JP2019525941A5

JP2019525941A5 -

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Publication number: JP2019525941A5
Authority: JP; Japan
Prior art keywords: dimethoxyphenyl; piperidin; indol; methyl; indole
Prior art date: 2017-07-27
Legal status : Granted

Application number

JP2019504954A

Other languages

English (en)

Japanese (ja)

Other versions

JP6995109B2 (ja

JP2019525941A (ja

Filing date

2017-07-27

Publication date

2020-08-20

2017-07-27 Application filed filed Critical

2017-07-27 Priority claimed from PCT/US2017/044091 external-priority patent/WO2018026620A1/en

2019-09-12 Publication of JP2019525941A publication Critical patent/JP2019525941A/ja

2020-08-20 Publication of JP2019525941A5 publication Critical patent/JP2019525941A5/ja

2022-01-14 Application granted granted Critical

2022-01-14 Publication of JP6995109B2 publication Critical patent/JP6995109B2/ja

Status Active legal-status Critical Current

2037-07-27 Anticipated expiration legal-status Critical

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125000000217 alkyl group Chemical group 0.000 claims 69
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 54
-1 2-oxa-6-azaspiro[3,3]heptanyl Chemical group 0.000 claims 39
125000003709 fluoroalkyl group Chemical group 0.000 claims 25
125000002768 hydroxyalkyl group Chemical group 0.000 claims 23
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 15
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 15
125000001412 tetrahydropyranyl group Chemical group 0.000 claims 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
125000000168 pyrrolyl group Chemical group 0.000 claims 12
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 12
125000004966 cyanoalkyl group Chemical group 0.000 claims 11
125000000719 pyrrolidinyl group Chemical group 0.000 claims 11
125000000714 pyrimidinyl group Chemical group 0.000 claims 10
229910052799 carbon Inorganic materials 0.000 claims 9
150000001875 compounds Chemical class 0.000 claims 9
125000003386 piperidinyl group Chemical group 0.000 claims 9
125000003226 pyrazolyl group Chemical group 0.000 claims 9
150000003839 salts Chemical class 0.000 claims 9
125000002541 furyl group Chemical group 0.000 claims 8
125000002883 imidazolyl group Chemical group 0.000 claims 8
125000001041 indolyl group Chemical group 0.000 claims 8
125000003566 oxetanyl group Chemical group 0.000 claims 8
125000004193 piperazinyl group Chemical group 0.000 claims 8
125000004076 pyridyl group Chemical group 0.000 claims 8
125000001424 substituent group Chemical group 0.000 claims 8
125000001113 thiadiazolyl group Chemical group 0.000 claims 8
125000000335 thiazolyl group Chemical group 0.000 claims 8
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 7
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 6
125000000842 isoxazolyl group Chemical group 0.000 claims 5
125000002757 morpholinyl group Chemical group 0.000 claims 5
125000002971 oxazolyl group Chemical group 0.000 claims 5
125000001425 triazolyl group Chemical group 0.000 claims 5
JKOVZZPEDUESEM-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-ethyl-6-methoxy-5-[1-(1-propan-2-ylpiperidin-4-yl)piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC(=C(C=C2C=1CC)C1CCN(CC1)C1CCN(CC1)C(C)C)OC JKOVZZPEDUESEM-UHFFFAOYSA-N 0.000 claims 4
JOFMIBPMPXFQHK-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-[1-(2-methylpropyl)piperidin-3-yl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CN(CCC1)CC(C)C JOFMIBPMPXFQHK-UHFFFAOYSA-N 0.000 claims 4
BTPYIYXVLIKHCL-UHFFFAOYSA-N 2-[[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]methyl]quinoline Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)CC1=NC2=CC=CC=C2C=C1 BTPYIYXVLIKHCL-UHFFFAOYSA-N 0.000 claims 4
SBBGJTRADGSBTI-UHFFFAOYSA-N 5-[1-(1-butan-2-ylpiperidin-4-yl)piperidin-4-yl]-2-(3,4-dimethoxyphenyl)-3-methyl-1H-indole Chemical compound C(C)(CC)N1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)C SBBGJTRADGSBTI-UHFFFAOYSA-N 0.000 claims 4
125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 4
XCZDEPOZCFYCQQ-UHFFFAOYSA-N FC(C(=O)O)(F)F.FC(C(=O)O)(F)F.COC=1C=C(C=CC1OC)C=1NC2=CC(=C(C=C2C1C(C)C)C1CCN(CC1)C1CCN(CC1)C(C)C)C Chemical compound FC(C(=O)O)(F)F.FC(C(=O)O)(F)F.COC=1C=C(C=CC1OC)C=1NC2=CC(=C(C=C2C1C(C)C)C1CCN(CC1)C1CCN(CC1)C(C)C)C XCZDEPOZCFYCQQ-UHFFFAOYSA-N 0.000 claims 4
125000003725 azepanyl group Chemical group 0.000 claims 4
125000004799 bromophenyl group Chemical group 0.000 claims 4
125000000753 cycloalkyl group Chemical group 0.000 claims 4
125000005959 diazepanyl group Chemical group 0.000 claims 4
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 4
125000001624 naphthyl group Chemical group 0.000 claims 4
239000008194 pharmaceutical composition Substances 0.000 claims 4
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 4
125000003373 pyrazinyl group Chemical group 0.000 claims 4
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 4
125000003831 tetrazolyl group Chemical group 0.000 claims 4
125000001544 thienyl group Chemical group 0.000 claims 4
BPYWXLLORBQURI-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[3-(hydroxymethyl)piperidin-1-yl]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1CC(CCC1)CO)=O BPYWXLLORBQURI-UHFFFAOYSA-N 0.000 claims 3
125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 3
125000004432 carbon atom Chemical group C* 0.000 claims 3
125000004965 chloroalkyl group Chemical group 0.000 claims 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 3
LPYYAODRWJUTJF-MRXNPFEDSA-N (3R)-1-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-3-hydroxybutan-1-one Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)C(C[C@@H](C)O)=O LPYYAODRWJUTJF-MRXNPFEDSA-N 0.000 claims 2
UUBRYRACQVGIQZ-RUZDIDTESA-N (3R)-N-(2-amino-2-oxoethyl)-1-[2-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-oxoethyl]piperidine-3-carboxamide Chemical compound NC(CNC(=O)[C@H]1CN(CCC1)CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)C(C)C)=O UUBRYRACQVGIQZ-RUZDIDTESA-N 0.000 claims 2
HXMGYSNKQUDWEN-AREMUKBSSA-N (3R)-N-(cyanomethyl)-1-[2-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-oxoethyl]piperidine-3-carboxamide Chemical compound C(#N)CNC(=O)[C@H]1CN(CCC1)CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)C(C)C HXMGYSNKQUDWEN-AREMUKBSSA-N 0.000 claims 2
FSSJZTDSHSFRES-LJAQVGFWSA-N (3S)-1-[2-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-oxoethyl]-N-[1-(hydroxymethyl)cyclopentyl]piperidine-3-carboxamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1C[C@H](CCC1)C(=O)NC1(CCCC1)CO)=O FSSJZTDSHSFRES-LJAQVGFWSA-N 0.000 claims 2
GMKCMRDNCXUNPA-MHZLTWQESA-N (3S)-1-[2-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-oxoethyl]-N-propan-2-ylpiperidine-3-carboxamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1C[C@H](CCC1)C(=O)NC(C)C)=O GMKCMRDNCXUNPA-MHZLTWQESA-N 0.000 claims 2
LPYYAODRWJUTJF-INIZCTEOSA-N (3S)-1-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-3-hydroxybutan-1-one Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)C(C[C@H](C)O)=O LPYYAODRWJUTJF-INIZCTEOSA-N 0.000 claims 2
JCPMNDYXNNPEPN-NDEPHWFRSA-N (3S)-N-(2-acetamidoethyl)-1-[2-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-oxoethyl]piperidine-3-carboxamide Chemical compound COC1=C(OC)C=C(C=C1)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CCN(CC1)C(=O)CN1CCC[C@@H](C1)C(=O)NCCNC(C)=O JCPMNDYXNNPEPN-NDEPHWFRSA-N 0.000 claims 2
HXMGYSNKQUDWEN-SANMLTNESA-N (3S)-N-(cyanomethyl)-1-[2-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-oxoethyl]piperidine-3-carboxamide Chemical compound C(#N)CNC(=O)[C@@H]1CN(CCC1)CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)C(C)C HXMGYSNKQUDWEN-SANMLTNESA-N 0.000 claims 2
GJJRTQQRYPFLKJ-UHFFFAOYSA-N 1-(4-acetylpiperazin-1-yl)-2-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound C(C)(=O)N1CCN(CC1)C(CN1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)CC(F)(F)F)=O GJJRTQQRYPFLKJ-UHFFFAOYSA-N 0.000 claims 2
BHEMIEXDMRFLDD-VWLOTQADSA-N 1-[(2S)-2-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidine-1-carbonyl]pyrrolidin-1-yl]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)C(=O)[C@H]1N(CCC1)C(C)=O BHEMIEXDMRFLDD-VWLOTQADSA-N 0.000 claims 2
ONWIXXBXAAUXTG-UHFFFAOYSA-N 1-[2-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-2-oxoethyl]-N,N-dimethylpiperidine-3-carboxamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)C(CN1CC(CCC1)C(=O)N(C)C)=O ONWIXXBXAAUXTG-UHFFFAOYSA-N 0.000 claims 2
XBBCSQIBQLQTLG-UHFFFAOYSA-N 1-[2-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]acetyl]piperidine-4-carboxamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)CC(=O)N1CCC(CC1)C(=O)N XBBCSQIBQLQTLG-UHFFFAOYSA-N 0.000 claims 2
FWSHCZFAYQNRNN-UHFFFAOYSA-N 1-[2-[4-[2-(3,4-dimethoxyphenyl)-3-ethyl-1H-indol-5-yl]piperidin-1-yl]-2-oxoethyl]piperidine-3-carboxylic acid Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C(CN1CC(CCC1)C(=O)O)=O FWSHCZFAYQNRNN-UHFFFAOYSA-N 0.000 claims 2
BFVHNMBPDDHQMB-UHFFFAOYSA-N 1-[2-[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]-2-oxoethyl]-N,N-diethylpiperidine-3-carboxamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C(CN1CC(CCC1)C(=O)N(CC)CC)=O BFVHNMBPDDHQMB-UHFFFAOYSA-N 0.000 claims 2
ALIAUSDVMZLDTD-UHFFFAOYSA-N 1-[2-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-oxoethyl]-N,N-diethylpiperidine-3-carboxamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1CC(CCC1)C(=O)N(CC)CC)=O ALIAUSDVMZLDTD-UHFFFAOYSA-N 0.000 claims 2
CYGAEMRWDAFBJK-UHFFFAOYSA-N 1-[2-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]acetyl]-N,N-diethylpiperidine-3-carboxamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(=O)N1CC(CCC1)C(=O)N(CC)CC CYGAEMRWDAFBJK-UHFFFAOYSA-N 0.000 claims 2
NLKBPPAAKMVCGC-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoro-1-hydroxyethyl)-1H-indol-5-yl]piperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C(F)(F)F)O)C1CCN(CC1)C(CN(C)C)=O NLKBPPAAKMVCGC-UHFFFAOYSA-N 0.000 claims 2
HLOSEPYMYCDAOA-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-2-(1H-indol-3-yl)ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)C(CC1=CNC2=CC=CC=C12)=O HLOSEPYMYCDAOA-UHFFFAOYSA-N 0.000 claims 2
