KR102506321B1 - Tlr7, tlr8 또는 tlr9 억제제로서의 디메톡시페닐 치환된 인돌 화합물 - Google Patents
Tlr7, tlr8 또는 tlr9 억제제로서의 디메톡시페닐 치환된 인돌 화합물 Download PDFInfo
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- KR102506321B1 KR102506321B1 KR1020197005484A KR20197005484A KR102506321B1 KR 102506321 B1 KR102506321 B1 KR 102506321B1 KR 1020197005484 A KR1020197005484 A KR 1020197005484A KR 20197005484 A KR20197005484 A KR 20197005484A KR 102506321 B1 KR102506321 B1 KR 102506321B1
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- KR
- South Korea
- Prior art keywords
- dimethoxyphenyl
- piperidin
- indol
- alkyl
- isopropyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 102100039390 Toll-like receptor 7 Human genes 0.000 title abstract description 28
- 102100033110 Toll-like receptor 8 Human genes 0.000 title abstract description 19
- 239000003112 inhibitor Substances 0.000 title abstract description 8
- 101000669402 Homo sapiens Toll-like receptor 7 Proteins 0.000 title description 21
- 102000008235 Toll-Like Receptor 9 Human genes 0.000 title description 18
- 108010060818 Toll-Like Receptor 9 Proteins 0.000 title description 18
- 101000800483 Homo sapiens Toll-like receptor 8 Proteins 0.000 title description 12
- 125000005805 dimethoxy phenyl group Chemical group 0.000 title description 4
- 150000002475 indoles Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 143
- 150000003839 salts Chemical class 0.000 claims abstract description 37
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 26
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 15
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 11
- 230000002757 inflammatory effect Effects 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 293
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 236
- -1 2-oxa-6-azaspiro[3,3]heptanyl Chemical group 0.000 claims description 223
- 201000006417 multiple sclerosis Diseases 0.000 claims description 123
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 109
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 104
- 239000000203 mixture Substances 0.000 claims description 83
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 57
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 54
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 54
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 53
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 52
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 42
- 125000003386 piperidinyl group Chemical group 0.000 claims description 40
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 37
- 229910052799 carbon Inorganic materials 0.000 claims description 36
- 125000001424 substituent group Chemical group 0.000 claims description 35
- 125000002883 imidazolyl group Chemical group 0.000 claims description 32
- 125000004193 piperazinyl group Chemical group 0.000 claims description 32
- 125000004076 pyridyl group Chemical group 0.000 claims description 32
- 125000002541 furyl group Chemical group 0.000 claims description 31
- 125000003566 oxetanyl group Chemical group 0.000 claims description 31
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 31
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 31
- 125000000335 thiazolyl group Chemical group 0.000 claims description 31
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 30
- 125000001041 indolyl group Chemical group 0.000 claims description 29
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 25
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 125000002971 oxazolyl group Chemical group 0.000 claims description 21
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 21
- 125000001425 triazolyl group Chemical group 0.000 claims description 21
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 20
- 229910052801 chlorine Inorganic materials 0.000 claims description 19
- 238000011282 treatment Methods 0.000 claims description 19
- 125000004799 bromophenyl group Chemical group 0.000 claims description 18
- 125000001544 thienyl group Chemical group 0.000 claims description 18
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 17
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 17
- 125000004965 chloroalkyl group Chemical group 0.000 claims description 16
- 125000002757 morpholinyl group Chemical group 0.000 claims description 16
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 15
- 239000003937 drug carrier Substances 0.000 claims description 13
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 13
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 13
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 125000005959 diazepanyl group Chemical group 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 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 description 8
