CA2619010C - Substituted-3-sulfonylindazole derivatives as 5-hydroxytryptamine-6 ligands - Google Patents
Substituted-3-sulfonylindazole derivatives as 5-hydroxytryptamine-6 ligands Download PDFInfo
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- CA2619010C CA2619010C CA2619010A CA2619010A CA2619010C CA 2619010 C CA2619010 C CA 2619010C CA 2619010 A CA2619010 A CA 2619010A CA 2619010 A CA2619010 A CA 2619010A CA 2619010 C CA2619010 C CA 2619010C
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- CA
- Canada
- Prior art keywords
- indazol
- oxy
- naphthylsulfonyl
- ethyl
- amine
- 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.)
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- -1 Substituted-3-sulfonylindazole Chemical class 0.000 title claims description 68
- 239000003446 ligand Substances 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 332
- 238000011282 treatment Methods 0.000 claims abstract description 37
- 208000015114 central nervous system disease Diseases 0.000 claims abstract description 14
- 208000012902 Nervous system disease Diseases 0.000 claims abstract description 9
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 89
- 238000000034 method Methods 0.000 claims description 77
- 235000010288 sodium nitrite Nutrition 0.000 claims description 46
- 150000003839 salts Chemical class 0.000 claims description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 229910052740 iodine Inorganic materials 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000002619 bicyclic group Chemical group 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- JOKVCTPPRWTZIZ-UHFFFAOYSA-N 2-(1-benzyl-3-naphthalen-1-ylsulfonylindazol-5-yl)oxy-n,n-dimethylethanamine Chemical compound N1=C(S(=O)(=O)C=2C3=CC=CC=C3C=CC=2)C2=CC(OCCN(C)C)=CC=C2N1CC1=CC=CC=C1 JOKVCTPPRWTZIZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- NXQGEDVQXVTCDA-UHFFFAOYSA-N n,n-dimethyl-3-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]propan-1-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCCN(C)C)=CC=CC2=C1 NXQGEDVQXVTCDA-UHFFFAOYSA-N 0.000 claims 2
- CIOWMQRPUTVJAD-UHFFFAOYSA-N 2-(1-benzyl-3-naphthalen-1-ylsulfonylindazol-5-yl)oxy-n-ethylethanamine Chemical compound N1=C(S(=O)(=O)C=2C3=CC=CC=C3C=CC=2)C2=CC(OCCNCC)=CC=C2N1CC1=CC=CC=C1 CIOWMQRPUTVJAD-UHFFFAOYSA-N 0.000 claims 1
- YUJDLCUEQASUOZ-UHFFFAOYSA-N 2-(1-benzyl-3-naphthalen-1-ylsulfonylindazol-5-yl)oxy-n-methylethanamine Chemical compound N1=C(S(=O)(=O)C=2C3=CC=CC=C3C=CC=2)C2=CC(OCCNC)=CC=C2N1CC1=CC=CC=C1 YUJDLCUEQASUOZ-UHFFFAOYSA-N 0.000 claims 1
- KOAGIWDJQAFEAU-UHFFFAOYSA-N 2-(1-methyl-3-naphthalen-1-ylsulfonylindazol-7-yl)oxyethanamine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NN(C4=C(OCCN)C=CC=C43)C)=CC=CC2=C1 KOAGIWDJQAFEAU-UHFFFAOYSA-N 0.000 claims 1
