NZ573371A - Indoles as 5-ht6 modulators - Google Patents

Info

Publication number

NZ573371A

NZ573371A NZ573371A NZ57337107A NZ573371A NZ 573371 A NZ573371 A NZ 573371A NZ 573371 A NZ573371 A NZ 573371A NZ 57337107 A NZ57337107 A NZ 57337107A NZ 573371 A NZ573371 A NZ 573371A

Authority

NZ

New Zealand

Prior art keywords

methyl

indole

phenylsulfonyl

methoxy

sulfonyl

Prior art date

2006-07-03

Links

• Espacenet
• Global Dossier
• Discuss

• 150000002475 indoles Chemical class 0.000 title abstract description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 279
• 238000000034 method Methods 0.000 claims abstract description 83
• 230000037396 body weight Effects 0.000 claims abstract description 38
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 32
• 208000035475 disorder Diseases 0.000 claims abstract description 28
• 238000011282 treatment Methods 0.000 claims abstract description 22
• 235000019786 weight gain Nutrition 0.000 claims abstract description 14
• 230000000694 effects Effects 0.000 claims abstract description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
• 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 8
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 8
• 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 7
• 208000019901 Anxiety disease Diseases 0.000 claims abstract description 7
• 208000023105 Huntington disease Diseases 0.000 claims abstract description 7
• 208000002193 Pain Diseases 0.000 claims abstract description 7
• 206010033664 Panic attack Diseases 0.000 claims abstract description 7
• 230000036506 anxiety Effects 0.000 claims abstract description 7
• 210000003169 central nervous system Anatomy 0.000 claims abstract description 7
• 230000036407 pain Effects 0.000 claims abstract description 7
• 208000019906 panic disease Diseases 0.000 claims abstract description 7
• 208000032841 Bulimia Diseases 0.000 claims abstract description 6
• 206010006550 Bulimia nervosa Diseases 0.000 claims abstract description 6
• 206010013654 Drug abuse Diseases 0.000 claims abstract description 6
• 208000026139 Memory disease Diseases 0.000 claims abstract description 6
• 208000019695 Migraine disease Diseases 0.000 claims abstract description 6
• 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims abstract description 6
• 208000018737 Parkinson disease Diseases 0.000 claims abstract description 6
• 208000028017 Psychotic disease Diseases 0.000 claims abstract description 6
• 208000022531 anorexia Diseases 0.000 claims abstract description 6
• 208000014679 binge eating disease Diseases 0.000 claims abstract description 6
• 208000010877 cognitive disease Diseases 0.000 claims abstract description 6
• 206010061428 decreased appetite Diseases 0.000 claims abstract description 6
• 230000006735 deficit Effects 0.000 claims abstract description 6
• 206010015037 epilepsy Diseases 0.000 claims abstract description 6
• 206010027599 migraine Diseases 0.000 claims abstract description 6
• 208000019116 sleep disease Diseases 0.000 claims abstract description 6
• 208000011117 substance-related disease Diseases 0.000 claims abstract description 6
• 108091005435 5-HT6 receptors Proteins 0.000 claims abstract description 5
• 239000000203 mixture Substances 0.000 claims description 306
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 272
• WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 239
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 198
• -1 (i) -CN Chemical class 0.000 claims description 194
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 162
• 239000001257 hydrogen Substances 0.000 claims description 95
• 229910052739 hydrogen Inorganic materials 0.000 claims description 95
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 90
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 84
• 238000006243 chemical reaction Methods 0.000 claims description 65
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 64
• 239000002904 solvent Substances 0.000 claims description 64
• 125000003118 aryl group Chemical group 0.000 claims description 60
• 150000003839 salts Chemical class 0.000 claims description 57
• 125000001072 heteroaryl group Chemical group 0.000 claims description 55
• 239000000047 product Substances 0.000 claims description 50
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 45
• 238000004128 high performance liquid chromatography Methods 0.000 claims description 42
• JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 claims description 40
• 229910052736 halogen Inorganic materials 0.000 claims description 39
• 150000002367 halogens Chemical class 0.000 claims description 39
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 35
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
• 229910052757 nitrogen Inorganic materials 0.000 claims description 29
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 26
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 25
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 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
• 125000001424 substituent group Chemical group 0.000 claims description 24
• 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 24
• 229910052799 carbon Inorganic materials 0.000 claims description 23
• 239000012321 sodium triacetoxyborohydride Substances 0.000 claims description 22
• 150000002431 hydrogen Chemical class 0.000 claims description 21
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 20
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 20
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 20
• 229910052731 fluorine Inorganic materials 0.000 claims description 20
• 239000011737 fluorine Substances 0.000 claims description 20
• 241001465754 Metazoa Species 0.000 claims description 19
• 239000003814 drug Substances 0.000 claims description 19
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 18
• 150000001412 amines Chemical class 0.000 claims description 17
• 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 15
• QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 claims description 15
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
• 238000004519 manufacturing process Methods 0.000 claims description 13
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
• 239000000460 chlorine Substances 0.000 claims description 12
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
• 229910052801 chlorine Inorganic materials 0.000 claims description 11
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 10
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[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 8
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 8
• 229910052794 bromium Inorganic materials 0.000 claims description 8
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 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
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 7
• GRJZJFUBQYULKL-UHFFFAOYSA-N 4-bromo-1h-indole Chemical class BrC1=CC=CC2=C1C=CN2 GRJZJFUBQYULKL-UHFFFAOYSA-N 0.000 claims description 7
• 230000000052 comparative effect Effects 0.000 claims description 7
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
• 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 7
• 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 7
• 239000003054 catalyst Substances 0.000 claims description 6
• 239000003085 diluting agent Substances 0.000 claims description 6
• 238000012360 testing method Methods 0.000 claims description 6
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 5
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 5
• 150000001299 aldehydes Chemical class 0.000 claims description 5
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
• 239000002537 cosmetic Substances 0.000 claims description 5
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
• GXAJIOMJXBWAHA-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-[(3-hydroxypyrrolidin-1-yl)methyl]indol-5-ol Chemical compound C1C(O)CCN1CC1=C(O)C=CC2=C1C=CN2S(=O)(=O)C1=CC=CC=C1 GXAJIOMJXBWAHA-UHFFFAOYSA-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
• BIUDHHGROGJSHN-UHFFFAOYSA-N 4-fluoro-3-(trifluoromethyl)benzaldehyde Chemical group FC1=CC=C(C=O)C=C1C(F)(F)F BIUDHHGROGJSHN-UHFFFAOYSA-N 0.000 claims description 4
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 4
• 239000004480 active ingredient Substances 0.000 claims description 4
• 239000003638 chemical reducing agent Substances 0.000 claims description 4
• 229940079593 drug Drugs 0.000 claims description 4
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
• QJPQVXSHYBGQGM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QJPQVXSHYBGQGM-UHFFFAOYSA-N 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
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 claims description 4
• 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 description 3
• 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 description 3
• XDMKVVVABSVLLZ-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-(1,4-diazepan-1-ylmethyl)indole Chemical compound C1=CC2=C(CN3CCNCCC3)C=CC=C2N1S(=O)(=O)C1=CC=CC=C1 XDMKVVVABSVLLZ-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• SKUWQHFAVXTGOM-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-(pyrrolidin-1-ylmethyl)indole Chemical compound C1=CC2=C(CN3CCCC3)C=CC=C2N1S(=O)(=O)C1=CC=CC=C1 SKUWQHFAVXTGOM-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
• 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 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
• NUNHASVOYPUZPP-UHFFFAOYSA-N 2-sulfonyl-1,3-dihydroindole Chemical class C1=CC=C2NC(=S(=O)=O)CC2=C1 NUNHASVOYPUZPP-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• LZFCKIGRFOMGMW-UHFFFAOYSA-N 4-(piperazin-1-ylmethyl)-1-thiophen-2-ylsulfonylindole Chemical compound C1=CC2=C(CN3CCNCC3)C=CC=C2N1S(=O)(=O)C1=CC=CS1 LZFCKIGRFOMGMW-UHFFFAOYSA-N 0.000 claims description 3
• FWNNVNPKOUDNKW-UHFFFAOYSA-N 4-(pyrrolidin-1-ylmethyl)-1-thiophen-2-ylsulfonylindole Chemical compound C1=CC2=C(CN3CCCC3)C=CC=C2N1S(=O)(=O)C1=CC=CS1 FWNNVNPKOUDNKW-UHFFFAOYSA-N 0.000 claims description 3
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 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
• 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
• 235000012631 food intake Nutrition 0.000 claims description 3
• 229910052763 palladium Inorganic materials 0.000 claims description 3
• 239000012279 sodium borohydride Substances 0.000 claims description 3
• 229910000033 sodium borohydride Inorganic materials 0.000 claims description 3
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 3
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 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 2
• 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 2
• 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 2
• USXYFVLZLANFJE-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-methyl-4-(pyrrolidin-1-ylmethyl)indole Chemical compound C=12C(C)=CN(S(=O)(=O)C=3C=CC=CC=3)C2=CC=CC=1CN1CCCC1 USXYFVLZLANFJE-UHFFFAOYSA-N 0.000 claims description 2
• OGYBTSUKACJHHH-UHFFFAOYSA-N 1-(benzenesulfonyl)-6-fluoro-4-[(4-methylpiperazin-1-yl)methyl]indole Chemical compound C1CN(C)CCN1CC1=CC(F)=CC2=C1C=CN2S(=O)(=O)C1=CC=CC=C1 OGYBTSUKACJHHH-UHFFFAOYSA-N 0.000 claims description 2
• ZIVWVEYAKZJTSL-UHFFFAOYSA-N 1-(benzenesulfonyl)-6-fluoro-5-methoxy-4-(pyrrolidin-1-ylmethyl)indole Chemical compound COC1=C(F)C=C2N(S(=O)(=O)C=3C=CC=CC=3)C=CC2=C1CN1CCCC1 ZIVWVEYAKZJTSL-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
• 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
• 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 2
• 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 2
• 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 2
• 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 description 2
• 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 2
• MDFFTHVYIQDWRV-UHFFFAOYSA-N 1-[[1-(benzenesulfonyl)indol-4-yl]methyl]pyrrolidin-3-amine Chemical compound C1C(N)CCN1CC1=CC=CC2=C1C=CN2S(=O)(=O)C1=CC=CC=C1 MDFFTHVYIQDWRV-UHFFFAOYSA-N 0.000 claims description 2
• 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 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
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 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
• 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 2
• 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 2
• 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 description 2
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
• 150000002500 ions Chemical class 0.000 claims description 2
• 238000004811 liquid chromatography Methods 0.000 claims description 2
• YQBMGOXSXLGTKH-UHFFFAOYSA-N n,n-dimethyl-1-(1-thiophen-2-ylsulfonylindol-4-yl)methanamine Chemical compound C1=CC=2C(CN(C)C)=CC=CC=2N1S(=O)(=O)C1=CC=CS1 YQBMGOXSXLGTKH-UHFFFAOYSA-N 0.000 claims description 2
• DWLVWMUCHSLGSU-UHFFFAOYSA-M n,n-dimethylcarbamate Chemical compound CN(C)C([O-])=O DWLVWMUCHSLGSU-UHFFFAOYSA-M 0.000 claims description 2
• BXGOEYIJDAOLGN-UHFFFAOYSA-N n-[[1-(benzenesulfonyl)-5-methoxyindol-4-yl]methyl]cyclopropanamine Chemical compound COC1=CC=C2N(S(=O)(=O)C=3C=CC=CC=3)C=CC2=C1CNC1CC1 BXGOEYIJDAOLGN-UHFFFAOYSA-N 0.000 claims description 2
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims 3
• 229920000858 Cyclodextrin Polymers 0.000 claims 2
• 238000004458 analytical method Methods 0.000 claims 2
• 238000001802 infusion Methods 0.000 claims 2
• 230000003204 osmotic effect Effects 0.000 claims 2
• HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
• 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
• 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
• 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 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
• 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
• 206010002091 Anaesthesia Diseases 0.000 claims 1
• 238000001282 Kruskal–Wallis one-way analysis of variance Methods 0.000 claims 1
• 238000000585 Mann–Whitney U test Methods 0.000 claims 1
• 239000002202 Polyethylene glycol Substances 0.000 claims 1
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 1
• 230000037005 anaesthesia Effects 0.000 claims 1
• 239000008280 blood Substances 0.000 claims 1
• 210000004369 blood Anatomy 0.000 claims 1
• 125000001309 chloro group Chemical group Cl* 0.000 claims 1
