BRPI0712898A2 - indàis como moduladores de 5-ht6 - Google Patents

Info

Publication number

BRPI0712898A2

BRPI0712898A2 BRPI0712898-3A BRPI0712898A BRPI0712898A2 BR PI0712898 A2 BRPI0712898 A2 BR PI0712898A2 BR PI0712898 A BRPI0712898 A BR PI0712898A BR PI0712898 A2 BRPI0712898 A2 BR PI0712898A2

Authority

BR

Brazil

Prior art keywords

indol

methyl

phenylsulfonyl

methoxy

sulfonyl

Prior art date

2006-07-03

Links

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• 150000001875 compounds Chemical class 0.000 claims abstract description 244
• 108091005435 5-HT6 receptors Proteins 0.000 claims abstract description 16
• 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 293
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 268
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 132
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 104
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 86
• 229910052739 hydrogen Inorganic materials 0.000 claims description 86
• 239000001257 hydrogen Substances 0.000 claims description 85
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 83
• 125000000217 alkyl group Chemical group 0.000 claims description 82
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 80
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 59
• 125000001072 heteroaryl group Chemical group 0.000 claims description 49
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 48
• 150000003839 salts Chemical class 0.000 claims description 45
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 41
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 39
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 34
• 230000037396 body weight Effects 0.000 claims description 32
• 229910052757 nitrogen Inorganic materials 0.000 claims description 30
• 125000003545 alkoxy group Chemical group 0.000 claims description 29
• 239000000460 chlorine Substances 0.000 claims description 29
• 229910052736 halogen Inorganic materials 0.000 claims description 29
• 150000002367 halogens Chemical class 0.000 claims description 29
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 28
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 27
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 26
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 26
• 125000003118 aryl group Chemical group 0.000 claims description 26
• 229910052799 carbon Inorganic materials 0.000 claims description 26
• 239000011737 fluorine Substances 0.000 claims description 26
• 229910052731 fluorine Inorganic materials 0.000 claims description 26
• 150000005840 aryl radicals Chemical class 0.000 claims description 25
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
• 125000001424 substituent group Chemical group 0.000 claims description 21
• 208000035475 disorder Diseases 0.000 claims description 19
• 150000002431 hydrogen Chemical class 0.000 claims description 19
• 238000011282 treatment Methods 0.000 claims description 19
• 125000003342 alkenyl group Chemical group 0.000 claims description 18
• 125000004414 alkyl thio group Chemical group 0.000 claims description 18
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 17
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 17
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
• 125000004432 carbon atom Chemical group C* 0.000 claims description 16
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
• 150000001412 amines 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
• 235000019786 weight gain Nutrition 0.000 claims description 12
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 11
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
• 206010013654 Drug abuse Diseases 0.000 claims description 10
• 229910052801 chlorine Inorganic materials 0.000 claims description 10
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
• 125000004435 hydrogen atom Chemical group [H]* 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
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 8
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 8
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 7
• 208000015114 central nervous system disease 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
• 230000000694 effects Effects 0.000 claims description 7
• 125000000623 heterocyclic group Chemical group 0.000 claims description 7
• JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 7
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 6
• 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 6
• 208000024827 Alzheimer disease Diseases 0.000 claims description 6
• 208000019901 Anxiety disease Diseases 0.000 claims description 6
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
• 208000023105 Huntington disease Diseases 0.000 claims description 6
• 208000018737 Parkinson disease Diseases 0.000 claims description 6
• 230000036506 anxiety Effects 0.000 claims description 6
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
• 229910052794 bromium Inorganic materials 0.000 claims description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 6
• 208000019906 panic disease Diseases 0.000 claims description 6
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
