JP5087171B2 - ５−ヒドロキシトリプタミン−６リガンドとしての１−（アリールスルホニル）−４−（ピペラジン−１−イル）−１ｈ−ベンズイミダゾール類 - Google Patents

Info

Publication number

JP5087171B2

JP5087171B2 JP2011536412A JP2011536412A JP5087171B2 JP 5087171 B2 JP5087171 B2 JP 5087171B2 JP 2011536412 A JP2011536412 A JP 2011536412A JP 2011536412 A JP2011536412 A JP 2011536412A JP 5087171 B2 JP5087171 B2 JP 5087171B2

Authority

JP

Japan

Prior art keywords

benzimidazole

alkyl

compound

sulfonyl

piperazin

Prior art date

2008-11-11

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Fee Related

Links

• Espacenet
• Global Dossier
• Discuss

• 239000003446 ligand Substances 0.000 title description 13
• 125000004391 aryl sulfonyl group Chemical group 0.000 title description 4
• 150000001875 compounds Chemical class 0.000 claims description 141
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 116
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 47
• 239000000203 mixture Substances 0.000 claims description 29
• 201000000980 schizophrenia Diseases 0.000 claims description 28
• 208000035475 disorder Diseases 0.000 claims description 25
• 239000003814 drug Substances 0.000 claims description 23
• 201000010099 disease Diseases 0.000 claims description 22
• 208000024827 Alzheimer disease Diseases 0.000 claims description 18
• 150000003839 salts Chemical class 0.000 claims description 18
• 208000010877 cognitive disease Diseases 0.000 claims description 17
• 210000003169 central nervous system Anatomy 0.000 claims description 14
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 11
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 10
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 10
• 208000028698 Cognitive impairment Diseases 0.000 claims description 9
• 208000019901 Anxiety disease Diseases 0.000 claims description 8
• 230000036506 anxiety Effects 0.000 claims description 8
• 229940079593 drug Drugs 0.000 claims description 8
• 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 6
• 208000018737 Parkinson disease Diseases 0.000 claims description 6
• 208000028017 Psychotic disease Diseases 0.000 claims description 6
• 230000007278 cognition impairment Effects 0.000 claims description 6
• 206010015037 epilepsy Diseases 0.000 claims description 6
• 208000002193 Pain Diseases 0.000 claims description 5
• 230000002950 deficient Effects 0.000 claims description 5
• 230000004770 neurodegeneration Effects 0.000 claims description 5
• 208000032841 Bulimia Diseases 0.000 claims description 4
• 206010006550 Bulimia nervosa Diseases 0.000 claims description 4
• 208000030814 Eating disease Diseases 0.000 claims description 4
• 208000019454 Feeding and Eating disease Diseases 0.000 claims description 4
• 208000018522 Gastrointestinal disease Diseases 0.000 claims description 4
• 208000019695 Migraine disease Diseases 0.000 claims description 4
• 206010033664 Panic attack Diseases 0.000 claims description 4
• 208000022531 anorexia Diseases 0.000 claims description 4
• 206010061428 decreased appetite Diseases 0.000 claims description 4
• 235000014632 disordered eating Nutrition 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 235000005686 eating Nutrition 0.000 claims description 4
• 230000006870 function Effects 0.000 claims description 4
• 230000012010 growth Effects 0.000 claims description 4
• 208000002551 irritable bowel syndrome Diseases 0.000 claims description 4
• 206010027599 migraine Diseases 0.000 claims description 4
• 210000005036 nerve Anatomy 0.000 claims description 4
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 4
• 208000019906 panic disease Diseases 0.000 claims description 4
• 208000019116 sleep disease Diseases 0.000 claims description 4
• MAYQIFVKVAUMPD-UHFFFAOYSA-N 1-(benzenesulfonyl)-2-methyl-4-piperazin-1-ylbenzimidazole Chemical group CC1=NC2=C(N3CCNCC3)C=CC=C2N1S(=O)(=O)C1=CC=CC=C1 MAYQIFVKVAUMPD-UHFFFAOYSA-N 0.000 claims description 3
• 208000023105 Huntington disease Diseases 0.000 claims description 3
• 208000026139 Memory disease Diseases 0.000 claims description 3
• 208000020685 sleep-wake disease Diseases 0.000 claims description 3
• 208000008589 Obesity Diseases 0.000 claims description 2
• 206010027175 memory impairment Diseases 0.000 claims description 2
• 235000020824 obesity Nutrition 0.000 claims description 2
• -1 2,5-dichlorophenyl Chemical group 0.000 description 83
• 238000000034 method Methods 0.000 description 50
• 125000005843 halogen group Chemical group 0.000 description 41
• 102000005962 receptors Human genes 0.000 description 31
• 108020003175 receptors Proteins 0.000 description 31
• 238000004949 mass spectrometry Methods 0.000 description 29
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 26
• 229910052799 carbon Inorganic materials 0.000 description 25
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 25
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
• 125000003118 aryl group Chemical group 0.000 description 19
• 239000000243 solution Substances 0.000 description 19
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
• 238000005481 NMR spectroscopy Methods 0.000 description 18
• 238000002360 preparation method Methods 0.000 description 18
• 125000001424 substituent group Chemical group 0.000 description 18
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
• 238000006243 chemical reaction Methods 0.000 description 15
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 14
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
• 230000000694 effects Effects 0.000 description 13
• 239000000047 product Substances 0.000 description 13
• 125000002252 acyl group Chemical group 0.000 description 12
• 125000000217 alkyl group Chemical group 0.000 description 12
• CGNBQYFXGQHUQP-UHFFFAOYSA-N 2,3-dinitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O CGNBQYFXGQHUQP-UHFFFAOYSA-N 0.000 description 11
• 150000001721 carbon Chemical group 0.000 description 11
• 229910052736 halogen Inorganic materials 0.000 description 11
• 150000002367 halogens Chemical class 0.000 description 11
• 230000008569 process Effects 0.000 description 11
• 125000006239 protecting group Chemical group 0.000 description 11
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 11
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 10
• 235000019439 ethyl acetate Nutrition 0.000 description 10
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 9
• OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 9
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
• 210000004556 brain Anatomy 0.000 description 9
• 210000004027 cell Anatomy 0.000 description 9
• 239000000460 chlorine Substances 0.000 description 9
• 239000000543 intermediate Substances 0.000 description 9
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 9
• 239000007787 solid Substances 0.000 description 9
• 229940124597 therapeutic agent Drugs 0.000 description 9
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 8
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 8
• 230000003920 cognitive function Effects 0.000 description 8
• 229910052739 hydrogen Inorganic materials 0.000 description 8
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
• 230000015654 memory Effects 0.000 description 8
• MSBYNICBNNNGHO-UHFFFAOYSA-N tert-butyl 4-(2,3-dinitrophenyl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O MSBYNICBNNNGHO-UHFFFAOYSA-N 0.000 description 8
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 7
• 230000003213 activating effect Effects 0.000 description 7
• 125000004432 carbon atom Chemical group C* 0.000 description 7
• 238000004811 liquid chromatography Methods 0.000 description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
• CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 7
• 230000001225 therapeutic effect Effects 0.000 description 7
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 6
• GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 6
• 241000282414 Homo sapiens Species 0.000 description 6
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
• 241000700159 Rattus Species 0.000 description 6
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
• 125000003277 amino group Chemical group 0.000 description 6
• 230000027455 binding Effects 0.000 description 6
• 230000037396 body weight Effects 0.000 description 6
• 208000015114 central nervous system disease Diseases 0.000 description 6
• 230000019771 cognition Effects 0.000 description 6
• 125000000392 cycloalkenyl group Chemical group 0.000 description 6
• 230000001965 increasing effect Effects 0.000 description 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
• 239000008194 pharmaceutical composition Substances 0.000 description 6
• 125000003107 substituted aryl group Chemical group 0.000 description 6
• 208000024891 symptom Diseases 0.000 description 6
• METKBMVDFPVNJQ-UHFFFAOYSA-N 1-azido-3-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=C(F)C=CC=C1N=[N+]=[N-] METKBMVDFPVNJQ-UHFFFAOYSA-N 0.000 description 5
• GEBJYRDABZFWLG-UHFFFAOYSA-N 1-bromo-2,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Br)=C1[N+]([O-])=O GEBJYRDABZFWLG-UHFFFAOYSA-N 0.000 description 5
• 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 5
• 241000282412 Homo Species 0.000 description 5
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 5
• 239000002585 base Substances 0.000 description 5
• MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical group C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 5
• 125000005349 heteroarylcycloalkyl group Chemical group 0.000 description 5
• 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 description 5
