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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| US201461931291P | 2014-01-24 | 2014-01-24 | |
| US61/931,291 | 2014-01-24 | ||
| 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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| JP2017503840A JP2017503840A (ja) | 2017-02-02 |
| JP2017503840A5 true JP2017503840A5 (OSRAM) | 2018-03-01 |
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| MX (1) | MX372772B (OSRAM) |
| TW (1) | TWI670263B (OSRAM) |
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Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
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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 |
| KR101735807B1 (ko) | 2008-04-18 | 2017-05-15 | 리타 파마슈티컬스 잉크. | Ｃ-17에 아미노 및 기타 변형을 갖는 올레아놀산 유도체를 포함하는 항산화 염증 조절제 |
| ME02926B (me) | 2012-04-27 | 2018-04-20 | Reata Pharmaceuticals Inc | 2,2-difluoropropionamidni derivati bardoksolon metila, polimorfni oblici i postupci za njihovu upotrebu |
| US9512094B2 (en) | 2012-09-10 | 2016-12-06 | Reata Pharmaceuticals, Inc. | C17-heteroaryl derivatives of oleanolic acid and methods of use thereof |
| UY39092A (es) | 2013-04-24 | 2021-03-26 | Abbvie Inc | Derivados de 2,2-difluoropropanamida y metil bardoxolona, formas polimórficas y métodos de uso |
| US11059792B2 (en) * | 2015-02-12 | 2021-07-13 | Reata Pharmaceuticals, Inc. | Imidazolyl tricyclic enones as antioxidant inflammation modulators |
| WO2018095953A1 (de) | 2016-11-23 | 2018-05-31 | Bayer Cropscience Aktiengesellschaft | 2-[3-(alkylsulfonyl)-2h-indazol-2-yl]-3h-imidazo[4,5-b]pyridin-derivate und ähnliche verbindungen als schädlingsbekämpfungsmittel |
| 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 |
| BR112020025605A2 (pt) * | 2018-06-15 | 2021-03-23 | Reata Pharmaceuticals, Inc. | compostos de pirazol e imidazol para inibição de il-17 e rorgama |
| EP3810141A1 (en) | 2018-06-20 | 2021-04-28 | 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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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP1142889A1 (en) * | 2000-04-03 | 2001-10-10 | Pfizer Products Inc. | Pyrazole derivatives as anti-inflammatory/analgesic agents |
| EP1438293A2 (en) * | 2001-09-19 | 2004-07-21 | Pharmacia Corporation | Substituted pyrazolyl benzenesulfamide compounds for the treatment of inflammation |
| MY163031A (en) | 2010-04-12 | 2017-07-31 | Reata Pharmaceuticals Inc | Method of treating obesity using antioxidant inflammation modulators |
| HUE038046T2 (hu) * | 2010-12-17 | 2018-09-28 | Reata Pharmaceuticals Inc | Antioxidáns gyulladáscsökkentõ pirazolil és pirimidinil triciklusos enonok |
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- 2015-01-23 US US14/604,129 patent/US9464082B2/en active Active
- 2015-01-23 TW TW104102426A patent/TWI670263B/zh active
- 2015-01-23 JP JP2016548158A patent/JP6530758B2/ja active Active
- 2015-01-23 WO PCT/US2015/012579 patent/WO2015112792A1/en not_active Ceased
- 2015-01-23 CN CN201580015069.4A patent/CN107074801B/zh active Active
- 2015-01-23 CA CA2936550A patent/CA2936550C/en active Active
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