Novel pyrimidine compounds, process for their preparation and compositions containing them
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Abstract
The present invention provides new heterocyclic compounds, particularly substituted pyrimidines, methods and compositions for making and using these heterocyclic compounds, and methods for treating a variety of diseases and disease states, including atherosclerosis, arthritis, restenosis, diabetic nephropathy, or dyslipidemia, or disease states mediated by the low expression of Perlecan.
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Citations
34 Claims
- 1. A compound having the formula:
- 6. A compound having the formula:
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11. A compounds having the formula:
- 13. A compound having the formula:
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14. A compound selected from:
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1-[2-(3-Chloro-4-methoxy-phenylamino)-6-cycloheptylamino-pyrimidin-4-yl]-piperidin-4-ol;
N2,N4-Bis-(3-chloro-4-methoxy-phenyl)-6-phenyl-pyrimidine-2,4-diamine;
N2-(3-Chloro-4-methoxy-phenyl)-N4-methyl-6-phenyl-pyrimidine-2,4-diamine;
N2-(3-Chloro-4-methoxy-phenyl)-N4-isopropyl-6-phenyl-pyrimidine-2,4-diamine;
N2-(3-Chloro-4-methoxy-phenyl)-N4-cycloheptyl-6-phenyl-pyrimidine-2,4-diamine;
N4-Benzyl-N2-(3-chloro-4-methoxy-phenyl)-6-phenyl-pyrimidine-2,4-diamine;
(3-Chloro-4-methoxy-phenyl)-[4-ethoxy-6-(4-methoxy-phenyl)-pyrimidin-2-yl]-amine;
(3-Chloro-4-methoxy-phenyl)-[4-isopropoxy-6-(4-methoxy-phenyl)-pyrimidin-2-yl]-amine;
[4-Benzyloxy-6-(4-methoxy-phenyl)-pyrimidin-2-yl]-(3-chloro-4-methoxy-phenyl)-amine;
(3-Chloro-4-methoxy-phenyl)-[4-(4-methoxy-phenyl)-6-(4-methyl-benzyloxy)-pyrimidin-2-yl]-amine;
[2-(3-Chloro-4-methoxy-phenylamino)-6-(4-methoxy-phenyl)-pyrimidin-4-yloxy]-acetic acid ethyl ester;
[2-(3-Chloro-4-methoxy-phenylamino)-6-(4-methoxy-phenyl)-pyrimidin-4-yloxy]-acetic acid;
1-[4-(3-Chloro-4-methoxy-phenylamino)-6-phenyl-pyrimidin-2-yl]-piperidin-4-ol;
1-[4-(3-Fluoro-4-methoxy-phenylamino)-6-phenyl-pyrimidin-2-yl]-piperidin-4-ol;
1-[4-(Methyl-phenyl-amino)-6-phenyl-pyrimidin-2-yl]-piperidin-4-ol;
1-[4-Phenyl-6-(3-trifluoromethyl-phenylamino)-pyrimidin-2-yl]-piperidin-4-ol;
1-[4-(4-Chloro-3-trifluoromethyl-phenylamino)-6-phenyl-pyrimidin-2-yl]-piperidin-4-ol;
1-[4-(Benzo[1,3]dioxol-5-ylamino)-6-phenyl-pyrimidin-2-yl]-piperidin-4-ol;
1-[4-Phenyl-6-(4-trifluoromethyl-phenylamino)-pyrimidin-2-yl]-piperidin-4-ol;
(2-Morpholin-4-yl-6-phenyl-pyrimidin-4-yl)-(3-rifluoromethyl-phenyl)-amine;
1-[4-Phenyl-6-(4-trifluoromethoxy-phenylamino)-pyrimidin-2-yl]-piperidin-4-ol;
1-[2-(3-Chloro-4-methoxy-phenylamino)-6-phenyl-pyrimidin-4-yl]-piperidin-4-ol;
(4-Morpholin-4-yl-6-phenyl-pyrimidin-2-yl)-(4-trifluoromethoxy-phenyl)-amine;
4-[4-(4-Hydroxy-piperidin-1-yl)-6-phenyl-pyrimidin-2-ylamino]-N-methyl-benzenesulfonamide;
1-{4-[4-(4-Hydroxy-piperidin-1-yl)-6-phenyl-pyrimidin-2-ylamino]-phenyl}-ethanone hydro chloride;
1-[2-(3-Chloro-4-hydroxy-phenylamino)-6-phenyl-pyrimidin-4-yl]-piperidin-4-ol;
1-[2-(3-Fluoro-4-methoxy-phenylamino)-6-phenyl-pyrimidin-4-yl]-piperidin-4-ol;
1-(6-Phenyl-2-phenylamino-pyrimidin-4-yl)-piperidin-4-ol;
