AU2007271188B2 - Indoles as 5-HT6 modulators - Google Patents

Info

Publication number

AU2007271188B2

AU2007271188B2 AU2007271188A AU2007271188A AU2007271188B2 AU 2007271188 B2 AU2007271188 B2 AU 2007271188B2 AU 2007271188 A AU2007271188 A AU 2007271188A AU 2007271188 A AU2007271188 A AU 2007271188A AU 2007271188 B2 AU2007271188 B2 AU 2007271188B2

Authority

AU

Australia

Prior art keywords

methyl

indol

phenylsulfonyl

methoxy

indole

Prior art date

2006-07-03

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.)

Ceased

Links

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• 150000002475 indoles Chemical class 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 249
• 238000000034 method Methods 0.000 claims abstract description 79
• 239000003814 drug Substances 0.000 claims abstract description 11
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 233
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 190
• -1 (i) -CN Chemical class 0.000 claims description 165
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 128
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 108
• 239000001257 hydrogen Substances 0.000 claims description 99
• 229910052739 hydrogen Inorganic materials 0.000 claims description 99
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 90
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 70
• 125000003118 aryl group Chemical group 0.000 claims description 61
• 125000001072 heteroaryl group Chemical group 0.000 claims description 56
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 49
• 150000003839 salts Chemical class 0.000 claims description 48
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 45
• 229910052757 nitrogen Inorganic materials 0.000 claims description 43
• 229910052736 halogen Inorganic materials 0.000 claims description 38
• 150000002367 halogens Chemical class 0.000 claims description 38
• 230000037396 body weight Effects 0.000 claims description 37
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 36
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 33
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 32
• 239000000460 chlorine Substances 0.000 claims description 31
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
• 208000035475 disorder Diseases 0.000 claims description 29
• 229910052799 carbon Inorganic materials 0.000 claims description 28
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
• 238000011282 treatment Methods 0.000 claims description 27
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 26
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 26
• 125000001424 substituent group Chemical group 0.000 claims description 25
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 23
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 23
• 229910052731 fluorine Inorganic materials 0.000 claims description 23
• 239000011737 fluorine Substances 0.000 claims description 23
• 150000002431 hydrogen Chemical class 0.000 claims description 23
• JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 22
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
• 125000004432 carbon atom Chemical group C* 0.000 claims description 17
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 16
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 15
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 15
• 235000019786 weight gain Nutrition 0.000 claims description 15
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 13
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 12
• 150000001412 amines Chemical class 0.000 claims description 12
• 229910052801 chlorine Inorganic materials 0.000 claims description 12
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 9
