-3-yl)-6-methoxy-2-methyl-9H pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(2-ethyl-4,5,6,7-tetrahydro-2H-indazol-3-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(4-cyclopropyl-1-ethyl-3-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-cyclopropyl-1-ethyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-cyclopropyl-1-ethyl-4-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(1-ethyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-cyclopropyl-1,4-dimethyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(2-cyclopropyl-2,4,5,6-tetrahydrocyclopenta[c]pyrazol-3-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-cyclopropyl-1-isopropyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

2-(3-((7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)amino)-5,6-dihydrocyclopenta[c]pyrazol-2(4H)-yl)ethanol;

7-(3,5-dimethylisoxazol-4-yl)-N-(2-(2-fluoroethyl)-2,4,5,6-tetrahydrocyclopenta[c]pyrazol-3-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(1,3-dicyclopropyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-cyclopropyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

1-(3-cyclopropyl-5-((7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)amino)-1H-pyrazol-1-yl)ethanone;

ethyl 3-cyclopropyl-5-((7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)amino)-1H-pyrazole-1-carboxylate;

N-(3-cyclopropyl-1-(2,2,2-trifluoroethyl)-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(2-(2,2,2-trifluoroethyl)-2,4,5,6-tetrahydrocyclopenta[c]pyrazol-3-yl)-9H-pyrimido[4,5-b]indol-4-amine;

2-(3-cyclopropyl-5-((7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)amino)-1H-pyrazol-1-yl)ethanol;

N-(3-cyclopropyl-1-(2-fluoroethyl)-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-cyclopropyl-1-(2-(dimethylamino)ethyl)-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(1-methyl-3-(1,1,1-trifluoro-2-methylpropan-2-yl)-1H-pyrazol-5-yl)-9H-pyrimido[4,5-b]indol-4-amine;

tert-butyl 3-(3-cyclopropyl-5-((7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)amino)-1H-pyrazol-1-yl)azetidine-1-carboxylate;

N-(1-(azetidin-3-yl)-3-cyclopropyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(1-methyl-1H-imidazol-4-yl)-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(3-ethyl-1,4-dimethyl-1H-pyrazol-5-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(1,5-dimethyl-1H-pyrazol-4-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(1,2-dimethyl-1H-imidazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(1-methyl-1H-pyrazol-5-yl)-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(1-ethyl-1H-pyrazol-5-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

5-((7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)amino)-1-methyl-1H-pyrazole-4-carbonitrile;

7-(3,5-dimethylisoxazol-4-yl)-N-(1-isopropyl-1H-pyrazol-5-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(1-ethyl-4-methyl-1H-pyrazol-5-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)-2,4-dimethylthiazol-5-amine;

N-(1-cyclopentyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(3-isopropyl-1-methyl-1H-pyrazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(3-ethyl-1-methyl-1H-pyrazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(1-(tert-butyl)-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(1-(tert-butyl)-3,4-dimethyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(1-ethyl-3,4-dimethyl-1H-pyrazol-5-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(1-cyclobutyl-3,4-dimethyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(1-cyclopropyl-3,4-dimethyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)-2-isopropyl-4-methylthiazol-5-amine;

N-(1-cyclopropyl-3-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-(tert-butyl)-1-methyl-1H-pyrazol-4-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(3-isopropyl-1,5-dimethyl-1H-pyrazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-cyclopropyl-1-methyl-1H-pyrazol-4-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(1-(tert-butyl)-4-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(1-cyclopropyl-4-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(1-cyclobutyl-4-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(1-ethyl-3-isopropyl-1H-pyrazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-cyclobutyl-1-methyl-1H-pyrazol-4-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-cyclobutyl-1-ethyl-1H-pyrazol-4-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

2-(tert-butyl)-N-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)-4-methylthiazol-5-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(1-ethyl-3-isopropyl-1H-pyrazol-5-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(1-cyclopropyl-3-isopropyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N4-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-9H-pyrimido[4,5-b]indole-2,4-diamine;

N-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-(methoxymethyl)-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(quinolin-8-yl)-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(quinolin-5-yl)-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-m-tolyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N-(3-methoxyphenyl)-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(3-(trifluoromethyl)phenyl)-9H-pyrimido[4,5-b]indol-4-amine;

N-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)-3,5-dimethylisoxazol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(3-ethylphenyl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-chloro-2-fluorophenyl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N-(3-methoxy-5-methylphenyl)-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)-3,4-dimethylisoxazol-5-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(1H-indol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(isoquinolin-5-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)-4,5-dimethylisoxazol-3-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(isoquinolin-8-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(5-chloro-2-fluorophenyl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-chloro-5-fluorophenyl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-phenyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(2-methylquinolin-5-yl)-9H-pyrimido[4,5-b]indol-4-amine;

N-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)benzo[d]thiazol-7-amine;

N1-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)-N3,N3-dimethylbenzene-1,3-diamine;

