RU2008148903A - Производные имидазол-пиримидина для лечения заболеваний, ассоциированных с киназой гликогенсинтазы 3 (gsk3) - Google Patents
Производные имидазол-пиримидина для лечения заболеваний, ассоциированных с киназой гликогенсинтазы 3 (gsk3) Download PDFInfo
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- RU2008148903A RU2008148903A RU2008148903/04A RU2008148903A RU2008148903A RU 2008148903 A RU2008148903 A RU 2008148903A RU 2008148903/04 A RU2008148903/04 A RU 2008148903/04A RU 2008148903 A RU2008148903 A RU 2008148903A RU 2008148903 A RU2008148903 A RU 2008148903A
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- Prior art keywords
- alkyl
- methyl
- heterocyclyl
- fluoro
- pyran
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims 4
- 201000010099 disease Diseases 0.000 title claims 2
- 102000001267 GSK3 Human genes 0.000 title 2
- 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 title 2
- KNDAOVHRTCJABP-UHFFFAOYSA-N 1h-imidazole;pyrimidine Chemical class C1=CNC=N1.C1=CN=CN=C1 KNDAOVHRTCJABP-UHFFFAOYSA-N 0.000 title 1
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 48
- -1 nitro, cyano, hydroxy, amino, sulfamoyl Chemical group 0.000 claims abstract 34
- 125000004452 carbocyclyl group Chemical group 0.000 claims abstract 30
- 150000001875 compounds Chemical class 0.000 claims abstract 30
- 125000005843 halogen group Chemical group 0.000 claims abstract 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 20
- 239000001257 hydrogen Substances 0.000 claims abstract 20
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 20
- 229910052799 carbon Inorganic materials 0.000 claims abstract 16
- 150000001721 carbon Chemical group 0.000 claims abstract 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract 11
- 150000002431 hydrogen Chemical group 0.000 claims abstract 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 11
- 150000002829 nitrogen Chemical class 0.000 claims abstract 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 11
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims abstract 10
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 7
- 150000002367 halogens Chemical group 0.000 claims abstract 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 4
- 125000004122 cyclic group Chemical group 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims 63
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 206010012289 Dementia Diseases 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000001589 carboacyl group Chemical group 0.000 claims 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- 208000010877 cognitive disease Diseases 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 3
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 3
- 125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 3
- 201000011240 Frontotemporal dementia Diseases 0.000 claims 3
- 210000000988 bone and bone Anatomy 0.000 claims 3
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- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
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- 125000005236 alkanoylamino group Chemical group 0.000 claims 2
- 125000005189 alkyl hydroxy group Chemical group 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 239000012458 free base Substances 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
- 208000027061 mild cognitive impairment Diseases 0.000 claims 2
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- 230000002265 prevention Effects 0.000 claims 2
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- 150000003839 salts Chemical class 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
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- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 1
- DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 claims 1
