DE60214990T2 - Benzolsulfonsäureester-indol-5-yl als 5-ht6 rezeptor-antagonisten - Google Patents

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Publication number

DE60214990T2

DE60214990T2 DE60214990T DE60214990T DE60214990T2 DE 60214990 T2 DE60214990 T2 DE 60214990T2 DE 60214990 T DE60214990 T DE 60214990T DE 60214990 T DE60214990 T DE 60214990T DE 60214990 T2 DE60214990 T2 DE 60214990T2

Authority

DE

Germany

Prior art keywords

indol

methylpiperidin

ester

acid

mmol

Prior art date

2001-01-30

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.)

Expired - Fee Related

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• -1 BENZOLSULFONIC ACID ESTERS INDOL-5-YL Chemical class 0.000 title claims description 26
• 108091005435 5-HT6 receptors Proteins 0.000 title abstract 2
• 229940044551 receptor antagonist Drugs 0.000 title description 11
• 239000002464 receptor antagonist Substances 0.000 title description 11
• 150000001875 compounds Chemical class 0.000 claims abstract description 203
• 238000011282 treatment Methods 0.000 claims description 41
• 239000001257 hydrogen Substances 0.000 claims description 35
• 229910052739 hydrogen Inorganic materials 0.000 claims description 35
• 239000003814 drug Substances 0.000 claims description 24
• XIMWTVNLJKSGBH-UHFFFAOYSA-N [3-(1-methylpiperidin-4-yl)-1h-indol-5-yl] benzenesulfonate Chemical compound C1CN(C)CCC1C(C1=C2)=CNC1=CC=C2OS(=O)(=O)C1=CC=CC=C1 XIMWTVNLJKSGBH-UHFFFAOYSA-N 0.000 claims description 23
• 150000003839 salts Chemical class 0.000 claims description 19
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
• 150000002367 halogens Chemical class 0.000 claims description 17
• 229910052736 halogen Inorganic materials 0.000 claims description 16
• 150000002431 hydrogen Chemical group 0.000 claims description 13
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
• 238000004519 manufacturing process Methods 0.000 claims description 10
• 125000000217 alkyl group Chemical group 0.000 claims description 9
• 125000004432 carbon atom Chemical group C* 0.000 claims description 9
• 208000010877 cognitive disease Diseases 0.000 claims description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims description 9
• JZUAGNKBVRSAJD-UHFFFAOYSA-N [3-(1-methylpiperidin-4-yl)-1h-indol-5-yl] 2,6-difluorobenzenesulfonate Chemical compound C1CN(C)CCC1C(C1=C2)=CNC1=CC=C2OS(=O)(=O)C1=C(F)C=CC=C1F JZUAGNKBVRSAJD-UHFFFAOYSA-N 0.000 claims description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
• 201000000980 schizophrenia Diseases 0.000 claims description 7