7-(3,5-dimethylisoxazol-4-yl)-N-(indolin-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(1-methylindolin-6-yl)-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(1H-indol-6-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(2,3-dihydrobenzofuran-4-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(1-methyl-1H-indazol-4-yl)-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(1-methyl-1H-indol-4-yl)-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(3,5-dimethylphenyl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(2,5-dimethylphenyl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(3,5-dicyclopropyl-1-methyl-1H-pyrazol-4-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(3,5-diethyl-1-methyl-1H-pyrazol-4-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(1,3,5-triethyl-1H-pyrazol-4-yl)-9H-pyrimido[4,5-b]indol-4-amine;

N-(3,5-diisopropyl-1-methyl-1H-pyrazol-4-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(2-isopropylphenyl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(quinolin-4-yl)-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(2-methylpyridin-4-yl)-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-cyclopropyl-4-fluoro-1-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-cyclopropyl-1-ethyl-4-fluoro-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(1-methyl-3-(1-methylcyclopropyl)-1H-pyrazol-5-yl)-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(1-ethyl-3-(1-methylcyclopropyl)-1H-pyrazol-5-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(1-isopropyl-3-(1-methylcyclopropyl)-1H-pyrazol-5-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-cyclopropyl-4-fluoro-1-isopropyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-cyclopropyl-1-(1-methylazetidin-3-yl)-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N,2,9-trimethyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(1H-pyrrolo[2,3-c]pyridin-3-yl)-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N-(3-(1-methoxycyclopropyl)-1-methyl-1H-pyrazol-5-yl)-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(1-methyl-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-5-yl)-9H-pyrimido[4,5-b]indol-4-amine;

2-(3-cyclopropyl-5-((7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)amino)-1H-pyrazol-1-yl)-N-ethylacetamide;

N-(3-cyclopropyl-1-(piperidin-4-yl)-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-cyclopropyl-1-(1-ethylpiperidin-4-yl)-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

1-(4-(3-cyclopropyl-5-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-ylamino)-1H-pyrazol-1-yl)piperidin-1-yl)ethanone;

N-(3-cyclopropyl-1-(2-methoxyethyl)-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-cyclopropyl-1-(1-methylpiperidin-4-yl)-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

1-(4-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-ylamino)-1-methyl-1H-pyrazol-3-yl)ethanone;

2-(4-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-ylamino)-1-methyl-1H-pyrazol-3-yl)propan-2-ol;

N-(3-tert-butyl-1,5-dimethyl-1H-pyrazol-4-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

methyl 5-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-ylamino)-1-methyl-1H-pyrazole-3-carboxylate;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(1-methyl-3-(prop-1-en-2-yl)-1H-pyrazol-5-yl)-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-(2-methoxyethyl)-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-((2-methoxyethoxy)methyl)-9H-pyrimido[4,5-b]indol-4-amine;

1-(3-(3-cyclopropyl-5-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-ylamino)-1H-pyrazol-1-yl)azetidin-1-yl)ethanone;

methyl 3-(3-cyclopropyl-5-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-ylamino)-1H-pyrazol-1-yl)azetidine-1-carboxylate;

N-(3-cyclopropyl-1-(1-ethylazetidin-3-yl)-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine; and

(2S)-4-(3-cyclopropyl-5-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-ylamino)-1H-pyrazol-1-yl)butane-1,2-diol.

17. The compound of claim 1 , or a pharmaceutically acceptable salt, hydrate, or solvate thereof, selected from the group consisting of:

(S)-3-(3-cyclopropyl-5-((7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)amino)-1H-pyrazol-1-yl)propane-1,2-diol;

N-(1-((1,4-dioxan-2-yl)methyl)-3-cyclopropyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-cyclopropyl-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-cyclopropyl-1-(2-morpholinoethyl)-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-(2-methoxyethyl)-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-((2-methoxyethoxy)methyl)-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-((methylsulfonyl)methyl)-9H-pyrimido[4,5-b]indol-4-amine;

N4-(3-cyclopropyl-1-ethyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-9H-pyrimido[4,5-b]indole-2,4-diamine;

N4-(1,3-dicyclopropyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-9H-pyrimido[4,5-b]indole-2,4-diamine;

7-(3,5-dimethylisoxazol-4-yl)-N4-(2-isopropyl-2,4,5,6-tetrahydrocyclopenta[c]pyrazol-3-yl)-6-methoxy-9H-pyrimido[4,5-b]indole-2,4-diamine;

3-(3-cyclopropyl-5-((7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)amino)-1H-pyrazol-1-yl)azetidine-1-carbaldehyde;

N-(3-cyclopropyl-1-(oxetan-3-ylmethyl)-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-cyclopropyl-1-(2-(methylsulfonyl)ethyl)-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrido[3′,2′:4,5]pyrrolo[2,3-d]pyrimidin-4-amine;

N-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-5-fluoro-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-5-fluoro-6-methoxy-N,2-dimethyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-8-fluoro-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-8-fluoro-6-methoxy-N,2-dimethyl-9H-pyrimido[4,5-b]indol-4-amine;

