JP6964343B2 - ユビキチン特異的プロテアーゼ１阻害剤としてのプリノン - Google Patents

Info

Publication number

JP6964343B2

JP6964343B2 JP2018526219A JP2018526219A JP6964343B2 JP 6964343 B2 JP6964343 B2 JP 6964343B2 JP 2018526219 A JP2018526219 A JP 2018526219A JP 2018526219 A JP2018526219 A JP 2018526219A JP 6964343 B2 JP6964343 B2 JP 6964343B2

Authority

JP

Japan

Prior art keywords

alkyl

methyl

dihydro

benzyl

purine

Prior art date

2015-11-20

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.)

Active

Links

• Espacenet
• Global Dossier
• Discuss

• 101000607909 Homo sapiens Ubiquitin carboxyl-terminal hydrolase 1 Proteins 0.000 title description 76
• 102100039865 Ubiquitin carboxyl-terminal hydrolase 1 Human genes 0.000 title description 67
• 239000003112 inhibitor Substances 0.000 title description 10
• 125000000217 alkyl group Chemical group 0.000 claims description 1068
• 229910052736 halogen Inorganic materials 0.000 claims description 418
• 150000002367 halogens Chemical class 0.000 claims description 417
• 125000003545 alkoxy group Chemical group 0.000 claims description 390
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 369
• -1 2-Isopropylpyridin-3-yl Chemical group 0.000 claims description 314
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 291
• 125000004429 atom Chemical group 0.000 claims description 242
• 125000001188 haloalkyl group Chemical group 0.000 claims description 203
• 125000003118 aryl group Chemical group 0.000 claims description 200
• 125000001072 heteroaryl group Chemical group 0.000 claims description 188
• 150000001875 compounds Chemical class 0.000 claims description 155
• 125000001424 substituent group Chemical group 0.000 claims description 153
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 144
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 127
• 125000003342 alkenyl group Chemical group 0.000 claims description 97
• 125000000304 alkynyl group Chemical group 0.000 claims description 84
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 67
• 150000003839 salts Chemical class 0.000 claims description 46
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 26
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
• 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 21
• 229910052757 nitrogen Inorganic materials 0.000 claims description 21
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
• 150000001345 alkine derivatives Chemical class 0.000 claims description 20
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 13
• 125000003003 spiro group Chemical group 0.000 claims description 12
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 6
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 6
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• LYFNAJACLPGPIK-UHFFFAOYSA-N 1-methyl-4-(trifluoromethyl)imidazole Chemical compound CN1C=NC(C(F)(F)F)=C1 LYFNAJACLPGPIK-UHFFFAOYSA-N 0.000 claims description 4
• 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 4
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
• 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 2
• SAVHBHBJVVELRJ-UHFFFAOYSA-N 2-(2,2,2-trifluoroethoxy)pyridine Chemical compound FC(F)(F)COC1=CC=CC=N1 SAVHBHBJVVELRJ-UHFFFAOYSA-N 0.000 claims description 2
• RWEFZQVROUUVNT-UHFFFAOYSA-N 2-(2-butan-2-yloxypyridin-3-yl)-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound C(C)(CC)OC1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O RWEFZQVROUUVNT-UHFFFAOYSA-N 0.000 claims description 2
• CAHLFTMTVJXPRG-UHFFFAOYSA-N 2-(2-cyclobutyloxypyridin-3-yl)-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound C1(CCC1)OC1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O CAHLFTMTVJXPRG-UHFFFAOYSA-N 0.000 claims description 2
• FAQZABJIPIGKQK-UHFFFAOYSA-N 2-(2-cyclopropyloxypyridin-3-yl)-7-methyl-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]purin-8-one Chemical compound C1(CC1)OC1=NC=CC=C1C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O)C FAQZABJIPIGKQK-UHFFFAOYSA-N 0.000 claims description 2
• YJZKRSLHNMCKJP-UHFFFAOYSA-N 2-(2-cyclopropyloxypyridin-3-yl)-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound C1(CC1)OC1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O YJZKRSLHNMCKJP-UHFFFAOYSA-N 0.000 claims description 2
• HFGMWYKAEXEOMP-UHFFFAOYSA-N 2-(2-cyclopropylpyridin-3-yl)-7-methyl-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]purin-8-one Chemical compound C1(CC1)C1=NC=CC=C1C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O)C HFGMWYKAEXEOMP-UHFFFAOYSA-N 0.000 claims description 2
• LSNJOUYKHUSCTD-UHFFFAOYSA-N 2-(2-cyclopropylpyridin-3-yl)-9-[[4-[1-(oxetan-3-yl)-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound C1(CC1)C1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C1COC1)=O LSNJOUYKHUSCTD-UHFFFAOYSA-N 0.000 claims description 2
• LUHWMPWGOKZFNM-UHFFFAOYSA-N 2-(2-cyclopropylpyridin-3-yl)-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound C1(CC1)C1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O LUHWMPWGOKZFNM-UHFFFAOYSA-N 0.000 claims description 2
• LYYDKBZASWUMBX-UHFFFAOYSA-N 2-(2-ethoxypyridin-3-yl)-9-[(4-pyrazol-1-ylphenyl)methyl]-7H-purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C=2C(=NC=CC=2)OCC)C=C1 LYYDKBZASWUMBX-UHFFFAOYSA-N 0.000 claims description 2
• OVRRRELUCKZHCT-UHFFFAOYSA-N 2-(2-ethylpyridin-3-yl)-7-methyl-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]purin-8-one Chemical compound C(C)C1=NC=CC=C1C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O)C OVRRRELUCKZHCT-UHFFFAOYSA-N 0.000 claims description 2
• MQEDYJCBYKWPAU-UHFFFAOYSA-N 2-(2-fluoro-6-methoxypyridin-3-yl)-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound FC1=NC(=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O)OC MQEDYJCBYKWPAU-UHFFFAOYSA-N 0.000 claims description 2
• VAXBJYFUNODPLM-UHFFFAOYSA-N 2-(2-fluoro-6-propan-2-yloxypyridin-3-yl)-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound FC1=NC(=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O)OC(C)C VAXBJYFUNODPLM-UHFFFAOYSA-N 0.000 claims description 2
• WXDQIMGSOLOXOE-UHFFFAOYSA-N 2-(2-propan-2-ylpyridin-3-yl)-9-[(4-pyrazol-1-ylphenyl)methyl]-7H-purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C=2C(=NC=CC=2)C(C)C)C=C1 WXDQIMGSOLOXOE-UHFFFAOYSA-N 0.000 claims description 2
• BNJNTVFLGHJRES-UHFFFAOYSA-N 2-(2-propan-2-ylpyridin-3-yl)-9-[[4-(triazol-2-yl)phenyl]methyl]-7H-purin-8-one Chemical compound N=1N(N=CC=1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C=2C(=NC=CC=2)C(C)C)C=C1 BNJNTVFLGHJRES-UHFFFAOYSA-N 0.000 claims description 2
• MTHNGFBEDBFABP-UHFFFAOYSA-N 2-(5-fluoro-2-propan-2-ylpyridin-3-yl)-7-methyl-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]purin-8-one Chemical compound FC=1C=C(C(=NC=1)C(C)C)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O)C MTHNGFBEDBFABP-UHFFFAOYSA-N 0.000 claims description 2
• IZGHMDXOLZWBBY-UHFFFAOYSA-N 2-(5-fluoro-2-propan-2-ylpyridin-3-yl)-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound FC=1C=C(C(=NC=1)C(C)C)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O IZGHMDXOLZWBBY-UHFFFAOYSA-N 0.000 claims description 2
• XXJAHWQZLWWFTR-UHFFFAOYSA-N 2-(6-fluoro-2-methylpyridin-3-yl)-7-methyl-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]purin-8-one Chemical compound FC1=CC=C(C(=N1)C)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O)C XXJAHWQZLWWFTR-UHFFFAOYSA-N 0.000 claims description 2
• GBINMQRYRGENOX-UHFFFAOYSA-N 2-(6-methoxy-2-methylpyridin-3-yl)-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound COC1=CC=C(C(=N1)C)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O GBINMQRYRGENOX-UHFFFAOYSA-N 0.000 claims description 2
• RNZXHCFYDBJLOT-UHFFFAOYSA-N 2-[2-(2-ethoxyethylamino)pyridin-3-yl]-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound C(C)OCCNC1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O RNZXHCFYDBJLOT-UHFFFAOYSA-N 0.000 claims description 2
• FXDSRJRURBTUHS-UHFFFAOYSA-N 2-[2-(2-methoxyethoxy)pyridin-3-yl]-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound COCCOC1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O FXDSRJRURBTUHS-UHFFFAOYSA-N 0.000 claims description 2
• WGJNDQRHXALTHJ-UHFFFAOYSA-N 2-[2-(2-methylpropoxy)pyridin-3-yl]-9-[[4-(triazol-2-yl)phenyl]methyl]-7H-purin-8-one Chemical compound N=1N(N=CC=1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C=2C(=NC=CC=2)OCC(C)C)C=C1 WGJNDQRHXALTHJ-UHFFFAOYSA-N 0.000 claims description 2
• XAWNDXDGTLCJDC-UHFFFAOYSA-N 2-[2-(2-methylpropoxy)pyridin-3-yl]-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound C(C(C)C)OC1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O XAWNDXDGTLCJDC-UHFFFAOYSA-N 0.000 claims description 2
• FQSWOIGSNIIBNR-UHFFFAOYSA-N 2-[2-(3-fluoroazetidin-1-yl)pyridin-3-yl]-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound FC1CN(C1)C1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O FQSWOIGSNIIBNR-UHFFFAOYSA-N 0.000 claims description 2
• DKAKYYLTMJXGNB-UHFFFAOYSA-N 2-[2-(3-methoxybutoxy)pyridin-3-yl]-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound COC(CCOC1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O)C DKAKYYLTMJXGNB-UHFFFAOYSA-N 0.000 claims description 2
• LYQXKDPHTPKLGK-UHFFFAOYSA-N 2-[2-(4-methylpiperazin-1-yl)pyridin-3-yl]-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound CN1C(=NC(=C1)C(F)(F)F)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C=2C(=NC=CC=2)N2CCN(CC2)C)C=C1 LYQXKDPHTPKLGK-UHFFFAOYSA-N 0.000 claims description 2
• WPIVWBLYPGFXOO-UHFFFAOYSA-N 2-[2-(azetidin-1-yl)pyridin-3-yl]-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound N1(CCC1)C1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O WPIVWBLYPGFXOO-UHFFFAOYSA-N 0.000 claims description 2
• MTWSNUBZMFNVJL-UHFFFAOYSA-N 2-[2-(cyclobutylamino)pyridin-3-yl]-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound C1(CCC1)NC1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O MTWSNUBZMFNVJL-UHFFFAOYSA-N 0.000 claims description 2
• YWWPWXKPZHQGER-UHFFFAOYSA-N 2-[2-(cyclopropylamino)pyridin-3-yl]-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound C1(CC1)NC1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O YWWPWXKPZHQGER-UHFFFAOYSA-N 0.000 claims description 2
• UIXYXTCARNDHPA-UHFFFAOYSA-N 2-[2-(cyclopropylmethoxy)pyridin-3-yl]-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound C1(CC1)COC1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O UIXYXTCARNDHPA-UHFFFAOYSA-N 0.000 claims description 2
• OMLYQTMGTUMFCB-UHFFFAOYSA-N 2-[2-(diethylamino)pyridin-3-yl]-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound C(C)N(C1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O)CC OMLYQTMGTUMFCB-UHFFFAOYSA-N 0.000 claims description 2
• DNGMLAXLAWXEGG-UHFFFAOYSA-N 2-[2-(difluoromethoxy)pyridin-3-yl]-7-methyl-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]purin-8-one Chemical compound FC(OC1=NC=CC=C1C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O)C)F DNGMLAXLAWXEGG-UHFFFAOYSA-N 0.000 claims description 2
• ZVUCCINDFSGCJY-UHFFFAOYSA-N 2-[2-(difluoromethoxy)pyridin-3-yl]-9-[[4-(3-fluoropyrazol-1-yl)phenyl]methyl]-7H-purin-8-one Chemical compound FC(OC1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)N1N=C(C=C1)F)=O)F ZVUCCINDFSGCJY-UHFFFAOYSA-N 0.000 claims description 2
• LSEGNYKXAIGRRB-UHFFFAOYSA-N 2-[2-(difluoromethoxy)pyridin-3-yl]-9-[[4-(triazol-2-yl)phenyl]methyl]-7H-purin-8-one Chemical compound N=1N(N=CC=1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C=2C(=NC=CC=2)OC(F)F)C=C1 LSEGNYKXAIGRRB-UHFFFAOYSA-N 0.000 claims description 2
• CVOAZWPTWVTGGS-UHFFFAOYSA-N 2-[2-(difluoromethoxy)pyridin-3-yl]-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound FC(OC1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O)F CVOAZWPTWVTGGS-UHFFFAOYSA-N 0.000 claims description 2
• QJIDFFOOFLUZAK-UHFFFAOYSA-N 2-[2-(difluoromethyl)pyridin-3-yl]-7-methyl-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]purin-8-one Chemical compound FC(C1=NC=CC=C1C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O)C)F QJIDFFOOFLUZAK-UHFFFAOYSA-N 0.000 claims description 2
• MKDKFDYZOQVHSK-UHFFFAOYSA-N 2-[2-(difluoromethyl)pyridin-3-yl]-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound FC(C1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O)F MKDKFDYZOQVHSK-UHFFFAOYSA-N 0.000 claims description 2
• LHKVKJRDZCUXRA-UHFFFAOYSA-N 2-[2-(ethylamino)pyridin-3-yl]-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound C(C)NC1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O LHKVKJRDZCUXRA-UHFFFAOYSA-N 0.000 claims description 2
• YRRXONHIRZZHBZ-UHFFFAOYSA-N 2-[2-(methylamino)pyridin-3-yl]-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound CN1C(=NC(=C1)C(F)(F)F)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C=2C(=NC=CC=2)NC)C=C1 YRRXONHIRZZHBZ-UHFFFAOYSA-N 0.000 claims description 2
• WKVVYMKNRKIHKC-UHFFFAOYSA-N 2-[2-[2-(dimethylamino)ethoxy]pyridin-3-yl]-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound CN(CCOC1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O)C WKVVYMKNRKIHKC-UHFFFAOYSA-N 0.000 claims description 2
• BDWXDEXONDNHSQ-UHFFFAOYSA-N 2-[2-[2-methoxyethyl(methyl)amino]pyridin-3-yl]-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound COCCN(C1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O)C BDWXDEXONDNHSQ-UHFFFAOYSA-N 0.000 claims description 2
• WRRGGCBUWMJWRN-UHFFFAOYSA-N 2-[2-[ethyl(methyl)amino]pyridin-3-yl]-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound C(C)N(C1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O)C WRRGGCBUWMJWRN-UHFFFAOYSA-N 0.000 claims description 2
• WVCICSQZHQXILA-UHFFFAOYSA-N 2-[2-[methyl(propan-2-yl)amino]pyridin-3-yl]-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound C(C)(C)N(C1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O)C WVCICSQZHQXILA-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
• KKPNLESKGMHWRP-UHFFFAOYSA-N 7-(2-hydroxyethyl)-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-2-(2-propan-2-ylpyridin-3-yl)purin-8-one Chemical compound OCCN1C(N(C2=NC(=NC=C12)C=1C(=NC=CC=1)C(C)C)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O KKPNLESKGMHWRP-UHFFFAOYSA-N 0.000 claims description 2
• GYHBGPIBXOWWJQ-UHFFFAOYSA-N 7-(2-methoxyethyl)-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-2-(2-propan-2-ylpyridin-3-yl)purin-8-one Chemical compound C(C)(C)C1=NC=CC=C1C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O)CCOC GYHBGPIBXOWWJQ-UHFFFAOYSA-N 0.000 claims description 2
• VPBDSNFXCOKMSI-UHFFFAOYSA-N 7-cyclopropyl-2-(2-cyclopropylpyridin-3-yl)-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]purin-8-one Chemical compound C1(CC1)N1C(N(C2=NC(=NC=C12)C=1C(=NC=CC=1)C1CC1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O VPBDSNFXCOKMSI-UHFFFAOYSA-N 0.000 claims description 2
• YQVLGKWRSLWLPE-UHFFFAOYSA-N 7-ethyl-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-2-(2-propan-2-ylpyridin-3-yl)purin-8-one Chemical compound C(C)N1C(N(C2=NC(=NC=C12)C=1C(=NC=CC=1)C(C)C)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O YQVLGKWRSLWLPE-UHFFFAOYSA-N 0.000 claims description 2
• IVXCDZBXNMMJIM-UHFFFAOYSA-N 7-methyl-2-(2-methylpyridin-3-yl)-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]purin-8-one Chemical compound CN1C(N(C2=NC(=NC=C12)C=1C(=NC=CC=1)C)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O IVXCDZBXNMMJIM-UHFFFAOYSA-N 0.000 claims description 2
• IIVJOSXOHOCXQS-UHFFFAOYSA-N 7-methyl-2-(2-propan-2-ylpyridin-3-yl)-9-[(4-pyrazol-1-ylphenyl)methyl]purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C=2C(=NC=CC=2)C(C)C)C=C1 IIVJOSXOHOCXQS-UHFFFAOYSA-N 0.000 claims description 2
• JXSHPDNOPUEAJI-UHFFFAOYSA-N 7-methyl-2-(3-propan-2-ylpyridin-2-yl)-9-[(4-pyrazol-1-ylphenyl)methyl]purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=NC=CC=C2C(C)C)C=C1 JXSHPDNOPUEAJI-UHFFFAOYSA-N 0.000 claims description 2
• FOGWAKRKRWFROP-UHFFFAOYSA-N 7-methyl-9-[[4-[1-(oxetan-3-yl)-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-2-(2-propan-2-ylpyridin-3-yl)purin-8-one Chemical compound C(C)(C)C1=NC=CC=C1C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C1COC1)=O)C FOGWAKRKRWFROP-UHFFFAOYSA-N 0.000 claims description 2
• XUWOGKVHRRBCRI-UHFFFAOYSA-N 7-methyl-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-2-(2-morpholin-4-ylpyridin-3-yl)purin-8-one Chemical compound CN1C(N(C2=NC(=NC=C12)C=1C(=NC=CC=1)N1CCOCC1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O XUWOGKVHRRBCRI-UHFFFAOYSA-N 0.000 claims description 2
• NNKQYERYUHKVPI-UHFFFAOYSA-N 7-methyl-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-2-(2-propan-2-ylpyridin-3-yl)purin-8-one Chemical compound C(C)(C)C1=NC=CC=C1C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O)C NNKQYERYUHKVPI-UHFFFAOYSA-N 0.000 claims description 2
• ORZXVXRPTWGDSR-UHFFFAOYSA-N 7-methyl-9-[[4-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]phenyl]methyl]-2-(2-propan-2-ylpyridin-3-yl)purin-8-one Chemical compound C(C)(C)C1=NC=CC=C1C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)N1N=C(C=C1C)C(F)(F)F)=O)C ORZXVXRPTWGDSR-UHFFFAOYSA-N 0.000 claims description 2
• JIHRNDINOJNCSK-UHFFFAOYSA-N 7-methyl-9-[[4-[5-morpholin-4-yl-3-(trifluoromethyl)pyrazol-1-yl]phenyl]methyl]-2-(2-propan-2-ylpyridin-3-yl)purin-8-one Chemical compound C(C)(C)C1=NC=CC=C1C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)N1N=C(C=C1N1CCOCC1)C(F)(F)F)=O)C JIHRNDINOJNCSK-UHFFFAOYSA-N 0.000 claims description 2
• KPIZZVXDRYUPKT-OAHLLOKOSA-N 9-[(1R)-1-[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]ethyl]-2-(2-propan-2-ylpyridin-3-yl)-7H-purin-8-one Chemical compound C(C)(C)C1=NC=CC=C1C1=NC=C2NC(N(C2=N1)[C@H](C)C1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O KPIZZVXDRYUPKT-OAHLLOKOSA-N 0.000 claims description 2
• KPIZZVXDRYUPKT-HNNXBMFYSA-N 9-[(1S)-1-[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]ethyl]-2-(2-propan-2-ylpyridin-3-yl)-7H-purin-8-one Chemical compound C(C)(C)C1=NC=CC=C1C1=NC=C2NC(N(C2=N1)[C@@H](C)C1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O KPIZZVXDRYUPKT-HNNXBMFYSA-N 0.000 claims description 2
• WZTFIZQQLDQTHV-UHFFFAOYSA-N 9-[(4-pyrazol-1-ylphenyl)methyl]-2-[2-(2,2,2-trifluoroethoxy)pyridin-3-yl]-7H-purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C=2C(=NC=CC=2)OCC(F)(F)F)C=C1 WZTFIZQQLDQTHV-UHFFFAOYSA-N 0.000 claims description 2
