ZA200504043B - N-arylsulfony; 3-substituted indoles having serotonin receptor affinity, process for their preparation and pharmaceutical compositions containing them - Google Patents

N-arylsulfony; 3-substituted indoles having serotonin receptor affinity, process for their preparation and pharmaceutical compositions containing them Download PDF

Info

Publication number: ZA200504043B
Authority: ZA; South Africa
Prior art keywords: indole; methylpiperazin; yimethyl; bromo; indol
Prior art date: 2002-11-28

Application number

ZA200504043A

Other languages

English (en)

Inventor

Venkata S N Ramakrishna

Vikas S Shirsath

Rama S Kambhampati

Venkata S V V Rao

Venkateswarlu Jasti

Original Assignee

Suven Life Sciences Ltd

Priority date (The priority date 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 date listed.)

2002-11-28

Filing date

2005-05-19

Publication date

2006-07-26

2005-05-19 Application filed by Suven Life Sciences Ltd filed Critical Suven Life Sciences Ltd

2006-07-26 Publication of ZA200504043B publication Critical patent/ZA200504043B/en

Links

-1 3-substituted indoles Chemical class 0.000 title claims description 58
238000000034 method Methods 0.000 title claims description 23
238000002360 preparation method Methods 0.000 title claims description 16
108091032151 5-hydroxytryptamine receptor family Proteins 0.000 title claims description 11
239000008194 pharmaceutical composition Substances 0.000 title claims description 9
102000040125 5-hydroxytryptamine receptor family Human genes 0.000 title claims description 7
150000003839 salts Chemical class 0.000 claims abstract description 20
150000001204 N-oxides Chemical class 0.000 claims abstract description 7
150000001875 compounds Chemical class 0.000 claims description 90
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 50
SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 48
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 32
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 32
229910052757 nitrogen Inorganic materials 0.000 claims description 31
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
125000005842 heteroatom Chemical group 0.000 claims description 28
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
238000011282 treatment Methods 0.000 claims description 24
208000035475 disorder Diseases 0.000 claims description 19
208000019695 Migraine disease Diseases 0.000 claims description 17
206010027599 migraine Diseases 0.000 claims description 17
125000004432 carbon atom Chemical group C* 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
239000011669 selenium Substances 0.000 claims description 15
229910052717 sulfur Inorganic materials 0.000 claims description 15
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 14
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 14
BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 14
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
125000003710 aryl alkyl group Chemical group 0.000 claims description 14
125000001072 heteroaryl group Chemical group 0.000 claims description 14
125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 14
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 14
229910052760 oxygen Inorganic materials 0.000 claims description 14
239000001301 oxygen Substances 0.000 claims description 14
229910052711 selenium Inorganic materials 0.000 claims description 14
239000011593 sulfur Substances 0.000 claims description 14
125000003545 alkoxy group Chemical group 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 13
125000000304 alkynyl group Chemical group 0.000 claims description 13
