JP2019530667A5

JP2019530667A5 -

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Publication number: JP2019530667A5
Authority: JP; Japan
Prior art keywords: isopropyl; piperidine; indole; indol; dimethylpyridine
Prior art date: 2017-09-08
Legal status : Granted

Application number

JP2019513033A

Other languages

English (en)

Japanese (ja)

Other versions

JP7028861B2 (ja

JP2019530667A (ja

Filing date

2017-09-08

Publication date

2020-10-08

2017-09-08 Application filed filed Critical

2017-09-08 Priority claimed from PCT/US2017/050577 external-priority patent/WO2018049089A1/en

2019-10-24 Publication of JP2019530667A publication Critical patent/JP2019530667A/ja

2020-10-08 Publication of JP2019530667A5 publication Critical patent/JP2019530667A5/ja

2022-03-02 Application granted granted Critical

2022-03-02 Publication of JP7028861B2 publication Critical patent/JP7028861B2/ja

Status Active legal-status Critical Current

2037-09-08 Anticipated expiration legal-status Critical

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-1 2 -cyclopropyl Chemical group 0.000 claims 612
KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims 161
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 139
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 64
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 42
125000000217 alkyl group Chemical group 0.000 claims 41
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 34
RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 32
125000003709 fluoroalkyl group Chemical group 0.000 claims 23
125000002768 hydroxyalkyl group Chemical group 0.000 claims 18
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims 14
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 13
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims 13
125000004966 cyanoalkyl group Chemical group 0.000 claims 12
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 11
229910052799 carbon Inorganic materials 0.000 claims 10
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 10
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 9
150000001875 compounds Chemical class 0.000 claims 8
125000002883 imidazolyl group Chemical group 0.000 claims 8
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 8
150000003839 salts Chemical class 0.000 claims 8
125000000335 thiazolyl group Chemical group 0.000 claims 8
125000001425 triazolyl group Chemical group 0.000 claims 8
150000001204 N-oxides Chemical class 0.000 claims 7
125000004076 pyridyl group Chemical group 0.000 claims 7
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 7
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 6
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
125000002757 morpholinyl group Chemical group 0.000 claims 6
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 6
125000000719 pyrrolidinyl group Chemical group 0.000 claims 6
XWKFPIODWVPXLX-UHFFFAOYSA-N 2,5-dimethylpyridine Chemical compound CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 claims 5
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims 5
JLAKCHGEEBPDQI-UHFFFAOYSA-N 4-(4-fluorobenzyl)piperidine Chemical compound C1=CC(F)=CC=C1CC1CCNCC1 JLAKCHGEEBPDQI-UHFFFAOYSA-N 0.000 claims 5
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims 5
125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims 5
125000000842 isoxazolyl group Chemical group 0.000 claims 5
125000002971 oxazolyl group Chemical group 0.000 claims 5
125000003566 oxetanyl group Chemical group 0.000 claims 5
125000004193 piperazinyl group Chemical group 0.000 claims 5
125000003386 piperidinyl group Chemical group 0.000 claims 5
125000003226 pyrazolyl group Chemical group 0.000 claims 5
125000000168 pyrrolyl group Chemical group 0.000 claims 5
125000001412 tetrahydropyranyl group Chemical group 0.000 claims 5
AOSVDOPPFPPBPS-UHFFFAOYSA-N 1-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[(1-methylcyclobutyl)amino]ethanone Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CNC1(CCC1)C)=O)C AOSVDOPPFPPBPS-UHFFFAOYSA-N 0.000 claims 4
RQEDXUKWSYJDPG-UHFFFAOYSA-N 1-piperidin-4-ylindole Chemical compound C1CNCCC1N1C2=CC=CC=C2C=C1 RQEDXUKWSYJDPG-UHFFFAOYSA-N 0.000 claims 4
125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims 4
HINPDWKQQUCHCX-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indole Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=CC=C2C=1C(C)C)C HINPDWKQQUCHCX-UHFFFAOYSA-N 0.000 claims 4
KHLXCSHZEYMJNN-UHFFFAOYSA-N 3-[4-[2-(2-methylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-3-oxopropanenitrile Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(CC#N)=O)C1=CC(=NC=C1)C KHLXCSHZEYMJNN-UHFFFAOYSA-N 0.000 claims 4
DUQGFIKXKISULR-UHFFFAOYSA-N 3-methyloxetane-3-carbaldehyde Chemical compound O=CC1(C)COC1 DUQGFIKXKISULR-UHFFFAOYSA-N 0.000 claims 4
125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 4
125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 4
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 4
DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims 4
UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims 4
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 4
125000000714 pyrimidinyl group Chemical group 0.000 claims 4
125000001424 substituent group Chemical group 0.000 claims 4
FEWLNYSYJNLUOO-UHFFFAOYSA-N 1-Piperidinecarboxaldehyde Chemical compound O=CN1CCCCC1 FEWLNYSYJNLUOO-UHFFFAOYSA-N 0.000 claims 3
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 3
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
RXTSZQDKKBHOAC-UHFFFAOYSA-N 4-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidine-1-carbonyl]-1-methylpyrrolidin-2-one Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(=O)C1CC(N(C1)C)=O)C RXTSZQDKKBHOAC-UHFFFAOYSA-N 0.000 claims 3
OIVLITBTBDPEFK-UHFFFAOYSA-N 5,6-dihydrouracil Chemical compound O=C1CCNC(=O)N1 OIVLITBTBDPEFK-UHFFFAOYSA-N 0.000 claims 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
102100036238 Dihydropyrimidinase Human genes 0.000 claims 3
125000003725 azepanyl group Chemical group 0.000 claims 3
125000002393 azetidinyl group Chemical group 0.000 claims 3
108091022884 dihydropyrimidinase Proteins 0.000 claims 3
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 3
WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 3
239000000203 mixture Substances 0.000 claims 3
125000001715 oxadiazolyl group Chemical group 0.000 claims 3
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 3
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 3
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 3
125000001113 thiadiazolyl group Chemical group 0.000 claims 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
RZCVBHZHGAXIBJ-UHFFFAOYSA-N (3,5-dimethyl-1H-pyrazol-4-yl)-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]methanone Chemical compound CC1=NNC(=C1C(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC(=C1)C)C)C(C)C)C RZCVBHZHGAXIBJ-UHFFFAOYSA-N 0.000 claims 2
UPAZVFTVNGNURA-UHFFFAOYSA-N 1,1,1-trifluoro-3-[4-[2-(2-methylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]propan-2-ol Chemical compound FC(C(CN1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC=C1)C)C(C)C)O)(F)F UPAZVFTVNGNURA-UHFFFAOYSA-N 0.000 claims 2
WNVZOHNNPDZYFN-UHFFFAOYSA-N 1,2-oxazole-3-carbaldehyde Chemical compound O=CC=1C=CON=1 WNVZOHNNPDZYFN-UHFFFAOYSA-N 0.000 claims 2
QDVBKXJMLILLLB-UHFFFAOYSA-N 1,4'-bipiperidine Chemical compound C1CCCCN1C1CCNCC1 QDVBKXJMLILLLB-UHFFFAOYSA-N 0.000 claims 2
KQMBHBNTRKZGBE-UHFFFAOYSA-N 1-(2-methylpropyl)-4-piperidin-1-ylpiperidine Chemical compound C1CN(CC(C)C)CCC1N1CCCCC1 KQMBHBNTRKZGBE-UHFFFAOYSA-N 0.000 claims 2
SZXZHDZXOAJTOX-UHFFFAOYSA-N 1-(4-fluoropiperidin-1-yl)ethanone Chemical compound CC(=O)N1CCC(F)CC1 SZXZHDZXOAJTOX-UHFFFAOYSA-N 0.000 claims 2
DGJCLUVWZJLPBW-UHFFFAOYSA-N 1-(methylamino)-3-[4-[2-(2-methylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]propan-2-one Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC(CNC)=O)C1=CC(=NC=C1)C DGJCLUVWZJLPBW-UHFFFAOYSA-N 0.000 claims 2
MNLKNVDNXSXBIZ-UHFFFAOYSA-N 1-[4-[2-(2,6-dimethylpyridin-4-yl)-3-ethyl-1H-indol-5-yl]piperidin-1-yl]-2-(methylamino)ethanone Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C(CNC)=O)C MNLKNVDNXSXBIZ-UHFFFAOYSA-N 0.000 claims 2
OUKKUKXUIREIPP-UHFFFAOYSA-N 1-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2,2-difluoroethanone Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(C(F)F)=O)C OUKKUKXUIREIPP-UHFFFAOYSA-N 0.000 claims 2
