HRP20000847A2 - 4,5,6 i 7 - INDOLE AND INDOLINE DERIVATIVES, THEIR PREPARATION AND USE - Google Patents
4,5,6 i 7 - INDOLE AND INDOLINE DERIVATIVES, THEIR PREPARATION AND USE Download PDFInfo
- Publication number
- HRP20000847A2 HRP20000847A2 HR20000847A HRP20000847A HRP20000847A2 HR P20000847 A2 HRP20000847 A2 HR P20000847A2 HR 20000847 A HR20000847 A HR 20000847A HR P20000847 A HRP20000847 A HR P20000847A HR P20000847 A2 HRP20000847 A2 HR P20000847A2
- Authority
- HR
- Croatia
- Prior art keywords
- indol
- piperazine
- ethyl
- chloro
- benzofuranyl
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 10
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title description 7
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title description 4
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title description 4
- 150000002476 indolines Chemical class 0.000 title description 3
- 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 42
- 238000000034 method Methods 0.000 claims description 34
- -1 C1-6-alk(en/yn)yl Chemical group 0.000 claims description 31
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 31
- 238000011282 treatment Methods 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 17
- 229940076279 serotonin Drugs 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 230000009103 reabsorption Effects 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 150000002367 halogens Chemical group 0.000 claims description 14
- 230000005764 inhibitory process Effects 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 13
- 101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 claims description 12
- 102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 229940079593 drug Drugs 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 7
- 208000035475 disorder Diseases 0.000 claims description 7
- 102000034527 Retinoid X Receptors Human genes 0.000 claims description 6
- 108010038912 Retinoid X Receptors Proteins 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 102000003702 retinoic acid receptors Human genes 0.000 claims description 6
- 108090000064 retinoic acid receptors Proteins 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 5
- IEAPSZTWAQJSLE-UHFFFAOYSA-N 4-chloro-3-[2-[4-(1h-indol-4-yl)piperazin-1-yl]ethyl]-1h-indole Chemical compound C1=2C(Cl)=CC=CC=2NC=C1CCN(CC1)CCN1C1=CC=CC2=C1C=CN2 IEAPSZTWAQJSLE-UHFFFAOYSA-N 0.000 claims description 5
- INSUHQMOGXBBBP-UHFFFAOYSA-N 7-bromo-3-[2-[4-(1h-indol-4-yl)piperazin-1-yl]ethyl]-1h-indole Chemical compound C=1NC=2C(Br)=CC=CC=2C=1CCN(CC1)CCN1C1=CC=CC2=C1C=CN2 INSUHQMOGXBBBP-UHFFFAOYSA-N 0.000 claims description 5
- 208000019901 Anxiety disease Diseases 0.000 claims description 5
- 241001465754 Metazoa Species 0.000 claims description 5
