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
239000000546 pharmaceutical excipient Substances 0.000 claims 1
239000000843 powder Substances 0.000 claims 1
229940002612 prodrug Drugs 0.000 claims 1
239000000651 prodrug Substances 0.000 claims 1
125000006239 protecting group Chemical group 0.000 claims 1
229910000033 sodium borohydride Inorganic materials 0.000 claims 1
239000012279 sodium borohydride Substances 0.000 claims 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 claims 1
239000000243 solution Substances 0.000 claims 1
239000000725 suspension Substances 0.000 claims 1
239000006188 syrup Substances 0.000 claims 1
235000020357 syrup Nutrition 0.000 claims 1
239000003826 tablet Substances 0.000 claims 1
150000002475 indoles Chemical class 0.000 abstract description 6
102000005962 receptors Human genes 0.000 description 12
108020003175 receptors Proteins 0.000 description 12
229940076279 serotonin Drugs 0.000 description 8
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
201000010099 disease Diseases 0.000 description 6
239000000018 receptor agonist Substances 0.000 description 5
229940044601 receptor agonist Drugs 0.000 description 5
206010020772 Hypertension Diseases 0.000 description 4
ZPUCINDJVBIVPJ-LJISPDSOSA-N ***e Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 4
230000008484 agonism Effects 0.000 description 3
239000000556 agonist Substances 0.000 description 3
210000003169 central nervous system Anatomy 0.000 description 3
CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 description 3
230000000862 serotonergic effect Effects 0.000 description 3
SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 2
206010003805 Autism Diseases 0.000 description 2
208000020706 Autistic disease Diseases 0.000 description 2
208000006561 Cluster Headache Diseases 0.000 description 2
206010019233 Headaches Diseases 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
208000002193 Pain Diseases 0.000 description 2
230000007000 age related cognitive decline Effects 0.000 description 2
239000005557 antagonist Substances 0.000 description 2
229940054051 antipsychotic indole derivative Drugs 0.000 description 2
229940049706 benzodiazepine Drugs 0.000 description 2
125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 description 2
208000015114 central nervous system disease Diseases 0.000 description 2
230000027288 circadian rhythm Effects 0.000 description 2
208000018912 cluster headache syndrome Diseases 0.000 description 2
229960003920 ***e Drugs 0.000 description 2
238000009826 distribution Methods 0.000 description 2
229940079593 drug Drugs 0.000 description 2
230000020595 eating behavior Effects 0.000 description 2
229960004756 ethanol Drugs 0.000 description 2
231100000869 headache Toxicity 0.000 description 2
208000003906 hydrocephalus Diseases 0.000 description 2
229960002715 nicotine Drugs 0.000 description 2
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 2
230000002093 peripheral effect Effects 0.000 description 2
208000019553 vascular disease Diseases 0.000 description 2
239000005526 vasoconstrictor agent Substances 0.000 description 2
230000008673 vomiting Effects 0.000 description 2
ZXHYBZYREQQHBQ-UHFFFAOYSA-N 1-(2-bromo-4-methoxyphenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]-5-nitroindole Chemical compound BrC1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=C([N+]([O-])=O)C=C2C(CN2CCN(C)CC2)=C1 ZXHYBZYREQQHBQ-UHFFFAOYSA-N 0.000 description 1
NNKGUYIRAAUQQI-UHFFFAOYSA-N 1-(2-bromo-4-methoxyphenyl)sulfonyl-3-[[4-(2-methoxyphenyl)piperazin-1-yl]methyl]indole Chemical compound BrC1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(CN2CCN(CC2)C=2C(=CC=CC=2)OC)=C1 NNKGUYIRAAUQQI-UHFFFAOYSA-N 0.000 description 1
ODNZUMAZIDCWJW-UHFFFAOYSA-N 1-(2-bromo-4-methoxyphenyl)sulfonyl-5-methoxy-3-[(4-methylpiperazin-1-yl)methyl]indole Chemical compound BrC1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=C(OC)C=C2C(CN2CCN(C)CC2)=C1 ODNZUMAZIDCWJW-UHFFFAOYSA-N 0.000 description 1
IEJPEGHXAWGYSQ-UHFFFAOYSA-N 1-(2-bromo-4-methoxyphenyl)sulfonyl-5-methoxy-3-[(4-methylpiperazin-1-yl)methyl]indole;hydrochloride Chemical compound Cl.BrC1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=C(OC)C=C2C(CN2CCN(C)CC2)=C1 IEJPEGHXAWGYSQ-UHFFFAOYSA-N 0.000 description 1
IILSVLGJNBXFHD-UHFFFAOYSA-N 1-(4-bromophenyl)sulfonyl-5-chloro-2-methyl-3-[(4-methylpiperazin-1-yl)methyl]indole Chemical compound C1CN(C)CCN1CC1=C(C)N(S(=O)(=O)C=2C=CC(Br)=CC=2)C2=CC=C(Cl)C=C12 IILSVLGJNBXFHD-UHFFFAOYSA-N 0.000 description 1
HNYJEEFFNIJUDN-UHFFFAOYSA-N 1-(4-methoxyphenyl)sulfonylindole-3-carboxylic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(C(O)=O)=C1 HNYJEEFFNIJUDN-UHFFFAOYSA-N 0.000 description 1
UFRHSFOOWGPAIC-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]-5-nitroindole Chemical compound C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C=CC(C)=CC=2)C2=CC=C([N+]([O-])=O)C=C12 UFRHSFOOWGPAIC-UHFFFAOYSA-N 0.000 description 1
KHMLBOHUMMRYRG-QGZVFWFLSA-N 1-(benzenesulfonyl)-3-[(1r)-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-QGZVFWFLSA-N 0.000 description 1
YHMDTEYVOAWFLZ-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-[(4-methylpiperazin-1-yl)methyl]-5-nitroindole Chemical compound C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C=CC=CC=2)C2=CC=C([N+]([O-])=O)C=C12 YHMDTEYVOAWFLZ-UHFFFAOYSA-N 0.000 description 1
NSGAYPUCLBNEFQ-UHFFFAOYSA-N 1-(benzenesulfonyl)-4,5,6-trichloro-3-[(4-methylpiperazin-1-yl)methyl]indole Chemical compound C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C=CC=CC=2)C2=CC(Cl)=C(Cl)C(Cl)=C12 NSGAYPUCLBNEFQ-UHFFFAOYSA-N 0.000 description 1