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 9
• 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 9
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
• 208000002193 Pain Diseases 0.000 claims description 8
• 125000000217 alkyl group Chemical group 0.000 claims description 8
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 8
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
• 229910052794 bromium Inorganic materials 0.000 claims description 8
• 210000003169 central nervous system Anatomy 0.000 claims description 8
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 8
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 8
• 125000000623 heterocyclic group Chemical group 0.000 claims description 8
• 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 8
• DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 8
• 230000036407 pain Effects 0.000 claims description 8
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 7
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 7
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
• 208000024827 Alzheimer disease Diseases 0.000 claims description 6
• 208000019901 Anxiety disease Diseases 0.000 claims description 6
• 206010013654 Drug abuse Diseases 0.000 claims description 6
• 208000023105 Huntington disease Diseases 0.000 claims description 6
• 206010033664 Panic attack Diseases 0.000 claims description 6
• 230000036506 anxiety Effects 0.000 claims description 6
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
• 230000000052 comparative effect Effects 0.000 claims description 6
• 208000019906 panic disease Diseases 0.000 claims description 6
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 5
• 208000032841 Bulimia Diseases 0.000 claims description 5
• 206010006550 Bulimia nervosa Diseases 0.000 claims description 5
• 208000026139 Memory disease Diseases 0.000 claims description 5
• 208000019695 Migraine disease Diseases 0.000 claims description 5
• 208000018737 Parkinson disease Diseases 0.000 claims description 5
• 208000028017 Psychotic disease Diseases 0.000 claims description 5
• 208000022531 anorexia Diseases 0.000 claims description 5
• 208000014679 binge eating disease Diseases 0.000 claims description 5
• 208000010877 cognitive disease Diseases 0.000 claims description 5
• 206010061428 decreased appetite Diseases 0.000 claims description 5
• 230000006735 deficit Effects 0.000 claims description 5
• 206010015037 epilepsy Diseases 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 206010027599 migraine Diseases 0.000 claims description 5
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• 201000000980 schizophrenia Diseases 0.000 claims description 5
• 208000019116 sleep disease Diseases 0.000 claims description 5
• 208000011117 substance-related disease Diseases 0.000 claims description 5
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 4
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 4
• 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 4
• 206010012601 diabetes mellitus Diseases 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
• WDWXGGQTKNYZFJ-UHFFFAOYSA-N 1-[1-(benzenesulfonyl)-3-methylindol-4-yl]-n,n-dimethylmethanamine Chemical compound C1=C(C)C=2C(CN(C)C)=CC=CC=2N1S(=O)(=O)C1=CC=CC=C1 WDWXGGQTKNYZFJ-UHFFFAOYSA-N 0.000 claims description 3
• NUNHASVOYPUZPP-UHFFFAOYSA-N 2-sulfonyl-1,3-dihydroindole Chemical compound C1=CC=C2NC(=S(=O)=O)CC2=C1 NUNHASVOYPUZPP-UHFFFAOYSA-N 0.000 claims description 3
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
• 208000012902 Nervous system disease Diseases 0.000 claims description 3
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
• 208000015114 central nervous system disease Diseases 0.000 claims description 3
