CZ20033444A3 - Azaindoles - Google Patents

Info

Publication number

CZ20033444A3

CZ20033444A3 CZ20033444A CZ20033444A CZ20033444A3 CZ 20033444 A3 CZ20033444 A3 CZ 20033444A3 CZ 20033444 A CZ20033444 A CZ 20033444A CZ 20033444 A CZ20033444 A CZ 20033444A CZ 20033444 A3 CZ20033444 A3 CZ 20033444A3

Authority

CZ

Czechia

Prior art keywords

pyrrolo

indol

methyl

pyridin

methoxy

Prior art date

2001-06-21

Links

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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 742
• 150000003839 salts Chemical class 0.000 claims abstract description 97
• 239000012453 solvate Substances 0.000 claims abstract description 64
• -1 cyclic acetal Chemical class 0.000 claims description 334
• 125000000217 alkyl group Chemical group 0.000 claims description 172
• 229910052739 hydrogen Inorganic materials 0.000 claims description 152
• 238000000034 method Methods 0.000 claims description 151
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 138
• 125000001072 heteroaryl group Chemical group 0.000 claims description 122
• 229910005965 SO 2 Inorganic materials 0.000 claims description 120
• 125000003118 aryl group Chemical group 0.000 claims description 118
• 239000001257 hydrogen Substances 0.000 claims description 86
• 229940002612 prodrug Drugs 0.000 claims description 84
• 239000000651 prodrug Substances 0.000 claims description 84
• 150000001204 N-oxides Chemical class 0.000 claims description 78
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 77
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 76
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 76
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 66
• 239000000203 mixture Substances 0.000 claims description 59
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 55
• 229910052736 halogen Inorganic materials 0.000 claims description 50
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 47
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 47
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 46
• 125000003342 alkenyl group Chemical group 0.000 claims description 42
• 125000005843 halogen group Chemical group 0.000 claims description 36
• 239000002253 acid Substances 0.000 claims description 35
• 230000002378 acidificating effect Effects 0.000 claims description 35
• 125000004432 carbon atom Chemical group C* 0.000 claims description 31
• 150000002367 halogens Chemical group 0.000 claims description 30
• 125000003545 alkoxy group Chemical group 0.000 claims description 29
• 229910052799 carbon Inorganic materials 0.000 claims description 29
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
• 125000001041 indolyl group Chemical group 0.000 claims description 24
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
• 229910052757 nitrogen Inorganic materials 0.000 claims description 24
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
• 235000019260 propionic acid Nutrition 0.000 claims description 21
• 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 20
• CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 claims description 20
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 20
• VAJOSPMTARTPKN-UHFFFAOYSA-N 2-[5-methoxy-3-(5h-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]-1-morpholin-4-ylethanone Chemical compound C1=C(C=2NC3=NC=CN=C3C=2)C2=CC(OC)=CC=C2N1CC(=O)N1CCOCC1 VAJOSPMTARTPKN-UHFFFAOYSA-N 0.000 claims description 19
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 19
• 125000001424 substituent group Chemical group 0.000 claims description 19
• 125000006414 CCl Chemical group ClC* 0.000 claims description 17
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 17
• 150000002431 hydrogen Chemical group 0.000 claims description 17
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 17
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 16
• 230000003197 catalytic effect Effects 0.000 claims description 15
• 229910052760 oxygen Inorganic materials 0.000 claims description 15
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
• 229910052717 sulfur Inorganic materials 0.000 claims description 15
• 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 14
• 206010028980 Neoplasm Diseases 0.000 claims description 14
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 14
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 13
