JP2013542265A5

JP2013542265A5 -

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Publication number: JP2013542265A5
Authority: JP; Japan
Prior art keywords: dihydro; carboxamide; phenyl; isoindole; carbamoyl
Prior art date: 2011-11-11
Legal status : Granted

Application number

JP2013538943A

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English (en)

Japanese (ja)

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JP6117104B2 (ja

JP2013542265A (ja

Filing date

2011-11-11

Publication date

2017-03-16

2011-11-11 Application filed filed Critical

2011-11-11 Priority claimed from PCT/US2011/060425 external-priority patent/WO2012067965A1/en

2013-11-21 Publication of JP2013542265A publication Critical patent/JP2013542265A/ja

2017-03-16 Publication of JP2013542265A5 publication Critical patent/JP2013542265A5/ja

2017-04-19 Application granted granted Critical

2017-04-19 Publication of JP6117104B2 publication Critical patent/JP6117104B2/ja

Status Active legal-status Critical Current

2031-11-11 Anticipated expiration legal-status Critical

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-1 1,3-benzodioxol-5-ylmethyl Chemical group 0.000 description 317
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 255
150000003857 carboxamides Chemical class 0.000 description 132
WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 98
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 49
IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 description 46
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 44
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 42
125000000070 5-oxo-L-proline group Chemical group [H]N1[C@@](C(=O)[*])([H])C([H])([H])C([H])([H])C1=O 0.000 description 20
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 10
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 10
125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 description 8
150000003839 salts Chemical class 0.000 description 8
UAGOLVFLAOSFHO-AWEZNQCLSA-N 5-fluoro-n-[4-[[(3s)-oxolan-3-yl]methylcarbamoyl]phenyl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC(F)=CC=C2CN1C(=O)NC(C=C1)=CC=C1C(=O)NC[C@@H]1CCOC1 UAGOLVFLAOSFHO-AWEZNQCLSA-N 0.000 description 7
150000001875 compounds Chemical class 0.000 description 7
BLZJCPAXCWJANZ-HNNXBMFYSA-N n-[4-[[(3s)-oxolan-3-yl]methylcarbamoyl]phenyl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(C=C1)=CC=C1C(=O)NC[C@@H]1CCOC1 BLZJCPAXCWJANZ-HNNXBMFYSA-N 0.000 description 7
PAZLERJGBJMLAZ-UHFFFAOYSA-N n-[4-(1-methoxypropan-2-ylcarbamoyl)phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1=CC(C(=O)NC(C)COC)=CC=C1NC(=O)N1CC2=CN=CC=C2C1 PAZLERJGBJMLAZ-UHFFFAOYSA-N 0.000 description 6
