JP2019515931A5

JP2019515931A5 -

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Publication number: JP2019515931A5
Authority: JP; Japan
Prior art keywords: isoquinoline; methyl; carboxamide; piperidine; acetamide
Prior art date: 2017-04-27
Legal status : Granted

Application number

JP2018556921A

Other languages

English (en)

Japanese (ja)

Other versions

JP2019515931A (ja

JP7023243B2 (ja

Filing date

2017-04-27

Publication date

2021-03-25

2017-04-27 Application filed filed Critical

2017-04-27 Priority claimed from PCT/US2017/029797 external-priority patent/WO2017189823A2/en

2019-06-13 Publication of JP2019515931A publication Critical patent/JP2019515931A/ja

2021-03-25 Publication of JP2019515931A5 publication Critical patent/JP2019515931A5/ja

2022-02-21 Application granted granted Critical

2022-02-21 Publication of JP7023243B2 publication Critical patent/JP7023243B2/ja

Status Active legal-status Critical Current

2037-04-27 Anticipated expiration legal-status Critical

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-1 substituted Chemical class 0.000 claims description 603
125000002947 alkylene group Chemical group 0.000 claims description 278
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 203
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 124
DPBWFNDFMCCGGJ-UHFFFAOYSA-N 4-Piperidine carboxamide Chemical compound NC(=O)C1CCNCC1 DPBWFNDFMCCGGJ-UHFFFAOYSA-N 0.000 claims description 119
125000000304 alkynyl group Chemical group 0.000 claims description 100
125000003342 alkenyl group Chemical group 0.000 claims description 96
125000001188 haloalkyl group Chemical group 0.000 claims description 96
125000004452 carbocyclyl group Chemical group 0.000 claims description 92
125000001424 substituent group Chemical group 0.000 claims description 90
150000001875 compounds Chemical class 0.000 claims description 88
150000004820 halides Chemical class 0.000 claims description 88
125000000623 heterocyclic group Chemical group 0.000 claims description 75
125000000217 alkyl group Chemical group 0.000 claims description 74
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 59
229910052799 carbon Inorganic materials 0.000 claims description 54
125000004432 carbon atom Chemical group C* 0.000 claims description 54
PNZXMIKHJXIPEK-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 claims description 50
VALZSZJVEFACEZ-UHFFFAOYSA-N azetidine-3-carboxamide Chemical compound NC(=O)C1CNC1 VALZSZJVEFACEZ-UHFFFAOYSA-N 0.000 claims description 34
201000010099 disease Diseases 0.000 claims description 30
208000035475 disorder Diseases 0.000 claims description 29
229910052757 nitrogen Inorganic materials 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 24
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
XAKZFQZFGKCPNZ-VVOJOOEHSA-N CN1N=CC(=C1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)[C@@H]1CC[C@H](CC1)N1CCOCC1 Chemical compound CN1N=CC(=C1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)[C@@H]1CC[C@H](CC1)N1CCOCC1 XAKZFQZFGKCPNZ-VVOJOOEHSA-N 0.000 claims description 17