• 125000004430 oxygen atom Chemical group O* 0.000 description 5
• 239000002953 phosphate buffered saline Substances 0.000 description 5
• 208000011117 substance-related disease Diseases 0.000 description 5
• 238000006467 substitution reaction Methods 0.000 description 5
• CWHNMQRUACPXSK-UHFFFAOYSA-N 4-(4-tert-butylpiperazin-1-yl)-2-methyl-1h-benzimidazole Chemical compound C1=CC=C2NC(C)=NC2=C1N1CCN(C(C)(C)C)CC1 CWHNMQRUACPXSK-UHFFFAOYSA-N 0.000 description 4
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
• 0 C*(C)(C(*)C1)C(*)C*1c1cccc2c1*=C(*)*2*c1c(CC=*)c(*)c(C(C)=*)c(*)c1* Chemical compound C*(C)(C(*)C1)C(*)C*1c1cccc2c1*=C(*)*2*c1c(CC=*)c(*)c(C(C)=*)c(*)c1* 0.000 description 4
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
• 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 4
• 241000124008 Mammalia Species 0.000 description 4
• 241001465754 Metazoa Species 0.000 description 4
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical group [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
• 239000004480 active ingredient Substances 0.000 description 4
• 125000005530 alkylenedioxy group Chemical group 0.000 description 4
• 239000005557 antagonist Substances 0.000 description 4
• 239000012131 assay buffer Substances 0.000 description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
• 230000008499 blood brain barrier function Effects 0.000 description 4
• 210000001218 blood-brain barrier Anatomy 0.000 description 4
• 239000003153 chemical reaction reagent Substances 0.000 description 4
• 229940125898 compound 5 Drugs 0.000 description 4
• 238000010511 deprotection reaction Methods 0.000 description 4
• GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 4
• VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 4
• 238000004817 gas chromatography Methods 0.000 description 4
• 125000001072 heteroaryl group Chemical group 0.000 description 4
• 229950002454 lysergide Drugs 0.000 description 4
• 239000008188 pellet Substances 0.000 description 4
• 238000006268 reductive amination reaction Methods 0.000 description 4
• 238000010992 reflux Methods 0.000 description 4
• 238000011160 research Methods 0.000 description 4
• 238000002821 scintillation proximity assay Methods 0.000 description 4
• 239000000741 silica gel Substances 0.000 description 4
• 229910002027 silica gel Inorganic materials 0.000 description 4
• 229910000104 sodium hydride Inorganic materials 0.000 description 4
• VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 4
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
• 239000002904 solvent Substances 0.000 description 4
• 239000000126 substance Substances 0.000 description 4
• XUYIHBQKVOXWSI-UHFFFAOYSA-N tert-butyl 4-(3-azido-2-nitrophenyl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=CC(N=[N+]=[N-])=C1[N+]([O-])=O XUYIHBQKVOXWSI-UHFFFAOYSA-N 0.000 description 4
• 238000004809 thin layer chromatography Methods 0.000 description 4
• SSNCMIDZGFCTST-UHFFFAOYSA-N 1,3-difluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=C(F)C=CC=C1F SSNCMIDZGFCTST-UHFFFAOYSA-N 0.000 description 3
• NRWDYKRDVGBLDG-UHFFFAOYSA-N 1-(2-fluorophenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound FC1=CC=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2N=C1 NRWDYKRDVGBLDG-UHFFFAOYSA-N 0.000 description 3
• NPSFFQLIPILIMZ-UHFFFAOYSA-N 1-(3-chlorophenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound ClC1=CC=CC(S(=O)(=O)N2C3=CC=CC(=C3N=C2)N2CCNCC2)=C1 NPSFFQLIPILIMZ-UHFFFAOYSA-N 0.000 description 3
• FQHFXGLATYEFEO-UHFFFAOYSA-N 1-(3-fluorophenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound FC1=CC=CC(S(=O)(=O)N2C3=CC=CC(=C3N=C2)N2CCNCC2)=C1 FQHFXGLATYEFEO-UHFFFAOYSA-N 0.000 description 3
• AGBNVYFCQLKPBX-UHFFFAOYSA-N 1-naphthalen-1-ylsulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound C=1C=CC2=CC=CC=C2C=1S(=O)(=O)N(C1=CC=C2)C=NC1=C2N1CCNCC1 AGBNVYFCQLKPBX-UHFFFAOYSA-N 0.000 description 3
• 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
• 206010012289 Dementia Diseases 0.000 description 3
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
• WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 3
• 229960000583 acetic acid Drugs 0.000 description 3
• 125000003342 alkenyl group Chemical group 0.000 description 3
• 150000001408 amides Chemical class 0.000 description 3
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
• 230000015572 biosynthetic process Effects 0.000 description 3
• 230000000903 blocking effect Effects 0.000 description 3
• 239000000872 buffer Substances 0.000 description 3
• MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 3
• 239000003638 chemical reducing agent Substances 0.000 description 3
• 238000004891 communication Methods 0.000 description 3
• 230000006735 deficit Effects 0.000 description 3
• 239000002552 dosage form Substances 0.000 description 3
• 125000001153 fluoro group Chemical group F* 0.000 description 3
• 229930195712 glutamate Natural products 0.000 description 3
• 125000000623 heterocyclic group Chemical group 0.000 description 3
• 238000004128 high performance liquid chromatography Methods 0.000 description 3
• 210000001320 hippocampus Anatomy 0.000 description 3
• 238000005984 hydrogenation reaction Methods 0.000 description 3
• 230000013016 learning Effects 0.000 description 3
• 125000002950 monocyclic group Chemical group 0.000 description 3
• YTGWKOHORKGMHD-UHFFFAOYSA-N n-(2,3-dinitrophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O YTGWKOHORKGMHD-UHFFFAOYSA-N 0.000 description 3
• KFTYNYHJHKCRKU-UHFFFAOYSA-N n-(3-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC([N+]([O-])=O)=C1 KFTYNYHJHKCRKU-UHFFFAOYSA-N 0.000 description 3
• 229910052757 nitrogen Inorganic materials 0.000 description 3
• 210000001009 nucleus accumben Anatomy 0.000 description 3
• 125000003367 polycyclic group Chemical group 0.000 description 3
• 239000002244 precipitate Substances 0.000 description 3
• 238000012545 processing Methods 0.000 description 3
• 230000009467 reduction Effects 0.000 description 3
• 238000006722 reduction reaction Methods 0.000 description 3
• 230000000087 stabilizing effect Effects 0.000 description 3
• 238000003786 synthesis reaction Methods 0.000 description 3
• 239000003826 tablet Substances 0.000 description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
• 238000012360 testing method Methods 0.000 description 3
• CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 3
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
• 239000003981 vehicle Substances 0.000 description 3
• CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
• YFTQVRYKNGZVNL-UHFFFAOYSA-N 1-(2-chlorophenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound ClC1=CC=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2N=C1 YFTQVRYKNGZVNL-UHFFFAOYSA-N 0.000 description 2
• DUTZUNNPEJCXSH-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2N=C1 DUTZUNNPEJCXSH-UHFFFAOYSA-N 0.000 description 2
• AOVAFWDBDUYYBS-UHFFFAOYSA-N 1-(benzenesulfonyl)-2-butyl-4-piperazin-1-ylbenzimidazole Chemical compound CCCCC1=NC2=C(N3CCNCC3)C=CC=C2N1S(=O)(=O)C1=CC=CC=C1 AOVAFWDBDUYYBS-UHFFFAOYSA-N 0.000 description 2
• VMTAFEHGBVKCGV-UHFFFAOYSA-N 1-(benzenesulfonyl)-2-ethyl-4-piperazin-1-ylbenzimidazole Chemical compound CCC1=NC2=C(N3CCNCC3)C=CC=C2N1S(=O)(=O)C1=CC=CC=C1 VMTAFEHGBVKCGV-UHFFFAOYSA-N 0.000 description 2
• LXZXYELCNWWCHJ-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-(4-ethylpiperazin-1-yl)benzimidazole Chemical compound C1CN(CC)CCN1C1=CC=CC2=C1N=CN2S(=O)(=O)C1=CC=CC=C1 LXZXYELCNWWCHJ-UHFFFAOYSA-N 0.000 description 2
• HUWFTRHLJJHGEF-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-(4-methylpiperazin-1-yl)benzimidazole Chemical compound C1CN(C)CCN1C1=CC=CC2=C1N=CN2S(=O)(=O)C1=CC=CC=C1 HUWFTRHLJJHGEF-UHFFFAOYSA-N 0.000 description 2
• QDCKMHZZSZNNNQ-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-piperazin-1-ylbenzimidazole Chemical compound C1=NC2=C(N3CCNCC3)C=CC=C2N1S(=O)(=O)C1=CC=CC=C1 QDCKMHZZSZNNNQ-UHFFFAOYSA-N 0.000 description 2
• LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
• 238000005160 1H NMR spectroscopy Methods 0.000 description 2
• RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 2
• XNMQEEKYCVKGBD-UHFFFAOYSA-N 2-butyne Chemical compound CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 2
• 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
• LRERDFJPYOAYKX-UHFFFAOYSA-N 2-methyl-1-naphthalen-1-ylsulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound C1=CC=C2N(S(=O)(=O)C=3C4=CC=CC=C4C=CC=3)C(C)=NC2=C1N1CCNCC1 LRERDFJPYOAYKX-UHFFFAOYSA-N 0.000 description 2
• XOISBGFUNDVODL-UHFFFAOYSA-N 2-methyl-4-(4-methylpiperazin-1-yl)-1-naphthalen-1-ylsulfonylbenzimidazole Chemical compound C1CN(C)CCN1C1=CC=CC2=C1N=C(C)N2S(=O)(=O)C1=CC=CC2=CC=CC=C12 XOISBGFUNDVODL-UHFFFAOYSA-N 0.000 description 2
• NKTDTMONXHODTI-UHFFFAOYSA-N 2-pentyne Chemical compound CCC#CC NKTDTMONXHODTI-UHFFFAOYSA-N 0.000 description 2
• MBBHQQSSVCCZOJ-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)-1-naphthalen-1-ylsulfonylbenzimidazole Chemical compound C1CN(C)CCN1C1=CC=CC2=C1N=CN2S(=O)(=O)C1=CC=CC2=CC=CC=C12 MBBHQQSSVCCZOJ-UHFFFAOYSA-N 0.000 description 2
• 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 2
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
• ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
• 241000283690 Bos taurus Species 0.000 description 2
• 206010013654 Drug abuse Diseases 0.000 description 2
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
• ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
• 102000014630 G protein-coupled serotonin receptor activity proteins Human genes 0.000 description 2
