Use of 8-amino-aryl-substituted imidazopyrazines as kinase inhibitors
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Abstract
The present invention relates to 8-amino-aryl-substituted imidazopyrazines which modulate the activity of protein kinases (“PKs”). The compounds of this invention are therefore useful in treating disorders related to abnormal PK activity. Pharmaceutical compositions comprising these compounds, methods of treating diseases utilizing pharmaceutical compositions comprising these compounds and methods of preparing them are also disclosed.
148 Citations
114 Claims
- 1. A compound of the formula I:
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14. A compound selected from the group consisting of:
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N-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-2-pyrrolidin-1-yl-acetamide;
N-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-2-morpholin-4-yl-acetamide;
2-Diethylamino-N-[4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-acetamide;
2-Benzylamino-N-[4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-acetamide;
N-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-2-(4-methyl-piperazin-1-yl)-acetamide;
2-(4-Hydroxy-piperidin-1-yl)-N-[4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-acetamide;
2-Benzylamino-N-[3-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-acetamide;
N-[3-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-2-(4-methyl-piperazin-1-yl)-acetamide;
N-[3-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-2-morpholin-4-yl-acetamide;
2-(4-Hydroxy-piperidin-1-yl)-N-[3-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-acetamide;
N-[3-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-2-pyrrolidin-1-yl-acetamide;
2-Hydroxy-N-[4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-acetamide;
N-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-2-(2-morpholin-4-yl-ethoxy)-acetamide;
N-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-2-morpholin-4-yl-acetamide;
1-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-2-morpholin-4-yl-ethanone;
2-Diethylamino-N-[4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-acetamide;
2-Benzylamino-N-[4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-acetamide;
N-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-2-(4-methyl-piperazin-1-yl)-acetamide;
1-(2-Hydroxy-3-morpholin-4-yl-propyl)-3-[4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-urea;
N-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-2-pyrrolidin-1-yl-acetamide;
2-Benzylamino-N-[3-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-acetamide;
N-[3-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-2-(4-methyl-piperazin-1-yl)-acetamide;
N-[3-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-2-morpholin-4-yl-acetamide;
2-(4-Hydroxy-piperidin-1-yl)-N-[3-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-acetamide;
N-[3-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-2-pyrrolidin-1-yl-acetamide;
1-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-3-(2-phenyl-propyl)-urea;
1-(2-Hydroxy-ethyl)-3-[4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-urea;
1-[4-(8-Cyclopropylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-(2-hydroxy-ethyl)-urea;
1-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-[2-(4-methyl-piperazin-1-yl)-ethyl]-urea;
1-(4-Chloro-benzyl)-3-[4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-urea;
1-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-phenethyl-urea;
1-(2-Fluoro-benzyl)-3-[4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-urea;
1-[2-(4-Hydroxy-phenyl)-ethyl]-3-[4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-urea;
1-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-{2-[4-(2-morpholin-4-yl-ethoxy)-phenyl]-ethyl}-urea;
1-(4-Hydroxy-benzyl)-3-[4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-urea;
1-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-[4-(2-morpholin-4-yl-ethoxy)-benzyl]-urea;
1-(3-Fluoro-benzyl)-3-[4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-urea;
1-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-(4-morpholin-4-yl-benzyl)-urea;
1-(4-Fluoro-benzyl)-3-[4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-urea;
1-(4-Methoxy-benzyl)-3-[4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-urea;
