CA2382247C - Azaindoles having serotonin receptor affinity - Google Patents
Azaindoles having serotonin receptor affinity Download PDFInfo
- Publication number
- CA2382247C CA2382247C CA2382247A CA2382247A CA2382247C CA 2382247 C CA2382247 C CA 2382247C CA 2382247 A CA2382247 A CA 2382247A CA 2382247 A CA2382247 A CA 2382247A CA 2382247 C CA2382247 C CA 2382247C
- Authority
- CA
- Canada
- Prior art keywords
- azaindole
- indolizinyl
- hexahydro
- octahydro
- naphthalenesulfonyl
- 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.)
- Expired - Fee Related
Links
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 title description 8
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 title description 8
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 131
- 108091005435 5-HT6 receptors Proteins 0.000 claims abstract description 30
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims description 25
- SHUJGWWKEOGIKB-UHFFFAOYSA-N 3-(1,2,3,5,6,7,8,8a-octahydroindolizin-7-yl)-1h-pyrrolo[3,2-c]pyridine Chemical compound C1=NC=C2C(C3CC4CCCN4CC3)=CNC2=C1 SHUJGWWKEOGIKB-UHFFFAOYSA-N 0.000 claims description 16
- VMSVWNATGMTCJN-UHFFFAOYSA-N 3-(1,2,3,5,8,8a-hexahydroindolizin-7-yl)-1h-pyrrolo[3,2-c]pyridine Chemical compound C1=NC=C2C(C=3CC4CCCN4CC=3)=CNC2=C1 VMSVWNATGMTCJN-UHFFFAOYSA-N 0.000 claims description 15
- PGAVHYCWYWOJFQ-UHFFFAOYSA-N 3-(1,2,3,5,8,8a-hexahydroindolizin-7-yl)-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CC=C2C(C=3CC4CCCN4CC=3)=CNC2=N1 PGAVHYCWYWOJFQ-UHFFFAOYSA-N 0.000 claims description 11
- 239000012453 solvate Substances 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- WGWMVQWFVUCIBS-UHFFFAOYSA-N 3-(1,2,3,5,6,7,8,8a-octahydroindolizin-7-yl)-1-naphthalen-2-ylsulfonylpyrrolo[2,3-b]pyridine Chemical compound C1=C(C2CC3CCCN3CC2)C2=CC=CN=C2N1S(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 WGWMVQWFVUCIBS-UHFFFAOYSA-N 0.000 claims description 8
- ALOYIHSIDZIWBV-UHFFFAOYSA-N 3-(1,2,3,5,6,7,8,8a-octahydroindolizin-7-yl)-1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CN=C2C(C3CC4CCCN4CC3)=CNC2=C1 ALOYIHSIDZIWBV-UHFFFAOYSA-N 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- VEPOXPKPYHBHDK-UHFFFAOYSA-N 2-[3-(1,2,3,5,6,7,8,8a-octahydroindolizin-7-yl)-2,5-dichlorophenyl]sulfonyl-1h-pyrrolo[3,2-c]pyridine Chemical compound N1=CC=C2NC(S(=O)(=O)C=3C(Cl)=C(C4CC5CCCN5CC4)C=C(C=3)Cl)=CC2=C1 VEPOXPKPYHBHDK-UHFFFAOYSA-N 0.000 claims description 7
- CICGWVYPAWNNIE-UHFFFAOYSA-N 3-(1,2,3,5,6,7,8,8a-octahydroindolizin-7-yl)-1-naphthalen-1-ylsulfonylpyrrolo[2,3-b]pyridine Chemical compound C1=C(C2CC3CCCN3CC2)C2=CC=CN=C2N1S(=O)(=O)C1=CC=CC2=CC=CC=C12 CICGWVYPAWNNIE-UHFFFAOYSA-N 0.000 claims description 6