• 239000003085 diluting agent Substances 0.000 claims description 6
• 125000001424 substituent group Chemical group 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
• 229910052731 fluorine Inorganic materials 0.000 claims description 5
• 239000011737 fluorine Substances 0.000 claims description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
• SCEHARXOKRVDBE-UHFFFAOYSA-N [3-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)-1h-indol-5-yl] benzenesulfonate Chemical compound C1N(C)CCC(C=2C3=CC(OS(=O)(=O)C=4C=CC=CC=4)=CC=C3NC=2)=C1 SCEHARXOKRVDBE-UHFFFAOYSA-N 0.000 claims description 4
• TUHDCYAJAMCYOE-UHFFFAOYSA-N [3-(1-methylpiperidin-4-yl)-1h-indol-5-yl] 4-aminobenzenesulfonate Chemical compound C1CN(C)CCC1C(C1=C2)=CNC1=CC=C2OS(=O)(=O)C1=CC=C(N)C=C1 TUHDCYAJAMCYOE-UHFFFAOYSA-N 0.000 claims description 4
• 125000005843 halogen group Chemical group 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 3
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
• QERFJVVHXQRMMQ-UHFFFAOYSA-N [1-butyl-3-(1-methylpiperidin-4-yl)indol-5-yl] benzenesulfonate Chemical compound C12=CC(OS(=O)(=O)C=3C=CC=CC=3)=CC=C2N(CCCC)C=C1C1CCN(C)CC1 QERFJVVHXQRMMQ-UHFFFAOYSA-N 0.000 claims description 3
• VGEUFDHJGPEZTP-UHFFFAOYSA-N [3-(1-methylpiperidin-4-yl)-1h-indol-5-yl] 4-nitrobenzenesulfonate Chemical compound C1CN(C)CCC1C(C1=C2)=CNC1=CC=C2OS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 VGEUFDHJGPEZTP-UHFFFAOYSA-N 0.000 claims description 3
• 125000001153 fluoro group Chemical group F* 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
• 229920002554 vinyl polymer Polymers 0.000 claims description 3
• VPMPOGSTMUSVRT-UHFFFAOYSA-N [1,7-dimethyl-3-(1-methylpiperidin-4-yl)indol-5-yl] 2,6-difluorobenzenesulfonate Chemical compound C1CN(C)CCC1C(C1=C2)=CN(C)C1=C(C)C=C2OS(=O)(=O)C1=C(F)C=CC=C1F VPMPOGSTMUSVRT-UHFFFAOYSA-N 0.000 claims description 2
• GFJSINCJLPAEBP-UHFFFAOYSA-N [1,7-dimethyl-3-(1-methylpiperidin-4-yl)indol-5-yl] benzenesulfonate Chemical compound C1CN(C)CCC1C(C1=C2)=CN(C)C1=C(C)C=C2OS(=O)(=O)C1=CC=CC=C1 GFJSINCJLPAEBP-UHFFFAOYSA-N 0.000 claims description 2
• SSURHDVTVNUXPU-UHFFFAOYSA-N [1-[(4-fluorophenyl)methyl]-3-(1-methylpiperidin-4-yl)indol-5-yl] benzenesulfonate Chemical compound C1CN(C)CCC1C(C1=CC(OS(=O)(=O)C=2C=CC=CC=2)=CC=C11)=CN1CC1=CC=C(F)C=C1 SSURHDVTVNUXPU-UHFFFAOYSA-N 0.000 claims description 2
• GPVHAPQRXUVNLQ-UHFFFAOYSA-N [1-benzyl-7-methyl-3-(1-methylpiperidin-4-yl)indol-5-yl] 2,6-difluorobenzenesulfonate Chemical compound C1CN(C)CCC1C(C1=CC(OS(=O)(=O)C=2C(=CC=CC=2F)F)=CC(C)=C11)=CN1CC1=CC=CC=C1 GPVHAPQRXUVNLQ-UHFFFAOYSA-N 0.000 claims description 2