UWEJXHVMUWRJIL-UHFFFAOYSA-N 1-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-(2-methylpropylamino)ethanone Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CNCC(C)C)=O)C UWEJXHVMUWRJIL-UHFFFAOYSA-N 0.000 claims 2
AWPLAXJDRYKKRT-UHFFFAOYSA-N 1-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-(3-hydroxypiperidin-1-yl)ethanone Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1CC(CCC1)O)=O)C AWPLAXJDRYKKRT-UHFFFAOYSA-N 0.000 claims 2
XKCGLNZQTVVYCM-UHFFFAOYSA-N 1-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-(3-methylbutylamino)ethanone Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CNCCC(C)C)=O)C XKCGLNZQTVVYCM-UHFFFAOYSA-N 0.000 claims 2
JBLGNICARDXWNY-UHFFFAOYSA-N 1-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-(oxan-4-ylamino)ethanone Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CNC1CCOCC1)=O)C JBLGNICARDXWNY-UHFFFAOYSA-N 0.000 claims 2
XHNFNKLHGHPNAA-UHFFFAOYSA-N 1-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-(propylamino)ethanone Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CNCCC)=O)C XHNFNKLHGHPNAA-UHFFFAOYSA-N 0.000 claims 2
ZAIKSTDGRPJAPV-UHFFFAOYSA-N 1-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[(2-hydroxy-2-methylpropyl)-methylamino]ethanone Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN(C)CC(C)(C)O)=O)C ZAIKSTDGRPJAPV-UHFFFAOYSA-N 0.000 claims 2
GOISWUPLQFHRTO-UHFFFAOYSA-N 1-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[(2-methoxypyrimidin-5-yl)methyl-methylamino]ethanone Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN(C)CC=1C=NC(=NC=1)OC)=O)C GOISWUPLQFHRTO-UHFFFAOYSA-N 0.000 claims 2
PKZUJBXLTAYXQF-VWLOTQADSA-N 1-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]ethanone Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1[C@@H](CCC1)CO)=O)C PKZUJBXLTAYXQF-VWLOTQADSA-N 0.000 claims 2
BOYQISFMSGADEN-DQEYMECFSA-N 1-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[(2S,4S)-2-(hydroxymethyl)-4-(trifluoromethyl)pyrrolidin-1-yl]ethanone Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1[C@@H](C[C@@H](C1)C(F)(F)F)CO)=O)C BOYQISFMSGADEN-DQEYMECFSA-N 0.000 claims 2
ZWHDQYZTTFDHBR-UHFFFAOYSA-N 1-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[(3-hydroxy-1-adamantyl)amino]ethanone Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CNC12CC3(CC(CC(C1)C3)C2)O)=O)C ZWHDQYZTTFDHBR-UHFFFAOYSA-N 0.000 claims 2
XHAWCXRULFKZGY-RUZDIDTESA-N 1-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[(3R)-3-(hydroxymethyl)morpholin-4-yl]ethanone Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1[C@@H](COCC1)CO)=O)C XHAWCXRULFKZGY-RUZDIDTESA-N 0.000 claims 2
CSESQWYRAUZSBE-UHFFFAOYSA-N 1-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[2-hydroxyethyl(methyl)amino]ethanone Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN(C)CCO)=O)C CSESQWYRAUZSBE-UHFFFAOYSA-N 0.000 claims 2
XWSHKUKXLYGRJW-UHFFFAOYSA-N 1-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[ethyl(methyl)amino]ethanone Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN(C)CC)=O)C XWSHKUKXLYGRJW-UHFFFAOYSA-N 0.000 claims 2
NOFZDNDYPWJSFV-UHFFFAOYSA-N 1-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[methyl(2-methylpropyl)amino]ethanone Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN(C)CC(C)C)=O)C NOFZDNDYPWJSFV-UHFFFAOYSA-N 0.000 claims 2
MNOVHAHGZMTNGR-UHFFFAOYSA-N 1-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-ethylbutan-1-one Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(C(CC)CC)=O)C MNOVHAHGZMTNGR-UHFFFAOYSA-N 0.000 claims 2
GQMXLJCGTZJQOS-UHFFFAOYSA-N 1-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-pyrrolidin-1-ylethanone Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1CCCC1)=O)C GQMXLJCGTZJQOS-UHFFFAOYSA-N 0.000 claims 2
TYOUNLBWIJBWEH-UHFFFAOYSA-N 1-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-3-methoxypropan-1-one Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CCOC)=O)C TYOUNLBWIJBWEH-UHFFFAOYSA-N 0.000 claims 2
DFEFMHCPJUMEOM-UHFFFAOYSA-N 1-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(C)=O)C DFEFMHCPJUMEOM-UHFFFAOYSA-N 0.000 claims 2
DBTJDELMJUCPMM-UHFFFAOYSA-N 1-[4-[2-(2-cyclopropyl-5-fluoropyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-(methylamino)ethanone Chemical compound C1(CC1)C1=NC=C(C(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CNC)=O)F DBTJDELMJUCPMM-UHFFFAOYSA-N 0.000 claims 2
KZRSZVVGUNHRLW-UHFFFAOYSA-N 1-[4-[2-(2-cyclopropyl-6-methylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound C1(CC1)C1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN(C)C)=O)C KZRSZVVGUNHRLW-UHFFFAOYSA-N 0.000 claims 2
NXUJBPZKKIUELL-UHFFFAOYSA-N 1-[4-[2-(2-fluoro-6-methylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound FC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(C)=O)C NXUJBPZKKIUELL-UHFFFAOYSA-N 0.000 claims 2
RSCAPQHZLJAENT-UHFFFAOYSA-N 1-[4-[2-(2-methylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-3-piperidin-4-ylpropan-1-one Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(CCC1CCNCC1)=O)C1=CC(=NC=C1)C RSCAPQHZLJAENT-UHFFFAOYSA-N 0.000 claims 2
BUQBARJCQAQNCW-UHFFFAOYSA-N 1-[4-[2-(3-fluoro-2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-(methylamino)ethanone Chemical compound FC=1C(=NC(=CC=1C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CNC)=O)C)C BUQBARJCQAQNCW-UHFFFAOYSA-N 0.000 claims 2
RZHBQUMVPTYJOX-UHFFFAOYSA-N 1-[4-[2-(5-fluoro-2-methylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-(methylamino)ethanone Chemical compound FC=1C(=CC(=NC=1)C)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CNC)=O RZHBQUMVPTYJOX-UHFFFAOYSA-N 0.000 claims 2
MZGGWBPTWFTLBU-UHFFFAOYSA-N 1-[4-[3-(2,2-difluoroethyl)-2-(2,6-dimethylpyridin-4-yl)-1H-indol-5-yl]piperidin-1-yl]-2-(methylamino)ethanone Chemical compound FC(CC1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(CNC)=O)C1=CC(=NC(=C1)C)C)F MZGGWBPTWFTLBU-UHFFFAOYSA-N 0.000 claims 2
UIDBYKZDZXGJLS-UHFFFAOYSA-N 1-[4-[3-cyclopropyl-2-(2,6-dimethylpyridin-4-yl)-1H-indol-5-yl]piperidin-1-yl]-2-methylpropan-2-ol Chemical compound C1(CC1)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC(C)(O)C)C1=CC(=NC(=C1)C)C UIDBYKZDZXGJLS-UHFFFAOYSA-N 0.000 claims 2
LKIYWJKEOOFVCV-UHFFFAOYSA-N 1-methylpiperidine-4-carbaldehyde Chemical compound CN1CCC(C=O)CC1 LKIYWJKEOOFVCV-UHFFFAOYSA-N 0.000 claims 2
KXIXHISTUVHOCY-UHFFFAOYSA-N 1-propan-2-ylpiperidine Chemical compound CC(C)N1CCCCC1 KXIXHISTUVHOCY-UHFFFAOYSA-N 0.000 claims 2
UWFVLKFCNIYHNT-UHFFFAOYSA-N 2,2-dimethyl-3-[4-[2-(2-methylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-3-oxopropanenitrile Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(C(C#N)(C)C)=O)C1=CC(=NC=C1)C UWFVLKFCNIYHNT-UHFFFAOYSA-N 0.000 claims 2
HJNPZYGKAYEAMO-UHFFFAOYSA-N 2,6-dimethyl-4-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)pyridin-3-amine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=C(C(=NC(=C1)C)C)N HJNPZYGKAYEAMO-UHFFFAOYSA-N 0.000 claims 2
PVMIYQMWQVUGDZ-UHFFFAOYSA-N 2-(1-adamantylamino)-1-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound C12(CC3CC(CC(C1)C3)C2)NCC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC(=C1)C)C)C(C)C PVMIYQMWQVUGDZ-UHFFFAOYSA-N 0.000 claims 2
SWSZXYADECBGDZ-UHFFFAOYSA-N 2-(2,3-dimethylpyridin-4-yl)-5-(1-methylpiperidin-4-yl)-3-propan-2-yl-1H-indole Chemical compound CC1=NC=CC(=C1C)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C SWSZXYADECBGDZ-UHFFFAOYSA-N 0.000 claims 2
SPVPBNOTYMSIKC-UHFFFAOYSA-N 2-(2,3-dimethylpyridin-4-yl)-5-piperidin-4-yl-3-propan-2-yl-1H-indole Chemical compound CC1=NC=CC(=C1C)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1 SPVPBNOTYMSIKC-UHFFFAOYSA-N 0.000 claims 2
OBADFAZWMAQJDJ-UHFFFAOYSA-N 2-(2,5-dimethylpyridin-4-yl)-3-methyl-5-[1-(1-propan-2-ylpiperidin-4-yl)piperidin-4-yl]-1H-indole Chemical compound CC1=NC=C(C(=C1)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CCN(CC1)C(C)C)C OBADFAZWMAQJDJ-UHFFFAOYSA-N 0.000 claims 2
XGUGXGJPWWMZGL-UHFFFAOYSA-N 2-(2,5-dimethylpyridin-4-yl)-5-[1-(1-fluoropropan-2-yl)piperidin-4-yl]-3-propan-2-yl-1H-indole Chemical compound CC1=NC=C(C(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CF)C)C XGUGXGJPWWMZGL-UHFFFAOYSA-N 0.000 claims 2
OXQMVIRFPJOOIU-UHFFFAOYSA-N 2-(2,6-difluoropyridin-4-yl)-3-ethyl-5-[1-[1-(2-methylpropyl)piperidin-4-yl]piperidin-4-yl]-1H-indole Chemical compound FC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C1CCN(CC1)CC(C)C)F OXQMVIRFPJOOIU-UHFFFAOYSA-N 0.000 claims 2
