JP2017503840A5 - - Google Patents
Download PDFInfo
- Publication number
- 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
Links
- 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
- BEXDMHJKPAPSBJ-CGLDCDAWSA-N (6aS,7S,10aR)-10a-(4-methoxyphenyl)-2,7-dimethyl-8-oxo-4-pyrimidin-5-yl-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)C=1C=NC=NC1)[C@@H](C(C(=C2)C#N)=O)C BEXDMHJKPAPSBJ-CGLDCDAWSA-N 0.000 claims 1
- BICOYUUCDPDTOT-LTBCBRHQSA-N (6aS,7S,10aR)-10a-(4-methoxyphenyl)-7-methyl-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@@H](C(C(=C2)C#N)=O)C BICOYUUCDPDTOT-LTBCBRHQSA-N 0.000 claims 1
- RBQFFNIVSKZMLY-YOKWENHESA-N (6aS,7S,10aR)-2,4-dimethoxy-7-methyl-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound COC1=NC=2[C@@]3([C@@H](CCC2C(=N1)OC)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 RBQFFNIVSKZMLY-YOKWENHESA-N 0.000 claims 1
- QDBBSZOCOJLFFY-ODLKPZKQSA-N (6aS,7S,10aR)-2,7-dimethyl-4,8-dioxo-10a-phenyl-5,6,6a,7-tetrahydro-3H-benzo[h]quinazoline-9-carbonitrile Chemical compound OC1=NC(=NC=2[C@@]3([C@@H](CCC12)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3)C QDBBSZOCOJLFFY-ODLKPZKQSA-N 0.000 claims 1
- OAUMCUYNOIUFQT-UWYNZWELSA-N (6aS,7S,10aR)-2,7-dimethyl-4-(1-methyl-6-oxopyridin-3-yl)-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound CC1=NC=2[C@@]3([C@@H](CCC2C(=N1)C1=CN(C(C=C1)=O)C)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 OAUMCUYNOIUFQT-UWYNZWELSA-N 0.000 claims 1
- GVHWFSOEITWPHB-HHCYOLOASA-N (6aS,7S,10aR)-2,7-dimethyl-4-(1-methylpyrazol-4-yl)-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound CC1=NC=2[C@@]3([C@@H](CCC2C(=N1)C=1C=NN(C1)C)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 GVHWFSOEITWPHB-HHCYOLOASA-N 0.000 claims 1
- MVJLHSDKBOXXIJ-ZZTIUOAXSA-N (6aS,7S,10aR)-2,7-dimethyl-4-(2-methyl-1,3-thiazol-5-yl)-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound CC1=NC=2[C@@]3([C@@H](CCC2C(=N1)C1=CN=C(S1)C)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 MVJLHSDKBOXXIJ-ZZTIUOAXSA-N 0.000 claims 1
- VNDSSHCOQBRZLE-PCKXHRCSSA-N (6aS,7S,10aR)-2,7-dimethyl-4-(3-methylimidazol-4-yl)-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound CC1=NC=2[C@@]3([C@@H](CCC2C(=N1)C1=CN=CN1C)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 VNDSSHCOQBRZLE-PCKXHRCSSA-N 0.000 claims 1
- UYTJTEJQMMZOFE-VVIOKTKKSA-N (6aS,7S,10aR)-2,7-dimethyl-4-[4-(3-methylimidazol-4-yl)phenyl]-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound CC1=NC=2[C@@]3([C@@H](CCC2C(=N1)C1=CC=C(C=C1)C1=CN=CN1C)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 UYTJTEJQMMZOFE-VVIOKTKKSA-N 0.000 claims 1
- WRXTUBIRBNDBIB-OSZRXVRWSA-N (6aS,7S,10aR)-2,7-dimethyl-8-oxo-10a-phenyl-4-(1H-pyrazol-4-yl)-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound CC1=NC=2[C@@]3([C@@H](CCC2C(=N1)C=1C=NNC1)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 WRXTUBIRBNDBIB-OSZRXVRWSA-N 0.000 claims 1
- MMQKRIUMHSPEMA-OAAQJRNLSA-N (6aS,7S,10aR)-2,7-dimethyl-8-oxo-10a-phenyl-4-(4-pyridin-4-ylphenyl)-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound CC1=NC=2[C@@]3([C@@H](CCC2C(=N1)C1=CC=C(C=C1)C1=CC=NC=C1)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 MMQKRIUMHSPEMA-OAAQJRNLSA-N 0.000 claims 1
- QOBOEIPOZGNLHK-FGBDQBTKSA-N (6aS,7S,10aR)-2,7-dimethyl-8-oxo-10a-phenyl-4-(4-pyrimidin-5-ylphenyl)-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound CC1=NC=2[C@@]3([C@@H](CCC2C(=N1)C1=CC=C(C=C1)C=1C=NC=NC1)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 QOBOEIPOZGNLHK-FGBDQBTKSA-N 0.000 claims 1
