JP2010540452A5 - - Google Patents
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- JP2010540452A5 JP2010540452A5 JP2010526003A JP2010526003A JP2010540452A5 JP 2010540452 A5 JP2010540452 A5 JP 2010540452A5 JP 2010526003 A JP2010526003 A JP 2010526003A JP 2010526003 A JP2010526003 A JP 2010526003A JP 2010540452 A5 JP2010540452 A5 JP 2010540452A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- oxo
- amino
- carboxamide
- phenyl
- 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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- -1 N- methylpiperazinyl Chemical group 0.000 claims 25
- 150000001875 compounds Chemical class 0.000 claims 22
- 229910052757 nitrogen Inorganic materials 0.000 claims 21
- VFDMDQYKXJRBOV-UHFFFAOYSA-N 7,8-dihydro-6h-cyclohepta[b]thiophene-2-carboxamide Chemical compound C1=CCCCC2=C1C=C(C(=O)N)S2 VFDMDQYKXJRBOV-UHFFFAOYSA-N 0.000 claims 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 6
- 230000000694 effects Effects 0.000 claims 5
- 230000005764 inhibitory process Effects 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- CDOOFZZILLRUQH-UHFFFAOYSA-N n-[3-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C=CC=2)C)=CN(C)C1=O CDOOFZZILLRUQH-UHFFFAOYSA-N 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- HXDMKCOWCGVXRQ-UHFFFAOYSA-N 4-tert-butyl-n-[3-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-2-methylbenzamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3C(=CC(=CC=3)C(C)(C)C)C)C=CC=2)C)=CN(C)C1=O HXDMKCOWCGVXRQ-UHFFFAOYSA-N 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 208000004736 B-Cell Leukemia Diseases 0.000 claims 1
- 208000003950 B-cell lymphoma Diseases 0.000 claims 1
- 208000020084 Bone disease Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 230000000172 allergic effect Effects 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 208000037979 autoimmune inflammatory disease Diseases 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- ZCVYIHRVDJPYRU-UHFFFAOYSA-N n-[2,6-dichloro-3-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]phenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C(Cl)=CC=2)Cl)=CN(C)C1=O ZCVYIHRVDJPYRU-UHFFFAOYSA-N 0.000 claims 1
- QSNOQZUSXCVMJX-UHFFFAOYSA-N n-[2-chloro-3-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-5-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C=C(C)C=2)Cl)=CN(C)C1=O QSNOQZUSXCVMJX-UHFFFAOYSA-N 0.000 claims 1
- PKWIAMVSYDJKQB-UHFFFAOYSA-N n-[2-chloro-3-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-6-fluorophenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C(F)=CC=2)Cl)=CN(C)C1=O PKWIAMVSYDJKQB-UHFFFAOYSA-N 0.000 claims 1
- NTIUJPKOSDQHQP-UHFFFAOYSA-N n-[2-chloro-3-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]phenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C=CC=2)Cl)=CN(C)C1=O NTIUJPKOSDQHQP-UHFFFAOYSA-N 0.000 claims 1
- WIWSXPUJWQMNFO-UHFFFAOYSA-N n-[2-chloro-5-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]phenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C=C(NC(=O)C=3SC=4CCCCC=4C=3)C(Cl)=CC=2)=CN(C)C1=O WIWSXPUJWQMNFO-UHFFFAOYSA-N 0.000 claims 1
- ZXRQSUPNXDUIPA-UHFFFAOYSA-N n-[2-cyano-5-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]phenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C=C(NC(=O)C=3SC=4CCCCC=4C=3)C(C#N)=CC=2)=CN(C)C1=O ZXRQSUPNXDUIPA-UHFFFAOYSA-N 0.000 claims 1
- KIPYMJBGXMRDDK-UHFFFAOYSA-N n-[2-fluoro-5-[4-methyl-6-[4-(4-methyl-3-oxopiperazin-2-yl)anilino]-5-oxopyrazin-2-yl]phenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound O=C1N(C)CCNC1C(C=C1)=CC=C1NC1=NC(C=2C=C(NC(=O)C=3SC=4CCCCC=4C=3)C(F)=CC=2)=CN(C)C1=O KIPYMJBGXMRDDK-UHFFFAOYSA-N 0.000 claims 1
- MEWGSAPDLZTFHM-UHFFFAOYSA-N n-[2-fluoro-5-[6-[4-[1-(2-hydroxyethyl)-4-methyl-3-oxopiperazin-2-yl]anilino]-4-methyl-5-oxopyrazin-2-yl]phenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound O=C1N(C)CCN(CCO)C1C(C=C1)=CC=C1NC1=NC(C=2C=C(NC(=O)C=3SC=4CCCCC=4C=3)C(F)=CC=2)=CN(C)C1=O MEWGSAPDLZTFHM-UHFFFAOYSA-N 0.000 claims 1
- CRGNSPVMPWPJLA-UHFFFAOYSA-N n-[2-methyl-3-[4-methyl-5-oxo-6-[4-(1,2,4-trimethyl-3-oxopiperazin-2-yl)anilino]pyrazin-2-yl]phenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound O=C1N(C)CCN(C)C1(C)C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C=CC=2)C)=CN(C)C1=O CRGNSPVMPWPJLA-UHFFFAOYSA-N 0.000 claims 1
- AEAKSHXFHONWPR-UHFFFAOYSA-N n-[2-methyl-3-[4-methyl-6-[4-(1-methyl-3-oxopiperazin-2-yl)anilino]-5-oxopyrazin-2-yl]phenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCNC(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C=CC=2)C)=CN(C)C1=O AEAKSHXFHONWPR-UHFFFAOYSA-N 0.000 claims 1
- JINSGDIPPJZWKV-UHFFFAOYSA-N n-[2-methyl-3-[4-methyl-6-[4-(4-methyl-3-oxo-1-propan-2-ylpiperazin-2-yl)anilino]-5-oxopyrazin-2-yl]phenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CC(C)N1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C=CC=2)C)=CN(C)C1=O JINSGDIPPJZWKV-UHFFFAOYSA-N 0.000 claims 1
- HHHKXAGYHPSJMB-UHFFFAOYSA-N n-[2-methyl-3-[4-methyl-6-[4-(4-methyl-3-oxo-1-propan-2-ylpiperazin-2-yl)anilino]-5-oxopyrazin-2-yl]phenyl]-5,6,7,8-tetrahydro-4h-cyclohepta[b]thiophene-2-carboxamide Chemical compound CC(C)N1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCCC=4C=3)C=CC=2)C)=CN(C)C1=O HHHKXAGYHPSJMB-UHFFFAOYSA-N 0.000 claims 1