• RFZPIGZGWQWNSD-UHFFFAOYSA-N 9-[[2,6-difluoro-4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-2-(2-propan-2-ylpyridin-3-yl)-7H-purin-8-one Chemical compound FC1=C(CN2C3=NC(=NC=C3NC2=O)C=2C(=NC=CC=2)C(C)C)C(=CC(=C1)C=1N(C=C(N=1)C(F)(F)F)C)F RFZPIGZGWQWNSD-UHFFFAOYSA-N 0.000 claims description 2
• DSXLIPNHLKVDQB-UHFFFAOYSA-N 9-[[2,6-difluoro-4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7-methyl-2-(2-propan-2-ylpyridin-3-yl)purin-8-one Chemical compound FC1=C(CN2C3=NC(=NC=C3N(C2=O)C)C=2C(=NC=CC=2)C(C)C)C(=CC(=C1)C=1N(C=C(N=1)C(F)(F)F)C)F DSXLIPNHLKVDQB-UHFFFAOYSA-N 0.000 claims description 2
• QBZRBQKFWYZKCU-UHFFFAOYSA-N 9-[[2-fluoro-4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7-methyl-2-(2-propan-2-ylpyridin-3-yl)purin-8-one Chemical compound FC1=C(CN2C3=NC(=NC=C3N(C2=O)C)C=2C(=NC=CC=2)C(C)C)C=CC(=C1)C=1N(C=C(N=1)C(F)(F)F)C QBZRBQKFWYZKCU-UHFFFAOYSA-N 0.000 claims description 2
• QFNIMARQTVZXDZ-UHFFFAOYSA-N 9-[[3,5-difluoro-4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-2-(2-propan-2-ylpyridin-3-yl)-7H-purin-8-one Chemical compound FC=1C=C(CN2C3=NC(=NC=C3NC2=O)C=2C(=NC=CC=2)C(C)C)C=C(C=1C=1N(C=C(N=1)C(F)(F)F)C)F QFNIMARQTVZXDZ-UHFFFAOYSA-N 0.000 claims description 2
• KWHVRRMUNMQDPR-UHFFFAOYSA-N 9-[[3,5-difluoro-4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7-methyl-2-(2-propan-2-ylpyridin-3-yl)purin-8-one Chemical compound FC=1C=C(CN2C3=NC(=NC=C3N(C2=O)C)C=2C(=NC=CC=2)C(C)C)C=C(C=1C=1N(C=C(N=1)C(F)(F)F)C)F KWHVRRMUNMQDPR-UHFFFAOYSA-N 0.000 claims description 2
• CPBQDBYQPOSPPK-UHFFFAOYSA-N 9-[[3-fluoro-4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-2-(2-propan-2-ylpyridin-3-yl)-7H-purin-8-one Chemical compound FC=1C=C(CN2C3=NC(=NC=C3NC2=O)C=2C(=NC=CC=2)C(C)C)C=CC=1C=1N(C=C(N=1)C(F)(F)F)C CPBQDBYQPOSPPK-UHFFFAOYSA-N 0.000 claims description 2
• UCEBQAURCFAMKL-UHFFFAOYSA-N 9-[[3-fluoro-4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7-methyl-2-(2-propan-2-ylpyridin-3-yl)purin-8-one Chemical compound FC=1C=C(CN2C3=NC(=NC=C3N(C2=O)C)C=2C(=NC=CC=2)C(C)C)C=CC=1C=1N(C=C(N=1)C(F)(F)F)C UCEBQAURCFAMKL-UHFFFAOYSA-N 0.000 claims description 2
• XWZMLBXQQMJMBV-UHFFFAOYSA-N 9-[[4-(1,4-dimethylpyrazol-3-yl)phenyl]methyl]-2-(2-propan-2-ylpyridin-3-yl)-7H-purin-8-one Chemical compound CN1N=C(C(=C1)C)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C=2C(=NC=CC=2)C(C)C)C=C1 XWZMLBXQQMJMBV-UHFFFAOYSA-N 0.000 claims description 2
• OMOAXQSAAMCWIT-UHFFFAOYSA-N 9-[[4-(1-methylpyrazol-3-yl)phenyl]methyl]-2-(2-propan-2-ylpyridin-3-yl)-7H-purin-8-one Chemical compound C(C)(C)C1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C1=NN(C=C1)C)=O OMOAXQSAAMCWIT-UHFFFAOYSA-N 0.000 claims description 2
• BLSDCZPNSZNPKF-UHFFFAOYSA-N 9-[[4-(2-methylpyrrol-1-yl)phenyl]methyl]-2-(2-propan-2-ylpyridin-3-yl)-7H-purin-8-one Chemical compound C(C)(C)C1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)N1C(=CC=C1)C)=O BLSDCZPNSZNPKF-UHFFFAOYSA-N 0.000 claims description 2
• QBTHBWNXTDXXRT-UHFFFAOYSA-N 9-[[4-(3-chloro-5-methylpyrazol-1-yl)phenyl]methyl]-2-(2-propan-2-ylpyridin-3-yl)-7H-purin-8-one Chemical compound ClC1=NN(C(=C1)C)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C=2C(=NC=CC=2)C(C)C)C=C1 QBTHBWNXTDXXRT-UHFFFAOYSA-N 0.000 claims description 2
• YMYMUGVRPKKZNP-UHFFFAOYSA-N 9-[[4-(3-fluoropyrazol-1-yl)phenyl]methyl]-2-(2-propan-2-ylpyridin-3-yl)-7H-purin-8-one Chemical compound FC1=NN(C=C1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C=2C(=NC=CC=2)C(C)C)C=C1 YMYMUGVRPKKZNP-UHFFFAOYSA-N 0.000 claims description 2
• COCYVFWOBDPXMF-UHFFFAOYSA-N 9-[[4-(3-methoxy-5-methylpyrazol-1-yl)phenyl]methyl]-2-(2-propan-2-ylpyridin-3-yl)-7H-purin-8-one Chemical compound C(C)(C)C1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)N1N=C(C=C1C)OC)=O COCYVFWOBDPXMF-UHFFFAOYSA-N 0.000 claims description 2
• XTLMEWGLMXEWBY-UHFFFAOYSA-N 9-[[4-(3-piperidin-4-ylpyrazol-1-yl)phenyl]methyl]-2-(2-propan-2-ylpyridin-3-yl)-7H-purin-8-one Chemical compound C(C)(C)C1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)N1N=C(C=C1)C1CCNCC1)=O XTLMEWGLMXEWBY-UHFFFAOYSA-N 0.000 claims description 2
• YKHOGSVHVANFTR-UHFFFAOYSA-N 9-[[4-(4-cyclopropyl-1-methylimidazol-2-yl)phenyl]methyl]-7-methyl-2-(2-propan-2-ylpyridin-3-yl)purin-8-one Chemical compound C1(CC1)C=1N=C(N(C=1)C)C1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C=2C(=NC=CC=2)C(C)C)C=C1 YKHOGSVHVANFTR-UHFFFAOYSA-N 0.000 claims description 2
• JIXARNHYLGUFOV-UHFFFAOYSA-N 9-[[4-(5-chloro-3-methylpyrazol-1-yl)phenyl]methyl]-2-(2-propan-2-ylpyridin-3-yl)-7H-purin-8-one Chemical compound ClC1=CC(=NN1C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C=2C(=NC=CC=2)C(C)C)C=C1)C JIXARNHYLGUFOV-UHFFFAOYSA-N 0.000 claims description 2
• WAHHFBXMGURARX-UHFFFAOYSA-N 9-[[4-[1-(1-methylazetidin-3-yl)-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-2-(2-propan-2-ylpyridin-3-yl)-7H-purin-8-one Chemical compound C(C)(C)C1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C1CN(C1)C)=O WAHHFBXMGURARX-UHFFFAOYSA-N 0.000 claims description 2
• NSXQTVYLDYEBQI-UHFFFAOYSA-N 9-[[4-[1-(2-methoxyethyl)-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-2-(2-propan-2-ylpyridin-3-yl)-7H-purin-8-one Chemical compound C(C)(C)C1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)CCOC)=O NSXQTVYLDYEBQI-UHFFFAOYSA-N 0.000 claims description 2
• PWANKFNRCDARTP-UHFFFAOYSA-N 9-[[4-[1-cyclopropyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-2-(2-propan-2-ylpyridin-3-yl)-7H-purin-8-one Chemical compound C1(CC1)N1C(=NC(=C1)C(F)(F)F)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C=2C(=NC=CC=2)C(C)C)C=C1 PWANKFNRCDARTP-UHFFFAOYSA-N 0.000 claims description 2
• WAKGLAHNMIZQLT-UHFFFAOYSA-N 9-[[4-[1-cyclopropyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7-methyl-2-(2-propan-2-ylpyridin-3-yl)purin-8-one Chemical compound C1(CC1)N1C(=NC(=C1)C(F)(F)F)C1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C=2C(=NC=CC=2)C(C)C)C=C1 WAKGLAHNMIZQLT-UHFFFAOYSA-N 0.000 claims description 2
• UQDBWSDKYPFYNF-UHFFFAOYSA-N 9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-2-(2-pentan-3-yloxypyridin-3-yl)-7H-purin-8-one Chemical compound CN1C(=NC(=C1)C(F)(F)F)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C=2C(=NC=CC=2)OC(CC)CC)C=C1 UQDBWSDKYPFYNF-UHFFFAOYSA-N 0.000 claims description 2
• SVWNOZCBPUHUAD-UHFFFAOYSA-N 9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-2-(2-piperidin-1-ylpyridin-3-yl)-7H-purin-8-one Chemical compound CN1C(=NC(=C1)C(F)(F)F)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C=2C(=NC=CC=2)N2CCCCC2)C=C1 SVWNOZCBPUHUAD-UHFFFAOYSA-N 0.000 claims description 2
• NJWPIQOCAIUYBJ-UHFFFAOYSA-N 9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-2-(2-propan-2-yloxypyridin-3-yl)-7H-purin-8-one Chemical compound C(C)(C)OC1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O NJWPIQOCAIUYBJ-UHFFFAOYSA-N 0.000 claims description 2
• PVDBEYNIPAEYPM-UHFFFAOYSA-N 9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-2-(2-pyrrolidin-1-ylpyridin-3-yl)-7H-purin-8-one Chemical compound CN1C(=NC(=C1)C(F)(F)F)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C=2C(=NC=CC=2)N2CCCC2)C=C1 PVDBEYNIPAEYPM-UHFFFAOYSA-N 0.000 claims description 2
• VINSZRHMYIQWAA-UHFFFAOYSA-N 9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-2-[2-(oxolan-2-ylmethoxy)pyridin-3-yl]-7H-purin-8-one Chemical compound CN1C(=NC(=C1)C(F)(F)F)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C=2C(=NC=CC=2)OCC2OCCC2)C=C1 VINSZRHMYIQWAA-UHFFFAOYSA-N 0.000 claims description 2
• FUNGKPZRMXSSKH-UHFFFAOYSA-N 9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-2-[2-(oxolan-3-ylmethoxy)pyridin-3-yl]-7H-purin-8-one Chemical compound CN1C(=NC(=C1)C(F)(F)F)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C=2C(=NC=CC=2)OCC2COCC2)C=C1 FUNGKPZRMXSSKH-UHFFFAOYSA-N 0.000 claims description 2
• LFKLFVWYYNNESX-UHFFFAOYSA-N 9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-2-[2-(propan-2-ylamino)pyridin-3-yl]-7H-purin-8-one Chemical compound C(C)(C)NC1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O LFKLFVWYYNNESX-UHFFFAOYSA-N 0.000 claims description 2
• VJJQMNCMDWKHFH-UHFFFAOYSA-N 9-[[4-[3-(azetidin-1-yl)-5-methylpyrazol-1-yl]phenyl]methyl]-7-methyl-2-(2-propan-2-ylpyridin-3-yl)purin-8-one Chemical compound N1(CCC1)C1=NN(C(=C1)C)C1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C=2C(=NC=CC=2)C(C)C)C=C1 VJJQMNCMDWKHFH-UHFFFAOYSA-N 0.000 claims description 2
• PUSFFCDFRDILFN-UHFFFAOYSA-N 9-[[4-[4-(difluoromethyl)-1-methylimidazol-2-yl]phenyl]methyl]-2-(2-propan-2-ylpyridin-3-yl)-7H-purin-8-one Chemical compound FC(C=1N=C(N(C=1)C)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C=2C(=NC=CC=2)C(C)C)C=C1)F PUSFFCDFRDILFN-UHFFFAOYSA-N 0.000 claims description 2
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 2
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
• 125000006300 thietan-3-yl group Chemical group [H]C1([H])SC([H])([H])C1([H])* 0.000 claims description 2
• XVBSOXXVQLJILH-HPRDVNIFSA-N 2-(2-propan-2-ylpyridin-3-yl)-9-[[4-[1-(trideuteriomethyl)-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound [2H]C([2H])([2H])N1C=C(N=C1C1=CC=C(CN2C(=O)NC3=CN=C(N=C23)C2=CC=CN=C2C(C)C)C=C1)C(F)(F)F XVBSOXXVQLJILH-HPRDVNIFSA-N 0.000 claims 1
• VSRFXNXPQNTJBZ-UHFFFAOYSA-N 2-[2-(difluoromethoxy)pyridin-3-yl]-6-(methylamino)-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound FC(OC1=NC=CC=C1C1=NC(=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O)NC)F VSRFXNXPQNTJBZ-UHFFFAOYSA-N 0.000 claims 1
• HZGJKSLZENBRDX-UHFFFAOYSA-N 2-[2-(dimethylamino)pyridin-3-yl]-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound CN(C1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O)C HZGJKSLZENBRDX-UHFFFAOYSA-N 0.000 claims 1
• NNKQYERYUHKVPI-HPRDVNIFSA-N 7-methyl-2-(2-propan-2-ylpyridin-3-yl)-9-[[4-[1-(trideuteriomethyl)-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]purin-8-one Chemical compound [2H]C([2H])([2H])N1C=C(N=C1C1=CC=C(CN2C(=O)N(C)C3=CN=C(N=C23)C2=CC=CN=C2C(C)C)C=C1)C(F)(F)F NNKQYERYUHKVPI-HPRDVNIFSA-N 0.000 claims 1
• DREGCCKZHRBYAQ-UHFFFAOYSA-N 9-[[2-fluoro-4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-2-(2-propan-2-ylpyridin-3-yl)-7H-purin-8-one Chemical compound FC1=C(CN2C3=NC(=NC=C3NC2=O)C=2C(=NC=CC=2)C(C)C)C=CC(=C1)C=1N(C=C(N=1)C(F)(F)F)C DREGCCKZHRBYAQ-UHFFFAOYSA-N 0.000 claims 1
• GIENKICLZNGENS-UHFFFAOYSA-N 9-[[4-[1-(oxetan-3-yl)-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-2-(2-propan-2-ylpyridin-3-yl)-7H-purin-8-one Chemical compound C(C)(C)C1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C1COC1)=O GIENKICLZNGENS-UHFFFAOYSA-N 0.000 claims 1
• NNKQYERYUHKVPI-GKOSEXJESA-N 9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-2-(2-propan-2-ylpyridin-3-yl)-7-(trideuteriomethyl)purin-8-one Chemical compound [2H]C([2H])([2H])N1C(=O)N(CC2=CC=C(C=C2)C2=NC(=CN2C)C(F)(F)F)C2=NC(=NC=C12)C1=CC=CN=C1C(C)C NNKQYERYUHKVPI-GKOSEXJESA-N 0.000 claims 1
• VWGKXCOATKJZOM-UHFFFAOYSA-N 9-[[4-[3-(difluoromethyl)-5-methylpyrazol-1-yl]phenyl]methyl]-2-(2-propan-2-ylpyridin-3-yl)-7H-purin-8-one Chemical compound FC(C1=NN(C(=C1)C)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C=2C(=NC=CC=2)C(C)C)C=C1)F VWGKXCOATKJZOM-UHFFFAOYSA-N 0.000 claims 1
• 238000000034 method Methods 0.000 description 54
• 206010028980 Neoplasm Diseases 0.000 description 47
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 47
• 235000002639 sodium chloride Nutrition 0.000 description 43
• 229910052799 carbon Inorganic materials 0.000 description 40
• 239000012453 solvate Substances 0.000 description 39
• 150000001721 carbon Chemical group 0.000 description 38
• 239000000651 prodrug Substances 0.000 description 38
• 229940002612 prodrug Drugs 0.000 description 38
• 201000011510 cancer Diseases 0.000 description 30
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 26
• 201000010099 disease Diseases 0.000 description 26
• 239000000203 mixture Substances 0.000 description 22
• 125000004432 carbon atom Chemical group C* 0.000 description 21
• 208000035475 disorder Diseases 0.000 description 21
• 125000004103 aminoalkyl group Chemical group 0.000 description 18
• 108090000623 proteins and genes Proteins 0.000 description 16
• 238000011282 treatment Methods 0.000 description 16
• 210000004027 cell Anatomy 0.000 description 15
• 235000018102 proteins Nutrition 0.000 description 15
• 102000004169 proteins and genes Human genes 0.000 description 15
• 125000004093 cyano group Chemical group *C#N 0.000 description 14
• 150000004677 hydrates Chemical class 0.000 description 14
• 230000002401 inhibitory effect Effects 0.000 description 13
• 101000607872 Homo sapiens Ubiquitin carboxyl-terminal hydrolase 21 Proteins 0.000 description 12
• 101000807540 Homo sapiens Ubiquitin carboxyl-terminal hydrolase 25 Proteins 0.000 description 12
• 102100037179 Ubiquitin carboxyl-terminal hydrolase 25 Human genes 0.000 description 12
• 125000004076 pyridyl group Chemical group 0.000 description 12
• 102000001477 Deubiquitinating Enzymes Human genes 0.000 description 11
• 108010093668 Deubiquitinating Enzymes Proteins 0.000 description 11
• 108010066496 Ubiquitin-Specific Proteases Proteins 0.000 description 11
• 102000018390 Ubiquitin-Specific Proteases Human genes 0.000 description 11
• 230000000694 effects Effects 0.000 description 10
• 229910052739 hydrogen Inorganic materials 0.000 description 10
• XOFJNFIYNSJCID-UHFFFAOYSA-N CON=C(C)C1=CC=C(C=C1)N1N=CC=C1.N1(N=CC=C1)C1=CC=C(C=C1)C(C)N Chemical compound CON=C(C)C1=CC=C(C=C1)N1N=CC=C1.N1(N=CC=C1)C1=CC=C(C=C1)C(C)N XOFJNFIYNSJCID-UHFFFAOYSA-N 0.000 description 9
• 206010053138 Congenital aplastic anaemia Diseases 0.000 description 9
• 201000004939 Fanconi anemia Diseases 0.000 description 9
• 239000003814 drug Substances 0.000 description 9
• 125000005842 heteroatom Chemical group 0.000 description 9
• 238000003786 synthesis reaction Methods 0.000 description 9
• 230000005778 DNA damage Effects 0.000 description 8
• 231100000277 DNA damage Toxicity 0.000 description 8
• 101000760210 Homo sapiens Ubiquitin carboxyl-terminal hydrolase 12 Proteins 0.000 description 8
• 102100024662 Ubiquitin carboxyl-terminal hydrolase 12 Human genes 0.000 description 8
• 230000005764 inhibitory process Effects 0.000 description 8
• 238000004519 manufacturing process Methods 0.000 description 8
• 101000939517 Homo sapiens Ubiquitin carboxyl-terminal hydrolase 2 Proteins 0.000 description 7
• 101000643890 Homo sapiens Ubiquitin carboxyl-terminal hydrolase 5 Proteins 0.000 description 7
• 101000841466 Homo sapiens Ubiquitin carboxyl-terminal hydrolase 8 Proteins 0.000 description 7
• 101150020913 USP7 gene Proteins 0.000 description 7
• 102100029643 Ubiquitin carboxyl-terminal hydrolase 2 Human genes 0.000 description 7
• 102100021017 Ubiquitin carboxyl-terminal hydrolase 5 Human genes 0.000 description 7
• 102100021013 Ubiquitin carboxyl-terminal hydrolase 7 Human genes 0.000 description 7
• 102100029088 Ubiquitin carboxyl-terminal hydrolase 8 Human genes 0.000 description 7
• 108700011958 Ubiquitin-Specific Peptidase 7 Proteins 0.000 description 7
• 229940126752 Ubiquitin-specific protease 7 inhibitor Drugs 0.000 description 7
• 230000033228 biological regulation Effects 0.000 description 7
• 230000001105 regulatory effect Effects 0.000 description 7
• 239000000126 substance Substances 0.000 description 7
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 6
• 230000033616 DNA repair Effects 0.000 description 6
• 101000809261 Homo sapiens Ubiquitin carboxyl-terminal hydrolase 11 Proteins 0.000 description 6
• 101000841477 Homo sapiens Ubiquitin carboxyl-terminal hydrolase 14 Proteins 0.000 description 6
• 101000841471 Homo sapiens Ubiquitin carboxyl-terminal hydrolase 15 Proteins 0.000 description 6
• 101000644815 Homo sapiens Ubiquitin carboxyl-terminal hydrolase 16 Proteins 0.000 description 6
• 101000644843 Homo sapiens Ubiquitin carboxyl-terminal hydrolase 19 Proteins 0.000 description 6
• 101000607865 Homo sapiens Ubiquitin carboxyl-terminal hydrolase 20 Proteins 0.000 description 6
• 101000939467 Homo sapiens Ubiquitin carboxyl-terminal hydrolase 28 Proteins 0.000 description 6
• 101000748132 Homo sapiens Ubiquitin carboxyl-terminal hydrolase 30 Proteins 0.000 description 6
• 101000748159 Homo sapiens Ubiquitin carboxyl-terminal hydrolase 35 Proteins 0.000 description 6
• 101000671819 Homo sapiens Ubiquitin carboxyl-terminal hydrolase 36 Proteins 0.000 description 6
• 101000760243 Homo sapiens Ubiquitin carboxyl-terminal hydrolase 45 Proteins 0.000 description 6
• 102100038462 Ubiquitin carboxyl-terminal hydrolase 11 Human genes 0.000 description 6
• 102100029163 Ubiquitin carboxyl-terminal hydrolase 14 Human genes 0.000 description 6
• 102100029164 Ubiquitin carboxyl-terminal hydrolase 15 Human genes 0.000 description 6
• 102100020728 Ubiquitin carboxyl-terminal hydrolase 19 Human genes 0.000 description 6
• 102100039920 Ubiquitin carboxyl-terminal hydrolase 20 Human genes 0.000 description 6
• 102100039918 Ubiquitin carboxyl-terminal hydrolase 21 Human genes 0.000 description 6
• 102100029821 Ubiquitin carboxyl-terminal hydrolase 28 Human genes 0.000 description 6
• 102100040052 Ubiquitin carboxyl-terminal hydrolase 30 Human genes 0.000 description 6
• 102100040048 Ubiquitin carboxyl-terminal hydrolase 35 Human genes 0.000 description 6
• 102100040109 Ubiquitin carboxyl-terminal hydrolase 36 Human genes 0.000 description 6
• 102100024718 Ubiquitin carboxyl-terminal hydrolase 45 Human genes 0.000 description 6
• 230000015572 biosynthetic process Effects 0.000 description 6
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
• 125000005843 halogen group Chemical group 0.000 description 6
• 230000037361 pathway Effects 0.000 description 6
• 230000002265 prevention Effects 0.000 description 6
• 229920006395 saturated elastomer Polymers 0.000 description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 description 5
• 125000002947 alkylene group Chemical group 0.000 description 5
• 125000000623 heterocyclic group Chemical group 0.000 description 5
• 201000008968 osteosarcoma Diseases 0.000 description 5
• 229910052760 oxygen Inorganic materials 0.000 description 5
• 239000002904 solvent Substances 0.000 description 5
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 4
• HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 4
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 4
• 108050006400 Cyclin Proteins 0.000 description 4
• 241000282414 Homo sapiens Species 0.000 description 4
• 102000043276 Oncogene Human genes 0.000 description 4