- 208000019022 Mood disease Diseases 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 230000008485 antagonism Effects 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 4
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 4
- 208000028017 Psychotic disease Diseases 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 208000019906 panic disease Diseases 0.000 claims description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 3
- KZBQKNHKHLMMIM-UHFFFAOYSA-N 1-benzyl-4-[4-[2-(1h-indol-3-yl)ethyl]piperazin-1-yl]indole Chemical compound C=1NC2=CC=CC=C2C=1CCN(CC1)CCN1C(C=1C=C2)=CC=CC=1N2CC1=CC=CC=C1 KZBQKNHKHLMMIM-UHFFFAOYSA-N 0.000 claims description 3
- YYTPZWYTPKXSFX-UHFFFAOYSA-N 1-benzyl-4-[4-[2-(5-fluoro-1h-indol-3-yl)ethyl]piperazin-1-yl]indole Chemical compound C12=CC(F)=CC=C2NC=C1CCN(CC1)CCN1C(C=1C=C2)=CC=CC=1N2CC1=CC=CC=C1 YYTPZWYTPKXSFX-UHFFFAOYSA-N 0.000 claims description 3
- YQPDLHQWAGGSDB-UHFFFAOYSA-N 1-benzyl-4-[4-[2-(6-chloro-1h-indol-3-yl)ethyl]piperazin-1-yl]indole Chemical compound C=1NC2=CC(Cl)=CC=C2C=1CCN(CC1)CCN1C(C=1C=C2)=CC=CC=1N2CC1=CC=CC=C1 YQPDLHQWAGGSDB-UHFFFAOYSA-N 0.000 claims description 3
- GRUDTMHMQAGHLH-UHFFFAOYSA-N 3-[2-[4-(1h-indol-4-yl)piperazin-1-yl]ethyl]-1h-indole Chemical compound C=1NC2=CC=CC=C2C=1CCN(CC1)CCN1C1=CC=CC2=C1C=CN2 GRUDTMHMQAGHLH-UHFFFAOYSA-N 0.000 claims description 3
- HHCBWJJRMRBBCB-UHFFFAOYSA-N 3-[2-[4-(1h-indol-4-yl)piperazin-1-yl]ethyl]-1h-indole-7-carbonitrile Chemical compound C=1NC=2C(C#N)=CC=CC=2C=1CCN(CC1)CCN1C1=CC=CC2=C1C=CN2 HHCBWJJRMRBBCB-UHFFFAOYSA-N 0.000 claims description 3
- MMOGIDGHFQGENT-UHFFFAOYSA-N 3-[2-[4-(1h-indol-4-yl)piperazin-1-yl]ethyl]-2h-indazole Chemical compound N=1NC2=CC=CC=C2C=1CCN(CC1)CCN1C1=CC=CC2=C1C=CN2 MMOGIDGHFQGENT-UHFFFAOYSA-N 0.000 claims description 3
- PJHWEBQBXPDXRE-UHFFFAOYSA-N 3-[3-[4-(1h-indol-4-yl)piperazin-1-yl]propyl]-1h-indole Chemical compound C1=CC=C2C(CCCN3CCN(CC3)C=3C=4C=CNC=4C=CC=3)=CNC2=C1 PJHWEBQBXPDXRE-UHFFFAOYSA-N 0.000 claims description 3
- DOUDAIRYOIPBNR-UHFFFAOYSA-N 4-[4-(1-benzofuran-3-ylmethyl)piperazin-1-yl]-1h-indole Chemical compound C1=CC=C2C(CN3CCN(CC3)C=3C=4C=CNC=4C=CC=3)=COC2=C1 DOUDAIRYOIPBNR-UHFFFAOYSA-N 0.000 claims description 3
- DVNUHRSTSJFZBG-UHFFFAOYSA-N 4-[4-[2-(1h-indol-3-yl)ethyl]piperazin-1-yl]-1-prop-2-ynylindole Chemical compound C1=CC=C2C(CCN3CCN(CC3)C3=C4C=CN(C4=CC=C3)CC#C)=CNC2=C1 DVNUHRSTSJFZBG-UHFFFAOYSA-N 0.000 claims description 3
- DOHAKZXOJZQTFL-UHFFFAOYSA-N 4-[4-[2-(1h-indol-3-yl)ethyl]piperazin-1-yl]-1h-indole-3-carbonitrile Chemical compound C1=CC=C2C(CCN3CCN(CC3)C=3C=CC=C4NC=C(C=34)C#N)=CNC2=C1 DOHAKZXOJZQTFL-UHFFFAOYSA-N 0.000 claims description 3
- WKGSILDXQBJVCC-UHFFFAOYSA-N 4-[4-[2-(5-bromo-1h-indol-3-yl)ethyl]piperazin-1-yl]-1-prop-2-ynylindole Chemical compound C12=CC(Br)=CC=C2NC=C1CCN(CC1)CCN1C1=CC=CC2=C1C=CN2CC#C WKGSILDXQBJVCC-UHFFFAOYSA-N 0.000 claims description 3
