BG108481A - Азаиндоли - Google Patents

Info

Publication number

BG108481A

BG108481A BG108481A BG10848103A BG108481A BG 108481 A BG108481 A BG 108481A BG 108481 A BG108481 A BG 108481A BG 10848103 A BG10848103 A BG 10848103A BG 108481 A BG108481 A BG 108481A

Authority

BG

Bulgaria

Prior art keywords

pyrrolo

methyl

indol

pyridin

methoxy

Prior art date

2001-06-21

Links

• Espacenet
• Global Dossier
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• 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 title description 11
• 150000001875 compounds Chemical class 0.000 claims abstract description 723
• 150000003839 salts Chemical class 0.000 claims abstract description 100
• 229940002612 prodrug Drugs 0.000 claims abstract description 84
• 239000000651 prodrug Substances 0.000 claims abstract description 84
• 239000000203 mixture Substances 0.000 claims abstract description 82
• 239000012453 solvate Substances 0.000 claims abstract description 63
• 108091000080 Phosphotransferase Proteins 0.000 claims abstract description 8
• 102000020233 phosphotransferase Human genes 0.000 claims abstract description 8
• -1 cyclic amine Chemical class 0.000 claims description 399
• 125000000217 alkyl group Chemical group 0.000 claims description 194
• 125000001072 heteroaryl group Chemical group 0.000 claims description 124
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 122
• 238000000034 method Methods 0.000 claims description 114
• 125000003118 aryl group Chemical group 0.000 claims description 113
• 229910052739 hydrogen Inorganic materials 0.000 claims description 113
• 239000001257 hydrogen Substances 0.000 claims description 108
• 229910005965 SO 2 Inorganic materials 0.000 claims description 93
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 79
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 78
• 150000001204 N-oxides Chemical class 0.000 claims description 66
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 65
• 125000005843 halogen group Chemical group 0.000 claims description 62
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 61
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 51
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 45
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 44
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 43
• 125000003342 alkenyl group Chemical group 0.000 claims description 43
• 239000002253 acid Substances 0.000 claims description 40
• 150000002431 hydrogen Chemical class 0.000 claims description 33
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 31
• 230000002378 acidificating effect Effects 0.000 claims description 31
• 125000003545 alkoxy group Chemical group 0.000 claims description 30
• NCODGTKJFCNVAH-UHFFFAOYSA-N 1-methyl-3-(5h-pyrrolo[2,3-b]pyrazin-6-yl)indole-5-carboxylic acid Chemical compound C12=CC(C(O)=O)=CC=C2N(C)C=C1C1=CC2=NC=CN=C2N1 NCODGTKJFCNVAH-UHFFFAOYSA-N 0.000 claims description 29
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 28
• 238000011282 treatment Methods 0.000 claims description 27
• 125000001041 indolyl group Chemical group 0.000 claims description 24
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 22
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