IQHXABCGSFAKPN-UHFFFAOYSA-N pyrrolidine-3-carboxamide Chemical compound NC(=O)C1CCNC1 IQHXABCGSFAKPN-UHFFFAOYSA-N 0.000 claims description 17
125000003118 aryl group Chemical group 0.000 claims description 16
125000001072 heteroaryl group Chemical group 0.000 claims description 16
206010016654 Fibrosis Diseases 0.000 claims description 14
201000011240 Frontotemporal dementia Diseases 0.000 claims description 14
230000004761 fibrosis Effects 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
125000003386 piperidinyl group Chemical group 0.000 claims description 12
206010028980 Neoplasm Diseases 0.000 claims description 9
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
208000005069 pulmonary fibrosis Diseases 0.000 claims description 9
206010018338 Glioma Diseases 0.000 claims description 8
GAQRHXBWMRGNST-UHFFFAOYSA-N N-[6-(1,3-thiazol-5-yl)isoquinolin-3-yl]piperidine-4-carboxamide Chemical compound S1C=NC=C1C=1C=C2C=C(N=CC2=CC=1)NC(=O)C1CCNCC1 GAQRHXBWMRGNST-UHFFFAOYSA-N 0.000 claims description 8
YMQORBMBDCILMV-UHFFFAOYSA-N N-[6-(1-methylpyrazol-4-yl)isoquinolin-3-yl]piperidine-4-carboxamide Chemical compound CN1N=CC(=C1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)C1CCNCC1 YMQORBMBDCILMV-UHFFFAOYSA-N 0.000 claims description 8
RDCZVBTWIJZRMX-UHFFFAOYSA-N N-[6-(1-methyltriazol-4-yl)isoquinolin-3-yl]piperidine-4-carboxamide Chemical compound CN1N=NC(=C1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)C1CCNCC1 RDCZVBTWIJZRMX-UHFFFAOYSA-N 0.000 claims description 8
CSYMBONWPUTWCC-UHFFFAOYSA-N N-[6-(1H-pyrazol-4-yl)isoquinolin-3-yl]piperidine-4-carboxamide Chemical compound N1N=CC(=C1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)C1CCNCC1 CSYMBONWPUTWCC-UHFFFAOYSA-N 0.000 claims description 8
NVZIMNZRBHGPIE-UHFFFAOYSA-N N-[6-(2,3-dimethylimidazol-4-yl)isoquinolin-3-yl]piperidine-4-carboxamide Chemical compound CN1C(=NC=C1C=1C=C2C=C(N=CC2=CC=1)NC(=O)C1CCNCC1)C NVZIMNZRBHGPIE-UHFFFAOYSA-N 0.000 claims description 8
BVEGKZCJXYTBDT-UHFFFAOYSA-N N-[6-(3-methylimidazol-4-yl)isoquinolin-3-yl]piperidine-4-carboxamide Chemical compound CN1C=NC=C1C=1C=C2C=C(N=CC2=CC=1)NC(=O)C1CCNCC1 BVEGKZCJXYTBDT-UHFFFAOYSA-N 0.000 claims description 8
FEMABIILBFFBOI-UHFFFAOYSA-N N-[6-[1-methyl-5-(piperidin-1-ylmethyl)pyrazol-4-yl]isoquinolin-3-yl]piperidine-4-carboxamide Chemical compound CN1N=CC(=C1CN1CCCCC1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)C1CCNCC1 FEMABIILBFFBOI-UHFFFAOYSA-N 0.000 claims description 8
201000001119 neuropathy Diseases 0.000 claims description 8
230000007823 neuropathy Effects 0.000 claims description 8
208000033808 peripheral neuropathy Diseases 0.000 claims description 8
NVKYLFYXSUDVML-UHFFFAOYSA-N N-[6-(1-methylpyrazol-4-yl)isoquinolin-3-yl]azetidine-3-carboxamide Chemical compound CN1N=CC(=C1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)C1CNC1 NVKYLFYXSUDVML-UHFFFAOYSA-N 0.000 claims description 7
AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims description 7
125000006545 (C1-C9) alkyl group Chemical group 0.000 claims description 6
201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 6
DMLQFIRSUXFCFO-UHFFFAOYSA-N N-[6-(1-methylpyrazol-4-yl)isoquinolin-3-yl]pyrrolidine-3-carboxamide Chemical compound CN1N=CC(=C1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)C1CNCC1 DMLQFIRSUXFCFO-UHFFFAOYSA-N 0.000 claims description 6
TTXLTJUWLZXODO-UHFFFAOYSA-N N-[6-(3-methyltriazol-4-yl)isoquinolin-3-yl]piperidine-4-carboxamide Chemical compound CN1N=NC=C1C=1C=C2C=C(N=CC2=CC=1)NC(=O)C1CCNCC1 TTXLTJUWLZXODO-UHFFFAOYSA-N 0.000 claims description 6
SBYALMZKJIQEAS-UHFFFAOYSA-N N-[6-(5-methyl-1,3,4-thiadiazol-2-yl)isoquinolin-3-yl]piperidine-4-carboxamide Chemical compound CC1=NN=C(S1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)C1CCNCC1 SBYALMZKJIQEAS-UHFFFAOYSA-N 0.000 claims description 6
206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 6
AWXXNEOTLRMFKW-UHFFFAOYSA-N bicyclo[1.1.1]pentane-3-carboxamide Chemical compound C1C2CC1(C(=O)N)C2 AWXXNEOTLRMFKW-UHFFFAOYSA-N 0.000 claims description 6
208000036971 interstitial lung disease 2 Diseases 0.000 claims description 6
125000003226 pyrazolyl group Chemical group 0.000 claims description 6
125000001425 triazolyl group Chemical group 0.000 claims description 6
206010012289 Dementia Diseases 0.000 claims description 5
208000032612 Glial tumor Diseases 0.000 claims description 5
206010027191 meningioma Diseases 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
HCPWCMYSBPNFMN-CQSZACIVSA-N (2R)-N-[6-(1,3-oxazol-5-yl)isoquinolin-3-yl]oxolane-2-carboxamide Chemical compound O1C=NC=C1C=1C=C2C=C(N=CC2=CC=1)NC(=O)[C@@H]1OCCC1 HCPWCMYSBPNFMN-CQSZACIVSA-N 0.000 claims description 4
OVYHPCXCJYJSCX-CQSZACIVSA-N (2R)-N-[6-(1,3-thiazol-5-yl)isoquinolin-3-yl]pyrrolidine-2-carboxamide Chemical compound S1C=NC=C1C=1C=C2C=C(N=CC2=CC=1)NC(=O)[C@@H]1NCCC1 OVYHPCXCJYJSCX-CQSZACIVSA-N 0.000 claims description 4
XBTQDQIJUCXGNQ-MRXNPFEDSA-N (2R)-N-[6-(1-methylpyrazol-4-yl)isoquinolin-3-yl]oxolane-2-carboxamide Chemical compound CN1N=CC(=C1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)[C@@H]1OCCC1 XBTQDQIJUCXGNQ-MRXNPFEDSA-N 0.000 claims description 4
PKPGVUVTMAVPEP-MRXNPFEDSA-N (2R)-N-[6-(1-methylpyrazol-4-yl)isoquinolin-3-yl]pyrrolidine-2-carboxamide Chemical compound CN1N=CC(=C1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)[C@@H]1NCCC1 PKPGVUVTMAVPEP-MRXNPFEDSA-N 0.000 claims description 4
QLAYOMMKCSGJCD-OAHLLOKOSA-N (2R)-N-[6-(1-methyltriazol-4-yl)isoquinolin-3-yl]oxolane-2-carboxamide Chemical compound CN1N=NC(=C1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)[C@@H]1OCCC1 QLAYOMMKCSGJCD-OAHLLOKOSA-N 0.000 claims description 4
