JP2011509280A5 - - Google Patents
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- Publication number
- JP2011509280A5 JP2011509280A5 JP2010541800A JP2010541800A JP2011509280A5 JP 2011509280 A5 JP2011509280 A5 JP 2011509280A5 JP 2010541800 A JP2010541800 A JP 2010541800A JP 2010541800 A JP2010541800 A JP 2010541800A JP 2011509280 A5 JP2011509280 A5 JP 2011509280A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- benzamide
- phenylamino
- phenyl
- diethylamino
- Prior art date
- 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.)
- Granted
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 43
- 150000001875 compounds Chemical class 0.000 claims 31
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 16
- 201000010099 disease Diseases 0.000 claims 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 14
- 125000000217 alkyl group Chemical group 0.000 claims 11
- 239000003795 chemical substances by application Substances 0.000 claims 11
- 229910052757 nitrogen Inorganic materials 0.000 claims 11
- 125000005843 halogen group Chemical group 0.000 claims 9
- 125000004432 carbon atom Chemical group C* 0.000 claims 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims 5
- -1 4-diethylaminomethyl- [1,2,3] triazol-1-yl Chemical group 0.000 claims 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 108091032973 (ribonucleotides)n+m Proteins 0.000 claims 2
- USZCQHMQZZEHAM-UHFFFAOYSA-N 2-[2-(diethylamino)ethylamino]-n-pyridin-4-ylbenzamide Chemical compound CCN(CC)CCNC1=CC=CC=C1C(=O)NC1=CC=NC=C1 USZCQHMQZZEHAM-UHFFFAOYSA-N 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 206010013801 Duchenne Muscular Dystrophy Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 2
- 206010060862 Prostate cancer Diseases 0.000 claims 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 2
- 208000002495 Uterine Neoplasms Diseases 0.000 claims 2
- 230000032683 aging Effects 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 208000029742 colonic neoplasm Diseases 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000003834 intracellular effect Effects 0.000 claims 2
- 201000007270 liver cancer Diseases 0.000 claims 2
- 208000014018 liver neoplasm Diseases 0.000 claims 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 2
- 208000037819 metastatic cancer Diseases 0.000 claims 2
- 208000011575 metastatic malignant neoplasm Diseases 0.000 claims 2
