CA2635899A1 - Fused heterobicyclic kinase inhibitors - Google Patents

Info

Publication number

CA2635899A1

CA2635899A1 CA002635899A CA2635899A CA2635899A1 CA 2635899 A1 CA2635899 A1 CA 2635899A1 CA 002635899 A CA002635899 A CA 002635899A CA 2635899 A CA2635899 A CA 2635899A CA 2635899 A1 CA2635899 A1 CA 2635899A1

Authority

CA

Canada

Prior art keywords

pyrrolo

pyridin

benzyl

phenyl

cr6a

Prior art date

2006-01-19

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 229940043355 kinase inhibitor Drugs 0.000 title description 5
• 239000003757 phosphotransferase inhibitor Substances 0.000 title description 5
• 125000002618 bicyclic heterocycle group Chemical group 0.000 title description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 147
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 66
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 50
• 150000003839 salts Chemical class 0.000 claims abstract description 46
• 201000011510 cancer Diseases 0.000 claims abstract description 38
• 238000011282 treatment Methods 0.000 claims abstract description 30
• 208000006673 asthma Diseases 0.000 claims abstract description 10
• 230000003463 hyperproliferative effect Effects 0.000 claims abstract description 10
• 201000006417 multiple sclerosis Diseases 0.000 claims abstract description 6
• 238000000034 method Methods 0.000 claims description 177
• -1 C0-10alkyl Chemical group 0.000 claims description 142
• 239000000203 mixture Substances 0.000 claims description 53
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 52
• 125000001424 substituent group Chemical group 0.000 claims description 32
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 24
• 125000005843 halogen group Chemical group 0.000 claims description 21
• 229910052757 nitrogen Inorganic materials 0.000 claims description 19
• 208000035475 disorder Diseases 0.000 claims description 14
• 125000005842 heteroatom Chemical group 0.000 claims description 14
• 230000033115 angiogenesis Effects 0.000 claims description 11
• 229910052760 oxygen Inorganic materials 0.000 claims description 11
• 229910052717 sulfur Inorganic materials 0.000 claims description 11
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
• 239000003937 drug carrier Substances 0.000 claims description 10
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 8
• 229910052799 carbon Inorganic materials 0.000 claims description 8
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
• FFILGYUMCLBXEU-UHFFFAOYSA-N 4-(1h-pyrrolo[2,3-b]pyridin-4-yl)aniline Chemical compound C1=CC(N)=CC=C1C1=CC=NC2=C1C=CN2 FFILGYUMCLBXEU-UHFFFAOYSA-N 0.000 claims description 7
• 201000001320 Atherosclerosis Diseases 0.000 claims description 7
• 208000036142 Viral infection Diseases 0.000 claims description 7
• 230000002401 inhibitory effect Effects 0.000 claims description 7
• 229920006395 saturated elastomer Polymers 0.000 claims description 7
• 230000009385 viral infection Effects 0.000 claims description 7
• 206010006187 Breast cancer Diseases 0.000 claims description 6
• 208000026310 Breast neoplasm Diseases 0.000 claims description 6
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
• DKMSFKYTBAROMV-UHFFFAOYSA-N 1-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C1=CC=NC2=C1C=CN2 DKMSFKYTBAROMV-UHFFFAOYSA-N 0.000 claims description 5
