CA2335711A1 - Derives de 4, 5, 6, et 7-indole ou d'indoline, leur preparation, et leur utilisation - Google Patents
Derives de 4, 5, 6, et 7-indole ou d'indoline, leur preparation, et leur utilisation Download PDFInfo
- Publication number
- CA2335711A1 CA2335711A1 CA002335711A CA2335711A CA2335711A1 CA 2335711 A1 CA2335711 A1 CA 2335711A1 CA 002335711 A CA002335711 A CA 002335711A CA 2335711 A CA2335711 A CA 2335711A CA 2335711 A1 CA2335711 A1 CA 2335711A1
- Authority
- CA
- Canada
- Prior art keywords
- indol
- piperazine
- ethyl
- chloro
- benzofuranyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 125000003387 indolinyl group Chemical class N1(CCC2=CC=CC=C12)* 0.000 title claims abstract 3
- 238000002360 preparation method Methods 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 99
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 97
- 238000000034 method Methods 0.000 claims description 33
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 230000005764 inhibitory process Effects 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 230000000697 serotonin reuptake Effects 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- -1 C1-6-alk(en/yn)yl Chemical group 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 150000002367 halogens Chemical group 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 9
- 208000019901 Anxiety disease Diseases 0.000 claims description 8
- 150000002431 hydrogen Chemical group 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 208000035475 disorder Diseases 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 241001465754 Metazoa Species 0.000 claims description 5
- 208000019022 Mood disease Diseases 0.000 claims description 5
- 230000008485 antagonism Effects 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 4
- 208000028017 Psychotic disease Diseases 0.000 claims description 4
- 125000002252 acyl group Chemical group 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 208000019906 panic disease Diseases 0.000 claims description 4
- 102000034527 Retinoid X Receptors Human genes 0.000 claims description 3
- 108010038912 Retinoid X Receptors Proteins 0.000 claims description 3
- 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 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000003441 thioacyl 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 2
- HEFXXFLAWUQZNG-UHFFFAOYSA-N 1-benzyl-4-[4-[2-(5-bromo-1h-indol-3-yl)ethyl]piperazin-1-yl]indole Chemical compound C12=CC(Br)=CC=C2NC=C1CCN(CC1)CCN1C(C=1C=C2)=CC=CC=1N2CC1=CC=CC=C1 HEFXXFLAWUQZNG-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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
- 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
- KHKMOERJTMSLFX-UHFFFAOYSA-N 3-[2-[4-(1h-indol-4-yl)piperazin-1-yl]ethyl]-7-methyl-1h-indole Chemical compound C=1NC=2C(C)=CC=CC=2C=1CCN(CC1)CCN1C1=CC=CC2=C1C=CN2 KHKMOERJTMSLFX-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
- 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
- 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
- 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
- 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 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
- 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 2
- 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 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
- 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 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
- 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 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
- 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 2
- 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 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
- 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 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
- 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 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
- 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 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
- HHSMYZNWCXZWEH-UHFFFAOYSA-N 5-fluoro-3-[2-[4-(1h-indol-4-yl)-3,6-dihydro-2h-pyridin-1-yl]ethyl]-1h-indole Chemical compound C12=CC(F)=CC=C2NC=C1CCN(CC=1)CCC=1C1=CC=CC2=C1C=CN2 HHSMYZNWCXZWEH-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
- WJEIGMPATUEZQV-UHFFFAOYSA-N 6-chloro-3-[2-[4-(1h-indol-4-yl)-3,6-dihydro-2h-pyridin-1-yl]ethyl]-1h-indole Chemical compound C=1NC2=CC(Cl)=CC=C2C=1CCN(CC=1)CCC=1C1=CC=CC2=C1C=CN2 WJEIGMPATUEZQV-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
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- 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
- 239000006260 foam Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 239000010437 gem Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical class C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 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
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 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
- TXQCEQACTNBDCU-UHFFFAOYSA-N methyl 4-piperazin-1-yl-1h-indole-6-carboxylate Chemical compound C=12C=CNC2=CC(C(=O)OC)=CC=1N1CCNCC1 TXQCEQACTNBDCU-UHFFFAOYSA-N 0.000 description 1
- LRKHQYYRUOJNRW-UHFFFAOYSA-N methyl 5-fluoro-1-benzofuran-3-carboxylate Chemical compound C1=C(F)C=C2C(C(=O)OC)=COC2=C1 LRKHQYYRUOJNRW-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000002156 mixing Methods 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