- 230000035772 mutation Effects 0.000 claims 2
- NOCSCLVSJBOTTB-UHFFFAOYSA-N n-[3-(diethylamino)propyl]-3-[3-[(3-methoxybenzoyl)amino]anilino]benzamide Chemical compound CCN(CC)CCCNC(=O)C1=CC=CC(NC=2C=C(NC(=O)C=3C=C(OC)C=CC=3)C=CC=2)=C1 NOCSCLVSJBOTTB-UHFFFAOYSA-N 0.000 claims 2
- 230000007171 neuropathology Effects 0.000 claims 2
- 229960003966 nicotinamide Drugs 0.000 claims 2
- 239000011570 nicotinamide Substances 0.000 claims 2
- 201000002528 pancreatic cancer Diseases 0.000 claims 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- 206010046766 uterine cancer Diseases 0.000 claims 2
- NMQCPIGNFXJPNZ-UHFFFAOYSA-N 2-(3-imidazol-1-ylpropylamino)-n-(3-methoxyphenyl)pyridine-3-carboxamide Chemical compound COC1=CC=CC(NC(=O)C=2C(=NC=CC=2)NCCCN2C=NC=C2)=C1 NMQCPIGNFXJPNZ-UHFFFAOYSA-N 0.000 claims 1
- GNJQUDMOXXKPIX-UHFFFAOYSA-N 2-(3-imidazol-1-ylpropylamino)-n-(4-methoxyphenyl)benzamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=CC=CC=C1NCCCN1C=NC=C1 GNJQUDMOXXKPIX-UHFFFAOYSA-N 0.000 claims 1
- SJEYVWNLCVTNLP-UHFFFAOYSA-N 2-(3-imidazol-1-ylpropylamino)-n-[4-(trifluoromethoxy)phenyl]benzamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)C1=CC=CC=C1NCCCN1C=NC=C1 SJEYVWNLCVTNLP-UHFFFAOYSA-N 0.000 claims 1
- OQDNVIOBMWGPRV-UHFFFAOYSA-N 2-(3-imidazol-1-ylpropylamino)-n-[4-(trifluoromethoxy)phenyl]pyridine-3-carboxamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)C1=CC=CN=C1NCCCN1C=NC=C1 OQDNVIOBMWGPRV-UHFFFAOYSA-N 0.000 claims 1
- LTPCCUQYOBVIRZ-UHFFFAOYSA-N 2-(3-imidazol-1-ylpropylamino)-n-pyridin-4-ylbenzamide Chemical compound C=1C=CC=C(NCCCN2C=NC=C2)C=1C(=O)NC1=CC=NC=C1 LTPCCUQYOBVIRZ-UHFFFAOYSA-N 0.000 claims 1
- KMWYKVYOUACXOJ-UHFFFAOYSA-N 2-(3-imidazol-1-ylpropylamino)-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C=1C=CN=C(NCCCN2C=NC=C2)C=1C(=O)NC1=CC=NC=C1 KMWYKVYOUACXOJ-UHFFFAOYSA-N 0.000 claims 1
- WYLLXNFJCIEZGL-UHFFFAOYSA-N 2-(4-hydroxybutylamino)-n-(3-methoxyphenyl)benzamide Chemical compound COC1=CC=CC(NC(=O)C=2C(=CC=CC=2)NCCCCO)=C1 WYLLXNFJCIEZGL-UHFFFAOYSA-N 0.000 claims 1
- KGFLIMXLAWGSBC-UHFFFAOYSA-N 2-(4-hydroxybutylamino)-n-(3-methoxyphenyl)pyridine-3-carboxamide Chemical compound COC1=CC=CC(NC(=O)C=2C(=NC=CC=2)NCCCCO)=C1 KGFLIMXLAWGSBC-UHFFFAOYSA-N 0.000 claims 1
- XFKRBVLYOLMZNC-UHFFFAOYSA-N 2-(4-hydroxybutylamino)-n-(4-methoxyphenyl)benzamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=CC=CC=C1NCCCCO XFKRBVLYOLMZNC-UHFFFAOYSA-N 0.000 claims 1