(3-Chloro-4-methoxy-phenyl)-(4-phenyl-6-thiomorpholin-4-yl-pyrimidin-2-yl)-amine;
Benzo[1,3]dioxol-5-yl-(4-phenyl-6-thiomorpholin-4-yl-pyrimidin-2-yl)-amine;
(3-Fluoro-4-methoxy-phenyl)-(4-phenyl-6-thiomorpholin-4-yl-pyrimidin-2-yl)-amine;
2-Chloro-4-(4-phenyl-6-thiomorpholin-4-yl-pyrimidin-2-ylamino)-phenol;
(3-Chloro-4-methoxy-phenyl)-(4-morpholin-4-yl-6-phenyl-pyrimidin-2-yl)-amine;
Benzo[1,3]dioxol-5-yl-(4-morpholin-4-yl-6-phenyl-pyrimidin-2-yl)-amine;
(3-Fluoro-4-methoxy-phenyl)-(4-morpholin-4-yl-6-phenyl-pyrimidin-2-yl)-amine;
2-Chloro-4-(4-morpholin-4-yl-6-phenyl-pyrimidin-2-ylamino)-phenol;
1-[6-Phenyl-2-(3-trifluoromethyl-phenylamino)-pyrimidin-4-yl]-piperidin-4-ol;
Benzo[1,3]dioxol-5-yl-[4-(4-fluoro-phenyl)-6-morpholin-4-yl-pyrimidin-2-yl]-amine;
1-[2-(Benzo[1,3]dioxol-5-ylamino)-6-phenyl-pyrimidin-4-yl]-piperidin-4-ol;
[4-(4-Fluoro-phenyl)-6-morpholin-4-yl-pyrimidin-2-yl]-(3-trifluoromethyl-phenyl)-amine;
(4-Fluoro-phenyl)-[4-(4-fluoro-phenyl)-6-morpholin-4-yl-pyrimidin-2-yl]-amine;
1-[2-(4-Chloro-3-trifluoromethyl-phenylamino)-6-phenyl-pyrimidin-4-yl]-piperidin-4-ol;
(4-Morpholin-4-yl-6-phenyl-pyrimidin-2-yl)-(3-trifluoromethyl-phenyl)-amine;
N-{4-[4-(4-Hydroxy-piperidin-1-yl)-6-phenyl-pyrimidin-2-ylamino]-phenyl}-methanesulfonamide;
N-[4-(4-Morpholin-4-yl-6-phenyl-pyrimidin-2-ylamino)-phenyl]-methanesulfonamide hydrochloride;
4-[4-(4-Fluoro-phenyl)-6-(4-hydroxy-piperidin-1-yl)-pyrimidin-2-ylamino]-N,N-dimethyl-benzenesulfonamide;
4-[4-(4-Fluoro-phenyl)-6-(4-hydroxy-piperidin-1-yl)-pyrimidin-2-ylamino]-benzenesulfonamide;
4-[4-(4-Hydroxy-piperidin-1-yl)-6-phenyl-pyrimidin-2-ylamino]-N,N-dimethyl-benzenesulfonamide;
4-[4-(4-Hydroxy-piperidin-1-yl)-6-phenyl-pyrimidin-2-ylamino]-benzenesulfonamide;
4-[4-(4-Fluoro-phenyl)-6-(4-hydroxy-piperidin-1-yl)-pyrimidin-2-ylamino]-N-methyl-benzenesulfonamide;
4-[4-(4-Hydroxy-piperidin-1-yl)-6-phenyl-pyrimidin-2-ylamino]-benzamide;
4-[4-(4-Hydroxy-piperidin-1-yl)-6-phenyl-pyrimidin-2-ylamino]-N-methyl-benzamide;
N-Methyl-4-(4-morpholin-4-yl-6-phenyl-pyrimidin-2-ylamino)-benzenesulfonamide;
N-Methyl-4-(4-morpholin-4-yl-6-phenyl-pyrimidin-2-ylamino)-benzamide;
3-[4-(4-Hydroxy-piperidin-1-yl)-6-phenyl-pyrimidin-2-ylamino]-benzamide;
1-{3-[4-(4-Hydroxy-piperidin-1-yl)-6-phenyl-pyrimidin-2-ylamino]-phenyl}-ethanone;
3-[4-(4-Hydroxy-piperidin-1-yl)-6-phenyl-pyrimidin-2-ylamino]-N-methyl-benzamide;
N-Methyl-3-(4-morpholin-4-yl-6-phenyl-pyrimidin-2-ylamino)-benzamide;
1-[4-(4-Morpholin-4-yl-6-phenyl-pyrimidin-2-ylamino)-phenyl]-ethanone;
3-(4-Morpholin-4-yl-6-phenyl-pyrimidin-2-ylamino)-benzamide;
1-[3-(4-Morpholin-4-yl-6-phenyl-pyrimidin-2-ylamino)-phenyl]-ethanone;
3-[4-(4-Hydroxy-piperidin-1-yl)-6-phenyl-pyrimidin-2-ylamino]-benzenesulfonamide;
3-(4-Morpholin-4-yl-6-phenyl-pyrimidin-2-ylamino)-benzenesulfonamide;
1-{4-[4-(4-Fluoro-phenyl)-6-morpholin-4-yl-pyrimidin-2-ylamino]-phenyl}-ethanone;
1-{4-[4-(4-Fluoro-phenyl)-6-(4-hydroxy-piperidin-1-yl)-pyrimidin-2-ylamino]-phenyl}-ethanone;
1-[6-Phenyl-2-(4-trifluoromethoxy-phenylamino)-pyrimidin-4-yl]-piperidin-4-ol;
1-(2-Indol-1-yl-6-phenyl-pyrimidin-4-yl)-piperidin-4-ol;
4-(6-Phenyl-2-pyrrol-1-yl-pyrimidin-4-ylamino)-cyclohexanol;
1-(4-Benzo[1,3]dioxol-5-yl-6-phenyl-pyrimidin-2-yl)-piperidin-4-ol;
1-(4,6-Diphenyl-pyrimidin-2-yl)-piperidin-4-ol;
