JP2014521620A5 - - Google Patents
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- Publication number
- JP2014521620A5 JP2014521620A5 JP2014522035A JP2014522035A JP2014521620A5 JP 2014521620 A5 JP2014521620 A5 JP 2014521620A5 JP 2014522035 A JP2014522035 A JP 2014522035A JP 2014522035 A JP2014522035 A JP 2014522035A JP 2014521620 A5 JP2014521620 A5 JP 2014521620A5
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- indazole
- carboxamide
- dihydro
- alkyl
- 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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- 150000001875 compounds Chemical class 0.000 claims 23
- 125000003118 aryl group Chemical group 0.000 claims 20
- 125000000623 heterocyclic group Chemical group 0.000 claims 20
- 125000001072 heteroaryl group Chemical group 0.000 claims 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 15
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 150000002431 hydrogen Chemical class 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- -1 substituents Halogen Chemical class 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 239000002246 antineoplastic agent Substances 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 229940127089 cytotoxic agent Drugs 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- YGWYOZIKVSOHMN-UHFFFAOYSA-N 1-ethyl-3-oxo-2-piperidin-4-ylindazole-4-carboxamide Chemical compound O=C1C2=C(C(N)=O)C=CC=C2N(CC)N1C1CCNCC1 YGWYOZIKVSOHMN-UHFFFAOYSA-N 0.000 claims 1
- QBPZRWOAIYPXFL-UHFFFAOYSA-N 1-ethyl-6-fluoro-3-oxo-2-piperidin-4-ylindazole-4-carboxamide Chemical compound O=C1C2=C(C(N)=O)C=C(F)C=C2N(CC)N1C1CCNCC1 QBPZRWOAIYPXFL-UHFFFAOYSA-N 0.000 claims 1
- VJFVDUPSYQILQW-UHFFFAOYSA-N 1-methyl-2-(1-methylpiperidin-4-yl)-3-oxoindazole-4-carboxamide Chemical compound C1CN(C)CCC1N1C(=O)C2=C(C(N)=O)C=CC=C2N1C VJFVDUPSYQILQW-UHFFFAOYSA-N 0.000 claims 1
- MGGYINOUFRKASP-UHFFFAOYSA-N 1-methyl-3-oxo-2-(1-phenylpiperidin-4-yl)indazole-4-carboxamide Chemical compound O=C1C2=C(C(N)=O)C=CC=C2N(C)N1C(CC1)CCN1C1=CC=CC=C1 MGGYINOUFRKASP-UHFFFAOYSA-N 0.000 claims 1
