CA2769151A1 - 5,6-bicyclic heteroaryl-containing urea compounds as kinase inhibitors - Google Patents

Info

Publication number

CA2769151A1

CA2769151A1 CA2769151A CA2769151A CA2769151A1 CA 2769151 A1 CA2769151 A1 CA 2769151A1 CA 2769151 A CA2769151 A CA 2769151A CA 2769151 A CA2769151 A CA 2769151A CA 2769151 A1 CA2769151 A1 CA 2769151A1

Authority

CA

Canada

Prior art keywords

indol

pyrrolo

urea

ylmethyl

pyridin

Prior art date

2009-08-24

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

• 150000003672 ureas Chemical class 0.000 title abstract 2
• 229940043355 kinase inhibitor Drugs 0.000 title description 4
• 239000003757 phosphotransferase inhibitor Substances 0.000 title description 4
• -1 CSFlR Proteins 0.000 claims abstract description 83
• 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 claims abstract description 36
• 101000851007 Homo sapiens Vascular endothelial growth factor receptor 2 Proteins 0.000 claims abstract description 33
• 102000001253 Protein Kinase Human genes 0.000 claims abstract description 18
• 108060006633 protein kinase Proteins 0.000 claims abstract description 18
• 102000016971 Proto-Oncogene Proteins c-kit Human genes 0.000 claims abstract description 15
• 108010014608 Proto-Oncogene Proteins c-kit Proteins 0.000 claims abstract description 15
• 102100030340 Ephrin type-A receptor 2 Human genes 0.000 claims abstract description 9
• 230000001404 mediated effect Effects 0.000 claims abstract description 9
• 108010055196 EphA2 Receptor Proteins 0.000 claims abstract description 7
• 150000001875 compounds Chemical class 0.000 claims description 173
• XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 97
• 206010028980 Neoplasm Diseases 0.000 claims description 50
• 239000004202 carbamide Substances 0.000 claims description 50
• 101000692455 Homo sapiens Platelet-derived growth factor receptor beta Proteins 0.000 claims description 29
• 102100026547 Platelet-derived growth factor receptor beta Human genes 0.000 claims description 29
• 125000000217 alkyl group Chemical group 0.000 claims description 29
• 125000003118 aryl group Chemical group 0.000 claims description 24
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 24
• 125000001072 heteroaryl group Chemical group 0.000 claims description 22
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
• 229910052757 nitrogen Inorganic materials 0.000 claims description 19
• 125000003342 alkenyl group Chemical group 0.000 claims description 16
• 125000005843 halogen group Chemical group 0.000 claims description 16
• 125000000304 alkynyl group Chemical group 0.000 claims description 15
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
• 125000002947 alkylene group Chemical group 0.000 claims description 14
• 150000003839 salts Chemical class 0.000 claims description 14
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
• LMFQUIVPCZHCPE-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)indol-4-yl]urea Chemical compound ClC1=CC=CC(NC(=O)NC=2C=3C=CN(CC=4C5=CC=CN=C5NC=4)C=3C=CC=2)=C1 LMFQUIVPCZHCPE-UHFFFAOYSA-N 0.000 claims description 12
• NEWQDFYRXAIOKV-UHFFFAOYSA-N 1-(3-cyanophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)indol-4-yl]urea Chemical compound C=1C=CC=2N(CC=3C=4C=CNC=4N=CC=3)C=CC=2C=1NC(=O)NC1=CC=CC(C#N)=C1 NEWQDFYRXAIOKV-UHFFFAOYSA-N 0.000 claims description 12
• HGAYDCRXKTWTAR-UHFFFAOYSA-N 1-(4-bromophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)indol-4-yl]urea Chemical compound C1=CC(Br)=CC=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CNC2=NC=CC=C12 HGAYDCRXKTWTAR-UHFFFAOYSA-N 0.000 claims description 12
• OADXSZAOHSDTIM-UHFFFAOYSA-N 1-(5-bromo-2-fluorophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)indol-4-yl]urea Chemical compound FC1=CC=C(Br)C=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CC=NC2=C1C=CN2 OADXSZAOHSDTIM-UHFFFAOYSA-N 0.000 claims description 12