- WZBFHKXPCGPMBM-UHFFFAOYSA-N 2-(4-hydroxybutylamino)-n-[4-(trifluoromethoxy)phenyl]benzamide Chemical compound OCCCCNC1=CC=CC=C1C(=O)NC1=CC=C(OC(F)(F)F)C=C1 WZBFHKXPCGPMBM-UHFFFAOYSA-N 0.000 claims 1
- DYPFRGBASAWOEN-UHFFFAOYSA-N 2-(4-hydroxybutylamino)-n-[4-(trifluoromethoxy)phenyl]pyridine-3-carboxamide Chemical compound OCCCCNC1=NC=CC=C1C(=O)NC1=CC=C(OC(F)(F)F)C=C1 DYPFRGBASAWOEN-UHFFFAOYSA-N 0.000 claims 1
- JFFIHEJJKXROJR-UHFFFAOYSA-N 2-(5-hydroxypentylamino)-n-(3-methoxyphenyl)pyridine-3-carboxamide Chemical compound COC1=CC=CC(NC(=O)C=2C(=NC=CC=2)NCCCCCO)=C1 JFFIHEJJKXROJR-UHFFFAOYSA-N 0.000 claims 1
- REGHLIZBPJTLDX-UHFFFAOYSA-N 2-(6-aminohexylamino)-n-(3-methoxyphenyl)pyridine-3-carboxamide Chemical compound COC1=CC=CC(NC(=O)C=2C(=NC=CC=2)NCCCCCCN)=C1 REGHLIZBPJTLDX-UHFFFAOYSA-N 0.000 claims 1
- DBRLDAZIPHQPNA-UHFFFAOYSA-N 2-(6-aminohexylamino)-n-[4-(trifluoromethoxy)phenyl]benzamide Chemical compound NCCCCCCNC1=CC=CC=C1C(=O)NC1=CC=C(OC(F)(F)F)C=C1 DBRLDAZIPHQPNA-UHFFFAOYSA-N 0.000 claims 1
- QGUGGCODWYLPCV-UHFFFAOYSA-N 2-[2-(diethylamino)ethylamino]-n-(3-methoxyphenyl)benzamide Chemical compound CCN(CC)CCNC1=CC=CC=C1C(=O)NC1=CC=CC(OC)=C1 QGUGGCODWYLPCV-UHFFFAOYSA-N 0.000 claims 1
- YMTWNLGBVZGFCB-UHFFFAOYSA-N 2-[2-(diethylamino)ethylamino]-n-(3-methoxyphenyl)pyridine-3-carboxamide Chemical compound CCN(CC)CCNC1=NC=CC=C1C(=O)NC1=CC=CC(OC)=C1 YMTWNLGBVZGFCB-UHFFFAOYSA-N 0.000 claims 1
- ZHRFWLXMFRPTAA-UHFFFAOYSA-N 2-[2-(diethylamino)ethylamino]-n-[4-(trifluoromethoxy)phenyl]benzamide Chemical compound CCN(CC)CCNC1=CC=CC=C1C(=O)NC1=CC=C(OC(F)(F)F)C=C1 ZHRFWLXMFRPTAA-UHFFFAOYSA-N 0.000 claims 1
- HXIOZFFLVOUFPT-UHFFFAOYSA-N 2-[2-(diethylamino)ethylamino]-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound CCN(CC)CCNC1=NC=CC=C1C(=O)NC1=CC=NC=C1 HXIOZFFLVOUFPT-UHFFFAOYSA-N 0.000 claims 1
- FNOJGPGVTOCRRD-UHFFFAOYSA-N 2-[2-(dimethylamino)ethylamino]-n-(3-methoxyphenyl)benzamide Chemical compound COC1=CC=CC(NC(=O)C=2C(=CC=CC=2)NCCN(C)C)=C1 FNOJGPGVTOCRRD-UHFFFAOYSA-N 0.000 claims 1
- TXQLNHYTRZUJGM-UHFFFAOYSA-N 2-[2-(dimethylamino)ethylamino]-n-(3-methoxyphenyl)pyridine-3-carboxamide Chemical compound COC1=CC=CC(NC(=O)C=2C(=NC=CC=2)NCCN(C)C)=C1 TXQLNHYTRZUJGM-UHFFFAOYSA-N 0.000 claims 1
- JIBVWNRZPCYONC-UHFFFAOYSA-N 2-[2-(dimethylamino)ethylamino]-n-(4-methoxyphenyl)benzamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=CC=CC=C1NCCN(C)C JIBVWNRZPCYONC-UHFFFAOYSA-N 0.000 claims 1
