JP5485894B2 - 置換アミド、その製造方法、及びその使用方法 - Google Patents

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Publication number

JP5485894B2

JP5485894B2 JP2010526003A JP2010526003A JP5485894B2 JP 5485894 B2 JP5485894 B2 JP 5485894B2 JP 2010526003 A JP2010526003 A JP 2010526003A JP 2010526003 A JP2010526003 A JP 2010526003A JP 5485894 B2 JP5485894 B2 JP 5485894B2

Authority

JP

Japan

Prior art keywords

methyl

oxo

amino

carboxamide

phenyl

Prior art date

2007-09-20

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.)

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• 238000000034 method Methods 0.000 title description 40
• 238000004519 manufacturing process Methods 0.000 title description 7
• 150000001408 amides Chemical class 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims description 220
• 229910052757 nitrogen Inorganic materials 0.000 claims description 105
• 239000000203 mixture Substances 0.000 claims description 102
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 99
• -1 N- methylpiperazinyl Chemical group 0.000 claims description 83
• 230000000694 effects Effects 0.000 claims description 61
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 51
• 229910052739 hydrogen Inorganic materials 0.000 claims description 46
• 201000010099 disease Diseases 0.000 claims description 35
• 230000005764 inhibitory process Effects 0.000 claims description 35
• 150000003839 salts Chemical class 0.000 claims description 31
• 229910052799 carbon Inorganic materials 0.000 claims description 29
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 26
• 239000012453 solvate Substances 0.000 claims description 24
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 23
• 239000008194 pharmaceutical composition Substances 0.000 claims description 22
• 238000011282 treatment Methods 0.000 claims description 22
• 206010028980 Neoplasm Diseases 0.000 claims description 21
• 208000010668 atopic eczema Diseases 0.000 claims description 19
• 201000011510 cancer Diseases 0.000 claims description 19
• 230000000172 allergic effect Effects 0.000 claims description 17
• 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 description 16
• 208000035475 disorder Diseases 0.000 claims description 16
• 208000027866 inflammatory disease Diseases 0.000 claims description 16
• 208000023275 Autoimmune disease Diseases 0.000 claims description 15
• 125000000217 alkyl group Chemical group 0.000 claims description 15
• 238000002360 preparation method Methods 0.000 claims description 14
• 229910052717 sulfur Inorganic materials 0.000 claims description 13
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
• 208000020084 Bone disease Diseases 0.000 claims description 11
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
• 125000001424 substituent group Chemical group 0.000 claims description 10
• 230000001154 acute effect Effects 0.000 claims description 9
• 206010061218 Inflammation Diseases 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 8
• 230000004054 inflammatory process Effects 0.000 claims description 8
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 8
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
• 239000002671 adjuvant Substances 0.000 claims description 6
• 230000014509 gene expression Effects 0.000 claims description 6
• 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 description 6
• 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 description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 208000003950 B-cell lymphoma Diseases 0.000 claims description 5
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
• 208000004736 B-Cell Leukemia Diseases 0.000 claims description 4
• 125000002393 azetidinyl group Chemical group 0.000 claims description 4
• 239000000969 carrier Substances 0.000 claims description 4
• 125000002757 morpholinyl group Chemical group 0.000 claims description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
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