- MVJAGLGXNLMRTO-UHFFFAOYSA-N 3-(1,2,3,5,6,7,8,8a-octahydroindolizin-7-yl)-1-naphthalen-1-ylsulfonylpyrrolo[3,2-b]pyridine Chemical compound C1=C(C2CC3CCCN3CC2)C2=NC=CC=C2N1S(=O)(=O)C1=CC=CC2=CC=CC=C12 MVJAGLGXNLMRTO-UHFFFAOYSA-N 0.000 claims description 6
- PRKUGFVPSCNSIB-UHFFFAOYSA-N 3-(1,2,3,5,6,7,8,8a-octahydroindolizin-7-yl)-1-naphthalen-2-ylsulfonylpyrrolo[3,2-b]pyridine Chemical compound C1=C(C2CC3CCCN3CC2)C2=NC=CC=C2N1S(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 PRKUGFVPSCNSIB-UHFFFAOYSA-N 0.000 claims description 6
- XPTMXVRFXINZSY-UHFFFAOYSA-N 3-(1,2,3,5,6,7,8,8a-octahydroindolizin-7-yl)-1-naphthalen-2-ylsulfonylpyrrolo[3,2-c]pyridine Chemical compound C1=C(C2CC3CCCN3CC2)C2=CN=CC=C2N1S(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 XPTMXVRFXINZSY-UHFFFAOYSA-N 0.000 claims description 6
- SAIMZEWINXIYCT-UHFFFAOYSA-N 3-(1,2,3,5,8,8a-hexahydroindolizin-7-yl)-1h-pyrrolo[2,3-c]pyridine Chemical compound N1=CC=C2C(C=3CC4CCCN4CC=3)=CNC2=C1 SAIMZEWINXIYCT-UHFFFAOYSA-N 0.000 claims description 6
- RVMWHFCJSMACCF-UHFFFAOYSA-N 3-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)-1h-pyrrolo[3,2-c]pyridine Chemical compound C1N(C)CCC(C=2C3=CN=CC=C3NC=2)=C1 RVMWHFCJSMACCF-UHFFFAOYSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- FXIXQCNASYENJN-UHFFFAOYSA-N 3-(1,2,3,5,6,7,8,8a-octahydroindolizin-7-yl)-1-(benzenesulfonyl)pyrrolo[3,2-c]pyridine Chemical compound C1=C(C2CC3CCCN3CC2)C2=CN=CC=C2N1S(=O)(=O)C1=CC=CC=C1 FXIXQCNASYENJN-UHFFFAOYSA-N 0.000 claims description 5
- YVNFPVDQZZAGMA-UHFFFAOYSA-N 3-(1,2,3,5,6,7,8,8a-octahydroindolizin-7-yl)-1-naphthalen-1-ylsulfonylpyrrolo[3,2-c]pyridine Chemical compound C1=C(C2CC3CCCN3CC2)C2=CN=CC=C2N1S(=O)(=O)C1=CC=CC2=CC=CC=C12 YVNFPVDQZZAGMA-UHFFFAOYSA-N 0.000 claims description 5
- BSYSGGLVESLGTK-UHFFFAOYSA-N 3-(1,2,3,5,8,8a-hexahydroindolizin-7-yl)-1-(benzenesulfonyl)pyrrolo[3,2-c]pyridine Chemical compound C1=C(C=2CC3CCCN3CC=2)C2=CN=CC=C2N1S(=O)(=O)C1=CC=CC=C1 BSYSGGLVESLGTK-UHFFFAOYSA-N 0.000 claims description 5
- VSLFARANIWFODR-UHFFFAOYSA-N 3-(1,2,3,5,8,8a-hexahydroindolizin-7-yl)-1-naphthalen-2-ylsulfonylpyrrolo[2,3-b]pyridine Chemical compound C1=C(C=2CC3CCCN3CC=2)C2=CC=CN=C2N1S(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 VSLFARANIWFODR-UHFFFAOYSA-N 0.000 claims description 5
- GAKAACVLHNWCAS-UHFFFAOYSA-N 3-(1-methylpiperidin-4-yl)-1h-pyrrolo[3,2-c]pyridine Chemical compound C1CN(C)CCC1C1=CNC2=CC=NC=C12 GAKAACVLHNWCAS-UHFFFAOYSA-N 0.000 claims description 5
- IJAWXADAXNQWQU-UHFFFAOYSA-N [3-(1,2,3,5,8,8a-hexahydroindolizin-7-yl)pyrrolo[2,3-b]pyridin-1-yl]-(2,6-dichlorophenyl)methanone Chemical compound ClC1=CC=CC(Cl)=C1C(=O)N1C2=NC=CC=C2C(C=2CC3CCCN3CC=2)=C1 IJAWXADAXNQWQU-UHFFFAOYSA-N 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- BJWXITQMNYHOQB-UHFFFAOYSA-N (2,6-dichlorophenyl)-[3-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)pyrrolo[3,2-c]pyridin-1-yl]methanone Chemical compound C1N(C)CCC(C=2C3=CN=CC=C3N(C(=O)C=3C(=CC=CC=3Cl)Cl)C=2)=C1 BJWXITQMNYHOQB-UHFFFAOYSA-N 0.000 claims description 4