- CVXDTJPCAIAUPP-UHFFFAOYSA-N n-[2-methyl-3-[4-methyl-6-[4-[2-(methylamino)-1-morpholin-4-yl-2-oxoethyl]anilino]-5-oxopyrazin-2-yl]phenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound C=1C=C(NC=2C(N(C)C=C(N=2)C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C=CC=2)C)=O)C=CC=1C(C(=O)NC)N1CCOCC1 CVXDTJPCAIAUPP-UHFFFAOYSA-N 0.000 claims 1
- KDBUSGJMBYCAFX-UHFFFAOYSA-N n-[2-methyl-3-[4-methyl-6-[4-[2-(methylamino)-1-morpholin-4-yl-2-oxoethyl]anilino]-5-oxopyrazin-2-yl]phenyl]-5,6,7,8-tetrahydro-4h-cyclohepta[b]thiophene-2-carboxamide Chemical compound C=1C=C(NC=2C(N(C)C=C(N=2)C=2C(=C(NC(=O)C=3SC=4CCCCCC=4C=3)C=CC=2)C)=O)C=CC=1C(C(=O)NC)N1CCOCC1 KDBUSGJMBYCAFX-UHFFFAOYSA-N 0.000 claims 1
- SKSKBPIRCOWKEE-UHFFFAOYSA-N n-[3-[5-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-6-oxo-1h-pyrazin-3-yl]-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C=CC=2)C)=CNC1=O SKSKBPIRCOWKEE-UHFFFAOYSA-N 0.000 claims 1
- NQHYDAORIKUPOZ-UHFFFAOYSA-N n-[3-[5-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-6-oxo-1h-pyrazin-3-yl]-2-methylphenyl]-n-methyl-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound C=1C=2CCCCC=2SC=1C(=O)N(C)C(C=1C)=CC=CC=1C(N=1)=CNC(=O)C=1NC(C=C1)=CC=C1C1N(C)CCN(C)C1=O NQHYDAORIKUPOZ-UHFFFAOYSA-N 0.000 claims 1
- ZDQYITFLOBEZOA-UHFFFAOYSA-N n-[3-[5-[[5-(1,4-dimethyl-3-oxopiperazin-2-yl)pyridin-2-yl]amino]-1-methyl-6-oxopyridin-3-yl]-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=N1)=CC=C1NC1=CC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C=CC=2)C)=CN(C)C1=O ZDQYITFLOBEZOA-UHFFFAOYSA-N 0.000 claims 1
- TZXXOACHUGBCLN-UHFFFAOYSA-N n-[3-[6-[4-(1,4-diethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2,6-difluorophenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CCN1CCN(CC)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C(F)=CC=2)F)=CN(C)C1=O TZXXOACHUGBCLN-UHFFFAOYSA-N 0.000 claims 1
- JDTVOFKWPMRQHZ-UHFFFAOYSA-N n-[3-[6-[4-(1,4-diethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-6-fluoro-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CCN1CCN(CC)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C(F)=CC=2)C)=CN(C)C1=O JDTVOFKWPMRQHZ-UHFFFAOYSA-N 0.000 claims 1
- SQKVSRQCXXJKNZ-UHFFFAOYSA-N n-[3-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2,5-difluorophenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C=C(F)C=2)F)=CN(C)C1=O SQKVSRQCXXJKNZ-UHFFFAOYSA-N 0.000 claims 1
- ZCQFYUGPGLMRFS-UHFFFAOYSA-N n-[3-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2,5-dimethylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C=C(C)C=2)C)=CN(C)C1=O ZCQFYUGPGLMRFS-UHFFFAOYSA-N 0.000 claims 1
- AWBQGALJVKBYPQ-UHFFFAOYSA-N n-[3-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2,6-difluorophenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C(F)=CC=2)F)=CN(C)C1=O AWBQGALJVKBYPQ-UHFFFAOYSA-N 0.000 claims 1
- SMVYUVVBZSDULV-UHFFFAOYSA-N n-[3-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2,6-dimethylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C(C)=CC=2)C)=CN(C)C1=O SMVYUVVBZSDULV-UHFFFAOYSA-N 0.000 claims 1
- BWRHOJMGEQDTTC-UHFFFAOYSA-N n-[3-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2-fluoro-5-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C=C(C)C=2)F)=CN(C)C1=O BWRHOJMGEQDTTC-UHFFFAOYSA-N 0.000 claims 1
- SNGYBTZSHDKBLP-UHFFFAOYSA-N n-[3-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2-fluoro-6-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C(C)=CC=2)F)=CN(C)C1=O SNGYBTZSHDKBLP-UHFFFAOYSA-N 0.000 claims 1
- CWJGFAKENKXHPE-UHFFFAOYSA-N n-[3-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2-fluorophenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C=CC=2)F)=CN(C)C1=O CWJGFAKENKXHPE-UHFFFAOYSA-N 0.000 claims 1
- FMHBOBZQZMPOPY-UHFFFAOYSA-N n-[3-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-4-hydroxy-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCC(O)C=4C=3)C=CC=2)C)=CN(C)C1=O FMHBOBZQZMPOPY-UHFFFAOYSA-N 0.000 claims 1
- HLFNROBMHOROFI-UHFFFAOYSA-N n-[3-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-5,6,7,8-tetrahydro-4h-cyclohepta[b]thiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCCC=4C=3)C=CC=2)C)=CN(C)C1=O HLFNROBMHOROFI-UHFFFAOYSA-N 0.000 claims 1
- SCUNQGSIJXVCNT-UHFFFAOYSA-N n-[3-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-7-hydroxy-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4C(O)CCCC=4C=3)C=CC=2)C)=CN(C)C1=O SCUNQGSIJXVCNT-UHFFFAOYSA-N 0.000 claims 1
- QLCMDJKMSUTUMQ-UHFFFAOYSA-N n-[3-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-7-oxo-5,6-dihydro-4h-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4C(=O)CCCC=4C=3)C=CC=2)C)=CN(C)C1=O QLCMDJKMSUTUMQ-UHFFFAOYSA-N 0.000 claims 1
- PKBFKUXUAAMZKA-UHFFFAOYSA-N n-[3-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-n-methyl-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound C=1C=2CCCCC=2SC=1C(=O)N(C)C(C=1C)=CC=CC=1C(N=1)=CN(C)C(=O)C=1NC(C=C1)=CC=C1C1N(C)CCN(C)C1=O PKBFKUXUAAMZKA-UHFFFAOYSA-N 0.000 claims 1