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 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
• 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
• 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 11
• 101100298295 Drosophila melanogaster flfl gene Proteins 0.000 claims description 11
• 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 11
• 239000003112 inhibitor Substances 0.000 claims description 11
• 125000004076 pyridyl group Chemical group 0.000 claims description 11
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 11
• 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 10
• LIZDNKRMTCXMAV-UHFFFAOYSA-N 3-[4-(3,5-dimethyl-1,2-oxazol-4-yl)-1h-pyrrolo[2,3-b]pyridin-2-yl]-1-methylindole-5-carboxylic acid Chemical compound CC1=NOC(C)=C1C1=CC=NC2=C1C=C(C=1C3=CC(=CC=C3N(C)C=1)C(O)=O)N2 LIZDNKRMTCXMAV-UHFFFAOYSA-N 0.000 claims description 10
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 10
• 108090000461 Aurora Kinase A Proteins 0.000 claims description 10
• 102100032311 Aurora kinase A Human genes 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
• 150000001412 amines Chemical class 0.000 claims description 10
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
• 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 10
• 229940080818 propionamide Drugs 0.000 claims description 10
• ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 claims description 9
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 9
• 150000001408 amides Chemical class 0.000 claims description 9
• TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 claims description 9
• 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 8
• 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
• FTJGHPGHUSLQAK-UHFFFAOYSA-N 2-(5-methoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridine-4-carbonitrile Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)OC)=CC2=C1C#N FTJGHPGHUSLQAK-UHFFFAOYSA-N 0.000 claims description 8
• CIDALPHOFCAXQR-UHFFFAOYSA-N 2-(5-methoxy-1h-indol-3-yl)-1h-pyrrolo[2,3-b]pyridine-4-carbonitrile Chemical compound C1=CN=C2NC(C3=CNC4=CC=C(C=C43)OC)=CC2=C1C#N CIDALPHOFCAXQR-UHFFFAOYSA-N 0.000 claims description 8
• CYGVUQDIFRECJA-UHFFFAOYSA-N 4-[2-(5-methoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridin-4-yl]-3,5-dimethyl-1,2-oxazole Chemical compound C12=CC(OC)=CC=C2N(C)C=C1C(NC1=NC=C2)=CC1=C2C=1C(C)=NOC=1C CYGVUQDIFRECJA-UHFFFAOYSA-N 0.000 claims description 8
• 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 8
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 8
• ZUHZMIKTWRJJLA-UHFFFAOYSA-N 1-[1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indol-5-yl]ethanone Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)C(=O)C)=CC2=C1 ZUHZMIKTWRJJLA-UHFFFAOYSA-N 0.000 claims description 7
• AZEKOCYKHUJNKS-UHFFFAOYSA-N 1-[1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indol-5-yl]oxycyclobutane-1-carboxylic acid Chemical compound C=1C=C2N(C)C=C(C=3NC4=NC=CC=C4C=3)C2=CC=1OC1(C(O)=O)CCC1 AZEKOCYKHUJNKS-UHFFFAOYSA-N 0.000 claims description 7
• 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 7
• 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 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 7
• 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 7
• FKDHQBOTZUDZEJ-UHFFFAOYSA-N 2-(5-methoxy-1-methylindol-3-yl)-4-pyridin-3-yl-1h-pyrrolo[2,3-b]pyridine Chemical compound C12=CC(OC)=CC=C2N(C)C=C1C(NC1=NC=C2)=CC1=C2C1=CC=CN=C1 FKDHQBOTZUDZEJ-UHFFFAOYSA-N 0.000 claims description 7
• 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 7
• SMCLLQQYFYBQQL-UHFFFAOYSA-N 2-[5-methoxy-3-(5h-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]ethanol Chemical compound C1=CN=C2NC(C3=CN(CCO)C4=CC=C(C=C43)OC)=CC2=N1 SMCLLQQYFYBQQL-UHFFFAOYSA-N 0.000 claims description 7
• JHUWLGXCOIMHHQ-UHFFFAOYSA-N 3-(1h-pyrrolo[2,3-b]pyridin-2-yl)-1h-indole-5-carboxylic acid Chemical compound C1=CN=C2NC(C3=CNC4=CC=C(C=C43)C(=O)O)=CC2=C1 JHUWLGXCOIMHHQ-UHFFFAOYSA-N 0.000 claims description 7
• HIWPOKJDACYAFJ-UHFFFAOYSA-N 3-(4-methoxy-1h-pyrrolo[2,3-b]pyridin-2-yl)-1-methylindole-5-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2C(C=3NC=4N=CC=C(C=4C=3)OC)=CN(C)C2=C1 HIWPOKJDACYAFJ-UHFFFAOYSA-N 0.000 claims description 7
• BZGCYSXNPHENAB-UHFFFAOYSA-N 3-[1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indol-5-yl]propanoic acid Chemical compound C12=CC(CCC(O)=O)=CC=C2N(C)C=C1C1=CC2=CC=CN=C2N1 BZGCYSXNPHENAB-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