UMAQHFAGJQAEBJ-UHFFFAOYSA-N 1-(benzenesulfonyl)-5-bromo-3-[(4-methylpiperazin-1-yl)methyl]indole Chemical compound C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C=CC=CC=2)C2=CC=C(Br)C=C12 UMAQHFAGJQAEBJ-UHFFFAOYSA-N 0.000 description 1
YURASQWGJHLNNE-UHFFFAOYSA-N 1-benzothiophene;piperazine Chemical class C1CNCCN1.C1=CC=C2SC=CC2=C1 YURASQWGJHLNNE-UHFFFAOYSA-N 0.000 description 1
XKLNOVWDVMWTOB-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazole Chemical class N1C2=CC=CC=C2C2=C1CCCC2 XKLNOVWDVMWTOB-UHFFFAOYSA-N 0.000 description 1
FROPHUURXFOJQT-UHFFFAOYSA-N 4,5,6-trichloro-3-[(4-methylpiperazin-1-yl)methyl]-1-(4-propan-2-ylphenyl)sulfonylindole Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)N1C2=CC(Cl)=C(Cl)C(Cl)=C2C(CN2CCN(C)CC2)=C1 FROPHUURXFOJQT-UHFFFAOYSA-N 0.000 description 1
RVYMTOQZUCHNHS-UHFFFAOYSA-N 5-bromo-1-(4-methoxyphenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]indole Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=C(Br)C=C2C(CN2CCN(C)CC2)=C1 RVYMTOQZUCHNHS-UHFFFAOYSA-N 0.000 description 1
VUNZTLUHGGDOCD-UHFFFAOYSA-N 5-bromo-3-[(4-methylpiperazin-1-yl)methyl]-1-(4-propan-2-ylphenyl)sulfonylindole Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)N1C2=CC=C(Br)C=C2C(CN2CCN(C)CC2)=C1 VUNZTLUHGGDOCD-UHFFFAOYSA-N 0.000 description 1
102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 description 1
101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 description 1
UCEZZZCAXZIWMA-UHFFFAOYSA-N 5-methoxy-1-(4-methylphenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]indole Chemical compound C12=CC(OC)=CC=C2N(S(=O)(=O)C=2C=CC(C)=CC=2)C=C1CN1CCN(C)CC1 UCEZZZCAXZIWMA-UHFFFAOYSA-N 0.000 description 1
208000007848 Alcoholism Diseases 0.000 description 1
206010002383 Angina Pectoris Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
SNIXRMIHFOIVBB-UHFFFAOYSA-N N-Hydroxyl-tryptamine Chemical compound C1=CC=C2C(CCNO)=CNC2=C1 SNIXRMIHFOIVBB-UHFFFAOYSA-N 0.000 description 1
208000008589 Obesity Diseases 0.000 description 1
229910019567 Re Re Inorganic materials 0.000 description 1
208000006011 Stroke Diseases 0.000 description 1
GAZVSNAEUUUDEK-JDSLSITLSA-N [(1r,3r,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-hydroxybenzoate Chemical compound O([C@H]1[C@@]2(C)CC[C@H](C1)C2(C)C)C(=O)C1=CC=CC=C1O GAZVSNAEUUUDEK-JDSLSITLSA-N 0.000 description 1
230000005856 abnormality Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000001800 adrenalinergic effect Effects 0.000 description 1
201000007930 alcohol dependence Diseases 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
239000000935 antidepressant agent Substances 0.000 description 1
229940005513 antidepressants Drugs 0.000 description 1
239000000164 antipsychotic agent Substances 0.000 description 1
239000003693 atypical antipsychotic agent Substances 0.000 description 1
229940127236 atypical antipsychotics Drugs 0.000 description 1
230000006399 behavior Effects 0.000 description 1
230000003542 behavioural effect Effects 0.000 description 1
230000000975 bioactive effect Effects 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
230000036760 body temperature Effects 0.000 description 1
150000003857 carboxamides Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
229940039227 diagnostic agent Drugs 0.000 description 1
239000000032 diagnostic agent Substances 0.000 description 1
QPMLSUSACCOBDK-UHFFFAOYSA-N diazepane Chemical compound C1CCNNCC1 QPMLSUSACCOBDK-UHFFFAOYSA-N 0.000 description 1
230000003291 dopaminomimetic effect Effects 0.000 description 1
206010013663 drug dependence Diseases 0.000 description 1
230000004064 dysfunction Effects 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
210000005095 gastrointestinal system Anatomy 0.000 description 1
150000002390 heteroarenes Chemical class 0.000 description 1
150000002460 imidazoles Chemical class 0.000 description 1
239000003446 ligand Substances 0.000 description 1
230000003340 mental effect Effects 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
LPPRLWFUMJHAKF-UHFFFAOYSA-N methyl 4-[4-[4-(1,1,3-trioxo-1,2-benzothiazol-2-yl)butyl]piperazin-1-yl]-1h-indole-2-carboxylate Chemical compound O=C1C2=CC=CC=C2S(=O)(=O)N1CCCCN(CC1)CCN1C1=C2C=C(C(=O)OC)NC2=CC=C1 LPPRLWFUMJHAKF-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
230000001537 neural effect Effects 0.000 description 1
239000002858 neurotransmitter agent Substances 0.000 description 1
235000020824 obesity Nutrition 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
238000012552 review Methods 0.000 description 1
230000003248 secreting effect Effects 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
239000013589 supplement Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
229940024986 topical antifungal imidazole and triazole derivative Drugs 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—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
- C07D403/06—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 carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Psychiatry (AREA)
Addiction (AREA)
Pain & Pain Management (AREA)
Psychology (AREA)
Epidemiology (AREA)
Hospice & Palliative Care (AREA)
Child & Adolescent Psychology (AREA)
Physical Education & Sports Medicine (AREA)
Anesthesiology (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Diabetes (AREA)
Otolaryngology (AREA)
Obesity (AREA)
Hematology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Steroid Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