HCFJYMXSYBHVGO-CQSZACIVSA-N (2R)-N-[6-(1-methyltriazol-4-yl)isoquinolin-3-yl]pyrrolidine-2-carboxamide Chemical compound CN1N=NC(=C1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)[C@@H]1NCCC1 HCFJYMXSYBHVGO-CQSZACIVSA-N 0.000 claims description 4
BJQUIDGFTVEPQU-OAHLLOKOSA-N (2R)-N-[6-(1H-pyrazol-4-yl)isoquinolin-3-yl]oxolane-2-carboxamide Chemical compound N1N=CC(=C1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)[C@@H]1OCCC1 BJQUIDGFTVEPQU-OAHLLOKOSA-N 0.000 claims description 4
VRCGBAIYSZHDID-OAHLLOKOSA-N (2R)-N-[6-(1H-pyrazol-4-yl)isoquinolin-3-yl]pyrrolidine-2-carboxamide Chemical compound N1N=CC(=C1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)[C@@H]1NCCC1 VRCGBAIYSZHDID-OAHLLOKOSA-N 0.000 claims description 4
FRBAERHJUYVRGF-QGZVFWFLSA-N (2R)-N-[6-(2,3-dimethylimidazol-4-yl)isoquinolin-3-yl]oxolane-2-carboxamide Chemical compound CN1C(=NC=C1C=1C=C2C=C(N=CC2=CC=1)NC(=O)[C@@H]1OCCC1)C FRBAERHJUYVRGF-QGZVFWFLSA-N 0.000 claims description 4
UCYWAPMVLBTZOX-MRXNPFEDSA-N (2R)-N-[6-(2,3-dimethylimidazol-4-yl)isoquinolin-3-yl]pyrrolidine-2-carboxamide Chemical compound CN1C(=NC=C1C=1C=C2C=C(N=CC2=CC=1)NC(=O)[C@@H]1NCCC1)C UCYWAPMVLBTZOX-MRXNPFEDSA-N 0.000 claims description 4
JFJDVUIXTFVSOA-MRXNPFEDSA-N (2R)-N-[6-(3-methylimidazol-4-yl)isoquinolin-3-yl]oxolane-2-carboxamide Chemical compound CN1C=NC=C1C=1C=C2C=C(N=CC2=CC=1)NC(=O)[C@@H]1OCCC1 JFJDVUIXTFVSOA-MRXNPFEDSA-N 0.000 claims description 4
OCRUEPNZNZHZEH-OAHLLOKOSA-N (2R)-N-[6-(3-methylimidazol-4-yl)isoquinolin-3-yl]pyrrolidine-2-carboxamide Chemical compound CN1C=NC=C1C=1C=C2C=C(N=CC2=CC=1)NC(=O)[C@@H]1NCCC1 OCRUEPNZNZHZEH-OAHLLOKOSA-N 0.000 claims description 4
POTVXOHWCKDTLV-CQSZACIVSA-N (2R)-N-[6-(5-methyl-1,3,4-thiadiazol-2-yl)isoquinolin-3-yl]oxolane-2-carboxamide Chemical compound CC1=NN=C(S1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)[C@@H]1OCCC1 POTVXOHWCKDTLV-CQSZACIVSA-N 0.000 claims description 4
MITUAIWNVAIEOQ-CQSZACIVSA-N (2R)-N-[6-(5-methyl-1,3,4-thiadiazol-2-yl)isoquinolin-3-yl]pyrrolidine-2-carboxamide Chemical compound CC1=NN=C(S1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)[C@@H]1NCCC1 MITUAIWNVAIEOQ-CQSZACIVSA-N 0.000 claims description 4
AKSUZKHVWFNTAA-JOCHJYFZSA-N (2R)-N-[6-[1-methyl-5-(piperidin-1-ylmethyl)pyrazol-4-yl]isoquinolin-3-yl]oxolane-2-carboxamide Chemical compound CN1N=CC(=C1CN1CCCCC1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)[C@@H]1OCCC1 AKSUZKHVWFNTAA-JOCHJYFZSA-N 0.000 claims description 4
XCCNYZVBLGMORF-OAQYLSRUSA-N (2R)-N-[6-[1-methyl-5-(piperidin-1-ylmethyl)pyrazol-4-yl]isoquinolin-3-yl]pyrrolidine-2-carboxamide Chemical compound CN1N=CC(=C1CN1CCCCC1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)[C@@H]1NCCC1 XCCNYZVBLGMORF-OAQYLSRUSA-N 0.000 claims description 4
IRCBBWLCPNJOSC-ZDUSSCGKSA-N (2S)-2-morpholin-4-yl-N-[6-(1H-pyrazol-4-yl)isoquinolin-3-yl]propanamide Chemical compound N1N=CC(=C1)C=1C=C2C=C(N=CC2=CC=1)NC([C@H](C)N1CCOCC1)=O IRCBBWLCPNJOSC-ZDUSSCGKSA-N 0.000 claims description 4