- QTAAMFZROWGTBV-UHFFFAOYSA-N 1-methyl-3-oxo-2-(1-propan-2-ylpiperidin-4-yl)indazole-4-carboxamide Chemical compound C1CN(C(C)C)CCC1N1C(=O)C2=C(C(N)=O)C=CC=C2N1C QTAAMFZROWGTBV-UHFFFAOYSA-N 0.000 claims 1
- DQUPPBNAKKNJCG-UHFFFAOYSA-N 1-methyl-3-oxo-2-(1-pyridin-3-ylpiperidin-4-yl)indazole-4-carboxamide Chemical compound O=C1C2=C(C(N)=O)C=CC=C2N(C)N1C(CC1)CCN1C1=CC=CN=C1 DQUPPBNAKKNJCG-UHFFFAOYSA-N 0.000 claims 1
- ISZXVGQBWFOMRH-UHFFFAOYSA-N 1-methyl-3-oxo-2-(1-pyridin-4-ylpiperidin-4-yl)indazole-4-carboxamide Chemical compound O=C1C2=C(C(N)=O)C=CC=C2N(C)N1C(CC1)CCN1C1=CC=NC=C1 ISZXVGQBWFOMRH-UHFFFAOYSA-N 0.000 claims 1
- OKQHBZNTIODWFQ-UHFFFAOYSA-N 1-methyl-3-oxo-2-(4-piperidin-4-ylphenyl)indazole-4-carboxamide Chemical compound O=C1C2=C(C(N)=O)C=CC=C2N(C)N1C(C=C1)=CC=C1C1CCNCC1 OKQHBZNTIODWFQ-UHFFFAOYSA-N 0.000 claims 1
- CRRYCTZISQQIEO-UHFFFAOYSA-N 1-methyl-3-oxo-2-(4-pyridin-4-ylphenyl)indazole-4-carboxamide Chemical compound O=C1C2=C(C(N)=O)C=CC=C2N(C)N1C(C=C1)=CC=C1C1=CC=NC=C1 CRRYCTZISQQIEO-UHFFFAOYSA-N 0.000 claims 1
- AFJWZGCQRIBDPC-UHFFFAOYSA-N 1-methyl-3-oxo-2-[1-(1h-pyrrol-2-ylmethyl)piperidin-4-yl]indazole-4-carboxamide Chemical compound O=C1C2=C(C(N)=O)C=CC=C2N(C)N1C(CC1)CCN1CC1=CC=CN1 AFJWZGCQRIBDPC-UHFFFAOYSA-N 0.000 claims 1
- YPXYVWLWTAQXOJ-UHFFFAOYSA-N 1-methyl-3-oxo-2-[1-(1h-pyrrol-3-ylmethyl)piperidin-4-yl]indazole-4-carboxamide Chemical compound O=C1C2=C(C(N)=O)C=CC=C2N(C)N1C(CC1)CCN1CC=1C=CNC=1 YPXYVWLWTAQXOJ-UHFFFAOYSA-N 0.000 claims 1
- TVMQVMPQEYUIGQ-UHFFFAOYSA-N 1-methyl-3-oxo-2-[1-(thiophen-2-ylmethyl)piperidin-4-yl]indazole-4-carboxamide Chemical compound O=C1C2=C(C(N)=O)C=CC=C2N(C)N1C(CC1)CCN1CC1=CC=CS1 TVMQVMPQEYUIGQ-UHFFFAOYSA-N 0.000 claims 1
- XCMZWTDSYWVLET-UHFFFAOYSA-N 1-methyl-3-oxo-2-piperidin-4-ylindazole-4-carboxamide Chemical compound O=C1C2=C(C(N)=O)C=CC=C2N(C)N1C1CCNCC1 XCMZWTDSYWVLET-UHFFFAOYSA-N 0.000 claims 1
- UUQRRSAKFTVLLN-UHFFFAOYSA-N 2-(1-benzylpiperidin-4-yl)-1-methyl-3-oxoindazole-4-carboxamide Chemical compound O=C1C2=C(C(N)=O)C=CC=C2N(C)N1C(CC1)CCN1CC1=CC=CC=C1 UUQRRSAKFTVLLN-UHFFFAOYSA-N 0.000 claims 1
