8-heteroarylpurine MNK2 inhibitors for treating metabolic disorders

1. A compound of formula I:

wherein

R 1 is chosen from aryl, heteroaryl, C 1 -C 10 alkyl, substituted aryl, substituted heteroaryl, and substituted C 1 -C 10 alkyl;

n is chosen from 0,1, and 2;

R 1a is hydrogen or methyl;

R 2 is chosen from;

hydrogen;

C 1 -C 6 alkyl; and

C 1 -C 6 alkyl substituted with CN or fluorine; and

R 3 is chosen from aryl substituted with one or two alkoxy, and heteroaryl optionally substituted with one to three substituents chosen from the group consisting of:

lower alkyl, hydroxyl, hydroxyloweralkyl, lower alkoxy, amino, alkylamino, dialkylamino, acylamino, alkoxycarbonyl, and halogen.

2. A compound according to claim 1 :

wherein

R 3 is chosen from heteroaryl optionally substituted with one to three substituents chosen from the group consisting of:

lower alkyl, hydroxy, lower alkoxy, amino, alkylamino, dialkylamino, and acylamino.

3. A compound according to claim 2 wherein:

R 1 is chosen from aryl, heteroaryl, and C 1 -C 10 alkyl, each optionally substituted with one to three substituent(s) chosen from the group consisting of:

alkyl, halo, lower alkoxy, haloalkyl, hydroxy, cyano, nitro, amino, alkylamino, dialkylamino, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, mercapto, alkylthio, alkylsulfinyl, alkylsulfonyl, acylamino, acylaminoalkyl, oxaalkyl, heterocyclylalkyl, dialkylaminoalkoxy, (alkyl)(acyl)aminoalkyl, trifluoromethoxy, acylaminoalkoxy, and heterocyclylalkoxy.

4. A compound according to claim 2 , wherein R 1 is phenyl substituted with one substitutent chosen from the group consisting of methylenedioxy, halogen, alkyl, aminomethyl, alkylaminomethyl, dialkylaminomethyl, oxaalkyl, dialkylaminoalkoxy, (alkyl)(acyl)aminoalkyl, trifluoromethoxy, acylaminoalkoxy, heterocyclylalkoxy, and

is a nitrogen heterocycle; and

q is 1-3.

5. A compound according to claim 2 , wherein R 1 is phenyl or phenyl substituted with methylenedioxy, lower alkyl, halogen, alkyl, aminomethyl, alkylaminomethyl, dialkylaminomethyl, acylamino, and acylaminoalkyl.

6. A compound according to claim 2 , wherein R 1 is thienyl and n is 2.

7. A compound according to claim 2 , wherein R 1 is lower alkyl and n is 0.

8. A compound according to claim 2 , wherein R 1a is H.

9. A compound according to claim 2 , wherein n is 0.

10. A compound according to claim 2 , wherein R 2 is chosen from C 1 -C 3 alkyl, fluorinated C 1 -C 3 alkyl, and cyano C 1 -C 3 alkyl.

11. A compound according to claim 2 , wherein R 2 is chosen from cyclopropyl, isopropyl, 2-cyanoethyl, ethyl, trifluoroethyl, hydrogen, and methyl.

12. A compound according to claim 2 , wherein R 3 is chosen from nitrogen heteroaryl and substituted nitrogen heteroaryl.

13. A compound according to claim 12 , wherein R 3 is formula II

wherein

X is chosen from CH, C-halogen, and nitrogen;

Y is chosen from H, halogen, NH 2 , NHMe, NHEt, NMe 2 , NHAc, OH, OMe, OEt, Me, and Et.

14. A compound according to claim 13 , wherein Y is chosen from H, NH 2 , and NHMe.

15. A compound according to claim 1 , wherein R 3 is substituted phenyl.

16. A compound according to claim 13 , wherein R 3 is chosen from 4-pyridinyl, 2-aminopyrimidin-4-yl and 2-(methylamino)pyrimidin-4-yl.

17. A compound according to claim 13 , wherein R 3 is chosen from 4-pyridyl, 4-pyrimidinyl, 4-(2-aminopyrimidyl), and 4-(2-aminopyridinyl).