• YBAOMYVOYKBGGN-UHFFFAOYSA-N [1-methyl-3-(1-methylpiperidin-4-yl)indol-5-yl] benzenesulfonate Chemical compound C1CN(C)CCC1C(C1=C2)=CN(C)C1=CC=C2OS(=O)(=O)C1=CC=CC=C1 YBAOMYVOYKBGGN-UHFFFAOYSA-N 0.000 claims description 2
• ROSXPNMCBNLKBE-UHFFFAOYSA-N [2-methyl-3-(1-methylpiperidin-4-yl)-1h-indol-5-yl] 2,6-difluorobenzenesulfonate Chemical compound C1CN(C)CCC1C(C1=C2)=C(C)NC1=CC=C2OS(=O)(=O)C1=C(F)C=CC=C1F ROSXPNMCBNLKBE-UHFFFAOYSA-N 0.000 claims description 2
• GXYCNBXUKZWYBI-UHFFFAOYSA-N [2-methyl-3-(1-methylpiperidin-4-yl)-1h-indol-5-yl] benzenesulfonate Chemical compound C1CN(C)CCC1C(C1=C2)=C(C)NC1=CC=C2OS(=O)(=O)C1=CC=CC=C1 GXYCNBXUKZWYBI-UHFFFAOYSA-N 0.000 claims description 2
• JGNHMHJWQIAPBN-UHFFFAOYSA-N [3-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)-1h-indol-5-yl] 2,6-difluorobenzenesulfonate Chemical compound C1N(C)CCC(C=2C3=CC(OS(=O)(=O)C=4C(=CC=CC=4F)F)=CC=C3NC=2)=C1 JGNHMHJWQIAPBN-UHFFFAOYSA-N 0.000 claims description 2
• WZEIFCRCNCUNTB-UHFFFAOYSA-N [3-(1-methylpiperidin-4-yl)-1-(2,2,2-trifluoroethyl)indol-5-yl] benzenesulfonate Chemical compound C1CN(C)CCC1C(C1=C2)=CN(CC(F)(F)F)C1=CC=C2OS(=O)(=O)C1=CC=CC=C1 WZEIFCRCNCUNTB-UHFFFAOYSA-N 0.000 claims description 2
• SGBLRMIQGXUDHH-UHFFFAOYSA-N [3-(1-methylpiperidin-4-yl)-1h-indol-5-yl] 2,3,4-trifluorobenzenesulfonate Chemical compound C1CN(C)CCC1C(C1=C2)=CNC1=CC=C2OS(=O)(=O)C1=CC=C(F)C(F)=C1F SGBLRMIQGXUDHH-UHFFFAOYSA-N 0.000 claims description 2
• WIOSJFRMWVIGMD-UHFFFAOYSA-N [3-(1-methylpiperidin-4-yl)-1h-indol-5-yl] 2,4-difluorobenzenesulfonate Chemical compound C1CN(C)CCC1C(C1=C2)=CNC1=CC=C2OS(=O)(=O)C1=CC=C(F)C=C1F WIOSJFRMWVIGMD-UHFFFAOYSA-N 0.000 claims description 2
• OTXXWTLWJFSVHO-UHFFFAOYSA-N [3-(1-methylpiperidin-4-yl)-1h-indol-5-yl] 2-fluorobenzenesulfonate Chemical compound C1CN(C)CCC1C(C1=C2)=CNC1=CC=C2OS(=O)(=O)C1=CC=CC=C1F OTXXWTLWJFSVHO-UHFFFAOYSA-N 0.000 claims description 2
• NFUJHHPNILEOEJ-UHFFFAOYSA-N [3-(1-methylpiperidin-4-yl)-1h-indol-5-yl] 4-(methanesulfonamido)benzenesulfonate Chemical compound C1CN(C)CCC1C(C1=C2)=CNC1=CC=C2OS(=O)(=O)C1=CC=C(NS(C)(=O)=O)C=C1 NFUJHHPNILEOEJ-UHFFFAOYSA-N 0.000 claims description 2
• AXZVGTHTHLKSDL-UHFFFAOYSA-N [3-(1-methylpiperidin-4-yl)-1h-indol-5-yl] 4-chlorobenzenesulfonate Chemical compound C1CN(C)CCC1C(C1=C2)=CNC1=CC=C2OS(=O)(=O)C1=CC=C(Cl)C=C1 AXZVGTHTHLKSDL-UHFFFAOYSA-N 0.000 claims description 2
• CFRATGPOLALVIY-UHFFFAOYSA-N [3-(1-methylpiperidin-4-yl)-1h-indol-5-yl] 4-fluorobenzenesulfonate Chemical compound C1CN(C)CCC1C(C1=C2)=CNC1=CC=C2OS(=O)(=O)C1=CC=C(F)C=C1 CFRATGPOLALVIY-UHFFFAOYSA-N 0.000 claims description 2
