JP2017503840A5 - - Google Patents
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- JP2017503840A5 JP2017503840A5 JP2016548158A JP2016548158A JP2017503840A5 JP 2017503840 A5 JP2017503840 A5 JP 2017503840A5 JP 2016548158 A JP2016548158 A JP 2016548158A JP 2016548158 A JP2016548158 A JP 2016548158A JP 2017503840 A5 JP2017503840 A5 JP 2017503840A5
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- phenyl
- carbonitrile
- methyl
- 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 52
- -1 C 1 -C 6 - alkoxy Chemical group 0.000 claims 44
- 229910052736 halogen Inorganic materials 0.000 claims 43
- 150000002367 halogens Chemical class 0.000 claims 43
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims 39
- 229910052739 hydrogen Inorganic materials 0.000 claims 38
- 239000001257 hydrogen Substances 0.000 claims 38
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 33
- 150000003839 salts Chemical class 0.000 claims 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims 22
- 150000002431 hydrogen Chemical class 0.000 claims 22
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 21
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 15
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 14
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 13
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 13
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 11
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 11
- 125000000623 heterocyclic group Chemical group 0.000 claims 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 7
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- 125000004043 oxo group Chemical group O=* 0.000 claims 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 3
- 125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- LUQVCHRDAGWYMG-UHFFFAOYSA-N 4-phenylbenzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=CC=CC=C1 LUQVCHRDAGWYMG-UHFFFAOYSA-N 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000004245 indazol-3-yl group Chemical group [H]N1N=C(*)C2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 2
- 230000002757 inflammatory effect Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 2
- 125000004546 quinazolin-4-yl group Chemical group N1=CN=C(C2=CC=CC=C12)* 0.000 claims 2
- NMMWZJOLCAXBSA-YSBYIQCSSA-N (5aS,6S,9aR)-1-[(4-bromophenyl)methyl]-6-methyl-7-oxo-9a-phenyl-4,5,5a,6-tetrahydrobenzo[g]indazole-8-carbonitrile Chemical compound BrC1=CC=C(CN2N=CC=3CC[C@@H]4[C@@](C23)(C=C(C([C@H]4C)=O)C#N)C4=CC=CC=C4)C=C1 NMMWZJOLCAXBSA-YSBYIQCSSA-N 0.000 claims 1
