NAPHTHYLPYRIMIDINE, NAPHTHYLPYRAZINE AND NAPHTHYLPYRIDAZINE ANALOGS AND THEIR USE AS AGONISTS OF THE WNT-BETA-CATENIN CELLULAR MESSAGING SYSTEM
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Abstract
The present invention relates to naphthylpyrimidine analogs, methods of making naphthylpyrimidine analogs, compositions comprising a naphthylpyrimidine analog, and methods for treating canonical Wnt-β-catenin cellular messaging system-related disorders comprising administering to a subject in need thereof an effective amount of a naphthylpyrimidine, naphthylpyrazine and naphthylpyridazine analog.
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Citations
46 Claims
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1. A compound of Formula (A):
- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 31, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 44, 45, 46)
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2. The compound of claim 1, wherein R7 is H or OR11.
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3. The compound of claim 1, wherein R5 is 5-10-membered heteroaryl.
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4. The compound of claim 3, wherein R5 is 5-7-membered heteroaryl
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5. The compound of claim 1, wherein Q is a bond or N(CH2)rR8.
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6. The compound of claim 5, wherein Q is a bond.
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7. The compound of claim 1, wherein r is 0, 1 or 2.
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8. The compound of claim 1, wherein R8 is H.
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9. The compound of claim 1, wherein Formula (A) is Formula (AI):
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10. The compound of claim 1, wherein the 3- to 7-membered heterocycle formed by R3 and R4 is a 5, 6, or 7-membered heteroaryl.
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11. The compound of claim 1, wherein the 3- to 7-membered heterocycle formed by R5 and R4 is a 5, 6, or 7-membered heteroaryl.
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12. The compound of claim 1, wherein the 3- to 7-membered heterocycle formed by R11 and R12 is a 5, 6, or 7-membered heteroaryl.
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13. The compound of claim 1, wherein 3- to 7-membered heterocycle formed by R13 and R14 is a 5, 6, or 7-membered heteroaryl.
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14. The compound of claim 1, wherein the R11 is Cl-C6 alkyl optionally substituted with a 5-7 membered heteroaryl.
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15. The compound of claim 1, wherein
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16. The compound of claim 1, wherein
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17. The compound of claim 16, wherein n=1 and m=1.
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18. The compound of claim 16, wherein n=1 and m=0.
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19. The compound of claim 16, where n=2 and m=0.
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20. The compound of claim 16, wherein R2 is CH2OR11.
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21. The compound of claim 16, wherein R3 is OR11 or CH2OR11.
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22. The compound of claim 16, wherein R4 is OR11.
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23. The compound of claim 16, wherein R5 is CN;
- N R11R12;
C(S)N R11R12;
or alkyl optionally substituted with N R11R12, monocyclic heterocycle, or bicyclic heterocycle.
- N R11R12;
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24. The compound of claim 16, wherein
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25. The compound of claim 16, wherein
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26. The compound of claim 25, wherein
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27. The compound of claim 15, wherein
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28. The compound of claim 1, wherein Formula (A) is
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29. The compound of claim 1, wherein Formula (A) is Formula (I):
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31. The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein the compound is
tert-butyl {(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}carbamate; -
(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-amine; 4-[4-(2-naphthyl)pyrimidin-2-yl]-1,4-diazepane-1-carbaldehyde; 1-[4-(2-naphthyl)pyrimidin-2-yl]-1,4-diazepane; 1-[4-(2-naphthyl)pyrimidin-2-yl]azepan-4-amine; tert-butyl {1-[4-(2-naphthyl)pyrimidin-2-yl]azepan-4-yl}carbamate; tert-butyl ({1-[4-(2-naphthyl)pyrimidin-2-yl]azetidin-3-yl}methyl)carbamate; 1-{1-[4-(2-naphthyl)pyrimidin-2-yl]azetidin-3-yl }methanamine; tert-butyl ({1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)carbamate; 1-{1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methanamine; 4-(2-{4-[4-(2-naphthyl)pyrimidin-2-yl]piperazin-1-yl}ethyl)morpholine; 4-({4-[4-(2-naphthyl)pyrimidin-2-yl]piperazin-1-yl}acetyl)morpholine; N,N-dimethyl-2-{4-[4-(2-naphthyl)pyrimidin-2-yl]piperazin-1-yl}ethanamine; 2-(4-methylpiperazin-1-yl)-4-(2-naphthyl)pyrimidine; 4-(2-naphthyl)-2-(4-pyridin-2-ylpiperazin-1-yl)pyrimidine; 4-(2-naphthyl)-2-(4-pyrimidin-2-ylpiperazin-1-yl)pyrimidine; 1-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}-1,3-dihydro-2H-benzimidazol-2-one; 2-[4-(2-naphthyl)pyrimidin-2-yl]-1,2,3,4-tetrahydroisoquinoline; (2-{4-[4-(2-naphthyl)pyrimidin-2-yl]piperazin-1-yl}ethyl)amine; N,N-dimethyl-3-{4-[4-(2-naphthyl)pyrimidin-2-yl]piperazin-1-yl}propan-1-amine; 4-(2-naphthyl)-2-(4-pyridin-4-ylpiperazin-1-yl)pyrimidine; 4-(3-{4-[4-(2-naphthyl)pyrimidin-2-yl]piperazin-1-yl}propyl)morpholine; 2-[4-(2-furoyl)piperazin-1-yl]-4-(2-naphthyl)pyrimidine; tert-butyl {(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}carbamate; (3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-amine; N,N-dimethyl-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-amine; N,N-diethyl-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-amine; (3R)-N-methyl-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-amine; (3S)-N-methyl-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-amine; (3S)-N,N-dimethyl-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-amine; (3R)-N,N-dimethyl-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-amine; N-methyl-N-{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}acetamide; {1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methanol; 2-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}ethanol; ethyl 1-[4-(2-naphthyl)pyrimidin-2-yl]piperidine-4-carboxylate; ethyl {1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}acetate; {(2S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-2-yl}methanol; 1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-ol; 4-[4-(2-naphthyl)pyrimidin-2-yl]morpholine; {1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-2-yl}methanol; {1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-3-yl}methanol; 1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-ol; 1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-3-ol; {(2R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-2-yl}methanol; 4-(2-naphthyl)-2-pyrrolidin-1-ylpyrimidine; 4-(2-naphthyl)-2-piperidin-1-ylpyrimidine; 2-(4-methylpiperidin-1-yl)-4-(2-naphthyl)pyrimidine; 1-[4-(2-naphthyl)pyrimidin-2-yl]azepane; tert-butyl {1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}carbamate; tert-butyl 4-[4-(2-naphthyl)pyrimidin-2-yl]piperazine-1-carboxylate; 1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-amine; 4-(2-naphthyl)-2-piperazin-1-ylpyrimidine; tert-butyl ({1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-3-yl}methyl)carbamate; ({1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-3-yl}methyl)amine; (1R,5S,6s)-3-[4-(2-naphthyl)pyrimidin-2-yl]-3-azabicyclo[3.1.0]hexan-6-amine; ({1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methyl)amine; 1-[4-(2-naphthyl)pyrimidin-2-yl]piperidine-4-carboxamide; 8-[4-(2-naphthyl)pyrimidin-2-yl]-1,4-dioxa-8-azaspiro[4.5]decane; methyl 1-[4-(2-naphthyl)pyrimidin-2-yl]piperidine-4-carboxylate; 1-[4-(2-naphthyl)pyrimidin-2-yl]piperidine-3-carboxamide; {(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-3-yl}methanol; {(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-3-yl}methanol; N-{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}acetamide; N-({1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methyl)guanidine; N-ethyl-4-[4-(2-naphthyl)pyrimidin-2-yl]-1,4-diazepane-1-carboxamide; methyl 4-[4-(2-naphthyl)pyrimidin-2-yl]-1,4-diazepane-1-carboxylate; ethyl 4-[4-(2-naphthyl)pyrimidin-2-yl]-1,4-diazepane-1-carboxylate; 1-acetyl-4-[4-(2-naphthyl)pyrimidin-2-yl]-1,4-diazepane; 1-[4-(2-naphthyl)pyrimidin-2-yl]-4-propionyl-1,4-diazepane; 1-[4-(2-naphthyl)pyrimidin-2-yl]-4-(trifluoroacetyl)-1,4-diazepane; N,N-diethyl-4-[4-(2-naphthyl)pyrimidin-2-yl]-1,4-diazepane-1-carboxamide; 1-(methylsulfonyl)-4-[4-(2-naphthyl)pyrimidin-2-yl]-1,4-diazepane; N,N-dimethyl-4-[4-(2-naphthyl)pyrimidin-2-yl]-1,4-diazepane-1-sulfonamide; N,N-dimethyl-4-[4-(2-naphthyl)pyrimidin-2-yl]-1,4-diazepane-1-carboxamide; 4-[4-(2-naphthyl)pyrimidin-2-yl]-1,4-diazepane-1-carboxamide; 1-benzoyl-4-[4-(2-naphthyl)pyrimidin-2-yl]-1,4-diazepane; 1-[(4-methylphenyl)sulfonyl]-4-[4-(2-naphthyl)pyrimidin-2-yl]-1,4-diazepane; N-{1-[4-(2-naphthyl)pyrimidin-2-yl]azepan-4-yl}acetamide; 2,2,2-trifluoro-N-{1-[4-(2-naphthyl)pyrimidin-2-yl]azepan-4-yl}acetamide; N,N-dimethyl-N′
-{1-[4-(2-naphthyl)pyrimidin-2-yl]azepan-4-yl}urea;N-{1-[4-(2-naphthyl)pyrimidin-2-yl]azepan-4-yl}benzamide; N-{1-[4-(2-naphthyl)pyrimidin-2-yl]azepan-4-yl}urea; N-ethyl-N′
-{1-[4-(2-naphthyl)pyrimidin-2-yl]azepan-4-yl}urea;N-{1-[4-(2-naphthyl)pyrimidin-2-yl]azepan-4-yl}methanesulfonamide; 4-methyl-N-{1-[4-(2-naphthyl)pyrimidin-2-yl]azepan-4-yl}benzenesulfonamide; N,N-dimethyl-N′
-{1-[4-(2-naphthyl)pyrimidin-2-yl]azepan-4-yl}sulfamide;N-({1-[4-(2-naphthyl)pyrimidin-2-yl]azetidin-3-yl}methyl)acetamide; 2,2,2-trifluoro-N-({1-[4-(2-naphthyl)pyrimidin-2-yl]azetidin-3-yl}methyl)acetamide; N,N-dimethyl-N′
-({1-[4-(2-naphthyl)pyrimidin-2-yl]azetidin-3-yl}methyl)urea;methyl ({1-[4-(2-naphthyl)pyrimidin-2-yl]azetidin-3-yl}methyl)carbamate; N-({1-[4-(2-naphthyl)pyrimidin-2-yl]azetidin-3-yl}methyl)urea; N-ethyl-N′
-({1-[4-(2-naphthyl)pyrimidin-2-yl]azetidin-3-yl}methyl)urea;N-({1-[4-(2-naphthyl)pyrimidin-2-yl]azetidin-3-yl}methyl)methanesulfonamide; 4-methyl-N-({1-[4-(2-naphthyl)pyrimidin-2-yl]azetidin-3-yl}methyl)benzenesulfonamide; {1-[4-(2-naphthyl)pyrimidin-2-yl]azepan-4-yl}formamide; N,N-dimethyl-N′
-(2-{4-[4-(2-naphthyl)pyrimidin-2-yl]piperazin-1-yl}ethyl)urea;N-(2-{4-[4-(2-naphthyl)pyrimidin-2-yl]piperazin-1-yl}ethyl)methanesulfonamide; N-(2-{4-[4-(2-naphthyl)pyrimidin-2-yl]piperazin-1-yl}ethyl)dicarbonimidic diamide; N-ethyl-N′
-(2-{4-[4-(2-naphthyl)pyrimidin-2-yl]piperazin-1-yl}ethyl)urea;N-isopropyl-N′
-(2-{4-[4-(2-naphthyl)pyrimidin-2-yl]piperazin-1-yl}ethyl)urea;diethyl (2-{4-[4-(2-naphthyl)pyrimidin-2-yl]piperazin-1-yl}ethyl)imidodicarbonate; N-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}acetamide; 2,2,2-trifluoro-N-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}acetamide; methyl {(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}carbamate; N,N-dimethyl-N′
-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}urea;N-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}pyrrolidine-1-carboxamide N-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}urea; N,N-dimethyl-N′
-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}sulfamide;N-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methanesulfonamide; 4-methyl-N-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}benzenesulfonamide; N-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}morpholine-4-carboxamide; ethyl {(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}carbamate; N-isopropyl-N′
-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}urea;N,N-diethyl-N′
-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}urea;N-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}guanidine; 4-chloro-N-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}benzamide; 4-cyano-N-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}benzamide; N-{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}acetamide; 2,2,2-trifluoro-N-{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}acetamide; N-{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}benzamide; methyl {(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}carbamate; N,N-dimethyl-N′
-{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}urea;N-{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}pyrrolidine-1-carboxamide N-ethyl-N′
-{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}urea;N-{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}urea; N,N-dimethyl-N′
-{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}sulfamide;N-{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methanesulfonamide; 4-methyl-N-{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}benzenesulfonamide; N-{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}morpholine-4-carboxamide; ethyl {(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}carbamate; N-isopropyl-N′
-{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}urea;N,N-diethyl-N′
-{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}urea;4-chloro-N-{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}benzamide; 4-cyano-N-{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}benzamide; N-({1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)acetamide; N-({1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)benzamide; methyl ({1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)carbamate; N,N-dimethyl-N′
-({1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)urea;N-ethyl-N′
-({1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)urea;N-({1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)urea; N,N-dimethyl-N′
-({1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)sulfamide;N-({1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)methanesulfonamide; N-({1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)formamide; N-(2-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}ethyl)acetamide; 2,2,2-trifluoro-N-(2-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}ethyl)acetamide; methyl (2-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}ethyl)carbamate; N,N-dimethyl-N′
-(2-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}ethyl)urea;N,N-diethyl-N′
-(2-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}ethyl)urea;N-ethyl-N′
-(2-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}ethyl)urea;N-isopropyl-N′
-(2-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}ethyl)urea;N-(2-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}ethyl)urea; N-cyclohexyl-N′
-(2-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}ethyl)urea;N-(2-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}ethyl)pyrrolidine-1-carboxamide; N-(2-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}ethyl)morpholine-4-carboxamide; N,N-dimethyl-N′
-(2-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}ethyl)sulfamide;N-(2-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}ethyl)methanesulfonamide; benzyl (2-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}ethyl)carbamate; N-(2-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}ethyl)-N′