- UIXDVQSRWYQJHJ-UHFFFAOYSA-N (2,6-dichlorophenyl)-[3-(1-methylpiperidin-4-yl)pyrrolo[3,2-c]pyridin-1-yl]methanone Chemical compound C1CN(C)CCC1C(C1=CN=CC=C11)=CN1C(=O)C1=C(Cl)C=CC=C1Cl UIXDVQSRWYQJHJ-UHFFFAOYSA-N 0.000 claims description 4
- TYNVLZIAWGVTJU-UHFFFAOYSA-N (4-fluorophenyl)-[3-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)pyrrolo[2,3-b]pyridin-1-yl]methanone Chemical compound C1N(C)CCC(C=2C3=CC=CN=C3N(C(=O)C=3C=CC(F)=CC=3)C=2)=C1 TYNVLZIAWGVTJU-UHFFFAOYSA-N 0.000 claims description 4
- WGFKJBUKBWWQRR-UHFFFAOYSA-N (4-methoxyphenyl)-[3-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)pyrrolo[2,3-b]pyridin-1-yl]methanone Chemical compound C1=CC(OC)=CC=C1C(=O)N1C2=NC=CC=C2C(C=2CCN(C)CC=2)=C1 WGFKJBUKBWWQRR-UHFFFAOYSA-N 0.000 claims description 4
- CSGQRPHJYSLUOB-UHFFFAOYSA-N 1-(4-fluorophenyl)sulfonyl-3-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)pyrrolo[2,3-b]pyridine Chemical compound C1N(C)CCC(C=2C3=CC=CN=C3N(C=2)S(=O)(=O)C=2C=CC(F)=CC=2)=C1 CSGQRPHJYSLUOB-UHFFFAOYSA-N 0.000 claims description 4
- PMWBNLNNRYVXEV-UHFFFAOYSA-N 1-(4-methoxyphenyl)sulfonyl-3-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)pyrrolo[2,3-b]pyridine Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=NC=CC=C2C(C=2CCN(C)CC=2)=C1 PMWBNLNNRYVXEV-UHFFFAOYSA-N 0.000 claims description 4
- MIDYODKZIIWWHK-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)pyrrolo[2,3-b]pyridine Chemical compound C1N(C)CCC(C=2C3=CC=CN=C3N(C=2)S(=O)(=O)C=2C=CC=CC=2)=C1 MIDYODKZIIWWHK-UHFFFAOYSA-N 0.000 claims description 4
- LIXZPQVPTSYTPT-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-(1-methylpiperidin-4-yl)pyrrolo[3,2-c]pyridine Chemical compound C1CN(C)CCC1C1=CN(S(=O)(=O)C=2C=CC=CC=2)C2=CC=NC=C12 LIXZPQVPTSYTPT-UHFFFAOYSA-N 0.000 claims description 4
- PMSPULBCDNOMJD-UHFFFAOYSA-N 3-(1,2,3,5,6,7,8,8a-octahydroindolizin-7-yl)-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CC=C2C(C3CC4CCCN4CC3)=CNC2=N1 PMSPULBCDNOMJD-UHFFFAOYSA-N 0.000 claims description 4
- NCAXBIMSXYSCKX-UHFFFAOYSA-N 3-(1,2,3,5,8,8a-hexahydroindolizin-7-yl)-1-(4-fluorophenyl)sulfonylpyrrolo[2,3-b]pyridine Chemical compound C1=CC(F)=CC=C1S(=O)(=O)N1C2=NC=CC=C2C(C=2CC3CCCN3CC=2)=C1 NCAXBIMSXYSCKX-UHFFFAOYSA-N 0.000 claims description 4
- GHWNZIPAARWORE-UHFFFAOYSA-N 3-(1,2,3,5,8,8a-hexahydroindolizin-7-yl)-1-(4-fluorophenyl)sulfonylpyrrolo[3,2-c]pyridine Chemical compound C1=CC(F)=CC=C1S(=O)(=O)N1C2=CC=NC=C2C(C=2CC3CCCN3CC=2)=C1 GHWNZIPAARWORE-UHFFFAOYSA-N 0.000 claims description 4
