CA2655694C - 1,4-substituted indoles useful for modulation of the 5-ht6 receptor - Google Patents

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Publication number

CA2655694C

CA2655694C CA2655694A CA2655694A CA2655694C CA 2655694 C CA2655694 C CA 2655694C CA 2655694 A CA2655694 A CA 2655694A CA 2655694 A CA2655694 A CA 2655694A CA 2655694 C CA2655694 C CA 2655694C

Authority

CA

Canada

Prior art keywords

methyl

methoxy

indol

indole

mmol

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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• 108091005435 5-HT6 receptors Proteins 0.000 title abstract description 21
• 150000002475 indoles Chemical class 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 258
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 184
• -1 6-chloroimidazo[2,1-b][1,3]thiazol-5-yl Chemical group 0.000 claims description 161
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 108
• 239000001257 hydrogen Substances 0.000 claims description 88
• 229910052739 hydrogen Inorganic materials 0.000 claims description 88
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 86
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 65
• 125000003118 aryl group Chemical group 0.000 claims description 61
• 125000001072 heteroaryl group Chemical group 0.000 claims description 51
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 51
• 150000003839 salts Chemical class 0.000 claims description 49
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 41
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 35
• 230000037396 body weight Effects 0.000 claims description 33
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 32
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 31
• 229910052736 halogen Inorganic materials 0.000 claims description 29
• 150000002367 halogens Chemical class 0.000 claims description 29
• 229910052757 nitrogen Inorganic materials 0.000 claims description 29
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 29
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 28
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 27
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 25
• 208000035475 disorder Diseases 0.000 claims description 25
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 24
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 24
• 229910052799 carbon Inorganic materials 0.000 claims description 23
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
• 125000001424 substituent group Chemical group 0.000 claims description 22
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 21
• 229910052731 fluorine Inorganic materials 0.000 claims description 21
• 239000011737 fluorine Substances 0.000 claims description 21
• 150000001412 amines Chemical class 0.000 claims description 19
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 18
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
• 150000001721 carbon Chemical group 0.000 claims description 16
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
• 238000011282 treatment Methods 0.000 claims description 15
• 150000002431 hydrogen Chemical class 0.000 claims description 14
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 12
• 125000004432 carbon atom Chemical group C* 0.000 claims description 12
• 239000000460 chlorine Substances 0.000 claims description 12