- FXJAYNBGQNTHQK-UHFFFAOYSA-N n-[3-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-5-fluoro-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C=C(F)C=2)C)=CN(C)C1=O FXJAYNBGQNTHQK-UHFFFAOYSA-N 0.000 claims 1
- OWRYUFXKKDVQDD-UHFFFAOYSA-N n-[3-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-5-methoxy-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound C=1C(OC)=CC(NC(=O)C=2SC=3CCCCC=3C=2)=C(C)C=1C(N=1)=CN(C)C(=O)C=1NC(C=C1)=CC=C1C1N(C)CCN(C)C1=O OWRYUFXKKDVQDD-UHFFFAOYSA-N 0.000 claims 1
- RKROEMYBMQHKQK-UHFFFAOYSA-N n-[3-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-6-fluoro-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C(F)=CC=2)C)=CN(C)C1=O RKROEMYBMQHKQK-UHFFFAOYSA-N 0.000 claims 1
- RAYABIUAYLVIIX-UHFFFAOYSA-N n-[3-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]phenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C=C(NC(=O)C=3SC=4CCCCC=4C=3)C=CC=2)=CN(C)C1=O RAYABIUAYLVIIX-UHFFFAOYSA-N 0.000 claims 1
- SOYAEGWTCNICRU-UHFFFAOYSA-N n-[3-[6-[4-(1-amino-2-morpholin-4-yl-2-oxoethyl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-4-tert-butylbenzamide Chemical compound C1=CC=C(C=2N=C(NC=3C=CC(=CC=3)C(N)C(=O)N3CCOCC3)C(=O)N(C)C=2)C(C)=C1NC(=O)C1=CC=C(C(C)(C)C)C=C1 SOYAEGWTCNICRU-UHFFFAOYSA-N 0.000 claims 1
- KVEBLBIKTSOFHR-UHFFFAOYSA-N n-[3-[6-[4-(1-ethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2,6-difluorophenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CCN1CCNC(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C(F)=CC=2)F)=CN(C)C1=O KVEBLBIKTSOFHR-UHFFFAOYSA-N 0.000 claims 1
- YRAVELZBDOTAPL-UHFFFAOYSA-N n-[3-[6-[4-(1-ethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-6-fluoro-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CCN1CCNC(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C(F)=CC=2)C)=CN(C)C1=O YRAVELZBDOTAPL-UHFFFAOYSA-N 0.000 claims 1
- KCVKGYZPURYKQC-UHFFFAOYSA-N n-[3-[6-[4-(1-ethyl-4-methyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2,6-difluorophenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CCN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C(F)=CC=2)F)=CN(C)C1=O KCVKGYZPURYKQC-UHFFFAOYSA-N 0.000 claims 1
- MRWOWFNZERQGQQ-UHFFFAOYSA-N n-[3-[6-[4-(1-ethyl-4-methyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CCN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C=CC=2)C)=CN(C)C1=O MRWOWFNZERQGQQ-UHFFFAOYSA-N 0.000 claims 1
- OISXKLVRVPQSLK-UHFFFAOYSA-N n-[3-[6-[4-(1-ethyl-4-methyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-5,6,7,8-tetrahydro-4h-cyclohepta[b]thiophene-2-carboxamide Chemical compound CCN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCCC=4C=3)C=CC=2)C)=CN(C)C1=O OISXKLVRVPQSLK-UHFFFAOYSA-N 0.000 claims 1
- DHNAPFCFZHUWCO-UHFFFAOYSA-N n-[3-[6-[4-(1-ethyl-4-methyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-6-fluoro-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CCN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C(F)=CC=2)C)=CN(C)C1=O DHNAPFCFZHUWCO-UHFFFAOYSA-N 0.000 claims 1
- IHLZEXWATBHHIT-UHFFFAOYSA-N n-[3-[6-[4-(4-ethyl-1-methyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2,6-difluorophenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound O=C1N(CC)CCN(C)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C(F)=CC=2)F)=CN(C)C1=O IHLZEXWATBHHIT-UHFFFAOYSA-N 0.000 claims 1
- CUDIEYCBSNFLSZ-UHFFFAOYSA-N n-[3-[6-[4-(4-ethyl-1-methyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound O=C1N(CC)CCN(C)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C=CC=2)C)=CN(C)C1=O CUDIEYCBSNFLSZ-UHFFFAOYSA-N 0.000 claims 1
- JIVVGSIIXWSEAQ-UHFFFAOYSA-N n-[3-[6-[4-(4-ethyl-1-methyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-5,6,7,8-tetrahydro-4h-cyclohepta[b]thiophene-2-carboxamide Chemical compound O=C1N(CC)CCN(C)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCCC=4C=3)C=CC=2)C)=CN(C)C1=O JIVVGSIIXWSEAQ-UHFFFAOYSA-N 0.000 claims 1
- KKMUBLXRAKGXOV-UHFFFAOYSA-N n-[3-[6-[4-(4-ethyl-1-methyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-6-fluoro-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound O=C1N(CC)CCN(C)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C(F)=CC=2)C)=CN(C)C1=O KKMUBLXRAKGXOV-UHFFFAOYSA-N 0.000 claims 1
- KNGKJQJHVUAPTP-HKBQPEDESA-N n-[3-[6-[4-[(1s)-2-(dimethylamino)-1-[methyl(propan-2-yl)amino]-2-oxoethyl]anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound C1=CC([C@@H](C(=O)N(C)C)N(C)C(C)C)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C=CC=2)C)=CN(C)C1=O KNGKJQJHVUAPTP-HKBQPEDESA-N 0.000 claims 1
- CDOOFZZILLRUQH-GDLZYMKVSA-N n-[3-[6-[4-[(2r)-1,4-dimethyl-3-oxopiperazin-2-yl]anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)[C@H]1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C=CC=2)C)=CN(C)C1=O CDOOFZZILLRUQH-GDLZYMKVSA-N 0.000 claims 1
- CDOOFZZILLRUQH-LJAQVGFWSA-N n-[3-[6-[4-[(2s)-1,4-dimethyl-3-oxopiperazin-2-yl]anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)[C@@H]1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C=CC=2)C)=CN(C)C1=O CDOOFZZILLRUQH-LJAQVGFWSA-N 0.000 claims 1