- AGVJFECVGZMPST-UHFFFAOYSA-N 4-[4-[2-(5-chloro-1-benzofuran-3-yl)ethyl]piperazin-1-yl]-1h-indole Chemical compound C12=CC(Cl)=CC=C2OC=C1CCN(CC1)CCN1C1=CC=CC2=C1C=CN2 AGVJFECVGZMPST-UHFFFAOYSA-N 0.000 claims description 3
- UQQVWSLOBRRCHZ-UHFFFAOYSA-N 4-[4-[2-(5-fluoro-1-benzofuran-3-yl)ethyl]piperazin-1-yl]-1h-indole Chemical compound C12=CC(F)=CC=C2OC=C1CCN(CC1)CCN1C1=CC=CC2=C1C=CN2 UQQVWSLOBRRCHZ-UHFFFAOYSA-N 0.000 claims description 3
- HTXUCZURQGCALZ-UHFFFAOYSA-N 4-[4-[2-(5-fluoro-1-benzofuran-3-yl)ethyl]piperazin-1-yl]-1h-indole-3-carbonitrile Chemical compound C12=CC(F)=CC=C2OC=C1CCN(CC1)CCN1C1=CC=CC2=C1C(C#N)=CN2 HTXUCZURQGCALZ-UHFFFAOYSA-N 0.000 claims description 3
- VBRDWACMHZFSLL-UHFFFAOYSA-N 4-[4-[2-(5-fluoro-1h-indol-3-yl)ethyl]piperazin-1-yl]-1-prop-2-ynylindole Chemical compound C12=CC(F)=CC=C2NC=C1CCN(CC1)CCN1C1=CC=CC2=C1C=CN2CC#C VBRDWACMHZFSLL-UHFFFAOYSA-N 0.000 claims description 3
- JKHASOQAHXASCK-UHFFFAOYSA-N 4-[4-[2-(6-chloro-1h-indol-3-yl)ethyl]piperazin-1-yl]-1-prop-2-ynylindole Chemical compound C=1NC2=CC(Cl)=CC=C2C=1CCN(CC1)CCN1C1=CC=CC2=C1C=CN2CC#C JKHASOQAHXASCK-UHFFFAOYSA-N 0.000 claims description 3
- CWCXSYDWHLRBLZ-UHFFFAOYSA-N 4-[4-[2-(6-chloro-1h-indol-3-yl)ethyl]piperazin-1-yl]-1h-indole-3-carbonitrile Chemical compound C=1NC2=CC(Cl)=CC=C2C=1CCN(CC1)CCN1C1=CC=CC2=C1C(C#N)=CN2 CWCXSYDWHLRBLZ-UHFFFAOYSA-N 0.000 claims description 3
- OOPAXCAOYWFOLB-UHFFFAOYSA-N 4-[4-[2-(6-methyl-1-benzofuran-3-yl)ethyl]piperazin-1-yl]-1h-indole Chemical compound C=1OC2=CC(C)=CC=C2C=1CCN(CC1)CCN1C1=CC=CC2=C1C=CN2 OOPAXCAOYWFOLB-UHFFFAOYSA-N 0.000 claims description 3
- BOXSMMZSRLUSCW-UHFFFAOYSA-N 4-[4-[2-(7-chloro-1-benzofuran-3-yl)ethyl]piperazin-1-yl]-1h-indole Chemical compound C=1OC=2C(Cl)=CC=CC=2C=1CCN(CC1)CCN1C1=CC=CC2=C1C=CN2 BOXSMMZSRLUSCW-UHFFFAOYSA-N 0.000 claims description 3
- SONZEIXSBAWMLA-UHFFFAOYSA-N 5-chloro-3-[2-[4-(1h-indol-5-yl)piperazin-1-yl]ethyl]-1h-indole Chemical compound C1=C2NC=CC2=CC(N2CCN(CC2)CCC2=CNC3=CC=C(C=C32)Cl)=C1 SONZEIXSBAWMLA-UHFFFAOYSA-N 0.000 claims description 3
- CCKRDWKRSKNOEN-UHFFFAOYSA-N 6-chloro-3-[2-[4-(1h-indol-4-yl)piperazin-1-yl]ethyl]-1h-indole Chemical compound C=1NC2=CC(Cl)=CC=C2C=1CCN(CC1)CCN1C1=CC=CC2=C1C=CN2 CCKRDWKRSKNOEN-UHFFFAOYSA-N 0.000 claims description 3
- GXWQDXLPDRHDCY-UHFFFAOYSA-N 6-chloro-3-[2-[4-(1h-indol-4-yl)piperazin-1-yl]ethyl]-2h-indazole Chemical compound N=1NC2=CC(Cl)=CC=C2C=1CCN(CC1)CCN1C1=CC=CC2=C1C=CN2 GXWQDXLPDRHDCY-UHFFFAOYSA-N 0.000 claims description 3
- HLNWTLBQXXXWBY-UHFFFAOYSA-N 6-fluoro-3-[3-[4-(1h-indol-4-yl)piperazin-1-yl]propyl]-1,2-benzoxazole Chemical compound N=1OC2=CC(F)=CC=C2C=1CCCN(CC1)CCN1C1=CC=CC2=C1C=CN2 HLNWTLBQXXXWBY-UHFFFAOYSA-N 0.000 claims description 3
- DWMYBRIWIIKWBJ-UHFFFAOYSA-N [4-[4-[2-(5-bromo-1h-indol-3-yl)ethyl]piperazin-1-yl]-1h-indol-6-yl]methanol Chemical compound C1=C(Br)C=C2C(CCN3CCN(CC3)C=3C=C(C=C4NC=CC4=3)CO)=CNC2=C1 DWMYBRIWIIKWBJ-UHFFFAOYSA-N 0.000 claims description 3