- ATHDFANAWRPRAZ-QFMFQJCFSA-N (5aS,6S,9aR)-1-benzyl-6-methyl-7-oxo-9a-phenyl-4,5,5a,6-tetrahydrobenzo[g]indazole-8-carbonitrile Chemical compound C(C1=CC=CC=C1)N1N=CC=2CC[C@@H]3[C@@](C12)(C=C(C([C@H]3C)=O)C#N)C3=CC=CC=C3 ATHDFANAWRPRAZ-QFMFQJCFSA-N 0.000 claims 1
- GTGHKFOYGLDTMC-YCYJEZDCSA-N (5aS,6S,9aR)-2,6-dimethyl-7-oxo-9a-phenyl-3-(3-pyridazin-4-ylphenyl)-4,5,5a,6-tetrahydrobenzo[g]indazole-8-carbonitrile Chemical compound CN1N=C2[C@@]3([C@@H](CCC2=C1C1=CC(=CC=C1)C1=CN=NC=C1)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 GTGHKFOYGLDTMC-YCYJEZDCSA-N 0.000 claims 1
- KMDYOZMRARBONF-XYQUQUKTSA-N (5aS,6S,9aR)-2,6-dimethyl-7-oxo-9a-phenyl-3-(4-pyridin-4-ylphenyl)-4,5,5a,6-tetrahydrobenzo[g]indazole-8-carbonitrile Chemical compound CN1N=C2[C@@]3([C@@H](CCC2=C1C1=CC=C(C=C1)C1=CC=NC=C1)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 KMDYOZMRARBONF-XYQUQUKTSA-N 0.000 claims 1
- OIATUVJFTWKQLG-YCYJEZDCSA-N (5aS,6S,9aR)-2,6-dimethyl-7-oxo-9a-phenyl-3-(4-pyrimidin-5-ylphenyl)-4,5,5a,6-tetrahydrobenzo[g]indazole-8-carbonitrile Chemical compound CN1N=C2[C@@]3([C@@H](CCC2=C1C1=CC=C(C=C1)C=1C=NC=NC1)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 OIATUVJFTWKQLG-YCYJEZDCSA-N 0.000 claims 1
- DJYICBIKGCEVCJ-DGSCHONISA-N (5aS,6S,9aR)-2,6-dimethyl-7-oxo-9a-phenyl-3-[3-(1H-pyrazol-4-yl)phenyl]-4,5,5a,6-tetrahydrobenzo[g]indazole-8-carbonitrile Chemical compound CN1N=C2[C@@]3([C@@H](CCC2=C1C1=CC(=CC=C1)C=1C=NNC1)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 DJYICBIKGCEVCJ-DGSCHONISA-N 0.000 claims 1
- YTFINPWBGPHHBL-QFMFQJCFSA-N (5aS,6S,9aR)-2-benzyl-6-methyl-7-oxo-9a-phenyl-4,5,5a,6-tetrahydrobenzo[g]indazole-8-carbonitrile Chemical compound C(C1=CC=CC=C1)N1N=C2[C@@]3([C@@H](CCC2=C1)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 YTFINPWBGPHHBL-QFMFQJCFSA-N 0.000 claims 1
- TTYXYQRALCHVAX-DGSCHONISA-N (5aS,6S,9aR)-3-[1-(4-cyanophenyl)pyrazol-4-yl]-6-methyl-7-oxo-9a-phenyl-4,5,5a,6-tetrahydro-1H-benzo[g]indazole-8-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)N1N=CC(=C1)C=1NN=C2[C@@]3([C@@H](CCC12)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 TTYXYQRALCHVAX-DGSCHONISA-N 0.000 claims 1
- OEIIAUFTELVOGV-VVIOKTKKSA-N (5aS,6S,9aR)-3-[3-(2-methoxypyrimidin-5-yl)phenyl]-2,6-dimethyl-7-oxo-9a-phenyl-4,5,5a,6-tetrahydrobenzo[g]indazole-8-carbonitrile Chemical compound COC1=NC=C(C=N1)C=1C=C(C=CC1)C=1N(N=C2[C@@]3([C@@H](CCC12)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3)C OEIIAUFTELVOGV-VVIOKTKKSA-N 0.000 claims 1