• 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 2
• 108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 2
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
• RLJFTICUTYVZDG-UHFFFAOYSA-N Methiothepine Chemical compound C12=CC(SC)=CC=C2SC2=CC=CC=C2CC1N1CCN(C)CC1 RLJFTICUTYVZDG-UHFFFAOYSA-N 0.000 description 2
• 208000016285 Movement disease Diseases 0.000 description 2
• MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 2
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
• 208000005793 Restless legs syndrome Diseases 0.000 description 2
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical group [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
• 230000009471 action Effects 0.000 description 2
• 230000004913 activation Effects 0.000 description 2
• 150000001299 aldehydes Chemical class 0.000 description 2
• 150000003973 alkyl amines Chemical class 0.000 description 2
• 238000004458 analytical method Methods 0.000 description 2
• 230000000561 anti-psychotic effect Effects 0.000 description 2
• 239000000010 aprotic solvent Substances 0.000 description 2
• 230000003542 behavioural effect Effects 0.000 description 2
• JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 2
• 238000004166 bioassay Methods 0.000 description 2
• 229910052796 boron Inorganic materials 0.000 description 2
• 229910052794 bromium Inorganic materials 0.000 description 2
• ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 2
• GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
• KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 125000002837 carbocyclic group Chemical group 0.000 description 2
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
• 229910052801 chlorine Inorganic materials 0.000 description 2
• 125000001309 chloro group Chemical group Cl* 0.000 description 2
• DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 2
• KQIADDMXRMTWHZ-UHFFFAOYSA-N chloro-tri(propan-2-yl)silane Chemical compound CC(C)[Si](Cl)(C(C)C)C(C)C KQIADDMXRMTWHZ-UHFFFAOYSA-N 0.000 description 2
• IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
• 230000001149 cognitive effect Effects 0.000 description 2
• 229940126214 compound 3 Drugs 0.000 description 2
• 125000004122 cyclic group Chemical group 0.000 description 2
• KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical group [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
• 229960003638 dopamine Drugs 0.000 description 2
• 206010013663 drug dependence Diseases 0.000 description 2
• 238000007876 drug discovery Methods 0.000 description 2
• 210000002889 endothelial cell Anatomy 0.000 description 2
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
• 239000000706 filtrate Substances 0.000 description 2
• 239000012458 free base Substances 0.000 description 2
• 239000007903 gelatin capsule Substances 0.000 description 2
• 230000036541 health Effects 0.000 description 2
• 238000010438 heat treatment Methods 0.000 description 2
• 150000002430 hydrocarbons Chemical group 0.000 description 2
• 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 description 2
• 238000001727 in vivo Methods 0.000 description 2
• 230000005764 inhibitory process Effects 0.000 description 2
• 238000001990 intravenous administration Methods 0.000 description 2
• 229910052740 iodine Inorganic materials 0.000 description 2
• 229940099584 lactobionate Drugs 0.000 description 2
• JYTUSYBCFIZPBE-AMTLMPIISA-M lactobionate Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O JYTUSYBCFIZPBE-AMTLMPIISA-M 0.000 description 2
• 239000007788 liquid Substances 0.000 description 2
• 230000004807 localization Effects 0.000 description 2
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
• 239000000463 material Substances 0.000 description 2
• 108020004999 messenger RNA Proteins 0.000 description 2
• 230000004048 modification Effects 0.000 description 2
• 238000012986 modification Methods 0.000 description 2
• 210000001577 neostriatum Anatomy 0.000 description 2
• 230000007107 neurocognitive deficit Effects 0.000 description 2
• 239000002547 new drug Substances 0.000 description 2
• 229910017604 nitric acid Inorganic materials 0.000 description 2
• 239000012454 non-polar solvent Substances 0.000 description 2
• 230000009871 nonspecific binding Effects 0.000 description 2
• 230000000269 nucleophilic effect Effects 0.000 description 2
• 230000003287 optical effect Effects 0.000 description 2
• 238000007911 parenteral administration Methods 0.000 description 2
• YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
• QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
• 239000000546 pharmaceutical excipient Substances 0.000 description 2
• 239000002798 polar solvent Substances 0.000 description 2
• 239000000843 powder Substances 0.000 description 2
• 239000003755 preservative agent Substances 0.000 description 2
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 239000003586 protic polar solvent Substances 0.000 description 2
• 238000000746 purification Methods 0.000 description 2
• 150000003254 radicals Chemical class 0.000 description 2
• 230000002829 reductive effect Effects 0.000 description 2
• 238000012552 review Methods 0.000 description 2
• 229940076279 serotonin Drugs 0.000 description 2
• 239000003751 serotonin 6 antagonist Substances 0.000 description 2
• 239000000377 silicon dioxide Substances 0.000 description 2
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
• 235000017557 sodium bicarbonate Nutrition 0.000 description 2
• 239000012312 sodium hydride Substances 0.000 description 2
• 239000004317 sodium nitrate Substances 0.000 description 2
• 235000010344 sodium nitrate Nutrition 0.000 description 2
• 235000010288 sodium nitrite Nutrition 0.000 description 2
• 230000009870 specific binding Effects 0.000 description 2
• 230000000638 stimulation Effects 0.000 description 2
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
• 239000006228 supernatant Substances 0.000 description 2
• 239000013589 supplement Substances 0.000 description 2
• 239000000375 suspending agent Substances 0.000 description 2
• 239000000725 suspension Substances 0.000 description 2
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
• 125000003396 thiol group Chemical group [H]S* 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
• 231100000027 toxicology Toxicity 0.000 description 2
• GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
• 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
• 229940070710 valerate Drugs 0.000 description 2
• NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
• 239000000080 wetting agent Substances 0.000 description 2
• SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
• SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
• GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 1
• 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 1
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
• XRNMRTYNRKLMPX-UHFFFAOYSA-N 1-(2,3-difluorophenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound FC1=CC=CC(S(=O)(=O)N2C3=CC=CC(=C3N=C2)N2CCNCC2)=C1F XRNMRTYNRKLMPX-UHFFFAOYSA-N 0.000 description 1
• JHUGXLUHMOJTEX-UHFFFAOYSA-N 1-(2,5-dichlorophenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound ClC1=CC=C(Cl)C(S(=O)(=O)N2C3=CC=CC(=C3N=C2)N2CCNCC2)=C1 JHUGXLUHMOJTEX-UHFFFAOYSA-N 0.000 description 1
• LTDGPDHSEDVTQD-UHFFFAOYSA-N 1-(2,5-difluorophenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound FC1=CC=C(F)C(S(=O)(=O)N2C3=CC=CC(=C3N=C2)N2CCNCC2)=C1 LTDGPDHSEDVTQD-UHFFFAOYSA-N 0.000 description 1
• CIQVAMQHEXBMSE-UHFFFAOYSA-N 1-(2,5-dimethoxyphenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound COC1=CC=C(OC)C(S(=O)(=O)N2C3=CC=CC(=C3N=C2)N2CCNCC2)=C1 CIQVAMQHEXBMSE-UHFFFAOYSA-N 0.000 description 1
• ZRYSOTBQOFLVQH-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound ClC1=CC=CC(Cl)=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2N=C1 ZRYSOTBQOFLVQH-UHFFFAOYSA-N 0.000 description 1
• FLUWTFYSTVFBFL-UHFFFAOYSA-N 1-(2-chloro-5-fluorophenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound FC1=CC=C(Cl)C(S(=O)(=O)N2C3=CC=CC(=C3N=C2)N2CCNCC2)=C1 FLUWTFYSTVFBFL-UHFFFAOYSA-N 0.000 description 1
• KSONKRMAFRDMGZ-UHFFFAOYSA-N 1-(2-chloro-6-methylphenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound CC1=CC=CC(Cl)=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2N=C1 KSONKRMAFRDMGZ-UHFFFAOYSA-N 0.000 description 1
• MSZUJTROIZQPPU-UHFFFAOYSA-N 1-(2-chlorophenyl)sulfonyl-2-methyl-4-(3-methylpiperazin-1-yl)benzimidazole Chemical compound C1CNC(C)CN1C1=CC=CC2=C1N=C(C)N2S(=O)(=O)C1=CC=CC=C1Cl MSZUJTROIZQPPU-UHFFFAOYSA-N 0.000 description 1
• WEZCQJKJHJIAPW-UHFFFAOYSA-N 1-(2-chlorophenyl)sulfonyl-2-methyl-4-piperazin-1-ylbenzimidazole Chemical compound CC1=NC2=C(N3CCNCC3)C=CC=C2N1S(=O)(=O)C1=CC=CC=C1Cl WEZCQJKJHJIAPW-UHFFFAOYSA-N 0.000 description 1
• KCPPJEJYOJBAKW-UHFFFAOYSA-N 1-(2-chlorophenyl)sulfonyl-4-(3-methylpiperazin-1-yl)benzimidazole Chemical compound C1CNC(C)CN1C1=CC=CC2=C1N=CN2S(=O)(=O)C1=CC=CC=C1Cl KCPPJEJYOJBAKW-UHFFFAOYSA-N 0.000 description 1
• CAFQOLUSGYOBJA-UHFFFAOYSA-N 1-(2-chlorophenyl)sulfonyl-4-(3-propan-2-ylpiperazin-1-yl)benzimidazole Chemical compound C1CNC(C(C)C)CN1C1=CC=CC2=C1N=CN2S(=O)(=O)C1=CC=CC=C1Cl CAFQOLUSGYOBJA-UHFFFAOYSA-N 0.000 description 1
• LWQKVGSIIWXZCA-KBPBESRZSA-N 1-(2-chlorophenyl)sulfonyl-4-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-2-methylbenzimidazole Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2C(C=1N=C2C)=CC=CC=1N2S(=O)(=O)C1=CC=CC=C1Cl LWQKVGSIIWXZCA-KBPBESRZSA-N 0.000 description 1