4-(2-Benzo[1,3]dioxol-5-yl-6-phenyl-pyrimidin-4-yl)-morpholine;
1-[2-(4-Fluoro-phenyl)-6-phenyl-pyrimidin-4-yl]-piperidin-4-ol;
1-[6-Phenyl-2-(4-trifluoromethoxy-phenyl)-pyrimidin-4-yl]-piperidin-4-ol;
1-(2-Benzo[1,3]dioxol-5-yl-6-phenyl-pyrimidin-4-yl)-piperidin-4-one;
1-[2-(3-Methanesulfonyl-phenyl)-6-phenyl-pyrimidin-4-yl]-piperidin-4-ol;
1-(6-Benzo[1,3]dioxol-5-yl-2-phenyl-pyrimidin-4-yl)-piperidin-4-ol;
1-[6-(3-Methanesulfonyl-phenyl)-2-phenyl-pyrimidin-4-yl]-piperidin-4-ol;
4-(4-Fluoro-phenyl)-6-(4-methyl-piperazin-1-yl)-2-phenyl-pyrimidine;
4-(4-Methyl-piperazin-1-yl)-2,6-diphenyl-pyrimidine;
2-[2-(3-Chloro-4-methoxy-phenylamino)-6-phenyl-pyrimidin-4-ylamino]-ethanol;
(3-Chloro-4-methoxy-phenyl)-(4-phenyl-6-piperazin-1-yl-pyrimidin-2-yl)-amine;
(6-Morpholin-4-yl-2-phenyl-pyrimidin-4-yl)-(4-trifluoromethoxy-phenyl)-amine;
1-[6-(3-Chloro-4-methoxy-phenylamino)-2-phenyl-pyrimidin-4-yl]-piperidin-4-ol;
Benzo[1,3]dioxol-5-yl-(6-morpholin-4-yl-2-phenyl-pyrimidin-4-yl)-amine;
Benzo[1,3]dioxol-5-yl-[6-(4-methyl-piperazin-1-yl)-2-phenyl-pyrimidin-4-yl]-amine;
(2-Phenyl-6-piperazin-1-yl-pyrimidin-4-yl)-(4-trifluoromethoxy-phenyl)-amine;
1-{3-[4-Morpholin-4-yl-6-(4-trifluoromethoxy-phenylamino)-pyrimidin-2-yl]-phenyl}-ethanone;
(2,6-Diphenyl-pyrimidin-4-yl)-(4-trifluoromethoxy-phenyl)-amine;
4-(2,6-Diphenyl-pyrimidin-4-ylamino)-N-methyl-benzenesulfonamide;
4-(4-Ethyl-piperazin-1-yl)-2,6-diphenyl-pyrimidine;
4-(2,6-Diphenyl-pyrimidin-4-yl)-morpholine;
4-(4-Methyl-piperazin-1-yl)-2,6-diphenyl-pyrimidine;
1-[4-(3-Chloro-4-hydroxy-phenylamino)-6-phenyl-pyrimidin-2-yl]-pyrrolidine-2,5-dione;
Succinic acid mono-{1-[2-(3-chloro-4-methoxy-phenylamino)-6-phenyl-pyrimidin-4-yl]-piperidin-4-yl}ester;
4-[4-(3-Chloro-4-methoxy-phenylamino)-6-phenyl-pyrimidin-2-ylamino]-cyclohexanol;
(3-Chloro-4-methoxy-phenyl)-[4-(4-ethyl-piperazin-1-yl)-6-phenyl-pyrimidin-2-yl]-amine;
(3-Chloro-4-methoxy-phenyl)-[4-(4-methyl-piperazin-1-yl)-6-phenyl-pyrimidin-2-yl]-amine;
[4-(1,1-Dioxo-1-lambda-6-thiomorpholin-4-yl)-6-phenyl-pyrimidin-2-yl]-(3-fluoro-4-methoxy-phenyl)-amine;
1-[2-(4-Methanesulfonyl-phenylamino)-6-phenyl-pyrimidin-4-yl]-piperidin-4-ol;
1-[4-(4-Methanesulfonyl-phenylamino)-6-phenyl-pyrimidin-2-yl]-piperidin-4-ol;
(2,6-Diphenyl-pyrimidin-4-yl)-(4-methanesulfonyl-phenyl)-amine;
1-[6-(4-Methanesulfonyl-phenylamino)-2-phenyl-pyrimidin-4-yl]-piperidin-4-ol;
(4-Methanesulfonyl-phenyl)-(6-morpholin-4-yl-2-phenyl-pyrimidin-4-yl)-amine;
(4-Methanesulfonyl-phenyl)-[2-phenyl-6-(4-trifluoromethoxy-phenyl)-pyrimidin-4-yl]-amine;
Phthalic acid mono-[1-(2,6-diphenyl-pyrimidin-4-yl)-piperidin-4-yl]ester;
[4,6-Bis-(4-fluoro-phenyl)-pyrimidin-2-yl]-(4-trifluoromethoxy-phenyl)-amine;
[4-(3-Methanesulfonyl-phenyl)-6-morpholin-4-yl-pyrimidin-2-yl]-(4-trifluoromethoxy-phenyl)-amine;
[2-(4-Fluoro-phenyl)-6-morpholin-4-yl-pyrimidin-4-yl]-(4-trifluoromethoxy-phenyl)-amine;
1-{4-[4-(4-Hydroxy-piperidin-1-yl)-6-phenyl-pyrimidin-2-ylamino]-phenyl}-ethanone;
1-[2-(4-methylsulfanyl-phenylamino)-6-phenyl-pyrimidin-4-yl]-piperidin-4-ol;
(2,6-diphenyl-pyrimidin-4-yl)-(4-methylsulfanyl-phenyl)-amine;
or any combination thereof;
or a salt, a prodrug, a diastereomeric mixture, an enantiomer, a tautomer, or a racemic mixture thereof.