- IVKVPTDHGYGGIE-OAAQJRNLSA-N (5aS,6S,9aR)-3-[3-(4-aminophenyl)phenyl]-2,6-dimethyl-7-oxo-9a-phenyl-4,5,5a,6-tetrahydrobenzo[g]indazole-8-carbonitrile Chemical compound NC1=CC=C(C=C1)C1=CC(=CC=C1)C=1N(N=C2[C@@]3([C@@H](CCC12)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3)C IVKVPTDHGYGGIE-OAAQJRNLSA-N 0.000 claims 1
- FWBITOVISMQCFJ-OAAQJRNLSA-N (5aS,6S,9aR)-3-[3-(4-hydroxyphenyl)phenyl]-2,6-dimethyl-7-oxo-9a-phenyl-4,5,5a,6-tetrahydrobenzo[g]indazole-8-carbonitrile Chemical compound OC1=CC=C(C=C1)C1=CC(=CC=C1)C=1N(N=C2[C@@]3([C@@H](CCC12)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3)C FWBITOVISMQCFJ-OAAQJRNLSA-N 0.000 claims 1
- UEMMLTWREZDAOT-FKHUDQKESA-N (5aS,6S,9aR)-6-methyl-7-oxo-9a-phenyl-3-pyridazin-4-yl-4,5,5a,6-tetrahydro-1H-benzo[g]indazole-8-carbonitrile Chemical compound C[C@@H]1C(C(=C[C@]2([C@H]1CCC1=C(NN=C21)C2=CN=NC=C2)C2=CC=CC=C2)C#N)=O UEMMLTWREZDAOT-FKHUDQKESA-N 0.000 claims 1
- BINSJSYDSMEWJB-WQFAYQGZSA-N (5aS,6S,9aR)-9a-(3-fluorophenyl)-6-methyl-7-oxo-4,5,5a,6-tetrahydro-1H-benzo[g]indazole-8-carbonitrile Chemical compound FC=1C=C(C=CC1)[C@]12[C@@H](CCC3=CNN=C13)[C@@H](C(C(=C2)C#N)=O)C BINSJSYDSMEWJB-WQFAYQGZSA-N 0.000 claims 1
- WWUZWZOMKLCHCW-WQFAYQGZSA-N (5aS,6S,9aR)-9a-(4-fluorophenyl)-6-methyl-7-oxo-4,5,5a,6-tetrahydro-1H-benzo[g]indazole-8-carbonitrile Chemical compound FC1=CC=C(C=C1)[C@]12[C@@H](CCC3=CNN=C13)[C@@H](C(C(=C2)C#N)=O)C WWUZWZOMKLCHCW-WQFAYQGZSA-N 0.000 claims 1
- SKVGEYUPPXIOGD-CYFODOTGSA-N (5aS,6S,9aR)-9a-(4-methoxyphenyl)-6-methyl-7-oxo-4,5,5a,6-tetrahydro-1H-benzo[g]indazole-8-carbonitrile Chemical compound COC1=CC=C(C=C1)[C@]12[C@@H](CCC3=CNN=C13)[C@@H](C(C(=C2)C#N)=O)C SKVGEYUPPXIOGD-CYFODOTGSA-N 0.000 claims 1
- GMYLFVJDSODESE-DOPOYZHKSA-N (6S,9aR)-2,6-dimethyl-7-oxo-9a-phenyl-4,5,5a,6-tetrahydrobenzo[g]indazole-8-carbonitrile Chemical compound CN1N=C2[C@@]3(C(CCC2=C1)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 GMYLFVJDSODESE-DOPOYZHKSA-N 0.000 claims 1
- BCZLHEKPDBAGID-BTOQJYRJSA-N (6S,9aR)-2-(2-hydroxyacetyl)-6-methyl-7-oxo-9a-phenyl-4,5,5a,6-tetrahydrobenzo[g]indazole-8-carbonitrile Chemical compound C(CO)(=O)N1N=C2[C@@]3(C(CCC2=C1)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 BCZLHEKPDBAGID-BTOQJYRJSA-N 0.000 claims 1
- MSKBQMXQARALCB-LJVBMILOSA-N (6S,9aR)-2-(benzenesulfonyl)-6-methyl-7-oxo-9a-phenyl-4,5,5a,6-tetrahydrobenzo[g]indazole-8-carbonitrile Chemical compound C[C@@H]1C(C(=C[C@]2(C1CCC1=CN(N=C21)S(=O)(=O)C2=CC=CC=C2)C2=CC=CC=C2)C#N)=O MSKBQMXQARALCB-LJVBMILOSA-N 0.000 claims 1
- UALACOPEMJMVGN-BISKEDJESA-N (6S,9aR)-2-benzoyl-6-methyl-7-oxo-9a-phenyl-4,5,5a,6-tetrahydrobenzo[g]indazole-8-carbonitrile Chemical compound C(C1=CC=CC=C1)(=O)N1N=C2[C@@]3(C(CCC2=C1)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 UALACOPEMJMVGN-BISKEDJESA-N 0.000 claims 1
