ZA200007157B - 4,5,6 and 7-indole and indoline derivatives, their preparation and use. - Google Patents
4,5,6 and 7-indole and indoline derivatives, their preparation and use. Download PDFInfo
- Publication number
- ZA200007157B ZA200007157B ZA200007157A ZA200007157A ZA200007157B ZA 200007157 B ZA200007157 B ZA 200007157B ZA 200007157 A ZA200007157 A ZA 200007157A ZA 200007157 A ZA200007157 A ZA 200007157A ZA 200007157 B ZA200007157 B ZA 200007157B
- Authority
- ZA
- South Africa
- Prior art keywords
- indol
- piperazine
- ethyl
- chloro
- benzofuranyl
- Prior art date
Links
- 125000003387 indolinyl group Chemical class N1(CCC2=CC=CC=C12)* 0.000 title claims description 5
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 58
- 150000001875 compounds Chemical class 0.000 claims description 54
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 38
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 108020003175 receptors Proteins 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 230000000697 serotonin reuptake Effects 0.000 claims description 9
- 208000019901 Anxiety disease Diseases 0.000 claims description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 230000005764 inhibitory process Effects 0.000 claims description 7
- -1 methylenedioxy group Chemical group 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 208000019022 Mood disease Diseases 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 208000035475 disorder Diseases 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 241001465754 Metazoa Species 0.000 claims description 5
- 230000008485 antagonism Effects 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 4
- 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 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 3
- 208000028017 Psychotic disease Diseases 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 208000019906 panic disease Diseases 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 2
- 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 2
- 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 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
- 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
- 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 2
- ULRFMFWYCTWWJP-UHFFFAOYSA-N 3-[4-[4-(1h-indol-4-yl)piperazin-1-yl]butyl]-1h-indole Chemical compound C=1NC2=CC=CC=C2C=1CCCCN(CC1)CCN1C1=CC=CC2=C1C=CN2 ULRFMFWYCTWWJP-UHFFFAOYSA-N 0.000 claims description 2
- 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 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
- KTOWLGUPFBOSIA-UHFFFAOYSA-N 4-[4-[2-(1-benzofuran-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)=COC2=C1 KTOWLGUPFBOSIA-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
- OCADYZTYZFYYSU-UHFFFAOYSA-N 4-[4-[2-(4,5-dichloro-1-benzofuran-3-yl)ethyl]piperazin-1-yl]-1h-indole Chemical compound C12=C(Cl)C(Cl)=CC=C2OC=C1CCN(CC1)CCN1C1=CC=CC2=C1C=CN2 OCADYZTYZFYYSU-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
- 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 2
- 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 2
- GOWWAPOSJWQAGR-UHFFFAOYSA-N 4-[4-[2-(5-methyl-1-benzofuran-3-yl)ethyl]piperazin-1-yl]-1h-indole Chemical compound C12=CC(C)=CC=C2OC=C1CCN(CC1)CCN1C1=CC=CC2=C1C=CN2 GOWWAPOSJWQAGR-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
- 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 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
- ZSRIARZGWRFDFJ-UHFFFAOYSA-N 4-[4-[4-(5-fluoro-1-benzofuran-3-yl)butyl]piperazin-1-yl]-1h-indole Chemical compound C12=CC(F)=CC=C2OC=C1CCCCN(CC1)CCN1C1=CC=CC2=C1C=CN2 ZSRIARZGWRFDFJ-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