125000003118 aryl group Chemical group 0.000 claims description 13
150000001602 bicycloalkyls Chemical group 0.000 claims description 13
FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 11
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 11
208000028017 Psychotic disease Diseases 0.000 claims description 11
125000003342 alkenyl group Chemical group 0.000 claims description 11
125000000392 cycloalkenyl group Chemical group 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 11
239000003814 drug Substances 0.000 claims description 10
230000000694 effects Effects 0.000 claims description 10
239000012453 solvate Substances 0.000 claims description 10
208000019901 Anxiety disease Diseases 0.000 claims description 9
229910052799 carbon Inorganic materials 0.000 claims description 9
125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 9
238000011321 prophylaxis Methods 0.000 claims description 9
208000024827 Alzheimer disease Diseases 0.000 claims description 8
230000036506 anxiety Effects 0.000 claims description 8
125000000623 heterocyclic group Chemical group 0.000 claims description 8
239000000543 intermediate Substances 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
201000000980 schizophrenia Diseases 0.000 claims description 8
125000002252 acyl group Chemical group 0.000 claims description 7
125000004442 acylamino group Chemical group 0.000 claims description 7
125000004423 acyloxy group Chemical group 0.000 claims description 7
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 7
125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 7
125000004414 alkyl thio group Chemical group 0.000 claims description 7
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 7
125000001769 aryl amino group Chemical group 0.000 claims description 7
125000005162 aryl oxy carbonyl amino group Chemical group 0.000 claims description 7
125000004104 aryloxy group Chemical group 0.000 claims description 7
125000004663 dialkyl amino group Chemical group 0.000 claims description 7
125000004986 diarylamino group Chemical group 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
125000004475 heteroaralkyl group Chemical group 0.000 claims description 7
125000005553 heteroaryloxy group Chemical group 0.000 claims description 7
125000005226 heteroaryloxycarbonyl group Chemical group 0.000 claims description 7
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
125000004043 oxo group Chemical group O=* 0.000 claims description 7
238000006467 substitution reaction Methods 0.000 claims description 7
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 7
150000003460 sulfonic acids Chemical class 0.000 claims description 7
125000004001 thioalkyl group Chemical group 0.000 claims description 7
208000023105 Huntington disease Diseases 0.000 claims description 6
208000027089 Parkinsonian disease Diseases 0.000 claims description 6
206010034010 Parkinsonism Diseases 0.000 claims description 6
125000004103 aminoalkyl group Chemical group 0.000 claims description 6
125000006598 aminocarbonylamino group Chemical group 0.000 claims description 6
125000001691 aryl alkyl amino group Chemical group 0.000 claims description 6
125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 6
OZEYXHPIKLICLU-UHFFFAOYSA-N hydrazinyl(hydroxy)carbamic acid Chemical compound N(N)N(O)C(=O)O OZEYXHPIKLICLU-UHFFFAOYSA-N 0.000 claims description 6
208000015122 neurodegenerative disease Diseases 0.000 claims description 6
208000011580 syndromic disease Diseases 0.000 claims description 6
125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 5