- LRVAITHUZJQQCR-LVAJYGNLSA-N (6aS,7S,10aR)-2,7-dimethyl-8-oxo-10a-phenyl-4-(4-pyrimidin-5-ylphenyl)-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carboxamide Chemical compound CC1=NC=2[C@@]3([C@@H](CCC2C(=N1)C1=CC=C(C=C1)C=1C=NC=NC1)[C@@H](C(C(=C3)C(=O)N)=O)C)C3=CC=CC=C3 LRVAITHUZJQQCR-LVAJYGNLSA-N 0.000 claims 1
- AGOPJXCKAORKLX-AWCXEYNZSA-N (6aS,7S,10aR)-2,7-dimethyl-8-oxo-10a-phenyl-4-(pyridin-3-ylamino)-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound CC1=NC=2[C@@]3([C@@H](CCC2C(=N1)NC=1C=NC=CC1)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 AGOPJXCKAORKLX-AWCXEYNZSA-N 0.000 claims 1
- QGJMJNAHYRQWNS-HHCYOLOASA-N (6aS,7S,10aR)-2,7-dimethyl-8-oxo-10a-phenyl-4-pyridazin-4-yl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound CC1=NC=2[C@@]3([C@@H](CCC2C(=N1)C1=CN=NC=C1)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 QGJMJNAHYRQWNS-HHCYOLOASA-N 0.000 claims 1
- BIULHOKVWZWKKS-AWCXEYNZSA-N (6aS,7S,10aR)-2,7-dimethyl-8-oxo-10a-phenyl-4-pyridin-4-yl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound CC1=NC=2[C@@]3([C@@H](CCC2C(=N1)C1=CC=NC=C1)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 BIULHOKVWZWKKS-AWCXEYNZSA-N 0.000 claims 1
- ARXIXFXMOMLXJL-HHCYOLOASA-N (6aS,7S,10aR)-2,7-dimethyl-8-oxo-10a-phenyl-4-pyrimidin-5-yl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound CC1=NC=2[C@@]3([C@@H](CCC2C(=N1)C=1C=NC=NC1)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 ARXIXFXMOMLXJL-HHCYOLOASA-N 0.000 claims 1
- AYUIBLHZJBAPPS-ZZTIUOAXSA-N (6aS,7S,10aR)-2,7-dimethyl-8-oxo-10a-phenyl-4-pyrimidin-5-yl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carboxamide Chemical compound CC1=NC=2[C@@]3([C@@H](CCC2C(=N1)C=1C=NC=NC1)[C@@H](C(C(=C3)C(=O)N)=O)C)C3=CC=CC=C3 AYUIBLHZJBAPPS-ZZTIUOAXSA-N 0.000 claims 1
- RUVKLIHXCHFMNF-JKLWDZIJSA-N (6aS,7S,10aR)-2,7-dimethyl-8-oxo-10a-phenyl-4-quinolin-6-yl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound CC1=NC=2[C@@]3([C@@H](CCC2C(=N1)C=1C=C2C=CC=NC2=CC1)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 RUVKLIHXCHFMNF-JKLWDZIJSA-N 0.000 claims 1
- RJPXQFKMMDJNCY-XMFBKKLCSA-N (6aS,7S,10aR)-2,7-dimethyl-8-oxo-4,10a-diphenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound CC1=NC=2[C@@]3([C@@H](CCC2C(=N1)C1=CC=CC=C1)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 RJPXQFKMMDJNCY-XMFBKKLCSA-N 0.000 claims 1
- NZKMABBBDCTPGQ-SRPFZCJZSA-N (6aS,7S,10aR)-2-(2,6-difluorophenyl)-7-methyl-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound FC1=C(C(=CC=C1)F)C1=NC=2[C@@]3([C@@H](CCC2C=N1)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 NZKMABBBDCTPGQ-SRPFZCJZSA-N 0.000 claims 1
- NITQHCGUFOLHNW-CHNWYSDESA-N (6aS,7S,10aR)-2-(2-fluorophenyl)-7-methyl-8-oxo-10a-phenyl-4-propan-2-yloxy-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound FC1=C(C=CC=C1)C1=NC=2[C@@]3([C@@H](CCC2C(=N1)OC(C)C)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 NITQHCGUFOLHNW-CHNWYSDESA-N 0.000 claims 1
- FKODXTCZCNVYCS-UWYNZWELSA-N (6aS,7S,10aR)-2-(4-bromoanilino)-4-methoxy-7-methyl-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound BrC1=CC=C(C=C1)NC1=NC=2[C@@]3([C@@H](CCC2C(=N1)OC)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 FKODXTCZCNVYCS-UWYNZWELSA-N 0.000 claims 1
- RJRBJAOPQXILTE-AWCXEYNZSA-N (6aS,7S,10aR)-2-(4-hydroxyphenyl)-7-methyl-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound OC1=CC=C(C=C1)C1=NC=2[C@@]3([C@@H](CCC2C=N1)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 RJRBJAOPQXILTE-AWCXEYNZSA-N 0.000 claims 1
- QNUXTPLSEPXYSR-GSMBIVSISA-N (6aS,7S,10aR)-2-(diethylamino)-7-methyl-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound C(C)N(C1=NC=2[C@@]3([C@@H](CCC2C=N1)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3)CC QNUXTPLSEPXYSR-GSMBIVSISA-N 0.000 claims 1
