JP2002518395A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2002518395A5 JP2002518395A5 JP2000554735A JP2000554735A JP2002518395A5 JP 2002518395 A5 JP2002518395 A5 JP 2002518395A5 JP 2000554735 A JP2000554735 A JP 2000554735A JP 2000554735 A JP2000554735 A JP 2000554735A JP 2002518395 A5 JP2002518395 A5 JP 2002518395A5
- Authority
- JP
- Japan
- Prior art keywords
- dihydro
- indolo
- benzazepin
- group
- hydrogen
- 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
- 229910052739 hydrogen Inorganic materials 0.000 description 42
- 239000001257 hydrogen Substances 0.000 description 42
- -1 nitro, Carboxyl Chemical group 0.000 description 35
- 150000001875 compounds Chemical class 0.000 description 33
- 150000002431 hydrogen Chemical class 0.000 description 25
- 238000000034 method Methods 0.000 description 25
- 239000000203 mixture Substances 0.000 description 24
- 229910052736 halogen Inorganic materials 0.000 description 18
- 150000002367 halogens Chemical class 0.000 description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 16
- 125000001931 aliphatic group Chemical group 0.000 description 15
- 125000003545 alkoxy group Chemical group 0.000 description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 15
- 125000002252 acyl group Chemical group 0.000 description 13
- 125000004093 cyano group Chemical group *C#N 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 12
- 229910052760 oxygen Inorganic materials 0.000 description 12
- 239000001301 oxygen Substances 0.000 description 12
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- 125000001841 imino group Chemical group [H]N=* 0.000 description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
- 239000004593 Epoxy Substances 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 125000001188 haloalkyl group Chemical group 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- MILILGJHFMDHIJ-UHFFFAOYSA-N 9-(trifluoromethyl)-7,12-dihydro-5h-indolo[3,2-d][1]benzazepin-6-one Chemical compound C1C(=O)NC2=CC=CC=C2C2=C1C1=CC(C(F)(F)F)=CC=C1N2 MILILGJHFMDHIJ-UHFFFAOYSA-N 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 125000001246 bromo group Chemical group Br* 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- LBVIZFWUIQSZHP-UHFFFAOYSA-N 6-oxo-7,12-dihydro-5h-indolo[3,2-d][1]benzazepine-9-carbonitrile Chemical compound C12=CC=CC=C2NC(=O)CC2=C1NC1=CC=C(C#N)C=C21 LBVIZFWUIQSZHP-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 229910052801 chlorine Chemical group 0.000 description 4
- 239000000460 chlorine Chemical group 0.000 description 4
- RVTOIQOTZUKDTE-UHFFFAOYSA-N 2,3-dimethoxy-9-(trifluoromethyl)-7,12-dihydro-5h-indolo[3,2-d][1]benzazepin-6-one Chemical compound C1=2C=C(OC)C(OC)=CC=2NC(=O)CC2=C1NC1=CC=C(C(F)(F)F)C=C21 RVTOIQOTZUKDTE-UHFFFAOYSA-N 0.000 description 3