FANWYSXLCNOMMR-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-5-(1-propylpiperidin-4-yl)-1H-indole Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CCC)C FANWYSXLCNOMMR-UHFFFAOYSA-N 0.000 claims 2
NNHJMGVORBPPFP-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-5-[1-(1H-pyrazol-4-ylmethyl)piperidin-4-yl]-1H-indole Chemical compound N1N=CC(=C1)CN1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC(=C1)C)C)C(C)C NNHJMGVORBPPFP-UHFFFAOYSA-N 0.000 claims 2
KTHPLUHTVNYZDJ-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-5-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]-1H-indole Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(F)(F)F)C KTHPLUHTVNYZDJ-UHFFFAOYSA-N 0.000 claims 2
MNKYYBJJCVKOMC-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-5-[1-(2H-tetrazol-5-ylmethyl)piperidin-4-yl]-1H-indole Chemical compound N=1NN=NC=1CN1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC(=C1)C)C)C(C)C MNKYYBJJCVKOMC-UHFFFAOYSA-N 0.000 claims 2
FMMWSLXPXFCRHA-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-5-[1-(pyridin-2-ylmethyl)piperidin-4-yl]-1H-indole Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC1=NC=CC=C1)C FMMWSLXPXFCRHA-UHFFFAOYSA-N 0.000 claims 2
IWXFHFRBJHAVDR-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-5-[1-(pyrimidin-2-ylmethyl)piperidin-4-yl]-1H-indole Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC1=NC=CC=N1)C IWXFHFRBJHAVDR-UHFFFAOYSA-N 0.000 claims 2
VCSMIPVBBBTQIR-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-4-fluoro-5-piperidin-4-yl-3-propan-2-yl-1H-indole Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C(=C2C=1C(C)C)F)C1CCNCC1)C VCSMIPVBBBTQIR-UHFFFAOYSA-N 0.000 claims 2
ZHVHTMWMTUNRIX-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-5-(1,2,2,6,6-pentamethylpiperidin-4-yl)-3-propan-2-yl-1H-indole Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CC(N(C(C1)(C)C)C)(C)C)C ZHVHTMWMTUNRIX-UHFFFAOYSA-N 0.000 claims 2
SXEGAKNNZHORFV-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-5-(1-ethylpiperidin-4-yl)-3-propan-2-yl-1H-indole Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC)C SXEGAKNNZHORFV-UHFFFAOYSA-N 0.000 claims 2
NXZNNRHGCGONRT-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-5-(1-pentan-3-ylpiperidin-4-yl)-3-propan-2-yl-1H-indole Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CC)CC)C NXZNNRHGCGONRT-UHFFFAOYSA-N 0.000 claims 2
IVIIDQGMMNXYQK-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-5-[1-(3-methoxypropyl)piperidin-4-yl]-3-propan-2-yl-1H-indole Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CCCOC)C IVIIDQGMMNXYQK-UHFFFAOYSA-N 0.000 claims 2
DXDUWEWJRWEDKV-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-5-[1-(oxetan-3-yl)piperidin-4-yl]-3-propan-2-yl-1H-indole Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C1COC1)C DXDUWEWJRWEDKV-UHFFFAOYSA-N 0.000 claims 2
RPRVQPYKNSMWGA-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-5-[1-[(2-methoxypyrimidin-5-yl)methyl]piperidin-4-yl]-3-propan-2-yl-1H-indole Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC=1C=NC(=NC=1)OC)C RPRVQPYKNSMWGA-UHFFFAOYSA-N 0.000 claims 2
YAQGQSZTCUPAKS-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-5-[1-[(2-methylpyrazol-3-yl)methyl]piperidin-4-yl]-3-propan-2-yl-1H-indole Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC1=CC=NN1C)C YAQGQSZTCUPAKS-UHFFFAOYSA-N 0.000 claims 2
QTXABJLYNQVHLH-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-5-[1-[(6-methoxypyridin-3-yl)methyl]piperidin-4-yl]-3-propan-2-yl-1H-indole Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC=1C=NC(=CC=1)OC)C QTXABJLYNQVHLH-UHFFFAOYSA-N 0.000 claims 2
GSBGSOCZCMYOFJ-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-5-piperidin-4-yl-1H-indole Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1)C1CCNCC1)C GSBGSOCZCMYOFJ-UHFFFAOYSA-N 0.000 claims 2
UMTJMBJASOONEX-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-5-piperidin-4-yl-3-(1,1,1-trifluoropropan-2-yl)-1H-indole Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C(F)(F)F)C)C1CCNCC1)C UMTJMBJASOONEX-UHFFFAOYSA-N 0.000 claims 2
URPSKXBPFVEIKR-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-5-piperidin-4-yl-3-(3,3,3-trifluoroprop-1-en-2-yl)-1H-indole Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(=C)C(F)(F)F)C1CCNCC1)C URPSKXBPFVEIKR-UHFFFAOYSA-N 0.000 claims 2
OPTBQBSQGDMWAG-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-5-piperidin-4-yl-3-propan-2-yl-1H-indole hydrochloride Chemical compound Cl.CC(C)c1c([nH]c2ccc(cc12)C1CCNCC1)-c1cc(C)nc(C)c1 OPTBQBSQGDMWAG-UHFFFAOYSA-N 0.000 claims 2
LGUNSIYJZKAVPR-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-6-fluoro-5-(1-methylpiperidin-4-yl)-3-propan-2-yl-1H-indole Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC(=C(C=C2C=1C(C)C)C1CCN(CC1)C)F)C LGUNSIYJZKAVPR-UHFFFAOYSA-N 0.000 claims 2
GUZLDCZVPRGDTN-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-6-fluoro-5-[1-(oxetan-3-yl)piperidin-4-yl]-3-propan-2-yl-1H-indole Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC(=C(C=C2C=1C(C)C)C1CCN(CC1)C1COC1)F)C GUZLDCZVPRGDTN-UHFFFAOYSA-N 0.000 claims 2
IKIFFPMEFNBHQV-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-6-fluoro-5-[1-[(1-methyl-1,2,4-triazol-3-yl)methyl]piperidin-4-yl]-3-propan-2-yl-1H-indole Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC(=C(C=C2C=1C(C)C)C1CCN(CC1)CC1=NN(C=N1)C)F)C IKIFFPMEFNBHQV-UHFFFAOYSA-N 0.000 claims 2
NYIAWFUKVDFUAU-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-6-fluoro-5-piperidin-4-yl-3-propan-2-yl-1H-indole Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC(=C(C=C2C=1C(C)C)C1CCNCC1)F)C NYIAWFUKVDFUAU-UHFFFAOYSA-N 0.000 claims 2
LMEWBCHKWZGKOQ-UHFFFAOYSA-N 2-(2-chloro-3-fluoropyridin-4-yl)-5-piperidin-4-yl-3-propan-2-yl-1H-indole Chemical compound ClC1=NC=CC(=C1F)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1 LMEWBCHKWZGKOQ-UHFFFAOYSA-N 0.000 claims 2
DFODNGJWWPEXRZ-UHFFFAOYSA-N 2-(2-chloro-3-methylpyridin-4-yl)-5-piperidin-4-yl-3-propan-2-yl-1H-indole Chemical compound ClC1=NC=CC(=C1C)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1 DFODNGJWWPEXRZ-UHFFFAOYSA-N 0.000 claims 2
KSXRLVQWUXLZCL-UHFFFAOYSA-N 2-(2-chloro-5-fluoropyridin-4-yl)-3-ethyl-5-[1-[1-(2-methylpropyl)piperidin-4-yl]piperidin-4-yl]-1H-indole Chemical compound ClC1=NC=C(C(=C1)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C1CCN(CC1)CC(C)C)F KSXRLVQWUXLZCL-UHFFFAOYSA-N 0.000 claims 2
YAIDWAMPVPDIBE-UHFFFAOYSA-N 2-(2-chloropyridin-4-yl)-3-(2,2-difluoroethyl)-5-piperidin-4-yl-1H-indole Chemical compound ClC1=NC=CC(=C1)C=1NC2=CC=C(C=C2C=1CC(F)F)C1CCNCC1 YAIDWAMPVPDIBE-UHFFFAOYSA-N 0.000 claims 2
JRNKBGXNCKBIRT-UHFFFAOYSA-N 2-(2-chloropyridin-4-yl)-3-ethyl-5-piperidin-4-yl-1H-indole Chemical compound ClC1=NC=CC(=C1)C=1NC2=CC=C(C=C2C=1CC)C1CCNCC1 JRNKBGXNCKBIRT-UHFFFAOYSA-N 0.000 claims 2
LOEHFHOKSPZHOX-UHFFFAOYSA-N 2-(2-cyclopropyl-5-fluoropyridin-4-yl)-5-piperidin-4-yl-3-propan-2-yl-1H-indole Chemical compound C1(CC1)C1=NC=C(C(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1)F LOEHFHOKSPZHOX-UHFFFAOYSA-N 0.000 claims 2
ZDFVZOBBLGUINS-UHFFFAOYSA-N 2-(2-cyclopropyl-6-methoxypyridin-4-yl)-5-piperidin-4-yl-3-propan-2-yl-1H-indole Chemical compound C1(CC1)C1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1)OC ZDFVZOBBLGUINS-UHFFFAOYSA-N 0.000 claims 2
KYTNVRKIVDPRDJ-UHFFFAOYSA-N 2-(2-cyclopropyl-6-methylpyridin-4-yl)-5-piperidin-4-yl-3-propan-2-yl-1H-indole Chemical compound C1(CC1)C1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1)C KYTNVRKIVDPRDJ-UHFFFAOYSA-N 0.000 claims 2
BLMILNNFLLFMJI-UHFFFAOYSA-N 2-(2-cyclopropylpyridin-4-yl)-5-[1-[(2-methyl-1H-imidazol-5-yl)methyl]piperidin-4-yl]-3-propan-2-yl-1H-indole Chemical compound C1(CC1)C1=NC=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC=1N=C(NC=1)C BLMILNNFLLFMJI-UHFFFAOYSA-N 0.000 claims 2
NAXCUEOPBFVRKE-UHFFFAOYSA-N 2-(2-cyclopropylpyridin-4-yl)-5-piperidin-4-yl-3-propan-2-yl-1H-indole Chemical compound C1(CC1)C1=NC=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1 NAXCUEOPBFVRKE-UHFFFAOYSA-N 0.000 claims 2
GNYAZQPKSPWQAG-UHFFFAOYSA-N 2-(2-ethyl-5-fluoropyridin-4-yl)-5-piperidin-4-yl-3-propan-2-yl-1H-indole Chemical compound C(C)C1=NC=C(C(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1)F GNYAZQPKSPWQAG-UHFFFAOYSA-N 0.000 claims 2
MSTNVPCHDVLSIT-UHFFFAOYSA-N 2-(2-ethyl-6-methylpyridin-4-yl)-5-piperidin-4-yl-3-propan-2-yl-1H-indole Chemical compound C(C)C1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1)C MSTNVPCHDVLSIT-UHFFFAOYSA-N 0.000 claims 2