• 229940125904 compound 1 Drugs 0.000 claims 1
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
• JPGQOUSTVILISH-UHFFFAOYSA-N enflurane Chemical compound FC(F)OC(F)(F)C(F)Cl JPGQOUSTVILISH-UHFFFAOYSA-N 0.000 claims 1
• 229960000305 enflurane Drugs 0.000 claims 1
• ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
• 238000002513 implantation Methods 0.000 claims 1
• 238000012417 linear regression Methods 0.000 claims 1
• RFKMCNOHBTXSMU-UHFFFAOYSA-N methoxyflurane Chemical compound COC(F)(F)C(Cl)Cl RFKMCNOHBTXSMU-UHFFFAOYSA-N 0.000 claims 1
• 229960002455 methoxyflurane Drugs 0.000 claims 1
• 238000002552 multiple reaction monitoring Methods 0.000 claims 1
• REPYDQBANAEROL-UHFFFAOYSA-N n-[[1-(benzenesulfonyl)indol-4-yl]methyl]-2-methoxyethanamine Chemical compound C1=CC=2C(CNCCOC)=CC=CC=2N1S(=O)(=O)C1=CC=CC=C1 REPYDQBANAEROL-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 229910052762 osmium Inorganic materials 0.000 claims 1
• SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims 1
• 239000008188 pellet Substances 0.000 claims 1
• 229920001223 polyethylene glycol Polymers 0.000 claims 1
• 108090000623 proteins and genes Proteins 0.000 claims 1
• 102000004169 proteins and genes Human genes 0.000 claims 1
• 239000011780 sodium chloride Substances 0.000 claims 1
• 238000010972 statistical evaluation Methods 0.000 claims 1
• 238000007920 subcutaneous administration Methods 0.000 claims 1
• 239000006228 supernatant Substances 0.000 claims 1
• 238000001356 surgical procedure Methods 0.000 claims 1
• 238000002360 preparation method Methods 0.000 abstract description 12
• 230000008569 process Effects 0.000 abstract description 9
• 201000000980 schizophrenia Diseases 0.000 abstract description 5
• 239000000543 intermediate Substances 0.000 description 315
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 282
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 274
• 238000004949 mass spectrometry Methods 0.000 description 241
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 169
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 162
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 154
• 239000007787 solid Substances 0.000 description 150
• 229910001868 water Inorganic materials 0.000 description 141
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 131
• 238000002953 preparative HPLC Methods 0.000 description 117
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 99
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 96
• 239000011541 reaction mixture Substances 0.000 description 92
• 239000000243 solution Substances 0.000 description 81
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 57
• 239000003921 oil Substances 0.000 description 56
• 229910000104 sodium hydride Inorganic materials 0.000 description 53
• 235000011054 acetic acid Nutrition 0.000 description 52
• 238000003756 stirring Methods 0.000 description 51
• 239000012071 phase Substances 0.000 description 50
• OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 49
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 48
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 44
• 239000012044 organic layer Substances 0.000 description 43
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 40
• 239000003480 eluent Substances 0.000 description 40
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
• 238000000746 purification Methods 0.000 description 36
• 239000012043 crude product Substances 0.000 description 35
• 238000003818 flash chromatography Methods 0.000 description 27
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
• SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 26
• 230000002829 reductive effect Effects 0.000 description 26
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 25
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 24
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 24
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 23
• 239000012074 organic phase Substances 0.000 description 22
• 235000019439 ethyl acetate Nutrition 0.000 description 20
• 102000005962 receptors Human genes 0.000 description 18
• 108020003175 receptors Proteins 0.000 description 18
• CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 18
• 229910000489 osmium tetroxide Inorganic materials 0.000 description 17
• 239000012267 brine Substances 0.000 description 16
• 239000000463 material Substances 0.000 description 16
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 16
• XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 15
• 238000001556 precipitation Methods 0.000 description 15
• FUHGQUQCMNTLLX-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1h-indole Chemical compound C=1C=CC=2NC=CC=2C=1CN1CCC1 FUHGQUQCMNTLLX-UHFFFAOYSA-N 0.000 description 14
• 239000000725 suspension Substances 0.000 description 14
• 239000002253 acid Substances 0.000 description 13
• 239000008346 aqueous phase Substances 0.000 description 13
• UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 13
• 239000000377 silicon dioxide Substances 0.000 description 13
• 239000007858 starting material Substances 0.000 description 13
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• 239000012230 colorless oil Substances 0.000 description 12
• XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 12
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 12
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 12
• 239000010410 layer Substances 0.000 description 12
• 239000003643 water by type Substances 0.000 description 12
• IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 11
• 230000009467 reduction Effects 0.000 description 11
• 238000006722 reduction reaction Methods 0.000 description 11
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 10
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
• CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 10
• 150000001721 carbon Chemical group 0.000 description 10
• 239000013058 crude material Substances 0.000 description 10
• 241000400611 Eucalyptus deanei Species 0.000 description 9
• 125000001041 indolyl group Chemical group 0.000 description 9
• 229910000027 potassium carbonate Inorganic materials 0.000 description 9
• 229920006395 saturated elastomer Polymers 0.000 description 9
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 8
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 8
• ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 8
• 229930040373 Paraformaldehyde Natural products 0.000 description 8
• 239000002585 base Substances 0.000 description 8
• 239000007788 liquid Substances 0.000 description 8
• 239000002480 mineral oil Substances 0.000 description 8
• 235000010446 mineral oil Nutrition 0.000 description 8
• 229920002866 paraformaldehyde Polymers 0.000 description 8
• 238000010992 reflux Methods 0.000 description 8
• 239000012258 stirred mixture Substances 0.000 description 8
• MYQDYZOVXVEVBW-UHFFFAOYSA-N 1-(benzenesulfonyl)-6-fluoroindol-5-ol Chemical compound C1=2C=C(F)C(O)=CC=2C=CN1S(=O)(=O)C1=CC=CC=C1 MYQDYZOVXVEVBW-UHFFFAOYSA-N 0.000 description 7
• 241000283690 Bos taurus Species 0.000 description 7
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
• 241000283073 Equus caballus Species 0.000 description 7
• 241000282326 Felis catus Species 0.000 description 7
• 208000008589 Obesity Diseases 0.000 description 7
• 241000009328 Perro Species 0.000 description 7
• 238000010511 deprotection reaction Methods 0.000 description 7
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
• 235000020824 obesity Nutrition 0.000 description 7
• 239000012285 osmium tetroxide Substances 0.000 description 7
• 238000011321 prophylaxis Methods 0.000 description 7
• 125000006239 protecting group Chemical group 0.000 description 7
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 6
• AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 6
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
• 235000012538 ammonium bicarbonate Nutrition 0.000 description 6
• 239000000872 buffer Substances 0.000 description 6
• 239000003153 chemical reaction reagent Substances 0.000 description 6
• ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 6
• JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 6
• 235000015320 potassium carbonate Nutrition 0.000 description 6
• 239000000741 silica gel Substances 0.000 description 6
• 229910002027 silica gel Inorganic materials 0.000 description 6
• 238000003786 synthesis reaction Methods 0.000 description 6
• CZZCMKKTAMXPTQ-UHFFFAOYSA-N tert-butyl 4-[(6-methoxy-1h-indol-4-yl)methyl]piperazine-1-carboxylate Chemical compound C=12C=CNC2=CC(OC)=CC=1CN1CCN(C(=O)OC(C)(C)C)CC1 CZZCMKKTAMXPTQ-UHFFFAOYSA-N 0.000 description 6
• KMVZDSQHLDGKGV-UHFFFAOYSA-N 2-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=CC=C1S(Cl)(=O)=O KMVZDSQHLDGKGV-UHFFFAOYSA-N 0.000 description 5
• ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 5
• 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 5
• 244000018764 Nyssa sylvatica Species 0.000 description 5
• 235000003339 Nyssa sylvatica Nutrition 0.000 description 5
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
• 125000000217 alkyl group Chemical group 0.000 description 5
• 239000001099 ammonium carbonate Substances 0.000 description 5
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 5
• 239000012467 final product Substances 0.000 description 5
• XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
• 239000000843 powder Substances 0.000 description 5
• WDPWEXWMQDRXAL-UHFFFAOYSA-N tert-butyl 1,4-diazepane-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCNCC1 WDPWEXWMQDRXAL-UHFFFAOYSA-N 0.000 description 5
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
• JOMNTHCQHJPVAZ-UHFFFAOYSA-N 2-methylpiperazine Chemical compound CC1CNCCN1 JOMNTHCQHJPVAZ-UHFFFAOYSA-N 0.000 description 4
• ZSIYKAQPQRTBPF-UHFFFAOYSA-N 3-chloro-2-methylbenzenesulfonyl chloride Chemical compound CC1=C(Cl)C=CC=C1S(Cl)(=O)=O ZSIYKAQPQRTBPF-UHFFFAOYSA-N 0.000 description 4
• WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 4
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 4
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
• 241000124008 Mammalia Species 0.000 description 4
• OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 4
• 238000005481 NMR spectroscopy Methods 0.000 description 4
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
• 239000005557 antagonist Substances 0.000 description 4
• 238000009835 boiling Methods 0.000 description 4
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
• 238000004440 column chromatography Methods 0.000 description 4
• 229960004132 diethyl ether Drugs 0.000 description 4
• 201000010099 disease Diseases 0.000 description 4
• 238000001914 filtration Methods 0.000 description 4
• 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 4
• 238000010438 heat treatment Methods 0.000 description 4
• 229910000042 hydrogen bromide Inorganic materials 0.000 description 4
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 4
• 239000003208 petroleum Substances 0.000 description 4
• BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical compound NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 description 4
• 125000006413 ring segment Chemical group 0.000 description 4
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
• VNNLHYZDXIBHKZ-UHFFFAOYSA-N thiophene-2-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CS1 VNNLHYZDXIBHKZ-UHFFFAOYSA-N 0.000 description 4
• SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 3
• KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 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 description 3
• ISNPSUWNBFGNLT-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-(1,4-diazepan-1-ylmethyl)indol-6-ol Chemical compound C=12C=CN(S(=O)(=O)C=3C=CC=CC=3)C2=CC(O)=CC=1CN1CCCNCC1 ISNPSUWNBFGNLT-UHFFFAOYSA-N 0.000 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 description 3
• XLQHITAMOGOKLB-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-bromo-3-methylindole Chemical compound C12=CC=CC(Br)=C2C(C)=CN1S(=O)(=O)C1=CC=CC=C1 XLQHITAMOGOKLB-UHFFFAOYSA-N 0.000 description 3
• CZEXVNDQUSHRPL-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-bromo-6-fluoroindole Chemical compound C12=CC(F)=CC(Br)=C2C=CN1S(=O)(=O)C1=CC=CC=C1 CZEXVNDQUSHRPL-UHFFFAOYSA-N 0.000 description 3
• VQEQGKUNHIZJQD-UHFFFAOYSA-N 1-(benzenesulfonyl)-5-phenylmethoxyindole-4-carbaldehyde Chemical compound C1=CC=2N(S(=O)(=O)C=3C=CC=CC=3)C=CC=2C(C=O)=C1OCC1=CC=CC=C1 VQEQGKUNHIZJQD-UHFFFAOYSA-N 0.000 description 3
• PFOZCVVYRJPANO-UHFFFAOYSA-N 1-(benzenesulfonyl)-6-fluoro-4-(pyrrolidin-1-ylmethyl)indol-5-ol Chemical compound OC1=C(F)C=C2N(S(=O)(=O)C=3C=CC=CC=3)C=CC2=C1CN1CCCC1 PFOZCVVYRJPANO-UHFFFAOYSA-N 0.000 description 3
• 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 description 3
• 238000005160 1H NMR spectroscopy Methods 0.000 description 3
• HTUNRWSWIRFPQX-UHFFFAOYSA-N 2-bromo-3-methyl-4-nitrophenol Chemical compound CC1=C(Br)C(O)=CC=C1[N+]([O-])=O HTUNRWSWIRFPQX-UHFFFAOYSA-N 0.000 description 3
• NQAYCMBZPAARNO-UHFFFAOYSA-N 2-cyanobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1C#N NQAYCMBZPAARNO-UHFFFAOYSA-N 0.000 description 3
• BJYNYQGJTZULJI-UHFFFAOYSA-N 2-methoxy-5-methylbenzenesulfonyl chloride Chemical compound COC1=CC=C(C)C=C1S(Cl)(=O)=O BJYNYQGJTZULJI-UHFFFAOYSA-N 0.000 description 3
• ONCAZCNPWWQQMW-UHFFFAOYSA-N 3-(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC(F)(F)C1=CC=CC(S(Cl)(=O)=O)=C1 ONCAZCNPWWQQMW-UHFFFAOYSA-N 0.000 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 description 3
• YCZIPDONHLRYHW-UHFFFAOYSA-N 4-[(4-propylpiperazin-1-yl)methyl]-1-thiophen-2-ylsulfonylindole Chemical compound C1CN(CCC)CCN1CC1=CC=CC2=C1C=CN2S(=O)(=O)C1=CC=CS1 YCZIPDONHLRYHW-UHFFFAOYSA-N 0.000 description 3
• HQYNWUZMWCHKGJ-UHFFFAOYSA-N 4-bromo-3-methyl-1h-indole Chemical compound C1=CC(Br)=C2C(C)=CNC2=C1 HQYNWUZMWCHKGJ-UHFFFAOYSA-N 0.000 description 3
• DMOWKZSCECYXSE-UHFFFAOYSA-N 4-bromo-6-fluoro-1h-indole Chemical compound FC1=CC(Br)=C2C=CNC2=C1 DMOWKZSCECYXSE-UHFFFAOYSA-N 0.000 description 3
• 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 3
• 229910004373 HOAc Inorganic materials 0.000 description 3
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
• YBBJMVIISYOWDZ-UHFFFAOYSA-N [1-(benzenesulfonyl)-4-bromo-6-(trifluoromethyl)indol-2-yl]methanol Chemical compound OCC1=CC2=C(Br)C=C(C(F)(F)F)C=C2N1S(=O)(=O)C1=CC=CC=C1 YBBJMVIISYOWDZ-UHFFFAOYSA-N 0.000 description 3