• ZBIUDKBISCRTAA-UHFFFAOYSA-N 1-(2,5-dimethoxyphenyl)sulfonyl-6-methoxy-4-(piperazin-1-ylmethyl)indole Chemical compound COC1=CC=C(OC)C(S(=O)(=O)N2C3=CC(OC)=CC(CN4CCNCC4)=C3C=C2)=C1 ZBIUDKBISCRTAA-UHFFFAOYSA-N 0.000 claims description 2
• BUZUVDQPNDGFIN-UHFFFAOYSA-N 1-(2-methoxy-5-methylphenyl)sulfonyl-4-(piperazin-1-ylmethyl)indole Chemical compound COC1=CC=C(C)C=C1S(=O)(=O)N1C2=CC=CC(CN3CCNCC3)=C2C=C1 BUZUVDQPNDGFIN-UHFFFAOYSA-N 0.000 claims description 2
• ZXCNDRKESNVQJH-UHFFFAOYSA-N 1-(5-methoxy-1-pyridin-3-ylsulfonylindol-4-yl)-n,n-dimethylmethanamine Chemical compound C1=CC2=C(CN(C)C)C(OC)=CC=C2N1S(=O)(=O)C1=CC=CN=C1 ZXCNDRKESNVQJH-UHFFFAOYSA-N 0.000 claims description 2
• BVECVCDRIQGKAT-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-(piperazin-1-ylmethyl)-5-propan-2-yloxyindole Chemical compound CC(C)OC1=CC=C2N(S(=O)(=O)C=3C=CC=CC=3)C=CC2=C1CN1CCNCC1 BVECVCDRIQGKAT-UHFFFAOYSA-N 0.000 claims description 2
• MDRSZVOMZNOCMI-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-[(dimethylamino)methyl]-6-methoxyindol-5-ol Chemical compound C1=CC=2C(CN(C)C)=C(O)C(OC)=CC=2N1S(=O)(=O)C1=CC=CC=C1 MDRSZVOMZNOCMI-UHFFFAOYSA-N 0.000 claims description 2
• JRFURBAKPVUNFN-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-[1-(dimethylamino)ethyl]-6-fluoroindol-5-ol Chemical compound C1=CC=2C(C(N(C)C)C)=C(O)C(F)=CC=2N1S(=O)(=O)C1=CC=CC=C1 JRFURBAKPVUNFN-UHFFFAOYSA-N 0.000 claims description 2
• XIPWIDNXUYGHAE-UHFFFAOYSA-N 1-(benzenesulfonyl)-5-ethoxy-4-(piperazin-1-ylmethyl)indole Chemical compound CCOC1=CC=C2N(S(=O)(=O)C=3C=CC=CC=3)C=CC2=C1CN1CCNCC1 XIPWIDNXUYGHAE-UHFFFAOYSA-N 0.000 claims description 2
• SUMVHUPAXRUQRJ-UHFFFAOYSA-N 1-(benzenesulfonyl)-5-methoxy-4-(piperazin-1-ylmethyl)indole Chemical compound COC1=CC=C2N(S(=O)(=O)C=3C=CC=CC=3)C=CC2=C1CN1CCNCC1 SUMVHUPAXRUQRJ-UHFFFAOYSA-N 0.000 claims description 2
• ZRLUDJHUMLXEOG-UHFFFAOYSA-N 1-(benzenesulfonyl)-5-phenylmethoxy-4-(piperazin-1-ylmethyl)indole Chemical compound C1=CC2=C(CN3CCNCC3)C(OCC=3C=CC=CC=3)=CC=C2N1S(=O)(=O)C1=CC=CC=C1 ZRLUDJHUMLXEOG-UHFFFAOYSA-N 0.000 claims description 2
• GSIPILFLFJOVDX-UHFFFAOYSA-N 1-(benzenesulfonyl)-6-fluoro-4-[1-(methylamino)ethyl]indol-5-ol Chemical compound C1=CC=2C(C(C)NC)=C(O)C(F)=CC=2N1S(=O)(=O)C1=CC=CC=C1 GSIPILFLFJOVDX-UHFFFAOYSA-N 0.000 claims description 2
• FVDXPCDMMFKPPD-UHFFFAOYSA-N 1-(benzenesulfonyl)-6-methoxy-4-(piperazin-1-ylmethyl)indole Chemical compound C=12C=CN(S(=O)(=O)C=3C=CC=CC=3)C2=CC(OC)=CC=1CN1CCNCC1 FVDXPCDMMFKPPD-UHFFFAOYSA-N 0.000 claims description 2
• BQKOSLCZBBTZFN-UHFFFAOYSA-N 1-(benzenesulfonyl)-6-methoxy-4-[(4-methylpiperazin-1-yl)methyl]indole Chemical compound C=12C=CN(S(=O)(=O)C=3C=CC=CC=3)C2=CC(OC)=CC=1CN1CCN(C)CC1 BQKOSLCZBBTZFN-UHFFFAOYSA-N 0.000 claims description 2
• QEIVMWXKPHLBGF-INIZCTEOSA-N 1-(benzenesulfonyl)-6-methoxy-4-[[(3s)-3-methylpiperazin-1-yl]methyl]indole Chemical compound C=12C=CN(S(=O)(=O)C=3C=CC=CC=3)C2=CC(OC)=CC=1CN1CCN[C@@H](C)C1 QEIVMWXKPHLBGF-INIZCTEOSA-N 0.000 claims description 2
• QGJVCYOPMQKVCJ-UHFFFAOYSA-N 1-[1-(2,5-dimethoxyphenyl)sulfonyl-5-methoxyindol-4-yl]-n,n-dimethylmethanamine Chemical compound COC1=CC=C(OC)C(S(=O)(=O)N2C3=CC=C(OC)C(CN(C)C)=C3C=C2)=C1 QGJVCYOPMQKVCJ-UHFFFAOYSA-N 0.000 claims description 2
• JWPYHHQWJQZARC-UHFFFAOYSA-N 1-[1-(2-chloro-6-methylphenyl)sulfonyl-5-methoxyindol-4-yl]-n,n-dimethylmethanamine Chemical compound C1=CC2=C(CN(C)C)C(OC)=CC=C2N1S(=O)(=O)C1=C(C)C=CC=C1Cl JWPYHHQWJQZARC-UHFFFAOYSA-N 0.000 claims description 2
• MIJWUZNMZKIMLV-UHFFFAOYSA-N 1-[1-(3-chloro-4-fluorophenyl)sulfonyl-5-methoxyindol-4-yl]-n,n-dimethylmethanamine Chemical compound C1=CC2=C(CN(C)C)C(OC)=CC=C2N1S(=O)(=O)C1=CC=C(F)C(Cl)=C1 MIJWUZNMZKIMLV-UHFFFAOYSA-N 0.000 claims description 2