RQKJLTRARRDAMK-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-2-(2H-tetrazol-5-yl)ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)C(CC1=NN=NN1)=O RQKJLTRARRDAMK-UHFFFAOYSA-N 0.000 claims 2
ZJENTZVKLKSSLD-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)C(CN(C)C)=O ZJENTZVKLKSSLD-UHFFFAOYSA-N 0.000 claims 2
VNWJOPHHAXNSKY-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-2-[4-(dimethylamino)phenyl]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)C(CC1=CC=C(C=C1)N(C)C)=O VNWJOPHHAXNSKY-UHFFFAOYSA-N 0.000 claims 2
UFTAMDKBIAGYKB-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-2-methylsulfonylethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)C(CS(=O)(=O)C)=O UFTAMDKBIAGYKB-UHFFFAOYSA-N 0.000 claims 2
MCULWRJPHWUADK-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-2-pyrazin-2-ylethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)C(CC1=NC=CN=C1)=O MCULWRJPHWUADK-UHFFFAOYSA-N 0.000 claims 2
ILAIDFYSTIOBFK-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-2-pyridin-3-ylethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)C(CC=1C=NC=CC=1)=O ILAIDFYSTIOBFK-UHFFFAOYSA-N 0.000 claims 2
RFAGGPNNBAZQRQ-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-2-pyridin-3-yloxyethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)C(COC=1C=NC=CC=1)=O RFAGGPNNBAZQRQ-UHFFFAOYSA-N 0.000 claims 2
HOZLHRHPRRMONM-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-3,3,3-trifluoropropan-1-one Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)C(CC(F)(F)F)=O HOZLHRHPRRMONM-UHFFFAOYSA-N 0.000 claims 2
YJQFKNHCVLOYOB-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-3-(dimethylamino)propan-1-one Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)C(CCN(C)C)=O YJQFKNHCVLOYOB-UHFFFAOYSA-N 0.000 claims 2
AOLPIKRZLZRQJN-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-3-indol-1-ylpropan-1-one Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)C(CCN1C=CC2=CC=CC=C12)=O AOLPIKRZLZRQJN-UHFFFAOYSA-N 0.000 claims 2
IHFREMAMHGTCDK-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-3-piperidin-1-ylpropan-1-one Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)C(CCN1CCCCC1)=O IHFREMAMHGTCDK-UHFFFAOYSA-N 0.000 claims 2
LNBRHKQCZDMLCI-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-3-pyridin-3-ylpropan-1-one Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)C(CCC=1C=NC=CC=1)=O LNBRHKQCZDMLCI-UHFFFAOYSA-N 0.000 claims 2
LGMDJGQAXWOOPF-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-3-pyrrol-1-ylpropan-1-one Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)C(CCN1C=CC=C1)=O LGMDJGQAXWOOPF-UHFFFAOYSA-N 0.000 claims 2
ZJRSPLGJDAOJCK-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-4-(dimethylamino)butan-1-one Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)C(CCCN(C)C)=O ZJRSPLGJDAOJCK-UHFFFAOYSA-N 0.000 claims 2
AAMKMTDGIXKTFC-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-4-imidazol-1-ylbutan-1-one Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)C(CCCN1C=NC=C1)=O AAMKMTDGIXKTFC-UHFFFAOYSA-N 0.000 claims 2
OZQONDZBFYEDFB-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-(oxan-4-yl)-1H-indol-5-yl]piperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C1CCOCC1)C1CCN(CC1)C(CN(C)C)=O OZQONDZBFYEDFB-UHFFFAOYSA-N 0.000 claims 2
CAVPIUZFQLUNCY-JOCHJYFZSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-(oxan-4-yl)-1H-indol-5-yl]piperidin-1-yl]-2-[[(2R)-3-methylbutan-2-yl]amino]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C1CCOCC1)C1CCN(CC1)C(CN[C@H](C)C(C)C)=O CAVPIUZFQLUNCY-JOCHJYFZSA-N 0.000 claims 2
AZVLYLMWXFUONO-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-ethyl-1H-indol-5-yl]piperidin-1-yl]-2-(1,3-thiazol-2-ylamino)ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C(CNC=1SC=CN=1)=O AZVLYLMWXFUONO-UHFFFAOYSA-N 0.000 claims 2
CLAOHSAMDMCFPW-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-ethyl-1H-indol-5-yl]piperidin-1-yl]-2-(2-hydroxyethylamino)ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C(CNCCO)=O CLAOHSAMDMCFPW-UHFFFAOYSA-N 0.000 claims 2
TYJCEIPNNXZGMQ-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-ethyl-1H-indol-5-yl]piperidin-1-yl]-2-(2-hydroxypropylamino)ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C(CNCC(C)O)=O TYJCEIPNNXZGMQ-UHFFFAOYSA-N 0.000 claims 2
MPANUBXQKJORIV-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-ethyl-1H-indol-5-yl]piperidin-1-yl]-2-(4-piperidin-1-ylpiperidin-1-yl)ethanone Chemical compound N1(CCCCC1)C1CCN(CC1)CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)CC MPANUBXQKJORIV-UHFFFAOYSA-N 0.000 claims 2
YYNSPUQZNQJRSN-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-ethyl-1H-indol-5-yl]piperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C(CN(C)C)=O YYNSPUQZNQJRSN-UHFFFAOYSA-N 0.000 claims 2
YWSKPBKOESZMPX-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-ethyl-1H-indol-5-yl]piperidin-1-yl]-2-[(3-hydroxy-2,2-dimethylpropyl)amino]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C(CNCC(CO)(C)C)=O YWSKPBKOESZMPX-UHFFFAOYSA-N 0.000 claims 2
KPTITZQEQVZLME-JOCHJYFZSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-ethyl-1H-indol-5-yl]piperidin-1-yl]-2-[(3R)-3-hydroxypyrrolidin-1-yl]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C(CN1C[C@@H](CC1)O)=O KPTITZQEQVZLME-JOCHJYFZSA-N 0.000 claims 2
YZJBRTJDWIMHBE-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-ethyl-1H-indol-5-yl]piperidin-1-yl]-2-[3-(hydroxymethyl)piperidin-1-yl]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C(CN1CC(CCC1)CO)=O YZJBRTJDWIMHBE-UHFFFAOYSA-N 0.000 claims 2
KCZDAPVDVQVOJR-DEOSSOPVSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-ethyl-1H-indol-5-yl]piperidin-1-yl]-2-[[(2S)-1-hydroxyhexan-2-yl]amino]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C(CN[C@H](CO)CCCC)=O KCZDAPVDVQVOJR-DEOSSOPVSA-N 0.000 claims 2
QBXGNUSPWDJAGZ-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-ethyl-1H-indol-5-yl]piperidin-1-yl]-2-[[1-(hydroxymethyl)cyclopentyl]amino]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C(CNC1(CCCC1)CO)=O QBXGNUSPWDJAGZ-UHFFFAOYSA-N 0.000 claims 2
OETCKWQCSMIDIQ-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-ethyl-1H-indol-5-yl]piperidin-1-yl]-2-[[4-(dimethylamino)cyclohexyl]amino]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C(CNC1CCC(CC1)N(C)C)=O OETCKWQCSMIDIQ-UHFFFAOYSA-N 0.000 claims 2
NBAAEFLRKQSKEG-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]-2-(3-hydroxybutylamino)ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C(CNCCC(C)O)=O NBAAEFLRKQSKEG-UHFFFAOYSA-N 0.000 claims 2
YMSDIDZTOBDYGL-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]-2-(4-methylpiperazin-1-yl)ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C(CN1CCN(CC1)C)=O YMSDIDZTOBDYGL-UHFFFAOYSA-N 0.000 claims 2
DNZQAGKXQJLINX-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C(CN(C)C)=O DNZQAGKXQJLINX-UHFFFAOYSA-N 0.000 claims 2
YPQBRQFEBAHHCR-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]-2-(ethylamino)ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C(CNCC)=O YPQBRQFEBAHHCR-UHFFFAOYSA-N 0.000 claims 2
CKAOHJKSPSMOIL-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]-2-[2-hydroxyethyl(methyl)amino]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C(CN(C)CCO)=O CKAOHJKSPSMOIL-UHFFFAOYSA-N 0.000 claims 2
DVJLVHDDNBIFTQ-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]-2-[4-(dimethylamino)piperidin-1-yl]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C(CN1CCC(CC1)N(C)C)=O DVJLVHDDNBIFTQ-UHFFFAOYSA-N 0.000 claims 2
OBPHKFAZRPOINF-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-(1-hydroxybutan-2-ylamino)ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CNC(CO)CC)=O OBPHKFAZRPOINF-UHFFFAOYSA-N 0.000 claims 2
ZUGZFXMXMDXMAK-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-(2,2,2-trifluoroethylamino)ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CNCC(F)(F)F)=O ZUGZFXMXMDXMAK-UHFFFAOYSA-N 0.000 claims 2
DGNSEWSPDKIUII-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-(2-hydroxyethylamino)ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CNCCO)=O DGNSEWSPDKIUII-UHFFFAOYSA-N 0.000 claims 2
KHTBMEKOFBGYQW-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-(2-hydroxypropylamino)ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CNCC(C)O)=O KHTBMEKOFBGYQW-UHFFFAOYSA-N 0.000 claims 2
GHQOWCGWMSKQKT-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-(3-hydroxybutylamino)ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CNCCC(C)O)=O GHQOWCGWMSKQKT-UHFFFAOYSA-N 0.000 claims 2
KRSKWANNOLYFKU-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-(4-hydroxypiperidin-1-yl)ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1CCC(CC1)O)=O KRSKWANNOLYFKU-UHFFFAOYSA-N 0.000 claims 2
FSKVJUVDNNBUQM-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-(4-methyl-1,4-diazepan-1-yl)ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1CCN(CCC1)C)=O FSKVJUVDNNBUQM-UHFFFAOYSA-N 0.000 claims 2
CPKSPCOBFYFDQC-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-(4-piperidin-1-ylpiperidin-1-yl)ethanone Chemical compound N1(CCCCC1)C1CCN(CC1)CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)C(C)C CPKSPCOBFYFDQC-UHFFFAOYSA-N 0.000 claims 2
KTMHFWCRZRJJSB-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-(4-propan-2-ylpiperazin-1-yl)ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1CCN(CC1)C(C)C)=O KTMHFWCRZRJJSB-UHFFFAOYSA-N 0.000 claims 2
SEBDIEQCLRQGJF-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN(C)C)=O SEBDIEQCLRQGJF-UHFFFAOYSA-N 0.000 claims 2
VNEYOMYPTSIECO-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-(methylamino)ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CNC)=O VNEYOMYPTSIECO-UHFFFAOYSA-N 0.000 claims 2
LRDZPWIDIRIPRZ-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[(2-hydroxycyclopentyl)amino]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CNC1C(CCC1)O)=O LRDZPWIDIRIPRZ-UHFFFAOYSA-N 0.000 claims 2