• CVDGAVDNVQNYQT-UHFFFAOYSA-N 1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indole-5-carboxylic acid Chemical compound C12=CC(C(O)=O)=CC=C2N(C)C=C1C1=CC2=CC=CN=C2N1 CVDGAVDNVQNYQT-UHFFFAOYSA-N 0.000 claims description 19
• 125000001475 halogen functional group Chemical group 0.000 claims description 19
• ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 claims description 18
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 18
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
• 125000001424 substituent group Chemical group 0.000 claims description 17
• MVXVYAKCVDQRLW-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 claims description 16
• 206010028980 Neoplasm Diseases 0.000 claims description 16
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 16
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
• 229940080818 propionamide Drugs 0.000 claims description 16
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 15
• 230000002401 inhibitory effect Effects 0.000 claims description 15
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 14
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 14
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 14
• 230000003197 catalytic effect Effects 0.000 claims description 14
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 13
• 108090000461 Aurora Kinase A Proteins 0.000 claims description 12
• 102100039688 Insulin-like growth factor 1 receptor Human genes 0.000 claims description 12
• 125000002252 acyl group Chemical group 0.000 claims description 12
• 125000005530 alkylenedioxy group Chemical group 0.000 claims description 12
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
• 229910052760 oxygen Inorganic materials 0.000 claims description 12
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 12
• 229910052717 sulfur Inorganic materials 0.000 claims description 12
• RVHRALDRJAGLNN-UHFFFAOYSA-N 1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indole-6-carboxylic acid Chemical compound C12=CC=C(C(O)=O)C=C2N(C)C=C1C1=CC2=CC=CN=C2N1 RVHRALDRJAGLNN-UHFFFAOYSA-N 0.000 claims description 11
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 11
• 102100032311 Aurora kinase A Human genes 0.000 claims description 11
• 125000006414 CCl Chemical group ClC* 0.000 claims description 11
• 101001034652 Homo sapiens Insulin-like growth factor 1 receptor Proteins 0.000 claims description 11
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 11
• 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 11
• 239000003112 inhibitor Substances 0.000 claims description 11
• 229960004063 propylene glycol Drugs 0.000 claims description 11
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
• XCLJFTFBHKDRHP-UHFFFAOYSA-N 2-(5-methoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridine-4-carboxylic acid Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)OC)=CC2=C1C(O)=O XCLJFTFBHKDRHP-UHFFFAOYSA-N 0.000 claims description 10
• MIJMZVTYIXYSDK-UHFFFAOYSA-N 6-(5-methoxy-1-methylindol-3-yl)-5h-pyrrolo[2,3-b]pyrazine Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)OC)=CC2=N1 MIJMZVTYIXYSDK-UHFFFAOYSA-N 0.000 claims description 10
• 229910014033 C-OH Inorganic materials 0.000 claims description 10
• 229910014570 C—OH Inorganic materials 0.000 claims description 10
• 125000004076 pyridyl group Chemical group 0.000 claims description 10