- ULDFQIUEDCUFEE-UHFFFAOYSA-N 5-bromo-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)Br)=C1 ULDFQIUEDCUFEE-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- LESVZAQYIYBRAU-UHFFFAOYSA-N 5-fluoro-3-[2-[4-(1h-indol-4-yl)piperazin-1-yl]ethyl]-1h-indole Chemical compound C12=CC(F)=CC=C2NC=C1CCN(CC1)CCN1C1=CC=CC2=C1C=CN2 LESVZAQYIYBRAU-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- FYOIADVSUOQQCR-UHFFFAOYSA-N 6-chloro-3-[2-[4-(1h-indol-6-yl)piperazin-1-yl]ethyl]-1h-indole Chemical compound C1=C2C=CNC2=CC(N2CCN(CC2)CCC=2C3=CC=C(C=C3NC=2)Cl)=C1 FYOIADVSUOQQCR-UHFFFAOYSA-N 0.000 claims description 2
- ADOICXFBZJAQLI-UHFFFAOYSA-N 6-chloro-3-[2-[4-(1h-indol-7-yl)piperazin-1-yl]ethyl]-1h-indole Chemical compound C=1NC2=CC(Cl)=CC=C2C=1CCN(CC1)CCN1C1=CC=CC2=C1NC=C2 ADOICXFBZJAQLI-UHFFFAOYSA-N 0.000 claims description 2
- GTNTWQDSNUCTOZ-UHFFFAOYSA-N 6-chloro-3-[2-[4-(6-chloro-1h-indol-4-yl)piperazin-1-yl]ethyl]-1h-indole Chemical compound C=1NC2=CC(Cl)=CC=C2C=1CCN(CC1)CCN1C1=CC(Cl)=CC2=C1C=CN2 GTNTWQDSNUCTOZ-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- 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 2
- 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 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical group C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 2
- 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 2
- 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 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 125000003441 thioacyl group Chemical group 0.000 claims description 2
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 2
- 208000017194 Affective disease Diseases 0.000 claims 4
- 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 1
- 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 1
- VMCIXZDRJYETAU-UHFFFAOYSA-N 4-[4-[(5-fluoro-1-benzofuran-3-yl)methyl]piperazin-1-yl]-1h-indole Chemical compound C12=CC(F)=CC=C2OC=C1CN(CC1)CCN1C1=CC=CC2=C1C=CN2 VMCIXZDRJYETAU-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 108091005482 5-HT4 receptors Proteins 0.000 claims 1
- KBVVSNDQPDIRET-UHFFFAOYSA-N 6-chloro-3-[2-[4-(7-chloro-1h-indol-4-yl)piperazin-1-yl]ethyl]-1h-indole Chemical compound C=1NC2=CC(Cl)=CC=C2C=1CCN(CC1)CCN1C1=CC=C(Cl)C2=C1C=CN2 KBVVSNDQPDIRET-UHFFFAOYSA-N 0.000 claims 1
- MVVBNAFDXGBTIE-UHFFFAOYSA-N 7-chloro-3-[[4-(1h-indol-5-yl)-3,6-dihydro-2h-pyridin-1-yl]methyl]-2h-indazole Chemical compound C1=C2NC=CC2=CC(C=2CCN(CC=2)CC=2C=3C=CC=C(C=3NN=2)Cl)=C1 MVVBNAFDXGBTIE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 102000005962 receptors Human genes 0.000 description 11
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 208000020401 Depressive disease Diseases 0.000 description 5
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 5
- 230000003042 antagnostic effect Effects 0.000 description 4
- 239000000935 antidepressant agent Substances 0.000 description 4
- 229940005513 antidepressants Drugs 0.000 description 4
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 4
- 238000010304 firing Methods 0.000 description 4
- 210000002348 5-ht neuron Anatomy 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000003772 serotonin uptake inhibitor Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000009825 accumulation Methods 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- 238000000586 desensitisation Methods 0.000 description 2
