HRP20171835T1 - Inhibitorni spojevi - Google Patents
Inhibitorni spojevi Download PDFInfo
- Publication number
- HRP20171835T1 HRP20171835T1 HRP20171835TT HRP20171835T HRP20171835T1 HR P20171835 T1 HRP20171835 T1 HR P20171835T1 HR P20171835T T HRP20171835T T HR P20171835TT HR P20171835 T HRP20171835 T HR P20171835T HR P20171835 T1 HRP20171835 T1 HR P20171835T1
- Authority
- HR
- Croatia
- Prior art keywords
- methyl
- methoxy
- pyrazol
- phenyl
- pyrido
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims 27
- 239000003112 inhibitor Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims 123
- 125000000753 cycloalkyl group Chemical group 0.000 claims 38
- 125000000623 heterocyclic group Chemical group 0.000 claims 30
- 229910052739 hydrogen Inorganic materials 0.000 claims 28
- 239000001257 hydrogen Substances 0.000 claims 28
- 125000003545 alkoxy group Chemical group 0.000 claims 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 22
- 125000001072 heteroaryl group Chemical group 0.000 claims 17
- 125000001424 substituent group Chemical group 0.000 claims 17
- 125000001309 chloro group Chemical group Cl* 0.000 claims 15
- 125000001153 fluoro group Chemical group F* 0.000 claims 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 14
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 12
- -1 trifluoromethoxy, cyano, nitro, hydroxy, amino, carboxy, carbamoyl Chemical group 0.000 claims 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims 10
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 7
- 239000012453 solvate Substances 0.000 claims 7
- 125000005647 linker group Chemical group 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 229910003827 NRaRb Inorganic materials 0.000 claims 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 3
- 125000001589 carboacyl group Chemical group 0.000 claims 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 239000001301 oxygen Chemical group 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- CDOLQNUQAVYWSO-UHFFFAOYSA-N (3-methoxyazetidin-1-yl)-[3-methoxy-4-[(5-pyridin-3-ylisoquinolin-3-yl)amino]phenyl]methanone Chemical compound C1C(OC)CN1C(=O)C(C=C1OC)=CC=C1NC1=CC2=C(C=3C=NC=CC=3)C=CC=C2C=N1 CDOLQNUQAVYWSO-UHFFFAOYSA-N 0.000 claims 1
- AXUBLMKYJQFBSV-UHFFFAOYSA-N (3-methoxyazetidin-1-yl)-[3-methoxy-4-[(5-pyrimidin-5-ylisoquinolin-3-yl)amino]phenyl]methanone Chemical compound C1C(OC)CN1C(=O)C(C=C1OC)=CC=C1NC1=CC2=C(C=3C=NC=NC=3)C=CC=C2C=N1 AXUBLMKYJQFBSV-UHFFFAOYSA-N 0.000 claims 1
- MDGZHKQHZCXJPC-UHFFFAOYSA-N (3-methoxyazetidin-1-yl)-[3-methoxy-4-[[5-(1-methylpyrazol-3-yl)isoquinolin-3-yl]amino]phenyl]methanone Chemical compound C1C(OC)CN1C(=O)C(C=C1OC)=CC=C1NC1=CC2=C(C3=NN(C)C=C3)C=CC=C2C=N1 MDGZHKQHZCXJPC-UHFFFAOYSA-N 0.000 claims 1
- MWMDRWOZUKCWOR-UHFFFAOYSA-N (3-methoxyazetidin-1-yl)-[3-methoxy-4-[[5-(1-methylpyrazol-4-yl)isoquinolin-3-yl]amino]phenyl]methanone Chemical compound C1C(OC)CN1C(=O)C(C=C1OC)=CC=C1NC1=CC2=C(C3=CN(C)N=C3)C=CC=C2C=N1 MWMDRWOZUKCWOR-UHFFFAOYSA-N 0.000 claims 1
- KNSSMLHMVQKSBT-UHFFFAOYSA-N (3-methoxyazetidin-1-yl)-[3-methoxy-4-[[5-(1-piperidin-4-ylpyrazol-4-yl)isoquinolin-3-yl]amino]phenyl]methanone Chemical compound C1C(OC)CN1C(=O)C(C=C1OC)=CC=C1NC1=CC2=C(C3=CN(N=C3)C3CCNCC3)C=CC=C2C=N1 KNSSMLHMVQKSBT-UHFFFAOYSA-N 0.000 claims 1
- CVCXKRQKUXTNCP-UHFFFAOYSA-N (3-methoxyazetidin-1-yl)-[3-methoxy-4-[[5-(1-propan-2-ylpyrazol-4-yl)isoquinolin-3-yl]amino]phenyl]methanone Chemical compound C1C(OC)CN1C(=O)C(C=C1OC)=CC=C1NC1=CC2=C(C3=CN(N=C3)C(C)C)C=CC=C2C=N1 CVCXKRQKUXTNCP-UHFFFAOYSA-N 0.000 claims 1
- XFDJSKUKGCTUDF-UHFFFAOYSA-N (3-methoxyazetidin-1-yl)-[3-methoxy-4-[[5-(2-methylpyrazol-3-yl)isoquinolin-3-yl]amino]phenyl]methanone Chemical compound C1C(OC)CN1C(=O)C(C=C1OC)=CC=C1NC1=CC2=C(C=3N(N=CC=3)C)C=CC=C2C=N1 XFDJSKUKGCTUDF-UHFFFAOYSA-N 0.000 claims 1
- LJSHPLPKDCEPTG-UHFFFAOYSA-N (3-methoxyazetidin-1-yl)-[3-methoxy-4-[[5-(3-methylimidazol-4-yl)isoquinolin-3-yl]amino]phenyl]methanone Chemical compound C1C(OC)CN1C(=O)C(C=C1OC)=CC=C1NC1=CC2=C(C=3N(C=NC=3)C)C=CC=C2C=N1 LJSHPLPKDCEPTG-UHFFFAOYSA-N 0.000 claims 1
- YHXOZAUTEWFRER-UHFFFAOYSA-N (3-methoxyazetidin-1-yl)-[3-methoxy-4-[[5-[1-(1-methylpiperidin-4-yl)pyrazol-4-yl]isoquinolin-3-yl]amino]phenyl]methanone Chemical compound C1C(OC)CN1C(=O)C(C=C1OC)=CC=C1NC1=CC2=C(C3=CN(N=C3)C3CCN(C)CC3)C=CC=C2C=N1 YHXOZAUTEWFRER-UHFFFAOYSA-N 0.000 claims 1
- OOWQQNLKTLHXPR-UHFFFAOYSA-N (3-methoxyazetidin-1-yl)-[3-methoxy-4-[[5-[1-(2-methoxyethyl)pyrazol-4-yl]isoquinolin-3-yl]amino]phenyl]methanone Chemical compound C1=NN(CCOC)C=C1C(C1=C2)=CC=CC1=CN=C2NC1=CC=C(C(=O)N2CC(C2)OC)C=C1OC OOWQQNLKTLHXPR-UHFFFAOYSA-N 0.000 claims 1
- JNOICPXAHVQUIV-UHFFFAOYSA-N (3-methoxyazetidin-1-yl)-[3-methoxy-4-[[8-(1-methylpyrazol-4-yl)pyrido[3,4-d]pyrimidin-2-yl]amino]phenyl]methanone Chemical compound C1C(OC)CN1C(=O)C(C=C1OC)=CC=C1NC1=NC=C(C=CN=C2C3=CN(C)N=C3)C2=N1 JNOICPXAHVQUIV-UHFFFAOYSA-N 0.000 claims 1
- DYMJWMGOGCSIJA-UHFFFAOYSA-N (3-methoxyazetidin-1-yl)-[3-methoxy-4-[[8-[(2-methoxy-2-methylpropyl)amino]pyrido[3,4-d]pyrimidin-2-yl]amino]phenyl]methanone Chemical compound C1C(OC)CN1C(=O)C(C=C1OC)=CC=C1NC1=NC=C(C=CN=C2NCC(C)(C)OC)C2=N1 DYMJWMGOGCSIJA-UHFFFAOYSA-N 0.000 claims 1
- LYHLZMPYIRFEBP-UHFFFAOYSA-N 1-[2-[2-methoxy-4-(1-methylpyrazol-4-yl)anilino]pyrido[3,4-d]pyrimidin-8-yl]azetidine-3-carbonitrile Chemical compound COC1=CC(C2=CN(C)N=C2)=CC=C1NC(N=C12)=NC=C1C=CN=C2N1CC(C#N)C1 LYHLZMPYIRFEBP-UHFFFAOYSA-N 0.000 claims 1
- KUNMZXUUNAOQPD-UHFFFAOYSA-N 1-[2-[2-methoxy-4-(1-methylpyrazol-4-yl)anilino]pyrido[3,4-d]pyrimidin-8-yl]piperidine-4-carbonitrile Chemical compound COC1=CC(C2=CN(C)N=C2)=CC=C1NC(N=C12)=NC=C1C=CN=C2N1CCC(C#N)CC1 KUNMZXUUNAOQPD-UHFFFAOYSA-N 0.000 claims 1
- ZEXFDYKYEXLWHS-UHFFFAOYSA-N 1-[2-[2-methoxy-4-(1-methylpyrazol-4-yl)anilino]pyrido[3,4-d]pyrimidin-8-yl]pyrrolidin-3-ol Chemical compound COC1=CC(C2=CN(C)N=C2)=CC=C1NC(N=C12)=NC=C1C=CN=C2N1CCC(O)C1 ZEXFDYKYEXLWHS-UHFFFAOYSA-N 0.000 claims 1
- NKLGUNXXPRNDHH-UHFFFAOYSA-N 1-[[2-[2-methoxy-4-(1-methylpyrazol-4-yl)anilino]pyrido[3,4-d]pyrimidin-8-yl]amino]-2-methylpropan-2-ol Chemical compound C=1C=C(NC=2N=C3C(NCC(C)(C)O)=NC=CC3=CN=2)C(OC)=CC=1C=1C=NN(C)C=1 NKLGUNXXPRNDHH-UHFFFAOYSA-N 0.000 claims 1
- CYTRCVJXFAZABO-UHFFFAOYSA-N 1-[[2-[2-methoxy-4-(1-methylpyrazol-4-yl)anilino]pyrido[3,4-d]pyrimidin-8-yl]amino]propan-2-ol Chemical compound C=1C=C(NC=2N=C3C(NCC(C)O)=NC=CC3=CN=2)C(OC)=CC=1C=1C=NN(C)C=1 CYTRCVJXFAZABO-UHFFFAOYSA-N 0.000 claims 1
- LPXUSZMCRKUWSV-UHFFFAOYSA-N 1-[[[2-[2-methoxy-4-(1-methylpyrazol-4-yl)anilino]pyrido[3,4-d]pyrimidin-8-yl]amino]methyl]cyclobutan-1-ol Chemical compound COC1=CC(C2=CN(C)N=C2)=CC=C1NC(N=C12)=NC=C1C=CN=C2NCC1(O)CCC1 LPXUSZMCRKUWSV-UHFFFAOYSA-N 0.000 claims 1
