OA11066A - 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 PDF

Info

Publication number: OA11066A
Authority: OA; OAPI
Prior art keywords: methoxy; phenyl; methylpiperazin; benzenesulfonamide; chloro
Prior art date: 1996-12-19

Application number

OA9900133A

Other languages

English (en)

Inventor

Steven Mark Bromidge

Francis David King

Paul Adrian Wyman

Original Assignee

Smithkline Beecham Plc

Priority date (The priority date 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 date listed.)

1996-12-19

Filing date

1999-06-18

Publication date

2003-03-10

1996-12-19 Priority claimed from GBGB9626377.7A external-priority patent/GB9626377D0/en

1997-01-17 Priority claimed from GBGB9700901.3A external-priority patent/GB9700901D0/en

1997-10-27 Priority claimed from GBGB9722757.3A external-priority patent/GB9722757D0/en

1999-06-18 Application filed by Smithkline Beecham Plc filed Critical Smithkline Beecham Plc

2003-03-10 Publication of OA11066A publication Critical patent/OA11066A/en

Links

238000000034 method Methods 0.000 title claims abstract description 31
239000003814 drug Substances 0.000 title abstract description 4
150000003456 sulfonamides Chemical class 0.000 title abstract 2
230000000694 effects Effects 0.000 claims abstract description 7
150000001875 compounds Chemical class 0.000 claims description 103
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 74
150000001408 amides Chemical class 0.000 claims description 48
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 36
-1 nitro, amino Chemical group 0.000 claims description 22
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 16
125000000217 alkyl group Chemical group 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 14
125000003118 aryl group Chemical group 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 9
150000002367 halogens Chemical class 0.000 claims description 9
125000001624 naphthyl group Chemical group 0.000 claims description 9
229910052760 oxygen Inorganic materials 0.000 claims description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
239000005864 Sulphur Substances 0.000 claims description 8
150000002431 hydrogen Chemical class 0.000 claims description 8
229940124530 sulfonamide Drugs 0.000 claims description 8
125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 7
125000005842 heteroatom Chemical group 0.000 claims description 7
125000000623 heterocyclic group Chemical group 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
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 6
239000001301 oxygen Substances 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
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 5
125000005843 halogen group Chemical group 0.000 claims description 5
125000006239 protecting group Chemical group 0.000 claims description 5
FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 5
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
BNTOKXVZDOERDS-UHFFFAOYSA-N 2,5-dichloro-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]thiophene-3-sulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C=1C=C(Cl)SC=1Cl BNTOKXVZDOERDS-UHFFFAOYSA-N 0.000 claims description 4
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
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
UCVPQLPCDDLJEJ-UHFFFAOYSA-N 3-bromo-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)C=1SC(Cl)=CC=1Br UCVPQLPCDDLJEJ-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
FOJBAYHRQHCRAZ-UHFFFAOYSA-N 3-chloro-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(Cl)=C1 FOJBAYHRQHCRAZ-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
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 4
QKLWJACYWLHEAQ-UHFFFAOYSA-N 4-bromo-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(Br)=C(Cl)S1 QKLWJACYWLHEAQ-UHFFFAOYSA-N 0.000 claims description 4
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 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
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 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
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
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
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 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
JFZVYBXFMIEONX-UHFFFAOYSA-N 5-chloro-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-2-methyl-1-benzothiophene-3-sulfonamide Chemical compound COC1=CC=C(NS(=O)(=O)C=2C3=CC(Cl)=CC=C3SC=2C)C=C1N1CCN(C)CC1 JFZVYBXFMIEONX-UHFFFAOYSA-N 0.000 claims description 4
ZINLARKOVIPOJW-UHFFFAOYSA-N 5-chloro-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-3-methyl-1-benzothiophene-2-sulfonamide Chemical compound COC1=CC=C(NS(=O)(=O)C2=C(C3=CC(Cl)=CC=C3S2)C)C=C1N1CCN(C)CC1 ZINLARKOVIPOJW-UHFFFAOYSA-N 0.000 claims description 4
OVNDJBOYMCAJFK-UHFFFAOYSA-N 5-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(Cl)=C3C=CC=2)C=C1N1CCN(C)CC1 OVNDJBOYMCAJFK-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
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 4
CXGJZEZEELOBCM-UHFFFAOYSA-N 7-chloro-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]naphthalene-1-sulfonamide Chemical compound COC1=CC=C(NS(=O)(=O)C=2C3=CC(Cl)=CC=C3C=CC=2)C=C1N1CCN(C)CC1 CXGJZEZEELOBCM-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