• YDAMWVYWTUIUGD-STQMWFEESA-N 1-(2-chlorophenyl)sulfonyl-4-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]benzimidazole Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2C(C=1N=C2)=CC=CC=1N2S(=O)(=O)C1=CC=CC=C1Cl YDAMWVYWTUIUGD-STQMWFEESA-N 0.000 description 1
• KCPPJEJYOJBAKW-CYBMUJFWSA-N 1-(2-chlorophenyl)sulfonyl-4-[(3r)-3-methylpiperazin-1-yl]benzimidazole Chemical compound C1CN[C@H](C)CN1C1=CC=CC2=C1N=CN2S(=O)(=O)C1=CC=CC=C1Cl KCPPJEJYOJBAKW-CYBMUJFWSA-N 0.000 description 1
• KRFUQKMOCVVLML-OKILXGFUSA-N 1-(2-chlorophenyl)sulfonyl-4-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-2-methylbenzimidazole Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=CC=CC2=C1N=C(C)N2S(=O)(=O)C1=CC=CC=C1Cl KRFUQKMOCVVLML-OKILXGFUSA-N 0.000 description 1
• KCPPJEJYOJBAKW-ZDUSSCGKSA-N 1-(2-chlorophenyl)sulfonyl-4-[(3s)-3-methylpiperazin-1-yl]benzimidazole Chemical compound C1CN[C@@H](C)CN1C1=CC=CC2=C1N=CN2S(=O)(=O)C1=CC=CC=C1Cl KCPPJEJYOJBAKW-ZDUSSCGKSA-N 0.000 description 1
• UZBVRHHSALHTHO-UHFFFAOYSA-N 1-(2-chlorophenyl)sulfonyl-4-[3-(2-methylpropyl)piperazin-1-yl]benzimidazole Chemical compound C1CNC(CC(C)C)CN1C1=CC=CC2=C1N=CN2S(=O)(=O)C1=CC=CC=C1Cl UZBVRHHSALHTHO-UHFFFAOYSA-N 0.000 description 1
• XXUNDIDKJNPTKR-UHFFFAOYSA-N 1-(2-chlorophenyl)sulfonyl-4-piperazin-1-yl-2-propan-2-ylbenzimidazole Chemical compound CC(C)C1=NC2=C(N3CCNCC3)C=CC=C2N1S(=O)(=O)C1=CC=CC=C1Cl XXUNDIDKJNPTKR-UHFFFAOYSA-N 0.000 description 1
• CJMIQJICHUKOAB-UHFFFAOYSA-N 1-(2-chlorophenyl)sulfonyl-6-fluoro-4-piperazin-1-ylbenzimidazole Chemical compound C=12N=CN(S(=O)(=O)C=3C(=CC=CC=3)Cl)C2=CC(F)=CC=1N1CCNCC1 CJMIQJICHUKOAB-UHFFFAOYSA-N 0.000 description 1
• OKASHSNCIWVEQG-UHFFFAOYSA-N 1-(2-ethoxyphenyl)sulfonyl-2-methyl-4-piperazin-1-ylbenzimidazole Chemical compound CCOC1=CC=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2N=C1C OKASHSNCIWVEQG-UHFFFAOYSA-N 0.000 description 1
• UHMDWLSBOFLTNQ-UHFFFAOYSA-N 1-(2-fluoro-3-methylphenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound CC1=CC=CC(S(=O)(=O)N2C3=CC=CC(=C3N=C2)N2CCNCC2)=C1F UHMDWLSBOFLTNQ-UHFFFAOYSA-N 0.000 description 1
• UOHNKMFVJAQPKV-UHFFFAOYSA-N 1-(2-fluoro-5-methylphenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound CC1=CC=C(F)C(S(=O)(=O)N2C3=CC=CC(=C3N=C2)N2CCNCC2)=C1 UOHNKMFVJAQPKV-UHFFFAOYSA-N 0.000 description 1
• ZFNAVGDDPOFANN-UHFFFAOYSA-N 1-(2-fluorophenyl)sulfonyl-2-methyl-4-piperazin-1-ylbenzimidazole Chemical compound CC1=NC2=C(N3CCNCC3)C=CC=C2N1S(=O)(=O)C1=CC=CC=C1F ZFNAVGDDPOFANN-UHFFFAOYSA-N 0.000 description 1
• QBDKJWXNFNUTKI-UHFFFAOYSA-N 1-(2-methoxy-4-methylphenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound COC1=CC(C)=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2N=C1 QBDKJWXNFNUTKI-UHFFFAOYSA-N 0.000 description 1
• DVTVDMSAFCWVMR-UHFFFAOYSA-N 1-(2-methoxy-5-methylphenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound COC1=CC=C(C)C=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2N=C1 DVTVDMSAFCWVMR-UHFFFAOYSA-N 0.000 description 1
• MNOJNMCLKRFVFU-UHFFFAOYSA-N 1-(2-methoxyphenyl)sulfonyl-2-methyl-4-piperazin-1-ylbenzimidazole Chemical compound COC1=CC=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2N=C1C MNOJNMCLKRFVFU-UHFFFAOYSA-N 0.000 description 1
• UPEGEYWUHUDBSE-UHFFFAOYSA-N 1-(2-methoxyphenyl)sulfonyl-4-(3-methylpiperazin-1-yl)benzimidazole Chemical compound COC1=CC=CC=C1S(=O)(=O)N1C2=CC=CC(N3CC(C)NCC3)=C2N=C1 UPEGEYWUHUDBSE-UHFFFAOYSA-N 0.000 description 1
• ISGXLLJTHQHBCC-UHFFFAOYSA-N 1-(2-methoxyphenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound COC1=CC=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2N=C1 ISGXLLJTHQHBCC-UHFFFAOYSA-N 0.000 description 1
• UQSYUYLKQPGDCM-UHFFFAOYSA-N 1-(2-methylphenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound CC1=CC=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2N=C1 UQSYUYLKQPGDCM-UHFFFAOYSA-N 0.000 description 1
• HSSFFDWWUSUMFB-UHFFFAOYSA-N 1-(3-chloro-2-methylphenyl)sulfonyl-2-methyl-4-(3-methylpiperazin-1-yl)benzimidazole Chemical compound C1CNC(C)CN1C1=CC=CC2=C1N=C(C)N2S(=O)(=O)C1=CC=CC(Cl)=C1C HSSFFDWWUSUMFB-UHFFFAOYSA-N 0.000 description 1
• OSINKNWDUIDVCG-UHFFFAOYSA-N 1-(3-chloro-2-methylphenyl)sulfonyl-4-(3-methylpiperazin-1-yl)benzimidazole Chemical compound C1CNC(C)CN1C1=CC=CC2=C1N=CN2S(=O)(=O)C1=CC=CC(Cl)=C1C OSINKNWDUIDVCG-UHFFFAOYSA-N 0.000 description 1
• BUZJIWPSGPSLDN-GJZGRUSLSA-N 1-(3-chloro-2-methylphenyl)sulfonyl-4-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-2-methylbenzimidazole Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2C(C=1N=C2C)=CC=CC=1N2S(=O)(=O)C1=CC=CC(Cl)=C1C BUZJIWPSGPSLDN-GJZGRUSLSA-N 0.000 description 1
• CDDFWIBFIXHGIS-KBPBESRZSA-N 1-(3-chloro-2-methylphenyl)sulfonyl-4-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]benzimidazole Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2C(C=1N=C2)=CC=CC=1N2S(=O)(=O)C1=CC=CC(Cl)=C1C CDDFWIBFIXHGIS-KBPBESRZSA-N 0.000 description 1
• OSINKNWDUIDVCG-CYBMUJFWSA-N 1-(3-chloro-2-methylphenyl)sulfonyl-4-[(3r)-3-methylpiperazin-1-yl]benzimidazole Chemical compound C1CN[C@H](C)CN1C1=CC=CC2=C1N=CN2S(=O)(=O)C1=CC=CC(Cl)=C1C OSINKNWDUIDVCG-CYBMUJFWSA-N 0.000 description 1
• SFURNCSAPADFDO-OKILXGFUSA-N 1-(3-chloro-2-methylphenyl)sulfonyl-4-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-2-methylbenzimidazole Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=CC=CC2=C1N=C(C)N2S(=O)(=O)C1=CC=CC(Cl)=C1C SFURNCSAPADFDO-OKILXGFUSA-N 0.000 description 1
• OSINKNWDUIDVCG-ZDUSSCGKSA-N 1-(3-chloro-2-methylphenyl)sulfonyl-4-[(3s)-3-methylpiperazin-1-yl]benzimidazole Chemical compound C1CN[C@@H](C)CN1C1=CC=CC2=C1N=CN2S(=O)(=O)C1=CC=CC(Cl)=C1C OSINKNWDUIDVCG-ZDUSSCGKSA-N 0.000 description 1
• HGPGCTNOAAZBSG-UHFFFAOYSA-N 1-(3-chloro-2-methylphenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2N=C1 HGPGCTNOAAZBSG-UHFFFAOYSA-N 0.000 description 1
• NJIZZEUODPMFPR-UHFFFAOYSA-N 1-(3-chloro-4-fluorophenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound C1=C(Cl)C(F)=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2N=C1 NJIZZEUODPMFPR-UHFFFAOYSA-N 0.000 description 1
• KNZDPEAMWOHLRP-UHFFFAOYSA-N 1-(3-chloro-5-fluorophenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound FC1=CC(Cl)=CC(S(=O)(=O)N2C3=CC=CC(=C3N=C2)N2CCNCC2)=C1 KNZDPEAMWOHLRP-UHFFFAOYSA-N 0.000 description 1
• JGRVFBOTHFMTIU-UHFFFAOYSA-N 1-(3-chlorophenyl)sulfonyl-2-methyl-4-piperazin-1-ylbenzimidazole Chemical compound CC1=NC2=C(N3CCNCC3)C=CC=C2N1S(=O)(=O)C1=CC=CC(Cl)=C1 JGRVFBOTHFMTIU-UHFFFAOYSA-N 0.000 description 1
• HUDHESIKHXHTKZ-UHFFFAOYSA-N 1-(3-chlorophenyl)sulfonyl-4-(3-methylpiperazin-1-yl)benzimidazole Chemical compound C1CNC(C)CN1C1=CC=CC2=C1N=CN2S(=O)(=O)C1=CC=CC(Cl)=C1 HUDHESIKHXHTKZ-UHFFFAOYSA-N 0.000 description 1
• HUDHESIKHXHTKZ-CYBMUJFWSA-N 1-(3-chlorophenyl)sulfonyl-4-[(3r)-3-methylpiperazin-1-yl]benzimidazole Chemical compound C1CN[C@H](C)CN1C1=CC=CC2=C1N=CN2S(=O)(=O)C1=CC=CC(Cl)=C1 HUDHESIKHXHTKZ-CYBMUJFWSA-N 0.000 description 1
• HUDHESIKHXHTKZ-ZDUSSCGKSA-N 1-(3-chlorophenyl)sulfonyl-4-[(3s)-3-methylpiperazin-1-yl]benzimidazole Chemical compound C1CN[C@@H](C)CN1C1=CC=CC2=C1N=CN2S(=O)(=O)C1=CC=CC(Cl)=C1 HUDHESIKHXHTKZ-ZDUSSCGKSA-N 0.000 description 1
• PMLYCWAFJBSFRF-UHFFFAOYSA-N 1-(3-chlorophenyl)sulfonyl-4-piperazin-1-yl-2-propan-2-ylbenzimidazole Chemical compound CC(C)C1=NC2=C(N3CCNCC3)C=CC=C2N1S(=O)(=O)C1=CC=CC(Cl)=C1 PMLYCWAFJBSFRF-UHFFFAOYSA-N 0.000 description 1
• PFHYKZOHBUONQE-UHFFFAOYSA-N 1-(3-fluoro-2-methoxyphenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound COC1=C(F)C=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2N=C1 PFHYKZOHBUONQE-UHFFFAOYSA-N 0.000 description 1
• MODOWPQDIGQJRQ-UHFFFAOYSA-N 1-(3-fluoro-2-methylphenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound CC1=C(F)C=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2N=C1 MODOWPQDIGQJRQ-UHFFFAOYSA-N 0.000 description 1
• HEPAYGHFOSDOFP-UHFFFAOYSA-N 1-(3-fluorophenyl)sulfonyl-2-methyl-4-(3-methylpiperazin-1-yl)benzimidazole Chemical compound C1CNC(C)CN1C1=CC=CC2=C1N=C(C)N2S(=O)(=O)C1=CC=CC(F)=C1 HEPAYGHFOSDOFP-UHFFFAOYSA-N 0.000 description 1
• FVDQJFZMSCNQDO-UHFFFAOYSA-N 1-(3-fluorophenyl)sulfonyl-2-methyl-4-piperazin-1-ylbenzimidazole Chemical compound CC1=NC2=C(N3CCNCC3)C=CC=C2N1S(=O)(=O)C1=CC=CC(F)=C1 FVDQJFZMSCNQDO-UHFFFAOYSA-N 0.000 description 1
• HMWTUPMSVZUKKB-UHFFFAOYSA-N 1-(3-methoxyphenyl)sulfonyl-2-methyl-4-piperazin-1-ylbenzimidazole Chemical compound COC1=CC=CC(S(=O)(=O)N2C3=CC=CC(=C3N=C2C)N2CCNCC2)=C1 HMWTUPMSVZUKKB-UHFFFAOYSA-N 0.000 description 1
• QEGLYRHSZJPWNM-UHFFFAOYSA-N 1-(3-methoxyphenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound COC1=CC=CC(S(=O)(=O)N2C3=CC=CC(=C3N=C2)N2CCNCC2)=C1 QEGLYRHSZJPWNM-UHFFFAOYSA-N 0.000 description 1
• XYNWHJMAIINCAF-UHFFFAOYSA-N 1-(3-methylphenyl)sulfonyl-4-(3-methylpiperazin-1-yl)benzimidazole Chemical compound C1CNC(C)CN1C1=CC=CC2=C1N=CN2S(=O)(=O)C1=CC=CC(C)=C1 XYNWHJMAIINCAF-UHFFFAOYSA-N 0.000 description 1
• SGMJIAWDNBSNDZ-UHFFFAOYSA-N 1-(3-methylphenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound CC1=CC=CC(S(=O)(=O)N2C3=CC=CC(=C3N=C2)N2CCNCC2)=C1 SGMJIAWDNBSNDZ-UHFFFAOYSA-N 0.000 description 1
• CUZZIJXKZHRGSK-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfonyl-2-methyl-4-piperazin-1-ylbenzimidazole Chemical compound CC1=NC2=C(N3CCNCC3)C=CC=C2N1S(=O)(=O)C1=CC=C(Cl)C=C1 CUZZIJXKZHRGSK-UHFFFAOYSA-N 0.000 description 1
• GENHLBHREKQWGH-UHFFFAOYSA-N 1-(4-fluorophenyl)sulfonyl-2-methyl-4-piperazin-1-ylbenzimidazole Chemical compound CC1=NC2=C(N3CCNCC3)C=CC=C2N1S(=O)(=O)C1=CC=C(F)C=C1 GENHLBHREKQWGH-UHFFFAOYSA-N 0.000 description 1
• ZUCWKKOMVMGKRR-UHFFFAOYSA-N 1-(4-fluorophenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound C1=CC(F)=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2N=C1 ZUCWKKOMVMGKRR-UHFFFAOYSA-N 0.000 description 1