- JQKHWBMOBOUEHF-UHFFFAOYSA-N 1-[3-[[5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]methylamino]propyl]pyrrolidin-2-one Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=N1)=CC=C1CNCCCN1CCCC1=O JQKHWBMOBOUEHF-UHFFFAOYSA-N 0.000 claims 1
- YJQMYAJLSLMRCL-UHFFFAOYSA-N 1-[4-[[5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]methyl]-1,4-diazepan-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCCN1CC(N=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 YJQMYAJLSLMRCL-UHFFFAOYSA-N 0.000 claims 1
- AGPQIAYITNTXBZ-UHFFFAOYSA-N 1-[4-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]piperidin-1-yl]-2-phenylethanone Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(CC1)CCN1C(=O)CC1=CC=CC=C1 AGPQIAYITNTXBZ-UHFFFAOYSA-N 0.000 claims 1
- WYXQLSUEACNNHD-UHFFFAOYSA-N 1-[4-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 WYXQLSUEACNNHD-UHFFFAOYSA-N 0.000 claims 1
- OABIVMOLIVHUJE-UHFFFAOYSA-N 1-[5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-3-yl]ethanone Chemical compound CC(=O)C1=CN=CC(NC=2N=C(C(F)=CN=2)C=2N(C(C)=NC=2)C2CCOCC2)=C1 OABIVMOLIVHUJE-UHFFFAOYSA-N 0.000 claims 1
- YWZMVPXYEIFISA-UHFFFAOYSA-N 2,2,2-trifluoro-1-[4-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]piperidin-1-yl]ethanone Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC1CCN(C(=O)C(F)(F)F)CC1 YWZMVPXYEIFISA-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- LCPSWIIFCQJWCM-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-(1-methylsulfonylpiperidin-4-yl)pyrimidin-2-amine Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC1CCN(S(C)(=O)=O)CC1 LCPSWIIFCQJWCM-UHFFFAOYSA-N 0.000 claims 1
- IWSKBHGMWURQLU-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-(6-methylpyridin-3-yl)pyrimidin-2-amine Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC1=CC=C(C)N=C1 IWSKBHGMWURQLU-UHFFFAOYSA-N 0.000 claims 1
- VOLRWAYKHIYLOQ-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-(oxan-4-yl)pyrimidin-2-amine Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC1CCOCC1 VOLRWAYKHIYLOQ-UHFFFAOYSA-N 0.000 claims 1
- WVFLBDFRUFKPLC-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-[5-(trifluoromethyl)pyridin-2-yl]pyrimidin-2-amine Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC1=CC=C(C(F)(F)F)C=N1 WVFLBDFRUFKPLC-UHFFFAOYSA-N 0.000 claims 1
- VTCQOLUUQCFBAL-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-[6-(1,4-oxazepan-4-ylmethyl)pyridin-3-yl]pyrimidin-2-amine Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=N1)=CC=C1CN1CCCOCC1 VTCQOLUUQCFBAL-UHFFFAOYSA-N 0.000 claims 1
- WYLNTNIPADSGEA-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-[6-(morpholin-4-ylmethyl)pyridin-3-yl]pyrimidin-2-amine Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=N1)=CC=C1CN1CCOCC1 WYLNTNIPADSGEA-UHFFFAOYSA-N 0.000 claims 1
- MTXTYDOQPWFVAZ-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-[6-(piperidin-1-ylmethyl)pyridin-3-yl]pyrimidin-2-amine Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=N1)=CC=C1CN1CCCCC1 MTXTYDOQPWFVAZ-UHFFFAOYSA-N 0.000 claims 1
- YFUPCFQYUGQWAL-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-[6-(pyrrolidin-1-ylmethyl)pyridin-3-yl]pyrimidin-2-amine Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=N1)=CC=C1CN1CCCC1 YFUPCFQYUGQWAL-UHFFFAOYSA-N 0.000 claims 1
- NSHLSXQXOYJABX-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-[6-[(4-pyrimidin-2-ylpiperazin-1-yl)methyl]pyridin-3-yl]pyrimidin-2-amine Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=N1)=CC=C1CN(CC1)CCN1C1=NC=CC=N1 NSHLSXQXOYJABX-UHFFFAOYSA-N 0.000 claims 1
- RKJKINHCDDDGQP-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-[6-[(4-pyrrolidin-1-ylpiperidin-1-yl)methyl]pyridin-3-yl]pyrimidin-2-amine Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=N1)=CC=C1CN(CC1)CCC1N1CCCC1 RKJKINHCDDDGQP-UHFFFAOYSA-N 0.000 claims 1