- CWZKSFMJWTXWJQ-UWRZYQEDSA-N (6S,9aR)-3-(3-hydroxyphenyl)-6-methyl-7-oxo-9a-phenyl-4,5,5a,6-tetrahydro-1H-benzo[g]indazole-8-carbonitrile Chemical compound OC=1C=C(C=CC1)C=1NN=C2[C@@]3(C(CCC12)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 CWZKSFMJWTXWJQ-UWRZYQEDSA-N 0.000 claims 1
- FYEMHADBQMHVMU-FJTYFYTASA-N (6S,9aR)-3-[1-(2-hydroxyethyl)pyrazol-4-yl]-6-methyl-7-oxo-9a-phenyl-4,5,5a,6-tetrahydro-1H-benzo[g]indazole-8-carbonitrile Chemical compound OCCN1N=CC(=C1)C=1NN=C2[C@@]3(C(CCC12)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 FYEMHADBQMHVMU-FJTYFYTASA-N 0.000 claims 1
- UULJTNDJXZKKKE-UWRZYQEDSA-N (6S,9aR)-3-[5-(hydroxymethyl)pyridin-3-yl]-6-methyl-7-oxo-9a-phenyl-4,5,5a,6-tetrahydro-1H-benzo[g]indazole-8-carbonitrile Chemical compound OCC=1C=C(C=NC1)C=1NN=C2[C@@]3(C(CCC12)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 UULJTNDJXZKKKE-UWRZYQEDSA-N 0.000 claims 1
- DIXMVNYQPGHELS-DOPOYZHKSA-N (6S,9aR)-6-methyl-2-methylsulfonyl-7-oxo-9a-phenyl-4,5,5a,6-tetrahydrobenzo[g]indazole-8-carbonitrile Chemical compound C[C@@H]1C(C(=C[C@]2(C1CCC1=CN(N=C21)S(=O)(=O)C)C2=CC=CC=C2)C#N)=O DIXMVNYQPGHELS-DOPOYZHKSA-N 0.000 claims 1
- IBCTVWRGHTZOCO-QKWRCOSUSA-N (6S,9aR)-6-methyl-3-(1-methylpyrazol-4-yl)-7-oxo-9a-phenyl-4,5,5a,6-tetrahydro-1H-benzo[g]indazole-8-carbonitrile Chemical compound C[C@@H]1C(C(=C[C@]2(C1CCC1=C(NN=C21)C=2C=NN(C2)C)C2=CC=CC=C2)C#N)=O IBCTVWRGHTZOCO-QKWRCOSUSA-N 0.000 claims 1
- NGVKWRPAMFNWRM-BRASLUBNSA-N (6S,9aR)-6-methyl-7-oxo-9a-phenyl-2-(1,3-thiazole-4-carbonyl)-4,5,5a,6-tetrahydrobenzo[g]indazole-8-carbonitrile Chemical compound C[C@@H]1C(C(=C[C@]2(C1CCC1=CN(N=C21)C(=O)C=2N=CSC2)C2=CC=CC=C2)C#N)=O NGVKWRPAMFNWRM-BRASLUBNSA-N 0.000 claims 1
- IPWFTHOLAOQTTB-FJTYFYTASA-N (6S,9aR)-6-methyl-7-oxo-9a-phenyl-3-pyridin-3-yl-4,5,5a,6-tetrahydro-1H-benzo[g]indazole-8-carbonitrile Chemical compound C[C@@H]1C(C(=C[C@]2(C1CCC1=C(NN=C21)C=2C=NC=CC2)C2=CC=CC=C2)C#N)=O IPWFTHOLAOQTTB-FJTYFYTASA-N 0.000 claims 1
- RAXMUQCAGTVAGT-QKWRCOSUSA-N (6S,9aR)-6-methyl-7-oxo-9a-phenyl-3-pyrimidin-5-yl-4,5,5a,6-tetrahydro-1H-benzo[g]indazole-8-carbonitrile Chemical compound C[C@@H]1C(C(=C[C@]2(C1CCC1=C(NN=C21)C=2C=NC=NC2)C2=CC=CC=C2)C#N)=O RAXMUQCAGTVAGT-QKWRCOSUSA-N 0.000 claims 1
- WWRYSJLVOMDRAJ-JFNNDOMUSA-N (6S,9aR)-6-methyl-7-oxo-9a-phenyl-4,5,5a,6-tetrahydro-1H-benzo[g]indazole-8-carbonitrile Chemical compound C[C@@H]1C(C(=C[C@]2(C1CCC1=CNN=C21)C2=CC=CC=C2)C#N)=O WWRYSJLVOMDRAJ-JFNNDOMUSA-N 0.000 claims 1
