JP2016515098A5 - - Google Patents
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- JP2016515098A5 JP2016515098A5 JP2015560285A JP2015560285A JP2016515098A5 JP 2016515098 A5 JP2016515098 A5 JP 2016515098A5 JP 2015560285 A JP2015560285 A JP 2015560285A JP 2015560285 A JP2015560285 A JP 2015560285A JP 2016515098 A5 JP2016515098 A5 JP 2016515098A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- alkyl
- dimethyl
- carbazole
- carboxamide
- 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.)
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 168
- 229910052739 hydrogen Inorganic materials 0.000 claims 126
- 239000001257 hydrogen Substances 0.000 claims 126
- 125000001072 heteroaryl group Chemical group 0.000 claims 103
- 150000002431 hydrogen Chemical group 0.000 claims 83
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 55
- 229910052736 halogen Inorganic materials 0.000 claims 51
- 150000002367 halogens Chemical class 0.000 claims 51
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 50
- 125000004093 cyano group Chemical group *C#N 0.000 claims 46
- 125000000623 heterocyclic group Chemical group 0.000 claims 46
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 43
- -1 Dimethyl-1,2-oxazol-4-yl Chemical group 0.000 claims 39
- 125000003107 substituted aryl group Chemical group 0.000 claims 33
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 31
- 229920001577 copolymer Chemical group 0.000 claims 30
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 26
- 125000000217 alkyl group Chemical group 0.000 claims 20
- 229910052757 nitrogen Inorganic materials 0.000 claims 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 16
- 125000003118 aryl group Chemical group 0.000 claims 10
- 150000003857 carboxamides Chemical class 0.000 claims 10
- 239000008194 pharmaceutical composition Substances 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 7
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 238000006467 substitution reaction Methods 0.000 claims 6
- 206010028980 Neoplasm Diseases 0.000 claims 5
- 201000011510 cancer Diseases 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- VEARIFFTYFXLCQ-UHFFFAOYSA-N 6-(3,3-difluoroazetidine-1-carbonyl)-2-(3,5-dimethyl-1,2-oxazol-4-yl)-9-(1-phenylethyl)carbazole-4-carboxamide Chemical compound C12=CC=C(C(=O)N3CC(F)(F)C3)C=C2C2=C(C(N)=O)C=C(C3=C(ON=C3C)C)C=C2N1C(C)C1=CC=CC=C1 VEARIFFTYFXLCQ-UHFFFAOYSA-N 0.000 claims 3
- PCROQKOTNKCDOP-UHFFFAOYSA-N 1-(3,5-dimethyl-1,2-oxazol-4-yl)-9-[(4-fluorophenyl)-(oxan-4-yl)methyl]-7-(2-hydroxypropan-2-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC=C(C(N)=O)C2=C1N(C(C1CCOCC1)C=1C=CC(F)=CC=1)C1=CC(C(C)(C)O)=CC=C12 PCROQKOTNKCDOP-UHFFFAOYSA-N 0.000 claims 2
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- PTXYHIKUWBROMP-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-methoxy-9-(1-phenylethyl)carbazole-4-carboxamide Chemical compound C12=CC(C3=C(ON=C3C)C)=CC(C(N)=O)=C2C2=CC(OC)=CC=C2N1C(C)C1=CC=CC=C1 PTXYHIKUWBROMP-UHFFFAOYSA-N 0.000 claims 2
- HNXIMTFHRGHUHY-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-7-(2-hydroxypropan-2-yl)-9-(4,4,4-trifluoro-1-pyridin-2-ylbutyl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC=C(C(C)(C)O)C=C3N(C(CCC(F)(F)F)C=3N=CC=CC=3)C2=C1 HNXIMTFHRGHUHY-UHFFFAOYSA-N 0.000 claims 2
