ES2863474T3 - Compuestos de indol sustituidos con dimetoxifenilo como inhibidores de TLR7, TLR8 o TLR9 - Google Patents
Compuestos de indol sustituidos con dimetoxifenilo como inhibidores de TLR7, TLR8 o TLR9 Download PDFInfo
- Publication number
- ES2863474T3 ES2863474T3 ES17764925T ES17764925T ES2863474T3 ES 2863474 T3 ES2863474 T3 ES 2863474T3 ES 17764925 T ES17764925 T ES 17764925T ES 17764925 T ES17764925 T ES 17764925T ES 2863474 T3 ES2863474 T3 ES 2863474T3
- Authority
- ES
- Spain
- Prior art keywords
- piperidin
- crxrx
- dimethoxyphenyl
- alkyl
- indol
- 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 description 31
- 101000669402 Homo sapiens Toll-like receptor 7 Proteins 0.000 title description 29
- 239000003112 inhibitor Substances 0.000 title description 13
- 102100033110 Toll-like receptor 8 Human genes 0.000 title description 12
- 101000800483 Homo sapiens Toll-like receptor 8 Proteins 0.000 title description 9
- 150000002475 indoles Chemical class 0.000 title description 7
- 125000005805 dimethoxy phenyl group Chemical group 0.000 title description 5
- 102000008235 Toll-Like Receptor 9 Human genes 0.000 title description 4
- 108010060818 Toll-Like Receptor 9 Proteins 0.000 title description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 361
- -1 2-oxa-6-azaspiro [3.3] heptanyl Chemical group 0.000 claims abstract description 304
- 150000001875 compounds Chemical class 0.000 claims abstract description 267
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 106
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 103
- 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 101
- 125000004966 cyanoalkyl group Chemical group 0.000 claims abstract description 59
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 58
- 150000003839 salts Chemical class 0.000 claims abstract description 54
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims abstract description 54
- 125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 52
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 52
- 125000000168 pyrrolyl group Chemical group 0.000 claims abstract description 49
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 44
- 125000003386 piperidinyl group Chemical group 0.000 claims abstract description 38
- 125000001424 substituent group Chemical group 0.000 claims abstract description 38
- 125000004193 piperazinyl group Chemical group 0.000 claims abstract description 34
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims abstract description 34
- 125000001113 thiadiazolyl group Chemical group 0.000 claims abstract description 33
- 125000000335 thiazolyl group Chemical group 0.000 claims abstract description 33
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 31
- 125000002541 furyl group Chemical group 0.000 claims abstract description 30
- 125000001041 indolyl group Chemical group 0.000 claims abstract description 30
- 125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 25
- 125000001425 triazolyl group Chemical group 0.000 claims abstract description 24
- 125000000842 isoxazolyl group Chemical group 0.000 claims abstract description 23
- 125000002971 oxazolyl group Chemical group 0.000 claims abstract description 23
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 20
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 20
- 125000004799 bromophenyl group Chemical group 0.000 claims abstract description 19
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 19
- 125000002757 morpholinyl group Chemical group 0.000 claims abstract description 18
- 125000004965 chloroalkyl group Chemical group 0.000 claims abstract description 16
- 125000003725 azepanyl group Chemical group 0.000 claims abstract description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 15
- 125000005959 diazepanyl group Chemical group 0.000 claims abstract description 14
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 14
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims abstract description 14
- 125000003831 tetrazolyl group Chemical group 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 9
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 9
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims abstract description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 7
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims abstract description 5
- 125000002393 azetidinyl group Chemical group 0.000 claims abstract description 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims abstract description 4
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims abstract description 4
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims abstract 2
- 201000006417 multiple sclerosis Diseases 0.000 claims description 130
- 239000000203 mixture Substances 0.000 claims description 108
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 67
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 60
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 50
- 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 45
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 36
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 25
- 239000008194 pharmaceutical composition Substances 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 125000003566 oxetanyl group Chemical group 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 19
- BVOCPVIXARZNQN-UHFFFAOYSA-N nipecotamide Chemical compound NC(=O)C1CCCNC1 BVOCPVIXARZNQN-UHFFFAOYSA-N 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 239000003937 drug carrier Substances 0.000 claims description 12
- 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 description 11
- 208000023275 Autoimmune disease Diseases 0.000 claims description 11
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 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 description 9
- 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 description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 9
- 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 8
- 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 8
- 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 description 8
- 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 description 8
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 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 7
- 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 7
- 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 description 7
- 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 description 7
- 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 description 7
- CQOXLNRQIAFKJD-UHFFFAOYSA-N FC(C(=O)O)(F)F.FC(C(=O)O)(F)F.C1(CC1)CN1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC1)C1=CC(=C(C=C1)OC)OC)C(C)C Chemical compound FC(C(=O)O)(F)F.FC(C(=O)O)(F)F.C1(CC1)CN1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC1)C1=CC(=C(C=C1)OC)OC)C(C)C CQOXLNRQIAFKJD-UHFFFAOYSA-N 0.000 claims description 7
- 208000027866 inflammatory disease Diseases 0.000 claims description 7
- 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 6
- 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 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
- APBNTWQDTVMMAM-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-(1-piperidin-4-ylpiperidin-4-yl)-3-propan-2-yl-1H-indole dihydrochloride Chemical compound Cl.Cl.COc1ccc(cc1OC)-c1[nH]c2ccc(cc2c1C(C)C)C1CCN(CC1)C1CCNCC1 APBNTWQDTVMMAM-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- 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 6
- 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 6
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
- 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 description 5
- 125000000979 2-amino-2-oxoethyl group Chemical group [H]C([*])([H])C(=O)N([H])[H] 0.000 claims description 5
- DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- 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
- ODHQVFPGHQBQSY-UHFFFAOYSA-N 1-(3-hydroxypyrrolidin-1-yl)ethanone Chemical compound CC(=O)N1CCC(O)C1 ODHQVFPGHQBQSY-UHFFFAOYSA-N 0.000 claims description 4
- 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 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
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- 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 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
- IAKJMKTZIBVDFE-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[3-(4-propan-2-ylpiperazine-1-carbonyl)piperidin-1-yl]ethanone Chemical compound COc1ccc(cc1OC)-c1[nH]c2ccc(cc2c1C(C)C)C1CCN(CC1)C(=O)CN1CCCC(C1)C(=O)N1CCN(CC1)C(C)C IAKJMKTZIBVDFE-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- GVNXOZLUVYRZHN-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-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(C)C)C1CCN(CC1)C(CN1CCC(CC1)N(C)C)=O GVNXOZLUVYRZHN-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
- 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
- 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
- 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 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
- 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 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
- 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 description 4
- 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 description 4
- QTLGIGBDOBOQHD-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-[1-[(1-methylpyrazol-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)CC=1C=NN(C=1)C QTLGIGBDOBOQHD-UHFFFAOYSA-N 0.000 claims description 4
- 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
- OKOWBQPAUMCDCM-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-[1-[(3-methylimidazol-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=CN=CN1C OKOWBQPAUMCDCM-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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
- 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
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- BFXHQIJUISCGNK-UHFFFAOYSA-N 2-[[2-[4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-oxoethyl]-methylamino]-N,N-diethylacetamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN(CC(=O)N(CC)CC)C)=O BFXHQIJUISCGNK-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 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 description 4
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Classifications
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- 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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- 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
- A61K31/40—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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- 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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- 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
- C07D401/14—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
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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
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- 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
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- 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
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- 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
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- Public Health (AREA)
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- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
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