- 229960003638 dopamine Drugs 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- PHUTUTUABXHXLW-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=NC=C[C]12 PHUTUTUABXHXLW-UHFFFAOYSA-N 0.000 description 2
- 229960002508 pindolol Drugs 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 239000002464 receptor antagonist Substances 0.000 description 2
- 229940044551 receptor antagonist Drugs 0.000 description 2
- 229940076279 serotonin Drugs 0.000 description 2
- AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 description 1
- WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-N 0.000 description 1
- RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 description 1
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- YVFVKJXNWLSCKB-UHFFFAOYSA-N 4-[4-[3-(5-fluoro-1-benzofuran-3-yl)propyl]piperazin-1-yl]-1h-indole Chemical compound C12=CC(F)=CC=C2OC=C1CCCN(CC1)CCN1C1=CC=CC2=C1C=CN2 YVFVKJXNWLSCKB-UHFFFAOYSA-N 0.000 description 1
- YPAVZUFUVXJNTF-UHFFFAOYSA-N 5-chloro-3-[2-[4-(1h-indol-4-yl)piperazin-1-yl]ethyl]-1h-indole Chemical compound C12=CC(Cl)=CC=C2NC=C1CCN(CC1)CCN1C1=CC=CC2=C1C=CN2 YPAVZUFUVXJNTF-UHFFFAOYSA-N 0.000 description 1
- LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan Chemical compound C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 description 1
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 1
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 1
- 102000007527 Autoreceptors Human genes 0.000 description 1
- 108010071131 Autoreceptors Proteins 0.000 description 1
- 206010010144 Completed suicide Diseases 0.000 description 1
- AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000674 adrenergic antagonist Substances 0.000 description 1
- 230000001270 agonistic effect Effects 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229960001653 citalopram Drugs 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000008713 feedback mechanism Effects 0.000 description 1
- 229960002464 fluoxetine Drugs 0.000 description 1
- 229960004038 fluvoxamine Drugs 0.000 description 1
- CJOFXWAVKWHTFT-XSFVSMFZSA-N fluvoxamine Chemical compound COCCCC\C(=N/OCCN)C1=CC=C(C(F)(F)F)C=C1 CJOFXWAVKWHTFT-XSFVSMFZSA-N 0.000 description 1
- 210000001624 hip Anatomy 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
- 230000001404 mediated effect Effects 0.000 description 1
- 230000036651 mood Effects 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
- 210000001577 neostriatum Anatomy 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 229940053544 other antidepressants in atc Drugs 0.000 description 1
- 229960002296 paroxetine Drugs 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 210000001609 raphe nuclei Anatomy 0.000 description 1
- 238000011084 recovery Methods 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
- 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
- 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
- 230000002459 sustained effect Effects 0.000 description 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 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
- 230000001225 therapeutic effect Effects 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
- A61P25/24—Antidepressants
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK82098 | 1998-06-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200007157B true ZA200007157B (en) | 2001-11-22 |
Family
ID=8097932
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200007157A ZA200007157B (en) | 1998-06-19 | 2000-12-04 | 4,5,6 and 7-indole and indoline derivatives, their preparation and use. |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US6391882B1 (cs) |