• 150000007513 acids Chemical class 0.000 description 3
• 239000013543 active substance Substances 0.000 description 3
• 125000003342 alkenyl group Chemical group 0.000 description 3
• 229940025084 amphetamine Drugs 0.000 description 3
• HGQULGDOROIPJN-UHFFFAOYSA-N azetidin-1-ium;chloride Chemical compound Cl.C1CNC1 HGQULGDOROIPJN-UHFFFAOYSA-N 0.000 description 3
• 230000009286 beneficial effect Effects 0.000 description 3
• 230000015572 biosynthetic process Effects 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• 229960003920 cocaine Drugs 0.000 description 3
• 238000007796 conventional method Methods 0.000 description 3
• 238000001704 evaporation Methods 0.000 description 3
• 230000008020 evaporation Effects 0.000 description 3
• 239000000706 filtrate Substances 0.000 description 3
• 125000001153 fluoro group Chemical group F* 0.000 description 3
• 238000009472 formulation Methods 0.000 description 3
• 230000006870 function Effects 0.000 description 3
• 239000005457 ice water Substances 0.000 description 3
• 230000001771 impaired effect Effects 0.000 description 3
• UEXQBEVWFZKHNB-UHFFFAOYSA-N intermediate 29 Natural products C1=CC(N)=CC=C1NC1=NC=CC=N1 UEXQBEVWFZKHNB-UHFFFAOYSA-N 0.000 description 3
• 125000002950 monocyclic group Chemical group 0.000 description 3
• IFYDWYVPVAMGRO-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]tetradecanamide Chemical compound CCCCCCCCCCCCCC(=O)NCCCN(C)C IFYDWYVPVAMGRO-UHFFFAOYSA-N 0.000 description 3
• 230000004770 neurodegeneration Effects 0.000 description 3
• 230000007514 neuronal growth Effects 0.000 description 3
• 229960002715 nicotine Drugs 0.000 description 3
• SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 3
• 230000003287 optical effect Effects 0.000 description 3
• 239000004031 partial agonist Substances 0.000 description 3
• 239000002244 precipitate Substances 0.000 description 3
• 238000006268 reductive amination reaction Methods 0.000 description 3
• 229910000029 sodium carbonate Inorganic materials 0.000 description 3
• 239000000126 substance Substances 0.000 description 3
• XYQUCHXSILOSEJ-UHFFFAOYSA-N tert-butyl 4-[[1-(benzenesulfonyl)-5-hydroxyindol-4-yl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC1=C(O)C=CC2=C1C=CN2S(=O)(=O)C1=CC=CC=C1 XYQUCHXSILOSEJ-UHFFFAOYSA-N 0.000 description 3
• LZRDHSFPLUWYAX-UHFFFAOYSA-N tert-butyl 4-aminopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(N)CC1 LZRDHSFPLUWYAX-UHFFFAOYSA-N 0.000 description 3
• 230000001225 therapeutic effect Effects 0.000 description 3
• 238000002560 therapeutic procedure Methods 0.000 description 3
• 125000000335 thiazolyl group Chemical group 0.000 description 3
• 230000009466 transformation Effects 0.000 description 3
• 229920002554 vinyl polymer Polymers 0.000 description 3
• JOMNTHCQHJPVAZ-RXMQYKEDSA-N (2r)-2-methylpiperazine Chemical compound C[C@@H]1CNCCN1 JOMNTHCQHJPVAZ-RXMQYKEDSA-N 0.000 description 2
• JOMNTHCQHJPVAZ-YFKPBYRVSA-N (2s)-2-methylpiperazine Chemical compound C[C@H]1CNCCN1 JOMNTHCQHJPVAZ-YFKPBYRVSA-N 0.000 description 2
• SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
• 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 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 description 2
• OUCPTUXUZLWTHY-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-4-[(4-propan-2-ylpiperazin-1-yl)methyl]indole Chemical compound C1CN(C(C)C)CCN1CC1=CC=CC2=C1C=CN2S(=O)(=O)C1=CC=C(C)C=C1 OUCPTUXUZLWTHY-UHFFFAOYSA-N 0.000 description 2
• KGPFIXHTENHMBN-UHFFFAOYSA-N 1-(benzenesulfonyl)-2-methyl-4-(piperazin-1-ylmethyl)indole;hydrochloride Chemical compound Cl.C1=CC=C2N(S(=O)(=O)C=3C=CC=CC=3)C(C)=CC2=C1CN1CCNCC1 KGPFIXHTENHMBN-UHFFFAOYSA-N 0.000 description 2
• IUTPZSNWQBJAJR-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-(1,4-diazepan-1-ylmethyl)-6-fluoroindole Chemical compound C=12C=CN(S(=O)(=O)C=3C=CC=CC=3)C2=CC(F)=CC=1CN1CCCNCC1 IUTPZSNWQBJAJR-UHFFFAOYSA-N 0.000 description 2
• KDAXVBPZELYLRB-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-(1,4-dimethylpiperazin-2-yl)indole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C1N(C)CCN(C)C1C1=CC=CC2=C1C=CN2S(=O)(=O)C1=CC=CC=C1 KDAXVBPZELYLRB-UHFFFAOYSA-N 0.000 description 2
• VOFLESICCSFQFW-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-(bromomethyl)indole Chemical compound C1=CC=2C(CBr)=CC=CC=2N1S(=O)(=O)C1=CC=CC=C1 VOFLESICCSFQFW-UHFFFAOYSA-N 0.000 description 2
• 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 description 2
• LKLMWMMGXMUJMQ-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-[(dimethylamino)methyl]-6-fluoroindol-5-ol;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC=2C(CN(C)C)=C(O)C(F)=CC=2N1S(=O)(=O)C1=CC=CC=C1 LKLMWMMGXMUJMQ-UHFFFAOYSA-N 0.000 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 description 2
• 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 description 2
• VVSYCQRIBGOXQL-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-[(dimethylamino)methyl]indol-5-ol;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC=2C(CN(C)C)=C(O)C=CC=2N1S(=O)(=O)C1=CC=CC=C1 VVSYCQRIBGOXQL-UHFFFAOYSA-N 0.000 description 2
• 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 description 2
• WCJCQQNFUXAMCY-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-bromo-5-methoxyindole Chemical compound C1=CC2=C(Br)C(OC)=CC=C2N1S(=O)(=O)C1=CC=CC=C1 WCJCQQNFUXAMCY-UHFFFAOYSA-N 0.000 description 2
• OHZRCLGTXAFAAR-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-bromo-7-methoxyindole Chemical compound C1=2C(OC)=CC=C(Br)C=2C=CN1S(=O)(=O)C1=CC=CC=C1 OHZRCLGTXAFAAR-UHFFFAOYSA-N 0.000 description 2
• HVBNJRFHUBWAPU-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-ethenyl-3-methylindole Chemical compound C12=CC=CC(C=C)=C2C(C)=CN1S(=O)(=O)C1=CC=CC=C1 HVBNJRFHUBWAPU-UHFFFAOYSA-N 0.000 description 2
• CZYYGDFLTYZABW-UHFFFAOYSA-N 1-(benzenesulfonyl)-6-fluoro-4-(pyrrolidin-1-ylmethyl)indole Chemical compound C=12C=CN(S(=O)(=O)C=3C=CC=CC=3)C2=CC(F)=CC=1CN1CCCC1 CZYYGDFLTYZABW-UHFFFAOYSA-N 0.000 description 2
• NSEDEDZWGZLOFH-UHFFFAOYSA-N 1-(benzenesulfonyl)-6-methoxy-4-(pyrrolidin-1-ylmethyl)indole Chemical compound C=12C=CN(S(=O)(=O)C=3C=CC=CC=3)C2=CC(OC)=CC=1CN1CCCC1 NSEDEDZWGZLOFH-UHFFFAOYSA-N 0.000 description 2
• RGHYYVXXCUUNLA-UHFFFAOYSA-N 1-(benzenesulfonyl)indole-4-carbaldehyde Chemical compound C1=CC=2C(C=O)=CC=CC=2N1S(=O)(=O)C1=CC=CC=C1 RGHYYVXXCUUNLA-UHFFFAOYSA-N 0.000 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 description 2
• RZOPBDDNOSELGK-UHFFFAOYSA-N 1-bromo-4-methoxy-2-methyl-3-nitrobenzene Chemical compound COC1=CC=C(Br)C(C)=C1[N+]([O-])=O RZOPBDDNOSELGK-UHFFFAOYSA-N 0.000 description 2
• FRXHSEOEFOMQAJ-UHFFFAOYSA-N 1-methylsulfonyl-7-phenylmethoxyindole-4-carbaldehyde Chemical compound C=12N(S(=O)(=O)C)C=CC2=C(C=O)C=CC=1OCC1=CC=CC=C1 FRXHSEOEFOMQAJ-UHFFFAOYSA-N 0.000 description 2
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
• YTPQLWVHCBATKO-UHFFFAOYSA-N 1-propylpiperazine;dihydrobromide Chemical compound Br.Br.CCCN1CCNCC1 YTPQLWVHCBATKO-UHFFFAOYSA-N 0.000 description 2
• 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 2
• SHELADVIRCCTFN-UHFFFAOYSA-N 2,5-dimethoxybenzenesulfonyl chloride Chemical compound COC1=CC=C(OC)C(S(Cl)(=O)=O)=C1 SHELADVIRCCTFN-UHFFFAOYSA-N 0.000 description 2
• MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 2
• 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 description 2
• JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 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 description 2
• BCDDQHXDORNHMC-UHFFFAOYSA-N 2-bromo-5-methyl-4-nitrophenol Chemical compound CC1=CC(O)=C(Br)C=C1[N+]([O-])=O BCDDQHXDORNHMC-UHFFFAOYSA-N 0.000 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 description 2
• 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 description 2
• WGGVGSZXNIRLNH-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-(2,5-difluorophenyl)sulfonylindole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC1=CC=C(F)C(S(=O)(=O)N2C3=CC=CC(CN4CCC4)=C3C=C2)=C1 WGGVGSZXNIRLNH-UHFFFAOYSA-N 0.000 description 2
• OQTCTYLLTMYACO-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-(2,6-difluorophenyl)sulfonylindole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC1=CC=CC(F)=C1S(=O)(=O)N1C2=CC=CC(CN3CCC3)=C2C=C1 OQTCTYLLTMYACO-UHFFFAOYSA-N 0.000 description 2
• VIIZLHQRPJHIPU-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-(2-chlorophenyl)sulfonylindole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.ClC1=CC=CC=C1S(=O)(=O)N1C2=CC=CC(CN3CCC3)=C2C=C1 VIIZLHQRPJHIPU-UHFFFAOYSA-N 0.000 description 2
• CHPUDSQAOZGOIM-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-(2-methoxy-5-methylphenyl)sulfonylindole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=C(C)C=C1S(=O)(=O)N1C2=CC=CC(CN3CCC3)=C2C=C1 CHPUDSQAOZGOIM-UHFFFAOYSA-N 0.000 description 2
• ANRQQBNHCSMGKK-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-(4-tert-butylphenyl)sulfonylindole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)N1C2=CC=CC(CN3CCC3)=C2C=C1 ANRQQBNHCSMGKK-UHFFFAOYSA-N 0.000 description 2
• LCFPOQUEGBAVCT-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-(5-chlorothiophen-2-yl)sulfonylindole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.S1C(Cl)=CC=C1S(=O)(=O)N1C2=CC=CC(CN3CCC3)=C2C=C1 LCFPOQUEGBAVCT-UHFFFAOYSA-N 0.000 description 2
• FENBAXNIIYULJD-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-(benzenesulfonyl)-6-fluoro-5-methoxyindole Chemical compound COC1=C(F)C=C2N(S(=O)(=O)C=3C=CC=CC=3)C=CC2=C1CN1CCC1 FENBAXNIIYULJD-UHFFFAOYSA-N 0.000 description 2
• PDNDTVDKGVYNFQ-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-(benzenesulfonyl)-6-fluoroindol-5-ol;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC1=C(F)C=C2N(S(=O)(=O)C=3C=CC=CC=3)C=CC2=C1CN1CCC1 PDNDTVDKGVYNFQ-UHFFFAOYSA-N 0.000 description 2
• WRAHOIZCWSVMHZ-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-(benzenesulfonyl)-7-methoxyindole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=2C=CN(S(=O)(=O)C=3C=CC=CC=3)C=2C(OC)=CC=C1CN1CCC1 WRAHOIZCWSVMHZ-UHFFFAOYSA-N 0.000 description 2
• KUPZAVADJCHOFY-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-[2-(trifluoromethyl)phenyl]sulfonylindole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC(F)(F)C1=CC=CC=C1S(=O)(=O)N1C2=CC=CC(CN3CCC3)=C2C=C1 KUPZAVADJCHOFY-UHFFFAOYSA-N 0.000 description 2
• 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 description 2
• YUWDCBAEWHWHSS-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-naphthalen-2-ylsulfonylindole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C2C=CC=CC2=CC=1S(=O)(=O)N(C1=CC=C2)C=CC1=C2CN1CCC1 YUWDCBAEWHWHSS-UHFFFAOYSA-N 0.000 description 2
• WNLCQUFATKCJLP-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-thiophen-2-ylsulfonylindole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC2=C(CN3CCC3)C=CC=C2N1S(=O)(=O)C1=CC=CS1 WNLCQUFATKCJLP-UHFFFAOYSA-N 0.000 description 2
• 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 description 2
• 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 description 2
• PATJMUYCUBCCGM-UHFFFAOYSA-N 4-bromo-1-(2-methoxy-5-methylphenyl)sulfonyl-2,3-dihydroindole Chemical compound COC1=CC=C(C)C=C1S(=O)(=O)N1C(C=CC=C2Br)=C2CC1 PATJMUYCUBCCGM-UHFFFAOYSA-N 0.000 description 2
• JSVUYJDYQIOIHO-UHFFFAOYSA-N 4-bromo-1-(2-methoxy-5-methylphenyl)sulfonylindole Chemical compound COC1=CC=C(C)C=C1S(=O)(=O)N1C2=CC=CC(Br)=C2C=C1 JSVUYJDYQIOIHO-UHFFFAOYSA-N 0.000 description 2
• IFXGNOAHTPHICQ-UHFFFAOYSA-N 4-bromo-1-pyridin-3-ylsulfonylindole Chemical compound C1=CC=2C(Br)=CC=CC=2N1S(=O)(=O)C1=CC=CN=C1 IFXGNOAHTPHICQ-UHFFFAOYSA-N 0.000 description 2
• PQORDMUEYBTGKB-UHFFFAOYSA-N 4-bromo-1-thiophen-2-ylsulfonylindole Chemical compound C1=CC=2C(Br)=CC=CC=2N1S(=O)(=O)C1=CC=CS1 PQORDMUEYBTGKB-UHFFFAOYSA-N 0.000 description 2
• IPAFHZDRYAWZOB-UHFFFAOYSA-N 4-bromo-1h-indole-3-carbaldehyde Chemical compound BrC1=CC=CC2=C1C(C=O)=CN2 IPAFHZDRYAWZOB-UHFFFAOYSA-N 0.000 description 2
• WCEJDYPAEFIBCD-UHFFFAOYSA-N 4-bromo-7-methoxy-1h-indole Chemical compound COC1=CC=C(Br)C2=C1NC=C2 WCEJDYPAEFIBCD-UHFFFAOYSA-N 0.000 description 2
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
• 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 2
• 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
• HVVNJUAVDAZWCB-RXMQYKEDSA-N D-prolinol Chemical compound OC[C@H]1CCCN1 HVVNJUAVDAZWCB-RXMQYKEDSA-N 0.000 description 2
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
• 206010033307 Overweight Diseases 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
• LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 2
• UUTGKHCSQBUCRG-UHFFFAOYSA-N [1-(benzenesulfonyl)-6-bromo-4-(trifluoromethyl)indol-2-yl]methanol Chemical compound OCC1=CC2=C(C(F)(F)F)C=C(Br)C=C2N1S(=O)(=O)C1=CC=CC=C1 UUTGKHCSQBUCRG-UHFFFAOYSA-N 0.000 description 2
• QGUBDAJUEIPMQA-UHFFFAOYSA-N [3-bromo-4-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical compound Cl.NNC1=CC=C(C(F)(F)F)C(Br)=C1 QGUBDAJUEIPMQA-UHFFFAOYSA-N 0.000 description 2
• GNPAWRGPJYLQAV-UHFFFAOYSA-N [N+](=O)([O-])C1=C(C=CC=C1C)O.BrC1=C(C(=C(C=C1)O)[N+](=O)[O-])C Chemical compound [N+](=O)([O-])C1=C(C=CC=C1C)O.BrC1=C(C(=C(C=C1)O)[N+](=O)[O-])C GNPAWRGPJYLQAV-UHFFFAOYSA-N 0.000 description 2
• 230000009471 action Effects 0.000 description 2
• 230000004913 activation Effects 0.000 description 2
• 150000001336 alkenes Chemical class 0.000 description 2
• 125000003545 alkoxy group Chemical group 0.000 description 2
• 235000019789 appetite Nutrition 0.000 description 2
• 230000036528 appetite Effects 0.000 description 2
• 239000012298 atmosphere Substances 0.000 description 2
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
• 125000002619 bicyclic group Chemical group 0.000 description 2
• 230000031709 bromination Effects 0.000 description 2
• 238000005893 bromination reaction Methods 0.000 description 2
• 238000004587 chromatography analysis Methods 0.000 description 2
• 238000010367 cloning Methods 0.000 description 2
• 239000013078 crystal Substances 0.000 description 2
• KZZKOVLJUKWSKX-UHFFFAOYSA-N cyclobutanamine Chemical compound NC1CCC1 KZZKOVLJUKWSKX-UHFFFAOYSA-N 0.000 description 2
• HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
• 239000000539 dimer Substances 0.000 description 2