- KIZLESRPUNYYNU-UHFFFAOYSA-N 2,9-dibromo-7,12-dihydro-5h-indolo[3,2-d][1]benzazepin-6-one Chemical compound C12=CC(Br)=CC=C2NC(=O)CC2=C1NC1=CC=C(Br)C=C21 KIZLESRPUNYYNU-UHFFFAOYSA-N 0.000 description 3
- CZOVMHCLKVCOEM-UHFFFAOYSA-N 2-bromo-9-(trifluoromethyl)-7,12-dihydro-5h-indolo[3,2-d][1]benzazepin-6-one Chemical compound C1C(=O)NC2=CC=C(Br)C=C2C2=C1C1=CC(C(F)(F)F)=CC=C1N2 CZOVMHCLKVCOEM-UHFFFAOYSA-N 0.000 description 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 3
- DUZUWJBAONJCTE-UHFFFAOYSA-N 9-bromo-2,3-dimethoxy-7,12-dihydro-5h-indolo[3,2-d][1]benzazepin-6-one Chemical compound C1=2C=C(OC)C(OC)=CC=2NC(=O)CC2=C1NC1=CC=C(Br)C=C21 DUZUWJBAONJCTE-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- XLKHCIUFNPNLIE-UHFFFAOYSA-N dnc004090 Chemical compound C12=CC(Br)=CC=C2NC2=C1CC(=O)NC1=C2SC=C1 XLKHCIUFNPNLIE-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- IGYURNWXVFOIOW-UHFFFAOYSA-N 10-bromo-7,12-dihydro-5h-indolo[3,2-d][1]benzazepin-6-one Chemical compound C1C(=O)NC2=CC=CC=C2C2=C1C1=CC=C(Br)C=C1N2 IGYURNWXVFOIOW-UHFFFAOYSA-N 0.000 description 2
- YAKJZHVHEIOVIR-UHFFFAOYSA-N 2,3-dimethoxy-7,12-dihydro-5h-indolo[3,2-d][1]benzazepin-6-one Chemical compound C1=2C=C(OC)C(OC)=CC=2NC(=O)CC2=C1NC1=CC=CC=C21 YAKJZHVHEIOVIR-UHFFFAOYSA-N 0.000 description 2
- SYGNSFGBDJEBOK-UHFFFAOYSA-N 8,10-dichloro-7,12-dihydro-5h-indolo[3,2-d][1]benzazepin-6-one Chemical compound C1C(=O)NC2=CC=CC=C2C2=C1C1=C(Cl)C=C(Cl)C=C1N2 SYGNSFGBDJEBOK-UHFFFAOYSA-N 0.000 description 2
- CYWSKAGHMPTBMS-UHFFFAOYSA-N 9-bromo-12-methyl-5,7-dihydroindolo[3,2-d][1]benzazepin-6-one Chemical compound C1C(=O)NC2=CC=CC=C2C2=C1C1=CC(Br)=CC=C1N2C CYWSKAGHMPTBMS-UHFFFAOYSA-N 0.000 description 2
- CSJPCQXZZVBCHG-UHFFFAOYSA-N 9-bromo-2,3-dihydroxy-7,12-dihydro-5h-indolo[3,2-d][1]benzazepin-6-one Chemical compound C1=2C=C(O)C(O)=CC=2NC(=O)CC2=C1NC1=CC=C(Br)C=C21 CSJPCQXZZVBCHG-UHFFFAOYSA-N 0.000 description 2
- MHKWLZUWJABEIX-UHFFFAOYSA-N 9-bromo-7,12-dihydro-5h-indolo[3,2-d][1]benzazepine-6-thione Chemical compound C1C(=S)NC2=CC=CC=C2C2=C1C1=CC(Br)=CC=C1N2 MHKWLZUWJABEIX-UHFFFAOYSA-N 0.000 description 2
- XOAKRYSSJJAKLL-UHFFFAOYSA-N 9-methoxy-7,12-dihydro-5h-indolo[3,2-d][1]benzazepin-6-one Chemical compound C1C(=O)NC2=CC=CC=C2C2=C1C1=CC(OC)=CC=C1N2 XOAKRYSSJJAKLL-UHFFFAOYSA-N 0.000 description 2
- FDMHWATUIRUWOF-UHFFFAOYSA-N 9-methyl-7,12-dihydro-5h-indolo[3,2-d][1]benzazepin-6-one Chemical compound C1C(=O)NC2=CC=CC=C2C2=C1C1=CC(C)=CC=C1N2 FDMHWATUIRUWOF-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- OLUKILHGKRVDCT-UHFFFAOYSA-N alsterpaullone Chemical compound C1C(=O)NC2=CC=CC=C2C2=C1C1=CC([N+](=O)[O-])=CC=C1N2 OLUKILHGKRVDCT-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- IGVYXSVOVAENJU-UHFFFAOYSA-N chembl118406 Chemical compound C12=CC(C)=CC=C2NC2=C1CC(=O)NC1=C2SC=C1 IGVYXSVOVAENJU-UHFFFAOYSA-N 0.000 description 2
