JP2013528591A5 - - Google Patents
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- Publication number
- JP2013528591A5 JP2013528591A5 JP2013509260A JP2013509260A JP2013528591A5 JP 2013528591 A5 JP2013528591 A5 JP 2013528591A5 JP 2013509260 A JP2013509260 A JP 2013509260A JP 2013509260 A JP2013509260 A JP 2013509260A JP 2013528591 A5 JP2013528591 A5 JP 2013528591A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- alkyl
- oxo
- indazole
- carboxamide
- 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 substituted Chemical class 0.000 claims description 120
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 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 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 2
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 54
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 49
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 44
- 125000001072 heteroaryl group Chemical group 0.000 claims 43
- 125000003118 aryl group Chemical group 0.000 claims 40
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 36
- 125000005843 halogen group Chemical group 0.000 claims 30
- 229910052739 hydrogen Inorganic materials 0.000 claims 27
- 125000004093 cyano group Chemical group *C#N 0.000 claims 26
- 239000001257 hydrogen Substances 0.000 claims 26
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 22
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 21
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 16
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 15
- 125000000217 alkyl group Chemical group 0.000 claims 14
- 150000001602 bicycloalkyls Chemical group 0.000 claims 14
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 12
- 150000002431 hydrogen Chemical class 0.000 claims 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 12
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 11
- 229910052760 oxygen Inorganic materials 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 11
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 8
- 125000003282 alkyl amino group Chemical group 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 7
- 150000003857 carboxamides Chemical class 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
- 125000003107 substituted aryl group Chemical group 0.000 claims 5
- 229910052717 sulfur Chemical group 0.000 claims 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 4
- 125000004442 acylamino group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 3
- 208000008770 Multiple Hamartoma Syndrome Diseases 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 239000011593 sulfur Chemical group 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims 2
- RCYCPGOMWYHJQG-UHFFFAOYSA-N 6-[3-[(dimethylamino)methyl]phenyl]-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-1-propan-2-ylindazole-4-carboxamide Chemical compound C1=C2N(C(C)C)N=CC2=C(C(=O)NCC=2C(NC(C)=CC=2C)=O)C=C1C1=CC=CC(CN(C)C)=C1 RCYCPGOMWYHJQG-UHFFFAOYSA-N 0.000 claims 2