- OOBOJZMKXLJTPT-MKVZMPEWSA-N (6S,9aR)-9a-(3-fluorophenyl)-3-[3-(3-hydroxypropyl)phenyl]-6-methyl-7-oxo-4,5,5a,6-tetrahydro-1H-benzo[g]indazole-8-carbonitrile Chemical compound FC=1C=C(C=CC1)[C@]12C(CCC3=C(NN=C13)C1=CC(=CC=C1)CCCO)[C@@H](C(C(=C2)C#N)=O)C OOBOJZMKXLJTPT-MKVZMPEWSA-N 0.000 claims 1
- DUFNFTYAGCSURQ-ODUJOWDVSA-N (6S,9aR)-9a-(4-hydroxyphenyl)-6-methyl-7-oxo-4,5,5a,6-tetrahydro-1H-benzo[g]indazole-8-carbonitrile Chemical compound OC1=CC=C(C=C1)[C@]12C(CCC3=CNN=C13)[C@@H](C(C(=C2)C#N)=O)C DUFNFTYAGCSURQ-ODUJOWDVSA-N 0.000 claims 1
- OMROOUUPQRXSJJ-OGLLEDLLSA-N (6aS,7S,10aR)-10a-(3-fluorophenyl)-2,7-dimethyl-8-oxo-4-pyrimidin-5-yl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound FC=1C=C(C=CC1)[C@]12[C@@H](CCC=3C(=NC(=NC13)C)C=1C=NC=NC1)[C@@H](C(C(=C2)C#N)=O)C OMROOUUPQRXSJJ-OGLLEDLLSA-N 0.000 claims 1
- OFLCZLMKGWREHS-CYFODOTGSA-N (6aS,7S,10aR)-10a-(3-hydroxyphenyl)-7-methyl-8-oxo-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound OC=1C=C(C=CC1)[C@]12[C@@H](CCC=3C=NC=NC13)[C@@H](C(C(=C2)C#N)=O)C OFLCZLMKGWREHS-CYFODOTGSA-N 0.000 claims 1
- IFPXBZQPRFUNKA-LWLGHBPASA-N (6aS,7S,10aR)-10a-(4-fluorophenyl)-2,7-dimethyl-8-oxo-4-[4-(1H-pyrazol-5-yl)phenyl]-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound FC1=CC=C(C=C1)[C@]12[C@@H](CCC=3C(=NC(=NC13)C)C1=CC=C(C=C1)C1=CC=NN1)[C@@H](C(C(=C2)C#N)=O)C IFPXBZQPRFUNKA-LWLGHBPASA-N 0.000 claims 1
- KDAZXMOWVRIKSJ-OGLLEDLLSA-N (6aS,7S,10aR)-10a-(4-fluorophenyl)-2,7-dimethyl-8-oxo-4-pyrimidin-5-yl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound FC1=CC=C(C=C1)[C@]12[C@@H](CCC=3C(=NC(=NC13)C)C=1C=NC=NC1)[C@@H](C(C(=C2)C#N)=O)C KDAZXMOWVRIKSJ-OGLLEDLLSA-N 0.000 claims 1
- KHMRQIYLSHTHMS-JOVVQLDHSA-N (6aS,7S,10aR)-10a-(4-fluorophenyl)-4-(1H-indazol-7-yl)-2,7-dimethyl-8-oxo-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound FC1=CC=C(C=C1)[C@]12[C@@H](CCC=3C(=NC(=NC13)C)C=1C=CC=C3C=NNC13)[C@@H](C(C(=C2)C#N)=O)C KHMRQIYLSHTHMS-JOVVQLDHSA-N 0.000 claims 1
- NYRNNPJDSUUDBB-HHCYOLOASA-N (6aS,7S,10aR)-10a-(4-fluorophenyl)-7-methyl-8-oxo-2-pyridin-3-yl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound FC1=CC=C(C=C1)[C@]12[C@@H](CCC=3C=NC(=NC13)C=1C=NC=CC1)[C@@H](C(C(=C2)C#N)=O)C NYRNNPJDSUUDBB-HHCYOLOASA-N 0.000 claims 1
- MQSBFKFVRQTWLX-CYFODOTGSA-N (6aS,7S,10aR)-10a-(4-fluorophenyl)-7-methyl-8-oxo-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound FC1=CC=C(C=C1)[C@]12[C@@H](CCC=3C=NC=NC13)[C@@H](C(C(=C2)C#N)=O)C MQSBFKFVRQTWLX-CYFODOTGSA-N 0.000 claims 1