- GXOJFGNCOHQOIG-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-7-(2-hydroxypropan-2-yl)-9-[(3-methoxyphenyl)-(oxan-4-yl)methyl]carbazole-4-carboxamide Chemical compound COC1=CC=CC(C(C2CCOCC2)N2C3=CC(=CC(=C3C3=CC=C(C=C32)C(C)(C)O)C(N)=O)C2=C(ON=C2C)C)=C1 GXOJFGNCOHQOIG-UHFFFAOYSA-N 0.000 claims 2
- QDNKGFASTDKESA-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-7-(2-hydroxypropan-2-yl)-9-[(4-methoxyphenyl)-(oxan-4-yl)methyl]carbazole-4-carboxamide Chemical compound C1=CC(OC)=CC=C1C(N1C2=CC(=CC(=C2C2=CC=C(C=C21)C(C)(C)O)C(N)=O)C1=C(ON=C1C)C)C1CCOCC1 QDNKGFASTDKESA-UHFFFAOYSA-N 0.000 claims 2
- VTHVPYFGFCBBJH-HKBQPEDESA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-7-(2-hydroxypropan-2-yl)-9-[(r)-oxan-4-yl(phenyl)methyl]carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC=C(C(C)(C)O)C=C3N([C@H](C3CCOCC3)C=3C=CC=CC=3)C2=C1 VTHVPYFGFCBBJH-HKBQPEDESA-N 0.000 claims 2
- GTAOHKMCIIWAQH-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-7-(2-hydroxypropan-2-yl)-9-[4,4,4-trifluoro-1-[2-(trifluoromethyl)phenyl]butyl]carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC=C(C(C)(C)O)C=C3N(C(CCC(F)(F)F)C=3C(=CC=CC=3)C(F)(F)F)C2=C1 GTAOHKMCIIWAQH-UHFFFAOYSA-N 0.000 claims 2
- BDEPUTYZLQHUPC-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-7-(2-hydroxypropan-2-yl)-9-[oxan-4-yl-(2,4,6-trifluorophenyl)methyl]carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC=C(C(C)(C)O)C=C3N(C(C3CCOCC3)C=3C(=CC(F)=CC=3F)F)C2=C1 BDEPUTYZLQHUPC-UHFFFAOYSA-N 0.000 claims 2
- PJQRKRQPRUJNBD-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-8-fluoro-7-(2-hydroxypropan-2-yl)-9-(4,4,4-trifluoro-1-phenylbutyl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC=C(C(C)(C)O)C(F)=C3N(C(CCC(F)(F)F)C=3C=CC=CC=3)C2=C1 PJQRKRQPRUJNBD-UHFFFAOYSA-N 0.000 claims 2
- GZPXPLRXQLLVER-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-8-fluoro-9-[(4-fluorophenyl)-(oxan-4-yl)methyl]-7-(2-hydroxypropan-2-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC=C(C(C)(C)O)C(F)=C3N(C(C3CCOCC3)C=3C=CC(F)=CC=3)C2=C1 GZPXPLRXQLLVER-UHFFFAOYSA-N 0.000 claims 2
- MDDROMACACANRC-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-9-[(1-fluorocyclobutyl)-phenylmethyl]-7-(2-hydroxypropan-2-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC=C(C(C)(C)O)C=C3N(C(C=3C=CC=CC=3)C3(F)CCC3)C2=C1 MDDROMACACANRC-UHFFFAOYSA-N 0.000 claims 2
- VHSJPTBYKKWDMX-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-9-[(2-fluorophenyl)-(oxan-4-yl)methyl]-7-(2-hydroxypropan-2-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC=C(C(C)(C)O)C=C3N(C(C3CCOCC3)C=3C(=CC=CC=3)F)C2=C1 VHSJPTBYKKWDMX-UHFFFAOYSA-N 0.000 claims 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 2
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 2
- RINFCFCAVYTZNQ-UHFFFAOYSA-N 9-[(2,4-difluorophenyl)-(oxan-4-yl)methyl]-2-(3,5-dimethyl-1,2-oxazol-4-yl)-7-(2-hydroxypropan-2-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC=C(C(C)(C)O)C=C3N(C(C3CCOCC3)C=3C(=CC(F)=CC=3)F)C2=C1 RINFCFCAVYTZNQ-UHFFFAOYSA-N 0.000 claims 2
- VUPVKCXZTKAVRO-UHFFFAOYSA-N 9-[(4,4-difluorocyclohexyl)-phenylmethyl]-2-(3,5-dimethyl-1,2-oxazol-4-yl)-8-fluoro-7-(2-hydroxypropan-2-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC=C(C(C)(C)O)C(F)=C3N(C(C3CCC(F)(F)CC3)C=3C=CC=CC=3)C2=C1 VUPVKCXZTKAVRO-UHFFFAOYSA-N 0.000 claims 2