- DXXVDXLMWJZUNV-VELBRHGASA-N (6aS,7S,10aR)-2-(ethylamino)-7-methyl-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound C(C)NC1=NC=2[C@@]3([C@@H](CCC2C=N1)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 DXXVDXLMWJZUNV-VELBRHGASA-N 0.000 claims 1
- QDVUBNTYGBPCTD-NIIFMQKASA-N (6aS,7S,10aR)-2-anilino-4-methoxy-7-methyl-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound N(C1=CC=CC=C1)C1=NC=2[C@@]3([C@@H](CCC2C(=N1)OC)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 QDVUBNTYGBPCTD-NIIFMQKASA-N 0.000 claims 1
- QVJTYCUNEMYKEI-MLIAIACYSA-N (6aS,7S,10aR)-2-anilino-7-methyl-8-oxo-10a-phenyl-4-pyrimidin-5-yl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound N(C1=CC=CC=C1)C1=NC=2[C@@]3([C@@H](CCC2C(=N1)C=1C=NC=NC1)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 QVJTYCUNEMYKEI-MLIAIACYSA-N 0.000 claims 1
- KBJFZRFLYHXCKK-LBJGKRIESA-N (6aS,7S,10aR)-2-chloro-4-methoxy-7-methyl-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound ClC1=NC=2[C@@]3([C@@H](CCC2C(=N1)OC)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 KBJFZRFLYHXCKK-LBJGKRIESA-N 0.000 claims 1
- ZIZMVRFNEAAAMO-QJQUAVMFSA-N (6aS,7S,10aR)-2-tert-butyl-7-methyl-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound C(C)(C)(C)C1=NC=2[C@@]3([C@@H](CCC2C=N1)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 ZIZMVRFNEAAAMO-QJQUAVMFSA-N 0.000 claims 1
- FIMLNLXFIPIGOZ-CGLDCDAWSA-N (6aS,7S,10aR)-4-(1-acetylpyrazol-4-yl)-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound C(C)(=O)N1N=CC(=C1)C1=NC(=NC=2[C@@]3([C@@H](CCC12)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3)C FIMLNLXFIPIGOZ-CGLDCDAWSA-N 0.000 claims 1
- LUBUCUGNQSSVMA-TXSNUYOVSA-N (6aS,7S,10aR)-4-(2,4-dioxo-1H-pyrimidin-5-yl)-10a-(4-fluorophenyl)-2,7-dimethyl-8-oxo-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound O=C1NC=C(C(N1)=O)C1=NC(=NC=2[C@@]3([C@@H](CCC12)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=C(C=C3)F)C LUBUCUGNQSSVMA-TXSNUYOVSA-N 0.000 claims 1
- WRXZAEVSVSSTKZ-QFCZIGNWSA-N (6aS,7S,10aR)-4-(3-bromo-2H-indazol-7-yl)-10a-(4-fluorophenyl)-2,7-dimethyl-8-oxo-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound BrC1=NNC2=C(C=CC=C12)C1=NC(=NC=2[C@@]3([C@@H](CCC12)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=C(C=C3)F)C WRXZAEVSVSSTKZ-QFCZIGNWSA-N 0.000 claims 1
- CWABTZFJZYEVTP-PFPXXSDYSA-N (6aS,7S,10aR)-4-(3-bromo-4-morpholin-4-ylphenyl)-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound BrC=1C=C(C=CC1N1CCOCC1)C1=NC(=NC=2[C@@]3([C@@H](CCC12)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3)C CWABTZFJZYEVTP-PFPXXSDYSA-N 0.000 claims 1
- CVPYJVFMUMSARN-HNVUPHGUSA-N (6aS,7S,10aR)-4-(3-hydroxyphenyl)-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound OC=1C=C(C=CC1)C1=NC(=NC=2[C@@]3([C@@H](CCC12)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3)C CVPYJVFMUMSARN-HNVUPHGUSA-N 0.000 claims 1
- GKCWXJQCCNPLKY-DGBBAZJCSA-N (6aS,7S,10aR)-4-(3-methoxyphenyl)-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound COC=1C=C(C=CC1)C1=NC(=NC=2[C@@]3([C@@H](CCC12)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3)C GKCWXJQCCNPLKY-DGBBAZJCSA-N 0.000 claims 1
- BASNPCGHWULDTL-DABBQTFLSA-N (6aS,7S,10aR)-4-(3H-benzimidazol-5-yl)-10a-(4-fluorophenyl)-2,7-dimethyl-8-oxo-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound N1C=NC2=C1C=CC(=C2)C2=NC(=NC=1[C@@]3([C@@H](CCC21)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=C(C=C3)F)C BASNPCGHWULDTL-DABBQTFLSA-N 0.000 claims 1
