JP2013534233A - 選択的ｊａｋ阻害剤としてのヘテロシクリルピラゾロピリミジン類似体 - Google Patents

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Publication number

JP2013534233A

JP2013534233A JP2013524421A JP2013524421A JP2013534233A JP 2013534233 A JP2013534233 A JP 2013534233A JP 2013524421 A JP2013524421 A JP 2013524421A JP 2013524421 A JP2013524421 A JP 2013524421A JP 2013534233 A JP2013534233 A JP 2013534233A

Authority

JP

Japan

Prior art keywords

methyl

pyrazol

pyrazolo

pyrimidin

amino

Prior art date

2010-08-20

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.)

Pending

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• 229940122245 Janus kinase inhibitor Drugs 0.000 title abstract description 7
• 150000001875 compounds Chemical class 0.000 claims abstract description 242
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 57
• 201000010099 disease Diseases 0.000 claims abstract description 32
• 238000011282 treatment Methods 0.000 claims abstract description 23
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 19
• 230000000172 allergic effect Effects 0.000 claims abstract description 9
• 208000010668 atopic eczema Diseases 0.000 claims abstract description 9
• 230000001363 autoimmune Effects 0.000 claims abstract description 9
• 230000002757 inflammatory effect Effects 0.000 claims abstract description 9
• 230000002265 prevention Effects 0.000 claims abstract description 8
• 239000008177 pharmaceutical agent Substances 0.000 claims abstract description 5
• 238000000034 method Methods 0.000 claims description 326
• -1 heterocyclyl compound Chemical class 0.000 claims description 89
• 125000000217 alkyl group Chemical group 0.000 claims description 82
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 56
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 55
• 229910052739 hydrogen Inorganic materials 0.000 claims description 41
• 229910052736 halogen Inorganic materials 0.000 claims description 40
• 150000003839 salts Chemical class 0.000 claims description 38
• 150000002367 halogens Chemical class 0.000 claims description 32
• 229920006395 saturated elastomer Polymers 0.000 claims description 30
• 208000035475 disorder Diseases 0.000 claims description 24
• 125000000623 heterocyclic group Chemical group 0.000 claims description 23
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
• 229910052757 nitrogen Inorganic materials 0.000 claims description 22
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
• 229910052799 carbon Inorganic materials 0.000 claims description 13
• 206010052779 Transplant rejections Diseases 0.000 claims description 10
• 208000024908 graft versus host disease Diseases 0.000 claims description 10
• 239000002207 metabolite Substances 0.000 claims description 10
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
• 229940002612 prodrug Drugs 0.000 claims description 9
• 239000000651 prodrug Substances 0.000 claims description 9
