NZ335970A - Sulphonamide derivatives and their pharmaceutical use as 5-HT6 antagonists - Google Patents
Sulphonamide derivatives and their pharmaceutical use as 5-HT6 antagonistsInfo
- Publication number
- NZ335970A NZ335970A NZ335970A NZ33597097A NZ335970A NZ 335970 A NZ335970 A NZ 335970A NZ 335970 A NZ335970 A NZ 335970A NZ 33597097 A NZ33597097 A NZ 33597097A NZ 335970 A NZ335970 A NZ 335970A
- Authority
- NZ
- New Zealand
- Prior art keywords
- methoxy
- phenyl
- methylpiperazin
- benzenesulfonamide
- amide
- Prior art date
Links
- 150000003456 sulfonamides Chemical class 0.000 title claims abstract 3
- 229940124801 5-HT6 antagonist Drugs 0.000 title 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 69
- -1 CO-alkyl Chemical group 0.000 claims abstract description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical group 0.000 claims abstract description 7
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 7
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims abstract description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000005864 Sulphur Chemical group 0.000 claims abstract description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims abstract description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 239000001301 oxygen Substances 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
- 108091005435 5-HT6 receptors Proteins 0.000 claims abstract description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 201000000980 schizophrenia Diseases 0.000 claims abstract description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 230000008485 antagonism Effects 0.000 claims abstract 2
- 230000009286 beneficial effect Effects 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 104
- 150000001408 amides Chemical class 0.000 claims description 41
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 34
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 19
- GXWGRQOMOLFZDN-UHFFFAOYSA-N 5-chloro-3-methyl-1-benzothiophene-2-sulfonic acid Chemical compound C1=C(Cl)C=C2C(C)=C(S(O)(=O)=O)SC2=C1 GXWGRQOMOLFZDN-UHFFFAOYSA-N 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 16
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 claims description 8
- 238000011282 treatment Methods 0.000 claims description 8
- LOCQRDBFWSXQQI-UHFFFAOYSA-N 5-chloro-n-(4-methoxy-3-piperazin-1-ylphenyl)-3-methyl-1-benzothiophene-2-sulfonamide Chemical compound COC1=CC=C(NS(=O)(=O)C2=C(C3=CC(Cl)=CC=C3S2)C)C=C1N1CCNCC1 LOCQRDBFWSXQQI-UHFFFAOYSA-N 0.000 claims description 7
- 125000006239 protecting group Chemical group 0.000 claims description 5
- ZFZRYSSNJATGEN-UHFFFAOYSA-N 2,3-dichloro-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]benzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl ZFZRYSSNJATGEN-UHFFFAOYSA-N 0.000 claims description 4
- LILAGPSTPBGPKR-UHFFFAOYSA-N 2,5-dichloro-n-(4-methoxy-3-piperazin-1-ylphenyl)thiophene-3-sulfonamide Chemical compound C1=C(N2CCNCC2)C(OC)=CC=C1NS(=O)(=O)C=1C=C(Cl)SC=1Cl LILAGPSTPBGPKR-UHFFFAOYSA-N 0.000 claims description 4
- VMSDCTMEXGQPAB-UHFFFAOYSA-N 2-chloro-4-fluoro-n-(4-methoxy-3-piperazin-1-ylphenyl)benzenesulfonamide Chemical compound C1=C(N2CCNCC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(F)C=C1Cl VMSDCTMEXGQPAB-UHFFFAOYSA-N 0.000 claims description 4