YKQKSHAMGPPETI-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[(3-hydroxy-2,2-dimethylpropyl)amino]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CNCC(CO)(C)C)=O YKQKSHAMGPPETI-UHFFFAOYSA-N 0.000 claims 2
IAKJMKTZIBVDFE-WJOKGBTCSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[(3R)-3-(4-propan-2-ylpiperazine-1-carbonyl)piperidin-1-yl]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1C[C@@H](CCC1)C(=O)N1CCN(CC1)C(C)C)=O IAKJMKTZIBVDFE-WJOKGBTCSA-N 0.000 claims 2
CWWMYLRVDOHEKP-MUUNZHRXSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[(3R)-3-(pyrrolidine-1-carbonyl)piperidin-1-yl]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1C[C@@H](CCC1)C(=O)N1CCCC1)=O CWWMYLRVDOHEKP-MUUNZHRXSA-N 0.000 claims 2
ZBUCYVDRYVMRBO-WJOKGBTCSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[(3R)-3-[4-(2-hydroxyethyl)piperidine-1-carbonyl]piperidin-1-yl]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1C[C@@H](CCC1)C(=O)N1CCC(CC1)CCO)=O ZBUCYVDRYVMRBO-WJOKGBTCSA-N 0.000 claims 2
OKAURHJSSLIVIV-UUWRZZSWSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[(3R)-3-[4-(2-pyrrolidin-1-ylethyl)piperazine-1-carbonyl]piperidin-1-yl]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1C[C@@H](CCC1)C(=O)N1CCN(CC1)CCN1CCCC1)=O OKAURHJSSLIVIV-UUWRZZSWSA-N 0.000 claims 2
KHPZJHXUCFIPRP-SSEXGKCCSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[(3R)-3-[4-(dimethylamino)piperidine-1-carbonyl]piperidin-1-yl]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1C[C@@H](CCC1)C(=O)N1CCC(CC1)N(C)C)=O KHPZJHXUCFIPRP-SSEXGKCCSA-N 0.000 claims 2
QSHLLSVRBSRRSS-SDZHOWIXSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[(3S)-3-(2,5-dimethylpyrrolidine-1-carbonyl)piperidin-1-yl]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1C[C@H](CCC1)C(=O)N1C(CCC1C)C)=O QSHLLSVRBSRRSS-SDZHOWIXSA-N 0.000 claims 2
IOZAWLWWWOUFQP-XLTVJXRZSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[(3S)-3-(3-hydroxypiperidine-1-carbonyl)piperidin-1-yl]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1C[C@H](CCC1)C(=O)N1CC(CCC1)O)=O IOZAWLWWWOUFQP-XLTVJXRZSA-N 0.000 claims 2
IAKJMKTZIBVDFE-HKBQPEDESA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[(3S)-3-(4-propan-2-ylpiperazine-1-carbonyl)piperidin-1-yl]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1C[C@H](CCC1)C(=O)N1CCN(CC1)C(C)C)=O IAKJMKTZIBVDFE-HKBQPEDESA-N 0.000 claims 2
CWWMYLRVDOHEKP-NDEPHWFRSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[(3S)-3-(pyrrolidine-1-carbonyl)piperidin-1-yl]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1C[C@H](CCC1)C(=O)N1CCCC1)=O CWWMYLRVDOHEKP-NDEPHWFRSA-N 0.000 claims 2
ZBUCYVDRYVMRBO-HKBQPEDESA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[(3S)-3-[4-(2-hydroxyethyl)piperidine-1-carbonyl]piperidin-1-yl]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1C[C@H](CCC1)C(=O)N1CCC(CC1)CCO)=O ZBUCYVDRYVMRBO-HKBQPEDESA-N 0.000 claims 2
OKAURHJSSLIVIV-UMSFTDKQSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[(3S)-3-[4-(2-pyrrolidin-1-ylethyl)piperazine-1-carbonyl]piperidin-1-yl]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1C[C@H](CCC1)C(=O)N1CCN(CC1)CCN1CCCC1)=O OKAURHJSSLIVIV-UMSFTDKQSA-N 0.000 claims 2
KHPZJHXUCFIPRP-PMERELPUSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[(3S)-3-[4-(dimethylamino)piperidine-1-carbonyl]piperidin-1-yl]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1C[C@H](CCC1)C(=O)N1CCC(CC1)N(C)C)=O KHPZJHXUCFIPRP-PMERELPUSA-N 0.000 claims 2
QCFZSAQLRFGVKF-YTTGMZPUSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[(3S)-3-[4-[3-(trifluoromethyl)phenyl]piperazine-1-carbonyl]piperidin-1-yl]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1C[C@H](CCC1)C(=O)N1CCN(CC1)C1=CC(=CC=C1)C(F)(F)F)=O QCFZSAQLRFGVKF-YTTGMZPUSA-N 0.000 claims 2
IKWJMYUJRSRRRQ-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[(4-hydroxycyclohexyl)amino]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CNC1CCC(CC1)O)=O IKWJMYUJRSRRRQ-UHFFFAOYSA-N 0.000 claims 2
RDMPYSJQDSVRJS-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[2-(2-hydroxyethoxy)ethylamino]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CNCCOCCO)=O RDMPYSJQDSVRJS-UHFFFAOYSA-N 0.000 claims 2
NTKKQTJEIXWJMN-UFXYQILXSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[2-[[(2S)-1-methylpyrrolidin-2-yl]methyl]piperidin-1-yl]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1C(CCCC1)C[C@H]1N(CCC1)C)=O NTKKQTJEIXWJMN-UFXYQILXSA-N 0.000 claims 2
BYHGHPUJMPUCHF-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[2-hydroxyethyl(methyl)amino]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN(C)CCO)=O BYHGHPUJMPUCHF-UHFFFAOYSA-N 0.000 claims 2
MENDGUXRGZOUBM-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1CCC(CC1)N1CCN(CC1)C)=O MENDGUXRGZOUBM-UHFFFAOYSA-N 0.000 claims 2
LWNOKHFGWMJJHG-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[4-(hydroxymethyl)piperidin-1-yl]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1CCC(CC1)CO)=O LWNOKHFGWMJJHG-UHFFFAOYSA-N 0.000 claims 2
HPWNBEHFDIETQB-HHHXNRCGSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[[(2R)-2-fluoro-3-hydroxy-3-methylbutyl]amino]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CNC[C@H](C(C)(C)O)F)=O HPWNBEHFDIETQB-HHHXNRCGSA-N 0.000 claims 2
LQJQHLCZLBVIHB-VWLOTQADSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[[(2S)-1-hydroxy-4-methylpentan-2-yl]amino]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN[C@H](CO)CC(C)C)=O LQJQHLCZLBVIHB-VWLOTQADSA-N 0.000 claims 2
IBDDHFNXIHKQPB-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[[1-(hydroxymethyl)cyclopentyl]amino]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CNC1(CCCC1)CO)=O IBDDHFNXIHKQPB-UHFFFAOYSA-N 0.000 claims 2
JQCHZSWNYYDKLM-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[[4-(2-hydroxypropan-2-yl)cyclohexyl]amino]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CNC1CCC(CC1)C(C)(C)O)=O JQCHZSWNYYDKLM-UHFFFAOYSA-N 0.000 claims 2
ZZSULESCKQYXJO-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[[4-(dimethylamino)cyclohexyl]amino]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CNC1CCC(CC1)N(C)C)=O ZZSULESCKQYXJO-UHFFFAOYSA-N 0.000 claims 2
QBLIYUFVWTYYHZ-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-hydroxyethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CO)=O QBLIYUFVWTYYHZ-UHFFFAOYSA-N 0.000 claims 2
PIAOCCKMIFFIAQ-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-morpholin-4-ylethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1CCOCC1)=O PIAOCCKMIFFIAQ-UHFFFAOYSA-N 0.000 claims 2
SUIYFKHKDUMGDR-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-propan-2-yloxyethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(COC(C)C)=O SUIYFKHKDUMGDR-UHFFFAOYSA-N 0.000 claims 2
DQUIRXURXAMELG-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-4-(propan-2-ylamino)butan-1-one Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CCCNC(C)C)=O DQUIRXURXAMELG-UHFFFAOYSA-N 0.000 claims 2
ZAFQYQGDKZHCHX-UHFFFAOYSA-N 1-[4-[3-(2,2-difluoroethyl)-2-(3,4-dimethoxyphenyl)-1H-indol-5-yl]piperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound FC(CC1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(CN(C)C)=O)C1=CC(=C(C=C1)OC)OC)F ZAFQYQGDKZHCHX-UHFFFAOYSA-N 0.000 claims 2
SRJCEBBUPXJJPT-UHFFFAOYSA-N 1-[4-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidine-1-carbonyl]piperidin-1-yl]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)C(=O)C1CCN(CC1)C(C)=O SRJCEBBUPXJJPT-UHFFFAOYSA-N 0.000 claims 2
CIDGGOOEVJOZIP-UHFFFAOYSA-N 2-(1,3-dihydroxypropan-2-ylamino)-1-[4-[2-(3,4-dimethoxyphenyl)-3-ethyl-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound OCC(CO)NCC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)CC CIDGGOOEVJOZIP-UHFFFAOYSA-N 0.000 claims 2
VLTDQXBIYGGXEV-UHFFFAOYSA-N 2-(1,3-dihydroxypropan-2-ylamino)-1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound OCC(CO)NCC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)C(C)C VLTDQXBIYGGXEV-UHFFFAOYSA-N 0.000 claims 2
ATDMIQRQAWIDIZ-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3,6-dimethyl-5-[1-(1-propan-2-ylpiperidin-4-yl)piperidin-4-yl]-1H-indole 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.COc1ccc(cc1OC)-c1[nH]c2cc(C)c(cc2c1C)C1CCN(CC1)C1CCN(CC1)C(C)C ATDMIQRQAWIDIZ-UHFFFAOYSA-N 0.000 claims 2
YHOITXUXJFIVDS-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-(oxan-4-yl)-5-piperidin-4-yl-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C1CCOCC1)C1CCNCC1 YHOITXUXJFIVDS-UHFFFAOYSA-N 0.000 claims 2
XSTIWMVHOAAMJN-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-ethyl-5-[1-(1-ethylpiperidin-4-yl)piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C1CCN(CC1)CC XSTIWMVHOAAMJN-UHFFFAOYSA-N 0.000 claims 2
IOVSZOPNTRZVEU-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-ethyl-5-[1-(1-methylpiperidin-4-yl)piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C1CCN(CC1)C IOVSZOPNTRZVEU-UHFFFAOYSA-N 0.000 claims 2
FHWQWPPSQHSTMT-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-ethyl-5-[1-(1-propan-2-ylpiperidin-4-yl)piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C1CCN(CC1)C(C)C FHWQWPPSQHSTMT-UHFFFAOYSA-N 0.000 claims 2
XGSOEEAMTATDMP-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-ethyl-5-[1-(3,3,3-trifluoro-2-methylpropyl)piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)CC(C(F)(F)F)C XGSOEEAMTATDMP-UHFFFAOYSA-N 0.000 claims 2
RAWBBGIGMAUFTO-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-ethyl-5-[1-[1-(1H-imidazol-5-ylmethyl)piperidin-4-yl]piperidin-4-yl]-1H-indole Chemical compound N1C=NC(=C1)CN1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)CC RAWBBGIGMAUFTO-UHFFFAOYSA-N 0.000 claims 2
IPOCTMZDJIBZLP-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-ethyl-5-[1-[1-(2-methylpropyl)piperidin-4-yl]piperidin-4-yl]-1H-indole 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.CCc1c([nH]c2ccc(cc12)C1CCN(CC1)C1CCN(CC(C)C)CC1)-c1ccc(OC)c(OC)c1 IPOCTMZDJIBZLP-UHFFFAOYSA-N 0.000 claims 2
BUFZMVBOIXPRFI-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-ethyl-5-[1-[1-(thiophen-3-ylmethyl)piperidin-4-yl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C1CCN(CC1)CC1=CSC=C1 BUFZMVBOIXPRFI-UHFFFAOYSA-N 0.000 claims 2