- 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 description 8
- 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 description 8
- BVOCPVIXARZNQN-UHFFFAOYSA-N nipecotamide Chemical compound NC(=O)C1CCCNC1 BVOCPVIXARZNQN-UHFFFAOYSA-N 0.000 claims description 8
- 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 description 7
- 125000003725 azepanyl group Chemical group 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 7
- 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 description 6
- 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 description 6
- 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 description 6
- CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical group N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 claims description 6
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 6
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 6
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 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 description 5
- MQYHOFPQZUHNHZ-MUUNZHRXSA-N (3R)-1-[2-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-oxoethyl]-N-methyl-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)N(C)C(C)C)=O MQYHOFPQZUHNHZ-MUUNZHRXSA-N 0.000 claims description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- MQYHOFPQZUHNHZ-NDEPHWFRSA-N (3S)-1-[2-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-oxoethyl]-N-methyl-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)N(C)C(C)C)=O MQYHOFPQZUHNHZ-NDEPHWFRSA-N 0.000 claims description 4
- 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 description 4
- 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 description 4
- XOYLGVGNEQWYEV-SFHVURJKSA-N (3S)-3-amino-1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]butan-1-one Chemical compound N[C@H](CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)C(C)C)C XOYLGVGNEQWYEV-SFHVURJKSA-N 0.000 claims description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- HKKXPMMWLNPDEN-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-2-(1H-imidazol-5-yl)ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)C(CC=1N=CNC=1)=O HKKXPMMWLNPDEN-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- XDKUNBKHKOKZTH-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-4,4,4-trifluorobutan-1-one Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC(F)(F)F)C1CCN(CC1)C(CCC(F)(F)F)=O XDKUNBKHKOKZTH-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- QSHLLSVRBSRRSS-GCPOPKDISA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[(3R)-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-GCPOPKDISA-N 0.000 claims description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- LQJQHLCZLBVIHB-RUZDIDTESA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[[(2R)-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-RUZDIDTESA-N 0.000 claims description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- WSENBNJBTJUPTQ-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[methyl(propan-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)C(C)C)=O WSENBNJBTJUPTQ-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
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- 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 description 4
- 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 description 4
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- 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 description 4
- 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 description 4
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- WAZKSPZZTKAUHD-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-[1-[(2-methyl-1H-imidazol-5-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=CN=C(N1)C WAZKSPZZTKAUHD-UHFFFAOYSA-N 0.000 claims description 4
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- 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 description 4
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- 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 description 4
- VYKVSTXZBJWVSP-UHFFFAOYSA-N 2-[(5-tert-butyl-1H-pyrazol-3-yl)amino]-1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound C(C)(C)(C)C1=NNC(=C1)NCC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)C(C)C VYKVSTXZBJWVSP-UHFFFAOYSA-N 0.000 claims description 4
- PDNMEJYPILEBAJ-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-1-(4-piperidin-1-ylpiperidin-1-yl)ethanone Chemical compound N1(CCCCC1)C1CCN(CC1)C(CN1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=C(C=C1)OC)OC)CC(F)(F)F)=O PDNMEJYPILEBAJ-UHFFFAOYSA-N 0.000 claims description 4
- JIHLDJDRYCUKDC-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-1H-indol-5-yl]piperidin-1-yl]-1-(4-propan-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)C(C)C JIHLDJDRYCUKDC-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