- IPXNIBQIWMLOIQ-UHFFFAOYSA-N 2-[(3-naphthalen-1-ylsulfonyl-2h-indazol-4-yl)oxy]ethanamine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC=4C=CC=C(C3=4)OCCN)=CC=CC2=C1 IPXNIBQIWMLOIQ-UHFFFAOYSA-N 0.000 claims 1
- UFKBOHNADIHYCJ-UHFFFAOYSA-N 2-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]ethanamine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCN)=CC=CC2=C1 UFKBOHNADIHYCJ-UHFFFAOYSA-N 0.000 claims 1
- OIWRJIJOAUHKGP-UHFFFAOYSA-N 2-[(3-naphthalen-1-ylsulfonyl-2h-indazol-6-yl)oxy]ethanamine Chemical compound C1=CC=C2C(S(=O)(=O)C=3C4=CC=C(C=C4NN=3)OCCN)=CC=CC2=C1 OIWRJIJOAUHKGP-UHFFFAOYSA-N 0.000 claims 1
- LBIXWNKQNFOROQ-UHFFFAOYSA-N 2-[(3-naphthalen-1-ylsulfonyl-2h-indazol-7-yl)oxy]ethanamine Chemical compound C1=CC=C2C(S(=O)(=O)C=3C=4C=CC=C(C=4NN=3)OCCN)=CC=CC2=C1 LBIXWNKQNFOROQ-UHFFFAOYSA-N 0.000 claims 1
- HMYUFCVGTBDGEL-UHFFFAOYSA-N 2-[(5-fluoro-3-naphthalen-1-ylsulfonyl-2h-indazol-7-yl)oxy]-n,n-dimethylethanamine Chemical compound C1=CC=C2C(S(=O)(=O)C=3C=4C=C(F)C=C(C=4NN=3)OCCN(C)C)=CC=CC2=C1 HMYUFCVGTBDGEL-UHFFFAOYSA-N 0.000 claims 1
- MKDGUGOLAULVEG-UHFFFAOYSA-N 2-[(5-fluoro-3-naphthalen-1-ylsulfonyl-2h-indazol-7-yl)oxy]-n-methylethanamine Chemical compound C1=CC=C2C(S(=O)(=O)C=3C=4C=C(F)C=C(C=4NN=3)OCCNC)=CC=CC2=C1 MKDGUGOLAULVEG-UHFFFAOYSA-N 0.000 claims 1
- PRINITFWFJYFNK-UHFFFAOYSA-N 2-[(5-methoxy-3-naphthalen-1-ylsulfonyl-2h-indazol-7-yl)oxy]-n,n-dimethylethanamine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=C(OCCN(C)C)C=C(C=C43)OC)=CC=CC2=C1 PRINITFWFJYFNK-UHFFFAOYSA-N 0.000 claims 1
- KELNGYBJXUYADG-UHFFFAOYSA-N 2-[(5-methoxy-3-naphthalen-1-ylsulfonyl-2h-indazol-7-yl)oxy]-n-methylethanamine Chemical compound C1=CC=C2C(S(=O)(=O)C=3C=4C=C(OC)C=C(C=4NN=3)OCCNC)=CC=CC2=C1 KELNGYBJXUYADG-UHFFFAOYSA-N 0.000 claims 1
- HVVHTDCEKSEIDP-UHFFFAOYSA-N 2-[1-[(3-chlorophenyl)methyl]-3-naphthalen-1-ylsulfonylindazol-5-yl]oxy-n,n-dimethylethanamine Chemical compound N1=C(S(=O)(=O)C=2C3=CC=CC=C3C=CC=2)C2=CC(OCCN(C)C)=CC=C2N1CC1=CC=CC(Cl)=C1 HVVHTDCEKSEIDP-UHFFFAOYSA-N 0.000 claims 1
- BCZIOHHWLJAHLB-UHFFFAOYSA-N 2-[1-[(3-chlorophenyl)methyl]-3-naphthalen-1-ylsulfonylindazol-5-yl]oxy-n-ethylethanamine Chemical compound N1=C(S(=O)(=O)C=2C3=CC=CC=C3C=CC=2)C2=CC(OCCNCC)=CC=C2N1CC1=CC=CC(Cl)=C1 BCZIOHHWLJAHLB-UHFFFAOYSA-N 0.000 claims 1
- PUECJZJYCKEXGK-UHFFFAOYSA-N 2-[1-[(3-chlorophenyl)methyl]-3-naphthalen-1-ylsulfonylindazol-7-yl]oxy-n-ethylethanamine Chemical compound C1=2C(OCCNCC)=CC=CC=2C(S(=O)(=O)C=2C3=CC=CC=C3C=CC=2)=NN1CC1=CC=CC(Cl)=C1 PUECJZJYCKEXGK-UHFFFAOYSA-N 0.000 claims 1
- GISNOEZWSXUMJI-UHFFFAOYSA-N 2-[1-[(3-chlorophenyl)methyl]-3-naphthalen-1-ylsulfonylindazol-7-yl]oxy-n-methylethanamine Chemical compound C1=2C(OCCNC)=CC=CC=2C(S(=O)(=O)C=2C3=CC=CC=C3C=CC=2)=NN1CC1=CC=CC(Cl)=C1 GISNOEZWSXUMJI-UHFFFAOYSA-N 0.000 claims 1