-phenylurea;N-(2-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}ethyl)benzamide; N-({1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methyl)acetamide; N-({1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methyl)acetamide; N-({1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methyl)benzamide; methyl ({1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methyl)carbamate; N,N-dimethyl-N′
-({1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methyl)urea;N-({1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methyl)pyrrolidine-1-carboxamide N-ethyl-N′
-({1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methyl)urea;N-({1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methyl)urea; N,N-dimethyl-N′
-({1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methyl)sulfamide;N-({1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methyl)methanesulfonamide; 4-methyl-N-({1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methyl)benzenesulfonamide; N-({1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methyl)pyrimidin-2-amine; di-tert-butyl {(Z)-[({1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methyl) amino]methylylidene}biscarbamate; di-tert-butyl ((E)-{4-[4-(2-naphthyl)pyrimidin-2-yl]piperazin-1-yl}methylylidene)biscarbamate; 4-[4-(2-naphthyl)pyrimidin-2-yl]piperazine-1-carboximidamide; {1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methyl 4-methylbenzenesulfonate; 2-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}ethyl methanesulfonate; 2-[4-(2-azidoethyl)piperidin-1-yl]-4-(2-naphthyl)pyrimidine; N,N-dimethyl-1-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methanamine; N-methyl-1-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methanamine; 2-[4-(1H-imidazol-1-ylmethyl)piperidin-1-yl]-4-(2-naphthyl)pyrimidine; 4-(2-naphthyl)-2-[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]pyrimidine; N-ethyl-N-({1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methyl)ethanamine; 4-(2-naphthyl)-2-[4-(piperidin-1-ylmethyl)piperidin-1-yl]pyrimidine; 4-(2-naphthyl)-2-[4-(piperidin-1-ylmethyl)piperidin-1-yl]pyrimidine; N-({1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methyl)ethanamine; 2-methyl-N-({1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methyl)propan-1-amine; 2-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}ethanamine; 1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-one; 1-[4-(2-naphthyl)pyrimidin-2-yl]piperidine-4-carbaldehyde; 1-[4-(2-naphthyl)pyrimidin-2-yl]piperidine-4-carboxylic acid; 4-methyl-1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-ol; 1-[4-(2-naphthyl)pyrimidin-2-yl]-4-(nitromethyl)piperidin-4-ol; 4-(aminomethyl)-1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-ol; 1-[4-(2-naphthyl)pyrimidin-2-yl]-4-(1-nitroethyl)piperidin-4-ol; 4-(2-naphthyl)-2-[4-(1-nitroethyl)piperidin-1-yl]pyrimidine; 4-(2-naphthyl)-2-[4-(nitromethyl)piperidin-1-yl]pyrimidine; tert-butyl ((1S)-1-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}ethyl)carbamate; tert-butyl (1-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}ethyl)carbamate; 1-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}ethanamine; (1R)-1-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}ethanamine; (1S)-1-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}ethanamine; 4-{[4-(2-naphthyl)pyrimidin-2-yl]methyl}-1,4-diazepane-1-carbaldehyde; 1-(1-{[4-(2-naphthyl)pyrimidin-2-yl]methyl}piperidin-4-yl)methanamine; 1-[4-(2-naphthyl)pyrimidin-2-yl]piperidine-4-carbonitrile; 1-[4-(2-naphthyl)pyrimidin-2-yl]piperidine-4-carbothioamide; 2-azetidin-1-yl-4-(2-naphthyl)pyrimidine; 2-azetidin-1-yl-4-(2-naphthyl)pyrimidine; 2-[4-(azidomethyl)piperidin-1-yl]-4-(2-naphthyl)pyrimidine; 1-[4-(2-naphthyl)pyrimidin-2-yl]piperidine-4-carboximidamide; methyl [(tert-butoxycarbonyl)amino]{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-ylidene}acetate; methyl [(tert-butoxycarbonyl)amino]{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}acetate; methyl (2R)-[(tert-butoxycarbonyl)amino]{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}acetate; methyl (2S)-[(tert-butoxycarbonyl)amino]{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}acetate; methyl amino {1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}acetate; methyl (2R)-amino {1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}acetate; methyl (2S)-amino {1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}acetate; (2R)-2-amino-2-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}ethanol; tert-butyl ((1R)-2-hydroxy-1-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}ethyl)carbamate; tert-butyl ((1S)-2-hydroxy-1-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}ethyl)carbamate; tert-butyl ((1R)-2-hydroxy-2-methyl-1-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}propyl)carbamate; (1R)-1-amino-2-methyl-1-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4yl}propan-2-ol; (4R)-5,5-dimethyl-4-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}-1,3-oxazolidin-2-one; (4R)-4-{1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}-1,3-oxazolidin-2-one;
or(1-(4-(naphthalen-2-yl)pyrimidin-2-yl)piperidin-4-yl)methanol.
-
-
33. A compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein the compound is:
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1-{1-[2-(2-naphthyl)pyrimidin-4-yl]piperidin-4-yl}methanamine; 1-{1-[6-(2-naphthyl)pyrimidin-4-yl]piperidin-4-yl}methanamine; 1-{1-[5-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methanamine; 1-{1-[6-(2-naphthyl)pyrazin-2-yl]piperidin-4-yl}methanamine; 1-{1-[5-(2-naphthyl)pyridazin-3-yl]piperidin-4-yl}methanamine; 1-{1-[4-(2-naphthyl)pyrimidin-2-yl]-1,2,3,4-tetrahydroquinolin-4-yl}methanamine; 1-{(4S)-1-[4-(2-naphthyl)pyrimidin-2-yl]azepan-4-yl}methanamine; 1-{(4R) 1-[4-(2-naphthyl)pyrimidin-2-yl]azepan-4-yl}methanamine; 1-[4-(2-naphthyl)pyrimidin-2-yl]azepan-4-amine; N-{1-[4-(2-naphthyl)pyrimidin-2-yl]azepan-4-yl}acetamide; 2,2,2-trifluoro-N-{1-[4-(2-naphthyl)pyrimidin-2-yl]azepan-4-yl}acetamide; N,N-dimethyl-N′
-{1-[4-(2-naphthyl)pyrimidin-2-yl]azepan-4-yl}urea;N-{1-[4-(2-naphthyl)pyrimidin-2-yl]azepan-4-yl}benzamide; N-{1-[4-(2-naphthyl)pyrimidin-2-yl]azepan-4-yl}urea; N-ethyl-N′
-{1-[4-(2-naphthyl)pyrimidin-2-yl]azepan-4-yl}urea;N-{1-[4-(2-naphthyl)pyrimidin-2-yl]azepan-4-yl}methanesulfonamide; 4-methyl-N-{1-[4-(2-naphthyl)pyrimidin-2-yl]azepan-4-yl}benzenesulfonamide; N,N-dimethyl-N′
-{1-[4-(2-naphthyl)pyrimidin-2-yl]azepan-4-yl}sulfamide;{(1S,4R)-2-[4-(2-naphthyl)pyrimidin-2-yl]-2-azabicyclo[2.2.1]heptane-5,5-diyl}dimethanamine; 1-{(1R,4R,5R)-2-[4-(2-naphthyl)pyrimidin-2-yl]-2-azabicyclo[2.2.1]hept-5-yl}methanamine; 1-{(1R,4R,5S)-2-[4-(2-naphthyl)pyrimidin-2-yl]-2-azabicyclo[2.2.1]hept-5-yl}methanamine; 1-{(1S,4S,5S)-2-[4-(2-naphthyl)pyrimidin-2-yl]-2-azabicyclo[2.2.1]hept-5-yl}methanamine; 1-{(1S,4S,5R)-2-[4-(2-naphthyl)pyrimidin-2-yl]-2-azabicyclo[2.2.1]hept-5-yl}methanamine; 1-{8-[4-(2-naphthyl)pyrimidin-2-yl]-8-azabicyclo[3.2.1]oct-3-yl}methanamine; 1-{8-[4-(2-naphthyl)pyrimidin-2-yl]-8-azabicyclo[3.2.1]oct-3-yl}methanamine; 2-[4-(2-naphthyl)pyrimidin-2-yl]-2, 8-diazaspiro[4.5]decane; N,N,N′
-trimethyl-N′
-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}ethane-1,2-diamine;(3aR* ,6aS)-2-[4-(2-naphthyl)pyrimidin-2-yl]octahydropyrrolo[3,4-c]pyrrole; 5-(4-naphthalen-2-ylpyrimidin-2-yl)octahydropyrrolo [3,4-b]pyrrole; 1-({1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)piperidin-4-ol; (3S)-1-({1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)piperidin-3-ol; (3R)-1-({1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)piperidin-3-ol; (3S)-1-({1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)pyrrolidin-3-ol; (3R)-1-({1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)pyrrolidin-3-ol; (3S,3′
R)-1′
-[4-(2-naphthyl)pyrimidin-2-yl]-1,3′