BXXOWWUBRXXLKH-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-ethyl-5-[1-[1-[(1-methylindol-2-yl)methyl]piperidin-4-yl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C1CCN(CC1)CC=1N(C2=CC=CC=C2C=1)C BXXOWWUBRXXLKH-UHFFFAOYSA-N 0.000 claims 2
BKDQZJUMLORUAS-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-ethyl-5-[1-[1-[(1-methylpyrazol-3-yl)methyl]piperidin-4-yl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C1CCN(CC1)CC1=NN(C=C1)C BKDQZJUMLORUAS-UHFFFAOYSA-N 0.000 claims 2
GGQUKIMQJJOJET-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-ethyl-5-[1-[1-[(2-methyl-1H-imidazol-5-yl)methyl]piperidin-4-yl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C1CCN(CC1)CC1=CN=C(N1)C GGQUKIMQJJOJET-UHFFFAOYSA-N 0.000 claims 2
YCOGZXSNGBNXHP-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-ethyl-5-[1-[1-[(2-methyl-1H-indol-3-yl)methyl]piperidin-4-yl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C1CCN(CC1)CC1=C(NC2=CC=CC=C12)C YCOGZXSNGBNXHP-UHFFFAOYSA-N 0.000 claims 2
ITKDZFAEXSOIPD-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-ethyl-5-[1-[1-[(3-methylthiophen-2-yl)methyl]piperidin-4-yl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C1CCN(CC1)CC=1SC=CC=1C ITKDZFAEXSOIPD-UHFFFAOYSA-N 0.000 claims 2
GQLMMKMUEKFOIJ-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-ethyl-5-[1-[1-[(5-methyl-1H-pyrazol-3-yl)methyl]piperidin-4-yl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C1CCN(CC1)CC1=CC(=NN1)C GQLMMKMUEKFOIJ-UHFFFAOYSA-N 0.000 claims 2
ISAVDUQWNRQDBS-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-ethyl-5-[1-[1-[(5-methylthiophen-2-yl)methyl]piperidin-4-yl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C1CCN(CC1)CC=1SC(=CC=1)C ISAVDUQWNRQDBS-UHFFFAOYSA-N 0.000 claims 2
LXMDTSSVCFNHSE-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-ethyl-5-[1-[1-[(5-phenylfuran-2-yl)methyl]piperidin-4-yl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C1CCN(CC1)CC=1OC(=CC=1)C1=CC=CC=C1 LXMDTSSVCFNHSE-UHFFFAOYSA-N 0.000 claims 2
LEENSISGXXSKKB-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-ethyl-5-[1-[1-[(5-phenylthiophen-2-yl)methyl]piperidin-4-yl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C1CCN(CC1)CC=1SC(=CC=1)C1=CC=CC=C1 LEENSISGXXSKKB-UHFFFAOYSA-N 0.000 claims 2
HPBQCFYGTNLAKB-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-ethyl-6-methoxy-5-piperidin-4-yl-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC(=C(C=C2C=1CC)C1CCNCC1)OC HPBQCFYGTNLAKB-UHFFFAOYSA-N 0.000 claims 2
UFGOXEDGKXBDBV-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-ethyl-7-fluoro-5-[1-[1-(2-methylpropyl)piperidin-4-yl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=C(C=C(C=C2C=1CC)C1CCN(CC1)C1CCN(CC1)CC(C)C)F UFGOXEDGKXBDBV-UHFFFAOYSA-N 0.000 claims 2
GEGKRPJWLCIYOZ-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-ethyl-7-fluoro-5-piperidin-4-yl-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=C(C=C(C=C2C=1CC)C1CCNCC1)F GEGKRPJWLCIYOZ-UHFFFAOYSA-N 0.000 claims 2
CWQSBUYFEJBWML-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-(1-piperidin-3-ylpiperidin-4-yl)-1H-indole Chemical compound N1(CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)C)C1CNCCC1 CWQSBUYFEJBWML-UHFFFAOYSA-N 0.000 claims 2
VGYPOFRRZXUWTP-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-(1-piperidin-4-ylpiperidin-4-yl)-1H-indole dihydrochloride Chemical compound Cl.Cl.COc1ccc(cc1OC)-c1[nH]c2ccc(cc2c1C)C1CCN(CC1)C1CCNCC1 VGYPOFRRZXUWTP-UHFFFAOYSA-N 0.000 claims 2
TUFADGLXRCQMGN-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-(1-pyrrolidin-3-ylpiperidin-4-yl)-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CNCC1 TUFADGLXRCQMGN-UHFFFAOYSA-N 0.000 claims 2
CDLYIDNAKVJICP-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-(1,2,2,6,6-pentamethylpiperidin-4-yl)piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CC(N(C(C1)(C)C)C)(C)C CDLYIDNAKVJICP-UHFFFAOYSA-N 0.000 claims 2
FRXGXHHMBXJZSF-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-(1-methylazepan-4-yl)piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CCN(CCC1)C FRXGXHHMBXJZSF-UHFFFAOYSA-N 0.000 claims 2
AULVCMBXTZGHFR-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-(1-methylpiperidin-4-yl)piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CCN(CC1)C AULVCMBXTZGHFR-UHFFFAOYSA-N 0.000 claims 2
YRLOAUNISAJRCI-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-(1-phenylethyl)piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C(C)C1=CC=CC=C1 YRLOAUNISAJRCI-UHFFFAOYSA-N 0.000 claims 2
OKFWNSRBERFZJZ-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-(1-phenylpyrrolidin-3-yl)piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CN(CC1)C1=CC=CC=C1 OKFWNSRBERFZJZ-UHFFFAOYSA-N 0.000 claims 2
QLQBGKPPSBQIGX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-(1-propan-2-ylazepan-4-yl)piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CCN(CCC1)C(C)C QLQBGKPPSBQIGX-UHFFFAOYSA-N 0.000 claims 2
WSFLTQAKAGYTQL-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-(1-propan-2-ylpiperidin-4-yl)piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CCN(CC1)C(C)C WSFLTQAKAGYTQL-UHFFFAOYSA-N 0.000 claims 2
DOMJGJCKHCJLAR-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-(2,2,6,6-tetramethylpiperidin-4-yl)piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CC(NC(C1)(C)C)(C)C DOMJGJCKHCJLAR-UHFFFAOYSA-N 0.000 claims 2
ZFFMQDCJOYLMIU-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-(oxan-4-ylmethyl)piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)CC1CCOCC1 ZFFMQDCJOYLMIU-UHFFFAOYSA-N 0.000 claims 2
QGGBCBYDGTVZRQ-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-(oxetan-3-yl)piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1COC1 QGGBCBYDGTVZRQ-UHFFFAOYSA-N 0.000 claims 2
YWRQPFBSBVPXMZ-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-(piperidin-2-ylmethyl)piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)CC1NCCCC1 YWRQPFBSBVPXMZ-UHFFFAOYSA-N 0.000 claims 2
ULSSWITWQLOCQL-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-(pyridin-3-ylmethyl)piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)CC=1C=NC=CC=1 ULSSWITWQLOCQL-UHFFFAOYSA-N 0.000 claims 2
VKPLAKFHDKXBKH-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-(pyridin-4-ylmethyl)piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)CC1=CC=NC=C1 VKPLAKFHDKXBKH-UHFFFAOYSA-N 0.000 claims 2
MBISYNWCQKRMSQ-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-[(1-methylimidazol-2-yl)methyl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)CC=1N(C=CN=1)C MBISYNWCQKRMSQ-UHFFFAOYSA-N 0.000 claims 2
OEOGNVCKOCRFMA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-[(1-methylindol-2-yl)methyl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)CC=1N(C2=CC=CC=C2C=1)C OEOGNVCKOCRFMA-UHFFFAOYSA-N 0.000 claims 2
WWGKZAKCINYBAU-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-[(1-methylpiperidin-2-yl)methyl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)CC1N(CCCC1)C WWGKZAKCINYBAU-UHFFFAOYSA-N 0.000 claims 2
HYSUMBYMHLYIKR-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-[(1-methylpyrrol-2-yl)methyl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)CC=1N(C=CC=1)C HYSUMBYMHLYIKR-UHFFFAOYSA-N 0.000 claims 2
XTPBWHISLHDICT-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-[(2-methyl-1H-imidazol-5-yl)methyl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)CC1=CN=C(N1)C XTPBWHISLHDICT-UHFFFAOYSA-N 0.000 claims 2
LJLDNBDPARVBON-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-[(3-methylimidazol-4-yl)methyl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)CC1=CN=CN1C LJLDNBDPARVBON-UHFFFAOYSA-N 0.000 claims 2
BQBOLHAKBYZCKC-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-[1-(2-methylbutyl)piperidin-4-yl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CCN(CC1)CC(CC)C BQBOLHAKBYZCKC-UHFFFAOYSA-N 0.000 claims 2
MSJKTDGECKEHHV-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-[1-(2-methylpropyl)azepan-4-yl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CCN(CCC1)CC(C)C MSJKTDGECKEHHV-UHFFFAOYSA-N 0.000 claims 2
BGMKTMDLWIMYOV-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-[1-(2-methylpropyl)piperidin-4-yl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CCN(CC1)CC(C)C BGMKTMDLWIMYOV-UHFFFAOYSA-N 0.000 claims 2
ZKPKOUXRPVHHIQ-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-[1-(2-methylpropyl)pyrrolidin-3-yl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CN(CC1)CC(C)C ZKPKOUXRPVHHIQ-UHFFFAOYSA-N 0.000 claims 2
CRNICQMBIPDRFK-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-[1-(3,3,3-trifluoropropyl)piperidin-4-yl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CCN(CC1)CCC(F)(F)F CRNICQMBIPDRFK-UHFFFAOYSA-N 0.000 claims 2
WXCSWNPTCCSPBN-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-[1-(3-methylbutyl)piperidin-4-yl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CCN(CC1)CCC(C)C WXCSWNPTCCSPBN-UHFFFAOYSA-N 0.000 claims 2
LZQKMFGCWOIWKO-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-[1-(3-methylcyclohexyl)piperidin-4-yl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CCN(CC1)C1CC(CCC1)C LZQKMFGCWOIWKO-UHFFFAOYSA-N 0.000 claims 2
WQOLRARJURSBLN-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-[1-(3-methylsulfanylpropyl)piperidin-4-yl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CCN(CC1)CCCSC WQOLRARJURSBLN-UHFFFAOYSA-N 0.000 claims 2
KKMCFEZVXYWYCQ-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-[1-(oxan-4-yl)piperidin-4-yl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CCN(CC1)C1CCOCC1 KKMCFEZVXYWYCQ-UHFFFAOYSA-N 0.000 claims 2
GTNQVZMLEZXNIY-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-[1-(oxetan-3-yl)azepan-4-yl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CCN(CCC1)C1COC1 GTNQVZMLEZXNIY-UHFFFAOYSA-N 0.000 claims 2
VIEYHZOUPJFPND-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-[1-(oxetan-3-yl)piperidin-4-yl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CCN(CC1)C1COC1 VIEYHZOUPJFPND-UHFFFAOYSA-N 0.000 claims 2
UWSXVBSPDNUYRG-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-[1-(oxolan-3-yl)piperidin-4-yl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CCN(CC1)C1COCC1 UWSXVBSPDNUYRG-UHFFFAOYSA-N 0.000 claims 2