• GOMYZJSYQNBNEZ-UHFFFAOYSA-N 1-(5-chloro-2-methoxyphenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)indol-4-yl]urea Chemical compound COC1=CC=C(Cl)C=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CC=NC2=C1C=CN2 GOMYZJSYQNBNEZ-UHFFFAOYSA-N 0.000 claims description 12
• NYVMOJYFOQUJRU-UHFFFAOYSA-N 1-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)indol-4-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C=3C=CN(CC=4C=5C=CNC=5N=CC=4)C=3C=CC=2)=C1 NYVMOJYFOQUJRU-UHFFFAOYSA-N 0.000 claims description 12
• CUWPZMAJAWALTC-UHFFFAOYSA-N 1-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)indol-4-yl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound C1=CC(C(F)(F)F)=CC=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CC=NC2=C1C=CN2 CUWPZMAJAWALTC-UHFFFAOYSA-N 0.000 claims description 12
• BTUMMBFNYNCTCY-UHFFFAOYSA-N 1-(2-fluorophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)indol-4-yl]urea Chemical compound FC1=CC=CC=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CNC2=NC=CC=C12 BTUMMBFNYNCTCY-UHFFFAOYSA-N 0.000 claims description 11
• HPFCMGWXOHGIMZ-UHFFFAOYSA-N 1-(3-cyanophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)indol-4-yl]urea Chemical compound C=1C=CC=2N(CC=3C4=CC=CN=C4NC=3)C=CC=2C=1NC(=O)NC1=CC=CC(C#N)=C1 HPFCMGWXOHGIMZ-UHFFFAOYSA-N 0.000 claims description 11
• HJHGQOIQVQXOFJ-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)indol-4-yl]urea Chemical compound C1=CC(F)=CC=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CC=NC2=C1C=CN2 HJHGQOIQVQXOFJ-UHFFFAOYSA-N 0.000 claims description 11
• CCSWRSNLOHOYGM-UHFFFAOYSA-N 1-(5-bromo-2-fluorophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)indol-4-yl]urea Chemical compound FC1=CC=C(Br)C=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CNC2=NC=CC=C12 CCSWRSNLOHOYGM-UHFFFAOYSA-N 0.000 claims description 11
• JRUKTWJJCBRWAE-UHFFFAOYSA-N 1-(5-chloro-2-methoxyphenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)indol-4-yl]urea Chemical compound COC1=CC=C(Cl)C=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CNC2=NC=CC=C12 JRUKTWJJCBRWAE-UHFFFAOYSA-N 0.000 claims description 11
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 11
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
• BPJVUSNCWPYXEV-UHFFFAOYSA-N 1-(2-chlorophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)indol-4-yl]urea Chemical compound ClC1=CC=CC=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CC=NC2=C1C=CN2 BPJVUSNCWPYXEV-UHFFFAOYSA-N 0.000 claims description 10
• TZJTWAKKFJOUAI-UHFFFAOYSA-N 1-(2-fluorophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)indol-4-yl]urea Chemical compound FC1=CC=CC=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CC=NC2=C1C=CN2 TZJTWAKKFJOUAI-UHFFFAOYSA-N 0.000 claims description 10
• HFVGNHXODSVGQJ-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)indol-4-yl]urea Chemical compound ClC1=CC=CC(NC(=O)NC=2C=3C=CN(CC=4C=5C=CNC=5N=CC=4)C=3C=CC=2)=C1 HFVGNHXODSVGQJ-UHFFFAOYSA-N 0.000 claims description 10
• GBVUPGLFOOANPY-UHFFFAOYSA-N 1-(3-fluorophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)indol-4-yl]urea Chemical compound FC1=CC=CC(NC(=O)NC=2C=3C=CN(CC=4C=5C=CNC=5N=CC=4)C=3C=CC=2)=C1 GBVUPGLFOOANPY-UHFFFAOYSA-N 0.000 claims description 10
• GFJCMZYJYNPTJO-UHFFFAOYSA-N 1-(4-chloro-2-fluorophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)indol-4-yl]urea Chemical compound FC1=CC(Cl)=CC=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CC=NC2=C1C=CN2 GFJCMZYJYNPTJO-UHFFFAOYSA-N 0.000 claims description 10
• VHHFAAMLVRYQRK-UHFFFAOYSA-N 1-(5-chloro-2-fluorophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)indol-4-yl]urea Chemical compound FC1=CC=C(Cl)C=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CC=NC2=C1C=CN2 VHHFAAMLVRYQRK-UHFFFAOYSA-N 0.000 claims description 10
• 125000004043 oxo group Chemical group O=* 0.000 claims description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
• 239000005441 aurora Substances 0.000 claims description 8