- YUSZLMCTDZGGMR-CYFODOTGSA-N (6aS,7S,10aR)-10a-(4-hydroxyphenyl)-7-methyl-8-oxo-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound OC1=CC=C(C=C1)[C@]12[C@@H](CCC=3C=NC=NC13)[C@@H](C(C(=C2)C#N)=O)C YUSZLMCTDZGGMR-CYFODOTGSA-N 0.000 claims 1
- CYFXOJBMPVPEGG-KCMSVQPVSA-N (6aS,7S,10aR)-10a-(4-methoxyphenyl)-2,7-dimethyl-4-(3-methylimidazol-4-yl)-8-oxo-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound COC1=CC=C(C=C1)[C@]12[C@@H](CCC=3C(=NC(=NC13)C)C1=CN=CN1C)[C@@H](C(C(=C2)C#N)=O)C CYFXOJBMPVPEGG-KCMSVQPVSA-N 0.000 claims 1
- WUFVVUNDFNJTKP-LVAJYGNLSA-N (6aS,7S,10aR)-10a-(4-methoxyphenyl)-2,7-dimethyl-8-oxo-4-[4-(1H-pyrazol-5-yl)phenyl]-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound COC1=CC=C(C=C1)[C@]12[C@@H](CCC=3C(=NC(=NC13)C)C1=CC=C(C=C1)C1=CC=NN1)[C@@H](C(C(=C2)C#N)=O)C WUFVVUNDFNJTKP-LVAJYGNLSA-N 0.000 claims 1
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- LBPIXTFUFFLXGD-UHFFFAOYSA-N 9a-benzyl-2,6-dimethyl-7-oxo-4,5,5a,6-tetrahydrobenzo[g]indazole-8-carbonitrile Chemical compound C(C1=CC=CC=C1)C12C(CCC3=CN(N=C13)C)C(C(C(=C2)C#N)=O)C LBPIXTFUFFLXGD-UHFFFAOYSA-N 0.000 claims 1
- RIZDPZXGBBFJOX-OJQANEPJSA-N N-[3-[(6S,9aR)-8-cyano-6-methyl-7-oxo-9a-phenyl-4,5,5a,6-tetrahydro-1H-benzo[g]indazol-3-yl]phenyl]methanesulfonamide Chemical compound C(#N)C1=C[C@]2(C(CCC3=C(NN=C23)C=2C=C(C=CC2)NS(=O)(=O)C)[C@@H](C1=O)C)C1=CC=CC=C1 RIZDPZXGBBFJOX-OJQANEPJSA-N 0.000 claims 1
- ABYIFLBMFNNLJL-UPPTWSTHSA-N N-[3-[3-[(5aS,6S,9aR)-8-cyano-2,6-dimethyl-7-oxo-9a-phenyl-4,5,5a,6-tetrahydrobenzo[g]indazol-3-yl]phenyl]phenyl]methanesulfonamide Chemical compound C(#N)C1=C[C@]2([C@@H](CCC3=C(N(N=C23)C)C=2C=C(C=CC2)C2=CC(=CC=C2)NS(=O)(=O)C)[C@@H](C1=O)C)C1=CC=CC=C1 ABYIFLBMFNNLJL-UPPTWSTHSA-N 0.000 claims 1
- XHLXCIQYKKKSSG-OJQANEPJSA-N N-[4-[(6S,9aR)-8-cyano-6-methyl-7-oxo-9a-phenyl-4,5,5a,6-tetrahydro-1H-benzo[g]indazol-3-yl]phenyl]methanesulfonamide Chemical compound C(#N)C1=C[C@]2(C(CCC3=C(NN=C23)C2=CC=C(C=C2)NS(=O)(=O)C)[C@@H](C1=O)C)C1=CC=CC=C1 XHLXCIQYKKKSSG-OJQANEPJSA-N 0.000 claims 1
- LHNWZXGZMUKWRY-UPPTWSTHSA-N N-[4-[3-[(5aS,6S,9aR)-8-cyano-2,6-dimethyl-7-oxo-9a-phenyl-4,5,5a,6-tetrahydrobenzo[g]indazol-3-yl]phenyl]phenyl]methanesulfonamide Chemical compound C(#N)C1=C[C@]2([C@@H](CCC3=C(N(N=C23)C)C=2C=C(C=CC2)C2=CC=C(C=C2)NS(=O)(=O)C)[C@@H](C1=O)C)C1=CC=CC=C1 LHNWZXGZMUKWRY-UPPTWSTHSA-N 0.000 claims 1
- ZIHSEDBXJYFWOF-DYCYAPRISA-N N-[[4-[3-[(5aS,6S,9aR)-8-cyano-2,6-dimethyl-7-oxo-9a-phenyl-4,5,5a,6-tetrahydrobenzo[g]indazol-3-yl]phenyl]phenyl]methyl]methanesulfonamide Chemical compound C(#N)C1=C[C@]2([C@@H](CCC3=C(N(N=C23)C)C=2C=C(C=CC2)C2=CC=C(C=C2)CNS(=O)(=O)C)[C@@H](C1=O)C)C1=CC=CC=C1 ZIHSEDBXJYFWOF-DYCYAPRISA-N 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 230000001363 autoimmune Effects 0.000 claims 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 1