• WCVLALOGDUHVQN-UHFFFAOYSA-N ethyl 1-(benzenesulfonyl)-4-bromo-5-methoxyindole-2-carboxylate Chemical compound CCOC(=O)C1=CC2=C(Br)C(OC)=CC=C2N1S(=O)(=O)C1=CC=CC=C1 WCVLALOGDUHVQN-UHFFFAOYSA-N 0.000 description 2
• FJXCEVUGUQSGEK-UHFFFAOYSA-N ethyl 1-(benzenesulfonyl)-4-bromo-6-(trifluoromethyl)indole-2-carboxylate Chemical compound CCOC(=O)C1=CC2=C(Br)C=C(C(F)(F)F)C=C2N1S(=O)(=O)C1=CC=CC=C1 FJXCEVUGUQSGEK-UHFFFAOYSA-N 0.000 description 2
• LNERQJRPNFDTFO-UHFFFAOYSA-N ethyl 1-(benzenesulfonyl)-4-ethenyl-5-methoxyindole-2-carboxylate Chemical compound CCOC(=O)C1=CC2=C(C=C)C(OC)=CC=C2N1S(=O)(=O)C1=CC=CC=C1 LNERQJRPNFDTFO-UHFFFAOYSA-N 0.000 description 2
• UFKTZUHEUYVSRI-UHFFFAOYSA-N ethyl 1-(benzenesulfonyl)-4-formyl-5-methoxyindole-2-carboxylate Chemical compound CCOC(=O)C1=CC2=C(C=O)C(OC)=CC=C2N1S(=O)(=O)C1=CC=CC=C1 UFKTZUHEUYVSRI-UHFFFAOYSA-N 0.000 description 2
• ZZFQTGKTWDHQOE-UHFFFAOYSA-N ethyl 1-(benzenesulfonyl)-6-bromo-4-(trifluoromethyl)indole-2-carboxylate Chemical compound CCOC(=O)C1=CC2=C(C(F)(F)F)C=C(Br)C=C2N1S(=O)(=O)C1=CC=CC=C1 ZZFQTGKTWDHQOE-UHFFFAOYSA-N 0.000 description 2
• NBTXRPQZVZUOGD-UHFFFAOYSA-N ethyl 4-bromo-5-methoxy-1h-indole-2-carboxylate Chemical compound COC1=CC=C2NC(C(=O)OCC)=CC2=C1Br NBTXRPQZVZUOGD-UHFFFAOYSA-N 0.000 description 2
• DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 description 2
• 238000000605 extraction Methods 0.000 description 2
• 230000037406 food intake Effects 0.000 description 2
• 239000012458 free base Substances 0.000 description 2
• 239000007789 gas Substances 0.000 description 2
• 229960004275 glycolic acid Drugs 0.000 description 2
• 239000008187 granular material Substances 0.000 description 2
• 230000036541 health Effects 0.000 description 2
• 150000004677 hydrates Chemical class 0.000 description 2
• 229910052740 iodine Inorganic materials 0.000 description 2
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
• 239000002207 metabolite Substances 0.000 description 2
• XETFBTXVGCQYBD-UHFFFAOYSA-N methanamine;2,2,2-trifluoroacetic acid Chemical compound [NH3+]C.[O-]C(=O)C(F)(F)F XETFBTXVGCQYBD-UHFFFAOYSA-N 0.000 description 2
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
• NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 2
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
• OPECTNGATDYLSS-UHFFFAOYSA-N naphthalene-2-sulfonyl chloride Chemical compound C1=CC=CC2=CC(S(=O)(=O)Cl)=CC=C21 OPECTNGATDYLSS-UHFFFAOYSA-N 0.000 description 2
• 230000007935 neutral effect Effects 0.000 description 2
• 239000012299 nitrogen atmosphere Substances 0.000 description 2
• 231100000252 nontoxic Toxicity 0.000 description 2
• 230000003000 nontoxic effect Effects 0.000 description 2
• KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
• 229910052760 oxygen Inorganic materials 0.000 description 2
• UVBXZOISXNZBLY-UHFFFAOYSA-L palladium(2+);triphenylphosphane;diacetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UVBXZOISXNZBLY-UHFFFAOYSA-L 0.000 description 2
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
• 239000000546 pharmaceutical excipient Substances 0.000 description 2
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
• 235000011181 potassium carbonates Nutrition 0.000 description 2
• JUYUYCIJACTHMK-UHFFFAOYSA-N quinoline-8-sulfonyl chloride Chemical compound C1=CN=C2C(S(=O)(=O)Cl)=CC=CC2=C1 JUYUYCIJACTHMK-UHFFFAOYSA-N 0.000 description 2
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
• 238000011160 research Methods 0.000 description 2
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
• 238000002821 scintillation proximity assay Methods 0.000 description 2
• 239000003751 serotonin 6 antagonist Substances 0.000 description 2
• 239000002002 slurry Substances 0.000 description 2
• 239000011734 sodium Substances 0.000 description 2
• 229910052708 sodium Inorganic materials 0.000 description 2
• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
• 239000012312 sodium hydride Substances 0.000 description 2
• 239000012453 solvate Substances 0.000 description 2
• 125000003107 substituted aryl group Chemical group 0.000 description 2
• 239000001117 sulphuric acid Substances 0.000 description 2
• 235000011149 sulphuric acid Nutrition 0.000 description 2
• 239000006188 syrup Substances 0.000 description 2
• 235000020357 syrup Nutrition 0.000 description 2
• 239000003826 tablet Substances 0.000 description 2
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• 238000000844 transformation Methods 0.000 description 2
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
• 229910052721 tungsten Inorganic materials 0.000 description 2
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
• VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
• QYYZXEPEVBXNNA-QGZVFWFLSA-N (1R)-2-acetyl-N-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl]-5-methylsulfonyl-1,3-dihydroisoindole-1-carboxamide Chemical compound C(C)(=O)N1[C@H](C2=CC=C(C=C2C1)S(=O)(=O)C)C(=O)NC1=CC=C(C=C1)C(C(F)(F)F)(C(F)(F)F)O QYYZXEPEVBXNNA-QGZVFWFLSA-N 0.000 description 1
• NBKZGRPRTQELKX-UHFFFAOYSA-N (2-methylpropan-2-yl)oxymethanone Chemical compound CC(C)(C)O[C]=O NBKZGRPRTQELKX-UHFFFAOYSA-N 0.000 description 1
• ITOFPJRDSCGOSA-KZLRUDJFSA-N (2s)-2-[[(4r)-4-[(3r,5r,8r,9s,10s,13r,14s,17r)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H](CC[C@]13C)[C@@H]2[C@@H]3CC[C@@H]1[C@H](C)CCC(=O)N[C@H](C(O)=O)CC1=CNC2=CC=CC=C12 ITOFPJRDSCGOSA-KZLRUDJFSA-N 0.000 description 1
• UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 1
• MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
• 125000006592 (C2-C3) alkenyl group Chemical group 0.000 description 1
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 description 1
• 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 description 1
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
• VLSDXINSOMDCBK-BQYQJAHWSA-N (E)-1,1'-azobis(N,N-dimethylformamide) Chemical compound CN(C)C(=O)\N=N\C(=O)N(C)C VLSDXINSOMDCBK-BQYQJAHWSA-N 0.000 description 1
• BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
• ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 1
• MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
• DMFPQQCIQDWBJK-UHFFFAOYSA-N 1,3-thiazole-5-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CN=CS1 DMFPQQCIQDWBJK-UHFFFAOYSA-N 0.000 description 1
• APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 description 1
• GGRWEYLDDHBSCJ-UHFFFAOYSA-N 1-(2,5-dimethoxyphenyl)sulfonyl-6-methoxy-4-(piperazin-1-ylmethyl)indole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.COC1=CC=C(OC)C(S(=O)(=O)N2C3=CC(OC)=CC(CN4CCNCC4)=C3C=C2)=C1 GGRWEYLDDHBSCJ-UHFFFAOYSA-N 0.000 description 1
• IBKQUPKABIPKTC-UHFFFAOYSA-N 1-(2-chlorophenyl)sulfonyl-6-methoxy-4-(piperazin-1-ylmethyl)indole Chemical compound C=12C=CN(S(=O)(=O)C=3C(=CC=CC=3)Cl)C2=CC(OC)=CC=1CN1CCNCC1 IBKQUPKABIPKTC-UHFFFAOYSA-N 0.000 description 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 description 1
• ULLCRIGGVSZEOB-UHFFFAOYSA-N 1-(2-methoxy-5-methylphenyl)sulfonyl-4-(pyrrolidin-1-ylmethyl)-2,3-dihydroindole Chemical compound COC1=CC=C(C)C=C1S(=O)(=O)N1C(C=CC=C2CN3CCCC3)=C2CC1 ULLCRIGGVSZEOB-UHFFFAOYSA-N 0.000 description 1
• ITYGVGWLUMXXHE-UHFFFAOYSA-N 1-(2-methoxy-5-methylphenyl)sulfonyl-4-[(2-methylpyrrolidin-1-yl)methyl]indole Chemical compound COC1=CC=C(C)C=C1S(=O)(=O)N1C2=CC=CC(CN3C(CCC3)C)=C2C=C1 ITYGVGWLUMXXHE-UHFFFAOYSA-N 0.000 description 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 description 1
• MHKSNQLPVWMCLL-UHFFFAOYSA-N 1-(2-methoxy-5-methylphenyl)sulfonyl-4-[(4-methylpiperazin-1-yl)methyl]-2,3-dihydroindole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.COC1=CC=C(C)C=C1S(=O)(=O)N1C(C=CC=C2CN3CCN(C)CC3)=C2CC1 MHKSNQLPVWMCLL-UHFFFAOYSA-N 0.000 description 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 description 1
• JUWQVKARXGHYRR-UHFFFAOYSA-N 1-(2-methylphenyl)sulfonyl-4-(pyrrolidin-1-ylmethyl)indole Chemical compound CC1=CC=CC=C1S(=O)(=O)N1C2=CC=CC(CN3CCCC3)=C2C=C1 JUWQVKARXGHYRR-UHFFFAOYSA-N 0.000 description 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 description 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 description 1
• 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 description 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 description 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 description 1
• CURGACQCSYXHKF-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-4-(pyrrolidin-1-ylmethyl)indole Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=CC=CC(CN3CCCC3)=C2C=C1 CURGACQCSYXHKF-UHFFFAOYSA-N 0.000 description 1
• QNXDZMOQLFTMFC-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-4-[(3-methylpiperazin-1-yl)methyl]indole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C1CNC(C)CN1CC1=CC=CC2=C1C=CN2S(=O)(=O)C1=CC=C(C)C=C1 QNXDZMOQLFTMFC-UHFFFAOYSA-N 0.000 description 1
• UAZGGPGJRIIPNB-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-4-[(4-methylpiperazin-1-yl)methyl]indole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C1CN(C)CCN1CC1=CC=CC2=C1C=CN2S(=O)(=O)C1=CC=C(C)C=C1 UAZGGPGJRIIPNB-UHFFFAOYSA-N 0.000 description 1
• FBCBXGXYAQNGAW-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-4-[(4-propan-2-ylpiperazin-1-yl)methyl]indole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C1CN(C(C)C)CCN1CC1=CC=CC2=C1C=CN2S(=O)(=O)C1=CC=C(C)C=C1 FBCBXGXYAQNGAW-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• XETWIUXPWFJTRG-UHFFFAOYSA-N 1-(5-ethoxy-1-naphthalen-1-ylsulfonylindol-4-yl)-n,n-dimethylmethanamine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC=C2C(S(=O)(=O)N3C4=CC=C(C(=C4C=C3)CN(C)C)OCC)=CC=CC2=C1 XETWIUXPWFJTRG-UHFFFAOYSA-N 0.000 description 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 description 1
• ZAURRXKQGRYBAR-UHFFFAOYSA-N 1-(5-ethoxy-1-naphthalen-2-ylsulfonylindol-4-yl)-n,n-dimethylmethanamine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC=CC2=CC(S(=O)(=O)N3C4=CC=C(C(=C4C=C3)CN(C)C)OCC)=CC=C21 ZAURRXKQGRYBAR-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• XZMPQQHWJXHILR-UHFFFAOYSA-N 1-(5-ethoxy-1-quinolin-8-ylsulfonylindol-4-yl)-n,n-dimethylmethanamine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C1=CN=C2C(S(=O)(=O)N3C4=CC=C(C(=C4C=C3)CN(C)C)OCC)=CC=CC2=C1 XZMPQQHWJXHILR-UHFFFAOYSA-N 0.000 description 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 description 1
• NCEKONSTJRDUQA-UHFFFAOYSA-N 1-(5-methoxy-1h-indol-4-yl)-n,n-dimethylmethanamine;1-[5-methoxy-1-[3-(trifluoromethyl)phenyl]sulfonylindol-4-yl]-n,n-dimethylmethanamine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=C2NC=CC2=C1CN(C)C.C1=CC2=C(CN(C)C)C(OC)=CC=C2N1S(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 NCEKONSTJRDUQA-UHFFFAOYSA-N 0.000 description 1
• SYYPBRKVYRCLJS-UHFFFAOYSA-N 1-(benzenesulfonyl)-2-(bromomethyl)indole Chemical compound BrCC1=CC2=CC=CC=C2N1S(=O)(=O)C1=CC=CC=C1 SYYPBRKVYRCLJS-UHFFFAOYSA-N 0.000 description 1
• QKQLHDNPBJQQLC-UHFFFAOYSA-N 1-(benzenesulfonyl)-2-(hydroxymethyl)-4-(trifluoromethyl)indole-6-carbaldehyde Chemical compound OCC1=CC2=C(C(F)(F)F)C=C(C=O)C=C2N1S(=O)(=O)C1=CC=CC=C1 QKQLHDNPBJQQLC-UHFFFAOYSA-N 0.000 description 1
• UZZVFFMNHNMMFH-UHFFFAOYSA-N 1-(benzenesulfonyl)-2-fluoroindol-5-ol Chemical compound FC=1N(C2=CC=C(C=C2C=1)O)S(=O)(=O)C1=CC=CC=C1 UZZVFFMNHNMMFH-UHFFFAOYSA-N 0.000 description 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 description 1
• ZTEGRDKDWRRHET-UHFFFAOYSA-N 1-(benzenesulfonyl)-2-methylindole-4-carbaldehyde Chemical compound CC1=CC2=C(C=O)C=CC=C2N1S(=O)(=O)C1=CC=CC=C1 ZTEGRDKDWRRHET-UHFFFAOYSA-N 0.000 description 1
• KHHCXCUCNHPEDE-UHFFFAOYSA-N 1-(benzenesulfonyl)-2-methylindole-4-carbaldehyde tert-butyl 4-[[1-(benzenesulfonyl)-2-methylindol-4-yl]methyl]piperazine-1-carboxylate Chemical compound CC=1N(C=2C=CC=C(C2C1)C=O)S(=O)(=O)C1=CC=CC=C1.CC=1N(C2=CC=CC(=C2C1)CN1CCN(CC1)C(=O)OC(C)(C)C)S(=O)(=O)C1=CC=CC=C1 KHHCXCUCNHPEDE-UHFFFAOYSA-N 0.000 description 1
• NTKHKTXPVFGWEY-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-methyl-4-(pyrrolidin-1-ylmethyl)indole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=12C(C)=CN(S(=O)(=O)C=3C=CC=CC=3)C2=CC=CC=1CN1CCCC1 NTKHKTXPVFGWEY-UHFFFAOYSA-N 0.000 description 1
• OAAOIRQWDAYTNL-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-methylindole-4-carbaldehyde Chemical compound C12=CC=CC(C=O)=C2C(C)=CN1S(=O)(=O)C1=CC=CC=C1 OAAOIRQWDAYTNL-UHFFFAOYSA-N 0.000 description 1
• RAJPFGLCRZDDCP-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-(1,4-diazepan-1-ylmethyl)-6-fluoroindole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C=12C=CN(S(=O)(=O)C=3C=CC=CC=3)C2=CC(F)=CC=1CN1CCCNCC1 RAJPFGLCRZDDCP-UHFFFAOYSA-N 0.000 description 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 description 1
• CRRVMNLUECQEBS-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-[(1-methylpyrrolidin-3-yl)oxymethyl]indole Chemical compound C1N(C)CCC1OCC1=CC=CC2=C1C=CN2S(=O)(=O)C1=CC=CC=C1 CRRVMNLUECQEBS-UHFFFAOYSA-N 0.000 description 1
• JDJJXWXQTZIZJY-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-[(1-methylpyrrolidin-3-yl)oxymethyl]indole;1-methylpyrrolidin-3-ol;2,2,2-trifluoroacetic acid Chemical compound CN1CCC(O)C1.OC(=O)C(F)(F)F.C1N(C)CCC1OCC1=CC=CC2=C1C=CN2S(=O)(=O)C1=CC=CC=C1 JDJJXWXQTZIZJY-UHFFFAOYSA-N 0.000 description 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 description 1
• JESZNCPVYDPJOR-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-[[4-(2-methoxyethyl)piperazin-1-yl]methyl]indole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C1CN(CCOC)CCN1CC1=CC=CC2=C1C=CN2S(=O)(=O)C1=CC=CC=C1 JESZNCPVYDPJOR-UHFFFAOYSA-N 0.000 description 1
• RHRUVKJRQPCJPX-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-bromo-5-phenylmethoxyindole Chemical compound C1=CC=2N(S(=O)(=O)C=3C=CC=CC=3)C=CC=2C(Br)=C1OCC1=CC=CC=C1 RHRUVKJRQPCJPX-UHFFFAOYSA-N 0.000 description 1
• IFYOPGJYFADOJJ-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-ethenyl-2-methylindole Chemical compound CC1=CC2=C(C=C)C=CC=C2N1S(=O)(=O)C1=CC=CC=C1 IFYOPGJYFADOJJ-UHFFFAOYSA-N 0.000 description 1
• XTZLGFKSRIQFEN-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-ethenyl-6-fluoroindole Chemical compound C12=CC(F)=CC(C=C)=C2C=CN1S(=O)(=O)C1=CC=CC=C1 XTZLGFKSRIQFEN-UHFFFAOYSA-N 0.000 description 1
• UKQRLQVJPVZGFI-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-ethenyl-6-fluoroindole tributyl(ethenyl)stannane Chemical compound C(CCC)[Sn](C=C)(CCCC)CCCC.FC1=CC(=C2C=CN(C2=C1)S(=O)(=O)C1=CC=CC=C1)C=C UKQRLQVJPVZGFI-UHFFFAOYSA-N 0.000 description 1