• 108700020796 Oncogene Proteins 0.000 description 4
• 102000009339 Proliferating Cell Nuclear Antigen Human genes 0.000 description 4
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
• 150000001412 amines Chemical class 0.000 description 4
• 125000004663 dialkyl amino group Chemical group 0.000 description 4
• 150000002148 esters Chemical class 0.000 description 4
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
• 125000002950 monocyclic group Chemical group 0.000 description 4
• 125000003386 piperidinyl group Chemical group 0.000 description 4
• 230000008569 process Effects 0.000 description 4
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 3
• 206010004593 Bile duct cancer Diseases 0.000 description 3
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
• 206010009944 Colon cancer Diseases 0.000 description 3
• 102000004190 Enzymes Human genes 0.000 description 3
• 108090000790 Enzymes Proteins 0.000 description 3
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
• 208000032612 Glial tumor Diseases 0.000 description 3
• 206010018338 Glioma Diseases 0.000 description 3
• 206010061252 Intraocular melanoma Diseases 0.000 description 3
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
• 208000034578 Multiple myelomas Diseases 0.000 description 3
• 206010061535 Ovarian neoplasm Diseases 0.000 description 3
• 102000035195 Peptidases Human genes 0.000 description 3
• 108091005804 Peptidases Proteins 0.000 description 3
• 206010035226 Plasma cell myeloma Diseases 0.000 description 3
• 239000004365 Protease Substances 0.000 description 3
• 206010039491 Sarcoma Diseases 0.000 description 3
• 201000005969 Uveal melanoma Diseases 0.000 description 3
• 102100039414 WD repeat-containing protein 48 Human genes 0.000 description 3
• 125000006193 alkinyl group Chemical group 0.000 description 3
• 235000010290 biphenyl Nutrition 0.000 description 3
• 239000004305 biphenyl Chemical group 0.000 description 3
• 208000029742 colonic neoplasm Diseases 0.000 description 3
• 125000004122 cyclic group Chemical group 0.000 description 3
• 230000034994 death Effects 0.000 description 3
• 239000003085 diluting agent Substances 0.000 description 3
• 208000037765 diseases and disorders Diseases 0.000 description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 3
• 125000001041 indolyl group Chemical group 0.000 description 3
• 208000032839 leukemia Diseases 0.000 description 3
• 230000003211 malignant effect Effects 0.000 description 3
• 239000000463 material Substances 0.000 description 3
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
• 125000001624 naphthyl group Chemical group 0.000 description 3
• 208000002154 non-small cell lung carcinoma Diseases 0.000 description 3
• 201000002575 ocular melanoma Diseases 0.000 description 3
• 210000000056 organ Anatomy 0.000 description 3
• 239000000546 pharmaceutical excipient Substances 0.000 description 3
• 125000004193 piperazinyl group Chemical group 0.000 description 3
• JSPCTNUQYWIIOT-UHFFFAOYSA-N piperidine-1-carboxamide Chemical compound NC(=O)N1CCCCC1 JSPCTNUQYWIIOT-UHFFFAOYSA-N 0.000 description 3
• 125000003367 polycyclic group Chemical group 0.000 description 3
• 125000006239 protecting group Chemical group 0.000 description 3
• 125000000714 pyrimidinyl group Chemical group 0.000 description 3
• 230000005855 radiation Effects 0.000 description 3
• 230000028617 response to DNA damage stimulus Effects 0.000 description 3
• 125000000547 substituted alkyl group Chemical group 0.000 description 3
• 239000000758 substrate Substances 0.000 description 3
• 229910052717 sulfur Inorganic materials 0.000 description 3
• 208000011580 syndromic disease Diseases 0.000 description 3
• 230000008685 targeting Effects 0.000 description 3
• 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 3
• 101150042041 wdr48 gene Proteins 0.000 description 3
• IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
• IDUSJBBWEKNWAK-UHFFFAOYSA-N 3,4-dihydro-2h-1,2-benzothiazine Chemical compound C1=CC=C2SNCCC2=C1 IDUSJBBWEKNWAK-UHFFFAOYSA-N 0.000 description 2
• 208000003200 Adenoma Diseases 0.000 description 2
• 206010001233 Adenoma benign Diseases 0.000 description 2
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
• 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 description 2
• 206010006187 Breast cancer Diseases 0.000 description 2
• 208000026310 Breast neoplasm Diseases 0.000 description 2
• XKPKNKNIPJYGTM-UHFFFAOYSA-N CC(C)C1=C(C(N(C(C)C(C=C2)=CC=C2N2N=CC=C2)C=C2N3)N=C2NC3=O)C=CC=C1 Chemical compound CC(C)C1=C(C(N(C(C)C(C=C2)=CC=C2N2N=CC=C2)C=C2N3)N=C2NC3=O)C=CC=C1 XKPKNKNIPJYGTM-UHFFFAOYSA-N 0.000 description 2
• 208000010833 Chronic myeloid leukaemia Diseases 0.000 description 2
• 230000000970 DNA cross-linking effect Effects 0.000 description 2
• 206010014733 Endometrial cancer Diseases 0.000 description 2
• 206010014759 Endometrial neoplasm Diseases 0.000 description 2
• 208000006168 Ewing Sarcoma Diseases 0.000 description 2
• 208000003445 Mouth Neoplasms Diseases 0.000 description 2
• 241000699666 Mus <mouse, genus> Species 0.000 description 2
• 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 description 2
• NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 2
• 208000010505 Nose Neoplasms Diseases 0.000 description 2
• 206010033128 Ovarian cancer Diseases 0.000 description 2
• 206010061902 Pancreatic neoplasm Diseases 0.000 description 2
• 206010060862 Prostate cancer Diseases 0.000 description 2
• 208000000236 Prostatic Neoplasms Diseases 0.000 description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
• MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 2
• 206010041067 Small cell lung cancer Diseases 0.000 description 2
• 108091027967 Small hairpin RNA Proteins 0.000 description 2
• 208000005718 Stomach Neoplasms Diseases 0.000 description 2
• 208000031673 T-Cell Cutaneous Lymphoma Diseases 0.000 description 2
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
• 208000024770 Thyroid neoplasm Diseases 0.000 description 2
• 102000044159 Ubiquitin Human genes 0.000 description 2
• 108090000848 Ubiquitin Proteins 0.000 description 2
• 208000027418 Wounds and injury Diseases 0.000 description 2
• 150000001242 acetic acid derivatives Chemical class 0.000 description 2
• 230000004913 activation Effects 0.000 description 2
• 201000000053 blastoma Diseases 0.000 description 2
• GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
• 239000004202 carbamide Substances 0.000 description 2
• 230000002490 cerebral effect Effects 0.000 description 2
• 238000006243 chemical reaction Methods 0.000 description 2
• 239000000460 chlorine Substances 0.000 description 2
• 210000004252 chorionic villi Anatomy 0.000 description 2
• 239000003431 cross linking reagent Substances 0.000 description 2
• 201000007241 cutaneous T cell lymphoma Diseases 0.000 description 2
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
• 230000009504 deubiquitination Effects 0.000 description 2
• 230000004069 differentiation Effects 0.000 description 2
• 125000005436 dihydrobenzothiophenyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 description 2
• 201000008184 embryoma Diseases 0.000 description 2
• 210000002308 embryonic cell Anatomy 0.000 description 2
• 230000002255 enzymatic effect Effects 0.000 description 2
• 201000008819 extrahepatic bile duct carcinoma Diseases 0.000 description 2
• 239000012467 final product Substances 0.000 description 2
• 229910052731 fluorine Inorganic materials 0.000 description 2
• 125000000524 functional group Chemical group 0.000 description 2
• 206010017758 gastric cancer Diseases 0.000 description 2
• 208000005017 glioblastoma Diseases 0.000 description 2
• 230000012010 growth Effects 0.000 description 2
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
• 230000002267 hypothalamic effect Effects 0.000 description 2
• 238000001727 in vivo Methods 0.000 description 2
• 208000014674 injury Diseases 0.000 description 2
• 239000000543 intermediate Substances 0.000 description 2
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
• 208000012987 lip and oral cavity carcinoma Diseases 0.000 description 2
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 2
• 201000001441 melanoma Diseases 0.000 description 2
• 125000002757 morpholinyl group Chemical group 0.000 description 2
• 201000005962 mycosis fungoides Diseases 0.000 description 2
• 208000037830 nasal cancer Diseases 0.000 description 2
• 201000002528 pancreatic cancer Diseases 0.000 description 2
• 208000008443 pancreatic carcinoma Diseases 0.000 description 2
• 230000026731 phosphorylation Effects 0.000 description 2
• 238000006366 phosphorylation reaction Methods 0.000 description 2
• 238000002360 preparation method Methods 0.000 description 2
• 208000025638 primary cutaneous T-cell non-Hodgkin lymphoma Diseases 0.000 description 2
• 125000003226 pyrazolyl group Chemical group 0.000 description 2
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
• 230000008439 repair process Effects 0.000 description 2
• 125000006413 ring segment Chemical group 0.000 description 2
• 229930195734 saturated hydrocarbon Natural products 0.000 description 2
• 208000037968 sinus cancer Diseases 0.000 description 2
• 239000004055 small Interfering RNA Substances 0.000 description 2
• 208000000587 small cell lung carcinoma Diseases 0.000 description 2
• 150000003384 small molecules Chemical class 0.000 description 2
• 239000007858 starting material Substances 0.000 description 2
• 201000011549 stomach cancer Diseases 0.000 description 2
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
• 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 2
• 125000004568 thiomorpholinyl group Chemical group 0.000 description 2
• 210000000115 thoracic cavity Anatomy 0.000 description 2
• 201000002510 thyroid cancer Diseases 0.000 description 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• 230000004614 tumor growth Effects 0.000 description 2
• 230000034512 ubiquitination Effects 0.000 description 2
• 238000010798 ubiquitination Methods 0.000 description 2
• 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
• FIARMZDBEGVMLV-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanolate Chemical group [O-]C(F)(F)C(F)(F)F FIARMZDBEGVMLV-UHFFFAOYSA-N 0.000 description 1
• YCEZZDNWLVQCRU-UHFFFAOYSA-N 1,2-diaminoethyl Chemical group N[CH]CN YCEZZDNWLVQCRU-UHFFFAOYSA-N 0.000 description 1
• XGTXVQQTESIWGC-UHFFFAOYSA-N 1,2-dimethyl-N-[4-[[7-methyl-8-oxo-2-(2-propan-2-ylphenyl)purin-9-yl]methyl]phenyl]imidazole-4-sulfonamide Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)NS(=O)(=O)C=1N=C(N(C=1)C)C)=O)C XGTXVQQTESIWGC-UHFFFAOYSA-N 0.000 description 1
• SILNNFMWIMZVEQ-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-one Chemical compound C1=CC=C2NC(O)=NC2=C1 SILNNFMWIMZVEQ-UHFFFAOYSA-N 0.000 description 1
• QYTUAGIHIXWZDR-UHFFFAOYSA-N 1-[4-[[2-(2-cyclopropylphenyl)-8-oxo-7H-purin-9-yl]methyl]phenyl]-N,N,5-trimethylpyrazole-3-carboxamide Chemical compound C1(CC1)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)N1N=C(C=C1C)C(=O)N(C)C)=O QYTUAGIHIXWZDR-UHFFFAOYSA-N 0.000 description 1
• JUHGNLJUNIGPDJ-UHFFFAOYSA-N 1-[4-[[7-methyl-8-oxo-2-(2-propan-2-ylphenyl)purin-9-yl]methyl]phenyl]-3-propan-2-ylurea Chemical compound C(C)(C)NC(=O)NC1=CC=C(C=C1)CN1C2=NC(=NC=C2N(C1=O)C)C1=C(C=CC=C1)C(C)C JUHGNLJUNIGPDJ-UHFFFAOYSA-N 0.000 description 1
• ORLPQVBFEDWLMQ-UHFFFAOYSA-N 1-[4-[[8-oxo-2-(2-propan-2-ylphenyl)-7H-purin-9-yl]methyl]phenyl]pyrazole-3,5-dicarbonitrile Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)N1N=C(C=C1C#N)C#N)=O ORLPQVBFEDWLMQ-UHFFFAOYSA-N 0.000 description 1
• NVRRCHMIZXBFFW-UHFFFAOYSA-N 1-cyclopropyl-3-[4-[[7-methyl-8-oxo-2-(2-propan-2-ylphenyl)purin-9-yl]methyl]phenyl]urea Chemical compound C1(CC1)NC(=O)NC1=CC=C(C=C1)CN1C2=NC(=NC=C2N(C1=O)C)C1=C(C=CC=C1)C(C)C NVRRCHMIZXBFFW-UHFFFAOYSA-N 0.000 description 1
• NVUUZIAFIMLWDB-UHFFFAOYSA-N 1-methyl-1-[4-[[7-methyl-8-oxo-2-(2-propan-2-ylphenyl)purin-9-yl]methyl]phenyl]-3-propan-2-ylurea Chemical compound C(C)(C)NC(N(C)C1=CC=C(C=C1)CN1C2=NC(=NC=C2N(C1=O)C)C1=C(C=CC=C1)C(C)C)=O NVUUZIAFIMLWDB-UHFFFAOYSA-N 0.000 description 1
• SMQBHHUGPPGOQN-UHFFFAOYSA-N 1-methyl-N-[4-[[7-methyl-8-oxo-2-(2-propan-2-ylphenyl)purin-9-yl]methyl]phenyl]imidazole-2-sulfonamide Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)NS(=O)(=O)C=1N(C=CN=1)C)=O)C SMQBHHUGPPGOQN-UHFFFAOYSA-N 0.000 description 1
• XRTYKBVMSPJAQW-UHFFFAOYSA-N 1-methyl-N-[4-[[7-methyl-8-oxo-2-(2-propan-2-ylphenyl)purin-9-yl]methyl]phenyl]pyrazole-3-sulfonamide Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)NS(=O)(=O)C1=NN(C=C1)C)=O)C XRTYKBVMSPJAQW-UHFFFAOYSA-N 0.000 description 1
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
• PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 description 1
• AWBOSXFRPFZLOP-UHFFFAOYSA-N 2,1,3-benzoxadiazole Chemical compound C1=CC=CC2=NON=C21 AWBOSXFRPFZLOP-UHFFFAOYSA-N 0.000 description 1
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
• KAFUQVXDOAKEDU-UHFFFAOYSA-N 2,5-dimethyl-N-[4-[[7-methyl-8-oxo-2-(2-propan-2-ylphenyl)purin-9-yl]methyl]phenyl]pyrazole-3-carboxamide Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)NC(=O)C1=CC(=NN1C)C)=O)C KAFUQVXDOAKEDU-UHFFFAOYSA-N 0.000 description 1
• IKARTXUKBAFPRU-UHFFFAOYSA-N 2-(1-methylindazol-7-yl)-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound CN1N=CC2=CC=CC(=C12)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O IKARTXUKBAFPRU-UHFFFAOYSA-N 0.000 description 1
• QJSILWNVVLTEIU-UHFFFAOYSA-N 2-(1-methylindol-7-yl)-9-[(4-pyrazol-1-ylphenyl)methyl]-7H-purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C=2C=CC=C3C=CN(C=23)C)C=C1 QJSILWNVVLTEIU-UHFFFAOYSA-N 0.000 description 1
• JERTXCSDVJLSGB-UHFFFAOYSA-N 2-(1-methylindol-7-yl)-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound CN1C=CC2=CC=CC(=C12)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O JERTXCSDVJLSGB-UHFFFAOYSA-N 0.000 description 1
• VAIAFQWANGXVOA-UHFFFAOYSA-N 2-(2,2-difluoro-1,3-benzodioxol-4-yl)-9-[(4-pyrazol-1-ylphenyl)methyl]-7H-purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=CC=CC=3OC(OC=32)(F)F)C=C1 VAIAFQWANGXVOA-UHFFFAOYSA-N 0.000 description 1
• KFTYMLGZBSXITL-UHFFFAOYSA-N 2-(2,2-difluoro-1,3-benzodioxol-4-yl)-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound FC1(OC2=C(O1)C=CC=C2C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O)F KFTYMLGZBSXITL-UHFFFAOYSA-N 0.000 description 1
• CZAJPMNSKUCPTK-UHFFFAOYSA-N 2-(2-acetylphenyl)-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound C(C)(=O)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O CZAJPMNSKUCPTK-UHFFFAOYSA-N 0.000 description 1
• ZIRFYWABJWQNPQ-UHFFFAOYSA-N 2-(2-cyclopropylphenyl)-9-[(4-pyrazol-1-ylphenyl)methyl]-7H-purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C2CC2)C=C1 ZIRFYWABJWQNPQ-UHFFFAOYSA-N 0.000 description 1
• IVRMALGQDLIRLN-UHFFFAOYSA-N 2-(2-cyclopropylphenyl)-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound C1(CC1)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O IVRMALGQDLIRLN-UHFFFAOYSA-N 0.000 description 1
• GJZBOIDRNWYKMF-UHFFFAOYSA-N 2-(2-cyclopropylphenyl)-9-[[4-[5-(hydroxymethyl)-3-methylpyrazol-1-yl]phenyl]methyl]-7H-purin-8-one Chemical compound C1(CC1)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)N1N=C(C=C1CO)C)=O GJZBOIDRNWYKMF-UHFFFAOYSA-N 0.000 description 1
• OGUAHVPNWIZOOG-UHFFFAOYSA-N 2-(2-ethylphenyl)-9-[(4-pyrazol-1-ylphenyl)methyl]-7H-purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)CC)C=C1 OGUAHVPNWIZOOG-UHFFFAOYSA-N 0.000 description 1
• UYDZPINWZXYXRL-UHFFFAOYSA-N 2-(2-fluoro-6-propan-2-ylphenyl)-7-methyl-9-[(4-pyrazol-1-ylphenyl)methyl]purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C=CC=C2C(C)C)F)C=C1 UYDZPINWZXYXRL-UHFFFAOYSA-N 0.000 description 1
• XFSZMIBMDWMFCY-UHFFFAOYSA-N 2-(2-fluoro-6-propan-2-ylphenyl)-9-[(4-pyrazol-1-ylphenyl)methyl]-7H-purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2C(C)C)F)C=C1 XFSZMIBMDWMFCY-UHFFFAOYSA-N 0.000 description 1
• CUEHKGCLESXCCJ-UHFFFAOYSA-N 2-(2-methylsulfinylphenyl)-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound CN1C(=NC(=C1)C(F)(F)F)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)S(=O)C)C=C1 CUEHKGCLESXCCJ-UHFFFAOYSA-N 0.000 description 1
• AYDLXHQGLQSMJV-UHFFFAOYSA-N 2-(2-propan-2-ylphenyl)-9-(1-pyridin-3-ylpiperidin-4-yl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)C1CCN(CC1)C=1C=NC=CC=1)=O AYDLXHQGLQSMJV-UHFFFAOYSA-N 0.000 description 1
• OHSRLVNCSFIDGN-UHFFFAOYSA-N 2-(2-propan-2-ylphenyl)-9-(2-propan-2-ylsulfonyl-2-azaspiro[3.3]heptan-7-yl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)C1C2(CN(C2)S(=O)(=O)C(C)C)CC1)=O OHSRLVNCSFIDGN-UHFFFAOYSA-N 0.000 description 1
• WQRQSAYRURYYRZ-UHFFFAOYSA-N 2-(2-propan-2-ylphenyl)-9-(2-pyridin-3-yl-2-azaspiro[3.3]heptan-7-yl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)C1C2(CN(C2)C=2C=NC=CC=2)CC1)=O WQRQSAYRURYYRZ-UHFFFAOYSA-N 0.000 description 1
• SQSPANKPFWVFCB-UHFFFAOYSA-N 2-(2-propan-2-ylphenyl)-9-[(1-pyridin-3-ylpiperidin-4-yl)methyl]-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1CCN(CC1)C=1C=NC=CC=1)=O SQSPANKPFWVFCB-UHFFFAOYSA-N 0.000 description 1
• SRGGWHSTWMBBIP-XUZZJYLKSA-N 2-(2-propan-2-ylphenyl)-9-[(1R,2S)-2-(4-pyrazol-1-ylphenyl)cyclobutyl]-7H-purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(C=C1)[C@H]1[C@@H](CC1)N1C2=NC(=NC=C2NC1=O)C1=C(C=CC=C1)C(C)C SRGGWHSTWMBBIP-XUZZJYLKSA-N 0.000 description 1
• SRGGWHSTWMBBIP-QPPBQGQZSA-N 2-(2-propan-2-ylphenyl)-9-[(1S,2R)-2-(4-pyrazol-1-ylphenyl)cyclobutyl]-7H-purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(C=C1)[C@@H]1[C@H](CC1)N1C2=NC(=NC=C2NC1=O)C1=C(C=CC=C1)C(C)C SRGGWHSTWMBBIP-QPPBQGQZSA-N 0.000 description 1
• VRSQUVMWLCPBPM-UHFFFAOYSA-N 2-(2-propan-2-ylphenyl)-9-[(3-pyrazol-1-ylphenyl)methyl]-7H-purin-8-one Chemical compound N1(N=CC=C1)C=1C=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=CC=1 VRSQUVMWLCPBPM-UHFFFAOYSA-N 0.000 description 1
• XZHXYWOYMPCVDU-UHFFFAOYSA-N 2-(2-propan-2-ylphenyl)-9-[(4-pyrazin-2-ylphenyl)methyl]-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C1=NC=CN=C1)=O XZHXYWOYMPCVDU-UHFFFAOYSA-N 0.000 description 1
• YJPVJGSRFKFSIN-UHFFFAOYSA-N 2-(2-propan-2-ylphenyl)-9-[(4-pyrazol-1-ylphenyl)methyl]-7H-purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 YJPVJGSRFKFSIN-UHFFFAOYSA-N 0.000 description 1