- KLJGXEJQJQJADT-UHFFFAOYSA-N 2-(1-benzylpiperidin-4-yl)-3-oxo-1h-indazole-4-carboxamide Chemical compound O=C1C=2C(C(=O)N)=CC=CC=2NN1C(CC1)CCN1CC1=CC=CC=C1 KLJGXEJQJQJADT-UHFFFAOYSA-N 0.000 claims 1
- QNLAVJXTBVYHBB-UHFFFAOYSA-N 2-(1-cyclobutylpiperidin-4-yl)-1-methyl-3-oxoindazole-4-carboxamide Chemical compound O=C1C2=C(C(N)=O)C=CC=C2N(C)N1C(CC1)CCN1C1CCC1 QNLAVJXTBVYHBB-UHFFFAOYSA-N 0.000 claims 1
- VPFGQWNBEHLGLL-UHFFFAOYSA-N 2-(1-cyclobutylpiperidin-4-yl)-3-oxo-1h-indazole-4-carboxamide Chemical compound O=C1C=2C(C(=O)N)=CC=CC=2NN1C(CC1)CCN1C1CCC1 VPFGQWNBEHLGLL-UHFFFAOYSA-N 0.000 claims 1
- WTZNVEJNRDYVFN-UHFFFAOYSA-N 2-(1-cyclobutylpiperidin-4-yl)-6-fluoro-1-methyl-3-oxoindazole-4-carboxamide Chemical compound O=C1C2=C(C(N)=O)C=C(F)C=C2N(C)N1C(CC1)CCN1C1CCC1 WTZNVEJNRDYVFN-UHFFFAOYSA-N 0.000 claims 1
- DHHMUTDEQQNNOC-UHFFFAOYSA-N 2-(1-cyclobutylpiperidin-4-yl)-6-fluoro-3-oxo-1h-indazole-4-carboxamide Chemical compound O=C1C=2C(C(=O)N)=CC(F)=CC=2NN1C(CC1)CCN1C1CCC1 DHHMUTDEQQNNOC-UHFFFAOYSA-N 0.000 claims 1
- LQCUWVHLGPGETP-UHFFFAOYSA-N 2-(1-cyclohexylazetidin-3-yl)-1-methyl-3-oxoindazole-4-carboxamide Chemical compound O=C1C2=C(C(N)=O)C=CC=C2N(C)N1C(C1)CN1C1CCCCC1 LQCUWVHLGPGETP-UHFFFAOYSA-N 0.000 claims 1
- UXDSIJGLPLQLFE-UHFFFAOYSA-N 2-(1-cyclohexylazetidin-3-yl)-3-oxo-1h-indazole-4-carboxamide Chemical compound O=C1C=2C(C(=O)N)=CC=CC=2NN1C(C1)CN1C1CCCCC1 UXDSIJGLPLQLFE-UHFFFAOYSA-N 0.000 claims 1
- FGIOTWXUGHYOKV-UHFFFAOYSA-N 2-(1-cyclohexylazetidin-3-yl)-6-fluoro-1-methyl-3-oxoindazole-4-carboxamide Chemical compound O=C1C2=C(C(N)=O)C=C(F)C=C2N(C)N1C(C1)CN1C1CCCCC1 FGIOTWXUGHYOKV-UHFFFAOYSA-N 0.000 claims 1
- FEKOIQNXQNTNKL-UHFFFAOYSA-N 2-(1-cyclohexylpiperidin-4-yl)-1-ethyl-3-oxoindazole-4-carboxamide Chemical compound O=C1C2=C(C(N)=O)C=CC=C2N(CC)N1C(CC1)CCN1C1CCCCC1 FEKOIQNXQNTNKL-UHFFFAOYSA-N 0.000 claims 1
- XPKUFZAKPWQMOR-UHFFFAOYSA-N 2-(1-cyclohexylpiperidin-4-yl)-1-methyl-3-oxoindazole-4-carboxamide Chemical compound O=C1C2=C(C(N)=O)C=CC=C2N(C)N1C(CC1)CCN1C1CCCCC1 XPKUFZAKPWQMOR-UHFFFAOYSA-N 0.000 claims 1
