EA002351B1 - Производные сульфонамида, способ их получения и их использование в качестве лекарственных средств - Google Patents
Производные сульфонамида, способ их получения и их использование в качестве лекарственных средств Download PDFInfo
- Publication number
- EA002351B1 EA002351B1 EA199900561A EA199900561A EA002351B1 EA 002351 B1 EA002351 B1 EA 002351B1 EA 199900561 A EA199900561 A EA 199900561A EA 199900561 A EA199900561 A EA 199900561A EA 002351 B1 EA002351 B1 EA 002351B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- methoxy
- phenyl
- methylpiperazin
- amide
- chloro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 53
- 238000002360 preparation method Methods 0.000 title description 11
- 239000003814 drug Substances 0.000 title description 3
- 150000003456 sulfonamides Chemical class 0.000 title description 2
- -1 izoxazolyl Chemical group 0.000 claims abstract description 188
- 150000001875 compounds Chemical class 0.000 claims abstract description 127
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims abstract description 106
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 78
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 31
- 150000001408 amides Chemical class 0.000 claims abstract description 29
- UWMHQNBQRWMRIX-UHFFFAOYSA-N 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=C1 UWMHQNBQRWMRIX-UHFFFAOYSA-N 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
- 150000002367 halogens Chemical class 0.000 claims abstract description 12
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 10
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- 125000005843 halogen group Chemical group 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims abstract description 4
- DHRIBEBTNXSRGD-UHFFFAOYSA-N 1-[(5-chloro-3-methyl-1-benzothiophen-2-yl)sulfonyl]-6-(4-methylpiperazin-1-yl)-2,3-dihydroindole Chemical compound C1CN(C)CCN1C1=CC=C(CCN2S(=O)(=O)C3=C(C4=CC(Cl)=CC=C4S3)C)C2=C1 DHRIBEBTNXSRGD-UHFFFAOYSA-N 0.000 claims abstract description 4
- 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 abstract description 4
- 125000004450 alkenylene group Chemical group 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 150000004885 piperazines Chemical group 0.000 claims abstract description 4
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 4
- 229940124530 sulfonamide Drugs 0.000 claims abstract description 4
- GTYQRUMJFLZBJP-UHFFFAOYSA-N 1-[(5-chloro-3-methyl-1-benzothiophen-2-yl)sulfonyl]-5-methoxy-4-(4-methylpiperazin-1-yl)-2,3-dihydroindole;hydrochloride Chemical compound Cl.COC1=CC=C2N(S(=O)(=O)C3=C(C4=CC(Cl)=CC=C4S3)C)CCC2=C1N1CCN(C)CC1 GTYQRUMJFLZBJP-UHFFFAOYSA-N 0.000 claims abstract 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 abstract description 3
- 229930192474 thiophene Natural products 0.000 claims abstract description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 4
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims abstract 3
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims abstract 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims abstract 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims abstract 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract 3
- 125000001041 indolyl group Chemical group 0.000 claims abstract 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 17
- PBIXGKIJQUGWAZ-UHFFFAOYSA-N 4-methoxy-3-piperazin-1-ylaniline Chemical compound COC1=CC=C(N)C=C1N1CCNCC1 PBIXGKIJQUGWAZ-UHFFFAOYSA-N 0.000 claims description 9