• ZPXQNAQBZJUMLM-UHFFFAOYSA-N 1-(4-methoxyphenyl)sulfonyl-2-methyl-4-piperazin-1-ylbenzimidazole Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2N=C1C ZPXQNAQBZJUMLM-UHFFFAOYSA-N 0.000 description 1
• HMNBVQJFNBGHPP-UHFFFAOYSA-N 1-(4-methoxyphenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2N=C1 HMNBVQJFNBGHPP-UHFFFAOYSA-N 0.000 description 1
• CWWDENOSSCVODR-UHFFFAOYSA-N 1-(4-methylnaphthalen-1-yl)sulfonyl-4-piperazin-1-yl-2-propan-2-ylbenzimidazole Chemical compound C1=CC=C2N(S(=O)(=O)C=3C4=CC=CC=C4C(C)=CC=3)C(C(C)C)=NC2=C1N1CCNCC1 CWWDENOSSCVODR-UHFFFAOYSA-N 0.000 description 1
• GRPHONFPJZIDSH-UHFFFAOYSA-N 1-(4-methylnaphthalen-1-yl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound C12=CC=CC=C2C(C)=CC=C1S(=O)(=O)N(C1=CC=C2)C=NC1=C2N1CCNCC1 GRPHONFPJZIDSH-UHFFFAOYSA-N 0.000 description 1
• SGCFXPXBQBNCRA-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2N=C1 SGCFXPXBQBNCRA-UHFFFAOYSA-N 0.000 description 1
• YQWMAGNEUURTBH-UHFFFAOYSA-N 1-(5-bromo-2-methoxyphenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound COC1=CC=C(Br)C=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2N=C1 YQWMAGNEUURTBH-UHFFFAOYSA-N 0.000 description 1
• CYCQLKMUUIJAOR-UHFFFAOYSA-N 1-(5-chloro-2-methoxy-4-methylphenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound COC1=CC(C)=C(Cl)C=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2N=C1 CYCQLKMUUIJAOR-UHFFFAOYSA-N 0.000 description 1
• IKVUOGFXIYMLRP-UHFFFAOYSA-N 1-(5-chloro-2-methoxyphenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound COC1=CC=C(Cl)C=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2N=C1 IKVUOGFXIYMLRP-UHFFFAOYSA-N 0.000 description 1
• FXAZNEDJZDDEAP-HNNXBMFYSA-N 1-(5-chloronaphthalen-1-yl)sulfonyl-2-methyl-4-[(3s)-3-methylpiperazin-1-yl]benzimidazole Chemical compound C1CN[C@@H](C)CN1C1=CC=CC2=C1N=C(C)N2S(=O)(=O)C1=CC=CC2=C(Cl)C=CC=C12 FXAZNEDJZDDEAP-HNNXBMFYSA-N 0.000 description 1
• DCDKFFLZCYGWSY-UHFFFAOYSA-N 1-(5-chloronaphthalen-1-yl)sulfonyl-4-piperazin-1-yl-2-propan-2-ylbenzimidazole Chemical compound C1=CC=C2N(S(=O)(=O)C=3C4=CC=CC(Cl)=C4C=CC=3)C(C(C)C)=NC2=C1N1CCNCC1 DCDKFFLZCYGWSY-UHFFFAOYSA-N 0.000 description 1
• FNZUMYPTQWHABK-UHFFFAOYSA-N 1-(5-chloronaphthalen-1-yl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1S(=O)(=O)N(C1=CC=C2)C=NC1=C2N1CCNCC1 FNZUMYPTQWHABK-UHFFFAOYSA-N 0.000 description 1
• REPZNMMRJYSEJD-UHFFFAOYSA-N 1-(benzenesulfonyl)-2-methyl-4-(3-methylpiperazin-1-yl)benzimidazole Chemical compound C1CNC(C)CN1C1=CC=CC2=C1N=C(C)N2S(=O)(=O)C1=CC=CC=C1 REPZNMMRJYSEJD-UHFFFAOYSA-N 0.000 description 1
• REPZNMMRJYSEJD-CQSZACIVSA-N 1-(benzenesulfonyl)-2-methyl-4-[(3r)-3-methylpiperazin-1-yl]benzimidazole Chemical compound C1CN[C@H](C)CN1C1=CC=CC2=C1N=C(C)N2S(=O)(=O)C1=CC=CC=C1 REPZNMMRJYSEJD-CQSZACIVSA-N 0.000 description 1
• REPZNMMRJYSEJD-AWEZNQCLSA-N 1-(benzenesulfonyl)-2-methyl-4-[(3s)-3-methylpiperazin-1-yl]benzimidazole Chemical compound C1CN[C@@H](C)CN1C1=CC=CC2=C1N=C(C)N2S(=O)(=O)C1=CC=CC=C1 REPZNMMRJYSEJD-AWEZNQCLSA-N 0.000 description 1
• APTNKQCKOBBOOZ-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-(3-ethylpiperazin-1-yl)benzimidazole Chemical compound C1CNC(CC)CN1C1=CC=CC2=C1N=CN2S(=O)(=O)C1=CC=CC=C1 APTNKQCKOBBOOZ-UHFFFAOYSA-N 0.000 description 1
• ZDKWSMJTECNGND-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-(3-methylpiperazin-1-yl)benzimidazole Chemical compound C1CNC(C)CN1C1=CC=CC2=C1N=CN2S(=O)(=O)C1=CC=CC=C1 ZDKWSMJTECNGND-UHFFFAOYSA-N 0.000 description 1
• ARWOLNSIBZDHEW-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-(3-propan-2-ylpiperazin-1-yl)benzimidazole Chemical compound C1CNC(C(C)C)CN1C1=CC=CC2=C1N=CN2S(=O)(=O)C1=CC=CC=C1 ARWOLNSIBZDHEW-UHFFFAOYSA-N 0.000 description 1
• IAFVJIZJZDFVMX-GJZGRUSLSA-N 1-(benzenesulfonyl)-4-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-2-methylbenzimidazole Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2C(C=1N=C2C)=CC=CC=1N2S(=O)(=O)C1=CC=CC=C1 IAFVJIZJZDFVMX-GJZGRUSLSA-N 0.000 description 1
• LNDBTDTYEJNZNS-KBPBESRZSA-N 1-(benzenesulfonyl)-4-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]benzimidazole Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2C(C=1N=C2)=CC=CC=1N2S(=O)(=O)C1=CC=CC=C1 LNDBTDTYEJNZNS-KBPBESRZSA-N 0.000 description 1
• HKGJAQKFKKATIV-GASCZTMLSA-N 1-(benzenesulfonyl)-4-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-2-methylbenzimidazole Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=CC=CC2=C1N=C(C)N2S(=O)(=O)C1=CC=CC=C1 HKGJAQKFKKATIV-GASCZTMLSA-N 0.000 description 1
• NYKMDPYQUKKUTL-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-[3-(2-methylpropyl)piperazin-1-yl]benzimidazole Chemical compound C1CNC(CC(C)C)CN1C1=CC=CC2=C1N=CN2S(=O)(=O)C1=CC=CC=C1 NYKMDPYQUKKUTL-UHFFFAOYSA-N 0.000 description 1
• KGAAUJRYRUHGCJ-UHFFFAOYSA-N 1-(benzenesulfonyl)-6-fluoro-4-piperazin-1-ylbenzimidazole Chemical compound C=12N=CN(S(=O)(=O)C=3C=CC=CC=3)C2=CC(F)=CC=1N1CCNCC1 KGAAUJRYRUHGCJ-UHFFFAOYSA-N 0.000 description 1
• BHNYDQGLLURBRJ-UHFFFAOYSA-N 1-[2-chloro-5-(trifluoromethyl)phenyl]sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound FC(F)(F)C1=CC=C(Cl)C(S(=O)(=O)N2C3=CC=CC(=C3N=C2)N2CCNCC2)=C1 BHNYDQGLLURBRJ-UHFFFAOYSA-N 0.000 description 1
• PPJVXZVTPWQOQS-UHFFFAOYSA-N 1-ethoxy-1-(1-ethoxyethoxy)ethane Chemical compound CCOC(C)OC(C)OCC PPJVXZVTPWQOQS-UHFFFAOYSA-N 0.000 description 1
• CGHIBGNXEGJPQZ-UHFFFAOYSA-N 1-hexyne Chemical compound CCCCC#C CGHIBGNXEGJPQZ-UHFFFAOYSA-N 0.000 description 1
• SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 description 1
• GPAAEZIXSQCCES-UHFFFAOYSA-N 1-methoxy-2-(2-methoxyethoxymethoxymethoxy)ethane Chemical compound COCCOCOCOCCOC GPAAEZIXSQCCES-UHFFFAOYSA-N 0.000 description 1
• RLAWQMKYBXXPDO-UHFFFAOYSA-N 1-naphthalen-1-ylsulfonyl-4-(3-propan-2-ylpiperazin-1-yl)benzimidazole Chemical compound C1CNC(C(C)C)CN1C1=CC=CC2=C1N=CN2S(=O)(=O)C1=CC=CC2=CC=CC=C12 RLAWQMKYBXXPDO-UHFFFAOYSA-N 0.000 description 1
• CSDVIXYRGTXNPU-UHFFFAOYSA-N 1-naphthalen-1-ylsulfonyl-4-piperazin-1-yl-2-propan-2-ylbenzimidazole Chemical compound C1=CC=C2N(S(=O)(=O)C=3C4=CC=CC=C4C=CC=3)C(C(C)C)=NC2=C1N1CCNCC1 CSDVIXYRGTXNPU-UHFFFAOYSA-N 0.000 description 1
• BEEBPZVWUDSUCX-UHFFFAOYSA-N 1-naphthalen-2-ylsulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound C=1C=C2C=CC=CC2=CC=1S(=O)(=O)N(C1=CC=C2)C=NC1=C2N1CCNCC1 BEEBPZVWUDSUCX-UHFFFAOYSA-N 0.000 description 1
• 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 1
• IBXNCJKFFQIKKY-UHFFFAOYSA-N 1-pentyne Chemical compound CCCC#C IBXNCJKFFQIKKY-UHFFFAOYSA-N 0.000 description 1
• 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 102000010400 1-phosphatidylinositol-3-kinase activity proteins Human genes 0.000 description 1
• NZJKEQFPRPAEPO-UHFFFAOYSA-N 1h-benzimidazol-4-amine Chemical compound NC1=CC=CC2=C1N=CN2 NZJKEQFPRPAEPO-UHFFFAOYSA-N 0.000 description 1
• NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 1
• MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
• MDFOIGCWCMAGKS-UHFFFAOYSA-N 2,3-dinitrobenzenediazonium Chemical compound [O-][N+](=O)C1=CC=CC([N+]#N)=C1[N+]([O-])=O MDFOIGCWCMAGKS-UHFFFAOYSA-N 0.000 description 1
• HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical class O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 1
• MLONYBFKXHEPCD-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(N)(CO)CO.OCC(N)(CO)CO MLONYBFKXHEPCD-UHFFFAOYSA-N 0.000 description 1
• QNUYOGVDLFQHHZ-UHFFFAOYSA-N 2-methyl-1-(2-methylphenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound CC1=NC2=C(N3CCNCC3)C=CC=C2N1S(=O)(=O)C1=CC=CC=C1C QNUYOGVDLFQHHZ-UHFFFAOYSA-N 0.000 description 1
• BYUFPDQCMZCJAO-UHFFFAOYSA-N 2-methyl-1-(3-methylphenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound CC1=NC2=C(N3CCNCC3)C=CC=C2N1S(=O)(=O)C1=CC=CC(C)=C1 BYUFPDQCMZCJAO-UHFFFAOYSA-N 0.000 description 1
• ANPJTDSLRZSNGZ-UHFFFAOYSA-N 2-methyl-1-(4-methylnaphthalen-1-yl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound C1=CC=C2N(S(=O)(=O)C=3C4=CC=CC=C4C(C)=CC=3)C(C)=NC2=C1N1CCNCC1 ANPJTDSLRZSNGZ-UHFFFAOYSA-N 0.000 description 1
• AMHOOHYTBAZYNX-UHFFFAOYSA-N 2-methyl-1-(4-methylphenyl)sulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound CC1=NC2=C(N3CCNCC3)C=CC=C2N1S(=O)(=O)C1=CC=C(C)C=C1 AMHOOHYTBAZYNX-UHFFFAOYSA-N 0.000 description 1
• HJYJXWUACRTTQY-UHFFFAOYSA-N 2-methyl-1-naphthalen-2-ylsulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound C1=CC=C2N(S(=O)(=O)C=3C=C4C=CC=CC4=CC=3)C(C)=NC2=C1N1CCNCC1 HJYJXWUACRTTQY-UHFFFAOYSA-N 0.000 description 1
• QCFAKTACICNQGT-UHFFFAOYSA-N 2-methyl-2-[(2-methylpropan-2-yl)oxymethoxymethoxy]propane Chemical compound CC(C)(C)OCOCOC(C)(C)C QCFAKTACICNQGT-UHFFFAOYSA-N 0.000 description 1
• TYFIQTYBSMOYQT-UHFFFAOYSA-N 2-methyl-4-(3-methylpiperazin-1-yl)-1-naphthalen-1-ylsulfonylbenzimidazole Chemical compound C1CNC(C)CN1C1=CC=CC2=C1N=C(C)N2S(=O)(=O)C1=CC=CC2=CC=CC=C12 TYFIQTYBSMOYQT-UHFFFAOYSA-N 0.000 description 1
• TYFIQTYBSMOYQT-MRXNPFEDSA-N 2-methyl-4-[(3r)-3-methylpiperazin-1-yl]-1-naphthalen-1-ylsulfonylbenzimidazole Chemical compound C1CN[C@H](C)CN1C1=CC=CC2=C1N=C(C)N2S(=O)(=O)C1=CC=CC2=CC=CC=C12 TYFIQTYBSMOYQT-MRXNPFEDSA-N 0.000 description 1
• TYFIQTYBSMOYQT-INIZCTEOSA-N 2-methyl-4-[(3s)-3-methylpiperazin-1-yl]-1-naphthalen-1-ylsulfonylbenzimidazole Chemical compound C1CN[C@@H](C)CN1C1=CC=CC2=C1N=C(C)N2S(=O)(=O)C1=CC=CC2=CC=CC=C12 TYFIQTYBSMOYQT-INIZCTEOSA-N 0.000 description 1
• QQRGBIRTLQJLKB-UHFFFAOYSA-N 2-methyl-4-piperazin-1-yl-1-[2-(trifluoromethoxy)phenyl]sulfonylbenzimidazole Chemical compound CC1=NC2=C(N3CCNCC3)C=CC=C2N1S(=O)(=O)C1=CC=CC=C1OC(F)(F)F QQRGBIRTLQJLKB-UHFFFAOYSA-N 0.000 description 1