• ALPPLOWFWATXSQ-UHFFFAOYSA-N [4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methanamine Chemical compound C1=CC(CN)=CC=C1C1=CC=NC2=C1C=CN2 ALPPLOWFWATXSQ-UHFFFAOYSA-N 0.000 claims description 5
• 239000002246 antineoplastic agent Substances 0.000 claims description 5
• 231100000433 cytotoxic Toxicity 0.000 claims description 5
• 230000001472 cytotoxic effect Effects 0.000 claims description 5
• SJPGGLKQQVIWJB-UHFFFAOYSA-N tert-butyl n-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]carbamate Chemical compound C1=CC(CNC(=O)OC(C)(C)C)=CC=C1C1=CC=NC2=C1C=CN2 SJPGGLKQQVIWJB-UHFFFAOYSA-N 0.000 claims description 5
• LSAAIXBCZXQBIF-CQSZACIVSA-N (2r)-3,3-dimethyl-n-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]butan-2-amine Chemical compound C1=CC(CN[C@H](C)C(C)(C)C)=CC=C1C1=CC=NC2=C1C=CN2 LSAAIXBCZXQBIF-CQSZACIVSA-N 0.000 claims description 4
• JBOWFZLIHYJIJV-UHFFFAOYSA-N 1-(2-fluorophenyl)-n-[[5-(1h-pyrrolo[2,3-b]pyridin-4-yl)thiophen-2-yl]methyl]methanamine Chemical compound FC1=CC=CC=C1CNCC1=CC=C(C=2C=3C=CNC=3N=CC=2)S1 JBOWFZLIHYJIJV-UHFFFAOYSA-N 0.000 claims description 4
• SHYZHDIDMSOIML-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]urea Chemical compound C1=CC(F)=CC=C1NC(=O)NC1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 SHYZHDIDMSOIML-UHFFFAOYSA-N 0.000 claims description 4
• QBRLCNKHXUBHAE-UHFFFAOYSA-N 1-[(3-fluorophenyl)methyl]-3-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]urea Chemical compound FC1=CC=CC(CNC(=O)NC=2C=CC(=CC=2)C=2C=3C=CNC=3N=CC=2)=C1 QBRLCNKHXUBHAE-UHFFFAOYSA-N 0.000 claims description 4
• HRYWBCMSSNOADX-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]-3-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]urea Chemical compound C1=CC(F)=CC=C1CNC(=O)NC1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 HRYWBCMSSNOADX-UHFFFAOYSA-N 0.000 claims description 4
• DHOBCFVLDNCPTP-UHFFFAOYSA-N 1-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]-n-(thiophen-2-ylmethyl)methanamine Chemical compound C=1C=C(C=2C=3C=CNC=3N=CC=2)C=CC=1CNCC1=CC=CS1 DHOBCFVLDNCPTP-UHFFFAOYSA-N 0.000 claims description 4
• MSAXTWFJXYJJPF-UHFFFAOYSA-N 1-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CC1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 MSAXTWFJXYJJPF-UHFFFAOYSA-N 0.000 claims description 4
• LEADQZKZEFERGP-UHFFFAOYSA-N 1-phenyl-3-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]urea Chemical compound C=1C=C(C=2C=3C=CNC=3N=CC=2)C=CC=1NC(=O)NC1=CC=CC=C1 LEADQZKZEFERGP-UHFFFAOYSA-N 0.000 claims description 4
• ARECOFLAJIWPKR-UHFFFAOYSA-N 2-methoxy-n-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]ethanamine Chemical compound C1=CC(CNCCOC)=CC=C1C1=CC=NC2=C1C=CN2 ARECOFLAJIWPKR-UHFFFAOYSA-N 0.000 claims description 4
• FJPFKKDTDZRSIR-UHFFFAOYSA-N 4-(1h-pyrrolo[2,3-b]pyridin-4-yl)benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=CC=NC2=C1C=CN2 FJPFKKDTDZRSIR-UHFFFAOYSA-N 0.000 claims description 4
• FVITYDQZVVVEBX-UHFFFAOYSA-N 4-(1h-pyrrolo[2,3-b]pyridin-4-yl)benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=CC=NC2=C1C=CN2 FVITYDQZVVVEBX-UHFFFAOYSA-N 0.000 claims description 4