- YDJRUAFRFBAMEA-UHFFFAOYSA-N 2-[1-[(3-chlorophenyl)methyl]-3-naphthalen-1-ylsulfonylindazol-7-yl]oxyethanamine Chemical compound C1=2C(OCCN)=CC=CC=2C(S(=O)(=O)C=2C3=CC=CC=C3C=CC=2)=NN1CC1=CC=CC(Cl)=C1 YDJRUAFRFBAMEA-UHFFFAOYSA-N 0.000 claims 1
- GLMCMWNITAAMIM-UHFFFAOYSA-N 2-[1-[(3-chlorophenyl)methyl]-5-fluoro-3-naphthalen-1-ylsulfonylindazol-7-yl]oxy-n,n-dimethylethanamine Chemical compound C1=2C(OCCN(C)C)=CC(F)=CC=2C(S(=O)(=O)C=2C3=CC=CC=C3C=CC=2)=NN1CC1=CC=CC(Cl)=C1 GLMCMWNITAAMIM-UHFFFAOYSA-N 0.000 claims 1
- JURYICOBMPOCAG-UHFFFAOYSA-N 2-[3-(benzenesulfonyl)-1-[(3-chlorophenyl)methyl]indazol-7-yl]oxy-n-ethylethanamine Chemical compound C1=2C(OCCNCC)=CC=CC=2C(S(=O)(=O)C=2C=CC=CC=2)=NN1CC1=CC=CC(Cl)=C1 JURYICOBMPOCAG-UHFFFAOYSA-N 0.000 claims 1
- URGWMZAHFHDSAB-UHFFFAOYSA-N 2-[3-(benzenesulfonyl)-1-[(3-chlorophenyl)methyl]indazol-7-yl]oxy-n-methylethanamine Chemical compound C1=2C(OCCNC)=CC=CC=2C(S(=O)(=O)C=2C=CC=CC=2)=NN1CC1=CC=CC(Cl)=C1 URGWMZAHFHDSAB-UHFFFAOYSA-N 0.000 claims 1
- LJNYDPDAMOHONR-UHFFFAOYSA-N 2-[3-(benzenesulfonyl)-1-methylindazol-7-yl]oxy-n-methylethanamine Chemical compound N=1N(C)C=2C(OCCNC)=CC=CC=2C=1S(=O)(=O)C1=CC=CC=C1 LJNYDPDAMOHONR-UHFFFAOYSA-N 0.000 claims 1
- HDXBREGAPLXGIS-UHFFFAOYSA-N 2-[[3-(benzenesulfonyl)-2h-indazol-5-yl]oxy]-n,n-dimethylethanamine Chemical compound C12=CC(OCCN(C)C)=CC=C2NN=C1S(=O)(=O)C1=CC=CC=C1 HDXBREGAPLXGIS-UHFFFAOYSA-N 0.000 claims 1
- NTWIXXNPWJCUKO-UHFFFAOYSA-N 2-[[3-(benzenesulfonyl)-2h-indazol-5-yl]oxy]-n-ethylethanamine Chemical compound C12=CC(OCCNCC)=CC=C2NN=C1S(=O)(=O)C1=CC=CC=C1 NTWIXXNPWJCUKO-UHFFFAOYSA-N 0.000 claims 1
- YRZHGGDYKODNJU-UHFFFAOYSA-N 2-[[3-(benzenesulfonyl)-2h-indazol-5-yl]oxy]-n-methylethanamine Chemical compound C12=CC(OCCNC)=CC=C2NN=C1S(=O)(=O)C1=CC=CC=C1 YRZHGGDYKODNJU-UHFFFAOYSA-N 0.000 claims 1
- WHXDIHVWZAGDKC-UHFFFAOYSA-N 2-[[3-(benzenesulfonyl)-2h-indazol-7-yl]oxy]-n,n-diethylethanamine Chemical compound N=1NC=2C(OCCN(CC)CC)=CC=CC=2C=1S(=O)(=O)C1=CC=CC=C1 WHXDIHVWZAGDKC-UHFFFAOYSA-N 0.000 claims 1
- AORXKAAXUHVTJR-UHFFFAOYSA-N 2-[[3-(benzenesulfonyl)-2h-indazol-7-yl]oxy]-n-ethylethanamine Chemical compound N=1NC=2C(OCCNCC)=CC=CC=2C=1S(=O)(=O)C1=CC=CC=C1 AORXKAAXUHVTJR-UHFFFAOYSA-N 0.000 claims 1
- DLEJEOYCUICQJI-UHFFFAOYSA-N 2-[[3-(benzenesulfonyl)-2h-indazol-7-yl]oxy]-n-methylethanamine Chemical compound N=1NC=2C(OCCNC)=CC=CC=2C=1S(=O)(=O)C1=CC=CC=C1 DLEJEOYCUICQJI-UHFFFAOYSA-N 0.000 claims 1
- MFTFRMAELXKCND-UHFFFAOYSA-N 2-[[3-(benzenesulfonyl)-2h-indazol-7-yl]oxy]ethanamine Chemical compound N=1NC=2C(OCCN)=CC=CC=2C=1S(=O)(=O)C1=CC=CC=C1 MFTFRMAELXKCND-UHFFFAOYSA-N 0.000 claims 1
- PVHHQFSLPRWAAC-UHFFFAOYSA-N 2-[[3-(benzenesulfonyl)-5-fluoro-2h-indazol-7-yl]oxy]ethanamine Chemical compound N=1NC=2C(OCCN)=CC(F)=CC=2C=1S(=O)(=O)C1=CC=CC=C1 PVHHQFSLPRWAAC-UHFFFAOYSA-N 0.000 claims 1