• NKDSXYHZUNGVID-UHFFFAOYSA-N [3-(1-methylpiperidin-4-yl)-1h-indol-5-yl] 4-iodobenzenesulfonate Chemical compound C1CN(C)CCC1C(C1=C2)=CNC1=CC=C2OS(=O)(=O)C1=CC=C(I)C=C1 NKDSXYHZUNGVID-UHFFFAOYSA-N 0.000 claims description 2
• BAMDDAOOKHBFHP-UHFFFAOYSA-N [6-fluoro-3-(1-methylpiperidin-4-yl)-1h-indol-5-yl] 2,6-difluorobenzenesulfonate Chemical compound C1CN(C)CCC1C(C1=C2)=CNC1=CC(F)=C2OS(=O)(=O)C1=C(F)C=CC=C1F BAMDDAOOKHBFHP-UHFFFAOYSA-N 0.000 claims description 2
• IBXFIXQLFFFHGD-UHFFFAOYSA-N [7-methyl-3-(1-methylpiperidin-4-yl)-1h-indol-5-yl] 2,6-dichlorobenzenesulfonate Chemical compound C1CN(C)CCC1C(C1=C2)=CNC1=C(C)C=C2OS(=O)(=O)C1=C(Cl)C=CC=C1Cl IBXFIXQLFFFHGD-UHFFFAOYSA-N 0.000 claims description 2
• FAOUPBYYGUBEBJ-UHFFFAOYSA-N [7-methyl-3-(1-methylpiperidin-4-yl)-1h-indol-5-yl] benzenesulfonate Chemical compound C1CN(C)CCC1C(C1=C2)=CNC1=C(C)C=C2OS(=O)(=O)C1=CC=CC=C1 FAOUPBYYGUBEBJ-UHFFFAOYSA-N 0.000 claims description 2
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
• SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims 3
• 229940092714 benzenesulfonic acid Drugs 0.000 claims 3
• JTBDAUNIHPKJQV-UHFFFAOYSA-N [1-benzyl-3-(1-methylpiperidin-4-yl)indol-5-yl] 2,6-difluorobenzenesulfonate Chemical compound C1CN(C)CCC1C(C1=CC(OS(=O)(=O)C=2C(=CC=CC=2F)F)=CC=C11)=CN1CC1=CC=CC=C1 JTBDAUNIHPKJQV-UHFFFAOYSA-N 0.000 claims 2
• LYHNZWIPSZUYDT-UHFFFAOYSA-N [1-methyl-3-(1-methylpiperidin-4-yl)indol-5-yl] 2,6-difluorobenzenesulfonate Chemical compound C1CN(C)CCC1C(C1=C2)=CN(C)C1=CC=C2OS(=O)(=O)C1=C(F)C=CC=C1F LYHNZWIPSZUYDT-UHFFFAOYSA-N 0.000 claims 2
• AUFIRGPROMANKW-UHFFFAOYSA-N 1-methyl-3,6-dihydro-2h-pyridine Chemical compound CN1CCC=CC1 AUFIRGPROMANKW-UHFFFAOYSA-N 0.000 claims 1
• JCRJDANSDJDMCG-UHFFFAOYSA-N 4-methylbenzenesulfonic acid;1-methylpiperidine Chemical compound CN1CCCCC1.CC1=CC=C(S(O)(=O)=O)C=C1 JCRJDANSDJDMCG-UHFFFAOYSA-N 0.000 claims 1
• YODIPMROGSPCJQ-UHFFFAOYSA-N C1=C(C2CCN(C)CC2)C2=CC(OS(=O)(=O)C=3C(=CC=CC=3F)F)=CC(C)=C2N1C(C)C1=CC=CC=C1 Chemical compound C1=C(C2CCN(C)CC2)C2=CC(OS(=O)(=O)C=3C(=CC=CC=3F)F)=CC(C)=C2N1C(C)C1=CC=CC=C1 YODIPMROGSPCJQ-UHFFFAOYSA-N 0.000 claims 1
• YOPYLHIKNWDPGJ-UHFFFAOYSA-N C1=C(C2CCN(C)CC2)C2=CC(OS(=O)(=O)C=3C(=CC=CC=3F)F)=CC=C2N1C(C)C1=CC=CC=C1 Chemical compound C1=C(C2CCN(C)CC2)C2=CC(OS(=O)(=O)C=3C(=CC=CC=3F)F)=CC=C2N1C(C)C1=CC=CC=C1 YOPYLHIKNWDPGJ-UHFFFAOYSA-N 0.000 claims 1