- NDWHDDHSRAPPGC-UHFFFAOYSA-N 3-(1,2,3,5,8,8a-hexahydroindolizin-7-yl)-1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=NC=CC=C2C(C=2CC3CCCN3CC=2)=C1 NDWHDDHSRAPPGC-UHFFFAOYSA-N 0.000 claims description 4
- FANGSOMZRLKCRU-UHFFFAOYSA-N 3-(1,2,3,5,8,8a-hexahydroindolizin-7-yl)-1-(4-methylphenyl)sulfonylpyrrolo[3,2-c]pyridine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=CC=NC=C2C(C=2CC3CCCN3CC=2)=C1 FANGSOMZRLKCRU-UHFFFAOYSA-N 0.000 claims description 4
- LFDOZYLVNQASGA-UHFFFAOYSA-N 3-(1,2,3,5,8,8a-hexahydroindolizin-7-yl)-1-naphthalen-1-ylsulfonylpyrrolo[2,3-b]pyridine Chemical compound C1=C(C=2CC3CCCN3CC=2)C2=CC=CN=C2N1S(=O)(=O)C1=CC=CC2=CC=CC=C12 LFDOZYLVNQASGA-UHFFFAOYSA-N 0.000 claims description 4
- DKMNUGORMDRDSC-UHFFFAOYSA-N 3-(1,2,3,5,8,8a-hexahydroindolizin-7-yl)-1-naphthalen-1-ylsulfonylpyrrolo[2,3-c]pyridine Chemical compound C1=C(C=2CC3CCCN3CC=2)C2=CC=NC=C2N1S(=O)(=O)C1=CC=CC2=CC=CC=C12 DKMNUGORMDRDSC-UHFFFAOYSA-N 0.000 claims description 4
- BQZSPRXNXIAPCX-UHFFFAOYSA-N 3-(1,2,3,5,8,8a-hexahydroindolizin-7-yl)-1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CN=C2C(C=3CC4CCCN4CC=3)=CNC2=C1 BQZSPRXNXIAPCX-UHFFFAOYSA-N 0.000 claims description 4
- RJPGZBOOXLUXIS-UHFFFAOYSA-N [3-(1,2,3,5,8,8a-hexahydroindolizin-7-yl)pyrrolo[2,3-b]pyridin-1-yl]-(2,6-dimethoxyphenyl)methanone Chemical compound COC1=CC=CC(OC)=C1C(=O)N1C2=NC=CC=C2C(C=2CC3CCCN3CC=2)=C1 RJPGZBOOXLUXIS-UHFFFAOYSA-N 0.000 claims description 4
- NRJBSWIXUSQBTR-UHFFFAOYSA-N [3-(1,2,3,5,8,8a-hexahydroindolizin-7-yl)pyrrolo[2,3-b]pyridin-1-yl]-phenylmethanone Chemical compound C1=C(C=2CC3CCCN3CC=2)C2=CC=CN=C2N1C(=O)C1=CC=CC=C1 NRJBSWIXUSQBTR-UHFFFAOYSA-N 0.000 claims description 4
- QTYPXLJOSPIRQV-UHFFFAOYSA-N [3-(1,2,3,5,8,8a-hexahydroindolizin-7-yl)pyrrolo[3,2-c]pyridin-1-yl]-(2,6-dimethoxyphenyl)methanone Chemical compound COC1=CC=CC(OC)=C1C(=O)N1C2=CC=NC=C2C(C=2CC3CCCN3CC=2)=C1 QTYPXLJOSPIRQV-UHFFFAOYSA-N 0.000 claims description 4
- GQFNRPSMGBVAET-UHFFFAOYSA-N [3-(1,2,3,5,8,8a-hexahydroindolizin-7-yl)pyrrolo[3,2-c]pyridin-1-yl]-phenylmethanone Chemical compound C1=C(C=2CC3CCCN3CC=2)C2=CN=CC=C2N1C(=O)C1=CC=CC=C1 GQFNRPSMGBVAET-UHFFFAOYSA-N 0.000 claims description 4
- RQCPJSGQGXUPTB-UHFFFAOYSA-N [3-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)pyrrolo[2,3-b]pyridin-1-yl]-phenylmethanone Chemical compound C1N(C)CCC(C=2C3=CC=CN=C3N(C(=O)C=3C=CC=CC=3)C=2)=C1 RQCPJSGQGXUPTB-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 239000003751 serotonin 6 antagonist Substances 0.000 claims description 4
- HIJXDWIOHRJBSG-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)pyrrolo[3,2-c]pyridine Chemical compound C1N(C)CCC(C=2C3=CN=CC=C3N(C=2)S(=O)(=O)C=2C=CC=CC=2)=C1 HIJXDWIOHRJBSG-UHFFFAOYSA-N 0.000 claims description 3