• MJARVIUDGOXMQC-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-ethenyl-6-methoxyindole 1-(benzenesulfonyl)-6-methoxyindole-4-carbaldehyde Chemical compound COC1=CC(=C2C=CN(C2=C1)S(=O)(=O)C1=CC=CC=C1)C=C.COC=1C=C(C=2C=CN(C2C1)S(=O)(=O)C1=CC=CC=C1)C=O MJARVIUDGOXMQC-UHFFFAOYSA-N 0.000 description 1
• QCHXZGHIIAGFTK-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-ethenyl-7-methoxyindole Chemical compound C1=2C(OC)=CC=C(C=C)C=2C=CN1S(=O)(=O)C1=CC=CC=C1 QCHXZGHIIAGFTK-UHFFFAOYSA-N 0.000 description 1
• ZZKLAWLCURLLBX-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-methylindole Chemical compound C1=CC=2C(C)=CC=CC=2N1S(=O)(=O)C1=CC=CC=C1 ZZKLAWLCURLLBX-UHFFFAOYSA-N 0.000 description 1
• LXYUECSIOIJKCK-UHFFFAOYSA-N 1-(benzenesulfonyl)-5-ethoxy-4-(piperazin-1-ylmethyl)indole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC1=CC=C2N(S(=O)(=O)C=3C=CC=CC=3)C=CC2=C1CN1CCNCC1 LXYUECSIOIJKCK-UHFFFAOYSA-N 0.000 description 1
• LXGLCSJDPJSVHD-UHFFFAOYSA-N 1-(benzenesulfonyl)-5-methoxy-4-(piperazin-1-ylmethyl)indole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.COC1=CC=C2N(S(=O)(=O)C=3C=CC=CC=3)C=CC2=C1CN1CCNCC1 LXGLCSJDPJSVHD-UHFFFAOYSA-N 0.000 description 1
• CJUUOTIWAASJHB-UHFFFAOYSA-N 1-(benzenesulfonyl)-5-methoxyindole-4-carbaldehyde Chemical compound C1=CC2=C(C=O)C(OC)=CC=C2N1S(=O)(=O)C1=CC=CC=C1 CJUUOTIWAASJHB-UHFFFAOYSA-N 0.000 description 1
• INELEEVRBOABGB-UHFFFAOYSA-N 1-(benzenesulfonyl)-5-methoxyindole-4-carbaldehyde tert-butyl 4-[[1-(benzenesulfonyl)-5-methoxyindol-4-yl]methyl]piperazine-1-carboxylate Chemical compound COC1=C(C=2C=CN(C2C=C1)S(=O)(=O)C1=CC=CC=C1)C=O.COC=1C(=C2C=CN(C2=CC1)S(=O)(=O)C1=CC=CC=C1)CN1CCN(CC1)C(=O)OC(C)(C)C INELEEVRBOABGB-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• JLSYIEKUHAJXKE-UHFFFAOYSA-N 1-(benzenesulfonyl)-5-phenylmethoxyindole Chemical compound C1=CC2=CC(OCC=3C=CC=CC=3)=CC=C2N1S(=O)(=O)C1=CC=CC=C1 JLSYIEKUHAJXKE-UHFFFAOYSA-N 0.000 description 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 description 1
• XILDQUHIQYTBNG-UHFFFAOYSA-N 1-(benzenesulfonyl)-6-fluoro-4-(methylaminomethyl)indol-5-ol;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC=2C(CNC)=C(O)C(F)=CC=2N1S(=O)(=O)C1=CC=CC=C1 XILDQUHIQYTBNG-UHFFFAOYSA-N 0.000 description 1
• ZCACTFMXPXUIJQ-UHFFFAOYSA-N 1-(benzenesulfonyl)-6-fluoro-4-(pyrrolidin-1-ylmethyl)indole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=12C=CN(S(=O)(=O)C=3C=CC=CC=3)C2=CC(F)=CC=1CN1CCCC1 ZCACTFMXPXUIJQ-UHFFFAOYSA-N 0.000 description 1
• AYAKEQQUXVYDIJ-UHFFFAOYSA-N 1-(benzenesulfonyl)-6-fluoro-4-[(4-methylpiperazin-1-yl)methyl]indole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C1CN(C)CCN1CC1=CC(F)=CC2=C1C=CN2S(=O)(=O)C1=CC=CC=C1 AYAKEQQUXVYDIJ-UHFFFAOYSA-N 0.000 description 1
• NTKWAKJJNRHQDB-UHFFFAOYSA-N 1-(benzenesulfonyl)-6-fluoro-4-[1-(methylamino)ethyl]indol-5-ol;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC=2C(C(C)NC)=C(O)C(F)=CC=2N1S(=O)(=O)C1=CC=CC=C1 NTKWAKJJNRHQDB-UHFFFAOYSA-N 0.000 description 1
• ZWDCTELOBCONES-QCUBGVIVSA-N 1-(benzenesulfonyl)-6-fluoro-4-[[(3r)-3-methylpiperazin-1-yl]methyl]indole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C1CN[C@H](C)CN1CC1=CC(F)=CC2=C1C=CN2S(=O)(=O)C1=CC=CC=C1 ZWDCTELOBCONES-QCUBGVIVSA-N 0.000 description 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 description 1
• FYWPIARACSEAJF-UHFFFAOYSA-N 1-(benzenesulfonyl)-6-fluoro-5-methoxy-4-(pyrrolidin-1-ylmethyl)indole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=C(F)C=C2N(S(=O)(=O)C=3C=CC=CC=3)C=CC2=C1CN1CCCC1 FYWPIARACSEAJF-UHFFFAOYSA-N 0.000 description 1
• OXYHPQBHDCKQAD-UHFFFAOYSA-N 1-(benzenesulfonyl)-6-fluoroindole-4-carbaldehyde Chemical compound C12=CC(F)=CC(C=O)=C2C=CN1S(=O)(=O)C1=CC=CC=C1 OXYHPQBHDCKQAD-UHFFFAOYSA-N 0.000 description 1
• FITNSVIPZHTMJF-UHFFFAOYSA-N 1-(benzenesulfonyl)-6-methoxy-4-(pyrrolidin-1-ylmethyl)indole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=12C=CN(S(=O)(=O)C=3C=CC=CC=3)C2=CC(OC)=CC=1CN1CCCC1 FITNSVIPZHTMJF-UHFFFAOYSA-N 0.000 description 1
• WIYDKHRDFRLJPP-UHFFFAOYSA-N 1-(benzenesulfonyl)-6-methoxy-4-[(4-methylpiperazin-1-yl)methyl]indole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C=12C=CN(S(=O)(=O)C=3C=CC=CC=3)C2=CC(OC)=CC=1CN1CCN(C)CC1 WIYDKHRDFRLJPP-UHFFFAOYSA-N 0.000 description 1
• LQUMCKZRKVIFIE-GGMCWBHBSA-N 1-(benzenesulfonyl)-6-methoxy-4-[[(3r)-3-methylpiperazin-1-yl]methyl]indole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C=12C=CN(S(=O)(=O)C=3C=CC=CC=3)C2=CC(OC)=CC=1CN1CCN[C@H](C)C1 LQUMCKZRKVIFIE-GGMCWBHBSA-N 0.000 description 1
• 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 description 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 description 1
• JUOFCAJDGWYKFU-UHFFFAOYSA-N 1-(benzenesulfonyl)-7-methoxy-4-(piperazin-1-ylmethyl)indole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C1=2C=CN(S(=O)(=O)C=3C=CC=CC=3)C=2C(OC)=CC=C1CN1CCNCC1 JUOFCAJDGWYKFU-UHFFFAOYSA-N 0.000 description 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 description 1
• WZZKPAGERZJVMV-UHFFFAOYSA-N 1-(benzenesulfonyl)indol-5-ol Chemical compound C1=CC2=CC(O)=CC=C2N1S(=O)(=O)C1=CC=CC=C1 WZZKPAGERZJVMV-UHFFFAOYSA-N 0.000 description 1
• QIWDUGKJAHJRAE-UHFFFAOYSA-N 1-(benzenesulfonyl)indole-2-carboxylic acid Chemical compound OC(=O)C1=CC2=CC=CC=C2N1S(=O)(=O)C1=CC=CC=C1 QIWDUGKJAHJRAE-UHFFFAOYSA-N 0.000 description 1
• CISRHMUOOJKICE-UHFFFAOYSA-N 1-(fluoromethyl)-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1CF CISRHMUOOJKICE-UHFFFAOYSA-N 0.000 description 1
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
• ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 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 description 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 description 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 description 1
• 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 description 1
• PJUOWVPQCKCZNJ-UHFFFAOYSA-N 1-[1-(benzenesulfonyl)-3-chloro-5-methoxyindol-4-yl]-n-methylmethanamine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(Cl)C=2C(CNC)=C(OC)C=CC=2N1S(=O)(=O)C1=CC=CC=C1 PJUOWVPQCKCZNJ-UHFFFAOYSA-N 0.000 description 1
• PGWGGJDLKVNGHL-UHFFFAOYSA-N 1-[1-(benzenesulfonyl)-5-ethoxyindol-4-yl]-n,n-dimethylmethanamine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC2=C(CN(C)C)C(OCC)=CC=C2N1S(=O)(=O)C1=CC=CC=C1 PGWGGJDLKVNGHL-UHFFFAOYSA-N 0.000 description 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 description 1
• WFRLAYOWOAOLLB-UHFFFAOYSA-N 1-[1-(benzenesulfonyl)-5-methoxyindol-4-yl]-n-methylmethanamine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC=2C(CNC)=C(OC)C=CC=2N1S(=O)(=O)C1=CC=CC=C1 WFRLAYOWOAOLLB-UHFFFAOYSA-N 0.000 description 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 description 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 description 1
• RJHYHLZVUYGAGO-UHFFFAOYSA-N 1-[1-(benzenesulfonyl)-6-fluoro-5-methoxyindol-4-yl]-n-methylmethanamine Chemical compound C1=CC=2C(CNC)=C(OC)C(F)=CC=2N1S(=O)(=O)C1=CC=CC=C1 RJHYHLZVUYGAGO-UHFFFAOYSA-N 0.000 description 1
• WAXMALYMQVVOLB-UHFFFAOYSA-N 1-[1-(benzenesulfonyl)-6-fluoro-5-methoxyindol-4-yl]-n-methylmethanamine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC=2C(CNC)=C(OC)C(F)=CC=2N1S(=O)(=O)C1=CC=CC=C1 WAXMALYMQVVOLB-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• ZCBOAFAOFBCKBR-UHFFFAOYSA-N 1-[1-(benzenesulfonyl)-6-fluoroindol-4-yl]-n,n-dimethylmethanamine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC=2C(CN(C)C)=CC(F)=CC=2N1S(=O)(=O)C1=CC=CC=C1 ZCBOAFAOFBCKBR-UHFFFAOYSA-N 0.000 description 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 description 1
• RECXMZBFQPOBNT-UHFFFAOYSA-N 1-[1-(benzenesulfonyl)-6-methoxyindol-4-yl]-n,n-dimethylmethanamine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=CC(OC)=CC(CN(C)C)=C2C=CN1S(=O)(=O)C1=CC=CC=C1 RECXMZBFQPOBNT-UHFFFAOYSA-N 0.000 description 1
• AMGDAQDROVVUOA-UHFFFAOYSA-N 1-[5-methoxy-1-[3-(trifluoromethyl)phenyl]sulfonylindol-4-yl]-n,n-dimethylmethanamine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC2=C(CN(C)C)C(OC)=CC=C2N1S(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 AMGDAQDROVVUOA-UHFFFAOYSA-N 0.000 description 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 description 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 description 1
• PWPGHGCTQNUWCL-UHFFFAOYSA-N 1-[[1-(benzenesulfonyl)indol-4-yl]methyl]azetidin-3-ol;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1C(O)CN1CC1=CC=CC2=C1C=CN2S(=O)(=O)C1=CC=CC=C1 PWPGHGCTQNUWCL-UHFFFAOYSA-N 0.000 description 1
• CXJDVHUNRZRAMS-UHFFFAOYSA-N 1-bromo-2-methyl-3-nitro-4-phenylmethoxybenzene Chemical compound CC1=C(Br)C=CC(OCC=2C=CC=CC=2)=C1[N+]([O-])=O CXJDVHUNRZRAMS-UHFFFAOYSA-N 0.000 description 1
• WDWRWXGEYFSQIJ-UHFFFAOYSA-N 1-bromo-4-methoxy-2-methyl-3-nitrobenzene 4-bromo-3-methyl-2-nitrophenol Chemical compound BrC1=C(C(=C(C=C1)O)[N+](=O)[O-])C.COC1=C(C(=C(C=C1)Br)C)[N+](=O)[O-] WDWRWXGEYFSQIJ-UHFFFAOYSA-N 0.000 description 1
• 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
• 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
• NPHKOAHNJIKDMM-UHFFFAOYSA-N 1-fluoro-4-methyl-5-nitro-2-phenylmethoxybenzene Chemical compound C1=C([N+]([O-])=O)C(C)=CC(OCC=2C=CC=CC=2)=C1F NPHKOAHNJIKDMM-UHFFFAOYSA-N 0.000 description 1
• 125000006039 1-hexenyl group Chemical group 0.000 description 1
• FXHRAKUEZPSMLJ-UHFFFAOYSA-N 1-methyl-1,4-diazepane Chemical compound CN1CCCNCC1 FXHRAKUEZPSMLJ-UHFFFAOYSA-N 0.000 description 1
• QGJBBIDVUIZEPJ-UHFFFAOYSA-N 1-o-tert-butyl 2-o-methyl 4-[[1-(benzenesulfonyl)indol-4-yl]methyl]piperazine-1,2-dicarboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)C(C(=O)OC)CN1CC1=CC=CC2=C1C=CN2S(=O)(=O)C1=CC=CC=C1 QGJBBIDVUIZEPJ-UHFFFAOYSA-N 0.000 description 1
• 125000006023 1-pentenyl group Chemical group 0.000 description 1
• WHKWMTXTYKVFLK-UHFFFAOYSA-N 1-propan-2-ylpiperazine Chemical compound CC(C)N1CCNCC1 WHKWMTXTYKVFLK-UHFFFAOYSA-N 0.000 description 1
• ZRQQXFMGYSOKDF-UHFFFAOYSA-N 1-propan-2-ylpiperidin-4-amine Chemical compound CC(C)N1CCC(N)CC1 ZRQQXFMGYSOKDF-UHFFFAOYSA-N 0.000 description 1
• 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
• JJXKNQDHUIMYAS-UHFFFAOYSA-N 1-pyridin-3-ylsulfonyl-4-(pyrrolidin-1-ylmethyl)indole Chemical compound C1=CC2=C(CN3CCCC3)C=CC=C2N1S(=O)(=O)C1=CC=CN=C1 JJXKNQDHUIMYAS-UHFFFAOYSA-N 0.000 description 1
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
• HCUARRIEZVDMPT-UHFFFAOYSA-M 1h-indole-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)[O-])=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-M 0.000 description 1
• BEUJAVGQOANFRI-UHFFFAOYSA-N 1h-indole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC=C2NC=CC2=C1 BEUJAVGQOANFRI-UHFFFAOYSA-N 0.000 description 1
• DZDYYBURGWYOAN-UNTBIKODSA-N 2,2,2-trifluoroacetic acid;[(2r)-1-[[1-[3-(trifluoromethyl)phenyl]sulfonylindol-4-yl]methyl]pyrrolidin-2-yl]methanol Chemical compound OC(=O)C(F)(F)F.OC[C@H]1CCCN1CC1=CC=CC2=C1C=CN2S(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 DZDYYBURGWYOAN-UNTBIKODSA-N 0.000 description 1
• 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
• PQODWTNHDKDHIW-UHFFFAOYSA-N 2,3-dichlorobenzenesulfonyl chloride Chemical compound ClC1=CC=CC(S(Cl)(=O)=O)=C1Cl PQODWTNHDKDHIW-UHFFFAOYSA-N 0.000 description 1
• WHJAQKAAIOHCGN-UHFFFAOYSA-N 2,4,6-trichlorobenzenesulfonyl chloride Chemical compound ClC1=CC(Cl)=C(S(Cl)(=O)=O)C(Cl)=C1 WHJAQKAAIOHCGN-UHFFFAOYSA-N 0.000 description 1
• GPWNWKWQOLEVEQ-UHFFFAOYSA-N 2,4-diaminopyrimidine-5-carbaldehyde Chemical compound NC1=NC=C(C=O)C(N)=N1 GPWNWKWQOLEVEQ-UHFFFAOYSA-N 0.000 description 1
• BXCOSWRSIISQSL-UHFFFAOYSA-N 2,5-dichlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(Cl)C(S(Cl)(=O)=O)=C1 BXCOSWRSIISQSL-UHFFFAOYSA-N 0.000 description 1
• CELLJWUVMKEJDY-UHFFFAOYSA-N 2,5-difluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(F)C(S(Cl)(=O)=O)=C1 CELLJWUVMKEJDY-UHFFFAOYSA-N 0.000 description 1
• QXWAUQMMMIMLTO-UHFFFAOYSA-N 2,6-difluorobenzenesulfonyl chloride Chemical compound FC1=CC=CC(F)=C1S(Cl)(=O)=O QXWAUQMMMIMLTO-UHFFFAOYSA-N 0.000 description 1
• BZOHHLMTCXVRJE-UHFFFAOYSA-N 2-(hydroxymethyl)-1,3-dihydroinden-2-ol Chemical compound C1=CC=C2CC(CO)(O)CC2=C1 BZOHHLMTCXVRJE-UHFFFAOYSA-N 0.000 description 1
• ZIZGWNOAHUCACM-UHFFFAOYSA-N 2-(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC(F)(F)C1=CC=CC=C1S(Cl)(=O)=O ZIZGWNOAHUCACM-UHFFFAOYSA-N 0.000 description 1
• LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
• JKGNHXYZSCQLCL-UHFFFAOYSA-N 2-[(2-thiophen-2-yl-1h-indol-3-yl)sulfanyl]acetic acid Chemical compound N1C2=CC=CC=C2C(SCC(=O)O)=C1C1=CC=CS1 JKGNHXYZSCQLCL-UHFFFAOYSA-N 0.000 description 1
• CDPJOMGTJLAJHI-UHFFFAOYSA-N 2-[1-(benzenesulfonyl)-7-methoxyindol-4-yl]-2-piperazin-1-ylacetonitrile;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=2C=CN(S(=O)(=O)C=3C=CC=CC=3)C=2C(OC)=CC=C1C(C#N)N1CCNCC1 CDPJOMGTJLAJHI-UHFFFAOYSA-N 0.000 description 1
• ZNJRONVKWRHYBF-UHFFFAOYSA-N 2-[2-[2-(1-azatricyclo[7.3.1.05,13]trideca-5,7,9(13)-trien-7-yl)ethenyl]-6-methylpyran-4-ylidene]propanedinitrile Chemical compound O1C(C)=CC(=C(C#N)C#N)C=C1C=CC1=CC(CCCN2CCC3)=C2C3=C1 ZNJRONVKWRHYBF-UHFFFAOYSA-N 0.000 description 1
• KBFUNEVMZYTPCT-UHFFFAOYSA-N 2-[6-methoxy-4-(piperazin-1-ylmethyl)indol-1-yl]sulfonylbenzonitrile;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C=12C=CN(S(=O)(=O)C=3C(=CC=CC=3)C#N)C2=CC(OC)=CC=1CN1CCNCC1 KBFUNEVMZYTPCT-UHFFFAOYSA-N 0.000 description 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 description 1
• OEOYZOPECMYHPI-UHFFFAOYSA-N 2-[[1-(benzenesulfonyl)-6-fluoroindol-4-yl]methyl-methylamino]ethanol;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC=2C(CN(CCO)C)=CC(F)=CC=2N1S(=O)(=O)C1=CC=CC=C1 OEOYZOPECMYHPI-UHFFFAOYSA-N 0.000 description 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 description 1
• HBLBQENMLCOPSC-UHFFFAOYSA-N 2-[[1-(benzenesulfonyl)-6-methoxyindol-4-yl]methyl-methylamino]ethanol;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=CC(OC)=CC(CN(C)CCO)=C2C=CN1S(=O)(=O)C1=CC=CC=C1 HBLBQENMLCOPSC-UHFFFAOYSA-N 0.000 description 1
• PNYYLMAGFFELEI-UHFFFAOYSA-N 2-[methyl-[[1-(2-methylphenyl)sulfonylindol-4-yl]methyl]amino]ethanol;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC=2C(CN(CCO)C)=CC=CC=2N1S(=O)(=O)C1=CC=CC=C1C PNYYLMAGFFELEI-UHFFFAOYSA-N 0.000 description 1
• REXUYBKPWIPONM-UHFFFAOYSA-N 2-bromoacetonitrile Chemical compound BrCC#N REXUYBKPWIPONM-UHFFFAOYSA-N 0.000 description 1
• 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