- IUCQPIROBHBEID-UHFFFAOYSA-N chembl334031 Chemical compound C12=CC(Cl)=CC=C2NC2=C1CC(=O)NC1=C2SC=C1 IUCQPIROBHBEID-UHFFFAOYSA-N 0.000 description 2
- LOOYKDRIOSVHMM-UHFFFAOYSA-N 11-ethyl-7,12-dihydro-5h-indolo[3,2-d][1]benzazepin-6-one Chemical compound C1C(=O)NC2=CC=CC=C2C2=C1C(C=CC=C1CC)=C1N2 LOOYKDRIOSVHMM-UHFFFAOYSA-N 0.000 description 1
- XWKMAJPZELTMLH-UHFFFAOYSA-N 11-methyl-7,12-dihydro-5h-indolo[3,2-d][1]benzazepin-6-one Chemical compound C1C(=O)NC2=CC=CC=C2C2=C1C(C=CC=C1C)=C1N2 XWKMAJPZELTMLH-UHFFFAOYSA-N 0.000 description 1
- IWTCPWHGHSZDRD-UHFFFAOYSA-N 13-(trifluoromethyl)-3-thia-7,17-diazatetracyclo[8.7.0.02,6.011,16]heptadeca-1(10),2(6),4,11(16),12,14-hexaen-8-one Chemical compound C12=CC(C(F)(F)F)=CC=C2NC2=C1CC(=O)NC1=C2SC=C1 IWTCPWHGHSZDRD-UHFFFAOYSA-N 0.000 description 1
- FZSXLUDKOYPBMM-UHFFFAOYSA-N 2,3-dihydroxy-7,12-dihydro-5h-indolo[3,2-d][1]benzazepin-6-one Chemical compound C1=2C=C(O)C(O)=CC=2NC(=O)CC2=C1NC1=CC=CC=C21 FZSXLUDKOYPBMM-UHFFFAOYSA-N 0.000 description 1
- TUMYZJPVQGGVEN-UHFFFAOYSA-N 2,3-dimethoxy-6-oxo-7,12-dihydro-5h-indolo[3,2-d][1]benzazepine-9-carbonitrile Chemical compound C1=2C=C(OC)C(OC)=CC=2NC(=O)CC2=C1NC1=CC=C(C#N)C=C21 TUMYZJPVQGGVEN-UHFFFAOYSA-N 0.000 description 1
- KYRQRRGDKAIFMA-UHFFFAOYSA-N 2,3-dimethoxy-9-nitro-7,12-dihydro-5h-indolo[3,2-d][1]benzazepin-6-one Chemical compound C1=2C=C(OC)C(OC)=CC=2NC(=O)CC2=C1NC1=CC=C([N+]([O-])=O)C=C21 KYRQRRGDKAIFMA-UHFFFAOYSA-N 0.000 description 1
- IAJGQMXAKJOLBA-UHFFFAOYSA-N 2-bromo-9-nitro-7,12-dihydro-5h-indolo[3,2-d][1]benzazepin-6-one Chemical compound C1C(=O)NC2=CC=C(Br)C=C2C2=C1C1=CC([N+](=O)[O-])=CC=C1N2 IAJGQMXAKJOLBA-UHFFFAOYSA-N 0.000 description 1
- ISVUJGXTZKJOGX-UHFFFAOYSA-N 2-iodo-7,12-dihydro-5h-indolo[3,2-d][1]benzazepin-6-one Chemical compound C12=CC(I)=CC=C2NC(=O)CC2=C1NC1=CC=CC=C21 ISVUJGXTZKJOGX-UHFFFAOYSA-N 0.000 description 1
- BHZJERIYLOTNFQ-UHFFFAOYSA-N 2-iodo-9-(trifluoromethyl)-7,12-dihydro-5h-indolo[3,2-d][1]benzazepin-6-one Chemical compound C1C(=O)NC2=CC=C(I)C=C2C2=C1C1=CC(C(F)(F)F)=CC=C1N2 BHZJERIYLOTNFQ-UHFFFAOYSA-N 0.000 description 1
- MVWNPTRDUDXOPY-UHFFFAOYSA-N 3-[6-oxo-9-(trifluoromethyl)-7,12-dihydro-5h-indolo[3,2-d][1]benzazepin-2-yl]prop-2-enenitrile Chemical compound C1C(=O)NC2=CC=C(C=CC#N)C=C2C2=C1C1=CC(C(F)(F)F)=CC=C1N2 MVWNPTRDUDXOPY-UHFFFAOYSA-N 0.000 description 1
- SHBOZSJPVRMXBA-UHFFFAOYSA-N 3-[6-oxo-9-(trifluoromethyl)-7,12-dihydro-5h-indolo[3,2-d][1]benzazepin-2-yl]propanenitrile Chemical compound C1C(=O)NC2=CC=C(CCC#N)C=C2C2=C1C1=CC(C(F)(F)F)=CC=C1N2 SHBOZSJPVRMXBA-UHFFFAOYSA-N 0.000 description 1
