JP5324437B2 - ５−ｈｔ６モジュレーターとしてのインドール - Google Patents

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Publication number

JP5324437B2

JP5324437B2 JP2009517258A JP2009517258A JP5324437B2 JP 5324437 B2 JP5324437 B2 JP 5324437B2 JP 2009517258 A JP2009517258 A JP 2009517258A JP 2009517258 A JP2009517258 A JP 2009517258A JP 5324437 B2 JP5324437 B2 JP 5324437B2

Authority

JP

Japan

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.)

Expired - Fee Related

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• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title description 43
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title description 22
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title description 22
• 150000001875 compounds Chemical class 0.000 claims abstract description 242
• 239000003814 drug Substances 0.000 claims abstract description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
• -1 (i) -CN Chemical class 0.000 claims description 192
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 93
• 239000001257 hydrogen Substances 0.000 claims description 88
• 229910052739 hydrogen Inorganic materials 0.000 claims description 88
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 77
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 61
• 150000003839 salts Chemical class 0.000 claims description 59
• 125000003118 aryl group Chemical group 0.000 claims description 53
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 44
• 125000001072 heteroaryl group Chemical group 0.000 claims description 44
• 239000000460 chlorine Substances 0.000 claims description 43
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 35
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 34
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 28
• 229910052757 nitrogen Inorganic materials 0.000 claims description 28
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 23
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 23
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 23
• 208000035475 disorder Diseases 0.000 claims description 22
• 229910052736 halogen Inorganic materials 0.000 claims description 22
• 150000002367 halogens Chemical class 0.000 claims description 22
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 21
• 239000011737 fluorine Substances 0.000 claims description 21
• 229910052731 fluorine Inorganic materials 0.000 claims description 21
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
• 229910052799 carbon Inorganic materials 0.000 claims description 20
• 125000001424 substituent group Chemical group 0.000 claims description 19
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
• 125000004432 carbon atom Chemical group C* 0.000 claims description 17
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
• 150000001412 amines Chemical class 0.000 claims description 13
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
• 238000011282 treatment Methods 0.000 claims description 13
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
• 229910052801 chlorine Inorganic materials 0.000 claims description 12
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 12
• 230000004584 weight gain Effects 0.000 claims description 12
• 235000019786 weight gain Nutrition 0.000 claims description 12
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
• 208000032841 Bulimia Diseases 0.000 claims description 10
• 206010006550 Bulimia nervosa Diseases 0.000 claims description 10
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 10
• 125000004076 pyridyl group Chemical group 0.000 claims description 10
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 9
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 8
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
• 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 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
• 125000001153 fluoro group Chemical group F* 0.000 claims description 8
• 150000002431 hydrogen Chemical class 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
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 7
• 206010013654 Drug abuse Diseases 0.000 claims description 7
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
• 125000000623 heterocyclic group Chemical group 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
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 7