- HQMBKNAPGSPRBU-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-pyridin-4-ylpyrimidin-2-amine Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC1=CC=NC=C1 HQMBKNAPGSPRBU-UHFFFAOYSA-N 0.000 claims 1
- SCUWIWDHUHCGJD-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-pyrimidin-5-ylpyrimidin-2-amine Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC1=CN=CN=C1 SCUWIWDHUHCGJD-UHFFFAOYSA-N 0.000 claims 1
- NXFHOIIAVLFCFI-UHFFFAOYSA-N 5-fluoro-n-(4-methoxypyridin-2-yl)-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine Chemical compound COC1=CC=NC(NC=2N=C(C(F)=CN=2)C=2N(C(C)=NC=2)C2CCOCC2)=C1 NXFHOIIAVLFCFI-UHFFFAOYSA-N 0.000 claims 1
- YDHCXAGOCMZILL-UHFFFAOYSA-N 5-fluoro-n-(6-methoxypyridin-2-yl)-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine Chemical compound COC1=CC=CC(NC=2N=C(C(F)=CN=2)C=2N(C(C)=NC=2)C2CCOCC2)=N1 YDHCXAGOCMZILL-UHFFFAOYSA-N 0.000 claims 1
- QICPUUKVRWQQPS-UHFFFAOYSA-N 5-fluoro-n-[6-[(4-methoxypiperidin-1-yl)methyl]pyridin-3-yl]-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine Chemical compound C1CC(OC)CCN1CC(N=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 QICPUUKVRWQQPS-UHFFFAOYSA-N 0.000 claims 1
- HIXSKACMNSCHGR-UHFFFAOYSA-N 5-fluoro-n-[6-[(4-methyl-1,4-diazepan-1-yl)methyl]pyridin-3-yl]-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine Chemical compound C1CN(C)CCCN1CC(N=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 HIXSKACMNSCHGR-UHFFFAOYSA-N 0.000 claims 1
- MCQIYEMLSAUITG-NRFANRHFSA-N 5-fluoro-n-[6-[[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]methyl]pyridin-3-yl]-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine Chemical compound COC[C@@H]1CCCN1CC(N=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 MCQIYEMLSAUITG-NRFANRHFSA-N 0.000 claims 1
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- VZNCNOZRGDJXLH-UHFFFAOYSA-N n-[6-[(2,6-dimethylmorpholin-4-yl)methyl]pyridin-3-yl]-5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine Chemical compound C1C(C)OC(C)CN1CC(N=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 VZNCNOZRGDJXLH-UHFFFAOYSA-N 0.000 claims 1
- ZQNGIEIMNHOKGW-UHFFFAOYSA-N n-[6-[(4,4-difluoropiperidin-1-yl)methyl]pyridin-3-yl]-5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=N1)=CC=C1CN1CCC(F)(F)CC1 ZQNGIEIMNHOKGW-UHFFFAOYSA-N 0.000 claims 1
- OCOYKVVJAMDHSK-UHFFFAOYSA-N n-[6-[[(6-chloropyridin-3-yl)methylamino]methyl]pyridin-3-yl]-5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=N1)=CC=C1CNCC1=CC=C(Cl)N=C1 OCOYKVVJAMDHSK-UHFFFAOYSA-N 0.000 claims 1
- ALVSKICBFQBLQE-UHFFFAOYSA-N n-[6-[[ethyl(2-methoxyethyl)amino]methyl]pyridin-3-yl]-5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine Chemical compound C1=NC(CN(CCOC)CC)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 ALVSKICBFQBLQE-UHFFFAOYSA-N 0.000 claims 1
- HKLCLECZZXBTND-UHFFFAOYSA-N n-cyclohexyl-5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC1CCCCC1 HKLCLECZZXBTND-UHFFFAOYSA-N 0.000 claims 1
- 230000011164 ossification Effects 0.000 claims 1
- 230000007170 pathology Effects 0.000 claims 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 1
- 208000022610 schizoaffective disease Diseases 0.000 claims 1
- 230000006641 stabilisation Effects 0.000 claims 1
- 238000011105 stabilization Methods 0.000 claims 1
- JAJMSUGMMRKEJS-UHFFFAOYSA-N tert-butyl 4-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]piperidine-1-carboxylate Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC1CCN(C(=O)OC(C)(C)C)CC1 JAJMSUGMMRKEJS-UHFFFAOYSA-N 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- CHDSPZPQDVZXJY-NCDLOWQHSA-N Cc1ncc(-c2c(C)cnc(N/C3=C/C=C\C=C/C=C\C=C/C=C3)n2)[n]1C Chemical compound Cc1ncc(-c2c(C)cnc(N/C3=C/C=C\C=C/C=C\C=C/C=C3)n2)[n]1C CHDSPZPQDVZXJY-NCDLOWQHSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Psychiatry (AREA)
