JP2018500376A5

JP2018500376A5 -

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Publication number: JP2018500376A5
Authority: JP; Japan
Prior art keywords: methyl; pyrazolo; alkyl; aryl; pyrimidin
Prior art date: 2015-12-29
Legal status : Granted

Application number

JP2017535007A

Other languages

English (en)

Japanese (ja)

Other versions

JP6649388B2 (ja

JP2018500376A (ja

Filing date

2015-12-29

Publication date

2019-01-31

2015-12-29 Application filed filed Critical

2015-12-29 Priority claimed from PCT/US2015/067831 external-priority patent/WO2016109515A1/en

2018-01-11 Publication of JP2018500376A publication Critical patent/JP2018500376A/ja

2019-01-31 Publication of JP2018500376A5 publication Critical patent/JP2018500376A5/ja

2020-02-19 Application granted granted Critical

2020-02-19 Publication of JP6649388B2 publication Critical patent/JP6649388B2/ja

Status Active legal-status Critical Current

2035-12-29 Anticipated expiration legal-status Critical

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125000000217 alkyl group Chemical group 0.000 claims description 373
-1 where Chemical group 0.000 claims description 352
125000003118 aryl group Chemical group 0.000 claims description 285
125000000753 cycloalkyl group Chemical group 0.000 claims description 203
125000000623 heterocyclic group Chemical group 0.000 claims description 198
125000001072 heteroaryl group Chemical group 0.000 claims description 168
125000004093 cyano group Chemical group *C#N 0.000 claims description 139
229910052736 halogen Inorganic materials 0.000 claims description 105
150000002367 halogens Chemical class 0.000 claims description 105
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 104
125000003545 alkoxy group Chemical group 0.000 claims description 92
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 90
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 85
125000001188 haloalkyl group Chemical group 0.000 claims description 72
125000003342 alkenyl group Chemical group 0.000 claims description 71
125000000304 alkynyl group Chemical group 0.000 claims description 71
125000001424 substituent group Chemical group 0.000 claims description 60
NKLCHDQGUHMCGL-UHFFFAOYSA-N cyclohexylidenemethanone Chemical group O=C=C1CCCCC1 NKLCHDQGUHMCGL-UHFFFAOYSA-N 0.000 claims description 59
125000004438 haloalkoxy group Chemical group 0.000 claims description 54
150000001875 compounds Chemical class 0.000 claims description 50
229910052799 carbon Inorganic materials 0.000 claims description 46
125000002947 alkylene group Chemical group 0.000 claims description 42
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 39
125000005275 alkylenearyl group Chemical group 0.000 claims description 35
125000005218 alkyleneheteroaryl group Chemical group 0.000 claims description 25
150000003839 salts Chemical class 0.000 claims description 23
229910052805 deuterium Inorganic materials 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 19
229910052717 sulfur Inorganic materials 0.000 claims description 7