- VOJRANLPQBBQCI-UHFFFAOYSA-N [4-[4-[2-(5-fluoro-1h-indol-3-yl)ethyl]piperazin-1-yl]-1h-indol-6-yl]methanol Chemical compound C1=C(F)C=C2C(CCN3CCN(CC3)C=3C=C(C=C4NC=CC4=3)CO)=CNC2=C1 VOJRANLPQBBQCI-UHFFFAOYSA-N 0.000 claims description 3
- FVHATTZHFQNZJP-UHFFFAOYSA-N [4-[4-[2-(6-chloro-1h-indol-3-yl)ethyl]piperazin-1-yl]-1h-indol-6-yl]methanol Chemical compound ClC1=CC=C2C(CCN3CCN(CC3)C=3C=C(C=C4NC=CC4=3)CO)=CNC2=C1 FVHATTZHFQNZJP-UHFFFAOYSA-N 0.000 claims description 3
- 230000036506 anxiety Effects 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- VPWYYLAXAUQFGH-UHFFFAOYSA-N methyl 4-[4-[2-(1h-indol-3-yl)ethyl]piperazin-1-yl]-1h-indole-6-carboxylate Chemical compound C1=CC=C2C(CCN3CCN(CC3)C=3C=C(C=C4NC=CC4=3)C(=O)OC)=CNC2=C1 VPWYYLAXAUQFGH-UHFFFAOYSA-N 0.000 claims description 3
- SYJFLCMSBJPPSG-UHFFFAOYSA-N methyl 4-[4-[2-(5-fluoro-1-benzofuran-3-yl)ethyl]piperazin-1-yl]-1h-indole-6-carboxylate Chemical compound C1=C(F)C=C2C(CCN3CCN(CC3)C=3C=C(C=C4NC=CC4=3)C(=O)OC)=COC2=C1 SYJFLCMSBJPPSG-UHFFFAOYSA-N 0.000 claims description 3
- OHLZRWXXNBGJLI-UHFFFAOYSA-N methyl 4-[4-[2-(6-chloro-1h-indol-3-yl)ethyl]piperazin-1-yl]-1h-indole-6-carboxylate Chemical compound ClC1=CC=C2C(CCN3CCN(CC3)C=3C=C(C=C4NC=CC4=3)C(=O)OC)=CNC2=C1 OHLZRWXXNBGJLI-UHFFFAOYSA-N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000003441 thioacyl group Chemical group 0.000 claims description 3
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- LMWGAMWDWHNJDN-UHFFFAOYSA-N 3-[2-[4-(1h-indol-4-yl)piperazin-1-yl]ethyl]-5-methyl-1h-indole Chemical compound C12=CC(C)=CC=C2NC=C1CCN(CC1)CCN1C1=CC=CC2=C1C=CN2 LMWGAMWDWHNJDN-UHFFFAOYSA-N 0.000 claims description 2
- KIOPWNRRUQEUTR-UHFFFAOYSA-N 3-[2-[4-(1h-indol-4-yl)piperazin-1-yl]ethyl]-6-(trifluoromethyl)-1h-indole Chemical compound C=1NC2=CC(C(F)(F)F)=CC=C2C=1CCN(CC1)CCN1C1=CC=CC2=C1C=CN2 KIOPWNRRUQEUTR-UHFFFAOYSA-N 0.000 claims description 2
- GRCKVWBWSWHGMB-UHFFFAOYSA-N 3-[2-[4-(1h-indol-4-yl)piperazin-1-yl]ethyl]-6-methyl-1h-indole Chemical compound C=1NC2=CC(C)=CC=C2C=1CCN(CC1)CCN1C1=CC=CC2=C1C=CN2 GRCKVWBWSWHGMB-UHFFFAOYSA-N 0.000 claims description 2
- PKBYZVAIOXKLQM-UHFFFAOYSA-N 3-[2-[4-(1h-indol-4-yl)piperidin-1-yl]ethyl]-1h-indole Chemical compound C=1NC2=CC=CC=C2C=1CCN(CC1)CCC1C1=CC=CC2=C1C=CN2 PKBYZVAIOXKLQM-UHFFFAOYSA-N 0.000 claims description 2
- LMBHNEPPNWMRPK-UHFFFAOYSA-N 3-[2-[4-(1h-indol-4-yl)piperidin-1-yl]ethyl]-5-methyl-1h-indole Chemical compound C12=CC(C)=CC=C2NC=C1CCN(CC1)CCC1C1=CC=CC2=C1C=CN2 LMBHNEPPNWMRPK-UHFFFAOYSA-N 0.000 claims description 2
- AYNLVGHMSHMAHD-UHFFFAOYSA-N 4-[1-[3-(4-methyl-1-benzofuran-3-yl)propyl]piperidin-4-yl]-1h-indole Chemical compound C1=2C(C)=CC=CC=2OC=C1CCCN(CC1)CCC1C1=CC=CC2=C1C=CN2 AYNLVGHMSHMAHD-UHFFFAOYSA-N 0.000 claims description 2
