AP1277A - Sulphonamide derivatives, process for their preparation, and their use as medicaments. - Google Patents
Sulphonamide derivatives, process for their preparation, and their use as medicaments. Download PDFInfo
- Publication number
- AP1277A AP1277A APAP/P/1999/001556A AP9901556A AP1277A AP 1277 A AP1277 A AP 1277A AP 9901556 A AP9901556 A AP 9901556A AP 1277 A AP1277 A AP 1277A
- Authority
- AP
- ARIPO
- Prior art keywords
- methoxy
- phenyl
- methylpiperazin
- amide
- chloro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 41
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 239000003814 drug Substances 0.000 title claims abstract description 7
- 150000003456 sulfonamides Chemical class 0.000 title claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 127
- 150000001875 compounds Chemical class 0.000 claims description 119
- 150000001408 amides Chemical class 0.000 claims description 79
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 70
- 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 24
- 150000003839 salts Chemical class 0.000 claims description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 19
- -1 nitro, amino Chemical group 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
- 239000005864 Sulphur Chemical group 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 150000002367 halogens Chemical group 0.000 claims description 11
- 150000002431 hydrogen Chemical group 0.000 claims description 11
- 125000001624 naphthyl group Chemical group 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- PBIXGKIJQUGWAZ-UHFFFAOYSA-N 4-methoxy-3-piperazin-1-ylaniline Chemical compound COC1=CC=C(N)C=C1N1CCNCC1 PBIXGKIJQUGWAZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 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 7
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 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 5
- 229940124530 sulfonamide Drugs 0.000 claims description 5
- BSXLLFUSNQCWJP-UHFFFAOYSA-N thiophene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CS1 BSXLLFUSNQCWJP-UHFFFAOYSA-N 0.000 claims description 5
- SJMBDQZKEQESDI-UHFFFAOYSA-N 2-bromo-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=C1Br SJMBDQZKEQESDI-UHFFFAOYSA-N 0.000 claims description 4
- 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 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
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- NUNRNGLRVSKPLF-UHFFFAOYSA-N n-(4-methoxy-3-piperazin-1-ylphenyl)-1-benzofuran-2-sulfonamide Chemical compound COC1=CC=C(NS(=O)(=O)C=2OC3=CC=CC=C3C=2)C=C1N1CCNCC1 NUNRNGLRVSKPLF-UHFFFAOYSA-N 0.000 claims description 4
- XLGJQORLYQFSHT-UHFFFAOYSA-N n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-1-methylindole-2-sulfonamide Chemical compound COC1=CC=C(NS(=O)(=O)C=2N(C3=CC=CC=C3C=2)C)C=C1N1CCN(C)CC1 XLGJQORLYQFSHT-UHFFFAOYSA-N 0.000 claims description 4
- ZYWKRENGSFEBSI-UHFFFAOYSA-N n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-1-phenylmethanesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)CC1=CC=CC=C1 ZYWKRENGSFEBSI-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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 201000000980 schizophrenia Diseases 0.000 claims description 4
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- LFQDZSZMCJKAHG-UHFFFAOYSA-N 1-benzofuran-2-sulfonic acid Chemical compound C1=CC=C2OC(S(=O)(=O)O)=CC2=C1 LFQDZSZMCJKAHG-UHFFFAOYSA-N 0.000 claims description 3
- LIQUPAWMSXBLKH-UHFFFAOYSA-N 2,3,4-trichloro-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(Cl)=C1Cl LIQUPAWMSXBLKH-UHFFFAOYSA-N 0.000 claims description 3
- 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 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
- 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
- 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 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
- 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 3
- 108091005435 5-HT6 receptors Proteins 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
- HQVZFRYJHNRSMU-UHFFFAOYSA-N 5-chloronaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1Cl HQVZFRYJHNRSMU-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
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- 101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 3
- LQVXSNNAFNGRAH-QHCPKHFHSA-N BMS-754807 Chemical compound C([C@@]1(C)C(=O)NC=2C=NC(F)=CC=2)CCN1C(=NN1C=CC=C11)N=C1NC(=NN1)C=C1C1CC1 LQVXSNNAFNGRAH-QHCPKHFHSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- VAEXXTRBLCNPTN-UHFFFAOYSA-N n-[3-(4-methylpiperazin-1-yl)phenyl]naphthalene-2-sulfonamide Chemical compound C1CN(C)CCN1C1=CC=CC(NS(=O)(=O)C=2C=C3C=CC=CC3=CC=2)=C1 VAEXXTRBLCNPTN-UHFFFAOYSA-N 0.000 claims description 3
- OWOHQAJEJVZGKC-UHFFFAOYSA-N n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-4-methylbenzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(C)C=C1 OWOHQAJEJVZGKC-UHFFFAOYSA-N 0.000 claims description 3
- RAUWVSCBYKHDGE-UHFFFAOYSA-N n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-4-propan-2-ylbenzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(C(C)C)C=C1 RAUWVSCBYKHDGE-UHFFFAOYSA-N 0.000 claims description 3
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 150000004885 piperazines Chemical group 0.000 claims description 3
- 125000004193 piperazinyl group Chemical group 0.000 claims description 3
- 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 2
- 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 2
- 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 2
- IHSKRXGUPGHJRL-UHFFFAOYSA-N 4-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=C(F)C=C1 IHSKRXGUPGHJRL-UHFFFAOYSA-N 0.000 claims description 2