JOXWSDNHLSQKCC-UHFFFAOYSA-N ethenesulfonamide Chemical compound NS(=O)(=O)C=C JOXWSDNHLSQKCC-UHFFFAOYSA-N 0.000 claims description 3
125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 42
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 22
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 21
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 16
125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 13
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 12
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 12
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 6
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 5
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 3
125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 3
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 229
DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 50
229910052757 nitrogen Inorganic materials 0.000 description 32
JSPCTNUQYWIIOT-UHFFFAOYSA-N piperidine-1-carboxamide Chemical compound NC(=O)N1CCCCC1 JSPCTNUQYWIIOT-UHFFFAOYSA-N 0.000 description 26
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 26
238000000034 method Methods 0.000 description 25
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 23
OOOBGFAUGXVKGI-UHFFFAOYSA-N 5,6-dihydropyrazolo[3,4-d]pyrimidin-4-one Chemical compound O=C1NCN=C2N=NC=C12 OOOBGFAUGXVKGI-UHFFFAOYSA-N 0.000 description 20
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 20
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 15
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 14
JLAKCHGEEBPDQI-UHFFFAOYSA-N 4-(4-fluorobenzyl)piperidine Chemical compound C1=CC(F)=CC=C1CC1CCNCC1 JLAKCHGEEBPDQI-UHFFFAOYSA-N 0.000 description 13
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 12
201000010099 disease Diseases 0.000 description 12
206010028980 Neoplasm Diseases 0.000 description 11
150000004677 hydrates Chemical class 0.000 description 11
239000000651 prodrug Substances 0.000 description 11
229940002612 prodrug Drugs 0.000 description 11
239000012453 solvate Substances 0.000 description 11
125000002768 hydroxyalkyl group Chemical group 0.000 description 9
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 8
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 8
108700011958 Ubiquitin-Specific Peptidase 7 Proteins 0.000 description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 7
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
201000011510 cancer Diseases 0.000 description 6
BQCBGAAIDUOCJL-UHFFFAOYSA-N 1-(4-fluorophenyl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=CC=C(C=C1)N1N=CC2=C1N=CNC2=O BQCBGAAIDUOCJL-UHFFFAOYSA-N 0.000 description 5
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 5
101150020913 USP7 gene Proteins 0.000 description 5
102100021013 Ubiquitin carboxyl-terminal hydrolase 7 Human genes 0.000 description 5
229940126752 Ubiquitin-speciﬁc protease 7 inhibitor Drugs 0.000 description 5
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 5
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
