JP2016517878A5 - - Google Patents
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- Publication number
- JP2016517878A5 JP2016517878A5 JP2016511152A JP2016511152A JP2016517878A5 JP 2016517878 A5 JP2016517878 A5 JP 2016517878A5 JP 2016511152 A JP2016511152 A JP 2016511152A JP 2016511152 A JP2016511152 A JP 2016511152A JP 2016517878 A5 JP2016517878 A5 JP 2016517878A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- methyl
- oxo
- dihydropyridin
- dimethyl
- 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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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 71
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 49
- 125000001072 heteroaryl group Chemical group 0.000 claims 43
- 125000003118 aryl group Chemical group 0.000 claims 37
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 31
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 30
- 229910052736 halogen Inorganic materials 0.000 claims 29
- 150000002367 halogens Chemical class 0.000 claims 29
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 24
- 150000003839 salts Chemical class 0.000 claims 22
- 229910052739 hydrogen Inorganic materials 0.000 claims 21
- 239000001257 hydrogen Substances 0.000 claims 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims 20
- 150000001875 compounds Chemical class 0.000 claims 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 16
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 15
- 150000001602 bicycloalkyls Chemical group 0.000 claims 14
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 229910052757 nitrogen Inorganic materials 0.000 claims 12
- -1 ethyl (tetrahydro-2H-pyran-4-yl) amino Chemical group 0.000 claims 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- 125000004043 oxo group Chemical group O=* 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 8
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- DAUYIKBTMNZABP-UHFFFAOYSA-N thiophene-3-carboxamide Chemical compound NC(=O)C=1C=CSC=1 DAUYIKBTMNZABP-UHFFFAOYSA-N 0.000 claims 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 6
- 125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims 6
- 125000006564 (C4-C8) cycloalkyl group Chemical group 0.000 claims 6
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 239000001301 oxygen Substances 0.000 claims 6
- 239000011593 sulfur Chemical group 0.000 claims 6
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 4
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 206010038389 Renal cancer Diseases 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 201000010982 kidney cancer Diseases 0.000 claims 4
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 3