- 125000001624 naphthyl group Chemical group 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
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229940053544 other antidepressants in atc Drugs 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 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
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000003053 piperidines Chemical class 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
- 239000002243 precursor Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 210000001609 raphe nuclei Anatomy 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000002829 reductive effect Effects 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
- 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
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002459 sustained effect Effects 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
- 238000004885 tandem mass spectrometry Methods 0.000 description 1
- 150000003892 tartrate salts Chemical class 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
- 238000012546 transfer Methods 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)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Abstract
L'invention concerne un dérivé de 4-, 5-, 6-, et 7-indole ou d'indoline substitué de formule (I), dans laquelle A représente un groupe de formule (IIA), (IIB), (IIC), dans laquelle X, U, Y, R?3¿ à R?12¿, Z, W, n et m sont tels que définis ci-dessus. Les composés de cette invention sont de puissants inhibiteurs du recaptage de la sérotonine, et présentent une action antagoniste du récepteur 5-HT¿1A?.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DK82098 | 1998-06-19 | ||
DKPA199800820 | 1998-06-19 | ||
US9282398P | 1998-07-14 | 1998-07-14 | |
US60/092,823 | 1998-07-14 | ||
PCT/DK1999/000326 WO1999067237A1 (fr) | 1998-06-19 | 1999-06-14 | Derives de 4, 5, 6, et 7-indole ou d'indoline, leur preparation, et leur utilisation |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2335711A1 true CA2335711A1 (fr) | 1999-12-29 |
Family
ID=26064717
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002335711A Abandoned CA2335711A1 (fr) | 1998-06-19 | 1999-06-14 | Derives de 4, 5, 6, et 7-indole ou d'indoline, leur preparation, et leur utilisation |
Country Status (10)
Country | Link |
---|---|
EP (1) | EP1089997A1 (fr) |
JP (1) | JP2003521443A (fr) |
AU (1) | AU765317C (fr) |
BG (1) | BG105136A (fr) |
CA (1) | CA2335711A1 (fr) |
HR (1) | HRP20000847A2 (fr) |
HU (1) | HUP0101475A3 (fr) |
NO (1) | NO20006460L (fr) |
NZ (1) | NZ508506A (fr) |
WO (1) | WO1999067237A1 (fr) |
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 |
SI1212320T1 (en) * | 1999-08-23 | 2005-10-31 | Solvay Pharmaceuticals B.V. | Phenylpiperazines as serotonin reuptake inhibitors |
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 |
ATE316523T1 (de) * | 2002-05-13 | 2006-02-15 | Hoffmann La Roche | Benzoxazinderivate als 5-ht6-modulatoren und deren verwendungen |
AR040967A1 (es) * | 2002-08-12 | 2005-04-27 | Janssen Pharmaceutica Nv | Derivados de isoxazolina triciclicos c- sustituidos y su uso como anti- depresivos |
CA2494557C (fr) | 2002-08-15 | 2011-10-18 | Janssen Pharmaceutica N.V. | Derives d'isoxazoline heterocycliques fusionnes et leur utilisation en tant qu'antidepresseurs |
AU2003257407A1 (en) * | 2002-08-29 | 2004-03-19 | 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 |
JP2008523030A (ja) * | 2004-12-08 | 2008-07-03 | ソルベイ・フアーマシユーチカルズ・ベー・ブイ | 部分的ドーパミン−d2受容体作動性とセロトニン再摂取阻害の組み合わせを示すフェニルピペラジン誘導体 |
US7807671B2 (en) * | 2006-04-25 | 2010-10-05 | Bristol-Myers Squibb Company | Diketo-piperazine and piperidine derivatives as antiviral agents |
CA2668959A1 (fr) | 2006-11-09 | 2008-05-15 | F. Hoffmann-La Roche Ag | Derives d'indole et de benzofuran 2-carboxamide |
CA2718138A1 (fr) * | 2008-03-14 | 2009-09-17 | Timo Heinrich | Composes d'azaindole pour le traitement de troubles du systeme nerveux central |
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 (fr) | 2013-07-29 | 2020-08-26 | Sunshine Lake Pharma Co., Ltd. | Composés hétéroaryliques substitués et procédés d'utilisation |
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 |
WO2017012579A1 (fr) * | 2015-07-23 | 2017-01-26 | 广东东阳光药业有限公司 | Composés d'indole substitués, méthodes d'utilisation et utilisations de ceux-ci |
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 AU AU43592/99A patent/AU765317C/en not_active Ceased
- 1999-06-14 EP EP99926281A patent/EP1089997A1/fr not_active Withdrawn
- 1999-06-14 WO PCT/DK1999/000326 patent/WO1999067237A1/fr not_active Application Discontinuation
- 1999-06-14 CA CA002335711A patent/CA2335711A1/fr not_active Abandoned
- 1999-06-14 JP JP2000555890A patent/JP2003521443A/ja not_active Withdrawn
- 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 |
---|---|
AU765317C (en) | 2004-05-20 |
AU765317B2 (en) | 2003-09-18 |
WO1999067237A1 (fr) | 1999-12-29 |
NO20006460D0 (no) | 2000-12-18 |
EP1089997A1 (fr) | 2001-04-11 |
JP2003521443A (ja) | 2003-07-15 |
HUP0101475A3 (en) | 2003-01-28 |
BG105136A (en) | 2001-09-28 |
HUP0101475A2 (hu) | 2001-10-28 |
HRP20000847A2 (en) | 2001-12-31 |
NZ508506A (en) | 2004-01-30 |
AU4359299A (en) | 2000-01-10 |
NO20006460L (no) | 2001-02-19 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
FZDE | Discontinued |