• WWDIUBYUTBZEAX-UHFFFAOYSA-N 2-methyl-4-piperazin-1-yl-1-[2-(trifluoromethyl)phenyl]sulfonylbenzimidazole Chemical compound CC1=NC2=C(N3CCNCC3)C=CC=C2N1S(=O)(=O)C1=CC=CC=C1C(F)(F)F WWDIUBYUTBZEAX-UHFFFAOYSA-N 0.000 description 1
• QRRHGUFMANJMSO-UHFFFAOYSA-N 2-methyl-4-piperazin-1-yl-1-[3-(trifluoromethoxy)phenyl]sulfonylbenzimidazole Chemical compound CC1=NC2=C(N3CCNCC3)C=CC=C2N1S(=O)(=O)C1=CC=CC(OC(F)(F)F)=C1 QRRHGUFMANJMSO-UHFFFAOYSA-N 0.000 description 1
• GICZABCELCJOQT-UHFFFAOYSA-N 2-methyl-4-piperazin-1-yl-1-[3-(trifluoromethyl)phenyl]sulfonylbenzimidazole Chemical compound CC1=NC2=C(N3CCNCC3)C=CC=C2N1S(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 GICZABCELCJOQT-UHFFFAOYSA-N 0.000 description 1
• HMJQMTQQHPKXHU-UHFFFAOYSA-N 2-methyl-4-piperazin-1-yl-1-[4-(trifluoromethoxy)phenyl]sulfonylbenzimidazole Chemical compound CC1=NC2=C(N3CCNCC3)C=CC=C2N1S(=O)(=O)C1=CC=C(OC(F)(F)F)C=C1 HMJQMTQQHPKXHU-UHFFFAOYSA-N 0.000 description 1
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
• ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
• FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 1
• ALKYHXVLJMQRLQ-UHFFFAOYSA-M 3-carboxynaphthalen-2-olate Chemical compound C1=CC=C2C=C(C([O-])=O)C(O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-M 0.000 description 1
• ZQDPJFUHLCOCRG-UHFFFAOYSA-N 3-hexene Chemical compound CCC=CCC ZQDPJFUHLCOCRG-UHFFFAOYSA-N 0.000 description 1
• DQQNMIPXXNPGCV-UHFFFAOYSA-N 3-hexyne Chemical compound CCC#CCC DQQNMIPXXNPGCV-UHFFFAOYSA-N 0.000 description 1
• YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 1
• 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• UCJXVBCNAWRFIB-UHFFFAOYSA-N 4-(3-ethylpiperazin-1-yl)-1-naphthalen-1-ylsulfonylbenzimidazole Chemical compound C1CNC(CC)CN1C1=CC=CC2=C1N=CN2S(=O)(=O)C1=CC=CC2=CC=CC=C12 UCJXVBCNAWRFIB-UHFFFAOYSA-N 0.000 description 1
• WPYDLBHQDDNQGT-UHFFFAOYSA-N 4-(3-methylpiperazin-1-yl)-1-[2-(trifluoromethoxy)phenyl]sulfonylbenzimidazole Chemical compound C1CNC(C)CN1C1=CC=CC2=C1N=CN2S(=O)(=O)C1=CC=CC=C1OC(F)(F)F WPYDLBHQDDNQGT-UHFFFAOYSA-N 0.000 description 1
• JISFAPGVDMBOSC-UHFFFAOYSA-N 4-(3-methylpiperazin-1-yl)-1-naphthalen-1-ylsulfonylbenzimidazole Chemical compound C1CNC(C)CN1C1=CC=CC2=C1N=CN2S(=O)(=O)C1=CC=CC2=CC=CC=C12 JISFAPGVDMBOSC-UHFFFAOYSA-N 0.000 description 1
• ILTBTUDDTRHBML-GJZGRUSLSA-N 4-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-1-(3-fluorophenyl)sulfonyl-2-methylbenzimidazole Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2C(C=1N=C2C)=CC=CC=1N2S(=O)(=O)C1=CC=CC(F)=C1 ILTBTUDDTRHBML-GJZGRUSLSA-N 0.000 description 1
• PBCDDVRIAYJODW-KBPBESRZSA-N 4-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-1-(3-fluorophenyl)sulfonylbenzimidazole Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2C(C=1N=C2)=CC=CC=1N2S(=O)(=O)C1=CC=CC(F)=C1 PBCDDVRIAYJODW-KBPBESRZSA-N 0.000 description 1
• WBGSUBKUEHRCKG-IRXDYDNUSA-N 4-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-1-naphthalen-1-ylsulfonylbenzimidazole Chemical compound C1=CC=C2C(S(=O)(=O)N3C=4C=CC=C(C=4N=C3)N3C[C@]4(NC[C@]3([H])C4)[H])=CC=CC2=C1 WBGSUBKUEHRCKG-IRXDYDNUSA-N 0.000 description 1
• UARHVVRYZNLNAM-ROUUACIJSA-N 4-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-2-methyl-1-naphthalen-1-ylsulfonylbenzimidazole Chemical compound C1=CC=C2C(S(=O)(=O)N3C=4C=CC=C(C=4N=C3C)N3C[C@]4(NC[C@]3([H])C4)[H])=CC=CC2=C1 UARHVVRYZNLNAM-ROUUACIJSA-N 0.000 description 1
• JISFAPGVDMBOSC-MRXNPFEDSA-N 4-[(3r)-3-methylpiperazin-1-yl]-1-naphthalen-1-ylsulfonylbenzimidazole Chemical compound C1CN[C@H](C)CN1C1=CC=CC2=C1N=CN2S(=O)(=O)C1=CC=CC2=CC=CC=C12 JISFAPGVDMBOSC-MRXNPFEDSA-N 0.000 description 1
• WQTJQEVHFCYEOQ-OKILXGFUSA-N 4-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-1-(3-fluorophenyl)sulfonyl-2-methylbenzimidazole Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=CC=CC2=C1N=C(C)N2S(=O)(=O)C1=CC=CC(F)=C1 WQTJQEVHFCYEOQ-OKILXGFUSA-N 0.000 description 1
• DTPVWMWMNPOHEJ-CALCHBBNSA-N 4-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-2-methyl-1-naphthalen-1-ylsulfonylbenzimidazole Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=CC=CC2=C1N=C(C)N2S(=O)(=O)C1=CC=CC2=CC=CC=C12 DTPVWMWMNPOHEJ-CALCHBBNSA-N 0.000 description 1
• JISFAPGVDMBOSC-INIZCTEOSA-N 4-[(3s)-3-methylpiperazin-1-yl]-1-naphthalen-1-ylsulfonylbenzimidazole Chemical compound C1CN[C@@H](C)CN1C1=CC=CC2=C1N=CN2S(=O)(=O)C1=CC=CC2=CC=CC=C12 JISFAPGVDMBOSC-INIZCTEOSA-N 0.000 description 1
• FCZRPEQXVWVVAQ-UHFFFAOYSA-N 4-[3-(2-methylpropyl)piperazin-1-yl]-1-naphthalen-1-ylsulfonylbenzimidazole Chemical compound C1CNC(CC(C)C)CN1C1=CC=CC2=C1N=CN2S(=O)(=O)C1=CC=CC2=CC=CC=C12 FCZRPEQXVWVVAQ-UHFFFAOYSA-N 0.000 description 1
• WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 1
• OXRWICUICBZVAE-UHFFFAOYSA-N 4-methylpent-1-yne Chemical compound CC(C)CC#C OXRWICUICBZVAE-UHFFFAOYSA-N 0.000 description 1
• RRBLAGDZHLKRLY-UHFFFAOYSA-N 4-piperazin-1-yl-1-[2-(trifluoromethoxy)phenyl]sulfonylbenzimidazole Chemical compound FC(F)(F)OC1=CC=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2N=C1 RRBLAGDZHLKRLY-UHFFFAOYSA-N 0.000 description 1
• LMEBIFMBOCYKCP-UHFFFAOYSA-N 4-piperazin-1-yl-1-[2-(trifluoromethyl)phenyl]sulfonylbenzimidazole Chemical compound FC(F)(F)C1=CC=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2N=C1 LMEBIFMBOCYKCP-UHFFFAOYSA-N 0.000 description 1
• NCRJOIGLHUFODP-UHFFFAOYSA-N 4-piperazin-1-yl-1-[3-(trifluoromethoxy)phenyl]sulfonylbenzimidazole Chemical compound FC(F)(F)OC1=CC=CC(S(=O)(=O)N2C3=CC=CC(=C3N=C2)N2CCNCC2)=C1 NCRJOIGLHUFODP-UHFFFAOYSA-N 0.000 description 1
• GKZKNNWWADDKED-UHFFFAOYSA-N 4-piperazin-1-yl-1-[3-(trifluoromethyl)phenyl]sulfonylbenzimidazole Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)N2C3=CC=CC(=C3N=C2)N2CCNCC2)=C1 GKZKNNWWADDKED-UHFFFAOYSA-N 0.000 description 1
• LIRDQDAWGKLZQY-UHFFFAOYSA-N 4-piperazin-1-yl-1-[4-(trifluoromethoxy)phenyl]sulfonylbenzimidazole Chemical compound C1=CC(OC(F)(F)F)=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2N=C1 LIRDQDAWGKLZQY-UHFFFAOYSA-N 0.000 description 1
• BHOBNQDOVWVAAL-UHFFFAOYSA-N 4-piperazin-1-yl-1-[4-(trifluoromethyl)phenyl]sulfonylbenzimidazole Chemical compound C1=CC(C(F)(F)F)=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2N=C1 BHOBNQDOVWVAAL-UHFFFAOYSA-N 0.000 description 1
• MBROKNNWSJWGFM-UHFFFAOYSA-N 4-piperazin-1-yl-2-propan-2-yl-1-[2-(trifluoromethoxy)phenyl]sulfonylbenzimidazole Chemical compound CC(C)C1=NC2=C(N3CCNCC3)C=CC=C2N1S(=O)(=O)C1=CC=CC=C1OC(F)(F)F MBROKNNWSJWGFM-UHFFFAOYSA-N 0.000 description 1
• VERUFXOALATMPS-UHFFFAOYSA-N 5,5-diamino-2-(2-phenylethenyl)cyclohex-3-ene-1,1-disulfonic acid Chemical compound C1=CC(N)(N)CC(S(O)(=O)=O)(S(O)(=O)=O)C1C=CC1=CC=CC=C1 VERUFXOALATMPS-UHFFFAOYSA-N 0.000 description 1
• 108091005435 5-HT6 receptors Proteins 0.000 description 1
• JYQJGQOJDPOHPB-UHFFFAOYSA-N 6-fluoro-1-naphthalen-1-ylsulfonyl-4-piperazin-1-ylbenzimidazole Chemical compound C=12N=CN(S(=O)(=O)C=3C4=CC=CC=C4C=CC=3)C2=CC(F)=CC=1N1CCNCC1 JYQJGQOJDPOHPB-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
• BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
• FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
• 125000005915 C6-C14 aryl group Chemical group 0.000 description 1
• 208000011597 CGF1 Diseases 0.000 description 1
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
• 241000700199 Cavia porcellus Species 0.000 description 1
• 241000282693 Cercopithecidae Species 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
• 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
• RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
• AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 description 1
• 208000020401 Depressive disease Diseases 0.000 description 1
• 241000283073 Equus caballus Species 0.000 description 1
• 241000282326 Felis catus Species 0.000 description 1
• 239000004606 Fillers/Extenders Substances 0.000 description 1
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
• BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
• 241000282575 Gorilla Species 0.000 description 1
• 206010019196 Head injury Diseases 0.000 description 1
• VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
• CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 1
• JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 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
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• 208000019430 Motor disease Diseases 0.000 description 1
• 241000699666 Mus <mouse, genus> Species 0.000 description 1
• 229910002651 NO3 Inorganic materials 0.000 description 1
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
• 108091007960 PI3Ks Proteins 0.000 description 1
• 229910019142 PO4 Inorganic materials 0.000 description 1
• 241000282577 Pan troglodytes Species 0.000 description 1
• 241001504519 Papio ursinus Species 0.000 description 1
• 241000009328 Perro Species 0.000 description 1
• 206010062519 Poor quality sleep Diseases 0.000 description 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
• 102000004257 Potassium Channel Human genes 0.000 description 1
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
• 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
• 208000006011 Stroke Diseases 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
• 241000282898 Sus scrofa Species 0.000 description 1
• 102000013530 TOR Serine-Threonine Kinases Human genes 0.000 description 1
• 108010065917 TOR Serine-Threonine Kinases Proteins 0.000 description 1
• 229920002253 Tannate Polymers 0.000 description 1
• YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