- XEWGITPSXRGTBO-UHFFFAOYSA-N 2-(1-cyclohexylpiperidin-4-yl)-3-oxo-1h-indazole-4-carboxamide Chemical compound O=C1C=2C(C(=O)N)=CC=CC=2NN1C(CC1)CCN1C1CCCCC1 XEWGITPSXRGTBO-UHFFFAOYSA-N 0.000 claims 1
- PQXUCBRUEQVEIZ-UHFFFAOYSA-N 2-(1-cyclohexylpiperidin-4-yl)-6-fluoro-1-methyl-3-oxoindazole-4-carboxamide Chemical compound O=C1C2=C(C(N)=O)C=C(F)C=C2N(C)N1C(CC1)CCN1C1CCCCC1 PQXUCBRUEQVEIZ-UHFFFAOYSA-N 0.000 claims 1
- OKBDXGNRRUXLQE-UHFFFAOYSA-N 2-(1-cyclohexylpiperidin-4-yl)-6-fluoro-3-oxo-1h-indazole-4-carboxamide Chemical compound O=C1C=2C(C(=O)N)=CC(F)=CC=2NN1C(CC1)CCN1C1CCCCC1 OKBDXGNRRUXLQE-UHFFFAOYSA-N 0.000 claims 1
- NPMKKPKCZJHHCM-UHFFFAOYSA-N 2-(1-cyclopentylpiperidin-4-yl)-1-methyl-3-oxoindazole-4-carboxamide Chemical compound O=C1C2=C(C(N)=O)C=CC=C2N(C)N1C(CC1)CCN1C1CCCC1 NPMKKPKCZJHHCM-UHFFFAOYSA-N 0.000 claims 1
- OVJIYLSTZRNOLG-UHFFFAOYSA-N 2-(1-cyclopentylpiperidin-4-yl)-3-oxo-1h-indazole-4-carboxamide Chemical compound O=C1C=2C(C(=O)N)=CC=CC=2NN1C(CC1)CCN1C1CCCC1 OVJIYLSTZRNOLG-UHFFFAOYSA-N 0.000 claims 1
- SAMGXLVBURJEJM-UHFFFAOYSA-N 2-(1-ethylpiperidin-4-yl)-1-methyl-3-oxoindazole-4-carboxamide Chemical compound C1CN(CC)CCC1N1C(=O)C2=C(C(N)=O)C=CC=C2N1C SAMGXLVBURJEJM-UHFFFAOYSA-N 0.000 claims 1
- ZQZRXPFBEJPPKJ-UHFFFAOYSA-N 2-(1-ethylpiperidin-4-yl)-3-oxo-1h-indazole-4-carboxamide Chemical compound C1CN(CC)CCC1N1C(=O)C2=C(C(N)=O)C=CC=C2N1 ZQZRXPFBEJPPKJ-UHFFFAOYSA-N 0.000 claims 1
- SBXCLTZHGFAEGE-UHFFFAOYSA-N 2-(1-methylpiperidin-4-yl)-3-oxo-1h-indazole-4-carboxamide Chemical compound C1CN(C)CCC1N1C(=O)C2=C(C(N)=O)C=CC=C2N1 SBXCLTZHGFAEGE-UHFFFAOYSA-N 0.000 claims 1
- NWULWFVQKLIALI-UHFFFAOYSA-N 2-[1-(4,4-dichlorocyclohexyl)piperidin-4-yl]-1-methyl-3-oxoindazole-4-carboxamide Chemical compound O=C1C2=C(C(N)=O)C=CC=C2N(C)N1C(CC1)CCN1C1CCC(Cl)(Cl)CC1 NWULWFVQKLIALI-UHFFFAOYSA-N 0.000 claims 1
- IMXAAXJRLKLQGB-UHFFFAOYSA-N 2-[1-(4,4-difluorocyclohexyl)piperidin-4-yl]-1-methyl-3-oxoindazole-4-carboxamide Chemical compound O=C1C2=C(C(N)=O)C=CC=C2N(C)N1C(CC1)CCN1C1CCC(F)(F)CC1 IMXAAXJRLKLQGB-UHFFFAOYSA-N 0.000 claims 1