- UOHDUGCCXMWYEE-UHFFFAOYSA-N 1-[[[2-[2-methoxy-4-(1-methylpyrazol-4-yl)anilino]pyrido[3,4-d]pyrimidin-8-yl]amino]methyl]cyclopropan-1-ol Chemical compound COC1=CC(C2=CN(C)N=C2)=CC=C1NC(N=C12)=NC=C1C=CN=C2NCC1(O)CC1 UOHDUGCCXMWYEE-UHFFFAOYSA-N 0.000 claims 1
- ORHOFZZOEONKQY-UHFFFAOYSA-N 1-n-(cyclopropylmethyl)-7-n-[2-methoxy-4-(1-methylpyrazol-4-yl)phenyl]-2,6-naphthyridine-1,7-diamine Chemical compound COC1=CC(C2=CN(C)N=C2)=CC=C1NC(N=CC1=CC=N2)=CC1=C2NCC1CC1 ORHOFZZOEONKQY-UHFFFAOYSA-N 0.000 claims 1
- PVABBEUUWZYSPV-UHFFFAOYSA-N 1-n-cyclohexyl-7-n-[2-methoxy-4-(1-methylpyrazol-4-yl)phenyl]-2,6-naphthyridine-1,7-diamine Chemical compound COC1=CC(C2=CN(C)N=C2)=CC=C1NC(N=CC1=CC=N2)=CC1=C2NC1CCCCC1 PVABBEUUWZYSPV-UHFFFAOYSA-N 0.000 claims 1
- WXBAASKSGKSOSZ-UHFFFAOYSA-N 2-[4-[3-methoxy-4-[[8-(oxan-4-ylamino)pyrido[3,4-d]pyrimidin-2-yl]amino]phenyl]pyrazol-1-yl]ethanol Chemical compound COC1=CC(C2=CN(CCO)N=C2)=CC=C1NC(N=C12)=NC=C1C=CN=C2NC1CCOCC1 WXBAASKSGKSOSZ-UHFFFAOYSA-N 0.000 claims 1
- WLDAXEWGKOPNLQ-UHFFFAOYSA-N 2-[4-[4-[[8-(cyclohexylamino)pyrido[3,4-d]pyrimidin-2-yl]amino]-3-methoxyphenyl]pyrazol-1-yl]ethanol Chemical compound COC1=CC(C2=CN(CCO)N=C2)=CC=C1NC(N=C12)=NC=C1C=CN=C2NC1CCCCC1 WLDAXEWGKOPNLQ-UHFFFAOYSA-N 0.000 claims 1
- MPEMZDUAUZJMOJ-UHFFFAOYSA-N 2-[[2-[2-methoxy-4-(1-methylpyrazol-4-yl)anilino]pyrido[3,4-d]pyrimidin-8-yl]amino]-2-methylpropan-1-ol Chemical compound C=1C=C(NC=2N=C3C(NC(C)(C)CO)=NC=CC3=CN=2)C(OC)=CC=1C=1C=NN(C)C=1 MPEMZDUAUZJMOJ-UHFFFAOYSA-N 0.000 claims 1
- YDMASSGDTTWIMX-UHFFFAOYSA-N 2-[[2-[2-methoxy-4-(1-methylpyrazol-4-yl)anilino]pyrido[3,4-d]pyrimidin-8-yl]amino]ethanol Chemical compound C=1C=C(NC=2N=C3C(NCCO)=NC=CC3=CN=2)C(OC)=CC=1C=1C=NN(C)C=1 YDMASSGDTTWIMX-UHFFFAOYSA-N 0.000 claims 1
- JKJBMSVBYHQRIO-UHFFFAOYSA-N 2-[[2-[2-methoxy-4-(1-methylpyrazol-4-yl)anilino]pyrido[3,4-d]pyrimidin-8-yl]amino]propan-1-ol Chemical compound C=1C=C(NC=2N=C3C(NC(C)CO)=NC=CC3=CN=2)C(OC)=CC=1C=1C=NN(C)C=1 JKJBMSVBYHQRIO-UHFFFAOYSA-N 0.000 claims 1
- VMNKAAXTWKTQBZ-UHFFFAOYSA-N 2-[[2-[2-methoxy-4-(1-methylpyrazol-4-yl)anilino]pyrido[3,4-d]pyrimidin-8-yl]amino]propane-1,3-diol Chemical compound C=1C=C(NC=2N=C3C(NC(CO)CO)=NC=CC3=CN=2)C(OC)=CC=1C=1C=NN(C)C=1 VMNKAAXTWKTQBZ-UHFFFAOYSA-N 0.000 claims 1
- YMIRQILCEJQAAK-UHFFFAOYSA-N 2-n-(2-chloro-4-morpholin-4-ylphenyl)-8-n-(2,2-dimethylpropyl)pyrido[3,4-d]pyrimidine-2,8-diamine Chemical compound N1=C2C(NCC(C)(C)C)=NC=CC2=CN=C1NC(C(=C1)Cl)=CC=C1N1CCOCC1 YMIRQILCEJQAAK-UHFFFAOYSA-N 0.000 claims 1
- XVWBYYWZQXVZLG-UHFFFAOYSA-N 2-n-[2-(difluoromethoxy)-4-(1-methylpyrazol-4-yl)phenyl]-8-n-(2-methoxy-2-methylpropyl)-6-methylpyrido[3,4-d]pyrimidine-2,8-diamine Chemical compound N1=C2C(NCC(C)(C)OC)=NC(C)=CC2=CN=C1NC(C(=C1)OC(F)F)=CC=C1C=1C=NN(C)C=1 XVWBYYWZQXVZLG-UHFFFAOYSA-N 0.000 claims 1
- MBMGZVRAAURXAC-UHFFFAOYSA-N 2-n-[2-(difluoromethoxy)-4-(1-methylpyrazol-4-yl)phenyl]-8-n-(2-methoxy-2-methylpropyl)pyrido[3,4-d]pyrimidine-2,8-diamine Chemical compound N1=C2C(NCC(C)(C)OC)=NC=CC2=CN=C1NC(C(=C1)OC(F)F)=CC=C1C=1C=NN(C)C=1 MBMGZVRAAURXAC-UHFFFAOYSA-N 0.000 claims 1
- XVMCFRTZSZRUTA-UHFFFAOYSA-N 2-n-[2-(difluoromethoxy)-4-fluorophenyl]-8-n-(2-methoxy-2-methylpropyl)pyrido[3,4-d]pyrimidine-2,8-diamine Chemical compound N1=C2C(NCC(C)(C)OC)=NC=CC2=CN=C1NC1=CC=C(F)C=C1OC(F)F XVMCFRTZSZRUTA-UHFFFAOYSA-N 0.000 claims 1
- XEQUNIUZQRDLMG-UHFFFAOYSA-N 2-n-[2-ethoxy-4-(1-methylpyrazol-4-yl)phenyl]-8-n-(oxan-4-yl)pyrido[3,4-d]pyrimidine-2,8-diamine Chemical compound CCOC1=CC(C2=CN(C)N=C2)=CC=C1NC(N=C12)=NC=C1C=CN=C2NC1CCOCC1 XEQUNIUZQRDLMG-UHFFFAOYSA-N 0.000 claims 1
- QUIQOCPVVLSGIC-UHFFFAOYSA-N 2-n-[2-ethoxy-4-(4-methyl-1,2,4-triazol-3-yl)phenyl]-8-n-(2-methoxy-2-methylpropyl)pyrido[3,4-d]pyrimidine-2,8-diamine Chemical compound C=1C=C(NC=2N=C3C(NCC(C)(C)OC)=NC=CC3=CN=2)C(OCC)=CC=1C1=NN=CN1C QUIQOCPVVLSGIC-UHFFFAOYSA-N 0.000 claims 1
- RXLSCAACZFVGJF-UHFFFAOYSA-N 2-n-[2-ethoxy-4-(4-methyl-1,2,4-triazol-3-yl)phenyl]-8-n-[(3-methyloxolan-3-yl)methyl]pyrido[3,4-d]pyrimidine-2,8-diamine Chemical compound CCOC1=CC(C=2N(C=NN=2)C)=CC=C1NC(N=C12)=NC=C1C=CN=C2NCC1(C)CCOC1 RXLSCAACZFVGJF-UHFFFAOYSA-N 0.000 claims 1
- GONPDSQILJJULJ-UHFFFAOYSA-N 2-n-[2-methoxy-4-(1-methylpyrazol-4-yl)phenyl]-8-n,8-n-dimethylpyrido[3,4-d]pyrimidine-2,8-diamine Chemical compound C=1C=C(NC=2N=C3C(N(C)C)=NC=CC3=CN=2)C(OC)=CC=1C=1C=NN(C)C=1 GONPDSQILJJULJ-UHFFFAOYSA-N 0.000 claims 1
- NSTSQWCQKNBBLI-UHFFFAOYSA-N 2-n-[2-methoxy-4-(1-methylpyrazol-4-yl)phenyl]-8-n-(1-methylcyclohexyl)pyrido[3,4-d]pyrimidine-2,8-diamine Chemical compound COC1=CC(C2=CN(C)N=C2)=CC=C1NC(N=C12)=NC=C1C=CN=C2NC1(C)CCCCC1 NSTSQWCQKNBBLI-UHFFFAOYSA-N 0.000 claims 1
- CNYJTBHMNLHACD-UHFFFAOYSA-N 2-n-[2-methoxy-4-(1-methylpyrazol-4-yl)phenyl]-8-n-(1-methylpiperidin-4-yl)pyrido[3,4-d]pyrimidine-2,8-diamine Chemical compound COC1=CC(C2=CN(C)N=C2)=CC=C1NC(N=C12)=NC=C1C=CN=C2NC1CCN(C)CC1 CNYJTBHMNLHACD-UHFFFAOYSA-N 0.000 claims 1
- YHFRXIUIHKRDLF-UHFFFAOYSA-N 2-n-[2-methoxy-4-(1-methylpyrazol-4-yl)phenyl]-8-n-(2,2,2-trifluoroethyl)pyrido[3,4-d]pyrimidine-2,8-diamine Chemical compound C=1C=C(NC=2N=C3C(NCC(F)(F)F)=NC=CC3=CN=2)C(OC)=CC=1C=1C=NN(C)C=1 YHFRXIUIHKRDLF-UHFFFAOYSA-N 0.000 claims 1
- QZZFLPGPIFLIDL-UHFFFAOYSA-N 2-n-[2-methoxy-4-(1-methylpyrazol-4-yl)phenyl]-8-n-(2-methylpropyl)pyrido[3,4-d]pyrimidine-2,8-diamine Chemical compound C=1C=C(NC=2N=C3C(NCC(C)C)=NC=CC3=CN=2)C(OC)=CC=1C=1C=NN(C)C=1 QZZFLPGPIFLIDL-UHFFFAOYSA-N 0.000 claims 1
- RNQJDYAGBGETGI-UHFFFAOYSA-N 2-n-[2-methoxy-4-(1-methylpyrazol-4-yl)phenyl]-8-n-(3-methylbutyl)pyrido[3,4-d]pyrimidine-2,8-diamine Chemical compound C=1C=C(NC=2N=C3C(NCCC(C)C)=NC=CC3=CN=2)C(OC)=CC=1C=1C=NN(C)C=1 RNQJDYAGBGETGI-UHFFFAOYSA-N 0.000 claims 1
- MJPOKEITVYMJIC-UHFFFAOYSA-N 2-n-[2-methoxy-4-(1-methylpyrazol-4-yl)phenyl]-8-n-(oxan-4-yl)pyrido[3,4-d]pyrimidine-2,8-diamine Chemical compound COC1=CC(C2=CN(C)N=C2)=CC=C1NC(N=C12)=NC=C1C=CN=C2NC1CCOCC1 MJPOKEITVYMJIC-UHFFFAOYSA-N 0.000 claims 1
- ZUXWJMBALSCMPR-UHFFFAOYSA-N 2-n-[2-methoxy-4-(1-methylpyrazol-4-yl)phenyl]-8-n-(oxetan-2-ylmethyl)pyrido[3,4-d]pyrimidine-2,8-diamine Chemical compound COC1=CC(C2=CN(C)N=C2)=CC=C1NC(N=C12)=NC=C1C=CN=C2NCC1CCO1 ZUXWJMBALSCMPR-UHFFFAOYSA-N 0.000 claims 1
- SATXVBGBRZGLLQ-UHFFFAOYSA-N 2-n-[2-methoxy-4-(1-methylpyrazol-4-yl)phenyl]-8-n-(oxetan-3-yl)pyrido[3,4-d]pyrimidine-2,8-diamine Chemical compound COC1=CC(C2=CN(C)N=C2)=CC=C1NC(N=C12)=NC=C1C=CN=C2NC1COC1 SATXVBGBRZGLLQ-UHFFFAOYSA-N 0.000 claims 1
- DRIQYXAZDRMKER-UHFFFAOYSA-N 2-n-[2-methoxy-4-(1-methylpyrazol-4-yl)phenyl]-8-n-(oxetan-3-ylmethyl)pyrido[3,4-d]pyrimidine-2,8-diamine Chemical compound COC1=CC(C2=CN(C)N=C2)=CC=C1NC(N=C12)=NC=C1C=CN=C2NCC1COC1 DRIQYXAZDRMKER-UHFFFAOYSA-N 0.000 claims 1