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)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IN884MA2002		2002-11-28

Publications (1)

Publication Number	Publication Date
ZA200504043B true ZA200504043B (en)	2006-07-26

Family

ID=40184827

Family Applications (1)

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

Country Status (22)

Country	Link
US (1)	US7875605B2 (xx)
EP (1)	EP1581492B1 (xx)
JP (1)	JP4559230B2 (xx)
KR (1)	KR100818508B1 (xx)
CN (2)	CN1720225B (xx)
AT (1)	ATE401307T1 (xx)
AU (1)	AU2003237599B2 (xx)
BR (2)	BRPI0318799B8 (xx)
CA (1)	CA2509982C (xx)
CY (1)	CY1108786T1 (xx)
DE (1)	DE60322266D1 (xx)
DK (1)	DK1581492T3 (xx)
EA (1)	EA011320B1 (xx)
ES (1)	ES2310243T3 (xx)
HK (2)	HK1083217A1 (xx)
MX (1)	MXPA05005701A (xx)
NO (2)	NO330341B1 (xx)
NZ (2)	NZ540840A (xx)
PT (1)	PT1581492E (xx)
SI (1)	SI1581492T1 (xx)
WO (1)	WO2004048330A1 (xx)
ZA (1)	ZA200504043B (xx)

Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7838518B2 (en) *	2002-02-12	2010-11-23	N.V. Organon	1-arylsulfonyl-3-substituted indole and indoline derivatives useful in the treatment of central nervous system disorders
WO2005005439A1 (en) *	2003-07-09	2005-01-20	Suven Life Sciences Limited	Benzothiazino indoles
AU2004312229B2 (en)	2004-01-02	2010-05-20	Suven Life Sciences Limited	Novel Indeno[2,1a]indenes and isoindolo[2,1-a]indoles
AU2006274884B2 (en)	2005-07-29	2012-04-05	F. Hoffmann-La Roche Ag	Indol-3-yl-carbonyl-piperidin and piperazin derivatives
CN101258144B (zh)	2005-08-12	2012-05-30	苏文生命科学有限公司	作为功能性5-ht6配体的氨基芳基磺酰胺衍生物
WO2007020653A1 (en) *	2005-08-12	2007-02-22	Suven Life Sciences Limited	Thioether derivatives as functional 5-ht6 ligands
WO2007020654A1 (en)	2005-08-16	2007-02-22	Suven Life Sciences	An improved process for the preparation of losartan
KR101176894B1 (ko) *	2007-01-08	2012-08-30	수벤 라이프 사이언시스 리미티드	４?（헤테로시클릴）알킬?ｎ?（아릴술포닐） 인돌 화합물 및 이들의 ５?ｈｔ６ 리간드로서 용도
MX2009006077A (es)	2007-01-08	2009-06-17	Suven Life Sciences Ltd	Compuestos de 5-(heterociclil)alquil-n-(arilsulfonil)indol y su uso como ligandos de la 5-hidroxitriptamina6.
CA2683124C (en)	2007-05-03	2012-09-25	Suven Life Sciences Limited	Aminoalkoxy aryl sulfonamide compounds and their use as 5-ht6 ligands
US7807705B2 (en)	2007-05-18	2010-10-05	The Ohio State University Research Foundation	Potent indole-3-carbinol-derived antitumor agents
ATE518833T1 (de)	2007-10-26	2011-08-15	Suven Life Sciences Ltd	Aminoarylsulfonamidverbindungen und ihre verwendung als 5-ht6-liganden
KR101308819B1 (ko)	2008-09-17	2013-09-13	수벤 라이프 사이언시스 리미티드	아릴 술폰아미드 아민 화합물 및 5-ｈｔ6 리간드로서의 용도
US8318725B2 (en)	2008-09-17	2012-11-27	Suven Life Sciences Limited	Aryl indolyl sulfonamide compounds and their use as 5-HT6 ligands