- FKGKKDDQAMSAKJ-UHFFFAOYSA-N n-[3-[6-[4-[1,2-bis(4-ethylpiperazin-1-yl)-2-oxoethyl]anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound C1CN(CC)CCN1C(C=1C=CC(NC=2C(N(C)C=C(N=2)C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C=CC=2)C)=O)=CC=1)C(=O)N1CCN(CC)CC1 FKGKKDDQAMSAKJ-UHFFFAOYSA-N 0.000 claims 1
- OZNIRIPMIGLAIU-UHFFFAOYSA-N n-[3-[6-[4-[1,2-bis(4-ethylpiperazin-1-yl)-2-oxoethyl]anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-4-tert-butylbenzamide Chemical compound C1CN(CC)CCN1C(C=1C=CC(NC=2C(N(C)C=C(N=2)C=2C(=C(NC(=O)C=3C=CC(=CC=3)C(C)(C)C)C=CC=2)C)=O)=CC=1)C(=O)N1CCN(CC)CC1 OZNIRIPMIGLAIU-UHFFFAOYSA-N 0.000 claims 1
- VBMIZPIKNFAOQM-UHFFFAOYSA-N n-[3-[6-[4-[1,2-bis(4-ethylpiperazin-1-yl)-2-oxoethyl]anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-5,6,7,8-tetrahydro-4h-cyclohepta[b]thiophene-2-carboxamide Chemical compound C1CN(CC)CCN1C(C=1C=CC(NC=2C(N(C)C=C(N=2)C=2C(=C(NC(=O)C=3SC=4CCCCCC=4C=3)C=CC=2)C)=O)=CC=1)C(=O)N1CCN(CC)CC1 VBMIZPIKNFAOQM-UHFFFAOYSA-N 0.000 claims 1
- JCDAPMXXCVOWFC-UHFFFAOYSA-N n-[3-[6-[4-[1-(4-ethylpiperazin-1-yl)-2-morpholin-4-yl-2-oxoethyl]anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound C1CN(CC)CCN1C(C=1C=CC(NC=2C(N(C)C=C(N=2)C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C=CC=2)C)=O)=CC=1)C(=O)N1CCOCC1 JCDAPMXXCVOWFC-UHFFFAOYSA-N 0.000 claims 1
- HYJFUWXVNKTRAZ-UHFFFAOYSA-N n-[3-[6-[4-[1-(azetidin-1-yl)-2-(dimethylamino)-2-oxoethyl]anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound C=1C=C(NC=2C(N(C)C=C(N=2)C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C=CC=2)C)=O)C=CC=1C(C(=O)N(C)C)N1CCC1 HYJFUWXVNKTRAZ-UHFFFAOYSA-N 0.000 claims 1
- CSINXDGSVGKOTC-UHFFFAOYSA-N n-[3-[6-[4-[1-(azetidin-1-yl)-2-(dimethylamino)-2-oxoethyl]anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-4-tert-butylbenzamide Chemical compound C=1C=C(NC=2C(N(C)C=C(N=2)C=2C(=C(NC(=O)C=3C=CC(=CC=3)C(C)(C)C)C=CC=2)C)=O)C=CC=1C(C(=O)N(C)C)N1CCC1 CSINXDGSVGKOTC-UHFFFAOYSA-N 0.000 claims 1
- ZUZMMYCDZVABKU-UHFFFAOYSA-N n-[3-[6-[4-[1-(azetidin-1-yl)-2-(dimethylamino)-2-oxoethyl]anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-5,6,7,8-tetrahydro-4h-cyclohepta[b]thiophene-2-carboxamide Chemical compound C=1C=C(NC=2C(N(C)C=C(N=2)C=2C(=C(NC(=O)C=3SC=4CCCCCC=4C=3)C=CC=2)C)=O)C=CC=1C(C(=O)N(C)C)N1CCC1 ZUZMMYCDZVABKU-UHFFFAOYSA-N 0.000 claims 1
- AKXPXSKCEOUQGM-UHFFFAOYSA-N n-[3-[6-[4-[1-(azetidin-1-yl)-2-[2-hydroxyethyl(methyl)amino]-2-oxoethyl]anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound C=1C=C(NC=2C(N(C)C=C(N=2)C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C=CC=2)C)=O)C=CC=1C(C(=O)N(CCO)C)N1CCC1 AKXPXSKCEOUQGM-UHFFFAOYSA-N 0.000 claims 1
- KDXQHCOCDLSIGO-UHFFFAOYSA-N n-[3-[6-[4-[1-(azetidin-1-yl)-2-morpholin-4-yl-2-oxoethyl]anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CC1=C(NC(=O)C=2SC=3CCCCC=3C=2)C=CC=C1C(N=1)=CN(C)C(=O)C=1NC(C=C1)=CC=C1C(C(=O)N1CCOCC1)N1CCC1 KDXQHCOCDLSIGO-UHFFFAOYSA-N 0.000 claims 1
- YTVGAFYNEZDMGP-UHFFFAOYSA-N n-[3-[6-[4-[2-(azetidin-1-yl)-1-[methyl(propan-2-yl)amino]-2-oxoethyl]anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-4-tert-butylbenzamide Chemical compound C=1C=C(NC=2C(N(C)C=C(N=2)C=2C(=C(NC(=O)C=3C=CC(=CC=3)C(C)(C)C)C=CC=2)C)=O)C=CC=1C(N(C)C(C)C)C(=O)N1CCC1 YTVGAFYNEZDMGP-UHFFFAOYSA-N 0.000 claims 1
- QAHUAOMMCGHCRG-UHFFFAOYSA-N n-[3-[6-[4-[2-(azetidin-1-yl)-1-morpholin-4-yl-2-oxoethyl]anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CC1=C(NC(=O)C=2SC=3CCCCC=3C=2)C=CC=C1C(N=1)=CN(C)C(=O)C=1NC(C=C1)=CC=C1C(C(=O)N1CCC1)N1CCOCC1 QAHUAOMMCGHCRG-UHFFFAOYSA-N 0.000 claims 1
- SUGMWRAMNWFIOP-UHFFFAOYSA-N n-[3-[6-[4-[2-(diethylamino)-1-(4-ethylpiperazin-1-yl)-2-oxoethyl]anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-5,6,7,8-tetrahydro-4h-cyclohepta[b]thiophene-2-carboxamide Chemical compound C=1C=C(NC=2C(N(C)C=C(N=2)C=2C(=C(NC(=O)C=3SC=4CCCCCC=4C=3)C=CC=2)C)=O)C=CC=1C(C(=O)N(CC)CC)N1CCN(CC)CC1 SUGMWRAMNWFIOP-UHFFFAOYSA-N 0.000 claims 1
- FLOACIQUMKEUFY-UHFFFAOYSA-N n-[3-[6-[4-[2-(diethylamino)-1-morpholin-4-yl-2-oxoethyl]anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound C=1C=C(NC=2C(N(C)C=C(N=2)C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C=CC=2)C)=O)C=CC=1C(C(=O)N(CC)CC)N1CCOCC1 FLOACIQUMKEUFY-UHFFFAOYSA-N 0.000 claims 1
- MJSKRJAHZOWCQY-UHFFFAOYSA-N n-[3-[6-[4-[2-(diethylamino)-1-morpholin-4-yl-2-oxoethyl]anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-5,6,7,8-tetrahydro-4h-cyclohepta[b]thiophene-2-carboxamide Chemical compound C=1C=C(NC=2C(N(C)C=C(N=2)C=2C(=C(NC(=O)C=3SC=4CCCCCC=4C=3)C=CC=2)C)=O)C=CC=1C(C(=O)N(CC)CC)N1CCOCC1 MJSKRJAHZOWCQY-UHFFFAOYSA-N 0.000 claims 1
- QCIZLWBSKLYDFL-UHFFFAOYSA-N n-[3-[6-[4-[2-(dimethylamino)-1-(4-ethylpiperazin-1-yl)-2-oxoethyl]anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound C1CN(CC)CCN1C(C(=O)N(C)C)C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C=CC=2)C)=CN(C)C1=O QCIZLWBSKLYDFL-UHFFFAOYSA-N 0.000 claims 1
- ITULLRFBSCFNNM-UHFFFAOYSA-N n-[3-[6-[4-[2-(dimethylamino)-1-morpholin-4-yl-2-oxoethyl]anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound C=1C=C(NC=2C(N(C)C=C(N=2)C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C=CC=2)C)=O)C=CC=1C(C(=O)N(C)C)N1CCOCC1 ITULLRFBSCFNNM-UHFFFAOYSA-N 0.000 claims 1