-bipyrrolidin-3-ol;2-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}octahydro-2H-pyrido[1,2-a]pyrazine; (3S,3′
R)-1′
-[4-(2-naphthyl)pyrimidin-2-yl]-1,3′
-bipyrrolidin-3-amine;3-(methyl {(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}amino)propan-1-ol; N,N-dimethyl-N′
-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}ethane-1,2-diamine;N,N′
-dimethyl-N-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}ethane-1,2-diamine;(3R,3′
R)-1′
-[4-(2-naphthyl)pyrimidin-2-yl]-1,3′
-bipyrrolidin-3-ol;(3R,3′
R)-1′
-[4-(2-naphthyl)pyrimidin-2-yl]-1,3′
-bipyrrolidin-3-amine;(1S,4S)-2-methyl-5-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}-2,5-diazabicyclo[2.2.1]heptane; 5-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}octahydropyrrolo[3,4b]-pyrrole; N,N,N′
-trimethyl-N′
-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}propane-1,3-diamine;(3R,3′
S)-1′
-[4-(2-naphthyl)pyrimidin-2-yl]-1,3′
-bipyrrolidin-3-ol;(3S,3′
S)-1′
-[4-(2-naphthyl)pyrimidin-2-yl]-1,3′
-bipyrrolidin-3-ol;N,N-dimethyl-N′
-{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}ethane-1,2-diamine;N,N,N′
-trimethyl-N′
-{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}ethane-1,2-diamine3-(methyl{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}amino)propan-1-ol; 5-{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}octahydropyrrolo[3,4-b]pyrrole; N,N,N′
-trimethyl-N′
-{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}propane-1,3-diamine;2-(ethyl{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}amino)ethanol; 2-[(3S)-3-(1H-imidazol-1-yl)pyrrolidin-1-yl]-4-(2-naphthyl)pyrimidine; (3S)-N-cyclohexyl-N-methyl-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-amine; (3S)-N-(tert-butyl)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-amine; 4-(2-naphthyl)-2-[(3S)-3-piperazin-1-ylpyrrolidin-1-yl]pyrimidine; 4-{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}morpholine; 4-{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}piperazin-2-one; 1-{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}azepane; (3′
S)-1′
-[4-(2-naphthyl)pyrimidin-2-yl]-1,3′
-bipyrrolidine;4-(2-naphthyl)-2-[(3S)-3-piperidin-1-ylpyrrolidin-1-yl]pyrimidine; 2-[(3S)-3-(4-methylpiperazin-1-yl)pyrrolidin-1-yl]-4-(2-naphthyl)pyrimidine; (1-{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}piperidin-3-yl)methanol; (1-{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}piperidin-4-yl)methanol; 1-{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}piperidin-3-ol; (3S)-N-(2-morpholin-4-ylethyl)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-amine; 1-{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}piperidin-4-ol; (3R,3′
S)-N,N-dimethyl-1′
-[4-(2-naphthyl)pyrimidin-2-yl]-1,3′
-bipyrrolidin-3-amine;(3S,3′
S)-N,N-dimethyl-1′
-[4-(2-naphthyl)pyrimidin-2-yl]-1,3′
-bipyrrolidin-3-amine;(3R)-1-{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}piperidin-3-ol; (3S)-1-{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}piperidin-3ol; 2-(ethyl{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}amino)ethanol; 2-[(3R)-3-(1H-imidazol-1-yl)pyrrolidin-1-yl]-4-(2-naphthyl)pyrimidine; (3R)-N-cyclohexyl-N-methyl-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-amine; (3R)-N-(tert-butyl)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-amine; 4-(2-naphthyl)-2-[(3R)-3-piperazin-1-ylpyrrolidin-1-yl]pyrimidine; 4-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}morpholine; 4-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}piperazin-2-one; 1-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}azepane; (3′
R)-1′
-[4-(2-naphthyl)pyrimidin-2-yl]-1,3′
-bipyrrolidine;4-(2-naphthyl)-2-[(3R)-3-piperidin-1-ylpyrrolidin-1-yl]pyrimidine; 2-[(3R)-3-(4-methylpiperazin-1-yl)pyrrolidin-1-yl]-4-(2-naphthyl)pyrimidine; (1-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}piperidin-3-yl)methanol; (1-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}piperidin-4-yl)methanol; 1-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}piperidin-3-ol; (3R)-N-(2-morpholin-4-ylethyl)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-amine; 1-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}piperidin-4-ol; (3R,3′
R)-N,N-dimethyl-1′
-[4-(2-naphthyl)pyrimidin-2-yl]-1,3′
-bipyrrolidin-3-amine;(3S,3′
R)-N,N-dimethyl-1′
-[4-(2-naphthyl)pyrimidin-2-yl]-1,3′
-bipyrrolidin-3-amine;(3R)-1-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}piperidin-3-ol; (3S)-1-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}piperidin-3-ol; {1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methanol; 1-({1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)azepane; 4-(2-naphthyl)-2-[3-(piperidin-1-ylmethyl)pyrrolidin-1-yl]pyrimidine; 4-(2-naphthyl)-2-[3-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]pyrimidine; 2-[3-(azetidin-1-ylmethyl)pyrrolidin-1-yl]-4-(2-naphthyl)pyrimidine; 4-({1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)morpholine; 4-({1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)thiomorpholine; N-ethyl-N-({1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)ethanamine; 2-methyl-N-({1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)propan-2-amine; 2-[ethyl({1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl) amino]ethanol; 2-{3-[(4-methylpiperazin-1-yl)methyl]pyrrolidin-1-yl}-4-(2-naphthyl)pyrimidine; 4-({1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)piperazin-2-one; 2-[3-(1H-imidazol-1-ylmethyl)pyrrolidin-1-yl]-4-(2-naphthyl)pyrimidine; 2-[3-(chloromethyl)pyrrolidin-1-yl]-4-(2-naphthyl)pyrimidine; N,N-dimethyl-1-{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methanamine; 4-(2-naphthyl)-2-[(3S)-3-(piperidin-1-ylmethyl)pyrrolidin-1-yl]pyrimidine; 4-(2-naphthyl)-2-[(3S)-3-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]pyrimidine; N-methyl-1-{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methanamine; N-methyl-N-({(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)cyclohexanamine; 1-({(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)piperidin-2-one; tert-butyl 4-({(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)piperazine-1-carboxylate; 2-methyl-N-({(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)propan-2-amine; 2-[ethyl({(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)amino]ethanol; 2-{(3S)-3-[(4-methylpiperazin-1-yl)methyl]pyrrolidin-1-yl}-4-(2-naphthyl)pyrimidine; (3S)-N,N-dimethyl-1-({(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)pyrrolidin-3-amine; 2-[(3R)-3-(1H-imidazol-1-ylmethyl)pyrrolidin-1-yl]-4-(2-naphthyl)pyrimidine; (3R)-N,N-dimethyl-1-({(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)pyrrolidin-3-amine; N,N-dimethyl-1-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methanamine; 4-(2-naphthyl)-2-[(3R)-3-(piperidin-1-ylmethyl)pyrrolidin-1-yl]pyrimidine; 4-(2-naphthyl)-2-[(3R)-3-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]pyrimidine; N-methyl-1-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methanamine; N-methyl-N-({(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)cyclohexanamine; 1-({(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)piperidin-2-one; tert-butyl 4-({(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)piperazine-1-carboxylate; 2-methyl-N-({(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)propan-2-amine; 2-[ethyl({(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)amino]ethanol; 2-{(3R)-3-[(4-methylpiperazin-1-yl)methyl]pyrrolidin-1-yl}-4-(2-naphthyl)pyrimidine; (3S)-N,N-dimethyl-1-({(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)pyrrolidin-3-amine; 2-[(3S)-3-(1H-imidazol-1-ylmethyl)pyrrolidin-1-yl]-4-(2-naphthyl)pyrimidine; (3R)-N,N-dimethyl-1-({(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}methyl)pyrrolidin-3-amine; N,N-dimethyl-1-[4-(2-naphthyl)pyrimidin-2-yl]-L-prolinamide; 4-(2-naphthyl)-2-[(2S)-2-(piperidin-1-ylcarbonyl)pyrrolidin-1-yl]pyrimidine; 4-(2-naphthyl)-2-[(2S)-2-(pyrrolidin-1-ylcarbonyl)pyrrolidin-1-yl]pyrimidine; N-tert-butyl-1-[4-(2-naphthyl)pyrimidin-2-yl]-L-prolinamide; N-ethyl-N-(2-hydroxyethyl)-1-[4-(2-naphthyl)pyrimidin-2-yl]-L-prolinamide; 2-{(2S)-2-[(4-methylpiperazin-1-yl)carbonyl]pyrrolidin-1-yl}-4-(2-naphthyl)pyrimidine; (3S)-N,N-dimethyl-1-{1-[4-(2-naphthyl)pyrimidin-2-yl]-L-prolyl}pyrrolidin-3-amine; (3R)-N,N-dimethyl-1-{1-[4-(2-naphthyl)pyrimidin-2-yl]-L-prolyl}pyrrolidin-3-amine; N,N-dimethyl-1-[4-(2-naphthyl)pyrimidin-2-yl]-D-prolinamide; 4-(2-naphthyl)-2-[(2R)-2-(piperidin-1-ylcarbonyl)pyrrolidin-1-yl]pyrimidine; 4-(2-naphthyl)-2-[(2R)-2-(pyrrolidin-1-ylcarbonyl)pyrrolidin-1-yl]pyrimidine; N-methyl-1-[4-(2-naphthyl)pyrimidin-2-yl]-D-prolinamide; N-tert-butyl-1-[4-(2-naphthyl)pyrimidin-2-yl]-D-prolinamide; 2-{(2R)-2-[(4-methylpiperazin-1-yl)carbonyl]pyrrolidin-1-yl}-4-(2-naphthyl)pyrimidine; (3S)-N,N-dimethyl-1-{1-[4-(2-naphthyl)pyrimidin-2-yl]-D-prolyl}pyrrolidin-3-amine; (3R)-N,N-dimethyl-1-{1-[4-(2-naphthyl)pyrimidin-2-yl]-D-prolyl}pyrrolidin-3-amine; (3′