GYHGSEBBBGQENM-AWEZNQCLSA-N (2S)-N-[6-(1-methylpyrazol-4-yl)isoquinolin-3-yl]-2-morpholin-4-ylpropanamide Chemical compound CN1N=CC(=C1)C=1C=C2C=C(N=CC2=CC=1)NC([C@H](C)N1CCOCC1)=O GYHGSEBBBGQENM-AWEZNQCLSA-N 0.000 claims description 4
XBTQDQIJUCXGNQ-INIZCTEOSA-N (2S)-N-[6-(1-methylpyrazol-4-yl)isoquinolin-3-yl]oxolane-2-carboxamide Chemical compound CN1N=CC(=C1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)[C@H]1OCCC1 XBTQDQIJUCXGNQ-INIZCTEOSA-N 0.000 claims description 4
MAVFVFHBSWXKJD-KRWDZBQOSA-N (2S)-N-[6-(1-methylpyrazol-4-yl)isoquinolin-3-yl]piperidine-2-carboxamide Chemical compound CN1N=CC(=C1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)[C@H]1NCCCC1 MAVFVFHBSWXKJD-KRWDZBQOSA-N 0.000 claims description 4
IMEXMSIKAABUSS-ZDUSSCGKSA-N (2S)-N-[6-(1-methyltriazol-4-yl)isoquinolin-3-yl]-2-morpholin-4-ylpropanamide Chemical compound CN1N=NC(=C1)C=1C=C2C=C(N=CC2=CC=1)NC([C@H](C)N1CCOCC1)=O IMEXMSIKAABUSS-ZDUSSCGKSA-N 0.000 claims description 4
IYLXYESMVJZHQI-AWEZNQCLSA-N (2S)-N-[6-(2,3-dimethylimidazol-4-yl)isoquinolin-3-yl]-2-morpholin-4-ylpropanamide Chemical compound CN1C(=NC=C1C=1C=C2C=C(N=CC2=CC=1)NC([C@H](C)N1CCOCC1)=O)C IYLXYESMVJZHQI-AWEZNQCLSA-N 0.000 claims description 4
FRBAERHJUYVRGF-KRWDZBQOSA-N (2S)-N-[6-(2,3-dimethylimidazol-4-yl)isoquinolin-3-yl]oxolane-2-carboxamide Chemical compound CN1C(=NC=C1C=1C=C2C=C(N=CC2=CC=1)NC(=O)[C@H]1OCCC1)C FRBAERHJUYVRGF-KRWDZBQOSA-N 0.000 claims description 4
SIQWXCAUWUMVLG-AWEZNQCLSA-N (2S)-N-[6-(3-methylimidazol-4-yl)isoquinolin-3-yl]-2-morpholin-4-ylpropanamide Chemical compound CN1C=NC=C1C=1C=C2C=C(N=CC2=CC=1)NC([C@H](C)N1CCOCC1)=O SIQWXCAUWUMVLG-AWEZNQCLSA-N 0.000 claims description 4
NRJUCELPGMBGTH-LBPRGKRZSA-N (2S)-N-[6-(5-methyl-1,3,4-thiadiazol-2-yl)isoquinolin-3-yl]-2-morpholin-4-ylpropanamide Chemical compound CC1=NN=C(S1)C=1C=C2C=C(N=CC2=CC=1)NC([C@H](C)N1CCOCC1)=O NRJUCELPGMBGTH-LBPRGKRZSA-N 0.000 claims description 4
FLEUOMGTUFBOHD-GOSISDBHSA-N (3R)-1-(2-methylpropyl)-N-[6-(1H-pyrazol-4-yl)isoquinolin-3-yl]piperidine-3-carboxamide Chemical compound N1N=CC(=C1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)[C@H]1CN(CCC1)CC(C)C FLEUOMGTUFBOHD-GOSISDBHSA-N 0.000 claims description 4
PUNWQCJQQRHKFQ-CQSZACIVSA-N (3R)-N-[6-(1,3-oxazol-5-yl)isoquinolin-3-yl]piperidine-3-carboxamide Chemical compound O1C=NC=C1C=1C=C2C=C(N=CC2=CC=1)NC(=O)[C@H]1CNCCC1 PUNWQCJQQRHKFQ-CQSZACIVSA-N 0.000 claims description 4
JRAHRNXMWOAZKC-OAHLLOKOSA-N (3R)-N-[6-(1-methylpyrazol-4-yl)isoquinolin-3-yl]piperidine-3-carboxamide Chemical compound CN1N=CC(=C1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)[C@H]1CNCCC1 JRAHRNXMWOAZKC-OAHLLOKOSA-N 0.000 claims description 4
DVORMWKQZVEZCD-CQSZACIVSA-N (3R)-N-[6-(1-methyltriazol-4-yl)isoquinolin-3-yl]piperidine-3-carboxamide Chemical compound CN1N=NC(=C1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)[C@H]1CNCCC1 DVORMWKQZVEZCD-CQSZACIVSA-N 0.000 claims description 4