- HLNLXECKTICCDT-UHFFFAOYSA-N 4-hydroxy-7,12-dihydro-5h-indolo[3,2-d][1]benzazepin-6-one Chemical compound C1=2NC3=CC=CC=C3C=2CC(=O)NC2=C1C=CC=C2O HLNLXECKTICCDT-UHFFFAOYSA-N 0.000 description 1
- ATOAEKSFKWKAIO-UHFFFAOYSA-N 4-methoxy-7,12-dihydro-5h-indolo[3,2-d][1]benzazepin-6-one Chemical compound C1=2NC3=CC=CC=C3C=2CC(=O)NC2=C1C=CC=C2OC ATOAEKSFKWKAIO-UHFFFAOYSA-N 0.000 description 1
- OLRJMJBCFIJRIT-UHFFFAOYSA-N 4H-azepino[4,5-b]indol-5-one Chemical compound O=C1CN=CC=C2C1=Nc1ccccc21 OLRJMJBCFIJRIT-UHFFFAOYSA-N 0.000 description 1
- UQYAOCPYYWTPID-UHFFFAOYSA-N 6-oxo-7,12-dihydro-5h-indolo[3,2-d][1]benzazepine-2-carbonitrile Chemical compound C12=CC(C#N)=CC=C2NC(=O)CC2=C1NC1=CC=CC=C21 UQYAOCPYYWTPID-UHFFFAOYSA-N 0.000 description 1
- YBTFSTRMFPNVDQ-UHFFFAOYSA-N 9-bromo-10-hydroxy-7,12-dihydro-5h-indolo[3,2-d][1]benzazepin-6-one Chemical compound C1C(=O)NC2=CC=CC=C2C(N2)=C1C1=C2C=C(O)C(Br)=C1 YBTFSTRMFPNVDQ-UHFFFAOYSA-N 0.000 description 1
- JGELUIOSDAYQLO-UHFFFAOYSA-N 9-bromo-11-(hydroxymethyl)-7,12-dihydro-5h-indolo[3,2-d][1]benzazepin-6-one Chemical compound C1C(=O)NC2=CC=CC=C2C2=C1C(C=C(Br)C=C1CO)=C1N2 JGELUIOSDAYQLO-UHFFFAOYSA-N 0.000 description 1
- GWFCNMFOAORLDH-UHFFFAOYSA-N 9-bromo-12-(2-hydroxyethyl)-5,7-dihydroindolo[3,2-d][1]benzazepin-6-one Chemical compound C1C(=O)NC2=CC=CC=C2C2=C1C1=CC(Br)=CC=C1N2CCO GWFCNMFOAORLDH-UHFFFAOYSA-N 0.000 description 1
- GJZCFRVBDYYNIV-UHFFFAOYSA-N 9-bromo-12-prop-2-enyl-5,7-dihydroindolo[3,2-d][1]benzazepin-6-one Chemical compound C1C(=O)NC2=CC=CC=C2C2=C1C1=CC(Br)=CC=C1N2CC=C GJZCFRVBDYYNIV-UHFFFAOYSA-N 0.000 description 1
- JKVBIBIZBZBAKL-UHFFFAOYSA-N 9-bromo-2-iodo-7,12-dihydro-5h-indolo[3,2-d][1]benzazepin-6-one Chemical compound C1C(=O)NC2=CC=C(I)C=C2C2=C1C1=CC(Br)=CC=C1N2 JKVBIBIZBZBAKL-UHFFFAOYSA-N 0.000 description 1
- VPNVMVMFLHEGBV-UHFFFAOYSA-N 9-bromo-4-hydroxy-7,12-dihydro-5h-indolo[3,2-d][1]benzazepin-6-one Chemical compound C1=2NC3=CC=C(Br)C=C3C=2CC(=O)NC2=C1C=CC=C2O VPNVMVMFLHEGBV-UHFFFAOYSA-N 0.000 description 1
- IZRNPQQLTKFPRZ-UHFFFAOYSA-N 9-bromo-4-methoxy-7,12-dihydro-5h-indolo[3,2-d][1]benzazepin-6-one Chemical compound C1=2NC3=CC=C(Br)C=C3C=2CC(=O)NC2=C1C=CC=C2OC IZRNPQQLTKFPRZ-UHFFFAOYSA-N 0.000 description 1
- ZNJYKYATCKBLHO-UHFFFAOYSA-N 9-bromo-5-methyl-7,12-dihydroindolo[3,2-d][1]benzazepin-6-one Chemical compound C1C(=O)N(C)C2=CC=CC=C2C2=C1C1=CC(Br)=CC=C1N2 ZNJYKYATCKBLHO-UHFFFAOYSA-N 0.000 description 1
- OKMGGPIYQLLQFZ-UHFFFAOYSA-N 9-chloro-7,12-dihydro-5h-indolo[3,2-d][1]benzazepin-6-one Chemical compound C1C(=O)NC2=CC=CC=C2C2=C1C1=CC(Cl)=CC=C1N2 OKMGGPIYQLLQFZ-UHFFFAOYSA-N 0.000 description 1
- OPGZTFCRUXGMRT-UHFFFAOYSA-N 9-fluoro-12-prop-2-enyl-5,7-dihydroindolo[3,2-d][1]benzazepin-6-one Chemical compound C1C(=O)NC2=CC=CC=C2C2=C1C1=CC(F)=CC=C1N2CC=C OPGZTFCRUXGMRT-UHFFFAOYSA-N 0.000 description 1