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
ZUAHTVLOPRODJH-UHFFFAOYSA-N n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-1-benzofuran-2-sulfonamide Chemical compound COC1=CC=C(NS(=O)(=O)C=2OC3=CC=CC=C3C=2)C=C1N1CCN(C)CC1 ZUAHTVLOPRODJH-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
BNHPPXTUWQTEEE-UHFFFAOYSA-N n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-2,3,5,6-tetramethylbenzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=C(C)C(C)=CC(C)=C1C BNHPPXTUWQTEEE-UHFFFAOYSA-N 0.000 claims description 4
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 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
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 4
LNIXJYNYVNHPCH-UHFFFAOYSA-N n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]quinoline-8-sulfonamide Chemical compound COC1=CC=C(NS(=O)(=O)C=2C3=NC=CC=C3C=CC=2)C=C1N1CCN(C)CC1 LNIXJYNYVNHPCH-UHFFFAOYSA-N 0.000 claims description 4
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 4
IUWQMRMULCDYLP-UHFFFAOYSA-N n-[7-(4-methylpiperazin-1-yl)-2,3-dihydro-1-benzofuran-5-yl]-5-pyridin-2-ylthiophene-2-sulfonamide Chemical compound C1CN(C)CCN1C1=CC(NS(=O)(=O)C=2SC(=CC=2)C=2N=CC=CC=2)=CC2=C1OCC2 IUWQMRMULCDYLP-UHFFFAOYSA-N 0.000 claims description 4
FTXRUQGGZYFPBQ-UHFFFAOYSA-N n-[7-(4-methylpiperazin-1-yl)-2,3-dihydro-1-benzofuran-5-yl]naphthalene-2-sulfonamide Chemical compound C1CN(C)CCN1C1=CC(NS(=O)(=O)C=2C=C3C=CC=CC3=CC=2)=CC2=C1OCC2 FTXRUQGGZYFPBQ-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
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
125000005913 (C3-C6) cycloalkyl group Chemical group 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
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 3
FPCXZHNKUCICKB-UHFFFAOYSA-N 3-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(Br)=C1 FPCXZHNKUCICKB-UHFFFAOYSA-N 0.000 claims description 3
NTNQMWDFADFBRC-UHFFFAOYSA-N 3-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=C(Br)C=CC=2)=CC2=C1OCC2 NTNQMWDFADFBRC-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
JVMYDAKCSRHLEK-UHFFFAOYSA-N 3-iodo-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(I)=C1 JVMYDAKCSRHLEK-UHFFFAOYSA-N 0.000 claims description 3
PBXGNYAIGYTWMO-UHFFFAOYSA-N 4-bromo-5-chlorothiophene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC(Br)=C(Cl)S1 PBXGNYAIGYTWMO-UHFFFAOYSA-N 0.000 claims description 3
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 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
OZYPUQNRUYTZDI-UHFFFAOYSA-N 4-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=C(Br)C=C1 OZYPUQNRUYTZDI-UHFFFAOYSA-N 0.000 claims description 3
ZDFSCYHQSBOQMG-UHFFFAOYSA-N 4-chloro-2,5-dimethyl-n-(7-piperazin-1-yl-2,3-dihydro-1-benzofuran-5-yl)benzenesulfonamide Chemical compound C1=C(Cl)C(C)=CC(S(=O)(=O)NC=2C=C(C=3OCCC=3C=2)N2CCNCC2)=C1C ZDFSCYHQSBOQMG-UHFFFAOYSA-N 0.000 claims description 3
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 3
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 3
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 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
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YNLFEVAOQLXINF-UHFFFAOYSA-N methylsulfanylmethane;tribromoborane Chemical compound CSC.BrB(Br)Br YNLFEVAOQLXINF-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
BPLWOIRQKQJYCW-UHFFFAOYSA-N n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-3-(trifluoromethyl)benzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 BPLWOIRQKQJYCW-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
229960002715 nicotine Drugs 0.000 description 1
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
239000002687 nonaqueous vehicle Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000001715 oxadiazolyl group Chemical group 0.000 description 1
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
239000004177 patent blue V Substances 0.000 description 1
235000012736 patent blue V Nutrition 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
239000004175 ponceau 4R Substances 0.000 description 1
235000012731 ponceau 4R Nutrition 0.000 description 1
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
239000000047 product Substances 0.000 description 1
238000000159 protein binding assay Methods 0.000 description 1
229940001470 psychoactive drug Drugs 0.000 description 1
239000004089 psychotropic agent Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
238000001525 receptor binding assay Methods 0.000 description 1
239000004180 red 2G Substances 0.000 description 1
239000002151 riboflavin Substances 0.000 description 1
238000007789 sealing Methods 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
108010006590 serotonin 5 receptor Proteins 0.000 description 1
239000003751 serotonin 6 antagonist Substances 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
208000011117 substance-related disease Diseases 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000002278 tabletting lubricant Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
VNNLHYZDXIBHKZ-UHFFFAOYSA-N thiophene-2-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CS1 VNNLHYZDXIBHKZ-UHFFFAOYSA-N 0.000 description 1
230000008733 trauma Effects 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1