- FWNJJCIQEURUTI-UHFFFAOYSA-N 6-bromo-1-cyclopentyl-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]indazole-4-carboxamide Chemical compound O=C1NC(C)=CC(C)=C1CNC(=O)C1=CC(Br)=CC2=C1C=NN2C1CCCC1 FWNJJCIQEURUTI-UHFFFAOYSA-N 0.000 claims 2
- RNEUKQLFDMRMOV-UHFFFAOYSA-N 6-bromo-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-1-propan-2-ylindazole-4-carboxamide Chemical compound C1=C(Br)C=C2N(C(C)C)N=CC2=C1C(=O)NCC1=C(C)C=C(C)NC1=O RNEUKQLFDMRMOV-UHFFFAOYSA-N 0.000 claims 2
- GYXRMOLRJODPHM-UHFFFAOYSA-N 6-bromo-n-[(6-methyl-2-oxo-4-propan-2-yl-1h-pyridin-3-yl)methyl]-1-propan-2-ylindazole-4-carboxamide Chemical compound C1=C(C)NC(=O)C(CNC(=O)C=2C=3C=NN(C=3C=C(Br)C=2)C(C)C)=C1C(C)C GYXRMOLRJODPHM-UHFFFAOYSA-N 0.000 claims 2
- IGRUIXGIDUANQR-UHFFFAOYSA-N 6-bromo-n-[(6-methyl-2-oxo-4-propyl-1h-pyridin-3-yl)methyl]-1-propan-2-ylindazole-4-carboxamide Chemical compound C1=C(C)NC(=O)C(CNC(=O)C=2C=3C=NN(C=3C=C(Br)C=2)C(C)C)=C1CCC IGRUIXGIDUANQR-UHFFFAOYSA-N 0.000 claims 2
- 201000002847 Cowden syndrome Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 2
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 claims 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims 2
- DFOGUQBUSZYUGI-UHFFFAOYSA-N n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-3-methyl-1-propan-2-yl-6-pyridin-3-ylindazole-4-carboxamide Chemical compound C1=C2N(C(C)C)N=C(C)C2=C(C(=O)NCC=2C(NC(C)=CC=2C)=O)C=C1C1=CC=CN=C1 DFOGUQBUSZYUGI-UHFFFAOYSA-N 0.000 claims 2
- UNEADCSXFLNROG-UHFFFAOYSA-N n-[(6-methyl-2-oxo-4-propyl-1h-pyridin-3-yl)methyl]-1-propan-2-yl-6-thiophen-3-ylindazole-4-carboxamide Chemical compound C1=C(C)NC(=O)C(CNC(=O)C=2C=3C=NN(C=3C=C(C=2)C2=CSC=C2)C(C)C)=C1CCC UNEADCSXFLNROG-UHFFFAOYSA-N 0.000 claims 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 2
- 150000003536 tetrazoles Chemical class 0.000 claims 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 2
- 229930192474 thiophene Natural products 0.000 claims 2
- 150000003852 triazoles Chemical class 0.000 claims 2
- JWEHQNHCUMVORM-UHFFFAOYSA-N 1-cyclopentyl-6-[4-[(dimethylamino)methyl]phenyl]-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]indazole-4-carboxamide Chemical compound C1=CC(CN(C)C)=CC=C1C1=CC(C(=O)NCC=2C(NC(C)=CC=2C)=O)=C(C=NN2C3CCCC3)C2=C1 JWEHQNHCUMVORM-UHFFFAOYSA-N 0.000 claims 1
- IHANFWVIJQVHTL-UHFFFAOYSA-N 1-cyclopentyl-6-cyclopropylsulfonyl-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]indazole-4-carboxamide Chemical compound O=C1NC(C)=CC(C)=C1CNC(=O)C1=CC(S(=O)(=O)C2CC2)=CC2=C1C=NN2C1CCCC1 IHANFWVIJQVHTL-UHFFFAOYSA-N 0.000 claims 1
- UPQLMUFNEBEHQI-UHFFFAOYSA-N 1-cyclopentyl-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-6-(1-methylpyrazol-4-yl)indazole-4-carboxamide Chemical compound O=C1NC(C)=CC(C)=C1CNC(=O)C1=CC(C2=CN(C)N=C2)=CC2=C1C=NN2C1CCCC1 UPQLMUFNEBEHQI-UHFFFAOYSA-N 0.000 claims 1
- BRXHWPIJWBNLHF-UHFFFAOYSA-N 1-cyclopentyl-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-6-(2-oxo-1,3-dihydrobenzimidazol-5-yl)indazole-4-carboxamide Chemical compound O=C1NC(C)=CC(C)=C1CNC(=O)C1=CC(C=2C=C3NC(=O)NC3=CC=2)=CC2=C1C=NN2C1CCCC1 BRXHWPIJWBNLHF-UHFFFAOYSA-N 0.000 claims 1