• 229910052720 vanadium Inorganic materials 0.000 claims description 8
• 208000023275 Autoimmune disease Diseases 0.000 claims description 7
• 102100028198 Macrophage colony-stimulating factor 1 receptor Human genes 0.000 claims description 7
• 208000002780 macular degeneration Diseases 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• 229920006395 saturated elastomer Polymers 0.000 claims description 7
• WQHIMZBISJFLOE-UHFFFAOYSA-N 1-(3-methylphenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)indol-4-yl]urea Chemical compound CC1=CC=CC(NC(=O)NC=2C=3C=CN(CC=4C=5C=CNC=5N=CC=4)C=3C=CC=2)=C1 WQHIMZBISJFLOE-UHFFFAOYSA-N 0.000 claims description 6
• 101100481408 Danio rerio tie2 gene Proteins 0.000 claims description 6
• 101100481410 Mus musculus Tek gene Proteins 0.000 claims description 6
• 201000004681 Psoriasis Diseases 0.000 claims description 6
• 229910052770 Uranium Inorganic materials 0.000 claims description 6
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
• 239000003814 drug Substances 0.000 claims description 6
• 125000005842 heteroatom Chemical group 0.000 claims description 6
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 6
• 238000002360 preparation method Methods 0.000 claims description 6
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
• ISHXFPIANRKVQL-UHFFFAOYSA-N 1-(2-fluoro-5-methoxyphenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)indol-4-yl]urea Chemical compound COC1=CC=C(F)C(NC(=O)NC=2C=3C=CN(CC=4C5=CC=CN=C5NC=4)C=3C=CC=2)=C1 ISHXFPIANRKVQL-UHFFFAOYSA-N 0.000 claims description 5
• YBLUYHUBOJNELT-UHFFFAOYSA-N 1-(3-methylphenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)indol-4-yl]urea Chemical compound CC1=CC=CC(NC(=O)NC=2C=3C=CN(CC=4C5=CC=CN=C5NC=4)C=3C=CC=2)=C1 YBLUYHUBOJNELT-UHFFFAOYSA-N 0.000 claims description 5
• LKRRNTPYYOYTTC-UHFFFAOYSA-N 1-(5-chloro-2-methoxyphenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)-2,3-dihydroindol-4-yl]urea Chemical compound COC1=CC=C(Cl)C=C1NC(=O)NC1=CC=CC2=C1CCN2CC1=CC=NC2=C1C=CN2 LKRRNTPYYOYTTC-UHFFFAOYSA-N 0.000 claims description 5
• 101000916644 Homo sapiens Macrophage colony-stimulating factor 1 receptor Proteins 0.000 claims description 5
• 208000038016 acute inflammation Diseases 0.000 claims description 5
• 230000006022 acute inflammation Effects 0.000 claims description 5
• 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 claims description 5
• 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 claims description 5
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 5
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
• YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 claims description 5
• FBIWFINTOBOZJS-UHFFFAOYSA-N 1-(2,5-dimethoxyphenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)indol-4-yl]urea Chemical compound COC1=CC=C(OC)C(NC(=O)NC=2C=3C=CN(CC=4C5=CC=CN=C5NC=4)C=3C=CC=2)=C1 FBIWFINTOBOZJS-UHFFFAOYSA-N 0.000 claims description 4
• OCHDYCZRGUQBQD-UHFFFAOYSA-N 1-(2-bromo-5-methylphenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)indol-4-yl]urea Chemical compound CC1=CC=C(Br)C(NC(=O)NC=2C=3C=CN(CC=4C=5C=CNC=5N=CC=4)C=3C=CC=2)=C1 OCHDYCZRGUQBQD-UHFFFAOYSA-N 0.000 claims description 4
• VQKDCIDRDIQIJX-UHFFFAOYSA-N 1-(2-bromophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)indol-4-yl]urea Chemical compound BrC1=CC=CC=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CNC2=NC=CC=C12 VQKDCIDRDIQIJX-UHFFFAOYSA-N 0.000 claims description 4
• HWYMNTDGBLBTRQ-UHFFFAOYSA-N 1-(2-bromophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)indol-4-yl]urea Chemical compound BrC1=CC=CC=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CC=NC2=C1C=CN2 HWYMNTDGBLBTRQ-UHFFFAOYSA-N 0.000 claims description 4
• CIYZHXAVRFDSEJ-UHFFFAOYSA-N 1-(2-chlorophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)indol-4-yl]urea Chemical compound ClC1=CC=CC=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CNC2=NC=CC=C12 CIYZHXAVRFDSEJ-UHFFFAOYSA-N 0.000 claims description 4
