CA2655444A1 - New compounds 385 - Google Patents
New compounds 385 Download PDFInfo
- Publication number
- CA2655444A1 CA2655444A1 CA002655444A CA2655444A CA2655444A1 CA 2655444 A1 CA2655444 A1 CA 2655444A1 CA 002655444 A CA002655444 A CA 002655444A CA 2655444 A CA2655444 A CA 2655444A CA 2655444 A1 CA2655444 A1 CA 2655444A1
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- 6alkyl
- optionally substituted
- heterocyclyl
- 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.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 212
- 238000000034 method Methods 0.000 claims abstract description 48
- 150000003839 salts Chemical class 0.000 claims abstract description 29
- 230000008569 process Effects 0.000 claims abstract description 11
- 239000012458 free base Substances 0.000 claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 4
- -1 nitro, cyano, hydroxy, amino, sulphamoyl Chemical group 0.000 claims description 186
- 125000000623 heterocyclic group Chemical group 0.000 claims description 126
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 76
- 125000005843 halogen group Chemical group 0.000 claims description 72
- 102000001267 GSK3 Human genes 0.000 claims description 57
- 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 claims description 57
- 238000011282 treatment Methods 0.000 claims description 57
- 239000001257 hydrogen Substances 0.000 claims description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 46
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 43
- 229910052799 carbon Inorganic materials 0.000 claims description 42
- 229910052757 nitrogen Inorganic materials 0.000 claims description 39
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 38
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 38
- 230000002265 prevention Effects 0.000 claims description 38
- 241000124008 Mammalia Species 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 29
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 29
- 208000024827 Alzheimer disease Diseases 0.000 claims description 26
- 150000002431 hydrogen Chemical group 0.000 claims description 24
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 23
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 22
- 210000000988 bone and bone Anatomy 0.000 claims description 21
- 206010012289 Dementia Diseases 0.000 claims description 20
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 20
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- 230000011164 ossification Effects 0.000 claims description 17
- 230000001965 increasing effect Effects 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 208000010392 Bone Fractures Diseases 0.000 claims description 14
- 206010017076 Fracture Diseases 0.000 claims description 14
- 208000001132 Osteoporosis Diseases 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 125000006239 protecting group Chemical group 0.000 claims description 14
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 13
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 13
- 201000011240 Frontotemporal dementia Diseases 0.000 claims description 13
- 208000010877 cognitive disease Diseases 0.000 claims description 13
- 201000000980 schizophrenia Diseases 0.000 claims description 13
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 12
- 208000020925 Bipolar disease Diseases 0.000 claims description 11
- 125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 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 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 208000019022 Mood disease Diseases 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 9
- 208000035475 disorder Diseases 0.000 claims description 9
- 238000001727 in vivo Methods 0.000 claims description 9
- 208000024714 major depressive disease Diseases 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- BDSBULQPKFMZDX-UHFFFAOYSA-N 2-bromo-5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidine Chemical compound C1COCCC1N1C(C)=NC=C1C1=NC(Br)=NC=C1F BDSBULQPKFMZDX-UHFFFAOYSA-N 0.000 claims description 8
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 7
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
- 206010028980 Neoplasm Diseases 0.000 claims description 7
- 208000018737 Parkinson disease Diseases 0.000 claims description 7
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 7
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 7
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 7
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 7
- 201000002212 progressive supranuclear palsy Diseases 0.000 claims description 7
- 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 description 7
- 230000009529 traumatic brain injury Effects 0.000 claims description 7
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 6
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 6
- 230000007000 age related cognitive decline Effects 0.000 claims description 6
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 6
- 230000007278 cognition impairment Effects 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 230000035876 healing Effects 0.000 claims description 6
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 6
- 208000027061 mild cognitive impairment Diseases 0.000 claims description 6
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 6
- 201000004384 Alopecia Diseases 0.000 claims description 5
- 208000011990 Corticobasal Degeneration Diseases 0.000 claims description 5
- 208000027089 Parkinsonian disease Diseases 0.000 claims description 5
- 206010034010 Parkinsonism Diseases 0.000 claims description 5
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 208000027866 inflammatory disease Diseases 0.000 claims description 5
- 208000005264 motor neuron disease Diseases 0.000 claims description 5
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 5
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 4
- 201000010374 Down Syndrome Diseases 0.000 claims description 4
- 208000023105 Huntington disease Diseases 0.000 claims description 4
- 206010026749 Mania Diseases 0.000 claims description 4
- 208000014060 Niemann-Pick disease Diseases 0.000 claims description 4
- 208000000609 Pick Disease of the Brain Diseases 0.000 claims description 4
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 231100000360 alopecia Toxicity 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- 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 description 4
- 208000017004 dementia pugilistica Diseases 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 230000036651 mood Effects 0.000 claims description 4
- 230000007170 pathology Effects 0.000 claims description 4
- 230000006641 stabilisation Effects 0.000 claims description 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 4