18. A compound according to claim 2 wherein:

R 1 is chosen from phenyl and phenyl substituted with alkoxy, halogen, aminoalkyl, or acylaminoalkyl;

n is chosen from 0,1, and 2;

R 1a is hydrogen;

R 2 is chosen from cyclopropyl, isopropyl, ethyl, 2-cyano-ethyl, hydrogen, and methyl; and

R 3 is chosen from 4-pyridyl, 4-pyrimidinyl, 4-(2-aminopyrimidyl), and 4-(2-aminopyridinyl).

19. A pharmaceutical formulation comprising a compound according to claim 1 and a pharmaceutically acceptable carrier.

20. A compound according to claim 1 chosen from:

9-Cyclopropyl-8-(2-(methylamino)pyrimidin-4-yl)-N-m-tolyl-9H-purin-2-amine;

N-(4-(9-Methyl-8-(pyridin-4-yl)-9H-purin-2-ylamino)benzyl)-N-methylacetamide;

8-(2-Aminopyridin-4-yl)-9-cyclopropyl-N-(3-methoxyphenyl)-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-9-ethyl-N-(4-fluoro -3-methylphenyl)-9H-purin-2-amine;

tert-Butyl 4-(9-cyclopropyl-8-(pyridin-4-yl)-9H-purin-2-ylamino) phenethylcarbamate;

9-Ethyl-N-(4-fluoro-3-methoxyphenyl)-8-(2-(methylamino)pyrimidin-4-yl)-9H-purin-2-amine;

9-Cyclopropyl-N-(3-fluorophenyl)-8-(2-(methylamino)pyrimidin-4-yl)-9H-purin-2-amine;

N-(4-(9-Ethyl-8-(pyridin-4-yl)-9H-purin-2-lamino)benzyl) -N-methylacetamide;

8-(2-Aminopyrimidin-4-yl)-9-ethyl-N-(4-ethylphenyl)-9H-purin -2-amine;

9-Methyl-N-(3-((4-methylpiperazin-1-yl)methyl)phenyl)-8-(pyridin-4-yl)-9H-purin -2-amine;

9-Cyclopropyl-8-(pyridin-4-yl)-N-(3-(trifluoromethoxy)phenyl)-9H-purin-2-amine;

9-Ethyl-N-(3-(2-morpholinoethoxy)phenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

9-Methyl-N-(4-(piperazin-1-ylmethyl)phenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

N-(3-(2-(Cyclopentylamino)ethyl)phenyl)-9-ethyl-8-(pyridin-4-yl)-9H-purin-2-amine;

N-(3-(Aminomethyl)phenyl)-9-cyclopropyl-8-(pyridin-4-yl)-9H-purin-2-amine;

9-Isopropyl-N-(3-methoxyphenyl)-8-(2-(methylamino)pyrimidin-4-yl)-9H-purin-2-amine;

N-(8-(2-Aminopyrimidin-4-yl)-9-cyclopropyl-9H-purin-2-yl)quinolin-6-amine;

N-(3-Chlorophenyl)-9-cyclopropyl-8-(2-(methylamino)pyrimidin-4-yl)-9H-purin-2-amine;

9-Cyclopropyl-N-(4-((methylamino)methyl)phenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

9-Cyclopropyl-N-phenethyl-8-(pyridin-4-yl)-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-9-ethyl-N-(3-fluorophenyl)-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-9-isopropyl-N-(3-methoxyphenyl)-9H-purin-2-amine ;

9-Cyclopropyl-N-(3-methoxyphenyl)-8-(2-(methylamino)pyrimidin-4-yl)-9H-purin -2-amine;

9-Ethyl-N-(3-(2-methoxyethoxy)phenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

N-(3,4-Difluorophenyl)-9-ethyl-8-(pyridin-4-yl)-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-N-(2,4-dimethylphenyl)-9-ethyl-9H-purin-2-amine;

9-Ethyl-N-(3-(2-(ethylamino)ethyl)phenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

9-Methyl-N-(3-(morpholinomethyl)phenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

9-Methyl-N-(4-(2-(piperidin-1-yl)ethyl)phenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

N-(4-(Aminomethyl)phenyl)-9-cyclopropyl-8-(pyridin-4-yl)-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-9-cyclopropyl-N-(4-fluorophenyl)-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-9-ethyl-N-o-tolyl-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-9-ethyl-N-(3-ethylphenyl)-9H-purin-2-amine;