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- ZIVDOZQFQXISLT-BTOQJYRJSA-N methyl (6S,9aR)-8-cyano-6-methyl-7-oxo-9a-phenyl-4,5,5a,6-tetrahydrobenzo[g]indazole-2-carboxylate Chemical compound C(#N)C1=C[C@]2(C(CCC3=CN(N=C23)C(=O)OC)[C@@H](C1=O)C)C1=CC=CC=C1 ZIVDOZQFQXISLT-BTOQJYRJSA-N 0.000 claims 1
- SOACHSBDLMIVKN-AXNJZRPJSA-N methyl 3-[(6aS,7S,10aR)-9-cyano-7-methyl-8-oxo-2-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazolin-10a-yl]benzoate Chemical compound C(#N)C1=C[C@]2([C@@H](CCC=3C=NC(=NC23)C2=CC=CC=C2)[C@@H](C1=O)C)C=1C=C(C(=O)OC)C=CC1 SOACHSBDLMIVKN-AXNJZRPJSA-N 0.000 claims 1
- RHGREININJHHLK-KVYZTJHFSA-N methyl 3-[(6aS,7S,10aR)-9-cyano-7-methyl-8-oxo-5,6,6a,7-tetrahydrobenzo[h]quinazolin-10a-yl]benzoate Chemical compound C(#N)C1=C[C@]2([C@@H](CCC=3C=NC=NC23)[C@@H](C1=O)C)C=1C=C(C(=O)OC)C=CC1 RHGREININJHHLK-KVYZTJHFSA-N 0.000 claims 1
- SLWJPQUNLBXMDY-KCMSVQPVSA-N methyl 4-[(6aS,7S,10aR)-9-cyano-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazolin-4-yl]pyrazole-1-carboxylate Chemical compound C(#N)C1=C[C@]2([C@@H](CCC=3C(=NC(=NC23)C)C=2C=NN(C2)C(=O)OC)[C@@H](C1=O)C)C1=CC=CC=C1 SLWJPQUNLBXMDY-KCMSVQPVSA-N 0.000 claims 1
- NDWQIUBNEQGUEP-KVYZTJHFSA-N methyl 4-[(6aS,7S,10aR)-9-cyano-7-methyl-8-oxo-5,6,6a,7-tetrahydrobenzo[h]quinazolin-10a-yl]benzoate Chemical compound C(#N)C1=C[C@]2([C@@H](CCC=3C=NC=NC23)[C@@H](C1=O)C)C1=CC=C(C(=O)OC)C=C1 NDWQIUBNEQGUEP-KVYZTJHFSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- SIICXYUWWUGVSZ-BISKEDJESA-N phenyl (6S,9aR)-8-cyano-6-methyl-7-oxo-9a-phenyl-4,5,5a,6-tetrahydrobenzo[g]indazole-2-carboxylate Chemical compound C(#N)C1=C[C@]2(C(CCC3=CN(N=C23)C(=O)OC2=CC=CC=C2)[C@@H](C1=O)C)C1=CC=CC=C1 SIICXYUWWUGVSZ-BISKEDJESA-N 0.000 claims 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims 1
- 125000004260 quinazolin-2-yl group Chemical group [H]C1=NC(*)=NC2=C1C([H])=C([H])C([H])=C2[H] 0.000 claims 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 1
- 0 *C(CC1(*)c2nc(*)nc(*)c2C*C11)CC1(*)I Chemical compound *C(CC1(*)c2nc(*)nc(*)c2C*C11)CC1(*)I 0.000 description 4
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| PCT/US2015/012579 WO2015112792A1 (en) | 2014-01-24 | 2015-01-23 | Aryl and arylalkyl substituted pyrazolyl and pyrimidinyl tricyclic enones as antioxidant inflammation modulators |
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| CA2721665C (en) | 2008-04-18 | 2017-01-24 | Reata Pharmaceuticals, Inc. | Compounds including an anti-inflammatory pharmacore and methods of use |