• JEGODMCUQQRKDA-UHFFFAOYSA-N 4-[4-(1,3-dihydroisoindol-2-ylmethyl)phenyl]-1h-pyrrolo[2,3-b]pyridine Chemical compound C1C2=CC=CC=C2CN1CC(C=C1)=CC=C1C1=CC=NC2=C1C=CN2 JEGODMCUQQRKDA-UHFFFAOYSA-N 0.000 claims description 4
• CGTOIZSPVAUDGG-UHFFFAOYSA-N 4-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]morpholine Chemical compound C1COCCN1C1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 CGTOIZSPVAUDGG-UHFFFAOYSA-N 0.000 claims description 4
• VYEQAVBDBQIUCM-UHFFFAOYSA-N 4-[4-(azocan-1-ylmethyl)phenyl]-1h-pyrrolo[2,3-b]pyridine Chemical compound C=1C=C(C=2C=3C=CNC=3N=CC=2)C=CC=1CN1CCCCCCC1 VYEQAVBDBQIUCM-UHFFFAOYSA-N 0.000 claims description 4
• WAZLMVMZVFZZFF-UHFFFAOYSA-N 4-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-1h-pyrrolo[2,3-b]pyridine Chemical compound C1CN(C)CCN1CC1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 WAZLMVMZVFZZFF-UHFFFAOYSA-N 0.000 claims description 4
• QDOHSHGYFXWVTK-UHFFFAOYSA-N 4-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]morpholine Chemical compound C=1C=C(C=2C=3C=CNC=3N=CC=2)C=CC=1CN1CCOCC1 QDOHSHGYFXWVTK-UHFFFAOYSA-N 0.000 claims description 4
• 208000035143 Bacterial infection Diseases 0.000 claims description 4
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
• 102100022631 Glutamate receptor ionotropic, NMDA 2C Human genes 0.000 claims description 4
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 4
• VJGPPGQUFNKDHH-UHFFFAOYSA-N [3-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methylamino]phenyl]methanol Chemical compound OCC1=CC=CC(NCC=2C=CC(=CC=2)C=2C=3C=CNC=3N=CC=2)=C1 VJGPPGQUFNKDHH-UHFFFAOYSA-N 0.000 claims description 4
• HVCZPJKYIPYOLB-UHFFFAOYSA-N [4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methanol Chemical compound C1=CC(CO)=CC=C1C1=CC=NC2=C1C=CN2 HVCZPJKYIPYOLB-UHFFFAOYSA-N 0.000 claims description 4
• 208000022362 bacterial infectious disease Diseases 0.000 claims description 4
• UCKQSOIWNOHEFH-UHFFFAOYSA-N methyl 3-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methylamino]benzoate Chemical compound COC(=O)C1=CC=CC(NCC=2C=CC(=CC=2)C=2C=3C=CNC=3N=CC=2)=C1 UCKQSOIWNOHEFH-UHFFFAOYSA-N 0.000 claims description 4
• UIENKUKKZRRBSY-UHFFFAOYSA-N methyl 4-(1h-pyrrolo[2,3-b]pyridin-4-yl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=NC2=C1C=CN2 UIENKUKKZRRBSY-UHFFFAOYSA-N 0.000 claims description 4
• YAIXIWGAQYBCKV-UHFFFAOYSA-N n,n-dimethyl-4-(1h-pyrrolo[2,3-b]pyridin-4-yl)benzamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1C1=CC=NC2=C1C=CN2 YAIXIWGAQYBCKV-UHFFFAOYSA-N 0.000 claims description 4
• VSFHSIQLKUBNAY-UHFFFAOYSA-N n-[(2-fluorophenyl)methyl]-4-(1h-pyrrolo[2,3-b]pyridin-4-yl)benzamide Chemical compound FC1=CC=CC=C1CNC(=O)C1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 VSFHSIQLKUBNAY-UHFFFAOYSA-N 0.000 claims description 4
• WQEMMQYBABGANL-UHFFFAOYSA-N n-[(2-fluorophenyl)methyl]-n-methyl-1-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methanamine Chemical compound C=1C=C(C=2C=3C=CNC=3N=CC=2)C=CC=1CN(C)CC1=CC=CC=C1F WQEMMQYBABGANL-UHFFFAOYSA-N 0.000 claims description 4
• QOTZWWCJRNISMJ-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-(1h-pyrrolo[2,3-b]pyridin-4-yl)benzamide Chemical compound C1=CC(F)=CC=C1CNC(=O)C1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 QOTZWWCJRNISMJ-UHFFFAOYSA-N 0.000 claims description 4