CA2770724A1 (en) *	2009-08-10	2011-02-17	Galenea Corporation	5-ht inhibiting indole compounds
US8153680B2 (en) *	2009-08-25	2012-04-10	The Ohio State University Research Foundation	Alkyl indole-3-carbinol-derived antitumor agents
MX2012007783A (es)	2010-01-05	2012-10-03	Suven Life Sciences Ltd	Compuestos sulfona que actuan como ligandos del receptor 5-ht6.
CN102093149A (zh) *	2010-12-08	2011-06-15	天津理工大学	一种促进氰基快速水解制备羧酸类化合物的方法
US8889730B2 (en)	2012-04-10	2014-11-18	Pfizer Inc.	Indole and indazole compounds that activate AMPK
CA2905242C (en)	2013-03-15	2016-11-29	Pfizer Inc.	Indole compounds that activate ampk
KR101534136B1 (ko) *	2013-06-11	2015-07-07	이화여자대학교 산학협력단	인돌 유도체 또는 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 유효성분으로 포함하는 5-ht6 수용체 관련 질환의 예방 또는 치료용 약학적 조성물
CA2929309C (en) *	2013-12-02	2018-07-03	Suven Life Sciences Limited	Process for large scale production of 1-[(2-bromophenyl)sulfonyl]-5-methoxy-3-[(4-methyl-1-piperazinyl)methyl]-1h-indole dimesylate monohydrate
JP6454346B2 (ja)	2013-12-20	2019-01-16	サンシャイン・レイク・ファーマ・カンパニー・リミテッドＳｕｎｓｈｉｎｅＬａｋｅＰｈａｒｍａＣｏ．，Ｌｔｄ．	芳香族複素環式化合物及び医薬におけるその応用
AU2015286049B2 (en)	2014-07-08	2018-03-01	Sunshine Lake Pharma Co., Ltd.	Aromatic heterocyclic derivatives and pharmaceutical applications thereof
JP6629322B2 (ja)	2014-08-16	2020-01-15	スヴェン・ライフ・サイエンシズ・リミテッド	１−［（２−ブロモフェニル）スルフォニル］−５−メトキシ−３−［（４−メチル−１−ピペラジニル）メチル］−１ｈ−インドールジメシレート一水和物の活性代謝産物及びその活性代謝産物のジメシレート二水和物の塩
KR102015484B1 (ko) *	2016-05-18	2019-08-28	수벤 라이프 사이언시스 리미티드	순수한 5-ht6 수용체 길항제와 아세틸콜린에스테라제 저해제의 조합물
CA3023828C (en) *	2016-05-18	2019-08-27	Suven Life Sciences Limited	Combination of pure 5-ht6 receptor antagonists with nmda receptor antagonist
CA3023836C (en) *	2016-05-18	2019-08-27	Suven Life Sciences Limited	Triple combination of pure 5-ht6 receptor antagonists, acetylcholinesterase inhibitors and nmda receptor antagonist
JP6669937B2 (ja) *	2016-10-03	2020-03-18	スヴェン・ライフ・サイエンシズ・リミテッド	５−ｈｔ６拮抗薬の医薬組成物
CN107174586B (zh) *	2017-02-21	2020-08-11	中国科学院昆明植物研究所	以芦竹碱衍生物为活性成分的药物组合物及其应用
US20210338661A1 (en) *	2017-07-03	2021-11-04	Suven Life Sciences Limited	New uses of a pure 5-ht 6 receptor antagonist
JP2023506724A (ja)	2019-12-02	2023-02-20	スヴェン・ライフ・サイエンシーズ・リミテッド	認知症患者の行動心理学的症状の治療
CA3162938A1 (en)	2019-12-02	2021-06-10	Suven Life Sciences Limited	Methods for treating behavioral and psychological symptoms in patients with dementia
CN111233737B (zh) *	2020-03-16	2021-05-11	东莞市东阳光新药研发有限公司	芳杂环类衍生物的盐及其用途
CN111362858B (zh) *	2020-03-16	2021-05-11	东莞市东阳光新药研发有限公司	芳杂环类衍生物的盐及其用途
KR102347372B1 (ko)	2020-12-14	2022-01-07	(주)케이메디켐	신규한 인돌 유도체, 이의 제조방법 및 이를 포함하는 인지기능 개선용 조성물
CN115504925B (zh) *	2021-06-22	2024-03-12	广东药科大学	一类ppar激动剂、其制备方法及其作为药物的用途