• 208000032841 Bulimia Diseases 0.000 claims description 5
• 206010006550 Bulimia nervosa Diseases 0.000 claims description 5
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 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
• 208000022531 anorexia Diseases 0.000 claims description 5
• 208000010877 cognitive disease Diseases 0.000 claims description 5
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
• 206010061428 decreased appetite Diseases 0.000 claims description 5
• 206010015037 epilepsy Diseases 0.000 claims description 5
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 5
• 125000001153 fluoro group Chemical group F* 0.000 claims description 5
• 206010027599 migraine Diseases 0.000 claims description 5
• 230000036407 pain Effects 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
• 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 description 4
• 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 description 4
• 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 4
• 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 4
• 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 description 4
• 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 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
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
• 208000012902 Nervous system disease Diseases 0.000 claims description 4
• PCGCBCWJZYUGFZ-UHFFFAOYSA-N [1-(benzenesulfonyl)-4-(pyrrolidin-1-ylmethyl)indol-6-yl] n,n-dimethylcarbamate Chemical compound C=12C=CN(S(=O)(=O)C=3C=CC=CC=3)C2=CC(OC(=O)N(C)C)=CC=1CN1CCCC1 PCGCBCWJZYUGFZ-UHFFFAOYSA-N 0.000 claims description 4
• JABTUVPXFSJNPU-UHFFFAOYSA-N [4-[[1-(benzenesulfonyl)indol-4-yl]methyl]piperazin-2-yl]methanol Chemical compound C1CNC(CO)CN1CC1=CC=CC2=C1C=CN2S(=O)(=O)C1=CC=CC=C1 JABTUVPXFSJNPU-UHFFFAOYSA-N 0.000 claims description 4
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 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
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• 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 3
• 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 description 3
• 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 description 3
• IAXQLEFJFNVZMC-UHFFFAOYSA-N 1-(4-fluorophenyl)sulfonyl-4-(pyrrolidin-1-ylmethyl)indole Chemical compound C1=CC(F)=CC=C1S(=O)(=O)N1C2=CC=CC(CN3CCCC3)=C2C=C1 IAXQLEFJFNVZMC-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 description 3
• 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 description 3
• XPIUTCHQBPOJON-UHFFFAOYSA-N 1-(5-ethoxy-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)OCC)=CC=CC2=C1 XPIUTCHQBPOJON-UHFFFAOYSA-N 0.000 claims description 3
• NARMRVKKIRIPOS-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-(1,4-diazepan-1-ylmethyl)-6-methoxyindole Chemical compound C=12C=CN(S(=O)(=O)C=3C=CC=CC=3)C2=CC(OC)=CC=1CN1CCCNCC1 NARMRVKKIRIPOS-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
• 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 3
• PZKFOYAEUTYYHK-UHFFFAOYSA-N 1-(benzenesulfonyl)-5-ethoxy-4-(piperazin-1-ylmethyl)-n-(thiophen-2-ylmethyl)indole-2-carboxamide Chemical compound CCOC1=CC=C2N(S(=O)(=O)C=3C=CC=CC=3)C(C(=O)NCC=3SC=CC=3)=CC2=C1CN1CCNCC1 PZKFOYAEUTYYHK-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 3
• 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 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
• 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 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
• RNWJCCUISZDRAE-UHFFFAOYSA-N 1-[1-(benzenesulfonyl)-6-fluoroindol-4-yl]-n,n-dimethylmethanamine Chemical compound C1=CC=2C(CN(C)C)=CC(F)=CC=2N1S(=O)(=O)C1=CC=CC=C1 RNWJCCUISZDRAE-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
• 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
• 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 3
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 3
• DAHWDHKRSKEPLD-UHFFFAOYSA-N 4-(1,4-diazepan-1-ylmethyl)-1-(4-fluorophenyl)sulfonylindole Chemical compound C1=CC(F)=CC=C1S(=O)(=O)N1C2=CC=CC(CN3CCNCCC3)=C2C=C1 DAHWDHKRSKEPLD-UHFFFAOYSA-N 0.000 claims description 3
• NHARQHZOUUQSTP-UHFFFAOYSA-N 4-(1,4-diazepan-1-ylmethyl)-1-(4-methylphenyl)sulfonylindole Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=CC=CC(CN3CCNCCC3)=C2C=C1 NHARQHZOUUQSTP-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• ZPWDYDPWYSNXGZ-UHFFFAOYSA-N 4-[(4-methyl-1,4-diazepan-1-yl)methyl]-1-(4-methylphenyl)sulfonylindole Chemical compound C1CN(C)CCCN1CC1=CC=CC2=C1C=CN2S(=O)(=O)C1=CC=C(C)C=C1 ZPWDYDPWYSNXGZ-UHFFFAOYSA-N 0.000 claims description 3
• JNASUXKHRXYXSQ-UHFFFAOYSA-N 6-methoxy-4-(piperazin-1-ylmethyl)-1-[3-(trifluoromethyl)phenyl]sulfonylindole Chemical compound C=12C=CN(S(=O)(=O)C=3C=C(C=CC=3)C(F)(F)F)C2=CC(OC)=CC=1CN1CCNCC1 JNASUXKHRXYXSQ-UHFFFAOYSA-N 0.000 claims description 3
• 125000000304 alkynyl group Chemical group 0.000 claims description 3
• 125000005018 aryl alkenyl group Chemical group 0.000 claims description 3
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
• 230000006735 deficit Effects 0.000 claims description 3
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
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