- WEUSDVLSZAFNCO-UHFFFAOYSA-N 2-[1-(4,4-difluorocyclohexyl)piperidin-4-yl]-3-oxo-1h-indazole-4-carboxamide Chemical compound O=C1C=2C(C(=O)N)=CC=CC=2NN1C(CC1)CCN1C1CCC(F)(F)CC1 WEUSDVLSZAFNCO-UHFFFAOYSA-N 0.000 claims 1
- DNUXFVBNRHFGHK-UHFFFAOYSA-N 2-[1-(4,4-difluorocyclohexyl)piperidin-4-yl]-6-fluoro-1-methyl-3-oxoindazole-4-carboxamide Chemical compound O=C1C2=C(C(N)=O)C=C(F)C=C2N(C)N1C(CC1)CCN1C1CCC(F)(F)CC1 DNUXFVBNRHFGHK-UHFFFAOYSA-N 0.000 claims 1
- SBDYFIHZQFQZCK-UHFFFAOYSA-N 2-[1-(cyclohex-3-en-1-ylmethyl)piperidin-4-yl]-1-methyl-3-oxoindazole-4-carboxamide Chemical compound O=C1C2=C(C(N)=O)C=CC=C2N(C)N1C(CC1)CCN1CC1CCC=CC1 SBDYFIHZQFQZCK-UHFFFAOYSA-N 0.000 claims 1
- MHOBIUHIHRMJRE-UHFFFAOYSA-N 2-[1-(cyclohex-3-en-1-ylmethyl)piperidin-4-yl]-3-oxo-1h-indazole-4-carboxamide Chemical compound O=C1C=2C(C(=O)N)=CC=CC=2NN1C(CC1)CCN1CC1CCC=CC1 MHOBIUHIHRMJRE-UHFFFAOYSA-N 0.000 claims 1
- HHODORPGMSMXQA-UHFFFAOYSA-N 2-[1-(cyclohexylmethyl)piperidin-4-yl]-1-methyl-3-oxoindazole-4-carboxamide Chemical compound O=C1C2=C(C(N)=O)C=CC=C2N(C)N1C(CC1)CCN1CC1CCCCC1 HHODORPGMSMXQA-UHFFFAOYSA-N 0.000 claims 1
- HTUDQMHOVIPNPF-UHFFFAOYSA-N 2-[1-(cyclohexylmethyl)piperidin-4-yl]-3-oxo-1h-indazole-4-carboxamide Chemical compound O=C1C=2C(C(=O)N)=CC=CC=2NN1C(CC1)CCN1CC1CCCCC1 HTUDQMHOVIPNPF-UHFFFAOYSA-N 0.000 claims 1
- FRGMDGKFVLOUCT-UHFFFAOYSA-N 2-[1-(furan-2-ylmethyl)piperidin-4-yl]-3-oxo-1h-indazole-4-carboxamide Chemical compound O=C1C=2C(C(=O)N)=CC=CC=2NN1C(CC1)CCN1CC1=CC=CO1 FRGMDGKFVLOUCT-UHFFFAOYSA-N 0.000 claims 1
- VFQDKRSLDGWGBS-UHFFFAOYSA-N 2-[1-(furan-3-ylmethyl)piperidin-4-yl]-1-methyl-3-oxoindazole-4-carboxamide Chemical compound O=C1C2=C(C(N)=O)C=CC=C2N(C)N1C(CC1)CCN1CC=1C=COC=1 VFQDKRSLDGWGBS-UHFFFAOYSA-N 0.000 claims 1
- QKJLENNBYDTENH-UHFFFAOYSA-N 2-[1-(furan-3-ylmethyl)piperidin-4-yl]-3-oxo-1h-indazole-4-carboxamide Chemical compound O=C1C=2C(C(=O)N)=CC=CC=2NN1C(CC1)CCN1CC=1C=COC=1 QKJLENNBYDTENH-UHFFFAOYSA-N 0.000 claims 1
- JHOLYZMPGXNVHM-UHFFFAOYSA-N 3-oxo-2-(1-phenylpiperidin-4-yl)-1h-indazole-4-carboxamide Chemical compound O=C1C=2C(C(=O)N)=CC=CC=2NN1C(CC1)CCN1C1=CC=CC=C1 JHOLYZMPGXNVHM-UHFFFAOYSA-N 0.000 claims 1