• 108010046516 Wheat Germ Agglutinins Proteins 0.000 description 1
• 125000004062 acenaphthenyl group Chemical group C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
• WJGAPUXHSQQWQF-UHFFFAOYSA-N acetic acid;hydrochloride Chemical compound Cl.CC(O)=O WJGAPUXHSQQWQF-UHFFFAOYSA-N 0.000 description 1
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
• OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
• 229960004373 acetylcholine Drugs 0.000 description 1
• 239000002253 acid Substances 0.000 description 1
• 230000009056 active transport 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
• 239000002671 adjuvant Substances 0.000 description 1
• 230000008484 agonism Effects 0.000 description 1
• 125000001931 aliphatic group Chemical group 0.000 description 1
• 125000003545 alkoxy group Chemical group 0.000 description 1
• 125000003282 alkyl amino group Chemical group 0.000 description 1
• 125000000304 alkynyl group Chemical group 0.000 description 1
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-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
• 150000001412 amines Chemical class 0.000 description 1
• 125000004103 aminoalkyl group Chemical group 0.000 description 1
• 229950003153 amsonate Drugs 0.000 description 1
• 150000001450 anions Chemical class 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
• 239000000883 anti-obesity agent Substances 0.000 description 1
• 239000000935 antidepressant agent Substances 0.000 description 1
• 229940005513 antidepressants Drugs 0.000 description 1
• 229940125710 antiobesity agent Drugs 0.000 description 1
• 239000000164 antipsychotic agent Substances 0.000 description 1
• 229940005529 antipsychotics Drugs 0.000 description 1
• 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
• 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 1
• 229940009098 aspartate Drugs 0.000 description 1
• 238000003556 assay Methods 0.000 description 1
• 125000004429 atom Chemical group 0.000 description 1
• OISFUZRUIGGTSD-LJTMIZJLSA-N azane;(2r,3r,4r,5s)-6-(methylamino)hexane-1,2,3,4,5-pentol Chemical compound N.CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO OISFUZRUIGGTSD-LJTMIZJLSA-N 0.000 description 1
• 239000011324 bead Substances 0.000 description 1
• 229940077388 benzenesulfonate Drugs 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
• 239000011230 binding agent Substances 0.000 description 1
• 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
• 229910052797 bismuth Inorganic materials 0.000 description 1
• JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 description 1
• 229910000085 borane Inorganic materials 0.000 description 1
• 239000012152 bradford reagent Substances 0.000 description 1
• 210000004781 brain capillary Anatomy 0.000 description 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
• IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
• 229910052792 caesium Inorganic materials 0.000 description 1
• TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
• 229910000024 caesium carbonate Inorganic materials 0.000 description 1
• 239000011575 calcium Substances 0.000 description 1
• 229910052791 calcium Inorganic materials 0.000 description 1
• FATUQANACHZLRT-KMRXSBRUSA-L calcium glucoheptonate Chemical compound [Ca+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O FATUQANACHZLRT-KMRXSBRUSA-L 0.000 description 1
• 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
• 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
• 150000001768 cations Chemical class 0.000 description 1
• 210000001159 caudate nucleus Anatomy 0.000 description 1
• 239000006285 cell suspension Substances 0.000 description 1
• 230000001413 cellular effect Effects 0.000 description 1
• 238000005119 centrifugation Methods 0.000 description 1
• 125000003636 chemical group Chemical group 0.000 description 1
• 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
• OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
• 229960001231 choline Drugs 0.000 description 1
• 238000004587 chromatography analysis 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
• 239000002475 cognitive enhancer Substances 0.000 description 1
• 239000003086 colorant Substances 0.000 description 1
• 229940125782 compound 2 Drugs 0.000 description 1
• 238000007796 conventional method Methods 0.000 description 1
• NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
• 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 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
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 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
• 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
• 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 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
• 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
• 230000001419 dependent effect Effects 0.000 description 1
• 238000011161 development Methods 0.000 description 1
• 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
• 239000012954 diazonium Substances 0.000 description 1
• 150000001989 diazonium salts Chemical class 0.000 description 1
• IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
• MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical class C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
• ACYGYJFTZSAZKR-UHFFFAOYSA-J dicalcium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Ca+2].[Ca+2].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O ACYGYJFTZSAZKR-UHFFFAOYSA-J 0.000 description 1
• ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
• 238000009792 diffusion process Methods 0.000 description 1
• SPCNPOWOBZQWJK-UHFFFAOYSA-N dimethoxy-(2-propan-2-ylsulfanylethylsulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound COP(=S)(OC)SCCSC(C)C SPCNPOWOBZQWJK-UHFFFAOYSA-N 0.000 description 1
• ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
• 239000001177 diphosphate Substances 0.000 description 1
• XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
• 235000011180 diphosphates Nutrition 0.000 description 1
• LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
• 239000007884 disintegrant Substances 0.000 description 1
• 238000010494 dissociation reaction Methods 0.000 description 1
• 230000005593 dissociations Effects 0.000 description 1
• 125000004119 disulfanediyl group Chemical group *SS* 0.000 description 1
• POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
• MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
• 229940043264 dodecyl sulfate Drugs 0.000 description 1
• 230000004064 dysfunction Effects 0.000 description 1
• 229940009662 edetate Drugs 0.000 description 1
• 229960001484 edetic acid Drugs 0.000 description 1
• 239000008157 edible vegetable oil Substances 0.000 description 1
• 239000012039 electrophile Substances 0.000 description 1
• 238000000132 electrospray ionisation Methods 0.000 description 1
• 238000000921 elemental analysis Methods 0.000 description 1
• 229950005627 embonate Drugs 0.000 description 1
• 239000003995 emulsifying agent Substances 0.000 description 1
• 239000000839 emulsion Substances 0.000 description 1
• 230000002708 enhancing effect Effects 0.000 description 1
• 150000002148 esters Chemical class 0.000 description 1
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
• 238000002474 experimental method Methods 0.000 description 1
• 238000000605 extraction Methods 0.000 description 1
• 230000002349 favourable effect Effects 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 238000003818 flash chromatography Methods 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
• 239000011737 fluorine Substances 0.000 description 1
• 229910052731 fluorine Inorganic materials 0.000 description 1
• 238000009472 formulation Methods 0.000 description 1
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
• 210000005153 frontal cortex Anatomy 0.000 description 1
• VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
• 238000010230 functional analysis Methods 0.000 description 1
• 108010074605 gamma-Globulins Proteins 0.000 description 1
• 239000012362 glacial acetic acid Substances 0.000 description 1
• 229960001731 gluceptate Drugs 0.000 description 1
• KWMLJOLKUYYJFJ-VFUOTHLCSA-N glucoheptonic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(O)=O KWMLJOLKUYYJFJ-VFUOTHLCSA-N 0.000 description 1
• 229940050410 gluconate Drugs 0.000 description 1
• 239000008103 glucose Substances 0.000 description 1
• 229940097042 glucuronate Drugs 0.000 description 1
• 229940049906 glutamate Drugs 0.000 description 1
• 125000001188 haloalkyl group Chemical group 0.000 description 1
• 230000026030 halogenation Effects 0.000 description 1
• 238000005658 halogenation reaction Methods 0.000 description 1
• 125000005842 heteroatom Chemical group 0.000 description 1
• MELUCTCJOARQQG-UHFFFAOYSA-N hex-2-yne Chemical compound CCCC#CC MELUCTCJOARQQG-UHFFFAOYSA-N 0.000 description 1
• IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 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
• XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
• 238000006197 hydroboration reaction Methods 0.000 description 1
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
• 208000013403 hyperactivity Diseases 0.000 description 1
• 150000003949 imides Chemical class 0.000 description 1
• 238000007901 in situ hybridization Methods 0.000 description 1
• 238000000099 in vitro assay Methods 0.000 description 1
• 238000005462 in vivo assay Methods 0.000 description 1
• 238000011534 incubation Methods 0.000 description 1
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