206010010904 Convulsion Diseases 0.000 claims description 5
206010026749 Mania Diseases 0.000 claims description 5
208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 5
206010033664 Panic attack Diseases 0.000 claims description 5
208000036752 Schizophrenia, paranoid type Diseases 0.000 claims description 5
206010047700 Vomiting Diseases 0.000 claims description 5
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 5
238000002512 chemotherapy Methods 0.000 claims description 5
239000003112 inhibitor Substances 0.000 claims description 5
208000024714 major depressive disease Diseases 0.000 claims description 5
208000019906 panic disease Diseases 0.000 claims description 5
208000022821 personality disease Diseases 0.000 claims description 5
208000019116 sleep disease Diseases 0.000 claims description 5
208000011117 substance-related disease Diseases 0.000 claims description 5
206010013654 Drug abuse Diseases 0.000 claims description 4
102000014630 G protein-coupled serotonin receptor activity proteins Human genes 0.000 claims description 4
206010019196 Head injury Diseases 0.000 claims description 4
208000026139 Memory disease Diseases 0.000 claims description 4
208000010877 cognitive disease Diseases 0.000 claims description 4
230000001149 cognitive effect Effects 0.000 claims description 4
230000002950 deficient Effects 0.000 claims description 4
230000006870 function Effects 0.000 claims description 4
208000013403 hyperactivity Diseases 0.000 claims description 4
208000014674 injury Diseases 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
208000027061 mild cognitive impairment Diseases 0.000 claims description 4
230000008733 trauma Effects 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 3
230000002496 gastric effect Effects 0.000 claims description 3
239000000203 mixture Substances 0.000 claims description 3
PLLVYYHPNFOESC-UHFFFAOYSA-N 1-(2-bromophenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]-5-nitroindole Chemical compound C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C(=CC=CC=2)Br)C2=CC=C([N+]([O-])=O)C=C12 PLLVYYHPNFOESC-UHFFFAOYSA-N 0.000 claims description 2
CUJACFWWRCFAMF-UHFFFAOYSA-N 1-(2-bromophenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]-5-nitroindole;hydrochloride Chemical compound Cl.C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C(=CC=CC=2)Br)C2=CC=C([N+]([O-])=O)C=C12 CUJACFWWRCFAMF-UHFFFAOYSA-N 0.000 claims description 2
HZFPOIDKRPOAAB-UHFFFAOYSA-N 1-(2-bromophenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]indole;hydrochloride Chemical compound Cl.C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C(=CC=CC=2)Br)C2=CC=CC=C12 HZFPOIDKRPOAAB-UHFFFAOYSA-N 0.000 claims description 2
ZYUBETKYUVIEIY-UHFFFAOYSA-N 1-(4-bromophenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]indole-5-carbonitrile Chemical compound C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C=CC(Br)=CC=2)C2=CC=C(C#N)C=C12 ZYUBETKYUVIEIY-UHFFFAOYSA-N 0.000 claims description 2
GQJYYUAGLADWPG-UHFFFAOYSA-N 1-(4-fluorophenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]-5-nitroindole Chemical compound C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C=CC(F)=CC=2)C2=CC=C([N+]([O-])=O)C=C12 GQJYYUAGLADWPG-UHFFFAOYSA-N 0.000 claims description 2
YDRLSTVVRBLOHG-UHFFFAOYSA-N 1-(4-fluorophenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]indole-5-carbonitrile Chemical compound C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C=CC(F)=CC=2)C2=CC=C(C#N)C=C12 YDRLSTVVRBLOHG-UHFFFAOYSA-N 0.000 claims description 2