- IKFXMVOWWQSOFN-ZQBRDIDQSA-N (6aS,7S,10aR)-4-(3H-benzimidazol-5-yl)-10a-(4-methoxyphenyl)-2,7-dimethyl-8-oxo-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound N1C=NC2=C1C=CC(=C2)C2=NC(=NC=1[C@@]3([C@@H](CCC21)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=C(C=C3)OC)C IKFXMVOWWQSOFN-ZQBRDIDQSA-N 0.000 claims 1
- NGCHVQWXDQFHPW-BOEYOXHFSA-N (6aS,7S,10aR)-4-(5-bromo-6-oxo-1H-pyridin-3-yl)-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound BrC=1C=C(C=NC1O)C1=NC(=NC=2[C@@]3([C@@H](CCC12)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3)C NGCHVQWXDQFHPW-BOEYOXHFSA-N 0.000 claims 1
- MRQXOPXGYXVUAB-HHCYOLOASA-N (6aS,7S,10aR)-4-(furan-3-yl)-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound O1C=C(C=C1)C1=NC(=NC=2[C@@]3([C@@H](CCC12)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3)C MRQXOPXGYXVUAB-HHCYOLOASA-N 0.000 claims 1
- KXXMGBXXDQIWBM-AWCXEYNZSA-N (6aS,7S,10aR)-4-[1-(2-hydroxyethyl)pyrazol-4-yl]-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound OCCN1N=CC(=C1)C1=NC(=NC=2[C@@]3([C@@H](CCC12)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3)C KXXMGBXXDQIWBM-AWCXEYNZSA-N 0.000 claims 1
- ALKGBZUHPNCVAJ-DGSCHONISA-N (6aS,7S,10aR)-4-[3-(2-hydroxyethyl)phenyl]-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound OCCC=1C=C(C=CC1)C1=NC(=NC=2[C@@]3([C@@H](CCC12)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3)C ALKGBZUHPNCVAJ-DGSCHONISA-N 0.000 claims 1
- NTCWMWVQIFTKNF-YCYJEZDCSA-N (6aS,7S,10aR)-4-[3-(3-hydroxypropyl)phenyl]-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound OCCCC=1C=C(C=CC1)C1=NC(=NC=2[C@@]3([C@@H](CCC12)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3)C NTCWMWVQIFTKNF-YCYJEZDCSA-N 0.000 claims 1
- LLFVKPYGUOXBBV-YEVGVYOWSA-N (6aS,7S,10aR)-4-[3-(4-aminophenyl)phenyl]-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound NC1=CC=C(C=C1)C1=CC(=CC=C1)C1=NC(=NC=2[C@@]3([C@@H](CCC12)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3)C LLFVKPYGUOXBBV-YEVGVYOWSA-N 0.000 claims 1
- IGDIHLFPUNSNFR-YEVGVYOWSA-N (6aS,7S,10aR)-4-[3-(4-hydroxyphenyl)phenyl]-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound OC1=CC=C(C=C1)C1=CC(=CC=C1)C1=NC(=NC=2[C@@]3([C@@H](CCC12)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3)C IGDIHLFPUNSNFR-YEVGVYOWSA-N 0.000 claims 1
- VMRASMNHLYOUFE-XXGHNEJDSA-N (6aS,7S,10aR)-4-[4-(4-bromo-1H-pyrazol-5-yl)phenyl]-10a-(4-fluorophenyl)-2,7-dimethyl-8-oxo-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound BrC=1C=NNC1C1=CC=C(C=C1)C1=NC(=NC=2[C@@]3([C@@H](CCC12)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=C(C=C3)F)C VMRASMNHLYOUFE-XXGHNEJDSA-N 0.000 claims 1
- OENWBMWFCNMJJL-OAEZYEPRSA-N (6aS,7S,10aR)-4-[4-(4-bromo-1H-pyrazol-5-yl)phenyl]-10a-(4-methoxyphenyl)-2,7-dimethyl-8-oxo-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound BrC=1C=NNC1C1=CC=C(C=C1)C1=NC(=NC=2[C@@]3([C@@H](CCC12)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=C(C=C3)OC)C OENWBMWFCNMJJL-OAEZYEPRSA-N 0.000 claims 1
- SIVMQBFVKKOFTJ-AXNJZRPJSA-N (6aS,7S,10aR)-4-imidazo[1,2-a]pyridin-6-yl-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound N=1C=CN2C1C=CC(=C2)C2=NC(=NC=1[C@@]3([C@@H](CCC21)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3)C SIVMQBFVKKOFTJ-AXNJZRPJSA-N 0.000 claims 1
- DVDLARXCLNYMRG-KVYZTJHFSA-N (6aS,7S,10aR)-4-methoxy-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound COC1=NC(=NC=2[C@@]3([C@@H](CCC12)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3)C DVDLARXCLNYMRG-KVYZTJHFSA-N 0.000 claims 1