1-[2-(1,1-Dioxo-λ
6-thiomorpholin-4-yl)-ethyl]-3-[4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-urea;
[4-(8-Cyclopropylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-methanol;
Methyl-{3-[4-(2-pyrrolidin-1-yl-ethylamino)-phenyl]-imidazo[1,2-a]pyrazin-8-yl}-amine;
Methyl-{3-[3-(2-morpholin-4-yl-ethylamino)-phenyl]-imidazo[1,2-a]pyrazin-8-yl}-amine;
N-Benzyl-N′
-[4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-ethane-1,2-diamine;
2-Piperidin-1-yl-ethanesulfonic acid [4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-amide;
2-Diethylamino-ethanesulfonic acid-[4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-amide;
2-Cyclopropylamino-ethanesulfonic acid [4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-amide;
N-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-methanesulfonamide;
3-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-benzenesulfonyl]-oxazolidin-2-one;
Methyl-{3-[4-(morpholine-4-sulfonyl)-phenyl]-imidazo[1,2-a]pyrazin-8-yl}-amine;
[3-(4-Methanesulfonyl-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine;
1-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-2-morpholin-4-yl-ethanone;
1-[4-(8-Cyclopropylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-2-morpholin-4-yl-ethanone;
1-[4-(8-Cyclopropylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-ethanol;
and a prodrug or pharmaceutically acceptable salt thereof. - View Dependent Claims (15, 16, 17, 18, 19, 20, 21, 22, 23)
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24. A compound selected from the group consisting of:
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2-(4-Chloro-benzylamino)-ethanesulfonic acid [4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-amide;
2-(2-Chloro-benzylamino)-ethanesulfonic acid [4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-amide;
1-(2,6-Difluoro-benzyl)-3-[4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-urea;
1-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-pyridin-4-ylmethyl-urea;
1-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-pyridin-2-ylmethyl-urea;
1-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-(2-pyridin-3-yl-ethyl)-urea;
1-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-(2-pyridin-2-yl-ethyl)-urea;
N-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-2-(2-phenyl-cyclopropylamino)-acetamide;
2-[1-(4-Chloro-phenyl)-ethylamino]-N-[4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-acetamide;
[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-carbamic acid 2-(4-fluoro-phenyl)-propyl ester;
[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-carbamic acid 2-(2-chloro-phenyl)-ethyl ester;
N-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-2-phenoxy-acetamide;
2-(2,6-Difluoro-benzyloxy)-N-[4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-acetamide;
2-[2-(2-Fluoro-phenyl)-ethoxy]-N-[4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-acetamide;
2-[2-(2,6-Difluoro-phenyl)-ethoxy]-N-[4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-acetamide;
1-(3-Hydroxy-benzyl)-3-[4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-urea;
2-(2-Fluoro-benzylamino)-N-[4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-acetamide;
N-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-2-(pyridin-3-ylmethoxy)-acetamide;
2-[2-(5-Chloro-2-fluoro-phenyl)-ethoxy]-N-[4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-acetamide;
1-(2-Chloro-4-fluoro-benzyl)-3-[4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-urea;
1-(2,4-Dichloro-phenyl)-3-[4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-urea;
1-Indan-1-yl-3-[4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-urea;
1-[2-(2,6-Dichloro-phenyl)-ethyl]-3-[4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-urea;
Ethyl-(3-thiophen-3-yl-imidazo[1,2-a]pyrazin-8-yl)-amine;
Methyl-(3-pyridin-4-yl-imidazo[1,2-a]pyrazin-8-yl)-amine;
[3-(6-Methoxy-pyridin-3-yl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine;
(3-Furan-3-yl-imidazo[1,2-a]pyrazin-8-yl)-methyl-amine;
3-Thiophen-3-yl-imidazo[1,2-a]pyrazin-8-ylamine;
Methyl-(3-thiophen-3-yl-imidazo[1,2-a]pyrazin-8-yl)-amine;
(3-Benzo[b]thiophen-2-yl-imidazo[1,2-a]pyrazin-8-yl)-methyl-amine;
(3-Benzo[b]thiophen-3-yl-imidazo[1,2-a]pyrazin-8-yl)-methyl-amine;