IVEJMRPOANPQGR-UHFFFAOYSA-N n-[4-(1-oxa-8-azaspiro[4.5]decan-2-ylmethylcarbamoyl)phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1C2=CC=NC=C2CN1C(=O)NC(C=C1)=CC=C1C(=O)NCC(O1)CCC21CCNCC2 IVEJMRPOANPQGR-UHFFFAOYSA-N 0.000 description 6
RACZACSNMXDFOE-UHFFFAOYSA-N n-[4-(2-methylpropylcarbamoyl)phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1=CC(C(=O)NCC(C)C)=CC=C1NC(=O)N1CC2=CN=CC=C2C1 RACZACSNMXDFOE-UHFFFAOYSA-N 0.000 description 6
FHNACHSLAHQRBN-UHFFFAOYSA-N n-[4-(2-oxa-9-azaspiro[5.5]undecan-3-ylmethylcarbamoyl)phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1C2=CC=NC=C2CN1C(=O)NC(C=C1)=CC=C1C(=O)NCC(OC1)CCC21CCNCC2 FHNACHSLAHQRBN-UHFFFAOYSA-N 0.000 description 6
IPWPYCHMWDRDDA-UHFFFAOYSA-N n-[4-(2-propan-2-yloxyethylcarbamoyl)phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1=CC(C(=O)NCCOC(C)C)=CC=C1NC(=O)N1CC2=CN=CC=C2C1 IPWPYCHMWDRDDA-UHFFFAOYSA-N 0.000 description 6
JDSMIJJTXRHLFN-UHFFFAOYSA-N n-[4-(3-hydroxypropylcarbamoyl)phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1=CC(C(=O)NCCCO)=CC=C1NC(=O)N1CC2=CN=CC=C2C1 JDSMIJJTXRHLFN-UHFFFAOYSA-N 0.000 description 6
LMYQDAFZILWDHN-UHFFFAOYSA-N n-[4-(3-methylbutylcarbamoyl)phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1=CC(C(=O)NCCC(C)C)=CC=C1NC(=O)N1CC2=CN=CC=C2C1 LMYQDAFZILWDHN-UHFFFAOYSA-N 0.000 description 6
HMBUWSKMCBOQRT-UHFFFAOYSA-N n-[4-(3-morpholin-4-ylpropylcarbamoyl)phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1C2=CC=NC=C2CN1C(=O)NC(C=C1)=CC=C1C(=O)NCCCN1CCOCC1 HMBUWSKMCBOQRT-UHFFFAOYSA-N 0.000 description 6
YEKMGBPSFMSEHW-UHFFFAOYSA-N n-[4-(3-piperidin-1-ylpropylcarbamoyl)phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1C2=CC=NC=C2CN1C(=O)NC(C=C1)=CC=C1C(=O)NCCCN1CCCCC1 YEKMGBPSFMSEHW-UHFFFAOYSA-N 0.000 description 6
PYHPKZNXFFDZRR-UHFFFAOYSA-N n-[4-(3-propan-2-yloxypropylcarbamoyl)phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1=CC(C(=O)NCCCOC(C)C)=CC=C1NC(=O)N1CC2=CN=CC=C2C1 PYHPKZNXFFDZRR-UHFFFAOYSA-N 0.000 description 6
FWTRAKZCXKGTCA-UHFFFAOYSA-N n-[4-(4-hydroxybutylcarbamoyl)phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1=CC(C(=O)NCCCCO)=CC=C1NC(=O)N1CC2=CN=CC=C2C1 FWTRAKZCXKGTCA-UHFFFAOYSA-N 0.000 description 6
OPGHEZZLELMVBJ-UHFFFAOYSA-N n-[4-(butylcarbamoyl)phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1=CC(C(=O)NCCCC)=CC=C1NC(=O)N1CC2=CN=CC=C2C1 OPGHEZZLELMVBJ-UHFFFAOYSA-N 0.000 description 6
GRKCUIQVKUTEAY-UHFFFAOYSA-N n-[4-(cyclopentylcarbamoyl)phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1C2=CC=NC=C2CN1C(=O)NC(C=C1)=CC=C1C(=O)NC1CCCC1 GRKCUIQVKUTEAY-UHFFFAOYSA-N 0.000 description 6
UPRIIMDETMWYKF-UHFFFAOYSA-N n-[4-(cyclopentylmethylcarbamoyl)phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1C2=CC=NC=C2CN1C(=O)NC(C=C1)=CC=C1C(=O)NCC1CCCC1 UPRIIMDETMWYKF-UHFFFAOYSA-N 0.000 description 6