• LXQMHOKEXZETKB-UHFFFAOYSA-N 1-amino-2-methylpropan-2-ol Chemical compound CC(C)(O)CN LXQMHOKEXZETKB-UHFFFAOYSA-N 0.000 claims description 9
• 239000004146 Propane-1,2-diol Substances 0.000 claims description 9
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 9
• 206010003246 arthritis Diseases 0.000 claims description 9
• 239000004202 carbamide Substances 0.000 claims description 9
• 235000019260 propionic acid Nutrition 0.000 claims description 9
• VZLHVQTYCPRPHS-UHFFFAOYSA-N 2-(5-methoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)OC)=CC2=C1 VZLHVQTYCPRPHS-UHFFFAOYSA-N 0.000 claims description 8
• 125000004122 cyclic group Chemical group 0.000 claims description 8
• XZRYCTLOGNCQDG-UHFFFAOYSA-N n-(2-hydroxy-1,1-dimethylethyl)-1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)-1h-indole-5-carboxamide Chemical compound C12=CC(C(=O)NC(C)(C)CO)=CC=C2N(C)C=C1C1=CC2=CC=CN=C2N1 XZRYCTLOGNCQDG-UHFFFAOYSA-N 0.000 claims description 8
• 125000003107 substituted aryl group Chemical group 0.000 claims description 8
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 8
• RPOHBQMVRIVWKP-UHFFFAOYSA-N 1-[1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indol-5-yl]oxypropan-2-ol Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)OCC(O)C)=CC2=C1 RPOHBQMVRIVWKP-UHFFFAOYSA-N 0.000 claims description 7
• KYWSGFFFDGCSES-UHFFFAOYSA-N 1-methyl-3-(5h-pyrrolo[2,3-b]pyrazin-6-yl)indol-5-ol Chemical compound C12=CC(O)=CC=C2N(C)C=C1C1=CC2=NC=CN=C2N1 KYWSGFFFDGCSES-UHFFFAOYSA-N 0.000 claims description 7
• VEKQEFMQDFQZSJ-UHFFFAOYSA-N 3-[3-(5h-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]propan-1-ol Chemical compound C12=CC=CC=C2N(CCCO)C=C1C1=CC2=NC=CN=C2N1 VEKQEFMQDFQZSJ-UHFFFAOYSA-N 0.000 claims description 7
• 125000000304 alkynyl group Chemical group 0.000 claims description 7
• 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 claims description 7
• 235000013772 propylene glycol Nutrition 0.000 claims description 7
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 7
• HVPYZVWMSSBUNJ-UHFFFAOYSA-N 2-(1-ethyl-5-methoxyindol-3-yl)-n-(1-hydroxy-2-methylpropan-2-yl)-1h-pyrrolo[2,3-b]pyridine-4-carboxamide Chemical compound C12=CC(OC)=CC=C2N(CC)C=C1C1=CC2=C(C(=O)NC(C)(C)CO)C=CN=C2N1 HVPYZVWMSSBUNJ-UHFFFAOYSA-N 0.000 claims description 6
• GZRCWJUTTURNJO-UHFFFAOYSA-N 2-(5,6-dimethoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC(C=3C=4C=C(C(=CC=4N(C)C=3)OC)OC)=CC2=C1 GZRCWJUTTURNJO-UHFFFAOYSA-N 0.000 claims description 6
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
• DYFHPNQRLTZBCB-UHFFFAOYSA-N 6-(4-methylsulfanylphenyl)-5h-pyrrolo[2,3-b]pyrazine Chemical compound C1=CC(SC)=CC=C1C1=CC2=NC=CN=C2N1 DYFHPNQRLTZBCB-UHFFFAOYSA-N 0.000 claims description 6
• GIJWLMVJORUCKS-UHFFFAOYSA-N 6-methoxy-1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indol-5-ol Chemical compound C1=CN=C2NC(C3=CN(C)C=4C=C(C(=CC=43)O)OC)=CC2=C1 GIJWLMVJORUCKS-UHFFFAOYSA-N 0.000 claims description 6
• TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 claims description 6
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
• 208000027866 inflammatory disease Diseases 0.000 claims description 6
• 229940124530 sulfonamide Drugs 0.000 claims description 6
• QBUASRVBPRBVRJ-UHFFFAOYSA-N 1-[1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indol-5-yl]oxycyclobutane-1-carboxamide Chemical compound C=1C=C2N(C)C=C(C=3NC4=NC=CC=C4C=3)C2=CC=1OC1(C(N)=O)CCC1 QBUASRVBPRBVRJ-UHFFFAOYSA-N 0.000 claims description 5