- WMGWRRMNUPHOTQ-UHFFFAOYSA-N 9-[1-(2-chlorophenyl)-4,4,4-trifluorobutyl]-2-(3,5-dimethyl-1,2-oxazol-4-yl)-7-(2-hydroxypropan-2-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC=C(C(C)(C)O)C=C3N(C(CCC(F)(F)F)C=3C(=CC=CC=3)Cl)C2=C1 WMGWRRMNUPHOTQ-UHFFFAOYSA-N 0.000 claims 2
- URPYZYLDIAFPSN-UHFFFAOYSA-N 9-benzhydryl-5-cyano-7-(3,5-dimethyl-1,2-oxazol-4-yl)carbazole-2-carboxylic acid Chemical compound CC1=NOC(C)=C1C1=CC(C#N)=C2C3=CC=C(C(O)=O)C=C3N(C(C=3C=CC=CC=3)C=3C=CC=CC=3)C2=C1 URPYZYLDIAFPSN-UHFFFAOYSA-N 0.000 claims 2
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 2
- 102000001805 Bromodomains Human genes 0.000 claims 2
- 108050009021 Bromodomains Proteins 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 2
- 208000034578 Multiple myelomas Diseases 0.000 claims 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 2
- 206010060862 Prostate cancer Diseases 0.000 claims 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 2
- 206010041067 Small cell lung cancer Diseases 0.000 claims 2
- 208000029052 T-cell acute lymphoblastic leukemia Diseases 0.000 claims 2
- 201000011176 T-cell adult acute lymphocytic leukemia Diseases 0.000 claims 2
- 208000003721 Triple Negative Breast Neoplasms Diseases 0.000 claims 2
- 229940125763 bromodomain inhibitor Drugs 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 2
- 201000001441 melanoma Diseases 0.000 claims 2
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 2
- 201000002528 pancreatic cancer Diseases 0.000 claims 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 2
- 208000000587 small cell lung carcinoma Diseases 0.000 claims 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 2
- 208000022679 triple-negative breast carcinoma Diseases 0.000 claims 2
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 2
- UDYYALMTRRVAJO-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(2-oxo-1,3-oxazinan-3-yl)-9-(1-phenylethyl)carbazole-4-carboxamide Chemical compound C12=CC=C(N3C(OCCC3)=O)C=C2C2=C(C(N)=O)C=C(C3=C(ON=C3C)C)C=C2N1C(C)C1=CC=CC=C1 UDYYALMTRRVAJO-UHFFFAOYSA-N 0.000 claims 1
- PIEGZRMSZHBJHE-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(2-oxo-1,3-oxazinan-3-yl)-9h-carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(N4C(OCCC4)=O)=CC=C3NC2=C1 PIEGZRMSZHBJHE-UHFFFAOYSA-N 0.000 claims 1
- HHYRMSDPWBCKTJ-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(2-oxo-1,3-oxazolidin-3-yl)-9-(1-phenylethyl)carbazole-4-carboxamide Chemical compound C12=CC=C(N3C(OCC3)=O)C=C2C2=C(C(N)=O)C=C(C3=C(ON=C3C)C)C=C2N1C(C)C1=CC=CC=C1 HHYRMSDPWBCKTJ-UHFFFAOYSA-N 0.000 claims 1
- CQRYHAYNFAANAL-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3-fluoroazetidine-1-carbonyl)-9-(1-phenylethyl)carbazole-4-carboxamide Chemical compound C12=CC=C(C(=O)N3CC(F)C3)C=C2C2=C(C(N)=O)C=C(C3=C(ON=C3C)C)C=C2N1C(C)C1=CC=CC=C1 CQRYHAYNFAANAL-UHFFFAOYSA-N 0.000 claims 1
- OAYBTVMVQHYZRO-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3-fluoroazetidine-1-carbonyl)-9-[(3-fluorophenyl)methyl]-n-methylcarbazole-4-carboxamide Chemical compound C12=CC=C(C(=O)N3CC(F)C3)C=C2C=2C(C(=O)NC)=CC(C3=C(ON=C3C)C)=CC=2N1CC1=CC=CC(F)=C1 OAYBTVMVQHYZRO-UHFFFAOYSA-N 0.000 claims 1
- HGMXUMBQBAMBKV-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3-fluoroazetidine-1-carbonyl)-9-[(3-fluorophenyl)methyl]carbazole-4-carbonitrile Chemical compound CC1=NOC(C)=C1C1=CC(C#N)=C2C3=CC(C(=O)N4CC(F)C4)=CC=C3N(CC=3C=C(F)C=CC=3)C2=C1 HGMXUMBQBAMBKV-UHFFFAOYSA-N 0.000 claims 1
