DK2493876T3 - Imidazole derivatives AS casein kinase inhibitors - Google Patents

Info

Publication number

DK2493876T3

DK2493876T3 DK10774282.7T DK10774282T DK2493876T3 DK 2493876 T3 DK2493876 T3 DK 2493876T3 DK 10774282 T DK10774282 T DK 10774282T DK 2493876 T3 DK2493876 T3 DK 2493876T3

Authority

DK

Denmark

Prior art keywords

imidazol

fluorophenyl

pyrimidin

pharmaceutically acceptable

amine

Prior art date

2009-10-28

Links

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• Global Dossier
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• 150000002460 imidazoles Chemical class 0.000 title description 3
• 102000005403 Casein Kinases Human genes 0.000 title 1
• 108010031425 Casein Kinases Proteins 0.000 title 1
• 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title 1
• 229940043355 kinase inhibitor Drugs 0.000 title 1
• 239000003757 phosphotransferase inhibitor Substances 0.000 title 1
• -1 pyrimidin-2-ylmethyl Chemical group 0.000 claims description 154
• 150000001875 compounds Chemical class 0.000 claims description 142
• 125000001424 substituent group Chemical group 0.000 claims description 81
• 150000003839 salts Chemical class 0.000 claims description 58
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 57
• 229910052739 hydrogen Inorganic materials 0.000 claims description 53
• 239000001257 hydrogen Substances 0.000 claims description 53
• 229910052736 halogen Inorganic materials 0.000 claims description 33
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 33
• 150000002367 halogens Chemical group 0.000 claims description 32
• 125000005842 heteroatom Chemical group 0.000 claims description 28
• 125000001072 heteroaryl group Chemical group 0.000 claims description 25
• 125000000217 alkyl group Chemical group 0.000 claims description 19
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 12
• 229910052731 fluorine Inorganic materials 0.000 claims description 10
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
• 239000011737 fluorine Substances 0.000 claims description 9
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
• 208000020925 Bipolar disease Diseases 0.000 claims description 8
• 208000019022 Mood disease Diseases 0.000 claims description 8
• 208000035475 disorder Diseases 0.000 claims description 8
• 230000000694 effects Effects 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 8
• 208000020016 psychiatric disease Diseases 0.000 claims description 8
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
• 230000000926 neurological effect Effects 0.000 claims description 7
• 208000019116 sleep disease Diseases 0.000 claims description 7
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 6
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 6
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
• 201000010099 disease Diseases 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000001153 fluoro group Chemical group F* 0.000 claims description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
• 230000002401 inhibitory effect Effects 0.000 claims description 5
• 230000005764 inhibitory process Effects 0.000 claims description 5
• 125000003545 alkoxy group Chemical group 0.000 claims description 4
• 208000020685 sleep-wake disease Diseases 0.000 claims description 4
• 208000020401 Depressive disease Diseases 0.000 claims description 3
• 230000027288 circadian rhythm Effects 0.000 claims description 3
• 125000005843 halogen group Chemical group 0.000 claims description 3
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 7
• 150000002431 hydrogen Chemical group 0.000 claims 4
• QLMXTWLZXLSYPY-UHFFFAOYSA-N 2-[[4-(4-phenyl-5-pyrimidin-4-ylimidazol-1-yl)piperidin-1-yl]methyl]pyrimidine Chemical compound N=1C=CC=NC=1CN(CC1)CCC1N1C=NC(C=2C=CC=CC=2)=C1C1=CC=NC=N1 QLMXTWLZXLSYPY-UHFFFAOYSA-N 0.000 claims 1
• RXNQNOUVAKIMHA-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-3-[1-(1,2-oxazol-3-ylmethyl)piperidin-4-yl]imidazol-4-yl]-n-methylpyrimidin-2-amine Chemical compound CNC1=NC=CC(C=2N(C=NC=2C=2C=CC(F)=CC=2)C2CCN(CC3=NOC=C3)CC2)=N1 RXNQNOUVAKIMHA-UHFFFAOYSA-N 0.000 claims 1