- BKJILQPVRNPUBB-UHFFFAOYSA-N 2-n-[2-methoxy-4-(1-methylpyrazol-4-yl)phenyl]-8-n-(oxolan-3-yl)pyrido[3,4-d]pyrimidine-2,8-diamine Chemical compound COC1=CC(C2=CN(C)N=C2)=CC=C1NC(N=C12)=NC=C1C=CN=C2NC1CCOC1 BKJILQPVRNPUBB-UHFFFAOYSA-N 0.000 claims 1
- BTQWDXDOIDSBEJ-UHFFFAOYSA-N 2-n-[2-methoxy-4-(1-methylpyrazol-4-yl)phenyl]-8-n-(oxolan-3-ylmethyl)pyrido[3,4-d]pyrimidine-2,8-diamine Chemical compound COC1=CC(C2=CN(C)N=C2)=CC=C1NC(N=C12)=NC=C1C=CN=C2NCC1CCOC1 BTQWDXDOIDSBEJ-UHFFFAOYSA-N 0.000 claims 1
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- SPPGGNPUFQYLST-UHFFFAOYSA-N 2-n-[2-methoxy-4-(1-methylpyrazol-4-yl)phenyl]-8-n-[(3-methyloxolan-3-yl)methyl]pyrido[3,4-d]pyrimidine-2,8-diamine Chemical compound COC1=CC(C2=CN(C)N=C2)=CC=C1NC(N=C12)=NC=C1C=CN=C2NCC1(C)CCOC1 SPPGGNPUFQYLST-UHFFFAOYSA-N 0.000 claims 1
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- LHKNBEJQZVTLFY-UHFFFAOYSA-N 8-[1-(2,2-difluoroethyl)pyrazol-4-yl]-n-[2-methoxy-4-(1-methylpyrazol-4-yl)phenyl]pyrido[3,4-d]pyrimidin-2-amine Chemical compound COC1=CC(C2=CN(C)N=C2)=CC=C1NC(N=C12)=NC=C1C=CN=C2C=1C=NN(CC(F)F)C=1 LHKNBEJQZVTLFY-UHFFFAOYSA-N 0.000 claims 1
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- OPRFPXSJYIUWOX-UHFFFAOYSA-N 8-cyclohexylsulfanyl-n-[2-methoxy-4-(1-methylpyrazol-4-yl)phenyl]pyrido[3,4-d]pyrimidin-2-amine Chemical compound COC1=CC(C2=CN(C)N=C2)=CC=C1NC(N=C12)=NC=C1C=CN=C2SC1CCCCC1 OPRFPXSJYIUWOX-UHFFFAOYSA-N 0.000 claims 1
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- ZBJKHBDXYYMSMW-UHFFFAOYSA-N 8-n-(2,2-dimethylpropyl)-2-n-(2-methoxy-4-morpholin-4-ylphenyl)pyrido[3,4-d]pyrimidine-2,8-diamine Chemical compound C=1C=C(NC=2N=C3C(NCC(C)(C)C)=NC=CC3=CN=2)C(OC)=CC=1N1CCOCC1 ZBJKHBDXYYMSMW-UHFFFAOYSA-N 0.000 claims 1
- KRCCOUOMNPOYTD-UHFFFAOYSA-N 8-n-(2,2-dimethylpropyl)-2-n-(2-methoxy-4-piperidin-1-ylphenyl)pyrido[3,4-d]pyrimidine-2,8-diamine Chemical compound C=1C=C(NC=2N=C3C(NCC(C)(C)C)=NC=CC3=CN=2)C(OC)=CC=1N1CCCCC1 KRCCOUOMNPOYTD-UHFFFAOYSA-N 0.000 claims 1
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- ZSURBDONNIPHHP-UHFFFAOYSA-N n-[2-methyl-4-(1-methylpyrazol-4-yl)phenyl]-8-(1-methylpyrazol-4-yl)pyrido[3,4-d]pyrimidin-2-amine Chemical compound CC1=CC(C2=CN(C)N=C2)=CC=C1NC(N=C12)=NC=C1C=CN=C2C=1C=NN(C)C=1 ZSURBDONNIPHHP-UHFFFAOYSA-N 0.000 claims 1
- BGKIQPZNBKWSPB-UHFFFAOYSA-N n-[4-(1,5-dimethylpyrazol-4-yl)-2-methoxyphenyl]-8-(2-oxa-7-azaspiro[3.4]octan-7-yl)pyrido[3,4-d]pyrimidin-2-amine Chemical compound COC1=CC(C2=C(N(C)N=C2)C)=CC=C1NC(N=C12)=NC=C1C=CN=C2N(C1)CCC21COC2 BGKIQPZNBKWSPB-UHFFFAOYSA-N 0.000 claims 1
- UWIDLGGKUDRQDW-UHFFFAOYSA-N n-[4-(2,3-dimethylimidazol-4-yl)-2-methoxyphenyl]-5-(1-methylpyrazol-4-yl)isoquinolin-3-amine Chemical compound COC1=CC(C=2N(C(C)=NC=2)C)=CC=C1NC(N=CC1=CC=C2)=CC1=C2C=1C=NN(C)C=1 UWIDLGGKUDRQDW-UHFFFAOYSA-N 0.000 claims 1
- GOOYGSNWAYBEDE-UHFFFAOYSA-N n-[4-(2,3-dimethylimidazol-4-yl)-2-methoxyphenyl]-8-(1-methylpyrazol-4-yl)pyrido[3,4-d]pyrimidin-2-amine Chemical compound COC1=CC(C=2N(C(C)=NC=2)C)=CC=C1NC(N=C12)=NC=C1C=CN=C2C=1C=NN(C)C=1 GOOYGSNWAYBEDE-UHFFFAOYSA-N 0.000 claims 1
- DIMUSNDMJAIZAQ-UHFFFAOYSA-N n-[4-(3,5-dimethyl-1,2-oxazol-4-yl)-2-methoxyphenyl]-5-(1-methylpyrazol-4-yl)isoquinolin-3-amine Chemical compound COC1=CC(C2=C(ON=C2C)C)=CC=C1NC(N=CC1=CC=C2)=CC1=C2C=1C=NN(C)C=1 DIMUSNDMJAIZAQ-UHFFFAOYSA-N 0.000 claims 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000003367 polycyclic group Chemical group 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- IHLHRPALSFYTBL-UHFFFAOYSA-N tert-butyl 4-[4-[3-[2-methoxy-4-(3-methoxyazetidine-1-carbonyl)anilino]isoquinolin-5-yl]pyrazol-1-yl]piperidine-1-carboxylate Chemical compound C1C(OC)CN1C(=O)C(C=C1OC)=CC=C1NC1=CC2=C(C3=CN(N=C3)C3CCN(CC3)C(=O)OC(C)(C)C)C=CC=C2C=N1 IHLHRPALSFYTBL-UHFFFAOYSA-N 0.000 claims 1
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- A61K31/00—Medicinal preparations containing organic active ingredients
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4375—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
- A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
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- 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
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- 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
- C07D405/02—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 two hetero rings
- C07D405/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Claims (15)
1. Spoj formule I prikazano dalje u tekstu:
[image]
gdje:
W je N ili C-R3;
X je CH ili N;
Z je N ili C-H;
R1 je odabran iz kloro, (1-6C)alkila, (1-8C)heteroalkila, arila, aril(1-2C)alkila, heteroarila, heteroaril(1-2C)alkila, heterociklila, heterociklil(1-2C)alkila, (3-8C)cikloalkila, (3-8C)cikloalkil(1-2C)alkila, NR7R8, OR9, C(O)R9, C(O)OR9, OC(O)R9, N(R10)OR9, N(R10)C(O)OR9, C(O)N(R10)R9, N(R10)C(O)R9, S(O)pR9 (gdje p je 0 ili 1), SO2N(R10)R9, N(R10)SO2R9, N(R10)SOR9 ili SON(R10)R9;
i gdje R1 je izborno supstituiran s jednim ili više skupina supstituenata odabranih iz fluoro, kloro, trifluorometila, trifluorometoksi, cijano, nitro, hidroksi, amino, karboksi, karbamoila, sulfamoila, (1-4C)alkila, (1-4C)alkoksi, S(O)qCH3 (gde q je 0, 1 ili 2), metilamino ili dimetilamino, arila, aril(1-2C)alkila, heteroarila, heteroaril(1-2C)alkila, heterociklila, heterociklil(1-2C)alkila, (3-8C)cikloalkila, ili (3-8C)cikloalkil(1-2C)alkila, i gdje je svaka (1-4C)alkil, (1-4C)alkoksi, aril, heteroaril, heterociklil, ili (3-8C)cikloalkil skupina prisutna unutar skupine supstituenta na R1 izborno dalje supstituirana s fluoro, kloro, trifluorometilom, trifluorometoksi, cijano, nitro, hidroksi, amino, karboksi, karbamoilom, sulfamoilom, (1-4C)alkilom, NRaRb, ORa, C(O)Ra, C(O)ORa, OC(O)Ra, N(Rb)ORa, C(O)N(Rb)Ra, N(Rb)C(O)Ra, S(O)pRa (gde p je 0, 1 ili 2), SO2N(Rb)Ra, ili N(Rb)SO2Ra,
gdje su Ra i Rb svaki neovisno odabran iz H ili (1-4C)alkila;
R3 je vodik, (1-4C)alkil, (3-6C)cikloalkil, halo, CF3, CN i (1-4C)alkoksi;
R4 je vodik, (1-3C)alkil, (1-3C)alkoksi, fluoro, kloro ili CF3;
Ar ima formulu:
[image]
gdje:
(i) svi od A1, A2 i A3 su CH;
(ii) jedan od A1, A2 i A3 je N i drugi su CH; ili
(iii) dva od A1, A2 i A3 su N i drugi je CH;
R5 je odabran iz vodika, cijano, (1-3C)alkila, (1-3C)fluoroalkila, (1-3C)alkoksi, (1-3C)fluoroalkoksi, halo, (1-3C)alkanoila, C(O)NR15R16 ili S(O)2NR15R16, i gdje R15 i R16 su svaki neovisno odabrani iz H ili (1-3C)alkila,
i gdje su bilo koje alkil ili alkoksi skupine prisutne unutar R5 skupine supstituenta izborno dalje supstituirane s hidroksi ili metoksi;