- NNDLCXNIMGREEF-UHFFFAOYSA-N 9-fluoro-7,12-dihydro-5h-indolo[3,2-d][1]benzazepin-6-one Chemical compound C1C(=O)NC2=CC=CC=C2C2=C1C1=CC(F)=CC=C1N2 NNDLCXNIMGREEF-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- IMVYUVOHSQUHJD-UHFFFAOYSA-N chembl331783 Chemical compound C12=CC=CC=C2NC(=O)CC2=C1NC1=NC=CC=C21 IMVYUVOHSQUHJD-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- XNVMFDGFXSZPDU-UHFFFAOYSA-N cyano nitroformate Chemical compound [O-][N+](=O)C(=O)OC#N XNVMFDGFXSZPDU-UHFFFAOYSA-N 0.000 description 1
- 238000007907 direct compression Methods 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- KZGUEWREZGMORL-UHFFFAOYSA-N ditert-butyl 9-bromo-6-oxo-7,12-dihydroindolo[3,2-d][1]benzazepine-5,7-dicarboxylate Chemical compound C12=CC=CC=C2N(C(=O)OC(C)(C)C)C(=O)C(C(=O)OC(C)(C)C)C2=C1NC1=CC=C(Br)C=C21 KZGUEWREZGMORL-UHFFFAOYSA-N 0.000 description 1
- MRTWJQDNVKEBIF-UHFFFAOYSA-N ditert-butyl 9-bromo-6-oxo-7h-indolo[3,2-d][1]benzazepine-5,12-dicarboxylate Chemical compound C1C(=O)N(C(=O)OC(C)(C)C)C2=CC=CC=C2C2=C1C1=CC(Br)=CC=C1N2C(=O)OC(C)(C)C MRTWJQDNVKEBIF-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000003463 hyperproliferative effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- FTHAZLWBEMCLBS-UHFFFAOYSA-N methyl 2-(9-bromo-6-oxo-5,7-dihydroindolo[3,2-d][1]benzazepin-12-yl)acetate Chemical compound C1C(=O)NC2=CC=CC=C2C2=C1C1=CC(Br)=CC=C1N2CC(=O)OC FTHAZLWBEMCLBS-UHFFFAOYSA-N 0.000 description 1
- GAHXUMGTOQYQMW-UHFFFAOYSA-N methyl 2-(9-bromo-6-oxo-7,12-dihydroindolo[3,2-d][1]benzazepin-5-yl)acetate Chemical compound C1C(=O)N(CC(=O)OC)C2=CC=CC=C2C2=C1C1=CC(Br)=CC=C1N2 GAHXUMGTOQYQMW-UHFFFAOYSA-N 0.000 description 1
- DJCQWLAUTLNODY-UHFFFAOYSA-N methyl 3-[6-oxo-9-(trifluoromethyl)-7,12-dihydro-5h-indolo[3,2-d][1]benzazepin-2-yl]prop-2-enoate Chemical compound C12=CC(C=CC(=O)OC)=CC=C2NC(=O)CC2=C1NC1=CC=C(C(F)(F)F)C=C21 DJCQWLAUTLNODY-UHFFFAOYSA-N 0.000 description 1
- VGMDAWVZNAXVDG-UHFFFAOYSA-N paullone Chemical compound C12=CC=CC=C2NC(=O)CC2=C1NC1=CC=CC=C21 VGMDAWVZNAXVDG-UHFFFAOYSA-N 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- XHZYYJIRPPAMPY-UHFFFAOYSA-N tert-butyl 9-bromo-6-oxo-5,7-dihydroindolo[3,2-d][1]benzazepine-12-carboxylate Chemical compound C1C(=O)NC2=CC=CC=C2C2=C1C1=CC(Br)=CC=C1N2C(=O)OC(C)(C)C XHZYYJIRPPAMPY-UHFFFAOYSA-N 0.000 description 1
- NJWBEJMJZBWMOO-UHFFFAOYSA-N tritert-butyl 9-bromo-6-oxo-7h-indolo[3,2-d][1]benzazepine-5,7,12-tricarboxylate Chemical compound C12=CC=CC=C2N(C(=O)OC(C)(C)C)C(=O)C(C(=O)OC(C)(C)C)C2=C1N(C(=O)OC(C)(C)C)C1=CC=C(Br)C=C21 NJWBEJMJZBWMOO-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8961998P | 1998-06-16 | 1998-06-16 | |
| US60/089,619 | 1998-06-16 | ||
| PCT/US1999/013579 WO1999065910A1 (en) | 1998-06-16 | 1999-06-16 | Fused azepinone cyclin dependent kinase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002518395A JP2002518395A (ja) | 2002-06-25 |
