JP2009523812A - 融合へテロ二環式キナーゼ阻害剤 - Google Patents

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Publication number

JP2009523812A

JP2009523812A JP2008551416A JP2008551416A JP2009523812A JP 2009523812 A JP2009523812 A JP 2009523812A JP 2008551416 A JP2008551416 A JP 2008551416A JP 2008551416 A JP2008551416 A JP 2008551416A JP 2009523812 A JP2009523812 A JP 2009523812A

Authority

JP

Japan

Prior art keywords

pyrrolo

pyridin

alkyl

benzyl

phenyl

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.)

Pending

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• 125000002618 bicyclic heterocycle group Chemical group 0.000 title description 4
• 229940043355 kinase inhibitor Drugs 0.000 title description 4
• 239000003757 phosphotransferase inhibitor Substances 0.000 title description 4
• 230000004927 fusion Effects 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 147
• 150000003839 salts Chemical class 0.000 claims abstract description 47
• 201000010099 disease Diseases 0.000 claims abstract description 45
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 45
• 238000011282 treatment Methods 0.000 claims abstract description 29
• 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 5
• 125000000217 alkyl group Chemical group 0.000 claims description 226
• 238000000034 method Methods 0.000 claims description 174
• -1 R 22a Chemical compound 0.000 claims description 153
• 125000000304 alkynyl group Chemical group 0.000 claims description 113
• 125000003342 alkenyl group Chemical group 0.000 claims description 51
• 239000000203 mixture Substances 0.000 claims description 50
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 35
• 125000003545 alkoxy group Chemical group 0.000 claims description 33
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 31
• 125000003118 aryl group Chemical group 0.000 claims description 30
• 125000000623 heterocyclic group Chemical group 0.000 claims description 30
• 125000004414 alkyl thio group Chemical group 0.000 claims description 29
• 125000005843 halogen group Chemical group 0.000 claims description 25
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 24
• 229910052757 nitrogen Inorganic materials 0.000 claims description 19
• 125000001424 substituent group Chemical group 0.000 claims description 18
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 16
• 125000005842 heteroatom Chemical group 0.000 claims description 15
• 125000001072 heteroaryl group Chemical group 0.000 claims description 13
• 229910052760 oxygen Inorganic materials 0.000 claims description 13
• 229910052717 sulfur Inorganic materials 0.000 claims description 12
• 230000033115 angiogenesis Effects 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
• 229920006395 saturated elastomer Polymers 0.000 claims description 10
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
• 201000001320 Atherosclerosis Diseases 0.000 claims description 7
• 208000036142 Viral infection Diseases 0.000 claims description 7
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 230000009385 viral infection Effects 0.000 claims description 7
• 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 6
• 206010006187 Breast cancer Diseases 0.000 claims description 6
• 208000026310 Breast neoplasm Diseases 0.000 claims description 6
• 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 6
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
• 230000002401 inhibitory effect Effects 0.000 claims description 6
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
• 239000002246 antineoplastic agent Substances 0.000 claims description 5
• 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 4
• 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 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
• 206010060862 Prostate cancer Diseases 0.000 claims description 4
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 4
• 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 4
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
• 208000022362 bacterial infectious disease Diseases 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
• ZZEFFMSKXSMLJJ-UHFFFAOYSA-N n-[(2-methoxyphenyl)methyl]-1-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methanamine Chemical compound COC1=CC=CC=C1CNCC1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 ZZEFFMSKXSMLJJ-UHFFFAOYSA-N 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 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 4
• LSAAIXBCZXQBIF-AWEZNQCLSA-N (2s)-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-AWEZNQCLSA-N 0.000 claims description 3
• RIBOCHYWSQMSPG-UHFFFAOYSA-N 1-(2-fluorophenyl)-3-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]urea Chemical compound FC1=CC=CC=C1NC(=O)NC1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 RIBOCHYWSQMSPG-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 3
• WHYZTAZVBTUCOH-UHFFFAOYSA-N 1-(4-methylphenyl)-n-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]methanamine Chemical compound C1=CC(C)=CC=C1CNCC1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 WHYZTAZVBTUCOH-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 3
• 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 3
• GAWDCFGDCVYXBM-UHFFFAOYSA-N 1-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]-n-[[4-(trifluoromethyl)phenyl]methyl]methanamine Chemical compound C1=CC(C(F)(F)F)=CC=C1CNCC1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 GAWDCFGDCVYXBM-UHFFFAOYSA-N 0.000 claims description 3