S)-1′
-[4-(2-naphthyl)pyrimidin-2-yl]-1,3′
-bipyrrolidin-2-one;(3′
R)-1′
-[4-(2-naphthyl)pyrimidin-2-yl]-1,3′
-bipyrrolidin-2-one;tert-butyl {(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}carbamate; 2-[(3R)-3-methoxypyrrolidin-1-yl]-4-(2-naphthyl)pyrimidine; 2-[(3S)-3-methoxypyrrolidin-1-yl]-4-(2-naphthyl)pyrimidine; 2,2,2-trifluoro-N-(2-{(2S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-2-yl}ethyl)acetamide; 2,2,2-trifluoro-N-(2-{(2R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-2-yl}ethyl)acetamide; (3R)-N-methyl-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-amine; (3S)-N-methyl-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-amine; (3R)-N,N-dimethyl-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-amine; (3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]-N-(2,2,2-trifluoroethyl)pyrrolidin-3-amine; N-{(3S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}-N-(2,2,2-trifluoroethyl)acetamide; 2-{(2R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-2-yl}ethanamine; 2-{(2S)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-2-yl}ethanamine; 2-{1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}ethanamine; N-methyl-N-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}acetamide; N-ethyl-N,N′
-dimethyl-N′
-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}ethane-1,2-diamine;N,N′
-dimethyl-N-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}-N′
-propylethane-1,2-diamine;N-isopropyl-N,N′
-dimethyl-N′
-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}ethane-1,2-diamine;N-benzyl-N,N′
-dimethyl-N′
-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}ethane-1,2-diamine;N-methyl-N-[2-(methyl{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}amino)ethyl]acetamide; 2,2,2-trifluoro-N-methyl-N-[2-(methyl{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}amino)ethyl]acetamide; N-methyl-N-[2-(methyl{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}amino)ethyl]propanamide; N,2-dimethyl-N-[2-(methyl{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}amino)ethyl]propanamide; N-methyl-N-[2-(methyl{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}amino)ethyl]methanesulfonamide; b 1,1-diethyl-3-methyl-3-[2-(methyl{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidine-3-yl}amino)ethyl]urea; methyl methyl[2-(methyl{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}amino)ethyl]carbamate; N-methyl-N-[2-(methyl{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}amino)ethyl]ethanesulfonamide; N,N,N′
-trimethyl-N′
-[2-(methyl{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}amino)ethyl]sulfamide;N-methyl-N-[2-(methyl{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}amino)ethyl]benzamide; N-methyl-N-[2-(methyl{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}amino)ethyl]benzenesulfonamide; tert-butyl ({1-[4-(2-naphthyl)pyrimidin-2-yl]azetidin-3-yl}methyl)carbamate; 1-{1-[4-(2-naphthyl)pyrimidin-2-yl]azetidin-3-yl}methanamine; methyl ({1-[4-(2-naphthyl)pyrimidin-2-yl]azetidin-3-yl}methyl)carbamate; 2,2,2-trifluoro-N-({1-[4-(2-naphthyl)pyrimidin-2-yl]azetidin-3-yl}methyl)acetamide; N,N-dimethyl-N′
-({1-[4-(2-naphthyl)pyrimidin-2-yl]azetidin-3-yl}methyl)urea;N-({1-[4-(2-naphthyl)pyrimidin-2-yl]azetidin-3-yl}methyl)urea; N-ethyl-N′
-({1-[4-(2-naphthyl)pyrimidin-2-yl]azetidin-3-yl}methyl)urea;N-({1-[4-(2-naphthyl)pyrimidin-2-yl]azetidin-3-yl}methyl)methanesulfonamide; 4-methyl-N-({1-[4-(2-naphthyl)pyrimidin-2-yl]azetidin-3-yl}methyl)benzenesulfonamide; tert-butyl {2-[1-(4-naphthalen-2-ylpyrimidin-2-yl)azetidin-3-yl]ethyl}carbamate; 2-[1-(4-naphthalen-2-ylpyrimidin-2-yl)azetidin-3-yl]ethanamine; tert-butyl [(trans-4-{[4-(2-naphthyl)pyrimidin-2-yl]oxy}cyclohexyl)methyl]carbamate; 1-(trans-4-{[4-(2-naphthyl)pyrimidin-2-yl]oxy}cyclohexyl)methanamine; tert-butyl ({cis-4-[(4-naphthalen-2-ylpyrimidin-2-yl)oxy]cyclohexyl}methyl)carbamate; 1-{cis-4-[(4-naphthalen-2-ylpyrimidin-2-yl)oxy]cyclohexyl}methanamine; N-[trans-4-(aminomethyl)cyclohexyl]-N-methyl-4-(2-naphthyl)pyrimidin-2-amine; benzyl [(cis-4-{methyl[4-(2-naphthyl)pyrimidin-2-yl]amino}cyclohexyl)methyl]carbamate; N-[cis-4-(aminomethyl)cyclohexyl]-N-methyl-4-(2-naphthyl)pyrimidin-2-amine; 1-{4-[4-(2-naphthyl)pyrimidin-2-yl]phenyl}methanamine; 1-[trans-4-(4-naphthalen-2-ylpyrimidin-2-yl)cyclohexyl]methanamine; 1-{cis-4-[4-(2-naphthyl)pyrimidin-2-yl]cyclohexyl}methanamine; 1-{1-[4-(6-methoxy-2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methanamine; 1-{1-[4-(6-propoxy-2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methanamine; 1-{1-[4-(6-isobutoxy-2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methanamine; 6-{2-[4-(aminomethyl)piperidin-1-yl]pyrimidin-4-yl}-2-naphthyl acetate; 6-{2-[4-(aminomethyl)piperidin-1-yl]pyrimidin-4-yl}-2-naphthol; 2,2,2-trifluoro-N-({1-[4-(6-hydroxy-2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methyl)acetamide; 2,2,2-trifluoro-N-({1-[4-(6-methoxy-2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methyl)acetamide; 1-(1-{4-[6-(2-thienyl)-2-naphthyl]pyrimidin-2-yl}piperidin-4-yl)methanamine; 1-(1-{4-[6-(2-methoxyphenyl)-2-naphthyl]pyrimidin-2-yl}piperidin-4-yl)methanamine; 1-(1-{4-[6-(4-methoxyphenyl)-2-naphthyl]pyrimidin-2-yl}piperidin-4-yl)methanamine; 1-{1-[4-(6-phenyl-2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methanamine; 2,2,2-trifluoro-N-({1-[4-(6-formyl-2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methyl)acetamide; 1-{1-[4-(6-vinyl-2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methanamine; 1-{1-[4-(6-methyl-2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methanamine; 1-(1-{4-[6-(piperidin-1-ylmethyl)-2-naphthyl]pyrimidin-2-yl}piperidin-4-yl)methanamine; 1-(1-{4-[6-(morpholin-4-ylmethyl)-2-naphthyl]pyrimidin-2-yl}piperidin-4-yl)methanamine; 2-{4-[(4-methylpiperazin-1-yl)methyl]piperidin-1-yl}-4-(2-naphthyl)pyrimidine; N-methyl-N-({1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methyl)cyclohexanamine; 1-({1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methyl)azepane; 2-[ethyl({1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methyl)amino]ethanol; 2-methyl-N-({1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methyl)propan-2-amine; 1-({1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methyl)pyrrolidin-2-one; 1-({1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methyl)piperidin-2-one; 4-(2-naphthyl)-2-[4-(piperazin-1-ylmethyl)piperidin-1-yl]pyrimidine; 4-({1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methyl)morpholine; 4-({1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methyl)piperazin-2-one; 1-(1-{[4-(2-naphthyl)pyrimidin-2-yl]carbonyl}piperidin-4-yl)methanamine;
or(3aR,7aS)-5-[4-(2-naphthyl)pyrimidin-2-yl]octahydro-1H-pyrrolo[3,4-c]pyridine.