- MDTBXIBQUGUCLK-UHFFFAOYSA-N n-[3-[6-[4-[2-(dimethylamino)-1-morpholin-4-yl-2-oxoethyl]anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-5,6,7,8-tetrahydro-4h-cyclohepta[b]thiophene-2-carboxamide Chemical compound C=1C=C(NC=2C(N(C)C=C(N=2)C=2C(=C(NC(=O)C=3SC=4CCCCCC=4C=3)C=CC=2)C)=O)C=CC=1C(C(=O)N(C)C)N1CCOCC1 MDTBXIBQUGUCLK-UHFFFAOYSA-N 0.000 claims 1
- FCVOOIWIFQGPEX-UHFFFAOYSA-N n-[3-[6-[4-[2-[ethyl(methyl)amino]-1-morpholin-4-yl-2-oxoethyl]anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound C=1C=C(NC=2C(N(C)C=C(N=2)C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C=CC=2)C)=O)C=CC=1C(C(=O)N(C)CC)N1CCOCC1 FCVOOIWIFQGPEX-UHFFFAOYSA-N 0.000 claims 1
- RIMRRODHDHOWLV-UHFFFAOYSA-N n-[3-[6-[4-[2-[ethyl(methyl)amino]-1-morpholin-4-yl-2-oxoethyl]anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-5,6,7,8-tetrahydro-4h-cyclohepta[b]thiophene-2-carboxamide Chemical compound C=1C=C(NC=2C(N(C)C=C(N=2)C=2C(=C(NC(=O)C=3SC=4CCCCCC=4C=3)C=CC=2)C)=O)C=CC=1C(C(=O)N(C)CC)N1CCOCC1 RIMRRODHDHOWLV-UHFFFAOYSA-N 0.000 claims 1
- RMQAPKDNJXRPGE-UHFFFAOYSA-N n-[3-[6-[4-[2-amino-1-[methyl(propan-2-yl)amino]-2-oxoethyl]anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound C1=CC(C(C(N)=O)N(C)C(C)C)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C=CC=2)C)=CN(C)C1=O RMQAPKDNJXRPGE-UHFFFAOYSA-N 0.000 claims 1
- WQSSIMBESOXRPF-UHFFFAOYSA-N n-[4-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-6-fluoropyridin-2-yl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C=C(NC(=O)C=3SC=4CCCCC=4C=3)N=C(F)C=2)=CN(C)C1=O WQSSIMBESOXRPF-UHFFFAOYSA-N 0.000 claims 1
- BDXBGFRKGQECBV-UHFFFAOYSA-N n-[5-[6-[4-(1,4-diethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2-fluorophenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CCN1CCN(CC)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C=C(NC(=O)C=3SC=4CCCCC=4C=3)C(F)=CC=2)=CN(C)C1=O BDXBGFRKGQECBV-UHFFFAOYSA-N 0.000 claims 1
- WHPGTHXHUZTUGM-UHFFFAOYSA-N n-[5-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2-fluorophenyl]-4,4-difluoro-6,7-dihydro-5h-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C=C(NC(=O)C=3SC4=C(C(CCC4)(F)F)C=3)C(F)=CC=2)=CN(C)C1=O WHPGTHXHUZTUGM-UHFFFAOYSA-N 0.000 claims 1
- ZGWZMIIQVITDKD-UHFFFAOYSA-N n-[5-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2-fluorophenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C=C(NC(=O)C=3SC=4CCCCC=4C=3)C(F)=CC=2)=CN(C)C1=O ZGWZMIIQVITDKD-UHFFFAOYSA-N 0.000 claims 1
- QJKSOCPZKQRWAU-UHFFFAOYSA-N n-[5-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2-fluorophenyl]-7,7-difluoro-5,6-dihydro-4h-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C=C(NC(=O)C=3SC=4C(F)(F)CCCC=4C=3)C(F)=CC=2)=CN(C)C1=O QJKSOCPZKQRWAU-UHFFFAOYSA-N 0.000 claims 1
- LTDOCWYGMAQBML-UHFFFAOYSA-N n-[5-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]pyridin-3-yl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C=C(NC(=O)C=3SC=4CCCCC=4C=3)C=NC=2)=CN(C)C1=O LTDOCWYGMAQBML-UHFFFAOYSA-N 0.000 claims 1
- RGWMXAZNPSZLHO-UHFFFAOYSA-N n-[5-[6-[4-(1-ethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2-fluorophenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CCN1CCNC(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C=C(NC(=O)C=3SC=4CCCCC=4C=3)C(F)=CC=2)=CN(C)C1=O RGWMXAZNPSZLHO-UHFFFAOYSA-N 0.000 claims 1
- BCUDZPQGNBYKNJ-UHFFFAOYSA-N n-[5-[6-[4-(1-ethyl-4-methyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2-fluorophenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CCN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C=C(NC(=O)C=3SC=4CCCCC=4C=3)C(F)=CC=2)=CN(C)C1=O BCUDZPQGNBYKNJ-UHFFFAOYSA-N 0.000 claims 1
- JQKBGTVFILBMRF-UHFFFAOYSA-N n-[5-[6-[4-(2,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2-fluorophenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound O=C1N(C)CCNC1(C)C(C=C1)=CC=C1NC1=NC(C=2C=C(NC(=O)C=3SC=4CCCCC=4C=3)C(F)=CC=2)=CN(C)C1=O JQKBGTVFILBMRF-UHFFFAOYSA-N 0.000 claims 1
- LNICIYAJUAWCCJ-UHFFFAOYSA-N n-[5-[6-[4-(4-ethyl-1-methyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2-fluorophenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound O=C1N(CC)CCN(C)C1C(C=C1)=CC=C1NC1=NC(C=2C=C(NC(=O)C=3SC=4CCCCC=4C=3)C(F)=CC=2)=CN(C)C1=O LNICIYAJUAWCCJ-UHFFFAOYSA-N 0.000 claims 1
- ZGWZMIIQVITDKD-MUUNZHRXSA-N n-[5-[6-[4-[(2r)-1,4-dimethyl-3-oxopiperazin-2-yl]anilino]-4-methyl-5-oxopyrazin-2-yl]-2-fluorophenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)[C@H]1C(C=C1)=CC=C1NC1=NC(C=2C=C(NC(=O)C=3SC=4CCCCC=4C=3)C(F)=CC=2)=CN(C)C1=O ZGWZMIIQVITDKD-MUUNZHRXSA-N 0.000 claims 1
- ZGWZMIIQVITDKD-NDEPHWFRSA-N n-[5-[6-[4-[(2s)-1,4-dimethyl-3-oxopiperazin-2-yl]anilino]-4-methyl-5-oxopyrazin-2-yl]-2-fluorophenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)[C@@H]1C(C=C1)=CC=C1NC1=NC(C=2C=C(NC(=O)C=3SC=4CCCCC=4C=3)C(F)=CC=2)=CN(C)C1=O ZGWZMIIQVITDKD-NDEPHWFRSA-N 0.000 claims 1
- BVTWUWXALAMUBH-UHFFFAOYSA-N n-[5-[6-[4-[2-(azetidin-1-yl)-1-(dimethylamino)-2-oxoethyl]anilino]-4-methyl-5-oxopyrazin-2-yl]-2-fluorophenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound C=1C=C(NC=2C(N(C)C=C(N=2)C=2C=C(NC(=O)C=3SC=4CCCCC=4C=3)C(F)=CC=2)=O)C=CC=1C(N(C)C)C(=O)N1CCC1 BVTWUWXALAMUBH-UHFFFAOYSA-N 0.000 claims 1