• 229910052801 chlorine Inorganic materials 0.000 claims description 12
• 125000006413 ring segment Chemical group 0.000 claims description 12
• 235000019786 weight gain Nutrition 0.000 claims description 12
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 10
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 10
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 10
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
• 125000000623 heterocyclic group Chemical group 0.000 claims description 9
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 8
• 229910052794 bromium Inorganic materials 0.000 claims description 8
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 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
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
• 125000002950 monocyclic group Chemical group 0.000 claims description 7
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
• 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
• 208000023105 Huntington 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
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 6
• 208000015122 neurodegenerative disease Diseases 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
• 208000032841 Bulimia Diseases 0.000 claims description 5
• 206010006550 Bulimia nervosa Diseases 0.000 claims description 5
• 206010013654 Drug abuse Diseases 0.000 claims description 5
• 208000026139 Memory 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
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
• 239000005864 Sulphur Substances 0.000 claims description 5
• 208000022531 anorexia Diseases 0.000 claims description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
• 208000014679 binge eating disease Diseases 0.000 claims description 5
• 210000003169 central nervous system Anatomy 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
• 206010027599 migraine Diseases 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 239000001301 oxygen Substances 0.000 claims description 5
• 230000036407 pain Effects 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
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 4
• 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
• 125000002619 bicyclic 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
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 3
• 208000012902 Nervous system disease Diseases 0.000 claims description 3
• BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 3
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
• 208000015114 central nervous system disease Diseases 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• 125000005842 heteroatom Chemical group 0.000 claims description 3
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
• 229910052711 selenium Inorganic materials 0.000 claims description 3
• 239000011669 selenium Substances 0.000 claims description 3
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 2
• XEGKCBXIZISEPU-UHFFFAOYSA-N 1-(4-fluorophenyl)sulfonyl-4-[(3-methylpiperazin-1-yl)methyl]indole Chemical compound C1CNC(C)CN1CC1=CC=CC2=C1C=CN2S(=O)(=O)C1=CC=C(F)C=C1 XEGKCBXIZISEPU-UHFFFAOYSA-N 0.000 claims description 2
• LSORBQZBNBYSHX-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-4-[(4-propylpiperazin-1-yl)methyl]indole Chemical compound C1CN(CCC)CCN1CC1=CC=CC2=C1C=CN2S(=O)(=O)C1=CC=C(C)C=C1 LSORBQZBNBYSHX-UHFFFAOYSA-N 0.000 claims description 2