YPUUEPDIVJYYTQ-UHFFFAOYSA-N n-[4-(cyclopropylmethylcarbamoyl)phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1C2=CC=NC=C2CN1C(=O)NC(C=C1)=CC=C1C(=O)NCC1CC1 YPUUEPDIVJYYTQ-UHFFFAOYSA-N 0.000 description 6
LMLAHQXYKBGDEV-UHFFFAOYSA-N n-[4-(oxan-2-ylmethylcarbamoyl)phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1C2=CC=NC=C2CN1C(=O)NC(C=C1)=CC=C1C(=O)NCC1CCCCO1 LMLAHQXYKBGDEV-UHFFFAOYSA-N 0.000 description 6
SGQLQPJPPTVIHP-UHFFFAOYSA-N n-[4-(oxan-3-ylmethylcarbamoyl)phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1C2=CC=NC=C2CN1C(=O)NC(C=C1)=CC=C1C(=O)NCC1CCCOC1 SGQLQPJPPTVIHP-UHFFFAOYSA-N 0.000 description 6
JBVXMCIEZXOXIU-UHFFFAOYSA-N n-[4-(oxan-4-ylmethylcarbamoyl)phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1C2=CC=NC=C2CN1C(=O)NC(C=C1)=CC=C1C(=O)NCC1CCOCC1 JBVXMCIEZXOXIU-UHFFFAOYSA-N 0.000 description 6
CAAZCWZYLWBLGF-UHFFFAOYSA-N n-[4-(oxolan-3-ylmethylcarbamoyl)phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1C2=CC=NC=C2CN1C(=O)NC(C=C1)=CC=C1C(=O)NCC1CCOC1 CAAZCWZYLWBLGF-UHFFFAOYSA-N 0.000 description 6
NGUFFFLPXYXVKZ-UHFFFAOYSA-N n-[4-(propylcarbamoyl)phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1=CC(C(=O)NCCC)=CC=C1NC(=O)N1CC2=CN=CC=C2C1 NGUFFFLPXYXVKZ-UHFFFAOYSA-N 0.000 description 6
PQEMTAYTMIRGEZ-UHFFFAOYSA-N n-[4-(pyridin-3-ylmethylcarbamoyl)phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1C2=CC=NC=C2CN1C(=O)NC(C=C1)=CC=C1C(=O)NCC1=CC=CN=C1 PQEMTAYTMIRGEZ-UHFFFAOYSA-N 0.000 description 6
CIKFUNYTOPIXIP-UHFFFAOYSA-N n-[4-(pyridin-4-ylmethylcarbamoyl)phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1C2=CC=NC=C2CN1C(=O)NC(C=C1)=CC=C1C(=O)NCC1=CC=NC=C1 CIKFUNYTOPIXIP-UHFFFAOYSA-N 0.000 description 6
QFQJOSGJGUBGOB-UHFFFAOYSA-N n-[4-(pyrrolidin-3-ylmethylcarbamoyl)phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1C2=CC=NC=C2CN1C(=O)NC(C=C1)=CC=C1C(=O)NCC1CCNC1 QFQJOSGJGUBGOB-UHFFFAOYSA-N 0.000 description 6
WZINUIBLYHNGIR-UHFFFAOYSA-N n-[4-(thiophen-2-ylmethylcarbamoyl)phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1C2=CC=NC=C2CN1C(=O)NC(C=C1)=CC=C1C(=O)NCC1=CC=CS1 WZINUIBLYHNGIR-UHFFFAOYSA-N 0.000 description 6
UEYJWRCDFKIIKF-UHFFFAOYSA-N n-[4-[(1-hydroxy-2-methylpropan-2-yl)carbamoyl]phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1=CC(C(=O)NC(C)(CO)C)=CC=C1NC(=O)N1CC2=CN=CC=C2C1 UEYJWRCDFKIIKF-UHFFFAOYSA-N 0.000 description 6
MIIOHLUVFCURCG-UHFFFAOYSA-N n-[4-[(1-methylpiperidin-4-yl)methylcarbamoyl]phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1CN(C)CCC1CNC(=O)C(C=C1)=CC=C1NC(=O)N1CC2=CN=CC=C2C1 MIIOHLUVFCURCG-UHFFFAOYSA-N 0.000 description 6
LWRPDLIPXWMHIH-UHFFFAOYSA-N n-[4-[(1-methylpyrrolidin-3-yl)methylcarbamoyl]phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1N(C)CCC1CNC(=O)C(C=C1)=CC=C1NC(=O)N1CC2=CN=CC=C2C1 LWRPDLIPXWMHIH-UHFFFAOYSA-N 0.000 description 6