- XTQOVBDMXJLDKF-UHFFFAOYSA-N 3-oxo-2-(1-propan-2-ylpiperidin-4-yl)-1h-indazole-4-carboxamide Chemical compound C1CN(C(C)C)CCC1N1C(=O)C2=C(C(N)=O)C=CC=C2N1 XTQOVBDMXJLDKF-UHFFFAOYSA-N 0.000 claims 1
- OSXUFLZXPJVGDL-UHFFFAOYSA-N 3-oxo-2-(1-propylpiperidin-4-yl)-1h-indazole-4-carboxamide Chemical compound C1CN(CCC)CCC1N1C(=O)C2=C(C(N)=O)C=CC=C2N1 OSXUFLZXPJVGDL-UHFFFAOYSA-N 0.000 claims 1
- WIZBDMUANSAVNW-UHFFFAOYSA-N 3-oxo-2-(1-pyridin-3-ylpiperidin-4-yl)-1h-indazole-4-carboxamide Chemical compound O=C1C=2C(C(=O)N)=CC=CC=2NN1C(CC1)CCN1C1=CC=CN=C1 WIZBDMUANSAVNW-UHFFFAOYSA-N 0.000 claims 1
- ZPNWGLVAEKFEGJ-UHFFFAOYSA-N 3-oxo-2-(1-pyridin-4-ylpiperidin-4-yl)-1h-indazole-4-carboxamide Chemical compound O=C1C=2C(C(=O)N)=CC=CC=2NN1C(CC1)CCN1C1=CC=NC=C1 ZPNWGLVAEKFEGJ-UHFFFAOYSA-N 0.000 claims 1
- RXSSHKKBZKSMAA-UHFFFAOYSA-N 3-oxo-2-(4-piperidin-4-ylphenyl)-1h-indazole-4-carboxamide Chemical compound O=C1C=2C(C(=O)N)=CC=CC=2NN1C(C=C1)=CC=C1C1CCNCC1 RXSSHKKBZKSMAA-UHFFFAOYSA-N 0.000 claims 1
- IXTUKDJLYHRMHS-UHFFFAOYSA-N 3-oxo-2-(4-pyridin-3-ylphenyl)-1h-indazole-4-carboxamide Chemical compound O=C1C=2C(C(=O)N)=CC=CC=2NN1C(C=C1)=CC=C1C1=CC=CN=C1 IXTUKDJLYHRMHS-UHFFFAOYSA-N 0.000 claims 1
- BIDBVMUJMSZKGL-UHFFFAOYSA-N 3-oxo-2-(4-pyridin-4-ylphenyl)-1h-indazole-4-carboxamide Chemical compound O=C1C=2C(C(=O)N)=CC=CC=2NN1C(C=C1)=CC=C1C1=CC=NC=C1 BIDBVMUJMSZKGL-UHFFFAOYSA-N 0.000 claims 1
- KZGFROWNSPDFSG-UHFFFAOYSA-N 3-oxo-2-[1-(1h-pyrrol-3-ylmethyl)piperidin-4-yl]-1h-indazole-4-carboxamide Chemical compound O=C1C=2C(C(=O)N)=CC=CC=2NN1C(CC1)CCN1CC=1C=CNC=1 KZGFROWNSPDFSG-UHFFFAOYSA-N 0.000 claims 1
- OLJDWQJXPVXMDC-UHFFFAOYSA-N 3-oxo-2-[1-(thiophen-2-ylmethyl)piperidin-4-yl]-1h-indazole-4-carboxamide Chemical compound O=C1C=2C(C(=O)N)=CC=CC=2NN1C(CC1)CCN1CC1=CC=CS1 OLJDWQJXPVXMDC-UHFFFAOYSA-N 0.000 claims 1
- IIMXWNUUYOPBPC-UHFFFAOYSA-N 3-oxo-2-[1-(thiophen-3-ylmethyl)piperidin-4-yl]-1h-indazole-4-carboxamide Chemical compound O=C1C=2C(C(=O)N)=CC=CC=2NN1C(CC1)CCN1CC=1C=CSC=1 IIMXWNUUYOPBPC-UHFFFAOYSA-N 0.000 claims 1
