JP2009542639A5 - - Google Patents
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- JP2009542639A5 JP2009542639A5 JP2009518045A JP2009518045A JP2009542639A5 JP 2009542639 A5 JP2009542639 A5 JP 2009542639A5 JP 2009518045 A JP2009518045 A JP 2009518045A JP 2009518045 A JP2009518045 A JP 2009518045A JP 2009542639 A5 JP2009542639 A5 JP 2009542639A5
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- JP
- Japan
- Prior art keywords
- alkyl
- methyl
- heterocycle
- fluoro
- pyran
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 125000000217 alkyl group Chemical group 0.000 claims 74
- 125000000623 heterocyclic group Chemical group 0.000 claims 46
- -1 nitro, cyano, hydroxy, amino, sulfamoyl Chemical group 0.000 claims 41
- 150000001875 compounds Chemical class 0.000 claims 30
- 125000005843 halogen group Chemical group 0.000 claims 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 18
- 229910052757 nitrogen Inorganic materials 0.000 claims 18
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 239000001257 hydrogen Substances 0.000 claims 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 14
- 229910052799 carbon Inorganic materials 0.000 claims 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 11
- 208000010877 cognitive disease Diseases 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 9
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 8
- 206010012289 Dementia Diseases 0.000 claims 8
- 201000011240 Frontotemporal dementia Diseases 0.000 claims 8
- 206010026749 Mania Diseases 0.000 claims 8
- 125000002837 carbocyclic group Chemical group 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 7
- 208000024827 Alzheimer disease Diseases 0.000 claims 6
- 208000020925 Bipolar disease Diseases 0.000 claims 6
- 208000028698 Cognitive impairment Diseases 0.000 claims 6
- 230000011164 ossification Effects 0.000 claims 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 6
- 125000001589 carboacyl group Chemical group 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 230000002265 prevention Effects 0.000 claims 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- 208000026072 Motor neurone disease Diseases 0.000 claims 4
- 208000018737 Parkinson disease Diseases 0.000 claims 4
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 4
- 230000007000 age related cognitive decline Effects 0.000 claims 4
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 4
- 208000027061 mild cognitive impairment Diseases 0.000 claims 4
- 230000036651 mood Effects 0.000 claims 4
- 208000005264 motor neuron disease Diseases 0.000 claims 4
- 201000002212 progressive supranuclear palsy Diseases 0.000 claims 4
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims 4
- 201000000980 schizophrenia Diseases 0.000 claims 4
- 230000009529 traumatic brain injury Effects 0.000 claims 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 3
- 125000000171 (C1-C6) haloalkyl 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
- 206010017076 Fracture Diseases 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 208000017194 Affective disease Diseases 0.000 claims 2
- 201000004384 Alopecia Diseases 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 2
- 208000010392 Bone Fractures Diseases 0.000 claims 2
- 208000011990 Corticobasal Degeneration Diseases 0.000 claims 2
- 208000020406 Creutzfeldt Jacob disease Diseases 0.000 claims 2
- 208000003407 Creutzfeldt-Jakob Syndrome Diseases 0.000 claims 2
- 208000010859 Creutzfeldt-Jakob disease Diseases 0.000 claims 2
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims 2
- 201000010374 Down Syndrome Diseases 0.000 claims 2
- 208000027534 Emotional disease Diseases 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 208000009829 Lewy Body Disease Diseases 0.000 claims 2
- 201000002832 Lewy body dementia Diseases 0.000 claims 2
- 208000019022 Mood disease Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 208000014060 Niemann-Pick disease Diseases 0.000 claims 2
- 206010034010 Parkinsonism Diseases 0.000 claims 2
- 208000000609 Pick Disease of the Brain Diseases 0.000 claims 2
- 208000024571 Pick disease Diseases 0.000 claims 2