R6 je odabran od halo, trifluorometila, trifluorometoksi, cijano, nitro, hidroksi, amino, karboksi, karbamoila, sulfamoila, ureido, (1-6C)alkila, (2-6C)alkenila, (2-6C)alkinila, ili R6 je skupina formule:
-L1-L2-R17
gdje
L1 je odsutan ili linker grupa formule -[CR18R19]n- u kojoj n je cijeli broj odabran od 1, 2, 3 ili 4, i R18 i R19 su svaki neovisno odabran iz vodika ili (1-2C)alkila;
L2 je odsutan ili je odabran od O, S, SO, SO2, N(R20), C(O), C(O)O, OC(O), CH(OR20), C(O)N(R20), N(R20)C(O), N(R20)C(O)N(R21), S(O)2N(R20), ili N(R21)SO2, gdje R20 i R21 su svaki neovisno odabrani od vodika ili (1-2C)alkila; i
R17 je (1-6C)alkil, aril, aril-(1-6C)alkil, (3-6C)cikloalkil, (3-6C)cikloalkil-(1-4C)alkil, heteroaril, heteroaril-(1-4C)alkil, heterociklil, heterociklil-(1-4C)alkil, i gdje R17 je izborno dalje supstituiran s jednim ili više skupina supstituenata neovisno odabranih od okso, halo, cijano, nitro, hidroksi, NR22R23, (1-4C)alkoksi, (1-4C)alkila, (3-8C)cikloalkila, (3-8C)cikloalkil-(1-3C)alkila, (1-5C)alkanoila, (1-5C)alkilsulfonila, heterociklila, heterociklil-(1-2C)alkila, heteroarila, heteroaril-(1-2C)alkila, CONR22R23, i SO2NR22R23; gde R22 i R23 su svaki neovisno odabrani iz vodika, (1-4C)alkila ili (3-6C)cikloalkila ili (3-6C)cikloalkil(1-2C)alkila;
i gdje kada navedena skupina supstituent sadrži alkil, cikloalkil, heterociklil ili heteroaril skupinu tada navedena skupina je izborno dalje supstituirana s hidroksi, fluoro, kloro, cijano, CF3, OCF3, (1-2C)alkil, (1-2C)alkoksi, SO2(1-2C)alkil ili NReRf (gde Re i Rf su svaki neovisno odabrani od vodika, (1-3C)alkila, (3-6C)cikloalkila, ili (3-6C)cikloalkil(1-2C)alkila);
ili R17 je skupina čija formula je:
-L3-L4-R24
L3 je odsutan ili linker skupina formule -[CR25R26]n- u kojoj n je cijeli broj odabran od 1, 2, 3 ili 4, i R25 i R26 su svaki neovisno odabrani od vodika ili (1-2C)alkila;
L4 je odsutan ili odabran od O, S, SO, SO2, N(R27), C(O), C(O)O, OC(O), CH(OR27), C(O)N(R27), N(R27)C(O), N(R27)C(O)N(R28), S(O)2N(R27), ili N(R28)SO2, gdje R27 i R28 su svaki neovisno odabran iz vodika ili (1-2C)alkila; i
R24 je (1-6C)alkil, aril, aril-(1-6C)alkil, (3-6C)cikloalkil, (3-6C)cikloalkil-(1-4C)alkil, heteroaril, heteroaril-(1-4C)alkil, heterociklil, heterociklil-(1-4C)alkil;
R8 i R9 su svaki neovisno odabran od vodika, (1-6C)alkila, (1-6C)alkoksi, (3-9C)cikloalkila, (3-9C)cikloalkil-(1-2C)alkila, arila, aril-(1-2C)alkila, heterociklila, heterociklil-(1-2C)alkila, heteroarila, heteroaril-(1-2C)alkila, i gdje R8 i R9 su izborno dalje supstituirani s jednim ili više supstituenata odabranih od hidroksi, fluoro, kloro, cijano, CF3, OCF3 (1-2C)alkila ili (1-2C)alkoksi;
R7 i R10 su neovisno odabrani iz vodika, (1-6C)alkila, (3-6C)cikloalkila, (3-6C)cikloalkil-(1-2C)alkila, i gdje su R7 i R10 izborno dalje supstituirani s jednim ili više supstituenata izabranih od hidroksi, fluoro, kloro, cijano, CF3, OCF3, (1-2C)alkila ili (1-2C)alkoksi;
gdje izraz "heterociklil" i "heterocikličan" označava nearomatizirani zasićeni ili djelomično zasićeni monociklični, fuzionirani, premošteni ili spiro biciklični heterociklički sustav(e) prstena; i
gdje izraz "heteroaril" označava aromatizirani mono-, bi- ili policiklički prsten koji obuhvaća jedan ili više heteroatoma odabranih iz dušika, kisika ili sumpora, i djelomično aromatizirane bi- ili policiklične sustave prstena gdje je najmanje jedan prsten aromatiziran prsten i jedan ili više od drugih prstenova je nearomatizirani, zasićeni ili djelomično zasićeni prsten, uz uvjet da najmanje jedan prsten sadrži jedan ili više heteroatoma odabranih iz dušika, kisika ili sumpora; i
uz uvjet da:
X je samo N kada je Z jednako N; i
W je samo N kada su X i Z oba N;
ili njegova farmaceutski prihvatljiva sol ili solvat.
2. Spoj u skladu s patentnim zahtjevom 1, naznačeno time što navedeni spoj ima strukturnu formulu Ib, Ic ili Id
[image]
3. Spoj u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačeno time što:
(i) R1 je odabran od (1-6C)alkila, fenila, fenil(1-2C)alkila, 5 ili 6 –članog heteroarila, 5 ili 6 –članog heteroaril(1-2C)alkila, 3 do 9 –članog heterociklila, 3 do 9 –članog heterociklil(1-2C)alkial, (3-6C)cikloalkila, (3-6C)cikloalkil(1-2C)alkila, NR7R8, OR9, C(O)R9, C(O)OR9, OC(O)R9, N(R10)OR9, N(R10)C(O)OR9, C(O)N(R10)R9, N(R10)C(O)R9, S(O)pR9(gdje p je 0 ili 1), SO2N(R10)R9, ili N(R10)SO2R9;
i gdje je R1 izborno supstituiran s jednim ili više skupina supstituenata odabranih od fluoro, kloro, trifluorometila, trifluorometoksi, cijano, hidroksi, amino, karbamoila, sulfamoila, (1-4C)alkila, (1-4C)alkoksi, S(O)qCH3(gde q je 0, 1 ili 2), metilamino ili dimetilamino, 5 ili 6 –članog heteroarila, 5 ili 6 –članog heteroaril(1-2C)alkila, 3 do 6 –članog heterociklila, 3 do 6 –članog heterociklil(1-2C)alkila, (3-6C)cikloalkila ili (3-6C)cikloalkil(1-2C)alkila,
i gdje je bilo koja (1-4C)alkil, (1-4C)alkoksi, heteroaril, heterociklil, ili (3-6C)cikloalkil skupina prisutna unutar skupine supstituenta na R1 izborno dalje supstituirana s fluoro, kloro, trifluorometil, trifluorometoksi, cijano, hidroksi, amino, karboksi, karbamoil, sulfamoil, (1-4C)alkil, NRaRb, ORa, C(O)Ra, C(O)ORa, OC(O)Ra, N(Rb)ORa, C(O)N(Rb)Ra, N(Rb)C(O)Ra, S(O)pRa(gdje p je 0, 1 ili 2), SO2N(Rb)Ra, ili N(Rb)SO2Ra, gdje su Ra i Rb svaki neovisno odabrani od H ili (1-4C)alkila; ili
(ii) R1 je odabran od (1-6C)alkila, fenil, fenil(1-2C)alkila, 5 ili 6 –članog heteroarila, 5 ili 6 –članog heteroaril(1-2C)alkila, 3 do 9 –članog heterociklila, 3 do 9 –članog heterociklil(1-2C)alkila, (3-6C)cikloalkila, (3-6C)cikloalkil(1-2C)alkila, NR7R8, OR9, C(O)R9, C(O)OR9, OC(O)R9, N(R10)OR9, N(R10)C(O)OR9, C(O)N(R10)R9, N(R10)C(O)R9, S(O)pR9(gdje p je 0 ili 1), SO2N(R10)R9, ili N(R10)SO2R9;
i gdje je R1 izborno supstituiran s jednim ili više skupina supstituenata odabranih od fluoro, kloro, trifluorometila, trifluorometoksi, cijano, hidroksi, amino, karbamoila, sulfamoila, (1-4C)alkila, (1-4C)alkoksi, S(O)qCH3(gde q je 0, 1 ili 2), metilamino ili dimetilamino, 5 ili 6 –članog heteroarila, ili 4 do 6 –članog heterociklila,
i gdje bilo koja (1-4C)alkil, (1-4C)alkoksi, heteroaril, ili heterociklil skupina prisutna unutar skupine supstituenta na R1 je izborno dalje supstituirana s fluoro, kloro, trifluorometil, trifluorometoksi, cijano, hidroksi, amino, karbamoila, sulfamoila, (1-4C)alkil, NRaRb, ORa, C(O)Ra, C(O)ORa, OC(O)Ra, C(O)N(Rb)Ra, N(Rb)C(O)Ra, S(O)pRa (gdje p je 0, 1 ili 2), SO2N(Rb)Ra, ili N(Rb)SO2Ra, gdje su Ra i Rb svaki neovisno odabrani od H ili (1-4C)alkila;
4. Spoj u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačeno time što R3 je vodik, (1-2C)alkil, ili (3-6C)cikloalkil.
5. Spoj u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačeno time što R4 je vodik, (1-2C)alkil, (1-2C)alkoksi, fluoro, kloro ili CF3.