USVWDJZKWLCKPU-UHFFFAOYSA-N 2-(2-fluoropyridin-4-yl)-5-[1-(1-methylpiperidin-4-yl)piperidin-4-yl]-3-propan-2-yl-1H-indole Chemical compound FC1=NC=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C1CCN(CC1)C USVWDJZKWLCKPU-UHFFFAOYSA-N 0.000 claims 2
RUCOQCQFEYHVOI-UHFFFAOYSA-N 2-(2-methoxy-6-methylpyridin-4-yl)-5-piperidin-4-yl-3-propan-2-yl-1H-indole Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC(=NC(=C1)C)OC RUCOQCQFEYHVOI-UHFFFAOYSA-N 0.000 claims 2
QCZOZCRXMSAFEY-UHFFFAOYSA-N 2-(2-methoxypyridin-4-yl)-3-methyl-5-[1-(1-methylpiperidin-4-yl)piperidin-4-yl]-1H-indole Chemical compound COC1=NC=CC(=C1)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CCN(CC1)C QCZOZCRXMSAFEY-UHFFFAOYSA-N 0.000 claims 2
ISRHLYWGNAPDHA-UHFFFAOYSA-N 2-(2-methoxypyridin-4-yl)-3-methyl-5-[1-(1-propan-2-ylpiperidin-4-yl)piperidin-4-yl]-1H-indole Chemical compound C(C)(C)N1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC=C1)OC)C ISRHLYWGNAPDHA-UHFFFAOYSA-N 0.000 claims 2
SNSRPIKBINQAHP-UHFFFAOYSA-N 2-(2-methoxypyridin-4-yl)-3-propan-2-yl-5-[1-(1-propan-2-ylpiperidin-4-yl)piperidin-4-yl]-1H-indole Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCN(CC1)C(C)C)C1=CC(=NC=C1)OC SNSRPIKBINQAHP-UHFFFAOYSA-N 0.000 claims 2
ISEUSTCEIUDIKL-UHFFFAOYSA-N 2-(2-methoxypyridin-4-yl)-5-(1-piperidin-4-ylpiperidin-4-yl)-3-propan-2-yl-1H-indole Chemical compound N1(CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC=C1)OC)C(C)C)C1CCNCC1 ISEUSTCEIUDIKL-UHFFFAOYSA-N 0.000 claims 2
JOHPVHOPKILDIX-UHFFFAOYSA-N 2-(2-methoxypyridin-4-yl)-5-[1-(1-methylpiperidin-4-yl)piperidin-4-yl]-3-propan-2-yl-1H-indole Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCN(CC1)C)C1=CC(=NC=C1)OC JOHPVHOPKILDIX-UHFFFAOYSA-N 0.000 claims 2
KAGSPINYGPNPCN-UHFFFAOYSA-N 2-(2-methoxypyridin-4-yl)-5-piperidin-4-yl-3-propan-2-yl-1H-indole Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC(=NC=C1)OC KAGSPINYGPNPCN-UHFFFAOYSA-N 0.000 claims 2
TYWKMKGFJWSJBU-UHFFFAOYSA-N 2-(2-methylpyridin-4-yl)-3-propan-2-yl-5-(1-propylsulfonylpiperidin-4-yl)-1H-indole Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)S(=O)(=O)CCC)C1=CC(=NC=C1)C TYWKMKGFJWSJBU-UHFFFAOYSA-N 0.000 claims 2
QROFWCQXBICXQL-UHFFFAOYSA-N 2-(2-methylpyridin-4-yl)-3-propan-2-yl-5-(1-pyridin-3-ylsulfonylpiperidin-4-yl)-1H-indole Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)S(=O)(=O)C=1C=NC=CC=1)C1=CC(=NC=C1)C QROFWCQXBICXQL-UHFFFAOYSA-N 0.000 claims 2
RXEGAQQYZQDQIL-UHFFFAOYSA-N 2-(2-methylpyridin-4-yl)-3-propan-2-yl-5-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]-1H-indole Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC(F)(F)F)C1=CC(=NC=C1)C RXEGAQQYZQDQIL-UHFFFAOYSA-N 0.000 claims 2
HJDLTXZOLZVAJR-UHFFFAOYSA-N 2-(2-methylpyridin-4-yl)-3-propan-2-yl-5-[1-(pyrrolidin-3-ylmethyl)piperidin-4-yl]-6-(trifluoromethyl)-1H-indole Chemical compound C(C)(C)C1=C(NC2=CC(=C(C=C12)C1CCN(CC1)CC1CNCC1)C(F)(F)F)C1=CC(=NC=C1)C HJDLTXZOLZVAJR-UHFFFAOYSA-N 0.000 claims 2
SCJLHGFKDYDWJO-UHFFFAOYSA-N 2-(2-methylpyridin-4-yl)-5-(1-methylsulfonylpiperidin-4-yl)-3-propan-2-yl-1H-indole Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)S(=O)(=O)C)C1=CC(=NC=C1)C SCJLHGFKDYDWJO-UHFFFAOYSA-N 0.000 claims 2
MLJIZXOQBGKWRG-UHFFFAOYSA-N 2-(2-methylpyridin-4-yl)-5-(1-piperidin-3-ylpiperidin-4-yl)-3-propan-2-yl-1H-indole Chemical compound N1(CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC=C1)C)C(C)C)C1CNCCC1 MLJIZXOQBGKWRG-UHFFFAOYSA-N 0.000 claims 2
AWTOMRPDGCOZIT-UHFFFAOYSA-N 2-(2-methylpyridin-4-yl)-5-[1-(oxetan-3-yl)piperidin-4-yl]-3-propan-2-yl-1H-indole Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1COC1)C1=CC(=NC=C1)C AWTOMRPDGCOZIT-UHFFFAOYSA-N 0.000 claims 2
XZDGZZFKEYIZAS-UHFFFAOYSA-N 2-(2-methylpyridin-4-yl)-5-piperidin-4-yl-3-propan-2-yl-1H-indole Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC(=NC=C1)C XZDGZZFKEYIZAS-UHFFFAOYSA-N 0.000 claims 2
LNUHSZBKNTVQIS-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-5-piperidin-4-yl-3-propan-2-yl-1H-indole Chemical compound ClC=1C=NC=C(C=1C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1)Cl LNUHSZBKNTVQIS-UHFFFAOYSA-N 0.000 claims 2
CTHIDUBDHNNWGD-UHFFFAOYSA-N 2-(3-fluoro-2,6-dimethylpyridin-4-yl)-5-[1-(oxetan-3-yl)piperidin-4-yl]-3-propan-2-yl-1H-indole Chemical compound FC=1C(=NC(=CC=1C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C1COC1)C)C CTHIDUBDHNNWGD-UHFFFAOYSA-N 0.000 claims 2
LAIREGQPLVBJPO-UHFFFAOYSA-N 2-(3-fluoro-2,6-dimethylpyridin-4-yl)-5-piperidin-4-yl-3-propan-2-yl-1H-indole Chemical compound FC=1C(=NC(=CC=1C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1)C)C LAIREGQPLVBJPO-UHFFFAOYSA-N 0.000 claims 2
LLSVSFFZISRQBW-UHFFFAOYSA-N 2-(3-fluoro-2-methylpyridin-4-yl)-5-[1-(oxetan-3-yl)piperidin-4-yl]-3-propan-2-yl-1H-indole Chemical compound FC=1C(=NC=CC=1C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C1COC1)C LLSVSFFZISRQBW-UHFFFAOYSA-N 0.000 claims 2
GAPMTODIKVVLAU-UHFFFAOYSA-N 2-(3-fluoro-2-methylpyridin-4-yl)-5-[1-[(1-methyl-1,2,4-triazol-3-yl)methyl]piperidin-4-yl]-3-propan-2-yl-1H-indole Chemical compound FC=1C(=NC=CC=1C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC1=NN(C=N1)C)C GAPMTODIKVVLAU-UHFFFAOYSA-N 0.000 claims 2
UBMFESXPMRXIMV-UHFFFAOYSA-N 2-(3-fluoro-2-methylpyridin-4-yl)-5-[1-[(2-methoxypyrimidin-5-yl)methyl]piperidin-4-yl]-3-propan-2-yl-1H-indole Chemical compound FC=1C(=NC=CC=1C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC=1C=NC(=NC=1)OC)C UBMFESXPMRXIMV-UHFFFAOYSA-N 0.000 claims 2
YWFHWWRZGWFBBT-UHFFFAOYSA-N 2-(3-fluoro-2-methylpyridin-4-yl)-5-piperidin-4-yl-3-propan-2-yl-1H-indole Chemical compound FC=1C(=NC=CC=1C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1)C YWFHWWRZGWFBBT-UHFFFAOYSA-N 0.000 claims 2
QWSDQZRWXHXPJG-UHFFFAOYSA-N 2-(3-fluoropyridin-4-yl)-5-piperidin-4-yl-3-propan-2-yl-1H-indole Chemical compound FC=1C=NC=CC=1C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1 QWSDQZRWXHXPJG-UHFFFAOYSA-N 0.000 claims 2
DQYLEYUDMWRAAZ-UHFFFAOYSA-N 2-(5-chloro-2-fluoropyridin-4-yl)-5-piperidin-4-yl-3-propan-2-yl-1H-indole Chemical compound ClC=1C(=CC(=NC=1)F)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1 DQYLEYUDMWRAAZ-UHFFFAOYSA-N 0.000 claims 2
BTDAZCLQDRMCFY-UHFFFAOYSA-N 2-(5-fluoro-2-methoxypyridin-4-yl)-5-piperidin-4-yl-3-propan-2-yl-1H-indole Chemical compound FC=1C(=CC(=NC=1)OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1 BTDAZCLQDRMCFY-UHFFFAOYSA-N 0.000 claims 2
ZREKYMWYYDBLTN-UHFFFAOYSA-N 2-(5-fluoro-2-methylpyridin-4-yl)-5-(1-methylpiperidin-4-yl)-3-propan-2-yl-1H-indole Chemical compound FC=1C(=CC(=NC=1)C)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C ZREKYMWYYDBLTN-UHFFFAOYSA-N 0.000 claims 2
JWZPAKRFTOPUQA-UHFFFAOYSA-N 2-(5-fluoro-2-methylpyridin-4-yl)-5-[1-(oxetan-3-ylmethyl)piperidin-4-yl]-3-propan-2-yl-1H-indole Chemical compound FC=1C(=CC(=NC=1)C)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC1COC1 JWZPAKRFTOPUQA-UHFFFAOYSA-N 0.000 claims 2
TXPKDGHRBWGGAJ-UHFFFAOYSA-N 2-(5-fluoro-2-methylpyridin-4-yl)-5-[1-[(1-methyl-1,2,4-triazol-3-yl)methyl]piperidin-4-yl]-3-propan-2-yl-1H-indole Chemical compound FC=1C(=CC(=NC=1)C)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC1=NN(C=N1)C TXPKDGHRBWGGAJ-UHFFFAOYSA-N 0.000 claims 2
IYZUSXCEQTVZRC-UHFFFAOYSA-N 2-(cyclopropylmethylamino)-1-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound C1(CC1)CNCC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC(=C1)C)C)C(C)C IYZUSXCEQTVZRC-UHFFFAOYSA-N 0.000 claims 2
LCIAPAISTXQVJK-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-(3-propan-2-yl-2-pyridin-4-yl-1H-indol-5-yl)piperidin-1-yl]ethanone Chemical compound CN(CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC=NC=C1)C(C)C)C LCIAPAISTXQVJK-UHFFFAOYSA-N 0.000 claims 2
STHJQKMQHQTIRT-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[2-(2,6-dimethylpyridin-4-yl)-3-ethyl-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound CN(CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC(=C1)C)C)CC)C STHJQKMQHQTIRT-UHFFFAOYSA-N 0.000 claims 2
OIDHXQGUBBCVCP-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound CN(CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC(=C1)C)C)C(C)C)C OIDHXQGUBBCVCP-UHFFFAOYSA-N 0.000 claims 2
MFDCNCRBGXXONK-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[2-(2-fluoro-6-methylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound CN(CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC(=C1)C)F)C(C)C)C MFDCNCRBGXXONK-UHFFFAOYSA-N 0.000 claims 2
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims 2