- IKIQTCNQNUBTTO-UHFFFAOYSA-N 1-cyclopentyl-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-6-(2-piperazin-1-ylpyrimidin-5-yl)indazole-4-carboxamide Chemical compound O=C1NC(C)=CC(C)=C1CNC(=O)C1=CC(C=2C=NC(=NC=2)N2CCNCC2)=CC2=C1C=NN2C1CCCC1 IKIQTCNQNUBTTO-UHFFFAOYSA-N 0.000 claims 1
- ZODCCNIZBNJOMW-UHFFFAOYSA-N 1-cyclopentyl-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-6-(3-hydroxy-3-methylbut-1-ynyl)indazole-4-carboxamide Chemical compound O=C1NC(C)=CC(C)=C1CNC(=O)C1=CC(C#CC(C)(C)O)=CC2=C1C=NN2C1CCCC1 ZODCCNIZBNJOMW-UHFFFAOYSA-N 0.000 claims 1
- PDAWBBBUAGXSFV-UHFFFAOYSA-N 1-cyclopentyl-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-6-(3-pyrrolidin-1-ylphenyl)indazole-4-carboxamide Chemical compound O=C1NC(C)=CC(C)=C1CNC(=O)C1=CC(C=2C=C(C=CC=2)N2CCCC2)=CC2=C1C=NN2C1CCCC1 PDAWBBBUAGXSFV-UHFFFAOYSA-N 0.000 claims 1
- YJMDLNMTFKVIFD-UHFFFAOYSA-N 1-cyclopentyl-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-6-(4-fluorophenyl)indazole-4-carboxamide Chemical compound O=C1NC(C)=CC(C)=C1CNC(=O)C1=CC(C=2C=CC(F)=CC=2)=CC2=C1C=NN2C1CCCC1 YJMDLNMTFKVIFD-UHFFFAOYSA-N 0.000 claims 1
- ADVCBSKDUUSYRU-UHFFFAOYSA-N 1-cyclopentyl-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-6-(4-methylthiophen-2-yl)indazole-4-carboxamide Chemical compound CC1=CSC(C=2C=C3N(C4CCCC4)N=CC3=C(C(=O)NCC=3C(NC(C)=CC=3C)=O)C=2)=C1 ADVCBSKDUUSYRU-UHFFFAOYSA-N 0.000 claims 1
- SDGGHUNWGPGWKS-UHFFFAOYSA-N 1-cyclopentyl-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-6-(6-methoxypyridin-3-yl)indazole-4-carboxamide Chemical compound C1=NC(OC)=CC=C1C1=CC(C(=O)NCC=2C(NC(C)=CC=2C)=O)=C(C=NN2C3CCCC3)C2=C1 SDGGHUNWGPGWKS-UHFFFAOYSA-N 0.000 claims 1
- WUVLORKOXWDSRM-UHFFFAOYSA-N 1-cyclopentyl-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-6-(6-methylpyridin-3-yl)indazole-4-carboxamide Chemical compound C1=NC(C)=CC=C1C1=CC(C(=O)NCC=2C(NC(C)=CC=2C)=O)=C(C=NN2C3CCCC3)C2=C1 WUVLORKOXWDSRM-UHFFFAOYSA-N 0.000 claims 1
- RFXJKNSXOOYXNC-UHFFFAOYSA-N 1-cyclopentyl-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-6-(6-morpholin-4-ylpyridin-3-yl)indazole-4-carboxamide Chemical compound O=C1NC(C)=CC(C)=C1CNC(=O)C1=CC(C=2C=NC(=CC=2)N2CCOCC2)=CC2=C1C=NN2C1CCCC1 RFXJKNSXOOYXNC-UHFFFAOYSA-N 0.000 claims 1
- FWBYCPAATXJYOH-UHFFFAOYSA-N 1-cyclopentyl-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-6-(6-piperazin-1-ylpyridin-3-yl)indazole-4-carboxamide Chemical compound O=C1NC(C)=CC(C)=C1CNC(=O)C1=CC(C=2C=NC(=CC=2)N2CCNCC2)=CC2=C1C=NN2C1CCCC1 FWBYCPAATXJYOH-UHFFFAOYSA-N 0.000 claims 1
- ZOYKFUMSDCMURV-UHFFFAOYSA-N 1-cyclopentyl-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-6-[2-(4-methylpiperazin-1-yl)pyridin-4-yl]indazole-4-carboxamide Chemical compound C1CN(C)CCN1C1=CC(C=2C=C3N(C4CCCC4)N=CC3=C(C(=O)NCC=3C(NC(C)=CC=3C)=O)C=2)=CC=N1 ZOYKFUMSDCMURV-UHFFFAOYSA-N 0.000 claims 1
- IROVPCVKFKQSBC-UHFFFAOYSA-N 1-cyclopentyl-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-6-[3-(trifluoromethoxy)phenyl]indazole-4-carboxamide Chemical compound O=C1NC(C)=CC(C)=C1CNC(=O)C1=CC(C=2C=C(OC(F)(F)F)C=CC=2)=CC2=C1C=NN2C1CCCC1 IROVPCVKFKQSBC-UHFFFAOYSA-N 0.000 claims 1