• GELVZYOEQVJIRR-UHFFFAOYSA-N 2-chloropyrazine Chemical compound ClC1=CN=CC=N1 GELVZYOEQVJIRR-UHFFFAOYSA-N 0.000 description 1
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
• ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
• HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
• RGHPCLZJAFCTIK-UHFFFAOYSA-N 2-methylpyrrolidine Chemical compound CC1CCCN1 RGHPCLZJAFCTIK-UHFFFAOYSA-N 0.000 description 1
• XHOHVIKZCDXJNK-UHFFFAOYSA-N 2-piperazin-1-ylacetonitrile Chemical compound N#CCN1CCNCC1 XHOHVIKZCDXJNK-UHFFFAOYSA-N 0.000 description 1
• JAASEHNFKZEABY-UHFFFAOYSA-N 2-piperazin-1-ylacetonitrile;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N#CCN1CCNCC1 JAASEHNFKZEABY-UHFFFAOYSA-N 0.000 description 1
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
• HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
• BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
• WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
• HHMSZUJBSONLHI-UHFFFAOYSA-N 3-[4-(azetidin-1-ylmethyl)indol-1-yl]sulfonylbenzonitrile;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC2=C(CN3CCC3)C=CC=C2N1S(=O)(=O)C1=CC=CC(C#N)=C1 HHMSZUJBSONLHI-UHFFFAOYSA-N 0.000 description 1
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 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 description 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 description 1
• 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 description 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 description 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 description 1
• MFCGHPFRWHZOAG-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-(benzenesulfonyl)-2-methylindole 1-(benzenesulfonyl)-2-methylindole-4-carbaldehyde 2,2,2-trifluoroacetic acid Chemical compound CC=1N(C=2C=CC=C(C2C1)C=O)S(=O)(=O)C1=CC=CC=C1.FC(C(=O)O)(F)F.N1(CCC1)CC1=C2C=C(N(C2=CC=C1)S(=O)(=O)C1=CC=CC=C1)C MFCGHPFRWHZOAG-UHFFFAOYSA-N 0.000 description 1
• GZSRJAUQECDTDX-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-(benzenesulfonyl)-2-methylindole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC=C2N(S(=O)(=O)C=3C=CC=CC=3)C(C)=CC2=C1CN1CCC1 GZSRJAUQECDTDX-UHFFFAOYSA-N 0.000 description 1
• NANWTYCATFTKJS-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-(benzenesulfonyl)-5-methoxyindole;1-(benzenesulfonyl)-5-methoxyindole-4-carbaldehyde;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC2=C(C=O)C(OC)=CC=C2N1S(=O)(=O)C1=CC=CC=C1.COC1=CC=C2N(S(=O)(=O)C=3C=CC=CC=3)C=CC2=C1CN1CCC1 NANWTYCATFTKJS-UHFFFAOYSA-N 0.000 description 1
• LWSIBOQDVXISQQ-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-(benzenesulfonyl)-5-methoxyindole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=C2N(S(=O)(=O)C=3C=CC=CC=3)C=CC2=C1CN1CCC1 LWSIBOQDVXISQQ-UHFFFAOYSA-N 0.000 description 1
• VRLDFUZIOXYKEH-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-(benzenesulfonyl)-6-fluoro-5-methoxyindole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=C(F)C=C2N(S(=O)(=O)C=3C=CC=CC=3)C=CC2=C1CN1CCC1 VRLDFUZIOXYKEH-UHFFFAOYSA-N 0.000 description 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 description 1
• AZBDQZSYQGVBQD-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-(benzenesulfonyl)-6-methoxyindole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=12C=CN(S(=O)(=O)C=3C=CC=CC=3)C2=CC(OC)=CC=1CN1CCC1 AZBDQZSYQGVBQD-UHFFFAOYSA-N 0.000 description 1
• RJUNJHRFUUSTCE-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-(benzenesulfonyl)indole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC2=C(CN3CCC3)C=CC=C2N1S(=O)(=O)C1=CC=CC=C1 RJUNJHRFUUSTCE-UHFFFAOYSA-N 0.000 description 1
• DVHMOGCWNDYMQU-UHFFFAOYSA-N 4-(azetidin-1-ylmethyl)-1-[4-bromo-2-(trifluoromethyl)phenyl]sulfonylindole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC(F)(F)C1=CC(Br)=CC=C1S(=O)(=O)N1C2=CC=CC(CN3CCC3)=C2C=C1 DVHMOGCWNDYMQU-UHFFFAOYSA-N 0.000 description 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 description 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 description 1
• IQHOKJFWALRJBB-UHFFFAOYSA-N 4-(piperazin-1-ylmethyl)-1-[3-(trifluoromethyl)phenyl]sulfonylindole Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)N2C3=CC=CC(CN4CCNCC4)=C3C=C2)=C1 IQHOKJFWALRJBB-UHFFFAOYSA-N 0.000 description 1
• ACSWDUCDKPSVKF-UHFFFAOYSA-N 4-(piperazin-1-ylmethyl)-1-pyridin-3-ylsulfonylindole 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C1=CC2=C(CN3CCNCC3)C=CC=C2N1S(=O)(=O)C1=CC=CN=C1 ACSWDUCDKPSVKF-UHFFFAOYSA-N 0.000 description 1
• VQCPQIPICXUWNF-UHFFFAOYSA-N 4-(piperazin-1-ylmethyl)-1-thiophen-2-ylsulfonylindole 1-thiophen-2-ylsulfonylindole-4-carbaldehyde 2,2,2-trifluoroacetic acid Chemical compound S1C(=CC=C1)S(=O)(=O)N1C=CC=2C(=CC=CC12)C=O.FC(C(=O)O)(F)F.FC(C(=O)O)(F)F.N1(CCNCC1)CC1=C2C=CN(C2=CC=C1)S(=O)(=O)C=1SC=CC1 VQCPQIPICXUWNF-UHFFFAOYSA-N 0.000 description 1
• NPQSETAGDQRHHL-UHFFFAOYSA-N 4-(pyrrolidin-1-ylmethyl)-1-[3-(trifluoromethyl)phenyl]sulfonylindole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC(F)(F)C1=CC=CC(S(=O)(=O)N2C3=CC=CC(CN4CCCC4)=C3C=C2)=C1 NPQSETAGDQRHHL-UHFFFAOYSA-N 0.000 description 1
• KXVUWPZAPVCCAQ-UHFFFAOYSA-N 4-[4-(azetidin-1-ylmethyl)indol-1-yl]sulfonylbenzonitrile;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC2=C(CN3CCC3)C=CC=C2N1S(=O)(=O)C1=CC=C(C#N)C=C1 KXVUWPZAPVCCAQ-UHFFFAOYSA-N 0.000 description 1
• QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
• KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
• WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
• ZQHMZEIDOGXHBN-UHFFFAOYSA-N 4-bromo-1-(2-methylphenyl)sulfonylindole 4-ethenyl-1-(2-methylphenyl)sulfonylindole Chemical compound BrC1=C2C=CN(C2=CC=C1)S(=O)(=O)C1=C(C=CC=C1)C.CC1=C(C=CC=C1)S(=O)(=O)N1C=CC2=C(C=CC=C12)C=C ZQHMZEIDOGXHBN-UHFFFAOYSA-N 0.000 description 1
• LLWDHSQCZPPQDY-UHFFFAOYSA-N 4-bromo-1-(4-methylphenyl)sulfonylindole Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=CC=CC(Br)=C2C=C1 LLWDHSQCZPPQDY-UHFFFAOYSA-N 0.000 description 1
• AIKSDGSRIAFVIG-UHFFFAOYSA-N 4-bromo-1H-indole 4-bromo-1-(4-methylphenyl)sulfonylindole Chemical compound BrC1=C2C=CNC2=CC=C1.BrC1=C2C=CN(C2=CC=C1)S(=O)(=O)C1=CC=C(C=C1)C AIKSDGSRIAFVIG-UHFFFAOYSA-N 0.000 description 1
• ACTCZAFYFKSGMW-UHFFFAOYSA-N 4-bromo-1h-indole;4-pyrazin-2-yl-1h-indole Chemical compound BrC1=CC=CC2=C1C=CN2.C1=CC=C2NC=CC2=C1C1=CN=CC=N1 ACTCZAFYFKSGMW-UHFFFAOYSA-N 0.000 description 1
• YFXYEMZYOMNQLD-UHFFFAOYSA-N 4-bromo-2-(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC(F)(F)C1=CC(Br)=CC=C1S(Cl)(=O)=O YFXYEMZYOMNQLD-UHFFFAOYSA-N 0.000 description 1
• HXNNJFUSAYWUFT-UHFFFAOYSA-N 4-bromo-3-methyl-2-nitrophenol Chemical compound CC1=C(Br)C=CC(O)=C1[N+]([O-])=O HXNNJFUSAYWUFT-UHFFFAOYSA-N 0.000 description 1
• LAXGAOAUMANSIN-UHFFFAOYSA-N 4-bromo-5-methoxy-1H-indole 2-bromo-3-methyl-4-nitrophenol Chemical compound BrC1=C(C=CC(=C1C)[N+](=O)[O-])O.BrC1=C2C=CNC2=CC=C1OC LAXGAOAUMANSIN-UHFFFAOYSA-N 0.000 description 1
• FPSVUEYKYLKRJL-UHFFFAOYSA-N 4-bromo-5-methoxy-1h-indole Chemical compound COC1=CC=C2NC=CC2=C1Br FPSVUEYKYLKRJL-UHFFFAOYSA-N 0.000 description 1
• CZJYKEPYJHPVOD-UHFFFAOYSA-N 4-bromo-6-methoxy-1h-indole Chemical compound COC1=CC(Br)=C2C=CNC2=C1 CZJYKEPYJHPVOD-UHFFFAOYSA-N 0.000 description 1
• HWDMSYHNPIYTJF-UHFFFAOYSA-N 4-bromo-7-phenylmethoxy-1h-indole Chemical compound C1=2NC=CC=2C(Br)=CC=C1OCC1=CC=CC=C1 HWDMSYHNPIYTJF-UHFFFAOYSA-N 0.000 description 1
• DBMFYTQPPBBKHI-UHFFFAOYSA-N 4-cyanobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(C#N)C=C1 DBMFYTQPPBBKHI-UHFFFAOYSA-N 0.000 description 1
• XDIUZLDVJUCFIE-UHFFFAOYSA-N 4-ethenyl-1-methylsulfonyl-7-phenylmethoxyindole Chemical compound C=12N(S(=O)(=O)C)C=CC2=C(C=C)C=CC=1OCC1=CC=CC=C1 XDIUZLDVJUCFIE-UHFFFAOYSA-N 0.000 description 1
• OEONKPQNWNPWNX-UHFFFAOYSA-N 4-ethenyl-1-pyridin-3-ylsulfonylindole Chemical compound C1=CC=2C(C=C)=CC=CC=2N1S(=O)(=O)C1=CC=CN=C1 OEONKPQNWNPWNX-UHFFFAOYSA-N 0.000 description 1
• IDNCPSOIKXCZNR-UHFFFAOYSA-N 4-ethenyl-1h-indole Chemical compound C=CC1=CC=CC2=C1C=CN2 IDNCPSOIKXCZNR-UHFFFAOYSA-N 0.000 description 1
• DQAZPZIYEOGZAF-UHFFFAOYSA-N 4-ethyl-n-[4-(3-ethynylanilino)-7-methoxyquinazolin-6-yl]piperazine-1-carboxamide Chemical compound C1CN(CC)CCN1C(=O)NC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=CC(C#C)=C1 DQAZPZIYEOGZAF-UHFFFAOYSA-N 0.000 description 1
• AYOKQWBPSUHEQU-UHFFFAOYSA-N 4-fluoro-3-(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC1=CC=C(S(Cl)(=O)=O)C=C1C(F)(F)F AYOKQWBPSUHEQU-UHFFFAOYSA-N 0.000 description 1
• BFXHJFKKRGVUMU-UHFFFAOYSA-N 4-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(S(Cl)(=O)=O)C=C1 BFXHJFKKRGVUMU-UHFFFAOYSA-N 0.000 description 1
• DTJVECUKADWGMO-UHFFFAOYSA-N 4-methoxybenzenesulfonyl chloride Chemical compound COC1=CC=C(S(Cl)(=O)=O)C=C1 DTJVECUKADWGMO-UHFFFAOYSA-N 0.000 description 1
• PIIZYNQECPTVEO-UHFFFAOYSA-N 4-nitro-m-cresol Chemical compound CC1=CC(O)=CC=C1[N+]([O-])=O PIIZYNQECPTVEO-UHFFFAOYSA-N 0.000 description 1
• OKTNKFJTSMJNNX-UHFFFAOYSA-N 4-pyrazin-2-yl-1h-indole Chemical compound C1=CC=C2NC=CC2=C1C1=CN=CC=N1 OKTNKFJTSMJNNX-UHFFFAOYSA-N 0.000 description 1
• YEZADZMMVHWFIY-UHFFFAOYSA-N 4-tert-butylbenzenesulfonyl chloride Chemical compound CC(C)(C)C1=CC=C(S(Cl)(=O)=O)C=C1 YEZADZMMVHWFIY-UHFFFAOYSA-N 0.000 description 1
• 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 description 1
• 229940124801 5-HT6 antagonist Drugs 0.000 description 1
• IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
• NXWQVJPUAQWVJD-UHFFFAOYSA-N 5-[4-(azetidin-1-ylmethyl)indol-1-yl]sulfonyl-6-chloroimidazo[2,1-b][1,3]thiazole Chemical compound ClC=1N=C2SC=CN2C=1S(=O)(=O)N(C1=CC=C2)C=CC1=C2CN1CCC1 NXWQVJPUAQWVJD-UHFFFAOYSA-N 0.000 description 1
• AKSFFWKIMJNMAJ-UHFFFAOYSA-N 5-benzylindol-2-one Chemical compound C1=CC2=NC(=O)C=C2C=C1CC1=CC=CC=C1 AKSFFWKIMJNMAJ-UHFFFAOYSA-N 0.000 description 1
• SORSTNOXGOXWAO-UHFFFAOYSA-N 5-chlorothiophene-2-sulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)S1 SORSTNOXGOXWAO-UHFFFAOYSA-N 0.000 description 1
• KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 1
• AWFDCTXCTHGORH-HGHGUNKESA-N 6-[4-[(6ar,9r,10ar)-5-bromo-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carbonyl]piperazin-1-yl]-1-methylpyridin-2-one Chemical compound O=C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4NC(Br)=C(C=34)C2)C1)C)N(CC1)CCN1C1=CC=CC(=O)N1C AWFDCTXCTHGORH-HGHGUNKESA-N 0.000 description 1
• VTDQUKKDBPQGSA-UHFFFAOYSA-N 6-fluoro-5-phenylmethoxy-1h-indole Chemical compound FC1=CC=2NC=CC=2C=C1OCC1=CC=CC=C1 VTDQUKKDBPQGSA-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• KAIHRXZLRJBGBR-UHFFFAOYSA-N 6-methoxy-4-(piperazin-1-ylmethyl)-1-[3-(trifluoromethyl)phenyl]sulfonylindole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C=12C=CN(S(=O)(=O)C=3C=C(C=CC=3)C(F)(F)F)C2=CC(OC)=CC=1CN1CCNCC1 KAIHRXZLRJBGBR-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
• 241000349731 Afzelia bipindensis Species 0.000 description 1
• 239000005695 Ammonium acetate Substances 0.000 description 1
• 108020000948 Antisense Oligonucleotides Proteins 0.000 description 1
• 239000004475 Arginine Substances 0.000 description 1
• 239000005711 Benzoic acid Substances 0.000 description 1
• 239000004342 Benzoyl peroxide Substances 0.000 description 1
• OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
• 208000031638 Body Weight Diseases 0.000 description 1
• DYNMEBGVYHVPCJ-UHFFFAOYSA-N BrC1=C2C=CN(C2=CC(=C1)OC)S(=O)(=O)C1=CC=CC=C1.COC1=CC(=C2C=CN(C2=C1)S(=O)(=O)C1=CC=CC=C1)C=C Chemical compound BrC1=C2C=CN(C2=CC(=C1)OC)S(=O)(=O)C1=CC=CC=C1.COC1=CC(=C2C=CN(C2=C1)S(=O)(=O)C1=CC=CC=C1)C=C DYNMEBGVYHVPCJ-UHFFFAOYSA-N 0.000 description 1
• SBSRJJRQCLPKSV-UHFFFAOYSA-N BrC1=C2C=CN(C2=CC=C1)S(=O)(=O)C1=CC=CC=C1.C1(=CC=CC=C1)S(=O)(=O)N1C=CC2=C(C=CC=C12)C=C Chemical compound BrC1=C2C=CN(C2=CC=C1)S(=O)(=O)C1=CC=CC=C1.C1(=CC=CC=C1)S(=O)(=O)N1C=CC2=C(C=CC=C12)C=C SBSRJJRQCLPKSV-UHFFFAOYSA-N 0.000 description 1
• PJAZONKRVWVWHF-UHFFFAOYSA-N BrC1=C2C=CNC2=CC(=C1)OC.BrC1=C2C=CN(C2=CC(=C1)OC)S(=O)(=O)C1=CC=CC=C1 Chemical compound BrC1=C2C=CNC2=CC(=C1)OC.BrC1=C2C=CN(C2=CC(=C1)OC)S(=O)(=O)C1=CC=CC=C1 PJAZONKRVWVWHF-UHFFFAOYSA-N 0.000 description 1
• XSDDMAIUKPKBKR-UHFFFAOYSA-N BrCC1=C2C=CN(C2=CC=C1)S(=O)(=O)C1=CC=CC=C1.Cl.N1(CCNCCC1)CC1=C2C=CN(C2=CC=C1)S(=O)(=O)C1=CC=CC=C1 Chemical compound BrCC1=C2C=CN(C2=CC=C1)S(=O)(=O)C1=CC=CC=C1.Cl.N1(CCNCCC1)CC1=C2C=CN(C2=CC=C1)S(=O)(=O)C1=CC=CC=C1 XSDDMAIUKPKBKR-UHFFFAOYSA-N 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
• MYWJZERWCFKVRD-UHFFFAOYSA-N C(CCC)[Sn](C=C)(CCCC)CCCC.CC1=CN(C2=CC=CC(=C12)C=C)S(=O)(=O)C1=CC=CC=C1 Chemical compound C(CCC)[Sn](C=C)(CCCC)CCCC.CC1=CN(C2=CC=CC(=C12)C=C)S(=O)(=O)C1=CC=CC=C1 MYWJZERWCFKVRD-UHFFFAOYSA-N 0.000 description 1
• LKUAWJQDVKISAD-UHFFFAOYSA-N CC1=CN(C=2C=CC=C(C12)C=O)S(=O)(=O)C1=CC=CC=C1.FC(C(=O)O)(F)F.FC(C(=O)O)(F)F Chemical compound CC1=CN(C=2C=CC=C(C12)C=O)S(=O)(=O)C1=CC=CC=C1.FC(C(=O)O)(F)F.FC(C(=O)O)(F)F LKUAWJQDVKISAD-UHFFFAOYSA-N 0.000 description 1
• FNNPWTUMUOWQDF-UHFFFAOYSA-N CC1=CN(C=2C=CC=C(C12)C=O)S(=O)(=O)C1=CC=CC=C1.FC(C(=O)O)(F)F.FC(C(=O)O)(F)F.CC1=CN(C2=CC=CC(=C12)CN1CCNCC1)S(=O)(=O)C1=CC=CC=C1 Chemical compound CC1=CN(C=2C=CC=C(C12)C=O)S(=O)(=O)C1=CC=CC=C1.FC(C(=O)O)(F)F.FC(C(=O)O)(F)F.CC1=CN(C2=CC=CC(=C12)CN1CCNCC1)S(=O)(=O)C1=CC=CC=C1 FNNPWTUMUOWQDF-UHFFFAOYSA-N 0.000 description 1
• QJBWLXLOKMFKFP-UHFFFAOYSA-N COC=1C=C(C=2C=CN(C2C1)S(=O)(=O)C1=CC=CC=C1)C=O.FC(C(=O)O)(F)F.FC(C(=O)O)(F)F Chemical compound COC=1C=C(C=2C=CN(C2C1)S(=O)(=O)C1=CC=CC=C1)C=O.FC(C(=O)O)(F)F.FC(C(=O)O)(F)F QJBWLXLOKMFKFP-UHFFFAOYSA-N 0.000 description 1
• YRVFKZSBQUWQSI-UHFFFAOYSA-N COC=1C=C(C=2C=CN(C2C1)S(=O)(=O)C1=CC=CC=C1)C=O.FC(C(=O)O)(F)F.N1(CCC1)CC1=C2C=CN(C2=CC(=C1)OC)S(=O)(=O)C1=CC=CC=C1 Chemical compound COC=1C=C(C=2C=CN(C2C1)S(=O)(=O)C1=CC=CC=C1)C=O.FC(C(=O)O)(F)F.N1(CCC1)CC1=C2C=CN(C2=CC(=C1)OC)S(=O)(=O)C1=CC=CC=C1 YRVFKZSBQUWQSI-UHFFFAOYSA-N 0.000 description 1
• CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
• 208000024172 Cardiovascular disease Diseases 0.000 description 1
• CTOMCTKRKATFPF-UHFFFAOYSA-N Cl.N1CC(C1)O.FC(C(=O)O)(F)F Chemical compound Cl.N1CC(C1)O.FC(C(=O)O)(F)F CTOMCTKRKATFPF-UHFFFAOYSA-N 0.000 description 1
• SGUZDFVXVKYYSP-UHFFFAOYSA-N Cl.N1CCC1.FC(C(=O)O)(F)F.N1(CCC1)CC1=C2C=CN(C2=C(C=C1)OCC1=CC=CC=C1)S(=O)(=O)C Chemical compound Cl.N1CCC1.FC(C(=O)O)(F)F.N1(CCC1)CC1=C2C=CN(C2=C(C=C1)OCC1=CC=CC=C1)S(=O)(=O)C SGUZDFVXVKYYSP-UHFFFAOYSA-N 0.000 description 1
• HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
• YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
• XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical compound CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 description 1
• 244000166102 Eucalyptus leucoxylon Species 0.000 description 1
• 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 1
• BKVMMSRMRLLPBX-UHFFFAOYSA-N FC(C(=O)O)(F)F.COC=1C(=C2C=CN(C2=CC1)S(=O)(=O)C1=CC=CC=C1)CN(C)C.FC(C(=O)O)(F)F.COC=1C(=C2C=CNC2=CC1)CN(C)C Chemical compound FC(C(=O)O)(F)F.COC=1C(=C2C=CN(C2=CC1)S(=O)(=O)C1=CC=CC=C1)CN(C)C.FC(C(=O)O)(F)F.COC=1C(=C2C=CNC2=CC1)CN(C)C BKVMMSRMRLLPBX-UHFFFAOYSA-N 0.000 description 1
• IXXMOYHRJJCMSG-UHFFFAOYSA-N FC=1C=C(C=2C=CN(C2C1)S(=O)(=O)C1=CC=CC=C1)C=O.FC(C(=O)O)(F)F.FC(C(=O)O)(F)F Chemical compound FC=1C=C(C=2C=CN(C2C1)S(=O)(=O)C1=CC=CC=C1)C=O.FC(C(=O)O)(F)F.FC(C(=O)O)(F)F IXXMOYHRJJCMSG-UHFFFAOYSA-N 0.000 description 1
• YMPQJMNAJIOFDB-UHFFFAOYSA-N FC=1C=C(C=2C=CN(C2C1)S(=O)(=O)C1=CC=CC=C1)C=O.FC(C(=O)O)(F)F.FC(C(=O)O)(F)F.FC1=CC(=C2C=CN(C2=C1)S(=O)(=O)C1=CC=CC=C1)CN1CCNCC1 Chemical compound FC=1C=C(C=2C=CN(C2C1)S(=O)(=O)C1=CC=CC=C1)C=O.FC(C(=O)O)(F)F.FC(C(=O)O)(F)F.FC1=CC(=C2C=CN(C2=C1)S(=O)(=O)C1=CC=CC=C1)CN1CCNCC1 YMPQJMNAJIOFDB-UHFFFAOYSA-N 0.000 description 1
• 108010010803 Gelatin Proteins 0.000 description 1
• 239000007995 HEPES buffer Substances 0.000 description 1
• 101001018064 Homo sapiens Lysosomal-trafficking regulator Proteins 0.000 description 1
• ZAGRKAFMISFKIO-UHFFFAOYSA-N Isolysergic acid Natural products C1=CC(C2=CC(CN(C2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-UHFFFAOYSA-N 0.000 description 1
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
• 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
• VAYOSLLFUXYJDT-RDTXWAMCSA-N Lysergic acid diethylamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N(CC)CC)C2)=C3C2=CNC3=C1 VAYOSLLFUXYJDT-RDTXWAMCSA-N 0.000 description 1
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
• 239000004472 Lysine Substances 0.000 description 1
• 102100033472 Lysosomal-trafficking regulator Human genes 0.000 description 1
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
• 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
• 244000038561 Modiola caroliniana Species 0.000 description 1
• 235000010703 Modiola caroliniana Nutrition 0.000 description 1
• AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
• 206010028980 Neoplasm Diseases 0.000 description 1
• 101100062121 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cyc-1 gene Proteins 0.000 description 1
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• OCQITIRPCRNGBE-UHFFFAOYSA-N OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C1=CC(F)=CC=C1S(=O)(=O)N1C2=CC=CC(CN3CCNCCC3)=C2C=C1 Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C1=CC(F)=CC=C1S(=O)(=O)N1C2=CC=CC(CN3CCNCCC3)=C2C=C1 OCQITIRPCRNGBE-UHFFFAOYSA-N 0.000 description 1
• MXFUKBZJOPYTNA-UHFFFAOYSA-N OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.FC(F)(F)C1=CC=CC(S(=O)(=O)N2C3=CC=CC(CN4CCNCC4)=C3C=C2)=C1 Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.FC(F)(F)C1=CC=CC(S(=O)(=O)N2C3=CC=CC(CN4CCNCC4)=C3C=C2)=C1 MXFUKBZJOPYTNA-UHFFFAOYSA-N 0.000 description 1
• IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
• 240000007817 Olea europaea Species 0.000 description 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
• 239000007868 Raney catalyst Substances 0.000 description 1
• NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
• 229910000564 Raney nickel Inorganic materials 0.000 description 1
• 241000700159 Rattus Species 0.000 description 1
• BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
• 229920002472 Starch Polymers 0.000 description 1
• 238000006619 Stille reaction Methods 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
• 239000005864 Sulphur Substances 0.000 description 1
• RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
• 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
• OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
• 239000007983 Tris buffer Substances 0.000 description 1
• IFTJCOHJPVOCIO-UHFFFAOYSA-N [1-(benzenesulfonyl)-4-(piperazin-1-ylmethyl)-6-(trifluoromethyl)indol-2-yl]methanol Chemical compound C1=C(C(F)(F)F)C=C2N(S(=O)(=O)C=3C=CC=CC=3)C(CO)=CC2=C1CN1CCNCC1 IFTJCOHJPVOCIO-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• YMUZVSPVMMGIEB-UHFFFAOYSA-N [1-(benzenesulfonyl)-6-ethenyl-4-(trifluoromethyl)indol-2-yl]methanol Chemical compound OCC1=CC2=C(C(F)(F)F)C=C(C=C)C=C2N1S(=O)(=O)C1=CC=CC=C1 YMUZVSPVMMGIEB-UHFFFAOYSA-N 0.000 description 1
• MIDWKJMHKFOZGO-UHFFFAOYSA-N [1-(benzenesulfonyl)-6-ethenyl-4-(trifluoromethyl)indol-2-yl]methanol tributyl(ethenyl)stannane Chemical compound C(CCC)[Sn](C=C)(CCCC)CCCC.C1(=CC=CC=C1)S(=O)(=O)N1C(=CC2=C(C=C(C=C12)C=C)C(F)(F)F)CO MIDWKJMHKFOZGO-UHFFFAOYSA-N 0.000 description 1
• ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 description 1
• 230000002159 abnormal effect Effects 0.000 description 1
• 239000000654 additive Substances 0.000 description 1
• 102000030621 adenylate cyclase Human genes 0.000 description 1
• 108060000200 adenylate cyclase Proteins 0.000 description 1
• 210000000577 adipose tissue Anatomy 0.000 description 1
• 230000016571 aggressive behavior Effects 0.000 description 1
• 239000000556 agonist Substances 0.000 description 1
• QBYJBZPUGVGKQQ-SJJAEHHWSA-N aldrin Chemical compound C1[C@H]2C=C[C@@H]1[C@H]1[C@@](C3(Cl)Cl)(Cl)C(Cl)=C(Cl)[C@@]3(Cl)[C@H]12 QBYJBZPUGVGKQQ-SJJAEHHWSA-N 0.000 description 1
• 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
• 150000003973 alkyl amines Chemical class 0.000 description 1
• 125000000304 alkynyl group Chemical group 0.000 description 1
• BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
• 229910052782 aluminium Inorganic materials 0.000 description 1
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 150000001408 amides Chemical class 0.000 description 1
• 150000001413 amino acids Chemical class 0.000 description 1
• 229960004909 aminosalicylic acid Drugs 0.000 description 1
• 229910021529 ammonia Inorganic materials 0.000 description 1
• 235000019257 ammonium acetate Nutrition 0.000 description 1
• 229940043376 ammonium acetate Drugs 0.000 description 1
• VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
• 239000000538 analytical sample Substances 0.000 description 1
• 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
• 239000000074 antisense oligonucleotide Substances 0.000 description 1
• 238000012230 antisense oligonucleotides Methods 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
• 235000010323 ascorbic acid Nutrition 0.000 description 1
• 239000011668 ascorbic acid Substances 0.000 description 1
• 229960005070 ascorbic acid Drugs 0.000 description 1
• 125000004429 atom Chemical group 0.000 description 1
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
• 125000002785 azepinyl group Chemical group 0.000 description 1
• 125000002393 azetidinyl group Chemical group 0.000 description 1
• JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
• 125000000928 benzodioxinyl group Chemical group O1C(=COC2=C1C=CC=C2)* 0.000 description 1
• 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 235000010233 benzoic acid Nutrition 0.000 description 1
• 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
• 235000019400 benzoyl peroxide Nutrition 0.000 description 1
• GZIVIWAYGVIPDJ-UHFFFAOYSA-N benzyl 2-[6-tert-butyl-3-cyano-4-(trifluoromethyl)pyridin-2-yl]sulfanylacetate Chemical compound CC(C)(C)C1=CC(C(F)(F)F)=C(C#N)C(SCC(=O)OCC=2C=CC=CC=2)=N1 GZIVIWAYGVIPDJ-UHFFFAOYSA-N 0.000 description 1
• AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
• 230000033228 biological regulation Effects 0.000 description 1
• 230000036983 biotransformation Effects 0.000 description 1
• IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 1
• KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
• FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
• 159000000007 calcium salts Chemical class 0.000 description 1
• 235000019577 caloric intake Nutrition 0.000 description 1
• 201000011510 cancer Diseases 0.000 description 1
• 239000002775 capsule Substances 0.000 description 1
• VNWKTOKETHGBQD-AKLPVKDBSA-N carbane Chemical group [15CH4] VNWKTOKETHGBQD-AKLPVKDBSA-N 0.000 description 1
• 150000003857 carboxamides Chemical class 0.000 description 1
• 150000007942 carboxylates Chemical class 0.000 description 1
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
• 230000008859 change Effects 0.000 description 1
• 239000003795 chemical substances by application Substances 0.000 description 1
• OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 1
• 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 1
• 238000013375 chromatographic separation Methods 0.000 description 1
• 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 1
• 235000015165 citric acid Nutrition 0.000 description 1
• 238000003776 cleavage reaction Methods 0.000 description 1
• QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 description 1
• 229960004170 clozapine Drugs 0.000 description 1
• 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
• 229940125773 compound 10 Drugs 0.000 description 1
• 229940125810 compound 20 Drugs 0.000 description 1
• 229940125936 compound 42 Drugs 0.000 description 1
• 229940125898 compound 5 Drugs 0.000 description 1
• 238000007906 compression Methods 0.000 description 1
• 230000006835 compression Effects 0.000 description 1
• 239000012084 conversion product Substances 0.000 description 1
• 238000005100 correlation spectroscopy Methods 0.000 description 1
• 239000002178 crystalline material Substances 0.000 description 1
• 238000002425 crystallisation Methods 0.000 description 1
• 230000008025 crystallization Effects 0.000 description 1
• 125000006165 cyclic alkyl group Chemical group 0.000 description 1
• 125000000753 cycloalkyl group Chemical group 0.000 description 1
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
• 238000002405 diagnostic procedure Methods 0.000 description 1
• 235000019700 dicalcium phosphate Nutrition 0.000 description 1
• SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
• 235000005911 diet Nutrition 0.000 description 1
• 230000037213 diet Effects 0.000 description 1
• 208000010643 digestive system disease Diseases 0.000 description 1
• 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
• IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
• 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
• IHFRJBOORJWYLK-UHFFFAOYSA-N dimethylcarbamic acid 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.CN(C(O)=O)C IHFRJBOORJWYLK-UHFFFAOYSA-N 0.000 description 1
• HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
• 229910001873 dinitrogen Inorganic materials 0.000 description 1
• 125000000532 dioxanyl group Chemical group 0.000 description 1
• 239000002552 dosage form Substances 0.000 description 1
• 239000000890 drug combination Substances 0.000 description 1
• 238000009510 drug design Methods 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 238000000132 electrospray ionisation Methods 0.000 description 1
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
• 230000008030 elimination Effects 0.000 description 1
• 238000003379 elimination reaction Methods 0.000 description 1
• 239000003995 emulsifying agent Substances 0.000 description 1
• 150000002148 esters Chemical class 0.000 description 1
• BADWIIDKTXQYLW-UHFFFAOYSA-N ethenylstannane Chemical compound [SnH3]C=C BADWIIDKTXQYLW-UHFFFAOYSA-N 0.000 description 1
• 150000002170 ethers Chemical class 0.000 description 1
• 229940052303 ethers for general anesthesia Drugs 0.000 description 1
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
• VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 1
• VTMUKFKAOAEYBX-UHFFFAOYSA-N ethyl 4-bromo-6-(trifluoromethyl)-1h-indole-2-carboxylate Chemical compound C1=C(C(F)(F)F)C=C2NC(C(=O)OCC)=CC2=C1Br VTMUKFKAOAEYBX-UHFFFAOYSA-N 0.000 description 1
• 229940117360 ethyl pyruvate Drugs 0.000 description 1
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
• UGRVUSWSAGRCSJ-UHFFFAOYSA-N ethylammonium trifluoroacetate Chemical compound CC[NH3+].[O-]C(=O)C(F)(F)F UGRVUSWSAGRCSJ-UHFFFAOYSA-N 0.000 description 1
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
• 230000029142 excretion Effects 0.000 description 1
• 238000002474 experimental method Methods 0.000 description 1
• 230000035611 feeding Effects 0.000 description 1
• 239000000796 flavoring agent Substances 0.000 description 1
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
• 239000006260 foam Substances 0.000 description 1
• 238000005187 foaming Methods 0.000 description 1
• 235000013355 food flavoring agent Nutrition 0.000 description 1
• 235000019253 formic acid Nutrition 0.000 description 1
• 238000001640 fractional crystallisation Methods 0.000 description 1
• 239000001530 fumaric acid Substances 0.000 description 1
• 235000011087 fumaric acid Nutrition 0.000 description 1
• 125000002541 furyl group Chemical group 0.000 description 1
• 239000008273 gelatin Substances 0.000 description 1
• 229920000159 gelatin Polymers 0.000 description 1
• 235000019322 gelatine Nutrition 0.000 description 1
• 235000011852 gelatine desserts Nutrition 0.000 description 1
• 239000011521 glass Substances 0.000 description 1
• 238000005469 granulation Methods 0.000 description 1
• 230000003179 granulation Effects 0.000 description 1
• 229940093915 gynecological organic acid Drugs 0.000 description 1
• 230000005802 health problem Effects 0.000 description 1
• 125000005842 heteroatom Chemical group 0.000 description 1
• 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 1
• 238000005570 heteronuclear single quantum coherence Methods 0.000 description 1
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
• 150000002430 hydrocarbons Chemical group 0.000 description 1
• 150000003840 hydrochlorides Chemical class 0.000 description 1
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
• 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
• DCPMPXBYPZGNDC-UHFFFAOYSA-N hydron;methanediimine;chloride Chemical compound Cl.N=C=N DCPMPXBYPZGNDC-UHFFFAOYSA-N 0.000 description 1
• UVNXNSUKKOLFBM-UHFFFAOYSA-N imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=CSC2=NC=CN21 UVNXNSUKKOLFBM-UHFFFAOYSA-N 0.000 description 1