| WO2009129546A1 (en) | 2008-04-18 | 2009-10-22 | Reata Pharmaceuticals, Inc. | Antioxidant inflammation modulators: oleanolic acid derivatives with amino and other modifications at c-17 |
| JP6410710B2 (ja) | 2012-04-27 | 2018-10-24 | リアタ ファーマシューティカルズ インコーポレイテッド | バルドキソロンメチルの２，２−ジフルオロプロピオンアミド誘導体、その多形体および使用方法 |
| US9512094B2 (en) | 2012-09-10 | 2016-12-06 | Reata Pharmaceuticals, Inc. | C17-heteroaryl derivatives of oleanolic acid and methods of use thereof |
| TWI649330B (zh) | 2013-04-24 | 2019-02-01 | 艾伯維有限公司 | 甲基巴多索龍之２，２－二氟丙醯胺衍生物、其多晶形及其使用方法 |
| CN107428698B (zh) * | 2015-02-12 | 2021-10-26 | 里亚塔医药公司 | 作为抗氧化炎症调节剂的咪唑基三环烯酮 |
| BR112019010511A2 (pt) | 2016-11-23 | 2019-09-17 | Bayer Ag | derivados de heterociclo bicíclico fundido como pesticidas |
| TWI831738B (zh) * | 2016-12-16 | 2024-02-11 | 美商瑞塔醫藥有限責任公司 | 用於抑制ＲＯＲγ及其他用途的嘧啶三環烯酮衍生物 |
| IL279348B2 (en) * | 2018-06-15 | 2026-01-01 | Reata Pharmaceuticals Inc | Decahydro-2h-naphth[1,2-d]imidazole compounds for inhibition of IL-17 and ROR-gamma |
| WO2019246461A1 (en) | 2018-06-20 | 2019-12-26 | Reata Pharmaceuticals, Inc. | Cysteine-dependent inverse agonists of nuclear receptors ror-gamma/ror-gamma-t and methods of treating diseases or disorders therewith |
| US20250025465A1 (en) * | 2021-11-17 | 2025-01-23 | Northwestern University | Wt-idh1 inhibition using a covalent and brain-penetrant small molecular inhibitor for ferroptosis induction in high-grade glioma |
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| EP1142889A1 (en) | 2000-04-03 | 2001-10-10 | Pfizer Products Inc. | Pyrazole derivatives as anti-inflammatory/analgesic agents |
| JP2005507892A (ja) * | 2001-09-19 | 2005-03-24 | ファルマシア・コーポレーション | 炎症の治療のための置換されたピラゾリルベンゼンスルファミド化合物 |
| MX357596B (es) | 2010-04-12 | 2018-07-16 | Reata Pharmaceuticals Inc | Método para tratar obesidad utilizando moduladores de inflamación con antioxidantes. |
| PL2651902T3 (pl) * | 2010-12-17 | 2018-04-30 | Reata Pharmaceuticals, Inc. | Pirazolilowe i pirymidynylowe tricykliczne enony jako modulatory zapalenia o działaniu przeciwutleniającym |
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- 2015-01-23 CN CN201580015069.4A patent/CN107074801B/zh active Active
- 2015-01-23 TW TW104102426A patent/TWI670263B/zh active
- 2015-01-23 WO PCT/US2015/012579 patent/WO2015112792A1/en not_active Ceased
- 2015-01-23 MX MX2016009589A patent/MX372772B/es active IP Right Grant
- 2015-01-23 CA CA2936550A patent/CA2936550C/en active Active
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