N-(8-(2-Aminopyrimidin-4-yl)-9-cyclopropyl-9H-purin-2-yl)quinolin-8-amine;

8-(2-Aminopyrimidin-4-yl)-N-(4-fluorophenyl)-9-(2,2,2-trifluoroethyl)-9H-purin-2-amine;

N-(4-(2-Aminoethyl)phenyl)-9-methyl-8-(pyridin-4-yl)-9H-purin-2-amine;

9-Ethyl-N-(3-ethylphenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

9-Isopropyl-N-(3-methoxyphenyl)-8-(pyrimidin-4-yl)-9H-purin-2-amine;

N-(4-(2-(Cyclopropylamino)ethyl)phenyl)-9-ethyl-8-(pyridin-4-yl)-9H-purin-2-amine;

N-(8-(2-Aminopyrimidin-4-yl)-9-cyclopropyl-9H-purin-2-yl)isoquinolin-5-amine;

N-(3-(2-(Dimethylamino)ethyl)phenyl)-9-ethyl-8-(pyridin-4-yl)-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-9-cyclopropyl-N-(3-methoxyphenyl)-9H-purin-2-amine;

9-Ethyl-N-(3-(2-(piperidin-1-yl)ethoxy)phenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

9-Methyl-N-(4-((methylamino)methyl)phenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

8-(2-Aminopyridin-4-yl)-9-ethyl-N-(3-ethylphenyl)-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-9-ethyl-N-p-tolyl-9H-purin-2-amine;

9-Cyclopropyl-N-(3,4-dimethoxyphenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

9-Methyl-8-(pyridin-4-yl)-N-(4-(2-(pyrrolidin-1-yl)ethyl)phenyl)-9H-purin-2-amine;

9-Ethyl-N-(4-fluorophenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-9-ethyl-N-(3-fluoro-2-methylphenyl)-9H-purin-2-amine;

9-Methyl-8-(pyridin-4-yl)-N-(3-(2-(pyrrolidin-1-yl)ethy)phenyl)-9H-purin-2-amine;

N-(3-(Aminomethyl)phenyl)-9-methyl-8-(pyridin-4-yl)-9H-purin-2-amine;

9-Cyclopropyl-N-(4-fluorophenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

N-(4-Methylbenzyl)-9-cyclopropyl-8-(pyridin-4-yl)-9H-purin-2-amine;

N-(4-(9-Ethyl-8-(pyridin-4-yl)-9H-purin-2-ylamino)benzy)acetamide;

N-(3-(9-Methyl-8-(pyridin-4-yl)-9H-purin-2-ylamino)benzyl)acetamide;

N-(4-(Aminomethyl)phenyl)-9-methyl-8-(pyridin-4-yl)-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-9-cyclopropyl-N-(2-(thiophen-2-yl)ethyl)-9H-purin-2amine;

8-(2-Aminopyridin-4-yl)-9-ethyl-N-(4-fluorophenyl)-9H-purin-2-amine, N-(3-(2-(Dimethylamino)ethoxy)phenyl)-9-ethyl-8-(pyridin-4-yl)-9H-purin-2-amine;

9-Methyl-N-(4-(piperidin-1-ylmethyl)phenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-N-(3,5-difluorophenyl)-9-ethyl-9H-purin-2-amine;

N-(4-(2-(Dimethylamino)ethyl)phenyl)-9-ethyl-8-(pyridin-4-yl)-9H-purin-2amine;

9-Cyclopropyl-8-(2-(methylamino)pyrimidin-4-yl)-N-phenyl-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-N-(2,5-difluorophenyl)-9-ethyl-9H-purin-2-amine;

9-Cyclopropyl-N-(3-(2-morpholinoethoxy)phenyl)-8-(pyridin-4-yl)-9H-purin-2amine;

8-(2-Aminopyrimidin-4-yl)-N-(3,4-difluorophenyl)-9-ethyl-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-N-(2,3-difluorophenyl)-9-ethyl-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-N-(4-fluorophenyl)-9-methyl-9H-purin-2-amine;

tert-Butyl 4-(9-cyclopropyl-8-(pyridin-4-yl)-9H-purin-2-ylamino) benzylcarbamate;