- RHODVADTHOPEOS-UHFFFAOYSA-N 2-[2-(dimethylamino)ethylamino]-n-(4-methoxyphenyl)pyridine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=CC=CN=C1NCCN(C)C RHODVADTHOPEOS-UHFFFAOYSA-N 0.000 claims 1
- QNRFETAIXFVWEM-UHFFFAOYSA-N 2-[2-(dimethylamino)ethylamino]-n-[4-(trifluoromethoxy)phenyl]pyridine-3-carboxamide Chemical compound CN(C)CCNC1=NC=CC=C1C(=O)NC1=CC=C(OC(F)(F)F)C=C1 QNRFETAIXFVWEM-UHFFFAOYSA-N 0.000 claims 1
- YEBCJENRTNXSSZ-UHFFFAOYSA-N 2-[3-(diethylamino)propylamino]-n-(3-methoxyphenyl)pyridine-3-carboxamide Chemical compound CCN(CC)CCCNC1=NC=CC=C1C(=O)NC1=CC=CC(OC)=C1 YEBCJENRTNXSSZ-UHFFFAOYSA-N 0.000 claims 1
- UOJNSUFAUJMTHW-UHFFFAOYSA-N 2-[3-(diethylamino)propylamino]-n-[4-(trifluoromethoxy)phenyl]benzamide Chemical compound CCN(CC)CCCNC1=CC=CC=C1C(=O)NC1=CC=C(OC(F)(F)F)C=C1 UOJNSUFAUJMTHW-UHFFFAOYSA-N 0.000 claims 1
- BRZATTRACHIJHI-UHFFFAOYSA-N 2-[3-(diethylamino)propylamino]-n-[4-(trifluoromethoxy)phenyl]pyridine-3-carboxamide Chemical compound CCN(CC)CCCNC1=NC=CC=C1C(=O)NC1=CC=C(OC(F)(F)F)C=C1 BRZATTRACHIJHI-UHFFFAOYSA-N 0.000 claims 1
- UKJMANVTJCAMAT-UHFFFAOYSA-N 2-[3-(diethylamino)propylamino]-n-pyridin-4-ylbenzamide Chemical compound CCN(CC)CCCNC1=CC=CC=C1C(=O)NC1=CC=NC=C1 UKJMANVTJCAMAT-UHFFFAOYSA-N 0.000 claims 1
- ZREMPGYRQSWPTH-UHFFFAOYSA-N 2-[3-(diethylamino)propylamino]-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound CCN(CC)CCCNC1=NC=CC=C1C(=O)NC1=CC=NC=C1 ZREMPGYRQSWPTH-UHFFFAOYSA-N 0.000 claims 1
- LANZFGWNGPWWNO-UHFFFAOYSA-N 2-[3-(dimethylamino)propylamino]-n-(3-methoxyphenyl)pyridine-3-carboxamide Chemical compound COC1=CC=CC(NC(=O)C=2C(=NC=CC=2)NCCCN(C)C)=C1 LANZFGWNGPWWNO-UHFFFAOYSA-N 0.000 claims 1
- VTXKUAGOFKFCNL-UHFFFAOYSA-N 2-[3-(dimethylamino)propylamino]-n-(4-methoxyphenyl)benzamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=CC=CC=C1NCCCN(C)C VTXKUAGOFKFCNL-UHFFFAOYSA-N 0.000 claims 1
- OUZLNSLVSSRMNU-UHFFFAOYSA-N 2-[3-(dimethylamino)propylamino]-n-[4-(trifluoromethoxy)phenyl]benzamide Chemical compound CN(C)CCCNC1=CC=CC=C1C(=O)NC1=CC=C(OC(F)(F)F)C=C1 OUZLNSLVSSRMNU-UHFFFAOYSA-N 0.000 claims 1
- RRFODRCTTKIXJQ-UHFFFAOYSA-N 2-[3-(dimethylamino)propylamino]-n-[4-(trifluoromethoxy)phenyl]pyridine-3-carboxamide Chemical compound CN(C)CCCNC1=NC=CC=C1C(=O)NC1=CC=C(OC(F)(F)F)C=C1 RRFODRCTTKIXJQ-UHFFFAOYSA-N 0.000 claims 1