- NIAKYZIDOHXFTG-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3-fluoroazetidine-1-carbonyl)-9-[(4-fluorophenyl)methyl]-n-(2-methylpropyl)carbazole-4-carboxamide Chemical compound C12=CC=C(C(=O)N3CC(F)C3)C=C2C=2C(C(=O)NCC(C)C)=CC(C3=C(ON=C3C)C)=CC=2N1CC1=CC=C(F)C=C1 NIAKYZIDOHXFTG-UHFFFAOYSA-N 0.000 claims 1
- UURDSNFOELPMLF-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3-fluoroazetidine-1-carbonyl)-9-[(4-fluorophenyl)methyl]-n-methylcarbazole-4-carboxamide Chemical compound C12=CC=C(C(=O)N3CC(F)C3)C=C2C=2C(C(=O)NC)=CC(C3=C(ON=C3C)C)=CC=2N1CC1=CC=C(F)C=C1 UURDSNFOELPMLF-UHFFFAOYSA-N 0.000 claims 1
- GBXZYBPHTGPKKV-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3-fluoroazetidine-1-carbonyl)-9-[(4-fluorophenyl)methyl]-n-propan-2-ylcarbazole-4-carboxamide Chemical compound C12=CC=C(C(=O)N3CC(F)C3)C=C2C=2C(C(=O)NC(C)C)=CC(C3=C(ON=C3C)C)=CC=2N1CC1=CC=C(F)C=C1 GBXZYBPHTGPKKV-UHFFFAOYSA-N 0.000 claims 1
- RNFGBEXMTCADHK-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3-fluoroazetidine-1-carbonyl)-9-[(4-fluorophenyl)methyl]-n-propylcarbazole-4-carboxamide Chemical compound C12=CC=C(C(=O)N3CC(F)C3)C=C2C=2C(C(=O)NCCC)=CC(C3=C(ON=C3C)C)=CC=2N1CC1=CC=C(F)C=C1 RNFGBEXMTCADHK-UHFFFAOYSA-N 0.000 claims 1
- CPALAFLOXDEHLR-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3-fluoroazetidine-1-carbonyl)-9-[(4-fluorophenyl)methyl]carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(C(=O)N4CC(F)C4)=CC=C3N(CC=3C=CC(F)=CC=3)C2=C1 CPALAFLOXDEHLR-UHFFFAOYSA-N 0.000 claims 1
- VKLQRHNQNBFNIG-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3-fluoroazetidine-1-carbonyl)-9-[1-(4-fluorophenyl)ethyl]-n-methylcarbazole-4-carboxamide Chemical compound C12=CC=C(C(=O)N3CC(F)C3)C=C2C=2C(C(=O)NC)=CC(C3=C(ON=C3C)C)=CC=2N1C(C)C1=CC=C(F)C=C1 VKLQRHNQNBFNIG-UHFFFAOYSA-N 0.000 claims 1
- WNAFFNIIHISTGI-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3-fluoroazetidine-1-carbonyl)-9-[1-(4-fluorophenyl)ethyl]carbazole-4-carboxamide Chemical compound C12=CC=C(C(=O)N3CC(F)C3)C=C2C2=C(C(N)=O)C=C(C3=C(ON=C3C)C)C=C2N1C(C)C1=CC=C(F)C=C1 WNAFFNIIHISTGI-UHFFFAOYSA-N 0.000 claims 1
- OJNPOEAKXOXCGR-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3-fluoroazetidine-1-carbonyl)-9-[1-[2-(trifluoromethyl)phenyl]ethyl]carbazole-4-carboxamide Chemical compound C12=CC=C(C(=O)N3CC(F)C3)C=C2C2=C(C(N)=O)C=C(C3=C(ON=C3C)C)C=C2N1C(C)C1=CC=CC=C1C(F)(F)F OJNPOEAKXOXCGR-UHFFFAOYSA-N 0.000 claims 1
- CPETVVDDMYSLFS-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3-fluoroazetidine-1-carbonyl)-9-[1-[3-(trifluoromethyl)phenyl]ethyl]carbazole-4-carboxamide Chemical compound C12=CC=C(C(=O)N3CC(F)C3)C=C2C2=C(C(N)=O)C=C(C3=C(ON=C3C)C)C=C2N1C(C)C1=CC=CC(C(F)(F)F)=C1 CPETVVDDMYSLFS-UHFFFAOYSA-N 0.000 claims 1
- VFGZHMFWKFAYNW-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3-fluoroazetidine-1-carbonyl)-n-methyl-9-(1-phenylethyl)carbazole-4-carboxamide Chemical compound C12=CC=C(C(=O)N3CC(F)C3)C=C2C=2C(C(=O)NC)=CC(C3=C(ON=C3C)C)=CC=2N1C(C)C1=CC=CC=C1 VFGZHMFWKFAYNW-UHFFFAOYSA-N 0.000 claims 1
- ZZGYLIUMKKQVCL-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3-fluoroazetidine-1-carbonyl)-n-methyl-9h-carbazole-4-carboxamide Chemical compound C1=C2C=3C(C(=O)NC)=CC(C4=C(ON=C4C)C)=CC=3NC2=CC=C1C(=O)N1CC(F)C1 ZZGYLIUMKKQVCL-UHFFFAOYSA-N 0.000 claims 1