- SCDMGXZJNGCGAB-UHFFFAOYSA-N 1-cyclopentyl-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]indazole-4-carboxamide Chemical compound O=C1NC(C)=CC(C)=C1CNC(=O)C1=CC=CC2=C1C=NN2C1CCCC1 SCDMGXZJNGCGAB-UHFFFAOYSA-N 0.000 claims 1
- FZEYQWAZDUSVJE-UHFFFAOYSA-N 1-cyclopentyl-n-[(6-methyl-2-oxo-4-propyl-1h-pyridin-3-yl)methyl]-6-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]indazole-4-carboxamide Chemical compound C1=C(C)NC(=O)C(CNC(=O)C=2C=3C=NN(C=3C=C(C=2)C=2C=NC(=CC=2)N2CCN(C)CC2)C2CCCC2)=C1CCC FZEYQWAZDUSVJE-UHFFFAOYSA-N 0.000 claims 1
- DRMFVKASEKEEQM-UHFFFAOYSA-N 1-cyclopentyl-n-[(6-methyl-2-oxo-4-propyl-1h-pyridin-3-yl)methyl]-6-pyridin-3-ylindazole-4-carboxamide Chemical compound C1=C(C)NC(=O)C(CNC(=O)C=2C=3C=NN(C=3C=C(C=2)C=2C=NC=CC=2)C2CCCC2)=C1CCC DRMFVKASEKEEQM-UHFFFAOYSA-N 0.000 claims 1
- UENYKKQGQNRWQE-UHFFFAOYSA-N 1-cyclopropyl-6-[4-[(dimethylamino)methyl]phenyl]-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]indazole-4-carboxamide Chemical compound C1=CC(CN(C)C)=CC=C1C1=CC(C(=O)NCC=2C(NC(C)=CC=2C)=O)=C(C=NN2C3CC3)C2=C1 UENYKKQGQNRWQE-UHFFFAOYSA-N 0.000 claims 1
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|---|---|---|---|---|
| MX2012012966A (es) * | 2010-05-07 | 2013-01-22 | Glaxosmithkline Llc | Indoles. |
| US20130102477A1 (en) | 2010-06-23 | 2013-04-25 | Ryan D. Morin | Biomarkers for non-hodgkin lymphomas and uses thereof |
| AU2011298987B2 (en) | 2010-09-10 | 2017-09-28 | Epizyme, Inc. | Inhibitors of human EZH2, and methods of use thereof |
| US9175331B2 (en) | 2010-09-10 | 2015-11-03 | Epizyme, Inc. | Inhibitors of human EZH2, and methods of use thereof |
| JP5908493B2 (ja) * | 2010-12-01 | 2016-04-26 | グラクソスミスクライン・リミテッド・ライアビリティ・カンパニーＧｌａｘｏＳｍｉｔｈＫｌｉｎｅ ＬＬＣ | インドール |
| EP3323820B1 (en) | 2011-02-28 | 2023-05-10 | Epizyme, Inc. | Substituted 6,5-fused bicyclic heteroaryl compounds |
| JO3438B1 (ar) * | 2011-04-13 | 2019-10-20 | 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 |
| AU2013203641B2 (en) * | 2011-04-13 | 2014-08-21 | Epizyme, Inc. | Aryl-or heteroaryl-substituted benzene compounds |
| EP2570125A1 (en) | 2011-09-16 | 2013-03-20 | Almirall, S.A. | Ep1 receptor ligands |
| JP2014534178A (ja) * | 2011-09-30 | 2014-12-18 | グラクソスミスクライン・リミテッド・ライアビリティ・カンパニーＧｌａｘｏＳｍｉｔｈＫｌｉｎｅ ＬＬＣ | 癌の処置方法 |
| CA2854447A1 (en) | 2011-11-04 | 2013-05-10 | Glaxosmithkline Intellectual Property (No.2) Limited | Method of treatment |
| EP2780014A4 (en) * | 2011-11-18 | 2015-07-01 | Constellation Pharmaceuticals Inc | MODULATORS OF METHYL MODIFYING ENZYMES, COMPOSITIONS AND USES THEREOF |
| EP2780013A4 (en) * | 2011-11-18 | 2015-07-01 | Constellation Pharmaceuticals Inc | MODULATORS OF METHYL MODIFYING ENZYMES, COMPOSITIONS AND USES THEREOF |
| NZ628762A (en) | 2012-02-10 | 2016-07-29 | Constellation Pharmaceuticals Inc | Modulators of methyl modifying enzymes, compositions and uses thereof |