- 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 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- ABOYDMHGKWRPFD-UHFFFAOYSA-N phenylmethanesulfonamide Chemical compound NS(=O)(=O)CC1=CC=CC=C1 ABOYDMHGKWRPFD-UHFFFAOYSA-N 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- FVXQWYNWAQEWFL-UHFFFAOYSA-N N-[7-(4-methylpiperazin-1-yl)-2,3-dihydro-1-benzofuran-5-yl]benzenesulfonamide Chemical compound CN1CCN(CC1)c1cc(NS(=O)(=O)c2ccccc2)cc2CCOc12 FVXQWYNWAQEWFL-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 201000000980 schizophrenia Diseases 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 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 2
- QWZZUZAIHNZLEN-UHFFFAOYSA-N 5-pyridin-2-ylthiophene-2-sulfonic acid Chemical compound S1C(S(=O)(=O)O)=CC=C1C1=CC=CC=N1 QWZZUZAIHNZLEN-UHFFFAOYSA-N 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 230000003993 interaction Effects 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- FMYGZWQMVZTQHK-UHFFFAOYSA-N N-(4-methoxy-3-piperazin-1-ylphenyl)benzenesulfonamide Chemical compound COC1=C(C=C(NS(=O)(=O)C2=CC=CC=C2)C=C1)N1CCNCC1 FMYGZWQMVZTQHK-UHFFFAOYSA-N 0.000 claims 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 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
- NGLSZSLUOMOKDP-UHFFFAOYSA-N 1-methylindole-2-sulfonamide Chemical compound C1=CC=C2N(C)C(S(N)(=O)=O)=CC2=C1 NGLSZSLUOMOKDP-UHFFFAOYSA-N 0.000 claims 1
- UCTYWFKQEPWXOI-UHFFFAOYSA-N 1-methylindole-2-sulfonic acid Chemical compound C1=CC=C2N(C)C(S(O)(=O)=O)=CC2=C1 UCTYWFKQEPWXOI-UHFFFAOYSA-N 0.000 claims 1
- UQCJZZJZIQJVPV-UHFFFAOYSA-N 2-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-3-(trifluoromethyl)benzenesulfonamide Chemical compound COC1=C(C=C(C=C1)C1=C(C=CC=C1C(F)(F)F)S(=O)(=O)N)N1CCN(CC1)C UQCJZZJZIQJVPV-UHFFFAOYSA-N 0.000 claims 1
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- WLQPUTXHTCZSFK-UHFFFAOYSA-N 5-bromothiophene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Br)S1 WLQPUTXHTCZSFK-UHFFFAOYSA-N 0.000 claims 1
- KWJUOHGLRMWVGG-UHFFFAOYSA-N 5-chloro-1-[(5-chloro-3-methyl-1-benzothiophen-2-yl)sulfonyl]-6-piperazin-1-yl-2,3-dihydroindole Chemical compound S1C2=CC=C(Cl)C=C2C(C)=C1S(=O)(=O)N(C1=C2)CCC1=CC(Cl)=C2N1CCNCC1 KWJUOHGLRMWVGG-UHFFFAOYSA-N 0.000 claims 1
- HYLQKFIJBOJPPH-UHFFFAOYSA-N 5-chloro-2-methyl-1-benzothiophene-3-sulfonic acid Chemical compound C1=C(Cl)C=C2C(S(O)(=O)=O)=C(C)SC2=C1 HYLQKFIJBOJPPH-UHFFFAOYSA-N 0.000 claims 1
- LYYUJWBCBHSOCQ-UHFFFAOYSA-N CN(CC1)CCN1C(C=C(C=C1)C(C(C=CC=C2)=C2O2)=C2S(N)(=O)=O)=C1OC Chemical compound CN(CC1)CCN1C(C=C(C=C1)C(C(C=CC=C2)=C2O2)=C2S(N)(=O)=O)=C1OC LYYUJWBCBHSOCQ-UHFFFAOYSA-N 0.000 claims 1
- KWVAOOFXASARHF-UHFFFAOYSA-N COC1=C(C=C(C=C1)C1=C(SC(=C1)C1=NC=CC=C1)S(=O)(=O)N)N1CCN(CC1)C Chemical compound COC1=C(C=C(C=C1)C1=C(SC(=C1)C1=NC=CC=C1)S(=O)(=O)N)N1CCN(CC1)C KWVAOOFXASARHF-UHFFFAOYSA-N 0.000 claims 1
- 239000005557 antagonist Substances 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 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 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- LPSAEQVQKRCXNC-UHFFFAOYSA-N 3-(4-benzylpiperazin-1-yl)-4-methoxyaniline Chemical compound COC1=CC=C(N)C=C1N1CCN(CC=2C=CC=CC=2)CC1 LPSAEQVQKRCXNC-UHFFFAOYSA-N 0.000 abstract description 3
- NGRRREPRVBZRID-UHFFFAOYSA-N 4-methoxy-3-(4-methylpiperazin-1-yl)aniline Chemical compound COC1=CC=C(N)C=C1N1CCN(C)CC1 NGRRREPRVBZRID-UHFFFAOYSA-N 0.000 abstract 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 abstract description 3
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 abstract description 3
- PAVQGEMIVJDBJU-UHFFFAOYSA-N 1-[(5-chloro-3-methyl-1-benzothiophen-2-yl)sulfonyl]-5-methoxy-6-(4-methylpiperazin-1-yl)-2,3-dihydroindole Chemical compound COC1=CC=2CCN(S(=O)(=O)C3=C(C4=CC(Cl)=CC=C4S3)C)C=2C=C1N1CCN(C)CC1 PAVQGEMIVJDBJU-UHFFFAOYSA-N 0.000 abstract description 2
- 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 abstract description 2