• 230000002062 proliferating effect Effects 0.000 claims description 9
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 8
• 208000009329 Graft vs Host Disease Diseases 0.000 claims description 8
• 125000000304 alkynyl group Chemical group 0.000 claims description 8
• 208000037765 diseases and disorders Diseases 0.000 claims description 8
• 125000005843 halogen group Chemical group 0.000 claims description 8
• 125000003342 alkenyl group Chemical group 0.000 claims description 7
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 229910052717 sulfur Inorganic materials 0.000 claims description 6
• ZVLOCMSXMRKPDV-UHFFFAOYSA-N 4-[3-[[6-[(1-methylpyrazol-4-yl)amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]phenyl]morpholin-3-one Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C=C(C=CC=3)N3C(COCC3)=O)C2=N1 ZVLOCMSXMRKPDV-UHFFFAOYSA-N 0.000 claims description 5
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• VSEAAEQOQBMPQF-UHFFFAOYSA-N morpholin-3-one Chemical compound O=C1COCCN1 VSEAAEQOQBMPQF-UHFFFAOYSA-N 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• LCLFUUUFFSKKRQ-UHFFFAOYSA-N 1-[(2-fluoro-3-piperazin-1-ylphenyl)methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=C(N4CCNCC4)C=CC=3)F)C2=N1 LCLFUUUFFSKKRQ-UHFFFAOYSA-N 0.000 claims description 4
• UTOMTFZIGBUZJC-UHFFFAOYSA-N 1-[(3-fluoro-5-morpholin-4-ylphenyl)methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C=C(C=C(F)C=3)N3CCOCC3)C2=N1 UTOMTFZIGBUZJC-UHFFFAOYSA-N 0.000 claims description 4
• KVSYZIDXSXHKCJ-UHFFFAOYSA-N 2-[4-(1h-pyrazolo[3,4-d]pyrimidin-6-ylamino)pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(C=NN2)C2=N1 KVSYZIDXSXHKCJ-UHFFFAOYSA-N 0.000 claims description 4
• YIEBDLBEOOYPKH-UHFFFAOYSA-N 4-[2,4,5-trifluoro-3-[[6-[(1-methylpyrazol-4-yl)amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]phenyl]morpholin-3-one Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=C(N4C(COCC4)=O)C=C(F)C=3F)F)C2=N1 YIEBDLBEOOYPKH-UHFFFAOYSA-N 0.000 claims description 4
• PUTTZUSRYCVDCO-UHFFFAOYSA-N 4-[3,4-difluoro-5-[[6-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]phenyl]morpholin-3-one Chemical compound C1=NN(CCO)C=C1NC1=NC=C(C=NN2CC=3C(=C(F)C=C(C=3)N3C(COCC3)=O)F)C2=N1 PUTTZUSRYCVDCO-UHFFFAOYSA-N 0.000 claims description 4
• MJHNNNYIOSCRRS-UHFFFAOYSA-N 4-[3-[[6-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]phenyl]morpholin-3-one Chemical compound C1=NN(CCO)C=C1NC1=NC=C(C=NN2CC=3C=C(C=CC=3)N3C(COCC3)=O)C2=N1 MJHNNNYIOSCRRS-UHFFFAOYSA-N 0.000 claims description 4
• POOPWPIOIMBTOH-UHFFFAOYSA-N 8-oxa-3-azabicyclo[3.2.1]octane Chemical compound C1NCC2CCC1O2 POOPWPIOIMBTOH-UHFFFAOYSA-N 0.000 claims description 4
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 4
• WHWXPCVUBTVRMO-UHFFFAOYSA-N [3-[[6-[(1-methylpyrazol-4-yl)amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]phenyl]-morpholin-4-ylmethanone Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C=C(C=CC=3)C(=O)N3CCOCC3)C2=N1 WHWXPCVUBTVRMO-UHFFFAOYSA-N 0.000 claims description 4