• LNQIOKZCXLIQEU-UHFFFAOYSA-N 2-[6-methoxy-4-(piperazin-1-ylmethyl)indol-1-yl]sulfonylbenzonitrile Chemical compound C=12C=CN(S(=O)(=O)C=3C(=CC=CC=3)C#N)C2=CC(OC)=CC=1CN1CCNCC1 LNQIOKZCXLIQEU-UHFFFAOYSA-N 0.000 claims description 2
• WHSALXIPVBTLMW-UHFFFAOYSA-N 3-[4-(azetidin-1-ylmethyl)indol-1-yl]sulfonylbenzonitrile Chemical compound C1=CC2=C(CN3CCC3)C=CC=C2N1S(=O)(=O)C1=CC=CC(C#N)=C1 WHSALXIPVBTLMW-UHFFFAOYSA-N 0.000 claims description 2
• DKNLHNLFDTYACO-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-(2-methoxy-5-methylphenyl)sulfonylindole Chemical compound COC1=CC=C(C)C=C1S(=O)(=O)N1C2=CC=CC(CN3CCC3)=C2C=C1 DKNLHNLFDTYACO-UHFFFAOYSA-N 0.000 claims description 2
• FNPXZPWBLYGDSC-UHFFFAOYSA-N 4-[4-(azetidin-1-ylmethyl)indol-1-yl]sulfonylbenzonitrile Chemical compound C1=CC2=C(CN3CCC3)C=CC=C2N1S(=O)(=O)C1=CC=C(C#N)C=C1 FNPXZPWBLYGDSC-UHFFFAOYSA-N 0.000 claims description 2
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
• 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 2
• 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 1
• 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 1
• PEGGDLMUWBEMNE-UHFFFAOYSA-N 1-(2-methoxy-5-methylphenyl)sulfonyl-4-[(3-methylpiperazin-1-yl)methyl]-2,3-dihydroindole Chemical compound COC1=CC=C(C)C=C1S(=O)(=O)N1C(C=CC=C2CN3CC(C)NCC3)=C2CC1 PEGGDLMUWBEMNE-UHFFFAOYSA-N 0.000 claims 1
• OTULMJSSIXTWBP-UHFFFAOYSA-N 1-(2-methoxy-5-methylphenyl)sulfonyl-4-[(3-methylpiperazin-1-yl)methyl]indole Chemical compound COC1=CC=C(C)C=C1S(=O)(=O)N1C2=CC=CC(CN3CC(C)NCC3)=C2C=C1 OTULMJSSIXTWBP-UHFFFAOYSA-N 0.000 claims 1
• PNAFAPBONDIUTL-UHFFFAOYSA-N 1-(2-methoxy-5-methylphenyl)sulfonyl-4-[(4-methylpiperazin-1-yl)methyl]-2,3-dihydroindole Chemical compound COC1=CC=C(C)C=C1S(=O)(=O)N1C(C=CC=C2CN3CCN(C)CC3)=C2CC1 PNAFAPBONDIUTL-UHFFFAOYSA-N 0.000 claims 1
• JCCDLZXAWMQOIB-UHFFFAOYSA-N 1-(2-methylphenyl)sulfonyl-4-(piperazin-1-ylmethyl)indole Chemical compound CC1=CC=CC=C1S(=O)(=O)N1C2=CC=CC(CN3CCNCC3)=C2C=C1 JCCDLZXAWMQOIB-UHFFFAOYSA-N 0.000 claims 1
• GNXGQUBBDFJTAV-UHFFFAOYSA-N 1-(2-methylphenyl)sulfonyl-4-[(4-methylpiperazin-1-yl)methyl]indole Chemical compound C1CN(C)CCN1CC1=CC=CC2=C1C=CN2S(=O)(=O)C1=CC=CC=C1C GNXGQUBBDFJTAV-UHFFFAOYSA-N 0.000 claims 1
• NTEFCLNBBJEXSN-UHFFFAOYSA-N 1-(3-chloro-2-methylphenyl)sulfonyl-6-methoxy-4-(piperazin-1-ylmethyl)indole Chemical compound C=12C=CN(S(=O)(=O)C=3C(=C(Cl)C=CC=3)C)C2=CC(OC)=CC=1CN1CCNCC1 NTEFCLNBBJEXSN-UHFFFAOYSA-N 0.000 claims 1
• OLBTVTXBTMHSKR-UHFFFAOYSA-N 1-(4-fluorophenyl)sulfonyl-4-(piperazin-1-ylmethyl)indole Chemical compound C1=CC(F)=CC=C1S(=O)(=O)N1C2=CC=CC(CN3CCNCC3)=C2C=C1 OLBTVTXBTMHSKR-UHFFFAOYSA-N 0.000 claims 1
• ORBVOLQEPCSMCA-UHFFFAOYSA-N 1-(4-fluorophenyl)sulfonyl-6-methoxy-4-(piperazin-1-ylmethyl)indole Chemical compound C=12C=CN(S(=O)(=O)C=3C=CC(F)=CC=3)C2=CC(OC)=CC=1CN1CCNCC1 ORBVOLQEPCSMCA-UHFFFAOYSA-N 0.000 claims 1
• VYSPSXPMDGBZAE-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-4-(piperazin-1-ylmethyl)indole Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=CC=CC(CN3CCNCC3)=C2C=C1 VYSPSXPMDGBZAE-UHFFFAOYSA-N 0.000 claims 1
• ADNLWJXLZBQPSC-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-4-[(3-methylpiperazin-1-yl)methyl]indole Chemical compound C1CNC(C)CN1CC1=CC=CC2=C1C=CN2S(=O)(=O)C1=CC=C(C)C=C1 ADNLWJXLZBQPSC-UHFFFAOYSA-N 0.000 claims 1