Cyclopropyl-(3-thiophen-3-yl-imidazo[1,2-a]pyrazin-8-yl)-amine;
Cyclopropyl-(3-furan-3-yl-imidazo[1,2-a]pyrazin-8-yl)-amine;
Cyclopropyl-[3-(6-methoxy-pyridin-3-yl)-imidazo[1,2-a]pyrazin-8-yl]-amine;
5-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-1H-pyridin-2-one;
Thiophen-2-yl-imidazo[1,2-a]pyrazin-8-ylamine;
(6-Methoxy-pyridin-3-yl)-imidazo[1,2-a]pyrazin-8-ylamine;
Methyl-(3-thiophen-2-yl-imidazo[1,2-a]pyrazin-8-yl)-amine;
3-(1H-Indol-4-yl)-imidazo[1,2-a]pyrazin-8-ylamine;
[3-(1H-Indol-5-yl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine;
Cyclopropyl-[3-(1H-indol-4-yl)-imidazo[1,2-a]pyrazin-8-yl]-amine;
[3-(1H-Indol-4-yl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine;
Methyl-(3-pyridin-2-yl-imidazo[1,2-a]pyrazin-8-yl)-amine;
Methyl-(3-thiazol-2-yl-imidazo[1,2-a]pyrazin-8-yl)-amine;
1-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-thiophen-2-yl]-ethanone;
1-[4-(8-Cyclopropylamino-imidazo[1,2-a]pyrazin-3-yl)-thiophen-2-yl]-ethanone;
[3-(6-Amino-pyridin-2-yl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine;
[3-(2-Amino-pyrimidin-5-yl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine;
Methyl-(3-thiophen-2-yl-imidazo[1,2-a]pyrazin-8-yl)-amine;
[3-(5-Chloro-thiophen-2-yl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine;
2-[5-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-1H-indol-3-yl]-acetamide;
[3-(3-Dimethylaminomethyl-1H-indol-5-yl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine;
and a prodrug or pharmaceutically acceptable salt thereof. - View Dependent Claims (25, 26, 27, 28, 29, 30, 31, 32, 33)
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34. A compound selected from the group consisting of:
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5-(Methylamino-imidazo[1,2-a]pyrazin-3-yl)-1H-indole-2-carboxylic acid(3-morpholine-4-yl-propyl)-amide;
5-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-1H-indole-2-carboxylic acid (3-morpholin-4-yl-propyl)-amide;
5-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-1H-indole-2-carboxylic acid (2-morpholin-4-yl-ethyl)-amide;
5-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-1H-indole-2-carboxylic acid (2-diethylamino-ethyl)-amide;
[5-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-1H-indol-2-yl]-morpholin-4-yl-methanone;
5-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-thiophene-2-carboxylic acid methyl ester;
[5-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-thiophen-2-yl]-(4-methyl-piperazin-1-yl)-methanone;
[5-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-thiophen-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone;
[5-(8-Methyl amino-imidazo[1,2-a]pyrazin-3-yl)-thiophen-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone;
[5-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-thiophen-2-yl]-(3-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone;
5-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-thiophene-2-carboxylic acid (2-diethylamino-ethyl)-amide;
5-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-thiophene-2-carboxylic acid (2-morpholin-4-yl-ethyl)-amide;
[5-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-thiophen-2-yl]-morpholin-4-yl-methanone;
{3-[1-(2-Diethylamino-ethyl)-1H-indol-5-yl]-imidazo[1,2-a]pyrazin-8-yl}-methyl-amine;
Methyl-{3-[1-(3-morpholin-4-yl-propyl)-1H-indol-5-yl]-imidazo[1,2-a]pyrazin-8-yl}-amine;
and a prodrug or pharmaceutically acceptable salt thereof. - View Dependent Claims (35, 36, 37, 38, 39, 40, 41, 42, 43)
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- 44. A compound of the formula I:
- 55. A compound of the formula I:
- 65. A compound of the formula I:
- 75. A compound of the formula I:
- 85. A compound of the formula I:
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95. A compound selected from the group consisting of:
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Methyl-(3-phenyl-imidazo[1,2-a]pyrazin-8-yl)-amine, 3-Phenyl-imidazo[1,2-a]pyrazin-8-ylamine, 3-(4-Amino-phenyl)-imidazo[1,2-a]pyrazin-8-ylamine, N-[4-(4-trifluoromethyl-benzamide-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-4-trifluoromethyl-benzamide, N-[4-(8-Amino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-4-trifluoromethyl-benzamide, (4-Methoxy-phenyl)-(3-phenyl-imidazo[1,2-a]pyrazin-8-yl)-amine, 4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenol, Dimethyl-(3-phenyl-imidazo[1,2-a]pyrazin-8-yl)-amine, Isopropyl-(3-phenyl-imidazo[1,2-a]pyrazin-8-yl)-amine, 4-(8-Isopropylamino-imidazo[1,2-a]pyrazin-3-yl)-phenol, Butyl-(3-phenyl-imidazo[1,2-a]pyrazin-8-yl)-amine, Ethyl-(3-phenyl-imidazo[1,2-a]pyrazin-8-yl)-amine, (2-Morpholin-4-yl-ethyl)-(3-phenyl-imidazo[1,2-a]pyrazin-8-yl)-amine, Benzyl-(3-phenyl-imidazo[1,2-a]pyrazin-8-yl)-amine, 2-(3-Phenyl-imidazo[1,2-a]pyrazin-8-ylamino)-ethanol, 1-Butyl-3-(3-phenyl-imidazo[1,2-a]pyrazin-8-yl)-urea, N-[3-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-acetamide, N-[4-(8-Cyclopropylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-acetamide, 2,6-Dimethyl-4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenol, 3-(4-Fluoro-phenyl)-imidazo[1,2-a]pyrazin-8-ylamine, Cyclopropyl-(3-phenyl-imidazo[1,2-a]pyrazin-8-yl)-amine, [3-(4-Fluoro-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine, Methyl-[3-(2-trifluoromethyl-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-amine, Methyl-[3-(3-trifluoromethyl-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-amine, Methyl-[3-(2-phenoxy-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-amine, (3-Biphenyl-2-yl-imidazo[1,2-a]pyrazin-8-yl)-methyl-amine, [3-(2-Benzyloxy-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine, 1-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-ethanone, 1-[3-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-ethanone, [3-(3-Isopropyl-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine, [3-(4-tert-Butyl-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine, [3-(4-Cyclohexyl-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine, [3-(3,5-Bis-trifluoromethyl-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine, 3-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-benzoic acid, 3-(8-Methylamino-imidazo[1,2-a]pyrazin-4-yl)-benzoic acid, Methyl-(3-o-tolyl-imidazo[1,2-a]pyrazin-8-yl)-amine, [4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-carbamic acid benzyl ester, Methyl-[3-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-amine, [3-(2,4-Difluoro-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine, [3-(3,4-Dichloro-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine, [3-(3-Fluoro-4-methoxy-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine, (3-Biphenyl-4-yl-imidazo[1,2-a]pyrazin-8-yl)-methyl-amine, (3-Biphenyl-3-yl-imidazo[1,2-a]pyrazin-8-yl)-methyl-amine, [3-(4-Benzyloxy-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine, Methyl-(3-naphthalen-1-yl-imidazo[1,2-a]pyrazin-8-yl)-amine, [3-(2-Chloro-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine, N-[3-(8-Cyclopropylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]acetamide, Methyl-[3-(2-trifluoromethoxy-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-amine, Methyl-[3-(3-trifluoromethoxy-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-amine, Cyclopropyl-{3-[3-(2-morpholin-4-yl-ethoxy)-phenyl]-imidazo[1,2-a]pyrazin-8-yl}-amine, 3-(8-Cyclopropylamino-imidazo[1,2-a]pyrazin-3-yl)-phenol, Methyl-[3-(4-trifluoromethoxy-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-amine, [3-(2-Fluoro-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine, [3-(3,4-Difluoro-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine, (3-Benzo[1,3]dioxol-5-yl-imidazo[1,2-a]pyrazin-8-yl)-methyl-amine, [3-(3-Chloro-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine, [3-(4-Methoxy-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine, [3-(2-Methoxy-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine, Methyl-[3-(4-phenoxy-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-amine, [3-(4-Benzyloxy-3-fluoro-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine, [3-(4-Isopropyl-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine, [3-(3,5-Bis-trifluoromethyl-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-cyclopropyl-amine, Cyclopropyl-[3-(3,4-dichloro-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-amine, 3-(8-Cyclopropylamino-imidazo[1,2-a]pyrazin-3-yl)-benzoic acid, Methyl-{3-[4-(2-morpholin-4-yl-ethoxy)-phenyl]-imidazo[1,2-a]pyrazin-8-yl}-amine, Cyclopropyl-{3-[4-(2-morpholin-4-yl-ethoxy)-phenyl]-imidazo[1,2-a]pyrazin-8-yl}-amine, Cyclopropyl-[3-(4-dimethylamino-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-amine, Cyclopropyl-[3-(4-phenoxy-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-amine, 