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- 15. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound selected from:
- 19. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound selected from:
- 23. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound selected from:
- 27. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound selected from:
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31. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound selected from:
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N4-(3-Chloro-4-methoxy-phenyl)-6-(4-methoxy-phenyl)-pyrimidine-2,4-diamine;
N4-(3-Chloro-4-methoxy-phenyl)-6-phenyl-pyrimidine-2,4-diamine;
N4-(3-Chloro-4-methoxy-phenyl)-6-(4-fluoro-phenyl)-pyrimidine-2,4-diamine;
N4-(3-Chloro-4-methoxy-phenyl)-6-(4-ethoxy-phenyl)-pyrimidine-2,4-diamine;
N4-(3-Chloro-4-methoxy-phenyl)-6-p-tolyl-pyrimidine-2,4-diamine;
N4-(3-Chloro-4-methoxy-phenyl)-6-(4-methylsulfanyl-phenyl)-pyrimidine-2,4-diamine;
N4-(3-Fluoro-4-methoxy-phenyl)-6-(4-methoxy-phenyl)-pyrimidine-2,4-diamine;
4-[2-Amino-6-(4-methoxy-phenyl)-pyrimidin-4-ylamino]-2-chloro-phenol;
N4-Benzo[1,3]dioxo-5yl-6-phenyl-pyrimidin-2,4-diamine;
N4-(4-Chloro-3-methoxy-phenyl)-6-phenyl-pyrimidine-2,4-diamine;
4-(2-Amino-6-phenyl-pyrimidin-4-ylamino)-2-chloro-phenol;
2-(2-Amino-6-phenyl-pyrimidin-4-ylamino)-benzoic acid ethyl ester;
N4-(3-Chloro-4-methoxy-phenyl)-6-methyl-pyrimidine-2,4-diamine;
5-[2-Amino-6-(4-methylsulfanylphenyl)pyrimidin-4-ylamino]-1-methyl-3-propyl-1H-pyrazole-4-carboxylic acid amide;
6-Chloro-N2-(3-chloro-4-methoxy-phenyl)-N4-cycloheptyl-pyrimidine-2,4-diamine;
1-[2-(3-Chloro-4-methoxy-phenylamino)-6-cycloheptylamino-pyrimidin-4-yl]-piperidin-4-ol;
N2,N4-Bis-(3-chloro-4-methoxy-phenyl)-6-phenyl-pyrimidine-2,4-diamine;
N-[4-(3-Chloro-4-methoxy-phenylamino)-6-(4-ethoxy-phenyl)-pyrimidin-2-yl]-acetamide;
N-[4-(3-Chloro-4-methoxy-phenylamino)-6-(4-methoxy-phenyl)-pyrimidin-2-yl]-acetamide;
N-[4-(3-Chloro-4-methoxy-phenylamino)-6-(4-methoxy-phenyl)-pyrimidin-2-yl]-propionamide;
[4-(3-Chloro-4-methoxy-phenylamino)-6-phenyl-pyrimidin-2-ylamino]-acetic acid ethyl ester;
N-[4-(3-Chloro-4-methoxy-phenylamino)-6-phenyl-pyrimidin-2-yl]-2,2,2-trifluoro-acetamide;
2,2,2-Trifluoro-N-(4-hydroxy-6-phenyl-pyrimidin-2-yl)-acetamide;
4-(4-Fluoro-phenylsulfanyl)-6-phenyl-pyrimidin-2-ylamine;
(3-Chloro-4-methoxy-phenyl)-(2-ethylsulfanyl-6-phenyl-pyrimidin-4-yl)-amine;
4-(3-Chloro-4-hydroxy-phenylamino)-6-phenyl-pyrimidin-2-ol;
N2-(3-Chloro-4-methoxy-phenyl)-N4-methyl-6-phenyl-pyrimidine-2,4-diamine;
N2-(3-Chloro-4-methoxy-phenyl)-N4-isopropyl-6-phenyl-pyrimidine-2,4-diamine;
N2-(3-Chloro-4-methoxy-phenyl)-N4-cycloheptyl-6-phenyl-pyrimidine-2,4-diamine;
N4-Benzyl-N2-(3-chloro-4-methoxy-phenyl)-6-phenyl-pyrimidine-2,4-diamine;
2-(3-Chloro-4-methoxy-phenylamino)-6-(4-methoxy-phenyl)-pyrimidin-4-ol;
2-(3-Chloro-4-methoxy-phenylamino)-6-phenyl-pyrimidin-4-ol;
(3-Chloro-4-methoxy-phenyl)-[4-ethoxy-6-(4-methoxy-phenyl)-pyrimidin-2-yl]-amine;
(3-Chloro-4-methoxy-phenyl)-[4-isopropoxy-6-(4-methoxy-phenyl)-pyrimidin-2-yl]-amine;
[4-Benzyloxy-6-(4-methoxy-phenyl)-pyrimidin-2-yl]-(3-chloro-4-methoxy-phenyl)-amine;
(3-Chloro-4-methoxy-phenyl)-[4-(4-methoxy-phenyl)-6-(4-methyl-benzyloxy)-pyrimidin-2-yl]-amine;