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000002619 bicyclic group Chemical group 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- XHROKJJCFRMCBT-UHFFFAOYSA-N 5-[[4-(dimethylamino)cyclohexyl]-ethylamino]-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-4-methylthiophene-3-carboxamide Chemical compound S1C=C(C(=O)NCC=2C(NC(C)=CC=2C)=O)C(C)=C1N(CC)C1CCC(N(C)C)CC1 XHROKJJCFRMCBT-UHFFFAOYSA-N 0.000 claims 2
- 206010005003 Bladder cancer Diseases 0.000 claims 2
- 208000003174 Brain Neoplasms Diseases 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- IDUHGUNBWPHVAI-YOFSQIOKSA-N CC1=C(C(NC(=C1)C)=O)CNC(=O)C1=CSC(=C1C)C(CC)[C@@H]1CC[C@@H](CC1)N(C)C Chemical compound CC1=C(C(NC(=C1)C)=O)CNC(=O)C1=CSC(=C1C)C(CC)[C@@H]1CC[C@@H](CC1)N(C)C IDUHGUNBWPHVAI-YOFSQIOKSA-N 0.000 claims 2
- IDUHGUNBWPHVAI-ORXZLVCASA-N CCC([C@H]1CC[C@@H](CC1)N(C)C)c1scc(C(=O)NCc2c(C)cc(C)[nH]c2=O)c1C Chemical compound CCC([C@H]1CC[C@@H](CC1)N(C)C)c1scc(C(=O)NCc2c(C)cc(C)[nH]c2=O)c1C IDUHGUNBWPHVAI-ORXZLVCASA-N 0.000 claims 2
- 201000009030 Carcinoma Diseases 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 208000012609 Cowden disease Diseases 0.000 claims 2
- 201000002847 Cowden syndrome Diseases 0.000 claims 2
- 208000006168 Ewing Sarcoma Diseases 0.000 claims 2
- 208000007569 Giant Cell Tumors Diseases 0.000 claims 2
- 208000032612 Glial tumor Diseases 0.000 claims 2
- 206010018338 Glioma Diseases 0.000 claims 2
- 208000005726 Inflammatory Breast Neoplasms Diseases 0.000 claims 2
- 206010021980 Inflammatory carcinoma of the breast Diseases 0.000 claims 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 2
- 206010025323 Lymphomas Diseases 0.000 claims 2
- 208000000172 Medulloblastoma Diseases 0.000 claims 2
- 208000008770 Multiple Hamartoma Syndrome Diseases 0.000 claims 2
- 206010033128 Ovarian cancer Diseases 0.000 claims 2
- 206010061535 Ovarian 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
- 206010039491 Sarcoma Diseases 0.000 claims 2
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 2
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 2
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 2
- 208000008383 Wilms tumor Diseases 0.000 claims 2
- 210000000988 bone and bone Anatomy 0.000 claims 2
- 208000029742 colonic neoplasm Diseases 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 206010017758 gastric cancer Diseases 0.000 claims 2
- 208000005017 glioblastoma Diseases 0.000 claims 2
- 201000010536 head and neck cancer Diseases 0.000 claims 2
- 208000014829 head and neck neoplasm Diseases 0.000 claims 2
- 201000004653 inflammatory breast carcinoma Diseases 0.000 claims 2
- 208000032839 leukemia Diseases 0.000 claims 2
- 201000007270 liver cancer Diseases 0.000 claims 2
- 208000014018 liver neoplasm Diseases 0.000 claims 2
- 201000005202 lung cancer Diseases 0.000 claims 2
- 208000020816 lung neoplasm Diseases 0.000 claims 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 2
- 201000001441 melanoma Diseases 0.000 claims 2
- 201000008026 nephroblastoma Diseases 0.000 claims 2