• MSWMICMNCQLQMA-UHFFFAOYSA-N 2-(2-propan-2-ylphenyl)-9-[(4-pyrimidin-2-ylphenyl)methyl]-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C1=NC=CC=N1)=O MSWMICMNCQLQMA-UHFFFAOYSA-N 0.000 description 1
• HQZHJBZESKMZCW-UHFFFAOYSA-N 2-(2-propan-2-ylphenyl)-9-[(5-pyrazol-1-ylpyrazin-2-yl)methyl]-7H-purin-8-one Chemical compound N1(N=CC=C1)C=1N=CC(=NC=1)CN1C2=NC(=NC=C2NC1=O)C1=C(C=CC=C1)C(C)C HQZHJBZESKMZCW-UHFFFAOYSA-N 0.000 description 1
• LPYBILDUTWVADS-UHFFFAOYSA-N 2-(2-propan-2-ylphenyl)-9-[(5-pyrazol-1-ylpyrimidin-2-yl)methyl]-7H-purin-8-one Chemical compound N1(N=CC=C1)C=1C=NC(=NC=1)CN1C2=NC(=NC=C2NC1=O)C1=C(C=CC=C1)C(C)C LPYBILDUTWVADS-UHFFFAOYSA-N 0.000 description 1
• INOZMTRYZDYSDP-UHFFFAOYSA-N 2-(2-propan-2-ylphenyl)-9-[(6-pyrazol-1-ylpyridin-3-yl)methyl]-7H-purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(C=N1)CN1C2=NC(=NC=C2NC1=O)C1=C(C=CC=C1)C(C)C INOZMTRYZDYSDP-UHFFFAOYSA-N 0.000 description 1
• LSOGXFLMOORPJU-UHFFFAOYSA-N 2-(2-propan-2-ylphenyl)-9-[2-(1-pyridin-3-ylpiperidin-4-yl)ethyl]-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CCC1CCN(CC1)C=1C=NC=CC=1)=O LSOGXFLMOORPJU-UHFFFAOYSA-N 0.000 description 1
• XBVAKLMIEUXVEC-UHFFFAOYSA-N 2-(2-propan-2-ylphenyl)-9-[[1-[4-(trifluoromethyl)pyrimidin-2-yl]azetidin-3-yl]methyl]-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1CN(C1)C1=NC=CC(=N1)C(F)(F)F)=O XBVAKLMIEUXVEC-UHFFFAOYSA-N 0.000 description 1
• XRYDWYNIXLMXLL-UHFFFAOYSA-N 2-(2-propan-2-ylphenyl)-9-[[4-(1,2,4-triazol-1-yl)phenyl]methyl]-7H-purin-8-one Chemical compound N1(N=CN=C1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 XRYDWYNIXLMXLL-UHFFFAOYSA-N 0.000 description 1
• GAGOVVJFJPOFCR-UHFFFAOYSA-N 2-(2-propan-2-ylphenyl)-9-[[4-(1H-pyrazol-4-yl)phenyl]methyl]-7H-purin-8-one Chemical compound N1N=CC(=C1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 GAGOVVJFJPOFCR-UHFFFAOYSA-N 0.000 description 1
• RSRODHVMPXJPLK-UHFFFAOYSA-N 2-(2-propan-2-ylphenyl)-9-[[4-(2-propan-2-ylpyrazol-3-yl)phenyl]methyl]-7H-purin-8-one Chemical compound C(C)(C)N1N=CC=C1C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 RSRODHVMPXJPLK-UHFFFAOYSA-N 0.000 description 1
• WXKAHACMTNEBAA-UHFFFAOYSA-N 2-(2-propan-2-ylphenyl)-9-[[4-(2H-tetrazol-5-yl)phenyl]methyl]-7H-purin-8-one Chemical compound N1N=NN=C1C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 WXKAHACMTNEBAA-UHFFFAOYSA-N 0.000 description 1
• PZZMCPDYMQJTSQ-UHFFFAOYSA-N 2-(2-propan-2-ylphenyl)-9-[[4-(2H-triazol-4-yl)phenyl]methyl]-7H-purin-8-one Chemical compound N1N=NC=C1C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 PZZMCPDYMQJTSQ-UHFFFAOYSA-N 0.000 description 1
• SLTPFCQHYIYPMM-UHFFFAOYSA-N 2-(2-propan-2-ylphenyl)-9-[[4-(3-pyrrolidin-3-ylpyrazol-1-yl)phenyl]methyl]-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)N1N=C(C=C1)C1CNCC1)=O SLTPFCQHYIYPMM-UHFFFAOYSA-N 0.000 description 1
• GIEMEONUHUXERO-UHFFFAOYSA-N 2-(2-propan-2-ylphenyl)-9-[[4-(pyrrolidine-1-carbonyl)phenyl]methyl]-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C(=O)N1CCCC1)=O GIEMEONUHUXERO-UHFFFAOYSA-N 0.000 description 1
• NGNJSMKEHMQJOB-UHFFFAOYSA-N 2-(2-propan-2-ylphenyl)-9-[[4-(triazol-1-yl)phenyl]methyl]-7H-purin-8-one Chemical compound N1(N=NC=C1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 NGNJSMKEHMQJOB-UHFFFAOYSA-N 0.000 description 1
• BOPHSCJLTGQUEP-UHFFFAOYSA-N 2-(2-propan-2-ylphenyl)-9-[[4-(triazol-2-yl)phenyl]methyl]-7H-purin-8-one Chemical compound N=1N(N=CC=1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 BOPHSCJLTGQUEP-UHFFFAOYSA-N 0.000 description 1
• GUIYJRKJPKIJCR-UHFFFAOYSA-N 2-(2-propan-2-ylphenyl)-9-[[4-[3-(trifluoromethyl)pyrazol-1-yl]phenyl]methyl]-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)N1N=C(C=C1)C(F)(F)F)=O GUIYJRKJPKIJCR-UHFFFAOYSA-N 0.000 description 1
• LJYDPECBUFZMFD-UHFFFAOYSA-N 2-(2-propoxyphenyl)-9-[(4-pyrazol-1-ylphenyl)methyl]-7H-purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)OCCC)C=C1 LJYDPECBUFZMFD-UHFFFAOYSA-N 0.000 description 1
• WFPZONVRUGWYEQ-UHFFFAOYSA-N 2-(3-chloro-2-propan-2-ylphenyl)-9-[(4-pyrazol-1-ylphenyl)methyl]-7H-purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C(=CC=C2)Cl)C(C)C)C=C1 WFPZONVRUGWYEQ-UHFFFAOYSA-N 0.000 description 1
• BVHDMTBCHBXUAE-UHFFFAOYSA-N 2-(3-fluoro-2-methoxyphenyl)-9-[[4-(triazol-2-yl)phenyl]methyl]-7H-purin-8-one Chemical compound N=1N(N=CC=1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C(=CC=C2)F)OC)C=C1 BVHDMTBCHBXUAE-UHFFFAOYSA-N 0.000 description 1
• NHFPBNRKHPUNPP-UHFFFAOYSA-N 2-(3-fluoro-2-propan-2-ylphenyl)-7-methyl-9-[(4-pyrazol-1-ylphenyl)methyl]purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C(=CC=C2)F)C(C)C)C=C1 NHFPBNRKHPUNPP-UHFFFAOYSA-N 0.000 description 1
• PZRQCFAPIUYXGV-UHFFFAOYSA-N 2-(3-fluoro-2-propan-2-ylphenyl)-7-methyl-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]purin-8-one Chemical compound FC=1C(=C(C=CC=1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O)C)C(C)C PZRQCFAPIUYXGV-UHFFFAOYSA-N 0.000 description 1
• RAACTOUOZZQJAN-UHFFFAOYSA-N 2-(3-fluoro-2-propan-2-ylphenyl)-9-[[4-(1-methylimidazol-2-yl)phenyl]methyl]-7H-purin-8-one Chemical compound FC=1C(=C(C=CC=1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=CN=1)C)=O)C(C)C RAACTOUOZZQJAN-UHFFFAOYSA-N 0.000 description 1
• LJCQOZJMVSNBPI-UHFFFAOYSA-N 2-(3-fluoro-2-propan-2-ylphenyl)-9-[[4-(1-methylimidazol-4-yl)phenyl]methyl]-7H-purin-8-one Chemical compound FC=1C(=C(C=CC=1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N=CN(C=1)C)=O)C(C)C LJCQOZJMVSNBPI-UHFFFAOYSA-N 0.000 description 1
• ZRTCRERQISUOQU-UHFFFAOYSA-N 2-(3-fluoro-2-propan-2-ylphenyl)-9-[[4-(3-piperidin-4-ylpyrazol-1-yl)phenyl]methyl]-7H-purin-8-one Chemical compound FC=1C(=C(C=CC=1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)N1N=C(C=C1)C1CCNCC1)=O)C(C)C ZRTCRERQISUOQU-UHFFFAOYSA-N 0.000 description 1
• XQVCJIOSDCGADW-UHFFFAOYSA-N 2-(3-fluoro-2-propan-2-ylphenyl)-9-[[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]methyl]-7H-purin-8-one Chemical compound FC=1C(=C(C=CC=1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C1=NOC(=N1)C)=O)C(C)C XQVCJIOSDCGADW-UHFFFAOYSA-N 0.000 description 1
• ZQJQOQRTGHOCOR-UHFFFAOYSA-N 2-(3-fluoro-2-propan-2-ylphenyl)-9-[[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]methyl]-7H-purin-8-one Chemical compound FC=1C(=C(C=CC=1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1OC(=NN=1)C)=O)C(C)C ZQJQOQRTGHOCOR-UHFFFAOYSA-N 0.000 description 1
• DBDOSHIOYSVJNO-UHFFFAOYSA-N 2-(3-fluoro-2-propan-2-ylphenyl)-9-[[4-(triazol-1-yl)phenyl]methyl]-7H-purin-8-one Chemical compound N1(N=NC=C1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C(=CC=C2)F)C(C)C)C=C1 DBDOSHIOYSVJNO-UHFFFAOYSA-N 0.000 description 1
• TVYKJXWFYZRGLP-UHFFFAOYSA-N 2-(3-fluoro-2-propan-2-ylphenyl)-9-[[4-(triazol-2-yl)phenyl]methyl]-7H-purin-8-one Chemical compound N=1N(N=CC=1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C(=CC=C2)F)C(C)C)C=C1 TVYKJXWFYZRGLP-UHFFFAOYSA-N 0.000 description 1
• ZJOZETCOKXIEOD-UHFFFAOYSA-N 2-(3-fluoro-2-propan-2-ylphenyl)-9-[[4-[1-(oxetan-3-yl)-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound FC=1C(=C(C=CC=1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C1COC1)=O)C(C)C ZJOZETCOKXIEOD-UHFFFAOYSA-N 0.000 description 1
• WJSIXINFOJKOEJ-UHFFFAOYSA-N 2-(3-methoxy-2-propan-2-ylphenyl)-9-[(4-pyrazol-1-ylphenyl)methyl]-7H-purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C(=CC=C2)OC)C(C)C)C=C1 WJSIXINFOJKOEJ-UHFFFAOYSA-N 0.000 description 1
• NEGWBFBHQKRFKL-UHFFFAOYSA-N 2-(3-methyl-2-propan-2-ylphenyl)-9-[(4-pyrazol-1-ylphenyl)methyl]-7H-purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C(=CC=C2)C)C(C)C)C=C1 NEGWBFBHQKRFKL-UHFFFAOYSA-N 0.000 description 1
• TZYDFUSRSPJZKB-UHFFFAOYSA-N 2-(4-fluoro-2-propan-2-yloxyphenyl)-9-[[4-(triazol-2-yl)phenyl]methyl]-7H-purin-8-one Chemical compound N=1N(N=CC=1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=C(C=C2)F)OC(C)C)C=C1 TZYDFUSRSPJZKB-UHFFFAOYSA-N 0.000 description 1
• SGZOCUXVAVEVSG-UHFFFAOYSA-N 2-(4-fluoro-2-propan-2-ylphenyl)-7-methyl-9-[(4-pyrazol-1-ylphenyl)methyl]purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C=C(C=C2)F)C(C)C)C=C1 SGZOCUXVAVEVSG-UHFFFAOYSA-N 0.000 description 1
• PAXILXMDLIJRRQ-UHFFFAOYSA-N 2-(4-propan-2-ylpyrimidin-5-yl)-9-[(4-pyrazol-1-ylphenyl)methyl]-7H-purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C=2C(=NC=NC=2)C(C)C)C=C1 PAXILXMDLIJRRQ-UHFFFAOYSA-N 0.000 description 1
• NOIHMKBQCPDICE-UHFFFAOYSA-N 2-(5-chloro-2-cyclopropylphenyl)-9-[(4-pyrazol-1-ylphenyl)methyl]-7H-purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC(=C2)Cl)C2CC2)C=C1 NOIHMKBQCPDICE-UHFFFAOYSA-N 0.000 description 1
• WFJMPEKZMYMQDS-UHFFFAOYSA-N 2-(5-fluoro-2-propan-2-ylphenyl)-7-methyl-9-[(4-pyrazol-1-ylphenyl)methyl]purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C=CC(=C2)F)C(C)C)C=C1 WFJMPEKZMYMQDS-UHFFFAOYSA-N 0.000 description 1
• KRXLWRGSCWRLTK-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)pyridin-3-yl]-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound C(C)OCCOC1=NC=CC=C1C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O KRXLWRGSCWRLTK-UHFFFAOYSA-N 0.000 description 1
• HRBIDAOSMHKCJR-UHFFFAOYSA-N 2-[2-(2-hydroxypropan-2-yl)phenyl]-7-methyl-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]purin-8-one Chemical compound OC(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O)C HRBIDAOSMHKCJR-UHFFFAOYSA-N 0.000 description 1
• FYYPTTHJEKDWSC-UHFFFAOYSA-N 2-[2-(2-hydroxypropan-2-yl)phenyl]-9-[(4-pyrazol-1-ylphenyl)methyl]-7H-purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)(C)O)C=C1 FYYPTTHJEKDWSC-UHFFFAOYSA-N 0.000 description 1
• RFGFNFANGOUDHH-UHFFFAOYSA-N 2-[2-(2-hydroxypropan-2-yl)phenyl]-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound OC(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O RFGFNFANGOUDHH-UHFFFAOYSA-N 0.000 description 1
• VECAZYVYFGARHU-UHFFFAOYSA-N 2-[2-(2-methoxyethoxy)phenyl]-9-[(4-pyrazol-1-ylphenyl)methyl]-7H-purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)OCCOC)C=C1 VECAZYVYFGARHU-UHFFFAOYSA-N 0.000 description 1
• CYKQMKOVALQYNV-UHFFFAOYSA-N 2-[2-(cyclopropylmethoxy)phenyl]-9-[(4-pyrazol-1-ylphenyl)methyl]-7H-purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)OCC2CC2)C=C1 CYKQMKOVALQYNV-UHFFFAOYSA-N 0.000 description 1
• SXEVIXSACDSRTH-UHFFFAOYSA-N 2-[2-(difluoromethoxy)phenyl]-9-[[4-(3-fluoropyrazol-1-yl)phenyl]methyl]-7H-purin-8-one Chemical compound FC(OC1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)N1N=C(C=C1)F)=O)F SXEVIXSACDSRTH-UHFFFAOYSA-N 0.000 description 1
• VVNJRWPVGLVOET-UHFFFAOYSA-N 2-[2-(difluoromethyl)phenyl]-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound FC(C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O)F VVNJRWPVGLVOET-UHFFFAOYSA-N 0.000 description 1
• PIXKIZZQBXWGJG-UHFFFAOYSA-N 2-[2-(dimethylamino)phenyl]-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound CN(C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O)C PIXKIZZQBXWGJG-UHFFFAOYSA-N 0.000 description 1
• ARAKRODGSVNHHJ-OAHLLOKOSA-N 2-[2-[(1R)-1-methoxyethyl]phenyl]-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound CO[C@H](C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O ARAKRODGSVNHHJ-OAHLLOKOSA-N 0.000 description 1
• ARAKRODGSVNHHJ-HNNXBMFYSA-N 2-[2-[(1S)-1-methoxyethyl]phenyl]-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7H-purin-8-one Chemical compound CO[C@@H](C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O ARAKRODGSVNHHJ-HNNXBMFYSA-N 0.000 description 1
• OYEQNWIHCISTEB-UHFFFAOYSA-N 2-[2-cyclopropyl-5-(trifluoromethyl)phenyl]-9-[(4-pyrazol-1-ylphenyl)methyl]-7H-purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC(=C2)C(F)(F)F)C2CC2)C=C1 OYEQNWIHCISTEB-UHFFFAOYSA-N 0.000 description 1
• QLVJGZCCFPGLOK-UHFFFAOYSA-N 2-[8-oxo-2-(2-propan-2-ylphenyl)-9-[(4-pyrazol-1-ylphenyl)methyl]purin-7-yl]propanoic acid Chemical compound N1(N=CC=C1)C1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C(C(=O)O)C)C2=C(C=CC=C2)C(C)C)C=C1 QLVJGZCCFPGLOK-UHFFFAOYSA-N 0.000 description 1
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
• PCDASJUPSYGQTR-UHFFFAOYSA-N 2-methyl-5-[4-[[7-methyl-8-oxo-2-(2-propan-2-ylphenyl)purin-9-yl]methyl]phenyl]-1,2,4-triazole-3-carboxamide Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)C1=NN(C(=N1)C(=O)N)C)=O)C PCDASJUPSYGQTR-UHFFFAOYSA-N 0.000 description 1
• NISRAYIXJFWOQD-UHFFFAOYSA-N 2-methyl-6-[[8-oxo-2-(2-propan-2-ylphenyl)-7H-purin-9-yl]methyl]-3,4-dihydroisoquinolin-1-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC=1C=C2CCN(C(C2=CC=1)=O)C)=O NISRAYIXJFWOQD-UHFFFAOYSA-N 0.000 description 1
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
• ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
• ALKYHXVLJMQRLQ-UHFFFAOYSA-M 3-carboxynaphthalen-2-olate Chemical compound C1=CC=C2C=C(C([O-])=O)C(O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-M 0.000 description 1
• BGPGMXTYSLNDCT-UHFFFAOYSA-N 3-cyclopropyl-1-methyl-1-[4-[[7-methyl-8-oxo-2-(2-propan-2-ylphenyl)purin-9-yl]methyl]phenyl]urea Chemical compound C1(CC1)NC(N(C)C1=CC=C(C=C1)CN1C2=NC(=NC=C2N(C1=O)C)C1=C(C=CC=C1)C(C)C)=O BGPGMXTYSLNDCT-UHFFFAOYSA-N 0.000 description 1
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
• NMHQSBILCWUIIO-UHFFFAOYSA-N 4-[[8-oxo-2-(2-propan-2-ylphenyl)-7H-purin-9-yl]methyl]benzonitrile Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C#N)C=C1)=O NMHQSBILCWUIIO-UHFFFAOYSA-N 0.000 description 1
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 1
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
• RJGRIVFXOGKBMZ-UHFFFAOYSA-N 6-(dimethylamino)-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound CN(C1=C2NC(N(C2=NC(=N1)C1=C(C=CC=C1)C(C)C)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O)C RJGRIVFXOGKBMZ-UHFFFAOYSA-N 0.000 description 1
• VPGFRMSAVWJRTB-UHFFFAOYSA-N 6-(methylamino)-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC(=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O)NC VPGFRMSAVWJRTB-UHFFFAOYSA-N 0.000 description 1
• IXOVXJNDSFFRCL-UHFFFAOYSA-N 7-[2-(dimethylamino)ethyl]-2-(2-propan-2-ylphenyl)-9-[(4-pyrazol-1-ylphenyl)methyl]purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(CN2C3=NC(=NC=C3N(C2=O)CCN(C)C)C2=C(C=CC=C2)C(C)C)C=C1 IXOVXJNDSFFRCL-UHFFFAOYSA-N 0.000 description 1
• QUCRMJOZIBMDAH-UHFFFAOYSA-N 7-methyl-2-(2-propan-2-ylphenyl)-9-[(1-propan-2-ylsulfonylpiperidin-4-yl)methyl]purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1CCN(CC1)S(=O)(=O)C(C)C)=O)C QUCRMJOZIBMDAH-UHFFFAOYSA-N 0.000 description 1
• GWNNLZPZSVOJIT-UHFFFAOYSA-N 7-methyl-2-(2-propan-2-ylphenyl)-9-[(1-pyridin-3-ylsulfonylpiperidin-4-yl)methyl]purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1CCN(CC1)S(=O)(=O)C=1C=NC=CC=1)=O)C GWNNLZPZSVOJIT-UHFFFAOYSA-N 0.000 description 1
• ILWYHNJILKTEJD-UHFFFAOYSA-N 7-methyl-2-(2-propan-2-ylphenyl)-9-[(1-pyrimidin-2-ylpiperidin-4-yl)methyl]purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1CCN(CC1)C1=NC=CC=N1)=O)C ILWYHNJILKTEJD-UHFFFAOYSA-N 0.000 description 1
• JAOMDWLHBQYDHS-UHFFFAOYSA-N 7-methyl-2-(2-propan-2-ylphenyl)-9-[(4-pyrazol-1-ylphenyl)methyl]purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C=CC=C2)C(C)C)C=C1 JAOMDWLHBQYDHS-UHFFFAOYSA-N 0.000 description 1
• ZKNHYWJXHNKKCF-UHFFFAOYSA-N 7-methyl-2-(2-propan-2-ylphenyl)-9-[[1-(1,3,4-thiadiazol-2-yl)piperidin-4-yl]methyl]purin-8-one Chemical compound S1C(=NN=C1)N1CCC(CC1)CN1C2=NC(=NC=C2N(C1=O)C)C1=C(C=CC=C1)C(C)C ZKNHYWJXHNKKCF-UHFFFAOYSA-N 0.000 description 1
• QZXAXCFKGIFZJS-UHFFFAOYSA-N 7-methyl-2-(2-propan-2-ylphenyl)-9-[[3-(pyridin-2-ylmethoxy)phenyl]methyl]purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC(=CC=C1)OCC1=NC=CC=C1)=O)C QZXAXCFKGIFZJS-UHFFFAOYSA-N 0.000 description 1
• DTQUVAVSMPGAHA-UHFFFAOYSA-N 7-methyl-2-(2-propan-2-ylphenyl)-9-[[4-(2-propan-2-ylpyrazol-3-yl)phenyl]methyl]purin-8-one Chemical compound C(C)(C)N1N=CC=C1C1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C=CC=C2)C(C)C)C=C1 DTQUVAVSMPGAHA-UHFFFAOYSA-N 0.000 description 1
• JUDVVPKOSNRRKU-UHFFFAOYSA-N 7-methyl-2-(2-propan-2-ylphenyl)-9-[[4-(pyridin-2-ylmethoxy)phenyl]methyl]purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)OCC1=NC=CC=C1)=O)C JUDVVPKOSNRRKU-UHFFFAOYSA-N 0.000 description 1
• YXWHMWVXWXVKDV-UHFFFAOYSA-N 7-methyl-2-(2-propan-2-ylphenyl)-9H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(NC2=N1)=O)C YXWHMWVXWXVKDV-UHFFFAOYSA-N 0.000 description 1
• FWABACVPXXVTBA-UHFFFAOYSA-N 7-methyl-2-(3-propan-2-ylpyridin-4-yl)-9-[(4-pyrazol-1-ylphenyl)methyl]purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C=NC=C2)C(C)C)C=C1 FWABACVPXXVTBA-UHFFFAOYSA-N 0.000 description 1
• CAJYQOLRJOWKKY-UHFFFAOYSA-N 7-methyl-2-(4-propan-2-ylpyridin-3-yl)-9-[(4-pyrazol-1-ylphenyl)methyl]purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C=2C=NC=CC=2C(C)C)C=C1 CAJYQOLRJOWKKY-UHFFFAOYSA-N 0.000 description 1
• JEMKCKBUJDBXAK-UHFFFAOYSA-N 7-methyl-9-[1-[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]cyclopropyl]-2-(2-propan-2-ylpyridin-3-yl)purin-8-one Chemical compound C(C)(C)C1=NC=CC=C1C1=NC=C2N(C(N(C2=N1)C1(CC1)C1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O)C JEMKCKBUJDBXAK-UHFFFAOYSA-N 0.000 description 1
• TWDDOHYCEKNOGP-UHFFFAOYSA-N 7-methyl-9-[[1-(2-methylpropanoyl)piperidin-4-yl]methyl]-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C(C(C)C)(=O)N1CCC(CC1)CN1C2=NC(=NC=C2N(C1=O)C)C1=C(C=CC=C1)C(C)C TWDDOHYCEKNOGP-UHFFFAOYSA-N 0.000 description 1
• XKZWUIGGGFXCPT-UHFFFAOYSA-N 7-methyl-9-[[3-(oxolan-3-ylmethoxy)phenyl]methyl]-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC(=CC=C1)OCC1COCC1)=O)C XKZWUIGGGFXCPT-UHFFFAOYSA-N 0.000 description 1
• PECUSPWKNJVAKX-UHFFFAOYSA-N 7-methyl-9-[[3-[(1-methylpiperidin-3-yl)methoxy]phenyl]methyl]-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC(=CC=C1)OCC1CN(CCC1)C)=O)C PECUSPWKNJVAKX-UHFFFAOYSA-N 0.000 description 1
• DWXSJIPGBJCYOY-UHFFFAOYSA-N 7-methyl-9-[[3-[(3-methylimidazol-4-yl)methoxy]phenyl]methyl]-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC(=CC=C1)OCC1=CN=CN1C)=O)C DWXSJIPGBJCYOY-UHFFFAOYSA-N 0.000 description 1
• OKOOHRFHYJOMQK-UHFFFAOYSA-N 7-methyl-9-[[4-(1-methyl-1,2,4-triazol-3-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)C1=NN(C=N1)C)=O)C OKOOHRFHYJOMQK-UHFFFAOYSA-N 0.000 description 1
• VCYCOBSJPVSWEM-UHFFFAOYSA-N 7-methyl-9-[[4-(1-methylimidazol-2-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=CN=1)C)=O)C VCYCOBSJPVSWEM-UHFFFAOYSA-N 0.000 description 1