SGTBWNNBOOPACZ-UHFFFAOYSA-N n-[4-[(1-morpholin-4-ylcyclopentyl)methylcarbamoyl]phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1C2=CC=NC=C2CN1C(=O)NC(C=C1)=CC=C1C(=O)NCC1(N2CCOCC2)CCCC1 SGTBWNNBOOPACZ-UHFFFAOYSA-N 0.000 description 6
DJMREHHFCMYNHJ-UHFFFAOYSA-N n-[4-[(2-hydroxy-2-methylpropyl)carbamoyl]phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1=CC(C(=O)NCC(C)(O)C)=CC=C1NC(=O)N1CC2=CN=CC=C2C1 DJMREHHFCMYNHJ-UHFFFAOYSA-N 0.000 description 6
BAVUXUFFHARBQR-UHFFFAOYSA-N n-[4-[(3,5-dimethoxyphenyl)methylcarbamoyl]phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound COC1=CC(OC)=CC(CNC(=O)C=2C=CC(NC(=O)N3CC4=CN=CC=C4C3)=CC=2)=C1 BAVUXUFFHARBQR-UHFFFAOYSA-N 0.000 description 6
NRBMYBPBHISIJE-UHFFFAOYSA-N n-[4-[(3-aminophenyl)methylcarbamoyl]phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound NC1=CC=CC(CNC(=O)C=2C=CC(NC(=O)N3CC4=CN=CC=C4C3)=CC=2)=C1 NRBMYBPBHISIJE-UHFFFAOYSA-N 0.000 description 6
XHDVJJAVDRSWRU-UHFFFAOYSA-N n-[4-[(3-methoxyphenyl)methylcarbamoyl]phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound COC1=CC=CC(CNC(=O)C=2C=CC(NC(=O)N3CC4=CN=CC=C4C3)=CC=2)=C1 XHDVJJAVDRSWRU-UHFFFAOYSA-N 0.000 description 6
GAJKKWPPUFCDON-UHFFFAOYSA-N n-[4-[(3-methyloxetan-3-yl)methylcarbamoyl]phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C=1C=C(NC(=O)N2CC3=CN=CC=C3C2)C=CC=1C(=O)NCC1(C)COC1 GAJKKWPPUFCDON-UHFFFAOYSA-N 0.000 description 6
VHQCZIIQTHRLRC-UHFFFAOYSA-N n-[4-[(4-chlorophenyl)methylcarbamoyl]phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1CNC(=O)C(C=C1)=CC=C1NC(=O)N1CC2=CN=CC=C2C1 VHQCZIIQTHRLRC-UHFFFAOYSA-N 0.000 description 6
HCYWKUPRVAVQGU-UHFFFAOYSA-N n-[4-[(4-methoxyphenyl)methylcarbamoyl]phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1=CC(OC)=CC=C1CNC(=O)C(C=C1)=CC=C1NC(=O)N1CC2=CN=CC=C2C1 HCYWKUPRVAVQGU-UHFFFAOYSA-N 0.000 description 6
WFLUFDLRKVGJFU-UHFFFAOYSA-N n-[4-[(6-methoxypyridin-3-yl)carbamoyl]phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1=NC(OC)=CC=C1NC(=O)C(C=C1)=CC=C1NC(=O)N1CC2=CN=CC=C2C1 WFLUFDLRKVGJFU-UHFFFAOYSA-N 0.000 description 6
FSBJXYBBHNHBEA-UHFFFAOYSA-N n-[4-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1CN(C(=O)C(C)(O)C)CCC1C(C=C1)=CC=C1NC(=O)N1CC2=CN=CC=C2C1 FSBJXYBBHNHBEA-UHFFFAOYSA-N 0.000 description 6
LWRDGKVJYLYWMY-UHFFFAOYSA-N n-[4-[1-(2-methylpropanoyl)-3,6-dihydro-2h-pyridin-4-yl]phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1N(C(=O)C(C)C)CCC(C=2C=CC(NC(=O)N3CC4=CN=CC=C4C3)=CC=2)=C1 LWRDGKVJYLYWMY-UHFFFAOYSA-N 0.000 description 6
DMFSPVRZNNUHMU-UHFFFAOYSA-N n-[4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1CN(C(=O)C(C)C)CCC1C(C=C1)=CC=C1NC(=O)N1CC2=CN=CC=C2C1 DMFSPVRZNNUHMU-UHFFFAOYSA-N 0.000 description 6