GNUBTJGXPJDHPD-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-[1-(thiophen-2-ylmethyl)piperidin-4-yl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CCN(CC1)CC=1SC=CC=1 GNUBTJGXPJDHPD-UHFFFAOYSA-N 0.000 claims 2
GFNKJOAWNYYFSK-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-[1-[(1-methylpyrrol-2-yl)methyl]piperidin-4-yl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CCN(CC1)CC=1N(C=CC=1)C GFNKJOAWNYYFSK-UHFFFAOYSA-N 0.000 claims 2
MLSBSSMSULTTGK-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-[1-[(3-methylimidazol-4-yl)methyl]piperidin-4-yl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CCN(CC1)CC1=CN=CN1C MLSBSSMSULTTGK-UHFFFAOYSA-N 0.000 claims 2
UYCCLUMALOQTDR-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-[1-[3-(trifluoromethyl)cyclohexyl]piperidin-4-yl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CCN(CC1)C1CC(CCC1)C(F)(F)F UYCCLUMALOQTDR-UHFFFAOYSA-N 0.000 claims 2
IZCLDRQUGBDFBU-JOCHJYFZSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-[[(2R)-pyrrolidin-2-yl]methyl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C[C@@H]1NCCC1 IZCLDRQUGBDFBU-JOCHJYFZSA-N 0.000 claims 2
IZCLDRQUGBDFBU-QFIPXVFZSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-[[(2S)-pyrrolidin-2-yl]methyl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C[C@H]1NCCC1 IZCLDRQUGBDFBU-QFIPXVFZSA-N 0.000 claims 2
KSLWDIFWYFSPAU-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-[[4-(1,2,4-triazol-1-yl)phenyl]methyl]piperidin-4-yl]-1H-indole Chemical compound N1(N=CN=C1)C1=CC=C(CN2CCC(CC2)C=2C=C3C(=C(NC3=CC=2)C2=CC(=C(C=C2)OC)OC)C)C=C1 KSLWDIFWYFSPAU-UHFFFAOYSA-N 0.000 claims 2
DOSLTQONZSWKFC-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-[[4-(4-methylpiperazin-1-yl)phenyl]methyl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)CC1=CC=C(C=C1)N1CCN(CC1)C DOSLTQONZSWKFC-UHFFFAOYSA-N 0.000 claims 2
PMUFFWKVPALHSA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-piperidin-4-yl-1H-indole hydrochloride Chemical compound Cl.COc1ccc(cc1OC)-c1[nH]c2ccc(cc2c1C)C1CCNCC1 PMUFFWKVPALHSA-UHFFFAOYSA-N 0.000 claims 2
DBAUOJGGQPPODV-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-propan-2-yl-5-[1-(1-propan-2-ylpiperidin-4-yl)piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C1CCN(CC1)C(C)C DBAUOJGGQPPODV-UHFFFAOYSA-N 0.000 claims 2
BYJYCBSYOXWJJM-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-propan-2-yl-5-[1-[[3-(trifluoromethyl)phenyl]methyl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC1=CC(=CC=C1)C(F)(F)F BYJYCBSYOXWJJM-UHFFFAOYSA-N 0.000 claims 2
UFFATCMDWOBZJM-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-propan-2-yl-5-[1-[[4-(trifluoromethoxy)phenyl]methyl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC1=CC=C(C=C1)OC(F)(F)F UFFATCMDWOBZJM-UHFFFAOYSA-N 0.000 claims 2
FMEQUNPYQVNLTI-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-(1-methylpiperidin-4-yl)-3-(2,2,2-trifluoroethyl)-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)C FMEQUNPYQVNLTI-UHFFFAOYSA-N 0.000 claims 2
OKZMVROCTUIWQL-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-(3-fluoropiperidin-4-yl)-3-propan-2-yl-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1C(CNCC1)F OKZMVROCTUIWQL-UHFFFAOYSA-N 0.000 claims 2
GIGDQPGPCYGXTJ-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-[1-(1-ethylazepan-4-yl)piperidin-4-yl]-3-methyl-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CCN(CCC1)CC GIGDQPGPCYGXTJ-UHFFFAOYSA-N 0.000 claims 2
CYHZVTTYZKTURJ-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-[1-(1-ethylpiperidin-3-yl)piperidin-4-yl]-3-methyl-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CN(CCC1)CC CYHZVTTYZKTURJ-UHFFFAOYSA-N 0.000 claims 2
ZUOMZKYCEIHPPS-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-[1-(1-methylpiperidin-4-yl)piperidin-4-yl]-3-propan-2-yl-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C1CCN(CC1)C ZUOMZKYCEIHPPS-UHFFFAOYSA-N 0.000 claims 2
SFGJEGHXYCTBBG-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-[1-(1-propan-2-ylpiperidin-4-yl)piperidin-4-yl]-3-(2,2,2-trifluoroethyl)-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)C1CCN(CC1)C(C)C SFGJEGHXYCTBBG-UHFFFAOYSA-N 0.000 claims 2
NVTWCQCSUPULDA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-[1-(1H-imidazol-5-ylmethyl)piperidin-4-yl]-3-propan-2-yl-1H-indole Chemical compound N1C=NC=C1CN1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)C(C)C NVTWCQCSUPULDA-UHFFFAOYSA-N 0.000 claims 2
GTGIYTYQJMHPEY-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-[1-(2-ethylbutyl)piperidin-4-yl]-3-propan-2-yl-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(CC)CC GTGIYTYQJMHPEY-UHFFFAOYSA-N 0.000 claims 2
KPDZGXMOAWJLLH-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-[1-[(1-methylimidazol-2-yl)methyl]piperidin-4-yl]-3-propan-2-yl-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC=1N(C=CN=1)C KPDZGXMOAWJLLH-UHFFFAOYSA-N 0.000 claims 2
MQAVNWMYLJBQID-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-[1-[(4-imidazol-1-ylphenyl)methyl]piperidin-4-yl]-3-methyl-1H-indole Chemical compound N1(C=NC=C1)C1=CC=C(CN2CCC(CC2)C=2C=C3C(=C(NC3=CC=2)C2=CC(=C(C=C2)OC)OC)C)C=C1 MQAVNWMYLJBQID-UHFFFAOYSA-N 0.000 claims 2
NGDZUNGHKTXPQG-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-[1-[(4-imidazol-1-ylphenyl)methyl]piperidin-4-yl]-3-propan-2-yl-1H-indole Chemical compound N1(C=NC=C1)C1=CC=C(CN2CCC(CC2)C=2C=C3C(=C(NC3=CC=2)C2=CC(=C(C=C2)OC)OC)C(C)C)C=C1 NGDZUNGHKTXPQG-UHFFFAOYSA-N 0.000 claims 2
XYYIENHVBQDCHO-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-[1-[(5-methyl-1H-imidazol-4-yl)methyl]piperidin-4-yl]-3-propan-2-yl-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC1=C(N=CN1)C XYYIENHVBQDCHO-UHFFFAOYSA-N 0.000 claims 2
HEAKWPWNYJIXAG-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-[1-[1-(2,2-dimethylpropyl)piperidin-4-yl]piperidin-4-yl]-3-methyl-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CCN(CC1)CC(C)(C)C HEAKWPWNYJIXAG-UHFFFAOYSA-N 0.000 claims 2
AQSPLTWUTZUGFY-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-[1-[1-(2-methylpropyl)piperidin-4-yl]piperidin-4-yl]-3-propan-2-yl-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C1CCN(CC1)CC(C)C AQSPLTWUTZUGFY-UHFFFAOYSA-N 0.000 claims 2
BNSHIZVAIKRMEK-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-[1-[1-(2-methylpropyl)piperidin-4-yl]piperidin-4-yl]-3-propyl-1H-indole 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.CCCc1c([nH]c2ccc(cc12)C1CCN(CC1)C1CCN(CC(C)C)CC1)-c1ccc(OC)c(OC)c1 BNSHIZVAIKRMEK-UHFFFAOYSA-N 0.000 claims 2
ZQJSSFWAUPDPRE-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-[1-[1-(5-methoxypentyl)piperidin-4-yl]piperidin-4-yl]-3-methyl-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CCN(CC1)CCCCCOC ZQJSSFWAUPDPRE-UHFFFAOYSA-N 0.000 claims 2
DFGOHXTYHIZCIW-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-[1-[1-(furan-2-ylmethyl)piperidin-4-yl]piperidin-4-yl]-3-methyl-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CCN(CC1)CC=1OC=CC=1 DFGOHXTYHIZCIW-UHFFFAOYSA-N 0.000 claims 2
HGVCAZWBOPDFNO-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-[1-[1-[(1,5-dimethylpyrazol-3-yl)methyl]piperidin-4-yl]piperidin-4-yl]-3-ethyl-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C1CCN(CC1)CC1=NN(C(=C1)C)C HGVCAZWBOPDFNO-UHFFFAOYSA-N 0.000 claims 2
YLNYEEGTHAICHC-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-[1-[1-[(2,5-dimethylpyrazol-3-yl)methyl]piperidin-4-yl]piperidin-4-yl]-3-ethyl-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C1CCN(CC1)CC1=CC(=NN1C)C YLNYEEGTHAICHC-UHFFFAOYSA-N 0.000 claims 2
DIGPOURJMIHMBT-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-[1-[2-(methylamino)ethyl]piperidin-4-yl]-1H-indole-3-carbonitrile 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.CNCCN1CCC(CC1)c1ccc2[nH]c(c(C#N)c2c1)-c1ccc(OC)c(OC)c1 DIGPOURJMIHMBT-UHFFFAOYSA-N 0.000 claims 2
CHUDUWCACFEYPQ-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-piperidin-4-yl-3-(2,2,2-trifluoroethyl)-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCNCC1 CHUDUWCACFEYPQ-UHFFFAOYSA-N 0.000 claims 2
ZBNNKKRWPDQXJD-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-piperidin-4-yl-3-propan-2-yl-1H-indole hydrochloride Chemical compound Cl.COc1ccc(cc1OC)-c1[nH]c2ccc(cc2c1C(C)C)C1CCNCC1 ZBNNKKRWPDQXJD-UHFFFAOYSA-N 0.000 claims 2
SQDHKFVTGUETKA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-6-methyl-5-piperidin-4-yl-3-propan-2-yl-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC(=C(C=C2C=1C(C)C)C1CCNCC1)C SQDHKFVTGUETKA-UHFFFAOYSA-N 0.000 claims 2
FDJZIRYWBWFAJK-UHFFFAOYSA-N 2-(4-acetyl-1,4-diazepan-1-yl)-1-[4-[2-(3,4-dimethoxyphenyl)-3-ethyl-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound C(C)(=O)N1CCN(CCC1)CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)CC FDJZIRYWBWFAJK-UHFFFAOYSA-N 0.000 claims 2
GLJOAVVVSXJXEA-UHFFFAOYSA-N 2-(4-acetyl-1,4-diazepan-1-yl)-1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound C(C)(=O)N1CCN(CCC1)CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)C(C)C GLJOAVVVSXJXEA-UHFFFAOYSA-N 0.000 claims 2
HZMGERHUQORIEV-UHFFFAOYSA-N 2-(4-acetylpiperazin-1-yl)-1-[4-[2-(3,4-dimethoxyphenyl)-3-ethyl-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound C(C)(=O)N1CCN(CC1)CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)CC HZMGERHUQORIEV-UHFFFAOYSA-N 0.000 claims 2
KLODPDHQEBWUIA-AYMNYOFFSA-N 2-[(3R)-3-(2,3,3a,4,6,6a-hexahydro-1H-pyrrolo[3,4-c]pyrrole-5-carbonyl)piperidin-1-yl]-1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1C[C@@H](CCC1)C(=O)N1CC2CNCC2C1)=O KLODPDHQEBWUIA-AYMNYOFFSA-N 0.000 claims 2
KLODPDHQEBWUIA-ZMTVJDMPSA-N 2-[(3S)-3-(2,3,3a,4,6,6a-hexahydro-1H-pyrrolo[3,4-c]pyrrole-5-carbonyl)piperidin-1-yl]-1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1C[C@H](CCC1)C(=O)N1CC2CNCC2C1)=O KLODPDHQEBWUIA-ZMTVJDMPSA-N 0.000 claims 2
IAPXWLOHSOYHTI-PMERELPUSA-N 2-[(3S)-3-(4-acetylpiperazine-1-carbonyl)piperidin-1-yl]-1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound C(C)(=O)N1CCN(CC1)C(=O)[C@@H]1CN(CCC1)CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)C(C)C IAPXWLOHSOYHTI-PMERELPUSA-N 0.000 claims 2