• 125000006413 ring segment Chemical group 0.000 claims description 7
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 6
• 208000019901 Anxiety disease Diseases 0.000 claims description 6
• 206010033664 Panic attack Diseases 0.000 claims description 6
• 208000018737 Parkinson disease Diseases 0.000 claims description 6
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 6
• 230000036506 anxiety Effects 0.000 claims description 6
• 125000002619 bicyclic group Chemical group 0.000 claims description 6
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 6
• 125000001041 indolyl group Chemical group 0.000 claims description 6
• 208000019906 panic disease Diseases 0.000 claims description 6
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 6
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 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 5
• 208000024827 Alzheimer disease Diseases 0.000 claims description 5
• 208000019695 Migraine disease Diseases 0.000 claims description 5
• 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 5
• 208000002193 Pain Diseases 0.000 claims description 5
• 208000028017 Psychotic disease Diseases 0.000 claims description 5
• 208000022531 anorexia Diseases 0.000 claims description 5
• 208000015114 central nervous system 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
• 229940079593 drug Drugs 0.000 claims description 5
• 206010015037 epilepsy Diseases 0.000 claims description 5
• 206010027599 migraine Diseases 0.000 claims description 5
• 125000002950 monocyclic group Chemical group 0.000 claims description 5
• 230000004770 neurodegeneration Effects 0.000 claims description 5
• 230000036407 pain Effects 0.000 claims description 5
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 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
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
• 125000001544 thienyl group Chemical group 0.000 claims description 5
• 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 4
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 4
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 4
• 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 4
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
• 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 4
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
• 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 4
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
• 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 4
• 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 4
• 125000002541 furyl group Chemical group 0.000 claims description 4
• 125000002883 imidazolyl group Chemical group 0.000 claims description 4
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
• 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 4
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 4
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
• 125000000842 isoxazolyl group Chemical group 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
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
• 125000002971 oxazolyl group Chemical group 0.000 claims description 4
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
• 125000000335 thiazolyl group Chemical group 0.000 claims description 4
• 230000004580 weight loss Effects 0.000 claims description 4
• 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 3
• XMQLIEFNZCSBMF-UHFFFAOYSA-N 1-(5-methoxy-1-quinolin-8-ylsulfonylindol-4-yl)-n,n-dimethylmethanamine Chemical compound C1=CN=C2C(S(=O)(=O)N3C4=CC=C(C(=C4C=C3)CN(C)C)OC)=CC=CC2=C1 XMQLIEFNZCSBMF-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• JXHQONKBONMSJE-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-[[2-hydroxyethyl(methyl)amino]methyl]indol-5-ol Chemical compound C1=CC=2C(CN(CCO)C)=C(O)C=CC=2N1S(=O)(=O)C1=CC=CC=C1 JXHQONKBONMSJE-UHFFFAOYSA-N 0.000 claims description 3
• SVZYSUDJSZYZOL-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-[[ethyl(methyl)amino]methyl]-6-fluoroindol-5-ol Chemical compound C1=CC=2C(CN(C)CC)=C(O)C(F)=CC=2N1S(=O)(=O)C1=CC=CC=C1 SVZYSUDJSZYZOL-UHFFFAOYSA-N 0.000 claims description 3
• XWOMMZRDERYHCJ-UHFFFAOYSA-N 1-[1-(1,2-dimethylimidazol-4-yl)sulfonyl-5-methoxyindol-4-yl]-n,n-dimethylmethanamine Chemical compound C1=CC2=C(CN(C)C)C(OC)=CC=C2N1S(=O)(=O)C1=CN(C)C(C)=N1 XWOMMZRDERYHCJ-UHFFFAOYSA-N 0.000 claims description 3