- CDPQAABIPTUSQM-UHFFFAOYSA-N 4-[1-[3-(5-fluoro-1-benzofuran-3-yl)propyl]-3,6-dihydro-2h-pyridin-4-yl]-1h-indole Chemical compound C12=CC(F)=CC=C2OC=C1CCCN(CC=1)CCC=1C1=CC=CC2=C1C=CN2 CDPQAABIPTUSQM-UHFFFAOYSA-N 0.000 claims description 2
- HDXTWLXCOPFXCP-UHFFFAOYSA-N 4-[4-[2-(1-benzofuran-3-yl)ethyl]piperazin-1-yl]-1h-indole Chemical compound C=1OC2=CC=CC=C2C=1CCN(CC1)CCN1C1=CC=CC2=C1C=CN2 HDXTWLXCOPFXCP-UHFFFAOYSA-N 0.000 claims description 2
- WHVKIZNJOFOVQB-UHFFFAOYSA-N 4-[4-[2-(4,5,6,7-tetrafluoro-2-methyl-1-benzofuran-3-yl)ethyl]piperazin-1-yl]-1h-indole Chemical compound CC=1OC2=C(F)C(F)=C(F)C(F)=C2C=1CCN(CC1)CCN1C1=CC=CC2=C1C=CN2 WHVKIZNJOFOVQB-UHFFFAOYSA-N 0.000 claims description 2
- OLAWEGKMWAGCSU-UHFFFAOYSA-N 4-[4-[2-(4-chloro-1h-indol-3-yl)ethyl]piperazin-1-yl]-1h-indole-3-carbonitrile Chemical compound C1=2C(Cl)=CC=CC=2NC=C1CCN(CC1)CCN1C1=CC=CC2=C1C(C#N)=CN2 OLAWEGKMWAGCSU-UHFFFAOYSA-N 0.000 claims description 2
- KOXLCYACERNFQT-UHFFFAOYSA-N 4-[4-[2-(4-methyl-1-benzofuran-3-yl)ethyl]piperazin-1-yl]-1h-indole Chemical compound C1=2C(C)=CC=CC=2OC=C1CCN(CC1)CCN1C1=CC=CC2=C1C=CN2 KOXLCYACERNFQT-UHFFFAOYSA-N 0.000 claims description 2
- ZSLMASYEALIUIK-UHFFFAOYSA-N 4-[4-[2-(5-bromo-1-benzofuran-3-yl)ethyl]piperazin-1-yl]-1h-indole Chemical compound C12=CC(Br)=CC=C2OC=C1CCN(CC1)CCN1C1=CC=CC2=C1C=CN2 ZSLMASYEALIUIK-UHFFFAOYSA-N 0.000 claims description 2
- DXCVKKBJZUQIBV-UHFFFAOYSA-N 4-[4-[2-(6-chloro-1h-indol-3-yl)ethyl]piperazin-1-yl]-1h-indole-2-carbonitrile Chemical compound C=1NC2=CC(Cl)=CC=C2C=1CCN(CC1)CCN1C1=CC=CC2=C1C=C(C#N)N2 DXCVKKBJZUQIBV-UHFFFAOYSA-N 0.000 claims description 2
- SEAQDHYGZRVZFZ-UHFFFAOYSA-N 4-[4-[2-(6-chloro-1h-indol-3-yl)ethyl]piperazin-1-yl]-1h-indole-6-carbonitrile Chemical compound C=1NC2=CC(Cl)=CC=C2C=1CCN(CC1)CCN1C1=CC(C#N)=CC2=C1C=CN2 SEAQDHYGZRVZFZ-UHFFFAOYSA-N 0.000 claims description 2
- RVLIODWZMRKBCS-UHFFFAOYSA-N 4-[4-[2-(6-chloro-1h-indol-3-yl)ethyl]piperazin-1-yl]-1h-indole-7-carbonitrile Chemical compound C=1NC2=CC(Cl)=CC=C2C=1CCN(CC1)CCN1C1=CC=C(C#N)C2=C1C=CN2 RVLIODWZMRKBCS-UHFFFAOYSA-N 0.000 claims description 2
- YTMJLTSIXRWRDH-UHFFFAOYSA-N 4-[4-[2-(6-chloro-1h-indol-3-yl)ethyl]piperazin-1-yl]-6-fluoro-1h-indole Chemical compound ClC1=CC=C2C(CCN3CCN(CC3)C=3C=C(C=C4NC=CC4=3)F)=CNC2=C1 YTMJLTSIXRWRDH-UHFFFAOYSA-N 0.000 claims description 2
- LXRCFKCRPSWFSI-UHFFFAOYSA-N 4-[4-[3-(4-chloro-1-benzofuran-3-yl)propyl]piperazin-1-yl]-1h-indole Chemical compound C1=2C(Cl)=CC=CC=2OC=C1CCCN(CC1)CCN1C1=CC=CC2=C1C=CN2 LXRCFKCRPSWFSI-UHFFFAOYSA-N 0.000 claims description 2
- LOZKUNKUFQIECJ-UHFFFAOYSA-N 4-[4-[3-(4-methyl-1-benzofuran-3-yl)propyl]piperazin-1-yl]-1h-indole Chemical compound C1=2C(C)=CC=CC=2OC=C1CCCN(CC1)CCN1C1=CC=CC2=C1C=CN2 LOZKUNKUFQIECJ-UHFFFAOYSA-N 0.000 claims description 2