• JWQUYZVFHRTCIP-UHFFFAOYSA-N 1-(2-methoxyphenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)indol-4-yl]urea Chemical compound COC1=CC=CC=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CNC2=NC=CC=C12 JWQUYZVFHRTCIP-UHFFFAOYSA-N 0.000 claims description 4
• QEWZQECXUSGQMM-UHFFFAOYSA-N 1-(2-methoxyphenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)indol-4-yl]urea Chemical compound COC1=CC=CC=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CC=NC2=C1C=CN2 QEWZQECXUSGQMM-UHFFFAOYSA-N 0.000 claims description 4
• ALXXKEHBATXOKX-UHFFFAOYSA-N 1-(3-bromophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)indol-4-yl]urea Chemical compound BrC1=CC=CC(NC(=O)NC=2C=3C=CN(CC=4C5=CC=CN=C5NC=4)C=3C=CC=2)=C1 ALXXKEHBATXOKX-UHFFFAOYSA-N 0.000 claims description 4
• HZIHJQLTQPYNLO-UHFFFAOYSA-N 1-(3-bromophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)indol-4-yl]urea Chemical compound BrC1=CC=CC(NC(=O)NC=2C=3C=CN(CC=4C=5C=CNC=5N=CC=4)C=3C=CC=2)=C1 HZIHJQLTQPYNLO-UHFFFAOYSA-N 0.000 claims description 4
• LDKDNIPHSKYVQW-UHFFFAOYSA-N 1-(3-fluoro-2-methylphenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)indol-4-yl]urea Chemical compound CC1=C(F)C=CC=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CC=NC2=C1C=CN2 LDKDNIPHSKYVQW-UHFFFAOYSA-N 0.000 claims description 4
• PJUNPWHHCBNLOQ-UHFFFAOYSA-N 1-(3-fluorophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)indol-4-yl]urea Chemical compound FC1=CC=CC(NC(=O)NC=2C=3C=CN(CC=4C5=CC=CN=C5NC=4)C=3C=CC=2)=C1 PJUNPWHHCBNLOQ-UHFFFAOYSA-N 0.000 claims description 4
• HTHTYDOPEXUVLL-UHFFFAOYSA-N 1-(4-bromophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)indol-4-yl]urea Chemical compound C1=CC(Br)=CC=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CC=NC2=C1C=CN2 HTHTYDOPEXUVLL-UHFFFAOYSA-N 0.000 claims description 4
• KJWAARPVVSXUSP-UHFFFAOYSA-N 1-(4-chloro-2-fluorophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)indol-4-yl]urea Chemical compound FC1=CC(Cl)=CC=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CNC2=NC=CC=C12 KJWAARPVVSXUSP-UHFFFAOYSA-N 0.000 claims description 4
• LNVGQZWLGXGZEL-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)indol-4-yl]urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CNC2=NC=CC=C12 LNVGQZWLGXGZEL-UHFFFAOYSA-N 0.000 claims description 4
• CBJNVMUDFCPBBG-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)indol-4-yl]urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CC=NC2=C1C=CN2 CBJNVMUDFCPBBG-UHFFFAOYSA-N 0.000 claims description 4
• HAMFLSMICPKYRW-UHFFFAOYSA-N 1-(4-cyanophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)indol-4-yl]urea Chemical compound C=1C=CC=2N(CC=3C4=CC=CN=C4NC=3)C=CC=2C=1NC(=O)NC1=CC=C(C#N)C=C1 HAMFLSMICPKYRW-UHFFFAOYSA-N 0.000 claims description 4
• QQDWBYZAEWFOBG-UHFFFAOYSA-N 1-(4-cyanophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)indol-4-yl]urea Chemical compound C=1C=CC=2N(CC=3C=4C=CNC=4N=CC=3)C=CC=2C=1NC(=O)NC1=CC=C(C#N)C=C1 QQDWBYZAEWFOBG-UHFFFAOYSA-N 0.000 claims description 4
• NGEVCHBCXYWWSJ-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)indol-4-yl]urea Chemical compound C1=CC(F)=CC=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CNC2=NC=CC=C12 NGEVCHBCXYWWSJ-UHFFFAOYSA-N 0.000 claims description 4
• XCEKREIPMPZQHH-UHFFFAOYSA-N 1-(4-methylphenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)indol-4-yl]urea Chemical compound C1=CC(C)=CC=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CC=NC2=C1C=CN2 XCEKREIPMPZQHH-UHFFFAOYSA-N 0.000 claims description 4
• SXEIDLNEGHHSNI-UHFFFAOYSA-N 1-(5-chloro-2-fluorophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)indol-4-yl]urea Chemical compound FC1=CC=C(Cl)C=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CNC2=NC=CC=C12 SXEIDLNEGHHSNI-UHFFFAOYSA-N 0.000 claims description 4