JYQLNICWPXPDQV-UHFFFAOYSA-N 2-[2,2-difluoroethyl(methyl)amino]-1-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound FC(CN(CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC(=C1)C)C)C(C)C)C)F JYQLNICWPXPDQV-UHFFFAOYSA-N 0.000 claims 2
BCQZTFRVRGGHDT-UHFFFAOYSA-N 2-[2-(difluoromethoxy)pyridin-4-yl]-3-ethyl-5-[1-[1-(2-methylpropyl)piperidin-4-yl]piperidin-4-yl]-1H-indole Chemical compound FC(OC1=NC=CC(=C1)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C1CCN(CC1)CC(C)C)F BCQZTFRVRGGHDT-UHFFFAOYSA-N 0.000 claims 2
KYYQIUXUPDSDKV-UHFFFAOYSA-N 2-[4-(3-ethyl-2-pyridin-4-yl-1H-indol-5-yl)piperidin-1-yl]-N-methylethanamine Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CCNC)C1=CC=NC=C1 KYYQIUXUPDSDKV-UHFFFAOYSA-N 0.000 claims 2
XBORVKXVXLMXGU-UHFFFAOYSA-N 2-[4-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)pyridin-2-yl]propan-2-ol Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC(=NC=C1)C(C)(C)O XBORVKXVXLMXGU-UHFFFAOYSA-N 0.000 claims 2
WBJWHSRANNPIIR-UHFFFAOYSA-N 2-[4-[2-(2,5-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-N-methylacetamide Chemical compound CC1=NC=C(C(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(=O)NC)C WBJWHSRANNPIIR-UHFFFAOYSA-N 0.000 claims 2
LCUMXPMTLNMLDL-UHFFFAOYSA-N 2-[4-[2-(2,6-dimethylpyridin-4-yl)-3-ethyl-1H-indol-5-yl]piperidin-1-yl]-N,N-dimethylacetamide Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)CC(=O)N(C)C)C LCUMXPMTLNMLDL-UHFFFAOYSA-N 0.000 claims 2
SHLCZWWNBDBPQU-UHFFFAOYSA-N 2-[4-[2-(2,6-dimethylpyridin-4-yl)-3-ethyl-1H-indol-5-yl]piperidin-1-yl]-N-methylacetamide Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)CC(=O)NC)C SHLCZWWNBDBPQU-UHFFFAOYSA-N 0.000 claims 2
VFTBQFQCPTTYPH-UHFFFAOYSA-N 2-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-1-(2-methylpiperidin-1-yl)ethanone Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(=O)N1C(CCCC1)C)C VFTBQFQCPTTYPH-UHFFFAOYSA-N 0.000 claims 2
GGXPZGMNNZGBBK-UHFFFAOYSA-N 2-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-1-(3-methoxyazetidin-1-yl)ethanone Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(=O)N1CC(C1)OC)C GGXPZGMNNZGBBK-UHFFFAOYSA-N 0.000 claims 2
CALFUCOCCNFCSD-UHFFFAOYSA-N 2-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-1-(3-methylpiperidin-1-yl)ethanone Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(=O)N1CC(CCC1)C)C CALFUCOCCNFCSD-UHFFFAOYSA-N 0.000 claims 2
MDWJYFXPGUETQC-CLJLJLNGSA-N 2-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-1-[(2R,4R)-2-(hydroxymethyl)-4-methoxypyrrolidin-1-yl]ethanone Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(=O)N1[C@H](C[C@H](C1)OC)CO)C MDWJYFXPGUETQC-CLJLJLNGSA-N 0.000 claims 2
VTHOOXQSMDGEDA-FQRUVTKNSA-N 2-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-1-[(2R,4R)-2-(hydroxymethyl)-4-methylpyrrolidin-1-yl]ethanone Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(=O)N1[C@H](C[C@H](C1)C)CO)C VTHOOXQSMDGEDA-FQRUVTKNSA-N 0.000 claims 2
XOXZYNYGKQHHKR-DEOSSOPVSA-N 2-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-1-[(3S)-3-hydroxypyrrolidin-1-yl]ethanone Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(=O)N1C[C@H](CC1)O)C XOXZYNYGKQHHKR-DEOSSOPVSA-N 0.000 claims 2
NIDBPHKWDNELSZ-UHFFFAOYSA-N 2-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-1-[4-(2-methoxyethyl)piperazin-1-yl]ethanone Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(=O)N1CCN(CC1)CCOC)C NIDBPHKWDNELSZ-UHFFFAOYSA-N 0.000 claims 2
LVCMRMFYKPGNIA-UHFFFAOYSA-N 2-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-oxoacetic acid Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(C(=O)O)=O)C LVCMRMFYKPGNIA-UHFFFAOYSA-N 0.000 claims 2
ZBKGPTOTLZCKSM-UHFFFAOYSA-N 2-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-N,N-di(propan-2-yl)acetamide Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(=O)N(C(C)C)C(C)C)C ZBKGPTOTLZCKSM-UHFFFAOYSA-N 0.000 claims 2
GTDJXHVZPKVOBZ-UHFFFAOYSA-N 2-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-N,N-dimethylacetamide Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(=O)N(C)C)C GTDJXHVZPKVOBZ-UHFFFAOYSA-N 0.000 claims 2
RRSYNQRWKAKWLQ-UHFFFAOYSA-N 2-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-N-(2-methoxyethyl)-N-methylacetamide Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(=O)N(C)CCOC)C RRSYNQRWKAKWLQ-UHFFFAOYSA-N 0.000 claims 2
GIZDZSFBTXBQKV-UHFFFAOYSA-N 2-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-N-ethylacetamide Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(=O)NCC)C GIZDZSFBTXBQKV-UHFFFAOYSA-N 0.000 claims 2
QCGNIBNISOBUKZ-UHFFFAOYSA-N 2-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-N-methylacetamide Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(=O)NC)C QCGNIBNISOBUKZ-UHFFFAOYSA-N 0.000 claims 2
HRMPPKRTFPBEGL-UHFFFAOYSA-N 2-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]acetonitrile Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC#N)C HRMPPKRTFPBEGL-UHFFFAOYSA-N 0.000 claims 2
KBGCTXMJKSEDCH-UHFFFAOYSA-N 2-[4-[2-(2-fluoro-6-methylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-N,N-dimethylacetamide Chemical compound FC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(=O)N(C)C)C KBGCTXMJKSEDCH-UHFFFAOYSA-N 0.000 claims 2
VZRIWIIYCYVWRK-UHFFFAOYSA-N 2-[4-[2-(2-fluoro-6-methylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-N-methylacetamide Chemical compound FC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(=O)NC)C VZRIWIIYCYVWRK-UHFFFAOYSA-N 0.000 claims 2
IWJLKZYCMOWZSZ-UHFFFAOYSA-N 2-[4-[2-(2-fluoropyridin-4-yl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]-N-methylethanamine Chemical compound FC1=NC=CC(=C1)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)CCNC IWJLKZYCMOWZSZ-UHFFFAOYSA-N 0.000 claims 2
MYXBEUCLMYJADF-UHFFFAOYSA-N 2-[4-[2-(2-methoxypyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-N-methylethanamine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CCNC)C1=CC(=NC=C1)OC MYXBEUCLMYJADF-UHFFFAOYSA-N 0.000 claims 2
SMPUMXPIGDHNFG-UHFFFAOYSA-N 2-[4-[2-(2-methylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-1-phenylethanol Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC(O)C1=CC=CC=C1)C1=CC(=NC=C1)C SMPUMXPIGDHNFG-UHFFFAOYSA-N 0.000 claims 2
MJZGHXZGDZKOEL-UHFFFAOYSA-N 2-[4-[2-(3-fluoro-2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-N-methylacetamide Chemical compound FC=1C(=NC(=CC=1C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(=O)NC)C)C MJZGHXZGDZKOEL-UHFFFAOYSA-N 0.000 claims 2
UMMDKSUKTIWOOO-UHFFFAOYSA-N 2-[4-[2-(5-fluoro-2-methoxypyridin-4-yl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]-N-methylethanamine Chemical compound FC=1C(=CC(=NC=1)OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)CCNC UMMDKSUKTIWOOO-UHFFFAOYSA-N 0.000 claims 2
KLDHHIADNSGEBS-UHFFFAOYSA-N 2-[4-[2-(5-fluoro-2-methylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-N,N-dimethylacetamide Chemical compound FC=1C(=CC(=NC=1)C)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(=O)N(C)C KLDHHIADNSGEBS-UHFFFAOYSA-N 0.000 claims 2
HOXUSDVZHNCSHR-UHFFFAOYSA-N 2-[4-[2-(5-fluoro-2-methylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-N-methylacetamide Chemical compound FC=1C(=CC(=NC=1)C)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(=O)NC HOXUSDVZHNCSHR-UHFFFAOYSA-N 0.000 claims 2
NJSWVIFWSIEFRR-UHFFFAOYSA-N 2-[4-[3-(2,2-difluoroethyl)-2-(2,6-dimethylpyridin-4-yl)-1H-indol-5-yl]piperidin-1-yl]-N,N-dimethylacetamide Chemical compound FC(CC1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC(=O)N(C)C)C1=CC(=NC(=C1)C)C)F NJSWVIFWSIEFRR-UHFFFAOYSA-N 0.000 claims 2
RKQRETHYYKXIND-UHFFFAOYSA-N 2-[4-[3-(cyclopropylmethyl)-2-(2-methoxypyridin-4-yl)-1H-indol-5-yl]piperidin-1-yl]-N-methylethanamine Chemical compound C1(CC1)CC1=C(NC2=CC=C(C=C12)C1CCN(CC1)CCNC)C1=CC(=NC=C1)OC RKQRETHYYKXIND-UHFFFAOYSA-N 0.000 claims 2
UPCMEHSVCKAHGV-UHFFFAOYSA-N 2-[4-[3-ethyl-2-(2-methylpyridin-4-yl)-1H-indol-5-yl]piperidin-1-yl]acetic acid Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC(=O)O)C1=CC(=NC=C1)C UPCMEHSVCKAHGV-UHFFFAOYSA-N 0.000 claims 2
NFANTQUNLDTLIT-UHFFFAOYSA-N 2-[4-[6-fluoro-2-(5-fluoro-2-methylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-N,N-dimethylacetamide Chemical compound FC1=C(C=C2C(=C(NC2=C1)C1=CC(=NC=C1F)C)C(C)C)C1CCN(CC1)CC(=O)N(C)C NFANTQUNLDTLIT-UHFFFAOYSA-N 0.000 claims 2
JPJNNZCUGXKYEC-UHFFFAOYSA-N 2-[[4-[2-(2,5-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]methyl]-1,3-oxazole Chemical compound CC1=NC=C(C(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC=1OC=CN=1)C JPJNNZCUGXKYEC-UHFFFAOYSA-N 0.000 claims 2