Family Cites Families (28)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1305458A (xx) *	1969-02-26	1973-01-31
ZA795239B (en)	1978-10-12	1980-11-26	Glaxo Group Ltd	Heterocyclic compounds
ZA815541B (en) *	1980-08-12	1983-03-30	Glaxo Group Ltd	Heterocyclic compounds
GB8600397D0 (en) *	1986-01-08	1986-02-12	Glaxo Group Ltd	Chemical compounds
GB8719167D0 (en)	1987-08-13	1987-09-23	Glaxo Group Ltd	Chemical compounds
GB8724912D0 (en)	1987-10-23	1987-11-25	Wellcome Found	Indole derivatives
GB8819024D0 (en)	1988-08-10	1988-09-14	Glaxo Group Ltd	Chemical compounds
JPH04208263A (ja) *	1990-01-02	1992-07-29	Fujisawa Pharmaceut Co Ltd	インドール誘導体およびそれらの製造法
IL96891A0 (en)	1990-01-17	1992-03-29	Merck Sharp & Dohme	Indole-substituted five-membered heteroaromatic compounds,their preparation and pharmaceutical compositions containing them
CA2042295A1 (fr) *	1990-05-15	1991-11-16	Jacques Chauveau	Derives de mediateurs endogenes, leurs sels, procede de preparation, applications, et compositions les renfermant
MC2210A1 (fr)	1990-06-07	1992-11-26	Wellcome Found	Composes heterocycliques therapeutiques,leur utilisation et procede pour les preparer
SK278998B6 (sk)	1991-02-01	1998-05-06	Merck Sharp & Dohme Limited	Deriváty imidazolu, triazolu a tetrazolu, spôsob i
TW263508B (xx) *	1991-02-12	1995-11-21	Pfizer
GB9113802D0 (en)	1991-06-26	1991-08-14	Smithkline Beecham Plc	Medicaments
JP3223193B2 (ja) *	1991-08-09	2001-10-29	株式会社日清製粉グループ本社	インドール誘導体およびそれらを有効成分とする抗癌剤耐性克服物質
GB9210400D0 (en)	1992-05-15	1992-07-01	Merck Sharp & Dohme	Therapeutic agents
KR940007001A (ko)	1992-09-16	1994-04-26	최승주	새로운 n-신나모일-2-메틸-5-메톡시-3-인돌 아세트산 에스테르, 그 제조방법 및 이를 함유하는 약학적 제제
EP0773942A1 (en) *	1994-07-26	1997-05-21	Pfizer Inc.	4-indole derivatives as serotonin agonists and antagonists
EP1173432B9 (en) *	1999-04-21	2008-10-15	NPS Allelix Corp.	Piperidine-indole compounds having 5-ht6 affinity
JP2000344744A (ja) *	1999-06-04	2000-12-12	Ss Pharmaceut Co Ltd	アセトフェノン誘導体およびその製法
PE20020276A1 (es) *	2000-06-30	2002-04-06	Elan Pharm Inc	COMPUESTOS DE AMINA SUSTITUIDA COMO INHIBIDORES DE ß-SECRETASA PARA EL TRATAMIENTO DE ALZHEIMER
CN1317276C (zh) *	2000-09-29	2007-05-23	中国科学院上海药物研究所	一类吲哚基哌啶类化合物及其制备方法和用途
KR100823908B1 (ko) *	2000-10-20	2008-04-21	바이오비트럼 에이비(피유비엘)	2-, 3-, 4-, 또는 5-치환-ｎ1-(벤젠술포닐)인돌 및 이의치료 용도
EP1335722B1 (en) *	2000-11-24	2006-08-30	Smithkline Beecham Plc	Indolyl-sulfonyl- compounds useful in the treatment of cns disorders
EP1351688A4 (en) *	2000-12-11	2006-01-04	Smithkline Beecham Corp	UROTENSIN-II RECEPTOR ANTAGONISTS
DK1355900T3 (da) *	2000-12-22	2006-09-11	Wyeth Corp	Heterocyclylalkylindol- eller -azaindolforbindelser som 5-hydroxytryptamin-6-ligander
JP2004524295A (ja) *	2001-01-26	2004-08-12	スミスクライン・ビーチャム・コーポレイション	ウロテンシン−ｉｉ受容体アンタゴニスト
US7838518B2 (en) *	2002-02-12	2010-11-23	N.V. Organon	1-arylsulfonyl-3-substituted indole and indoline derivatives useful in the treatment of central nervous system disorders