GLDNEAXLNPJKIT-HXUWFJFHSA-N (3R)-N-[6-[1-methyl-5-(piperidin-1-ylmethyl)pyrazol-4-yl]isoquinolin-3-yl]piperidine-3-carboxamide Chemical compound CN1N=CC(=C1CN1CCCCC1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)[C@H]1CNCCC1 GLDNEAXLNPJKIT-HXUWFJFHSA-N 0.000 claims description 4
BCGDIWRWMJLDBO-AWEZNQCLSA-N (3S)-N-[6-(1,3-thiazol-5-yl)isoquinolin-3-yl]piperidine-3-carboxamide Chemical compound S1C=NC=C1C=1C=C2C=C(N=CC2=CC=1)NC(=O)[C@@H]1CNCCC1 BCGDIWRWMJLDBO-AWEZNQCLSA-N 0.000 claims description 4
JRAHRNXMWOAZKC-HNNXBMFYSA-N (3S)-N-[6-(1-methylpyrazol-4-yl)isoquinolin-3-yl]piperidine-3-carboxamide Chemical compound CN1N=CC(=C1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)[C@@H]1CNCCC1 JRAHRNXMWOAZKC-HNNXBMFYSA-N 0.000 claims description 4
SGJWINSCOXKPTJ-AWEZNQCLSA-N (3S)-N-[6-(1H-pyrazol-4-yl)isoquinolin-3-yl]piperidine-3-carboxamide Chemical compound N1N=CC(=C1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)[C@@H]1CNCCC1 SGJWINSCOXKPTJ-AWEZNQCLSA-N 0.000 claims description 4
LEUCPWSJWMCMGM-INIZCTEOSA-N (3S)-N-[6-(2,3-dimethylimidazol-4-yl)isoquinolin-3-yl]piperidine-3-carboxamide Chemical compound CN1C(=NC=C1C=1C=C2C=C(N=CC2=CC=1)NC(=O)[C@@H]1CNCCC1)C LEUCPWSJWMCMGM-INIZCTEOSA-N 0.000 claims description 4
QBMCCGMVHWCFKO-HNNXBMFYSA-N (3S)-N-[6-(3-methylimidazol-4-yl)isoquinolin-3-yl]piperidine-3-carboxamide Chemical compound CN1C=NC=C1C=1C=C2C=C(N=CC2=CC=1)NC(=O)[C@@H]1CNCCC1 QBMCCGMVHWCFKO-HNNXBMFYSA-N 0.000 claims description 4
GJCUWYHBMKCPCK-UHFFFAOYSA-N 1-(1-methylpiperidin-4-yl)-3-[6-(1-methylpyrazol-4-yl)isoquinolin-3-yl]urea Chemical compound CN1CCC(CC1)NC(=O)NC=1N=CC2=CC=C(C=C2C=1)C=1C=NN(C=1)C GJCUWYHBMKCPCK-UHFFFAOYSA-N 0.000 claims description 4
BFAQTTOHVDQMAG-UHFFFAOYSA-N 1-(1-methylpiperidin-4-yl)-N-[6-(1,3-oxazol-5-yl)isoquinolin-3-yl]piperidine-4-carboxamide Chemical compound CN1CCC(CC1)N1CCC(CC1)C(=O)NC=1N=CC2=CC=C(C=C2C=1)C1=CN=CO1 BFAQTTOHVDQMAG-UHFFFAOYSA-N 0.000 claims description 4
SCVORHIPJWJLNS-UHFFFAOYSA-N 1-(1-methylpiperidin-4-yl)-N-[6-(1,3-thiazol-5-yl)isoquinolin-3-yl]piperidine-4-carboxamide Chemical compound CN1CCC(CC1)N1CCC(CC1)C(=O)NC=1N=CC2=CC=C(C=C2C=1)C1=CN=CS1 SCVORHIPJWJLNS-UHFFFAOYSA-N 0.000 claims description 4
CGTURZNGZBYAFY-UHFFFAOYSA-N 1-(1-methylpiperidin-4-yl)-N-[6-(1-methylpyrazol-4-yl)isoquinolin-3-yl]piperidine-4-carboxamide Chemical compound CN1CCC(CC1)N1CCC(CC1)C(=O)NC=1N=CC2=CC=C(C=C2C=1)C=1C=NN(C=1)C CGTURZNGZBYAFY-UHFFFAOYSA-N 0.000 claims description 4
CXQYIRXQJJWARW-UHFFFAOYSA-N 1-(1-methylpiperidin-4-yl)-N-[6-(1H-pyrazol-4-yl)isoquinolin-3-yl]piperidine-4-carboxamide Chemical compound N1N=CC(=C1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)C1CCN(CC1)C1CCN(CC1)C CXQYIRXQJJWARW-UHFFFAOYSA-N 0.000 claims description 4
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HIDTVZDPVWDGDT-UHFFFAOYSA-N N-[6-(1,3-thiazol-5-yl)isoquinolin-3-yl]cyclopropanecarboxamide Chemical compound S1C=NC=C1C=1C=C2C=C(N=CC2=CC=1)NC(=O)C1CC1 HIDTVZDPVWDGDT-UHFFFAOYSA-N 0.000 claims description 4