• WGKKYMUQVIMYCX-UHFFFAOYSA-N 1-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)indol-4-yl]-3-[2-(trifluoromethoxy)phenyl]urea Chemical compound FC(F)(F)OC1=CC=CC=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CNC2=NC=CC=C12 WGKKYMUQVIMYCX-UHFFFAOYSA-N 0.000 claims description 4
• RSVKEOAFDKPPJT-UHFFFAOYSA-N 1-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)indol-4-yl]-3-[2-(trifluoromethyl)phenyl]urea Chemical compound FC(F)(F)C1=CC=CC=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CNC2=NC=CC=C12 RSVKEOAFDKPPJT-UHFFFAOYSA-N 0.000 claims description 4
• BZOIVUFYQSMAQR-UHFFFAOYSA-N 1-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)indol-4-yl]-3-[3-(trifluoromethoxy)phenyl]urea Chemical compound FC(F)(F)OC1=CC=CC(NC(=O)NC=2C=3C=CN(CC=4C5=CC=CN=C5NC=4)C=3C=CC=2)=C1 BZOIVUFYQSMAQR-UHFFFAOYSA-N 0.000 claims description 4
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• WNYOBSRTOURYPN-UHFFFAOYSA-N 1-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)indol-4-yl]-3-[4-(trifluoromethoxy)phenyl]urea Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CNC2=NC=CC=C12 WNYOBSRTOURYPN-UHFFFAOYSA-N 0.000 claims description 4
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• JQOKCHRBIGMIRC-UHFFFAOYSA-N 1-(3-bromophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)-2,3-dihydroindol-4-yl]urea Chemical compound BrC1=CC=CC(NC(=O)NC=2C=3CCN(CC=4C5=CC=CN=C5NC=4)C=3C=CC=2)=C1 JQOKCHRBIGMIRC-UHFFFAOYSA-N 0.000 claims description 2
• PZUODWGRDIMFSM-UHFFFAOYSA-N 1-(3-bromophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)-2,3-dihydroindol-4-yl]urea Chemical compound BrC1=CC=CC(NC(=O)NC=2C=3CCN(CC=4C=5C=CNC=5N=CC=4)C=3C=CC=2)=C1 PZUODWGRDIMFSM-UHFFFAOYSA-N 0.000 claims description 2
• MIHVJAOXGOEBLG-UHFFFAOYSA-N 1-(3-chloro-2-methylphenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)indol-4-yl]urea Chemical compound CC1=C(Cl)C=CC=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CNC2=NC=CC=C12 MIHVJAOXGOEBLG-UHFFFAOYSA-N 0.000 claims description 2
• CWPVEQJFBDIFRG-UHFFFAOYSA-N 1-(3-chloro-2-methylphenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)indol-4-yl]urea Chemical compound CC1=C(Cl)C=CC=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CC=NC2=C1C=CN2 CWPVEQJFBDIFRG-UHFFFAOYSA-N 0.000 claims description 2
• KHVZNPVZZACBSL-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)-2,3-dihydroindol-4-yl]urea Chemical compound ClC1=CC=CC(NC(=O)NC=2C=3CCN(CC=4C5=CC=CN=C5NC=4)C=3C=CC=2)=C1 KHVZNPVZZACBSL-UHFFFAOYSA-N 0.000 claims description 2
• LDNJYRUUUPNPGG-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)-2,3-dihydroindol-4-yl]urea Chemical compound ClC1=CC=CC(NC(=O)NC=2C=3CCN(CC=4C=5C=CNC=5N=CC=4)C=3C=CC=2)=C1 LDNJYRUUUPNPGG-UHFFFAOYSA-N 0.000 claims description 2
• BZCNDHWCSSXFLO-UHFFFAOYSA-N 1-(3-cyanophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)-2,3-dihydroindol-4-yl]urea Chemical compound C=1C=CC=2N(CC=3C4=CC=CN=C4NC=3)CCC=2C=1NC(=O)NC1=CC=CC(C#N)=C1 BZCNDHWCSSXFLO-UHFFFAOYSA-N 0.000 claims description 2
• HOJWYIORFIYEIQ-UHFFFAOYSA-N 1-(3-cyanophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)-2,3-dihydroindol-4-yl]urea Chemical compound C=1C=CC=2N(CC=3C=4C=CNC=4N=CC=3)CCC=2C=1NC(=O)NC1=CC=CC(C#N)=C1 HOJWYIORFIYEIQ-UHFFFAOYSA-N 0.000 claims description 2
• DRMPQWCVWNZYQX-UHFFFAOYSA-N 1-(3-fluoro-2-methylphenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)indol-4-yl]urea Chemical compound CC1=C(F)C=CC=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CNC2=NC=CC=C12 DRMPQWCVWNZYQX-UHFFFAOYSA-N 0.000 claims description 2
• DYQYIPMHUMZQED-UHFFFAOYSA-N 1-(3-fluorophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)-2,3-dihydroindol-4-yl]urea Chemical compound FC1=CC=CC(NC(=O)NC=2C=3CCN(CC=4C5=CC=CN=C5NC=4)C=3C=CC=2)=C1 DYQYIPMHUMZQED-UHFFFAOYSA-N 0.000 claims description 2
• OPJRQDWNHYYOGT-UHFFFAOYSA-N 1-(3-fluorophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)-2,3-dihydroindol-4-yl]urea Chemical compound FC1=CC=CC(NC(=O)NC=2C=3CCN(CC=4C=5C=CNC=5N=CC=4)C=3C=CC=2)=C1 OPJRQDWNHYYOGT-UHFFFAOYSA-N 0.000 claims description 2