• SKNVKUGIOYNMGH-UHFFFAOYSA-N [1-(1,2-diphenylpropan-2-yl)-3-(1-methylpiperidin-4-yl)indol-5-yl] benzenesulfonate Chemical compound C(C1=CC=CC=C1)C(C)(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)OS(=O)(=O)C1=CC=CC=C1)C1CCN(CC1)C SKNVKUGIOYNMGH-UHFFFAOYSA-N 0.000 claims 1
• YSHATEOKSXWNON-UHFFFAOYSA-N [1-(cyclohexylmethyl)-3-(1-methylpiperidin-4-yl)indol-5-yl] benzenesulfonate Chemical compound C1CN(C)CCC1C(C1=CC(OS(=O)(=O)C=2C=CC=CC=2)=CC=C11)=CN1CC1CCCCC1 YSHATEOKSXWNON-UHFFFAOYSA-N 0.000 claims 1
• AKXUEKLFNOGZAB-UHFFFAOYSA-N [1-[(2,4-difluorophenyl)methyl]-3-(1-methylpiperidin-4-yl)indol-5-yl] benzenesulfonate Chemical compound C1CN(C)CCC1C(C1=CC(OS(=O)(=O)C=2C=CC=CC=2)=CC=C11)=CN1CC1=CC=C(F)C=C1F AKXUEKLFNOGZAB-UHFFFAOYSA-N 0.000 claims 1
• RCSARYZHFBLLNG-UHFFFAOYSA-N [1-[(2-fluorophenyl)methyl]-3-(1-methylpiperidin-4-yl)indol-5-yl] benzenesulfonate Chemical compound C1CN(C)CCC1C(C1=CC(OS(=O)(=O)C=2C=CC=CC=2)=CC=C11)=CN1CC1=CC=CC=C1F RCSARYZHFBLLNG-UHFFFAOYSA-N 0.000 claims 1
• AIMQSRJVQBQZGT-UHFFFAOYSA-N [1-[(3-fluorophenyl)methyl]-3-(1-methylpiperidin-4-yl)indol-5-yl] benzenesulfonate Chemical compound C1CN(C)CCC1C(C1=CC(OS(=O)(=O)C=2C=CC=CC=2)=CC=C11)=CN1CC1=CC=CC(F)=C1 AIMQSRJVQBQZGT-UHFFFAOYSA-N 0.000 claims 1
• AYNBKSWTHRGLAY-UHFFFAOYSA-N [1-[(4-fluorophenyl)methyl]-3-(1-methylpiperidin-4-yl)indol-5-yl] 2,6-difluorobenzenesulfonate Chemical compound C1CN(C)CCC1C(C1=CC(OS(=O)(=O)C=2C(=CC=CC=2F)F)=CC=C11)=CN1CC1=CC=C(F)C=C1 AYNBKSWTHRGLAY-UHFFFAOYSA-N 0.000 claims 1
• DWQOVEHUJOVFIE-UHFFFAOYSA-N [1-cyclohexyl-3-(1-methylpiperidin-4-yl)indol-5-yl] benzenesulfonate Chemical compound C1CN(C)CCC1C(C1=CC(OS(=O)(=O)C=2C=CC=CC=2)=CC=C11)=CN1C1CCCCC1 DWQOVEHUJOVFIE-UHFFFAOYSA-N 0.000 claims 1
• JURBNJGMKDCGPC-UHFFFAOYSA-N [1-cyclopentyl-3-(1-methylpiperidin-4-yl)indol-5-yl] benzenesulfonate Chemical compound C1CN(C)CCC1C(C1=CC(OS(=O)(=O)C=2C=CC=CC=2)=CC=C11)=CN1C1CCCC1 JURBNJGMKDCGPC-UHFFFAOYSA-N 0.000 claims 1
• CKOJBANBXKJJNP-UHFFFAOYSA-N [1-ethyl-3-(1-methylpiperidin-4-yl)indol-5-yl] 2,6-difluorobenzenesulfonate Chemical compound C12=CC(OS(=O)(=O)C=3C(=CC=CC=3F)F)=CC=C2N(CC)C=C1C1CCN(C)CC1 CKOJBANBXKJJNP-UHFFFAOYSA-N 0.000 claims 1
• GJZIZYFFTUJUTJ-UHFFFAOYSA-N [1-ethyl-3-(1-methylpiperidin-4-yl)indol-5-yl] benzenesulfonate Chemical compound C12=CC(OS(=O)(=O)C=3C=CC=CC=3)=CC=C2N(CC)C=C1C1CCN(C)CC1 GJZIZYFFTUJUTJ-UHFFFAOYSA-N 0.000 claims 1
• SFSUYMKRBGCOMD-UHFFFAOYSA-N [1-ethyl-7-methyl-3-(1-methylpiperidin-4-yl)indol-5-yl] 2,6-difluorobenzenesulfonate Chemical compound C12=CC(OS(=O)(=O)C=3C(=CC=CC=3F)F)=CC(C)=C2N(CC)C=C1C1CCN(C)CC1 SFSUYMKRBGCOMD-UHFFFAOYSA-N 0.000 claims 1