- 201000008968 osteosarcoma Diseases 0.000 claims 2
- 201000002528 pancreatic cancer Diseases 0.000 claims 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 2
- 201000009410 rhabdomyosarcoma Diseases 0.000 claims 2
- 201000011549 stomach cancer Diseases 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 201000002510 thyroid cancer Diseases 0.000 claims 2
- 201000005112 urinary bladder cancer Diseases 0.000 claims 2
- FOOXUZRFPGZBNI-UHFFFAOYSA-N 2-bromo-5-(diethylamino)-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-4-methylthiophene-3-carboxamide Chemical compound CC1=C(N(CC)CC)SC(Br)=C1C(=O)NCC1=C(C)C=C(C)NC1=O FOOXUZRFPGZBNI-UHFFFAOYSA-N 0.000 claims 1
- XVRVJNZQOATEAP-UHFFFAOYSA-N 2-bromo-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-5-[ethyl(oxan-4-yl)amino]-4-methylthiophene-3-carboxamide Chemical compound S1C(Br)=C(C(=O)NCC=2C(NC(C)=CC=2C)=O)C(C)=C1N(CC)C1CCOCC1 XVRVJNZQOATEAP-UHFFFAOYSA-N 0.000 claims 1
- VPWRXOUDVYAELQ-UHFFFAOYSA-N 2-chloro-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-5-[ethyl(oxan-4-yl)amino]-4-methylthiophene-3-carboxamide Chemical compound S1C(Cl)=C(C(=O)NCC=2C(NC(C)=CC=2C)=O)C(C)=C1N(CC)C1CCOCC1 VPWRXOUDVYAELQ-UHFFFAOYSA-N 0.000 claims 1
- FRTKPKWRJMIGMN-UHFFFAOYSA-N 2-cyano-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-5-[ethyl(oxan-4-yl)amino]-4-methylthiophene-3-carboxamide Chemical compound S1C(C#N)=C(C(=O)NCC=2C(NC(C)=CC=2C)=O)C(C)=C1N(CC)C1CCOCC1 FRTKPKWRJMIGMN-UHFFFAOYSA-N 0.000 claims 1
- LVGCTQDARMZPSW-OAQYLSRUSA-N 5-[(1r)-1-[4-(dimethylamino)piperidin-1-yl]propyl]-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-4-methylthiophene-3-carboxamide Chemical compound N1([C@H](CC)C2=C(C(C(=O)NCC=3C(NC(C)=CC=3C)=O)=CS2)C)CCC(N(C)C)CC1 LVGCTQDARMZPSW-OAQYLSRUSA-N 0.000 claims 1
- LVGCTQDARMZPSW-NRFANRHFSA-N 5-[(1s)-1-[4-(dimethylamino)piperidin-1-yl]propyl]-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-4-methylthiophene-3-carboxamide Chemical compound N1([C@@H](CC)C2=C(C(C(=O)NCC=3C(NC(C)=CC=3C)=O)=CS2)C)CCC(N(C)C)CC1 LVGCTQDARMZPSW-NRFANRHFSA-N 0.000 claims 1
- LZBICHWHSABGJQ-YXSASFKJSA-N 5-[(z)-6-[4-(dimethylamino)piperidin-1-yl]hex-2-en-3-yl]-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-4-methylthiophene-3-carboxamide Chemical compound S1C=C(C(=O)NCC=2C(NC(C)=CC=2C)=O)C(C)=C1C(=C/C)\CCCN1CCC(N(C)C)CC1 LZBICHWHSABGJQ-YXSASFKJSA-N 0.000 claims 1
- OCVFHWCDYDBBRP-UHFFFAOYSA-N 5-[1-[4-(dimethylamino)piperidin-1-yl]ethyl]-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-4-methylthiophene-3-carboxamide Chemical compound S1C=C(C(=O)NCC=2C(NC(C)=CC=2C)=O)C(C)=C1C(C)N1CCC(N(C)C)CC1 OCVFHWCDYDBBRP-UHFFFAOYSA-N 0.000 claims 1
- MMBRIKLEHZRKNB-UHFFFAOYSA-N 5-[1-[4-(dimethylamino)piperidin-1-yl]ethyl]-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]thiophene-3-carboxamide Chemical compound C=1C(C(=O)NCC=2C(NC(C)=CC=2C)=O)=CSC=1C(C)N1CCC(N(C)C)CC1 MMBRIKLEHZRKNB-UHFFFAOYSA-N 0.000 claims 1