- LVFWTBJPVUYJFU-UHFFFAOYSA-N 5-iodo-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(I)=CC=C1C LVFWTBJPVUYJFU-UHFFFAOYSA-N 0.000 claims description 2
- XVRYEZXBBGTHQE-UHFFFAOYSA-N 7-chloronaphthalene-1-sulfonic acid Chemical compound C1=C(Cl)C=C2C(S(=O)(=O)O)=CC=CC2=C1 XVRYEZXBBGTHQE-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 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 2
- 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 2
- LFCAFAUBHUEPPF-UHFFFAOYSA-N n-[4-bromo-3-(4-methylpiperazin-1-yl)phenyl]naphthalene-2-sulfonamide Chemical compound C1CN(C)CCN1C1=CC(NS(=O)(=O)C=2C=C3C=CC=CC3=CC=2)=CC=C1Br LFCAFAUBHUEPPF-UHFFFAOYSA-N 0.000 claims description 2
- BEPNNIXIAODVKF-UHFFFAOYSA-N n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-2-(trifluoromethyl)benzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=CC=C1C(F)(F)F BEPNNIXIAODVKF-UHFFFAOYSA-N 0.000 claims description 2
- ODETWRWNUJHYEY-UHFFFAOYSA-N n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-5-pyridin-2-ylthiophene-2-sulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C(S1)=CC=C1C1=CC=CC=N1 ODETWRWNUJHYEY-UHFFFAOYSA-N 0.000 claims description 2
- OKVWITMLXQZAIF-UHFFFAOYSA-N 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=CS1 OKVWITMLXQZAIF-UHFFFAOYSA-N 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 6
- 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 2
- 230000008485 antagonism Effects 0.000 claims 2
- 230000009286 beneficial effect Effects 0.000 claims 2
- ZNJDFLLJJASPLY-UHFFFAOYSA-N 1-[(5-chloro-3-methyl-1-benzothiophen-2-yl)sulfonyl]-7-piperazin-1-yl-3,4-dihydro-2h-quinoline Chemical compound S1C2=CC=C(Cl)C=C2C(C)=C1S(=O)(=O)N(C1=C2)CCCC1=CC=C2N1CCNCC1 ZNJDFLLJJASPLY-UHFFFAOYSA-N 0.000 claims 1
- ILWQWVQWLKTNFH-UHFFFAOYSA-N 2,3,4-trichloro-n-(4-methoxy-3-piperazin-1-ylphenyl)benzenesulfonamide Chemical compound C1=C(N2CCNCC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1Cl ILWQWVQWLKTNFH-UHFFFAOYSA-N 0.000 claims 1
- LXHVNXMVOAXVPC-UHFFFAOYSA-N 2,5-dibromo-3,6-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=C(F)C(Br)=CC(F)=C1Br LXHVNXMVOAXVPC-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- SZOKIHNIXBVZLV-UHFFFAOYSA-N 3-bromo-5-chlorothiophene-2-sulfonic acid Chemical compound OS(=O)(=O)C=1SC(Cl)=CC=1Br SZOKIHNIXBVZLV-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
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- YNLFEVAOQLXINF-UHFFFAOYSA-N methylsulfanylmethane;tribromoborane Chemical compound CSC.BrB(Br)Br YNLFEVAOQLXINF-UHFFFAOYSA-N 0.000 description 1
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- SPWDRGXBRZSIHU-UHFFFAOYSA-N n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-2,1,3-benzothiadiazole-4-sulfonamide Chemical compound COC1=CC=C(NS(=O)(=O)C=2C3=NSN=C3C=CC=2)C=C1N1CCN(C)CC1 SPWDRGXBRZSIHU-UHFFFAOYSA-N 0.000 description 1
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
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- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
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- 239000012312 sodium hydride Substances 0.000 description 1
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- 230000000707 stereoselective effect Effects 0.000 description 1
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- 239000000126 substance Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
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- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- LRGLFIGRZTYOJU-UHFFFAOYSA-N thiophene-3-sulfonic acid Chemical compound OS(=O)(=O)C=1C=CSC=1 LRGLFIGRZTYOJU-UHFFFAOYSA-N 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
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- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
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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
- C07D295/205—Radicals derived from carbonic acid
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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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
- C07D261/14—Nitrogen atoms
- C07D261/16—Benzene-sulfonamido isoxazoles
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- 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
- C07D295/04—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
- C07D295/135—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 with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- 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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- C—CHEMISTRY; METALLURGY
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- 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
- C07D333/34—Sulfur atoms
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- C07—ORGANIC CHEMISTRY
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- 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
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
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| GBGB9626377.7A GB9626377D0 (en) | 1996-12-19 | 1996-12-19 | Novel compounds |
| GBGB9700901.3A GB9700901D0 (en) | 1997-01-17 | 1997-01-17 | Novel compounds |
| 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AP9901556A0 AP9901556A0 (en) | 1999-06-30 |
| AP1277A true AP1277A (en) | 2004-05-05 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| APAP/P/1999/001556A AP1277A (en) | 1996-12-19 | 1997-12-15 | Sulphonamide derivatives, process for their preparation, and their use as medicaments. |
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