- IZFVEYQUDHGHKE-XNTDXEJSSA-N (e)-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-2-phenylethenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)\C=C\C1=CC=CC=C1 IZFVEYQUDHGHKE-XNTDXEJSSA-N 0.000 abstract 1
- 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 abstract 1
- DIERBSMYNZCZIF-UHFFFAOYSA-N 2,5-dibromo-3,6-difluoro-n-(4-methoxy-3-piperazin-1-ylphenyl)benzenesulfonamide Chemical compound C1=C(N2CCNCC2)C(OC)=CC=C1NS(=O)(=O)C1=C(F)C(Br)=CC(F)=C1Br DIERBSMYNZCZIF-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- 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 abstract 1
- 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 abstract 1
- ZTNYZNUQQHDEBR-UHFFFAOYSA-N 2,5-dichloro-n-[7-(4-methylpiperazin-1-yl)-2,3-dihydro-1-benzofuran-5-yl]thiophene-3-sulfonamide Chemical compound C1CN(C)CCN1C1=CC(NS(=O)(=O)C2=C(SC(Cl)=C2)Cl)=CC2=C1OCC2 ZTNYZNUQQHDEBR-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 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 abstract 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- LBGJGZQLAGBTQV-UHFFFAOYSA-N 3,4-dichloro-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)=C1 LBGJGZQLAGBTQV-UHFFFAOYSA-N 0.000 abstract 1
- MIYNDVOEMLLEQH-UHFFFAOYSA-N 3,4-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=C(Cl)C(Cl)=C1 MIYNDVOEMLLEQH-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- TXBZLOLLOHEAOS-UHFFFAOYSA-N 3,5-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(Cl)=CC(Cl)=C1 TXBZLOLLOHEAOS-UHFFFAOYSA-N 0.000 abstract 1
- UKXWUJQCCUZLAQ-UHFFFAOYSA-N 3,5-dichloro-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(Cl)C=C(Cl)C=2)=CC2=C1OCC2 UKXWUJQCCUZLAQ-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- 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 abstract 1
- 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 abstract 1
- 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 abstract 1
- 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 abstract 1
- 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 abstract 1
- 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 abstract 1
- 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 abstract 1
- 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 abstract 1
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- 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 abstract 1
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- IJTDYSPHKVDMFO-UHFFFAOYSA-N tert-butyl 4-(2-methoxy-5-nitrophenyl)piperazine-1-carboxylate Chemical compound COC1=CC=C([N+]([O-])=O)C=C1N1CCN(C(=O)OC(C)(C)C)CC1 IJTDYSPHKVDMFO-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000759 toxicological effect Toxicity 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
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 235000019235 yellow 2G Nutrition 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)
- Indole 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)
Applications Claiming Priority (4)
| 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 |
| 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 |
|---|---|
| EA199900561A1 EA199900561A1 (ru) | 2000-02-28 |
| EA002351B1 true EA002351B1 (ru) | 2002-04-25 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA199900561A EA002351B1 (ru) | 1996-12-19 | 1997-12-15 | Производные сульфонамида, способ их получения и их использование в качестве лекарственных средств |
Country Status (31)
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| EP (1) | EP0946539B1 (enExample) |
| JP (1) | JP2001506646A (enExample) |
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| CN (1) | CN1246116A (enExample) |
| AP (1) | AP1277A (enExample) |
| AR (1) | AR010795A1 (enExample) |
| AT (1) | ATE247099T1 (enExample) |
| AU (1) | AU729056B2 (enExample) |
| BG (1) | BG103530A (enExample) |
