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 PDFInfo
- Publication number
- ZA200504043B ZA200504043B ZA200504043A ZA200504043A ZA200504043B ZA 200504043 B ZA200504043 B ZA 200504043B ZA 200504043 A ZA200504043 A ZA 200504043A ZA 200504043 A ZA200504043 A ZA 200504043A ZA 200504043 B ZA200504043 B ZA 200504043B
- Authority
- ZA
- South Africa
- Prior art keywords
- indole
- methylpiperazin
- yimethyl
- bromo
- indol
- Prior art date
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- -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
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- 208000010877 cognitive disease Diseases 0.000 claims description 4
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- 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
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- 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
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- 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
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- 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
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- 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
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- RJTZUHVCZIGJMB-UHFFFAOYSA-N hydron;1h-indole;chloride Chemical compound Cl.C1=CC=C2NC=CC2=C1 RJTZUHVCZIGJMB-UHFFFAOYSA-N 0.000 claims 1
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- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims 1
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- 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
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- 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
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- 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
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- 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
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- 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
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| IN884MA2002 | 2002-11-28 |
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| JP (1) | JP4559230B2 (ja) |
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| CN (2) | CN101544592B (ja) |
| AT (1) | ATE401307T1 (ja) |
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| BR (2) | BRPI0318799B8 (ja) |
| CA (1) | CA2509982C (ja) |
| CY (1) | CY1108786T1 (ja) |
| DE (1) | DE60322266D1 (ja) |
| DK (1) | DK1581492T3 (ja) |
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| NZ (2) | NZ540840A (ja) |
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| DE60322186D1 (de) * | 2002-02-12 | 2008-08-28 | Organon Nv | 1-arylsulfonyl-3-substituierte indol und indolinederivate verwendbar zur behandlung von erkrankungen des zentralnervensystem |
| WO2005005439A1 (en) * | 2003-07-09 | 2005-01-20 | Suven Life Sciences Limited | Benzothiazino indoles |
| CA2552106C (en) | 2004-01-02 | 2011-10-11 | Suven Life Sciences Limited | Novel indeno[2,1a]indenes and isoindol[2,1-a]indoles |
| EP1917255A2 (en) | 2005-07-29 | 2008-05-07 | F. Hoffmann-Roche AG | Indol-3-yl-carbonyl-piperidin and piperazin derivatives |
| MX2008002018A (es) | 2005-08-12 | 2008-03-27 | Suven Life Sciences Ltd | Derivados de aminoaril sulfonamida como ligandos funcionales del 5-ht6. |
| WO2007020653A1 (en) * | 2005-08-12 | 2007-02-22 | Suven Life Sciences Limited | Thioether derivatives as functional 5-ht6 ligands |
| US7923566B2 (en) | 2005-08-16 | 2011-04-12 | Suven Life Sciences Limited | Alternative process for the preparation of losartan |
| AU2007343063B2 (en) | 2007-01-08 | 2011-02-17 | Suven Life Sciences Limited | 5-(Heterocyclyl)alkyl-N-(arylsulfonyl)indole compounds and their use as 5-HT6 ligands |
| ES2533902T3 (es) * | 2007-01-08 | 2015-04-15 | Suven Life Sciences Limited | Compuestos de 4-(heterociclil)alquil-N-(arilsulfonil)indol y su uso como ligandos del 5-HT6 |
| DK2155674T3 (da) | 2007-05-03 | 2011-09-26 | Suven Life Sciences Ltd | Aminoalkoxy-aryl-sulfonamidforbindelser og anvendelse heraf som 5-HT6-ligander |
| US7807705B2 (en) | 2007-05-18 | 2010-10-05 | The Ohio State University Research Foundation | Potent indole-3-carbinol-derived antitumor agents |