• SEDQCRMWPZSILA-UHFFFAOYSA-N n-[2-(4-fluorophenyl)ethyl]-4-(1h-pyrrolo[2,3-b]pyridin-4-yl)benzamide Chemical compound C1=CC(F)=CC=C1CCNC(=O)C1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 SEDQCRMWPZSILA-UHFFFAOYSA-N 0.000 claims description 4
• BYWMDXJKSPNUOT-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-(1h-pyrrolo[2,3-b]pyridin-4-yl)benzamide Chemical compound C1=CC(C(=O)NCCN(C)C)=CC=C1C1=CC=NC2=C1C=CN2 BYWMDXJKSPNUOT-UHFFFAOYSA-N 0.000 claims description 4
• QEUXBJNLUFUYRA-UHFFFAOYSA-N n-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=CC=NC2=C1C=CN2 QEUXBJNLUFUYRA-UHFFFAOYSA-N 0.000 claims description 4
• HFQGJSOHLRSYET-UHFFFAOYSA-N n-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]benzamide Chemical compound C=1C=C(C=2C=3C=CNC=3N=CC=2)C=CC=1NC(=O)C1=CC=CC=C1 HFQGJSOHLRSYET-UHFFFAOYSA-N 0.000 claims description 4
• IFMGHQLFXCZIPH-UHFFFAOYSA-N n-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]benzamide Chemical compound C=1C=C(C=2C=3C=CNC=3N=CC=2)C=CC=1CNC(=O)C1=CC=CC=C1 IFMGHQLFXCZIPH-UHFFFAOYSA-N 0.000 claims description 4
• IWSJDKPOXSMFKM-UHFFFAOYSA-N n-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]cyclopentanamine Chemical compound C=1C=C(C=2C=3C=CNC=3N=CC=2)C=CC=1CNC1CCCC1 IWSJDKPOXSMFKM-UHFFFAOYSA-N 0.000 claims description 4
• TVDGADGRHFSEFF-UHFFFAOYSA-N n-ethyl-4-(1h-pyrrolo[2,3-b]pyridin-4-yl)benzamide Chemical compound C1=CC(C(=O)NCC)=CC=C1C1=CC=NC2=C1C=CN2 TVDGADGRHFSEFF-UHFFFAOYSA-N 0.000 claims description 4
• GMJDYXBSDPZXHN-UHFFFAOYSA-N n-ethyl-n-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]ethanamine Chemical compound C1=CC(CN(CC)CC)=CC=C1C1=CC=NC2=C1C=CN2 GMJDYXBSDPZXHN-UHFFFAOYSA-N 0.000 claims description 4
• LVVXWPYRFQZKIQ-UHFFFAOYSA-N n-methoxy-4-(1h-pyrrolo[2,3-b]pyridin-4-yl)benzamide Chemical compound C1=CC(C(=O)NOC)=CC=C1C1=CC=NC2=C1C=CN2 LVVXWPYRFQZKIQ-UHFFFAOYSA-N 0.000 claims description 4
• XXISXRBDAPWWTF-UHFFFAOYSA-N n-methyl-4-(1h-pyrrolo[2,3-b]pyridin-4-yl)benzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=CC=NC2=C1C=CN2 XXISXRBDAPWWTF-UHFFFAOYSA-N 0.000 claims description 4
• MQRQAMBUVXMCFW-UHFFFAOYSA-N n-phenyl-4-(1h-pyrrolo[2,3-b]pyridin-4-yl)benzamide Chemical compound C=1C=C(C=2C=3C=CNC=3N=CC=2)C=CC=1C(=O)NC1=CC=CC=C1 MQRQAMBUVXMCFW-UHFFFAOYSA-N 0.000 claims description 4
• LUCFQQRSTMLNCA-UHFFFAOYSA-N pyrrolidin-1-yl-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methanone Chemical compound C=1C=C(C=2C=3C=CNC=3N=CC=2)C=CC=1C(=O)N1CCCC1 LUCFQQRSTMLNCA-UHFFFAOYSA-N 0.000 claims description 4
• VWFUKPXNNAEHKC-UHFFFAOYSA-N tert-butyl 4-(1h-pyrrolo[2,3-b]pyridin-4-yl)-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C=2C=3C=CNC=3N=CC=2)=C1 VWFUKPXNNAEHKC-UHFFFAOYSA-N 0.000 claims description 4
• JKMCDHICNZZMFD-UHFFFAOYSA-N tert-butyl n-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1C1=CC=NC2=C1C=CN2 JKMCDHICNZZMFD-UHFFFAOYSA-N 0.000 claims description 4
• 108091008646 testicular receptors Proteins 0.000 claims description 4
• CGNCOVJZQRWUQN-UHFFFAOYSA-N 1-benzyl-3-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]urea Chemical compound C=1C=C(C=2C=3C=CNC=3N=CC=2)C=CC=1NC(=O)NCC1=CC=CC=C1 CGNCOVJZQRWUQN-UHFFFAOYSA-N 0.000 claims description 3