- 208000024777 Prion disease Diseases 0.000 claims 2
- 206010044688 Trisomy 21 Diseases 0.000 claims 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 2
- 201000004810 Vascular dementia Diseases 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims 2
- 125000005189 alkyl hydroxy group Chemical group 0.000 claims 2
- 231100000360 alopecia Toxicity 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 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
- 210000000988 bone and bone Anatomy 0.000 claims 2
- 230000037182 bone density Effects 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 210000004720 cerebrum Anatomy 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 208000017004 dementia pugilistica Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 239000003814 drug Substances 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
- 230000035876 healing Effects 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
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 230000003902 lesion Effects 0.000 claims 2
- 238000012423 maintenance Methods 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 206010027175 memory impairment Diseases 0.000 claims 2
- 238000000034 method Methods 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
- 210000002682 neurofibrillary tangle Anatomy 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 230000001737 promoting effect Effects 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 230000000698 schizophrenic effect Effects 0.000 claims 2
- 230000006641 stabilisation Effects 0.000 claims 2
- 238000011105 stabilization Methods 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 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 class 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
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- MHEBDXHZPBEPLO-UHFFFAOYSA-N 3-[[5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]methyl-(oxolan-2-ylmethyl)amino]propanenitrile Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=N1)=CC=C1CN(CCC#N)CC1CCCO1 MHEBDXHZPBEPLO-UHFFFAOYSA-N 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 class C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC1=CC=C(C)N=C1 IWSKBHGMWURQLU-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 class 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 class 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
- QHSBRUYXWQWEKE-UHFFFAOYSA-N [1-[[5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]methyl]piperidin-3-yl]methanol Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=N1)=CC=C1CN1CCCC(CO)C1 QHSBRUYXWQWEKE-UHFFFAOYSA-N 0.000 claims 1
- ZGFJPECICPWLOK-UHFFFAOYSA-N [4-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]piperidin-1-yl]-phenylmethanone Chemical class C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(CC1)CCN1C(=O)C1=CC=CC=C1 ZGFJPECICPWLOK-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- OCWQUBAHRGYPMX-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine Chemical class C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(CC1)CCN1CC1=CC=CC=C1 OCWQUBAHRGYPMX-UHFFFAOYSA-N 0.000 claims 1
- FASXTYBIMSSRNM-UHFFFAOYSA-N n-(1-benzylsulfonylpiperidin-4-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(CC1)CCN1S(=O)(=O)CC1=CC=CC=C1 FASXTYBIMSSRNM-UHFFFAOYSA-N 0.000 claims 1
- CZPPZXPERUBYEI-UHFFFAOYSA-N n-[1-(benzenesulfonyl)piperidin-4-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(CC1)CCN1S(=O)(=O)C1=CC=CC=C1 CZPPZXPERUBYEI-UHFFFAOYSA-N 0.000 claims 1
- BNDHBGXAAXHECU-UHFFFAOYSA-N n-[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]isoquinolin-4-amine Chemical compound CC1=NC=C(C=2C(=CN=C(NC=3C4=CC=CC=C4C=NC=3)N=2)F)N1C1CCOCC1 BNDHBGXAAXHECU-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
- 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
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 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
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81675506P | 2006-06-27 | 2006-06-27 | |
| PCT/SE2007/000621 WO2008002245A2 (en) | 2006-06-27 | 2007-06-26 | Imidazol-pyrimidine derivatives for treatment of diseases related to glycogen synthase kinase (gsk3) |