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MIXAIARLQCQSJY-UHFFFAOYSA-N N-[6-(1-methylpyrazol-4-yl)isoquinolin-3-yl]-1-azabicyclo[2.2.2]octane-4-carboxamide Chemical compound CN1N=CC(=C1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)C12CCN(CC1)CC2 MIXAIARLQCQSJY-UHFFFAOYSA-N 0.000 claims description 4
NNRRUVRJOVYLIC-UHFFFAOYSA-N N-[6-(1-methylpyrazol-4-yl)isoquinolin-3-yl]-2-(2,2,2-trifluoroacetyl)-2-azaspiro[3.3]heptane-6-carboxamide Chemical compound CN1N=CC(=C1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)C1CC2(CN(C2)C(C(F)(F)F)=O)C1 NNRRUVRJOVYLIC-UHFFFAOYSA-N 0.000 claims description 4
CHKNEDZXGBZESY-UHFFFAOYSA-N N-[6-(1-methylpyrazol-4-yl)isoquinolin-3-yl]-2-morpholin-4-ylacetamide Chemical compound CN1N=CC(=C1)C=1C=C2C=C(N=CC2=CC=1)NC(CN1CCOCC1)=O CHKNEDZXGBZESY-UHFFFAOYSA-N 0.000 claims description 4
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QOOZZDKPHONCPI-UHFFFAOYSA-N N-[6-(1-methylpyrazol-4-yl)isoquinolin-3-yl]cyclohexanecarboxamide Chemical compound CN1N=CC(=C1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)C1CCCCC1 QOOZZDKPHONCPI-UHFFFAOYSA-N 0.000 claims description 4
XXHMYJNPMZZGMF-UHFFFAOYSA-N N-[6-(1-methylpyrazol-4-yl)isoquinolin-3-yl]cyclopropanecarboxamide Chemical compound CN1N=CC(=C1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)C1CC1 XXHMYJNPMZZGMF-UHFFFAOYSA-N 0.000 claims description 4
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CQVIKPPHCIOSJV-UHFFFAOYSA-N N-[6-(1-methyltriazol-4-yl)isoquinolin-3-yl]-2-morpholin-4-ylacetamide Chemical compound CN1N=NC(=C1)C=1C=C2C=C(N=CC2=CC=1)NC(CN1CCOCC1)=O CQVIKPPHCIOSJV-UHFFFAOYSA-N 0.000 claims description 4
TWWIPMPLDCRMPK-UHFFFAOYSA-N N-[6-(1-methyltriazol-4-yl)isoquinolin-3-yl]azetidine-3-carboxamide Chemical compound CN1N=NC(=C1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)C1CNC1 TWWIPMPLDCRMPK-UHFFFAOYSA-N 0.000 claims description 4
LETZRMJUBWQCKB-UHFFFAOYSA-N N-[6-(1-methyltriazol-4-yl)isoquinolin-3-yl]cyclopropanecarboxamide Chemical compound C1(CC1)C(=O)NC=1N=CC2=CC=C(C=C2C=1)C=1N=NN(C=1)C LETZRMJUBWQCKB-UHFFFAOYSA-N 0.000 claims description 4
KVDDYPDRRGMWRB-UHFFFAOYSA-N N-[6-(1-methyltriazol-4-yl)isoquinolin-3-yl]oxane-4-carboxamide Chemical compound CN1N=NC(=C1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)C1CCOCC1 KVDDYPDRRGMWRB-UHFFFAOYSA-N 0.000 claims description 4
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BLUVFWOVTNBYEJ-UHFFFAOYSA-N N-[6-(1H-pyrazol-4-yl)isoquinolin-3-yl]cyclopropanecarboxamide Chemical compound C1(CC1)C(=O)NC=1N=CC2=CC=C(C=C2C=1)C=1C=NNC=1 BLUVFWOVTNBYEJ-UHFFFAOYSA-N 0.000 claims description 4
NIOMVSLBZWGGTG-UHFFFAOYSA-N N-[6-(2,3-dimethylimidazol-4-yl)isoquinolin-3-yl]-1-(1-methylpiperidin-4-yl)piperidine-4-carboxamide Chemical compound CN1C(=NC=C1C=1C=C2C=C(N=CC2=CC=1)NC(=O)C1CCN(CC1)C1CCN(CC1)C)C NIOMVSLBZWGGTG-UHFFFAOYSA-N 0.000 claims description 4