[2-(3-Chloro-4-methoxy-phenylamino)-6-(4-methoxy-phenyl)-pyrimidin-4-yloxy]-acetic acid ethyl ester;
[2-(3-Chloro-4-methoxy-phenylamino)-6-(4-methoxy-phenyl)-pyrimidin-4-yloxy]-acetic acid;
4-(3-Chloro-4-methoxy-phenyl)-6-phenyl-pyrimidin-2-ylamine;
1-[4-(3-Chloro-4-methoxy-phenylamino)-6-phenyl-pyrimidin-2-yl]-piperidin-4-ol;
1-[4-(3-Fluoro-4-methoxy-phenylamino)-6-phenyl-pyrimidin-2-yl]-piperidin-4-ol;
1-[4-(Methyl-phenyl-amino)-6-phenyl-pyrimidin-2-yl]-piperidin-4-ol;
1-[4-Phenyl-6-(3-trifluoromethyl-phenylamino)-pyrimidin-2-yl]-piperidin-4-ol;
1-[4-(4-Chloro-3-trifluoromethyl-phenylamino)-6-phenyl-pyrimidin-2-yl]-piperidin-4-ol;
1-[4-(Benzo[1,3]dioxol-5-ylamino)-6-phenyl-pyrimidin-2-yl]-piperidin-4-ol;
1-[4-Phenyl-6-(4-trifluoromethyl-phenylamino)-pyrimidin-2-yl]-piperidin-4-ol;
(2-Morpholin-4-yl-6-phenyl-pyrimidin-4-yl)-(3-rifluoromethyl-phenyl)-amine;
1-[4-Phenyl-6-(4-trifluoromethoxy-phenylamino)-pyrimidin-2-yl]-piperidin-4-ol;
1-[2-(3-Chloro-4-methoxy-phenylamino)-6-phenyl-pyrimidin-4-yl]-piperidin-4-ol;
(4-Morpholin-4-yl-6-phenyl-pyrimidin-2-yl)-(4-trifluoromethoxy-phenyl)-amine;
4-[4-(4-Hydroxy-piperidin-1-yl)-6-phenyl-pyrimidin-2-ylamino]-N-methyl-benzenesulfonamide;
1-{4-[4-(4-Hydroxy-piperidin-1-yl)-6-phenyl-pyrimidin-2-ylamino]-phenyl}-ethanone hydro chloride;
1-[2-(3-Chloro-4-hydroxy-phenylamino)-6-phenyl-pyrimidin-4-yl]-piperidin-4-ol;
1-[2-(3-Fluoro-4-methoxy-phenylamino)-6-phenyl-pyrimidin-4-yl]-piperidin-4-ol;
1-(6-Phenyl-2-phenylamino-pyrimidin-4-yl)-piperidin-4-ol;
(3-Chloro-4-methoxy-phenyl)-(4-phenyl-6-thiomorpholin-4-yl-pyrimidin-2-yl)-amine;
Benzo[1,3]dioxol-5-yl-(4-phenyl-6-thiomorpholin-4-yl-pyrimidin-2-yl)-amine;
(3-Fluoro-4-methoxy-phenyl)-(4-phenyl-6-thiomorpholin-4-yl-pyrimidin-2-yl)-amine;
2-Chloro-4-(4-phenyl-6-thiomorpholin-4-yl-pyrimidin-2-ylamino)-phenol;
(3-Chloro-4-methoxy-phenyl)-(4-morpholin-4-yl-6-phenyl-pyrimidin-2-yl)-amine;
Benzo[1,3]dioxol-5-yl-(4-morpholin-4-yl-6-phenyl-pyrimidin-2-yl)-amine;
(3-Fluoro-4-methoxy-phenyl)-(4-morpholin-4-yl-6-phenyl-pyrimidin-2-yl)-amine;
2-Chloro-4-(4-morpholin-4-yl-6-phenyl-pyrimidin-2-ylamino)-phenol;
1-[6-Phenyl-2-(3-trifluoromethyl-phenylamino)-pyrimidin-4-yl]-piperidin-4-ol;
Benzo[1,3]dioxol-5-yl-[4-(4-fluoro-phenyl)-6-morpholin-4-yl-pyrimidin-2-yl]-amine;
1-[2-(Benzo[1,3]dioxol-5-ylamino)-6-phenyl-pyrimidin-4-yl]-piperidin-4-ol;
[4-(4-Fluoro-phenyl)-6-morpholin-4-yl-pyrimidin-2-yl]-(3-trifluoromethyl-phenyl)-amine;
(4-Fluoro-phenyl)-[4-(4-fluoro-phenyl)-6-morpholin-4-yl-pyrimidin-2-yl]-amine;
1-[2-(4-Chloro-3-trifluoromethyl-phenylamino)-6-phenyl-pyrimidin-4-yl]-piperidin-4-ol;
(4-Morpholin-4-yl-6-phenyl-pyrimidin-2-yl)-(3-trifluoromethyl-phenyl)-amine;
N-{4-[4-(4-Hydroxy-piperidin-1-yl)-6-phenyl-pyrimidin-2-ylamino]-phenyl}-methanesulfonamide;
N-[4-(4-Morpholin-4-yl-6-phenyl-pyrimidin-2-ylamino)-phenyl]-methanesulfonamide hydrochloride;
4-[4-(4-Fluoro-phenyl)-6-(4-hydroxy-piperidin-1-yl)-pyrimidin-2-ylamino]-N,N-dimethyl-benzenesulfonamide;
4-[4-(4-Fluoro-phenyl)-6-(4-hydroxy-piperidin-1-yl)-pyrimidin-2-ylamino]-benzenesulfonamide;
4-[4-(4-Hydroxy-piperidin-1-yl)-6-phenyl-pyrimidin-2-ylamino]-N,N-dimethyl-benzenesulfonamide;
4-[4-(4-Hydroxy-piperidin-1-yl)-6-phenyl-pyrimidin-2-ylamino]-benzenesulfonamide;