• MIJGAIKJGYXJSB-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-4-[(4-methylpiperazin-1-yl)methyl]indole Chemical compound C1CN(C)CCN1CC1=CC=CC2=C1C=CN2S(=O)(=O)C1=CC=C(C)C=C1 MIJGAIKJGYXJSB-UHFFFAOYSA-N 0.000 claims 1
• RIIPVKTUWNNGDG-UHFFFAOYSA-N 1-(5-ethoxy-1-naphthalen-1-ylsulfonylindol-4-yl)-n,n-dimethylmethanamine Chemical compound C1=CC=C2C(S(=O)(=O)N3C4=CC=C(C(=C4C=C3)CN(C)C)OCC)=CC=CC2=C1 RIIPVKTUWNNGDG-UHFFFAOYSA-N 0.000 claims 1
• WIYZFKDUSPTRHJ-UHFFFAOYSA-N 1-(5-ethoxy-1-naphthalen-2-ylsulfonylindol-4-yl)-n,n-dimethylmethanamine Chemical compound C1=CC=CC2=CC(S(=O)(=O)N3C4=CC=C(C(=C4C=C3)CN(C)C)OCC)=CC=C21 WIYZFKDUSPTRHJ-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• BHFMMKFNNMTLQD-UHFFFAOYSA-N 1-(benzenesulfonyl)-2-methyl-4-(piperazin-1-ylmethyl)indole Chemical compound C1=CC=C2N(S(=O)(=O)C=3C=CC=CC=3)C(C)=CC2=C1CN1CCNCC1 BHFMMKFNNMTLQD-UHFFFAOYSA-N 0.000 claims 1
• URRIVCFHQGNMOQ-UHFFFAOYSA-N 1-(benzenesulfonyl)-2-methylindole Chemical compound CC1=CC2=CC=CC=C2N1S(=O)(=O)C1=CC=CC=C1 URRIVCFHQGNMOQ-UHFFFAOYSA-N 0.000 claims 1
• IGHRSINTSQEHJN-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-methyl-4-(piperazin-1-ylmethyl)indole Chemical compound C=12C(C)=CN(S(=O)(=O)C=3C=CC=CC=3)C2=CC=CC=1CN1CCNCC1 IGHRSINTSQEHJN-UHFFFAOYSA-N 0.000 claims 1
• QAMGXYDGQMJJBV-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-methyl-4-[(4-methylpiperazin-1-yl)methyl]indole Chemical compound C1CN(C)CCN1CC1=CC=CC2=C1C(C)=CN2S(=O)(=O)C1=CC=CC=C1 QAMGXYDGQMJJBV-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• AMODRIWGBMZHMI-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-(piperazin-1-ylmethyl)indol-5-ol Chemical compound OC1=CC=C2N(S(=O)(=O)C=3C=CC=CC=3)C=CC2=C1CN1CCNCC1 AMODRIWGBMZHMI-UHFFFAOYSA-N 0.000 claims 1
• URWFTQOKDRKKAY-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-(piperazin-1-ylmethyl)indole Chemical compound C1=CC2=C(CN3CCNCC3)C=CC=C2N1S(=O)(=O)C1=CC=CC=C1 URWFTQOKDRKKAY-UHFFFAOYSA-N 0.000 claims 1
• WUOWTIPELQCMAT-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-[(dimethylamino)methyl]-6-fluoroindol-5-ol Chemical compound C1=CC=2C(CN(C)C)=C(O)C(F)=CC=2N1S(=O)(=O)C1=CC=CC=C1 WUOWTIPELQCMAT-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• AZTXUGZCTXMNPJ-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-[(dimethylamino)methyl]indol-5-ol Chemical compound C1=CC=2C(CN(C)C)=C(O)C=CC=2N1S(=O)(=O)C1=CC=CC=C1 AZTXUGZCTXMNPJ-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• LBHADFQNSORGIP-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-[[4-(2-methoxyethyl)piperazin-1-yl]methyl]indole Chemical compound C1CN(CCOC)CCN1CC1=CC=CC2=C1C=CN2S(=O)(=O)C1=CC=CC=C1 LBHADFQNSORGIP-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• XIVGELFNOUCTPO-UHFFFAOYSA-N 1-(benzenesulfonyl)-5-methoxy-n-methyl-4-(piperazin-1-ylmethyl)indole-2-carboxamide Chemical compound COC1=CC=C2N(S(=O)(=O)C=3C=CC=CC=3)C(C(=O)NC)=CC2=C1CN1CCNCC1 XIVGELFNOUCTPO-UHFFFAOYSA-N 0.000 claims 1
• HLSDYGCQCRMNEL-UHFFFAOYSA-N 1-(benzenesulfonyl)-6-fluoro-4-(methylaminomethyl)indol-5-ol Chemical compound C1=CC=2C(CNC)=C(O)C(F)=CC=2N1S(=O)(=O)C1=CC=CC=C1 HLSDYGCQCRMNEL-UHFFFAOYSA-N 0.000 claims 1