9-Cyclopropyl-N-(2,4-dimethoxyphenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

9-Methyl-N-(3-(2-(piperidin- 1 -yl)ethyl)phenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

N-(4-(2-Aminoethyl)phenyl)-9-ethyl-8-(pyridin-4-yl)-9H-purin-2-amine;

9-Ethyl-N-(3-((ethylamino)methyl)phenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-9-cyclopropyl-N-m-tolyl-9H-purin-2-amine;

N-(4-(9-Methyl-8-(pyridin-4-yl)-9H-purin-2-ylamino)phenethyl)acetamide;

8-(2-Aminopyrimidin-4-yl)-N-(3,4-dimethylphenyl)-9-ethyl-9H-purin-2-amine;

N-(4-Fluorophenyl)-8-(2-(methylamino)pyrimidin-4-yl)-9-(2,2,2-trifluoroethyl)-9H-purin-2-amine;

N-(3-(9-Cyclopropyl-8-(pyridin-4-yl)-9H-purin-2-ylamino)benzyl)acetamide;

(4-(2-(4-Fluorophenylamino)-9-methyl-9H-purin-8-yl)pyridin-2-yl)methanol;

N-(4-((Cyclopentylamino)methyl)phenyl)-9-ethyl-8-(pyridin-4-yl)-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-N-(2-chloro-5-fluorophenyl)-9-cyclopropyl-9H-purin-2-amine;

N-(4-Fluorophenyl)-9-methyl-8-(2-(methylamino)pyrimidin-4-yl)-9H-purin-2-amine;

9-Cyclopropyl-N-(3-methoxyphenyl)-8-(pyrimidin-4-yl)-9H-purin-2-amine;

N 1 -(8-(2-Aminopyrimidin-4-yl)-9-cyclopropyl-9H-purin-2-yl)-N 4 , N 4 -dimethylbenzene-1,4-diamine;

9-Methyl-8-(pyridin-4-yl)-N-(2-(thiophen-2-y)ethyl)-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-N-(2,3-dimethylphenyl)-9-ethyl-9H-purin-2-amine;

N-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-9-ethyl-8-(pyridin-4-yl)-9H-purin-2-amine;

3-(2-(3-Methoxyphenylamino)-8-(pyrimidin-4-yl)-9H-purin-9-yl)propanenitrile;

9-Ethyl-N-(3-ethylphenyl)-8-(2-(methylamino)pyrimidin-4-yl)-9H-purin-2-amine;

9-Ethyl-N-(4-((ethylamino)methyl)phenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

9-Methyl-N-(4-(2-morpholinoethyl)phenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

8-(2-Chloropyridin-4-yl)-9-cyclopropyl-N-phenyl-9H-purin-2-amine;

9-Cyclopropyl-8-(1-methyl-1H-pynol-2-yl)-N-(2-(thiophen-2-yl)ethyl)-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-9-ethyl-N-(3-fluoro-4-methylphenyl)-9H-purin-2amine;

9-Methyl-N-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-N-(3,5-dimethylphenyl)-9-ethyl-9H-purin-2-amine;

9-Methyl-N-(4-(morpholinomethyl)phenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

N-(3-((Dimethylamino)methyl)phenyl)-9-ethyl-8-(pyridin-4-yl)-9H-purin-2-amine;

8-(2-Aminopyridin-4-yl)-9-ethyl-N-(4-fluoro-3-methoxyphenyl)-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-N-(3-chlorophenyl)-9-ethyl-9H-purin-2-amine;

N-(4-(9-Methyl-8-(pyridin-4-yl)-9H-purin-2-ylamino)phenethyl)-N-methylacetamide;

8-(2-Aminopyrimidin-4-yl)-N-(4-chloro-2-fluorophenyl)-9-cyclopropyl-9H-purin-2-amine;

9-Cyclopropyl-N-(4-(2-(methylamino)ethyl)phenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

9-Cyclopropyl-N-(2-fluorophenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

9-Ethyl-N-(4-(2-(ethylamino)ethyl)phenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

9-Ethyl-N-(4-((isopropylamino)methyl)phenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

9-Methyl-N-(4-(2-(4-methylpiperazin-1-yl)ethyl)phenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