- RGZDQBSNWHXSAD-GSMBIVSISA-N (6aS,7S,10aR)-7-methyl-2-morpholin-4-yl-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound C[C@@H]1C(C(=C[C@]2([C@H]1CCC=1C=NC(=NC21)N2CCOCC2)C2=CC=CC=C2)C#N)=O RGZDQBSNWHXSAD-GSMBIVSISA-N 0.000 claims 1
- XDSSCKYVBCXICM-RTFHYFGRSA-N (6aS,7S,10aR)-7-methyl-8-oxo-10a-(3-phenylmethoxyphenyl)-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound C(C1=CC=CC=C1)OC=1C=C(C=CC1)[C@]12[C@@H](CCC=3C=NC=NC13)[C@@H](C(C(=C2)C#N)=O)C XDSSCKYVBCXICM-RTFHYFGRSA-N 0.000 claims 1
- YYQGDOWAMUVYNW-RTFHYFGRSA-N (6aS,7S,10aR)-7-methyl-8-oxo-10a-(4-phenylmethoxyphenyl)-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound C(C1=CC=CC=C1)OC1=CC=C(C=C1)[C@]12[C@@H](CCC=3C=NC=NC13)[C@@H](C(C(=C2)C#N)=O)C YYQGDOWAMUVYNW-RTFHYFGRSA-N 0.000 claims 1
- ZLEIPYCQQKXNEK-WZSOFCAESA-N (6aS,7S,10aR)-7-methyl-8-oxo-10a-[4-(pyrrolidine-1-carbonyl)phenyl]-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound C[C@@H]1C(C(=C[C@]2([C@H]1CCC=1C=NC=NC21)C2=CC=C(C=C2)C(=O)N2CCCC2)C#N)=O ZLEIPYCQQKXNEK-WZSOFCAESA-N 0.000 claims 1
- ASIWHZPRECAEPW-QJQUAVMFSA-N (6aS,7S,10aR)-7-methyl-8-oxo-10a-phenyl-2-pyrazin-2-yl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound C[C@@H]1C(C(=C[C@]2([C@H]1CCC=1C=NC(=NC21)C2=NC=CN=C2)C2=CC=CC=C2)C#N)=O ASIWHZPRECAEPW-QJQUAVMFSA-N 0.000 claims 1
- JPKXNSZRGTVQMX-WZSOFCAESA-N (6aS,7S,10aR)-7-methyl-8-oxo-10a-phenyl-2-pyridin-3-yl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound C[C@@H]1C(C(=C[C@]2([C@H]1CCC=1C=NC(=NC21)C=2C=NC=CC2)C2=CC=CC=C2)C#N)=O JPKXNSZRGTVQMX-WZSOFCAESA-N 0.000 claims 1
- XWCIKCYPCGYNSX-WZSOFCAESA-N (6aS,7S,10aR)-7-methyl-8-oxo-10a-phenyl-2-pyridin-4-yl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound C[C@@H]1C(C(=C[C@]2([C@H]1CCC=1C=NC(=NC21)C2=CC=NC=C2)C2=CC=CC=C2)C#N)=O XWCIKCYPCGYNSX-WZSOFCAESA-N 0.000 claims 1
- JPRUCQHKNWDOFD-IJHUGTEESA-N (6aS,7S,10aR)-7-methyl-8-oxo-10a-phenyl-2-pyrimidin-5-yl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound C[C@@H]1C(C(=C[C@]2([C@H]1CCC=1C=NC(=NC21)C=2C=NC=NC2)C2=CC=CC=C2)C#N)=O JPRUCQHKNWDOFD-IJHUGTEESA-N 0.000 claims 1
- AZVFCRSFDDZELR-QKMWGZLOSA-N (6aS,7S,10aR)-7-methyl-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound C[C@@H]1C(C(=C[C@]2([C@H]1CCC=1C=NC=NC21)C2=CC=CC=C2)C#N)=O AZVFCRSFDDZELR-QKMWGZLOSA-N 0.000 claims 1
- MZQSWUIVOXWEAD-SLSDUTBNSA-N (6aS,7S,10aR)-7-methyl-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carboxamide Chemical compound C[C@@H]1C(C(=C[C@]2([C@H]1CCC=1C=NC=NC21)C2=CC=CC=C2)C(=O)N)=O MZQSWUIVOXWEAD-SLSDUTBNSA-N 0.000 claims 1
- QDWUPYYJUZLBLZ-USZVYGKESA-N (7S)-4-methoxy-7-methyl-8-oxo-2,10a-diphenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound COC1=NC(=NC=2C3(C(CCC12)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3)C3=CC=CC=C3 QDWUPYYJUZLBLZ-USZVYGKESA-N 0.000 claims 1
- GHKPJOWGIPXVBB-QOGZIUHUSA-N (7S)-7-methyl-8-oxo-2,10a-diphenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound C[C@@H]1C(C(=CC2(C1CCC=1C=NC(=NC21)C2=CC=CC=C2)C2=CC=CC=C2)C#N)=O GHKPJOWGIPXVBB-QOGZIUHUSA-N 0.000 claims 1
- BCWIIGSNDGENBB-YEVCRYSQSA-N (7S,10aS)-2-anilino-7-methyl-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound N(C1=CC=CC=C1)C1=NC=2[C@]3(C(CCC2C=N1)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3 BCWIIGSNDGENBB-YEVCRYSQSA-N 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- HUHJYNHOCNVMFH-UHFFFAOYSA-N 1,6-dimethyl-7-oxo-3,9a-diphenyl-4,5,5a,6-tetrahydrobenzo[g]indazole-8-carbonitrile Chemical compound CN1N=C(C=2CCC3C(C12)(C=C(C(C3C)=O)C#N)C3=CC=CC=C3)C3=CC=CC=C3 HUHJYNHOCNVMFH-UHFFFAOYSA-N 0.000 claims 1
- GIFQBPVNDBZOSO-UHFFFAOYSA-N 1,6-dimethyl-7-oxo-9a-phenyl-4,5,5a,6-tetrahydrobenzo[g]indazole-8-carbonitrile Chemical compound CN1N=CC=2CCC3C(C12)(C=C(C(C3C)=O)C#N)C3=CC=CC=C3 GIFQBPVNDBZOSO-UHFFFAOYSA-N 0.000 claims 1