• BNRZNIOJUKNFIO-UHFFFAOYSA-N 2-methoxy-n-(2-methoxyethyl)-n-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]ethanamine Chemical compound C1=CC(CN(CCOC)CCOC)=CC=C1C1=CC=NC2=C1C=CN2 BNRZNIOJUKNFIO-UHFFFAOYSA-N 0.000 claims description 3
• XDQIWAHXYZZLKB-UHFFFAOYSA-N 2-phenyl-n-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]acetamide Chemical compound C=1C=C(C=2C=3C=CNC=3N=CC=2)C=CC=1NC(=O)CC1=CC=CC=C1 XDQIWAHXYZZLKB-UHFFFAOYSA-N 0.000 claims description 3
• AOGGPHNNNOAVJW-UHFFFAOYSA-N 2-phenyl-n-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]propan-2-amine Chemical compound C=1C=C(C=2C=3C=CNC=3N=CC=2)C=CC=1CNC(C)(C)C1=CC=CC=C1 AOGGPHNNNOAVJW-UHFFFAOYSA-N 0.000 claims description 3
• VOPHLJYKEMJYCJ-UHFFFAOYSA-N 2-pyrrolidin-1-yl-n-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]ethanamine Chemical compound C=1C=C(C=2C=3C=CNC=3N=CC=2)C=CC=1CNCCN1CCCC1 VOPHLJYKEMJYCJ-UHFFFAOYSA-N 0.000 claims description 3
• ZASNOVPELXAJLV-UHFFFAOYSA-N 3-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methylamino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NCC=2C=CC(=CC=2)C=2C=3C=CNC=3N=CC=2)=C1 ZASNOVPELXAJLV-UHFFFAOYSA-N 0.000 claims description 3
• ZSMRIWSMVPTAQV-UHFFFAOYSA-N 3-bromo-4-(4-phenylphenyl)-1h-pyrrolo[2,3-b]pyridine Chemical compound C=12C(Br)=CNC2=NC=CC=1C(C=C1)=CC=C1C1=CC=CC=C1 ZSMRIWSMVPTAQV-UHFFFAOYSA-N 0.000 claims description 3
• IQIMIVGEUAMPKB-UHFFFAOYSA-N 3-bromo-4-phenyl-1h-pyrrolo[2,3-b]pyridine Chemical compound C=12C(Br)=CNC2=NC=CC=1C1=CC=CC=C1 IQIMIVGEUAMPKB-UHFFFAOYSA-N 0.000 claims description 3
• POSMXMUTMPXPSP-UHFFFAOYSA-N 3-chloro-4-phenyl-1h-pyrrolo[2,3-b]pyridine Chemical compound C=12C(Cl)=CNC2=NC=CC=1C1=CC=CC=C1 POSMXMUTMPXPSP-UHFFFAOYSA-N 0.000 claims description 3
• QHWSVRLUWHOMMO-UHFFFAOYSA-N 4-(2-fluoro-3-methoxyphenyl)-1h-pyrrolo[2,3-b]pyridine Chemical compound COC1=CC=CC(C=2C=3C=CNC=3N=CC=2)=C1F QHWSVRLUWHOMMO-UHFFFAOYSA-N 0.000 claims description 3
• ZEBGHGKFEHDRKK-UHFFFAOYSA-N 4-(2-fluorophenyl)-1h-pyrrolo[2,3-b]pyridine Chemical compound FC1=CC=CC=C1C1=CC=NC2=C1C=CN2 ZEBGHGKFEHDRKK-UHFFFAOYSA-N 0.000 claims description 3
• JMSMESSLISOXTQ-UHFFFAOYSA-N 4-(3-fluorophenyl)-1h-pyrrolo[2,3-b]pyridine Chemical compound FC1=CC=CC(C=2C=3C=CNC=3N=CC=2)=C1 JMSMESSLISOXTQ-UHFFFAOYSA-N 0.000 claims description 3
• JNKPFYGHHWTGQG-UHFFFAOYSA-N 4-(4-methylphenyl)-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CC(C)=CC=C1C1=CC=NC2=C1C=CN2 JNKPFYGHHWTGQG-UHFFFAOYSA-N 0.000 claims description 3
• 101100516563 Caenorhabditis elegans nhr-6 gene Proteins 0.000 claims description 3
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
• 206010060862 Prostate cancer Diseases 0.000 claims description 3
• 206010052779 Transplant rejections Diseases 0.000 claims description 3
• 125000001153 fluoro group Chemical group F* 0.000 claims description 3
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 3
• 201000005202 lung cancer Diseases 0.000 claims description 3
• 208000020816 lung neoplasm Diseases 0.000 claims description 3
• LLUIHXVYAXKGDO-UHFFFAOYSA-N n-(pyridin-2-ylmethyl)-1-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methanamine Chemical compound C=1C=C(C=2C=3C=CNC=3N=CC=2)C=CC=1CNCC1=CC=CC=N1 LLUIHXVYAXKGDO-UHFFFAOYSA-N 0.000 claims description 3
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