- LVGCTQDARMZPSW-UHFFFAOYSA-N 5-[1-[4-(dimethylamino)piperidin-1-yl]propyl]-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-4-methylthiophene-3-carboxamide Chemical compound S1C=C(C(=O)NCC=2C(NC(C)=CC=2C)=O)C(C)=C1C(CC)N1CCC(N(C)C)CC1 LVGCTQDARMZPSW-UHFFFAOYSA-N 0.000 claims 1
- VSNXIWYGHMHREB-UHFFFAOYSA-N 5-[ethyl(oxan-4-yl)amino]-4-methyl-n-[(1,4,6-trimethyl-2-oxopyridin-3-yl)methyl]thiophene-3-carboxamide Chemical compound S1C=C(C(=O)NCC=2C(N(C)C(C)=CC=2C)=O)C(C)=C1N(CC)C1CCOCC1 VSNXIWYGHMHREB-UHFFFAOYSA-N 0.000 claims 1
- PIUDMQZOXJMZKR-UHFFFAOYSA-N 5-chloro-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-4-[ethyl(oxan-4-yl)amino]-3-methylthiophene-2-carboxamide Chemical compound ClC=1SC(C(=O)NCC=2C(NC(C)=CC=2C)=O)=C(C)C=1N(CC)C1CCOCC1 PIUDMQZOXJMZKR-UHFFFAOYSA-N 0.000 claims 1
- DULCDCQEAIHKPM-IYARVYRRSA-N BrC=1SC(=C(C1C(=O)NCC=1C(NC(=CC1C)C)=O)C)N(CC)[C@@H]1CC[C@H](CC1)N(C)C Chemical compound BrC=1SC(=C(C1C(=O)NCC=1C(NC(=CC1C)C)=O)C)N(CC)[C@@H]1CC[C@H](CC1)N(C)C DULCDCQEAIHKPM-IYARVYRRSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- XCDDMQLPMMUTOY-WGSAOQKQSA-N CC1=C(C(NC(=C1)C)=O)CNC(=O)C1=CSC(=C1C)C(=CC)[C@@H]1CC[C@H](CC1)N(C)C Chemical compound CC1=C(C(NC(=C1)C)=O)CNC(=O)C1=CSC(=C1C)C(=CC)[C@@H]1CC[C@H](CC1)N(C)C XCDDMQLPMMUTOY-WGSAOQKQSA-N 0.000 claims 1
- LLXDKFMURVBHJV-IWZNKUOBSA-N CC1=C(C(NC(=C1)C)=O)CNC(=O)C1=CSC(=C1C)C(O)[C@@H]1CC[C@H](CC1)N(C)C Chemical compound CC1=C(C(NC(=C1)C)=O)CNC(=O)C1=CSC(=C1C)C(O)[C@@H]1CC[C@H](CC1)N(C)C LLXDKFMURVBHJV-IWZNKUOBSA-N 0.000 claims 1
- OEOBFVJMSOTVQD-KDURUIRLSA-N CC1=C(C(NC(=C1)C)=O)CNC(=O)C=1SC=C(C1C)N(CC)[C@@H]1CC[C@@H](CC1)N(C)C Chemical compound CC1=C(C(NC(=C1)C)=O)CNC(=O)C=1SC=C(C1C)N(CC)[C@@H]1CC[C@@H](CC1)N(C)C OEOBFVJMSOTVQD-KDURUIRLSA-N 0.000 claims 1
- OEOBFVJMSOTVQD-WGSAOQKQSA-N CC1=C(C(NC(=C1)C)=O)CNC(=O)C=1SC=C(C1C)N(CC)[C@@H]1CC[C@H](CC1)N(C)C Chemical compound CC1=C(C(NC(=C1)C)=O)CNC(=O)C=1SC=C(C1C)N(CC)[C@@H]1CC[C@H](CC1)N(C)C OEOBFVJMSOTVQD-WGSAOQKQSA-N 0.000 claims 1
- LQRSUXVZQNCRKZ-JHJOSGQCSA-N CCC([C@H]1CC[C@H](N)CC1)c1scc(C(=O)NCc2c(C)cc(C)[nH]c2=O)c1C Chemical compound CCC([C@H]1CC[C@H](N)CC1)c1scc(C(=O)NCc2c(C)cc(C)[nH]c2=O)c1C LQRSUXVZQNCRKZ-JHJOSGQCSA-N 0.000 claims 1
- ANOOOFTUEHAIIC-HZCBDIJESA-N CCN([C@H]1CC[C@@H](CC1)N(C)C)c1sc(-c2ccoc2)c(C(=O)NCc2c(C)cc(C)[nH]c2=O)c1C Chemical compound CCN([C@H]1CC[C@@H](CC1)N(C)C)c1sc(-c2ccoc2)c(C(=O)NCc2c(C)cc(C)[nH]c2=O)c1C ANOOOFTUEHAIIC-HZCBDIJESA-N 0.000 claims 1
- XXQHACAXRPGDPN-WGSAOQKQSA-N CCN([C@H]1CC[C@@H](CC1)N(C)C)c1sc(C#N)c(C(=O)NCc2c(C)cc(C)[nH]c2=O)c1C Chemical compound CCN([C@H]1CC[C@@H](CC1)N(C)C)c1sc(C#N)c(C(=O)NCc2c(C)cc(C)[nH]c2=O)c1C XXQHACAXRPGDPN-WGSAOQKQSA-N 0.000 claims 1
- OPQWDNJKKMJJBB-IYARVYRRSA-N CN([C@@H]1CC[C@H](CC1)N(C1=C(C(=CS1)C(=O)NCC=1C(NC(=CC1OC)C)=O)C)CC)C Chemical compound CN([C@@H]1CC[C@H](CC1)N(C1=C(C(=CS1)C(=O)NCC=1C(NC(=CC1OC)C)=O)C)CC)C OPQWDNJKKMJJBB-IYARVYRRSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 102100038970 Histone-lysine N-methyltransferase EZH2 Human genes 0.000 claims 1