| JP2002518395A5 true JP2002518395A5 (https=) | 2006-04-20 |
| JP4555476B2 JP4555476B2 (ja) | 2010-09-29 |
Family
ID=22218651
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000554735A Expired - Fee Related JP4555476B2 (ja) | 1998-06-16 | 1999-06-16 | 縮合アゼピノン型サイクリン依存性キナーゼ阻害物質 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6610684B2 (https=) |
| EP (1) | EP1086105B1 (https=) |
| JP (1) | JP4555476B2 (https=) |
| AT (1) | ATE318818T1 (https=) |
| AU (1) | AU778735B2 (https=) |
| CA (1) | CA2335115C (https=) |
| DE (1) | DE69930120T2 (https=) |
| WO (1) | WO1999065910A1 (https=) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2804959B1 (fr) * | 2000-02-15 | 2006-04-28 | Centre Nat Rech Scient | Utilisation de derives de paullones pour la fabrication de medicaments |
| JP4527404B2 (ja) | 2002-04-04 | 2010-08-18 | エンゾン，インコーポレーテッド | インドールのポリマー性アシル誘導体 |
| DE10260618B4 (de) * | 2002-12-23 | 2005-06-09 | Faustus Forschungs Cie. Translational Cancer Research Gmbh | Tumorhemmende annellierte Azepinonderivate |
| PL1748691T3 (pl) * | 2004-05-12 | 2011-04-29 | Bayer Cropscience Ag | Sposób regulacji wzrostu roślin |
| WO2006089874A1 (en) * | 2005-02-22 | 2006-08-31 | Gpc Biotech Ag | Benzo[2,3]azepino[4,5-b]indol-6-ones |
| EP1757607A1 (en) | 2005-08-24 | 2007-02-28 | Molisa GmbH | N5-substituted benzo¬2,3|azepino¬4,5-b|indol-6-ones for treating tropical diseases |
| FR2899107B1 (fr) * | 2006-03-30 | 2008-06-13 | Neurokin Entpr Unipersonnelle | Utilisation de la (s)-roscovitine pour la fabrication d'un medicament |
| WO2009010298A2 (en) * | 2007-07-18 | 2009-01-22 | Technische Universität Carolo-Wilhelmina Zu Braunschweig | Paullone derivatives and its use |
| US8716308B2 (en) | 2008-01-11 | 2014-05-06 | Albany Molecular Research, Inc. | (1-azinone)-substituted pyridoindoles |
| JP2012504646A (ja) * | 2008-10-01 | 2012-02-23 | ザ ユニバーシティ オブ ノース カロライナ アット チャペル ヒル | 選択的サイクリン依存性キナーゼ４／６阻害剤を用いた化学療法化合物に対する造血系の防護 |
| CN102231983A (zh) * | 2008-10-01 | 2011-11-02 | 北卡罗来纳大学查珀尔希尔分校 | 使用选择性细胞周期蛋白依赖性激酶4/6抑制剂对抗电离辐射的造血防护 |
| EP2414358A1 (en) * | 2009-03-31 | 2012-02-08 | ArQule, Inc. | Substituted tetrahydropyrazolo-pyrido-azepin compounds |
| EP3406260B1 (en) | 2009-05-13 | 2020-09-23 | The University of North Carolina at Chapel Hill | Cyclin dependent kinase inhibitors and methods of use |
| WO2011003012A1 (en) * | 2009-07-01 | 2011-01-06 | Albany Molecular Research, Inc. | Azinone-substituted azapolycycle mch-1 antagonists, methods of making, and use thereof |
| US8637501B2 (en) * | 2009-07-01 | 2014-01-28 | Albany Molecular Research, Inc. | Azinone-substituted azepino[b]indole and pyrido-pyrrolo-azepine MCH-1 antagonists, methods of making, and use thereof |