6. Spoj u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačeno time što:
(i) Ar formula je:
[image]
gdje:
(i) svi od A1, A2 i A3 su CH; ili
(ii) jedan od A1, A2 i A3 je N i drugi su CH;
R5 je vodik, cijano, (1-3C)alkil, (1-3C)perfluoroalkil, (1-3C)alkoksi, (1-3C)fluoroalkoksi, i halo, i
gdje su bilo koje alkil ili alkoksi skupine prisutne unutar R5 skupine supstituenta izborno dalje supstituirane s hidroksi ili metoksi; i
R6 je halogeno, trifluorometil, trifluorometoksi, cijano, hidroksi, amino, karboksi, karbamoil, sulfamoil,
ili R6 je skupina formule:
-L1-L2-R17
gdje
L1 je odsutan ili linker skupina formule -[CR18R19]n- u kojoj n je cijeli broj odabran od 1 ili 2,
i R18 i R19 su svaki neovisno odabrani iz vodika ili metila;
L2 je odsutan ili odabran od O, S, SO, SO2, N(R20), C(O), C(O)O, OC(O), CH(OR20), C(O)N(R20), N(R20)C(O), N(R20)C(O)N(R21), S(O)2N(R20), ili N(R20)SO2, gdje su R20 i R21 svaki neovisno odabrani iz vodika ili (1-2C)alkila; i
R17 je (1-6C)alkil, aril, (3-6C)cikloalkil, 5 ili 6 –člani heteroaril, ili 3 do 8 –člani heterociklil,
i gdje je R17 izborno dalje supstituiran s jednom ili više skupina supstituenata neovisno odabranih od okso, halo, cijano, nitro, hidroksi, NR22R23, (1-4C)alkoksi, (1-4C)alkila, (3-8C)cikloalkila, (3-8C)cikloalkil-(1-3C)alkila, (1-5C)alkanoila, (1-5C)alkilsulfonila, 3 do 6 -članog heterociklila, 3 do 6 -članog heterociklil-(1-2C)alkila, 5 ili 6 –članog heteroarila, 5 ili 6 –članog heteroaril-(1-2C)alkila, CONR22R23, i SO2NR22R23; gdje su R22 i R23 svaki neovisno odabrani iz vodika, (1-4C)alkila ili (3-6C)cikloalkila ili (3-6C)cikloalkil(1-2C)alkila; ili R22i R23 mogu biti vezani na način da, zajedno s atomom dušika za koji su vezani, tvore 4-6 –člani heterociklični prsten;
i gdje kada navedena skupina supstituent sadrži alkil, cikloalkil, heterociklil ili heteroaril skupinu tada je navedena skupina izborno dalje supstituirana s hidroksi, fluoro, kloro, cijano, CF3, OCF3, (1-2C)alkil, (1-2C)alkoksi, SO2(1-2C)alkil ili NReRf (gde su Re i Rf svaki neovisno odabrani iz vodika, (1-3C)alkila, (3-6C)cikloalkila, ili (3-6C)cikloalkil(1-2C)alkila);
ili R17 je skupina čija formula je:
-L3-L4-R24
L3 je odsutan ili linker skupina formule -[CR25R26]n- u kojoj n je cijeli broj odabran od 1, 2, 3 ili 4, i R25 i R26 su svaki neovisno odabran iz vodika ili (1-2C)alkila;
L4 je odsutan ili je odabran od O, S, SO, SO2, N(R27), C(O), C(O)O, OC(O), CH(OR27), C(O)N(R27), N(R27)C(O), N(R27)C(O)N(R28), S(O)2N(R27), ili N(R28)SO2, gdje su R27 i R28 svaki neovisno odabran iz vodika ili (1-2C)alkila; i R24 je (1-6C)alkil, aril, aril-(1-6C)alkil, (3-6C)cikloalkil, (3-6C)cikloalkil-(1-4C)alkil, heteroaril, heteroaril-(1-4C)alkil, heterociklil, heterociklil-(1-4C)alkil; ili
(ii) Ar formula je:
[image]
gdje:
(i) svi od A1, A2 i A3 su CH; ili
(ii) A3 je CH i jedan od A1 ili A2 je N i drugi je CH;
i R5 i R6 su svaki kao što su definirani u patentnom zahtjevu 1 ili u (i) u prethodnom tekstu.
7. Spoj u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što R5 je (1-2C)alkil, CF3, (1-2C)alkoksi, -OCF3, -OCF2H ili Cl.
8. Spoj u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačeno time što R6 je skupina formule:
-L1-L2-R17
gdje
L1 je odsutan ili linker skupina formule -[CR18R19]n- u kojoj n je cijeli broj odabran iz 1 ili 2, i R18 i R19 su oba vodik;
L2 je odsutan ili odabran od O, S, SO, SO2, N(R20), C(O), C(O)O, OC(O), CH(OR20), C(O)N(R20), N(R20)C(O), N(R20)C(O)N(R21), S(O)2N(R20), ili N(R20)SO2, gdje su R20 i R21 svaki neovisno odabrani iz vodika ili (1-2C)alkil; i
R17 je (1-6C)alkil, aril, (3-6C)cikloalkil, 5 ili 6 -člani heteroaril, ili 3 do 8 –člani heterociklil,
i gdje je R17 izborno dalje supstituiran s jednom ili više skupina supstituenta neovisno odabranih od okso, halo, cijano, hidroksi, NR22R23, (1-4C)alkoksi, (1-4C)alkila, (1-5C)alkilsulfonila, 3 do 6 –članog heterociklila, 3 do 6 –članog heterociklil-(1-2C)alkila, 5 ili 6 –članog heteroarila, 5 ili 6 –članog heteroaril-(1-2C)alkila, CONR22R23, i SO2NR22R23; gdje su R22 i R23 svaki neovisno odabrani iz vodika, (1-4C)alkila ili (3-6C)cikloalkila ili (3-6C)cikloalkil(1-2C)alkila; ili R22 i R23 mogu biti vezani tako da, zajedno sa atomom dušika za koji su vezani, tvore 4-6 –člani heterociklički prsten;
i gdje kada navedena skupina supstituent sadrži alkil, cikloalkil, heterociklil ili heteroaril skupina tada je navedena skupina izborno dalje supstituirana s hidroksi, fluoro, kloro, cijano, CF3, OCF3, (1-2C)alkil, (1-2C)alkoksi, SO2(1-2C)alkil ili NReRf (gde Re i Rf su svaki neovisno odabrani iz vodika ili (1-2C)alkila).
ili R17 je skupina koja sadrži formulu:
-L3-L4-R24
L3 je odsutan ili linker skupina formule -[CR25R26]n- u kojoj n je cijeli broj odabran iz 1,
2, 3 ili 4, i R25 i R26 su svaki neovisno odabrani iz vodika ili (1-2C)alkila;
L4 je odsutan ili je odabran iz O, S, SO, SO2, N(R27), C(O), C(O)O, OC(O), CH(OR27), C(O)N(R27), N(R27)C(O), N(R27)C(O)N(R28), S(O)2N(R27), ili N(R28)SO2, gdje su R27 i R28 svaki neovisno odabrani iz vodika ili (1-2C)alkila; i
R24 je (1-6C)alkil, aril, aril-(1-6C)alkil, (3-6C)cikloalkil, (3-6C)cikloalkil-(1-4C)alkil, heteroaril, heteroaril-(1-4C)alkil, heterociklil, heterociklil-(1-4C)alkil.
9. Spoj u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačeno time što R8 i R9 su svaki neovisno odabrani od vodika, (1-6C)alkila, (3-9C)cikloalkila, (3-6C)cikloalkil-(1-2C)alkila, fenila, 3 do 9 –članog heterociklila, 3 do 9 -članog heterociklil-(1-2C)alkila, 5 ili 6 -članog heteroarila, 5 ili 6 –članog heteroaril-(1-2C)alkila, i gdje su R8 i R9 izborno dalje supstiturani s jednim ili više supstituenta odabrani od hidroksi, fluoro, kloro, cijano, CF3, OCF3, (1-2C)alkila ili (1-2C)alkoksi.
10. Spoj u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačeno time što R7 i R10 su neovisno odabrani od vodika ili (1-4C)alkila.