2003
- 2003-06-05 JP JP2004554900A patent/JP4559230B2/ja not_active Expired - Lifetime
- 2003-06-05 NZ NZ540840A patent/NZ540840A/en not_active IP Right Cessation
- 2003-06-05 EP EP03735970A patent/EP1581492B1/en not_active Expired - Lifetime
- 2003-06-05 AT AT03735970T patent/ATE401307T1/de active
- 2003-06-05 SI SI200331342T patent/SI1581492T1/sl unknown
- 2003-06-05 NZ NZ572186A patent/NZ572186A/en not_active IP Right Cessation
- 2003-06-05 DE DE60322266T patent/DE60322266D1/de not_active Expired - Lifetime
- 2003-06-05 AU AU2003237599A patent/AU2003237599B2/en not_active Expired
- 2003-06-05 EA EA200500881A patent/EA011320B1/ru unknown
- 2003-06-05 BR BRPI0318799A patent/BRPI0318799B8/pt active IP Right Grant
- 2003-06-05 CN CN038254883A patent/CN1720225B/zh not_active Expired - Lifetime
- 2003-06-05 WO PCT/IN2003/000209 patent/WO2004048330A1/en active IP Right Grant
- 2003-06-05 CA CA2509982A patent/CA2509982C/en not_active Expired - Lifetime
- 2003-06-05 DK DK03735970T patent/DK1581492T3/da active
- 2003-06-05 KR KR1020057009512A patent/KR100818508B1/ko active IP Right Grant
- 2003-06-05 ES ES03735970T patent/ES2310243T3/es not_active Expired - Lifetime
- 2003-06-05 US US10/536,618 patent/US7875605B2/en active Active
- 2003-06-05 CN CN200910134498XA patent/CN101544592B/zh not_active Expired - Lifetime
- 2003-06-05 PT PT03735970T patent/PT1581492E/pt unknown
- 2003-06-05 BR BRPI0315959A patent/BRPI0315959C1/pt not_active IP Right Cessation
- 2003-06-05 MX MXPA05005701A patent/MXPA05005701A/es active IP Right Grant
2005
- 2005-05-19 ZA ZA200504043A patent/ZA200504043B/en unknown
- 2005-06-08 NO NO20052737A patent/NO330341B1/no not_active IP Right Cessation
2006
- 2006-03-10 HK HK06103107.8A patent/HK1083217A1/xx not_active IP Right Cessation
- 2006-03-10 HK HK09111134.5A patent/HK1133002A1/xx not_active IP Right Cessation
2008
- 2008-09-17 CY CY20081100999T patent/CY1108786T1/el unknown
- 2008-12-05 NO NO20085054A patent/NO335015B1/no not_active IP Right Cessation