VGQYUSVUBFPBOX-UMSFTDKQSA-N 2-[(3S)-3-[4-[(4-bromophenyl)methyl]piperazine-1-carbonyl]piperidin-1-yl]-1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound BrC1=CC=C(CN2CCN(CC2)C(=O)[C@@H]2CN(CCC2)CC(=O)N2CCC(CC2)C=2C=C3C(=C(NC3=CC=2)C2=CC(=C(C=C2)OC)OC)C(C)C)C=C1 VGQYUSVUBFPBOX-UMSFTDKQSA-N 0.000 claims 2
UIGKWPGDGKSDGW-UHFFFAOYSA-N 2-[1-[4-[4-[2-(3,4-dimethoxyphenyl)-3-ethyl-1H-indol-5-yl]piperidin-1-yl]piperidin-1-yl]ethyl]-1,3-oxazole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C1CCN(CC1)C(C)C=1OC=CN=1 UIGKWPGDGKSDGW-UHFFFAOYSA-N 0.000 claims 2
BURIGXCCUMGPAA-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-1,3-dimethylindol-5-yl]piperidin-1-yl]-N-methylethanamine Chemical compound COC=1C=C(C=CC=1OC)C=1N(C2=CC=C(C=C2C=1C)C1CCN(CC1)CCNC)C BURIGXCCUMGPAA-UHFFFAOYSA-N 0.000 claims 2
WWJINMFNLJJJAJ-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-1-(4-pyridin-4-ylpiperazin-1-yl)ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)CC(=O)N1CCN(CC1)C1=CC=NC=C1 WWJINMFNLJJJAJ-UHFFFAOYSA-N 0.000 claims 2
FSHJBOMKMTWHFW-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-1-(4-pyrimidin-2-ylpiperazin-1-yl)ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)CC(=O)N1CCN(CC1)C1=NC=CC=N1 FSHJBOMKMTWHFW-UHFFFAOYSA-N 0.000 claims 2
YSMUDVWLEYSBHR-JOCHJYFZSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-1-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)CC(=O)N1[C@H](CCC1)CO YSMUDVWLEYSBHR-JOCHJYFZSA-N 0.000 claims 2
IKDSHQYXBMSJDM-HSZRJFAPSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-1-[(3R)-3-(dimethylamino)pyrrolidin-1-yl]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)CC(=O)N1C[C@@H](CC1)N(C)C IKDSHQYXBMSJDM-HSZRJFAPSA-N 0.000 claims 2
IKDSHQYXBMSJDM-QHCPKHFHSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-1-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)CC(=O)N1C[C@H](CC1)N(C)C IKDSHQYXBMSJDM-QHCPKHFHSA-N 0.000 claims 2
KLZJZZSTFQNQAY-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-1-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)CC(=O)N1CCC(CC1)N1CCN(CC1)C KLZJZZSTFQNQAY-UHFFFAOYSA-N 0.000 claims 2
HVAOIJVHDLTQLP-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-1-[4-(dimethylamino)piperidin-1-yl]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)CC(=O)N1CCC(CC1)N(C)C HVAOIJVHDLTQLP-UHFFFAOYSA-N 0.000 claims 2
XDYMREJIOWPTKT-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-N-(2-pyrrolidin-1-ylethyl)acetamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)CC(=O)NCCN1CCCC1 XDYMREJIOWPTKT-UHFFFAOYSA-N 0.000 claims 2
UTEAGRABIDGFHY-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-N-(3-imidazol-1-ylpropyl)acetamide Chemical compound N1(C=NC=C1)CCCNC(CN1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)CC(F)(F)F)=O UTEAGRABIDGFHY-UHFFFAOYSA-N 0.000 claims 2
AYOVGWYPMMFYDO-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-N-(4-pyrrolidin-1-ylbutyl)acetamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)CC(=O)NCCCCN1CCCC1 AYOVGWYPMMFYDO-UHFFFAOYSA-N 0.000 claims 2
AAOQRJRLOLVRID-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-N-[2-(dimethylamino)ethyl]-N-methylacetamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)CC(=O)N(C)CCN(C)C AAOQRJRLOLVRID-UHFFFAOYSA-N 0.000 claims 2
ZHNMNPCRTKWIOW-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-N-[2-(dimethylamino)ethyl]acetamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)CC(=O)NCCN(C)C ZHNMNPCRTKWIOW-UHFFFAOYSA-N 0.000 claims 2
NYVAQICJYIROSY-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-N-[3-(2-oxopyrrolidin-1-yl)propyl]acetamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)CC(=O)NCCCN1C(CCC1)=O NYVAQICJYIROSY-UHFFFAOYSA-N 0.000 claims 2
BHLVSBFFVITIIG-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-N-[3-(dimethylamino)propyl]-N-methylacetamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)CC(=O)N(C)CCCN(C)C BHLVSBFFVITIIG-UHFFFAOYSA-N 0.000 claims 2
QNNVSEBCTOOXQJ-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-N-[3-(dimethylamino)propyl]acetamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)CC(=O)NCCCN(C)C QNNVSEBCTOOXQJ-UHFFFAOYSA-N 0.000 claims 2
QNWMDGQILVJKFE-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-N-methyl-N-(1-methylpyrrolidin-3-yl)acetamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)CC(=O)N(C1CN(CC1)C)C QNWMDGQILVJKFE-UHFFFAOYSA-N 0.000 claims 2
YGHYAKNOJJPZBC-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-3-ethyl-1H-indol-5-yl]piperidin-1-yl]-N-methylethanamine 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.CCc1c([nH]c2ccc(cc12)C1CCN(CCNC)CC1)-c1ccc(OC)c(OC)c1 YGHYAKNOJJPZBC-UHFFFAOYSA-N 0.000 claims 2
FATQGLVQOMYEBY-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-3-ethyl-6-methoxy-1H-indol-5-yl]piperidin-1-yl]-N-methylethanamine Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC(=C(C=C2C=1CC)C1CCN(CC1)CCNC)OC FATQGLVQOMYEBY-UHFFFAOYSA-N 0.000 claims 2
MGXVSXAHLZQSDV-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-3-ethyl-6-methyl-1H-indol-5-yl]piperidin-1-yl]-N-methylethanamine 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.CCc1c([nH]c2cc(C)c(cc12)C1CCN(CCNC)CC1)-c1ccc(OC)c(OC)c1 MGXVSXAHLZQSDV-UHFFFAOYSA-N 0.000 claims 2
BKQBJBXHMXNYNQ-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-3-ethyl-7-fluoro-1H-indol-5-yl]piperidin-1-yl]-N-methylethanamine Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=C(C=C(C=C2C=1CC)C1CCN(CC1)CCNC)F BKQBJBXHMXNYNQ-UHFFFAOYSA-N 0.000 claims 2
SEAASZXMLLEGGU-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]-N,N-dimethylethanamine Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)CCN(C)C SEAASZXMLLEGGU-UHFFFAOYSA-N 0.000 claims 2
XLIWKGBDRCTGSB-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]-N,N-dimethylpropan-1-amine Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C(CN(C)C)C XLIWKGBDRCTGSB-UHFFFAOYSA-N 0.000 claims 2
DBOADQSXFJYNHT-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]-N-ethyl-N-methylethanamine Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)CCN(C)CC DBOADQSXFJYNHT-UHFFFAOYSA-N 0.000 claims 2
OZKODZCUKHECFI-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]ethanamine Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)CCN OZKODZCUKHECFI-UHFFFAOYSA-N 0.000 claims 2
JIQFGHPSBKEPTL-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-1-(4-methylpiperazin-1-yl)ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(=O)N1CCN(CC1)C JIQFGHPSBKEPTL-UHFFFAOYSA-N 0.000 claims 2
BTUKMAUMWRZLKJ-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-1-[3-(hydroxymethyl)piperidin-1-yl]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(=O)N1CC(CCC1)CO BTUKMAUMWRZLKJ-UHFFFAOYSA-N 0.000 claims 2
BKTXFRJTXDUJOE-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-N,N-dimethylacetamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(=O)N(C)C BKTXFRJTXDUJOE-UHFFFAOYSA-N 0.000 claims 2
OOLVIHHCAWJJII-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-N-(1-propan-2-ylpiperidin-4-yl)acetamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(=O)NC1CCN(CC1)C(C)C OOLVIHHCAWJJII-UHFFFAOYSA-N 0.000 claims 2
PUZUAGSOZBHQSR-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-N-(3-hydroxypropyl)acetamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(=O)NCCCO PUZUAGSOZBHQSR-UHFFFAOYSA-N 0.000 claims 2
UKYUETHIPBXYBQ-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-N-methylethanamine Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CCNC UKYUETHIPBXYBQ-UHFFFAOYSA-N 0.000 claims 2
OIFOYLUMWREYOV-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-6-fluoro-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-N-methylethanamine Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC(=C(C=C2C=1C(C)C)C1CCN(CC1)CCNC)F OIFOYLUMWREYOV-UHFFFAOYSA-N 0.000 claims 2
OTYNVTIGGOEUDJ-UHFFFAOYSA-N 2-[4-[2-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-oxoethyl]piperazin-1-yl]-N-propan-2-ylacetamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1CCN(CC1)CC(=O)NC(C)C)=O OTYNVTIGGOEUDJ-UHFFFAOYSA-N 0.000 claims 2
VBKZKOQEJYXUDY-UHFFFAOYSA-N 2-[4-[3-(2,2-difluoroethyl)-2-(3,4-dimethoxyphenyl)-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(=C(C=C1)OC)OC)F VBKZKOQEJYXUDY-UHFFFAOYSA-N 0.000 claims 2
RJMUVXCXVKPOGH-UHFFFAOYSA-N 2-[4-[3-(2,2-difluoroethyl)-2-(3,4-dimethoxyphenyl)-1H-indol-5-yl]piperidin-1-yl]-N-methylacetamide Chemical compound FC(CC1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC(=O)NC)C1=CC(=C(C=C1)OC)OC)F RJMUVXCXVKPOGH-UHFFFAOYSA-N 0.000 claims 2
YYRMZSMTUIYKJT-UHFFFAOYSA-N 2-[4-[3-(cyclopropylmethyl)-2-(3,4-dimethoxyphenyl)-1H-indol-5-yl]piperidin-1-yl]-N-methylethanamine 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.CNCCN1CCC(CC1)c1ccc2[nH]c(c(CC3CC3)c2c1)-c1ccc(OC)c(OC)c1 YYRMZSMTUIYKJT-UHFFFAOYSA-N 0.000 claims 2
CHBRVGAYYYAVDH-OAQYLSRUSA-N 2-[[(2R)-2,3-dihydroxypropyl]amino]-1-[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound O[C@H](CNCC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)C)CO CHBRVGAYYYAVDH-OAQYLSRUSA-N 0.000 claims 2
WWQBPJYXYGFQOH-QFIPXVFZSA-N 2-[[(2S)-2,3-dihydroxypropyl]amino]-1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound O[C@@H](CNCC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)C(C)C)CO WWQBPJYXYGFQOH-QFIPXVFZSA-N 0.000 claims 2
DFJVYARGIMEANF-UHFFFAOYSA-N 2-[[2-[4-[2-(3,4-dimethoxyphenyl)-3-ethyl-1H-indol-5-yl]piperidin-1-yl]-2-oxoethyl]amino]acetonitrile Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C(CNCC#N)=O DFJVYARGIMEANF-UHFFFAOYSA-N 0.000 claims 2
RXVPLMHAVFGOHS-UHFFFAOYSA-N 2-[[2-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-oxoethyl]amino]acetamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CNCC(=O)N)=O RXVPLMHAVFGOHS-UHFFFAOYSA-N 0.000 claims 2
GUWNTDZRXXMVRJ-UHFFFAOYSA-N 2-[[2-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-oxoethyl]amino]acetonitrile Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CNCC#N)=O GUWNTDZRXXMVRJ-UHFFFAOYSA-N 0.000 claims 2