WCMKMNBKLDQDMF-UHFFFAOYSA-N 1-(4-methoxyphenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]-5-nitroindole Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=C([N+]([O-])=O)C=C2C(CN2CCN(C)CC2)=C1 WCMKMNBKLDQDMF-UHFFFAOYSA-N 0.000 claims description 2
RGTQOVPAOBVRLI-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-3-[1-(4-methylpiperazin-1-yl)ethyl]indole Chemical compound C=1N(S(=O)(=O)C=2C=CC(C)=CC=2)C2=CC=CC=C2C=1C(C)N1CCN(C)CC1 RGTQOVPAOBVRLI-UHFFFAOYSA-N 0.000 claims description 2
QLXFEJIRXVMHNH-UHFFFAOYSA-N 1-(4-propan-2-ylphenyl)sulfonyl-3-[(4-pyridin-2-ylpiperazin-1-yl)methyl]indole Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(CN2CCN(CC2)C=2N=CC=CC=2)=C1 QLXFEJIRXVMHNH-UHFFFAOYSA-N 0.000 claims description 2
XCUQQNRWWCWVOP-UHFFFAOYSA-N 2-(4-methylpiperazin-1-yl)acetonitrile Chemical compound CN1CCN(CC#N)CC1 XCUQQNRWWCWVOP-UHFFFAOYSA-N 0.000 claims description 2
WZOIYLIDQGPBSD-UHFFFAOYSA-N 3-[1-(4-methylpiperazin-1-yl)ethyl]-1-(4-propan-2-ylphenyl)sulfonylindole Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(C(C)N2CCN(C)CC2)=C1 WZOIYLIDQGPBSD-UHFFFAOYSA-N 0.000 claims description 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 2
GDRMZOHMLQZYPY-UHFFFAOYSA-N 5-methoxy-3-[[4-(2-methoxyphenyl)piperazin-1-yl]methyl]-1-(4-propan-2-ylphenyl)sulfonylindole Chemical compound C12=CC(OC)=CC=C2N(S(=O)(=O)C=2C=CC(=CC=2)C(C)C)C=C1CN(CC1)CCN1C1=CC=CC=C1OC GDRMZOHMLQZYPY-UHFFFAOYSA-N 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
125000005160 aryl oxy alkyl group Chemical group 0.000 claims 6
125000004070 6 membered heterocyclic group Chemical group 0.000 claims 4
239000002253 acid Substances 0.000 claims 4
125000001246 bromo group Chemical group Br* 0.000 claims 4
125000001309 chloro group Chemical group Cl* 0.000 claims 4
125000005843 halogen group Chemical group 0.000 claims 4
125000002346 iodo group Chemical group I* 0.000 claims 4
208000002551 irritable bowel syndrome Diseases 0.000 claims 4
125000002373 5 membered heterocyclic group Chemical group 0.000 claims 3
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims 2
230000002265 prevention Effects 0.000 claims 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
DKFJMSXDIDGXEM-UHFFFAOYSA-N 1-(4-bromophenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]-5-nitroindole Chemical compound C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C=CC(Br)=CC=2)C2=CC=C([N+]([O-])=O)C=C12 DKFJMSXDIDGXEM-UHFFFAOYSA-N 0.000 claims 1
JQSOUZQNWRSGCT-UHFFFAOYSA-N 1-(4-fluorophenyl)sulfonyl-5-methoxy-3-[(4-pyridin-2-ylpiperazin-1-yl)methyl]indole Chemical compound C12=CC(OC)=CC=C2N(S(=O)(=O)C=2C=CC(F)=CC=2)C=C1CN(CC1)CCN1C1=CC=CC=N1 JQSOUZQNWRSGCT-UHFFFAOYSA-N 0.000 claims 1
AVIQOMXISMYLAD-QGZVFWFLSA-N 1-(4-methoxyphenyl)sulfonyl-3-[(1r)-1-(4-methylpiperazin-1-yl)ethyl]indole Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C([C@@H](C)N2CCN(C)CC2)=C1 AVIQOMXISMYLAD-QGZVFWFLSA-N 0.000 claims 1
CYEZCUPFDACBTO-UHFFFAOYSA-N 1-(4-propan-2-ylphenyl)sulfonylindole-3-carboxylic acid Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(C(O)=O)=C1 CYEZCUPFDACBTO-UHFFFAOYSA-N 0.000 claims 1
KHMLBOHUMMRYRG-KRWDZBQOSA-N 1-(benzenesulfonyl)-3-[(1s)-1-(4-methylpiperazin-1-yl)ethyl]indole Chemical compound N1([C@@H](C)C=2C3=CC=CC=C3N(C=2)S(=O)(=O)C=2C=CC=CC=2)CCN(C)CC1 KHMLBOHUMMRYRG-KRWDZBQOSA-N 0.000 claims 1
KHMLBOHUMMRYRG-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-[1-(4-methylpiperazin-1-yl)ethyl]indole Chemical compound C=1N(S(=O)(=O)C=2C=CC=CC=2)C2=CC=CC=C2C=1C(C)N1CCN(C)CC1 KHMLBOHUMMRYRG-UHFFFAOYSA-N 0.000 claims 1
