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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| PCT/US2014/018820 WO2014134232A1 (en) | 2013-02-27 | 2014-02-27 | Carbazole compounds useful as bromodomain inhibitors |
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| EP2802608A4 (en) | 2012-01-12 | 2015-08-05 | Univ Yale | COMPOUNDS AND METHODS FOR ENHANCED DEGRADATION OF TARGET PROTEINS AND OTHER POLYPEPTIDES BY E3 UBIQUITIN LIGASE |
| WO2014080291A2 (en) | 2012-11-21 | 2014-05-30 | Rvx Therapeutics Inc. | Biaryl derivatives as bromodomain inhibitors |
| WO2014080290A2 (en) | 2012-11-21 | 2014-05-30 | Rvx Therapeutics Inc. | Cyclic amines as bromodomain inhibitors |
| CA2895905A1 (en) | 2012-12-21 | 2014-06-26 | Zenith Epigenetics Corp. | Novel heterocyclic compounds as bromodomain inhibitors |
| 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 |
| EP2970282B1 (en) | 2013-03-15 | 2019-08-21 | Incyte Holdings Corporation | Tricyclic heterocycles as bet protein inhibitors |
| HRP20200854T1 (hr) | 2013-06-21 | 2020-08-21 | Zenith Epigenetics Ltd. | Novi biciklički inhibitori bromodomene |
| WO2015004534A2 (en) | 2013-06-21 | 2015-01-15 | Zenith Epigenetics Corp. | Novel substituted bicyclic compounds as bromodomain inhibitors |
| AR096837A1 (es) | 2013-07-08 | 2016-02-03 | Incyte Corp | Heterociclos tricíclicos como inhibidores de proteínas bet |
| JP6542212B2 (ja) | 2013-07-31 | 2019-07-10 | 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新規キナゾリノン |
| US9399640B2 (en) | 2013-11-26 | 2016-07-26 | Incyte Corporation | Substituted pyrrolo[2,3-c]pyridines and pyrazolo[3,4-c]pyridines as BET protein inhibitors |
| US9315501B2 (en) | 2013-11-26 | 2016-04-19 | Incyte Corporation | Bicyclic heterocycles as BET protein inhibitors |
| US9309246B2 (en) | 2013-12-19 | 2016-04-12 | Incyte Corporation | Tricyclic heterocycles as BET protein inhibitors |
| US9458156B2 (en) | 2014-12-23 | 2016-10-04 | Bristol-Myers Squibb Company | Tricyclic compounds as anticancer agents |
| EA032469B1 (ru) * | 2013-12-24 | 2019-05-31 | Бристол-Маерс Сквибб Компани | Новые трициклические соединения в качестве противораковых средств |
| 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 |
| US20180228907A1 (en) | 2014-04-14 | 2018-08-16 | Arvinas, Inc. | Cereblon ligands and bifunctional compounds comprising the same |
| MY207899A (en) | 2014-04-23 | 2025-03-27 | Incyte Holdings Corp | 1h-pyrrolo[2,3-c]pyridin-7(6h)-ones and pyrazolo[3,4-c]pyridin-7(6h)-ones as inhibitors of bet proteins |
| RU2016147946A (ru) | 2014-05-08 | 2018-06-08 | Онкоэтикс Гмбх | Способ лечения трижды негативного рака молочной железы с использованием тиенотриазолодиазепиновых соединений |
| ES2855225T3 (es) | 2014-09-15 | 2021-09-23 | Incyte Corp | Heterociclos tricíclicos para su uso como inhibidores de proteínas BET |
| AU2015326910B2 (en) * | 2014-10-02 | 2018-03-01 | Glaxosmithkline Intellectual Property (No.2) Limited | Compound |
| US10179125B2 (en) | 2014-12-01 | 2019-01-15 | Zenith Epigenetics Ltd. | Substituted pyridines as bromodomain inhibitors |
| US10710992B2 (en) | 2014-12-01 | 2020-07-14 | Zenith Epigenetics Ltd. | Substituted pyridinones as bromodomain inhibitors |
| US10292968B2 (en) | 2014-12-11 | 2019-05-21 | Zenith Epigenetics Ltd. | Substituted heterocycles as bromodomain inhibitors |
| WO2016097863A1 (en) | 2014-12-17 | 2016-06-23 | Zenith Epigenetics Corp. | Inhibitors of bromodomains |
| AU2016232705C1 (en) | 2015-03-18 | 2021-06-17 | Arvinas, Inc. | Compounds and methods for the enhanced degradation of targeted proteins |
| GB201504694D0 (en) | 2015-03-19 | 2015-05-06 | Glaxosmithkline Ip Dev Ltd | Covalent conjugates |
| WO2016183114A1 (en) * | 2015-05-11 | 2016-11-17 | Bristol-Myers Squibb Company | Tricyclic compounds as anticancer agents |
| EP3307740B1 (en) * | 2015-05-12 | 2019-12-18 | Bristol-Myers Squibb Company | 5h-pyrido[3,2-b]indole compounds as anticancer agents |