- PTCSHLCQBWNEIT-UHFFFAOYSA-N 3-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]-n-propan-2-ylpropan-1-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCCNC(C)C)=CC=CC2=C1 PTCSHLCQBWNEIT-UHFFFAOYSA-N 0.000 claims 1
- JGMZQHZCMQDYQE-UHFFFAOYSA-N 3-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]propan-1-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCCN)=CC=CC2=C1 JGMZQHZCMQDYQE-UHFFFAOYSA-N 0.000 claims 1
- KAWWRYOKLNMCFP-UHFFFAOYSA-N 3-[1-[(3-chlorophenyl)methyl]-3-naphthalen-1-ylsulfonylindazol-7-yl]oxy-n,n-diethylpropan-1-amine Chemical compound C1=2C(OCCCN(CC)CC)=CC=CC=2C(S(=O)(=O)C=2C3=CC=CC=C3C=CC=2)=NN1CC1=CC=CC(Cl)=C1 KAWWRYOKLNMCFP-UHFFFAOYSA-N 0.000 claims 1
- OAMHSABPVYGYOU-UHFFFAOYSA-N 4-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]butan-1-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCCCN)=CC=CC2=C1 OAMHSABPVYGYOU-UHFFFAOYSA-N 0.000 claims 1
- IXSMRKQJNLSAEU-UHFFFAOYSA-N N,N-dimethyl-4-[(3-naphthalen-1-ylsulfonyl-2H-indazol-5-yl)oxy]butan-1-amine N-methyl-4-[(3-naphthalen-1-ylsulfonyl-2H-indazol-5-yl)oxy]butan-1-amine Chemical compound CNCCCCOc1ccc2[nH]nc(c2c1)S(=O)(=O)c1cccc2ccccc12.CN(C)CCCCOc1ccc2[nH]nc(c2c1)S(=O)(=O)c1cccc2ccccc12 IXSMRKQJNLSAEU-UHFFFAOYSA-N 0.000 claims 1
- OIGKUILSSYMBFJ-UHFFFAOYSA-N n,n-diethyl-2-(1-methyl-3-naphthalen-1-ylsulfonylindazol-5-yl)oxyethanamine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NN(C)C4=CC=C(C=C43)OCCN(CC)CC)=CC=CC2=C1 OIGKUILSSYMBFJ-UHFFFAOYSA-N 0.000 claims 1
- JEYSUQQUTIWEEF-UHFFFAOYSA-N n,n-diethyl-2-(1-methyl-3-naphthalen-1-ylsulfonylindazol-7-yl)oxyethanamine Chemical compound C1=CC=C2C(S(=O)(=O)C=3C=4C=CC=C(C=4N(C)N=3)OCCN(CC)CC)=CC=CC2=C1 JEYSUQQUTIWEEF-UHFFFAOYSA-N 0.000 claims 1
- DMCNDPIVSZOUSA-UHFFFAOYSA-N n,n-diethyl-2-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]ethanamine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCN(CC)CC)=CC=CC2=C1 DMCNDPIVSZOUSA-UHFFFAOYSA-N 0.000 claims 1
- FLRJCYWJZNJPAJ-UHFFFAOYSA-N n,n-diethyl-2-[(5-fluoro-3-naphthalen-1-ylsulfonyl-2h-indazol-7-yl)oxy]ethanamine Chemical compound C1=CC=C2C(S(=O)(=O)C=3C=4C=C(F)C=C(C=4NN=3)OCCN(CC)CC)=CC=CC2=C1 FLRJCYWJZNJPAJ-UHFFFAOYSA-N 0.000 claims 1
- FSUSRKMBYMEREP-UHFFFAOYSA-N n,n-diethyl-3-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]propan-1-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCCN(CC)CC)=CC=CC2=C1 FSUSRKMBYMEREP-UHFFFAOYSA-N 0.000 claims 1
- BGRBBWMOYJRGSK-UHFFFAOYSA-N n,n-diethyl-3-[(3-naphthalen-1-ylsulfonyl-2h-indazol-7-yl)oxy]propan-1-amine Chemical compound C1=CC=C2C(S(=O)(=O)C=3C=4C=CC=C(C=4NN=3)OCCCN(CC)CC)=CC=CC2=C1 BGRBBWMOYJRGSK-UHFFFAOYSA-N 0.000 claims 1
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- PFGDRVIOICUAIA-UHFFFAOYSA-N n,n-dimethyl-2-(1-methyl-3-naphthalen-1-ylsulfonylindazol-5-yl)oxyethanamine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NN(C)C4=CC=C(C=C43)OCCN(C)C)=CC=CC2=C1 PFGDRVIOICUAIA-UHFFFAOYSA-N 0.000 claims 1