- Diabetes (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hospice & Palliative Care (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81675506P | 2006-06-27 | 2006-06-27 | |
| US60/816,755 | 2006-06-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2008148903A true RU2008148903A (ru) | 2010-08-10 |
Family
ID=38846128
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2008148903/04A RU2008148903A (ru) | 2006-06-27 | 2007-06-26 | Производные имидазол-пиримидина для лечения заболеваний, ассоциированных с киназой гликогенсинтазы 3 (gsk3) |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US20080188503A1 (https=) |
| EP (1) | EP2046783A4 (https=) |
| JP (1) | JP2009542639A (https=) |
| KR (1) | KR20090024295A (https=) |
| CN (1) | CN101511824A (https=) |
| AR (1) | AR061653A1 (https=) |
| AU (1) | AU2007265732A1 (https=) |
| BR (1) | BRPI0713578A2 (https=) |
| CA (1) | CA2655444A1 (https=) |
| CL (1) | CL2007001882A1 (https=) |
| EC (1) | ECSP088974A (https=) |
| IL (1) | IL195665A0 (https=) |
| MX (1) | MX2008015721A (https=) |
| NO (1) | NO20090328L (https=) |
| RU (1) | RU2008148903A (https=) |
| TW (1) | TW200815417A (https=) |
| UY (1) | UY30438A1 (https=) |
| WO (1) | WO2008002245A2 (https=) |
| ZA (1) | ZA200810577B (https=) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2007036732A1 (en) | 2005-09-30 | 2007-04-05 | Astrazeneca Ab | Imidazo [1,2-a] pyridine having anti-cell-proliferation activity |
| TW200811169A (en) * | 2006-05-26 | 2008-03-01 | Astrazeneca Ab | Chemical compounds |
| TW200815418A (en) * | 2006-06-27 | 2008-04-01 | Astrazeneca Ab | New compounds I |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| JP2012524063A (ja) | 2009-04-15 | 2012-10-11 | アストラゼネカ・アクチエボラーグ | アルツハイマー病などのグリコーゲンシンターゼキナーゼ３関連障害の治療に有用なイミダゾール置換ピリミジン |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2011157827A1 (de) | 2010-06-18 | 2011-12-22 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| WO2012050517A1 (en) * | 2010-10-14 | 2012-04-19 | Astrazeneca Ab | Imidazole substituted pyrimidine having a high gsk3 inhibiting potency as well as pan-kinase selectivity |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP2760862B1 (en) | 2011-09-27 | 2015-10-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| JP2017524739A (ja) | 2014-07-17 | 2017-08-31 | アンセルムＩｎｓｅｒｍ | 神経筋接合部関連疾患の処置方法 |
| WO2016207366A1 (en) | 2015-06-26 | 2016-12-29 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and pharmaceutical compositions for the treatment of viral infections |
| GB201519573D0 (en) | 2015-11-05 | 2015-12-23 | King S College London | Combination |
| US11066404B2 (en) | 2018-10-11 | 2021-07-20 | Incyte Corporation | Dihydropyrido[2,3-d]pyrimidinone compounds as CDK2 inhibitors |
| WO2020168197A1 (en) | 2019-02-15 | 2020-08-20 | Incyte Corporation | Pyrrolo[2,3-d]pyrimidinone compounds as cdk2 inhibitors |
| WO2020180959A1 (en) | 2019-03-05 | 2020-09-10 | Incyte Corporation | Pyrazolyl pyrimidinylamine compounds as cdk2 inhibitors |
| WO2020205560A1 (en) | 2019-03-29 | 2020-10-08 | Incyte Corporation | Sulfonylamide compounds as cdk2 inhibitors |
| KR102206111B1 (ko) | 2019-04-01 | 2021-01-22 | 박광호 | 목욕탕용 담수 및 해수 가열시스템 |
| US11440914B2 (en) | 2019-05-01 | 2022-09-13 | Incyte Corporation | Tricyclic amine compounds as CDK2 inhibitors |
| WO2020223558A1 (en) | 2019-05-01 | 2020-11-05 | Incyte Corporation | Tricyclic amine compounds as cdk2 inhibitors |
| TW202115024A (zh) | 2019-08-14 | 2021-04-16 | 美商英塞特公司 | 作為cdk2 抑制劑之咪唑基嘧啶基胺化合物 |
| AU2020364007A1 (en) | 2019-10-11 | 2022-04-28 | Incyte Corporation | Bicyclic amines as CDK2 inhibitors |
| CA3207392A1 (en) * | 2021-02-05 | 2022-08-11 | Xiaoxia Yan | Cdk inhibitor |
| US11981671B2 (en) | 2021-06-21 | 2024-05-14 | Incyte Corporation | Bicyclic pyrazolyl amines as CDK2 inhibitors |
| WO2023107705A1 (en) | 2021-12-10 | 2023-06-15 | Incyte Corporation | Bicyclic amines as cdk12 inhibitors |