ITNPWSAYFAFXOK-UHFFFAOYSA-N 2-[[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]methyl]-1,3-oxazole Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC=1OC=CN=1)C ITNPWSAYFAFXOK-UHFFFAOYSA-N 0.000 claims 2
FIMGQFRJBNOXOX-UHFFFAOYSA-N 2-[butyl(2-hydroxyethyl)amino]-1-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound C(CCC)N(CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC(=C1)C)C)C(C)C)CCO FIMGQFRJBNOXOX-UHFFFAOYSA-N 0.000 claims 2
AYHDGDSWLRHOPX-UHFFFAOYSA-N 2-[tert-butyl(methyl)amino]-1-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound C(C)(C)(C)N(CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC(=C1)C)C)C(C)C)C AYHDGDSWLRHOPX-UHFFFAOYSA-N 0.000 claims 2
KKGNFWXWOZESLY-UHFFFAOYSA-N 2-amino-4-(3-ethyl-5-piperidin-4-yl-1H-indol-2-yl)pyridin-3-ol Chemical compound NC1=NC=CC(=C1O)C=1NC2=CC=C(C=C2C=1CC)C1CCNCC1 KKGNFWXWOZESLY-UHFFFAOYSA-N 0.000 claims 2
WNVBIRQMFDAGOI-UHFFFAOYSA-N 2-chloro-4-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)pyridine-3-carbonitrile Chemical compound ClC1=C(C#N)C(=CC=N1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1 WNVBIRQMFDAGOI-UHFFFAOYSA-N 0.000 claims 2
FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims 2
LTCVRNKOZSJLTA-UHFFFAOYSA-N 2-methyl-4-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)pyridin-3-amine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=C(C(=NC=C1)C)N LTCVRNKOZSJLTA-UHFFFAOYSA-N 0.000 claims 2
KFXJMCXUMDOSFK-UHFFFAOYSA-N 2-propan-2-yloxane-4-carbaldehyde Chemical compound CC(C)C1CC(C=O)CCO1 KFXJMCXUMDOSFK-UHFFFAOYSA-N 0.000 claims 2
SNHIONSTKAFDNL-UHFFFAOYSA-N 3-(2,2-difluoroethyl)-2-(2,6-dimethylpyridin-4-yl)-5-(1-methylpiperidin-4-yl)-1H-indole Chemical compound FC(CC1=C(NC2=CC=C(C=C12)C1CCN(CC1)C)C1=CC(=NC(=C1)C)C)F SNHIONSTKAFDNL-UHFFFAOYSA-N 0.000 claims 2
UGKWTDWUBNNILH-UHFFFAOYSA-N 3-(2,2-difluoroethyl)-2-(2,6-dimethylpyridin-4-yl)-5-(1-propan-2-ylpiperidin-4-yl)-1H-indole Chemical compound FC(CC1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(C)C)C1=CC(=NC(=C1)C)C)F UGKWTDWUBNNILH-UHFFFAOYSA-N 0.000 claims 2
XQKKNQMKIWIAEW-UHFFFAOYSA-N 3-(2,2-difluoroethyl)-2-(2,6-dimethylpyridin-4-yl)-5-[1-(1H-imidazol-5-ylmethyl)piperidin-4-yl]-1H-indole Chemical compound N1C=NC(=C1)CN1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC(=C1)C)C)CC(F)F XQKKNQMKIWIAEW-UHFFFAOYSA-N 0.000 claims 2
YPTSVRWGGJIMGF-UHFFFAOYSA-N 3-(2,2-difluoroethyl)-2-(2,6-dimethylpyridin-4-yl)-5-[1-[(2-methyl-1H-imidazol-5-yl)methyl]piperidin-4-yl]-1H-indole Chemical compound FC(CC1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC=1N=C(NC=1)C)C1=CC(=NC(=C1)C)C)F YPTSVRWGGJIMGF-UHFFFAOYSA-N 0.000 claims 2
XZRQXOLVASUWOI-UHFFFAOYSA-N 3-(2,2-difluoroethyl)-2-(2,6-dimethylpyridin-4-yl)-5-piperidin-4-yl-1H-indole Chemical compound FC(CC1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC(=NC(=C1)C)C)F XZRQXOLVASUWOI-UHFFFAOYSA-N 0.000 claims 2
RUFLVSBMOLEGFN-UHFFFAOYSA-N 3-(2,2-difluoroethyl)-2-(2-methylpyridin-4-yl)-5-piperidin-4-yl-1H-indole Chemical compound FC(CC1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC(=NC=C1)C)F RUFLVSBMOLEGFN-UHFFFAOYSA-N 0.000 claims 2
RNTKJPWFHGARBX-UHFFFAOYSA-N 3-(cyclopropylmethyl)-2-(2-methylpyridin-4-yl)-5-piperidin-4-yl-1H-indole Chemical compound C1(CC1)CC1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC(=NC=C1)C RNTKJPWFHGARBX-UHFFFAOYSA-N 0.000 claims 2
WKBOLHLPKYNOMI-UHFFFAOYSA-N 3-[2-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-oxoethyl]-1-methylimidazolidine-2,4-dione Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1C(N(CC1=O)C)=O)=O)C WKBOLHLPKYNOMI-UHFFFAOYSA-N 0.000 claims 2
HDDVAKCWZRGYLB-UHFFFAOYSA-N 3-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-N,N-diethylpropan-1-amine Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CCCN(CC)CC)C HDDVAKCWZRGYLB-UHFFFAOYSA-N 0.000 claims 2
YSKYDFDYWHUUEP-UHFFFAOYSA-N 3-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]propan-1-ol Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CCCO)C YSKYDFDYWHUUEP-UHFFFAOYSA-N 0.000 claims 2
BPZWDUXGZNPJNT-UHFFFAOYSA-N 3-[4-[2-(5-fluoro-2-methylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]propanenitrile Chemical compound FC=1C(=CC(=NC=1)C)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CCC#N BPZWDUXGZNPJNT-UHFFFAOYSA-N 0.000 claims 2
MTGHXAUFOKLGQO-UHFFFAOYSA-N 3-[4-[3-ethyl-2-(2-methylpyridin-4-yl)-1H-indol-5-yl]piperidin-1-yl]-N,N-dimethylpropan-1-amine Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CCCN(C)C)C1=CC(=NC=C1)C MTGHXAUFOKLGQO-UHFFFAOYSA-N 0.000 claims 2
XBWMGBYLPSIXJZ-UHFFFAOYSA-N 3-[[4-[2-(2,5-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]methyl]-1,2,4-oxadiazole Chemical compound CC1=NC=C(C(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC1=NOC=N1)C XBWMGBYLPSIXJZ-UHFFFAOYSA-N 0.000 claims 2
NUMXMNHTVCBMAX-UHFFFAOYSA-N 3-cyclopropyl-2-(2-methylpyridin-4-yl)-5-piperidin-4-yl-1H-indole Chemical compound C1(CC1)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC(=NC=C1)C NUMXMNHTVCBMAX-UHFFFAOYSA-N 0.000 claims 2
WKWFINYPPIJKKF-UHFFFAOYSA-N 3-ethyl-2-(2-fluoropyridin-4-yl)-5-[1-[1-(2-methylpropyl)piperidin-4-yl]piperidin-4-yl]-1H-indole Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCN(CC1)CC(C)C)C1=CC(=NC=C1)F WKWFINYPPIJKKF-UHFFFAOYSA-N 0.000 claims 2
ORYVASGEPKPOTH-UHFFFAOYSA-N 3-ethyl-2-(2-imidazol-1-ylpyridin-4-yl)-5-piperidin-4-yl-1H-indole Chemical compound N1(C=NC=C1)C1=NC=CC(=C1)C=1NC2=CC=C(C=C2C=1CC)C1CCNCC1 ORYVASGEPKPOTH-UHFFFAOYSA-N 0.000 claims 2
LIYBRDJQFIVMKY-UHFFFAOYSA-N 3-ethyl-2-(2-methoxypyridin-4-yl)-5-(1-piperidin-4-ylpiperidin-4-yl)-1H-indole Chemical compound N1(CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC=C1)OC)CC)C1CCNCC1 LIYBRDJQFIVMKY-UHFFFAOYSA-N 0.000 claims 2
BIWCYUUFIZURDQ-UHFFFAOYSA-N 3-ethyl-2-(2-methoxypyridin-4-yl)-5-[1-(1-methylpiperidin-4-yl)piperidin-4-yl]-1H-indole Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCN(CC1)C)C1=CC(=NC=C1)OC BIWCYUUFIZURDQ-UHFFFAOYSA-N 0.000 claims 2
MXEPXLWGKXWYBF-UHFFFAOYSA-N 3-ethyl-2-(2-methoxypyridin-4-yl)-5-[1-(1-propan-2-ylpiperidin-4-yl)piperidin-4-yl]-1H-indole Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCN(CC1)C(C)C)C1=CC(=NC=C1)OC MXEPXLWGKXWYBF-UHFFFAOYSA-N 0.000 claims 2
WYOUMPGNHMBVPB-UHFFFAOYSA-N 3-ethyl-2-(2-methoxypyridin-4-yl)-5-[1-[1-(2-methylpropyl)piperidin-4-yl]piperidin-4-yl]-1H-indole Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCN(CC1)CC(C)C)C1=CC(=NC=C1)OC WYOUMPGNHMBVPB-UHFFFAOYSA-N 0.000 claims 2
KPFYVTQBGUGUQJ-UHFFFAOYSA-N 3-ethyl-2-(2-methylpyridin-4-yl)-5-(1-propan-2-ylpiperidin-4-yl)-1H-indole Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(C)C)C1=CC(=NC=C1)C KPFYVTQBGUGUQJ-UHFFFAOYSA-N 0.000 claims 2
NMMRXHOPVAZNMM-UHFFFAOYSA-N 3-ethyl-2-(2-methylpyridin-4-yl)-5-[1-[(1-propan-2-ylpiperidin-4-yl)methyl]piperidin-4-yl]-1H-indole Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC1CCN(CC1)C(C)C)C1=CC(=NC=C1)C NMMRXHOPVAZNMM-UHFFFAOYSA-N 0.000 claims 2
FGMBGTFCAHQPPT-VWLOTQADSA-N 3-ethyl-2-(2-methylpyridin-4-yl)-5-[1-[[(2S)-1-propan-2-ylpyrrolidin-2-yl]methyl]piperidin-4-yl]-1H-indole Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C[C@H]1N(CCC1)C(C)C)C1=CC(=NC=C1)C FGMBGTFCAHQPPT-VWLOTQADSA-N 0.000 claims 2
IRZIVYDRLKLPQM-LJQANCHMSA-N 3-ethyl-2-(2-methylpyridin-4-yl)-5-[1-[[(3R)-pyrrolidin-3-yl]methyl]piperidin-4-yl]-1H-indole Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C[C@H]1CNCC1)C1=CC(=NC=C1)C IRZIVYDRLKLPQM-LJQANCHMSA-N 0.000 claims 2
YLTQYNWFZDDEKQ-UHFFFAOYSA-N 3-ethyl-2-(2-methylpyridin-4-yl)-5-piperidin-4-yl-1H-indole Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC(=NC=C1)C YLTQYNWFZDDEKQ-UHFFFAOYSA-N 0.000 claims 2
RMNJXKAFVFWQBG-UHFFFAOYSA-N 3-ethyl-2-pyridin-4-yl-5-[1-(2,2,6,6-tetramethylpiperidin-4-yl)piperidin-4-yl]-1H-indole Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CC(NC(C1)(C)C)(C)C)C1=CC=NC=C1 RMNJXKAFVFWQBG-UHFFFAOYSA-N 0.000 claims 2
AFETVRWREHOYTD-UHFFFAOYSA-N 3-ethyl-4,6-difluoro-2-(2-methylpyridin-4-yl)-5-piperidin-4-yl-1H-indole Chemical compound C(C)C1=C(NC2=CC(=C(C(=C12)F)C1CCNCC1)F)C1=CC(=NC=C1)C AFETVRWREHOYTD-UHFFFAOYSA-N 0.000 claims 2
ITGQZMUWGUGBOI-UHFFFAOYSA-N 3-ethyl-5-(1-methylpiperidin-4-yl)-2-(2-methylpyridin-4-yl)-1H-indole Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C)C1=CC(=NC=C1)C ITGQZMUWGUGBOI-UHFFFAOYSA-N 0.000 claims 2