N-(1-(tert-butyl)-3-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrido[2′,3′:4,5]pyrrolo[2,3-d]pyrimidin-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(1-methyl-1H-pyrazolo[3,4-b]pyridin-3-yl)-9H-pyrido[2′,3′:4,5]pyrrolo[2,3-d]pyrimidin-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(1-isopropyl-4-methyl-1H-pyrazol-5-yl)-6-methoxy-2-methyl-9H-pyrido[2′,3′:4,5]pyrrolo[2,3-d]pyrimidin-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-N-(m-tolyl)-9H-pyrido[2′,3′:4,5]pyrrolo[2,3-d]pyrimidin-4-amine;

N-(3-(tert-butyl)-1-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrido[2′,3′:4,5]pyrrolo[2,3-d]pyrimidin-4-amine;

N-(3-(tert-butyl)-1-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N,2-dimethyl-9H-pyrido[2′,3′:4,5]pyrrolo[2,3-d]pyrimidin-4-amine;

N-(1-(tert-butyl)-3-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N,2-dimethyl-9H -pyrido[2′,3′:4,5]pyrrolo[2,3-d]pyrimidin-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N,2-dimethyl-N-(m-tolyl)-9H-pyrido[2′,3′:4,5]pyrrolo[2,3-d]pyrimidin-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N,2-dimethyl-N-(1-methyl-1H-pyrazolo[3,4-b]pyridin-3-yl)-9H-pyrido[2′,3′:4,5]pyrrolo[2,3-d]pyrimidin-4-amine;

7-(3,5-dimethylisoxazol-4-yl)-N-(1-isopropyl-4-methyl-1H-pyrazol-5-yl)-6-methoxy-N,2-dimethyl-9H -pyrido[2′,3′:4,5]pyrrolo[2,3-d]pyrimidin-4-amine;

N-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N,2-dimethyl-9H-pyrido[2′,3′:4,5]pyrrolo[2,3-d]pyrimidin-4-amine;

N-cyclopentyl-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N,2-dimethyl-9H-pyrido[2′,3′:4,5]pyrrolo[2,3-d]pyrimidin-4-amine;

N-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrido[2′,3′:4,5]pyrrolo[2,3-d]pyrimidin-4-amine;

4-(6-methoxy-2-methyl-4-(quinolin-4-yl)-9H-pyrido[2′,3′:4,5]pyrrolo[2,3-d]pyrimidin-7-yl)-3,5-dimethylisoxazole;

methyl 4-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrido[2′,3′:4,5]pyrrolo[2,3-d]pyrimidin-4-yl)-1-naphthoate;

2-(3-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrido[2′,3′:4,5]pyrrolo[2,3-d]pyrimidin-4-yl)phenyl)propan-2-ol;

4-(4-(3,5-diethyl-1-methyl-1H-pyrazol-4-yl)-6-methoxy-2-methyl-9H-pyrido[2′,3′:4,5]pyrrolo[2,3-d]pyrimidin-7-yl)-3,5-dimethylisoxazole;

5-cyclopropyl-4-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrido[2′,3′:4,5]pyrrolo[2,3-d]pyrimidin-4-yl)-3-methylisoxazole;

4-(4-(5-cyclopropyl-1,3-dimethyl-1H-pyrazol-4-yl)-6-methoxy-2-methyl-9H-pyrido[2′,3′:4,5]pyrrolo[2,3-d]pyrimidin-7-yl)-3,5-dimethylisoxazole;

4-(4-(3-cyclopropyl-1,5-dimethyl-1H-pyrazol-4-yl)-6-methoxy-2-methyl-9H-pyrido[2′,3′:4,5]pyrrolo[2,3-d]pyrimidin-7-yl)-3,5-dimethylisoxazole; and

N-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-6-methoxy-2-methyl-7-(1,3,5-trimethyl-1H-pyrazol-4-yl)-9H-pyrimido[4,5-b]indol-4-amine.

18. A pharmaceutical composition comprising the compound of claim 2 , or a pharmaceutically acceptable salt, hydrate, or solvate thereof, and a pharmaceutically acceptable carrier or vehicle.

Assignments (3)
CONFIRMATORY LICENSE Recorded Feb 28, 2017
From: UNIVERSITY OF MICHIGAN
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 041825/0675 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 18, 2016
From: HU, YANG
To: THE REGENTS OF THE UNIVERSITY OF MICHIGAN\
Reel/Frame 040048/0728 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 3, 2015
From: WANG, SHAOMENG; ZHAO, YUJUN; ZHOU, BING; AGUILAR, ANGELO; LIU, LIU; BAI, LONGCHUAN; MCEACHERN, DONNA; SUN, DUXIN; WEN, BO; LUO, RUIJUAN; ZHAO, TING; CHINNAIYAN, ARUL; ASANGANI, IRFAN A.; STUCKEY, JEANNE; MEAGHER, JENNIFER LYNN; RAN, XU
To: THE REGENTS OF THE UNIVERSITY OF MICHIGAN
Reel/Frame 035330/0426 →
Continuity (5)
Provisional Application 62048388 · Sep 10, 2014
Provisional Application 62031640 · Jul 31, 2014
Provisional Application 61950406 · Mar 10, 2014
Provisional Application 61946501 · Feb 28, 2014
Related Publication 20150246923A1 · Sep 3, 2015