- JZJVVXUVKTVXSC-UHFFFAOYSA-N n,n-dimethyl-2-[(3-naphthalen-1-ylsulfonyl-2h-indazol-4-yl)oxy]ethanamine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC=4C=CC=C(C3=4)OCCN(C)C)=CC=CC2=C1 JZJVVXUVKTVXSC-UHFFFAOYSA-N 0.000 claims 1
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- KIIXTMKHCQBIED-UHFFFAOYSA-N n,n-dimethyl-2-[(3-naphthalen-1-ylsulfonyl-2h-indazol-7-yl)oxy]ethanamine Chemical compound C1=CC=C2C(S(=O)(=O)C=3C=4C=CC=C(C=4NN=3)OCCN(C)C)=CC=CC2=C1 KIIXTMKHCQBIED-UHFFFAOYSA-N 0.000 claims 1
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- VUKPWKNVDTZIIO-UHFFFAOYSA-N n-[2-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]ethyl]butan-1-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCNCCCC)=CC=CC2=C1 VUKPWKNVDTZIIO-UHFFFAOYSA-N 0.000 claims 1
- YAYVSICZNRZOGT-UHFFFAOYSA-N n-[2-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]ethyl]cyclopentanamine Chemical compound C=1C=CC2=CC=CC=C2C=1S(=O)(=O)C(C1=C2)=NNC1=CC=C2OCCNC1CCCC1 YAYVSICZNRZOGT-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- 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
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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- 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
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Landscapes
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- Health & Medical Sciences (AREA)
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| US70831505P | 2005-08-15 | 2005-08-15 | |
| US60/708,315 | 2005-08-15 | ||
| PCT/US2006/030965 WO2007021711A2 (en) | 2005-08-15 | 2006-08-08 | Substituted-3-sulfonylindazole derivatives as 5-hydroxytryptamine-6 ligands |
Publications (2)
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| CA2619010A1 CA2619010A1 (en) | 2007-02-22 |
| CA2619010C true CA2619010C (en) | 2013-10-01 |
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| CA2619010A Expired - Fee Related CA2619010C (en) | 2005-08-15 | 2006-08-08 | Substituted-3-sulfonylindazole derivatives as 5-hydroxytryptamine-6 ligands |
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| UA (1) | UA94053C2 (enExample) |
| WO (1) | WO2007021711A2 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20080114688A (ko) * | 2006-01-13 | 2008-12-31 | 와이어쓰 | 5-히드록시트립타민 수용체에 대한 리간드로서의 술포닐 치환된 1ｈ-인돌 |
| PE20071143A1 (es) * | 2006-01-13 | 2008-01-20 | Wyeth Corp | Composicion farmaceutica que comprende un inhibidor de acetilcolinesterasa y un antagonista 5-hidroxitriptamina-6 |
| CA2647141A1 (en) * | 2006-04-12 | 2007-10-25 | Wyeth | Substituted-dihydro[1,4]oxazino[2,3,4-hi]indazole derivatives as 5-hydroxytryptamine-6 ligands |
| WO2007120599A2 (en) * | 2006-04-12 | 2007-10-25 | Wyeth | Dihydro[1,4]oxazino[2,3,4-hi]indazole derivatives as 5-hydroxytryptamine-6 ligands |