- KUYBTFPEERPPTD-UHFFFAOYSA-N 2-(1-naphthalen-1-ylsulfonylpyrrolo[3,2-c]pyridin-3-yl)-2,3,4,6,7,8,9,9a-octahydro-1h-quinolizine Chemical compound C1=C(C2CC3CCCCN3CC2)C2=CN=CC=C2N1S(=O)(=O)C1=CC=CC2=CC=CC=C12 KUYBTFPEERPPTD-UHFFFAOYSA-N 0.000 claims description 3
- GXIKJOYLWCYVQN-UHFFFAOYSA-N 3-(1,2,3,5,6,7,8,8a-octahydroindolizin-7-yl)-1h-pyrrolo[2,3-c]pyridine Chemical compound N1=CC=C2C(C3CC4CCCN4CC3)=CNC2=C1 GXIKJOYLWCYVQN-UHFFFAOYSA-N 0.000 claims description 3
- NSQLQBSRFTUZMT-UHFFFAOYSA-N 3-(1,2,3,5,8,8a-hexahydroindolizin-7-yl)-1-naphthalen-1-ylsulfonylpyrrolo[3,2-c]pyridine Chemical compound C1=C(C=2CC3CCCN3CC=2)C2=CN=CC=C2N1S(=O)(=O)C1=CC=CC2=CC=CC=C12 NSQLQBSRFTUZMT-UHFFFAOYSA-N 0.000 claims description 3
- XGDVMSACWHVPTH-UHFFFAOYSA-N 3-(1,2,3,5,8,8a-hexahydroindolizin-7-yl)-1-naphthalen-2-ylsulfonylpyrrolo[3,2-c]pyridine Chemical compound C1=C(C=2CC3CCCN3CC=2)C2=CN=CC=C2N1S(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 XGDVMSACWHVPTH-UHFFFAOYSA-N 0.000 claims description 3
- 229940124801 5-HT6 antagonist Drugs 0.000 claims description 3
- NJGJYYJRKPMKJU-UHFFFAOYSA-N [3-(1,2,3,5,8,8a-hexahydroindolizin-7-yl)pyrrolo[3,2-c]pyridin-1-yl]-(2,6-dichlorophenyl)methanone Chemical compound ClC1=CC=CC(Cl)=C1C(=O)N1C2=CC=NC=C2C(C=2CC3CCCN3CC=2)=C1 NJGJYYJRKPMKJU-UHFFFAOYSA-N 0.000 claims description 3
- IOWGFNLEWKXDGN-UHFFFAOYSA-N [3-(1,2,3,5,8,8a-hexahydroindolizin-7-yl)pyrrolo[3,2-c]pyridin-1-yl]-(2-chlorophenyl)methanone Chemical compound ClC1=CC=CC=C1C(=O)N1C2=CC=NC=C2C(C=2CC3CCCN3CC=2)=C1 IOWGFNLEWKXDGN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004001 thioalkyl group Chemical group 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 abstract description 9
- 239000003814 drug Substances 0.000 abstract description 5
- 201000000980 schizophrenia Diseases 0.000 abstract description 5
- 125000003107 substituted aryl group Chemical group 0.000 abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 54
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 44
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- -1 alkyl radicals Chemical class 0.000 description 17
- 238000000034 method Methods 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- DASJFYAPNPUBGG-UHFFFAOYSA-N naphthalene-1-sulfonyl chloride Chemical compound C1=CC=C2C(S(=O)(=O)Cl)=CC=CC2=C1 DASJFYAPNPUBGG-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 125000006239 protecting group Chemical group 0.000 description 10
- 229940076279 serotonin Drugs 0.000 description 10
- 102000030621 adenylate cyclase Human genes 0.000 description 9
- 108060000200 adenylate cyclase Proteins 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 8
- 230000002285 radioactive effect Effects 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicinal Preparation (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14834399P | 1999-08-12 | 1999-08-12 | |