- OVRVKGKPURKVHI-UHFFFAOYSA-N 2-chloro-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]benzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=CC=C1Cl OVRVKGKPURKVHI-UHFFFAOYSA-N 0.000 claims description 4
- XWZKCRAOVMNSDF-UHFFFAOYSA-N 3,4-difluoro-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]benzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(F)C(F)=C1 XWZKCRAOVMNSDF-UHFFFAOYSA-N 0.000 claims description 4
- UDJMZYLDIFOZMO-UHFFFAOYSA-N 3,5-dichloro-n-(4-methoxy-3-piperazin-1-ylphenyl)benzenesulfonamide Chemical compound C1=C(N2CCNCC2)C(OC)=CC=C1NS(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 UDJMZYLDIFOZMO-UHFFFAOYSA-N 0.000 claims description 4
- FGKOHVCNMZHHPT-UHFFFAOYSA-N 3-bromo-n-(4-methoxy-3-piperazin-1-ylphenyl)benzenesulfonamide Chemical compound C1=C(N2CCNCC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=CC(Br)=C1 FGKOHVCNMZHHPT-UHFFFAOYSA-N 0.000 claims description 4
- RUWCPIWOUKKUHW-UHFFFAOYSA-N 3-chloro-n-(4-methoxy-3-piperazin-1-ylphenyl)-4-methylbenzenesulfonamide Chemical compound C1=C(N2CCNCC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(C)C(Cl)=C1 RUWCPIWOUKKUHW-UHFFFAOYSA-N 0.000 claims description 4
- VIOUGUUYIYJHFB-UHFFFAOYSA-N 3-chloro-n-(4-methoxy-3-piperazin-1-ylphenyl)benzenesulfonamide Chemical compound C1=C(N2CCNCC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=CC(Cl)=C1 VIOUGUUYIYJHFB-UHFFFAOYSA-N 0.000 claims description 4
- ZPMXLMGYUMUHFY-UHFFFAOYSA-N 3-chloro-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]benzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=CC(Cl)=C1 ZPMXLMGYUMUHFY-UHFFFAOYSA-N 0.000 claims description 4
- GMGHATXHJRZOAP-UHFFFAOYSA-N 3-fluoro-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]benzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=CC(F)=C1 GMGHATXHJRZOAP-UHFFFAOYSA-N 0.000 claims description 4
- RAVLHYAEBDDJHM-UHFFFAOYSA-N 3-iodo-n-(4-methoxy-3-piperazin-1-ylphenyl)benzenesulfonamide Chemical compound C1=C(N2CCNCC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=CC(I)=C1 RAVLHYAEBDDJHM-UHFFFAOYSA-N 0.000 claims description 4
- HKFCBHKPSFXBIQ-UHFFFAOYSA-N 4-bromo-5-chloro-n-(4-methoxy-3-piperazin-1-ylphenyl)thiophene-2-sulfonamide Chemical compound C1=C(N2CCNCC2)C(OC)=CC=C1NS(=O)(=O)C1=CC(Br)=C(Cl)S1 HKFCBHKPSFXBIQ-UHFFFAOYSA-N 0.000 claims description 4
- DWHKVXJWQJGGJM-UHFFFAOYSA-N 4-bromo-5-chloro-n-[7-(4-methylpiperazin-1-yl)-2,3-dihydro-1-benzofuran-5-yl]thiophene-2-sulfonamide Chemical compound C1CN(C)CCN1C1=CC(NS(=O)(=O)C=2SC(Cl)=C(Br)C=2)=CC2=C1OCC2 DWHKVXJWQJGGJM-UHFFFAOYSA-N 0.000 claims description 4
- NHCPWIQLVKLJSJ-UHFFFAOYSA-N 4-bromo-n-(4-methoxy-3-piperazin-1-ylphenyl)benzenesulfonamide Chemical compound C1=C(N2CCNCC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(Br)C=C1 NHCPWIQLVKLJSJ-UHFFFAOYSA-N 0.000 claims description 4
- HNJGKPSEJHVKDE-UHFFFAOYSA-N 4-butoxy-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]benzenesulfonamide Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)NC1=CC=C(OC)C(N2CCN(C)CC2)=C1 HNJGKPSEJHVKDE-UHFFFAOYSA-N 0.000 claims description 4
- WRCNMPZLPANNGB-UHFFFAOYSA-N 4-butyl-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]benzenesulfonamide Chemical compound C1=CC(CCCC)=CC=C1S(=O)(=O)NC1=CC=C(OC)C(N2CCN(C)CC2)=C1 WRCNMPZLPANNGB-UHFFFAOYSA-N 0.000 claims description 4