• MOTXBVRCPDBYAY-UHFFFAOYSA-N 1-[1-(3-chlorophenyl)sulfonyl-5-methoxyindol-4-yl]-n,n-dimethylmethanamine Chemical compound C1=CC2=C(CN(C)C)C(OC)=CC=C2N1S(=O)(=O)C1=CC=CC(Cl)=C1 MOTXBVRCPDBYAY-UHFFFAOYSA-N 0.000 claims description 2
• KWBOGYUZYJNKSC-UHFFFAOYSA-N 1-[1-(5-bromo-2-methoxyphenyl)sulfonyl-5-methoxyindol-4-yl]-n,n-dimethylmethanamine Chemical compound C1=CC2=C(CN(C)C)C(OC)=CC=C2N1S(=O)(=O)C1=CC(Br)=CC=C1OC KWBOGYUZYJNKSC-UHFFFAOYSA-N 0.000 claims description 2
• NHJPXQBGPNNFKX-UHFFFAOYSA-N 1-[1-(benzenesulfonyl)-3-chloro-5-methoxyindol-4-yl]-n,n-dimethylmethanamine Chemical compound C1=C(Cl)C2=C(CN(C)C)C(OC)=CC=C2N1S(=O)(=O)C1=CC=CC=C1 NHJPXQBGPNNFKX-UHFFFAOYSA-N 0.000 claims description 2
• JBHQRUQPHNUURR-UHFFFAOYSA-N 1-[1-(benzenesulfonyl)-3-chloro-5-methoxyindol-4-yl]-n-methylmethanamine Chemical compound C1=C(Cl)C=2C(CNC)=C(OC)C=CC=2N1S(=O)(=O)C1=CC=CC=C1 JBHQRUQPHNUURR-UHFFFAOYSA-N 0.000 claims description 2
• MPUYJAJFEDFBSE-UHFFFAOYSA-N 1-[1-(benzenesulfonyl)-5,6-dimethoxyindol-4-yl]-n,n-dimethylmethanamine Chemical compound C1=CC=2C(CN(C)C)=C(OC)C(OC)=CC=2N1S(=O)(=O)C1=CC=CC=C1 MPUYJAJFEDFBSE-UHFFFAOYSA-N 0.000 claims description 2
• VDLUIHXOHVNPMM-UHFFFAOYSA-N 1-[1-(benzenesulfonyl)-6-fluoro-5-methoxyindol-4-yl]-n,n-dimethylethanamine Chemical compound C1=CC2=C(C(C)N(C)C)C(OC)=C(F)C=C2N1S(=O)(=O)C1=CC=CC=C1 VDLUIHXOHVNPMM-UHFFFAOYSA-N 0.000 claims description 2
• BNEOAKSMJWFSRL-UHFFFAOYSA-N 1-[1-(benzenesulfonyl)-6-fluoro-5-methoxyindol-4-yl]-n-methylethanamine Chemical compound C1=CC=2C(C(C)NC)=C(OC)C(F)=CC=2N1S(=O)(=O)C1=CC=CC=C1 BNEOAKSMJWFSRL-UHFFFAOYSA-N 0.000 claims description 2
• SHGHPTBBSUVTLN-UHFFFAOYSA-N 1-[1-(benzenesulfonyl)-6-methoxyindol-4-yl]-n,n-dimethylmethanamine Chemical compound C12=CC(OC)=CC(CN(C)C)=C2C=CN1S(=O)(=O)C1=CC=CC=C1 SHGHPTBBSUVTLN-UHFFFAOYSA-N 0.000 claims description 2
• VFEQGZFRNBVMQQ-UHFFFAOYSA-N 1-[1-(benzenesulfonyl)indol-4-yl]-n-methylmethanamine Chemical compound C1=CC=2C(CNC)=CC=CC=2N1S(=O)(=O)C1=CC=CC=C1 VFEQGZFRNBVMQQ-UHFFFAOYSA-N 0.000 claims description 2
• BOCMIDNHRZEYPV-UHFFFAOYSA-N 1-[5-methoxy-1-(2-methylphenyl)sulfonylindol-4-yl]-n,n-dimethylmethanamine Chemical compound C1=CC2=C(CN(C)C)C(OC)=CC=C2N1S(=O)(=O)C1=CC=CC=C1C BOCMIDNHRZEYPV-UHFFFAOYSA-N 0.000 claims description 2
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 2
• SUJMNXBMSQHMJY-UHFFFAOYSA-N 2-[4-[(dimethylamino)methyl]-5-methoxyindol-1-yl]sulfonylbenzonitrile Chemical compound C1=CC2=C(CN(C)C)C(OC)=CC=C2N1S(=O)(=O)C1=CC=CC=C1C#N SUJMNXBMSQHMJY-UHFFFAOYSA-N 0.000 claims description 2
• SVJIEPAQFDLYQS-UHFFFAOYSA-N 2-[[1-(benzenesulfonyl)-6-methoxyindol-4-yl]methyl-methylamino]ethanol Chemical compound C12=CC(OC)=CC(CN(C)CCO)=C2C=CN1S(=O)(=O)C1=CC=CC=C1 SVJIEPAQFDLYQS-UHFFFAOYSA-N 0.000 claims description 2
• ZXGBBWAJEAFBSB-UHFFFAOYSA-N 3-[4-[(dimethylamino)methyl]-5-methoxyindol-1-yl]sulfonylbenzonitrile Chemical compound C1=CC2=C(CN(C)C)C(OC)=CC=C2N1S(=O)(=O)C1=CC=CC(C#N)=C1 ZXGBBWAJEAFBSB-UHFFFAOYSA-N 0.000 claims description 2
• HSPBHYODRZPHRS-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-(2,5-difluorophenyl)sulfonylindole Chemical compound FC1=CC=C(F)C(S(=O)(=O)N2C3=CC=CC(CN4CCC4)=C3C=C2)=C1 HSPBHYODRZPHRS-UHFFFAOYSA-N 0.000 claims description 2
• HMRNEIRRJSZGLE-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-(2,6-difluorophenyl)sulfonylindole Chemical compound FC1=CC=CC(F)=C1S(=O)(=O)N1C2=CC=CC(CN3CCC3)=C2C=C1 HMRNEIRRJSZGLE-UHFFFAOYSA-N 0.000 claims description 2
• GDYNQUNLJOKWIZ-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-(2-chlorophenyl)sulfonylindole Chemical compound ClC1=CC=CC=C1S(=O)(=O)N1C2=CC=CC(CN3CCC3)=C2C=C1 GDYNQUNLJOKWIZ-UHFFFAOYSA-N 0.000 claims description 2
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