- 101000882127 Homo sapiens Histone-lysine N-methyltransferase EZH2 Proteins 0.000 claims 1
- JMYOSDLLACUDBE-QAQDUYKDSA-N N[C@@H]1CC[C@H](CC1)/C(=CC)/C1=C(C(=CS1)C(=O)NCC=1C(NC(=CC1C)C)=O)C Chemical compound N[C@@H]1CC[C@H](CC1)/C(=CC)/C1=C(C(=CS1)C(=O)NCC=1C(NC(=CC1C)C)=O)C JMYOSDLLACUDBE-QAQDUYKDSA-N 0.000 claims 1
- SELHOZRPYAMUKI-OSPTYYIOSA-N N[C@@H]1CC[C@H](CC1)C(C1=C(C(=CS1)C(=O)NCC=1C(NC(=CC1C)C)=O)C)O Chemical compound N[C@@H]1CC[C@H](CC1)C(C1=C(C(=CS1)C(=O)NCC=1C(NC(=CC1C)C)=O)C)O SELHOZRPYAMUKI-OSPTYYIOSA-N 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- ZZWWTDIYKHELAP-UHFFFAOYSA-N n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-3-methyl-4-propan-2-yloxythiophene-2-carboxamide Chemical compound CC(C)OC1=CSC(C(=O)NCC=2C(NC(C)=CC=2C)=O)=C1C ZZWWTDIYKHELAP-UHFFFAOYSA-N 0.000 claims 1
- DNSRVUFQXXUPCK-UHFFFAOYSA-N n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-4-[ethyl(oxan-4-yl)amino]-3-methylthiophene-2-carboxamide Chemical compound C=1SC(C(=O)NCC=2C(NC(C)=CC=2C)=O)=C(C)C=1N(CC)C1CCOCC1 DNSRVUFQXXUPCK-UHFFFAOYSA-N 0.000 claims 1
- GZHOTTJMYDUDKU-UHFFFAOYSA-N n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-4-methyl-5-(1,2,3,4-tetrahydroisoquinolin-5-yl)thiophene-3-carboxamide Chemical compound C=1SC(C=2C=3CCNCC=3C=CC=2)=C(C)C=1C(=O)NCC1=C(C)C=C(C)NC1=O GZHOTTJMYDUDKU-UHFFFAOYSA-N 0.000 claims 1
- OBWHFTGGXGNDQX-UHFFFAOYSA-N n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-4-methyl-5-(1-piperidin-4-ylidenepropyl)thiophene-3-carboxamide Chemical compound C1CNCCC1=C(CC)C(=C1C)SC=C1C(=O)NCC1=C(C)C=C(C)NC1=O OBWHFTGGXGNDQX-UHFFFAOYSA-N 0.000 claims 1
- PJCORCKTZOPQIB-UHFFFAOYSA-N n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-4-methyl-5-(1-piperidin-4-ylpropyl)thiophene-3-carboxamide Chemical compound S1C=C(C(=O)NCC=2C(NC(C)=CC=2C)=O)C(C)=C1C(CC)C1CCNCC1 PJCORCKTZOPQIB-UHFFFAOYSA-N 0.000 claims 1
- HREMAGBXPZHMJC-UHFFFAOYSA-N n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-4-methyl-5-(2-methylpyrrolidin-1-yl)thiophene-3-carboxamide Chemical compound CC1CCCN1C1=C(C)C(C(=O)NCC=2C(NC(C)=CC=2C)=O)=CS1 HREMAGBXPZHMJC-UHFFFAOYSA-N 0.000 claims 1
- QTGCEAWJQNDFCV-UHFFFAOYSA-N n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-4-methyl-5-(2-piperidin-4-ylpiperidin-1-yl)thiophene-3-carboxamide Chemical compound CC=1C(C(=O)NCC=2C(NC(C)=CC=2C)=O)=CSC=1N1CCCCC1C1CCNCC1 QTGCEAWJQNDFCV-UHFFFAOYSA-N 0.000 claims 1
- SPEWFOBJMMAASC-UHFFFAOYSA-N n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-4-methyl-5-(2-piperidin-4-ylpyrrolidin-1-yl)thiophene-3-carboxamide Chemical compound CC=1C(C(=O)NCC=2C(NC(C)=CC=2C)=O)=CSC=1N1CCCC1C1CCNCC1 SPEWFOBJMMAASC-UHFFFAOYSA-N 0.000 claims 1