• AVNBDKGXTGVKOZ-UHFFFAOYSA-N 1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indol-5-ol Chemical compound C12=CC(O)=CC=C2N(C)C=C1C1=CC2=CC=CN=C2N1 AVNBDKGXTGVKOZ-UHFFFAOYSA-N 0.000 claims description 5
• UVGZNKUGQAZSFE-UHFFFAOYSA-N 1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indole-5-carboxamide Chemical compound C12=CC(C(N)=O)=CC=C2N(C)C=C1C1=CC2=CC=CN=C2N1 UVGZNKUGQAZSFE-UHFFFAOYSA-N 0.000 claims description 5
• QSZHVPFODMPGOS-UHFFFAOYSA-N 2-(5-methoxy-1h-indol-3-yl)-1h-pyrrolo[2,3-b]pyridine-4-carboxylic acid Chemical compound C1=CN=C2NC(C3=CNC4=CC=C(C=C43)OC)=CC2=C1C(O)=O QSZHVPFODMPGOS-UHFFFAOYSA-N 0.000 claims description 5
• MCTZIYPXXHBZEW-UHFFFAOYSA-N 2-[1-methyl-5-(2-methyltetrazol-5-yl)indol-3-yl]-1h-pyrrolo[2,3-b]pyridine Chemical compound CN1N=NC(C=2C=C3C(C=4NC5=NC=CC=C5C=4)=CN(C)C3=CC=2)=N1 MCTZIYPXXHBZEW-UHFFFAOYSA-N 0.000 claims description 5
• JODRAEBPOHRJGI-UHFFFAOYSA-N 2-[1-methyl-5-(2h-tetrazol-5-yl)indol-3-yl]-1h-pyrrolo[2,3-b]pyridine Chemical compound C=1C=C2N(C)C=C(C=3NC4=NC=CC=C4C=3)C2=CC=1C=1N=NNN=1 JODRAEBPOHRJGI-UHFFFAOYSA-N 0.000 claims description 5
• BSONOAQXFAIGPB-UHFFFAOYSA-N 3-[5-methoxy-3-(5h-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]propan-1-ol Chemical compound C1=CN=C2NC(C3=CN(CCCO)C4=CC=C(C=C43)OC)=CC2=N1 BSONOAQXFAIGPB-UHFFFAOYSA-N 0.000 claims description 5
• NWCNXQNJIZEBTG-UHFFFAOYSA-N 3-[6-(4-hydroxyphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]propanoic acid Chemical compound N1C2=NC=CN=C2C(CCC(=O)O)=C1C1=CC=C(O)C=C1 NWCNXQNJIZEBTG-UHFFFAOYSA-N 0.000 claims description 5
• FEAXJWJFDJCIMM-UHFFFAOYSA-N 3-[6-(4-methoxyphenyl)-5h-pyrrolo[2,3-b]pyrazin-7-yl]propanoic acid Chemical compound C1=CC(OC)=CC=C1C1=C(CCC(O)=O)C2=NC=CN=C2N1 FEAXJWJFDJCIMM-UHFFFAOYSA-N 0.000 claims description 5
• PAWSEASAGCSQHU-UHFFFAOYSA-N 4-(5h-pyrrolo[2,3-b]pyrazin-6-yl)aniline Chemical compound C1=CC(N)=CC=C1C1=CC2=NC=CN=C2N1 PAWSEASAGCSQHU-UHFFFAOYSA-N 0.000 claims description 5
• LMHHYPOKWRDJTP-UHFFFAOYSA-N 4-chloro-2-(5-methoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)OC)=CC2=C1Cl LMHHYPOKWRDJTP-UHFFFAOYSA-N 0.000 claims description 5
• QFSGJFOPYOPYRB-UHFFFAOYSA-N 4-methoxy-2-(5-methoxy-1h-indol-3-yl)-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC(C3=CNC4=CC=C(C=C43)OC)=CC2=C1OC QFSGJFOPYOPYRB-UHFFFAOYSA-N 0.000 claims description 5
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
• OPIPFYKXYNLMGL-UHFFFAOYSA-N 6-(1-methyl-4-phenylpyrrol-3-yl)-5h-pyrrolo[2,3-b]pyrazine Chemical compound C=1N(C)C=C(C=2NC3=NC=CN=C3C=2)C=1C1=CC=CC=C1 OPIPFYKXYNLMGL-UHFFFAOYSA-N 0.000 claims description 5
• WGWNCAKNPSBPPM-UHFFFAOYSA-N 6-(1-methylindol-3-yl)-5h-pyrrolo[2,3-b]pyrazine Chemical compound C12=CC=CC=C2N(C)C=C1C1=CC2=NC=CN=C2N1 WGWNCAKNPSBPPM-UHFFFAOYSA-N 0.000 claims description 5
• IZFZUQZBYVWIHC-UHFFFAOYSA-N 6-(1-methylpyrrol-2-yl)-5h-pyrrolo[2,3-b]pyrazine Chemical compound CN1C=CC=C1C1=CC2=NC=CN=C2N1 IZFZUQZBYVWIHC-UHFFFAOYSA-N 0.000 claims description 5
• XQYJBGKMIPFFJS-UHFFFAOYSA-N 6-(4-methoxyphenyl)-5h-pyrrolo[2,3-b]pyrazine Chemical compound C1=CC(OC)=CC=C1C1=CC2=NC=CN=C2N1 XQYJBGKMIPFFJS-UHFFFAOYSA-N 0.000 claims description 5
