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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|---|---|---|---|---|
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- 2011-05-05 US US13/696,436 patent/US8846935B2/en not_active Expired - Fee Related
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- 2011-05-05 EP EP11778335.7A patent/EP2566328B1/en not_active Not-in-force
- 2011-05-05 ES ES11778335.7T patent/ES2534804T3/es active Active
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2014
- 2014-08-13 US US14/458,305 patent/US9018382B2/en not_active Expired - Fee Related
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