OVKXSERHEFSIBO-UHFFFAOYSA-N N-[6-(2,3-dimethylimidazol-4-yl)isoquinolin-3-yl]-1-(2,2-dimethylpropyl)-4-fluoropiperidine-4-carboxamide Chemical compound CN1C(=NC=C1C=1C=C2C=C(N=CC2=CC=1)NC(=O)C1(CCN(CC1)CC(C)(C)C)F)C OVKXSERHEFSIBO-UHFFFAOYSA-N 0.000 claims description 4
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HGALHCICURXXAS-UHFFFAOYSA-N N-[6-(2,3-dimethylimidazol-4-yl)isoquinolin-3-yl]-1-ethyl-3-fluoroazetidine-3-carboxamide Chemical compound CN1C(=NC=C1C=1C=C2C=C(N=CC2=CC=1)NC(=O)C1(CN(C1)CC)F)C HGALHCICURXXAS-UHFFFAOYSA-N 0.000 claims description 4
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VYOBTUUAAVYBQL-UHFFFAOYSA-N N-[6-(2,3-dimethylimidazol-4-yl)isoquinolin-3-yl]-2-(2,2,2-trifluoroacetyl)-2-azaspiro[3.3]heptane-6-carboxamide Chemical compound CN1C(=NC=C1C=1C=C2C=C(N=CC2=CC=1)NC(=O)C1CC2(CN(C2)C(C(F)(F)F)=O)C1)C VYOBTUUAAVYBQL-UHFFFAOYSA-N 0.000 claims description 4
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AICRLRHPCNDHKK-UHFFFAOYSA-N N-[6-(2,3-dimethylimidazol-4-yl)isoquinolin-3-yl]-2-morpholin-4-ylacetamide Chemical compound CN1C(=NC=C1C=1C=C2C=C(N=CC2=CC=1)NC(CN1CCOCC1)=O)C AICRLRHPCNDHKK-UHFFFAOYSA-N 0.000 claims description 4
XYPMKAHFXCNOAF-UHFFFAOYSA-N N-[6-(2,3-dimethylimidazol-4-yl)isoquinolin-3-yl]-3,3-difluorocyclobutane-1-carboxamide Chemical compound CN1C(=NC=C1C=1C=C2C=C(N=CC2=CC=1)NC(=O)C1CC(C1)(F)F)C XYPMKAHFXCNOAF-UHFFFAOYSA-N 0.000 claims description 4
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JIJBCBUJSRFZRM-UHFFFAOYSA-N N-[6-(2,3-dimethylimidazol-4-yl)isoquinolin-3-yl]-4,4-difluorocyclohexane-1-carboxamide Chemical compound CN1C(=NC=C1C=1C=C2C=C(N=CC2=CC=1)NC(=O)C1CCC(CC1)(F)F)C JIJBCBUJSRFZRM-UHFFFAOYSA-N 0.000 claims description 4
GXWJELFUVVYLCL-UHFFFAOYSA-N N-[6-(2,3-dimethylimidazol-4-yl)isoquinolin-3-yl]-4-fluoro-1-(2-methylpropyl)piperidine-4-carboxamide Chemical compound CC(C)CN1CCC(F)(CC1)C(=O)NC1=CC2=CC(=CC=C2C=N1)C1=CN=C(C)N1C GXWJELFUVVYLCL-UHFFFAOYSA-N 0.000 claims description 4
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KFBZXPPMIWBUDV-UHFFFAOYSA-N N-[6-(2,3-dimethylimidazol-4-yl)isoquinolin-3-yl]-4-fluoropiperidine-4-carboxamide Chemical compound CN1C(=NC=C1C=1C=C2C=C(N=CC2=CC=1)NC(=O)C1(CCNCC1)F)C KFBZXPPMIWBUDV-UHFFFAOYSA-N 0.000 claims description 4
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DTTRGDMMSSHCHO-UHFFFAOYSA-N N-[6-(3-methylimidazol-4-yl)isoquinolin-3-yl]-2-(2,2,2-trifluoroacetyl)-2-azaspiro[3.3]heptane-6-carboxamide Chemical compound CN1C=NC=C1C=1C=C2C=C(N=CC2=CC=1)NC(=O)C1CC2(CN(C2)C(C(F)(F)F)=O)C1 DTTRGDMMSSHCHO-UHFFFAOYSA-N 0.000 claims description 4
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JQHKXKZTAWAGKD-UHFFFAOYSA-N N-[6-(3-methylimidazol-4-yl)isoquinolin-3-yl]azetidine-3-carboxamide Chemical compound CN1C=NC=C1C=1C=C2C=C(N=CC2=CC=1)NC(=O)C1CNC1 JQHKXKZTAWAGKD-UHFFFAOYSA-N 0.000 claims description 4
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JP2018556921A 2016-04-27 2017-04-27 イソキノリン－３イル－カルボキサミドならびにその調製および使用の方法 Active JP7023243B2 (ja)