• 125000002636 imidazolinyl group Chemical group 0.000 description 1
• 125000002883 imidazolyl group Chemical group 0.000 description 1
• 239000012535 impurity Substances 0.000 description 1
• 238000001727 in vivo Methods 0.000 description 1
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
• JFDDFGLNZWNJTK-UHFFFAOYSA-N indole-4-carbaldehyde Chemical compound O=CC1=CC=CC2=C1C=CN2 JFDDFGLNZWNJTK-UHFFFAOYSA-N 0.000 description 1
• 150000002476 indolines Chemical class 0.000 description 1
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
• 230000002401 inhibitory effect Effects 0.000 description 1
• 239000003999 initiator Substances 0.000 description 1
• 239000007924 injection Substances 0.000 description 1
• 238000002347 injection Methods 0.000 description 1
• 229940030980 inova Drugs 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
• 229910052742 iron Inorganic materials 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
• 125000001786 isothiazolyl group Chemical group 0.000 description 1
• 125000000842 isoxazolyl group Chemical group 0.000 description 1
• ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
• 239000004310 lactic acid Substances 0.000 description 1
• 235000014655 lactic acid Nutrition 0.000 description 1
• 229960000448 lactic acid Drugs 0.000 description 1
• 239000008101 lactose Substances 0.000 description 1
• 229960001375 lactose Drugs 0.000 description 1
• 230000000670 limiting effect Effects 0.000 description 1
• 239000012669 liquid formulation Substances 0.000 description 1
• 239000012280 lithium aluminium hydride Substances 0.000 description 1
• HAUIPIYBUVHIFK-UHFFFAOYSA-M lithium;1-(benzenesulfonyl)-5-methoxy-4-[[4-[(2-methylpropan-2-yl)oxycarbonyl]piperazin-1-yl]methyl]indole-2-carboxylate Chemical compound [Li+].COC1=CC=C2N(S(=O)(=O)C=3C=CC=CC=3)C(C([O-])=O)=CC2=C1CN1CCN(C(=O)OC(C)(C)C)CC1 HAUIPIYBUVHIFK-UHFFFAOYSA-M 0.000 description 1
• IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 1
• 208000020442 loss of weight Diseases 0.000 description 1
• ZAGRKAFMISFKIO-QMTHXVAHSA-N lysergic acid Chemical compound C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-QMTHXVAHSA-N 0.000 description 1
• 235000019359 magnesium stearate Nutrition 0.000 description 1
• 230000014759 maintenance of location Effects 0.000 description 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• 239000011976 maleic acid Substances 0.000 description 1
• 229940098895 maleic acid Drugs 0.000 description 1
• 239000001630 malic acid Substances 0.000 description 1
• 235000011090 malic acid Nutrition 0.000 description 1
• 239000003550 marker Substances 0.000 description 1
• 238000005259 measurement Methods 0.000 description 1
• 230000002503 metabolic effect Effects 0.000 description 1
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
• OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 1
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
• OFXSXYCSPVKZPF-UHFFFAOYSA-N methoxyperoxymethane Chemical compound COOOC OFXSXYCSPVKZPF-UHFFFAOYSA-N 0.000 description 1
• CHNOQXRIMCFHKZ-BYPYZUCNSA-N methyl (2s)-azetidine-2-carboxylate Chemical compound COC(=O)[C@@H]1CCN1 CHNOQXRIMCFHKZ-BYPYZUCNSA-N 0.000 description 1
• 229940016286 microcrystalline cellulose Drugs 0.000 description 1
• 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
• 239000008108 microcrystalline cellulose Substances 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• 150000004682 monohydrates Chemical class 0.000 description 1
• 239000000178 monomer Substances 0.000 description 1
• 125000002757 morpholinyl group Chemical group 0.000 description 1
• CLVCTWTZACMHFX-UHFFFAOYSA-N n,n-dimethyl-1-(1-pyridin-3-ylsulfonylindol-4-yl)methanamine Chemical compound C1=CC=2C(CN(C)C)=CC=CC=2N1S(=O)(=O)C1=CC=CN=C1 CLVCTWTZACMHFX-UHFFFAOYSA-N 0.000 description 1
• CSLJKWFAWKKCEB-UHFFFAOYSA-N n,n-dimethyl-1-[1-(2-methylphenyl)sulfonylindol-4-yl]methanamine Chemical compound C1=CC=2C(CN(C)C)=CC=CC=2N1S(=O)(=O)C1=CC=CC=C1C CSLJKWFAWKKCEB-UHFFFAOYSA-N 0.000 description 1
• GFKZLUFGLZDNSN-UHFFFAOYSA-N n,n-dimethyl-1-[1-[3-(trifluoromethyl)phenyl]sulfonylindol-4-yl]methanamine Chemical compound C1=CC=2C(CN(C)C)=CC=CC=2N1S(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 GFKZLUFGLZDNSN-UHFFFAOYSA-N 0.000 description 1
• DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
• GAGLWASADSGLFB-UHFFFAOYSA-N n-[[1-(2-methoxy-5-methylphenyl)sulfonylindol-4-yl]methyl]-1-propan-2-ylpiperidin-4-amine Chemical compound COC1=CC=C(C)C=C1S(=O)(=O)N1C2=CC=CC(CNC3CCN(CC3)C(C)C)=C2C=C1 GAGLWASADSGLFB-UHFFFAOYSA-N 0.000 description 1
• URYBCQLDWPXKAU-UHFFFAOYSA-N n-[[1-(2-methoxy-5-methylphenyl)sulfonylindol-4-yl]methyl]piperidin-4-amine Chemical compound COC1=CC=C(C)C=C1S(=O)(=O)N1C2=CC=CC(CNC3CCNCC3)=C2C=C1 URYBCQLDWPXKAU-UHFFFAOYSA-N 0.000 description 1
• ORNXZDQFVCDXNS-UHFFFAOYSA-N n-[[1-(benzenesulfonyl)-5-methoxyindol-4-yl]methyl]-n-methylcyclobutanamine Chemical compound COC1=CC=C2N(S(=O)(=O)C=3C=CC=CC=3)C=CC2=C1CN(C)C1CCC1 ORNXZDQFVCDXNS-UHFFFAOYSA-N 0.000 description 1
• QPQLRFDLNQTSCN-UHFFFAOYSA-N n-[[1-(benzenesulfonyl)-5-methoxyindol-4-yl]methyl]cyclobutanamine Chemical compound COC1=CC=C2N(S(=O)(=O)C=3C=CC=CC=3)C=CC2=C1CNC1CCC1 QPQLRFDLNQTSCN-UHFFFAOYSA-N 0.000 description 1
• FOQNWYOHXIHWQB-UHFFFAOYSA-N n-[[1-(benzenesulfonyl)-6-fluoro-5-methoxyindol-4-yl]methyl]-n-methylethanamine Chemical compound C1=CC=2C(CN(C)CC)=C(OC)C(F)=CC=2N1S(=O)(=O)C1=CC=CC=C1 FOQNWYOHXIHWQB-UHFFFAOYSA-N 0.000 description 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• PFFZTPGDNRINSP-UHFFFAOYSA-N n-ethyl-n-[(1-thiophen-2-ylsulfonylindol-4-yl)methyl]ethanamine Chemical compound C1=CC=2C(CN(CC)CC)=CC=CC=2N1S(=O)(=O)C1=CC=CS1 PFFZTPGDNRINSP-UHFFFAOYSA-N 0.000 description 1
• DASJFYAPNPUBGG-UHFFFAOYSA-N naphthalene-1-sulfonyl chloride Chemical compound C1=CC=C2C(S(=O)(=O)Cl)=CC=CC2=C1 DASJFYAPNPUBGG-UHFFFAOYSA-N 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
• 150000002832 nitroso derivatives Chemical class 0.000 description 1
• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
• 208000030212 nutrition disease Diseases 0.000 description 1
• 239000012053 oil suspension Substances 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 235000006408 oxalic acid Nutrition 0.000 description 1
• 125000002971 oxazolyl group Chemical group 0.000 description 1
• 230000003647 oxidation Effects 0.000 description 1
• 238000007254 oxidation reaction Methods 0.000 description 1
• 238000007248 oxidative elimination reaction Methods 0.000 description 1
• 239000001301 oxygen Substances 0.000 description 1
• 125000004430 oxygen atom Chemical group O* 0.000 description 1
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
• 238000010651 palladium-catalyzed cross coupling reaction Methods 0.000 description 1
• WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
• FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
• 238000007911 parenteral administration Methods 0.000 description 1
• 230000001575 pathological effect Effects 0.000 description 1
• 235000019371 penicillin G benzathine Nutrition 0.000 description 1
• 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
• 230000002093 peripheral effect Effects 0.000 description 1
• 210000001428 peripheral nervous system Anatomy 0.000 description 1
• 229940124531 pharmaceutical excipient Drugs 0.000 description 1
• 230000000144 pharmacologic effect Effects 0.000 description 1
• 238000005191 phase separation Methods 0.000 description 1
• 239000003444 phase transfer catalyst Substances 0.000 description 1
• NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical compound OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 1
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
• UXWKNNJFYZFNDI-UHFFFAOYSA-N piperazine;dihydrobromide Chemical compound Br.Br.C1CNCCN1 UXWKNNJFYZFNDI-UHFFFAOYSA-N 0.000 description 1
• 125000004193 piperazinyl group Chemical group 0.000 description 1
• 125000005936 piperidyl group Chemical group 0.000 description 1
• 239000002798 polar solvent Substances 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 235000011056 potassium acetate Nutrition 0.000 description 1
• 230000036515 potency Effects 0.000 description 1
• 230000003389 potentiating effect Effects 0.000 description 1
• 239000000651 prodrug Substances 0.000 description 1
• 229940002612 prodrug Drugs 0.000 description 1
• 235000019260 propionic acid Nutrition 0.000 description 1
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
• 125000003373 pyrazinyl group Chemical group 0.000 description 1
• 125000003226 pyrazolyl group Chemical group 0.000 description 1
• 125000002098 pyridazinyl group Chemical group 0.000 description 1
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
• XMOBZSXTLUDPEE-UHFFFAOYSA-N pyridine-3-sulfonic acid;pyridine-3-sulfonyl chloride;hydrochloride Chemical compound Cl.OS(=O)(=O)C1=CC=CN=C1.ClS(=O)(=O)C1=CC=CN=C1 XMOBZSXTLUDPEE-UHFFFAOYSA-N 0.000 description 1
• VIVPWOMJFLICOZ-UHFFFAOYSA-N pyridine-3-sulfonyl chloride;hydrochloride Chemical compound Cl.ClS(=O)(=O)C1=CC=CN=C1 VIVPWOMJFLICOZ-UHFFFAOYSA-N 0.000 description 1
• 125000000714 pyrimidinyl group Chemical group 0.000 description 1
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• 229940107700 pyruvic acid Drugs 0.000 description 1
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
• 239000000018 receptor agonist Substances 0.000 description 1
• 229940044601 receptor agonist Drugs 0.000 description 1
• 229940044551 receptor antagonist Drugs 0.000 description 1
• 239000002464 receptor antagonist Substances 0.000 description 1
• 239000013557 residual solvent Substances 0.000 description 1
• 208000023504 respiratory system disease Diseases 0.000 description 1
• 230000002441 reversible effect Effects 0.000 description 1
• 229960004889 salicylic acid Drugs 0.000 description 1
• 239000000523 sample Substances 0.000 description 1
• 239000012047 saturated solution Substances 0.000 description 1
• 230000007017 scission Effects 0.000 description 1
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 229910052711 selenium Inorganic materials 0.000 description 1
• 239000011669 selenium Substances 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 229940076279 serotonin Drugs 0.000 description 1
• 108010006590 serotonin 5 receptor Proteins 0.000 description 1
• 230000000697 serotonin reuptake Effects 0.000 description 1
• 230000002295 serotoninergic effect Effects 0.000 description 1
• XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
• 239000001632 sodium acetate Substances 0.000 description 1
• 235000017281 sodium acetate Nutrition 0.000 description 1
• 229940079832 sodium starch glycolate Drugs 0.000 description 1
• 229920003109 sodium starch glycolate Polymers 0.000 description 1
• 239000008109 sodium starch glycolate Substances 0.000 description 1
• 239000011343 solid material Substances 0.000 description 1
• 238000001228 spectrum Methods 0.000 description 1
• 238000005507 spraying Methods 0.000 description 1
• 239000003381 stabilizer Substances 0.000 description 1
• 238000010561 standard procedure Methods 0.000 description 1
• 235000011150 stannous chloride Nutrition 0.000 description 1
• 229940032147 starch Drugs 0.000 description 1
• 235000019698 starch Nutrition 0.000 description 1
• 239000008107 starch Substances 0.000 description 1
• 125000005504 styryl group Chemical group 0.000 description 1
• FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
• 229940124530 sulfonamide Drugs 0.000 description 1
• 229910052717 sulfur Inorganic materials 0.000 description 1
• 125000004434 sulfur atom Chemical group 0.000 description 1
• 229910021653 sulphate ion Inorganic materials 0.000 description 1
• 239000000829 suppository Substances 0.000 description 1
• 230000002459 sustained effect Effects 0.000 description 1
• 230000002194 synthesizing effect Effects 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 235000012222 talc Nutrition 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• CMIBWIAICVBURI-UHFFFAOYSA-N tert-butyl 3-aminopyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(N)C1 CMIBWIAICVBURI-UHFFFAOYSA-N 0.000 description 1
• MJKGWHVPMFCVFK-UHFFFAOYSA-N tert-butyl 4-[[1-(benzenesulfonyl)-2-(ethylcarbamoyl)-5-methoxyindol-4-yl]methyl]piperazine-1-carboxylate Chemical compound COC1=CC=C2N(S(=O)(=O)C=3C=CC=CC=3)C(C(=O)NCC)=CC2=C1CN1CCN(C(=O)OC(C)(C)C)CC1 MJKGWHVPMFCVFK-UHFFFAOYSA-N 0.000 description 1
• SWRZWSRUPKTAPK-UHFFFAOYSA-N tert-butyl 4-[[1-(benzenesulfonyl)-2-methylindol-4-yl]methyl]piperazine-1-carboxylate Chemical compound C1=CC=C2N(S(=O)(=O)C=3C=CC=CC=3)C(C)=CC2=C1CN1CCN(C(=O)OC(C)(C)C)CC1 SWRZWSRUPKTAPK-UHFFFAOYSA-N 0.000 description 1
• HLCMYUTYCWIYST-UHFFFAOYSA-N tert-butyl 4-[[1-(benzenesulfonyl)-5-methoxy-2-(thiophen-2-ylmethylcarbamoyl)indol-4-yl]methyl]piperazine-1-carboxylate Chemical compound COC1=CC=C2N(S(=O)(=O)C=3C=CC=CC=3)C(C(=O)NCC=3SC=CC=3)=CC2=C1CN1CCN(C(=O)OC(C)(C)C)CC1 HLCMYUTYCWIYST-UHFFFAOYSA-N 0.000 description 1
• UFOSXCDYUJWTTQ-UHFFFAOYSA-N tert-butyl 4-[[1-(benzenesulfonyl)-5-phenylmethoxyindol-4-yl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC(C=1C=CN(C=1C=C1)S(=O)(=O)C=2C=CC=CC=2)=C1OCC1=CC=CC=C1 UFOSXCDYUJWTTQ-UHFFFAOYSA-N 0.000 description 1
• MGOJYRKRGPQEJX-UHFFFAOYSA-N tert-butyl 4-[[1-(benzenesulfonyl)-7-methoxyindol-4-yl]methyl]piperazine-1-carboxylate Chemical compound C1=2C=CN(S(=O)(=O)C=3C=CC=CC=3)C=2C(OC)=CC=C1CN1CCN(C(=O)OC(C)(C)C)CC1 MGOJYRKRGPQEJX-UHFFFAOYSA-N 0.000 description 1
• DQQJBEAXSOOCPG-UHFFFAOYSA-N tert-butyl n-pyrrolidin-3-ylcarbamate Chemical compound CC(C)(C)OC(=O)NC1CCNC1 DQQJBEAXSOOCPG-UHFFFAOYSA-N 0.000 description 1
• 238000010998 test method Methods 0.000 description 1
• ZXUCBXRTRRIBSO-UHFFFAOYSA-L tetrabutylazanium;sulfate Chemical compound [O-]S([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC ZXUCBXRTRRIBSO-UHFFFAOYSA-L 0.000 description 1
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
• WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
• 125000001544 thienyl group Chemical group 0.000 description 1
• 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
• AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
• 125000003944 tolyl group Chemical group 0.000 description 1
• LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1
• 238000010626 work up procedure Methods 0.000 description 1
• 229910052727 yttrium Inorganic materials 0.000 description 1