- NDMUORRVNRLHAH-UHFFFAOYSA-N 4-chloro-3-[2-[4-(1h-indol-4-yl)piperidin-1-yl]ethyl]-1h-indole Chemical compound C1=2C(Cl)=CC=CC=2NC=C1CCN(CC1)CCC1C1=CC=CC2=C1C=CN2 NDMUORRVNRLHAH-UHFFFAOYSA-N 0.000 claims description 2
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- 238000001727 in vivo Methods 0.000 description 1
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 description 1
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical class C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- WZHJKEUHNJHDLS-QTGUNEKASA-N metergoline Chemical compound C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4N(C)C=C(C=34)C2)C1)C)NC(=O)OCC1=CC=CC=C1 WZHJKEUHNJHDLS-QTGUNEKASA-N 0.000 description 1
- 229960004650 metergoline Drugs 0.000 description 1
- WLXQZCQWRQKPTC-UHFFFAOYSA-N methyl 2-(5-fluoro-1-benzofuran-3-yl)acetate Chemical compound C1=C(F)C=C2C(CC(=O)OC)=COC2=C1 WLXQZCQWRQKPTC-UHFFFAOYSA-N 0.000 description 1
- LXPJDFYUYVHZGX-UHFFFAOYSA-N methyl 4-[4-[2-(5-fluoro-1h-indol-3-yl)-2-oxoacetyl]piperazin-1-yl]-1h-indole-6-carboxylate Chemical compound C1=C(F)C=C2C(C(=O)C(=O)N3CCN(CC3)C=3C=C(C=C4NC=CC4=3)C(=O)OC)=CNC2=C1 LXPJDFYUYVHZGX-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000002899 monoamine oxidase inhibitor Substances 0.000 description 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
- 230000036651 mood Effects 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000010807 negative regulation of binding Effects 0.000 description 1
- 210000001577 neostriatum Anatomy 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 229960002296 paroxetine Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 210000001609 raphe nuclei Anatomy 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 1
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 1
- 239000003723 serotonin 1A agonist Substances 0.000 description 1
- 229940126570 serotonin reuptake inhibitor Drugs 0.000 description 1
- 229960002073 sertraline Drugs 0.000 description 1
- VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- DKGZKTPJOSAWFA-UHFFFAOYSA-N spiperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 DKGZKTPJOSAWFA-UHFFFAOYSA-N 0.000 description 1
- 229950001675 spiperone Drugs 0.000 description 1
- 238000011272 standard treatment Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 238000004885 tandem mass spectrometry Methods 0.000 description 1
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
- OEAMZRWFIQSVJQ-UHFFFAOYSA-N tert-butyl 4-(1h-indol-4-yl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=CC2=C1C=CN2 OEAMZRWFIQSVJQ-UHFFFAOYSA-N 0.000 description 1
- YDUXKTCAHJCIGB-UHFFFAOYSA-N tert-butyl 4-(3-cyano-1h-indol-4-yl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=CC2=C1C(C#N)=CN2 YDUXKTCAHJCIGB-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- 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