- CRMIBYQSSWUBLW-UHFFFAOYSA-N 4-chloro-n-(4-methoxy-3-piperazin-1-ylphenyl)-2,5-dimethylbenzenesulfonamide Chemical compound C1=C(N2CCNCC2)C(OC)=CC=C1NS(=O)(=O)C1=CC(C)=C(Cl)C=C1C CRMIBYQSSWUBLW-UHFFFAOYSA-N 0.000 claims description 4
- UTVBHODAPYYDFB-UHFFFAOYSA-N 4-chloro-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-2,5-dimethylbenzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC(C)=C(Cl)C=C1C UTVBHODAPYYDFB-UHFFFAOYSA-N 0.000 claims description 4
- FRASUHRYTBHUSF-UHFFFAOYSA-N 4-chloro-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]benzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 FRASUHRYTBHUSF-UHFFFAOYSA-N 0.000 claims description 4
- VJYKWLRHFJNUNH-UHFFFAOYSA-N 4-chloro-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]naphthalene-1-sulfonamide Chemical compound COC1=CC=C(NS(=O)(=O)C=2C3=CC=CC=C3C(Cl)=CC=2)C=C1N1CCN(C)CC1 VJYKWLRHFJNUNH-UHFFFAOYSA-N 0.000 claims description 4
- XXNCVBPTKUKJQA-UHFFFAOYSA-N 4-ethyl-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]benzenesulfonamide Chemical compound C1=CC(CC)=CC=C1S(=O)(=O)NC1=CC=C(OC)C(N2CCN(C)CC2)=C1 XXNCVBPTKUKJQA-UHFFFAOYSA-N 0.000 claims description 4
- MWNFFPVWBIUIPM-UHFFFAOYSA-N 4-iodo-n-(4-methoxy-3-piperazin-1-ylphenyl)benzenesulfonamide Chemical compound C1=C(N2CCNCC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(I)C=C1 MWNFFPVWBIUIPM-UHFFFAOYSA-N 0.000 claims description 4
- FKHDVURVQRRQMC-UHFFFAOYSA-N 5-chloro-2-methoxy-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]benzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC(Cl)=CC=C1OC FKHDVURVQRRQMC-UHFFFAOYSA-N 0.000 claims description 4
- IZNFRDRWOOSYSH-UHFFFAOYSA-N 5-chloro-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]naphthalene-2-sulfonamide Chemical compound COC1=CC=C(NS(=O)(=O)C=2C=C3C=CC=C(Cl)C3=CC=2)C=C1N1CCN(C)CC1 IZNFRDRWOOSYSH-UHFFFAOYSA-N 0.000 claims description 4
- RGYOLLJNULUYJC-UHFFFAOYSA-N 5-chloro-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]thiophene-2-sulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(Cl)S1 RGYOLLJNULUYJC-UHFFFAOYSA-N 0.000 claims description 4
- RXONLMREDIZGSE-UHFFFAOYSA-N C1=C(N2CCNCC2)C(OC)=CC=C1NS(=O)(=O)C1(Br)CC=C(Cl)S1 Chemical compound C1=C(N2CCNCC2)C(OC)=CC=C1NS(=O)(=O)C1(Br)CC=C(Cl)S1 RXONLMREDIZGSE-UHFFFAOYSA-N 0.000 claims description 4
- MHKNCOHNGUGIBK-UHFFFAOYSA-N n-(4-methoxy-3-piperazin-1-ylphenyl)-2-(trifluoromethyl)benzenesulfonamide Chemical compound C1=C(N2CCNCC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=CC=C1C(F)(F)F MHKNCOHNGUGIBK-UHFFFAOYSA-N 0.000 claims description 4
- GIKQZTMPXWUSTD-UHFFFAOYSA-N n-(4-methoxy-3-piperazin-1-ylphenyl)-3-(trifluoromethyl)benzenesulfonamide Chemical compound C1=C(N2CCNCC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 GIKQZTMPXWUSTD-UHFFFAOYSA-N 0.000 claims description 4
- ZKJUPSKJWLXQTN-UHFFFAOYSA-N n-(4-methoxy-3-piperazin-1-ylphenyl)-5-pyridin-2-ylthiophene-2-sulfonamide Chemical compound C1=C(N2CCNCC2)C(OC)=CC=C1NS(=O)(=O)C(S1)=CC=C1C1=CC=CC=N1 ZKJUPSKJWLXQTN-UHFFFAOYSA-N 0.000 claims description 4
- JKIJNTDPOAOXBP-UHFFFAOYSA-N n-(4-methoxy-3-piperazin-1-ylphenyl)naphthalene-1-sulfonamide Chemical compound COC1=CC=C(NS(=O)(=O)C=2C3=CC=CC=C3C=CC=2)C=C1N1CCNCC1 JKIJNTDPOAOXBP-UHFFFAOYSA-N 0.000 claims description 4