9-Ethyl-N-(3-fluorophenyl)-8-(2-(methylamino)pyrimidin-4-yl)-9H-purin-2amine;

N-(4-Fluorophenyl)-9-methyl-8-(pyridin-4-yl)-9H-purin-2-amine;

9-Cyclopropyl-N-phenyl-8-(pyridin-4-yl)-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-N-(2,3-dihydro-1H-inden-5-yl)-9-ethyl-9H-purin-2amine;

9-Ethyl-N-(4-(2-methoxyethoxy)phenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

N-(3-(Aminomethyl)phenyl)-9-ethyl-8-(pyridin-4-yl)-9H-purin-2-amine;

N-(3-((Cyclopentylamino)methyl)phenyl)-9-ethyl-8-(pyridin-4-yl)-9H-purin-2amine;

9-Methyl-N-(4-(2-(methylamino)ethyl)phenyl)-8-(pyridin-4-yl)-9H-purin-2amine;

N-(4-(2-(Cyclopentylamino)ethyl)phenyl)-9-ethyl-8-(pyridin-4-yl)-9H-purin-2-amine;

9-Methyl-N-(3-(2-(piperazin-1-yl)ethyl)phenyl)-8-(pyridin-4-yl)-9H-purin-2amine;

N-(2-Fluorophenethyl)-9-cyclopropyl-8-(pyridin-4-yl)-9H-purin-2-amine;

9-Cyclopropyl-N-(4-fluorophenyl)-8-(2-(methylamino)pyrimidin-4-yl)-9H-purin-2-amine;

9-Cyclopropyl-8-(pyridin-4-yl)-N-(3,4,5-trimethoxyphenyl)-9H-purin-2-amine;

9-Methyl-8-(pyridin-4-yl)-N-(4-(pyrrolidin-1-ylmethyl)phenyl)-9H-purin-2-amine;

9-Cyclopropyl-N-(3-ethylphenyl)-8-(2-(methylamino)pyrimidin-4-yl)-9H-purin-2-amine;

8-(6-Aminopyridin-3-yl)-9-ethyl-N-(4-fluorophenyl)-9H-purin-2-amine;

N 1 -(8-(2-Aminopyrimidin-4-yl)-9-cyclopropyl-9H-purin-2-yl)-N 3 ,N 3 -dimethylbenzene-1 ,3-diamine;

N-(3-((Cyclopropylamino)methyl)phenyl)-9-ethyl-8-(pyridin-4-yl)-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-N-(2,4-difluorophenyl)-9-ethyl-9H-purin-2-amine;

9-Cyclopropyl-N-(3,5-dimethoxyphenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

N-(4-(9-Cyclopropyl-8-(pyridin-4-yl)-9H-purin-2-ylamino)phenethyl)acetamide;

N-(4-(9-Ethyl-8-(pyridin-4-yl)-9H-purin-2-ylamino)phenethyl)-N-methylacetamide;

N-(4-(9-Methyl-8-(pyridin-4-yl)-9H-purin-2-ylamino)benzyl)acetamide;

9-Ethyl-N-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

N-(4-(2-Methoxyethoxy)phenyl)-9-methyl-8-(pyridin-4-yl)-9H-purin-2-amine;

8-(2-Chloropyridin-4-yl)-9-isopropyl-N-(3-methoxyphenyl)-9H-purin-2-amine;

8-(2-Aminopyridin-4-yl)-9-isopropyl-N-(3-methoxyphenyl)-9H-purin-2-amine;

9-Ethyl-N-(4-(2-(methylamino)ethyl)phenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

9-Ethyl-N-(4-(2-morpholinoethoxy)phenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

8-(2-Aminopyridin-4-yl)-N-(3,4-difluorophenyl)-9-ethyl-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-N-(2-chlorophenyl)-9-ethyl-9H-purin-2-amine;

9-Methyl-N-(3-(piperidin-1-ylmethyl)phenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

8-(6-Aminopyridin-3-yl)-9-ethyl-N-(3-ethylphenyl)-9H-purin-2-amine;

N-(4-(9-Cyclopropyl-8-(pyridin-4-yl)-9H-purin-2-ylamino)benzyl)-N-methylacetamide;