-
-
34. A compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein the compound is N,N,N′
- -trimethyl-N′
-{(3R)-1-[4-(2-naphthyl)pyrimidin-2-yl]pyrrolidin-3-yl}ethane-1,2-diamine.
- -trimethyl-N′
-
35. A compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein the compound is ({1-[4-(2-naphthyl)pyrimidin-2-yl]piperidin-4-yl}methyl)amine.
-
36. A composition comprising the compound or pharmaceutically acceptable salt of the compound of claim 1 or 30 and a pharmaceutically acceptable carrier.
-
37. The composition of claim 36, wherein the pharmaceutically acceptable carrier is suitable for oral administration and the composition comprises an oral dosage form.
-
38. A method of treating a canonical Wnt-β
- -catenin cellular messaging system related disorder, comprising administering to a mammal in need thereof a compound or a pharmaceutically acceptable salt thereof the compound of claim 1 or 30 in an amount effect to treat a canonical Wnt-β
-catenin cellular messaging system related disorder.
- -catenin cellular messaging system related disorder, comprising administering to a mammal in need thereof a compound or a pharmaceutically acceptable salt thereof the compound of claim 1 or 30 in an amount effect to treat a canonical Wnt-β
-
39. The method of claim 38, wherein the canonical Wnt-β
- -catenin cellular messaging system related disorder is selected from the group consisting of bone disorders, cancer, and Alzheimer'"'"'s disease.
-
40. The method of claim 39, wherein the cancer is selected from the group consisting of leukemia, skin cancer, bladder cancer, breast cancer, uterus cancer, ovary cancer, prostate cancer, lung cancer, colon cancer, pancreas cancer, renal cancer, gastric cancer, and brain cancer.
-
41. The method of claim 39, wherein the bone disorder is selected from the group consisting of osteoarthritis, osteolysis from multiple myeloma, osteoporosis, and rheumatoid arthritis.
-
42. The method of claim 38, wherein the mammal is human.
-
44. A process for preparing a compound of Formula (a)
-
45. The process of claim 44, the process further comprising preparing a compound of Formula (c)
-
46. The process of claim 44, wherein the base is EtONa.
-
2. The compound of claim 1, wherein R7 is H or OR11.
-
30. A compound of the Formula (II):
- View Dependent Claims (32, 43)
-
32. The compound of claim 30, or a pharmaceutically acceptable salt thereof, wherein the compound is
N-[4-(2-naphthyl)pyrimidin-2-yl]azepan-4-amine; -
tert-butyl 3-({[4-(2-naphthyl)pyrimidin-2-yl]amino }methyl)azetidine-1-carboxylate; N-(azetidin-3-ylmethyl)-4-(2-naphthyl)pyrimidin-2-amine; tert-butyl (3S)-3-({[4-(2-naphthyl)pyrimidin-2-yl]amino }methyl)pyrrolidine-1-carboxylate; 4-(2-naphthyl)-N-[(3R)-pyrrolidin-3-ylmethyl]pyrimidin-2-amine; N-(2-morpholin-4-ylethyl)-4-(2-naphthyl)pyrimidin-2-amine; N-(3-morpholin-4-ylpropyl)-4-(2-naphthyl)pyrimidin-2-amine; 4-(2-naphthyl)-N-(pyridin-3-ylmethyl)pyrimidin-2-amine; 4-(2-naphthyl)-N-(pyridin-4-ylmethyl)pyrimidin-2-amine; 4-(2-naphthyl)-N-(pyridin-2-ylmethyl)pyrimidin-2-amine; 4-({[4-(2-naphthyl)pyrimidin-2-yl]amino }methyl)benzenesulfonamide; 4-(2-naphthyl)-N-(2-pyridin-3-ylethyl)pyrimidin-2-amine; 4-(2-naphthyl)-N-(2-pyridin-4-ylethyl)pyrimidin-2-amine; tert-butyl (3S)-3-{[4-(2-naphthyl)pyrimidin-2-yl]amino}pyrrolidine-1-carboxylate; tert-butyl (3R)-3-{[4-(2-naphthyl)pyrimidin-2-yl]amino}pyrrolidine-1-carboxylate; 4-(2-naphthyl)-N-[(3S)-pyrrolidin-3-yl]pyrimidin-2-amine; 4-(2-naphthyl)-N-[(3R)-pyrrolidin-3-yl]pyrimidin-2-amine; tert-butyl (3R)-3-({[4-(2-naphthyl)pyrimidin-2-yl]amino }methyl)pyrrolidine-1-carboxylate; 4-(2-naphthyl)-N-[(3S)-pyrrolidin-3-ylmethyl]pyrimidin-2-amine; 4-(2-naphthyl)-N-(piperidin-4-ylmethyl)pyrimidin-2-amine; tert-butyl 4-({[4-(2-naphthyl)pyrimidin-2-yl]amino }methyl)piperidine-1-carboxylate; trans-N-[4-(2-naphthyl)pyrimidin-2-yl]cyclohexane-1,4-diamine; N-(4-methoxybenzyl)-4-(2-naphthyl)pyrimidin-2-amine; N-[2-(4-methylphenyl)ethyl]-4-(2-naphthyl)pyrimidin-2-amine; 2-{methyl[4-(2-naphthyl)pyrimidin-2-yl]amino}ethanol; N-(2-methoxyethyl)-4-(2-naphthyl)pyrimidin-2-amine; 2-{[4-(2-naphthyl)pyrimidin-2-yl]amino }ethanol; N-(2-methoxyethyl)-N-methyl-4-(2-naphthyl)pyrimidin-2-amine; N-methyl-4-(2-naphthyl)pyrimidin-2-amine; N,N-diethyl-4-(2-naphthyl)pyrimidin-2-amine; 4-(2-naphthyl)-N-propylpyrimidin-2-amine; N-butyl-4-(2-naphthyl)pyrimidin-2-amine; N-isopropyl-4-(2-naphthyl)pyrimidin-2-amine; N-(sec-butyl)-4-(2-naphthyl)pyrimidin-2-amine; N-isobutyl-4-(2-naphthyl)pyrimidin-2-amine; N-(tert-butyl)-4-(2-naphthyl)pyrimidin-2-amine; N-benzyl-4-(2-naphthyl)pyrimidin-2-amine; 4-(2-naphthyl)-N-(2-phenylethyl)pyrimidin-2-amine; N-cyclopentyl-4-(2-naphthyl)pyrimidin-2-amine; N-cyclohexyl-4-(2-naphthyl)pyrimidin-2-amine; tert-butyl 