• LLUCABACISDVEJ-UHFFFAOYSA-N 1-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]ethanol Chemical compound C1=CC(C(O)C)=CC=C1C1=CC=NC2=C1C=CN2 LLUCABACISDVEJ-UHFFFAOYSA-N 0.000 claims description 3
• XYBBXNCSGCKWCF-UHFFFAOYSA-N 1-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]piperidin-3-ol Chemical compound C1C(O)CCCN1CC1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 XYBBXNCSGCKWCF-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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
• 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 3
• MSYBXEOBAGBLFM-UHFFFAOYSA-N 1-phenyl-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=1CNC(C)C1=CC=CC=C1 MSYBXEOBAGBLFM-UHFFFAOYSA-N 0.000 claims description 3
• AOALFLLKUJAMFJ-UHFFFAOYSA-N 1-phenyl-n-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]methanamine Chemical compound C=1C=C(C=2C=3C=CNC=3N=CC=2)C=CC=1CNCC1=CC=CC=C1 AOALFLLKUJAMFJ-UHFFFAOYSA-N 0.000 claims description 3
• LVRUNIIPCOTYHD-UHFFFAOYSA-N 2-(2-fluorophenyl)-n-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]acetamide Chemical compound FC1=CC=CC=C1CC(=O)NC1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 LVRUNIIPCOTYHD-UHFFFAOYSA-N 0.000 claims description 3
• NHHCELHSUFIGDY-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]acetamide Chemical compound C1=CC(F)=CC=C1CC(=O)NC1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 NHHCELHSUFIGDY-UHFFFAOYSA-N 0.000 claims description 3
• NMSIBJORXPUOKW-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]ethanamine Chemical compound C1=CC(F)=CC=C1CCNCC1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 NMSIBJORXPUOKW-UHFFFAOYSA-N 0.000 claims description 3
• YVHWYZNRVTVJDU-UHFFFAOYSA-N 2-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]-3,4-dihydro-1h-isoquinoline Chemical compound C1CC2=CC=CC=C2CN1CC(C=C1)=CC=C1C1=CC=NC2=C1C=CN2 YVHWYZNRVTVJDU-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
• 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 3
• RGBVBBZZZQWGOJ-UHFFFAOYSA-N 2-phenyl-n-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]acetamide Chemical compound C=1C=C(C=2C=3C=CNC=3N=CC=2)C=CC=1CNC(=O)CC1=CC=CC=C1 RGBVBBZZZQWGOJ-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
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• KAWDWMNGQTVNLF-UHFFFAOYSA-N 4-[4-(piperidin-1-ylmethyl)phenyl]-1h-pyrrolo[2,3-b]pyridine Chemical compound C=1C=C(C=2C=3C=CNC=3N=CC=2)C=CC=1CN1CCCCC1 KAWDWMNGQTVNLF-UHFFFAOYSA-N 0.000 claims description 3
• OYXIMFPCANLVPE-UHFFFAOYSA-N 4-[4-(pyrrolidin-1-ylmethyl)phenyl]-1h-pyrrolo[2,3-b]pyridine Chemical compound C=1C=C(C=2C=3C=CNC=3N=CC=2)C=CC=1CN1CCCC1 OYXIMFPCANLVPE-UHFFFAOYSA-N 0.000 claims description 3
• LFWHTAIHAOWRLD-UHFFFAOYSA-N 4-[4-[(4-butylpiperazin-1-yl)methyl]phenyl]-1h-pyrrolo[2,3-b]pyridine Chemical compound C1CN(CCCC)CCN1CC1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 LFWHTAIHAOWRLD-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 3
• CZIVYQYQBGEICQ-UHFFFAOYSA-N 4-fluoro-n-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]aniline Chemical compound C1=CC(F)=CC=C1NCC1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 CZIVYQYQBGEICQ-UHFFFAOYSA-N 0.000 claims description 3
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
• HLQVULNQEAUHCD-UHFFFAOYSA-N [3-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methanamine Chemical compound NCC1=CC=CC(C=2C=3C=CNC=3N=CC=2)=C1 HLQVULNQEAUHCD-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 3
• 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 3
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
• 125000005087 alkynylcarbonyl group Chemical group 0.000 claims description 3
• 125000004122 cyclic group Chemical group 0.000 claims description 3
• 231100000433 cytotoxic Toxicity 0.000 claims description 3
• 229940127089 cytotoxic agent Drugs 0.000 claims description 3
• 230000001472 cytotoxic effect Effects 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
• 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 3
• JJPVQJUMLNOOFA-UHFFFAOYSA-N morpholin-4-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)N1CCOCC1 JJPVQJUMLNOOFA-UHFFFAOYSA-N 0.000 claims description 3
• IDOYLBQFDVFJFG-UHFFFAOYSA-N n,n-dimethyl-2-[4-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]piperazin-1-yl]ethanamine Chemical compound C1CN(CCN(C)C)CCN1CC1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 IDOYLBQFDVFJFG-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• BAVUDFIWZJGWJT-UHFFFAOYSA-N n,n-dimethyl-4-[[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methylamino]methyl]aniline Chemical compound C1=CC(N(C)C)=CC=C1CNCC1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 BAVUDFIWZJGWJT-UHFFFAOYSA-N 0.000 claims description 3
• VAPKPKVMFNHWHZ-UHFFFAOYSA-N n-(4-fluorophenyl)-4-(1h-pyrrolo[2,3-b]pyridin-4-yl)benzamide Chemical compound C1=CC(F)=CC=C1NC(=O)C1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 VAPKPKVMFNHWHZ-UHFFFAOYSA-N 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
• KMMIYAJRKFDVJE-UHFFFAOYSA-N n-(pyridin-2-ylmethyl)-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)NCC1=CC=CC=N1 KMMIYAJRKFDVJE-UHFFFAOYSA-N 0.000 claims description 3
• IFKNPSICEVSZHE-UHFFFAOYSA-N n-(pyridin-3-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=CN=C1 IFKNPSICEVSZHE-UHFFFAOYSA-N 0.000 claims description 3
• OXUSFSHOXUORDG-UHFFFAOYSA-N n-(pyridin-3-ylmethyl)-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)NCC1=CC=CN=C1 OXUSFSHOXUORDG-UHFFFAOYSA-N 0.000 claims description 3
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