- RAWIZVKDCOKRFG-UHFFFAOYSA-N 2,6-dimethyl-7-oxo-3,9a-diphenyl-4,5,5a,6-tetrahydrobenzo[g]indazole-8-carbonitrile Chemical compound CN1N=C2C3(C(CCC2=C1C1=CC=CC=C1)C(C(C(=C3)C#N)=O)C)C3=CC=CC=C3 RAWIZVKDCOKRFG-UHFFFAOYSA-N 0.000 claims 1
- GMYLFVJDSODESE-UHFFFAOYSA-N 2,6-dimethyl-7-oxo-9a-phenyl-4,5,5a,6-tetrahydrobenzo[g]indazole-8-carbonitrile Chemical compound CN1N=C2C3(C(CCC2=C1)C(C(C(=C3)C#N)=O)C)C3=CC=CC=C3 GMYLFVJDSODESE-UHFFFAOYSA-N 0.000 claims 1
- ZPFDRRYXRCESEP-UHFFFAOYSA-N 2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound CC1=NC=2C3(C(CCC2C=N1)C(C(C(=C3)C#N)=O)C)C3=CC=CC=C3 ZPFDRRYXRCESEP-UHFFFAOYSA-N 0.000 claims 1
- MMSPOKRYOLGYHR-LXFBUAEQSA-N 2-[4-[(6S,9aR)-8-cyano-6-methyl-7-oxo-9a-phenyl-4,5,5a,6-tetrahydro-1H-benzo[g]indazol-3-yl]pyrazol-1-yl]acetic acid Chemical compound C(#N)C1=C[C@]2(C(CCC3=C(NN=C23)C=2C=NN(C2)CC(=O)O)[C@@H](C1=O)C)C1=CC=CC=C1 MMSPOKRYOLGYHR-LXFBUAEQSA-N 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- PQYHRHMVFNEJQT-XITNVPRNSA-N 3-[(5aS,6S,9aR)-8-cyano-6-methyl-7-oxo-4,5,5a,6-tetrahydro-1H-benzo[g]indazol-9a-yl]benzoic acid Chemical compound C(#N)C1=C[C@]2([C@@H](CCC3=CNN=C23)[C@@H](C1=O)C)C=1C=C(C(=O)O)C=CC1 PQYHRHMVFNEJQT-XITNVPRNSA-N 0.000 claims 1
- OTWDUBVWKFUKMS-DABBQTFLSA-N 3-[(6aS,7S,10aR)-2-(4-carboxyphenyl)-9-cyano-7-methyl-8-oxo-5,6,6a,7-tetrahydrobenzo[h]quinazolin-10a-yl]benzoic acid Chemical compound C(=O)(O)C1=CC=C(C=C1)C1=NC=2[C@@]3([C@@H](CCC2C=N1)[C@@H](C(C(=C3)C#N)=O)C)C=3C=C(C(=O)O)C=CC3 OTWDUBVWKFUKMS-DABBQTFLSA-N 0.000 claims 1
- LHMQUBJXHJBAJU-UWYNZWELSA-N 3-[(6aS,7S,10aR)-9-cyano-7-methyl-8-oxo-2-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazolin-10a-yl]benzoic acid 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)O)C=CC1 LHMQUBJXHJBAJU-UWYNZWELSA-N 0.000 claims 1
- LLWALXROCMJIGS-XMFBKKLCSA-N 3-[(6aS,7S,10aR)-9-cyano-7-methyl-8-oxo-5,6,6a,7-tetrahydrobenzo[h]quinazolin-10a-yl]-N-phenylbenzamide Chemical compound C(#N)C1=C[C@]2([C@@H](CCC=3C=NC=NC23)[C@@H](C1=O)C)C=1C=C(C(=O)NC2=CC=CC=C2)C=CC1 LLWALXROCMJIGS-XMFBKKLCSA-N 0.000 claims 1
- CEHGFWKFOZHJQS-IJHUGTEESA-N 3-[(6aS,7S,10aR)-9-cyano-7-methyl-8-oxo-5,6,6a,7-tetrahydrobenzo[h]quinazolin-10a-yl]-N-propylbenzamide Chemical compound C(#N)C1=C[C@]2([C@@H](CCC=3C=NC=NC23)[C@@H](C1=O)C)C=1C=C(C(=O)NCCC)C=CC1 CEHGFWKFOZHJQS-IJHUGTEESA-N 0.000 claims 1
- FVOOPHFZDHXTMP-ODLKPZKQSA-N 3-[(6aS,7S,10aR)-9-cyano-7-methyl-8-oxo-5,6,6a,7-tetrahydrobenzo[h]quinazolin-10a-yl]benzoic acid Chemical compound C(#N)C1=C[C@]2([C@@H](CCC=3C=NC=NC23)[C@@H](C1=O)C)C=1C=C(C(=O)O)C=CC1 FVOOPHFZDHXTMP-ODLKPZKQSA-N 0.000 claims 1
- HRSICWWAJFYAOX-STTYJXNMSA-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]benzoic acid 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)C(=O)O)[C@@H](C1=O)C)C1=CC=CC=C1 HRSICWWAJFYAOX-STTYJXNMSA-N 0.000 claims 1
- JIHBOTCQSLUVRJ-JKLWDZIJSA-N 3-[3-[(6aS,7S,10aR)-9-cyano-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazolin-4-yl]phenyl]propanamide Chemical compound C(#N)C1=C[C@]2([C@@H](CCC=3C(=NC(=NC23)C)C=2C=C(C=CC2)CCC(=O)N)[C@@H](C1=O)C)C1=CC=CC=C1 JIHBOTCQSLUVRJ-JKLWDZIJSA-N 0.000 claims 1
- SWBFZBFHERGDKI-JKLWDZIJSA-N 3-[3-[(6aS,7S,10aR)-9-cyano-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazolin-4-yl]phenyl]propanoic acid Chemical compound C(#N)C1=C[C@]2([C@@H](CCC=3C(=NC(=NC23)C)C=2C=C(C=CC2)CCC(=O)O)[C@@H](C1=O)C)C1=CC=CC=C1 SWBFZBFHERGDKI-JKLWDZIJSA-N 0.000 claims 1