1-[4-(8-Cyclopropylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-ethanone, [4-(8-Cyclopropylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-carbamic acid benzyl ester, N-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-acetamide, [3-(3-Amino-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-cyclopropyl-amine, [3-(4-Amino-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine, Methyl-(3-naphthalen-2-yl-imidazo[1,2-a]pyrazin-8-yl)-amine, 4-(8-Cyclopropylamino-imidazo[1,2-a]pyrazin-3-yl)-benzoic acid, [3-(4-Amino-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-cyclopropyl-amine, Methyl-{3-[3-(2-morpholin-4-yl-ethoxy)-phenyl]-imidazo[1,2-a]pyrazin-8-yl}-amine, [3-(3-Amino-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine, 3-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenol, 4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-N-(2-morpholin-4-yl-ethyl)-benzamide, 4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-N-(3-morpholin-4-yl-propyl)-benzamide, 4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-N-(3-pyrrolidin-1-yl-propyl)-benzamide, 1-[3-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-(3-morpholin-4-yl-propyl)-urea, (R)-2-Pyrrolidin-1-ylmethyl-pyrrolidine-1-carboxylic acid [4-(8-cyclopropylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-amide, (S)-2-Pyrrolidin-1-ylmethyl-pyrrolidine-1-carboxylic acid [4-(8-cyclopropylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-amide, (S)-2-Pyrrolidin-1-ylmethyl-pyrrolidine-1-carboxylic acid [4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-amide, 1-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-(3-morpholin-4-yl-propyl)-urea, (S)-3-Hydroxy-pyrrolidine-1-carboxylic acid [4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-amide, (R)-2-Pyrrolidin-1-ylmethyl-pyrrolidine-1-carboxylic acid [3-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-amide, 1-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-(3-pyrrolidin-1-yl-propyl)-urea, 4-Pyrrolidin-1-yl-piperidine-1-carboxylic acid [4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-amide, 1-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-(2-morpholin-4-yl-ethyl)-urea, 4-Hydroxy-piperidine-1-carboxylic acid [4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-amide (R)-2-Pyrrolidin-1-ylmethyl-pyrrolidine-1-carboxylic acid [3-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-amide, 4-Hydroxy-piperidine-1-carboxylic acid [3-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-amide, 1-[3-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-(2-morpholin-4-yl-ethyl)-urea, 1-[3-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-(2-pyrrolidin-1-yl-ethyl)-urea, 1-[3-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-(3-pyrrolidin-1-yl-propyl)-urea, 1-[3-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-(3-morpholin-4-yl-propyl)-urea, (R)-2-Pyrrolidin-1-ylmethyl-pyrrolidine-1-carboxylic acid [4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-amide, (R)-2-Dimethylaminomethyl-pyrrolidine-1-carboxylic acid [4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-amide, 1-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-(2-pyrrolidin-1-yl-ethyl)-urea, (R)-3-Hydroxy-pyrrolidine-1-carboxylic acid [4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-amide, 1-[4-(8-Cyclopropylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-(3-pyrrolidin-1-yl-propyl)-urea, 1-[4-(8-Cyclopropylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-(3-morpholin-4-yl-propyl)-urea, 1-[4-(8-Cyclopropylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-(2-pyrrolidin-1-yl-ethyl)-urea, 1-[4-(8-Cyclopropylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-(2-morpholin-4-yl-ethyl)-urea, [5-(4-Fluoro-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine, Methyl-(5-phenyl-imidazo[1,2-a]pyrazin-8-yl)-amine, Methyl-(5-thiophen-3-yl-imidazo[1,2-a]pyrazin-8-yl)-amine, 4-(8-Methylamino-imidazo[1,2-a]pyrazin-5-yl)-phenol, N-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-5-yl)-phenyl]-acetamide, [3,5-Bis-(4-fluoro-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine, (3,5-Diphenyl-imidazo[1,2-a]pyrazin-8-yl)-methyl-amine, Methyl-(6-phenyl-imidazo[1,2-a]pyrazin-8-yl)-amine, 4-(8-Methylamino-imidazo[1,2-a]pyrazin-6-yl)-phenol, 6-Phenyl-imidazo[1,2-a]pyrazin-8-ylamine;