- OTVLWPXUFAKHPL-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(5,5-dimethyl-2-oxo-1,3-oxazinan-3-yl)-9-[(4-fluorophenyl)methyl]carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(N4C(OCC(C)(C)C4)=O)=CC=C3N(CC=3C=CC(F)=CC=3)C2=C1 OTVLWPXUFAKHPL-UHFFFAOYSA-N 0.000 claims 1
- HGMPAMUARIRGOH-IMMUGOHXSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-[(3s)-3-fluoropyrrolidine-1-carbonyl]-9-(1-phenylethyl)carbazole-4-carboxamide Chemical compound C12=CC=C(C(=O)N3C[C@@H](F)CC3)C=C2C2=C(C(N)=O)C=C(C3=C(ON=C3C)C)C=C2N1C(C)C1=CC=CC=C1 HGMPAMUARIRGOH-IMMUGOHXSA-N 0.000 claims 1
- DZYQBYAJEJXEIM-IBGZPJMESA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-[(3s)-3-fluoropyrrolidine-1-carbonyl]-9-[(4-methyl-1,3-thiazol-2-yl)methyl]carbazole-4-carboxamide Chemical compound CC1=CSC(CN2C3=CC(=CC(=C3C3=CC(=CC=C32)C(=O)N2C[C@@H](F)CC2)C(N)=O)C2=C(ON=C2C)C)=N1 DZYQBYAJEJXEIM-IBGZPJMESA-N 0.000 claims 1
- YPTAOBVCBZIKKT-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-7-(2-hydroxypropan-2-yl)-9-(oxan-4-ylmethyl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC=C(C(C)(C)O)C=C3N(CC3CCOCC3)C2=C1 YPTAOBVCBZIKKT-UHFFFAOYSA-N 0.000 claims 1
- WTSYNQKJRDIJTQ-JGCGQSQUSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-7-(2-methoxypropan-2-yl)-9-[(s)-oxan-4-yl(phenyl)methyl]carbazole-4-carboxamide Chemical compound C1([C@H](N2C=3C(C4=C(C(N)=O)C=C(C=C42)C2=C(ON=C2C)C)=CC=C(C=3)C(C)(C)OC)C=2C=CC=CC=2)CCOCC1 WTSYNQKJRDIJTQ-JGCGQSQUSA-N 0.000 claims 1
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- GHMOHECUZWFSDI-KDURUIRLSA-N [(2r,6s)-2,6-dimethylmorpholin-4-yl]-[7-(3,5-dimethyl-1,2-oxazol-4-yl)-9-[(3-fluorophenyl)methyl]carbazol-3-yl]methanone Chemical compound C1[C@@H](C)O[C@@H](C)CN1C(=O)C1=CC=C(N(CC=2C=C(F)C=CC=2)C=2C3=CC=C(C=2)C2=C(ON=C2C)C)C3=C1 GHMOHECUZWFSDI-KDURUIRLSA-N 0.000 claims 1
- GCKOGZSMAOWLRK-BGYRXZFFSA-N [(2r,6s)-2,6-dimethylmorpholin-4-yl]-[7-(3,5-dimethyl-1,2-oxazol-4-yl)-9-[(3-methoxyphenyl)methyl]carbazol-3-yl]methanone Chemical compound COC1=CC=CC(CN2C3=CC(=CC=C3C3=CC(=CC=C32)C(=O)N2C[C@@H](C)O[C@@H](C)C2)C2=C(ON=C2C)C)=C1 GCKOGZSMAOWLRK-BGYRXZFFSA-N 0.000 claims 1
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- JHWUSROQQAGOON-KDURUIRLSA-N [(2r,6s)-2,6-dimethylmorpholin-4-yl]-[7-(3,5-dimethyl-1,2-oxazol-4-yl)-9-[(4-fluorophenyl)methyl]carbazol-3-yl]methanone Chemical compound C1[C@@H](C)O[C@@H](C)CN1C(=O)C1=CC=C(N(CC=2C=CC(F)=CC=2)C=2C3=CC=C(C=2)C2=C(ON=C2C)C)C3=C1 JHWUSROQQAGOON-KDURUIRLSA-N 0.000 claims 1
- CVQSFKVIWFDMOQ-OYRHEFFESA-N [(2r,6s)-2,6-dimethylmorpholin-4-yl]-[7-(3,5-dimethyl-1,2-oxazol-4-yl)-9-[(4-methylphenyl)methyl]carbazol-3-yl]methanone Chemical compound C1[C@@H](C)O[C@@H](C)CN1C(=O)C1=CC=C(N(CC=2C=CC(C)=CC=2)C=2C3=CC=C(C=2)C2=C(ON=C2C)C)C3=C1 CVQSFKVIWFDMOQ-OYRHEFFESA-N 0.000 claims 1
- JMIUNFHRLOUABQ-IYBDPMFKSA-N [(2r,6s)-2,6-dimethylmorpholin-4-yl]-[7-(3,5-dimethyl-1,2-oxazol-4-yl)-9-ethylcarbazol-3-yl]methanone Chemical compound C1=C2N(CC)C3=CC=C(C(=O)N4C[C@@H](C)O[C@@H](C)C4)C=C3C2=CC=C1C=1C(C)=NOC=1C JMIUNFHRLOUABQ-IYBDPMFKSA-N 0.000 claims 1
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- IFNZZAMDGDHLGV-IYBDPMFKSA-N [(2s,6r)-2,6-dimethylmorpholin-4-yl]-[7-(3,5-dimethyl-1,2-oxazol-4-yl)-9-(2-fluoroethyl)carbazol-3-yl]methanone Chemical compound C1[C@@H](C)O[C@@H](C)CN1C(=O)C1=CC=C(N(CCF)C=2C3=CC=C(C=2)C2=C(ON=C2C)C)C3=C1 IFNZZAMDGDHLGV-IYBDPMFKSA-N 0.000 claims 1