- KVWSOQMUSXAHGJ-YAXRCOADSA-N n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-4-methyl-5-[(e)-1-piperidin-4-ylprop-1-enyl]thiophene-3-carboxamide Chemical compound S1C=C(C(=O)NCC=2C(NC(C)=CC=2C)=O)C(C)=C1C(=C/C)/C1CCNCC1 KVWSOQMUSXAHGJ-YAXRCOADSA-N 0.000 claims 1
- XPVCBYVRTZJYLK-UHFFFAOYSA-N n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-5-[ethyl(oxan-4-yl)amino]-2,4-dimethylthiophene-3-carboxamide Chemical compound S1C(C)=C(C(=O)NCC=2C(NC(C)=CC=2C)=O)C(C)=C1N(CC)C1CCOCC1 XPVCBYVRTZJYLK-UHFFFAOYSA-N 0.000 claims 1
- FPNCHTAWQWSLNX-UHFFFAOYSA-N n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-5-[ethyl(oxan-4-yl)amino]-2-(furan-2-yl)-4-methylthiophene-3-carboxamide Chemical compound S1C(C=2OC=CC=2)=C(C(=O)NCC=2C(NC(C)=CC=2C)=O)C(C)=C1N(CC)C1CCOCC1 FPNCHTAWQWSLNX-UHFFFAOYSA-N 0.000 claims 1
- DPMPQZDRSNAUCN-UHFFFAOYSA-N n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-5-[ethyl(oxan-4-yl)amino]-2-(furan-3-yl)-4-methylthiophene-3-carboxamide Chemical compound S1C(C2=COC=C2)=C(C(=O)NCC=2C(NC(C)=CC=2C)=O)C(C)=C1N(CC)C1CCOCC1 DPMPQZDRSNAUCN-UHFFFAOYSA-N 0.000 claims 1
- HYFUXDXOXFKDQJ-UHFFFAOYSA-N n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-5-[ethyl(oxan-4-yl)amino]-4-methyl-2-(1-methylsulfonylpyrrolidin-3-yl)thiophene-3-carboxamide Chemical compound S1C(C2CN(CC2)S(C)(=O)=O)=C(C(=O)NCC=2C(NC(C)=CC=2C)=O)C(C)=C1N(CC)C1CCOCC1 HYFUXDXOXFKDQJ-UHFFFAOYSA-N 0.000 claims 1
- DWNBXLZQSMCDBO-UHFFFAOYSA-N n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-5-[ethyl(oxan-4-yl)amino]-4-methyl-2-(4-methylpiperazin-1-yl)thiophene-3-carboxamide Chemical compound S1C(N2CCN(C)CC2)=C(C(=O)NCC=2C(NC(C)=CC=2C)=O)C(C)=C1N(CC)C1CCOCC1 DWNBXLZQSMCDBO-UHFFFAOYSA-N 0.000 claims 1
- SMVSONNNCOXRPA-UHFFFAOYSA-N n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-5-[ethyl(oxan-4-yl)amino]-4-methyl-2-pyrrolidin-3-ylthiophene-3-carboxamide Chemical compound S1C(C2CNCC2)=C(C(=O)NCC=2C(NC(C)=CC=2C)=O)C(C)=C1N(CC)C1CCOCC1 SMVSONNNCOXRPA-UHFFFAOYSA-N 0.000 claims 1
- JCQDRGZRLNNKJK-UHFFFAOYSA-N n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-5-[ethyl(oxan-4-yl)amino]-4-methylthiophene-3-carboxamide Chemical compound S1C=C(C(=O)NCC=2C(NC(C)=CC=2C)=O)C(C)=C1N(CC)C1CCOCC1 JCQDRGZRLNNKJK-UHFFFAOYSA-N 0.000 claims 1
- KUJUZLBGRRXLMH-UHFFFAOYSA-N n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-5-[ethyl(piperidin-4-yl)amino]-4-methylthiophene-3-carboxamide Chemical compound S1C=C(C(=O)NCC=2C(NC(C)=CC=2C)=O)C(C)=C1N(CC)C1CCNCC1 KUJUZLBGRRXLMH-UHFFFAOYSA-N 0.000 claims 1
- PUAMXEYBUKFNAB-UHFFFAOYSA-N n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-5-[ethyl-(1-propan-2-ylpiperidin-4-yl)amino]-4-methylthiophene-3-carboxamide Chemical compound S1C=C(C(=O)NCC=2C(NC(C)=CC=2C)=O)C(C)=C1N(CC)C1CCN(C(C)C)CC1 PUAMXEYBUKFNAB-UHFFFAOYSA-N 0.000 claims 1
- FZYCWJYPPHUYEK-UHFFFAOYSA-N n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-5-[ethyl-(3-fluoropiperidin-4-yl)amino]-4-methylthiophene-3-carboxamide Chemical compound S1C=C(C(=O)NCC=2C(NC(C)=CC=2C)=O)C(C)=C1N(CC)C1CCNCC1F FZYCWJYPPHUYEK-UHFFFAOYSA-N 0.000 claims 1