- C07D401/14—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 three or more hetero rings
-
- 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
- A61P25/18—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
- A61P25/22—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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D403/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DK82098 | 1998-06-19 | ||
US9282398P | 1998-07-14 | 1998-07-14 | |
PCT/DK1999/000326 WO1999067237A1 (en) | 1998-06-19 | 1999-06-14 | 4,5,6 and 7-indole and indoline derivatives, their preparation and use |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20000847A2 true HRP20000847A2 (en) | 2001-12-31 |
Family
ID=26064717
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR20000847A HRP20000847A2 (en) | 1998-06-19 | 2000-12-11 | 4,5,6 i 7 - INDOLE AND INDOLINE DERIVATIVES, THEIR PREPARATION AND USE |
Country Status (10)
Country | Link |
---|---|
EP (1) | EP1089997A1 (ja) |
JP (1) | JP2003521443A (ja) |
AU (1) | AU765317C (ja) |
BG (1) | BG105136A (ja) |
CA (1) | CA2335711A1 (ja) |
HR (1) | HRP20000847A2 (ja) |
HU (1) | HUP0101475A3 (ja) |
NO (1) | NO20006460L (ja) |
NZ (1) | NZ508506A (ja) |
WO (1) | WO1999067237A1 (ja) |
Families Citing this family (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ZA9711376B (en) * | 1996-12-20 | 1998-07-21 | Lundbeck & Co As H | Indole or dihydroindole derivatives |
GB9912417D0 (en) | 1999-05-28 | 1999-07-28 | Pfizer Ltd | Compounds useful in therapy |
GB9912413D0 (en) | 1999-05-28 | 1999-07-28 | Pfizer Ltd | Compounds useful in therapy |
DE60021194T2 (de) * | 1999-08-23 | 2005-12-22 | Solvay Pharmaceuticals B.V. | Phenylpiperazin-derivate als inhibitoren der serotonin-wiederaufnahme |
AR032712A1 (es) | 2001-02-21 | 2003-11-19 | Solvay Pharm Bv | Un mesilato de derivados de fenilpiperazina y composiciones farmaceuticas que lo contienen |
AR032711A1 (es) * | 2001-02-21 | 2003-11-19 | Solvay Pharm Bv | Derivados de fenilpiperazina, un metodo para la preparacion de los mismos y una composicion farmaceutica que los contiene |
AU2003233231B2 (en) * | 2002-05-13 | 2009-02-26 | F. Hoffmann-La Roche Ag | Benzoxazine derivatives as 5-HT6 modulators and uses thereof |
TW200409777A (en) * | 2002-08-12 | 2004-06-16 | Janssen Pharmaceutica Nv | C-substituted tricyclic isoxazoline derivatives and their use as anti-depressants |
EP1554286B1 (en) | 2002-08-15 | 2010-01-27 | Janssen Pharmaceutica N.V. | Fused heterocyclic isoxazoline derivatives and their use as anti-depressants |
WO2004020437A1 (en) * | 2002-08-29 | 2004-03-11 | H. Lundbeck A/S | S-(+)-3-{1-[2-(2,3-dihydro-1h-indol-3-yl)ethyl]-3,6-dihydro-2h-pyridin-4-yl}-6-chloro-1h-indole and acid addition salts thereof |
GB0227240D0 (en) * | 2002-11-21 | 2002-12-31 | Glaxo Group Ltd | Compounds |