- SOWIKOWHEHKWLA-OAAQJRNLSA-N 3-[3-[(6aS,7S,10aR)-9-cyano-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazolin-4-yl]phenyl]propyl acetate Chemical compound C(C)(=O)OCCCC1=CC(=CC=C1)C1=NC(=NC=2[C@@]3([C@@H](CCC12)[C@@H](C(C(=C3)C#N)=O)C)C3=CC=CC=C3)C SOWIKOWHEHKWLA-OAAQJRNLSA-N 0.000 claims 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 1
- XTYKUTIUXQWKPR-BGYVWJHVSA-N 4-[(6aS,7S,10aR)-9-cyano-7-methyl-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazolin-2-yl]-N,N-dimethylbenzamide Chemical compound C(#N)C1=C[C@]2([C@@H](CCC=3C=NC(=NC23)C2=CC=C(C(=O)N(C)C)C=C2)[C@@H](C1=O)C)C1=CC=CC=C1 XTYKUTIUXQWKPR-BGYVWJHVSA-N 0.000 claims 1
- KIDIEKJEMRPDLX-UWYNZWELSA-N 4-[(6aS,7S,10aR)-9-cyano-7-methyl-8-oxo-10a-phenyl-5,6,6a,7-tetrahydrobenzo[h]quinazolin-2-yl]benzoic acid Chemical compound C(#N)C1=C[C@]2([C@@H](CCC=3C=NC(=NC23)C2=CC=C(C(=O)O)C=C2)[C@@H](C1=O)C)C1=CC=CC=C1 KIDIEKJEMRPDLX-UWYNZWELSA-N 0.000 claims 1
- WUTHCLRZBUHGBR-ODLKPZKQSA-N 4-[(6aS,7S,10aR)-9-cyano-7-methyl-8-oxo-5,6,6a,7-tetrahydrobenzo[h]quinazolin-10a-yl]benzoic acid Chemical compound C(#N)C1=C[C@]2([C@@H](CCC=3C=NC=NC23)[C@@H](C1=O)C)C1=CC=C(C(=O)O)C=C1 WUTHCLRZBUHGBR-ODLKPZKQSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- NNJMFJSKMRYHSR-UHFFFAOYSA-N 4-phenylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1 NNJMFJSKMRYHSR-UHFFFAOYSA-N 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- VTGVRRKEMBVCLK-UHFFFAOYSA-N 6-methyl-7-oxo-3,9a-diphenyl-4,5,5a,6-tetrahydro-1H-benzo[g]indazole-8-carbonitrile Chemical compound CC1C(C(=CC2(C1CCC=1C(=NNC21)C2=CC=CC=C2)C2=CC=CC=C2)C#N)=O VTGVRRKEMBVCLK-UHFFFAOYSA-N 0.000 claims 1
- RXHVTWCAQPLESB-UHFFFAOYSA-N 9a-(4-methoxyphenyl)-1,6-dimethyl-7-oxo-4,5,5a,6-tetrahydrobenzo[g]indazole-8-carbonitrile Chemical compound COC1=CC=C(C=C1)C12C(CCC=3C=NN(C13)C)C(C(C(=C2)C#N)=O)C RXHVTWCAQPLESB-UHFFFAOYSA-N 0.000 claims 1
- HSAVWYODKBCJEV-UHFFFAOYSA-N 9a-(4-methoxyphenyl)-2,6-dimethyl-7-oxo-4,5,5a,6-tetrahydrobenzo[g]indazole-8-carbonitrile Chemical compound COC1=CC=C(C=C1)C12C(CCC3=CN(N=C13)C)C(C(C(=C2)C#N)=O)C HSAVWYODKBCJEV-UHFFFAOYSA-N 0.000 claims 1
- CEUCESICTVVGIB-UHFFFAOYSA-N 9a-benzyl-1,6-dimethyl-7-oxo-4,5,5a,6-tetrahydrobenzo[g]indazole-8-carbonitrile Chemical compound C(C1=CC=CC=C1)C12C(CCC=3C=NN(C13)C)C(C(C(=C2)C#N)=O)C CEUCESICTVVGIB-UHFFFAOYSA-N 0.000 claims 1
- JBNLUSJYYZYSEA-UHFFFAOYSA-N 9a-benzyl-2,6-dimethyl-7-oxo-3-phenyl-4,5,5a,6-tetrahydrobenzo[g]indazole-8-carbonitrile Chemical compound C(C1=CC=CC=C1)C12C(CCC3=C(N(N=C13)C)C1=CC=CC=C1)C(C(C(=C2)C#N)=O)C JBNLUSJYYZYSEA-UHFFFAOYSA-N 0.000 claims 1
- CTXLLQCWLBAODS-UHFFFAOYSA-N 9a-benzyl-2,6-dimethyl-7-oxo-3-phenyl-4,5,5a,6-tetrahydrobenzo[g]indazole-8-carboxamide Chemical compound C(C1=CC=CC=C1)C12C(CCC3=C(N(N=C13)C)C1=CC=CC=C1)C(C(C(=C2)C(=O)N)=O)C CTXLLQCWLBAODS-UHFFFAOYSA-N 0.000 claims 1
- 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
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017503840A JP2017503840A (ja) | 2017-02-02 |
| JP2017503840A5 true JP2017503840A5 (cg-RX-API-DMAC7.html) | 2018-03-01 |
| JP6530758B2 JP6530758B2 (ja) | 2019-06-12 |
Family
ID=52484552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016548158A Active JP6530758B2 (ja) | 2014-01-24 | 2015-01-23 | 抗酸化性炎症調節剤としてのアリールおよびアリールアルキル置換されたピラゾリルおよびピリミジニル三環式エノン類 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9464082B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP3097089B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP6530758B2 (cg-RX-API-DMAC7.html) |
| CN (1) | CN107074801B (cg-RX-API-DMAC7.html) |
| CA (1) | CA2936550C (cg-RX-API-DMAC7.html) |
| MX (1) | MX372772B (cg-RX-API-DMAC7.html) |
| TW (1) | TWI670263B (cg-RX-API-DMAC7.html) |