XGOYLDONAGPTCS-QFIPXVFZSA-N n-[4-[1-[(2s)-oxolane-2-carbonyl]-3,6-dihydro-2h-pyridin-4-yl]phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1C2=CC=NC=C2CN1C(=O)NC(C=C1)=CC=C1C(CC1)=CCN1C(=O)[C@@H]1CCCO1 XGOYLDONAGPTCS-QFIPXVFZSA-N 0.000 description 6
DMAGLJBHHVJXBB-FQEVSTJZSA-N n-[4-[1-[(3s)-oxolane-3-carbonyl]-3,6-dihydro-2h-pyridin-4-yl]phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1C2=CC=NC=C2CN1C(=O)NC(C=C1)=CC=C1C(CC1)=CCN1C(=O)[C@H]1CCOC1 DMAGLJBHHVJXBB-FQEVSTJZSA-N 0.000 description 6
LZCBLVDGEVWMFC-FQEVSTJZSA-N n-[4-[1-[(3s)-oxolane-3-carbonyl]piperidin-4-yl]phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1C2=CC=NC=C2CN1C(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)[C@H]1CCOC1 LZCBLVDGEVWMFC-FQEVSTJZSA-N 0.000 description 6
VWHAMLOFQJOJDR-UHFFFAOYSA-N n-[4-[2-(3,4-dimethoxyphenyl)ethylcarbamoyl]phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1CCNC(=O)C(C=C1)=CC=C1NC(=O)N1CC2=CN=CC=C2C1 VWHAMLOFQJOJDR-UHFFFAOYSA-N 0.000 description 6
REDTYASTIUBDAW-UHFFFAOYSA-N n-[4-[2-(4-methylpiperazin-1-yl)ethylcarbamoyl]phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1CN(C)CCN1CCNC(=O)C(C=C1)=CC=C1NC(=O)N1CC2=CN=CC=C2C1 REDTYASTIUBDAW-UHFFFAOYSA-N 0.000 description 6
UTEYNYMXLGEHKM-UHFFFAOYSA-N n-[4-[3-(2-methylpropoxy)propylcarbamoyl]phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1=CC(C(=O)NCCCOCC(C)C)=CC=C1NC(=O)N1CC2=CN=CC=C2C1 UTEYNYMXLGEHKM-UHFFFAOYSA-N 0.000 description 6
COMHSVLJJUYQDE-UHFFFAOYSA-N n-[4-[3-(2-oxopyrrolidin-1-yl)propylcarbamoyl]phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1C2=CC=NC=C2CN1C(=O)NC(C=C1)=CC=C1C(=O)NCCCN1CCCC1=O COMHSVLJJUYQDE-UHFFFAOYSA-N 0.000 description 6
MTLUZHRCAWSVJV-UHFFFAOYSA-N n-[4-[3-(dimethylamino)propylcarbamoyl]phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1=CC(C(=O)NCCCN(C)C)=CC=C1NC(=O)N1CC2=CN=CC=C2C1 MTLUZHRCAWSVJV-UHFFFAOYSA-N 0.000 description 6
JVQBSMUVYJNDLD-UHFFFAOYSA-N n-[4-[4-(dimethylamino)butylcarbamoyl]phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1=CC(C(=O)NCCCCN(C)C)=CC=C1NC(=O)N1CC2=CN=CC=C2C1 JVQBSMUVYJNDLD-UHFFFAOYSA-N 0.000 description 6
IPBDVNKCRIHUGN-OAQYLSRUSA-N n-[4-[[(1s)-1-(4-fluorophenyl)-2-hydroxyethyl]carbamoyl]phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1([C@H](NC(=O)C=2C=CC(NC(=O)N3CC4=CN=CC=C4C3)=CC=2)CO)=CC=C(F)C=C1 IPBDVNKCRIHUGN-OAQYLSRUSA-N 0.000 description 6
PKDOWSPMBKSODP-JOCHJYFZSA-N n-[4-[[(1s)-2-hydroxy-1-(4-methoxyphenyl)ethyl]carbamoyl]phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1=CC(OC)=CC=C1[C@@H](CO)NC(=O)C(C=C1)=CC=C1NC(=O)N1CC2=CN=CC=C2C1 PKDOWSPMBKSODP-JOCHJYFZSA-N 0.000 description 6
NAVFJMLXKQDHNK-GFCCVEGCSA-N n-[4-[[(2r)-2-hydroxypropyl]carbamoyl]phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1=CC(C(=O)NC[C@H](O)C)=CC=C1NC(=O)N1CC2=CN=CC=C2C1 NAVFJMLXKQDHNK-GFCCVEGCSA-N 0.000 description 6