- NFDULIOCPNFQTF-UHFFFAOYSA-N n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-3,5-dimethyl-1,2-oxazole-4-sulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C=1C(C)=NOC=1C NFDULIOCPNFQTF-UHFFFAOYSA-N 0.000 claims description 4
- ZAUCQVUCRQZMRT-UHFFFAOYSA-N n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-3-methylbenzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=CC(C)=C1 ZAUCQVUCRQZMRT-UHFFFAOYSA-N 0.000 claims description 4
- XYKOEYVUPFAGKY-UHFFFAOYSA-N n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-4-phenylbenzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 XYKOEYVUPFAGKY-UHFFFAOYSA-N 0.000 claims description 4
- UREUVCXONTWIPA-UHFFFAOYSA-N n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]naphthalene-2-sulfonamide Chemical compound COC1=CC=C(NS(=O)(=O)C=2C=C3C=CC=CC3=CC=2)C=C1N1CCN(C)CC1 UREUVCXONTWIPA-UHFFFAOYSA-N 0.000 claims description 4
- MNBUYYFUFDJDRM-UHFFFAOYSA-N n-[7-(4-methylpiperazin-1-yl)-2,3-dihydro-1-benzofuran-5-yl]thiophene-2-sulfonamide Chemical compound C1CN(C)CCN1C1=CC(NS(=O)(=O)C=2SC=CC=2)=CC2=C1OCC2 MNBUYYFUFDJDRM-UHFFFAOYSA-N 0.000 claims description 4
- 229940124530 sulfonamide Drugs 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- WUBQJUKKTUUYSA-UHFFFAOYSA-N 2,5-dibromo-3,6-difluoro-n-(7-piperazin-1-yl-2,3-dihydro-1-benzofuran-5-yl)benzenesulfonamide Chemical compound FC1=CC(Br)=C(F)C(S(=O)(=O)NC=2C=C(C=3OCCC=3C=2)N2CCNCC2)=C1Br WUBQJUKKTUUYSA-UHFFFAOYSA-N 0.000 claims description 3
- LWAXBVXEBNAMEM-UHFFFAOYSA-N 2,5-dibromo-3,6-difluoro-n-[7-(4-methylpiperazin-1-yl)-2,3-dihydro-1-benzofuran-5-yl]benzenesulfonamide Chemical compound C1CN(C)CCN1C1=CC(NS(=O)(=O)C=2C(=C(F)C=C(Br)C=2F)Br)=CC2=C1OCC2 LWAXBVXEBNAMEM-UHFFFAOYSA-N 0.000 claims description 3
- ZGQQPCNPKWFNJZ-UHFFFAOYSA-N 3,4-dimethoxy-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]benzenesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)NC1=CC=C(OC)C(N2CCN(C)CC2)=C1 ZGQQPCNPKWFNJZ-UHFFFAOYSA-N 0.000 claims description 3
- CNIJKPUBLUZAPL-UHFFFAOYSA-N 3-chloro-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-2-methylbenzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=CC(Cl)=C1C CNIJKPUBLUZAPL-UHFFFAOYSA-N 0.000 claims description 3
- SCIAZBXOVPXAAS-UHFFFAOYSA-N 3-iodo-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]benzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=CC(I)=C1 SCIAZBXOVPXAAS-UHFFFAOYSA-N 0.000 claims description 3
- OUTSIUGMFSQICJ-UHFFFAOYSA-N 4-amino-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]benzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(N)C=C1 OUTSIUGMFSQICJ-UHFFFAOYSA-N 0.000 claims description 3
- AGIBDLSPCBZKDV-UHFFFAOYSA-N 4-bromo-n-[3-(4-ethylpiperazin-1-yl)-4-methoxyphenyl]benzenesulfonamide Chemical compound C1CN(CC)CCN1C1=CC(NS(=O)(=O)C=2C=CC(Br)=CC=2)=CC=C1OC AGIBDLSPCBZKDV-UHFFFAOYSA-N 0.000 claims description 3
- LBWINZNVFOVEAU-UHFFFAOYSA-N 4-bromo-n-[7-(4-methylpiperazin-1-yl)-2,3-dihydro-1-benzofuran-5-yl]benzenesulfonamide Chemical compound C1CN(C)CCN1C1=CC(NS(=O)(=O)C=2C=CC(Br)=CC=2)=CC2=C1OCC2 LBWINZNVFOVEAU-UHFFFAOYSA-N 0.000 claims description 3