208000027866 inflammatory disease Diseases 0.000 description 5
230000009385 viral infection Effects 0.000 description 5
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
102100025064 Cellular tumor antigen p53 Human genes 0.000 description 4
208000036142 Viral infection Diseases 0.000 description 4
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
230000004770 neurodegeneration Effects 0.000 description 4
208000015122 neurodegenerative disease Diseases 0.000 description 4
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
VOCYBPAFPZYKDN-UHFFFAOYSA-N 4-hydroxy-n,n-dimethylpiperidine-1-carboxamide Chemical compound CN(C)C(=O)N1CCC(O)CC1 VOCYBPAFPZYKDN-UHFFFAOYSA-N 0.000 description 3
208000035143 Bacterial infection Diseases 0.000 description 3
102100021573 Bcl-2-binding component 3, isoforms 3/4 Human genes 0.000 description 3
208000024172 Cardiovascular disease Diseases 0.000 description 3
108050002772 E3 ubiquitin-protein ligase Mdm2 Proteins 0.000 description 3
102000012199 E3 ubiquitin-protein ligase Mdm2 Human genes 0.000 description 3
101000971203 Homo sapiens Bcl-2-binding component 3, isoforms 1/2 Proteins 0.000 description 3
101000971209 Homo sapiens Bcl-2-binding component 3, isoforms 3/4 Proteins 0.000 description 3
208000022362 bacterial infectious disease Diseases 0.000 description 3
230000022131 cell cycle Effects 0.000 description 3
230000003833 cell viability Effects 0.000 description 3
208000035475 disorder Diseases 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
HCJTYESURSHXNB-UHFFFAOYSA-N propynamide Chemical compound NC(=O)C#C HCJTYESURSHXNB-UHFFFAOYSA-N 0.000 description 3
0 *C(N(CC1)CCC1(CN(C=Nc1c2cn[n]1*)C2=O)O)=O Chemical compound *C(N(CC1)CCC1(CN(C=Nc1c2cn[n]1*)C2=O)O)=O 0.000 description 2
DUYBKXMBOOMDFJ-UHFFFAOYSA-N 1-(4-chlorophenyl)-5-[[1-(cyclopropanecarbonyl)-4-hydroxypiperidin-4-yl]methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound ClC1=CC=C(C=C1)N1N=CC2=C1N=CN(C2=O)CC1(CCN(CC1)C(=O)C1CC1)O DUYBKXMBOOMDFJ-UHFFFAOYSA-N 0.000 description 2
OHKNFFOLOANCFL-UHFFFAOYSA-N 1-(4-fluorophenyl)-5-[1-[4-hydroxy-1-(4-methoxybenzoyl)piperidin-4-yl]ethyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=CC=C(C=C1)N1N=CC2=C1N=CN(C2=O)C(C)C1(CCN(CC1)C(=O)C1=CC=C(C=C1)OC)O OHKNFFOLOANCFL-UHFFFAOYSA-N 0.000 description 2
FTIQRDHBKQUSAK-UHFFFAOYSA-N 1-(4-fluorophenyl)-5-[[4-hydroxy-1-(4-methoxybenzoyl)piperidin-4-yl]methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=CC=C(C=C1)N1N=CC2=C1N=CN(C2=O)CC1(CCN(CC1)C(C1=CC=C(C=C1)OC)=O)O FTIQRDHBKQUSAK-UHFFFAOYSA-N 0.000 description 2
PZIPRQVMWBLZJR-UHFFFAOYSA-N 1-(4-fluorophenyl)-5-[[4-hydroxy-1-(4-methylbenzoyl)piperidin-4-yl]methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=CC=C(C=C1)N1N=CC2=C1N=CN(C2=O)CC1(CCN(CC1)C(C1=CC=C(C=C1)C)=O)O PZIPRQVMWBLZJR-UHFFFAOYSA-N 0.000 description 2
TVPPCRLYDOHKHV-UHFFFAOYSA-N 1-(4-fluorophenyl)-5-[[4-hydroxy-1-[3-(trifluoromethyl)bicyclo[1.1.1]pentane-1-carbonyl]piperidin-4-yl]methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=CC=C(C=C1)N1N=CC2=C1N=CN(C2=O)CC1(CCN(CC1)C(=O)C12CC(C1)(C2)C(F)(F)F)O TVPPCRLYDOHKHV-UHFFFAOYSA-N 0.000 description 2