Dimethyl-(3-phenyl-imidazo[1,2-a]pyrazin-5-yl-amine, and a prodrug or pharmaceutically acceptable salt thereof. - View Dependent Claims (96, 97, 98, 99, 100, 101, 102, 103, 104)
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105. A compound selected from the group consisting of:
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Methyl-(3-phenyl-imidazo[1,2-a]pyrazin-8-yl)-amine, 4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenol, Ethyl-(3-phenyl-imidazo[1,2-a]pyrazin-8-yl)-amine, Cyclopropyl-(3-phenyl-imidazo[1,2-a]pyrazin-8-yl)-amine, 1-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-ethanone, [4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-carbamic acid benzyl ester, [3-(3-Fluoro-4-methoxy-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine, 3-(8-Cyclopropylamino-imidazo[1,2-a]pyrazin-3-yl)-phenol, Methyl-[3-(4-trifluoromethoxy-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-amine, [3-(4-Benzyloxy-3-fluoro-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine, Cyclopropyl-[3-(4-dimethylamino-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-amine, 1-[4-(8-Cyclopropylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-ethanone, [4-(8-Cyclopropylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-carbamic acid benzyl ester, [3-(3-Amino-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-cyclopropyl-amine, [3-(4-Amino-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine, Methyl-(3-naphthalen-2-yl-imidazo[1,2-a]pyrazin-8-yl)-amine, [3-(4-Amino-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-cyclopropyl-amine, [3-(3-Amino-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-methyl-amine, 3-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenol, 1-[3-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-(3-morpholin-4-yl-propyl)-urea, (R)-2-Pyrrolidin-1-ylmethyl-pyrrolidine-1-carboxylic acid [4-(8-cyclopropylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-amide, (S)-2-Pyrrolidin-1-ylmethyl-pyrrolidine-1-carboxylic acid [4-(8-cyclopropylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-amide, (S)-2-Pyrrolidin-1-ylmethyl-pyrrolidine-1-carboxylic acid [4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-amide, 1-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-(3-morpholin-4-yl-propyl)-urea, (S)-3-Hydroxy-pyrrolidine-1-carboxylic acid [4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-amide, (R)-2-Pyrrolidin-1-ylmethyl-pyrrolidine-1-carboxylic acid [3-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-amide, 1-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-(3-pyrrolidin-1-yl-propyl)-urea, 4-Pyrrolidin-1-yl-piperidine-1-carboxylic acid [4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-amide, 1-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-(2-morpholin-4-yl-ethyl)-urea, 4-Hydroxy-piperidine-1-carboxylic acid [4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-amide, 1-[3-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-(2-morpholin-4-yl-ethyl)-urea, 1-[3-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-(2-pyrrolidin-1-yl-ethyl)-urea, 1-[3-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-(3-pyrrolidin-1-yl-propyl)-urea, 1-[3-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-(3-morpholin-4-yl-propyl)-urea, 1-[4-(8-Methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-(2-pyrrolidin-1-yl-ethyl)-urea, (R)-3-Hydroxy-pyrrolidine-1-carboxylic acid [4-(8-methylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-amide, 1-[4-(8-Cyclopropylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-(3-pyrrolidin-1-yl-propyl)-urea, 1-[4-(8-Cyclopropylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-(3-morpholin-4-yl-propyl)-urea, 1-[4-(8-Cyclopropylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-(2-pyrrolidin-1-yl-ethyl)-urea;
1-[4-(8-Cyclopropylamino-imidazo[1,2-a]pyrazin-3-yl)-phenyl]-3-(2-morpholin-4-yl-ethyl)-urea;
and a prodrug or pharmaceutically acceptable salt thereof. - View Dependent Claims (106, 107, 108, 109, 110, 111, 112, 113, 114)
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Specification