9-Cyclopropyl-8-(pyridin-3-yl)-N-(2-(thiophen-2-yl)ethyl)-9H-purin-2-amine;

N-(2,2-Dimethylbenzo[d][1,3]dioxol-5-yl)-9-ethyl-8-(pyridin-4-yl)-9H-purin-2-amine;

N-(4-(9-Cyclopropyl-8-(pyridin-4-yl)-9H-purin-2-ylamino)phenethyl)-N-methylacetarnide;

9-Cyclopropyl-8-(thiazol-2-yl)-N-(2-(thiophen-2-yl)ethyl)-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-N-(2,6-difluorophenyl)-9-ethyl-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-9-ethyl-N-(2-fluoro-4-methylphenyl)-9H-purin-2amine;

8-(2-Aminopyrimidin-4-yl)-N-(4-chlorophenyl)-9-ethyl-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-N-(3-chloro-4-fluorophenyl)-9-cyclopropyl-9H-purin-2-amine;

9-Methyl-N-(3-(2-(4-methylpiperazin-1-yl)ethyl)phenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

9-Ethyl-N-(3-((isopropylamino)methyl)phenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

N-(8-(2-Aminopyrimidin-4-yl)-9-cyclopropyl-9H-purin-2-yl)quinolin-5-amine;

N-(2-(4-(9-Methyl-8-(pyridin-4-yl)-9H-purin-2-ylamino)phenoxy) ethyl)acetamide;

8-(2-Chloropyridin-4-yl)-9-cyclopropyl-N-(3-methoxyphenyl)-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-N-(2,5-dimethylphenyl)-9-ethyl-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-9-ethyl-N-(4-fluoro-2-methylphenyl)-9H-purin-2amine ;

N-(4-((Cyclopropylamino)methyl)phenyl)-9-ethyl-8-(pyridin-4-yl)-9H-purin-2amine;

8-(2-Aminopyrimidin-4-yl)-9-ethyl-N-(2-ethylphenyl)-9H-purin-2-amine;

N-(4-Methoxyphenyl)-9-methyl-8-(pyridin-4-yl)-9H-purin-2-amine;

9-Cyclopropyl-8-(pyrimidin-4-yl)-N-(2-(thiophen-2-yl)ethyl)-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-9-ethyl-N-(4-fluoro-3-methoxyphenyl)-9H-purin-2-amine;

9-Cyclopropyl-8-(1-methyl-1H-imidazol-5-yl)-N-(2-(thiophen-2-yl)ethyl)-9H-purin-2-amine;

N-(Benzo[d][1,3]dioxol-5-yl)-9-cyclopropyl-8-(pyridin-4-yl)-9H-purin-2-amine;

N-(4-(2-(Dimethylamino)ethoxy)phenyl)-9-ethyl-8-(pyridin-4-yl)-9H-purin-2amine;

N-(Benzo[d]thiazol-6-yl)-9-cyclopropyl-8-(pyridin-4-yl)-9H-purin-2-amine;

9-Ethyl-N-(4-fluoro-3-methoxyphenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-N-(2,3-dihydro-1H-inden-4-yl)-9-ethyl-9H-purin-2amine;

N-(3-(2-(Cyclopropylamino)ethyl)phenyl)-9-ethyl-8-(pyridin-4-yl)-9H-purin-2amine;

9-Ethyl-N-(4-fluorophenyl)-8-(2-(methylamino)pyrimidin-4-yl)-9H-purin-2amine;

9-Ethyl-N-(4-(2-(isopropylamino)ethyl)phenyl)-8-(pyridin-4-yl)-9H-purin-2amine;

8-(2-Aminopyrimidin-4-yl)-N-(3-chloro-2-fluorophenyl)-9-cyclopropyl-9H-purin-2-amine;

3-(8-(2-Aminopyrimidin-4-yl)-2-(3-methoxyphenylamino)-9H-purin-9yl)propanenitrile;

8-(2-Aminopyridin-4-yl)-N-(4-fluorophenyl)-9-methyl-9H-purin-2-amine;

N-(4-Fluorophenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

N-(4-Chlorophenyl)-9-cyclopropyl-8-(pyridin-4-yl)-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-9-cyclopropyl-N-(3-ethylphenyl)-9H-purin-2-amine;