FVXFRBHQSTZMMU-UHFFFAOYSA-N 1-[3-(3-chlorophenyl)phenyl]-5-[[1-(cyclopropanecarbonyl)-4-hydroxypiperidin-4-yl]methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound ClC=1C=C(C=CC=1)C=1C=C(C=CC=1)N1N=CC2=C1N=CN(C2=O)CC1(CCN(CC1)C(=O)C1CC1)O FVXFRBHQSTZMMU-UHFFFAOYSA-N 0.000 description 2
WBTARBUWJSXINV-UHFFFAOYSA-N 1-[3-(5-chloropyridin-3-yl)phenyl]-5-[[1-(cyclopropanecarbonyl)-4-hydroxypiperidin-4-yl]methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound ClC=1C=C(C=NC=1)C=1C=C(C=CC=1)N1N=CC2=C1N=CN(C2=O)CC1(CCN(CC1)C(=O)C1CC1)O WBTARBUWJSXINV-UHFFFAOYSA-N 0.000 description 2
CNYADHJIXOPTPL-UHFFFAOYSA-N 1-[3-[(4-acetylpiperazin-1-yl)methyl]phenyl]-5-[[1-(cyclopropanecarbonyl)-4-hydroxypiperidin-4-yl]methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C(C)(=O)N1CCN(CC1)CC=1C=C(C=CC=1)N1N=CC2=C1N=CN(C2=O)CC1(CCN(CC1)C(=O)C1CC1)O CNYADHJIXOPTPL-UHFFFAOYSA-N 0.000 description 2
NHSHEZJIRKENEH-UHFFFAOYSA-N 1-[3-[[benzyl(methyl)amino]methyl]phenyl]-5-[[1-(cyclopropanecarbonyl)-4-hydroxypiperidin-4-yl]methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C(C1=CC=CC=C1)N(C)CC=1C=C(C=CC=1)N1N=CC2=C1N=CN(C2=O)CC1(CCN(CC1)C(=O)C1CC1)O NHSHEZJIRKENEH-UHFFFAOYSA-N 0.000 description 2
YDJGRRUKNPWLRY-UHFFFAOYSA-N 1-[3-[[cyclohexyl(ethyl)amino]methyl]phenyl]-5-[[1-(cyclopropanecarbonyl)-4-hydroxypiperidin-4-yl]methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1(CCCCC1)N(CC)CC=1C=C(C=CC=1)N1N=CC2=C1N=CN(C2=O)CC1(CCN(CC1)C(=O)C1CC1)O YDJGRRUKNPWLRY-UHFFFAOYSA-N 0.000 description 2
XKSZJQJDAKKVBQ-UHFFFAOYSA-N 1-[4-[(4-acetylpiperazin-1-yl)methyl]phenyl]-5-[[1-(cyclopropanecarbonyl)-4-hydroxypiperidin-4-yl]methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C(C)(=O)N1CCN(CC1)CC1=CC=C(C=C1)N1N=CC2=C1N=CN(C2=O)CC1(CCN(CC1)C(=O)C1CC1)O XKSZJQJDAKKVBQ-UHFFFAOYSA-N 0.000 description 2
NJQOWNQXCLLVBO-UHFFFAOYSA-N 1-[4-[[benzyl(methyl)amino]methyl]phenyl]-5-[[1-(cyclopropanecarbonyl)-4-hydroxypiperidin-4-yl]methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C(C1=CC=CC=C1)N(C)CC1=CC=C(C=C1)N1N=CC2=C1N=CN(C2=O)CC1(CCN(CC1)C(=O)C1CC1)O NJQOWNQXCLLVBO-UHFFFAOYSA-N 0.000 description 2
TYQFDGVJFMEMKX-UHFFFAOYSA-N 1-[4-[[cyclohexyl(ethyl)amino]methyl]phenyl]-5-[[1-(cyclopropanecarbonyl)-4-hydroxypiperidin-4-yl]methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1(CCCCC1)N(CC)CC1=CC=C(C=C1)N1N=CC2=C1N=CN(C2=O)CC1(CCN(CC1)C(=O)C1CC1)O TYQFDGVJFMEMKX-UHFFFAOYSA-N 0.000 description 2
BMJJYKSMRQVHJD-UHFFFAOYSA-N 1-[[3-[5-[[1-(cyclopropanecarbonyl)-4-hydroxypiperidin-4-yl]methyl]-4-oxopyrazolo[3,4-d]pyrimidin-1-yl]phenyl]methyl]piperidine-4-carbonitrile Chemical compound C1(CC1)C(=O)N1CCC(CC1)(O)CN1C=NC2=C(C1=O)C=NN2C=1C=C(C=CC=1)CN1CCC(CC1)C#N BMJJYKSMRQVHJD-UHFFFAOYSA-N 0.000 description 2
PCDOQRRMQHUUBO-UHFFFAOYSA-N 1-[[4-[5-[[1-(cyclopropanecarbonyl)-4-hydroxypiperidin-4-yl]methyl]-4-oxopyrazolo[3,4-d]pyrimidin-1-yl]phenyl]methyl]piperidine-4-carbonitrile Chemical compound C1(CC1)C(=O)N1CCC(CC1)(O)CN1C=NC2=C(C1=O)C=NN2C1=CC=C(C=C1)CN1CCC(CC1)C#N PCDOQRRMQHUUBO-UHFFFAOYSA-N 0.000 description 2