GZISCDFYXJHFBQ-UHFFFAOYSA-N 1-(benzenesulfonyl)-5-methoxy-3-[(4-methylpiperazin-1-yl)methyl]indole Chemical compound C12=CC(OC)=CC=C2N(S(=O)(=O)C=2C=CC=CC=2)C=C1CN1CCN(C)CC1 GZISCDFYXJHFBQ-UHFFFAOYSA-N 0.000 claims 1
MHICIMUCVFSNDN-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-1-(4-propan-2-ylphenyl)sulfonylindole-5-carbonitrile Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)N1C2=CC=C(C#N)C=C2C(CN2CCN(C)CC2)=C1 MHICIMUCVFSNDN-UHFFFAOYSA-N 0.000 claims 1
SERXWDAUKDFLTJ-UHFFFAOYSA-N 4-bromo-1-(4-fluorophenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]indole Chemical compound C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C=CC(F)=CC=2)C2=CC=CC(Br)=C12 SERXWDAUKDFLTJ-UHFFFAOYSA-N 0.000 claims 1
DGNZIOXFWMMBAM-UHFFFAOYSA-N 5-bromo-1-(2-bromo-4-methoxyphenyl)sulfonyl-3-(1,4-diazepan-1-ylmethyl)indole Chemical compound BrC1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=C(Br)C=C2C(CN2CCNCCC2)=C1 DGNZIOXFWMMBAM-UHFFFAOYSA-N 0.000 claims 1
OESDAVYRNYTCPX-UHFFFAOYSA-N 5-bromo-1-(2-bromophenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]indole;hydrochloride Chemical compound Cl.C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C(=CC=CC=2)Br)C2=CC=C(Br)C=C12 OESDAVYRNYTCPX-UHFFFAOYSA-N 0.000 claims 1
XTUUHRQZGUKXFK-BTJKTKAUSA-N 5-bromo-1-(4-fluorophenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]indole;(z)-but-2-enedioic acid Chemical compound OC(=O)\C=C/C(O)=O.C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C=CC(F)=CC=2)C2=CC=C(Br)C=C12 XTUUHRQZGUKXFK-BTJKTKAUSA-N 0.000 claims 1
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 claims 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims 1
BJQGJPQIONVXFR-UHFFFAOYSA-N [1-(2-bromophenyl)sulfonylindol-3-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CN(S(=O)(=O)C=2C(=CC=CC=2)Br)C2=CC=CC=C12 BJQGJPQIONVXFR-UHFFFAOYSA-N 0.000 claims 1
UEMFHQFJMMNSGC-UHFFFAOYSA-N [1-(4-fluorophenyl)sulfonyl-5-nitroindol-3-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CN(S(=O)(=O)C=2C=CC(F)=CC=2)C2=CC=C([N+]([O-])=O)C=C12 UEMFHQFJMMNSGC-UHFFFAOYSA-N 0.000 claims 1
HKMILLJQIWROSA-UHFFFAOYSA-N [1-(4-methoxyphenyl)sulfonyl-5-nitroindol-3-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=C([N+]([O-])=O)C=C2C(C(=O)N2CCN(C)CC2)=C1 HKMILLJQIWROSA-UHFFFAOYSA-N 0.000 claims 1
PUQJKTXLWAKUET-UHFFFAOYSA-N [1-(benzenesulfonyl)-5-nitroindol-3-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CN(S(=O)(=O)C=2C=CC=CC=2)C2=CC=C([N+]([O-])=O)C=C12 PUQJKTXLWAKUET-UHFFFAOYSA-N 0.000 claims 1
239000007864 aqueous solution Substances 0.000 claims 1
239000002775 capsule Substances 0.000 claims 1
150000001860 citric acid derivatives Chemical class 0.000 claims 1
238000010511 deprotection reaction Methods 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
230000002140 halogenating effect Effects 0.000 claims 1
RJTZUHVCZIGJMB-UHFFFAOYSA-N hydron;1h-indole;chloride Chemical compound Cl.C1=CC=C2NC=CC2=C1 RJTZUHVCZIGJMB-UHFFFAOYSA-N 0.000 claims 1
125000001041 indolyl group Chemical group 0.000 claims 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims 1
IMLOBUGYKCAVKW-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-1-(4-fluorophenyl)sulfonyl-n-methylindole-3-carboxamide Chemical compound C12=CC=CC=C2C(C(=O)N(C)CCN(C)C)=CN1S(=O)(=O)C1=CC=C(F)C=C1 IMLOBUGYKCAVKW-UHFFFAOYSA-N 0.000 claims 1
IZLRAWMHRUFEKL-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-1-(4-methoxyphenyl)sulfonyl-n-methylindole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(C(=O)N(C)CCN(C)C)=C1 IZLRAWMHRUFEKL-UHFFFAOYSA-N 0.000 claims 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
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Classifications