4-{[4-(2-naphthyl)pyrimidin-2-yl]amino}piperidine-1-carboxylate; 4-(2-naphthyl)-N-piperidin-4-ylpyrimidin-2-amine; tert-butyl 4- {methyl[4-(2-naphthyl)pyrimidin-2-yl]amino}piperidine-1-carboxylate; N-methyl-4-(2-naphthyl)-N-piperidin-4-ylpyrimidin-2-amine; tert-butyl 4-(2-methoxy-1-{[4-(2-naphthyl)pyrimidin-2-yl]amino}-2-oxoethyl)piperidine-1-carboxylate; 4-{methyl[4-(2-naphthyl)pyrimidin-2-yl]amino}piperidine-1-carbaldehyde; N-(1-benzylpiperidin-4-yl)-N-methyl-4-(2-naphthyl)pyrimidin-2-amine; N-[(1-acetylazetidin-3-yl)methyl]-4-(2-naphthyl)pyrimidin-2-amine; 4-(2-naphthyl)-N-{[1-(trifluoroacetyl)azetidin-3-yl]methyl}pyrimidin-2-amine; N-[(1-benzoylazetidin-3-yl)methyl]-4-(2-naphthyl)pyrimidin-2-amine; 3-({[4-(2-naphthyl)pyrimidin-2-yl]amino}methyl)azetidine-1-carboxamide; N-ethyl-3-({[4-(2-naphthyl)pyrimidin-2-yl]amino}methyl)azetidine-1-carboxamide; N-{[1-(methylsulfonyl)azetidin-3-yl]methyl}-4-(2-naphthyl)pyrimidin-2-amine; N-({1-[(4-methylphenyl)sulfonyl]azetidin-3-yl}methyl)-4-(2-naphthyl)pyrimidin-2-amine; N,N-dimethyl-3-({[4-(2-naphthyl)pyrimidin-2-yl]amino}methyl)azetidine-1-sulfonamide; N-[(3S)-1-acetylpyrrolidin-3-yl]-4-(2-naphthyl)pyrimidin-2-amine; N-[(3S)-1-benzoylpyrrolidin-3-yl]-4-(2-naphthyl)pyrimidin-2-amine; methyl (3S)-3-{[4-(2-naphthyl)pyrimidin-2-yl]amino}pyrrolidine-1-carboxylate; (3S)-N,N-dimethyl-3-{[4-(2-naphthyl)pyrimidin-2-yl]amino}pyrrolidine-1-carboxamide; (3S)-N-ethyl-3-{[4-(2-naphthyl)pyrimidin-2-yl]amino}pyrrolidine-1-carboxamide; (3S)-3-{[4-(2-naphthyl)pyrimidin-2-yl]amino}pyrrolidine-1-carboxamide; (3S)-N,N-dimethyl-3-{[4-(2-naphthyl)pyrimidin-2-yl]amino}pyrrolidine-1-sulfonamide; N-[(3S)-1-(methylsulfonyl)pyrrolidin-3-yl]-4-(2-naphthyl)pyrimidin-2-amine; N-{(3S)-1-[(4-methylphenyl)sulfonyl]pyrrolidin-3-yl}-4-(2-naphthyl)pyrimidin-2-amine; (3S)-3-{[4-(2-naphthyl)pyrimidin-2-yl]amino}pyrrolidine-1-carbaldehyde; N-[(3S)-1-(morpholin-4-ylcarbonyl)pyrrolidin-3-yl]-4-(2-naphthyl)pyrimidin-2-amine; ethyl (3S)-3-{[4-(2-naphthyl)pyrimidin-2-yl]amino}pyrrolidine-1-carboxylate; N-[(3R)-1-acetylpyrrolidin-3-yl]-4-(2-naphthyl)pyrimidin-2-amine; N-[(3R)-1-benzoylpyrrolidin-3-yl]-4-(2-naphthyl)pyrimidin-2-amine; methyl (3R)-3-{[4-(2-naphthyl)pyrimidin-2-yl]amino}pyrrolidine-1-carboxylate; (3R)-N,N-dimethyl-3-{[4-(2-naphthyl)pyrimidin-2-yl]amino}pyrrolidine-1-carboxamide; (3R)-N-ethyl-3-{[4-(2-naphthyl)pyrimidin-2-yl]amino}pyrrolidine-1-carboxamide; (3R)-3-{[4-(2-naphthyl)pyrimidin-2-yl]amino}pyrrolidine-1-carboxamide; (3R)-N,N-dimethyl-3-{[4-(2-naphthyl)pyrimidin-2-yl]amino}pyrrolidine-1-sulfonamide; N-[(3R)-1-(methylsulfonyl)pyrrolidin-3-yl]-4-(2-naphthyl)pyrimidin-2-amine; N-{(3R)-1-[(4-methylphenyl)sulfonyl]pyrrolidin-3-yl}-4-(2-naphthyl)pyrimidin-2-amine; (3R)-3-{[4-(2-naphthyl)pyrimidin-2-yl]amino}pyrrolidine-1-carbaldehyde; N-[(3R)-1-(morpholin-4-ylcarbonyl)pyrrolidin-3-yl]-4-(2-naphthyl)pyrimidin-2-amine; ethyl (3R)-3-{[4-(2-naphthyl)pyrimidin-2-yl]amino}pyrrolidine-1-carboxylate; N-{[(3R)-1-acetylpyrrolidin-3-yl]methyl}-4-(2-naphthyl)pyrimidin-2-amine; methyl (3R)-3-({[4-(2-naphthyl)pyrimidin-2-yl]amino}methyl)pyrrolidine-1-carboxylate; (3R)-3-({[4-(2-naphthyl)pyrimidin-2-yl]amino}methyl)pyrrolidine-1-carbaldehyde; N-{[(3S)-1-acetylpyrrolidin-3-yl]methyl}-4-(2-naphthyl)pyrimidin-2-amine; methyl (3S)-3-({[4-(2-naphthyl)pyrimidin-2-yl]amino}methyl)pyrrolidine-1-carboxylate; (3S)-3-({[4-(2-naphthyl)pyrimidin-2-yl]amino}methyl)pyrrolidine-1-carbaldehyde; N-[(1-acetylpiperidin-4-yl)methyl]-4-(2-naphthyl)pyrimidin-2-amine; N,N-dimethyl-4-({[4-(2-naphthyl)pyrimidin-2-yl]amino}methyl)piperidine-1-carboxamide; N,N-diethyl-4-({[4-(2-naphthyl)pyrimidin-2-yl]amino}methyl)piperidine-1-carboxamide; 4-(2-naphthyl)-N-{[1-(pyrrolidin-1-ylcarbonyl)piperidin-4-yl]methyl}pyrimidin-2-amine; N-{[1-(methylsulfonyl)piperidin-4-yl]methyl}-4-(2-naphthyl)pyrimidin-2-amine; N,N-dimethyl-4-({[4-(2-naphthyl)pyrimidin-2-yl]amino}methyl)piperidine-1-sulfonamide; 4-({[4-(2-naphthyl)pyrimidin-2-yl]amino}methyl)piperidine-1-carboxamide; N-ethyl-4-({[4-(2-naphthyl)pyrimidin-2-yl]amino}methyl)piperidine-1-carboxamide; N-isopropyl-4-({[4-(2-naphthyl)pyrimidin-2-yl]amino}methyl)piperidine-1-carboxamide; N-cyclohexyl-4-({[4-(2-naphthyl)pyrimidin-2-yl]amino}methyl)piperidine-1-carboxamide; N-[(1-benzoylpiperidin-4-yl)methyl]-4-(2-naphthyl)pyrimidin-2-amine; N-[(1-ethylpiperidin-4-yl)methyl]-4-(2-naphthyl)pyrimidin-2-amine; N-[(1-benzylpiperidin-4-yl)methyl]-4-(2-naphthyl)pyrimidin-2-amine; 4-(2-naphthyl)-N-{[1-(phenylacetyl)piperidin-4-yl]methyl}pyrimidin-2-amine; N-({1-[(4-methylphenyl)sulfonyl]piperidin-4-yl}methyl)-4-(2-naphthyl)pyrimidin-2-amine; N-(trans-4-{[4-(2-naphthyl)pyrimidin-2-yl]amino}cyclohexyl)acetamide; methyl (trans-4-{[4-(2-naphthyl)pyrimidin-2-yl]amino}cyclohexyl)carbamate; N,N-dimethyl-N′