Also Published As

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

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 (xx)	2009-03-05
FI105812B (fi)	2000-10-13	Menetelmä terapeuttisesti käyttökelpoisten indolijohdannaisten valmistamiseksi
CN106170288B (zh)	2019-07-19	药物化合物
JP6761413B2 (ja)	2020-09-23	シグマ受容体結合剤
MXPA02002799A (es)	2003-02-27	Indolinas sustituidas en posicion 6, su preparacion y su utilizacion como medicamentos.
HU208132B (en)	1993-08-30	Process for producing 3-arylcarbonyl-1h-indole derivatives and pharmaceutical compositions comprising same
ZA200500021B (en)	2006-06-28	1-(Aminoalkyl)-3-sylfonnylindole and -indazole derivatives as 5-hydroxytryptamine-5 ligands
CN109219594A (zh)	2019-01-15	吲哚啉类似物及其用途
Cao et al.	2021	Indazole scaffold: A generalist for marketed and clinical drugs
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
CN113412262A (zh)	2021-09-17	包含杂环蛋白激酶抑制剂的制剂
BR112018007068B1 (pt)	2024-01-02	Derivados de quinoxalina e piridopirazina como inibidores de pi3kbeta, seu uso e composição farmacêutica que os compreende
TW201022247A (en)	2010-06-16	1-(arylsulfonyl)-4-(piperazin-1-yl)-1H-benzimidazoles as 5-hydroxytryptamine-6 ligands
CA2507923A1 (en)	2004-07-01	Tetracyclic 3-substituted indoles having serotonin receptor affinity
US6362196B1 (en)	2002-03-26	Method to treat pain utilizing benzimidazole NMDA/NR2B antagonists
EP1412028B1 (en)	2007-10-17	Tetrahydroindolone derivatives linked to arylpiperazines
ZA200409886B (en)	2006-07-26	Tetracylclic aryfulsonyl indoles having serotonin receptor affinity
US9642851B2 (en)	2017-05-09	Indolinone derivative as tyrosine kinase inhibitor
US6770638B2 (en)	2004-08-03	Tetrahydroindolone and purine derivatives linked to arylpiperazines
ZA200409888B (en)	2006-07-26	Arylakyl indoles having sertonin receptor affinity useful as therapeutic agents process for their preparation and pharmaceutical compositions containing them
KR20010031520A (ko)	2001-04-16	피페라진류-시클로덱스트린 복합체
BR112021001939A2 (pt)	2021-04-27	inibidores de cdk8/19