| US9073925B2 (en) * | 2009-07-01 | 2015-07-07 | Albany Molecular Research, Inc. | Azinone-substituted azabicycloalkane-indole and azabicycloalkane-pyrrolo-pyridine MCH-1 antagonists, methods of making, and use thereof |
| US8629158B2 (en) * | 2009-07-01 | 2014-01-14 | Albany Molecular Research, Inc. | Azabicycloalkane-indole and azabicycloalkane-pyrrolo-pyridine MCH-1 antagonists, methods of making, and use thereof |
| KR20120060201A (ko) | 2009-07-08 | 2012-06-11 | 인쎄름 (엥스띠뛰 나씨오날 드 라 쌍떼 에 드 라 흐쉐르슈 메디깔) | 기능적으로 분화된 체세포의 연장된 자기재생을 유도하는 방법 |
| WO2011112635A1 (en) | 2010-03-08 | 2011-09-15 | Sloan-Kettering Institute For Cancer Research | Cdc7 kinase inhibitors and uses thereof |
| EP2640394A4 (en) | 2010-11-17 | 2015-02-25 | Univ North Carolina | PROTECTION OF KIDNEY TISSUE FROM ISCHEMIA BY THE INHIBITION OF PROLEVERATIVE KINASES CDK4 AND CDK6 |
| WO2012088038A2 (en) | 2010-12-21 | 2012-06-28 | Albany Molecular Research, Inc. | Piperazinone-substituted tetrahydro-carboline mch-1 antagonists, methods of making, and uses thereof |
| US8993765B2 (en) | 2010-12-21 | 2015-03-31 | Albany Molecular Research, Inc. | Tetrahydro-azacarboline MCH-1 antagonists, methods of making, and uses thereof |
| HK1222766A1 (zh) | 2013-03-15 | 2017-07-14 | G1治疗公司 | 高效的抗赘生剂和抗增生剂 |
| DK2968290T3 (da) | 2013-03-15 | 2019-11-25 | G1 Therapeutics Inc | Transient beskyttelse af normale celler under kemoterapi |
| WO2015161285A1 (en) | 2014-04-17 | 2015-10-22 | G1 Therapeutics, Inc. | Tricyclic lactams for use in the protection of hematopoietic stem and progenitor cells against ionizing radiation |
| WO2016040858A1 (en) | 2014-09-12 | 2016-03-17 | G1 Therapeutics, Inc. | Combinations and dosing regimes to treat rb-positive tumors |
| WO2016040848A1 (en) | 2014-09-12 | 2016-03-17 | G1 Therapeutics, Inc. | Treatment of rb-negative tumors using topoisomerase inhibitors in combination with cyclin dependent kinase 4/6 inhibitors |
| EA201891170A1 (ru) | 2015-11-18 | 2018-11-30 | Джензим Корпорейшн | Биомаркер поликистозной болезни почек и варианты его применения |
| US10988479B1 (en) | 2020-06-15 | 2021-04-27 | G1 Therapeutics, Inc. | Morphic forms of trilaciclib and methods of manufacture thereof |
| WO2022104206A1 (en) * | 2020-11-13 | 2022-05-19 | Neuron23, Inc. | Kinase modulators and methods of use thereof |
| EP4277897A1 (en) * | 2021-01-12 | 2023-11-22 | Chengdu Anticancer Bioscience, Ltd. | Fused azepine compounds and their use in the treatment of cancer |
| US12258345B1 (en) | 2023-12-12 | 2025-03-25 | King Faisal University | Pyrrolo[3,2-c]isoquinoline-2,3-dione compounds as CK2 inhibitors |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3642779A (en) * | 1969-10-22 | 1972-02-15 | Robins Co Inc A H | Indolo(1 2-d)(1 4)benzodiazepin-6-ones |