- ALLWWQDFXORBGO-HDICACEKSA-N [(2s,6r)-2,6-dimethylmorpholin-4-yl]-[7-(3,5-dimethyl-1,2-oxazol-4-yl)-9-(2-methylpropyl)carbazol-3-yl]methanone Chemical compound C1=C2N(CC(C)C)C3=CC=C(C(=O)N4C[C@@H](C)O[C@@H](C)C4)C=C3C2=CC=C1C=1C(C)=NOC=1C ALLWWQDFXORBGO-HDICACEKSA-N 0.000 claims 1
- ZWCSKIACDITOHO-GASCZTMLSA-N [(2s,6r)-2,6-dimethylmorpholin-4-yl]-[7-(3,5-dimethyl-1,2-oxazol-4-yl)-9-methylsulfonylcarbazol-3-yl]methanone Chemical compound C1[C@@H](C)O[C@@H](C)CN1C(=O)C1=CC=C(N(C=2C3=CC=C(C=2)C2=C(ON=C2C)C)S(C)(=O)=O)C3=C1 ZWCSKIACDITOHO-GASCZTMLSA-N 0.000 claims 1
- MYZQINULMLOYKC-KDURUIRLSA-N [6-[(2s,6r)-2,6-dimethylmorpholine-4-carbonyl]-2-(3,5-dimethyl-1,2-oxazol-4-yl)carbazol-9-yl]-phenylmethanone Chemical compound C1[C@@H](C)O[C@@H](C)CN1C(=O)C1=CC=C(N(C(=O)C=2C=CC=CC=2)C=2C3=CC=C(C=2)C2=C(ON=C2C)C)C3=C1 MYZQINULMLOYKC-KDURUIRLSA-N 0.000 claims 1
- HPAIGTBNYZVHCU-UHFFFAOYSA-N [7-(3,5-dimethyl-1,2-oxazol-4-yl)-5-(3-fluoroazetidine-1-carbonyl)-9-[(4-fluorophenyl)methyl]carbazol-3-yl]-(3-fluoroazetidin-1-yl)methanone Chemical compound CC1=NOC(C)=C1C1=CC(C(=O)N2CC(F)C2)=C2C3=CC(C(=O)N4CC(F)C4)=CC=C3N(CC=3C=CC(F)=CC=3)C2=C1 HPAIGTBNYZVHCU-UHFFFAOYSA-N 0.000 claims 1
- JYBWZOGNOBBOPI-UHFFFAOYSA-N [7-(3,5-dimethyl-1,2-oxazol-4-yl)-9h-carbazol-3-yl]-morpholin-4-ylmethanone Chemical compound CC1=NOC(C)=C1C1=CC=C2C3=CC(C(=O)N4CCOCC4)=CC=C3NC2=C1 JYBWZOGNOBBOPI-UHFFFAOYSA-N 0.000 claims 1
- QXVWJHUAMHLXQN-GASCZTMLSA-N [9-(2,2-difluoroethyl)-7-(3,5-dimethyl-1,2-oxazol-4-yl)carbazol-3-yl]-[(2r,6s)-2,6-dimethylmorpholin-4-yl]methanone Chemical compound C1[C@@H](C)O[C@@H](C)CN1C(=O)C1=CC=C(N(CC(F)F)C=2C3=CC=C(C=2)C2=C(ON=C2C)C)C3=C1 QXVWJHUAMHLXQN-GASCZTMLSA-N 0.000 claims 1
- QJMNMOWOXNWASG-CALCHBBNSA-N [9-(cyclopropylmethyl)-7-(3,5-dimethyl-1,2-oxazol-4-yl)carbazol-3-yl]-[(2r,6s)-2,6-dimethylmorpholin-4-yl]methanone Chemical compound C1[C@@H](C)O[C@@H](C)CN1C(=O)C1=CC=C(N(CC2CC2)C=2C3=CC=C(C=2)C2=C(ON=C2C)C)C3=C1 QJMNMOWOXNWASG-CALCHBBNSA-N 0.000 claims 1
- DEKWESIDZKELOZ-UHFFFAOYSA-N [9-(cyclopropylmethyl)-7-(3,5-dimethyl-1,2-oxazol-4-yl)carbazol-3-yl]-morpholin-4-ylmethanone Chemical compound CC1=NOC(C)=C1C1=CC=C2C3=CC(C(=O)N4CCOCC4)=CC=C3N(CC3CC3)C2=C1 DEKWESIDZKELOZ-UHFFFAOYSA-N 0.000 claims 1
- XPBJPDRICFOTMT-KDURUIRLSA-N [9-[(2-chlorophenyl)methyl]-7-(3,5-dimethyl-1,2-oxazol-4-yl)carbazol-3-yl]-[(2r,6s)-2,6-dimethylmorpholin-4-yl]methanone Chemical compound C1[C@@H](C)O[C@@H](C)CN1C(=O)C1=CC=C(N(CC=2C(=CC=CC=2)Cl)C=2C3=CC=C(C=2)C2=C(ON=C2C)C)C3=C1 XPBJPDRICFOTMT-KDURUIRLSA-N 0.000 claims 1
- IQOGDTCEUOPSPB-KDURUIRLSA-N [9-[(3-chlorophenyl)methyl]-7-(3,5-dimethyl-1,2-oxazol-4-yl)carbazol-3-yl]-[(2r,6s)-2,6-dimethylmorpholin-4-yl]methanone Chemical compound C1[C@@H](C)O[C@@H](C)CN1C(=O)C1=CC=C(N(CC=2C=C(Cl)C=CC=2)C=2C3=CC=C(C=2)C2=C(ON=C2C)C)C3=C1 IQOGDTCEUOPSPB-KDURUIRLSA-N 0.000 claims 1
- TWYDWEPGIPTGDG-KDURUIRLSA-N [9-[(4-chlorophenyl)methyl]-7-(3,5-dimethyl-1,2-oxazol-4-yl)carbazol-3-yl]-[(2s,6r)-2,6-dimethylmorpholin-4-yl]methanone Chemical compound C1[C@@H](C)O[C@@H](C)CN1C(=O)C1=CC=C(N(CC=2C=CC(Cl)=CC=2)C=2C3=CC=C(C=2)C2=C(ON=C2C)C)C3=C1 TWYDWEPGIPTGDG-KDURUIRLSA-N 0.000 claims 1