US7235569B2 (en) | 2003-05-02 | 2007-06-26 | Wyeth | Piperidinyl indole and tetrohydropyridinyl indole derivatives and method of their use |
US7276603B2 (en) | 2003-05-02 | 2007-10-02 | Wyeth | Benzofuranyl-and benzothienyl-piperazinyl quinolines and methods of their use |
AU2005313390A1 (en) * | 2004-12-08 | 2006-06-15 | Solvay Pharmaceuticals B.V. | Aryloxyethylamine derivatives with a combination of partial dopamine-D2 receptor agonism and serotonin reuptake inhibition |
US7807671B2 (en) * | 2006-04-25 | 2010-10-05 | Bristol-Myers Squibb Company | Diketo-piperazine and piperidine derivatives as antiviral agents |
MX2009004898A (es) | 2006-11-09 | 2009-05-19 | Hoffmann La Roche | Derivados de indol y de benzofurano-2-carboxamida. |
KR20100134664A (ko) * | 2008-03-14 | 2010-12-23 | 메르크 파텐트 게엠베하 | 중추신경계 장애들의 치료를 위한 아자인돌 화합물들 |
CN103420989B (zh) * | 2012-05-15 | 2016-03-23 | 华中科技大学 | 苯并二噁烷类衍生物及其应用 |
EP3027607B1 (en) | 2013-07-29 | 2020-08-26 | Sunshine Lake Pharma Co., Ltd. | Substituted heteroaryl compounds and methods of use thereof |
CN105732591B (zh) * | 2014-12-31 | 2019-10-25 | 广东东阳光药业有限公司 | 取代的哌嗪化合物及其使用方法和用途 |
CN106795160B (zh) * | 2015-07-23 | 2019-04-19 | 广东东阳光药业有限公司 | 取代的吲哚化合物及其使用方法和用途 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9305641D0 (en) * | 1993-03-18 | 1993-05-05 | Merck Sharp & Dohme | Therapeutic agents |
DE4414113A1 (de) * | 1994-04-22 | 1995-10-26 | Merck Patent Gmbh | 3-Indolylpiperidine |
ZA9711376B (en) * | 1996-12-20 | 1998-07-21 | Lundbeck & Co As H | Indole or dihydroindole derivatives |
-
1999
- 1999-06-14 EP EP99926281A patent/EP1089997A1/en not_active Withdrawn
- 1999-06-14 JP JP2000555890A patent/JP2003521443A/ja not_active Withdrawn
- 1999-06-14 CA CA002335711A patent/CA2335711A1/en not_active Abandoned
- 1999-06-14 WO PCT/DK1999/000326 patent/WO1999067237A1/en not_active Application Discontinuation
- 1999-06-14 AU AU43592/99A patent/AU765317C/en not_active Ceased
- 1999-06-14 HU HU0101475A patent/HUP0101475A3/hu unknown
- 1999-06-14 NZ NZ508506A patent/NZ508506A/en unknown
-
2000
- 2000-12-11 HR HR20000847A patent/HRP20000847A2/hr not_active Application Discontinuation
- 2000-12-18 NO NO20006460A patent/NO20006460L/no not_active Application Discontinuation
-
2001
- 2001-01-10 BG BG105136A patent/BG105136A/xx unknown
Also Published As
Publication number | Publication date |
---|---|
CA2335711A1 (en) | 1999-12-29 |
AU765317C (en) | 2004-05-20 |
WO1999067237A1 (en) | 1999-12-29 |
NO20006460D0 (no) | 2000-12-18 |
HUP0101475A3 (en) | 2003-01-28 |
EP1089997A1 (en) | 2001-04-11 |
NZ508506A (en) | 2004-01-30 |
NO20006460L (no) | 2001-02-19 |
JP2003521443A (ja) | 2003-07-15 |
HUP0101475A2 (hu) | 2001-10-28 |
AU4359299A (en) | 2000-01-10 |
BG105136A (en) | 2001-09-28 |
AU765317B2 (en) | 2003-09-18 |
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