• HFSICMMMGZMGFH-UHFFFAOYSA-N 1-(3-methoxyphenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)indol-4-yl]urea Chemical compound COC1=CC=CC(NC(=O)NC=2C=3C=CN(CC=4C5=CC=CN=C5NC=4)C=3C=CC=2)=C1 HFSICMMMGZMGFH-UHFFFAOYSA-N 0.000 claims description 2
• BJRLKCMQIWHZMK-UHFFFAOYSA-N 1-(4-bromophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)-2,3-dihydroindol-4-yl]urea Chemical compound C1=CC(Br)=CC=C1NC(=O)NC1=CC=CC2=C1CCN2CC1=CNC2=NC=CC=C12 BJRLKCMQIWHZMK-UHFFFAOYSA-N 0.000 claims description 2
• OISANPDASKHVKC-UHFFFAOYSA-N 1-(4-bromophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)-2,3-dihydroindol-4-yl]urea Chemical compound C1=CC(Br)=CC=C1NC(=O)NC1=CC=CC2=C1CCN2CC1=CC=NC2=C1C=CN2 OISANPDASKHVKC-UHFFFAOYSA-N 0.000 claims description 2
• YORIWCJBERKOHI-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)-2,3-dihydroindol-4-yl]urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=CC=CC2=C1CCN2CC1=CNC2=NC=CC=C12 YORIWCJBERKOHI-UHFFFAOYSA-N 0.000 claims description 2
• ZDBCQZLIOBNWRG-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)-2,3-dihydroindol-4-yl]urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=CC=CC2=C1CCN2CC1=CC=NC2=C1C=CN2 ZDBCQZLIOBNWRG-UHFFFAOYSA-N 0.000 claims description 2
• UZGAVKOVNMZDBJ-UHFFFAOYSA-N 1-(4-cyanophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)-2,3-dihydroindol-4-yl]urea Chemical compound C=1C=CC=2N(CC=3C4=CC=CN=C4NC=3)CCC=2C=1NC(=O)NC1=CC=C(C#N)C=C1 UZGAVKOVNMZDBJ-UHFFFAOYSA-N 0.000 claims description 2
• MDNFIVXPRNXQAJ-UHFFFAOYSA-N 1-(4-cyanophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)-2,3-dihydroindol-4-yl]urea Chemical compound C=1C=CC=2N(CC=3C=4C=CNC=4N=CC=3)CCC=2C=1NC(=O)NC1=CC=C(C#N)C=C1 MDNFIVXPRNXQAJ-UHFFFAOYSA-N 0.000 claims description 2
• IOTCTFYHZCMNNX-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)-2,3-dihydroindol-4-yl]urea Chemical compound C1=CC(F)=CC=C1NC(=O)NC1=CC=CC2=C1CCN2CC1=CNC2=NC=CC=C12 IOTCTFYHZCMNNX-UHFFFAOYSA-N 0.000 claims description 2
• SAJXTZODAKDDSW-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)-2,3-dihydroindol-4-yl]urea Chemical compound C1=CC(F)=CC=C1NC(=O)NC1=CC=CC2=C1CCN2CC1=CC=NC2=C1C=CN2 SAJXTZODAKDDSW-UHFFFAOYSA-N 0.000 claims description 2
• FHLIVDVEKXTWNA-UHFFFAOYSA-N 1-(4-methoxyphenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)-2,3-dihydroindol-4-yl]urea Chemical compound C1=CC(OC)=CC=C1NC(=O)NC1=CC=CC2=C1CCN2CC1=CNC2=NC=CC=C12 FHLIVDVEKXTWNA-UHFFFAOYSA-N 0.000 claims description 2
• JMTNZDWUZBNFIG-UHFFFAOYSA-N 1-(4-methoxyphenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)-2,3-dihydroindol-4-yl]urea Chemical compound C1=CC(OC)=CC=C1NC(=O)NC1=CC=CC2=C1CCN2CC1=CC=NC2=C1C=CN2 JMTNZDWUZBNFIG-UHFFFAOYSA-N 0.000 claims description 2
• GBHRTQXMNAEZHQ-UHFFFAOYSA-N 1-(4-methoxyphenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)indol-4-yl]urea Chemical compound C1=CC(OC)=CC=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CC=NC2=C1C=CN2 GBHRTQXMNAEZHQ-UHFFFAOYSA-N 0.000 claims description 2
• PZDXYHOKBYRZCF-UHFFFAOYSA-N 1-(4-methylphenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)-2,3-dihydroindol-4-yl]urea Chemical compound C1=CC(C)=CC=C1NC(=O)NC1=CC=CC2=C1CCN2CC1=CNC2=NC=CC=C12 PZDXYHOKBYRZCF-UHFFFAOYSA-N 0.000 claims description 2
• CIDPDYJDABTBHS-UHFFFAOYSA-N 1-(4-methylphenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)-2,3-dihydroindol-4-yl]urea Chemical compound C1=CC(C)=CC=C1NC(=O)NC1=CC=CC2=C1CCN2CC1=CC=NC2=C1C=CN2 CIDPDYJDABTBHS-UHFFFAOYSA-N 0.000 claims description 2
• JSYLBQPNMLUAKG-UHFFFAOYSA-N 1-(5-bromo-2-fluorophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)-2,3-dihydroindol-4-yl]urea Chemical compound FC1=CC=C(Br)C=C1NC(=O)NC1=CC=CC2=C1CCN2CC1=CNC2=NC=CC=C12 JSYLBQPNMLUAKG-UHFFFAOYSA-N 0.000 claims description 2