- USTOFZVWKVCABF-UHFFFAOYSA-N n-[5-chloro-3-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2-fluorophenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C=C(Cl)C=2)F)=CN(C)C1=O USTOFZVWKVCABF-UHFFFAOYSA-N 0.000 claims 1
- AAOPHDODYQDGCC-UHFFFAOYSA-N n-[5-chloro-3-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C=C(Cl)C=2)C)=CN(C)C1=O AAOPHDODYQDGCC-UHFFFAOYSA-N 0.000 claims 1
- QTVPLNPLKUSJHJ-UHFFFAOYSA-N n-[6-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-3-fluoropyridin-2-yl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2N=C(NC(=O)C=3SC=4CCCCC=4C=3)C(F)=CC=2)=CN(C)C1=O QTVPLNPLKUSJHJ-UHFFFAOYSA-N 0.000 claims 1
- QAOQIGJSQKLLMM-UHFFFAOYSA-N n-[6-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-5-fluoropyridin-2-yl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=CC=C(NC(=O)C=3SC=4CCCCC=4C=3)N=2)F)=CN(C)C1=O QAOQIGJSQKLLMM-UHFFFAOYSA-N 0.000 claims 1
- TVLUDPIOSXBJBB-UHFFFAOYSA-N n-[6-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]pyridin-2-yl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2N=C(NC(=O)C=3SC=4CCCCC=4C=3)C=CC=2)=CN(C)C1=O TVLUDPIOSXBJBB-UHFFFAOYSA-N 0.000 claims 1
- NWOMRMQBFVWNFP-UHFFFAOYSA-N n-[6-[6-[4-(1-ethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-3-fluoropyridin-2-yl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CCN1CCNC(=O)C1C(C=C1)=CC=C1NC1=NC(C=2N=C(NC(=O)C=3SC=4CCCCC=4C=3)C(F)=CC=2)=CN(C)C1=O NWOMRMQBFVWNFP-UHFFFAOYSA-N 0.000 claims 1
- IRLSFOIRLQBCHA-UHFFFAOYSA-N n-[6-[6-[4-(1-ethyl-4-methyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-3-fluoropyridin-2-yl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CCN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2N=C(NC(=O)C=3SC=4CCCCC=4C=3)C(F)=CC=2)=CN(C)C1=O IRLSFOIRLQBCHA-UHFFFAOYSA-N 0.000 claims 1
- RNTQOVMBSLZDIP-UHFFFAOYSA-N n-[6-[6-[4-(4-ethyl-1-methyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-3-fluoropyridin-2-yl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound O=C1N(CC)CCN(C)C1C(C=C1)=CC=C1NC1=NC(C=2N=C(NC(=O)C=3SC=4CCCCC=4C=3)C(F)=CC=2)=CN(C)C1=O RNTQOVMBSLZDIP-UHFFFAOYSA-N 0.000 claims 1
- QTVPLNPLKUSJHJ-AREMUKBSSA-N n-[6-[6-[4-[(2r)-1,4-dimethyl-3-oxopiperazin-2-yl]anilino]-4-methyl-5-oxopyrazin-2-yl]-3-fluoropyridin-2-yl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)[C@H]1C(C=C1)=CC=C1NC1=NC(C=2N=C(NC(=O)C=3SC=4CCCCC=4C=3)C(F)=CC=2)=CN(C)C1=O QTVPLNPLKUSJHJ-AREMUKBSSA-N 0.000 claims 1
- QTVPLNPLKUSJHJ-SANMLTNESA-N n-[6-[6-[4-[(2s)-1,4-dimethyl-3-oxopiperazin-2-yl]anilino]-4-methyl-5-oxopyrazin-2-yl]-3-fluoropyridin-2-yl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)[C@@H]1C(C=C1)=CC=C1NC1=NC(C=2N=C(NC(=O)C=3SC=4CCCCC=4C=3)C(F)=CC=2)=CN(C)C1=O QTVPLNPLKUSJHJ-SANMLTNESA-N 0.000 claims 1
- OILKPXUBRGRVPF-UHFFFAOYSA-N n-[6-chloro-3-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2-fluorophenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C(Cl)=CC=2)F)=CN(C)C1=O OILKPXUBRGRVPF-UHFFFAOYSA-N 0.000 claims 1
- CMFMSYJMERDRPZ-UHFFFAOYSA-N n-[6-chloro-3-[6-[4-(1,4-dimethyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C(Cl)=CC=2)C)=CN(C)C1=O CMFMSYJMERDRPZ-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
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Families Citing this family (79)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR063706A1 (es) * | 2006-09-11 | 2009-02-11 | Cgi Pharmaceuticals Inc | Determinadas amidas sustituidas, el uso de las mismas para el tratamiento de enfermedades mediadas por la inhibicion de la actividad de btk y composiciones farmaceuticas que las comprenden. |
| US7838523B2 (en) * | 2006-09-11 | 2010-11-23 | Cgi Pharmaceuticals, Inc. | Certain substituted amides, method of making, and method of use thereof |
| US7683064B2 (en) | 2008-02-05 | 2010-03-23 | Roche Palo Alto Llc | Inhibitors of Bruton's tyrosine kinase |
| UA103319C2 (en) | 2008-05-06 | 2013-10-10 | Глаксосмитклайн Ллк | Thiazole- and oxazole-benzene sulfonamide compounds |
| US8426424B2 (en) * | 2008-05-06 | 2013-04-23 | Cgi Pharmaceuticals, Inc. | Certain substituted amides, method of making, and method of use thereof |
| UA103327C2 (en) | 2008-06-24 | 2013-10-10 | Ф. Хоффманн-Ля Рош Аг | Substituted pyridin-2-ones and pyridazin-3-ones |
| MX2010013478A (es) | 2008-07-02 | 2010-12-20 | Hoffmann La Roche | Nuevas fenilpirazinonas como inhibidores de cinasa. |
| SG185462A1 (en) | 2010-05-07 | 2012-12-28 | Gilead Connecticut Inc | Pyridone and aza-pyridone compounds and methods of use |
| CN106220614B (zh) * | 2010-09-01 | 2019-07-16 | 吉利德康涅狄格有限公司 | 吡啶酮/吡嗪酮、其制备方法及使用方法 |
| UA111756C2 (uk) | 2011-11-03 | 2016-06-10 | Ф. Хоффманн-Ля Рош Аг | Сполуки гетероарилпіридону та азапіридону як інгібітори тирозинкінази брутона |
| BR112014010439A2 (pt) * | 2011-11-03 | 2017-04-18 | F Hoffmann - La Roche Ag | compostos, composição farmacêutica, processo de produção, método de tratamento de uma doença ou distúrbio, métodos, kit e uso de uma composição farmacêutica |
| TWI553004B (zh) | 2011-11-03 | 2016-10-11 | 建南德克公司 | ８－氟基呔－１（２ｈ）－酮化合物 |