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 4
• 125000002757 morpholinyl group Chemical group 0.000 claims description 4
• XFWXERCRRYGSOY-UHFFFAOYSA-N n-(1-methylpyrazol-4-yl)-1-[[3-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)phenyl]methyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C=C(C=CC=3)N3CC4CCC(O4)C3)C2=N1 XFWXERCRRYGSOY-UHFFFAOYSA-N 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• WIAQVEOZEVXBLK-UHFFFAOYSA-N 1-(dimethylamino)-3-[4-[[1-[(3-morpholin-4-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]pyrazol-1-yl]propan-2-ol Chemical compound C1=NN(CC(O)CN(C)C)C=C1NC1=NC=C(C=NN2CC=3C=C(C=CC=3)N3CCOCC3)C2=N1 WIAQVEOZEVXBLK-UHFFFAOYSA-N 0.000 claims description 3
• AIPWKMARVVQHIZ-UHFFFAOYSA-N 1-[(2,3-difluoro-5-morpholin-4-ylphenyl)methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=C(F)C=C(C=3)N3CCOCC3)F)C2=N1 AIPWKMARVVQHIZ-UHFFFAOYSA-N 0.000 claims description 3
• IOHPHOVOIWXLOQ-UHFFFAOYSA-N 1-[(2,3-difluoro-5-piperazin-1-ylphenyl)methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=C(F)C=C(C=3)N3CCNCC3)F)C2=N1 IOHPHOVOIWXLOQ-UHFFFAOYSA-N 0.000 claims description 3
• IBJINTQEVNSIPA-UHFFFAOYSA-N 1-[(2,6-difluoro-3-morpholin-4-ylphenyl)methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=C(N4CCOCC4)C=CC=3F)F)C2=N1 IBJINTQEVNSIPA-UHFFFAOYSA-N 0.000 claims description 3
• TTXQDRDDHYSWCG-UHFFFAOYSA-N 1-[(2-fluoro-3-morpholin-4-ylphenyl)methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=C(N4CCOCC4)C=CC=3)F)C2=N1 TTXQDRDDHYSWCG-UHFFFAOYSA-N 0.000 claims description 3
• DXJLNSJZOYPILI-UHFFFAOYSA-N 1-[(2-fluoro-5-morpholin-4-ylphenyl)methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=CC=C(C=3)N3CCOCC3)F)C2=N1 DXJLNSJZOYPILI-UHFFFAOYSA-N 0.000 claims description 3
• XPNKQYYVMWJGIP-UHFFFAOYSA-N 1-[(2-methyl-3-morpholin-4-ylphenyl)methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC=C(N2CCOCC2)C(C)=C1CN(C1=N2)N=CC1=CN=C2NC=1C=NN(C)C=1 XPNKQYYVMWJGIP-UHFFFAOYSA-N 0.000 claims description 3
• KQFDSKUATBKDQT-UHFFFAOYSA-N 1-[(3-morpholin-4-ylphenyl)methyl]-n-[1-(piperidin-3-ylmethyl)pyrazol-4-yl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=C(NC=2N=C3N(CC=4C=C(C=CC=4)N4CCOCC4)N=CC3=CN=2)C=NN1CC1CCCNC1 KQFDSKUATBKDQT-UHFFFAOYSA-N 0.000 claims description 3
• JMLXWLDQGXMEHE-UHFFFAOYSA-N 1-[(3-morpholin-4-ylphenyl)methyl]-n-[1-(pyrrolidin-3-ylmethyl)pyrazol-4-yl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=C(NC=2N=C3N(CC=4C=C(C=CC=4)N4CCOCC4)N=CC3=CN=2)C=NN1CC1CCNC1 JMLXWLDQGXMEHE-UHFFFAOYSA-N 0.000 claims description 3
• QJIWPIMERUHTCJ-UHFFFAOYSA-N 1-[2,4-difluoro-3-[[6-[(1-methylpyrazol-4-yl)amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]phenyl]piperazin-2-one Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=C(N4C(CNCC4)=O)C=CC=3F)F)C2=N1 QJIWPIMERUHTCJ-UHFFFAOYSA-N 0.000 claims description 3