• JTKOFKQBJPUYRQ-UHFFFAOYSA-N 7-methyl-9-[[4-(1-methylimidazol-4-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)C=1N=CN(C=1)C)=O)C JTKOFKQBJPUYRQ-UHFFFAOYSA-N 0.000 description 1
• ALYLAGSPTIQEKV-UHFFFAOYSA-N 7-methyl-9-[[4-(1-methyltriazol-4-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)C=1N=NN(C=1)C)=O)C ALYLAGSPTIQEKV-UHFFFAOYSA-N 0.000 description 1
• LSCQGVXBMUGFDP-UHFFFAOYSA-N 7-methyl-9-[[4-(1-piperidin-4-ylimidazol-2-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=CN=1)C1CCNCC1)=O)C LSCQGVXBMUGFDP-UHFFFAOYSA-N 0.000 description 1
• PKVLSAWCPWZKRW-UHFFFAOYSA-N 7-methyl-9-[[4-(1-propan-2-ylimidazol-2-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C(C)(C)N1C(=NC=C1)C1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C=CC=C2)C(C)C)C=C1 PKVLSAWCPWZKRW-UHFFFAOYSA-N 0.000 description 1
• JTJMLDUEYOOGOG-UHFFFAOYSA-N 7-methyl-9-[[4-(1-propan-2-ylimidazol-4-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C(C)(C)N1C=NC(=C1)C1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C=CC=C2)C(C)C)C=C1 JTJMLDUEYOOGOG-UHFFFAOYSA-N 0.000 description 1
• ZTAHTRJBAKLRGB-UHFFFAOYSA-N 7-methyl-9-[[4-(3-methylimidazol-4-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)C1=CN=CN1C)=O)C ZTAHTRJBAKLRGB-UHFFFAOYSA-N 0.000 description 1
• KEYQNLYNEOYIKI-UHFFFAOYSA-N 7-methyl-9-[[4-(3-methyltriazol-4-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)C1=CN=NN1C)=O)C KEYQNLYNEOYIKI-UHFFFAOYSA-N 0.000 description 1
• MTIGCPNEKGGGNQ-UHFFFAOYSA-N 7-methyl-9-[[4-(3-piperidin-4-ylpyrazol-1-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)N1N=C(C=C1)C1CCNCC1)=O)C MTIGCPNEKGGGNQ-UHFFFAOYSA-N 0.000 description 1
• SDUOPTVHSYJCDG-UHFFFAOYSA-N 7-methyl-9-[[4-(4-methyl-1,3-oxazol-2-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)C=1OC=C(N=1)C)=O)C SDUOPTVHSYJCDG-UHFFFAOYSA-N 0.000 description 1
• ICNPEQXBBTXDJE-UHFFFAOYSA-N 7-methyl-9-[[4-(5-methyl-1,3-thiazol-4-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)C=1N=CSC=1C)=O)C ICNPEQXBBTXDJE-UHFFFAOYSA-N 0.000 description 1
• NQXFFSDYEWGTLH-UHFFFAOYSA-N 7-methyl-9-[[4-(6-morpholin-4-ylpyrimidin-4-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)C1=NC=NC(=C1)N1CCOCC1)=O)C NQXFFSDYEWGTLH-UHFFFAOYSA-N 0.000 description 1
• MNRQHQAPQCHXCG-UHFFFAOYSA-N 7-methyl-9-[[4-(oxan-4-yloxy)phenyl]methyl]-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)OC1CCOCC1)=O)C MNRQHQAPQCHXCG-UHFFFAOYSA-N 0.000 description 1
• XRYCABJKSNWMNG-UHFFFAOYSA-N 7-methyl-9-[[4-(oxolan-3-ylmethoxy)phenyl]methyl]-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)OCC1COCC1)=O)C XRYCABJKSNWMNG-UHFFFAOYSA-N 0.000 description 1
• OTMBDANQIXSLRP-UHFFFAOYSA-N 7-methyl-9-[[4-[(1-methylpiperidin-3-yl)methoxy]phenyl]methyl]-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)OCC1CN(CCC1)C)=O)C OTMBDANQIXSLRP-UHFFFAOYSA-N 0.000 description 1
• QMQNKSFWAWGEKN-UHFFFAOYSA-N 7-methyl-9-[[4-[(3-methylimidazol-4-yl)methoxy]phenyl]methyl]-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)OCC1=CN=CN1C)=O)C QMQNKSFWAWGEKN-UHFFFAOYSA-N 0.000 description 1
• CTVUGKGNUPKWQT-UHFFFAOYSA-N 7-methyl-9-[[4-[(5-methyl-1,2-oxazol-3-yl)methoxy]phenyl]methyl]-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)OCC1=NOC(=C1)C)=O)C CTVUGKGNUPKWQT-UHFFFAOYSA-N 0.000 description 1
• ARRYFAVWQLDCTP-UHFFFAOYSA-N 7-methyl-9-[[4-[1-(1-methylazetidin-3-yl)-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C1CN(C1)C)=O)C ARRYFAVWQLDCTP-UHFFFAOYSA-N 0.000 description 1
• FKUZJWQVEOWKFS-UHFFFAOYSA-N 7-methyl-9-[[4-[1-(oxetan-3-yl)-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C1COC1)=O)C FKUZJWQVEOWKFS-UHFFFAOYSA-N 0.000 description 1
• BXYQFRASIIQQGS-UHFFFAOYSA-N 7-methyl-9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-2-[2-(trifluoromethoxy)phenyl]purin-8-one Chemical compound CN1C(N(C2=NC(=NC=C12)C1=C(C=CC=C1)OC(F)(F)F)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O BXYQFRASIIQQGS-UHFFFAOYSA-N 0.000 description 1
• YICIEIRLIGVZAN-UHFFFAOYSA-N 7-methyl-9-[[4-[1-methyl-5-(trifluoromethyl)-1,2,4-triazol-3-yl]phenyl]methyl]-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)C1=NN(C(=N1)C(F)(F)F)C)=O)C YICIEIRLIGVZAN-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• PSSNXNASBJNKDR-UHFFFAOYSA-N 9-[(1-cyclopropylsulfonyl-4-fluoropiperidin-4-yl)methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C1(CC1)S(=O)(=O)N1CCC(CC1)(F)CN1C2=NC(=NC=C2NC1=O)C1=C(C=CC=C1)C(C)C PSSNXNASBJNKDR-UHFFFAOYSA-N 0.000 description 1
• FXNPTBKNKIJNQZ-UHFFFAOYSA-N 9-[(1-cyclopropylsulfonylpiperidin-4-yl)methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C1(CC1)S(=O)(=O)N1CCC(CC1)CN1C2=NC(=NC=C2NC1=O)C1=C(C=CC=C1)C(C)C FXNPTBKNKIJNQZ-UHFFFAOYSA-N 0.000 description 1
• WCXMFDBXQGQFCR-UHFFFAOYSA-N 9-[(1-methylbenzimidazol-5-yl)methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC2=C(N(C=N2)C)C=C1)=O WCXMFDBXQGQFCR-UHFFFAOYSA-N 0.000 description 1
• GWFMHAOARYKEDP-CQSZACIVSA-N 9-[(1R)-1-(4-fluorophenyl)ethyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound FC1=CC=C(C=C1)[C@@H](C)N1C2=NC(=NC=C2NC1=O)C1=C(C=CC=C1)C(C)C GWFMHAOARYKEDP-CQSZACIVSA-N 0.000 description 1
• AHGZHJBQQHDICO-QGZVFWFLSA-N 9-[(1R)-1-[4-(1-methylimidazol-2-yl)phenyl]ethyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)[C@H](C)C1=CC=C(C=C1)C=1N(C=CN=1)C)=O AHGZHJBQQHDICO-QGZVFWFLSA-N 0.000 description 1
• ACTYVDNKCSSLLO-LJQANCHMSA-N 9-[(1R)-1-[4-(3,5-dimethylpyrazol-1-yl)phenyl]ethyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound CC1=NN(C(=C1)C)C1=CC=C(C=C1)[C@@H](C)N1C2=NC(=NC=C2NC1=O)C1=C(C=CC=C1)C(C)C ACTYVDNKCSSLLO-LJQANCHMSA-N 0.000 description 1
• PHRMVYQMXDLTKZ-MRXNPFEDSA-N 9-[(1R)-1-[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]ethyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)[C@H](C)C1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O PHRMVYQMXDLTKZ-MRXNPFEDSA-N 0.000 description 1
• SEOLBYWIIXJKDN-OAHLLOKOSA-N 9-[(1R)-1-phenylethyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)[C@H](C)C1=CC=CC=C1)=O SEOLBYWIIXJKDN-OAHLLOKOSA-N 0.000 description 1
• VRCIZGDHCQVOEY-FXAWDEMLSA-N 9-[(1R,2S)-2-(4-pyrazol-1-ylphenyl)cyclobutyl]-2-[2-(2,2,2-trifluoroethoxy)pyridin-3-yl]-7H-purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(C=C1)[C@H]1[C@@H](CC1)N1C2=NC(=NC=C2NC1=O)C=1C(=NC=CC=1)OCC(F)(F)F VRCIZGDHCQVOEY-FXAWDEMLSA-N 0.000 description 1
• MZNISAXJJGFBJH-LJQANCHMSA-N 9-[(1S)-1-(4-fluorophenyl)-2-hydroxyethyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound FC1=CC=C(C=C1)[C@@H](CO)N1C2=NC(=NC=C2NC1=O)C1=C(C=CC=C1)C(C)C MZNISAXJJGFBJH-LJQANCHMSA-N 0.000 description 1
• GWFMHAOARYKEDP-AWEZNQCLSA-N 9-[(1S)-1-(4-fluorophenyl)ethyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound FC1=CC=C(C=C1)[C@H](C)N1C2=NC(=NC=C2NC1=O)C1=C(C=CC=C1)C(C)C GWFMHAOARYKEDP-AWEZNQCLSA-N 0.000 description 1
• AHGZHJBQQHDICO-KRWDZBQOSA-N 9-[(1S)-1-[4-(1-methylimidazol-2-yl)phenyl]ethyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)[C@@H](C)C1=CC=C(C=C1)C=1N(C=CN=1)C)=O AHGZHJBQQHDICO-KRWDZBQOSA-N 0.000 description 1
• ACTYVDNKCSSLLO-IBGZPJMESA-N 9-[(1S)-1-[4-(3,5-dimethylpyrazol-1-yl)phenyl]ethyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound CC1=NN(C(=C1)C)C1=CC=C(C=C1)[C@H](C)N1C2=NC(=NC=C2NC1=O)C1=C(C=CC=C1)C(C)C ACTYVDNKCSSLLO-IBGZPJMESA-N 0.000 description 1
• PHRMVYQMXDLTKZ-INIZCTEOSA-N 9-[(1S)-1-[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]ethyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)[C@@H](C)C1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O PHRMVYQMXDLTKZ-INIZCTEOSA-N 0.000 description 1
• SEOLBYWIIXJKDN-HNNXBMFYSA-N 9-[(1S)-1-phenylethyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)[C@@H](C)C1=CC=CC=C1)=O SEOLBYWIIXJKDN-HNNXBMFYSA-N 0.000 description 1
• RMSMNOHPYNTUAS-LJQANCHMSA-N 9-[(1S)-2-hydroxy-1-phenylethyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound OC[C@H](C1=CC=CC=C1)N1C2=NC(=NC=C2NC1=O)C1=C(C=CC=C1)C(C)C RMSMNOHPYNTUAS-LJQANCHMSA-N 0.000 description 1
• KQFXBOUJHLLRLS-UHFFFAOYSA-N 9-[(2-chloro-4-pyrazol-1-ylphenyl)methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound ClC1=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=CC(=C1)N1N=CC=C1 KQFXBOUJHLLRLS-UHFFFAOYSA-N 0.000 description 1
• NIPJAYQPIXPSLZ-UHFFFAOYSA-N 9-[(2-fluoro-4-pyrazol-1-ylphenyl)methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound FC1=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=CC(=C1)N1N=CC=C1 NIPJAYQPIXPSLZ-UHFFFAOYSA-N 0.000 description 1
• VMAWGDHHRUGRNY-UHFFFAOYSA-N 9-[(2-methyl-1-oxo-3H-isoindol-5-yl)methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC=1C=C2CN(C(C2=CC=1)=O)C)=O VMAWGDHHRUGRNY-UHFFFAOYSA-N 0.000 description 1
• FUADOLWBQXXXEY-UHFFFAOYSA-N 9-[(3-cyclobutyloxyphenyl)methyl]-7-methyl-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C1(CCC1)OC=1C=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C=CC=C2)C(C)C)C=CC=1 FUADOLWBQXXXEY-UHFFFAOYSA-N 0.000 description 1
• KFUCYMFPJAFTDQ-UHFFFAOYSA-N 9-[(3-fluoro-4-pyrazol-1-ylphenyl)methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound FC=1C=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=CC=1N1N=CC=C1 KFUCYMFPJAFTDQ-UHFFFAOYSA-N 0.000 description 1
• UTRKOYWLERIQOT-UHFFFAOYSA-N 9-[(4-cyclobutyloxyphenyl)methyl]-7-methyl-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C1(CCC1)OC1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C=CC=C2)C(C)C)C=C1 UTRKOYWLERIQOT-UHFFFAOYSA-N 0.000 description 1
• ARKAMNUBYNVMSR-UHFFFAOYSA-N 9-[(4-fluoro-1-pyridin-3-ylpiperidin-4-yl)methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound FC1(CCN(CC1)C=1C=NC=CC=1)CN1C2=NC(=NC=C2NC1=O)C1=C(C=CC=C1)C(C)C ARKAMNUBYNVMSR-UHFFFAOYSA-N 0.000 description 1
• JVXSJTZEUKSLNL-UHFFFAOYSA-N 9-[(4-imidazo[1,2-a]pyrazin-8-ylphenyl)methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound N=1C=CN2C=1C(=NC=C2)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 JVXSJTZEUKSLNL-UHFFFAOYSA-N 0.000 description 1
• QTDFINNFWQRFQX-UHFFFAOYSA-N 9-[(4-imidazo[1,2-a]pyrazin-8-ylphenyl)methyl]-7-methyl-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound N=1C=CN2C=1C(=NC=C2)C1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C=CC=C2)C(C)C)C=C1 QTDFINNFWQRFQX-UHFFFAOYSA-N 0.000 description 1
• NTWNHYPJFNEIDG-UHFFFAOYSA-N 9-[(4-imidazo[1,2-a]pyridin-5-ylphenyl)methyl]-7-methyl-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound N=1C=CN2C=1C=CC=C2C1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C=CC=C2)C(C)C)C=C1 NTWNHYPJFNEIDG-UHFFFAOYSA-N 0.000 description 1
• KCGVGLWMNZRQHD-UHFFFAOYSA-N 9-[(4-imidazo[1,2-a]pyridin-8-ylphenyl)methyl]-7-methyl-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound N=1C=CN2C=1C(=CC=C2)C1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C=CC=C2)C(C)C)C=C1 KCGVGLWMNZRQHD-UHFFFAOYSA-N 0.000 description 1
• RGFOKPWAPZBONW-UHFFFAOYSA-N 9-[(4-methylsulfonylphenyl)methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)S(=O)(=O)C)=O RGFOKPWAPZBONW-UHFFFAOYSA-N 0.000 description 1
• INNHJKMPZHZMEM-UHFFFAOYSA-N 9-[(4-pyrazol-1-ylphenyl)methyl]-2-[2-(2,2,2-trifluoroethoxy)phenyl]-7H-purin-8-one Chemical compound N1(N=CC=C1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)OCC(F)(F)F)C=C1 INNHJKMPZHZMEM-UHFFFAOYSA-N 0.000 description 1
• HKXBRFVWKRZQMZ-LJQANCHMSA-N 9-[(4R)-3,4-dihydro-2H-chromen-4-yl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound O1CC[C@H](C2=CC=CC=C12)N1C2=NC(=NC=C2NC1=O)C1=C(C=CC=C1)C(C)C HKXBRFVWKRZQMZ-LJQANCHMSA-N 0.000 description 1
• RJVQKGJURMDSRS-UHFFFAOYSA-N 9-[1-(4-fluorophenyl)cyclopropyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound FC1=CC=C(C=C1)C1(CC1)N1C2=NC(=NC=C2NC1=O)C1=C(C=CC=C1)C(C)C RJVQKGJURMDSRS-UHFFFAOYSA-N 0.000 description 1
• HILKFMTWZNIGDU-UHFFFAOYSA-N 9-[1-[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]cyclopropyl]-2-(2-propan-2-ylpyridin-3-yl)-7H-purin-8-one Chemical compound C(C)(C)C1=NC=CC=C1C1=NC=C2NC(N(C2=N1)C1(CC1)C1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O HILKFMTWZNIGDU-UHFFFAOYSA-N 0.000 description 1
• CCENAIOBMSWINB-UHFFFAOYSA-N 9-[[1-(2,5-dimethyl-1,3-thiazol-4-yl)-4-fluoropiperidin-4-yl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound CC=1SC(=C(N=1)N1CCC(CC1)(F)CN1C2=NC(=NC=C2NC1=O)C1=C(C=CC=C1)C(C)C)C CCENAIOBMSWINB-UHFFFAOYSA-N 0.000 description 1
• MMSKLCBFPXYWEQ-UHFFFAOYSA-N 9-[[1-(2,5-dimethyl-1,3-thiazol-4-yl)piperidin-4-yl]methyl]-7-methyl-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound CC=1SC(=C(N=1)N1CCC(CC1)CN1C2=NC(=NC=C2N(C1=O)C)C1=C(C=CC=C1)C(C)C)C MMSKLCBFPXYWEQ-UHFFFAOYSA-N 0.000 description 1
• UJORFMCCUDZAJK-UHFFFAOYSA-N 9-[[3-(cyclopropylmethoxy)phenyl]methyl]-7-methyl-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C1(CC1)COC=1C=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C=CC=C2)C(C)C)C=CC=1 UJORFMCCUDZAJK-UHFFFAOYSA-N 0.000 description 1
• YWSFBXARESLBME-UHFFFAOYSA-N 9-[[3-[2-(dimethylamino)ethoxy]phenyl]methyl]-7-methyl-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound CN(CCOC=1C=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C=CC=C2)C(C)C)C=CC=1)C YWSFBXARESLBME-UHFFFAOYSA-N 0.000 description 1
• NJDCDGOENMQFFB-UHFFFAOYSA-N 9-[[3-[3-(dimethylamino)propoxy]phenyl]methyl]-7-methyl-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound CN(CCCOC=1C=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C=CC=C2)C(C)C)C=CC=1)C NJDCDGOENMQFFB-UHFFFAOYSA-N 0.000 description 1
• XBHCWRVXDMRZKM-UHFFFAOYSA-N 9-[[4-(1,2-benzoxazol-7-yl)phenyl]methyl]-7-methyl-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound O1N=CC2=C1C(=CC=C2)C1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C=CC=C2)C(C)C)C=C1 XBHCWRVXDMRZKM-UHFFFAOYSA-N 0.000 description 1
• UAXKVDJMVMZRQW-UHFFFAOYSA-N 9-[[4-(1,2-dimethylimidazol-4-yl)phenyl]methyl]-7-methyl-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound CN1C(=NC(=C1)C1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C=CC=C2)C(C)C)C=C1)C UAXKVDJMVMZRQW-UHFFFAOYSA-N 0.000 description 1
• MKYSEBGOWCALQF-UHFFFAOYSA-N 9-[[4-(1,3-oxazol-2-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1OC=CN=1)=O MKYSEBGOWCALQF-UHFFFAOYSA-N 0.000 description 1
• LMHNTSIOEBVGQU-UHFFFAOYSA-N 9-[[4-(1,4-dimethylimidazol-2-yl)phenyl]methyl]-2-(3-fluoro-2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound CN1C(=NC(=C1)C)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C(=CC=C2)F)C(C)C)C=C1 LMHNTSIOEBVGQU-UHFFFAOYSA-N 0.000 description 1
• SKAUHODTEXFEER-UHFFFAOYSA-N 9-[[4-(1,4-dimethylimidazol-2-yl)phenyl]methyl]-7-methyl-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound CN1C(=NC(=C1)C)C1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C=CC=C2)C(C)C)C=C1 SKAUHODTEXFEER-UHFFFAOYSA-N 0.000 description 1
• JTVMFAFOFOOVAZ-UHFFFAOYSA-N 9-[[4-(1,5-dimethyl-1,2,4-triazol-3-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound CN1N=C(N=C1C)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 JTVMFAFOFOOVAZ-UHFFFAOYSA-N 0.000 description 1
• BNBXGUPTHHKKAA-UHFFFAOYSA-N 9-[[4-(1,5-dimethylpyrazol-4-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound CN1N=CC(=C1C)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 BNBXGUPTHHKKAA-UHFFFAOYSA-N 0.000 description 1
• OCUKIQQANLFTOE-UHFFFAOYSA-N 9-[[4-(1-ethylimidazol-2-yl)phenyl]methyl]-7-methyl-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C(C)N1C(=NC=C1)C1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C=CC=C2)C(C)C)C=C1 OCUKIQQANLFTOE-UHFFFAOYSA-N 0.000 description 1
• KIEJADLEJDVLJC-UHFFFAOYSA-N 9-[[4-(1-methyl-1,2,4-triazol-3-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C1=NN(C=N1)C)=O KIEJADLEJDVLJC-UHFFFAOYSA-N 0.000 description 1
• HLZCGXIXSNPXQZ-UHFFFAOYSA-N 9-[[4-(1-methyl-5-morpholin-4-yl-1,2,4-triazol-3-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C1=NN(C(=N1)N1CCOCC1)C)=O HLZCGXIXSNPXQZ-UHFFFAOYSA-N 0.000 description 1
• UMRSOOYEKVAFAK-UHFFFAOYSA-N 9-[[4-(1-methylimidazol-2-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=CN=1)C)=O UMRSOOYEKVAFAK-UHFFFAOYSA-N 0.000 description 1
• IEQBHNVJKHUODX-UHFFFAOYSA-N 9-[[4-(1-methylimidazol-4-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N=CN(C=1)C)=O IEQBHNVJKHUODX-UHFFFAOYSA-N 0.000 description 1
• FCLPAYYOPHCSTC-UHFFFAOYSA-N 9-[[4-(1-piperidin-4-ylpyrazol-4-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1C=NN(C=1)C1CCNCC1)=O FCLPAYYOPHCSTC-UHFFFAOYSA-N 0.000 description 1
• UYDUEIGTDPUVEZ-UHFFFAOYSA-N 9-[[4-(1-propan-2-ylimidazol-4-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)N1C=NC(=C1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 UYDUEIGTDPUVEZ-UHFFFAOYSA-N 0.000 description 1
• NVFBJGXSFZXCMS-UHFFFAOYSA-N 9-[[4-(1H-imidazol-2-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound N1C(=NC=C1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 NVFBJGXSFZXCMS-UHFFFAOYSA-N 0.000 description 1
• GDBASHXUBCLJGU-UHFFFAOYSA-N 9-[[4-(1H-imidazol-2-yl)phenyl]methyl]-7-methyl-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound N1C(=NC=C1)C1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C=CC=C2)C(C)C)C=C1 GDBASHXUBCLJGU-UHFFFAOYSA-N 0.000 description 1
• CEYYLUKDNSSBMQ-UHFFFAOYSA-N 9-[[4-(1H-indazol-7-yl)phenyl]methyl]-7-methyl-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound N1N=CC2=CC=CC(=C12)C1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C=CC=C2)C(C)C)C=C1 CEYYLUKDNSSBMQ-UHFFFAOYSA-N 0.000 description 1
• VBQDPLWVFBHMEZ-UHFFFAOYSA-N 9-[[4-(2,5-dimethyl-1,2,4-triazol-3-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound CN1N=C(N=C1C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1)C VBQDPLWVFBHMEZ-UHFFFAOYSA-N 0.000 description 1
• NVLNPUKICVACQI-UHFFFAOYSA-N 9-[[4-(2,5-dimethyl-1,3-oxazol-4-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound CC=1OC(=C(N=1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1)C NVLNPUKICVACQI-UHFFFAOYSA-N 0.000 description 1
• XUMSZKXSGQIHJK-UHFFFAOYSA-N 9-[[4-(2,5-dimethyl-1,3-thiazol-4-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound CC=1SC(=C(N=1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1)C XUMSZKXSGQIHJK-UHFFFAOYSA-N 0.000 description 1
• ATKWSLZEZWBVQD-UHFFFAOYSA-N 9-[[4-(2,5-dimethyl-1,3-thiazol-4-yl)phenyl]methyl]-7-methyl-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound CC=1SC(=C(N=1)C1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C=CC=C2)C(C)C)C=C1)C ATKWSLZEZWBVQD-UHFFFAOYSA-N 0.000 description 1
• ICPYJFLNEAOYRA-UHFFFAOYSA-N 9-[[4-(2-ethoxyethoxy)phenyl]methyl]-7-methyl-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C(C)OCCOC1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C=CC=C2)C(C)C)C=C1 ICPYJFLNEAOYRA-UHFFFAOYSA-N 0.000 description 1