• XPWHRQHBPRSUAW-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-3-[1-(1,2-oxazol-3-ylmethyl)piperidin-4-yl]imidazol-4-yl]pyrimidin-2-amine Chemical compound NC1=NC=CC(C=2N(C=NC=2C=2C=CC(F)=CC=2)C2CCN(CC3=NOC=C3)CC2)=N1 XPWHRQHBPRSUAW-UHFFFAOYSA-N 0.000 claims 1
• SMYILHSDBTWVCE-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-3-[1-(1,2-oxazol-3-ylmethyl)pyrrolidin-3-yl]imidazol-4-yl]pyrimidin-2-amine Chemical compound NC1=NC=CC(C=2N(C=NC=2C=2C=CC(F)=CC=2)C2CN(CC3=NOC=C3)CC2)=N1 SMYILHSDBTWVCE-UHFFFAOYSA-N 0.000 claims 1
• LNSKPRAKVGLVRO-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-3-[1-(1,3-thiazol-5-ylmethyl)piperidin-4-yl]imidazol-4-yl]pyrimidin-2-amine Chemical compound NC1=NC=CC(C=2N(C=NC=2C=2C=CC(F)=CC=2)C2CCN(CC=3SC=NC=3)CC2)=N1 LNSKPRAKVGLVRO-UHFFFAOYSA-N 0.000 claims 1
• DWIZPJMTGPAZME-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-3-[1-(pyridazin-4-ylmethyl)piperidin-4-yl]imidazol-4-yl]pyrimidin-2-amine Chemical compound NC1=NC=CC(C=2N(C=NC=2C=2C=CC(F)=CC=2)C2CCN(CC=3C=NN=CC=3)CC2)=N1 DWIZPJMTGPAZME-UHFFFAOYSA-N 0.000 claims 1
• KNSHMBXGEPKKPY-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-3-[1-[(2-methylpyridin-4-yl)methyl]piperidin-4-yl]imidazol-4-yl]pyrimidin-2-amine Chemical compound C1=NC(C)=CC(CN2CCC(CC2)N2C(=C(N=C2)C=2C=CC(F)=CC=2)C=2N=C(N)N=CC=2)=C1 KNSHMBXGEPKKPY-UHFFFAOYSA-N 0.000 claims 1
• BEPDMFYDDOZELL-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-3-[1-[(2-methylpyrimidin-5-yl)methyl]piperidin-4-yl]imidazol-4-yl]pyrimidin-2-amine Chemical compound C1=NC(C)=NC=C1CN1CCC(N2C(=C(N=C2)C=2C=CC(F)=CC=2)C=2N=C(N)N=CC=2)CC1 BEPDMFYDDOZELL-UHFFFAOYSA-N 0.000 claims 1
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 1
• PNZSCTKQBAZEQU-UHFFFAOYSA-N n-methyl-4-[3-[1-(1,2-oxazol-3-ylmethyl)piperidin-4-yl]-5-phenylimidazol-4-yl]pyrimidin-2-amine Chemical compound CNC1=NC=CC(C=2N(C=NC=2C=2C=CC=CC=2)C2CCN(CC3=NOC=C3)CC2)=N1 PNZSCTKQBAZEQU-UHFFFAOYSA-N 0.000 claims 1
• YLKRIZZCCGCJKZ-UHFFFAOYSA-N n-methyl-4-[5-phenyl-3-[1-(pyrimidin-2-ylmethyl)piperidin-4-yl]imidazol-4-yl]pyrimidin-2-amine Chemical compound CNC1=NC=CC(C=2N(C=NC=2C=2C=CC=CC=2)C2CCN(CC=3N=CC=CN=3)CC2)=N1 YLKRIZZCCGCJKZ-UHFFFAOYSA-N 0.000 claims 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
• 239000000203 mixture Substances 0.000 description 67
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
• 239000007787 solid Substances 0.000 description 54
• 239000000243 solution Substances 0.000 description 50
• 125000004429 atom Chemical group 0.000 description 47
• 239000000047 product Substances 0.000 description 46
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
• 238000006243 chemical reaction Methods 0.000 description 40
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
• 238000000034 method Methods 0.000 description 39
• 238000005160 1H NMR spectroscopy Methods 0.000 description 37
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 25
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 24
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
• 125000003118 aryl group Chemical group 0.000 description 22
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 22
• 239000012044 organic layer Substances 0.000 description 22
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
• 239000002904 solvent Substances 0.000 description 21
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
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• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 18
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 17
• 238000003786 synthesis reaction Methods 0.000 description 17
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• 241000124008 Mammalia Species 0.000 description 13
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• 150000001299 aldehydes Chemical class 0.000 description 11
• 125000000753 cycloalkyl group Chemical group 0.000 description 11
• 239000003814 drug Substances 0.000 description 11
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 11
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
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