HUKQLRIIAYRCBJ-GOSISDBHSA-N n-[4-[[(2r)-oxolan-2-yl]methylcarbamoyl]phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1C2=CC=NC=C2CN1C(=O)NC(C=C1)=CC=C1C(=O)NC[C@H]1CCCO1 HUKQLRIIAYRCBJ-GOSISDBHSA-N 0.000 description 6
RSMNRCBFRQQEGJ-GOSISDBHSA-N n-[4-[[(2s)-1-hydroxy-3-methylbutan-2-yl]carbamoyl]phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1=CC(C(=O)N[C@H](CO)C(C)C)=CC=C1NC(=O)N1CC2=CN=CC=C2C1 RSMNRCBFRQQEGJ-GOSISDBHSA-N 0.000 description 6
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FFLNRICJYUDWLZ-UHFFFAOYSA-N n-[4-(1,8-diazaspiro[4.5]decane-8-carbonyl)phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1C2=CC=NC=C2CN1C(=O)NC(C=C1)=CC=C1C(=O)N(CC1)CCC21CCCN2 FFLNRICJYUDWLZ-UHFFFAOYSA-N 0.000 description 5
LUEYPJOXSVWQLW-UHFFFAOYSA-N n-[4-(1,8-diazaspiro[5.5]undecane-8-carbonyl)phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1C2=CC=NC=C2CN1C(=O)NC(C=C1)=CC=C1C(=O)N(C1)CCCC21CCCCN2 LUEYPJOXSVWQLW-UHFFFAOYSA-N 0.000 description 5
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GDCAGOKLQHQGMJ-UHFFFAOYSA-N n-[4-(1-cyanoethylcarbamoyl)phenyl]-5,7-dihydropyrrolo[3,4-b]pyridine-6-carboxamide Chemical compound C1=CC(C(=O)NC(C)C#N)=CC=C1NC(=O)N1CC2=NC=CC=C2C1 GDCAGOKLQHQGMJ-UHFFFAOYSA-N 0.000 description 5
HQCPMHWICKAVEY-UHFFFAOYSA-N n-[4-(1-cyanoethylcarbamoyl)phenyl]-5-fluoro-1,3-dihydroisoindole-2-carboxamide Chemical compound C1=CC(C(=O)NC(C)C#N)=CC=C1NC(=O)N1CC2=CC(F)=CC=C2C1 HQCPMHWICKAVEY-UHFFFAOYSA-N 0.000 description 5
HNUPZLDGHHUUIK-UHFFFAOYSA-N n-[4-(1-methoxybutan-2-ylcarbamoyl)phenyl]-5,7-dihydropyrrolo[3,4-b]pyridine-6-carboxamide Chemical compound C1=CC(C(=O)NC(COC)CC)=CC=C1NC(=O)N1CC2=NC=CC=C2C1 HNUPZLDGHHUUIK-UHFFFAOYSA-N 0.000 description 5
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VUWDCMUNOHVZHZ-UHFFFAOYSA-N n-[4-(1-oxa-4,8-diazaspiro[5.5]undecane-4-carbonyl)phenyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1C2=CC=NC=C2CN1C(=O)NC(C=C1)=CC=C1C(=O)N(C1)CCOC21CCCNC2 VUWDCMUNOHVZHZ-UHFFFAOYSA-N 0.000 description 5
TUKKVYPKKLHNCF-UHFFFAOYSA-N n-[4-(1-oxa-8-azaspiro[4.5]decan-3-ylcarbamoyl)phenyl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(C=C1)=CC=C1C(=O)NC(C1)COC21CCNCC2 TUKKVYPKKLHNCF-UHFFFAOYSA-N 0.000 description 5
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SKLZKSCEYWXITG-UHFFFAOYSA-N n-[4-(2,2-dimethylpropylcarbamoyl)phenyl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1=CC(C(=O)NCC(C)(C)C)=CC=C1NC(=O)N1CC2=CC=CC=C2C1 SKLZKSCEYWXITG-UHFFFAOYSA-N 0.000 description 5
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GESIBHORGNKVPG-UHFFFAOYSA-N n-[4-(2-ethoxypropylcarbamoyl)phenyl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1=CC(C(=O)NCC(C)OCC)=CC=C1NC(=O)N1CC2=CC=CC=C2C1 GESIBHORGNKVPG-UHFFFAOYSA-N 0.000 description 5