• FZLSUYPEXXSVCQ-UHFFFAOYSA-N 9-[[4-(2-ethylpiperidine-1-carbonyl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)C1N(CCCC1)C(=O)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 FZLSUYPEXXSVCQ-UHFFFAOYSA-N 0.000 description 1
• LLSPLJVOHUTEJA-UHFFFAOYSA-N 9-[[4-(2-methoxyethylamino)phenyl]methyl]-7-methyl-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)NCCOC)=O)C LLSPLJVOHUTEJA-UHFFFAOYSA-N 0.000 description 1
• VQOHCLBXMHTJHM-UHFFFAOYSA-N 9-[[4-(2-methyl-5-oxopyrazol-1-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)N1N(C=CC1=O)C)=O VQOHCLBXMHTJHM-UHFFFAOYSA-N 0.000 description 1
• UFTPYZCEAJYNHQ-UHFFFAOYSA-N 9-[[4-(2-methylpiperidine-1-carbonyl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C(=O)N1C(CCCC1)C)=O UFTPYZCEAJYNHQ-UHFFFAOYSA-N 0.000 description 1
• HUTIPJIYHFWFAP-UHFFFAOYSA-N 9-[[4-(2-methylpyrazol-3-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C1=CC=NN1C)=O HUTIPJIYHFWFAP-UHFFFAOYSA-N 0.000 description 1
• WUJKCSSUEYXAQO-UHFFFAOYSA-N 9-[[4-(2-methylpyrrolidine-1-carbonyl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C(=O)N1C(CCC1)C)=O WUJKCSSUEYXAQO-UHFFFAOYSA-N 0.000 description 1
• JBEYRKRMMSPMEL-UHFFFAOYSA-N 9-[[4-(2-oxa-5-azaspiro[3.4]octane-5-carbonyl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C1OCC11N(CCC1)C(=O)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 JBEYRKRMMSPMEL-UHFFFAOYSA-N 0.000 description 1
• DKVGEBDSMMSSDB-UHFFFAOYSA-N 9-[[4-(2-oxopyrrolidin-1-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)N1C(CCC1)=O)=O DKVGEBDSMMSSDB-UHFFFAOYSA-N 0.000 description 1
• HKDACUANWRYQSY-UHFFFAOYSA-N 9-[[4-(3,3-difluoropyrrolidine-1-carbonyl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound FC1(CN(CC1)C(=O)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1)F HKDACUANWRYQSY-UHFFFAOYSA-N 0.000 description 1
• WDHVCVPFUBCZQV-UHFFFAOYSA-N 9-[[4-(3,3-dimethyloxetan-2-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound CC1(C(OC1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1)C WDHVCVPFUBCZQV-UHFFFAOYSA-N 0.000 description 1
• FTOSEGDRSMTLQW-UHFFFAOYSA-N 9-[[4-(3,5-dimethyl-1,2-oxazol-4-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound CC1=NOC(=C1C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1)C FTOSEGDRSMTLQW-UHFFFAOYSA-N 0.000 description 1
• UINAAHUQDMZGIL-UHFFFAOYSA-N 9-[[4-(3,5-dimethylpyrazol-1-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound CC1=NN(C(=C1)C)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 UINAAHUQDMZGIL-UHFFFAOYSA-N 0.000 description 1
• FUETZVUETPLSNG-UHFFFAOYSA-N 9-[[4-(3-chloro-5-methylpyrazol-1-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound ClC1=NN(C(=C1)C)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 FUETZVUETPLSNG-UHFFFAOYSA-N 0.000 description 1
• XABXFYMFYJJKTK-UHFFFAOYSA-N 9-[[4-(3-fluoroazetidine-1-carbonyl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound FC1CN(C1)C(=O)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 XABXFYMFYJJKTK-UHFFFAOYSA-N 0.000 description 1
• MGQBHVDXXAYHRH-UHFFFAOYSA-N 9-[[4-(3-hydroxyazetidine-1-carbonyl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound OC1CN(C1)C(=O)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 MGQBHVDXXAYHRH-UHFFFAOYSA-N 0.000 description 1
• YVTNMMYCRWVGTN-UHFFFAOYSA-N 9-[[4-(3-methoxypiperidine-1-carbonyl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C(=O)N1CC(CCC1)OC)=O YVTNMMYCRWVGTN-UHFFFAOYSA-N 0.000 description 1
• XBMTXDHNJZYFQB-UHFFFAOYSA-N 9-[[4-(3-methoxypyrazol-1-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)N1N=C(C=C1)OC)=O XBMTXDHNJZYFQB-UHFFFAOYSA-N 0.000 description 1
• CMKPYKOQKZDBGN-UHFFFAOYSA-N 9-[[4-(3-methylimidazol-4-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C1=CN=CN1C)=O CMKPYKOQKZDBGN-UHFFFAOYSA-N 0.000 description 1
• YMLUTMFLBNKHLP-UHFFFAOYSA-N 9-[[4-(3-methylpiperidine-1-carbonyl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C(=O)N1CC(CCC1)C)=O YMLUTMFLBNKHLP-UHFFFAOYSA-N 0.000 description 1
• CJLCHFIZGCZPTM-UHFFFAOYSA-N 9-[[4-(3-methyltriazol-4-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C1=CN=NN1C)=O CJLCHFIZGCZPTM-UHFFFAOYSA-N 0.000 description 1
• RTLHFMMTPSJNRX-UHFFFAOYSA-N 9-[[4-(3-morpholin-4-ylpyrazol-1-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)N1N=C(C=C1)N1CCOCC1)=O RTLHFMMTPSJNRX-UHFFFAOYSA-N 0.000 description 1
• ZWGLJHBMNMBIIM-UHFFFAOYSA-N 9-[[4-(3-piperazin-1-ylpyrazol-1-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)N1N=C(C=C1)N1CCNCC1)=O ZWGLJHBMNMBIIM-UHFFFAOYSA-N 0.000 description 1
• WILPFCRARDPVEH-UHFFFAOYSA-N 9-[[4-(3-piperidin-3-ylpyrazol-1-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)N1N=C(C=C1)C1CNCCC1)=O WILPFCRARDPVEH-UHFFFAOYSA-N 0.000 description 1
• CUBYCLSXCZJUEW-UHFFFAOYSA-N 9-[[4-(3-piperidin-4-ylpyrazol-1-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)N1N=C(C=C1)C1CCNCC1)=O CUBYCLSXCZJUEW-UHFFFAOYSA-N 0.000 description 1
• JSTMLJGOTMJPLU-UHFFFAOYSA-N 9-[[4-(4,4-difluoropiperidine-1-carbonyl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound FC1(CCN(CC1)C(=O)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1)F JSTMLJGOTMJPLU-UHFFFAOYSA-N 0.000 description 1
• BKGNPIQVLAQKQO-UHFFFAOYSA-N 9-[[4-(4-acetylpiperazine-1-carbonyl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(=O)N1CCN(CC1)C(=O)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 BKGNPIQVLAQKQO-UHFFFAOYSA-N 0.000 description 1
• LCLRPLNEJHBDBM-UHFFFAOYSA-N 9-[[4-(4-chloro-1-methylimidazol-2-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound ClC=1N=C(N(C=1)C)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 LCLRPLNEJHBDBM-UHFFFAOYSA-N 0.000 description 1
• CGAVHHLRQKXEQZ-UHFFFAOYSA-N 9-[[4-(4-cyclopropyltriazol-1-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C1(CC1)C=1N=NN(C=1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 CGAVHHLRQKXEQZ-UHFFFAOYSA-N 0.000 description 1
• HTCIVVIXRUWIAV-UHFFFAOYSA-N 9-[[4-(4-methyl-1-propan-2-ylimidazol-2-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)N1C(=NC(=C1)C)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 HTCIVVIXRUWIAV-UHFFFAOYSA-N 0.000 description 1
• DGJVUUCZIQZXLX-UHFFFAOYSA-N 9-[[4-(4-methylpiperazine-1-carbonyl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C(=O)N1CCN(CC1)C)=O DGJVUUCZIQZXLX-UHFFFAOYSA-N 0.000 description 1
• MOSUJVXSRNXCAC-UHFFFAOYSA-N 9-[[4-(4-methylpiperidine-1-carbonyl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C(=O)N1CCC(CC1)C)=O MOSUJVXSRNXCAC-UHFFFAOYSA-N 0.000 description 1
• GFICFJKBBVGIAN-UHFFFAOYSA-N 9-[[4-(4-methyltriazol-1-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)N1N=NC(=C1)C)=O GFICFJKBBVGIAN-UHFFFAOYSA-N 0.000 description 1
• FCZXRPCBBNOKEQ-UHFFFAOYSA-N 9-[[4-(4-phenyltriazol-1-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound CC(C)C1=C(C=CC=C1)C1=NC2=C(NC(=O)N2CC2=CC=C(C=C2)N2C=C(N=N2)C2=CC=CC=C2)C=N1 FCZXRPCBBNOKEQ-UHFFFAOYSA-N 0.000 description 1
• WSADMMYLOUFJPS-UHFFFAOYSA-N 9-[[4-(5,6-dihydro-4H-pyrrolo[3,4-c]pyrazol-1-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound N1(N=CC2=C1CNC2)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 WSADMMYLOUFJPS-UHFFFAOYSA-N 0.000 description 1
• NCVKKSWLUYNUHO-UHFFFAOYSA-N 9-[[4-(5-chloro-3-methylpyrazol-1-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound ClC1=CC(=NN1C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1)C NCVKKSWLUYNUHO-UHFFFAOYSA-N 0.000 description 1
• ZUBJZZDYBBPANO-UHFFFAOYSA-N 9-[[4-(5-fluoro-1-methylimidazol-2-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound FC1=CN=C(N1C)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 ZUBJZZDYBBPANO-UHFFFAOYSA-N 0.000 description 1
• AVYAVWZDCIFKHX-UHFFFAOYSA-N 9-[[4-(5-methoxy-1-methyl-1,2,4-triazol-3-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C1=NN(C(=N1)OC)C)=O AVYAVWZDCIFKHX-UHFFFAOYSA-N 0.000 description 1
• RASKRQVFJBWKDF-UHFFFAOYSA-N 9-[[4-(5-methoxypyrazol-1-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)N1N=CC=C1OC)=O RASKRQVFJBWKDF-UHFFFAOYSA-N 0.000 description 1
• RUCNTUYITSDWOY-UHFFFAOYSA-N 9-[[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C1=NOC(=N1)C)=O RUCNTUYITSDWOY-UHFFFAOYSA-N 0.000 description 1
• KZCXYNXTKZLZEC-UHFFFAOYSA-N 9-[[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1OC(=NN=1)C)=O KZCXYNXTKZLZEC-UHFFFAOYSA-N 0.000 description 1
• ZCIPXPZLKXHHGE-UHFFFAOYSA-N 9-[[4-(5-methyl-1,3-thiazol-4-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N=CSC=1C)=O ZCIPXPZLKXHHGE-UHFFFAOYSA-N 0.000 description 1
• UZRPFZZMVVGZLF-UHFFFAOYSA-N 9-[[4-(5-methyl-1-propan-2-ylimidazol-2-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)N1C(=NC=C1C)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 UZRPFZZMVVGZLF-UHFFFAOYSA-N 0.000 description 1
• YPGRUCUPXQGRLH-UHFFFAOYSA-N 9-[[4-(5-methylpyrazol-1-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)N1N=CC=C1C)=O YPGRUCUPXQGRLH-UHFFFAOYSA-N 0.000 description 1
• IDGICNFLDSTBHT-UHFFFAOYSA-N 9-[[4-(5-methyltetrazol-2-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)N1N=C(N=N1)C)=O IDGICNFLDSTBHT-UHFFFAOYSA-N 0.000 description 1
• AFHDRKAQSZZUFC-UHFFFAOYSA-N 9-[[4-(5-methyltriazol-1-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)N1N=NC=C1C)=O AFHDRKAQSZZUFC-UHFFFAOYSA-N 0.000 description 1
• RAQGJODOLACLDV-UHFFFAOYSA-N 9-[[4-(5-oxa-2-azaspiro[3.4]octane-2-carbonyl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C1N(CC11OCCC1)C(=O)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 RAQGJODOLACLDV-UHFFFAOYSA-N 0.000 description 1
• ZTKLXDSVNKRYLV-UHFFFAOYSA-N 9-[[4-(6-morpholin-4-ylpyrimidin-4-yl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C1=NC=NC(=C1)N1CCOCC1)=O ZTKLXDSVNKRYLV-UHFFFAOYSA-N 0.000 description 1
• CURPKGAMJCKDMB-UHFFFAOYSA-N 9-[[4-(6-oxa-2-azaspiro[3.4]octane-2-carbonyl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C1N(CC11COCC1)C(=O)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 CURPKGAMJCKDMB-UHFFFAOYSA-N 0.000 description 1
• ZVHFSTBLJTWXNM-UHFFFAOYSA-N 9-[[4-(cyclopropylmethoxy)phenyl]methyl]-7-methyl-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C1(CC1)COC1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C=CC=C2)C(C)C)C=C1 ZVHFSTBLJTWXNM-UHFFFAOYSA-N 0.000 description 1
• WANJTDSCQHYQHY-UHFFFAOYSA-N 9-[[4-(cyclopropylmethylamino)phenyl]methyl]-7-methyl-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C1(CC1)CNC1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C=CC=C2)C(C)C)C=C1 WANJTDSCQHYQHY-UHFFFAOYSA-N 0.000 description 1
• FDAPVBSMIMVKTB-UHFFFAOYSA-N 9-[[4-(morpholin-4-ylmethyl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)CN1CCOCC1)=O FDAPVBSMIMVKTB-UHFFFAOYSA-N 0.000 description 1
• RVYNWIXRSOCXNG-UHFFFAOYSA-N 9-[[4-(morpholine-4-carbonyl)phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C(=O)N1CCOCC1)=O RVYNWIXRSOCXNG-UHFFFAOYSA-N 0.000 description 1
• XTMXVWCRVVLBGW-OAQYLSRUSA-N 9-[[4-[(2R)-2-(methoxymethyl)pyrrolidine-1-carbonyl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C(=O)N1[C@H](CCC1)COC)=O XTMXVWCRVVLBGW-OAQYLSRUSA-N 0.000 description 1
• WUJKCSSUEYXAQO-GOSISDBHSA-N 9-[[4-[(2R)-2-methylpyrrolidine-1-carbonyl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C(=O)N1[C@@H](CCC1)C)=O WUJKCSSUEYXAQO-GOSISDBHSA-N 0.000 description 1
• GQJJJRMAAZFJRO-KDURUIRLSA-N 9-[[4-[(2R,6S)-2,6-dimethylmorpholine-4-carbonyl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C[C@@H]1CN(C[C@@H](O1)C)C(=O)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 GQJJJRMAAZFJRO-KDURUIRLSA-N 0.000 description 1
• XTMXVWCRVVLBGW-NRFANRHFSA-N 9-[[4-[(2S)-2-(methoxymethyl)pyrrolidine-1-carbonyl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C(=O)N1[C@@H](CCC1)COC)=O XTMXVWCRVVLBGW-NRFANRHFSA-N 0.000 description 1
• WUJKCSSUEYXAQO-SFHVURJKSA-N 9-[[4-[(2S)-2-methylpyrrolidine-1-carbonyl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C(=O)N1[C@H](CCC1)C)=O WUJKCSSUEYXAQO-SFHVURJKSA-N 0.000 description 1
• JZMUSDAPXNFROW-GOSISDBHSA-N 9-[[4-[(3R)-3-methylmorpholine-4-carbonyl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C(=O)N1[C@@H](COCC1)C)=O JZMUSDAPXNFROW-GOSISDBHSA-N 0.000 description 1
• SABCCZMDGRSTNF-QFIPXVFZSA-N 9-[[4-[(3S)-3-(2-methoxyethoxy)pyrrolidine-1-carbonyl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C(=O)N1C[C@H](CC1)OCCOC)=O SABCCZMDGRSTNF-QFIPXVFZSA-N 0.000 description 1
• JBIFHDVDTIUAJS-IBGZPJMESA-N 9-[[4-[(3S)-3-hydroxypyrrolidine-1-carbonyl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound O[C@@H]1CN(CC1)C(=O)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 JBIFHDVDTIUAJS-IBGZPJMESA-N 0.000 description 1
• JZMUSDAPXNFROW-SFHVURJKSA-N 9-[[4-[(3S)-3-methylmorpholine-4-carbonyl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C(=O)N1[C@H](COCC1)C)=O JZMUSDAPXNFROW-SFHVURJKSA-N 0.000 description 1
• UXIHOJROWKHOHQ-UHFFFAOYSA-N 9-[[4-[1-(1-acetylazetidin-3-yl)-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(=O)N1CC(C1)N1C(=NC(=C1)C(F)(F)F)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 UXIHOJROWKHOHQ-UHFFFAOYSA-N 0.000 description 1
• VQSCBHFSPIDASV-UHFFFAOYSA-N 9-[[4-[1-(1-methylazetidin-3-yl)-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C1CN(C1)C)=O VQSCBHFSPIDASV-UHFFFAOYSA-N 0.000 description 1
• NTIJHMYSIAIOEK-UHFFFAOYSA-N 9-[[4-[1-(2-hydroxyethyl)-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7-methyl-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound OCCN1C(=NC(=C1)C(F)(F)F)C1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C=CC=C2)C(C)C)C=C1 NTIJHMYSIAIOEK-UHFFFAOYSA-N 0.000 description 1
• VVKVEKJXWSRMBS-UHFFFAOYSA-N 9-[[4-[1-(2-hydroxyethyl)triazol-4-yl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound OCCN1N=NC(=C1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 VVKVEKJXWSRMBS-UHFFFAOYSA-N 0.000 description 1
• OFTXWNIHVFZYDX-UHFFFAOYSA-N 9-[[4-[1-(2-methoxyethyl)imidazol-2-yl]phenyl]methyl]-7-methyl-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=CN=1)CCOC)=O)C OFTXWNIHVFZYDX-UHFFFAOYSA-N 0.000 description 1
• ZGRFGIXWXJZCQX-UHFFFAOYSA-N 9-[[4-[1-(2-methoxyethyl)pyrazol-4-yl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1C=NN(C=1)CCOC)=O ZGRFGIXWXJZCQX-UHFFFAOYSA-N 0.000 description 1
• IBATXDAZVAKOBC-UHFFFAOYSA-N 9-[[4-[1-(azetidin-3-yl)-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-7-methyl-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound N1CC(C1)N1C(=NC(=C1)C(F)(F)F)C1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C=CC=C2)C(C)C)C=C1 IBATXDAZVAKOBC-UHFFFAOYSA-N 0.000 description 1
• HMCFZHKDXYRXMJ-UHFFFAOYSA-N 9-[[4-[1-(difluoromethyl)imidazol-2-yl]phenyl]methyl]-7-methyl-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound FC(N1C(=NC=C1)C1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C=CC=C2)C(C)C)C=C1)F HMCFZHKDXYRXMJ-UHFFFAOYSA-N 0.000 description 1
• DIEHUOHKGRJIAP-UHFFFAOYSA-N 9-[[4-[1-(oxan-4-yl)pyrazol-4-yl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1C=NN(C=1)C1CCOCC1)=O DIEHUOHKGRJIAP-UHFFFAOYSA-N 0.000 description 1
• FDRQZUNDNNWOBP-UHFFFAOYSA-N 9-[[4-[1-[2-(dimethylamino)ethyl]pyrazol-4-yl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound CN(CCN1N=CC(=C1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1)C FDRQZUNDNNWOBP-UHFFFAOYSA-N 0.000 description 1
• MVCJEDLGJGHLJM-UHFFFAOYSA-N 9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C)=O MVCJEDLGJGHLJM-UHFFFAOYSA-N 0.000 description 1
• FAKNBZDQQKIDCO-UHFFFAOYSA-N 9-[[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-2-(2-propanoylphenyl)-7H-purin-8-one Chemical compound CN1C(=NC(=C1)C(F)(F)F)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(CC)=O)C=C1 FAKNBZDQQKIDCO-UHFFFAOYSA-N 0.000 description 1
• CLYBAWRSGVNMKC-UHFFFAOYSA-N 9-[[4-[1-methyl-5-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C=1N(C(=CN=1)C(F)(F)F)C)=O CLYBAWRSGVNMKC-UHFFFAOYSA-N 0.000 description 1
• BAGKNGRIJKNCPR-UHFFFAOYSA-N 9-[[4-[2-(methoxymethyl)piperidine-1-carbonyl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C(=O)N1C(CCCC1)COC)=O BAGKNGRIJKNCPR-UHFFFAOYSA-N 0.000 description 1
• FCKGKKVWZRQPQN-UHFFFAOYSA-N 9-[[4-[2-[2-(dimethylamino)ethoxy]phenyl]phenyl]methyl]-7-methyl-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound CN(CCOC1=C(C=CC=C1)C1=CC=C(C=C1)CN1C2=NC(=NC=C2N(C1=O)C)C1=C(C=CC=C1)C(C)C)C FCKGKKVWZRQPQN-UHFFFAOYSA-N 0.000 description 1
• FLSYRYSRRRGVFC-UHFFFAOYSA-N 9-[[4-[2-methoxyethyl(methyl)amino]phenyl]methyl]-7-methyl-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)N(C)CCOC)=O)C FLSYRYSRRRGVFC-UHFFFAOYSA-N 0.000 description 1
• MQVXOOVCKPMLJI-UHFFFAOYSA-N 9-[[4-[3-(1-acetylpiperidin-3-yl)pyrazol-1-yl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(=O)N1CC(CCC1)C1=NN(C=C1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 MQVXOOVCKPMLJI-UHFFFAOYSA-N 0.000 description 1
• HBUGRFYTJVVACQ-UHFFFAOYSA-N 9-[[4-[3-(1-acetylpiperidin-4-yl)pyrazol-1-yl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(=O)N1CCC(CC1)C1=NN(C=C1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 HBUGRFYTJVVACQ-UHFFFAOYSA-N 0.000 description 1
• SFYMVJJUYJWMOV-UHFFFAOYSA-N 9-[[4-[3-(1-acetylpyrrolidin-3-yl)pyrazol-1-yl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(=O)N1CC(CC1)C1=NN(C=C1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 SFYMVJJUYJWMOV-UHFFFAOYSA-N 0.000 description 1
• ASUGCNSJKPZCIK-UHFFFAOYSA-N 9-[[4-[3-(1-methylpiperidin-3-yl)pyrazol-1-yl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)N1N=C(C=C1)C1CN(CCC1)C)=O ASUGCNSJKPZCIK-UHFFFAOYSA-N 0.000 description 1
• SWAUNHOZTDLBOR-UHFFFAOYSA-N 9-[[4-[3-(1-methylpyrrolidin-3-yl)pyrazol-1-yl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)N1N=C(C=C1)C1CN(CC1)C)=O SWAUNHOZTDLBOR-UHFFFAOYSA-N 0.000 description 1
• KPJCEJMLLJZXJY-UHFFFAOYSA-N 9-[[4-[3-(4-methylpiperazin-1-yl)pyrazol-1-yl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)N1N=C(C=C1)N1CCN(CC1)C)=O KPJCEJMLLJZXJY-UHFFFAOYSA-N 0.000 description 1
• RJBASSSQYGKQGB-UHFFFAOYSA-N 9-[[4-[3-(dimethylamino)propoxy]phenyl]methyl]-7-methyl-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound CN(CCCOC1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C=CC=C2)C(C)C)C=C1)C RJBASSSQYGKQGB-UHFFFAOYSA-N 0.000 description 1
• GOXXKUGJAVKRIH-UHFFFAOYSA-N 9-[[4-[3-(methoxymethyl)piperidine-1-carbonyl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)C(=O)N1CC(CCC1)COC)=O GOXXKUGJAVKRIH-UHFFFAOYSA-N 0.000 description 1