- PLFNNYYAFAZJTH-BGYRXZFFSA-N [9-benzyl-7-(3,5-dimethyl-1,2-oxazol-4-yl)carbazol-3-yl]-[(2r,6s)-2,6-dimethylmorpholin-4-yl]methanone Chemical compound C1[C@@H](C)O[C@@H](C)CN1C(=O)C1=CC=C(N(CC=2C=CC=CC=2)C=2C3=CC=C(C=2)C2=C(ON=C2C)C)C3=C1 PLFNNYYAFAZJTH-BGYRXZFFSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 238000003556 assay Methods 0.000 claims 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000002866 fluorescence resonance energy transfer Methods 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- WDVBBZXERNHBNP-UHFFFAOYSA-N methyl 9-benzhydryl-5-carbamoyl-7-(3,5-dimethyl-1,2-oxazol-4-yl)carbazole-2-carboxylate Chemical compound C=1C(C(=O)OC)=CC=C(C2=C(C(N)=O)C=C(C=C22)C3=C(ON=C3C)C)C=1N2C(C=1C=CC=CC=1)C1=CC=CC=C1 WDVBBZXERNHBNP-UHFFFAOYSA-N 0.000 claims 1
- DVYNFYBBONTKLE-UHFFFAOYSA-N methyl 9-benzyl-5-carbamoyl-7-(3,5-dimethyl-1,2-oxazol-4-yl)carbazole-2-carboxylate Chemical compound C=1C(C(=O)OC)=CC=C(C2=C(C(N)=O)C=C(C=C22)C3=C(ON=C3C)C)C=1N2CC1=CC=CC=C1 DVYNFYBBONTKLE-UHFFFAOYSA-N 0.000 claims 1
- DAHMGJCFYANPJX-UHFFFAOYSA-N methyl 9-benzyl-5-cyano-7-(3,5-dimethyl-1,2-oxazol-4-yl)carbazole-2-carboxylate Chemical compound C=1C(C(=O)OC)=CC=C(C2=C(C#N)C=C(C=C22)C3=C(ON=C3C)C)C=1N2CC1=CC=CC=C1 DAHMGJCFYANPJX-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- CRKCGNJIKMXEMN-UHFFFAOYSA-N n-[9-benzyl-5-carbamoyl-7-(3,5-dimethyl-1,2-oxazol-4-yl)carbazol-3-yl]morpholine-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(NC(=O)N4CCOCC4)=CC=C3N(CC=3C=CC=CC=3)C2=C1 CRKCGNJIKMXEMN-UHFFFAOYSA-N 0.000 claims 1
- VEBDTZDIRBNUAV-UHFFFAOYSA-N n-cyclopropyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3-fluoroazetidine-1-carbonyl)-9-[(4-fluorophenyl)methyl]carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(=O)NC2CC2)=C2C3=CC(C(=O)N4CC(F)C4)=CC=C3N(CC=3C=CC(F)=CC=3)C2=C1 VEBDTZDIRBNUAV-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 1
- 0 CCCC(*)(*C)N Chemical compound CCCC(*)(*C)N 0.000 description 4
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| US9073878B2 (en) | 2012-11-21 | 2015-07-07 | Zenith Epigenetics Corp. | Cyclic amines as bromodomain inhibitors |
| US9765039B2 (en) | 2012-11-21 | 2017-09-19 | Zenith Epigenetics Ltd. | Biaryl derivatives as bromodomain inhibitors |
| CN105073744B (zh) | 2012-12-21 | 2019-11-08 | 齐尼思表观遗传学有限公司 | 作为溴结构域抑制剂的新型杂环化合物 |
| CN105189488B (zh) | 2013-02-27 | 2018-07-24 | 百时美施贵宝公司 | 用作溴区结构域抑制剂的咔唑化合物 |
| JP6401773B2 (ja) * | 2013-03-11 | 2018-10-10 | ザ リージェンツ オブ ザ ユニヴァシティ オブ ミシガン | Ｂｅｔブロモドメイン阻害剤およびこれを用いる治療方法 |
| BR112015022942B1 (pt) | 2013-03-15 | 2022-02-22 | Incyte Holdings Corporation | Compostos heterocíciclos tricíclicos, método para inibir proteína bet in vitro e composição farmacêutica compreendendo os referidos compostos |
| WO2015004533A2 (en) | 2013-06-21 | 2015-01-15 | Zenith Epigenetics Corp. | Novel substituted bicyclic compounds as bromodomain inhibitors |
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| EP3027604B1 (en) | 2013-07-31 | 2019-02-20 | Zenith Epigenetics Ltd. | Novel quinazolinones as bromodomain inhibitors |
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| SI3466949T1 (sl) * | 2013-12-24 | 2021-03-31 | Bristol-Myers Squibb Company | Triciklična spojina kot sredstvo proti raku |
| EP3110818B1 (en) | 2014-02-28 | 2019-10-23 | The Regents of The University of Michigan | 9h-pyrimido[4,5-b]indoles and related analogs as bet bromodomain inhibitors |