- FBXFKRLTSXFVRZ-UHFFFAOYSA-N n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-5-[ethyl-[4-[ethyl(methyl)amino]cyclohexyl]amino]-4-methylthiophene-3-carboxamide Chemical compound C1CC(N(C)CC)CCC1N(CC)C1=C(C)C(C(=O)NCC=2C(NC(C)=CC=2C)=O)=CS1 FBXFKRLTSXFVRZ-UHFFFAOYSA-N 0.000 claims 1
- YGPOYOZOXJDGSV-UHFFFAOYSA-N n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-5-[hydroxy(piperidin-4-yl)methyl]-4-methylthiophene-3-carboxamide Chemical compound CC=1C(C(=O)NCC=2C(NC(C)=CC=2C)=O)=CSC=1C(O)C1CCNCC1 YGPOYOZOXJDGSV-UHFFFAOYSA-N 0.000 claims 1
- XBXCNNQPRYLIDE-UHFFFAOYSA-M n-tert-butylcarbamate Chemical compound CC(C)(C)NC([O-])=O XBXCNNQPRYLIDE-UHFFFAOYSA-M 0.000 claims 1
- 125000003566 oxetanyl group Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims 1
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- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
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| CA2862289C (en) * | 2012-02-10 | 2019-11-26 | Constellation Pharmaceuticals, Inc. | Modulators of methyl modifying enzymes, compositions and uses thereof |
| KR102021642B1 (ko) | 2012-10-15 | 2019-09-16 | 에피자임, 인코포레이티드 | 암을 치료하는 방법 |
| US9505745B2 (en) * | 2013-04-30 | 2016-11-29 | Glaxosmithkline Intellectual Property (No. 2) Limited | Enhancer of zeste homolog 2 inhibitors |
| EP3019494B1 (en) | 2013-07-10 | 2017-06-21 | Glaxosmithkline Intellectual Property (No. 2) Limited | Enhancer of zeste homolog 2 inhibitors |
| EP3102568B1 (en) | 2014-02-06 | 2018-06-27 | Heptares Therapeutics Limited | Bicyclic aza compounds as muscarinic m1 receptor agonists. |
| CN107148419A (zh) * | 2014-10-28 | 2017-09-08 | 葛兰素史密斯克莱知识产权（第2 号）有限公司 | Zeste增强子同源物2抑制剂 |
| TW201636344A (zh) | 2014-12-05 | 2016-10-16 | 美國禮來大藥廠 | Ｅｚｈ２抑制劑 |
| UY36758A (es) * | 2015-06-30 | 2016-12-30 | Glaxosmithkline Ip No 2 Ltd | Inhibidores del potenciador del homólogo zeste 2 |
| CN108025191A (zh) | 2015-08-24 | 2018-05-11 | Epizyme股份有限公司 | 治疗癌症的方法 |
| TW201718598A (zh) * | 2015-08-27 | 2017-06-01 | 美國禮來大藥廠 | Ｅｚｈ２抑制劑 |
| US20190070188A1 (en) * | 2015-11-06 | 2019-03-07 | Epizyme, Inc. | Pediatric dosing for treatment of cancer with an ezh2 inhibitor |
| WO2017084494A1 (zh) | 2015-11-19 | 2017-05-26 | 江苏恒瑞医药股份有限公司 | 苯并呋喃类衍生物、其制备方法及其在医药上的应用 |
| MX2018013519A (es) * | 2016-05-05 | 2019-03-14 | Glaxosmithkline Ip No 2 Ltd | Inhibidores del potenciador del homologo zeste 2. |
| US20170337814A1 (en) * | 2016-05-20 | 2017-11-23 | Donald Edward Morgan | Safety alerting drivers device and system |
| AU2017323112B2 (en) | 2016-09-07 | 2020-11-26 | Haihe Biopharma Co., Ltd. | Pyrido five-element aromatic ring compound, preparation method therefor and use thereof |
| WO2018125983A1 (en) | 2016-12-30 | 2018-07-05 | Mitobridge, Inc. | Oxopyridine derivatives useful as aminocarboxymuconate semialdehyde decarboxylase (acmsd) inhibitors |