- KDWOPRGKLIGEMV-UHFFFAOYSA-N 4-chloro-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-3-nitrobenzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 KDWOPRGKLIGEMV-UHFFFAOYSA-N 0.000 claims description 3
- BDHMSYNBSBZCAF-UHFFFAOYSA-N 4-iodo-N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]benzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(I)C=C1 BDHMSYNBSBZCAF-UHFFFAOYSA-N 0.000 claims description 3
- GRTSLVZCKXCJSA-UHFFFAOYSA-N 4-methoxy-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC1=CC=C(OC)C(N2CCN(C)CC2)=C1 GRTSLVZCKXCJSA-UHFFFAOYSA-N 0.000 claims description 3
- HUJQYGNBKNUWRN-UHFFFAOYSA-N 5-(dimethylamino)-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]naphthalene-1-sulfonamide Chemical compound COC1=CC=C(NS(=O)(=O)C=2C3=CC=CC(=C3C=CC=2)N(C)C)C=C1N1CCN(C)CC1 HUJQYGNBKNUWRN-UHFFFAOYSA-N 0.000 claims description 3
- MEEWSHKGZZEATG-UHFFFAOYSA-N 5-bromo-n-(4-methoxy-3-piperazin-1-ylphenyl)thiophene-2-sulfonamide Chemical compound C1=C(N2CCNCC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(Br)S1 MEEWSHKGZZEATG-UHFFFAOYSA-N 0.000 claims description 3
- MKPZRCLLYIMGFB-UHFFFAOYSA-N 5-chloro-n-[4-hydroxy-3-(4-methylpiperazin-1-yl)phenyl]-3-methyl-1-benzothiophene-2-sulfonamide Chemical compound C1CN(C)CCN1C1=CC(NS(=O)(=O)C2=C(C3=CC(Cl)=CC=C3S2)C)=CC=C1O MKPZRCLLYIMGFB-UHFFFAOYSA-N 0.000 claims description 3
- KKCLKUZUEPGDDC-UHFFFAOYSA-N 5-chloro-n-[7-(4-methylpiperazin-1-yl)-2,3-dihydro-1-benzofuran-5-yl]thiophene-2-sulfonamide Chemical compound C1CN(C)CCN1C1=CC(NS(=O)(=O)C=2SC(Cl)=CC=2)=CC2=C1OCC2 KKCLKUZUEPGDDC-UHFFFAOYSA-N 0.000 claims description 3
- HLTFWAMWYXUXEO-UHFFFAOYSA-N 5-chloronaphthalene-2-sulfonic acid Chemical compound ClC1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 HLTFWAMWYXUXEO-UHFFFAOYSA-N 0.000 claims description 3
- CKORXXHYPDBHMC-UHFFFAOYSA-N 7-(4-methylpiperazin-1-yl)-2,3-dihydro-1-benzofuran-5-amine Chemical compound C1CN(C)CCN1C1=CC(N)=CC2=C1OCC2 CKORXXHYPDBHMC-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
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- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/36—Sulfur atoms
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- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
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- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
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- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
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- C—CHEMISTRY; METALLURGY
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Steroid Compounds (AREA)
- Pyrrole Compounds (AREA)
- Indole Compounds (AREA)
- Furan Compounds (AREA)
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| GBGB9722757.3A GB9722757D0 (en) | 1997-10-27 | 1997-10-27 | Novel compounds |
| PCT/EP1997/007159 WO1998027081A1 (en) | 1996-12-19 | 1997-12-15 | Sulphonamide derivatives, process for their preparation, and their use as medicaments |
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| NZ335970A true NZ335970A (en) | 2001-10-26 |
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| NZ335970A NZ335970A (en) | 1996-12-19 | 1997-12-15 | Sulphonamide derivatives and their pharmaceutical use as 5-HT6 antagonists |
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