- IAFAOPWJFZTZQK-UHFFFAOYSA-N 2-[3-(dimethylamino)propylamino]-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound CN(C)CCCNC1=NC=CC=C1C(=O)NC1=CC=NC=C1 IAFAOPWJFZTZQK-UHFFFAOYSA-N 0.000 claims 1
- WJGLFEUAYGIPRN-UHFFFAOYSA-N 2-[4-(dimethylamino)anilino]-n-(3-imidazol-1-ylpropyl)benzamide Chemical compound C1=CC(N(C)C)=CC=C1NC1=CC=CC=C1C(=O)NCCCN1C=NC=C1 WJGLFEUAYGIPRN-UHFFFAOYSA-N 0.000 claims 1
- RWRPQAAVWLLUAU-UHFFFAOYSA-N 2-[5-(diethylamino)pentan-2-ylamino]-n-(3-methoxyphenyl)benzamide Chemical compound CCN(CC)CCCC(C)NC1=CC=CC=C1C(=O)NC1=CC=CC(OC)=C1 RWRPQAAVWLLUAU-UHFFFAOYSA-N 0.000 claims 1
- GYNKBIZJQNDMGT-UHFFFAOYSA-N 2-[5-(diethylamino)pentan-2-ylamino]-n-[4-(trifluoromethoxy)phenyl]benzamide Chemical compound CCN(CC)CCCC(C)NC1=CC=CC=C1C(=O)NC1=CC=C(OC(F)(F)F)C=C1 GYNKBIZJQNDMGT-UHFFFAOYSA-N 0.000 claims 1
- KJBDNSBCXSIQMA-UHFFFAOYSA-N 2-bromo-N-(3-methoxyphenyl)benzamide Chemical compound COC1=CC=CC(NC(=O)C=2C(=CC=CC=2)Br)=C1 KJBDNSBCXSIQMA-UHFFFAOYSA-N 0.000 claims 1
- AKEQDKIMDBCGSA-UHFFFAOYSA-N 2-bromo-n-[4-(dimethylamino)phenyl]benzamide Chemical compound C1=CC(N(C)C)=CC=C1NC(=O)C1=CC=CC=C1Br AKEQDKIMDBCGSA-UHFFFAOYSA-N 0.000 claims 1
- PAFQKZAUYMWWHG-UHFFFAOYSA-N 2-bromo-n-[4-(trifluoromethoxy)phenyl]benzamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)C1=CC=CC=C1Br PAFQKZAUYMWWHG-UHFFFAOYSA-N 0.000 claims 1
- REDJPCIUXHKTFR-UHFFFAOYSA-N 2-bromo-n-pyridin-4-ylbenzamide Chemical compound BrC1=CC=CC=C1C(=O)NC1=CC=NC=C1 REDJPCIUXHKTFR-UHFFFAOYSA-N 0.000 claims 1
- CVCAWLQDFRMHFV-UHFFFAOYSA-N 2-chloro-n-(3-methoxyphenyl)pyridine-3-carboxamide Chemical compound COC1=CC=CC(NC(=O)C=2C(=NC=CC=2)Cl)=C1 CVCAWLQDFRMHFV-UHFFFAOYSA-N 0.000 claims 1
- WGNNXHGHEGCGDV-UHFFFAOYSA-N 2-chloro-n-[4-(dimethylamino)phenyl]pyridine-3-carboxamide Chemical compound C1=CC(N(C)C)=CC=C1NC(=O)C1=CC=CN=C1Cl WGNNXHGHEGCGDV-UHFFFAOYSA-N 0.000 claims 1
- SHMTXVLNVCIHGF-UHFFFAOYSA-N 2-chloro-n-[4-(trifluoromethoxy)phenyl]pyridine-3-carboxamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)C1=CC=CN=C1Cl SHMTXVLNVCIHGF-UHFFFAOYSA-N 0.000 claims 1
- YMMKGFFYVNSGPC-UHFFFAOYSA-N 2-chloro-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=NC=C1 YMMKGFFYVNSGPC-UHFFFAOYSA-N 0.000 claims 1
- GNISBZMJFHJXNU-MDZDMXLPSA-N 3-[1-[3-[3-[(e)-2-pyridin-4-ylethenyl]anilino]phenyl]triazol-4-yl]propan-1-ol Chemical compound N1=NC(CCCO)=CN1C1=CC=CC(NC=2C=C(\C=C\C=3C=CN=CC=3)C=CC=2)=C1 GNISBZMJFHJXNU-MDZDMXLPSA-N 0.000 claims 1