- SKAQUBBZLUGQFR-UHFFFAOYSA-N 5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridine-2-carbaldehyde Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC1=CC=C(C=O)N=C1 SKAQUBBZLUGQFR-UHFFFAOYSA-N 0.000 claims description 3
- 206010067889 Dementia with Lewy bodies Diseases 0.000 claims description 3
- 206010061818 Disease progression Diseases 0.000 claims description 3
- 201000002832 Lewy body dementia Diseases 0.000 claims description 3
- 208000024777 Prion disease Diseases 0.000 claims description 3
- 208000028017 Psychotic disease Diseases 0.000 claims description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- 206010044688 Trisomy 21 Diseases 0.000 claims description 3
- 201000004810 Vascular dementia Diseases 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 208000028683 bipolar I disease Diseases 0.000 claims description 3
- 208000025307 bipolar depression Diseases 0.000 claims description 3
- 230000001149 cognitive effect Effects 0.000 claims description 3
- 230000005750 disease progression Effects 0.000 claims description 3
- 208000024732 dysthymic disease Diseases 0.000 claims description 3
- 230000002708 enhancing effect Effects 0.000 claims description 3
- 238000012423 maintenance Methods 0.000 claims description 3
- 206010027175 memory impairment Diseases 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 238000011105 stabilization Methods 0.000 claims description 3
- 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 description 2
- 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 description 2
- 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 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 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 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- RJDAGIUPPBVRNW-UHFFFAOYSA-N benzyl 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=1NC(CC1)CCN1C(=O)OCC1=CC=CC=C1 RJDAGIUPPBVRNW-UHFFFAOYSA-N 0.000 claims description 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- 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
- 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
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical class [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 1
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- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
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- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 229960004431 quetiapine Drugs 0.000 description 1
- URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
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- 229910052705 radium Inorganic materials 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000007634 remodeling Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 230000000698 schizophrenic effect Effects 0.000 description 1
- 210000001732 sebaceous gland Anatomy 0.000 description 1
- 230000007781 signaling event Effects 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940083542 sodium Drugs 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
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- 239000008223 sterile water Substances 0.000 description 1
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- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
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- 230000004654 survival pathway Effects 0.000 description 1
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- 230000009885 systemic effect Effects 0.000 description 1
- 229940037128 systemic glucocorticoids Drugs 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
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- LZRDHSFPLUWYAX-UHFFFAOYSA-N tert-butyl 4-aminopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(N)CC1 LZRDHSFPLUWYAX-UHFFFAOYSA-N 0.000 description 1
- 239000012414 tert-butyl nitrite Substances 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 150000003527 tetrahydropyrans Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
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- 210000001519 tissue Anatomy 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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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
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- 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
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- 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
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- 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
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- A—HUMAN NECESSITIES
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- 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
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- A61P25/00—Drugs for disorders of the nervous system
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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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
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- A—HUMAN NECESSITIES
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- 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
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- 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
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- A—HUMAN NECESSITIES
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- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
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- 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81675506P | 2006-06-27 | 2006-06-27 | |
| US60/816,755 | 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) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2655444A1 true CA2655444A1 (en) | 2008-01-03 |
Family
ID=38846128
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002655444A Abandoned CA2655444A1 (en) | 2006-06-27 | 2007-06-26 | New compounds 385 |
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=) |
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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 |
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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
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- 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
-
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 |
| 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 |
| RU2008148903A (ru) | 2010-08-10 |
| NO20090328L (no) | 2009-01-26 |
| TW200815417A (en) | 2008-04-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued | ||
| FZDE | Discontinued |
Effective date: 20120626 |