| AU2013232229B2 (en) | 2012-03-12 | 2017-11-23 | Epizyme, Inc. | Inhibitors of human EZH2, and methods of use thereof |
| LT2836491T (lt) | 2012-04-13 | 2017-03-27 | Epizyme, Inc. | Žmogaus histono metiltransferazės ezh2 slopiklio druskos forma |
| US9562041B2 (en) | 2012-05-16 | 2017-02-07 | Glaxosmithkline Llc | Enhancer of zeste homolog 2 inhibitors |
| WO2013188848A2 (en) * | 2012-06-15 | 2013-12-19 | The Regents Of The University Of California | Antiviral compounds and methods of use |
| JP6254169B2 (ja) * | 2012-09-28 | 2017-12-27 | ファイザー・インク | ベンズアミドおよびヘテロベンズアミド化合物 |
| RU2018145311A (ru) | 2012-10-15 | 2019-02-18 | Эпизайм, Инк. | Способы лечения рака |
| JP6461802B2 (ja) | 2012-10-15 | 2019-01-30 | エピザイム，インコーポレイティド | 置換ベンゼン化合物 |
| SMT201800070T1 (it) | 2012-12-19 | 2018-03-08 | Celgene Quanticel Res Inc | Inibiorti di istone demetilasi |
| WO2014100080A1 (en) * | 2012-12-19 | 2014-06-26 | Glaxosmithkline Llc | Combination |
| EP2935264B1 (en) | 2012-12-21 | 2017-10-18 | Epizyme, Inc. | 1,4-pyridone bicyclic heteroaryl compounds |
| UA111305C2 (uk) | 2012-12-21 | 2016-04-11 | Пфайзер Інк. | Конденсовані лактами арилу та гетероарилу |
| KR20150127216A (ko) | 2013-03-14 | 2015-11-16 | 제넨테크, 인크. | 암의 치료 및 암 약물 내성의 예방 방법 |
| EP2970305B1 (en) | 2013-03-15 | 2017-02-22 | Constellation Pharmaceuticals, Inc. | Modulators of methyl modifying enzymes, compositions and uses thereof |
| HK1214815A1 (zh) | 2013-04-30 | 2016-08-05 | Glaxosmithkline Intellectual Property (No. 2) Limited | Zeste增强子同源物2的抑制剂 |
| CN105473580A (zh) | 2013-07-10 | 2016-04-06 | 葛兰素史密斯克莱知识产权（第2号）有限公司 | Zeste同源物增强子2抑制剂 |
| EP3033334A1 (en) | 2013-08-15 | 2016-06-22 | Constellation Pharmaceuticals, Inc. | Indole derivatives as modulators of methyl modifying enzymes, compositions and uses thereof |
| HUE063984T2 (hu) | 2013-10-16 | 2024-02-28 | Epizyme Inc | Hidroklorid só forma az EZH2 gátlásához |
| US9822103B2 (en) | 2013-11-22 | 2017-11-21 | Bristol-Myers Squibb Company | Inhibitors of lysine methyl transferase |
| US20160361309A1 (en) | 2014-02-26 | 2016-12-15 | Glaxosmithkline Intellectual Property (No.2) Limited | Methods of treating cancer patients responding to ezh2 inhibitor gsk126 |
| CN105017221B (zh) * | 2014-04-30 | 2019-05-28 | 中国医学科学院药物研究所 | 苯并咪唑衍生物及其制法和药物组合物与用途 |
| CN107207464B (zh) | 2014-06-17 | 2019-10-22 | 辉瑞大药厂 | 被取代的二氢异喹啉酮化合物 |
| ES2751464T3 (es) | 2014-09-17 | 2020-03-31 | Celgene Quanticel Res Inc | Inhibidores de histona desmetilasa |
| EP3885343A1 (en) * | 2014-11-06 | 2021-09-29 | Dana-Farber Cancer Institute, Inc. | Indole compounds as ezh2 inhibitors and uses thereof |
| TW201636344A (zh) | 2014-12-05 | 2016-10-16 | 美國禮來大藥廠 | Ｅｚｈ２抑制劑 |
| MA41140A (fr) | 2014-12-12 | 2017-10-17 | Cancer Research Tech Ltd | Dérivés de 2,4-dioxo-quinazoline-6-sulfonamide en tant qu'inhibiteurs de la parg |
| MA41179A (fr) * | 2014-12-19 | 2017-10-24 | Cancer Research Tech Ltd | Composés inhibiteurs de parg |
| WO2016101956A2 (en) | 2014-12-23 | 2016-06-30 | University Of Copenhagen | Treatment of cancer by inhibiting ezh2 activity |