- DIIZSPAUXGEYBF-UHFFFAOYSA-N 3-[1-[3-[4-(dimethylamino)anilino]phenyl]triazol-4-yl]propan-1-ol Chemical compound C1=CC(N(C)C)=CC=C1NC1=CC=CC(N2N=NC(CCCO)=C2)=C1 DIIZSPAUXGEYBF-UHFFFAOYSA-N 0.000 claims 1
- VHXLOICSLKMMJZ-UHFFFAOYSA-N 3-[1-[3-[4-(trifluoromethoxy)anilino]phenyl]triazol-4-yl]propan-1-ol Chemical compound N1=NC(CCCO)=CN1C1=CC=CC(NC=2C=CC(OC(F)(F)F)=CC=2)=C1 VHXLOICSLKMMJZ-UHFFFAOYSA-N 0.000 claims 1
- QDVCMXVFTFQFBN-VOTSOKGWSA-N 3-[1-[3-[4-[(e)-2-pyridin-4-ylethenyl]anilino]phenyl]triazol-4-yl]propan-1-ol Chemical compound N1=NC(CCCO)=CN1C1=CC=CC(NC=2C=CC(\C=C\C=3C=CN=CC=3)=CC=2)=C1 QDVCMXVFTFQFBN-VOTSOKGWSA-N 0.000 claims 1
- RYZMHJCWSQMDPT-UHFFFAOYSA-N 3-[1-[4-(4-methoxyanilino)phenyl]triazol-4-yl]propan-1-ol Chemical compound C1=CC(OC)=CC=C1NC1=CC=C(N2N=NC(CCCO)=C2)C=C1 RYZMHJCWSQMDPT-UHFFFAOYSA-N 0.000 claims 1
- VOQKSODWFALURE-ONEGZZNKSA-N 3-[1-[4-[4-[(e)-2-pyridin-4-ylethenyl]anilino]phenyl]triazol-4-yl]propan-1-ol Chemical compound N1=NC(CCCO)=CN1C(C=C1)=CC=C1NC(C=C1)=CC=C1\C=C\C1=CC=NC=C1 VOQKSODWFALURE-ONEGZZNKSA-N 0.000 claims 1
- QSAZGUXUFYSUFB-UHFFFAOYSA-N 3-[4-[(3-methoxybenzoyl)amino]anilino]-n-(3-methylbutyl)benzamide Chemical compound COC1=CC=CC(C(=O)NC=2C=CC(NC=3C=C(C=CC=3)C(=O)NCCC(C)C)=CC=2)=C1 QSAZGUXUFYSUFB-UHFFFAOYSA-N 0.000 claims 1
- UEUHRHHHIWCCFK-UHFFFAOYSA-N 3-[4-[diethylamino(methyl)amino]triazol-1-yl]-n-(4-methoxyphenyl)aniline Chemical compound N1=NC(N(C)N(CC)CC)=CN1C1=CC=CC(NC=2C=CC(OC)=CC=2)=C1 UEUHRHHHIWCCFK-UHFFFAOYSA-N 0.000 claims 1
- ZEJFPRRKAYPBRR-UHFFFAOYSA-N 3-methoxy-n-[3-[4-(3-methylbutylcarbamoyl)anilino]phenyl]benzamide Chemical compound COC1=CC=CC(C(=O)NC=2C=C(NC=3C=CC(=CC=3)C(=O)NCCC(C)C)C=CC=2)=C1 ZEJFPRRKAYPBRR-UHFFFAOYSA-N 0.000 claims 1
- IKKACGVZFOLYAM-ZRDIBKRKSA-N 3-methyl-n-(3-methylbutyl)-4-[3-[(e)-2-pyridin-2-ylethenyl]anilino]benzamide Chemical compound CC1=CC(C(=O)NCCC(C)C)=CC=C1NC1=CC=CC(\C=C\C=2N=CC=CC=2)=C1 IKKACGVZFOLYAM-ZRDIBKRKSA-N 0.000 claims 1
- RRNFHBAWFDBTBS-UHFFFAOYSA-N 3-methyl-n-(3-methylbutyl)-4-[4-(trifluoromethoxy)anilino]benzamide Chemical compound CC1=CC(C(=O)NCCC(C)C)=CC=C1NC1=CC=C(OC(F)(F)F)C=C1 RRNFHBAWFDBTBS-UHFFFAOYSA-N 0.000 claims 1
- VXOLWJRLEHQZSP-SNAWJCMRSA-N 3-methyl-n-(3-methylbutyl)-4-[4-[(e)-2-pyridin-4-ylethenyl]anilino]benzamide Chemical compound CC1=CC(C(=O)NCCC(C)C)=CC=C1NC(C=C1)=CC=C1\C=C\C1=CC=NC=C1 VXOLWJRLEHQZSP-SNAWJCMRSA-N 0.000 claims 1