• 239000003112 inhibitor Substances 0.000 description 1
• 238000002347 injection Methods 0.000 description 1
• 239000007924 injection Substances 0.000 description 1
• 229910052500 inorganic mineral Inorganic materials 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 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
• 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 229940070765 laurate Drugs 0.000 description 1
• 239000012669 liquid formulation Substances 0.000 description 1
• 239000006194 liquid suspension Substances 0.000 description 1
• 229910052744 lithium Inorganic materials 0.000 description 1
• 229960001078 lithium Drugs 0.000 description 1
• 230000033001 locomotion Effects 0.000 description 1
• 230000007774 longterm Effects 0.000 description 1
• 239000007937 lozenge Substances 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 239000006166 lysate Substances 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• 229940091250 magnesium supplement Drugs 0.000 description 1
• IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
• GWCYPEHWIZXYFZ-UHFFFAOYSA-N masupirdine Chemical compound C12=CC(OC)=CC=C2N(S(=O)(=O)C=2C(=CC=CC=2)Br)C=C1CN1CCN(C)CC1 GWCYPEHWIZXYFZ-UHFFFAOYSA-N 0.000 description 1
• 230000001404 mediated effect Effects 0.000 description 1
• 238000002483 medication Methods 0.000 description 1
• 229960003194 meglumine Drugs 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• 238000003328 mesylation reaction Methods 0.000 description 1
• NSPJNIDYTSSIIY-UHFFFAOYSA-N methoxy(methoxymethoxy)methane Chemical compound COCOCOC NSPJNIDYTSSIIY-UHFFFAOYSA-N 0.000 description 1
• 229940102396 methyl bromide Drugs 0.000 description 1
• LRMHVVPPGGOAJQ-UHFFFAOYSA-N methyl nitrate Chemical compound CO[N+]([O-])=O LRMHVVPPGGOAJQ-UHFFFAOYSA-N 0.000 description 1
• JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
• CPZBTYRIGVOOMI-UHFFFAOYSA-N methylsulfanyl(methylsulfanylmethoxy)methane Chemical compound CSCOCSC CPZBTYRIGVOOMI-UHFFFAOYSA-N 0.000 description 1
• 238000003801 milling Methods 0.000 description 1
• 235000010755 mineral Nutrition 0.000 description 1
• 239000011707 mineral Substances 0.000 description 1
• NXQGEDVQXVTCDA-UHFFFAOYSA-N n,n-dimethyl-3-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]propan-1-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCCN(C)C)=CC=CC2=C1 NXQGEDVQXVTCDA-UHFFFAOYSA-N 0.000 description 1
• PILCQJJJAFRKHO-UHFFFAOYSA-N n-[1-(5-chloro-2,3-dimethoxyphenyl)ethyl]-2-methylsulfonyl-5-piperazin-1-ylaniline;hydrochloride Chemical compound Cl.COC1=CC(Cl)=CC(C(C)NC=2C(=CC=C(C=2)N2CCNCC2)S(C)(=O)=O)=C1OC PILCQJJJAFRKHO-UHFFFAOYSA-N 0.000 description 1
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 230000001722 neurochemical effect Effects 0.000 description 1
• 238000002610 neuroimaging Methods 0.000 description 1
• 239000003176 neuroleptic agent Substances 0.000 description 1
• 230000000701 neuroleptic effect Effects 0.000 description 1
• 229960002715 nicotine Drugs 0.000 description 1
• SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
• 238000006396 nitration reaction Methods 0.000 description 1
• 239000002687 nonaqueous vehicle Substances 0.000 description 1
• SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
• 229960002748 norepinephrine Drugs 0.000 description 1
• 239000012038 nucleophile Substances 0.000 description 1
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
• 239000003921 oil Substances 0.000 description 1
• 229940049964 oleate Drugs 0.000 description 1
• ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 1
• 239000006186 oral dosage form Substances 0.000 description 1
• 150000002894 organic compounds Chemical class 0.000 description 1
• 239000007800 oxidant agent Substances 0.000 description 1
• 125000004043 oxo group Chemical group O=* 0.000 description 1
• 229910052760 oxygen Inorganic materials 0.000 description 1
• 125000005440 p-toluyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C(*)=O)C([H])([H])[H] 0.000 description 1
• 229940014662 pantothenate Drugs 0.000 description 1
• 235000019161 pantothenic acid Nutrition 0.000 description 1
• 239000011713 pantothenic acid Substances 0.000 description 1
• 239000006201 parenteral dosage form Substances 0.000 description 1
• 230000035515 penetration Effects 0.000 description 1
• 235000019371 penicillin G benzathine Nutrition 0.000 description 1
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
• 230000000144 pharmacologic effect Effects 0.000 description 1
• FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical compound OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 description 1
• TYZYRCHEVXXLSJ-UHFFFAOYSA-N phenylmethoxymethoxymethoxymethylbenzene Chemical compound C=1C=CC=CC=1COCOCOCC1=CC=CC=C1 TYZYRCHEVXXLSJ-UHFFFAOYSA-N 0.000 description 1
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
• 239000010452 phosphate Substances 0.000 description 1
• XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
• 230000037081 physical activity Effects 0.000 description 1
• 229940075930 picrate Drugs 0.000 description 1
• OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
• 229920000642 polymer Polymers 0.000 description 1
• 230000008092 positive effect Effects 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 108020001213 potassium channel Proteins 0.000 description 1
• VLYFRFHWUBBLRR-UHFFFAOYSA-L potassium;sodium;carbonate Chemical compound [Na+].[K+].[O-]C([O-])=O VLYFRFHWUBBLRR-UHFFFAOYSA-L 0.000 description 1
• 230000003389 potentiating effect Effects 0.000 description 1
• 210000002442 prefrontal cortex Anatomy 0.000 description 1
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
• MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
• 210000004129 prosencephalon Anatomy 0.000 description 1
• 238000000159 protein binding assay Methods 0.000 description 1
• 102000004169 proteins and genes Human genes 0.000 description 1
• 108090000623 proteins and genes Proteins 0.000 description 1
• 239000012264 purified product Substances 0.000 description 1
• 210000002637 putamen Anatomy 0.000 description 1
• 230000002285 radioactive effect Effects 0.000 description 1
• 239000011541 reaction mixture Substances 0.000 description 1
• 230000009257 reactivity Effects 0.000 description 1
• 238000011084 recovery Methods 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 238000000611 regression analysis Methods 0.000 description 1
• 230000001105 regulatory effect Effects 0.000 description 1
• 230000004044 response Effects 0.000 description 1
• XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
• 229920006395 saturated elastomer Polymers 0.000 description 1
• 229930195734 saturated hydrocarbon Natural products 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
• 208000012201 sexual and gender identity disease Diseases 0.000 description 1
• 208000015891 sexual disease Diseases 0.000 description 1
• 230000007781 signaling event Effects 0.000 description 1
• 230000004039 social cognition Effects 0.000 description 1
• 239000011734 sodium Substances 0.000 description 1
• 229910052938 sodium sulfate Inorganic materials 0.000 description 1
• 235000011152 sodium sulphate Nutrition 0.000 description 1
• 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
• ABBQHOQBGMUPJH-UHFFFAOYSA-N sodium;2-hydroxybenzoic acid Chemical compound [Na+].OC(=O)C1=CC=CC=C1O ABBQHOQBGMUPJH-UHFFFAOYSA-N 0.000 description 1
• 230000003595 spectral effect Effects 0.000 description 1
• 239000007858 starting material Substances 0.000 description 1
• 239000008223 sterile water Substances 0.000 description 1
• 239000012258 stirred mixture Substances 0.000 description 1
• 238000003860 storage Methods 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• 201000009032 substance abuse Diseases 0.000 description 1
• 231100000736 substance abuse Toxicity 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
• 238000000967 suction filtration Methods 0.000 description 1
• 150000003457 sulfones Chemical class 0.000 description 1
• 229910052717 sulfur Inorganic materials 0.000 description 1
• 239000011593 sulfur Substances 0.000 description 1
• 230000016978 synaptic transmission, cholinergic Effects 0.000 description 1
• 238000001308 synthesis method Methods 0.000 description 1
• 230000002194 synthesizing effect Effects 0.000 description 1
• 239000006188 syrup Substances 0.000 description 1
• 235000020357 syrup Nutrition 0.000 description 1
• 229940095064 tartrate Drugs 0.000 description 1
• 229950002757 teoclate Drugs 0.000 description 1
• BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
• 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
• 238000002560 therapeutic procedure Methods 0.000 description 1
• 150000003568 thioethers Chemical group 0.000 description 1
• 210000001578 tight junction Anatomy 0.000 description 1
• 238000007070 tosylation reaction Methods 0.000 description 1
• 229940066528 trichloroacetate Drugs 0.000 description 1
• YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
• UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
• 239000005051 trimethylchlorosilane Substances 0.000 description 1
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
• 229910052722 tritium Inorganic materials 0.000 description 1
• 229960000281 trometamol Drugs 0.000 description 1
• 230000031836 visual learning Effects 0.000 description 1
• RYBOXBBYCVOYNO-UHFFFAOYSA-N way-181,187 Chemical compound C1=CC=C2C(CCN)=CN(S(=O)(=O)C=3N4C=CSC4=NC=3Cl)C2=C1 RYBOXBBYCVOYNO-UHFFFAOYSA-N 0.000 description 1
• 230000003936 working memory Effects 0.000 description 1
• 150000003751 zinc Chemical class 0.000 description 1