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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07—ORGANIC CHEMISTRY
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- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

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ZA200504043A 2002-11-28 2005-05-19 N-arylsulfony; 3-substituted indoles having serotonin receptor affinity, process for their preparation and pharmaceutical compositions containing them ZA200504043B (en)

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KR (1)	KR100818508B1 (pt)
CN (2)	CN101544592B (pt)
AT (1)	ATE401307T1 (pt)
AU (1)	AU2003237599B2 (pt)
BR (2)	BRPI0315959C1 (pt)
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Publication number	Publication date
PT1581492E (pt)	2008-09-19
EA011320B1 (ru)	2009-02-27
EP1581492B1 (en)	2008-07-16
KR100818508B1 (ko)	2008-03-31
JP2006514011A (ja)	2006-04-27
CN101544592B (zh)	2013-08-21
NO20052737D0 (no)	2005-06-08
JP4559230B2 (ja)	2010-10-06
CY1108786T1 (el)	2014-04-09
CN1720225A (zh)	2006-01-11
ES2310243T3 (es)	2009-01-01
BR0315959A (pt)	2005-09-13
NZ572186A (en)	2010-02-26
EP1581492A1 (en)	2005-10-05
BRPI0315959B8 (pt)	2018-01-16
CA2509982C (en)	2011-11-08
US20060223890A1 (en)	2006-10-05
SI1581492T1 (sl)	2008-12-31
CN1720225B (zh)	2011-05-18
AU2003237599A1 (en)	2004-06-18
BRPI0318799B1 (pt)	2019-06-25
NO20085054L (no)	2005-08-25
BRPI0318799B8 (pt)	2021-05-25
MXPA05005701A (es)	2005-08-16
CA2509982A1 (en)	2004-06-10
CN101544592A (zh)	2009-09-30
US7875605B2 (en)	2011-01-25
KR20050086868A (ko)	2005-08-30
BRPI0315959B1 (pt)	2017-12-19
WO2004048330A8 (en)	2005-10-27
DE60322266D1 (de)	2008-08-28
NO20052737L (no)	2005-08-25
NZ540840A (en)	2008-12-24
WO2004048330A1 (en)	2004-06-10
HK1083217A1 (en)	2006-06-30
DK1581492T3 (da)	2008-11-10
NO335015B1 (no)	2014-08-25
EA200500881A1 (ru)	2005-12-29
ATE401307T1 (de)	2008-08-15
BRPI0315959C1 (pt)	2021-05-25
NO330341B1 (no)	2011-03-28
HK1133002A1 (pt)	2010-03-12
AU2003237599B2 (en)	2009-06-18

Publication	Publication Date	Title
ZA200504043B (en)	2006-07-26	N-arylsulfony; 3-substituted indoles having serotonin receptor affinity, process for their preparation and pharmaceutical compositions containing them
ZA200504044B (en)	2006-07-26	N-arylsufonyl-3-aminoalkoxyindoles
JP2006514011A5 (pt)	2009-03-05
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CN106170288B (zh)	2019-07-19	药物化合物
JP6761413B2 (ja)	2020-09-23	シグマ受容体結合剤
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CN109219594A (zh)	2019-01-15	吲哚啉类似物及其用途
ZA200405731B (en)	2007-02-28	Indolylalkylamine derivatives as 5-hydroxytryptamine-6 ligands
CN107108580A (zh)	2017-08-29	吲哚酮化合物及其用途
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TW201022247A (en)	2010-06-16	1-(arylsulfonyl)-4-(piperazin-1-yl)-1H-benzimidazoles as 5-hydroxytryptamine-6 ligands
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