• BOAWWCKJPHLVFL-UHFFFAOYSA-N 6-(5-methoxy-1h-indol-3-yl)-5h-pyrrolo[2,3-b]pyrazine Chemical compound C1=CN=C2NC(C3=CNC4=CC=C(C=C43)OC)=CC2=N1 BOAWWCKJPHLVFL-UHFFFAOYSA-N 0.000 claims description 5
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 5
• 150000001408 amides Chemical class 0.000 claims description 5
• 208000010668 atopic eczema Diseases 0.000 claims description 5
• 201000011510 cancer Diseases 0.000 claims description 5
• 201000010099 disease Diseases 0.000 claims description 5
• SUVBMZUNTFWEAN-UHFFFAOYSA-N ethyl 2-[2-methoxy-5-(5h-pyrrolo[2,3-b]pyrazin-6-yl)phenoxy]acetate Chemical compound C1=C(OC)C(OCC(=O)OCC)=CC(C=2NC3=NC=CN=C3C=2)=C1 SUVBMZUNTFWEAN-UHFFFAOYSA-N 0.000 claims description 5
• 125000002883 imidazolyl group Chemical group 0.000 claims description 5
• OOVNCCJSGHIIQT-UHFFFAOYSA-N n,1-dimethyl-3-(5h-pyrrolo[2,3-b]pyrazin-6-yl)indole-5-carboxamide Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)C(=O)NC)=CC2=N1 OOVNCCJSGHIIQT-UHFFFAOYSA-N 0.000 claims description 5
• AMECZOITPGYJEM-UHFFFAOYSA-N n-(1-hydroxy-2-methylpropan-2-yl)-2-(5-methoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridine-4-carboxamide Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)OC)=CC2=C1C(=O)NC(C)(C)CO AMECZOITPGYJEM-UHFFFAOYSA-N 0.000 claims description 5
• QXSNZHAWKYWAKB-UHFFFAOYSA-N n-(2-hydroxypropyl)-2-(5-methoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridine-4-carboxamide Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)OC)=CC2=C1C(=O)NCC(C)O QXSNZHAWKYWAKB-UHFFFAOYSA-N 0.000 claims description 5
• VUISMYNHSHYGNC-UHFFFAOYSA-N n-(2-methoxyethyl)-2-(5-methoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridine-4-carboxamide Chemical compound C1=C(OC)C=C2C(C=3NC=4N=CC=C(C=4C=3)C(=O)NCCOC)=CN(C)C2=C1 VUISMYNHSHYGNC-UHFFFAOYSA-N 0.000 claims description 5
• PWQQTIQWOQXEMI-UHFFFAOYSA-N n-(3-amino-3-oxopropyl)-1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indole-5-carboxamide Chemical compound C12=CC(C(=O)NCCC(N)=O)=CC=C2N(C)C=C1C1=CC2=CC=CN=C2N1 PWQQTIQWOQXEMI-UHFFFAOYSA-N 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 5
• VGGBMWRHJWCWBG-UHFFFAOYSA-N 1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)-n-(1h-1,2,4-triazol-5-yl)indole-6-carboxamide Chemical compound C1=C2N(C)C=C(C=3NC4=NC=CC=C4C=3)C2=CC=C1C(=O)NC=1N=CNN=1 VGGBMWRHJWCWBG-UHFFFAOYSA-N 0.000 claims description 4
• NNASJUQMUFFFPP-UHFFFAOYSA-N 1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indol-5-amine Chemical compound C12=CC(N)=CC=C2N(C)C=C1C1=CC2=CC=CN=C2N1 NNASJUQMUFFFPP-UHFFFAOYSA-N 0.000 claims description 4
• QPQYJHKPANJWSN-UHFFFAOYSA-N 2-(1-ethyl-5-methoxyindol-3-yl)-1h-pyrrolo[2,3-b]pyridine-4-carboxylic acid Chemical compound C12=CC(OC)=CC=C2N(CC)C=C1C1=CC2=C(C(O)=O)C=CN=C2N1 QPQYJHKPANJWSN-UHFFFAOYSA-N 0.000 claims description 4
• DFPXZCFFGKSGGH-UHFFFAOYSA-N 2-(1-methylpyrrol-2-yl)-1h-pyrrolo[2,3-b]pyridine Chemical compound CN1C=CC=C1C1=CC2=CC=CN=C2N1 DFPXZCFFGKSGGH-UHFFFAOYSA-N 0.000 claims description 4
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• KELLLGDNFSNCIO-UHFFFAOYSA-N 2-(2-phenyl-1h-pyrrolo[2,3-b]pyridin-3-yl)acetonitrile Chemical compound N1C2=NC=CC=C2C(CC#N)=C1C1=CC=CC=C1 KELLLGDNFSNCIO-UHFFFAOYSA-N 0.000 claims description 4
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• 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
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