| US60/148,343 | 1999-08-12 | ||
| PCT/IB2000/001122 WO2001012629A1 (en) | 1999-08-12 | 2000-08-14 | Azaindoles having serotonin receptor affinity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2382247A1 CA2382247A1 (en) | 2001-02-22 |
| CA2382247C true CA2382247C (en) | 2010-09-28 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2382247A Expired - Fee Related CA2382247C (en) | 1999-08-12 | 2000-08-14 | Azaindoles having serotonin receptor affinity |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP1204662B1 (enExample) |
| JP (1) | JP4969004B2 (enExample) |
| AT (1) | ATE268330T1 (enExample) |
| AU (1) | AU779832B2 (enExample) |
| CA (1) | CA2382247C (enExample) |
| DE (1) | DE60011269T2 (enExample) |
| DK (1) | DK1204662T3 (enExample) |
| ES (1) | ES2222219T3 (enExample) |
| MX (1) | MXPA02001473A (enExample) |
| WO (1) | WO2001012629A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10030037A1 (de) | 2000-06-17 | 2001-12-20 | Mann & Hummel Filter | Zylindrische Filterpatrone mit Stützrohr |
| ITRM20010356A1 (it) * | 2001-06-21 | 2002-12-23 | Sigma Tau Ind Farmaceuti | "5-alogeno derivati della triptamina utili come ligandi del recettore5-ht6 e/o 5-ht7 della serotonina. |
| HUP0402640A3 (en) * | 2001-12-20 | 2012-09-28 | Wyeth Corp | Indolylalkylamine derivatives as 5-hydroxytryptamine-6 ligands, process for their preparation and pharmaceutical compositions thereof |
| TW200301251A (en) * | 2001-12-20 | 2003-07-01 | Wyeth Corp | Azaindolylalkylamine derivatives as 5-hydroxytryptamine-6 ligands |
| GB0202679D0 (en) * | 2002-02-05 | 2002-03-20 | Glaxo Group Ltd | Novel compounds |
| ATE346068T1 (de) * | 2002-03-27 | 2006-12-15 | Glaxo Group Ltd | Chinolin- und aza-indolderivate und deren verwendung als 5-ht6 liganden |
| UA78999C2 (en) * | 2002-06-04 | 2007-05-10 | Wyeth Corp | 1-(aminoalkyl)-3-sulfonylazaindoles as ligands of 5-hydroxytryptamine-6 |
| EP1897876A3 (en) | 2002-06-20 | 2009-03-18 | Biovitrum AB (publ) | Compounds useful for the treatment of obesity, type II diabetes and CNS disorders |
| TW200403243A (en) | 2002-07-18 | 2004-03-01 | Wyeth Corp | 1-Heterocyclylalkyl-3-sulfonylazaindole or-azaindazole derivatives as 5-hydroxytryptamine-6 ligands |
| EP1592772A2 (en) * | 2003-01-31 | 2005-11-09 | Pfizer Products Incorporated | 5ht7 antagonists and inverse agonists |
| CN100482662C (zh) * | 2003-02-14 | 2009-04-29 | 惠氏公司 | 作为5-羟基色胺-6配体的杂环基-3-磺酰基氮杂吲哚或-氮杂吲唑衍生物 |
| JP2006528186A (ja) * | 2003-07-23 | 2006-12-14 | ワイス | ５−ヒドロキシトリプタミン−６リガンドとしてのスルホニルジヒドロベンゾイミダゾロン化合物 |
| ES2222828B1 (es) * | 2003-07-30 | 2006-04-16 | Laboratorios Del Dr. Esteve, S.A. | Derivados de 1-sulfonilindoles, su preparacion y su aplicacion como medicamentos. |