4-[4-(4-Fluoro-phenyl)-6-(4-hydroxy-piperidin-1-yl)-pyrimidin-2-ylamino]-N-methyl-benzenesulfonamide;
4-[4-(4-Hydroxy-piperidin-1-yl)-6-phenyl-pyrimidin-2-ylamino]-benzamide;
4-[4-(4-Hydroxy-piperidin-1-yl)-6-phenyl-pyrimidin-2-ylamino]-N-methyl-benzamide;
N-Methyl-4-(4-morpholin-4-yl-6-phenyl-pyrimidin-2-ylamino)-benzenesulfonamide;
N-Methyl-4-(4-morpholin-4-yl-6-phenyl-pyrimidin-2-ylamino)-benzamide;
3-[4-(4-Hydroxy-piperidin-1-yl)-6-phenyl-pyrimidin-2-ylamino]-benzamide;
1-{3-[4-(4-Hydroxy-piperidin-1-yl)-6-phenyl-pyrimidin-2-ylamino]-phenyl}-ethanone;
3-[4-(4-Hydroxy-piperidin-1-yl)-6-phenyl-pyrimidin-2-ylamino]-N-methyl-benzamide;
N-Methyl-3-(4-morpholin-4-yl-6-phenyl-pyrimidin-2-ylamino)-benzamide;
1-[4-(4-Morpholin-4-yl-6-phenyl-pyrimidin-2-ylamino)-phenyl]-ethanone;
3-(4-Morpholin-4-yl-6-phenyl-pyrimidin-2-ylamino)-benzamide;
1-[3-(4-Morpholin-4-yl-6-phenyl-pyrimidin-2-ylamino)-phenyl]-ethanone;
3-[4-(4-Hydroxy-piperidin-1-yl)-6-phenyl-pyrimidin-2-ylamino]-benzenesulfonamide;
3-(4-Morpholin-4-yl-6-phenyl-pyrimidin-2-ylamino)-benzenesulfonamide;
1-{4-[4-(4-Fluoro-phenyl)-6-morpholin-4-yl-pyrimidin-2-ylamino]-phenyl}-ethanone;
1-{4-[4-(4-Fluoro-phenyl)-6-(4-hydroxy-piperidin-1-yl)-pyrimidin-2-ylamino]-phenyl}-ethanone;
1-[6-Phenyl-2-(4-trifluoromethoxy-phenylamino)-pyrimidin-4-yl]-piperidin-4-ol;
1-(2-Indol-1-yl-6-phenyl-pyrimidin-4-yl)-piperidin-4-ol;
4-(6-Phenyl-2-pyrrol-1-yl-pyrimidin-4-ylamino)-cyclohexanol;
1-(4-Benzo[1,3]dioxol-5-yl-6-phenyl-pyrimidin-2-yl)-piperidin-4-ol;
1-(4,6-Diphenyl-pyrimidin-2-yl)-piperidin-4-ol;
1-(2,6-Diphenyl-pyrimidin-4-yl)-piperidin-4-ol;
1-(2-Benzo[1,3]dioxol-5-yl-6-phenyl-pyrimidin-4-yl)-piperidin-4-ol;
4-(2-Benzo[1,3]dioxol-5-yl-6-phenyl-pyrimidin-4-yl)-morpholine;
1-[2-(4-Fluoro-phenyl)-6-phenyl-pyrimidin-4-yl]-piperidin-4-ol;
1-[6-Phenyl-2-(4-trifluoromethoxy-phenyl)-pyrimidin-4-yl]-piperidin-4-ol;
1-(2-Benzo[1,3]dioxol-5-yl-6-phenyl-pyrimidin-4-yl)-piperidin-4-one;
1-[2-(3-Methanesulfonyl-phenyl)-6-phenyl-pyrimidin-4-yl]-piperidin-4-ol;
1-(6-Benzo[1,3]dioxol-5-yl-2-phenyl-pyrimidin-4-yl)-piperidin-4-ol;
1-[6-(3-Methanesulfonyl-phenyl)-2-phenyl-pyrimidin-4-yl]-piperidin-4-ol;
4-(4-Fluoro-phenyl)-6-(4-methyl-piperazin-1-yl)-2-phenyl-pyrimidine;
4-(4-Methyl-piperazin-1-yl)-2,6-diphenyl-pyrimidine;
4,6-Bis-(4-fluoro-phenyl)-pyrimidin-2-ylamine;
(3-Chloro-4-methoxy-phenyl)-(4-phenyl-6-phenylethynyl-pyrimidin-2-yl)-amine;
2-[2-(3-Chloro-4-methoxy-phenylamino)-6-phenyl-pyrimidin-4-ylamino]-ethanol;
4-Phenyl-6-phenylethynyl-pyrimidin-2-ylamine;
(3-Chloro-4-methoxy-phenyl)-(4-phenyl-6-piperazin-1-yl-pyrimidin-2-yl)-amine;
(6-Morpholin-4-yl-2-phenyl-pyrimidin-4-yl)-(4-trifluoromethoxy-phenyl)-amine;
1-[6-(3-Chloro-4-methoxy-phenylamino)-2-phenyl-pyrimidin-4-yl]-piperidin-4-ol;
Benzo[1,3]dioxol-5-yl-(6-morpholin-4-yl-2-phenyl-pyrimidin-4-yl)-amine;
Benzo[1,3]dioxol-5-yl-[6-(4-methyl-piperazin-1-yl)-2-phenyl-pyrimidin-4-yl]-amine;
(2-Phenyl-6-piperazin-1-yl-pyrimidin-4-yl)-(4-trifluoromethoxy-phenyl)-amine;
(6-Phenyl-pyrimidin-4-yl)-(4-trifluoromethoxy-phenyl)-amine;
1-{3-[2-Morpholin-4-yl-6-(4-trifluoromethoxy-phenylamino)-pyrimidin-4-yl]-phenyl}-ethanone;
1-{3-[4-Morpholin-4-yl-6-(4-trifluoromethoxy-phenylamino)-pyrimidin-2-yl]-phenyl}-ethanone;
(2,6-Diphenyl-pyrimidin-4-yl)-(4-trifluoromethoxy-phenyl)-amine;