| EP3283502A4 (en) | 2015-04-07 | 2019-04-03 | The General Hospital Corporation | METHOD FOR REACTIVATING GENES ON THE INACTIVE X-CHROMOSOME |
| 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 |
| US10577350B2 (en) | 2015-08-28 | 2020-03-03 | Constellation Pharmaceuticals, Inc. | Crystalline forms of (R)-N-((4-methoxy-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-methyl-1-(1-(1-(2,2,2-trifluoroethyl)piperidin-4-yl)ethyl)-1H-indole-3-carboxamide |
| US11059817B2 (en) | 2015-09-23 | 2021-07-13 | The Regents Of The University Of California | Potent antiviral pyrazolopyridine compounds |
| CN108699046A (zh) * | 2015-10-06 | 2018-10-23 | Epizyme股份有限公司 | 用ezh2抑制剂治疗成神经管细胞瘤的方法 |
| DK3378859T3 (da) | 2015-11-19 | 2020-01-20 | Jiangsu Hengrui Medicine Co | Benzofuranderivater, fremgangsmåde til fremstilling deraf og anvendelse deraf i medicin |
| KR102852334B1 (ko) | 2016-02-10 | 2025-09-01 | 웨이크 포리스트 유니버시티 헬스 사이언시즈 | 간 섬유화의 모델 시스템 및 그의 제조 및 사용 방법 |
| WO2017157825A1 (en) | 2016-03-15 | 2017-09-21 | F. Hoffmann-La Roche Ag | Combinations of lsd1 inhibitors for use in the treatment of solid tumors |
| WO2017192290A1 (en) | 2016-05-04 | 2017-11-09 | The Wistar Institute Of Anatomy And Biology | Methods of treating cancers overexpressing carm1 with ezh2 inhibitors and platinum-based antineoplastic drugs |
| CN107573327B (zh) * | 2016-07-05 | 2020-03-31 | 四川大学 | 吲唑-甲酰胺-吡啶酮衍生物及其制备方法和用途 |
| MA46199A (fr) * | 2016-09-07 | 2019-07-17 | Shanghai Haihe Pharmaceutical Co Ltd | Composé cyclique aromatique de pyrido à cinq éléments, son procédé de préparation et son utilisation |
| WO2018075598A1 (en) | 2016-10-19 | 2018-04-26 | Constellation Pharmaceuticals, Inc. | Synthesis of inhibitors of ezh2 |
| WO2018086592A1 (zh) * | 2016-11-11 | 2018-05-17 | 上海海雁医药科技有限公司 | 4,5,6-三取代吲唑类衍生物、其制法与医药上的用途 |
| US10266542B2 (en) | 2017-03-15 | 2019-04-23 | Mirati Therapeutics, Inc. | EZH2 inhibitors |
| MX386586B (es) | 2017-05-18 | 2025-03-19 | Jiangsu Hengrui Medicine Co | Cristal de base libre de derivados benzofurano y método de preparación. |
| WO2019057946A1 (en) | 2017-09-25 | 2019-03-28 | F. Hoffmann-La Roche Ag | MULTI-CYCLIC AROMATIC COMPOUNDS AS D-FACTOR INHIBITORS |
| EP3708567A4 (en) * | 2017-11-10 | 2021-07-07 | Jiangsu Hengrui Medicine Co., Ltd. | PROCESS FOR THE PREPARATION OF A BENZOFURANE DERIVATIVE |
| BR112020008325A2 (pt) | 2017-11-14 | 2020-10-20 | Pfizer Inc. | terapias de combinação com o inibidor de ezh2 |
| CN110016014B (zh) * | 2018-01-08 | 2023-02-17 | 中国科学院上海药物研究所 | Ezh2抑制剂及其制备和抗肿瘤治疗中的应用 |
| WO2019152419A1 (en) | 2018-01-31 | 2019-08-08 | Mirati Therapeutics, Inc | Prc2 inhibitors |
| CN110229157B (zh) * | 2018-03-06 | 2022-06-21 | 上海海和药物研究开发股份有限公司 | 嘧啶并五元芳香杂环类化合物、其制备方法及用途 |
| CZ308400B6 (cs) * | 2018-04-11 | 2020-07-29 | Univerzita Karlova | Farmaceutický přípravek pro léčení maligního melanomu |
| EP3823671B1 (en) | 2018-07-09 | 2024-02-07 | Fondation Asile Des Aveugles | Inhibition of prc2 subunits to treat eye disorders |