• WILPFCRARDPVEH-OAQYLSRUSA-N 9-[[4-[3-[(3R)-piperidin-3-yl]pyrazol-1-yl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)N1N=C(C=C1)[C@H]1CNCCC1)=O WILPFCRARDPVEH-OAQYLSRUSA-N 0.000 description 1
• WILPFCRARDPVEH-NRFANRHFSA-N 9-[[4-[3-[(3S)-piperidin-3-yl]pyrazol-1-yl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)N1N=C(C=C1)[C@@H]1CNCCC1)=O WILPFCRARDPVEH-NRFANRHFSA-N 0.000 description 1
• KMLCHMNKCMZWNM-UHFFFAOYSA-N 9-[[4-[3-[2-(dimethylamino)ethoxy]phenyl]phenyl]methyl]-7-methyl-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound CN(CCOC=1C=C(C=CC=1)C1=CC=C(C=C1)CN1C2=NC(=NC=C2N(C1=O)C)C1=C(C=CC=C1)C(C)C)C KMLCHMNKCMZWNM-UHFFFAOYSA-N 0.000 description 1
• ANVCELXRSLHAAL-UHFFFAOYSA-N 9-[[4-[3-methyl-5-(trifluoromethyl)pyrazol-1-yl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)N1N=C(C=C1C(F)(F)F)C)=O ANVCELXRSLHAAL-UHFFFAOYSA-N 0.000 description 1
• RLIUDQXNETWJQR-UHFFFAOYSA-N 9-[[4-[4-(2-aminopropan-2-yl)triazol-1-yl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound NC(C)(C)C=1N=NN(C=1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 RLIUDQXNETWJQR-UHFFFAOYSA-N 0.000 description 1
• QRMFJQQNUDBOIB-UHFFFAOYSA-N 9-[[4-[4-(2-hydroxyethyl)triazol-1-yl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound OCCC=1N=NN(C=1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 QRMFJQQNUDBOIB-UHFFFAOYSA-N 0.000 description 1
• RUZPGQJKVBUSNP-UHFFFAOYSA-N 9-[[4-[4-(2-hydroxypropan-2-yl)triazol-1-yl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound OC(C)(C)C=1N=NN(C=1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 RUZPGQJKVBUSNP-UHFFFAOYSA-N 0.000 description 1
• LBQMWACCBAAVRX-UHFFFAOYSA-N 9-[[4-[4-(3-aminopentan-3-yl)triazol-1-yl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound NC(CC)(CC)C=1N=NN(C=1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 LBQMWACCBAAVRX-UHFFFAOYSA-N 0.000 description 1
• FSMYSXRRACMHDO-UHFFFAOYSA-N 9-[[4-[4-(4-methoxyphenyl)triazol-1-yl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)N1N=NC(=C1)C1=CC=C(C=C1)OC)=O FSMYSXRRACMHDO-UHFFFAOYSA-N 0.000 description 1
• IUKPVXRIDWQEMN-UHFFFAOYSA-N 9-[[4-[4-(diethylaminomethyl)triazol-1-yl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)N(CC)CC=1N=NN(C=1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 IUKPVXRIDWQEMN-UHFFFAOYSA-N 0.000 description 1
• JDNXBEFLVVMKGA-UHFFFAOYSA-N 9-[[4-[4-(methoxymethyl)triazol-1-yl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)N1N=NC(=C1)COC)=O JDNXBEFLVVMKGA-UHFFFAOYSA-N 0.000 description 1
• IFHGGKGZHPPXJL-MRXNPFEDSA-N 9-[[4-[4-[(1R)-1-hydroxyethyl]triazol-1-yl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound O[C@H](C)C=1N=NN(C=1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 IFHGGKGZHPPXJL-MRXNPFEDSA-N 0.000 description 1
• GYKVWRNBZXFZMO-UHFFFAOYSA-N 9-[[4-[4-[2-(dimethylamino)ethoxy]phenyl]phenyl]methyl]-7-methyl-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound CN(CCOC1=CC=C(C=C1)C1=CC=C(C=C1)CN1C2=NC(=NC=C2N(C1=O)C)C1=C(C=CC=C1)C(C)C)C GYKVWRNBZXFZMO-UHFFFAOYSA-N 0.000 description 1
• UUEGAEKNKKQXIW-UHFFFAOYSA-N 9-[[4-[4-[2-(dimethylamino)ethyl]phenyl]phenyl]methyl]-7-methyl-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound CN(CCC1=CC=C(C=C1)C1=CC=C(C=C1)CN1C2=NC(=NC=C2N(C1=O)C)C1=C(C=CC=C1)C(C)C)C UUEGAEKNKKQXIW-UHFFFAOYSA-N 0.000 description 1
• ADPXNNMMYRAOPO-UHFFFAOYSA-N 9-[[4-[5-(hydroxymethyl)-1,3-thiazol-4-yl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound OCC1=C(N=CS1)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 ADPXNNMMYRAOPO-UHFFFAOYSA-N 0.000 description 1
• DMLNHNKLGCHFLH-UHFFFAOYSA-N 9-[[4-[5-(hydroxymethyl)-1,3-thiazol-4-yl]phenyl]methyl]-7-methyl-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound OCC1=C(N=CS1)C1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C=CC=C2)C(C)C)C=C1 DMLNHNKLGCHFLH-UHFFFAOYSA-N 0.000 description 1
• HBAKKNOUSLXVDN-UHFFFAOYSA-N 9-[[4-[5-(hydroxymethyl)-1-methylimidazol-4-yl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound OCC1=C(N=CN1C)C1=CC=C(CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)C=C1 HBAKKNOUSLXVDN-UHFFFAOYSA-N 0.000 description 1
• ZBCNOOOHBVATBQ-UHFFFAOYSA-N 9-[[4-[5-(hydroxymethyl)-1-methylimidazol-4-yl]phenyl]methyl]-7-methyl-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound OCC1=C(N=CN1C)C1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C=CC=C2)C(C)C)C=C1 ZBCNOOOHBVATBQ-UHFFFAOYSA-N 0.000 description 1
• LNKIFRQLYDNRJA-UHFFFAOYSA-N 9-[[4-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]phenyl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)N1N=C(C=C1C)C(F)(F)F)=O LNKIFRQLYDNRJA-UHFFFAOYSA-N 0.000 description 1
• LVWVPKKTCGGGNF-UHFFFAOYSA-N 9-[[4-[cyclopropylmethyl(methyl)amino]phenyl]methyl]-7-methyl-2-(2-propan-2-ylphenyl)purin-8-one Chemical compound C1(CC1)CN(C1=CC=C(CN2C3=NC(=NC=C3N(C2=O)C)C2=C(C=CC=C2)C(C)C)C=C1)C LVWVPKKTCGGGNF-UHFFFAOYSA-N 0.000 description 1
• MEWSEYHQHCSYIE-UHFFFAOYSA-N 9-[[4-fluoro-1-(2-methylpropanoyl)piperidin-4-yl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound FC1(CCN(CC1)C(C(C)C)=O)CN1C2=NC(=NC=C2NC1=O)C1=C(C=CC=C1)C(C)C MEWSEYHQHCSYIE-UHFFFAOYSA-N 0.000 description 1
• KXRVCABEAMHUIQ-UHFFFAOYSA-N 9-[[5-(3,5-dimethylpyrazol-1-yl)pyrazin-2-yl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound CC1=NN(C(=C1)C)C=1N=CC(=NC=1)CN1C2=NC(=NC=C2NC1=O)C1=C(C=CC=C1)C(C)C KXRVCABEAMHUIQ-UHFFFAOYSA-N 0.000 description 1
• ZUTOYMDBTRXUKT-UHFFFAOYSA-N 9-[[5-(3,5-dimethylpyrazol-1-yl)pyrimidin-2-yl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound CC1=NN(C(=C1)C)C=1C=NC(=NC=1)CN1C2=NC(=NC=C2NC1=O)C1=C(C=CC=C1)C(C)C ZUTOYMDBTRXUKT-UHFFFAOYSA-N 0.000 description 1
• KKBCOUDMODWCPD-UHFFFAOYSA-N 9-[[6-(1,4-dimethylimidazol-2-yl)pyridin-3-yl]methyl]-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound CN1C(=NC(=C1)C)C1=CC=C(C=N1)CN1C2=NC(=NC=C2NC1=O)C1=C(C=CC=C1)C(C)C KKBCOUDMODWCPD-UHFFFAOYSA-N 0.000 description 1
• UVRIXLRDTXJHTC-UHFFFAOYSA-N 9-benzyl-2-(2-propan-2-ylphenyl)-7H-purin-8-one Chemical compound C(C1=CC=CC=C1)N1C2=NC(=NC=C2NC1=O)C1=C(C=CC=C1)C(C)C UVRIXLRDTXJHTC-UHFFFAOYSA-N 0.000 description 1
• 208000030507 AIDS Diseases 0.000 description 1
• 208000002008 AIDS-Related Lymphoma Diseases 0.000 description 1
• 208000031261 Acute myeloid leukaemia Diseases 0.000 description 1
• 208000006468 Adrenal Cortex Neoplasms Diseases 0.000 description 1
• 206010061424 Anal cancer Diseases 0.000 description 1
• 208000007860 Anus Neoplasms Diseases 0.000 description 1
• 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 description 1
• 206010061692 Benign muscle neoplasm Diseases 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
• 206010052384 Biliary cyst Diseases 0.000 description 1
• 206010005003 Bladder cancer Diseases 0.000 description 1
• BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
• 241000283690 Bos taurus Species 0.000 description 1
• 206010006143 Brain stem glioma Diseases 0.000 description 1
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
• FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
• 239000004215 Carbon black (E152) Substances 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
• 241000700199 Cavia porcellus Species 0.000 description 1
• 206010007953 Central nervous system lymphoma Diseases 0.000 description 1
• 241000282693 Cercopithecidae Species 0.000 description 1
• 206010008342 Cervix carcinoma Diseases 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• 108010077544 Chromatin Proteins 0.000 description 1
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
• 206010073140 Clear cell sarcoma of soft tissue Diseases 0.000 description 1
• RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
• 230000004568 DNA-binding Effects 0.000 description 1
• 102000016928 DNA-directed DNA polymerase Human genes 0.000 description 1
• 108010014303 DNA-directed DNA polymerase Proteins 0.000 description 1
• ZFIVKAOQEXOYFY-UHFFFAOYSA-N Diepoxybutane Chemical compound C1OC1C1OC1 ZFIVKAOQEXOYFY-UHFFFAOYSA-N 0.000 description 1
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
• 208000001976 Endocrine Gland Neoplasms Diseases 0.000 description 1
• 241000283073 Equus caballus Species 0.000 description 1
• 208000000461 Esophageal Neoplasms Diseases 0.000 description 1
• 241000282326 Felis catus Species 0.000 description 1
• 206010053717 Fibrous histiocytoma Diseases 0.000 description 1
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
• 241000287828 Gallus gallus Species 0.000 description 1
• 201000003741 Gastrointestinal carcinoma Diseases 0.000 description 1
• 206010051066 Gastrointestinal stromal tumour Diseases 0.000 description 1
• 208000017604 Hodgkin disease Diseases 0.000 description 1
• 208000010747 Hodgkins lymphoma Diseases 0.000 description 1
• 101000777293 Homo sapiens Serine/threonine-protein kinase Chk1 Proteins 0.000 description 1
• 101000809257 Homo sapiens Ubiquitin carboxyl-terminal hydrolase 4 Proteins 0.000 description 1
• 101000759984 Homo sapiens Ubiquitin carboxyl-terminal hydrolase 46 Proteins 0.000 description 1
• 101000643895 Homo sapiens Ubiquitin carboxyl-terminal hydrolase 6 Proteins 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
• 206010020751 Hypersensitivity Diseases 0.000 description 1
• 206010021042 Hypopharyngeal cancer Diseases 0.000 description 1
• 206010056305 Hypopharyngeal neoplasm Diseases 0.000 description 1
• 208000008839 Kidney Neoplasms Diseases 0.000 description 1
• WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-M L-tartrate(1-) Chemical compound OC(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-M 0.000 description 1
• JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
• 206010062038 Lip neoplasm Diseases 0.000 description 1
• 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 description 1
• 206010025312 Lymphoma AIDS related Diseases 0.000 description 1
• 241000282560 Macaca mulatta Species 0.000 description 1
• 208000006644 Malignant Fibrous Histiocytoma Diseases 0.000 description 1
• 206010025997 Malignant neoplasm of islets of Langerhans Diseases 0.000 description 1
• 241000124008 Mammalia Species 0.000 description 1
• 208000002030 Merkel cell carcinoma Diseases 0.000 description 1
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
• QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 1
• 241000699670 Mus sp. Species 0.000 description 1
• 208000033776 Myeloid Acute Leukemia Diseases 0.000 description 1
• 201000004458 Myoma Diseases 0.000 description 1
• XWCLOIFPLCLHOG-UHFFFAOYSA-N N,1,2-trimethyl-N-[4-[[7-methyl-8-oxo-2-(2-propan-2-ylphenyl)purin-9-yl]methyl]phenyl]imidazole-4-sulfonamide Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)N(S(=O)(=O)C=1N=C(N(C=1)C)C)C)=O)C XWCLOIFPLCLHOG-UHFFFAOYSA-N 0.000 description 1
• FRCBGKPRINYBRY-UHFFFAOYSA-N N,1-dimethyl-N-[4-[[7-methyl-8-oxo-2-(2-propan-2-ylphenyl)purin-9-yl]methyl]phenyl]imidazole-2-sulfonamide Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)N(S(=O)(=O)C=1N(C=CN=1)C)C)=O)C FRCBGKPRINYBRY-UHFFFAOYSA-N 0.000 description 1
• NDEBDSMLHODCKC-UHFFFAOYSA-N N,1-dimethyl-N-[4-[[7-methyl-8-oxo-2-(2-propan-2-ylphenyl)purin-9-yl]methyl]phenyl]pyrazole-3-sulfonamide Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)N(S(=O)(=O)C1=NN(C=C1)C)C)=O)C NDEBDSMLHODCKC-UHFFFAOYSA-N 0.000 description 1
• GJEKQGYCWHSUPP-UHFFFAOYSA-N N,2,5-trimethyl-N-[4-[[7-methyl-8-oxo-2-(2-propan-2-ylphenyl)purin-9-yl]methyl]phenyl]pyrazole-3-carboxamide Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)N(C(=O)C1=CC(=NN1C)C)C)=O)C GJEKQGYCWHSUPP-UHFFFAOYSA-N 0.000 description 1
• FRCDHRXNAFLBJF-UHFFFAOYSA-N N,5-dimethyl-N-[4-[[7-methyl-8-oxo-2-(2-propan-2-ylphenyl)purin-9-yl]methyl]phenyl]-1H-pyrazole-3-carboxamide Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)N(C(=O)C1=NNC(=C1)C)C)=O)C FRCDHRXNAFLBJF-UHFFFAOYSA-N 0.000 description 1
• KKWSBHUQMURJCA-UHFFFAOYSA-N N,N-dimethyl-4-[[8-oxo-2-(2-propan-2-ylphenyl)-7H-purin-9-yl]methyl]benzamide Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C(=O)N(C)C)C=C1)=O KKWSBHUQMURJCA-UHFFFAOYSA-N 0.000 description 1
• BPINENSXOVLASV-UHFFFAOYSA-N N-(2-hydroxyethyl)-N-methyl-4-[[8-oxo-2-(2-propan-2-ylphenyl)-7H-purin-9-yl]methyl]benzamide Chemical compound OCCN(C(C1=CC=C(C=C1)CN1C2=NC(=NC=C2NC1=O)C1=C(C=CC=C1)C(C)C)=O)C BPINENSXOVLASV-UHFFFAOYSA-N 0.000 description 1
• OSVWWANGPOHDLF-UHFFFAOYSA-N N-(2-methoxyethyl)-N-methyl-4-[[8-oxo-2-(2-propan-2-ylphenyl)-7H-purin-9-yl]methyl]benzamide Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C(=O)N(C)CCOC)C=C1)=O OSVWWANGPOHDLF-UHFFFAOYSA-N 0.000 description 1
• BSFPWMZFMLNHOC-UHFFFAOYSA-N N-[(4-fluorophenyl)methyl]-N-methyl-4-[[8-oxo-2-(2-propan-2-ylphenyl)-7H-purin-9-yl]methyl]benzamide Chemical compound FC1=CC=C(CN(C(C2=CC=C(C=C2)CN2C3=NC(=NC=C3NC2=O)C2=C(C=CC=C2)C(C)C)=O)C)C=C1 BSFPWMZFMLNHOC-UHFFFAOYSA-N 0.000 description 1
• KCMLWGBOJFAQGF-UHFFFAOYSA-N N-[2-(dimethylamino)-2-oxoethyl]-N-methyl-4-[[8-oxo-2-(2-propan-2-ylphenyl)-7H-purin-9-yl]methyl]benzamide Chemical compound CN(C(CN(C(C1=CC=C(C=C1)CN1C2=NC(=NC=C2NC1=O)C1=C(C=CC=C1)C(C)C)=O)C)=O)C KCMLWGBOJFAQGF-UHFFFAOYSA-N 0.000 description 1
• ORMHLPFERGIHQC-UHFFFAOYSA-N N-[3-[[8-oxo-2-(2-propan-2-ylphenyl)-7H-purin-9-yl]methyl]phenyl]acetamide Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC=1C=C(C=CC=1)NC(C)=O)=O ORMHLPFERGIHQC-UHFFFAOYSA-N 0.000 description 1
• IKEVCAKRJRXYIE-UHFFFAOYSA-N N-[4-[[8-oxo-2-(2-propan-2-ylphenyl)-7H-purin-9-yl]methyl]phenyl]acetamide Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C=C1)NC(C)=O)=O IKEVCAKRJRXYIE-UHFFFAOYSA-N 0.000 description 1
• SIYLPIZAPVCJCD-UHFFFAOYSA-N N-cyclohexyl-N-methyl-4-[[8-oxo-2-(2-propan-2-ylphenyl)-7H-purin-9-yl]methyl]benzamide Chemical compound C1(CCCCC1)N(C(C1=CC=C(C=C1)CN1C2=NC(=NC=C2NC1=O)C1=C(C=CC=C1)C(C)C)=O)C SIYLPIZAPVCJCD-UHFFFAOYSA-N 0.000 description 1
• ROKOOZXAHDYOTN-UHFFFAOYSA-N N-cyclopropyl-N-methyl-4-[[8-oxo-2-(2-propan-2-ylphenyl)-7H-purin-9-yl]methyl]benzamide Chemical compound C1(CC1)N(C(C1=CC=C(C=C1)CN1C2=NC(=NC=C2NC1=O)C1=C(C=CC=C1)C(C)C)=O)C ROKOOZXAHDYOTN-UHFFFAOYSA-N 0.000 description 1
• OLQGWZURUQHEBN-UHFFFAOYSA-N N-ethyl-N-methyl-4-[[8-oxo-2-(2-propan-2-ylphenyl)-7H-purin-9-yl]methyl]benzamide Chemical compound C(C)N(C(C1=CC=C(C=C1)CN1C2=NC(=NC=C2NC1=O)C1=C(C=CC=C1)C(C)C)=O)C OLQGWZURUQHEBN-UHFFFAOYSA-N 0.000 description 1
• QTTLHGRXQOUBGE-UHFFFAOYSA-N N-methyl-4-[[8-oxo-2-(2-propan-2-ylphenyl)-7H-purin-9-yl]methyl]-N-propan-2-ylbenzamide Chemical compound C(C)(C)N(C(C1=CC=C(C=C1)CN1C2=NC(=NC=C2NC1=O)C1=C(C=CC=C1)C(C)C)=O)C QTTLHGRXQOUBGE-UHFFFAOYSA-N 0.000 description 1
• CEJKCWKIAGAPIS-UHFFFAOYSA-N N-methyl-4-[[8-oxo-2-(2-propan-2-ylphenyl)-7H-purin-9-yl]methyl]-N-propylbenzamide Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C(=O)N(CCC)C)C=C1)=O CEJKCWKIAGAPIS-UHFFFAOYSA-N 0.000 description 1
• JCWSMJARBKYWRQ-UHFFFAOYSA-N N-methyl-4-[[8-oxo-2-(2-propan-2-ylphenyl)-7H-purin-9-yl]methyl]benzamide Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2NC(N(C2=N1)CC1=CC=C(C(=O)NC)C=C1)=O JCWSMJARBKYWRQ-UHFFFAOYSA-N 0.000 description 1
• QWAUCHDOPAIJMU-UHFFFAOYSA-N N-methyl-N-[4-[[7-methyl-8-oxo-2-(2-propan-2-ylphenyl)purin-9-yl]methyl]phenyl]methanesulfonamide Chemical compound C(C)(C)C1=C(C=CC=C1)C1=NC=C2N(C(N(C2=N1)CC1=CC=C(C=C1)N(S(=O)(=O)C)C)=O)C QWAUCHDOPAIJMU-UHFFFAOYSA-N 0.000 description 1
• 229910002651 NO3 Inorganic materials 0.000 description 1
• 208000001894 Nasopharyngeal Neoplasms Diseases 0.000 description 1
• 206010061306 Nasopharyngeal cancer Diseases 0.000 description 1
• 206010029260 Neuroblastoma Diseases 0.000 description 1
• 206010029266 Neuroendocrine carcinoma of the skin Diseases 0.000 description 1
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
• 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
• OALKWIPCBJPRNY-UHFFFAOYSA-N O=C1NC2=CN=CNC2(CC(C=C2)=CC=C2N2N=CC(C3CCNCC3)=C2)N1 Chemical compound O=C1NC2=CN=CNC2(CC(C=C2)=CC=C2N2N=CC(C3CCNCC3)=C2)N1 OALKWIPCBJPRNY-UHFFFAOYSA-N 0.000 description 1
• 206010030155 Oesophageal carcinoma Diseases 0.000 description 1
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
• 229910019142 PO4 Inorganic materials 0.000 description 1
• 241000282577 Pan troglodytes Species 0.000 description 1
• 241001504519 Papio ursinus Species 0.000 description 1
• 208000000821 Parathyroid Neoplasms Diseases 0.000 description 1
• 208000002471 Penile Neoplasms Diseases 0.000 description 1
• 206010034299 Penile cancer Diseases 0.000 description 1
• 241000009328 Perro Species 0.000 description 1
• 208000009565 Pharyngeal Neoplasms Diseases 0.000 description 1
• 206010034811 Pharyngeal cancer Diseases 0.000 description 1
• 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
• 235000011613 Pinus brutia Nutrition 0.000 description 1
• 241000018646 Pinus brutia Species 0.000 description 1
• 208000007913 Pituitary Neoplasms Diseases 0.000 description 1
• 208000033014 Plasma cell tumor Diseases 0.000 description 1
• 208000007452 Plasmacytoma Diseases 0.000 description 1
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
• 201000008183 Pulmonary blastoma Diseases 0.000 description 1
• 241000700159 Rattus Species 0.000 description 1
• 208000015634 Rectal Neoplasms Diseases 0.000 description 1
• 206010038389 Renal cancer Diseases 0.000 description 1
• 201000000582 Retinoblastoma Diseases 0.000 description 1
• 102100031081 Serine/threonine-protein kinase Chk1 Human genes 0.000 description 1
• 208000000453 Skin Neoplasms Diseases 0.000 description 1
• 108020004459 Small interfering RNA Proteins 0.000 description 1
• 208000021712 Soft tissue sarcoma Diseases 0.000 description 1
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
• 241000282898 Sus scrofa Species 0.000 description 1
• 229920002253 Tannate Polymers 0.000 description 1
• 208000024313 Testicular Neoplasms Diseases 0.000 description 1
• 206010057644 Testis cancer Diseases 0.000 description 1
• 101150096719 USP1 gene Proteins 0.000 description 1
• 102100038463 Ubiquitin carboxyl-terminal hydrolase 4 Human genes 0.000 description 1
• 102100025025 Ubiquitin carboxyl-terminal hydrolase 46 Human genes 0.000 description 1
• 102100021015 Ubiquitin carboxyl-terminal hydrolase 6 Human genes 0.000 description 1
• 208000015778 Undifferentiated pleomorphic sarcoma Diseases 0.000 description 1
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
• 208000006593 Urologic Neoplasms Diseases 0.000 description 1
• 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 1
• 208000033559 Waldenström macroglobulinemia Diseases 0.000 description 1