• PMHQZXWFKPTXLI-UHFFFAOYSA-N 1-(5-bromo-2-fluorophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)-2,3-dihydroindol-4-yl]urea Chemical compound FC1=CC=C(Br)C=C1NC(=O)NC1=CC=CC2=C1CCN2CC1=CC=NC2=C1C=CN2 PMHQZXWFKPTXLI-UHFFFAOYSA-N 0.000 claims description 2
• FULYJOYGTXHOCB-UHFFFAOYSA-N 1-(5-bromo-2-methoxyphenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)-2,3-dihydroindol-4-yl]urea Chemical compound COC1=CC=C(Br)C=C1NC(=O)NC1=CC=CC2=C1CCN2CC1=CNC2=NC=CC=C12 FULYJOYGTXHOCB-UHFFFAOYSA-N 0.000 claims description 2
• ZEEQXTGBUHLHFK-UHFFFAOYSA-N 1-(5-bromo-2-methoxyphenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)indol-4-yl]urea Chemical compound COC1=CC=C(Br)C=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CNC2=NC=CC=C12 ZEEQXTGBUHLHFK-UHFFFAOYSA-N 0.000 claims description 2
• ZBHUZTDZINNNTC-UHFFFAOYSA-N 1-(5-bromo-2-methoxyphenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)indol-4-yl]urea Chemical compound COC1=CC=C(Br)C=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CC=NC2=C1C=CN2 ZBHUZTDZINNNTC-UHFFFAOYSA-N 0.000 claims description 2
• LSUBPMUMBOMZMP-UHFFFAOYSA-N 1-(5-chloro-2-fluorophenyl)-3-[1-(1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)indol-4-yl]urea 1-[2-fluoro-5-(trifluoromethyl)phenyl]-3-[1-(1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)indol-4-yl]urea Chemical compound FC1=C(C=C(C=C1)Cl)NC(=O)NC1=C2C=CN(C2=CC=C1)CC1=C2C(=NC=C1)NC=C2.FC2=C(C=C(C=C2)C(F)(F)F)NC(=O)NC2=C1C=CN(C1=CC=C2)CC2=C1C(=NC=C2)NC=C1 LSUBPMUMBOMZMP-UHFFFAOYSA-N 0.000 claims description 2
• GPBGCAKOXYCHOH-UHFFFAOYSA-N 1-(5-chloro-2-fluorophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)-2,3-dihydroindol-4-yl]urea Chemical compound FC1=CC=C(Cl)C=C1NC(=O)NC1=CC=CC2=C1CCN2CC1=CNC2=NC=CC=C12 GPBGCAKOXYCHOH-UHFFFAOYSA-N 0.000 claims description 2
• CCQFSTYFHXRJBJ-UHFFFAOYSA-N 1-(5-chloro-2-fluorophenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)-2,3-dihydroindol-4-yl]urea Chemical compound FC1=CC=C(Cl)C=C1NC(=O)NC1=CC=CC2=C1CCN2CC1=CC=NC2=C1C=CN2 CCQFSTYFHXRJBJ-UHFFFAOYSA-N 0.000 claims description 2
• IPEFZDQTXPXJLL-UHFFFAOYSA-N 1-(5-chloro-2-methoxyphenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)-2,3-dihydroindol-4-yl]urea Chemical compound COC1=CC=C(Cl)C=C1NC(=O)NC1=CC=CC2=C1CCN2CC1=CNC2=NC=CC=C12 IPEFZDQTXPXJLL-UHFFFAOYSA-N 0.000 claims description 2
• CGGKAGQYZSIMHN-UHFFFAOYSA-N 1-(5-fluoro-2-methoxyphenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)-2,3-dihydroindol-4-yl]urea Chemical compound COC1=CC=C(F)C=C1NC(=O)NC1=CC=CC2=C1CCN2CC1=CNC2=NC=CC=C12 CGGKAGQYZSIMHN-UHFFFAOYSA-N 0.000 claims description 2
• RFIQSNFPEHFVAD-UHFFFAOYSA-N 1-(5-fluoro-2-methoxyphenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)indol-4-yl]urea Chemical compound COC1=CC=C(F)C=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CNC2=NC=CC=C12 RFIQSNFPEHFVAD-UHFFFAOYSA-N 0.000 claims description 2
• FGMQJLVKKHGKAN-UHFFFAOYSA-N 1-(5-fluoro-2-methoxyphenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)-2,3-dihydroindol-4-yl]urea Chemical compound COC1=CC=C(F)C=C1NC(=O)NC1=CC=CC2=C1CCN2CC1=CC=NC2=C1C=CN2 FGMQJLVKKHGKAN-UHFFFAOYSA-N 0.000 claims description 2
• JHYPPUZRQHGVLH-UHFFFAOYSA-N 1-(5-fluoro-2-methoxyphenyl)-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)indol-4-yl]urea Chemical compound COC1=CC=C(F)C=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CC=NC2=C1C=CN2 JHYPPUZRQHGVLH-UHFFFAOYSA-N 0.000 claims description 2
• JNRGSQDVVCJVLA-UHFFFAOYSA-N 1-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)-2,3-dihydroindol-4-yl]-3-[2-(trifluoromethoxy)phenyl]urea Chemical compound FC(F)(F)OC1=CC=CC=C1NC(=O)NC1=CC=CC2=C1CCN2CC1=CNC2=NC=CC=C12 JNRGSQDVVCJVLA-UHFFFAOYSA-N 0.000 claims description 2
• KDVRROBTCFDYDW-UHFFFAOYSA-N 1-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)-2,3-dihydroindol-4-yl]-3-[3-(trifluoromethoxy)phenyl]urea Chemical compound FC(F)(F)OC1=CC=CC(NC(=O)NC=2C=3CCN(CC=4C5=CC=CN=C5NC=4)C=3C=CC=2)=C1 KDVRROBTCFDYDW-UHFFFAOYSA-N 0.000 claims description 2