4-(2,6-Diphenyl-pyrimidin-4-ylamino)-N-methyl-benzenesulfonamide;
4-(4-Ethyl-piperazin-1-yl)-2,6-diphenyl-pyrimidine;
4-(2,6-Diphenyl-pyrimidin-4-yl)-morpholine;
4-(4-Methyl-piperazin-1-yl)-2,6-diphenyl-pyrimidine;
N4-(3-Chloro-4-methoxy-phenyl)-6-(phenyl-pyrimidin-2-yl]-pyrrolidine-diamine;
1-[4-(3-Chloro-4-hydroxy-phenylamino)-6-phenyl-pyrimidin-2-yl]-pyrrolidine-2,5-dione;
2-(2-Amino-6-phenyl-pyrimidin-4-ylamino)-benzoic acid;
Succinic acid mono-{1-[2-(3-chloro-4-methoxy-phenylamino)-6-phenyl-pyrimidin-4-yl]-piperidin-4-yl}ester;
[4-(3-Chloro-4-methoxy-phenylamino)-6-phenyl-pyrimidin-2-ylsulfanyl]-acetic acid ethyl ester;
4-(3-Chloro-4-methoxy-phenyl)-6-pyridin-3-yl-pyrimidin-2-ylamine;
4-[2-(3-Chloro-4-methoxy-phenylamino)-6-phenyl-pyrimidin-4-ylamino]-cyclohexanol;
4-[4-(3-Chloro-4-methoxy-phenylamino)-6-phenyl-pyrimidin-2-ylamino]-cyclohexanol;
(3-Chloro-4-methoxy-phenyl)-[4-(4-ethyl-piperazin-1-yl)-6-phenyl-pyrimidin-2-yl]-amine;
(3-Chloro-4-methoxy-phenyl)-[4-(4-methyl-piperazin-1-yl)-6-phenyl-pyrimidin-2-yl]-amine;
[4-(1,1-Dioxo-1-lambda-6-thiomorpholin-4-yl)-6-phenyl-pyrimidin-2-yl]-(3-fluoro-4-methoxy-phenyl)-amine;
1-[2-(4-Methanesulfonyl-phenylamino)-6-phenyl-pyrimidin-4-yl]-piperidin-4-ol;
1-[4-(4-Methanesulfonyl-phenylamino)-6-phenyl-pyrimidin-2-yl]-piperidin-4-ol;
(2,6-Diphenyl-pyrimidin-4-yl)-(4-methanesulfonyl-phenyl)-amine;
1-[6-(4-Methanesulfonyl-phenylamino)-2-phenyl-pyrimidin-4-yl]-piperidin-4-ol;
(4-Methanesulfonyl-phenyl)-(6-morpholin-4-yl-2-phenyl-pyrimidin-4-yl)-amine;
(4-Methanesulfonyl-phenyl)-[2-phenyl-6-(4-trifluoromethoxy-phenyl)-pyrimidin-4-yl]-amine;
Phthalic acid mono-[1-(2,6-diphenyl-pyrimidin-4-yl)-piperidin-4-yl] ester;
[4,6-Bis-(4-fluoro-phenyl)-pyrimidin-2-yl]-(4-trifluoromethoxy-phenyl)-amine;
[4-(3-Methanesulfonyl-phenyl)-6-morpholin-4-yl-pyrimidin-2-yl]-(4-trifluoromethoxy-phenyl)-amine;
[2-(4-Fluoro-phenyl)-6-morpholin-4-yl-pyrimidin-4-yl]-(4-trifluoromethoxy-phenyl)-amine;
1-{4-[4-(4-Hydroxy-piperidin-1-yl)-6-phenyl-pyrimidin-2-ylamino]-phenyl}-ethanone;
2-amino-6-(4-methoxy-phenyl)-pyrimidin-4-ol;
2-Amino-6-phenyl-pyrimidin-4-ol;
2-Amino-6-(4-fluoro-phenyl)-pyrimidin-4-ol;
2-Amino-6-(4-ethoxy-phenyl)-pyrimidin-4-ol;
2-Amino-6-p-tolyl-pyrimidin-4-ol;
2-Amino-6-(4-methylsulfanyl-phenyl)-pyrimidin-4-ol;
4-chloro-6-(4-methoxy-phenyl)-pyrimidin-2-ylamine 4-Chloro-6-phenyl-pyrimidin-2-ylamine;
4-Chloro-6-(4-fluoro-phenyl)-pyrimidin-2-ylamine;
4-chloro-6-(4-ethoxy-phenyl)-pyrimidin-2-ylamine;
4-Chloro-6-p-tolyl-pyrimidin-2-ylamine;
4-chloro-6-(4-methylsulfanylphenyl)pyrimidin-2-ylamine;
(3-chloro-4-methoxy-phenyl)-(4,6-dichloro-pyrimidin-2-yl)-amine;
2,4-Dichloro-6-(4-methoxy-phenyl)-pyrimidine;
2,4-Dichloro-6-phenyl-pyrimidine;
4,6-dichloro-2-phenyl-pyrimidine;
2,4-Dichloro-6-(4-ethoxy-phenyl)-pyrimidine;
2,4-Dichloro-6-p-tolyl-pyrimidine;
2,4-Dichloro-6-(4-methylsulfanyl-phenyl)-pyrimidine;
N-[4-chloro-6-(4-ethoxy-phenyl)-pyrimidin-2-yl]-formamide;
N-[4-Chloro-6-(4-methoxy-phenyl)-pyrimidin-2-yl]-acetamide;
N-[4-Chloro-6-(4-methoxy-phenyl)-pyrimidin-2-yl]-propionamide;
(4-Chloro-6-phenyl-pyrimidin-2-ylamino)-acetic acid ethyl ester;
2-mercapto-6-phenyl-pyrimidin-4-ol;
2-ethylsulfanyl-6-arylpyrimidin-4-ol;
4-chloro-2-ethylsulfanyl-6-phenylpyrimidine;
(2-ethylsulfanyl-6-phenylpyrimidin-4-yl) methylamine;