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VZDKIYYJBVBNJD-UHFFFAOYSA-N n-[4-(2-methoxybutylcarbamoyl)phenyl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1=CC(C(=O)NCC(CC)OC)=CC=C1NC(=O)N1CC2=CC=CC=C2C1 VZDKIYYJBVBNJD-UHFFFAOYSA-N 0.000 description 5
RDCYADGBLXWGNC-UHFFFAOYSA-N n-[4-(2-methoxybutylcarbamoyl)phenyl]-5,7-dihydropyrrolo[3,4-b]pyridine-6-carboxamide Chemical compound C1=CC(C(=O)NCC(CC)OC)=CC=C1NC(=O)N1CC2=NC=CC=C2C1 RDCYADGBLXWGNC-UHFFFAOYSA-N 0.000 description 5
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VXBKAZYFZUQFDA-UHFFFAOYSA-N n-[4-(2-methylbutan-2-ylcarbamoyl)phenyl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1=CC(C(=O)NC(C)(C)CC)=CC=C1NC(=O)N1CC2=CC=CC=C2C1 VXBKAZYFZUQFDA-UHFFFAOYSA-N 0.000 description 5
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DDWGZODGKBAHTO-UHFFFAOYSA-N n-[4-(3-imidazol-1-ylpropylcarbamoyl)phenyl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(C=C1)=CC=C1C(=O)NCCCN1C=CN=C1 DDWGZODGKBAHTO-UHFFFAOYSA-N 0.000 description 5
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LXHVQOVXCAZNPJ-HXUWFJFHSA-N n-[4-[[(2r)-1-hydroxy-4-methylpentan-2-yl]carbamoyl]phenyl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1=CC(C(=O)N[C@@H](CO)CC(C)C)=CC=C1NC(=O)N1CC2=CC=CC=C2C1 LXHVQOVXCAZNPJ-HXUWFJFHSA-N 0.000 description 1
LXHVQOVXCAZNPJ-FQEVSTJZSA-N n-[4-[[(2s)-1-hydroxy-4-methylpentan-2-yl]carbamoyl]phenyl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1=CC(C(=O)N[C@H](CO)CC(C)C)=CC=C1NC(=O)N1CC2=CC=CC=C2C1 LXHVQOVXCAZNPJ-FQEVSTJZSA-N 0.000 description 1
BOOJWQFVWCUNAH-UHFFFAOYSA-N n-[5-[1-(oxolane-2-carbonyl)-3,6-dihydro-2h-pyridin-4-yl]pyridin-2-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(N=C1)=CC=C1C(CC1)=CCN1C(=O)C1CCCO1 BOOJWQFVWCUNAH-UHFFFAOYSA-N 0.000 description 1
AOEIVOCLZPZEHN-UHFFFAOYSA-N n-[6-(oxan-4-ylmethylcarbamoyl)pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(N=N1)=CC=C1C(=O)NCC1CCOCC1 AOEIVOCLZPZEHN-UHFFFAOYSA-N 0.000 description 1
OQGPEBXEXSSERJ-UHFFFAOYSA-N n-[6-[1-(2-hydroxy-2-methylpropanoyl)-3,6-dihydro-2h-pyridin-4-yl]pyridin-3-yl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1N(C(=O)C(C)(O)C)CCC(C=2N=CC(NC(=O)N3CC4=CN=CC=C4C3)=CC=2)=C1 OQGPEBXEXSSERJ-UHFFFAOYSA-N 0.000 description 1
UOHTTZGCBWTDAM-UHFFFAOYSA-N n-[6-[1-(3-methylbutanoyl)piperidin-4-yl]oxypyridin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1CN(C(=O)CC(C)C)CCC1OC(N=C1)=CC=C1NC(=O)N1CC2=CC=CC=C2C1 UOHTTZGCBWTDAM-UHFFFAOYSA-N 0.000 description 1
HKSQZEGSMBFHGC-UHFFFAOYSA-N pyrimidine-4-carboxamide Chemical compound NC(=O)C1=CC=NC=N1 HKSQZEGSMBFHGC-UHFFFAOYSA-N 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1

JP2013538943A 2010-11-15 2011-11-11 Ｎａｍｐｔおよびｒｏｃｋ阻害薬 Active JP6117104B2 (ja)