• HBTYRQCQPUYERW-UHFFFAOYSA-N 1-(benzenesulfonyl)-6-fluoro-4-(piperazin-1-ylmethyl)indole Chemical compound C=12C=CN(S(=O)(=O)C=3C=CC=CC=3)C2=CC(F)=CC=1CN1CCNCC1 HBTYRQCQPUYERW-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• IZYCNTYWDAPGAN-HNNXBMFYSA-N 1-(benzenesulfonyl)-6-fluoro-4-[[(3s)-3-methylpiperazin-1-yl]methyl]indole Chemical compound C1CN[C@@H](C)CN1CC1=CC(F)=CC2=C1C=CN2S(=O)(=O)C1=CC=CC=C1 IZYCNTYWDAPGAN-HNNXBMFYSA-N 0.000 claims 1
• 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 1
• 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 1
• MHJMUZQCGFOIJD-UHFFFAOYSA-N 1-(benzenesulfonyl)-7-methoxy-4-(piperazin-1-ylmethyl)indole Chemical compound C1=2C=CN(S(=O)(=O)C=3C=CC=CC=3)C=2C(OC)=CC=C1CN1CCNCC1 MHJMUZQCGFOIJD-UHFFFAOYSA-N 0.000 claims 1
• ZRBAJQCNPRRPOH-UHFFFAOYSA-N 1-(benzenesulfonyl)-n-ethyl-5-methoxy-4-(piperazin-1-ylmethyl)indole-2-carboxamide Chemical compound COC1=CC=C2N(S(=O)(=O)C=3C=CC=CC=3)C(C(=O)NCC)=CC2=C1CN1CCNCC1 ZRBAJQCNPRRPOH-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• XBLYICGZWYEXDM-UHFFFAOYSA-N 1-[1-(benzenesulfonyl)-5-ethoxyindol-4-yl]-n,n-dimethylmethanamine Chemical compound C1=CC2=C(CN(C)C)C(OCC)=CC=C2N1S(=O)(=O)C1=CC=CC=C1 XBLYICGZWYEXDM-UHFFFAOYSA-N 0.000 claims 1
• AUQKISZHAJMLKZ-UHFFFAOYSA-N 1-[1-(benzenesulfonyl)-5-methoxyindol-4-yl]-n,n-dimethylmethanamine Chemical compound C1=CC2=C(CN(C)C)C(OC)=CC=C2N1S(=O)(=O)C1=CC=CC=C1 AUQKISZHAJMLKZ-UHFFFAOYSA-N 0.000 claims 1
• MHXVSAKJAZJUTL-UHFFFAOYSA-N 1-[1-(benzenesulfonyl)-5-methoxyindol-4-yl]-n-methylmethanamine Chemical compound C1=CC=2C(CNC)=C(OC)C=CC=2N1S(=O)(=O)C1=CC=CC=C1 MHXVSAKJAZJUTL-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• UOMKLPVGAVCQRJ-UHFFFAOYSA-N 1-[1-(benzenesulfonyl)indol-4-yl]-n,n-dimethylmethanamine Chemical compound C1=CC=2C(CN(C)C)=CC=CC=2N1S(=O)(=O)C1=CC=CC=C1 UOMKLPVGAVCQRJ-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• AIQSVCNEUIZTOM-UHFFFAOYSA-N 1-[5-methoxy-1-[3-(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(C(F)(F)F)=C1 AIQSVCNEUIZTOM-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• BAYFYVLPBMQJTQ-UHFFFAOYSA-N 1-[[1-(benzenesulfonyl)indol-4-yl]methyl]azetidin-3-ol Chemical compound C1C(O)CN1CC1=CC=CC2=C1C=CN2S(=O)(=O)C1=CC=CC=C1 BAYFYVLPBMQJTQ-UHFFFAOYSA-N 0.000 claims 1
• FHYGBNUGUFSCSY-FQEVSTJZSA-N 2-[(2s)-1-[[1-(benzenesulfonyl)indol-4-yl]methyl]azetidin-2-yl]propan-2-ol Chemical compound CC(C)(O)[C@@H]1CCN1CC1=CC=CC2=C1C=CN2S(=O)(=O)C1=CC=CC=C1 FHYGBNUGUFSCSY-FQEVSTJZSA-N 0.000 claims 1
• 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 1
• KFNXEQZUEDUABU-UHFFFAOYSA-N 2-[1-(benzenesulfonyl)-7-methoxyindol-4-yl]-2-piperazin-1-ylacetonitrile Chemical compound C1=2C=CN(S(=O)(=O)C=3C=CC=CC=3)C=2C(OC)=CC=C1C(C#N)N1CCNCC1 KFNXEQZUEDUABU-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• IVIJHTZGWNSELQ-UHFFFAOYSA-N 2-[[1-(benzenesulfonyl)-6-fluoroindol-4-yl]methyl-methylamino]ethanol Chemical compound C1=CC=2C(CN(CCO)C)=CC(F)=CC=2N1S(=O)(=O)C1=CC=CC=C1 IVIJHTZGWNSELQ-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• IKYPSRXKAVFYKE-UHFFFAOYSA-N 2-[methyl-[[1-(2-methylphenyl)sulfonylindol-4-yl]methyl]amino]ethanol Chemical compound C1=CC=2C(CN(CCO)C)=CC=CC=2N1S(=O)(=O)C1=CC=CC=C1C IKYPSRXKAVFYKE-UHFFFAOYSA-N 0.000 claims 1