| US10266542B2 (en) | 2017-03-15 | 2019-04-23 | Mirati Therapeutics, Inc. | EZH2 inhibitors |
| NZ766447A (en) | 2018-01-31 | 2021-12-24 | Mirati Therapeutics Inc | Prc2 inhibitors |
| JP2021531340A (ja) | 2018-07-09 | 2021-11-18 | フォンダシヨン、アジール、デ、アブグルスFondation Asile Des Aveugles | 眼障害を治療するためのｐｒｃ２サブユニットの阻害 |
| JP7624404B2 (ja) | 2019-04-22 | 2025-01-30 | ミラティ セラピューティクス，インク． | Ｐｒｃ２阻害剤としてのナフチリジン誘導体 |
| CN113544130B (zh) * | 2019-05-31 | 2024-01-09 | 西藏海思科制药有限公司 | 一种btk抑制剂环衍生物及其制备方法和药学上的应用 |
| AU2020288563A1 (en) | 2019-06-05 | 2022-01-06 | Mirati Therapeutics, Inc. | Imidazo(1,2-c)pyrimidine derivatives as PRC2 inhibitors for treating cancer |
| CN114555112A (zh) | 2019-08-22 | 2022-05-27 | 朱诺治疗学股份有限公司 | T细胞疗法和zeste增强子同源物2(ezh2)抑制剂的组合疗法及相关方法 |
| CN110964200A (zh) * | 2019-12-19 | 2020-04-07 | 新纳奇材料科技江苏有限公司 | 一种基于聚硅氧烷馏出物的羟基封端聚硅氧烷的制备方法 |
| WO2021129629A1 (zh) * | 2019-12-23 | 2021-07-01 | 四川海思科制药有限公司 | Zeste增强子同源物2抑制剂及其用途 |
| CN111233768B (zh) * | 2020-03-18 | 2021-08-03 | 徐州圣元化工有限公司 | 一种3-(二氟甲基)-1-甲基-1h-吡唑-4-羧酸乙酯的制备方法 |
| KR20250040894A (ko) | 2022-05-25 | 2025-03-25 | 이케나 온콜로지, 인코포레이티드 | Mek 억제제 및 이의 용도 |
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| CN1989131A (zh) * | 2004-03-30 | 2007-06-27 | 希龙公司 | 取代的噻吩衍生物用作抗癌药 |
| US7696352B2 (en) * | 2004-06-18 | 2010-04-13 | Millennium Pharmaceuticals, Inc. | Factor Xa inhibitors |
| AU2006325746A1 (en) | 2005-12-14 | 2007-06-21 | Bristol-Myers Squibb Company | Six-membered heterocycles useful as serine protease inhibitors |
| BR112012002336A2 (pt) * | 2009-08-07 | 2016-05-31 | Merck Patent Gmbh | compostos aza-heterocíclicos |
| ES2528269T3 (es) | 2010-05-07 | 2015-02-06 | Glaxosmithkline Llc | Azaindazoles |
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| WO2011140325A1 (en) * | 2010-05-07 | 2011-11-10 | Glaxosmithkline Llc | Indazoles |
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| EP3323820B1 (en) | 2011-02-28 | 2023-05-10 | Epizyme, Inc. | Substituted 6,5-fused bicyclic heteroaryl compounds |
| JO3363B1 (ar) | 2011-04-13 | 2019-03-13 | Epizyme Inc | مركبات بنزين مستبدلة بأريل أو أريل غير متجانس |
| TW201733984A (zh) | 2011-04-13 | 2017-10-01 | 雅酶股份有限公司 | 經取代之苯化合物 |
| BR112014007603A2 (pt) * | 2011-09-30 | 2017-06-13 | Glaxosmithkline Llc | métodos de tratamento do câncer |
| CA2862289C (en) | 2012-02-10 | 2019-11-26 | Constellation Pharmaceuticals, Inc. | Modulators of methyl modifying enzymes, compositions and uses thereof |
| DK3628670T3 (da) | 2012-04-13 | 2022-12-05 | Epizyme Inc | Saltform til ezh2-hæmning |
| US9562041B2 (en) | 2012-05-16 | 2017-02-07 | Glaxosmithkline Llc | Enhancer of zeste homolog 2 inhibitors |
| US9505745B2 (en) * | 2013-04-30 | 2016-11-29 | Glaxosmithkline Intellectual Property (No. 2) Limited | Enhancer of zeste homolog 2 inhibitors |
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