(2-Ethylsulfanyl-6-phenyl-pyrimidin-4-yl)-isopropyl-amine;
Cycloheptyl-(2-ethylsulfanyl-6-phenyl-pyrimidin-4-yl)-amine;
Benzyl-(2-ethylsulfanyl-6-phenyl-pyrimidin-4-yl)-amine;
4-methylamino-6-phenylpyrimidin-2-ol;
4-Isopropylamino-6-phenyl-pyrimidin-2-ol;
4-Cycloheptylamino-6-phenyl-pyrimidin-2-ol;
4-Benzylamino-6-phenyl-pyrimidin-2-ol;
(2-chloro-6-phenylpyrimidin-4-yl) alkylamine;
(2-Chloro-6-phenyl-pyrimidin-4-yl)-isopropyl-amine;
(2-Chloro-6-phenyl-pyrimidin-4-yl)-cycloheptyl-amine;
Benzyl-(2-chloro-6-phenyl-pyrimidin-4-yl)-amine;
2-ethylsulfanyl-6-(4-methoxy-phenyl)-pyrimidin-4-ol;
6-phenyl-pyrimidine-2,4-diol;
2-phenyl-pyrimidine-4,6-diol;
1-(4-chloro-6-phenyl-pyrimidin-2-yl)-piperidin-4-ol;
4-(4-Chloro-6-phenyl-pyrimidin-2-yl)-morpholine;
4-(4-Chloro-6-phenyl-pyrimidin-2-yl)-thiomorpholine;
1-(2-chloro-6-phenyl-pyrimidin-4-yl)-piperidin-4-ol;
4-(2-chloro-6-phenyl-pyrimidin-4-yl)-morpholine;
4-(2-chloro-6-phenyl-pyrimidin-4-yl)-thiomorpholine;
1-(2-Chloro-6-phenyl-pyrimidin-4-yl)-piperidin-4-one;
2-Chloro-4-(4-methyl-piperazin-1-yl)-6-phenyl-pyrimidine;
6-(4-Fluoro-phenyl)-pyrimidine-2,4-diol;
2,4-Dichloro-6-(4-fluoro-phenyl)-pyrimidine;
1-[4-Chloro-6-(4-fluoro-phenyl)-pyrimidin-2-yl]-piperidin-4-ol;
4-[4-Chloro-6-(4-fluoro-phenyl)-pyrimidin-2-yl]-morpholine;
1-[2-Chloro-6-(4-fluoro-phenyl)-pyrimidin-4-yl]-piperidin-4-ol;
4-[2-Chloro-6-(4-fluoro-phenyl)-pyrimidin-4-yl]-morpholine;
(3-chloro-4-methoxy-phenyl)-(4-chloro-6-phenyl-pyrimidin-2-yl)-amine;
(6-chloro-2-phenyl-pyrimidin-4-yl)-(4-trifluoromethoxy-phenyl)-amine;
(3-Chloro-4-methoxy-phenyl)-(6-chloro-2-phenyl-pyrimidin-4-yl)-amine;
Benzo[1,3]dioxol-5-yl-(6-chloro-2-phenyl-pyrimidin-4-yl)-amine;
(6-Chloro-2-phenyl-pyrimidin-4-yl)-(4-trifluoromethoxy-phenyl)-amine;
6-phenyl-pyrimidin-4-ol;
4-chloro-6-phenyl-pyrimidine;
(2,6-dichloro-pyrimidin-4-yl)-(4-trifluoromethoxy-phenyl)-amine;
(6-chloro-2-morpholin-4-yl-pyrimidin-4-yl)-(4-trifluoromethoxy-phenyl)-amine;
1-{3-[4-chloro-6-(4-trifluoromethoxy-phenylamino)-pyrimidin-2-yl]-phenyl}-ethanone;
2,6-Diphenyl-pyrimidin-4-ol;
4-Chloro-2,6-diphenyl-pyrimidine;
4-hydroxy-6-phenyl-pyrimidin-2-ylsulfanyl)-acetic acid ethyl ester;
4-chloro-6-phenyl-pyrimidin-2-ylsulfanyl)-acetic acid ethyl ester;
4-(2-chloro-6-phenyl-pyrimidin-4-ylamino)-cyclohexanol;
4-(4-chloro-6-phenyl-pyrimidin-2-ylamino)-cyclohexanol;
1-[2-(4-methylsulfanyl-phenylamino)-6-phenyl-pyrimidin-4-yl]-piperidin-4-ol;
1-[4-(4-methylsulfanyl-phenylamino)-6-phenyl-pyrimidin-2-yl]-piperidin-4-ol;
(2,6-diphenyl-pyrimidin-4-yl)-(4-methylsulfanyl-phenyl)-amine;
(6-chloro-2-phenyl-pyrimidin-4-yl)-(4-methylsulfanyl-phenyl)-amine;
(6-chloro-2-phenyl-pyrimidin-4-yl)-(4-methanesulfonyl-phenyl)-amine;
(4,6-dichloro-pyrimidin-2-yl)-(4-trifluoromethoxy-phenyl)-amine;
[4-chloro-6-(3-methanesulfonyl-phenyl)-pyrimidin-2-yl]-(4-trifluoromethoxy-phenyl)-amine;
2-(4-fluoro-phenyl)-pyrimidine-4,6-diol;
4,6-dichloro-2-(4-fluoro-phenyl)-pyrimidine;
[6-chloro-2-(4-fluoro-phenyl)-pyrimidin-4-yl]-(4-trifluoromethoxy-phenyl)-amine;
or any combination thereof;
or a pharmaceutically acceptable salt, a prodrug, a diastereomeric mixture, an enantiomer, a tautomer, or a racemic mixture thereof. - View Dependent Claims (32, 33, 34)
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Specification