| WO2009053997A1 (en) | 2007-10-26 | 2009-04-30 | Suven Life Sciences Limited | Amino arylsulfonamide compounds and their use as 5-ht6 ligands |
| 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 |
| WO2011019738A1 (en) * | 2009-08-10 | 2011-02-17 | Galenea Corporation | Compounds and methods of use thereof |
| US8153680B2 (en) | 2009-08-25 | 2012-04-10 | The Ohio State University Research Foundation | Alkyl indole-3-carbinol-derived antitumor agents |
| KR101463190B1 (ko) | 2010-01-05 | 2014-11-18 | 수벤 라이프 사이언시스 리미티드 | ５ｈｔ６ 수용체 리간드인 술폰 화합물 |
| 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 |
| JP6064062B2 (ja) | 2013-03-15 | 2017-01-18 | ファイザー・インク | Ａｍｐｋを活性化させるインダゾール化合物 |
| 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 |
| NZ719671A (en) * | 2013-12-02 | 2017-03-31 | Suven Life Sciences Ltd | 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Ｓｕｎｓｈｉｎｅ Ｌａｋｅ Ｐｈａｒｍａ Ｃｏ．，Ｌｔｄ． | 芳香族複素環式化合物及び医薬におけるその応用 |
| EP3166924B1 (en) | 2014-07-08 | 2019-02-20 | Sunshine Lake Pharma Co., Ltd. | Aromatic heterocyclic derivatives and pharmaceutical applications thereof |
| PL3180001T3 (pl) * | 2014-08-16 | 2019-07-31 | Suven Life Sciences Limited | Aktywny metabolit monohydrat dimesylanu 1-[(2-bromofenylo)sulfonylo]-5-metoksy-3-[(4-metylo-1-piperazynylo)metylo]-1h-indolu oraz sól dihydrat dimesylanu aktywnego metabolitu |
| EA038087B1 (ru) * | 2016-05-18 | 2021-07-05 | Сувен Лайф Сайенсиз Лимитед | Трехкомпонентная фармацевтическая комбинация чистых антагонистов 5-ht6 рецепторов, ингибиторов ацетилхолинэстеразы и антагониста nmda рецептора, применение указанной комбинации и содержащей ее фармацевтической композиции в лечении когнитивных расстройств и способ такого лечения |
| CN109069449A (zh) * | 2016-05-18 | 2018-12-21 | 苏文生命科学有限公司 | 纯5-ht6受体拮抗剂与nmda受体拮抗剂的组合 |
| SI3484467T1 (sl) | 2016-05-18 | 2020-10-30 | Suven Life Sciences Limited | Kombinacija čistih 5-HT receptor antagonistov z inhibitorji acetilholinesteraze |
| US20190336497A1 (en) * | 2016-10-03 | 2019-11-07 | Suven Life Sciences Limited | Pharmaceutical compositions of 5-ht6 antagonist |
| 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 |
| US20230000859A1 (en) | 2019-12-02 | 2023-01-05 | Suven Life Sciences Limited | Methods for treating behavioral and psychological symptoms in patients with dementia |
| CN114901282B (zh) | 2019-12-02 | 2024-06-25 | 苏文生命科学有限公司 | 在痴呆患者中治疗行为和精神症状 |
| 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 |
| 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 |
| 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 |
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| BE889931A (fr) | 1980-08-12 | 1982-02-11 | Glaxo Group Ltd | Derives indoliques, leur preparation et leurs applications en tant que medicaments |
| 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 |
| IL114690A (en) | 1990-06-07 | 1997-02-18 | Wellcome Found | Antimigraine oxazolidinone substituted indole derivatives |
| CZ283018B6 (cs) | 1991-02-01 | 1997-12-17 | Merck Sharp And Dohme Limited | Deriváty imidazolu, triazolu a tetrazolu a farmaceutické přípravky na jejich bázi |
| TW263508B (ja) * | 1991-02-12 | 1995-11-21 | Pfizer | |
| GB9113802D0 (en) | 1991-06-26 | 1991-08-14 | Smithkline Beecham Plc | Medicaments |
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| 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 |
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| AU2002220715A1 (en) * | 2000-11-24 | 2002-06-03 | Smithkline Beecham Plc | Indolsulfonyl compounds useful in the treatment of cns disorders |
| JP2004515530A (ja) | 2000-12-11 | 2004-05-27 | 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 |
| DK1355900T3 (da) * | 2000-12-22 | 2006-09-11 | Wyeth Corp | Heterocyclylalkylindol- eller -azaindolforbindelser som 5-hydroxytryptamin-6-ligander |
| US6818655B2 (en) * | 2001-01-26 | 2004-11-16 | Smithkline Beecham Corporation | Urotensin-II receptor antagonists |
| DE60322186D1 (de) * | 2002-02-12 | 2008-08-28 | Organon Nv | 1-arylsulfonyl-3-substituierte indol und indolinederivate verwendbar zur behandlung von erkrankungen des zentralnervensystem |
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