- OQWUKVQDDJFORM-UHFFFAOYSA-N 3-oxo-2-piperidin-4-yl-1h-indazole-4-carboxamide Chemical compound O=C1C=2C(C(=O)N)=CC=CC=2NN1C1CCNCC1 OQWUKVQDDJFORM-UHFFFAOYSA-N 0.000 claims 1
- OYACMDIHHCFBEK-UHFFFAOYSA-N 6-chloro-2-(1-cyclohexylpiperidin-4-yl)-1-methyl-3-oxoindazole-4-carboxamide Chemical compound O=C1C2=C(C(N)=O)C=C(Cl)C=C2N(C)N1C(CC1)CCN1C1CCCCC1 OYACMDIHHCFBEK-UHFFFAOYSA-N 0.000 claims 1
- VHKWRLIBQRSCLB-UHFFFAOYSA-N 6-chloro-2-(1-cyclohexylpiperidin-4-yl)-3-oxo-1h-indazole-4-carboxamide Chemical compound O=C1C=2C(C(=O)N)=CC(Cl)=CC=2NN1C(CC1)CCN1C1CCCCC1 VHKWRLIBQRSCLB-UHFFFAOYSA-N 0.000 claims 1
- VNNYGCPDAUKGHU-UHFFFAOYSA-N 6-fluoro-1-methyl-3-oxo-2-(1-pyridin-3-ylpiperidin-4-yl)indazole-4-carboxamide Chemical compound O=C1C2=C(C(N)=O)C=C(F)C=C2N(C)N1C(CC1)CCN1C1=CC=CN=C1 VNNYGCPDAUKGHU-UHFFFAOYSA-N 0.000 claims 1
- ZSHKOFQSHKXRRJ-UHFFFAOYSA-N 6-fluoro-1-methyl-3-oxo-2-(1-pyridin-4-ylpiperidin-4-yl)indazole-4-carboxamide Chemical compound O=C1C2=C(C(N)=O)C=C(F)C=C2N(C)N1C(CC1)CCN1C1=CC=NC=C1 ZSHKOFQSHKXRRJ-UHFFFAOYSA-N 0.000 claims 1
- NRYJYZXKRNBMDC-UHFFFAOYSA-N 6-fluoro-1-methyl-3-oxo-2-(4-piperidin-4-ylphenyl)indazole-4-carboxamide Chemical compound O=C1C2=C(C(N)=O)C=C(F)C=C2N(C)N1C(C=C1)=CC=C1C1CCNCC1 NRYJYZXKRNBMDC-UHFFFAOYSA-N 0.000 claims 1
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| US9879016B2 (en) | 2015-04-17 | 2018-01-30 | Abbvie Inc. | Indazolones as modulators of TNF signaling |
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| UY36630A (es) | 2015-04-17 | 2016-11-30 | Abbvie Inc | Moduladores tricíclicos de la señalización por tnf |
| CN117980307A (zh) | 2021-08-27 | 2024-05-03 | 上海瑛派药业有限公司 | 取代的三环类化合物作为parp抑制剂及其应用 |
| US20250352539A1 (en) | 2022-06-15 | 2025-11-20 | Astrazeneca Ab | Combination therapy for treating cancer |
| KR20260010420A (ko) | 2023-05-11 | 2026-01-20 | 아스트라제네카 아베 | 암 치료를 위한 parp1 억제제 및 선택적 에스트로겐 분해제의 병용 |
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| US20090275619A1 (en) * | 2006-04-03 | 2009-11-05 | BOUERES Julia | Amide Substituted Indazole and Benzotriazole Derivatives as Poly(ADP-Ribose)Polymerase (PARP) Inhibitors |
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