• NUNHASVOYPUZPP-UHFFFAOYSA-N 2-sulfonyl-1,3-dihydroindole Chemical compound C1=CC=C2NC(=S(=O)=O)CC2=C1 NUNHASVOYPUZPP-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• KKCYKVSPQMQKJK-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-(4-tert-butylphenyl)sulfonylindole Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)N1C2=CC=CC(CN3CCC3)=C2C=C1 KKCYKVSPQMQKJK-UHFFFAOYSA-N 0.000 claims 1
• HZXVRGNSMLMYAU-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-(5-chlorothiophen-2-yl)sulfonylindole Chemical compound S1C(Cl)=CC=C1S(=O)(=O)N1C2=CC=CC(CN3CCC3)=C2C=C1 HZXVRGNSMLMYAU-UHFFFAOYSA-N 0.000 claims 1
• JJRDGIOIICEBDH-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-(benzenesulfonyl)-2,3-dichloro-5-methoxyindole Chemical compound COC1=CC=C2N(S(=O)(=O)C=3C=CC=CC=3)C(Cl)=C(Cl)C2=C1CN1CCC1 JJRDGIOIICEBDH-UHFFFAOYSA-N 0.000 claims 1
• CVBDDOXPYNHQAE-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-(benzenesulfonyl)-2-methylindole Chemical compound C1=CC=C2N(S(=O)(=O)C=3C=CC=CC=3)C(C)=CC2=C1CN1CCC1 CVBDDOXPYNHQAE-UHFFFAOYSA-N 0.000 claims 1
• PYWSRKCKKQWGAW-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-(benzenesulfonyl)-5-methoxyindole Chemical compound COC1=CC=C2N(S(=O)(=O)C=3C=CC=CC=3)C=CC2=C1CN1CCC1 PYWSRKCKKQWGAW-UHFFFAOYSA-N 0.000 claims 1
• HMUYFEDCKMUECZ-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-(benzenesulfonyl)-6-fluoroindol-5-ol Chemical compound OC1=C(F)C=C2N(S(=O)(=O)C=3C=CC=CC=3)C=CC2=C1CN1CCC1 HMUYFEDCKMUECZ-UHFFFAOYSA-N 0.000 claims 1
• REEJKLUSKZHQIH-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-(benzenesulfonyl)-6-methoxyindole Chemical compound C=12C=CN(S(=O)(=O)C=3C=CC=CC=3)C2=CC(OC)=CC=1CN1CCC1 REEJKLUSKZHQIH-UHFFFAOYSA-N 0.000 claims 1
• IDUXIGFPGVVWDB-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-(benzenesulfonyl)-7-methoxyindole Chemical compound C1=2C=CN(S(=O)(=O)C=3C=CC=CC=3)C=2C(OC)=CC=C1CN1CCC1 IDUXIGFPGVVWDB-UHFFFAOYSA-N 0.000 claims 1
• RGPKVBBDGZZVHA-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-(benzenesulfonyl)indole Chemical compound C1=CC2=C(CN3CCC3)C=CC=C2N1S(=O)(=O)C1=CC=CC=C1 RGPKVBBDGZZVHA-UHFFFAOYSA-N 0.000 claims 1
• GLAACGOVGAKGMP-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-[2-(trifluoromethyl)phenyl]sulfonylindole Chemical compound FC(F)(F)C1=CC=CC=C1S(=O)(=O)N1C2=CC=CC(CN3CCC3)=C2C=C1 GLAACGOVGAKGMP-UHFFFAOYSA-N 0.000 claims 1
• LNBIDTNFDLYCFU-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-[4-bromo-2-(trifluoromethyl)phenyl]sulfonylindole Chemical compound FC(F)(F)C1=CC(Br)=CC=C1S(=O)(=O)N1C2=CC=CC(CN3CCC3)=C2C=C1 LNBIDTNFDLYCFU-UHFFFAOYSA-N 0.000 claims 1
• KXUKYMMPUDCSGE-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-methylsulfonyl-7-phenylmethoxyindole Chemical compound C1=CC(OCC=2C=CC=CC=2)=C2N(S(=O)(=O)C)C=CC2=C1CN1CCC1 KXUKYMMPUDCSGE-UHFFFAOYSA-N 0.000 claims 1
• GIDMFZJFALJIAH-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-naphthalen-2-ylsulfonylindole Chemical compound C=1C=C2C=CC=CC2=CC=1S(=O)(=O)N(C1=CC=C2)C=CC1=C2CN1CCC1 GIDMFZJFALJIAH-UHFFFAOYSA-N 0.000 claims 1
• BOUFQBZCYLSEKK-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-thiophen-2-ylsulfonylindole Chemical compound C1=CC2=C(CN3CCC3)C=CC=C2N1S(=O)(=O)C1=CC=CS1 BOUFQBZCYLSEKK-UHFFFAOYSA-N 0.000 claims 1
• QQGBYIVSAIBWDD-UHFFFAOYSA-N 4-(piperazin-1-ylmethyl)-1-pyridin-3-ylsulfonylindole Chemical compound C1=CC2=C(CN3CCNCC3)C=CC=C2N1S(=O)(=O)C1=CC=CN=C1 QQGBYIVSAIBWDD-UHFFFAOYSA-N 0.000 claims 1
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