XZDWBYRIKFPWKV-UHFFFAOYSA-N 2-[[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]methyl]-1,3-thiazole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC=1SC=CN=1 XZDWBYRIKFPWKV-UHFFFAOYSA-N 0.000 claims 2
VRJNDHHBQLDOBD-UHFFFAOYSA-N 2-[[4-[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]piperidin-1-yl]methyl]-1,3-thiazole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CCN(CC1)CC=1SC=CN=1 VRJNDHHBQLDOBD-UHFFFAOYSA-N 0.000 claims 2
FURJUWMKGQHYAK-UHFFFAOYSA-N 3-(2,2-difluoroethyl)-2-(3,4-dimethoxyphenyl)-5-piperidin-4-yl-1H-indole Chemical compound FC(CC1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC(=C(C=C1)OC)OC)F FURJUWMKGQHYAK-UHFFFAOYSA-N 0.000 claims 2
PIUGQICSTXBERZ-UHFFFAOYSA-N 3-[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]-N,N-dimethylcyclohexan-1-amine Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CC(CCC1)N(C)C PIUGQICSTXBERZ-UHFFFAOYSA-N 0.000 claims 2
OEKRBUYTIPRPII-UHFFFAOYSA-N 3-[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]-N-(2-methylpropyl)cyclohexan-1-amine Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CC(CCC1)NCC(C)C OEKRBUYTIPRPII-UHFFFAOYSA-N 0.000 claims 2
BNZJHLFSMUQTKR-UHFFFAOYSA-N 3-[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]-N-methyl-N-(2-methylpropyl)cyclohexan-1-amine Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CC(CCC1)N(C)CC(C)C BNZJHLFSMUQTKR-UHFFFAOYSA-N 0.000 claims 2
TYLJCVXTYLPRPG-UHFFFAOYSA-N 3-[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]-N-methylpropan-1-amine Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)CCCNC TYLJCVXTYLPRPG-UHFFFAOYSA-N 0.000 claims 2
SBKVWBWSAKWOLL-UHFFFAOYSA-N 3-[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]cyclohexan-1-amine Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CC(CCC1)N SBKVWBWSAKWOLL-UHFFFAOYSA-N 0.000 claims 2
OAOCHJFPWIFXPA-UHFFFAOYSA-N 3-[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]propan-1-ol Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)CCCO OAOCHJFPWIFXPA-UHFFFAOYSA-N 0.000 claims 2
UUANIZFQDZMENJ-UHFFFAOYSA-N 3-[4-[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]piperidin-1-yl]propane-1,2-diol Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CCN(CC1)CC(CO)O UUANIZFQDZMENJ-UHFFFAOYSA-N 0.000 claims 2
NCKCRYCXFBMMDK-UHFFFAOYSA-N 3-[4-[[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]methyl]phenoxy]-N,N-dimethylpropan-1-amine Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)CC1=CC=C(OCCCN(C)C)C=C1 NCKCRYCXFBMMDK-UHFFFAOYSA-N 0.000 claims 2
OUUKYJDNAWWQTC-UHFFFAOYSA-N 3-[[2-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-oxoethyl]-methylamino]-N,N-diethylpropanamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN(CCC(=O)N(CC)CC)C)=O OUUKYJDNAWWQTC-UHFFFAOYSA-N 0.000 claims 2
UBIXCHZYCHHLML-UHFFFAOYSA-N 3-chloro-2-(3,4-dimethoxyphenyl)-5-[1-[1-(2-methylpropyl)piperidin-4-yl]piperidin-4-yl]-1H-indole 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.COc1ccc(cc1OC)-c1[nH]c2ccc(cc2c1Cl)C1CCN(CC1)C1CCN(CC(C)C)CC1 UBIXCHZYCHHLML-UHFFFAOYSA-N 0.000 claims 2
NIPIVFKZKKGQQJ-UHFFFAOYSA-N 4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]-N-(2-phenylethyl)piperidine-1-carboxamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)C(=O)NCCC1=CC=CC=C1 NIPIVFKZKKGQQJ-UHFFFAOYSA-N 0.000 claims 2
KZRQMHJWEAROMZ-UHFFFAOYSA-N 4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]-N-(furan-2-ylmethyl)piperidine-1-carboxamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)C(=O)NCC=1OC=CC=1 KZRQMHJWEAROMZ-UHFFFAOYSA-N 0.000 claims 2
DQILBLZVLNCUCB-UHFFFAOYSA-N 4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]-N-ethylpiperidine-1-carboxamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)C(=O)NCC DQILBLZVLNCUCB-UHFFFAOYSA-N 0.000 claims 2
JOUATMXLSKEACO-UHFFFAOYSA-N 4-[2-(3,4-dimethoxyphenyl)-3-ethyl-1H-indol-5-yl]-N-propan-2-ylpiperidine-1-carboxamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C(=O)NC(C)C JOUATMXLSKEACO-UHFFFAOYSA-N 0.000 claims 2
UNXHRHIPNPRMQD-UHFFFAOYSA-N 4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-2-one Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CC(NCC1)=O UNXHRHIPNPRMQD-UHFFFAOYSA-N 0.000 claims 2
ODRKAZAPVPOUFQ-UHFFFAOYSA-N 4-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-N,N-dimethyl-4-oxobutanamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)C(CCC(=O)N(C)C)=O ODRKAZAPVPOUFQ-UHFFFAOYSA-N 0.000 claims 2
JYDNKXCLFLSMGQ-UHFFFAOYSA-N 4-[4-[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]piperidin-1-yl]butanoic acid Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CCN(CC1)CCCC(=O)O JYDNKXCLFLSMGQ-UHFFFAOYSA-N 0.000 claims 2
YUTXAKUMAAFHEH-UHFFFAOYSA-N 4-[4-[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]piperidin-1-yl]cyclohexan-1-ol Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)C1CCN(CC1)C1CCC(CC1)O YUTXAKUMAAFHEH-UHFFFAOYSA-N 0.000 claims 2
WONIZFGRRREDPF-UHFFFAOYSA-N 4-[[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]methyl]-1,3-thiazol-2-amine Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)CC=1N=C(SC=1)N WONIZFGRRREDPF-UHFFFAOYSA-N 0.000 claims 2
VHOQOFOPPONQFR-UHFFFAOYSA-N 4-[[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]methyl]-N,N-dimethylaniline Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)CC1=CC=C(N(C)C)C=C1 VHOQOFOPPONQFR-UHFFFAOYSA-N 0.000 claims 2
DWAOFMKSHWGVGC-UHFFFAOYSA-N 4-[[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]methyl]-N,N-dimethylnaphthalen-1-amine Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)CC1=CC=C(C2=CC=CC=C12)N(C)C DWAOFMKSHWGVGC-UHFFFAOYSA-N 0.000 claims 2
ZCRZDQIPJBCBDM-UHFFFAOYSA-N 4-[[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]methyl]quinoline Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)CC1=CC=NC2=CC=CC=C12 ZCRZDQIPJBCBDM-UHFFFAOYSA-N 0.000 claims 2
SAKKTICGZBBCNM-UHFFFAOYSA-N 4-[[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]methyl]-N,N-dimethylaniline Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC1=CC=C(N(C)C)C=C1 SAKKTICGZBBCNM-UHFFFAOYSA-N 0.000 claims 2
TXYIPLOTCZSOMI-UHFFFAOYSA-N 4-[[4-[4-[2-(3,4-dimethoxyphenyl)-3-ethyl-1H-indol-5-yl]piperidin-1-yl]piperidin-1-yl]methyl]-2-methyl-1,3-oxazole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C1CCN(CC1)CC=1N=C(OC=1)C TXYIPLOTCZSOMI-UHFFFAOYSA-N 0.000 claims 2
QHDKDSATHFSXKZ-UHFFFAOYSA-N 4-[[4-[4-[2-(3,4-dimethoxyphenyl)-3-ethyl-1H-indol-5-yl]piperidin-1-yl]piperidin-1-yl]methyl]-3,5-dimethyl-1,2-oxazole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C1CCN(CC1)CC=1C(=NOC=1C)C QHDKDSATHFSXKZ-UHFFFAOYSA-N 0.000 claims 2
CQJZCZJZOGBTOZ-UHFFFAOYSA-N 4-[[4-[4-[2-(3,4-dimethoxyphenyl)-3-ethyl-1H-indol-5-yl]piperidin-1-yl]piperidin-1-yl]methyl]thiadiazole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C1CCN(CC1)CC=1N=NSC=1 CQJZCZJZOGBTOZ-UHFFFAOYSA-N 0.000 claims 2
FCLKEXJIZNWLTN-UHFFFAOYSA-N 5-(3,3-difluoropiperidin-4-yl)-2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indole Chemical compound FC1(CNCCC1C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)C(C)C)F FCLKEXJIZNWLTN-UHFFFAOYSA-N 0.000 claims 2
YAXMFUQYJKQPMA-UHFFFAOYSA-N 5-[1-(1-benzylpiperidin-4-yl)piperidin-4-yl]-2-(3,4-dimethoxyphenyl)-3-ethyl-1H-indole Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)CC YAXMFUQYJKQPMA-UHFFFAOYSA-N 0.000 claims 2
OIMVOUATAILURI-UHFFFAOYSA-N 5-[1-(1-benzylpiperidin-4-yl)piperidin-4-yl]-2-(3,4-dimethoxyphenyl)-3-methyl-1H-indole Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)C OIMVOUATAILURI-UHFFFAOYSA-N 0.000 claims 2
PDFGTHSVJIUDAO-UHFFFAOYSA-N 5-[1-(1-cyclobutylpiperidin-4-yl)piperidin-4-yl]-2-(3,4-dimethoxyphenyl)-3-methyl-1H-indole Chemical compound C1(CCC1)N1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)C PDFGTHSVJIUDAO-UHFFFAOYSA-N 0.000 claims 2
ARODASQFLRJWHZ-UHFFFAOYSA-N 5-[1-(1-cyclohexylpiperidin-4-yl)piperidin-4-yl]-2-(3,4-dimethoxyphenyl)-3-methyl-1H-indole Chemical compound C1(CCCCC1)N1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)C ARODASQFLRJWHZ-UHFFFAOYSA-N 0.000 claims 2
HQCUVSQHCPCITR-UHFFFAOYSA-N 5-[1-(1-cyclopentylazepan-4-yl)piperidin-4-yl]-2-(3,4-dimethoxyphenyl)-3-methyl-1H-indole Chemical compound C1(CCCC1)N1CCC(CCC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)C HQCUVSQHCPCITR-UHFFFAOYSA-N 0.000 claims 2
OBYJFOXNMFRBCN-UHFFFAOYSA-N 5-[1-(1-cyclopentylpiperidin-4-yl)piperidin-4-yl]-2-(3,4-dimethoxyphenyl)-3-ethyl-1H-indole Chemical compound C1(CCCC1)N1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)CC OBYJFOXNMFRBCN-UHFFFAOYSA-N 0.000 claims 2
BLOSMSKCYRCPNK-UHFFFAOYSA-N 5-[1-(1-cyclopentylpiperidin-4-yl)piperidin-4-yl]-2-(3,4-dimethoxyphenyl)-3-methyl-1H-indole Chemical compound C1(CCCC1)N1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)C BLOSMSKCYRCPNK-UHFFFAOYSA-N 0.000 claims 2
AOAULTJJQGAKJK-UHFFFAOYSA-N 5-[1-(1-cyclopropylpiperidin-4-yl)piperidin-4-yl]-2-(3,4-dimethoxyphenyl)-3-methyl-1H-indole Chemical compound C1(CC1)N1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)C AOAULTJJQGAKJK-UHFFFAOYSA-N 0.000 claims 2
XQWDOAPKAHDNRB-UHFFFAOYSA-N 5-[1-(azepan-4-yl)piperidin-4-yl]-2-(3,4-dimethoxyphenyl)-3-methyl-1H-indole Chemical compound N1CCC(CCC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)C XQWDOAPKAHDNRB-UHFFFAOYSA-N 0.000 claims 2
SQOJGWPBHQXGST-UHFFFAOYSA-N 5-[1-[(1-benzylpyrrolidin-3-yl)methyl]piperidin-4-yl]-2-(3,4-dimethoxyphenyl)-3-methyl-1H-indole Chemical compound C(C1=CC=CC=C1)N1CC(CC1)CN1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)C SQOJGWPBHQXGST-UHFFFAOYSA-N 0.000 claims 2
NONTYSKWSLSAFN-UHFFFAOYSA-N 5-[1-[1-(cyclohexylmethyl)piperidin-4-yl]piperidin-4-yl]-2-(3,4-dimethoxyphenyl)-3-methyl-1H-indole Chemical compound C1(CCCCC1)CN1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)C NONTYSKWSLSAFN-UHFFFAOYSA-N 0.000 claims 2
LVCVYMMDHWCUDR-UHFFFAOYSA-N 5-[1-[1-(cyclopentylmethyl)piperidin-4-yl]piperidin-4-yl]-2-(3,4-dimethoxyphenyl)-3-methyl-1H-indole Chemical compound C1(CCCC1)CN1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)C LVCVYMMDHWCUDR-UHFFFAOYSA-N 0.000 claims 2
KRPNVOYUZUGOAA-UHFFFAOYSA-N 5-[1-[1-(cyclopropylmethyl)azepan-4-yl]piperidin-4-yl]-2-(3,4-dimethoxyphenyl)-3-methyl-1H-indole Chemical compound C1(CC1)CN1CCC(CCC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)C KRPNVOYUZUGOAA-UHFFFAOYSA-N 0.000 claims 2