FLHBJMGJLNGEQB-UHFFFAOYSA-N 3-ethyl-5-[1-(1-ethylpiperidin-4-yl)piperidin-4-yl]-2-pyridin-4-yl-1H-indole Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCN(CC1)CC)C1=CC=NC=C1 FLHBJMGJLNGEQB-UHFFFAOYSA-N 0.000 claims 2
AJXIVGLWDSOZKJ-UHFFFAOYSA-N 3-ethyl-5-[1-(1-methylpiperidin-4-yl)piperidin-4-yl]-2-pyridin-4-yl-1H-indole Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCN(CC1)C)C1=CC=NC=C1 AJXIVGLWDSOZKJ-UHFFFAOYSA-N 0.000 claims 2
DDANJXNNXTZWFI-UHFFFAOYSA-N 3-ethyl-5-[1-[(1-methylpyrrol-2-yl)methyl]piperidin-4-yl]-2-pyridin-4-yl-1H-indole Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC=1N(C=CC=1)C)C1=CC=NC=C1 DDANJXNNXTZWFI-UHFFFAOYSA-N 0.000 claims 2
BZKKHCIMWAFYFR-UHFFFAOYSA-N 3-ethyl-5-[1-[1-(2-methylpropyl)piperidin-4-yl]piperidin-4-yl]-2-(2-propan-2-yloxypyridin-4-yl)-1H-indole Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCN(CC1)CC(C)C)C1=CC(=NC=C1)OC(C)C BZKKHCIMWAFYFR-UHFFFAOYSA-N 0.000 claims 2
UJXQNXWZNFWQSY-UHFFFAOYSA-N 3-ethyl-5-[1-[1-(2-methylpropyl)piperidin-4-yl]piperidin-4-yl]-2-pyridin-4-yl-1H-indole Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCN(CC1)CC(C)C)C1=CC=NC=C1 UJXQNXWZNFWQSY-UHFFFAOYSA-N 0.000 claims 2
LNKLQLFWNRZCLO-UHFFFAOYSA-N 3-ethyl-5-piperidin-4-yl-2-pyridin-4-yl-1H-indole Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC=NC=C1 LNKLQLFWNRZCLO-UHFFFAOYSA-N 0.000 claims 2
JCKVOBRFDMLCNM-UHFFFAOYSA-N 3-methoxy-1-[4-[2-(2-methylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]propan-1-one Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(CCOC)=O)C1=CC(=NC=C1)C JCKVOBRFDMLCNM-UHFFFAOYSA-N 0.000 claims 2
GKENUMJCKKDCSN-UHFFFAOYSA-N 3-methyl-2-(2-methylpyridin-4-yl)-5-[1-(1-propan-2-ylpiperidin-4-yl)piperidin-4-yl]-1H-indole Chemical compound C(C)(C)N1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC=C1)C)C GKENUMJCKKDCSN-UHFFFAOYSA-N 0.000 claims 2
YHCJNYZGNCFDQM-UHFFFAOYSA-N 3-methyl-5-[1-(1-methylpiperidin-4-yl)piperidin-4-yl]-2-pyridin-4-yl-1H-indole Chemical compound CC1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCN(CC1)C)C1=CC=NC=C1 YHCJNYZGNCFDQM-UHFFFAOYSA-N 0.000 claims 2
AQQGARNXTBEFMU-UHFFFAOYSA-N 3-methyl-5-[1-(1-propan-2-ylpiperidin-4-yl)piperidin-4-yl]-2-pyridin-4-yl-1H-indole Chemical compound C(C)(C)N1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC=NC=C1)C AQQGARNXTBEFMU-UHFFFAOYSA-N 0.000 claims 2
CHHBUJKGMOEBSW-UHFFFAOYSA-N 3-methyl-5-[1-[1-(2-methylpropyl)piperidin-4-yl]piperidin-4-yl]-2-(2-methylpyridin-4-yl)-1H-indole Chemical compound C(C(C)C)N1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC=C1)C)C CHHBUJKGMOEBSW-UHFFFAOYSA-N 0.000 claims 2
AWUOQLZOTLZXAZ-UHFFFAOYSA-N 3-methyl-5-[1-[1-(2-methylpropyl)piperidin-4-yl]piperidin-4-yl]-2-pyridin-4-yl-1H-indole Chemical compound C(C(C)C)N1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC=NC=C1)C AWUOQLZOTLZXAZ-UHFFFAOYSA-N 0.000 claims 2
VJQHJNIGWOABDZ-UHFFFAOYSA-N 3-methyloxetane Chemical compound CC1COC1 VJQHJNIGWOABDZ-UHFFFAOYSA-N 0.000 claims 2
125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
QDCHKAZDDBXOTA-UHFFFAOYSA-N 3-tert-butyl-2-(2,6-dimethylpyridin-4-yl)-5-piperidin-4-yl-1H-indole Chemical compound C(C)(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC(=NC(=C1)C)C QDCHKAZDDBXOTA-UHFFFAOYSA-N 0.000 claims 2
UIONGSXEQHQEDA-UHFFFAOYSA-N 3-tert-butyl-2-(2-methylpyridin-4-yl)-5-piperidin-4-yl-1H-indole Chemical compound C(C)(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC(=NC=C1)C UIONGSXEQHQEDA-UHFFFAOYSA-N 0.000 claims 2
KDUQRIBTNIQDMU-UHFFFAOYSA-N 4-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-3-(trifluoromethyl)pyridine-2-carbonitrile Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=C(C(=NC=C1)C#N)C(F)(F)F KDUQRIBTNIQDMU-UHFFFAOYSA-N 0.000 claims 2
CAJUDZLSXHQKIH-UHFFFAOYSA-N 4-[2-(2-methylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-2-one Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CC(NCC1)=O)C1=CC(=NC=C1)C CAJUDZLSXHQKIH-UHFFFAOYSA-N 0.000 claims 2
DLROEZYRZNBJPO-UHFFFAOYSA-N 4-[2-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-oxoethyl]piperazin-2-one Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1CC(NCC1)=O)=O)C DLROEZYRZNBJPO-UHFFFAOYSA-N 0.000 claims 2
JRGAXLGFQIZWHP-UHFFFAOYSA-N 4-[3-ethyl-5-[1-[1-(2-methylpropyl)piperidin-4-yl]piperidin-4-yl]-1H-indol-2-yl]-1H-pyridin-2-one Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCN(CC1)CC(C)C)C1=CC(=NC=C1)O JRGAXLGFQIZWHP-UHFFFAOYSA-N 0.000 claims 2
FVPUVKQWRCWCOU-UHFFFAOYSA-N 4-[3-ethyl-5-[1-[1-(2-methylpropyl)piperidin-4-yl]piperidin-4-yl]-1H-indol-2-yl]-N,N-dimethylpyridin-2-amine Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCN(CC1)CC(C)C)C1=CC(=NC=C1)N(C)C FVPUVKQWRCWCOU-UHFFFAOYSA-N 0.000 claims 2
NXSBHHRFHJNDGK-UHFFFAOYSA-N 4-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]thiane 1,1-dioxide Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C1CCS(CC1)(=O)=O)C NXSBHHRFHJNDGK-UHFFFAOYSA-N 0.000 claims 2
YUKZPSPHUPXBAR-UHFFFAOYSA-N 4-[4-[2-(2-cyclopropyl-5-fluoropyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidine-1-carbonyl]-1-methylpyrrolidin-2-one Chemical compound C1(CC1)C1=NC=C(C(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(=O)C1CC(N(C1)C)=O)F YUKZPSPHUPXBAR-UHFFFAOYSA-N 0.000 claims 2
AVYLXZDFYNQJKT-UHFFFAOYSA-N 4-[4-[2-(2-methylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidine-1-carbonyl]pyrrolidin-2-one Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(=O)C1CC(NC1)=O)C1=CC(=NC=C1)C AVYLXZDFYNQJKT-UHFFFAOYSA-N 0.000 claims 2
LICGTDVEDOKCAT-UHFFFAOYSA-N 4-[4-[2-(3-fluoro-2-methylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidine-1-carbonyl]-1-methylpyrrolidin-2-one Chemical compound FC=1C(=NC=CC=1C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(=O)C1CC(N(C1)C)=O)C LICGTDVEDOKCAT-UHFFFAOYSA-N 0.000 claims 2
IVJZFRQTUCNMBK-UHFFFAOYSA-N 4-[4-[2-(5-fluoro-2-methylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidine-1-carbonyl]-1-methylpyrrolidin-2-one Chemical compound FC=1C(=CC(=NC=1)C)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(=O)C1CC(N(C1)C)=O IVJZFRQTUCNMBK-UHFFFAOYSA-N 0.000 claims 2
XILPCSMEKCBYFO-UHFFFAOYSA-N 4-methyl-1,2,4-triazole Chemical compound CN1C=NN=C1 XILPCSMEKCBYFO-UHFFFAOYSA-N 0.000 claims 2
VXWCTQZREYJEMU-UHFFFAOYSA-N 4-methylpiperidine-4-carbaldehyde Chemical compound O=CC1(C)CCNCC1 VXWCTQZREYJEMU-UHFFFAOYSA-N 0.000 claims 2
YGCREQMWFNHBHG-UHFFFAOYSA-N 5-(1-benzylsulfonylpiperidin-4-yl)-2-(2-methylpyridin-4-yl)-3-propan-2-yl-1H-indole Chemical compound C(C1=CC=CC=C1)S(=O)(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC=C1)C)C(C)C YGCREQMWFNHBHG-UHFFFAOYSA-N 0.000 claims 2
GRPVTFYMRUUOCF-UHFFFAOYSA-N 5-(1-cyclopentylpiperidin-4-yl)-2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indole Chemical compound C1(CCCC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC(=C1)C)C)C(C)C GRPVTFYMRUUOCF-UHFFFAOYSA-N 0.000 claims 2
YNUXJHCVLNKRTC-UHFFFAOYSA-N 5-(1-ethylsulfonylpiperidin-4-yl)-2-(2-methylpyridin-4-yl)-3-propan-2-yl-1H-indole Chemical compound C(C)S(=O)(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC=C1)C)C(C)C YNUXJHCVLNKRTC-UHFFFAOYSA-N 0.000 claims 2
DHRRNCQEPHWLNT-UHFFFAOYSA-N 5-(3,3-difluoropiperidin-4-yl)-2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indole Chemical compound FC1(CNCCC1C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC(=C1)C)C)C(C)C)F DHRRNCQEPHWLNT-UHFFFAOYSA-N 0.000 claims 2
XDCQPYBUBZZPJE-UHFFFAOYSA-N 5-[1-(1,3-difluoropropan-2-yl)piperidin-4-yl]-2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indole Chemical compound FCC(CF)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC(=C1)C)C)C(C)C XDCQPYBUBZZPJE-UHFFFAOYSA-N 0.000 claims 2
XVTNJRJHHHGPMP-UHFFFAOYSA-N 5-[1-(1-cyclopentylpiperidin-4-yl)piperidin-4-yl]-3-ethyl-2-(2-methoxypyridin-4-yl)-1H-indole Chemical compound C1(CCCC1)N1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC=C1)OC)CC XVTNJRJHHHGPMP-UHFFFAOYSA-N 0.000 claims 2
FBRBOZCIJIBDSK-UHFFFAOYSA-N 5-[1-(1-ethylpiperidin-4-yl)piperidin-4-yl]-2-(2-methoxypyridin-4-yl)-3-methyl-1H-indole Chemical compound C(C)N1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC=C1)OC)C FBRBOZCIJIBDSK-UHFFFAOYSA-N 0.000 claims 2
BLNVBYKQQBHYJP-UHFFFAOYSA-N 5-[1-(1-ethylpiperidin-4-yl)piperidin-4-yl]-2-(2-methoxypyridin-4-yl)-3-propan-2-yl-1H-indole Chemical compound C(C)N1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC=C1)OC)C(C)C BLNVBYKQQBHYJP-UHFFFAOYSA-N 0.000 claims 2
YDJKOMNMFAJHOT-UHFFFAOYSA-N 5-[1-(1-ethylpiperidin-4-yl)piperidin-4-yl]-3-methyl-2-pyridin-4-yl-1H-indole Chemical compound C(C)N1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC=NC=C1)C YDJKOMNMFAJHOT-UHFFFAOYSA-N 0.000 claims 2