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- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
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- A—HUMAN NECESSITIES
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
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- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Immunology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (3)
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| IN201611026137 | 2016-07-30 | ||
| IN11026137 | 2016-07-30 | ||
| PCT/US2017/044091 WO2018026620A1 (en) | 2016-07-30 | 2017-07-27 | Dimethoxyphenyl substituted indole compounds as tlr7, tlr8 or tlr9 inhibitors |
Publications (2)
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| KR20190034264A KR20190034264A (ko) | 2019-04-01 |
| KR102506321B1 true KR102506321B1 (ko) | 2023-03-03 |
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| CA3031675A1 (en) | 2016-07-30 | 2018-02-08 | Bristol-Myers Squibb Company | Dimethoxyphenyl substituted indole compounds as tlr7, tlr8 or tlr9 inhibitors |
| WO2018049089A1 (en) | 2016-09-09 | 2018-03-15 | Bristol-Myers Squibb Company | Pyridyl substituted indole compounds |
| BR112019007450A2 (pt) | 2016-10-14 | 2020-07-07 | Precision Biosciences, Inc. | meganucleases modificadas específicas para sequências de reconhecimento no genoma do vírus da hepatite b |
| JP7266576B2 (ja) * | 2017-08-04 | 2023-04-28 | ブリストル-マイヤーズ スクイブ カンパニー | [1,2,4]トリアゾロ[4,3-a]ピリジニル置換のインドール化合物 |
| JP7104775B2 (ja) | 2017-08-04 | 2022-07-21 | ブリストル-マイヤーズ スクイブ カンパニー | Tlr7/8/9の阻害剤として有用な置換インドール化合物 |
| WO2019099336A1 (en) | 2017-11-14 | 2019-05-23 | Bristol-Myers Squibb Company | Substituted indole compounds |
| JP2021505555A (ja) * | 2017-12-01 | 2021-02-18 | タイワンジェ ファーマシューティカルズ カンパニー リミテッドTaiwanj Pharmaceuticals Co., Ltd. | ベンゼン縮合複素環化合物およびその使用 |
| KR102781141B1 (ko) * | 2017-12-15 | 2025-03-13 | 브리스톨-마이어스 스큅 컴퍼니 | 치환된 인돌 에테르 화합물 |
| LT3728252T (lt) | 2017-12-18 | 2023-10-25 | Bristol-Myers Squibb Company | 4-azaindolo junginiai |
| SG11202005700SA (en) | 2017-12-19 | 2020-07-29 | Bristol Myers Squibb Co | Amide substituted indole compounds useful as tlr inhibitors |
| AU2018390820A1 (en) * | 2017-12-19 | 2020-08-06 | Bristol-Myers Squibb Company | Substituted indole compounds useful as TLR inhibitors |
| SG11202005704RA (en) | 2017-12-19 | 2020-07-29 | Bristol Myers Squibb Co | 6-azaindole compounds |
| EP3728282B1 (en) | 2017-12-20 | 2023-11-22 | Institute of Organic Chemistry and Biochemistry ASCR, V.V.I. | 2'3' cyclic dinucleotides with phosphonate bond activating the sting adaptor protein |
| CN111566120B (zh) | 2017-12-20 | 2023-09-29 | 捷克共和国有机化学与生物化学研究所 | 活化sting转接蛋白的具有膦酸酯键的3’3’环状二核苷酸 |
| KR102730859B1 (ko) | 2017-12-20 | 2024-11-15 | 브리스톨-마이어스 스큅 컴퍼니 | 아릴 및 헤테로아릴 치환된 인돌 화합물 |
| ES2904773T3 (es) | 2017-12-20 | 2022-04-06 | Bristol Myers Squibb Co | Compuestos de diazaindol |
| BR112020011984A2 (pt) | 2017-12-20 | 2020-11-17 | Bristol-Myers Squibb Company | compostos de amino indol úteis como inibidores de tlr |
| JP7328977B2 (ja) | 2018-02-12 | 2023-08-17 | エフ. ホフマン-ラ ロシュ アーゲー | ウイルス感染の処置および予防のための新規のスルホン化合物および誘導体 |
| CA3091142C (en) | 2018-02-26 | 2023-04-11 | Gilead Sciences, Inc. | Substituted pyrrolizine compounds and uses thereof |
| WO2019195181A1 (en) | 2018-04-05 | 2019-10-10 | Gilead Sciences, Inc. | Antibodies and fragments thereof that bind hepatitis b virus protein x |
| TWI818007B (zh) | 2018-04-06 | 2023-10-11 | 捷克科學院有機化學與生物化學研究所 | 2'3'-環二核苷酸 |
| TW202005654A (zh) | 2018-04-06 | 2020-02-01 | 捷克科學院有機化學與生物化學研究所 | 2,2,─環二核苷酸 |
| TWI833744B (zh) | 2018-04-06 | 2024-03-01 | 捷克科學院有機化學與生物化學研究所 | 3'3'-環二核苷酸 |
| US11142750B2 (en) | 2018-04-12 | 2021-10-12 | Precision Biosciences, Inc. | Optimized engineered meganucleases having specificity for a recognition sequence in the Hepatitis B virus genome |
| WO2019211799A1 (en) | 2018-05-03 | 2019-11-07 | Institute Of Organic Chemistry And Biochemistry Ascr, V.V.I. | 2'3'-cyclic dinucleotide analogue comprising a cyclopentanyl modified nucleotide |
| PE20210131A1 (es) | 2018-06-05 | 2021-01-19 | Hoffmann La Roche | COMPUESTOS TETRAHIDRO-1H-PIRAZINO[2,1-a]ISOINDOLILQUINOLINA PARA EL TRATAMIENTO DE ENFERMEDADES AUTOINMUNES |
| EP3807270B1 (en) | 2018-06-12 | 2023-09-13 | F. Hoffmann-La Roche AG | Novel heteroaryl heterocyclyl compounds for the treatment of autoimmune disease |
| EP3826724B1 (en) | 2018-07-23 | 2022-10-05 | F. Hoffmann-La Roche AG | Novel piperazine compounds for the treatment of autoimmune disease |
| WO2020028097A1 (en) | 2018-08-01 | 2020-02-06 | Gilead Sciences, Inc. | Solid forms of (r)-11-(methoxymethyl)-12-(3-methoxypropoxy)-3,3-dimethyl-8-0x0-2,3,8,13b-tetrahydro-1h-pyrido[2,1-a]pyrrolo[1,2-c] phthalazine-7-c arboxylic acid |
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