• 208000008383 Wilms tumor Diseases 0.000 description 1
• GUWTXVUFNXVQMT-UHFFFAOYSA-N [N]1C=2N(CCC1)C=CC2 Chemical compound [N]1C=2N(CCC1)C=CC2 GUWTXVUFNXVQMT-UHFFFAOYSA-N 0.000 description 1
• 230000001154 acute effect Effects 0.000 description 1
• 208000009956 adenocarcinoma Diseases 0.000 description 1
• 201000002454 adrenal cortex cancer Diseases 0.000 description 1
• 125000003282 alkyl amino group Chemical group 0.000 description 1
• 150000001350 alkyl halides Chemical class 0.000 description 1
• 208000026935 allergic disease Diseases 0.000 description 1
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
• 125000003368 amide group Chemical group 0.000 description 1
• 150000001408 amides Chemical class 0.000 description 1
• 235000001014 amino acid Nutrition 0.000 description 1
• 150000001413 amino acids Chemical class 0.000 description 1
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
• 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
• 230000000259 anti-tumor effect Effects 0.000 description 1
• 201000011165 anus cancer Diseases 0.000 description 1
• 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
• 238000003556 assay Methods 0.000 description 1
• 210000001130 astrocyte Anatomy 0.000 description 1
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
• OISFUZRUIGGTSD-LJTMIZJLSA-N azane;(2r,3r,4r,5s)-6-(methylamino)hexane-1,2,3,4,5-pentol Chemical compound N.CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO OISFUZRUIGGTSD-LJTMIZJLSA-N 0.000 description 1
• 125000002785 azepinyl group Chemical group 0.000 description 1
• 125000002393 azetidinyl group Chemical group 0.000 description 1
• 230000008901 benefit Effects 0.000 description 1
• 208000001119 benign fibrous histiocytoma Diseases 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
• 125000005605 benzo group Chemical group 0.000 description 1
• 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
• 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 description 1
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 150000005347 biaryls Chemical class 0.000 description 1
• 125000002619 bicyclic group Chemical group 0.000 description 1
• 208000026900 bile duct neoplasm Diseases 0.000 description 1
• 230000004071 biological effect Effects 0.000 description 1
• 150000003842 bromide salts Chemical class 0.000 description 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
• 229910052794 bromium Inorganic materials 0.000 description 1
• 201000002143 bronchus adenoma Diseases 0.000 description 1
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 159000000007 calcium salts Chemical class 0.000 description 1
• 125000002837 carbocyclic group Chemical group 0.000 description 1
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
• 239000000969 carrier Substances 0.000 description 1
• 230000015556 catabolic process Effects 0.000 description 1
• 230000003197 catalytic effect Effects 0.000 description 1
• 230000022131 cell cycle Effects 0.000 description 1
• 230000025084 cell cycle arrest Effects 0.000 description 1
• 230000024245 cell differentiation Effects 0.000 description 1
• 230000001413 cellular effect Effects 0.000 description 1
• 230000033077 cellular process Effects 0.000 description 1
• 201000007455 central nervous system cancer Diseases 0.000 description 1
• 201000010881 cervical cancer Diseases 0.000 description 1
• 201000006612 cervical squamous cell carcinoma Diseases 0.000 description 1
• 239000003795 chemical substances by application Substances 0.000 description 1
• 238000004296 chiral HPLC Methods 0.000 description 1
• 150000003841 chloride salts Chemical class 0.000 description 1
• 229910052801 chlorine Inorganic materials 0.000 description 1
• 208000006990 cholangiocarcinoma Diseases 0.000 description 1
• 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 1
• 210000003483 chromatin Anatomy 0.000 description 1
• 238000004587 chromatography analysis Methods 0.000 description 1
• 208000032852 chronic lymphocytic leukemia Diseases 0.000 description 1
• DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
• 229960004316 cisplatin Drugs 0.000 description 1
• 201000000292 clear cell sarcoma Diseases 0.000 description 1
• 230000000295 complement effect Effects 0.000 description 1
• 208000017763 cutaneous neuroendocrine carcinoma Diseases 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
• 235000018417 cysteine Nutrition 0.000 description 1
• 230000006378 damage Effects 0.000 description 1
• 230000007547 defect Effects 0.000 description 1
• 230000002950 deficient Effects 0.000 description 1
• 238000006731 degradation reaction Methods 0.000 description 1
• 230000001419 dependent effect Effects 0.000 description 1
• 230000002074 deregulated effect Effects 0.000 description 1
• 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 description 1
• UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 1
• ACYGYJFTZSAZKR-UHFFFAOYSA-J dicalcium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Ca+2].[Ca+2].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O ACYGYJFTZSAZKR-UHFFFAOYSA-J 0.000 description 1
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
• 230000029087 digestion Effects 0.000 description 1
• 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 description 1
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
• 239000001177 diphosphate Substances 0.000 description 1
• XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical class [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
• 235000011180 diphosphates Nutrition 0.000 description 1
• POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
• 230000034431 double-strand break repair via homologous recombination Effects 0.000 description 1
• 229940079593 drug Drugs 0.000 description 1
• 229940009662 edetate Drugs 0.000 description 1
• 235000013399 edible fruits Nutrition 0.000 description 1
• 229950005627 embonate Drugs 0.000 description 1
• 201000011523 endocrine gland cancer Diseases 0.000 description 1
• 230000002708 enhancing effect Effects 0.000 description 1
• 229950007655 esilate Drugs 0.000 description 1
• 201000004101 esophageal cancer Diseases 0.000 description 1
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
• 208000024519 eye neoplasm Diseases 0.000 description 1
• 210000002950 fibroblast Anatomy 0.000 description 1
• 239000000945 filler Substances 0.000 description 1
• 239000011737 fluorine Substances 0.000 description 1
• 125000001153 fluoro group Chemical group F* 0.000 description 1
• 238000001640 fractional crystallisation Methods 0.000 description 1
• 125000002541 furyl group Chemical group 0.000 description 1
• 230000002496 gastric effect Effects 0.000 description 1
• 201000011243 gastrointestinal stromal tumor Diseases 0.000 description 1
• 230000002518 glial effect Effects 0.000 description 1
• 229960001731 gluceptate Drugs 0.000 description 1
• KWMLJOLKUYYJFJ-VFUOTHLCSA-N glucoheptonic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(O)=O KWMLJOLKUYYJFJ-VFUOTHLCSA-N 0.000 description 1
• 229940050410 gluconate Drugs 0.000 description 1
• 229930195712 glutamate Natural products 0.000 description 1
• 229940049906 glutamate Drugs 0.000 description 1
• 125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 description 1
• 210000002768 hair cell Anatomy 0.000 description 1
• 201000010536 head and neck cancer Diseases 0.000 description 1
• 208000014829 head and neck neoplasm Diseases 0.000 description 1
• 230000035876 healing Effects 0.000 description 1
• 125000004415 heterocyclylalkyl group Chemical group 0.000 description 1
• IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
• 125000006038 hexenyl group Chemical group 0.000 description 1
• 125000005980 hexynyl group Chemical group 0.000 description 1
• 102000054399 human USP1 Human genes 0.000 description 1
• 210000005260 human cell Anatomy 0.000 description 1
• XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical class C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
• 229930195733 hydrocarbon Natural products 0.000 description 1
• 150000002430 hydrocarbons Chemical class 0.000 description 1
• 239000001257 hydrogen Substances 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
• 230000007062 hydrolysis Effects 0.000 description 1
• 238000006460 hydrolysis reaction Methods 0.000 description 1
• 230000003301 hydrolyzing effect Effects 0.000 description 1
• 230000009610 hypersensitivity Effects 0.000 description 1
• 201000006866 hypopharynx cancer Diseases 0.000 description 1
• 150000002463 imidates Chemical class 0.000 description 1
• 125000002883 imidazolyl group Chemical group 0.000 description 1
• 230000001771 impaired effect Effects 0.000 description 1
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
• 230000003993 interaction Effects 0.000 description 1
• 201000002313 intestinal cancer Diseases 0.000 description 1
• 201000008893 intraocular retinoblastoma Diseases 0.000 description 1
• XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
• 229910052740 iodine Chemical group 0.000 description 1
• 239000011630 iodine Chemical group 0.000 description 1
• 230000005865 ionizing radiation Effects 0.000 description 1
• SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
• 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
• 108010076401 isopeptidase Proteins 0.000 description 1
• 125000001786 isothiazolyl group Chemical group 0.000 description 1
• 201000010982 kidney cancer Diseases 0.000 description 1
• 210000000244 kidney pelvis Anatomy 0.000 description 1
• 229940001447 lactate Drugs 0.000 description 1
• 229940099584 lactobionate Drugs 0.000 description 1
• JYTUSYBCFIZPBE-AMTLMPIISA-N lactobionic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O JYTUSYBCFIZPBE-AMTLMPIISA-N 0.000 description 1
• 229940070765 laurate Drugs 0.000 description 1
• 230000003902 lesion Effects 0.000 description 1
• 230000000670 limiting effect Effects 0.000 description 1
• 201000006721 lip cancer Diseases 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• 201000007270 liver cancer Diseases 0.000 description 1
• 208000014018 liver neoplasm Diseases 0.000 description 1
• 210000002751 lymph Anatomy 0.000 description 1
• 201000000564 macroglobulinemia Diseases 0.000 description 1
• 229940053326 magnesium salt Drugs 0.000 description 1
• 159000000003 magnesium salts Chemical class 0.000 description 1
• 238000012423 maintenance Methods 0.000 description 1
• 229940049920 malate Drugs 0.000 description 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
• 208000025854 malignant tumor of adrenal cortex Diseases 0.000 description 1
• 208000026045 malignant tumor of parathyroid gland Diseases 0.000 description 1
• IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
• 230000010534 mechanism of action Effects 0.000 description 1
• 230000001404 mediated effect Effects 0.000 description 1
• 230000002503 metabolic effect Effects 0.000 description 1
• 230000001394 metastastic effect Effects 0.000 description 1
• 206010061289 metastatic neoplasm Diseases 0.000 description 1
• 229940095102 methyl benzoate Drugs 0.000 description 1
• 229940102396 methyl bromide Drugs 0.000 description 1
• LRMHVVPPGGOAJQ-UHFFFAOYSA-N methyl nitrate Chemical compound CO[N+]([O-])=O LRMHVVPPGGOAJQ-UHFFFAOYSA-N 0.000 description 1
• YKFLJYAKACCWMH-UHFFFAOYSA-N methyl piperidine-1-carboxylate Chemical compound COC(=O)N1CCCCC1 YKFLJYAKACCWMH-UHFFFAOYSA-N 0.000 description 1
• JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
• 229960004857 mitomycin Drugs 0.000 description 1
• 208000025113 myeloid leukemia Diseases 0.000 description 1
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
• 125000004370 n-butenyl group Chemical group [H]\C([H])=C(/[H])C([H])([H])C([H])([H])* 0.000 description 1
• 229950006327 napsilate Drugs 0.000 description 1
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 201000008026 nephroblastoma Diseases 0.000 description 1
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
• 201000008106 ocular cancer Diseases 0.000 description 1
• 229940049964 oleate Drugs 0.000 description 1
• ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
• 230000003287 optical effect Effects 0.000 description 1
• 150000002894 organic compounds Chemical class 0.000 description 1
• 210000000963 osteoblast Anatomy 0.000 description 1
• 208000021284 ovarian germ cell tumor Diseases 0.000 description 1
• 125000001715 oxadiazolyl group Chemical group 0.000 description 1
• 125000000160 oxazolidinyl group Chemical group 0.000 description 1
• 125000005968 oxazolinyl group Chemical group 0.000 description 1
• 125000002971 oxazolyl group Chemical group 0.000 description 1
• 125000003566 oxetanyl group Chemical group 0.000 description 1
• 239000001301 oxygen Substances 0.000 description 1
• 150000002948 pantothenic acids Chemical class 0.000 description 1
• 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
• 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
• 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
• 125000005981 pentynyl group Chemical group 0.000 description 1
• 230000000144 pharmacologic effect Effects 0.000 description 1
• 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
• 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
• 235000021317 phosphate Nutrition 0.000 description 1
• 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
• 208000010916 pituitary tumor Diseases 0.000 description 1
• 208000010626 plasma cell neoplasm Diseases 0.000 description 1
• 230000010287 polarization Effects 0.000 description 1
• 230000003389 potentiating effect Effects 0.000 description 1
• 208000016800 primary central nervous system lymphoma Diseases 0.000 description 1
• 239000000047 product Substances 0.000 description 1
• 230000002062 proliferating effect Effects 0.000 description 1
• 230000035755 proliferation Effects 0.000 description 1
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
• 125000003373 pyrazinyl group Chemical group 0.000 description 1
• UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
• 125000001422 pyrrolinyl group Chemical group 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
• 125000005493 quinolyl group Chemical group 0.000 description 1
• 230000007115 recruitment Effects 0.000 description 1
• 206010038038 rectal cancer Diseases 0.000 description 1
• 201000001275 rectum cancer Diseases 0.000 description 1
• 230000004044 response Effects 0.000 description 1
• 201000006845 reticulosarcoma Diseases 0.000 description 1
• 208000029922 reticulum cell sarcoma Diseases 0.000 description 1
• 230000002207 retinal effect Effects 0.000 description 1
• 230000002441 reversible effect Effects 0.000 description 1
• 150000003873 salicylate salts Chemical class 0.000 description 1
• MOODSJOROWROTO-UHFFFAOYSA-N salicylsulfuric acid Chemical class OC(=O)C1=CC=CC=C1OS(O)(=O)=O MOODSJOROWROTO-UHFFFAOYSA-N 0.000 description 1
• 230000001568 sexual effect Effects 0.000 description 1
• 201000000849 skin cancer Diseases 0.000 description 1
• 239000007787 solid Substances 0.000 description 1
• FYGUBWKMMCWIKB-UHFFFAOYSA-N spiro[2.3]hexane Chemical compound C1CC11CCC1 FYGUBWKMMCWIKB-UHFFFAOYSA-N 0.000 description 1
• LBJQKYPPYSCCBH-UHFFFAOYSA-N spiro[3.3]heptane Chemical compound C1CCC21CCC2 LBJQKYPPYSCCBH-UHFFFAOYSA-N 0.000 description 1
• CTDQAGUNKPRERK-UHFFFAOYSA-N spirodecane Chemical compound C1CCCC21CCCCC2 CTDQAGUNKPRERK-UHFFFAOYSA-N 0.000 description 1
• 230000006641 stabilisation Effects 0.000 description 1
• 238000011105 stabilization Methods 0.000 description 1
• 230000000087 stabilizing effect Effects 0.000 description 1
• 238000010561 standard procedure Methods 0.000 description 1
• 210000004500 stellate cell Anatomy 0.000 description 1
• 210000000130 stem cell Anatomy 0.000 description 1
• 230000023895 stem cell maintenance Effects 0.000 description 1
• 230000000707 stereoselective effect Effects 0.000 description 1
• 238000006467 substitution reaction Methods 0.000 description 1
• 150000003890 succinate salts Chemical class 0.000 description 1
• NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical group NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
• 239000011593 sulfur Substances 0.000 description 1
• 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
• 239000004094 surface-active agent Substances 0.000 description 1
• 230000004083 survival effect Effects 0.000 description 1
• 208000024891 symptom Diseases 0.000 description 1
• 230000002194 synthesizing effect Effects 0.000 description 1
• 150000003892 tartrate salts Chemical class 0.000 description 1
• 210000002435 tendon Anatomy 0.000 description 1
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 201000003120 testicular cancer Diseases 0.000 description 1
• 238000012360 testing method Methods 0.000 description 1
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
• 229940124597 therapeutic agent Drugs 0.000 description 1
• VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
• 125000001984 thiazolidinyl group Chemical group 0.000 description 1
• 125000002769 thiazolinyl group Chemical group 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 1
• 125000001544 thienyl group Chemical group 0.000 description 1
• 229930192474 thiophene Natural products 0.000 description 1
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
• 125000005490 tosylate group Chemical group 0.000 description 1
• 238000013518 transcription Methods 0.000 description 1
• 230000035897 transcription Effects 0.000 description 1
• 206010044412 transitional cell carcinoma Diseases 0.000 description 1
• 125000004306 triazinyl group Chemical group 0.000 description 1
• 125000001425 triazolyl group Chemical group 0.000 description 1
• 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 1
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
• 230000000381 tumorigenic effect Effects 0.000 description 1
• 201000005112 urinary bladder cancer Diseases 0.000 description 1
• 210000001635 urinary tract Anatomy 0.000 description 1
• 208000037965 uterine sarcoma Diseases 0.000 description 1
• 206010046885 vaginal cancer Diseases 0.000 description 1
• 208000013139 vaginal neoplasm Diseases 0.000 description 1
• 229940070710 valerate Drugs 0.000 description 1
• NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
• 239000003981 vehicle Substances 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1