- MJNPBAIZWHGFQN-UHFFFAOYSA-N 4-(4-methoxyanilino)-3-methyl-n-(3-methylbutyl)benzamide Chemical compound C1=CC(OC)=CC=C1NC1=CC=C(C(=O)NCCC(C)C)C=C1C MJNPBAIZWHGFQN-UHFFFAOYSA-N 0.000 claims 1
- ARKWELBWICHKGK-UHFFFAOYSA-N 4-(4-methoxyanilino)-n-(3-methylbutyl)benzamide Chemical compound C1=CC(OC)=CC=C1NC1=CC=C(C(=O)NCCC(C)C)C=C1 ARKWELBWICHKGK-UHFFFAOYSA-N 0.000 claims 1
- QUEACOJWZZCAIP-UHFFFAOYSA-N 4-(5-chloro-1h-imidazol-2-yl)-n-(4-methoxyphenyl)-2-methylaniline Chemical compound C1=CC(OC)=CC=C1NC1=CC=C(C=2NC(Cl)=CN=2)C=C1C QUEACOJWZZCAIP-UHFFFAOYSA-N 0.000 claims 1
- ZCRNEOWAENGMKO-UHFFFAOYSA-N 4-[3-[(4-methoxybenzoyl)amino]anilino]-3-methyl-n-(3-methylbutyl)benzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=CC=CC(NC=2C(=CC(=CC=2)C(=O)NCCC(C)C)C)=C1 ZCRNEOWAENGMKO-UHFFFAOYSA-N 0.000 claims 1
- LWHFMYOAENSUMW-UHFFFAOYSA-N 4-[4-(dimethylamino)anilino]-n-[2-(dimethylamino)ethyl]benzamide Chemical compound C1=CC(C(=O)NCCN(C)C)=CC=C1NC1=CC=C(N(C)C)C=C1 LWHFMYOAENSUMW-UHFFFAOYSA-N 0.000 claims 1
- ODJWKTMPQRXFOP-UHFFFAOYSA-N 4-[4-[(3-methoxybenzoyl)amino]anilino]-3-methyl-n-(3-methylbutyl)benzamide Chemical compound COC1=CC=CC(C(=O)NC=2C=CC(NC=3C(=CC(=CC=3)C(=O)NCCC(C)C)C)=CC=2)=C1 ODJWKTMPQRXFOP-UHFFFAOYSA-N 0.000 claims 1
- OLQDONPZUXJKHK-UHFFFAOYSA-N 4-[4-[diethylamino(methyl)amino]triazol-1-yl]-n-(4-methoxyphenyl)aniline Chemical compound N1=NC(N(C)N(CC)CC)=CN1C(C=C1)=CC=C1NC1=CC=C(OC)C=C1 OLQDONPZUXJKHK-UHFFFAOYSA-N 0.000 claims 1
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| US9133212B1 (en) | 2005-06-15 | 2015-09-15 | Vanderbilt University | Inhibitors of hemeprotein-catalyzed lipid peroxidation |
| FR2926297B1 (fr) | 2008-01-10 | 2013-03-08 | Centre Nat Rech Scient | Molecules chimiques inhibitrices du mecanisme d'epissage pour traiter des maladies resultant d'anomalies d'epissage. |
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| EP2266972A1 (en) * | 2009-06-12 | 2010-12-29 | Splicos | New chemical molecules that inhibit the splicing mechanism for treating diseases resulting from splicing anomalies |
| CN102625804B (zh) | 2009-06-12 | 2015-04-08 | Abivax公司 | 用于治疗aids的化合物 |
| US10253020B2 (en) | 2009-06-12 | 2019-04-09 | Abivax | Compounds for preventing, inhibiting, or treating cancer, AIDS and/or premature aging |
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| WO2012001941A1 (ja) * | 2010-06-28 | 2012-01-05 | Hagiwara Masatoshi | 遺伝性疾患の予防・改善剤 |