| US11976073B2 (en) | 2021-12-10 | 2024-05-07 | Incyte Corporation | Bicyclic amines as CDK2 inhibitors |
Family Cites Families (9)
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| GB0021726D0 (en) * | 2000-09-05 | 2000-10-18 | Astrazeneca Ab | Chemical compounds |
| CA2491895C (en) * | 2002-07-09 | 2011-01-18 | Vertex Pharmaceuticals Incorporated | Inhibitors of c-jun n-terminal kinases (jnk) and other protein kinases |
| JP2007500178A (ja) * | 2003-07-30 | 2007-01-11 | サイクラセル・リミテッド | プロテインキナーゼ阻害剤としてのピリジニルアミノ−ピリミジン誘導体 |
| CA2542880A1 (en) * | 2003-10-21 | 2005-05-12 | Cyclacel Limited | Pyrimidin-4-yl-3, 4-thione compounds and their use in therapy |
| GB0402653D0 (en) * | 2004-02-06 | 2004-03-10 | Cyclacel Ltd | Compounds |
| NZ555474A (en) * | 2004-12-17 | 2010-10-29 | Astrazeneca Ab | 4-(4-(imidazol-4-yl) pyrimidin-2-ylamino) benzamides as CDK inhibitors |
| GB0504753D0 (en) * | 2005-03-08 | 2005-04-13 | Astrazeneca Ab | Chemical compounds |
| UY29827A1 (es) * | 2005-10-03 | 2007-05-31 | Astrazeneca Ab | 2-amina-pirimidina-4-(2-metil-1-(tetrahidro-2h-piran-4-il)-1-imidazol-5-y1) sustituidas y sus derivados, composiciones farmacéuticas que las contienen, procesos para su preparación y aplicaciones |
| TW200815418A (en) * | 2006-06-27 | 2008-04-01 | Astrazeneca Ab | New compounds I |
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2007
- 2007-06-21 TW TW096122335A patent/TW200815417A/zh unknown
- 2007-06-26 RU RU2008148903/04A patent/RU2008148903A/ru not_active Application Discontinuation
- 2007-06-26 WO PCT/SE2007/000621 patent/WO2008002245A2/en not_active Ceased
- 2007-06-26 BR BRPI0713578-5A patent/BRPI0713578A2/pt not_active IP Right Cessation
- 2007-06-26 EP EP07748282A patent/EP2046783A4/en not_active Withdrawn
- 2007-06-26 CL CL200701882A patent/CL2007001882A1/es unknown
- 2007-06-26 MX MX2008015721A patent/MX2008015721A/es not_active Application Discontinuation
- 2007-06-26 CN CNA2007800320192A patent/CN101511824A/zh active Pending
- 2007-06-26 KR KR1020097001643A patent/KR20090024295A/ko not_active Withdrawn
- 2007-06-26 AR ARP070102832A patent/AR061653A1/es not_active Application Discontinuation
- 2007-06-26 AU AU2007265732A patent/AU2007265732A1/en not_active Abandoned
- 2007-06-26 CA CA002655444A patent/CA2655444A1/en not_active Abandoned
- 2007-06-26 JP JP2009518045A patent/JP2009542639A/ja active Pending
- 2007-06-26 UY UY30438A patent/UY30438A1/es unknown
- 2007-06-27 US US11/769,113 patent/US20080188503A1/en not_active Abandoned
-
2008
- 2008-12-02 IL IL195665A patent/IL195665A0/en unknown
- 2008-12-12 ZA ZA200810577A patent/ZA200810577B/xx unknown
- 2008-12-12 EC EC2008008974A patent/ECSP088974A/es unknown
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2009
- 2009-01-21 NO NO20090328A patent/NO20090328L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP2046783A4 (en) | 2010-08-04 |
| BRPI0713578A2 (pt) | 2012-10-23 |
| IL195665A0 (en) | 2009-09-01 |
| JP2009542639A (ja) | 2009-12-03 |
| ZA200810577B (en) | 2009-08-26 |
| MX2008015721A (es) | 2009-01-08 |
| EP2046783A2 (en) | 2009-04-15 |
| KR20090024295A (ko) | 2009-03-06 |
| CA2655444A1 (en) | 2008-01-03 |
| ECSP088974A (es) | 2009-01-30 |
| WO2008002245A8 (en) | 2008-10-09 |
| UY30438A1 (es) | 2008-01-31 |
| CN101511824A (zh) | 2009-08-19 |
| AR061653A1 (es) | 2008-09-10 |
| WO2008002245A3 (en) | 2008-02-14 |
| WO2008002245A2 (en) | 2008-01-03 |
| AU2007265732A1 (en) | 2008-01-03 |
| CL2007001882A1 (es) | 2008-02-08 |
| US20080188503A1 (en) | 2008-08-07 |
| NO20090328L (no) | 2009-01-26 |
| TW200815417A (en) | 2008-04-01 |
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| Date | Code | Title | Description |
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| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
Effective date: 20110913 |