| CA3106589A1 (en) | 2018-07-27 | 2020-01-30 | Suzhou Sinovent Pharma Co., Ltd. | Polysubstituted benzene compound and preparation method and use thereof |
| EP3841062A4 (en) * | 2018-08-24 | 2022-06-01 | Shanghai Tetrels Material Technology Co., Ltd. | Devices and methods for water-filtration membranes |
| EP3959214A1 (en) | 2019-04-22 | 2022-03-02 | Mirati Therapeutics, Inc. | Naphthyridine derivatives as prc2 inhibitors |
| CA3142711A1 (en) | 2019-06-05 | 2020-12-10 | 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 |
| WO2023025856A1 (en) | 2021-08-25 | 2023-03-02 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Use of ezh2 inhibitors for the treatment of aortic valve stenosis |
| CN116768857A (zh) * | 2022-03-09 | 2023-09-19 | 中国药科大学 | Ezh2/hdac双靶点抑制剂及其制备方法和医药用途 |
| WO2023183850A1 (en) | 2022-03-23 | 2023-09-28 | Ideaya Biosciences, Inc. | Piperazine substituted indazole compounds as inhibitors of parg |
| US20250270191A1 (en) | 2022-06-13 | 2025-08-28 | Treeline Biosciences, Inc. | Quinolone bcl6 bifunctional degraders |
| WO2023244917A1 (en) | 2022-06-13 | 2023-12-21 | Treeline Biosciences, Inc. | 1,8-naphthyridin-2-one heterobifunctional bcl6 degraders |
| WO2025064745A1 (en) * | 2023-09-20 | 2025-03-27 | Ideaya Biosciences, Inc. | Parg inhibitor |
| CN117362277B (zh) * | 2023-10-13 | 2025-02-11 | 沈阳药科大学 | 含咪唑啉酮结构的苯甲酰胺类化合物及其制备方法和应用 |
| WO2025248032A1 (en) | 2024-05-31 | 2025-12-04 | Syngenta Crop Protection Ag | Pesticidally active indazole compounds |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU771928B2 (en) * | 1999-05-19 | 2004-04-08 | Pharmacia Corporation | Substituted polycyclic aryl and heteroaryl pyridones useful for selective inhibition of the coagulation cascade |
| TW200303304A (en) * | 2002-02-18 | 2003-09-01 | Astrazeneca Ab | Chemical compounds |
| WO2004112719A2 (en) | 2003-06-19 | 2004-12-29 | Smithkline Beecham Corporation | Chemical compounds |
| US20090012031A1 (en) * | 2007-07-03 | 2009-01-08 | The Regents Of The University Of Michigan | EZH2 Cancer Markers |
| JP5364875B2 (ja) | 2007-07-16 | 2013-12-11 | アッヴィ・インコーポレイテッド | タンパク質キナーゼ阻害薬としてのインダゾール類、ベンゾイソオキサゾール類およびベンゾイソチアゾール類 |
| JP5216912B2 (ja) * | 2008-04-29 | 2013-06-19 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃｃｒ１受容体拮抗薬としてのインダゾール化合物 |
| CN102369204A (zh) | 2008-09-26 | 2012-03-07 | 新加坡科技研究局 | 3-脱氮瓶菌素衍生物 |
| ES2528269T3 (es) | 2010-05-07 | 2015-02-06 | Glaxosmithkline Llc | Azaindazoles |
| MX2012012966A (es) | 2010-05-07 | 2013-01-22 | Glaxosmithkline Llc | Indoles. |
| EP3323820B1 (en) | 2011-02-28 | 2023-05-10 | Epizyme, Inc. | Substituted 6,5-fused bicyclic heteroaryl compounds |
-
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- 2011-05-05 WO PCT/US2011/035340 patent/WO2011140325A1/en not_active Ceased
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- 2011-05-05 ES ES11778335.7T patent/ES2534804T3/es active Active
- 2011-05-05 EP EP11778335.7A patent/EP2566328B1/en not_active Not-in-force
-
2014
- 2014-08-13 US US14/458,305 patent/US9018382B2/en not_active Expired - Fee Related
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