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| ES2855225T3 (es) | 2014-09-15 | 2021-09-23 | Incyte Corp | Heterociclos tricíclicos para su uso como inhibidores de proteínas BET |
| BR112017006342A2 (pt) * | 2014-10-02 | 2017-12-19 | Glaxosmithkline Ip No 2 Ltd | composto de sal de ácido benzenossulfônico, forma em estado sólido cristalino, composição farmacêutica, produto farmacêutico de combinação, método de tratamento de doenças ou condições, uso de um composto de sal de ácido benzenossulfônico, e, processo para preparação de um composto de sal de ácido benzenossulfônico. |
| HK1245246A1 (zh) | 2014-12-01 | 2018-08-24 | 恒翼生物医药科技(上海)有限公司 | 作为溴域抑制剂的取代吡啶酮 |
| HK1246273B (en) | 2014-12-01 | 2019-12-06 | 恒翼生物医药(上海)股份有限公司 | Substituted pyridines as bromodomain inhibitors |
| JP2017537946A (ja) | 2014-12-11 | 2017-12-21 | ゼニス・エピジェネティクス・リミテッドＺｅｎｉｔｈ Ｅｐｉｇｅｎｅｔｉｃｓ Ｌｔｄ． | ブロモドメイン阻害剤としての置換複素環 |
| CA2966450A1 (en) | 2014-12-17 | 2016-06-23 | Olesya KHARENKO | Inhibitors of bromodomains |
| KR20230175343A (ko) | 2015-03-18 | 2023-12-29 | 아비나스 오퍼레이션스, 인코포레이티드 | 타겟화된 단백질들의 향상된 분해를 위한 화합물들 및 방법들 |
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| WO2017165139A1 (en) | 2016-03-25 | 2017-09-28 | St. Jude Children's Research Hospital | 1,4,5-substituted 1,2,3-triazole analogues as antagonists of the pregnane x receptor |
| WO2017172914A1 (en) | 2016-03-30 | 2017-10-05 | Wisconsin Alumni Research Foundation | Methods and compositions for modulating frataxin expression |
| EP3472157B1 (en) | 2016-06-20 | 2023-04-12 | Incyte Corporation | Crystalline solid forms of a bet inhibitor |
| AU2018215212B2 (en) | 2017-01-31 | 2022-06-02 | Arvinas Operations, Inc. | Cereblon ligands and bifunctional compounds comprising the same |
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| CN118059104A (zh) | 2019-12-19 | 2024-05-24 | 阿尔维纳斯运营股份有限公司 | 用于雄激素受体的靶向降解的化合物和方法 |
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| GB9310635D0 (en) * | 1993-05-21 | 1993-07-07 | Glaxo Group Ltd | Chemical compounds |
| US6177440B1 (en) | 1996-10-30 | 2001-01-23 | Eli Lilly And Company | Substituted tricyclics |
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| JP5842630B2 (ja) | 2011-03-16 | 2016-01-13 | 株式会社リコー | カルバゾール誘導体、及び半導体ナノ結晶 |
| WO2012150826A1 (en) * | 2011-05-03 | 2012-11-08 | Rohm And Haas Electronic Materials Korea Ltd. | Novel organic electroluminescent compounds and an organic electroluminescent device using the same |
| UA115576C2 (uk) * | 2012-12-06 | 2017-11-27 | Байєр Фарма Акцієнгезелльшафт | Похідні бензимідазолу як антагоністи ер4 |
-
2014
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- 2014-02-27 CN CN201480010613.1A patent/CN105008352B/zh active Active
- 2014-02-27 MX MX2015010921A patent/MX2015010921A/es unknown
- 2014-02-27 WO PCT/US2014/018820 patent/WO2014134232A1/en not_active Ceased
- 2014-02-27 CA CA2902737A patent/CA2902737A1/en not_active Abandoned
- 2014-02-27 EA EA201591591A patent/EA027345B1/ru not_active IP Right Cessation
- 2014-02-27 EP EP14712815.1A patent/EP2961748B1/en active Active
- 2014-02-27 ES ES14712815.1T patent/ES2669189T3/es active Active
- 2014-02-27 JP JP2015560285A patent/JP6395731B2/ja active Active
- 2014-02-27 BR BR112015020389A patent/BR112015020389A8/pt not_active Application Discontinuation
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