9-Ethyl-N-(4-((methylamino)methyl)phenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

N-(4-Fluorophenyl)-8-(pyridin-4-yl)-9-(2,2,2-trifluoroethyl)-9H-purin-2-amine, N-(3-(9-Ethyl-8-(pyridin-4-yl)-9H-purin-2-ylamino)benzyl)acetamide;

9-Methyl-8-(pyridin-4-yl)-N-(3-(pyrrolidin-1-ylmethyl)phenyl)-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-9-ethyl-N-(5-fluoro-2-methylphenyl)-9H-purin-2amine;

8-(2-Chloropyridin-4-yl)-9-cyclopropyl-N-(2-(thiophen-2-yl)ethyl)-9H-purin-2amine;

8-(2-Aminopyrimidin-4-yl)-N-(5-chloro-2-fluorophenyl)-9-cyclopropyl-9H-purin-2-amine;

9-Methyl-N-(3-(2-morpholinoethyl)phenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

9-Cyclopropyl-N-(2-methoxyphenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

8-(2-Chloropyridin-4-yl)-9-ethyl-N-(3-ethylphenyl)-9H-purin-2-amine;

9-Cyclopropyl-N-(3-methoxyphenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

N-(2-Methoxyphenethyl)-9-cyclopropyl-8-(pyridin-4-yl)-9H-purin-2-amine;

Ethyl-4-(2-(4-fluorophenylamino)-9-methyl-9H-purin-8-yl)picolinate;

8-(2-Aminopyrimidin-4-yl)-N-(2-chloro-4-fluorophenyl)-9-cyclopropyl-9H-purin-2-amine;

N-(4-(2-Aminoethyl)phenyl)-9-cyclopropyl-8-(pyridin-4-yl)-9H-purin-2-amine;

N-Cyclopentyl-9-cyclopropyl-8-(pyridin-4-yl)-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-9-cyclopropyl-N-(3-fluorophenyl)-9H-purin-2-amine;

9-Cyclopropyl-8-(pyridin-4-yl)-N-(2-(thiophen-2-yl)ethyl)-9H-purin-2-amine;

8-(2-Aminopyridin-4-yl)-9-cyclopropyl-N-phenyl-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-N-(3-chlorophenyl)-9-cyclopropyl-9H-purin-2-amine;

N-(4-(Aminomethyl)phenyl)-9-ethyl-8-(pyridin-4-yl)-9H-purin-2-amine;

N-(4-(9-Methyl-8-(pyridin-4-yl)-9H-purin-2-ylamino)benzyl)-2,2,2trifluoroacetamide;

9-Ethyl-N-(3-(2-(isopropylamino)ethyl)phenyl)-8-(pyridin-4-yl)-9H-purin-2amine;

N-(3,4-Difluorophenyl)-9-ethyl-8-(2-(methylamino)pyrimidin-4-yl)-9H-purin-2amine;

9-Methyl-N-(3-(piperazin-1-ylmethyl)phenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

9-Cyclopropyl-N-isobutyl-8-(pyridin-4-yl)-9H-purin-2-amine;

9-Ethyl-8-(2-(methylamino)pyrimidin-4-yl)-N-m-tolyl-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-9-cyclopropyl-N-phenyl-9H-purin-2-amine;

9-Cyclopropyl-8-(1H-pyrrol-2-yl)-N-(2-(thiophen-2-yl)ethyl)-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-9-ethyl-N-(4-fluorophenyl)-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-9-ethyl-N-m-tolyl-9H-purin-2-amine;

9-Methyl-N-(4-(2-(piperazin-1-yl)ethyl)phenyl)-8-(pyridin-4-yl)-9H-purin-2amine ;

8-(Pyridin-4-yl)-N-(2-(thiophen-2-yl)ethyl)-9H-purin-2-amine;

N-(44(Dimethylamino)methyl)phenyl)-9-ethyl-8-(pyridin-4-yl)-9H-purin-2amine;

9-Cyclopropyl-N-(4-methoxyphenyl)-8-(pyridin-4-yl)-9H-purin-2-amine;

8-(2-Aminopyrimidin-4-yl)-9-ethyl-N-(5,6,7,8-tetrahydronaphthalen-1-yl)-9H-purin-2-amine.