| BR112014010391A2 (pt) | 2011-11-03 | 2017-04-18 | Hoffmann La Roche | composto, composição farmacêutica, processo de produção de uma composição farmacêutica, método de tratamento, kit e uso de uma composição farmacêutica |
| WO2013097052A1 (en) | 2011-12-30 | 2013-07-04 | Abbott Laboratories | Bromodomain inhibitors |
| JP6248048B2 (ja) | 2012-01-09 | 2017-12-13 | エックス−アールエックス，インコーポレーテッド | キナーゼ阻害活性を有するトリプトリン誘導体及びその使用 |
| WO2013157021A1 (en) | 2012-04-20 | 2013-10-24 | Advinus Therapeutics Limited | Bicyclic compounds, compositions and medicinal applications thereof |
| WO2014108820A1 (en) * | 2013-01-08 | 2014-07-17 | Aurigene Discovery Technologies Limited | Substituted 2-pyrazinone derivatives as kinase inhibitors |
| WO2014125410A1 (en) * | 2013-02-12 | 2014-08-21 | Aurigene Discovery Technologies Limited | N-substituted heterocyclic derivatives as kinase inhibitors |
| CA2903288C (en) * | 2013-03-15 | 2021-09-21 | Deciphera Pharmaceuticals, Llc | N-acyl-n'-(pyridin-2-yl) ureas and analogs exhibiting anti-cancer and anti-proliferative activities |
| BR112015025260B1 (pt) | 2013-04-25 | 2021-11-03 | Beigene, Ltd | Compostos heterocíclicos fundidos como inibidores da proteína quinase, sua composição, combinação e uso |
| DK3010543T3 (da) * | 2013-06-19 | 2025-12-01 | Som Innovation Biotech S A | Terapeutiske midler til anvendelse i profylakse og/eller behandling af hyperkinetiske bevægelsesforstyrrelser |
| CA2912359A1 (en) * | 2013-07-03 | 2015-01-08 | F. Hoffmann-La Roche Ag | Heteroaryl pyridone and aza-pyridone amide compounds |
| PT3027171T (pt) | 2013-07-30 | 2020-06-18 | Gilead Connecticut Inc | Formulação de inibidores da syk |
| KR101810798B1 (ko) | 2013-07-30 | 2017-12-19 | 질레드 코네티컷 인코포레이티드 | Ｓｙｋ 억제제의 다형체 |
| HRP20221262T1 (hr) | 2013-09-13 | 2022-12-09 | Beigene Switzerland Gmbh | Protutijela anti-pd1 i njihova uporaba kao terapeutskih i dijagnostičkih sredstava |
| EA035727B1 (ru) * | 2013-10-18 | 2020-07-31 | Селджен Квонтисел Рисёрч, Инк. | Ингибиторы бромодомена |
| EP2876124B1 (de) | 2013-11-20 | 2019-01-09 | Uhde Inventa-Fischer GmbH | Verfahren sowie vorrichtung zur herstellung einer kristallisierbaren polymilchsäuremischung sowie polymilchsäuremischung |
| MX375752B (es) | 2013-12-05 | 2025-03-06 | Pharmacyclics Llc | Inhibidores de tirosina quinasa de bruton. |
| CA2929918C (en) | 2013-12-05 | 2018-01-23 | F. Hoffmann-La Roche Ag | Heteroaryl pyridone and aza-pyridone compounds with electrophilic functionality |
| TWI735853B (zh) | 2013-12-23 | 2021-08-11 | 美商克洛諾斯生技有限公司 | 脾酪胺酸激酶抑制劑 |
| WO2015151006A1 (en) | 2014-03-29 | 2015-10-08 | Lupin Limited | Substituted purine compounds as btk inhibitors |
| WO2015170266A1 (en) | 2014-05-07 | 2015-11-12 | Lupin Limited | Substituted pyrimidine compounds as btk inhibitors |
| ES2812626T3 (es) | 2014-06-27 | 2021-03-17 | Celgene Quanticel Res Inc | Inhibidores de la desmetilasa 1 específica de lisina |
| SG11201610975RA (en) * | 2014-07-03 | 2017-01-27 | Celgene Quanticel Res Inc | Inhibitors of lysine specific demethylase-1 |
| CN110156892B (zh) | 2014-07-03 | 2023-05-16 | 百济神州有限公司 | 抗pd-l1抗体及其作为治疗剂及诊断剂的用途 |
| EP3265453B1 (en) * | 2015-03-05 | 2022-06-29 | Boehringer Ingelheim International GmbH | New pyridinones and isoquinolinones as inhibitors of the bromodomain brd9 |
| MA52119A (fr) | 2015-10-19 | 2018-08-29 | Ncyte Corp | Composés hétérocycliques utilisés comme immunomodulateurs |
| PT3377488T (pt) | 2015-11-19 | 2022-11-21 | Incyte Corp | Compostos heterocíclicos como imunomoduladores |
| SI3394033T1 (sl) | 2015-12-22 | 2021-03-31 | Incyte Corporation | Heterociklične spojine kot imunomodulatorji |
| CN107033069B (zh) | 2016-02-04 | 2022-03-04 | 中国科学院合肥物质科学研究院 | 一种新型布鲁顿酪氨酸激酶不可逆抑制剂 |
| KR20200118507A (ko) | 2016-02-29 | 2020-10-15 | 에프. 호프만-라 로슈 아게 | 브루톤 티로신 키나제의 억제제를 포함하는 투여량 형태 조성물 |
| SG11201808003RA (en) | 2016-04-15 | 2018-10-30 | Abbvie Inc | Bromodomain inhibitors |
| WO2017192961A1 (en) | 2016-05-06 | 2017-11-09 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| EP3464279B1 (en) | 2016-05-26 | 2021-11-24 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| PL3472167T3 (pl) * | 2016-06-20 | 2022-12-19 | Incyte Corporation | Związki heterocykliczne jako immunomodulatory |
| NZ749997A (en) | 2016-07-05 | 2022-11-25 | Beigene Ltd | Combination of a pd-l antagonist and a raf inhibitor for treating cancer |
| EP3484866B1 (en) | 2016-07-14 | 2022-09-07 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| WO2018033853A2 (en) | 2016-08-16 | 2018-02-22 | Beigene, Ltd. | Crystalline form of (s)-7-(1-acryloylpiperidin-4-yl)-2-(4-phenoxyphenyl)-4,5,6,7-tetra-hydropyrazolo[1,5-a]pyrimidine-3-carboxamide, preparation, and uses thereof |
| TWI739887B (zh) | 2016-08-19 | 2021-09-21 | 英屬開曼群島商百濟神州有限公司 | 使用包含btk抑制劑的組合產品治療癌症 |
| ES2941716T3 (es) | 2016-08-29 | 2023-05-25 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
| AU2017326558B2 (en) | 2016-09-19 | 2022-01-06 | Mei Pharma, Inc. | Combination therapy |
| US10842878B2 (en) | 2016-11-22 | 2020-11-24 | Dana-Farber Cancer Institute, Inc. | Degradation of Bruton's tyrosine kinase (BTK) by conjugation of BTK inhibitors with E3 ligase ligand and methods of use |