| WO2007120596A1 (en) * | 2006-04-12 | 2007-10-25 | Wyeth | DIHYDRO[1,4]DIOXINO[2,3-e]INDAZOLE DERIVATIVES AS 5-HYDROXYTRYPTAMINE-6 LIGANDS |
| US20090012308A1 (en) * | 2007-06-13 | 2009-01-08 | Wyeth | Process for the manufacture of benzylsulfonylarenes |
| CN103102322B (zh) * | 2011-11-14 | 2016-02-24 | 上海交通大学 | 噁唑类化合物及其制备方法、药物组合物及其用途 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001521926A (ja) | 1997-11-04 | 2001-11-13 | ファイザー・プロダクツ・インク | 治療上活性の化合物におけるカテコールのインダゾール生物学的等価物置換 |
| EP1196380A2 (en) | 1999-07-15 | 2002-04-17 | NPS Allelix Corp. | Indoles and indazoles for the treatment of migraine |
| WO2002036562A2 (en) * | 2000-11-02 | 2002-05-10 | Wyeth | 1-aryl- or 1-alkylsulfonyl-heterocyclylbenzazoles as 5-hydroxytryptamine-6 ligands |
| KR20030062442A (ko) | 2000-12-22 | 2003-07-25 | 와이어쓰 | 5-하이드록시트립타민-6-리간드로서의 헤테로사이클인다졸및 아자인다졸 화합물 |
| DK1355900T3 (da) | 2000-12-22 | 2006-09-11 | Wyeth Corp | Heterocyclylalkylindol- eller -azaindolforbindelser som 5-hydroxytryptamin-6-ligander |
| TW593278B (en) | 2001-01-23 | 2004-06-21 | Wyeth Corp | 1-aryl-or 1-alkylsulfonylbenzazole derivatives as 5-hydroxytryptamine-6 ligands |
| KR20030088508A (ko) | 2001-04-20 | 2003-11-19 | 와이어쓰 | 5-하이드록시트립타민-6 리간드로서의헤테로사이클릴옥시-, -티옥시- 및 -아미노벤즈아졸 유도체 |
| CN1293073C (zh) | 2001-04-20 | 2007-01-03 | 惠氏公司 | 作为5－羟色胺－6配体的杂环基烷氧基－、－烷硫基－和－烷基氨基吲哚衍生物 |
| PL367305A1 (en) * | 2001-06-07 | 2005-02-21 | F.Hoffmann-La Roche Ag | New indole derivatives with 5-ht6 receptor affinity |
| EP1403255A4 (en) | 2001-06-12 | 2005-04-06 | Sumitomo Pharma | RHO KINASE INHIBITORS |
| US20050113283A1 (en) | 2002-01-18 | 2005-05-26 | David Solow-Cordero | Methods of treating conditions associated with an EDG-4 receptor |
| TW200400177A (en) * | 2002-06-04 | 2004-01-01 | Wyeth Corp | 1-(Aminoalkyl)-3-sulfonylindole and-indazole derivatives as 5-hydroxytryptamine-6 ligands |
| US7943639B2 (en) | 2002-06-20 | 2011-05-17 | Proximagen Limited | Compounds |
| TW200401641A (en) * | 2002-07-18 | 2004-02-01 | Wyeth Corp | 1-Heterocyclylalkyl-3-sulfonylindole or-indazole derivatives as 5-hydroxytryptamine-6 ligands |
| TW200403243A (en) | 2002-07-18 | 2004-03-01 | Wyeth Corp | 1-Heterocyclylalkyl-3-sulfonylazaindole or-azaindazole derivatives as 5-hydroxytryptamine-6 ligands |
| RU2324693C2 (ru) * | 2002-10-18 | 2008-05-20 | Ф.Хоффманн-Ля Рош Аг | 4-пиперазинилбензолсульфонилиндолы, характеризующиеся сродством к рецептору 5-нт6 |
| CA2508315A1 (en) * | 2002-12-03 | 2004-06-17 | F. Hoffmann-La Roche Ag | Aminoalkoxyindoles as 5-ht6-receptor ligands for the treatment of cns-disorders |
| EP1592683A2 (en) | 2003-02-14 | 2005-11-09 | Wyeth | Heterocyclyl-3-sulfonylindazoles as 5-hydroxytryptamine-6 ligands |
| TW200418830A (en) * | 2003-02-14 | 2004-10-01 | Wyeth Corp | Heterocyclyl-3-sulfonylazaindole or-azaindazole derivatives as 5-hydroxytryptamine-6 ligands |