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| US9388185B2 (en) | 2012-08-10 | 2016-07-12 | Incyte Holdings Corporation | Substituted pyrrolo[2,3-b]pyrazines as FGFR inhibitors |
| EP2712862A1 (en) * | 2012-09-28 | 2014-04-02 | Splicos | New anti-invasive compounds |
| US9266892B2 (en) | 2012-12-19 | 2016-02-23 | Incyte Holdings Corporation | Fused pyrazoles as FGFR inhibitors |
| EP2757161A1 (en) | 2013-01-17 | 2014-07-23 | Splicos | miRNA-124 as a biomarker of viral infection |
| ITMI20130444A1 (it) * | 2013-03-22 | 2014-09-23 | S B M Science Of Biology In Medici Ne Srl | Composto di inclusione comprendente adjudin [1-(2,4-diclorobenzil) - 1h-indazolo-3-carboidrazide] e ciclodestrina, sua preparazione e utilizzo. |
| PH12015502383B1 (en) | 2013-04-19 | 2023-02-03 | Incyte Holdings Corp | Bicyclic heterocycles as fgfr inhibitors |
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| EA032355B1 (ru) * | 2013-12-24 | 2019-05-31 | Онкотартис, Инк. | Бензамидные и никотинамидные соединения и способы их применения |
| EP2974729A1 (en) | 2014-07-17 | 2016-01-20 | Abivax | Quinoline derivatives for use in the treatment of inflammatory diseases |
| US20170204089A1 (en) | 2014-08-04 | 2017-07-20 | Drexel University | Novel compounds and methods of treating or ameliorating an il-1r-mediated disease or disorder using same |
| US20160058889A1 (en) * | 2014-08-11 | 2016-03-03 | The Board Of Regents Of The University Of Texas System | Prevention of muscular dystrophy by crispr/cas9-mediated gene editing |
| US10851105B2 (en) | 2014-10-22 | 2020-12-01 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| US9580423B2 (en) | 2015-02-20 | 2017-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| CA2976790C (en) | 2015-02-20 | 2024-02-27 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| MA41551A (fr) | 2015-02-20 | 2017-12-26 | Incyte Corp | Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4 |
| CN110892069B (zh) | 2017-03-30 | 2024-02-09 | 国立大学法人京都大学 | 基于基因组编辑的外显子跳跃诱导方法 |
| AR111960A1 (es) | 2017-05-26 | 2019-09-04 | Incyte Corp | Formas cristalinas de un inhibidor de fgfr y procesos para su preparación |
| JP2021521200A (ja) * | 2018-04-10 | 2021-08-26 | スカイホーク・セラピューティクス・インコーポレーテッド | 癌の処置のための化合物 |
| KR102956194B1 (ko) | 2018-05-04 | 2026-04-23 | 인사이트 코포레이션 | Fgfr 억제제의 염 |
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