• OXCGLSVOGFFREO-UHFFFAOYSA-N [3-(1-methylpiperidin-4-yl)-1-(2-methylpropyl)indol-5-yl] benzenesulfonate Chemical compound C12=CC(OS(=O)(=O)C=3C=CC=CC=3)=CC=C2N(CC(C)C)C=C1C1CCN(C)CC1 OXCGLSVOGFFREO-UHFFFAOYSA-N 0.000 claims 1
• UAPHXSVMRKEIMU-UHFFFAOYSA-N [3-(1-methylpiperidin-4-yl)-1-(3-phenylpropyl)indol-5-yl] benzenesulfonate Chemical compound C1CN(C)CCC1C(C1=CC(OS(=O)(=O)C=2C=CC=CC=2)=CC=C11)=CN1CCCC1=CC=CC=C1 UAPHXSVMRKEIMU-UHFFFAOYSA-N 0.000 claims 1
• ZWNRADRHWRNYME-UHFFFAOYSA-N [3-(1-methylpiperidin-4-yl)-1-(4-phenylbutyl)indol-5-yl] benzenesulfonate Chemical compound C1CN(C)CCC1C(C1=CC(OS(=O)(=O)C=2C=CC=CC=2)=CC=C11)=CN1CCCCC1=CC=CC=C1 ZWNRADRHWRNYME-UHFFFAOYSA-N 0.000 claims 1
• IDGWQZSAMKQGHJ-UHFFFAOYSA-N [3-(1-methylpiperidin-4-yl)-1-(pyridin-2-ylmethyl)indol-5-yl] benzenesulfonate Chemical compound C1CN(C)CCC1C(C1=CC(OS(=O)(=O)C=2C=CC=CC=2)=CC=C11)=CN1CC1=CC=CC=N1 IDGWQZSAMKQGHJ-UHFFFAOYSA-N 0.000 claims 1
• ARZUHZLIMLZRTA-UHFFFAOYSA-N [3-(1-methylpiperidin-4-yl)-1-propan-2-ylindol-5-yl] 2,6-difluorobenzenesulfonate Chemical compound C12=CC(OS(=O)(=O)C=3C(=CC=CC=3F)F)=CC=C2N(C(C)C)C=C1C1CCN(C)CC1 ARZUHZLIMLZRTA-UHFFFAOYSA-N 0.000 claims 1
• OUTVFQCENMAWKE-UHFFFAOYSA-N [3-(1-methylpiperidin-4-yl)-1-propan-2-ylindol-5-yl] benzenesulfonate Chemical compound C12=CC(OS(=O)(=O)C=3C=CC=CC=3)=CC=C2N(C(C)C)C=C1C1CCN(C)CC1 OUTVFQCENMAWKE-UHFFFAOYSA-N 0.000 claims 1
• JOBZMYQSDSPXHL-UHFFFAOYSA-N [3-(1-methylpiperidin-4-yl)-1-propylindol-5-yl] 2,6-difluorobenzenesulfonate Chemical compound C12=CC(OS(=O)(=O)C=3C(=CC=CC=3F)F)=CC=C2N(CCC)C=C1C1CCN(C)CC1 JOBZMYQSDSPXHL-UHFFFAOYSA-N 0.000 claims 1
• BMDNGXPXZQYBBN-UHFFFAOYSA-N [4-(1-methylpiperidin-4-yl)-2,3-dihydro-1h-pyrrolo[1,2-a]indol-6-yl] 2,6-difluorobenzenesulfonate Chemical compound C1CN(C)CCC1C(C1=CC(OS(=O)(=O)C=2C(=CC=CC=2F)F)=CC=C11)=C2N1CCC2 BMDNGXPXZQYBBN-UHFFFAOYSA-N 0.000 claims 1
• XISVOUZVHNCYFO-UHFFFAOYSA-N [4-(1-methylpiperidin-4-yl)-2,3-dihydro-1h-pyrrolo[1,2-a]indol-6-yl] benzenesulfonate Chemical compound C1CN(C)CCC1C(C1=CC(OS(=O)(=O)C=2C=CC=CC=2)=CC=C11)=C2N1CCC2 XISVOUZVHNCYFO-UHFFFAOYSA-N 0.000 claims 1
• BUVWOSLGQLYZLV-UHFFFAOYSA-N [7-methyl-3-(1-methylpiperidin-4-yl)-1-propylindol-5-yl] 2,6-difluorobenzenesulfonate Chemical compound C12=CC(OS(=O)(=O)C=3C(=CC=CC=3F)F)=CC(C)=C2N(CCC)C=C1C1CCN(C)CC1 BUVWOSLGQLYZLV-UHFFFAOYSA-N 0.000 claims 1
• 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims 1
• 239000005557 antagonist Substances 0.000 abstract description 12
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 261
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 209
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