| KR (1) | KR20010071513A (cs) |
| CN (1) | CN1336925A (cs) |
| AR (1) | AR018899A1 (cs) |
| BR (1) | BR9911843A (cs) |
| CZ (1) | CZ20004780A3 (cs) |
| EA (1) | EA004248B1 (cs) |
| HK (1) | HK1044339A1 (cs) |
| ID (1) | ID27976A (cs) |
| IL (1) | IL139962A0 (cs) |
| IS (1) | IS5731A (cs) |
| PL (1) | PL344978A1 (cs) |
| SK (1) | SK19412000A3 (cs) |
| TR (1) | TR200003858T2 (cs) |
| YU (1) | YU78100A (cs) |
| ZA (1) | ZA200007157B (cs) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60021194T2 (de) * | 1999-08-23 | 2005-12-22 | Solvay Pharmaceuticals B.V. | Phenylpiperazin-derivate als inhibitoren der serotonin-wiederaufnahme |
| DE10219035A1 (de) * | 2002-04-29 | 2003-11-13 | Bayer Cropscience Ag | Biphenylcarboxamide |
| US7153858B2 (en) * | 2003-01-31 | 2006-12-26 | Epix Delaware, Inc. | Arylpiperazinyl compounds |
| KR20090076962A (ko) | 2006-11-09 | 2009-07-13 | 에프. 호프만-라 로슈 아게 | 인돌 및 벤조퓨란 2-카복스아마이드 유도체 |
| AU2009308687A1 (en) * | 2008-11-03 | 2010-05-06 | Chemocentryx, Inc. | Compounds for the treatment of osteoporosis and cancers |
| BR112012024380A2 (pt) | 2010-03-25 | 2015-09-15 | Glaxosmithkline Llc | compostos químicos |
| WO2016192657A1 (en) | 2015-06-03 | 2016-12-08 | Sunshine Lake Pharma Co., Ltd. | Substituted piperazine compounds and methods of use and use thereof |
Family Cites Families (4)
| 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 |
| IL114026A (en) * | 1994-06-08 | 1999-06-20 | Lundbeck & Co As H | 4-aryl-1-(indanmethyl dihydrobenzofuranmethyl or dihydrobenzo thiophenemethyl) piperidines tetrahydropyridines or piperazines and pharmaceutical compositions containing them |
| ZA9711376B (en) * | 1996-12-20 | 1998-07-21 | Lundbeck & Co As H | Indole or dihydroindole derivatives |
-
1999
- 1999-06-14 ID IDW20010126A patent/ID27976A/id unknown
- 1999-06-14 CN CN99809740A patent/CN1336925A/zh active Pending
- 1999-06-14 US US09/719,849 patent/US6391882B1/en not_active Expired - Fee Related
- 1999-06-14 SK SK1941-2000A patent/SK19412000A3/sk unknown
- 1999-06-14 IL IL13996299A patent/IL139962A0/xx unknown
- 1999-06-14 CZ CZ20004780A patent/CZ20004780A3/cs unknown
- 1999-06-14 TR TR2000/03858T patent/TR200003858T2/xx unknown
- 1999-06-14 YU YU78100A patent/YU78100A/sh unknown
- 1999-06-14 BR BR9911843-2A patent/BR9911843A/pt not_active IP Right Cessation
- 1999-06-14 PL PL99344978A patent/PL344978A1/xx not_active Application Discontinuation
- 1999-06-14 EA EA200100056A patent/EA004248B1/ru not_active IP Right Cessation
- 1999-06-14 KR KR1020007014399A patent/KR20010071513A/ko not_active Withdrawn
- 1999-06-14 HK HK02105927.5A patent/HK1044339A1/zh unknown
- 1999-06-18 AR ARP990102954A patent/AR018899A1/es not_active Application Discontinuation
-
2000
- 2000-11-24 IS IS5731A patent/IS5731A/is unknown
- 2000-12-04 ZA ZA200007157A patent/ZA200007157B/en unknown
-
2002
- 2002-01-15 US US10/053,168 patent/US20020128272A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CZ20004780A3 (cs) | 2001-08-15 |
| IS5731A (is) | 2000-11-24 |
| IL139962A0 (en) | 2002-02-10 |
| CN1336925A (zh) | 2002-02-20 |
| US6391882B1 (en) | 2002-05-21 |
| BR9911843A (pt) | 2001-03-20 |
| EA200100056A1 (ru) | 2001-06-25 |
| US20020128272A1 (en) | 2002-09-12 |
| PL344978A1 (en) | 2001-11-19 |
| YU78100A (sh) | 2003-04-30 |
| KR20010071513A (ko) | 2001-07-28 |
| SK19412000A3 (sk) | 2001-07-10 |
| ID27976A (id) | 2001-05-03 |
| EA004248B1 (ru) | 2004-02-26 |
| AR018899A1 (es) | 2001-12-12 |
| TR200003858T2 (tr) | 2001-06-21 |
| HK1044339A1 (zh) | 2002-10-18 |
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