| BR (1) | BR9713734A (enExample) |
| CA (1) | CA2275492A1 (enExample) |
| CZ (1) | CZ220399A3 (enExample) |
| DE (1) | DE69724142T2 (enExample) |
| DZ (1) | DZ2376A1 (enExample) |
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| ES (1) | ES2203831T3 (enExample) |
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| ID (1) | ID22821A (enExample) |
| IL (1) | IL130297A0 (enExample) |
| MA (1) | MA24426A1 (enExample) |
| NO (1) | NO993003L (enExample) |
| NZ (1) | NZ335970A (enExample) |
| OA (1) | OA11066A (enExample) |
| PE (1) | PE46899A1 (enExample) |
| PL (1) | PL334337A1 (enExample) |
| SK (1) | SK80899A3 (enExample) |
| TR (1) | TR199901361T2 (enExample) |
| TW (1) | TW418205B (enExample) |
| UY (1) | UY24819A1 (enExample) |
| WO (1) | WO1998027081A1 (enExample) |
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|---|---|---|---|---|
| DZ2376A1 (fr) * | 1996-12-19 | 2002-12-28 | Smithkline Beecham Plc | Dérivés de sulfonamides nouveaux procédé pour leurpréparation et compositions pharmaceutiques les c ontenant. |
| WO1999002502A2 (en) * | 1997-07-11 | 1999-01-21 | Smithkline Beecham Plc | Sulphonamide derivatives being 5-ht6 receptor antagonists and process for their preparation |
| ES2317688T3 (es) | 1998-01-29 | 2009-04-16 | Amgen Inc. | Moduladores ppar-gamma. |
| GB9803411D0 (en) * | 1998-02-18 | 1998-04-15 | Smithkline Beecham Plc | Novel compounds |
| US6194410B1 (en) | 1998-03-11 | 2001-02-27 | Hoffman-La Roche Inc. | Pyrazolopyrimidine and pyrazolines and process for preparation thereof |
| GB9810671D0 (en) * | 1998-05-18 | 1998-07-15 | Pfizer Ltd | Anti-pruritic agents |
| GB9818914D0 (en) * | 1998-08-28 | 1998-10-21 | Smithkline Beecham Plc | Use |
| GB9818916D0 (en) | 1998-08-28 | 1998-10-21 | Smithkline Beecham Plc | Use |
| GB9820113D0 (en) | 1998-09-15 | 1998-11-11 | Merck Sharp & Dohme | Therapeutic agents |
| US7041691B1 (en) | 1999-06-30 | 2006-05-09 | Amgen Inc. | Compounds for the modulation of PPARγ activity |
| GB9926302D0 (en) * | 1999-11-05 | 2000-01-12 | Smithkline Beecham Plc | Novel compounds |
| EP1248607A4 (en) * | 1999-12-21 | 2004-10-06 | Smithkline Beecham Corp | UROTENSIN II RECEPTOR ANTAGONISTS |
| SE9904723D0 (sv) * | 1999-12-22 | 1999-12-22 | Carlsson A Research Ab | New modulators of dopamine neurotransmission II |
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| US20030171399A1 (en) | 2000-06-28 | 2003-09-11 | Tularik Inc. | Quinolinyl and benzothiazolyl modulators |
| SE0002739D0 (sv) * | 2000-07-21 | 2000-07-21 | Pharmacia & Upjohn Ab | New use |
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| SE0002754D0 (sv) * | 2000-07-21 | 2000-07-21 | Pharmacia & Upjohn Ab | New pharmaceutical combination formulation and method of treatment with the combination |
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| JP2004529164A (ja) * | 2001-05-07 | 2004-09-24 | スミスクライン・ビーチャム・コーポレイション | スルホンアミド |
| WO2002090337A1 (en) * | 2001-05-07 | 2002-11-14 | Smithkline Beecham Corporation | Sulfonamides |
| US6743796B2 (en) * | 2001-05-07 | 2004-06-01 | Wyeth | Piperazinyl-isatins |
| AR033879A1 (es) * | 2001-05-07 | 2004-01-07 | Smithkline Beecham Corp | Compuesto sulfonamida, composicion farmaceutica que lo comprende, su uso para preparar dicha composicion y procedimiento para la obtencion de dicho compuesto |
| US20050043536A1 (en) * | 2001-05-07 | 2005-02-24 | Dashyant Dhanak | Sulfonamides |
| US6849635B2 (en) * | 2001-05-07 | 2005-02-01 | Smithkline Beecham Corporation | Sulfonamides |
| GB0111186D0 (en) * | 2001-05-08 | 2001-06-27 | Smithkline Beecham Plc | Novel compounds |
| KR100922486B1 (ko) * | 2001-05-11 | 2009-10-20 | 바이오비트럼 에이비(피유비엘) | 비만, 제 ⅱ 형 당뇨병 및 ｃｎｓ 장애의 치료를 위한신규한 아릴술폰아미드 화합물 |
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