| US5866702A (en) * | 1996-08-02 | 1999-02-02 | Cv Therapeutics, Incorporation | Purine inhibitors of cyclin dependent kinase 2 |
| ATE239020T1 (de) * | 1996-10-09 | 2003-05-15 | Schering Corp | Tricyclische verbindungen als ras-fpt inhibitoren |
-
1999
- 1999-06-16 WO PCT/US1999/013579 patent/WO1999065910A1/en not_active Ceased
- 1999-06-16 AT AT99928715T patent/ATE318818T1/de not_active IP Right Cessation
- 1999-06-16 JP JP2000554735A patent/JP4555476B2/ja not_active Expired - Fee Related
- 1999-06-16 AU AU45714/99A patent/AU778735B2/en not_active Ceased
- 1999-06-16 CA CA002335115A patent/CA2335115C/en not_active Expired - Fee Related
- 1999-06-16 DE DE69930120T patent/DE69930120T2/de not_active Expired - Lifetime
- 1999-06-16 EP EP99928715A patent/EP1086105B1/en not_active Expired - Lifetime
-
2000
- 2000-12-14 US US09/739,534 patent/US6610684B2/en not_active Expired - Lifetime
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2002518395A5 (https=) | ||
| AU2002226674B2 (en) | Tricyclic and heterocyclic derivative compounds and drugs containing these compounds as the active ingredient | |
| RU2394826C2 (ru) | Дизамещенные пиразолобензодиазепины, используемые в качестве ингибиторов cdk2 и ангиогенеза, а также для лечения злокачественных новообразований молочной железы, толстого кишечника, легкого и предстательной железы | |
| JP2005537248A5 (https=) | ||
| JP2002508375A5 (https=) | ||
| HUP0400828A2 (hu) | Kondenzált heterociklikus aminopirimidinek, alkalmazásuk és az ezeket tartalmazó gyógyszerkészítmények | |
| JP2007505933A5 (https=) | ||
| JP2003518115A5 (https=) | ||
| JP2004520285A5 (https=) | ||
| RU2009101298A (ru) | Гетероциклические соединения в качестве усилителей подслащивающего вещества | |
| US20030225092A1 (en) | Chemical compounds | |
| RU2005132308A (ru) | Производные гуанидина и их применение в качестве антагонистов рецептора нейропептида ff | |
| US6825197B2 (en) | Cyclic GMP-specific phosphodiesterase inhibitors | |
| JPWO2006135080A1 (ja) | チエノピリミジン誘導体 | |
| RU98117245A (ru) | 2-(арилфенил)аминоимидазолиновые производные | |
| JP2008510755A (ja) | ビシクロノネン誘導体 | |
| EP2981527B1 (en) | Derivatives of luciferin. | |
| JP2656201B2 (ja) | ４，５−ジヒドロピラゾロ〔３，４−ａ〕アクリジン類、それらの製造方法およびそれらからなる鎮痛剤 | |
| EP0348891A2 (en) | Lactamimides as calcium antagonists | |
| FR2812636A1 (fr) | Nouveaux derives 2-phenyl imidazo[1.2-a]pyrimidin-5-ones et 2-phenyl 2,3-dihydro imidazo[1,2-a]pyrimidin-5-ones | |
| US5198433A (en) | Lactamimides as calcium antagonists | |
| US5128337A (en) | Lactamimides as calcium antagonists | |
| US5158945A (en) | Lactamimides as calcium antagonists | |
| IL99441A0 (en) | Heterocyclic acids | |
| AU2017364804A1 (en) | Therapeutic drug or prophylactic drug for diabetic nephropathy |