• WXELJEBIOJRVCJ-UHFFFAOYSA-N 1-[2-fluoro-3-[[6-[(1-methylpyrazol-4-yl)amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]phenyl]piperazin-2-one Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=C(N4C(CNCC4)=O)C=CC=3)F)C2=N1 WXELJEBIOJRVCJ-UHFFFAOYSA-N 0.000 claims description 3
• BTVOZQZBAOSNOE-UHFFFAOYSA-N 1-[2-fluoro-3-[[6-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]phenyl]piperazin-2-one Chemical compound C1=NN(CCO)C=C1NC1=NC=C(C=NN2CC=3C(=C(N4C(CNCC4)=O)C=CC=3)F)C2=N1 BTVOZQZBAOSNOE-UHFFFAOYSA-N 0.000 claims description 3
• JQUASVYSBGGPMN-UHFFFAOYSA-N 1-[3,4-difluoro-5-[[6-[(1-methylpyrazol-4-yl)amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]phenyl]piperazin-2-one Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=C(F)C=C(C=3)N3C(CNCC3)=O)F)C2=N1 JQUASVYSBGGPMN-UHFFFAOYSA-N 0.000 claims description 3
• RDBOBWQYTXNMOO-UHFFFAOYSA-N 1-[3,4-difluoro-5-[[6-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]phenyl]piperazin-2-one Chemical compound C1=NN(CCO)C=C1NC1=NC=C(C=NN2CC=3C(=C(F)C=C(C=3)N3C(CNCC3)=O)F)C2=N1 RDBOBWQYTXNMOO-UHFFFAOYSA-N 0.000 claims description 3
• SPYBDNGMYOLKKT-UHFFFAOYSA-N 1-[3-[4-[[1-[(3-morpholin-4-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]pyrazol-1-yl]propyl]pyrrolidin-2-one Chemical compound O=C1CCCN1CCCN1N=CC(NC=2N=C3N(CC=4C=C(C=CC=4)N4CCOCC4)N=CC3=CN=2)=C1 SPYBDNGMYOLKKT-UHFFFAOYSA-N 0.000 claims description 3
• BNTKLVFPGMSLPS-UHFFFAOYSA-N 1-[3-[[6-[(1-methylpyrazol-4-yl)amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]phenyl]piperazin-2-one Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C=C(C=CC=3)N3C(CNCC3)=O)C2=N1 BNTKLVFPGMSLPS-UHFFFAOYSA-N 0.000 claims description 3
• WRQWPHAULJEKEJ-UHFFFAOYSA-N 1-[3-[[6-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]phenyl]piperazin-2-one Chemical compound C1=NN(CCO)C=C1NC1=NC=C(C=NN2CC=3C=C(C=CC=3)N3C(CNCC3)=O)C2=N1 WRQWPHAULJEKEJ-UHFFFAOYSA-N 0.000 claims description 3
• HLHPEQUSUXNOGX-UHFFFAOYSA-N 1-[3-fluoro-5-[[6-[(1-methylpyrazol-4-yl)amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]phenyl]piperazin-2-one Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C=C(C=C(F)C=3)N3C(CNCC3)=O)C2=N1 HLHPEQUSUXNOGX-UHFFFAOYSA-N 0.000 claims description 3
• RQAUXJQYPZFDHH-UHFFFAOYSA-N 1-[3-fluoro-5-[[6-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]phenyl]piperazin-2-one Chemical compound C1=NN(CCO)C=C1NC1=NC=C(C=NN2CC=3C=C(C=C(F)C=3)N3C(CNCC3)=O)C2=N1 RQAUXJQYPZFDHH-UHFFFAOYSA-N 0.000 claims description 3
• OJFIRFVBSDGLRA-UHFFFAOYSA-N 1-[[2-fluoro-3-(2-oxa-6-azaspiro[3.3]heptan-6-yl)phenyl]methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C(=C(N4CC5(COC5)C4)C=CC=3)F)C2=N1 OJFIRFVBSDGLRA-UHFFFAOYSA-N 0.000 claims description 3
• WFJVTASXQBMCIJ-UHFFFAOYSA-N 1-[[3-(1,1-dioxo-1,4-thiazinan-4-yl)phenyl]methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C=C(C=CC=3)N3CCS(=O)(=O)CC3)C2=N1 WFJVTASXQBMCIJ-UHFFFAOYSA-N 0.000 claims description 3