11. Spoj u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačeno time što je navedeni spoj bilo koji od slijedećih:
5-(furan-2-il)-N-(4-metoksifenil)izokinolin-3-amin;
N-(4-metoksifenil)-5-(1-metil-1H-pirazol-4-il)izokinolin-3-amin;
N-(2-metoksi-4-((1-metilpiperidin-4-il)oksi)fenil)-5-(1-metil-1H-pirazol-4-il)izokinolin-3-amin;
N-(2,4-dimetoksifenil)-5-(1-metil-1H-pirazol-4-il)izokinolin-3-amin;
3-kloro-N,N-dimetil-4-((5-(1-metil-1H-pirazol-4-il)izokinolin-3-il)amino)benzamid;
3-metoksi-N,N-dimetil-4-((5-(1-metil-1H-pirazol-4-il)izokinolin-3-il)amino)benzamid;
(3-metoksi-4-((5-(1-metil-1H-pirazol-4-il)izokinolin-3-il)amino)fenil)(3-metoksiazetidin-1-il)metanon;
N-(2-kloro-4-(1-metil-1H-pirazol-4-il)fenil)-5-(1-metil-1H-pirazol-4-il)izokinolin-3-amin;
(3-kloro-4-((5-(1-metil-1H-pirazol-4-il)izokinolin-3-il)amino)fenil)(3-metoksiazetidin-1-il)metanon;
(3-metoksi-4-((5-(piridin-3-il)izokinolin-3-il)amino)fenil)(3-metoksiazetidin-1-il)metanon;
N-(4-(3,5-dimetilizoksazol-4-il)-2-metoksifenil)-5-(1-metil-1H-pirazol-4-il)izokinolin-3-amin;
(3-metoksi-4-((8-(1-metil-1H-pirazol-4-il)pirido[3,4-d]pirimidin-2-il)amino)fenil)(3-metoksiazetidin-1-il)metanon;
N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-8-(1-metil-1H-pirazol-4-il)pirido[3,4-d]pirimidin-2-amin;
N-(2-kloro-4-(1-metil-1H-pirazol-4-il)fenil)-8-(1-metil-1H-pirazol-4-il)pirido[3,4-d]pirimidin-2-amin;
N-(2-kloro-4-(1-metil-1H-imidazol-5-il)fenil)-5-(1-metil-1H-pirazol-4-il)izokinolin-3-amin;
N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-5-(1-metil-1H-pirazol-4-il)izokinolin-3-amin;
(3-metoksi-4-((5-(pirimidin-5-il)izokinolin-3-il)amino)fenil)(3-metoksiazetidin-1-il)metanon;
N-(2-metoksi-4-(1-metil-1H-imidazol-5-il)fenil)-5-(1-metil-1H-pirazol-4-il)izokinolin-3-amin;
(4-((5-(1,5-dimetil-1H-pirazol-4-il)izokinolin-3-il)amino)-3-metoksifenil)(3-metoksiazetidin-1-il)metanon;
(3-metoksi-4-((5-(1-metil-1H-pirazol-3-il)izokinolin-3-il)amino)fenil)(3-metoksiazetidin-1-il)metanon;
N-(2-kloro-4-(1,2-dimetil-1H-imidazol-5-il)fenil)-5-(1-metil-1H-pirazol-4-il)izokinolin-3-amin;
N-(4-(1,2-dimetil-1H-imidazol-5-il)-2-metoksifenil)-5-(1-metil-1H-pirazol-4-il)izohinolin-3-amin;
N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-8-fenilpirido[3,4-d]pirimidin-2-amin;
8-ciklopropil-N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)pirido[3,4-d]pirimidin-2-amin;
N-(2-metoksi-5-metil-4-(1-metil-1H-pirazol-4-il)fenil)-8-(1-metil-1H-pirazol-4-il)pirido[3,4-d]pirimidin-2-amin;
(3-metoksi-4-((5-(1-metil-1H-pirazol-5-il)izokinolin-3-il)amino)fenil)(3-metoksiazetidin-1-il)metanon;
(4-((5-(1,3-dimetil-1H-pirazol-4-il)izokinolin-3-il)amino)-3-metoksifenil)(3-metoksiazetidin-1-il)metanon;
(4-((5-(1-izopropil-1H-pirazol-4-il)izokinolin-3-il)amino)-3-metoksifenil)(3-metoksiazetidin-1-il)metanon;
4-((5-(1-metil-1H-pirazol-4-il)izokinolin-3-il)amino)-N-(1-metilpiperidin-4-il)-3-(trifluorometoksi)benzamid;
(4-((5-(3,5-dimetilizoksazol-4-il)izokinolin-3-il)amino)-3-metoksifenil)(3-metoksiazetidin-1-il)metanon;
(3-metoksi-4-((5-(1-metil-1H-imidazol-5-il)izokinolin-3-il)amino)fenil)(3-metoksiazetidin-1-il)metanon;
N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-8-(pirolidin-1-il)pirido[3,4-d]pirimidin-2-amin;
N-(4-(1,2-dimetil-1H-imidazol-5-il)-2-metoksifenil)-8-(1-metil-1H-pirazol-4-il)pirido[3,4-d]pirimidin-2-amin;
terc-butil 4-(4-(3-((2-metoksi-4-(3-metoksiazetidin-1-karbonil)fenil)amino)izokinolin-5-il)-1H-pirazol-1-il)piperidin-1-karboksilat;
(3-metoksi-4-((5-(1-(piperidin-4-il)-1H-pirazol-4-il)izokinolin-3-il)amino)fenil)(3-metoksiazetidin-1-il)metanon;
(3-metoksi-4-((5-(1-(1-metilpiperidin-4-il)-1H-pirazol-4-il)izokinolin-3-il)amino)fenil)(3-metoksiazetidin-1-il)metanon;
(3-metoksi-4-((5-(1-(2-metoksietil)-1H-pirazol-4-il)izokinolin-3-il)amino)fenil)(3-metoksiazetidin-1-il)metanon;
N8,N8-dietil-N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)pirido[3,4-d]pirimidin-2,8-diamin;
N8-ciklopentil-N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)pirido[3,4-d]pirimidin-2,8-diamin;
(4-((5-(1-(2-(dimetilamino)etil)-1H-pirazol-4-il)izokinolin-3-il)amino)-3-metoksifenil)(3-metoksiazetidin-1-il)metanon;
N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-5-(1-metil-1H-pirazol-4-il)-2,6-naftiridin-3-amin;
N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-8-(piperidin-1-il)pirido[3,4-d]pirimidin-2-amin;
N8-cikloheksil-N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)pirido[3,4-d]pirimidin-2,8-diamin;
N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-8-(3-metilpirolidin-1-il)pirido[3,4-d]pirimidin-2-amin;
8-(3,3-difluoropirolidin-1-il)-N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)pirido[3,4-d]pirimidin-2-amin;
N-(4-(1,2-dimetil-1H-imidazol-5-il)-2-metoksifenil)-5-(1-metil-1H-pirazol-4-il)-2,6-naftiridin-3-amin;
N8-(ciklopropilmetil)-N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)pirido[3,4-d]pirimidin-2,8-diamin;
8-(1-metil-1H-pirazol-4-il)-N-(2-metil-4-(1-metil-1H-pirazol-4-il)fenil)pirido[3,4-d]pirimidin-2-amin;
N8-ciklopentil-N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-N8-metilpirido[3,4-d]pirimidin-2,8-diamin;
N-(2-etoksi-4-(1-metil-1H-pirazol-4-il)fenil)-8-(1-metil-1H-pirazol-4-il)pirido[3,4-d]pirimidin-2-amin;
N-(2-izopropoksi-4-(1-metil-1H-pirazol-4-il)fenil)-8-(1-metil-1H-pirazol-4-il)pirido[3,4-d]pirimidin-2-amin;
N-(2-(2-metoksietoksi)-4-(1-metil-1H-pirazol-4-il)fenil)-8-(1-metil-1H-pirazol-4-il)pirido[3,4-d]pirimidin-2-amin;
N8-isopentil-N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)pirido[3,4-d]pirimidin-2,8-diamin;
N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-8-morfolinopirido[3,4-d]pirimidin-2-amin;
N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-8-(4-metilpiperazin-1-il)pirido[3,4-d]pirimidin-2-amin;
8-(3,3-difluoroazetidin-1-il)-N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)pirido[3,4-d]pirimidin-2-amin;
N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-8-(2-metilpirolidin-1-il)pirido[3,4-d]pirimidin-2-amin;
N8-izobutil-N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)pirido[3,4-d]pirimidin-2,8-diamin;
8-(cikloheksiltio)-N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)pirido[3,4-d]pirimidin-2-amin;
N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-8-(6-azaspiro[3.4]oktan-6-il)pirido[3,4-d]pirimidin-2-amin;
N8-cikloheksil-N2-(2-metoksi-4-(1-(2-(4-metilpiperazin-1-il)etil)-1H-pirazol-4-il)fenil)pirido[3,4-d]pirimidin-2,8-diamin;
8-(1-etil-1H-pirazol-4-il)-N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)pirido[3,4-d]pirimidin-2-amin;
8-(1-izopropil-1H-pirazol-4-il)-N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)pirido[3,4-d]pirimidin-2-amin;
N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-8-(3-metoksiazetidin-1-il)pirido[3,4-d]pirimidin-2-amin;
N1-(ciklopropilmetil)-N7-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-2,6-naftiridin-1,7-diamin;
N1-cikloheksil-N7-(2-metoksi-4-(-metil-1H-pirazol-4-il)fenil)-2,6-naftiridin-1,7-diamin;
N8-cikloheksil-N2-(4-(1-(2-(dimetilamino)etil)-1H-pirazol-4-il)-2-metoksifenil)pirido[3,4-d]pirimidin-2,8-diamin;
N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-N8-neopentilpirido[3,4-d]pirimidin-2,8-diamin;
N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-N8-(tetrahidro-2H-piran-4-il)pirido[3,4-d]pirimidin-2,8-diamin;
N8-(ciklopropilmetil)-N2-(2-metil-4-(1-metil-1H-pirazol-4-il)fenil)pirido[3,4-d]pirimidin-2,8-diamin;
N8-cikloheksil-N2-(2-metil-4-(1-metil-1H-pirazol-4-il)fenil)pirido[3,4-d]pirimidin-2,8-diamin;
N8-(ciklopropilmetil)-N2-(2-etoksi-4-(1-metil-1H-pirazol-4-il)fenil)pirido[3,4-d]pirimidin-2,8-diamin;
N8-(cikloheksilmetil)-N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)pirido[3,4-d]pirimidin-2,8-diamin;
2-(4-(4-((8-(cikloheksilamino)pirido[3,4-d]pirimidin-2-il)amino)-3-metoksifenil)-1H-pirazol-1-il)etanol;
8-(ciklopropilmetoksi)-N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)pirido[3,4-d]pirimidin-2-amin;
1-((2-((2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)amino)pirido[3,4-d]pirimidin-8-il)amino)-2-metilpropan-2-ol;
N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-N8-(oksetan-3-ilmetil)pirido[3,4-d]pirimidin-2,8-diamin;
N8-(3,3-dimetilbutan-2-il)-N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)pirido[3,4-d]pirimidin-2,8-diamin;
3-((2-((2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)amino)pirido[3,4-d]pirimidin-8-il)amino)-2,2-dimetilpropan-1-ol;
N2-(2-etoksi-4-(1-metil-1H-pirazol-4-il)fenil)-N8-(tetrahidro-2H-piran-4-il)pirido[3,4-d]pirimidin-2,8-diamin;
N2-(2-metoksi-6-morfolinopiridin -3-il)-N8-neopentilpirido[3,4-d]pirimidin-2,8-diamin;
N2-(2-metoksi-6-(metilsulfonil)piridin -3-il)-N8-neopentilpirido[3,4-d]pirimidin-2,8-diamin;
N2-(2-metoksi-4-(1-metil-1H-imidazol-5-il)fenil)-N8-neopentilpirido[3,4-d]pirimidin-2,8-diamin;