• SESZZCLVQVJJRL-UHFFFAOYSA-N 1-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)-2,3-dihydroindol-4-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C=3CCN(CC=4C5=CC=CN=C5NC=4)C=3C=CC=2)=C1 SESZZCLVQVJJRL-UHFFFAOYSA-N 0.000 claims description 2
• JITUCHWYZFJJCY-UHFFFAOYSA-N 1-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)-2,3-dihydroindol-4-yl]-3-[4-(trifluoromethoxy)phenyl]urea Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC1=CC=CC2=C1CCN2CC1=CNC2=NC=CC=C12 JITUCHWYZFJJCY-UHFFFAOYSA-N 0.000 claims description 2
• TZFXKYLNUAFZCQ-UHFFFAOYSA-N 1-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)-2,3-dihydroindol-4-yl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound C1=CC(C(F)(F)F)=CC=C1NC(=O)NC1=CC=CC2=C1CCN2CC1=CNC2=NC=CC=C12 TZFXKYLNUAFZCQ-UHFFFAOYSA-N 0.000 claims description 2
• UGEKHUJLGTUEKU-UHFFFAOYSA-N 1-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)-2,3-dihydroindol-4-yl]-3-[2-(trifluoromethoxy)phenyl]urea Chemical compound FC(F)(F)OC1=CC=CC=C1NC(=O)NC1=CC=CC2=C1CCN2CC1=CC=NC2=C1C=CN2 UGEKHUJLGTUEKU-UHFFFAOYSA-N 0.000 claims description 2
• NCOSQINLLUYQDV-UHFFFAOYSA-N 1-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)-2,3-dihydroindol-4-yl]-3-[2-(trifluoromethyl)phenyl]urea Chemical compound FC(F)(F)C1=CC=CC=C1NC(=O)NC1=CC=CC2=C1CCN2CC1=CC=NC2=C1C=CN2 NCOSQINLLUYQDV-UHFFFAOYSA-N 0.000 claims description 2
• UKILXILXDQNKCG-UHFFFAOYSA-N 1-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)-2,3-dihydroindol-4-yl]-3-[3-(trifluoromethoxy)phenyl]urea Chemical compound FC(F)(F)OC1=CC=CC(NC(=O)NC=2C=3CCN(CC=4C=5C=CNC=5N=CC=4)C=3C=CC=2)=C1 UKILXILXDQNKCG-UHFFFAOYSA-N 0.000 claims description 2
• DIVVSYGITIGVIA-UHFFFAOYSA-N 1-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)-2,3-dihydroindol-4-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C=3CCN(CC=4C=5C=CNC=5N=CC=4)C=3C=CC=2)=C1 DIVVSYGITIGVIA-UHFFFAOYSA-N 0.000 claims description 2
• FHZMLBLVSIACJR-UHFFFAOYSA-N 1-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)-2,3-dihydroindol-4-yl]-3-[4-(trifluoromethoxy)phenyl]urea Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC1=CC=CC2=C1CCN2CC1=CC=NC2=C1C=CN2 FHZMLBLVSIACJR-UHFFFAOYSA-N 0.000 claims description 2
• SVRYDPWJUDYQTO-UHFFFAOYSA-N 1-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)-2,3-dihydroindol-4-yl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound C1=CC(C(F)(F)F)=CC=C1NC(=O)NC1=CC=CC2=C1CCN2CC1=CC=NC2=C1C=CN2 SVRYDPWJUDYQTO-UHFFFAOYSA-N 0.000 claims description 2
• MAIZKQKJEFSXLY-UHFFFAOYSA-N 1-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)indol-4-yl]-3-[3-(trifluoromethoxy)phenyl]urea Chemical compound FC(F)(F)OC1=CC=CC(NC(=O)NC=2C=3C=CN(CC=4C=5C=CNC=5N=CC=4)C=3C=CC=2)=C1 MAIZKQKJEFSXLY-UHFFFAOYSA-N 0.000 claims description 2
• BLDGLNHLRHLTOT-UHFFFAOYSA-N 1-[2-fluoro-5-(trifluoromethyl)phenyl]-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)-2,3-dihydroindol-4-yl]urea Chemical compound FC1=CC=C(C(F)(F)F)C=C1NC(=O)NC1=CC=CC2=C1CCN2CC1=CNC2=NC=CC=C12 BLDGLNHLRHLTOT-UHFFFAOYSA-N 0.000 claims description 2
• USMRKYPTOCEPLG-UHFFFAOYSA-N 1-[2-fluoro-5-(trifluoromethyl)phenyl]-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)indol-4-yl]urea Chemical compound FC1=CC=C(C(F)(F)F)C=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CNC2=NC=CC=C12 USMRKYPTOCEPLG-UHFFFAOYSA-N 0.000 claims description 2
• SOMYWRCZDMWNRK-UHFFFAOYSA-N 1-[2-fluoro-5-(trifluoromethyl)phenyl]-3-[1-(1h-pyrrolo[2,3-b]pyridin-4-ylmethyl)-2,3-dihydroindol-4-yl]urea Chemical compound FC1=CC=C(C(F)(F)F)C=C1NC(=O)NC1=CC=CC2=C1CCN2CC1=CC=NC2=C1C=CN2 SOMYWRCZDMWNRK-UHFFFAOYSA-N 0.000 claims description 2
• PWIVORJJNOFZNX-UHFFFAOYSA-N 1-[4-(5-oxopyrrolidin-2-yl)phenyl]-3-[1-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)-2,3-dihydroindol-4-yl]urea Chemical compound C=1C=CC=2N(CC=3C4=CC=CN=C4NC=3)CCC=2C=1NC(=O)NC(C=C1)=CC=C1C1CCC(=O)N1 PWIVORJJNOFZNX-UHFFFAOYSA-N 0.000 claims description 2
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