PQGUZZYEWMZUAP-UHFFFAOYSA-N 5-[1-(1-fluoropropan-2-yl)piperidin-4-yl]-2-(2-methylpyridin-4-yl)-3-propan-2-yl-1H-indole Chemical compound FCC(C)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC=C1)C)C(C)C PQGUZZYEWMZUAP-UHFFFAOYSA-N 0.000 claims 2
FLTWHXLFOSAIOO-UHFFFAOYSA-N 5-[1-(1-methylpiperidin-4-yl)piperidin-4-yl]-3-propan-2-yl-2-pyridin-4-yl-1H-indole Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCN(CC1)C)C1=CC=NC=C1 FLTWHXLFOSAIOO-UHFFFAOYSA-N 0.000 claims 2
DLMKBIAYLVQKQR-UHFFFAOYSA-N 5-[1-(2,2-difluoroethyl)piperidin-4-yl]-2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indole Chemical compound FC(CN1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC(=C1)C)C)C(C)C)F DLMKBIAYLVQKQR-UHFFFAOYSA-N 0.000 claims 2
AFGCAOPGLCLMNL-UHFFFAOYSA-N 5-[1-(2,2-difluoroethyl)piperidin-4-yl]-2-(2-methylpyridin-4-yl)-3-propan-2-yl-1H-indole Chemical compound FC(CN1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC=C1)C)C(C)C)F AFGCAOPGLCLMNL-UHFFFAOYSA-N 0.000 claims 2
PYWBPEBSDCPESD-UHFFFAOYSA-N 5-[1-(2,2-dimethylpropyl)piperidin-4-yl]-2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indole Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(C)(C)C)C PYWBPEBSDCPESD-UHFFFAOYSA-N 0.000 claims 2
RHLBUVISQVSFKQ-UHFFFAOYSA-N 5-[1-(2,3,4,4a,5,6,7,7a-octahydrocyclopenta[b]pyran-4-yl)piperidin-4-yl]-2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indole Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C1C2C(OCC1)CCC2)C RHLBUVISQVSFKQ-UHFFFAOYSA-N 0.000 claims 2
NUQRLTATSFTTDM-UHFFFAOYSA-N 5-[1-(2,6-dimethyloxan-4-yl)piperidin-4-yl]-2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indole Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C1CC(OC(C1)C)C)C NUQRLTATSFTTDM-UHFFFAOYSA-N 0.000 claims 2
MCNAKRHUCFUTGW-UHFFFAOYSA-N 5-[1-(2-ethoxyethyl)piperidin-4-yl]-2-(2-methoxypyridin-4-yl)-3-propan-2-yl-1H-indole Chemical compound C(C)OCCN1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC=C1)OC)C(C)C MCNAKRHUCFUTGW-UHFFFAOYSA-N 0.000 claims 2
CKVGHMFAENMPGA-UHFFFAOYSA-N 5-[1-(2-ethoxyethyl)piperidin-4-yl]-2-(2-methylpyridin-4-yl)-3-propan-2-yl-1H-indole Chemical compound C(C)OCCN1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC=C1)C)C(C)C CKVGHMFAENMPGA-UHFFFAOYSA-N 0.000 claims 2
WKABIKXMCLQVBM-UHFFFAOYSA-N 5-[1-(2-methylpropylsulfonyl)piperidin-4-yl]-2-(2-methylpyridin-4-yl)-3-propan-2-yl-1H-indole Chemical compound C(C(C)C)S(=O)(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC=C1)C)C(C)C WKABIKXMCLQVBM-UHFFFAOYSA-N 0.000 claims 2
VLPCWDIBKUEXRO-UHFFFAOYSA-N 5-[1-(3-fluoro-1-propan-2-ylpiperidin-4-yl)piperidin-4-yl]-2-(2-methylpyridin-4-yl)-3-propan-2-yl-1H-indole Chemical compound FC1CN(CCC1N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC=C1)C)C(C)C)C(C)C VLPCWDIBKUEXRO-UHFFFAOYSA-N 0.000 claims 2
WOQJNYGCAAQSQV-UHFFFAOYSA-N 5-[1-(3-fluoropiperidin-4-yl)piperidin-4-yl]-2-(2-methylpyridin-4-yl)-3-propan-2-yl-1H-indole Chemical compound FC1CNCCC1N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC=C1)C)C(C)C WOQJNYGCAAQSQV-UHFFFAOYSA-N 0.000 claims 2
BFJZXMMZBJPLNV-UHFFFAOYSA-N 5-[1-(3-methylpiperidin-4-yl)piperidin-4-yl]-2-(2-methylpyridin-4-yl)-3-propan-2-yl-1H-indole Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1C(CNCC1)C)C1=CC(=NC=C1)C BFJZXMMZBJPLNV-UHFFFAOYSA-N 0.000 claims 2
HYRDVWVZCQFMHA-UHFFFAOYSA-N 5-[1-(4-chlorophenyl)sulfonylpiperidin-4-yl]-2-(2-methylpyridin-4-yl)-3-propan-2-yl-1H-indole Chemical compound ClC1=CC=C(C=C1)S(=O)(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC=C1)C)C(C)C HYRDVWVZCQFMHA-UHFFFAOYSA-N 0.000 claims 2
VTYFDQQWVRTXGV-UHFFFAOYSA-N 5-[1-(benzenesulfonyl)piperidin-4-yl]-2-(2-methylpyridin-4-yl)-3-propan-2-yl-1H-indole Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)S(=O)(=O)C1=CC=CC=C1)C1=CC(=NC=C1)C VTYFDQQWVRTXGV-UHFFFAOYSA-N 0.000 claims 2
RQHJQGNHJOFREY-UHFFFAOYSA-N 5-[1-(cyclobutylmethyl)piperidin-4-yl]-2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indole Chemical compound C1(CCC1)CN1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC(=C1)C)C)C(C)C RQHJQGNHJOFREY-UHFFFAOYSA-N 0.000 claims 2
NSAUIIACEKGXLU-UHFFFAOYSA-N 5-[1-(cyclohexylmethyl)piperidin-4-yl]-2-(2-methylpyridin-4-yl)-3-propan-2-yl-1H-indole Chemical compound C1(CCCCC1)CN1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC=C1)C)C(C)C NSAUIIACEKGXLU-UHFFFAOYSA-N 0.000 claims 2
DNQWQQGOJIGANI-UHFFFAOYSA-N 5-[1-[(3-methyloxetan-3-yl)methyl]piperidin-4-yl]-2-(2-methylpyridin-4-yl)-3-propan-2-yl-1H-indole Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC1(COC1)C)C1=CC(=NC=C1)C DNQWQQGOJIGANI-UHFFFAOYSA-N 0.000 claims 2
UXTWDUSWRPSOII-UHFFFAOYSA-N 5-[1-[(5-methyl-1H-imidazol-4-yl)methyl]piperidin-4-yl]-2-(2-methylpyridin-4-yl)-3-propan-2-yl-1H-indole Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC1=C(N=CN1)C)C1=CC(=NC=C1)C UXTWDUSWRPSOII-UHFFFAOYSA-N 0.000 claims 2
YJOYIEKLEVHYHI-UHFFFAOYSA-N 5-[1-[1-(cyclopropylmethyl)piperidin-4-yl]piperidin-4-yl]-2-(2-methoxypyridin-4-yl)-3-propan-2-yl-1H-indole Chemical compound C1(CC1)CN1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC=C1)OC)C(C)C YJOYIEKLEVHYHI-UHFFFAOYSA-N 0.000 claims 2
DPVITICGZQWHLI-UHFFFAOYSA-N 5-[1-[1-(cyclopropylmethyl)piperidin-4-yl]piperidin-4-yl]-3-ethyl-2-(2-methoxypyridin-4-yl)-1H-indole Chemical compound C1(CC1)CN1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC=C1)OC)CC DPVITICGZQWHLI-UHFFFAOYSA-N 0.000 claims 2
AXUFXBHVXJWNOH-UHFFFAOYSA-N 5-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidine-1-carbonyl]-3-methyl-1H-pyridazin-6-one Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(=O)C=1C(NN=C(C=1)C)=O)C AXUFXBHVXJWNOH-UHFFFAOYSA-N 0.000 claims 2
NXFUKSZBRKWOFX-UHFFFAOYSA-N 5-methyl-4-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)pyridin-2-amine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC(=NC=C1C)N NXFUKSZBRKWOFX-UHFFFAOYSA-N 0.000 claims 2
VXASVEDHEJYYKS-UHFFFAOYSA-N 5-piperidin-4-yl-3-propan-2-yl-2-(2,3,5,6-tetramethylpyridin-4-yl)-1H-indole Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=C(C(=NC(=C1C)C)C)C VXASVEDHEJYYKS-UHFFFAOYSA-N 0.000 claims 2
OBRKVPBKOLUWIL-UHFFFAOYSA-N 5-piperidin-4-yl-3-propan-2-yl-2-(2,3,6-trimethylpyridin-4-yl)-1H-indole Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=C(C(=NC(=C1)C)C)C OBRKVPBKOLUWIL-UHFFFAOYSA-N 0.000 claims 2
AQGAQCUFGPSJCB-UHFFFAOYSA-N 5-piperidin-4-yl-3-propan-2-yl-2-[2-(trifluoromethyl)pyridin-4-yl]-1H-indole Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC(=NC=C1)C(F)(F)F AQGAQCUFGPSJCB-UHFFFAOYSA-N 0.000 claims 2
LZBQEOOGVHEDRW-UHFFFAOYSA-N 5-piperidin-4-yl-3-propan-2-yl-2-pyridin-4-yl-1H-indole Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC=NC=C1 LZBQEOOGVHEDRW-UHFFFAOYSA-N 0.000 claims 2
PRDFESRDFZXCRA-UHFFFAOYSA-N 6-chloro-4-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)pyridine-3-carbonitrile Chemical compound ClC1=NC=C(C#N)C(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1 PRDFESRDFZXCRA-UHFFFAOYSA-N 0.000 claims 2
PKOZZHZIEOPBFC-UHFFFAOYSA-N 6-fluoro-2-(2-methylpyridin-4-yl)-3-propan-2-yl-5-[1-(1-propan-2-ylpiperidin-4-yl)piperidin-4-yl]-1H-indole Chemical compound FC1=C(C=C2C(=C(NC2=C1)C1=CC(=NC=C1)C)C(C)C)C1CCN(CC1)C1CCN(CC1)C(C)C PKOZZHZIEOPBFC-UHFFFAOYSA-N 0.000 claims 2
MFBSGNLSOOTPMO-UHFFFAOYSA-N 6-fluoro-2-(2-methylpyridin-4-yl)-5-piperidin-4-yl-3-propan-2-yl-1H-indole Chemical compound FC1=C(C=C2C(=C(NC2=C1)C1=CC(=NC=C1)C)C(C)C)C1CCNCC1 MFBSGNLSOOTPMO-UHFFFAOYSA-N 0.000 claims 2
KPHQFONMSKYHLU-UHFFFAOYSA-N 6-fluoro-2-(5-fluoro-2-methylpyridin-4-yl)-5-piperidin-4-yl-3-propan-2-yl-1H-indole Chemical compound FC1=C(C=C2C(=C(NC2=C1)C1=CC(=NC=C1F)C)C(C)C)C1CCNCC1 KPHQFONMSKYHLU-UHFFFAOYSA-N 0.000 claims 2
KHGUMMRVFBLTOH-UHFFFAOYSA-N 6-methyl-4-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)pyridin-2-amine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC(=NC(=C1)C)N KHGUMMRVFBLTOH-UHFFFAOYSA-N 0.000 claims 2
CIZUBUALYUNNSD-UHFFFAOYSA-N 6-methyl-4-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)pyridine-3-carboxamide Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC(=NC=C1C(=O)N)C CIZUBUALYUNNSD-UHFFFAOYSA-N 0.000 claims 2
208000023275 Autoimmune disease Diseases 0.000 claims 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 2
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JP2019513033A 2016-09-09 2017-09-08 ピリジル置換のインドール化合物 Active JP7028861B2 (ja)