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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- 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
- C07D295/04—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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
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)
Furan Compounds (AREA)
Hydrogenated Pyridines (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Indole Compounds (AREA)

OA9900133A 1996-12-19 1999-06-18 Sulphonamide derivatives process for their preparation and their use as medicaments OA11066A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
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

Publications (1)

Publication Number	Publication Date
OA11066A true OA11066A (en)	2003-03-10

Family

ID=27268644

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA9900133A OA11066A (en)	1996-12-19	1999-06-18	Sulphonamide derivatives process for their preparation and their use as medicaments

Country Status (31)

Country	Link
US (2)	US6423717B1 (id)
EP (1)	EP0946539B1 (id)
JP (1)	JP2001506646A (id)
KR (1)	KR20000069554A (id)
CN (1)	CN1246116A (id)
AP (1)	AP1277A (id)
AR (1)	AR010795A1 (id)
AT (1)	ATE247099T1 (id)
AU (1)	AU729056B2 (id)
BG (1)	BG103530A (id)
BR (1)	BR9713734A (id)
CA (1)	CA2275492A1 (id)
CZ (1)	CZ220399A3 (id)
DE (1)	DE69724142T2 (id)
DZ (1)	DZ2376A1 (id)
EA (1)	EA002351B1 (id)
ES (1)	ES2203831T3 (id)
HU (1)	HUP0000658A3 (id)
ID (1)	ID22821A (id)
IL (1)	IL130297A0 (id)
MA (1)	MA24426A1 (id)
NO (1)	NO993003D0 (id)
NZ (1)	NZ335970A (id)
OA (1)	OA11066A (id)
PE (1)	PE46899A1 (id)
PL (1)	PL334337A1 (id)
SK (1)	SK80899A3 (id)
TR (1)	TR199901361T2 (id)
TW (1)	TW418205B (id)
UY (1)	UY24819A1 (id)
WO (1)	WO1998027081A1 (id)

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1997
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Publication number	Publication date
CN1246116A (zh)	2000-03-01
TW418205B (en)	2001-01-11
WO1998027081A1 (en)	1998-06-25
IL130297A0 (en)	2000-06-01
ES2203831T3 (es)	2004-04-16
JP2001506646A (ja)	2001-05-22
DZ2376A1 (fr)	2002-12-28
PE46899A1 (es)	1999-06-24
AP9901556A0 (en)	1999-06-30
US6599904B2 (en)	2003-07-29
US6423717B1 (en)	2002-07-23
DE69724142D1 (de)	2003-09-18
AU729056B2 (en)	2001-01-25
KR20000069554A (ko)	2000-11-25
ATE247099T1 (de)	2003-08-15
NO993003L (no)	1999-06-18
AR010795A1 (es)	2000-07-12
UY24819A1 (es)	2001-08-27
PL334337A1 (en)	2000-02-28
BR9713734A (pt)	2000-03-28
HUP0000658A3 (en)	2001-03-28
SK80899A3 (en)	2000-02-14
HUP0000658A2 (hu)	2001-02-28
NZ335970A (en)	2001-10-26
AU6090498A (en)	1998-07-15
EA002351B1 (ru)	2002-04-25
US20030069233A1 (en)	2003-04-10
AP1277A (en)	2004-05-05
EP0946539B1 (en)	2003-08-13
CA2275492A1 (en)	1998-06-25
EA199900561A1 (ru)	2000-02-28
ID22821A (id)	1999-12-09
NO993003D0 (no)	1999-06-18
BG103530A (bg)	2000-01-31
TR199901361T2 (xx)	1999-08-23
EP0946539A1 (en)	1999-10-06
CZ220399A3 (cs)	1999-11-17
DE69724142T2 (de)	2004-06-03
MA24426A1 (fr)	1998-07-01

Publication	Publication Date	Title
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