DNBBOFJOMWUUCI-UHFFFAOYSA-N 2-[1-[[3-[5-[[1-(cyclopropanecarbonyl)-4-hydroxypiperidin-4-yl]methyl]-4-oxopyrazolo[3,4-d]pyrimidin-1-yl]phenyl]methyl]piperidin-3-yl]acetonitrile Chemical compound C1(CC1)C(=O)N1CCC(CC1)(O)CN1C=NC2=C(C1=O)C=NN2C=1C=C(C=CC=1)CN1CC(CCC1)CC#N DNBBOFJOMWUUCI-UHFFFAOYSA-N 0.000 description 2
WQLCSZCNDAYIAJ-UHFFFAOYSA-N 3-[(1-benzoyl-4-hydroxypiperidin-4-yl)methyl]-7-(4-fluorophenyl)-6-methylpyrrolo[2,3-d]pyrimidin-4-one Chemical compound C(C1=CC=CC=C1)(=O)N1CCC(CC1)(O)CN1C=NC2=C(C1=O)C=C(N2C1=CC=C(C=C1)F)C WQLCSZCNDAYIAJ-UHFFFAOYSA-N 0.000 description 2
HQTCXEOOQMZTCE-UHFFFAOYSA-N 3-[(1-benzoyl-4-hydroxypiperidin-4-yl)methyl]-7-(4-fluorophenyl)pyrrolo[2,3-d]pyrimidin-4-one Chemical compound C(C1=CC=CC=C1)(=O)N1CCC(CC1)(O)CN1C=NC2=C(C1=O)C=CN2C1=CC=C(C=C1)F HQTCXEOOQMZTCE-UHFFFAOYSA-N 0.000 description 2
QTZUBBWFJIGPHA-UHFFFAOYSA-N 3-[3-[5-[[1-(cyclopropanecarbonyl)-4-hydroxypiperidin-4-yl]methyl]-4-oxopyrazolo[3,4-d]pyrimidin-1-yl]phenyl]-N,N-dimethylbenzamide Chemical compound C1(CC1)C(=O)N1CCC(CC1)(O)CN1C=NC2=C(C1=O)C=NN2C=1C=C(C=CC=1)C=1C=C(C(=O)N(C)C)C=CC=1 QTZUBBWFJIGPHA-UHFFFAOYSA-N 0.000 description 2
MFDXVVQSJSWLKY-UHFFFAOYSA-N 3-[3-[5-[[1-(cyclopropanecarbonyl)-4-hydroxypiperidin-4-yl]methyl]-4-oxopyrazolo[3,4-d]pyrimidin-1-yl]phenyl]-N,N-dimethylbenzenesulfonamide Chemical compound C1(CC1)C(=O)N1CCC(CC1)(O)CN1C=NC2=C(C1=O)C=NN2C=1C=C(C=CC=1)C=1C=C(C=CC=1)S(=O)(=O)N(C)C MFDXVVQSJSWLKY-UHFFFAOYSA-N 0.000 description 2
WCUIZBJLRKKRAX-UHFFFAOYSA-N 3-[3-[5-[[1-(cyclopropanecarbonyl)-4-hydroxypiperidin-4-yl]methyl]-4-oxopyrazolo[3,4-d]pyrimidin-1-yl]phenyl]-N-methylbenzamide Chemical compound C1(CC1)C(=O)N1CCC(CC1)(O)CN1C=NC2=C(C1=O)C=NN2C=1C=C(C=CC=1)C=1C=C(C(=O)NC)C=CC=1 WCUIZBJLRKKRAX-UHFFFAOYSA-N 0.000 description 2
NBVKYWIFZMFATD-UHFFFAOYSA-N 3-[3-[5-[[1-(cyclopropanecarbonyl)-4-hydroxypiperidin-4-yl]methyl]-4-oxopyrazolo[3,4-d]pyrimidin-1-yl]phenyl]benzonitrile Chemical compound C1(CC1)C(=O)N1CCC(CC1)(O)CN1C=NC2=C(C1=O)C=NN2C=1C=C(C=CC=1)C=1C=C(C#N)C=CC=1 NBVKYWIFZMFATD-UHFFFAOYSA-N 0.000 description 2
UHNZQPODYVOHCO-UHFFFAOYSA-N 4-[3-[5-[[1-(cyclopropanecarbonyl)-4-hydroxypiperidin-4-yl]methyl]-4-oxopyrazolo[3,4-d]pyrimidin-1-yl]phenyl]-N,N-dimethylbenzamide Chemical compound C1(CC1)C(=O)N1CCC(CC1)(O)CN1C=NC2=C(C1=O)C=NN2C=1C=C(C=CC=1)C1=CC=C(C(=O)N(C)C)C=C1 UHNZQPODYVOHCO-UHFFFAOYSA-N 0.000 description 2
NUFCUGQGJHGIAT-UHFFFAOYSA-N 4-[3-[5-[[1-(cyclopropanecarbonyl)-4-hydroxypiperidin-4-yl]methyl]-4-oxopyrazolo[3,4-d]pyrimidin-1-yl]phenyl]-N-methylbenzamide Chemical compound C1(CC1)C(=O)N1CCC(CC1)(O)CN1C=NC2=C(C1=O)C=NN2C=1C=C(C=CC=1)C1=CC=C(C(=O)NC)C=C1 NUFCUGQGJHGIAT-UHFFFAOYSA-N 0.000 description 2
UAHSMCQZLUFJRI-UHFFFAOYSA-N 4-[3-[5-[[1-(cyclopropanecarbonyl)-4-hydroxypiperidin-4-yl]methyl]-4-oxopyrazolo[3,4-d]pyrimidin-1-yl]phenyl]benzonitrile Chemical compound C1(CC1)C(=O)N1CCC(CC1)(O)CN1C=NC2=C(C1=O)C=NN2C=1C=C(C=CC=1)C1=CC=C(C#N)C=C1 UAHSMCQZLUFJRI-UHFFFAOYSA-N 0.000 description 2