• FZUQWVGDWXAYGD-UHFFFAOYSA-N 1-[1-(2,1,3-benzothiadiazol-4-ylsulfonyl)-5-methoxyindol-4-yl]-n,n-dimethylmethanamine Chemical compound C1=CC2=NSN=C2C(S(=O)(=O)N2C3=CC=C(C(=C3C=C2)CN(C)C)OC)=C1 FZUQWVGDWXAYGD-UHFFFAOYSA-N 0.000 claims description 3
• OOSSCOCAQKZRLC-UHFFFAOYSA-N 1-[1-(2,4-dichlorophenyl)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(Cl)C=C1Cl OOSSCOCAQKZRLC-UHFFFAOYSA-N 0.000 claims description 3
• DDCHTTYAJKKZMS-UHFFFAOYSA-N 1-[1-(2,5-difluorophenyl)sulfonyl-5-methoxyindol-4-yl]-n,n-dimethylmethanamine Chemical compound C1=CC2=C(CN(C)C)C(OC)=CC=C2N1S(=O)(=O)C1=CC(F)=CC=C1F DDCHTTYAJKKZMS-UHFFFAOYSA-N 0.000 claims description 3
• RJUXVRPEOQMKNG-UHFFFAOYSA-N 1-[1-(2,6-difluorophenyl)sulfonyl-5-methoxyindol-4-yl]-n,n-dimethylmethanamine Chemical compound C1=CC2=C(CN(C)C)C(OC)=CC=C2N1S(=O)(=O)C1=C(F)C=CC=C1F RJUXVRPEOQMKNG-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• YJNHPYHEVNTFJJ-UHFFFAOYSA-N 1-[1-(2-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=C1Cl YJNHPYHEVNTFJJ-UHFFFAOYSA-N 0.000 claims description 3
• HDWKZEVXDHCBCA-UHFFFAOYSA-N 1-[1-(3,4-dihydro-2h-1,5-benzodioxepin-7-ylsulfonyl)-5-methoxyindol-4-yl]-n,n-dimethylmethanamine Chemical compound O1CCCOC2=CC(S(=O)(=O)N3C4=CC=C(C(=C4C=C3)CN(C)C)OC)=CC=C21 HDWKZEVXDHCBCA-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 3
• VDAOHBMOVUDOFR-UHFFFAOYSA-N 1-[1-(benzenesulfonyl)-6-fluoro-5-methoxyindol-4-yl]-n,n-dimethylmethanamine Chemical compound C1=CC2=C(CN(C)C)C(OC)=C(F)C=C2N1S(=O)(=O)C1=CC=CC=C1 VDAOHBMOVUDOFR-UHFFFAOYSA-N 0.000 claims description 3
• PCBCDQFVWRSLLX-UHFFFAOYSA-N 1-[1-(benzenesulfonyl)indol-4-yl]-n,n-dimethylethanamine Chemical compound C1=CC=2C(C(N(C)C)C)=CC=CC=2N1S(=O)(=O)C1=CC=CC=C1 PCBCDQFVWRSLLX-UHFFFAOYSA-N 0.000 claims description 3
• JKKQKRUJNZAKJC-UHFFFAOYSA-N 1-[1-(benzenesulfonyl)indol-4-yl]-n-methylethanamine Chemical compound C1=CC=2C(C(C)NC)=CC=CC=2N1S(=O)(=O)C1=CC=CC=C1 JKKQKRUJNZAKJC-UHFFFAOYSA-N 0.000 claims description 3
• GONMNFSTBUWOKN-UHFFFAOYSA-N 1-[1-[4-fluoro-3-(trifluoromethyl)phenyl]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(C(F)(F)F)=C1 GONMNFSTBUWOKN-UHFFFAOYSA-N 0.000 claims description 3
• DPWVZHGVXQYIAJ-UHFFFAOYSA-N 1-[5-methoxy-1-(2-methoxy-4-methylphenyl)sulfonylindol-4-yl]-n,n-dimethylmethanamine Chemical compound C1=CC2=C(CN(C)C)C(OC)=CC=C2N1S(=O)(=O)C1=CC=C(C)C=C1OC DPWVZHGVXQYIAJ-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• LTGUYWLGTUQNET-UHFFFAOYSA-N 1-[5-methoxy-1-(4-methoxyphenyl)sulfonylindol-4-yl]-n,n-dimethylmethanamine Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=C(OC)C(CN(C)C)=C2C=C1 LTGUYWLGTUQNET-UHFFFAOYSA-N 0.000 claims description 3
• IIALYDOVTLNKKN-UHFFFAOYSA-N 1-[5-methoxy-1-[(5-methyl-1-benzothiophen-2-yl)sulfonyl]indol-4-yl]-n,n-dimethylmethanamine Chemical compound CC1=CC=C2SC(S(=O)(=O)N3C4=CC=C(C(=C4C=C3)CN(C)C)OC)=CC2=C1 IIALYDOVTLNKKN-UHFFFAOYSA-N 0.000 claims description 3
• NLCPRBXFPQXRPX-UHFFFAOYSA-N 1-[5-methoxy-1-[2-(trifluoromethyl)phenyl]sulfonylindol-4-yl]-n,n-dimethylmethanamine Chemical compound C1=CC2=C(CN(C)C)C(OC)=CC=C2N1S(=O)(=O)C1=CC=CC=C1C(F)(F)F NLCPRBXFPQXRPX-UHFFFAOYSA-N 0.000 claims description 3
• NNHAEUHRYRXWMZ-UHFFFAOYSA-N 1-[5-methoxy-1-[4-(trifluoromethoxy)phenyl]sulfonylindol-4-yl]-n,n-dimethylmethanamine Chemical compound C1=CC2=C(CN(C)C)C(OC)=CC=C2N1S(=O)(=O)C1=CC=C(OC(F)(F)F)C=C1 NNHAEUHRYRXWMZ-UHFFFAOYSA-N 0.000 claims description 3
• NXRGBWBZNZCXCN-UHFFFAOYSA-N 2-[1-(benzenesulfonyl)-4-(piperazin-1-ylmethyl)indol-5-yl]oxyacetonitrile Chemical compound C1=CC2=C(CN3CCNCC3)C(OCC#N)=CC=C2N1S(=O)(=O)C1=CC=CC=C1 NXRGBWBZNZCXCN-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 3
• 208000012902 Nervous system disease Diseases 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• YWNXGUDCMIPDNZ-UHFFFAOYSA-N ethyl 1-(benzenesulfonyl)-5-methoxy-4-(piperazin-1-ylmethyl)indole-2-carboxylate Chemical compound COC1=CC=C2N(S(=O)(=O)C=3C=CC=CC=3)C(C(=O)OCC)=CC2=C1CN1CCNCC1 YWNXGUDCMIPDNZ-UHFFFAOYSA-N 0.000 claims description 3
• ZURVEKSFULETLE-UHFFFAOYSA-N n-[[1-(4-fluorophenyl)sulfonylindol-4-yl]methyl]ethanamine Chemical class C1=CC=2C(CNCC)=CC=CC=2N1S(=O)(=O)C1=CC=C(F)C=C1 ZURVEKSFULETLE-UHFFFAOYSA-N 0.000 claims description 3
• RLKXATWDWIFRAE-UHFFFAOYSA-N n-[[1-(benzenesulfonyl)indol-4-yl]methyl]propan-2-amine Chemical compound C1=CC=2C(CNC(C)C)=CC=CC=2N1S(=O)(=O)C1=CC=CC=C1 RLKXATWDWIFRAE-UHFFFAOYSA-N 0.000 claims description 3
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