• DLEKHBZBTGJFAS-UHFFFAOYSA-N 1-[[3-(3-methoxyazetidin-1-yl)phenyl]methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1C(OC)CN1C1=CC=CC(CN2C3=NC(NC4=CN(C)N=C4)=NC=C3C=N2)=C1 DLEKHBZBTGJFAS-UHFFFAOYSA-N 0.000 claims description 3
• DLTRTXBWIQHSTB-UHFFFAOYSA-N 1-[[3-(4,4-difluoropiperidin-1-yl)phenyl]methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical class C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C=C(C=CC=3)N3CCC(F)(F)CC3)C2=N1 DLTRTXBWIQHSTB-UHFFFAOYSA-N 0.000 claims description 3
• FSMNQKHHJYPTFO-UHFFFAOYSA-N 1-[[3-(4-methoxypiperidin-1-yl)phenyl]methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CC(OC)CCN1C1=CC=CC(CN2C3=NC(NC4=CN(C)N=C4)=NC=C3C=N2)=C1 FSMNQKHHJYPTFO-UHFFFAOYSA-N 0.000 claims description 3
• UEBQTSPICQTRGC-UHFFFAOYSA-N 1-[[3-(4-methylpiperazin-1-yl)phenyl]methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CN(C)CCN1C1=CC=CC(CN2C3=NC(NC4=CN(C)N=C4)=NC=C3C=N2)=C1 UEBQTSPICQTRGC-UHFFFAOYSA-N 0.000 claims description 3
• NKSBPJOOITYGIE-UHFFFAOYSA-N 1-[[3-fluoro-5-(2-oxa-6-azaspiro[3.3]heptan-6-yl)phenyl]methyl]-n-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=NN2CC=3C=C(C=C(F)C=3)N3CC4(COC4)C3)C2=N1 NKSBPJOOITYGIE-UHFFFAOYSA-N 0.000 claims description 3
• IDHAVUSUUCAQSL-UHFFFAOYSA-N 2-[4-[[1-[(2,3-difluoro-5-morpholin-4-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(C=NN2CC=3C(=C(F)C=C(C=3)N3CCOCC3)F)C2=N1 IDHAVUSUUCAQSL-UHFFFAOYSA-N 0.000 claims description 3
• PLMVRZSABYUHTI-UHFFFAOYSA-N 2-[4-[[1-[(2,3-difluoro-5-piperazin-1-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(C=NN2CC=3C(=C(F)C=C(C=3)N3CCNCC3)F)C2=N1 PLMVRZSABYUHTI-UHFFFAOYSA-N 0.000 claims description 3
• LBZVZBGLGGAFIE-UHFFFAOYSA-N 2-[4-[[1-[(2,6-difluoro-3-morpholin-4-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(C=NN2CC=3C(=C(N4CCOCC4)C=CC=3F)F)C2=N1 LBZVZBGLGGAFIE-UHFFFAOYSA-N 0.000 claims description 3
• XVEQQWBZJQGFSC-UHFFFAOYSA-N 2-[4-[[1-[(2-fluoro-3-morpholin-4-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(C=NN2CC=3C(=C(N4CCOCC4)C=CC=3)F)C2=N1 XVEQQWBZJQGFSC-UHFFFAOYSA-N 0.000 claims description 3
• AMLWWPHPIOSFIP-UHFFFAOYSA-N 2-[4-[[1-[(2-fluoro-5-morpholin-4-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(C=NN2CC=3C(=CC=C(C=3)N3CCOCC3)F)C2=N1 AMLWWPHPIOSFIP-UHFFFAOYSA-N 0.000 claims description 3
• IVFMRWYEJNNOSL-UHFFFAOYSA-N 2-[4-[[1-[(3-fluoro-5-morpholin-4-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(C=NN2CC=3C=C(C=C(F)C=3)N3CCOCC3)C2=N1 IVFMRWYEJNNOSL-UHFFFAOYSA-N 0.000 claims description 3
• ADHYCGHWYPLLIU-UHFFFAOYSA-N 2-[4-[[1-[(3-morpholin-4-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(C=NN2CC=3C=C(C=CC=3)N3CCOCC3)C2=N1 ADHYCGHWYPLLIU-UHFFFAOYSA-N 0.000 claims description 3
• NWJHQZYVBOJLSD-UHFFFAOYSA-N 2-[4-[[1-[(3-piperazin-1-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(C=NN2CC=3C=C(C=CC=3)N3CCNCC3)C2=N1 NWJHQZYVBOJLSD-UHFFFAOYSA-N 0.000 claims description 3
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