JOTRISPTJMOSMV-UHFFFAOYSA-N 4-[[1-(4-fluorophenyl)-4-oxopyrazolo[3,4-d]pyrimidin-5-yl]methyl]-4-hydroxy-N,N-dimethylpiperidine-1-carboxamide Chemical compound FC1=CC=C(C=C1)N1N=CC2=C1N=CN(C2=O)CC1(CCN(CC1)C(=O)N(C)C)O JOTRISPTJMOSMV-UHFFFAOYSA-N 0.000 description 2
RLODEGGGRQSAAX-UHFFFAOYSA-N 4-[[1-(4-fluorophenyl)-4-oxopyrazolo[3,4-d]pyrimidin-5-yl]methyl]-4-hydroxy-N-methylpiperidine-1-carboxamide Chemical class FC1=CC=C(C=C1)N1N=CC2=C1N=CN(C2=O)CC1(CCN(CC1)C(=O)NC)O RLODEGGGRQSAAX-UHFFFAOYSA-N 0.000 description 2
125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 2
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CPJNBZASMDGFKR-UHFFFAOYSA-N 1-[4-(cyclobutylmethoxy)phenyl]-5-[[1-(4-fluorobenzoyl)-4-hydroxypiperidin-4-yl]methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1(CCC1)COC1=CC=C(C=C1)N1N=CC2=C1N=CN(C2=O)CC1(CCN(CC1)C(C1=CC=C(C=C1)F)=O)O CPJNBZASMDGFKR-UHFFFAOYSA-N 0.000 description 1
XRXJYKMESMDXEG-UHFFFAOYSA-N 1-[4-(cyclohexylamino)phenyl]-5-[[1-(cyclopropanecarbonyl)-4-hydroxypiperidin-4-yl]methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1(CCCCC1)NC1=CC=C(C=C1)N1N=CC2=C1N=CN(C2=O)CC1(CCN(CC1)C(=O)C1CC1)O XRXJYKMESMDXEG-UHFFFAOYSA-N 0.000 description 1
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AEASOSUPLINRSF-UHFFFAOYSA-N 1-[4-(dimethylamino)phenyl]-5-[[1-(4-fluorobenzoyl)-4-hydroxypiperidin-4-yl]methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC=C(C=C1)N1N=CC2=C1N=CN(C2=O)CC1(CCN(CC1)C(=O)C1=CC=C(C=C1)F)O)C AEASOSUPLINRSF-UHFFFAOYSA-N 0.000 description 1
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FQTJMVFSSSBXMA-UHFFFAOYSA-N 1-[4-[(1-fluorocyclobutyl)methoxy]phenyl]-5-[[4-hydroxy-1-(1-methylcyclobutanecarbonyl)piperidin-4-yl]methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1(CCC1)COC1=CC=C(C=C1)N1N=CC2=C1N=CN(C2=O)CC1(CCN(CC1)C(=O)C1(CCC1)C)O FQTJMVFSSSBXMA-UHFFFAOYSA-N 0.000 description 1
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AKMYUIILHUFAKN-UHFFFAOYSA-N 1-[4-[(5-tert-butyl-1H-pyrazol-3-yl)amino]phenyl]-5-[[1-(cyclopropanecarbonyl)-4-hydroxypiperidin-4-yl]methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C(C)(C)(C)C1=CC(=NN1)NC1=CC=C(C=C1)N1N=CC2=C1N=CN(C2=O)CC1(CCN(CC1)C(=O)C1CC1)O AKMYUIILHUFAKN-UHFFFAOYSA-N 0.000 description 1
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WCRNADYQGOXFHI-UHFFFAOYSA-N 1-[4-[benzyl(methyl)amino]phenyl]-5-[[1-(cyclopropanecarbonyl)-4-hydroxypiperidin-4-yl]methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C(C1=CC=CC=C1)N(C1=CC=C(C=C1)N1N=CC2=C1N=CN(C2=O)CC1(CCN(CC1)C(=O)C1CC1)O)C WCRNADYQGOXFHI-UHFFFAOYSA-N 0.000 description 1
WEPUPPMRNULYKW-UHFFFAOYSA-N 1-[4-fluoro-3-(hydroxymethyl)phenyl]-5-[[4-hydroxy-1-(4-pyridin-2-yloxybenzoyl)piperidin-4-yl]methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=C(C=C(C=C1)N1N=CC2=C1N=CN(C2=O)CC1(CCN(CC1)C(C1=CC=C(C=C1)OC1=NC=CC=C1)=O)O)CO WEPUPPMRNULYKW-UHFFFAOYSA-N 0.000 description 1
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JP2017535007A 2014-12-30 2015-12-29 ユビキチン特異的プロテアーゼ７阻害薬としてのピロロ及びピラゾロピリミジン Active JP6649388B2 (ja)