| US9725449B2 (en) * | 2015-05-12 | 2017-08-08 | Bristol-Myers Squibb Company | Tricyclic compounds as anticancer agents |
| WO2017030814A1 (en) | 2015-08-19 | 2017-02-23 | Arvinas, Inc. | Compounds and methods for the targeted degradation of bromodomain-containing proteins |
| US20170121347A1 (en) | 2015-10-29 | 2017-05-04 | Incyte Corporation | Amorphous solid form of a bet protein inhibitor |
| 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 |
| EP3436006B1 (en) | 2016-03-30 | 2025-07-30 | Wisconsin Alumni Research Foundation | Methods and compositions for modulating frataxin expression |
| DK3472157T3 (da) | 2016-06-20 | 2023-05-01 | Incyte Corp | Krystallinske faste former af en bet-inhibitor |
| JP2020506922A (ja) | 2017-01-31 | 2020-03-05 | アルビナス・オペレーションズ・インコーポレイテッドＡｒｖｉｎａｓ Ｏｐｅｒａｔｉｏｎｓ， Ｉｎｃ． | セレブロンリガンド、およびセレブロンリガンドを含有する二官能性化合物 |
| WO2018183679A1 (en) | 2017-03-29 | 2018-10-04 | Wisconsin Alumni Research Foundation | Methods and compositions for modulating gene expression |
| JP2021512153A (ja) | 2018-01-26 | 2021-05-13 | イエール ユニバーシティ | タンパク質分解のイミド系モジュレーターおよび使用方法 |
| CR20220353A (es) | 2019-12-19 | 2022-10-20 | Arvinas Operations Inc | Compuestos y métodos para la degradación dirigida del receptor de andrógenos |
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| CN111809182B (zh) * | 2020-07-08 | 2025-04-18 | 江苏和达电子科技有限公司 | 一种用于铜/钼（铌）/igzo膜层的刻蚀液及其制备方法和应用 |
| US12016847B2 (en) | 2021-03-12 | 2024-06-25 | Bristol-Myers Squibb Company | Methods of treating prostate cancer |
| EP4525863A1 (en) * | 2022-05-20 | 2025-03-26 | University Of Puerto Rico | 1,4,5-trisubstituted-1,2,3-triazoles and uses thereof |
| WO2025049555A1 (en) | 2023-08-31 | 2025-03-06 | Oerth Bio Llc | Compositions and methods for targeted inhibition and degradation of proteins in an insect cell |
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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 |
| DE60130891T2 (de) * | 2000-06-29 | 2008-07-17 | Anthera Pharmaceuticals Inc., San Mateo | Heilmittel für krebs |
| US6933313B2 (en) * | 2001-03-28 | 2005-08-23 | Eli Lilly And Company | Substituted carbazoles as inhibitors of sPLA2 |
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| EP1677786A1 (en) | 2003-10-18 | 2006-07-12 | Bayer HealthCare AG | 5-substituted 2-(phenylmethyl)thio-4-phenyl-4h-1,2,4-triazole derivatives and related compounds as gaba-agonists for the treatment of urinary incontinence and related diseases |
| WO2006012310A2 (en) * | 2004-06-25 | 2006-02-02 | Genzyme Corporation | Carbazole derivatives for treating polycystic kidney disease |
| EP2370407B1 (en) * | 2008-12-19 | 2014-06-18 | Bristol-Myers Squibb Company | Carbazole and carboline kinase inhibitors |
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| CA2796967C (en) | 2010-05-04 | 2015-12-01 | Pfizer Inc. | Heterocyclic derivatives as alk inhibitors |
| JP5623996B2 (ja) | 2010-09-21 | 2014-11-12 | 株式会社半導体エネルギー研究所 | カルバゾール誘導体 |
| 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 |
| EP2694619A4 (en) * | 2011-05-03 | 2014-10-22 | Rohm & Haas Elect Mat | NEW ORGANIC ELECTROLUMINESCENSE COMPOUNDS AND ORGANIC ELECTROLUMINESCENCE DEVICE THEREWITH |
| UA115576C2 (uk) * | 2012-12-06 | 2017-11-27 | Байєр Фарма Акцієнгезелльшафт | Похідні бензимідазолу як антагоністи ер4 |
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- 2014-02-27 WO PCT/US2014/018820 patent/WO2014134232A1/en not_active Ceased
- 2014-02-27 MX MX2015010921A patent/MX2015010921A/es unknown
- 2014-02-27 BR BR112015020389A patent/BR112015020389A8/pt not_active Application Discontinuation
- 2014-02-27 JP JP2015560285A patent/JP6395731B2/ja active Active
- 2014-02-27 ES ES14712815.1T patent/ES2669189T3/es active Active
- 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
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