-(trans-4-{[4-(2-naphthyl)pyrimidin-2-yl]amino}cyclohexyl)urea;N-ethyl-N′
-(trans-4-{[4-(2-naphthyl)pyrimidin-2-yl]amino}cyclohexyl)urea;N,N-dimethyl-N′
-(trans-4-{[4-(2-naphthyl)pyrimidin-2-yl]amino}cyclohexyl)sulfamide;N-(trans-4-{[4-(2-naphthyl)pyrimidin-2-yl]amino}cyclohexyl)methanesulfonamide; 4-methyl-N-(trans-4-{[4-(2-naphthyl)pyrimidin-2-yl]amino}cyclohexyl)benzenesulfonamide; 5-(dimethylamino)-N-(trans-4-{[4-(2-naphthyl)pyrimidin-2-yl]amino}cyclohexyl)naphthalene-1-sulfonamide; 4-cyano-N-(3-{[4-(2-naphthyl)pyrimidin-2-yl]amino}cyclohexyl)benzamide; N-(1-acetylpiperidin-4-yl)-4-(2-naphthyl)pyrimidin-2-amine; N,N-dimethyl-4-{[4-(2-naphthyl)pyrimidin-2-yl]amino}piperidine-1-carboxamide; N,N-diethyl-4-{[4-(2-naphthyl)pyrimidin-2-yl]amino}piperidine-1-carboxamide; 4-(2-naphthyl)-N-[1-(pyrrolidin-1-ylcarbonyl)piperidin-4-yl]pyrimidin-2-amine; N-[1-(morpholin-4-ylcarbonyl)piperidin-4-yl]-4-(2-naphthyl)pyrimidin-2-amine; N-[1-(methylsulfonyl)piperidin-4-yl]-4-(2-naphthyl)pyrimidin-2-amine; N,N-dimethyl-4-{[4-(2-naphthyl)pyrimidin-2-yl]amino}piperidine-1-sulfonamide; 4-{[4-(2-naphthyl)pyrimidin-2-yl]amino}piperidine-1-carboxamide; N-ethyl-4-{[4-(2-naphthyl)pyrimidin-2-yl]amino}piperidine-1-carboxamide; N-isopropyl-4-{[4-(2-naphthyl)pyrimidin-2-yl]amino}piperidine-1-carboxamide; N-cyclohexyl-4-{[4-(2-naphthyl)pyrimidin-2-yl]amino}piperidine-1-carboxamide; N-(1-benzoylpiperidin-4-yl)-4-(2-naphthyl)pyrimidin-2-amine; N-(1-acetylpiperidin-4-yl)-N-methyl-4-(2-naphthyl)pyrimidin-2-amine; N-methyl-4-(2-naphthyl)-N-[1-(trifluoroacetyl)piperidin-4-yl]pyrimidin-2-amine; N-(1-benzoylpiperidin-4-yl)-N-methyl-4-(2-naphthyl)pyrimidin-2-amine; methyl 4-{methyl[4-(2-naphthyl)pyrimidin-2-yl]amino}piperidine-1-carboxylate; N,N-dimethyl-4-{methyl[4-(2-naphthyl)pyrimidin-2-yl]amino}piperidine-1-carboxamide; N-methyl-4-(2-naphthyl)-N-[1-(pyrrolidin-1-ylcarbonyl)piperidin-4-yl]pyrimidin-2-amine; N,N-diethyl-4-{methyl[4-(2-naphthyl)pyrimidin-2-yl]amino}piperidine-1-carboxamide; N-ethyl-4-{methyl[4-(2-naphthyl)pyrimidin-2-yl]amino}piperidine-1-carboxamide; 4-{methyl[4-(2-naphthyl)pyrimidin-2-yl]amino}piperidine-1-carboxamide; N-methyl-N-[1-(methylsulfonyl)piperidin-4-yl]-4-(2-naphthyl)pyrimidin-2-amine; N-methyl-N-{1-[(4-methylphenyl)sulfonyl]piperidin-4-yl}-4-(2-naphthyl)pyrimidin-2-amine; N-methyl-4-(2-naphthyl)-N-(1-pyrimidin-2-ylpiperidin-4-yl)pyrimidin-2-amine; N-methyl-4-(2-naphthyl)-N-(1-propylpiperidin-4-yl)pyrimidin-2-amine; 2-(4-{methyl[4-(2-naphthyl)pyrimidin-2-yl]amino}piperidin-1-yl)acetamide; N-methyl-4-(2-naphthyl)-N-{1-[2-(trityloxy)ethyl]piperidin-4-yl}pyrimidin-2-amine; 4-{methyl[4-(2-naphthyl)pyrimidin-2-yl]amino}piperidine-1-carboximidamide; tert-butyl (3-{[4-(2-naphthyl)pyrimidin-2-yl]amino}cyclohexyl)carbamate;
or4-(2-naphthyl)-2-[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]pyrimidine.
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43. A method of synthesizing a compound of claim 9 or 30, comprising:
- reacting a compound of the Formula 4;
- reacting a compound of the Formula 4;
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32. The compound of claim 30, or a pharmaceutically acceptable salt thereof, wherein the compound is
Specification
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Current AssigneeWyeth LLC (Pfizer Inc.)
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Original AssigneeWyeth (Pfizer Inc.)
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InventorsVera, Matthew Douglas, Rogers, John Francis JR., Molinari, Albert John, Mehlmann, John Francis, Lundquist, Joseph Theodore IV, Pelletier, Jeffrey Claude, Mann, Charles William, Hauze, Diane Barbara, Green, Daniel Michael, Felix, Luciana de Araujo
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Application NumberUS12/194,235Publication NumberTime in Patent OfficeDaysField of SearchUS Class Current514/210.200CPC Class CodesA61P 19/02 for joint disorders, e.g. a...A61P 19/08 for bone diseases, e.g. rac...A61P 19/10 for osteoporosisA61P 25/00 Drugs for disorders of the ...A61P 25/28 for treating neurodegenerat...A61P 29/00 Non-central analgesic, anti...A61P 35/00 Antineoplastic agentsA61P 35/02 specific for leukemiaA61P 43/00 Drugs for specific purposes...C07D 239/26 with only hydrogen atoms, h...C07D 239/34 One oxygen atomC07D 401/06 linked by a carbon chain co...C07D 403/04 directly linked by a ring-m...C07D 451/02 containing not further cond...C07D 471/04 Ortho-condensed systemsC07D 471/10 Spiro-condensed systemsC07D 487/04 Ortho-condensed systemsC07D 487/08 Bridged systems