N2-(4-(1,3-dimetil-1H-pirazol-4-il)-2-metoksifenil)-N8-neopentilpirido[3,4-d]pirimidin-2,8-diamin;
N8-(1-ciklopropiletil)-N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)pirido[3,4-d]pirimidin-2,8-diamin;
2-(4-(3-metoksi-4-((8-((tetrahidro-2H-piran-4-il)amino)pirido[3,4-d]pirimidin-2-il)amino)fenil)-1H-pirazol-1-il)etanol;
N2-(4-(1,5-dimetil-1H-pirazol-4-il)-2-metoksifenil)-N8-neopentilpirido[3,4-d]pirimidin-2,8-diamin;
(R)-N8-(3,3-dimetilbutan-2-il)-N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)pirido[3,4-d]pirimidin-2,8-diamin;
(S)-N8-(3,3-dimetilbutan-2-il)-N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)pirido[3,4-d]pirimidin-2,8-diamin;
N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-N8-(tetrahidrofuran-3-il)pirido[3,4-d]pirimidin-2,8-diamin;
N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-N8-((tetrahidrofuran-3-il)metil)pirido[3,4-d]pirimidin-2,8-diamin;
1-(2-((2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)amino)pirido[3,4-d]pirimidin-8-il)pirolidin-3-ol;
N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-N8-metil-N8-(tetrahidro-2H-piran-4-il)pirido[3,4-d]pirimidin-2,8-diamin;
N8-(terc-butil)-N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)pirido[3,4-d]pirimidin-2,8-diamin;
N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-N8-(1-metilcikloheksil)pirido[3,4-d]pirimidin-2,8-diamin;
8-(1-(2,2-difluoroetil)-1H-pirazol-4-il)-N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)pirido[3,4-d]pirimidin-2-amin;
N2-(4-(1,2-dimetil-1H-imidazol-5-il)-2-metoksifenil)-N8-neopentilpirido[3,4-d]pirimidin-2,8-diamin;
N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-6-metil-N8-neopentilpirido[3,4-d]pirimidin-2,8-diamin;
N2-(2-metoksi-4-morfolinofenil)-N8-neopentilpirido[3,4-d]pirimidin-2,8-diamin;
N8-(2,2-difluoropropil)-N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)pirido[3,4-d]pirimidin-2,8-diamin;
N8-(3-metoksi-2,2-dimetilpropil)-N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)pirido[3,4-d]pirimidin-2,8-diamin;
N8-(2-metoksi-2-metilpropil)-N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)pirido[3,4-d]pirimidin-2,8-diamin;
N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-N8-(2,2,2-trifluoroetil)pirido[3,4-d]pirimidin-2,8-diamin;
N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-8-(2-oksa-6-azaspiro[3.4]oktan-6-il)pirido[3,4-d]pirimidin-2-amin;
1-(((2-((2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)amino)pirido[3,4-d]pirimidin-8-il)amino)metil)ciklobutanol;
8-hloro-N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)pirido[3,4-d]pirimidin-2-amin;
N2-(2-etil-4-(1-metil-1H-pirazol-4-il)fenil)-N8-neopentilpirido[3,4-d]pirimidin-2,8-diamin;
N2-(4-(1-metil-1H-pirazol-4-il)-2-(trifluorometoksi)fenil)-N8-neopentilpirido[3,4-d]pirimidin-2,8-diamin;
N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-N8-metilpirido[3,4-d]pirimidin-2,8-diamin;
N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-N8,N8-dimetilpirido[3,4-d]pirimidin-2,8-diamin;
N-(2-((2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)amino)pirido[3,4-d]pirimidin-8-il)-2-metilpropan-2-sulfinamid;
N2-(2-metoksi-4-(4-morfolinopiperidin-1-il)fenil)-N8-neopentilpirido[3,4-d]pirimidin-2,8-diamin;
N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-N8-((3-metiloksetan-3-il)metil)pirido[3,4-d]pirimidin-2,8-diamin;
N2-(2-metoksi-4-(piperidin-1-il)fenil)-N8-neopentilpirido[3,4-d]pirimidin-2,8-diamin;
N-(2-((2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)amino)pirido[3,4-d]pirimidin-8-il)-2-metilpropan-2-sulfonamid;
N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-N8-(oksetan-3-il)pirido[3,4-d]pirimidin-2,8-diamin;
(1-(3-metoksi-4-((8-(neopentilamino)pirido[3,4-d]pirimidin-2-il)amino)fenil)piperidin-4-il)(morfolino)metanon;
N2-(2-metoksi-4-(4-metilpiperazin-1-il)fenil)-N8-neopentilpirido[3,4-d]pirimidin-2,8-diamin;
1-(((2-((2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)amino)pirido[3,4-d]pirimidin-8-il)amino)metil)ciklopropanol;
N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-N8-(1-metilpiperidin-4-il)pirido[3,4-d]pirimidin-2,8-diamin;
2-((2-((2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)amino)pirido[3,4-d]pirimidin-8-il)amino)-2-metilpropan-1-ol;
N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-8-(2-oksa-6-azaspiro[3.3]heptan-6-il)pirido[3,4-d]pirimidin-2-amin;
N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-N8-(oksetan-2-ilmetil)pirido[3,4-d]pirimidin-2,8-diamin;
N2-(2-kloro-4-morfolinofenil)-N8-neopentilpirido[3,4-d]pirimidin-2,8-diamin
N2-(2-metoksi-4-(4-metil-4H-1,2,4-triazol-3-il)fenil)-N8-neopentilpirido[3,4-d]pirimidin-2,8-diamin;
N2-(2-metoksi-4-(4-(metilsulfonil)piperazin-1-il)fenil)-N8-neopentilpirido[3,4-d]pirimidin-2,8-diamin;
N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-N8-((3-metiltetrahidrofuran-3-il)metil)pirido[3,4-d]pirimidin-2,8-diamin;
N-(4-(1,5-dimetil-1H-pirazol-4-il)-2-metoksifenil)-8-(2-oksa-6-azaspiro[3.4]oktan-6-il)pirido[3,4-d]pirimidin-2-amin;
N2-(4-(1,5-dimetil-1H-pirazol-4-il)-2-metoksifenil)-N8-((3-metiloksetan-3-il)metil)pirido[3,4-d]pirimidin-2,8-diamin;
N2-(4-(1,5-dimetil-1H-pirazol-4-il)-2-metoksifenil)-N8-(2-metoksi-2-metilpropil)pirido[3,4-d]pirimidin-2,8-diamin;
N2-(4-(1,2-dimetil-1H-imidazol-5-il)-2-metoksifenil)-N8-(2-metoksi-2-metilpropil)-6-metilpirido[3,4-d]pirimidin-2,8-diamin;
N2-(4-(1,2-dimetil-1H-imidazol-5-il)-2-metoksifenil)-6-metil-N8-neopentilpirido[3,4-d]pirimidin-2,8-diamin;
N2-(2-metoksi-4-(4-metil-4H-1,2,4-triazol-3-il)fenil)-6-metil-N8-neopentilpirido[3,4-d]pirimidin-2,8-diamin;
N-(2-etoksi-4-(1-metil-1H-pirazol-4-il)fenil)-8-(2-oksa-6-azaspiro[3.4]oktan-6-il)pirido[3,4-d]pirimidin-2-amin;
2-((2-((2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)amino)pirido[3,4-d]pirimidin-8-il)amino)etanol;
N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-N8-(2-metoksietil)pirido[3,4-d]pirimidin-2,8-diamin;
1-((2-((2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)amino)pirido[3,4-d]pirimidin-8-il)amino)propan-2-ol;
2-((2-((2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)amino)pirido[3,4-d]pirimidin-8-il)amino)propan-1-ol;
N2-(4-(1,5-dimetil-1H-pirazol-4-il)-2-metoksifenil)-N8-((3-metiltetrahidrofuran-3-il)metil)pirido[3,4-d]pirimidin-2,8-diamin;
4-(2-((2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)amino)pirido[3,4-d]pirimidin-8-il)tiomorfolin 1.1-dioksid;
N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-8-(7-oksa-2-azaspiro[3.5]nonan-2-il)pirido[3,4-d]pirimidin-2-amin;
N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-5-metil-N8-neopentilpirido[3,4-d]pirimidin-2,8-diamin;
N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-8-(6-oksa-2-azaspiro[3.4]oktan-2-il)pirido[3,4-d]pirimidin-2-amin;
1-(2-((2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)amino)pirido[3,4-d]pirimidin-8-il)azetidin-3-karbonitril;
N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-8-(2-oksa-7-azaspiro[4.4]nonan-7-il)pirido[3,4-d]pirimidin-2-amin;
N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-8-(2-oksa-6-azaspiro[3.5]nonan-6-il)pirido[3,4-d]pirimidin-2-amin;
N8-((3-fluorooksetan-3-il)metil)-N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)pirido[3,4-d]pirimidin-2,8-diamin;
N-(4-kloro-2-metoksifenil)-8-(2-oksa-6-azaspiro[3.4]oktan-6-il)pirido[3,4-d]pirimidin-2-amin;
N-(2,4-diklorofenil)-8-(2-oksa-6-azaspiro[3.4]oktan-6-il)pirido[3,4-d]pirimidin-2-amin;
4-((8-(2-oksa-6-azaspiro[3.4]oktan-6-il)pirido[3,4-d]pirimidin-2-il)amino)-3-metoksibenzonitril;
N-(2-kloro-4-(metilsulfonil)fenil)-8-(2-oksa-6-azaspiro[3.4]oktan-6-il)pirido[3,4-d]pirimidin-2-amin;
N-(2-kloro-4-(pirimidin-5-il)fenil)-8-(2-oksa-6-azaspiro[3.4]oktan-6-il)pirido[3,4-d]pirimidin-2-amin;
N-(2-kloro-4-(5-metil-1,3,4-oksadiazol-2-il)fenil)-8-(2-oksa-6-azaspiro[3.4]oktan-6-il)pirido[3,4-d]pirimidin-2-amin;
N8-(2-metoksi-2-metilpropil)-N2-(2-metoksi-4-(4-metil-4H-1,2,4-triazol-3-il)fenil)-6-metilpirido[3,4-d]pirimidin-2,8-diamin;
6-ciklopropil-N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-8-(2-oksa-6-azaspiro[3.4]oktan-6-il)pirido[3,4-d]pirimidin-2-amin;
2-((2-((2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)amino)pirido[3,4-d]pirimidin-8-il)amino)propan-1,3-diol;
3-metoksi-2-((2-((2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)amino)pirido[3,4-d]pirimidin-8-il)amino)propan-1-ol;
(3-(((2-((2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)amino)pirido[3,4-d]pirimidin-8-il)amino)metil)oksetan-3-il)metanol;
(S)-N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-N8-((3-metiltetrahidrofuran-3-il)metil)pirido[3,4-d]pirimidin-2,8-diamin;
(R)-N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-N8-((3-metiltetrahidrofuran-3-il)metil)pirido[3,4-d]pirimidin-2,8-diamin;
N-(4-kloro-2-fluorofenil)-8-(2-oksa-6-azaspiro[3.4]oktan-6-il)pirido[3,4-d]pirimidin-2-amin;