| AU2007217040A1 (en) * | 2006-02-17 | 2007-08-30 | Memory Pharmaceuticals Corporation | Compounds having 5-HT6 receptor affinity |
| EP2046741B1 (en) * | 2006-07-03 | 2012-10-31 | Proximagen Ltd. | Indoles as 5-ht6 modulators |
| WO2012160464A1 (en) * | 2011-05-26 | 2012-11-29 | Daiichi Sankyo Company, Limited | Heterocyclic compounds as protein kinase inhibitors |
| EP3083588B1 (en) | 2013-12-20 | 2020-12-09 | Sunshine Lake Pharma Co., Ltd. | Aromatic heterocyclic compounds and their application in pharmaceuticals |
| EP3166924B1 (en) | 2014-07-08 | 2019-02-20 | Sunshine Lake Pharma Co., Ltd. | Aromatic heterocyclic derivatives and pharmaceutical applications thereof |
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| BR9406128A (pt) * | 1993-03-01 | 1996-02-27 | Merck Sharp & Dohme | Uso de um composto processo para o tratamento e/ou prevençao de distúrbios psicóticos composto composiçao farmacêutica processos para a preparaçao de um composto e de uma composiçao farmacêutica |
| US5846982A (en) * | 1996-06-14 | 1998-12-08 | Eli Lilly And Company | Inhibition of serotonin reuptake |
| EP0875513A1 (en) * | 1997-04-14 | 1998-11-04 | Eli Lilly And Company | Substituted heteroaromatic 5-HT 1F agonists |
| US5905084A (en) * | 1997-11-14 | 1999-05-18 | Eli Lilly And Company | 5-HTIF -agonists effective in treating migraine |
| US6562809B1 (en) * | 1998-09-18 | 2003-05-13 | Nps Allelix Corp. | 3-bicycloindole compounds |
-
2000
- 2000-08-14 MX MXPA02001473A patent/MXPA02001473A/es active IP Right Grant
- 2000-08-14 AT AT00949846T patent/ATE268330T1/de active
- 2000-08-14 ES ES00949846T patent/ES2222219T3/es not_active Expired - Lifetime
- 2000-08-14 WO PCT/IB2000/001122 patent/WO2001012629A1/en not_active Ceased
- 2000-08-14 EP EP00949846A patent/EP1204662B1/en not_active Expired - Lifetime
- 2000-08-14 AU AU63103/00A patent/AU779832B2/en not_active Ceased
- 2000-08-14 DK DK00949846T patent/DK1204662T3/da active
- 2000-08-14 DE DE60011269T patent/DE60011269T2/de not_active Expired - Lifetime
- 2000-08-14 JP JP2001517527A patent/JP4969004B2/ja not_active Expired - Fee Related
- 2000-08-14 CA CA2382247A patent/CA2382247C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP4969004B2 (ja) | 2012-07-04 |
| JP2003507380A (ja) | 2003-02-25 |
| DE60011269T2 (de) | 2005-06-23 |
| ES2222219T3 (es) | 2005-02-01 |
| WO2001012629A1 (en) | 2001-02-22 |
| DE60011269D1 (de) | 2004-07-08 |
| DK1204662T3 (da) | 2004-10-04 |
| CA2382247A1 (en) | 2001-02-22 |
| EP1204662B1 (en) | 2004-06-02 |
| AU6310300A (en) | 2001-03-13 |
| MXPA02001473A (es) | 2003-07-21 |
| EP1204662A1 (en) | 2002-05-15 |
| AU779832B2 (en) | 2005-02-10 |
| ATE268330T1 (de) | 2004-06-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20140814 |