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| US7745428B2 (en) | 2005-09-30 | 2010-06-29 | 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 |
| RU2011140238A (ru) * | 2009-04-15 | 2013-05-20 | Астразенека Аб | Имидазол-замещенные пиримидины, полезные в лечении заболеваний, ассоциированных с киназой-3 гликогенсинтазы, таких как болезнь альцгеймера |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8933024B2 (en) | 2010-06-18 | 2015-01-13 | Sanofi | Azolopyridin-3-one derivatives as inhibitors of lipases and phospholipases |
| 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 |
| 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 |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process 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 |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2016008966A1 (en) | 2014-07-17 | 2016-01-21 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for treating neuromuscular junction-related diseases |
| 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 |
| TW202100520A (zh) | 2019-03-05 | 2021-01-01 | 美商英塞特公司 | 作為cdk2 抑制劑之吡唑基嘧啶基胺化合物 |
| 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 |
| WO2020223558A1 (en) | 2019-05-01 | 2020-11-05 | Incyte Corporation | Tricyclic amine compounds as cdk2 inhibitors |
| US11440914B2 (en) | 2019-05-01 | 2022-09-13 | 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 |
| CN119930610A (zh) | 2019-10-11 | 2025-05-06 | 因赛特公司 | 作为cdk2抑制剂的双环胺 |
| EP4289835A4 (en) * | 2021-02-05 | 2024-08-28 | Shanghai Qilu Pharmaceutical Research and Development Centre Ltd. | CDK INHIBITORS |
| US11981671B2 (en) | 2021-06-21 | 2024-05-14 | Incyte Corporation | Bicyclic pyrazolyl amines as CDK2 inhibitors |
| US11976073B2 (en) | 2021-12-10 | 2024-05-07 | Incyte Corporation | Bicyclic amines as CDK2 inhibitors |
| WO2023107705A1 (en) | 2021-12-10 | 2023-06-15 | Incyte Corporation | Bicyclic amines as cdk12 inhibitors |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB0021726D0 (en) * | 2000-09-05 | 2000-10-18 | Astrazeneca Ab | Chemical compounds |
| JP4570955B2 (ja) * | 2002-07-09 | 2010-10-27 | バーテクス ファーマスーティカルズ インコーポレイテッド | プロテインキナーゼ阻害活性を持つイミダゾール類 |
| 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 |
| JP5164380B2 (ja) * | 2003-10-21 | 2013-03-21 | サイクラセル リミテッド | ピリミジン−４−イル−３，４−チオン化合物及び治療におけるその使用 |
| GB0402653D0 (en) * | 2004-02-06 | 2004-03-10 | Cyclacel Ltd | Compounds |
| AU2005315392B2 (en) * | 2004-12-17 | 2010-03-11 | 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 |
| AR058073A1 (es) * | 2005-10-03 | 2008-01-23 | Astrazeneca Ab | Derivados de imidazol 5-il-pirimidina, procesos de obtencion, composiciones farmaceuticas y usos |
| 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 WO PCT/SE2007/000621 patent/WO2008002245A2/en not_active Ceased
- 2007-06-26 CA CA002655444A patent/CA2655444A1/en not_active Abandoned
- 2007-06-26 CL CL200701882A patent/CL2007001882A1/es unknown
- 2007-06-26 BR BRPI0713578-5A patent/BRPI0713578A2/pt not_active IP Right Cessation
- 2007-06-26 UY UY30438A patent/UY30438A1/es unknown
- 2007-06-26 AR ARP070102832A patent/AR061653A1/es not_active Application Discontinuation
- 2007-06-26 CN CNA2007800320192A patent/CN101511824A/zh active Pending
- 2007-06-26 EP EP07748282A patent/EP2046783A4/en not_active Withdrawn
- 2007-06-26 JP JP2009518045A patent/JP2009542639A/ja active Pending
- 2007-06-26 AU AU2007265732A patent/AU2007265732A1/en not_active Abandoned
- 2007-06-26 MX MX2008015721A patent/MX2008015721A/es not_active Application Discontinuation
- 2007-06-26 KR KR1020097001643A patent/KR20090024295A/ko not_active Withdrawn
- 2007-06-26 RU RU2008148903/04A patent/RU2008148903A/ru not_active Application Discontinuation
- 2007-06-27 US US11/769,113 patent/US20080188503A1/en not_active Abandoned
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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
-
2009
- 2009-01-21 NO NO20090328A patent/NO20090328L/no not_active Application Discontinuation
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