4-((8-(2-oksa-6-azaspiro[3.4]oktan-6-il)pirido[3,4-d]pirimidin-2-il)amino)-3-klorobenzonitril;
N2-(2-metoksi-4-(1-(2-metoksietil)-2-metil-1H-imidazol-5-il)fenil)-6-metil-N8-neopentilpirido[3,4-d]pirimidin-2,8-diamin;
N2-(2-etoksi-4-(4-metil-4H-1,2,4-triazol-3-il)fenil)-6-metil-N8-neopentilpirido[3,4-d]pirimidin-2,8-diamin;
N2-(2-metoksi-4-(4-(metilsulfonil)piperazin-1-il)fenil)-6-metil-N8-neopentilpirido[3,4-d]pirimidin-2,8-diamin;
N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-8-(piridin -4-il)pirido[3,4-d]pirimidin-2-amin;
N8-(2-metoksi-2-metilpropil)-N2-(2-metoksi-4-(4-metil-4H-1,2,4-triazol-3-il)fenil)-5-metilpirido[3,4-d]pirimidin-2,8-diamin;
N2-(2-metoksi-4-(4-metil-4H-1,2,4-triazol-3-il)fenil)-5-metil-N8-neopentilpirido[3,4-d]pirimidin-2,8-diamin;
N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-8-(2-metilmorfolino)pirido[3,4-d]pirimidin-2-amin;
(4-(3-metoksi-4-((8-((2-metoksi-2-metilpropil)amino)pirido[3,4-d]pirimidin-2-il)amino)fenil)-1-metil-1H-pirazol-5-il)metanol;
(4-(3-metoksi-4-((8-(((3-metiltetrahidrofuran-3-il)metil)amino)pirido[3,4-d]pirimidin-2-il)amino)fenil)-1-metil-1H-pirazol-5-il)metanol;
N8-(2-metoksi-2-metilpropil)-N2-(2-metoksi-4-(1-(2-metoksietil)-2-metil-1H-imidazol-5-il)fenil)pirido[3,4-d]pirimidin-2,8-diamin;
N2-(2-metoksi-4-(1-(2-metoksietil)-2-metil-1H-imidazol-5-il)fenil)-N8-((3-metiltetrahidrofuran-3-il)metil)pirido[3,4-d]pirimidin-2,8-diamin;
N2-(2-etoksi-4-(4-metil-4H-1,2,4-triazol-3-il)fenil)-N8-(2-metoksi-2-metilpropil)pirido[3,4-d]pirimidin-2,8-diamin;
N2-(2-etoksi-4-(4-metil-4H-1,2,4-triazol-3-il)fenil)-N8-((3-metiltetrahidrofuran-3-il)metil)pirido[3,4-d]pirimidin-2,8-diamin;
8-(3,6-dihidro-2H-piran-4-il)-N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)pirido[3,4-d]pirimidin-2-amin;
N8-(2-metoksi-2-metilpropil)-N2-(2-metoksi-6-(1-metil-1H-tetrazol-5-il)piridin-3-il)pirido[3,4-d]pirimidin-2,8-diamin;
N2-(6-(1,2-dimetil-1H-imidazol-5-il)-2-metoksipiridin-3-il)-N8-(2-metoksi-2-metilpropil)pirido[3,4-d]pirimidin-2,8-diamin;
N8-(2-metoksi-2-metilpropil)-N2-(2-metoksi-4-(1-metil-1H-tetrazol-5-il)fenil)pirido[3,4-d]pirimidin-2,8-diamin;
N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-8-(pirimidin-5-il)pirido[3,4-d]pirimidin-2-amin;
N2-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-N8-(1-(tetrahidrofuran-3-il)etil)pirido[3,4-d]pirimidin-2,8-diamin;
N2-(4-(1,3-dimetil-1H-pirazol-4-il)-2-metoksifenil)-N8-(2-metoksi-2-metilpropil)pirido[3,4-d]pirimidin-2,8-diamin;
N2-(4-(1,3-dimetil-1H-pirazol-4-il)-2-metoksifenil)-N8-((3-metiltetrahidrofuran-3-il)metil)pirido[3,4-d]pirimidin-2,8-diamin;
N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-8-(4-metoksipiperidin-1-il)pirido[3,4-d]pirimidin-2-amin;
1-(2-((2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)amino)pirido[3,4-d]pirimidin-8-il)piperidin-4-karbonitril;
N-(2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)-8-(4-(metilsulfonil)piperazin-1-il)pirido[3,4-d]pirimidin-2-amin;
N2-(4-(1,3-dimetil-1H-pirazol-4-il)-2-metoksifenil)-N8-(2-metoksi-2-metilpropil)-6-metilpirido[3,4-d]pirimidin-2,8-diamin;
N-(2-etoksi-4-(4-metil-4H-1,2,4-triazol-3-il)fenil)-6-metil-8-(6-oksa-2-azaspiro[3.4]oktan-2-il)pirido[3,4-d]pirimidin-2-amin;
N2-(6-(1,3-dimetil-1H-pirazol-4-il)-2-metoksipiridin-3-il)-N8-(2-metoksi-2-metilpropil)pirido[3,4-d]pirimidin-2,8-diamin;
N2-(6-(1,5-dimetil-1H-pirazol-4-il)-2-metoksipiridin-3-il)-N8-(2-metoksi-2-metilpropil)pirido[3,4-d]pirimidin-2,8-diamin;
N8-(2-metoksi-2-metilpropil)-N2-(2-metoksi-6-(1-metil-1H-1,2,3-triazol-5-il)piridin-3-il)pirido[3,4-d]pirimidin-2,8-diamin;
N8-(2-metoksi-2-metilpropil)-N2-(2-metoksi-6-(2-metil-2H-1,2,3-triazol-4-il)piridin-3-il)pirido[3,4-d]pirimidin-2,8-diamin;
(3-metoksi-4-((8-((2-metoksi-2-metilpropil)amino)pirido[3,4-d]pirimidin-2-il)amino)fenil)(3-metoksiazetidin-1-il)metanon;
3-metoksi-4-((8-((2-metoksi-2-metilpropil)amino)pirido[3,4-d]pirimidin-2-il)amino)-N,N-dimetilbenzamid;
(3-metoksi-4-((8-((2-metoksi-2-metilpropil)amino)pirido[3,4-d]pirimidin-2-il)amino)fenil)(4-metilpiperazin-1-il)metanon;
(1-(2-((2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)amino)pirido[3,4-d]pirimidin-8-il)pirolidin-3-il)metanol;
(1-(2-((2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)amino)pirido[3,4-d]pirimidin-8-il)piperidin-3-il)metanol;
(4-(2-((2-metoksi-4-(1-metil-1H-pirazol-4-il)fenil)amino)pirido[3,4-d]pirimidin-8-il)morfolin-2-il)metanol;
N2-(2-(difluorometoksi)-4-(1-metil-1H-pirazol-4-il)fenil)-N8-(2-metoksi-2-metilpropil)pirido[3,4-d]pirimidin-2,8-diamin;
N2-(2-(difluorometoksi)-4-fluorofenil)-N8-(2-metoksi-2-metilpropil)pirido[3,4-d]pirimidin-2,8-diamin;
N2-(4-(1-etil-1H-pirazol-4-il)-2-metoksifenil)-N8-(2-metoksi-2-metilpropil)pirido[3,4-d]pirimidin-2,8-diamin;
(3-metoksi-4-((8-(neopentilamino)pirido[3,4-d]pirimidin-2-il)amino)fenil)(3-metoksiazetidin-1-il)metanon;
N2-(2-metoksi-4-(tetrahidro-2H-piran-4-il)fenil)-N8-((3-metiltetrahidrofuran-3-il)metil)pirido[3,4-d]pirimidin-2,8-diamin;
N2-(4-kloro-2-(difluorometoksi)fenil)-N8-(2-metoksi-2-metilpropil)pirido[3,4-d]pirimidin-2,8-diamin;
N2-(2-metoksi-4-(4-metil-4H-1,2,4-triazol-3-il)fenil)-5-metil-N8-((3-metiloksetan-3-il)metil)pirido[3,4-d]pirimidin-2,8-diamin;
N2-(2-metoksi-4-(4-metil-4H-1,2,4-triazol-3-il)fenil)-5-metil-N8-((3-metiltetrahidrofuran-3-il)metil)pirido[3,4-d]pirimidin-2,8-diamin;
N-(2-metoksi-4-(4-metil-4H-1,2,4-triazol-3-il)fenil)-5-metil-8-(6-oksa-2-azaspiro[3.4]oktan-2-il)pirido[3,4-d]pirimidin-2-amin;
N8-(2-metoksi-2-metilpropil)-N2-(2-metoksi-4-(1-metil-1H-1,2,4-triazol-3-il)fenil)-6-metilpirido[3,4-d]pirimidin-2,8-diamin;
N2-(2-(difluorometoksi)-4-(1-metil-1H-pirazol-4-il)fenil)-N8-(2-metoksi-2-metilpropil)-6-metilpirido[3,4-d]pirimidin-2,8-diamin;
(4-(3-metoksi-4-((8-((2-metoksi-2-metilpropil)amino)-6-metilpirido[3,4-d]pirimidin-2-il)amino)fenil)-1-metil-1H-pirazol-5-il)metanol;
ili njegova farmaceutski prihvatljiva sol ili solvat.
12. Spoj u skladu s bilo kojim od prethodnih patentnih zahtjeva 1 do 11, ili njegova farmaceutski prihvatljiva sol ili solvat, koji se koriste pri liječenju.
13. Spoj u skladu s bilo kojim od prethodnih patentnih zahtjeva 1 do 11, ili njegova farmaceutski prihvatljiva sol ili solvat, koji se koriste pri liječenju karcinoma.
14. Farmaceutski pripravak koji sadrži spoj u skladu s patentnim zahtjevima 1 do 11, ili njegovu farmaceutski prihvatljivu sol ili solvat, u sjmesi s farmaceutski prihvatljivim otapalom ili nosačem.
15. Postupak za sintetiziranje spoja formule I, ili njegove farmaceutski prihvatljive soli ili solvata, sukladno patentnom zahtjevu 1, pri čemu postupak sadrži:
a) reakciju spoja formule A:
[image]
gdje W, X, Z, R1 i R4 su svaki kao što su definirani u patentnom zahtjevu 1, i LGA je pogodna odlazeća skupina;
sa spojem formule B:
H2N-Ar Formula B
gdje Ar je kao što je definiran u patentnom zahtjevu 1; ili
b) reakcija spoja formule C:
[image]
gdje W, X, Z, R1 i R4 su kao što su definirani u patentnom zahtjevu 1;
sa spojem formule B kao što je definirano u (a) u prethodnom tekstu, ili spoj formule D:
HC(O)HN-Ar Formula D
gdje Ar je kao što je definiran u patentnom zahtjevu 1; ili
a) reakcija spoja formule E:
[image]
gdje W, X, Z, Ar i R4 su kao što su definirani u patentnom zahtjevu 1, i LGA je pogodna odlazeća skupina kao što je ovjde u prethodnom tekstu definirana;
sa spojem formule F:
H2N-R1 Formula F
gdje R1 je kao što je definiran u patentnom zahtjevu 1;
i izborno zatim, i ako je neophodno:
i) uklanjanje svih prisutnih zaštitnih skupina;
ii) prevođenje spoja formule I u drugi spoj formule I; i/ili
iii) tvorba njegove farmaceutski prihvatljive soli ili solvata.
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GBGB1216017.2A GB201216017D0 (en) | 2012-09-07 | 2012-09-07 | Inhibitor compounds |
EP13760106.8A EP2892889B1 (en) | 2012-09-07 | 2013-09-09 | Inhibitor compounds |
PCT/GB2013/052360 WO2014037750A1 (en) | 2012-09-07 | 2013-09-09 | Inhibitor compounds |
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HRP20171835T1 true HRP20171835T1 (hr) | 2017-12-29 |
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HRP20171835TT HRP20171835T1 (hr) | 2012-09-07 | 2017-11-24 | Inhibitorni spojevi |
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US (6) | US9409907B2 (hr) |
EP (2) | EP3293183B1 (hr) |
JP (2) | JP6216791B2 (hr) |
CN (1) | CN104837829B (hr) |
AU (2) | AU2013311434B2 (hr) |
BR (1) | BR112015004489B1 (hr) |
CA (1) | CA2884006C (hr) |
CY (1) | CY1119714T1 (hr) |
DK (2) | DK3293183T3 (hr) |
ES (2) | ES2655194T3 (hr) |
GB (1) | GB201216017D0 (hr) |
HK (1) | HK1211921A1 (hr) |
HR (1) | HRP20171835T1 (hr) |
HU (1) | HUE036259T2 (hr) |
LT (1) | LT2892889T (hr) |
NO (1) | NO2892889T3 (hr) |
PL (1) | PL2892889T3 (hr) |
PT (1) | PT2892889T (hr) |
RS (1) | RS56750B1 (hr) |
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