| WO (1) | WO2015112792A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2009237579C1 (en) | 2008-04-18 | 2016-05-12 | Reata Pharmaceuticals Holdings, LLC | Antioxidant inflammation modulators: oleanolic acid derivatives with amino and other modifications at C-17 |
| CN103588678A (zh) | 2008-04-18 | 2014-02-19 | 里亚塔医药公司 | 包含抗炎症药效团的化合物以及使用方法 |
| PE20150160A1 (es) | 2012-04-27 | 2015-02-19 | Reata Pharmaceuticals Inc | Derivados de 2,2-difluoropropionamida de bardoxolona metilo, formas polimorficas y metodos de uso de los mismos |
| 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 |
| NZ734292A (en) * | 2015-02-12 | 2022-09-30 | Reata Pharmaceuticals Inc | Imidazolyl tricyclic enones as antioxidant inflammation modulators |
| 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 |
| US11993574B2 (en) * | 2018-06-15 | 2024-05-28 | Reata Pharmaceuticals, Inc | Pyrazole and imidazole compounds for inhibition of IL-17 and RORgamma |
| 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 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1142889A1 (en) * | 2000-04-03 | 2001-10-10 | Pfizer Products Inc. | Pyrazole derivatives as anti-inflammatory/analgesic agents |
| BR0212661A (pt) | 2001-09-19 | 2004-08-24 | Pharmacia Corp | Compostos de pirazolil benzenossulfamida substituìdos para o tratamento de inflamação |
| TWI558724B (zh) | 2010-04-12 | 2016-11-21 | 瑞塔醫藥有限責任公司 | 利用抗氧化發炎調節劑治療肥胖之方法 |
| KR102000301B1 (ko) * | 2010-12-17 | 2019-07-15 | 리아타 파마슈티컬즈, 아이엔씨. | 산화방지성 염증 조절제로서의 피라졸릴 및 피리미디닐 트리사이클릭 엔온 |
-
2015
- 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 EP EP15705409.9A patent/EP3097089B1/en active Active
- 2015-01-23 CA CA2936550A patent/CA2936550C/en active Active
- 2015-01-23 MX MX2016009589A patent/MX372772B/es active IP Right Grant
- 2015-01-23 CN CN201580015069.4A patent/CN107074801B/zh active Active
- 2015-01-23 WO PCT/US2015/012579 patent/WO2015112792A1/en not_active Ceased
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2017503840A5 (cg-RX-API-DMAC7.html) | ||
| JP2005536475A5 (cg-RX-API-DMAC7.html) | ||
| JP2009529047A5 (cg-RX-API-DMAC7.html) | ||
| WO2017090002A4 (en) | Inhibitors of pi3 kinases | |
| RU2014152790A (ru) | Пирролопиразоновые ингибиторы танкиразы | |
| JP2015528018A5 (cg-RX-API-DMAC7.html) | ||
| JP2015503507A5 (cg-RX-API-DMAC7.html) | ||
| EA201391815A1 (ru) | Замещенные производные бензамида | |
| JP2016538313A5 (cg-RX-API-DMAC7.html) | ||
| JP2017515844A5 (cg-RX-API-DMAC7.html) | ||
| AU2013213260A1 (en) | Imidazopyrrolidinone compounds | |
| RU2350616C2 (ru) | Производные пиразоло- и имидазопиримидина | |
| JP2013509392A5 (cg-RX-API-DMAC7.html) | ||
| CY1110676T1 (el) | ΠΥΡΑΖΟΛΟ[3,4-b]ΠΥΡΙΔΙΝΙΚΕΣ ΕΝΩΣΕΙΣ, ΚΑΙ Η ΧΡΗΣΗ ΤΟΥΣ ΩΣ ΑΝΑΣΤΟΛΕΙΣ ΤΗΣ ΦΩΣΦΟΔΙΕΣΤΕΡΑΣΗΣ | |
| JP2017533968A5 (cg-RX-API-DMAC7.html) | ||
| RU2013148405A (ru) | Ингибиторы киназ | |
| NZ630721A (en) | Pyrazolo[1,5-a]pyrimidine-based compounds, compositions comprising them, and methods of their use | |
| RU2018112237A (ru) | Новые бициклические соединения в качестве дуальных ингибиторов atx/ca | |
| RU2012112050A (ru) | Производные дигидроптеридинона, способ их получения и фармацевтическое применение | |
| JP2017502940A5 (cg-RX-API-DMAC7.html) | ||
| JP2014500265A5 (cg-RX-API-DMAC7.html) | ||
| JP2016519685A5 (cg-RX-API-DMAC7.html) | ||
| RU2015131110A (ru) | Производные 1-(замещенный бензоил)-5-фтор-4-имино-3-метил-3,4-дигидропиримидин-2(1h)-она | |
| CA2495661A1 (en) | Inhibition of phosphoinositide 3-kinase beta | |
| RU2016141646A (ru) | Ингибиторы trka киназы, основанные на них композиции и способы |