UJHDSRJKQIPJFN-UHFFFAOYSA-N 5-[1-[1-(cyclopropylmethyl)piperidin-4-yl]piperidin-4-yl]-2-(3,4-dimethoxyphenyl)-3-methyl-1H-indole Chemical compound C1(CC1)CN1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)C UJHDSRJKQIPJFN-UHFFFAOYSA-N 0.000 claims 2
BOUZKHDHJAZUCH-UHFFFAOYSA-N 5-[[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]methyl]quinoline Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)CC1=C2C=CC=NC2=CC=C1 BOUZKHDHJAZUCH-UHFFFAOYSA-N 0.000 claims 2
YQYPMBKCECFNRH-UHFFFAOYSA-N 5-[[4-[4-[2-(3,4-dimethoxyphenyl)-3-ethyl-1H-indol-5-yl]piperidin-1-yl]piperidin-1-yl]methyl]-1,3-oxazole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C1CCN(CC1)CC1=CN=CO1 YQYPMBKCECFNRH-UHFFFAOYSA-N 0.000 claims 2
IHPVVNQQERJJSY-UHFFFAOYSA-N 5-[[4-[4-[2-(3,4-dimethoxyphenyl)-3-ethyl-1H-indol-5-yl]piperidin-1-yl]piperidin-1-yl]methyl]-2-methyl-1,3-oxazole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C1CCN(CC1)CC1=CN=C(O1)C IHPVVNQQERJJSY-UHFFFAOYSA-N 0.000 claims 2
JFZVJARWMMLPKV-UHFFFAOYSA-N 6-[[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]methyl]isoquinoline Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)CC=1C=C2C=CN=CC2=CC=1 JFZVJARWMMLPKV-UHFFFAOYSA-N 0.000 claims 2
IZJIDTVCCBLOBA-UHFFFAOYSA-N 8-[[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]methyl]quinoline Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)CC=1C=CC=C2C=CC=NC=12 IZJIDTVCCBLOBA-UHFFFAOYSA-N 0.000 claims 2
208000023275 Autoimmune disease Diseases 0.000 claims 2
UURNQQZAQATLIZ-UHFFFAOYSA-N FC(C(=O)O)(F)F.COC=1C=C(C=CC1OC)C=1NC2=CC=C(C=C2C1CC(C)C)C1CCN(CC1)C(CNCC)=O Chemical compound FC(C(=O)O)(F)F.COC=1C=C(C=CC1OC)C=1NC2=CC=C(C=C2C1CC(C)C)C1CCN(CC1)C(CNCC)=O UURNQQZAQATLIZ-UHFFFAOYSA-N 0.000 claims 2
POOOVVQPTNLPEB-UHFFFAOYSA-N N-(2-acetamidoethyl)-2-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]acetamide Chemical compound C(C)(=O)NCCNC(CN1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)CC(F)(F)F)=O POOOVVQPTNLPEB-UHFFFAOYSA-N 0.000 claims 2
GRNSXDLXPMPUOB-UHFFFAOYSA-N N-(5-tert-butyl-1H-pyrazol-3-yl)-2-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]acetamide Chemical compound C(C)(C)(C)C1=CC(=NN1)NC(CN1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)CC(F)(F)F)=O GRNSXDLXPMPUOB-UHFFFAOYSA-N 0.000 claims 2
LNWZIQSBOZOHKM-UHFFFAOYSA-N N-(cyanomethyl)-2-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]acetamide Chemical compound C(#N)CNC(CN1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)CC(F)(F)F)=O LNWZIQSBOZOHKM-UHFFFAOYSA-N 0.000 claims 2
FKOWIOZNZWBWSX-UHFFFAOYSA-N N-(cyclopropylmethyl)-2-[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]-N-methylethanamine Chemical compound C1(CC1)CN(CCN1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)C)C FKOWIOZNZWBWSX-UHFFFAOYSA-N 0.000 claims 2
XRMAVBIRDVMGTF-UHFFFAOYSA-N N-[2-[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]ethyl]-N,2-dimethylpropan-1-amine Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)CCN(CC(C)C)C XRMAVBIRDVMGTF-UHFFFAOYSA-N 0.000 claims 2
SATSSUHGGXGJDG-UHFFFAOYSA-N N-[2-[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]ethyl]-N-methyloxetan-3-amine Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)CCN(C1COC1)C SATSSUHGGXGJDG-UHFFFAOYSA-N 0.000 claims 2
NTDNXEBUDCSLDF-UHFFFAOYSA-N N-[3-[[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]methyl]phenyl]methanesulfonamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC=1C=C(C=CC=1)NS(=O)(=O)C NTDNXEBUDCSLDF-UHFFFAOYSA-N 0.000 claims 2
DUDJMKMGSVKIGT-UHFFFAOYSA-N N-[4-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-4-oxobutyl]acetamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)C(CCCNC(C)=O)=O DUDJMKMGSVKIGT-UHFFFAOYSA-N 0.000 claims 2
FISAFHOHBMJNCR-UHFFFAOYSA-N [1-[4-[2-(3,4-dimethoxyphenyl)-3-ethyl-1H-indol-5-yl]piperidin-1-yl]-2-methyl-1-oxopropan-2-yl] acetate Chemical compound C(C)(=O)OC(C(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)CC)(C)C FISAFHOHBMJNCR-UHFFFAOYSA-N 0.000 claims 2
PXSOIAHTRHJZGY-UHFFFAOYSA-N [4-[2-(3,4-dimethoxyphenyl)-3-ethyl-1H-indol-5-yl]piperidin-1-yl]-(4-methylpiperidin-4-yl)methanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C(=O)C1(CCNCC1)C PXSOIAHTRHJZGY-UHFFFAOYSA-N 0.000 claims 2
OYHCWDGJCJTMBR-UHFFFAOYSA-N [4-[2-(3,4-dimethoxyphenyl)-3-ethyl-1H-indol-5-yl]piperidin-1-yl]-piperidin-4-ylmethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C(=O)C1CCNCC1 OYHCWDGJCJTMBR-UHFFFAOYSA-N 0.000 claims 2
KQPACRAINOJQBE-UHFFFAOYSA-N [4-[2-(3,4-dimethoxyphenyl)-3-ethyl-1H-indol-5-yl]piperidin-1-yl]-pyridin-4-ylmethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C(=O)C1=CC=NC=C1 KQPACRAINOJQBE-UHFFFAOYSA-N 0.000 claims 2
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
KFMDLJWPDJEVTR-UHFFFAOYSA-N ethyl 5-[[4-[4-[2-(3,4-dimethoxyphenyl)-3-ethyl-1H-indol-5-yl]piperidin-1-yl]piperidin-1-yl]methyl]-2,4-dimethyl-1H-pyrrole-3-carboxylate Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C1CCN(CC1)CC1=C(C(=C(N1)C)C(=O)OCC)C KFMDLJWPDJEVTR-UHFFFAOYSA-N 0.000 claims 2
201000006417 multiple sclerosis Diseases 0.000 claims 2
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 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 2
201000000596 systemic lupus erythematosus Diseases 0.000 claims 2
KZYILSYZFIDVLR-UHFFFAOYSA-N tert-butyl 2-(3,4-dimethoxyphenyl)-5-[3-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]-3-propan-2-ylindole-1-carboxylate Chemical compound C(C)(C)(C)OC(=O)N1CC(C(CC1)C=1C=C2C(=C(N(C2=CC=1)C(=O)OC(C)(C)C)C1=CC(=C(C=C1)OC)OC)C(C)C)O KZYILSYZFIDVLR-UHFFFAOYSA-N 0.000 claims 2
HQVLBNDMOKXVOH-UHFFFAOYSA-N tert-butyl 3-[4-[2-(3,4-dimethoxyphenyl)-3-ethyl-1H-indol-5-yl]piperidine-1-carbonyl]piperidine-1-carboxylate Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C(=O)C1CN(CCC1)C(=O)OC(C)(C)C HQVLBNDMOKXVOH-UHFFFAOYSA-N 0.000 claims 2
YHOFVPYDJZMTCI-UHFFFAOYSA-N tert-butyl N-[2-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-2-oxoethyl]-N-methylcarbamate Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)C(CN(C(OC(C)(C)C)=O)C)=O YHOFVPYDJZMTCI-UHFFFAOYSA-N 0.000 claims 2
UIVPAUSUCXIFKA-UHFFFAOYSA-N tert-butyl N-[2-[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]ethyl]carbamate Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C)C1CCN(CC1)CCNC(OC(C)(C)C)=O UIVPAUSUCXIFKA-UHFFFAOYSA-N 0.000 claims 2
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GMMFRFRIHHKRIW-UHFFFAOYSA-N 1-[2-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-2-oxoethyl]-N,N-diethylpiperidine-3-carboxamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)C(CN1CC(CCC1)C(=O)N(CC)CC)=O GMMFRFRIHHKRIW-UHFFFAOYSA-N 0.000 claims 1
QWQWGZNDNYUSII-UHFFFAOYSA-N 1-[2-[4-[2-(3,4-dimethoxyphenyl)-3-(oxan-4-yl)-1H-indol-5-yl]piperidin-1-yl]-2-oxoethyl]-N,N-diethylpiperidine-3-carboxamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C1CCOCC1)C1CCN(CC1)C(CN1CC(CCC1)C(=O)N(CC)CC)=O QWQWGZNDNYUSII-UHFFFAOYSA-N 0.000 claims 1
SKJWDLBPFUSZAD-UHFFFAOYSA-N 1-[2-[4-[2-(3,4-dimethoxyphenyl)-3-ethyl-1H-indol-5-yl]piperidin-1-yl]-2-oxoethyl]-N,N-diethylpiperidine-3-carboxamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C(CN1CC(CCC1)C(=O)N(CC)CC)=O SKJWDLBPFUSZAD-UHFFFAOYSA-N 0.000 claims 1
VRNTYBSDKNXMAZ-UHFFFAOYSA-N 1-[2-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-oxoethyl]-N-(1-propan-2-ylpiperidin-4-yl)piperidine-3-carboxamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1CC(CCC1)C(=O)NC1CCN(CC1)C(C)C)=O VRNTYBSDKNXMAZ-UHFFFAOYSA-N 0.000 claims 1
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CBAGUEIGPOTERP-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-(1-methylpiperidin-4-yl)oxyethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(COC1CCN(CC1)C)=O CBAGUEIGPOTERP-UHFFFAOYSA-N 0.000 claims 1
BOUQRPPKFNKECS-NSOVKSMOSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[(3S)-3-[(3S)-3-hydroxypyrrolidine-1-carbonyl]piperidin-1-yl]ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN1C[C@H](CCC1)C(=O)N1C[C@H](CC1)O)=O BOUQRPPKFNKECS-NSOVKSMOSA-N 0.000 claims 1
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IBGHUYWWDMPUKJ-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-ethyl-5-[1-[1-[(1-methylimidazol-2-yl)methyl]piperidin-4-yl]piperidin-4-yl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C1CCN(CC1)CC=1N(C=CN=1)C IBGHUYWWDMPUKJ-UHFFFAOYSA-N 0.000 claims 1
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SUCRQWCGFFVMNH-UHFFFAOYSA-N 3-[[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]methyl]benzonitrile Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC=1C=C(C#N)C=CC=1 SUCRQWCGFFVMNH-UHFFFAOYSA-N 0.000 claims 1
CMQISCNONRUGCA-UHFFFAOYSA-N 4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-3-ol 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COc1ccc(cc1OC)-c1[nH]c2ccc(cc2c1C(C)C)C1CCNCC1O CMQISCNONRUGCA-UHFFFAOYSA-N 0.000 claims 1
102100036238 Dihydropyrimidinase Human genes 0.000 claims 1
208000021386 Sjogren Syndrome Diseases 0.000 claims 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
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125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
PCDHSSHKDZYLLI-UHFFFAOYSA-N butan-1-one Chemical compound CCC[C]=O PCDHSSHKDZYLLI-UHFFFAOYSA-N 0.000 claims 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
208000037976 chronic inflammation Diseases 0.000 claims 1
208000037893 chronic inflammatory disorder Diseases 0.000 claims 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
108091022884 dihydropyrimidinase Proteins 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
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BVOCPVIXARZNQN-UHFFFAOYSA-N nipecotamide Chemical compound NC(=O)C1CCCNC1 BVOCPVIXARZNQN-UHFFFAOYSA-N 0.000 claims 1
125000001715 oxadiazolyl group Chemical group 0.000 claims 1
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206010039073 rheumatoid arthritis Diseases 0.000 claims 1

JP2019504954A 2016-07-30 2017-07-27 ジメトキシフェニル置換インドール化合物 Active JP6995109B2 (ja)