• 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 7
• YHKXZXWIOPNPDS-UHFFFAOYSA-N 3-[[1-methyl-3-(5h-pyrrolo[2,3-b]pyrazin-6-yl)indole-5-carbonyl]amino]propanoic acid Chemical compound C12=CC(C(=O)NCCC(O)=O)=CC=C2N(C)C=C1C1=CC2=NC=CN=C2N1 YHKXZXWIOPNPDS-UHFFFAOYSA-N 0.000 claims description 7
• AZZIWMRQTCNYEQ-UHFFFAOYSA-N 4-chloro-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=C1Cl AZZIWMRQTCNYEQ-UHFFFAOYSA-N 0.000 claims description 7
• 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 7
• IKISMFQWQNPZGJ-UHFFFAOYSA-N 6-(1h-indol-3-yl)-5h-pyrrolo[2,3-b]pyrazine Chemical compound C1=CN=C2NC(C=3C4=CC=CC=C4NC=3)=CC2=N1 IKISMFQWQNPZGJ-UHFFFAOYSA-N 0.000 claims description 7
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Natural products C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 7
• RKSSWPMEKJQARM-UHFFFAOYSA-N [3-(5h-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]methanol Chemical compound C12=CC=CC=C2N(CO)C=C1C1=CC2=NC=CN=C2N1 RKSSWPMEKJQARM-UHFFFAOYSA-N 0.000 claims description 7
• 125000000304 alkynyl group Chemical group 0.000 claims description 7
• 201000011510 cancer Diseases 0.000 claims description 7
• 229910052740 iodine Inorganic materials 0.000 claims description 7
• JOZNPCHRNZOWDU-UHFFFAOYSA-N n-(2-hydroxyethyl)-1-methyl-3-(5h-pyrrolo[2,3-b]pyrazin-6-yl)indole-5-carboxamide Chemical compound C12=CC(C(=O)NCCO)=CC=C2N(C)C=C1C1=CC2=NC=CN=C2N1 JOZNPCHRNZOWDU-UHFFFAOYSA-N 0.000 claims description 7
• CJEABCXNJXZHHG-UHFFFAOYSA-N n-(2-methoxyethyl)-1-methyl-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)NCCOC)=CC2=N1 CJEABCXNJXZHHG-UHFFFAOYSA-N 0.000 claims description 7
• IFEWOIRZUBHZIP-UHFFFAOYSA-N n-[1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indol-5-yl]acetamide Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)NC(=O)C)=CC2=C1 IFEWOIRZUBHZIP-UHFFFAOYSA-N 0.000 claims description 7
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 7
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
• 125000003107 substituted aryl group Chemical group 0.000 claims description 7
• MUQFTYHVZUPXES-CYBMUJFWSA-N (2r)-3-[1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indol-5-yl]oxypropane-1,2-diol Chemical compound C12=CC(OC[C@H](O)CO)=CC=C2N(C)C=C1C1=CC2=CC=CN=C2N1 MUQFTYHVZUPXES-CYBMUJFWSA-N 0.000 claims description 6
• SAYAZSFRHPSZLZ-CYBMUJFWSA-N (2r)-3-[6-methoxy-1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indol-5-yl]oxypropane-1,2-diol Chemical compound C1=CN=C2NC(C3=CN(C)C=4C=C(C(=CC=43)OC[C@H](O)CO)OC)=CC2=C1 SAYAZSFRHPSZLZ-CYBMUJFWSA-N 0.000 claims description 6
• 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 6
• NGRLVNLOYHSCOT-UHFFFAOYSA-N 2-[1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indol-5-yl]oxyethanol Chemical compound C12=CC(OCCO)=CC=C2N(C)C=C1C1=CC2=CC=CN=C2N1 NGRLVNLOYHSCOT-UHFFFAOYSA-N 0.000 claims description 6
• COKIRTGHADVGEP-UHFFFAOYSA-N 2-[1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indol-5-yl]oxypropan-1-ol Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)OC(CO)C)=CC2=C1 COKIRTGHADVGEP-UHFFFAOYSA-N 0.000 claims description 6
• FPFNTCBEXLWOSS-UHFFFAOYSA-N 2-[1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indol-5-yl]oxypropanoic acid Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)OC(C)C(O)=O)=CC2=C1 FPFNTCBEXLWOSS-UHFFFAOYSA-N 0.000 claims description 6
• BJBMPYZXKSTFJM-UHFFFAOYSA-N 2-[5-(1-methoxypropan-2-yloxy)-1-methylindol-3-yl]-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)OC(C)COC)=CC2=C1 BJBMPYZXKSTFJM-UHFFFAOYSA-N 0.000 claims description 6
• KQPOMDOVRNSQIS-UHFFFAOYSA-N 2-[5-methoxy-1-(2-morpholin-4-yl-2-oxoethyl)indol-3-yl]-1h-pyrrolo[2,3-b]pyridine-4-carbonitrile Chemical compound C1=C(C=2NC3=NC=CC(=C3C=2)C#N)C2=CC(OC)=CC=C2N1CC(=O)N1CCOCC1 KQPOMDOVRNSQIS-UHFFFAOYSA-N 0.000 claims description 6
• JJTVNLBIXOXIQR-UHFFFAOYSA-N 4-[2-(5-methoxy-1h-indol-3-yl)-1h-pyrrolo[2,3-b]pyridin-4-yl]-3,5-dimethyl-1,2-oxazole Chemical compound C12=CC(OC)=CC=C2NC=C1C(NC1=NC=C2)=CC1=C2C=1C(C)=NOC=1C JJTVNLBIXOXIQR-UHFFFAOYSA-N 0.000 claims description 6
• NMMCYAVAWKMNJH-UHFFFAOYSA-N 5-methyl-3-[1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indol-5-yl]-1,2,4-oxadiazole Chemical compound O1C(C)=NC(C=2C=C3C(C=4NC5=NC=CC=C5C=4)=CN(C)C3=CC=2)=N1 NMMCYAVAWKMNJH-UHFFFAOYSA-N 0.000 claims description 6
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