| BRPI0508107A (pt) | 2004-02-27 | 2007-07-17 | Hoffmann La Roche | derivados de indazol e composições farmacêuticas contendo os mesmos |
| KR20080034497A (ko) | 2005-08-15 | 2008-04-21 | 와이어쓰 | 5-히드록시트립타민-6 리간드로서의 아지닐-3-설포닐인다졸유도체 |
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2006
- 2006-08-08 BR BRPI0614343-1A patent/BRPI0614343A2/pt not_active IP Right Cessation
- 2006-08-08 CA CA2619010A patent/CA2619010C/en not_active Expired - Fee Related
- 2006-08-08 UA UAA200801842A patent/UA94053C2/ru unknown
- 2006-08-08 JP JP2008526995A patent/JP5146766B2/ja not_active Expired - Fee Related
- 2006-08-08 AU AU2006280091A patent/AU2006280091A1/en not_active Abandoned
- 2006-08-08 EP EP06801007A patent/EP1931640A2/en not_active Withdrawn
- 2006-08-08 CN CNA2006800374446A patent/CN101282938A/zh active Pending
- 2006-08-08 WO PCT/US2006/030965 patent/WO2007021711A2/en not_active Ceased
- 2006-08-08 RU RU2008105807/04A patent/RU2429231C2/ru not_active IP Right Cessation
- 2006-08-08 KR KR1020087006267A patent/KR20080039994A/ko not_active Ceased
- 2006-08-08 NZ NZ565872A patent/NZ565872A/en unknown
- 2006-08-14 US US11/504,350 patent/US7723329B2/en not_active Expired - Fee Related
- 2006-08-14 PE PE2006000984A patent/PE20070354A1/es not_active Application Discontinuation
- 2006-08-14 GT GT200600376A patent/GT200600376A/es unknown
- 2006-08-14 TW TW095129795A patent/TW200740766A/zh unknown
- 2006-08-14 AR ARP060103549A patent/AR057756A1/es unknown
- 2006-09-09 SA SA6270314A patent/SA06270314B1/ar unknown
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2008
- 2008-02-12 IL IL189476A patent/IL189476A0/en unknown
- 2008-02-15 CR CR9734A patent/CR9734A/es not_active Application Discontinuation
- 2008-02-15 EC EC2008008189A patent/ECSP088189A/es unknown
- 2008-02-25 NO NO20080937A patent/NO20080937L/no not_active Application Discontinuation
Also Published As
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|---|---|
| SA06270314B1 (ar) | 2011-07-20 |
| US7723329B2 (en) | 2010-05-25 |
| US20070037802A1 (en) | 2007-02-15 |
| GT200600376A (es) | 2007-03-29 |
| IL189476A0 (en) | 2008-08-07 |
| PE20070354A1 (es) | 2007-04-04 |
| AU2006280091A1 (en) | 2007-02-22 |
| JP2009504739A (ja) | 2009-02-05 |
| CN101282938A (zh) | 2008-10-08 |
| UA94053C2 (ru) | 2011-04-11 |
| RU2008105807A (ru) | 2009-09-27 |
| EP1931640A2 (en) | 2008-06-18 |
| NO20080937L (no) | 2008-04-30 |
| RU2429231C2 (ru) | 2011-09-20 |
| WO2007021711A2 (en) | 2007-02-22 |
| NZ565872A (en) | 2011-06-30 |
| CA2619010A1 (en) | 2007-02-22 |
| BRPI0614343A2 (pt) | 2011-03-22 |
| WO2007021711A3 (en) | 2007-05-03 |
| CR9734A (es) | 2008-04-03 |
| JP5146766B2 (ja) | 2013-02-20 |
| TW200740766A (en) | 2007-11-01 |
| ECSP088189A (es) | 2008-04-28 |
| KR20080039994A (ko) | 2008-05-07 |
| AR057756A1 (es) | 2007-12-19 |
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