| WO2018119286A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Bicyclic heteroaromatic compounds as immunomodulators |
| EP3558973B1 (en) | 2016-12-22 | 2021-09-15 | Incyte Corporation | Pyridine derivatives as immunomodulators |
| KR102696516B1 (ko) | 2016-12-22 | 2024-08-22 | 인사이트 코포레이션 | 면역조절제로서의 벤조옥사졸 유도체 |
| MY197501A (en) | 2016-12-22 | 2023-06-19 | Incyte Corp | Tetrahydro imidazo[4,5-c]pyridine derivatives as pd-l1 internalization inducers |
| US20180179201A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| CN110139641B (zh) * | 2016-12-28 | 2022-09-09 | 富士胶片富山化学株式会社 | 外用组合物 |
| EP3573989A4 (en) | 2017-01-25 | 2020-11-18 | Beigene, Ltd. | CRYSTALLINE FORMS OF (S) -7- (1- (BUT-2-YNOYL) PIPERIDIN-4-YL) -2- (4-PHENOXYPHENYL) -4, 5, 6, 7-TETRAHY DROPYRAZOLO [1, 5-A ] PYRIMIDINE-3-CARBOXAMIDE, PREPARATION AND ASSOCIATED USES |
| CN110709702A (zh) | 2017-03-24 | 2020-01-17 | 豪夫迈·罗氏有限公司 | 治疗自身免疫性疾病和炎性疾病的方法 |
| TWI877099B (zh) | 2017-06-26 | 2025-03-21 | 英屬開曼群島商百濟神州有限公司 | 抗ｐｄ－１抗體或其抗原結合片段在製備治療用於患有肝細胞癌（ｈｃｃ）之藥物的用途 |
| WO2019034009A1 (en) | 2017-08-12 | 2019-02-21 | Beigene, Ltd. | BTK INHIBITOR WITH ENHANCED DOUBLE SELECTIVITY |
| KR20220070056A (ko) | 2017-08-25 | 2022-05-27 | 길리애드 사이언시즈, 인코포레이티드 | Syk 억제제의 다형체 |
| KR102613433B1 (ko) | 2017-10-11 | 2023-12-13 | 주식회사 대웅제약 | 신규한 페닐피리딘 유도체 및 이를 포함하는 약학 조성물 |
| US11786529B2 (en) | 2017-11-29 | 2023-10-17 | Beigene Switzerland Gmbh | Treatment of indolent or aggressive B-cell lymphomas using a combination comprising BTK inhibitors |
| WO2019148150A1 (en) * | 2018-01-29 | 2019-08-01 | Dana-Farber Cancer Institute, Inc. | Degradation of bruton's tyrosine kinase (btk) by conjugation of btk inhibitors with e3 ligase ligand and methods of use |
| EP4212529B1 (en) | 2018-03-30 | 2025-01-29 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| FI4219492T3 (fi) | 2018-05-11 | 2025-02-17 | Incyte Corp | Heterosyklisiä yhdisteitä immunomodulaattoreina |
| JP2022521413A (ja) | 2019-02-22 | 2022-04-07 | クロノス バイオ インコーポレイテッド | Ｓｙｋ阻害剤としての縮合ピラジンの固体形態 |
| TWI856111B (zh) | 2019-06-10 | 2024-09-21 | 瑞士商百濟神州瑞士有限責任公司 | 一種含有布魯頓氏酪胺酸激酶抑制劑的口服固體錠劑及其製備方法 |
| CA3150434A1 (en) | 2019-08-09 | 2021-02-18 | Incyte Corporation | Salts of a pd-1/pd-l1 inhibitor |
| AR120109A1 (es) | 2019-09-30 | 2022-02-02 | Incyte Corp | Compuestos de pirido[3,2-d]pirimidina como inmunomoduladores |
| IL292524A (en) | 2019-11-11 | 2022-06-01 | Incyte Corp | Salts and crystalline forms of a pd-1/pd-l1 inhibitor |
| WO2021093817A1 (zh) * | 2019-11-15 | 2021-05-20 | 杭州和正医药有限公司 | 免疫调节化合物、组合物及其应用 |
| CN114380841A (zh) * | 2020-10-19 | 2022-04-22 | 南京正大天晴制药有限公司 | 作为akt抑制剂的三环喹唑啉或二氢喹唑啉化合物 |
| US11780836B2 (en) | 2020-11-06 | 2023-10-10 | Incyte Corporation | Process of preparing a PD-1/PD-L1 inhibitor |
| WO2022099075A1 (en) | 2020-11-06 | 2022-05-12 | Incyte Corporation | Crystalline form of a pd-1/pd-l1 inhibitor |
| PE20231438A1 (es) | 2020-11-06 | 2023-09-14 | Incyte Corp | Proceso para hacer un inhibidor de pd-1/pd-l1 y sales y formas cristalinas del mismo |
| US11786531B1 (en) | 2022-06-08 | 2023-10-17 | Beigene Switzerland Gmbh | Methods of treating B-cell proliferative disorder |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR042586A1 (es) * | 2001-02-15 | 2005-06-29 | Sugen Inc | 3-(4-amidopirrol-2-ilmetiliden)-2-indolinona como inhibidores de la protein quinasa; sus composiciones farmaceuticas; un metodo para la modulacion de la actividad catalitica de la proteinquinasa; un metodo para tratar o prevenir una afeccion relacionada con la proteinquinasa |
| US7405295B2 (en) * | 2003-06-04 | 2008-07-29 | Cgi Pharmaceuticals, Inc. | Certain imidazo[1,2-a]pyrazin-8-ylamines and method of inhibition of Bruton's tyrosine kinase by such compounds |
| CN101223141A (zh) * | 2005-03-10 | 2008-07-16 | Cgi药品股份有限公司 | 特定取代的酰胺，其制备方法和使用方法 |
| AR063706A1 (es) * | 2006-09-11 | 2009-02-11 | Cgi Pharmaceuticals Inc | Determinadas amidas sustituidas, el uso de las mismas para el tratamiento de enfermedades mediadas por la inhibicion de la actividad de btk y composiciones farmaceuticas que las comprenden. |
| US20100160292A1 (en) * | 2006-09-11 | 2010-06-24 | Cgi Pharmaceuticals, Inc | Kinase Inhibitors, and Methods of Using and Identifying Kinase Inhibitors |
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2008
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- 2008-09-19 BR BRPI0817130 patent/BRPI0817130A2/pt not_active Application Discontinuation
- 2008-09-19 KR KR1020107008468A patent/KR20100072032A/ko not_active Withdrawn
- 2008-09-19 CA CA2700443A patent/CA2700443A1/en not_active Abandoned
- 2008-09-19 AR ARP080104094A patent/AR068503A1/es unknown
- 2008-09-19 JP JP2010526003A patent/JP5485894B2/ja active Active
- 2008-09-19 TW TW097136216A patent/TWI423966B/zh not_active IP Right Cessation
- 2008-09-19 PE PE2008001640A patent/PE20091201A1/es not_active Application Discontinuation
- 2008-09-19 US US12/234,281 patent/US7884108B2/en active Active
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- 2008-09-19 CN CN2008801161200A patent/CN101861307B/zh active Active
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