CA2394603A1 - Antagonistes des recepteurs de l'urotensine ii - Google Patents
Antagonistes des recepteurs de l'urotensine ii Download PDFInfo
- Publication number
- CA2394603A1 CA2394603A1 CA002394603A CA2394603A CA2394603A1 CA 2394603 A1 CA2394603 A1 CA 2394603A1 CA 002394603 A CA002394603 A CA 002394603A CA 2394603 A CA2394603 A CA 2394603A CA 2394603 A1 CA2394603 A1 CA 2394603A1
- Authority
- CA
- Canada
- Prior art keywords
- chloro
- phenyl
- ethoxy
- dimethylamino
- benzenesulfonamide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 102000012327 Urotensin II receptors Human genes 0.000 title claims description 4
- 108050002984 Urotensin II receptors Proteins 0.000 title claims description 4
- 229940044551 receptor antagonist Drugs 0.000 title description 2
- 239000002464 receptor antagonist Substances 0.000 title description 2
- 108010018369 Urotensin II Proteins 0.000 claims abstract description 8
- 102000050488 Urotensin II Human genes 0.000 claims abstract description 8
- HFNHAPQMXICKCF-USJMABIRSA-N urotensin-ii Chemical compound N([C@@H](CC(O)=O)C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC=2C3=CC=CC=C3NC=2)NC(=O)[C@H](CC=2C=CC=CC=2)NC1=O)C(=O)N[C@@H](C(C)C)C(O)=O)C(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@@H](N)CCC(O)=O)[C@@H](C)O HFNHAPQMXICKCF-USJMABIRSA-N 0.000 claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 47
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 208000031225 myocardial ischemia Diseases 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 6
- NBUQXTPZDAPOQY-UHFFFAOYSA-N 2-bromo-n-[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]-4,5-dimethoxybenzenesulfonamide Chemical compound C1=C(OC)C(OC)=CC(Br)=C1S(=O)(=O)NC1=CC=C(Cl)C(OCCN(C)C)=C1 NBUQXTPZDAPOQY-UHFFFAOYSA-N 0.000 claims description 5
- 101100266755 Cyanidium caldarium ycf39 gene Proteins 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- KKHFVDWKDGPRJF-UHFFFAOYSA-N n-[3-[2-(dimethylamino)ethoxy]-4-iodophenyl]-3,4-dimethoxybenzenesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)NC1=CC=C(I)C(OCCN(C)C)=C1 KKHFVDWKDGPRJF-UHFFFAOYSA-N 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 101150008351 ycf3 gene Proteins 0.000 claims description 5
- HVXFXDBJQOAELE-UHFFFAOYSA-N 2,4,6-trichloro-n-[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]benzenesulfonamide Chemical compound C1=C(Cl)C(OCCN(C)C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2Cl)Cl)=C1 HVXFXDBJQOAELE-UHFFFAOYSA-N 0.000 claims description 4
- DBPUOGXTUOXEEL-UHFFFAOYSA-N 2,4-dibromo-n-[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]-5-methoxybenzenesulfonamide Chemical compound C1=C(Br)C(OC)=CC(S(=O)(=O)NC=2C=C(OCCN(C)C)C(Cl)=CC=2)=C1Br DBPUOGXTUOXEEL-UHFFFAOYSA-N 0.000 claims description 4
- DQRJEORUKMINJB-UHFFFAOYSA-N 2,4-dichloro-n-[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]-5-methylbenzenesulfonamide Chemical compound C1=C(Cl)C(OCCN(C)C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(C)C=2)Cl)=C1 DQRJEORUKMINJB-UHFFFAOYSA-N 0.000 claims description 4
- SZQKZEVDKGHWCX-UHFFFAOYSA-N 2,4-dichloro-n-[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]benzenesulfonamide Chemical compound C1=C(Cl)C(OCCN(C)C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2)Cl)=C1 SZQKZEVDKGHWCX-UHFFFAOYSA-N 0.000 claims description 4
- YSXHWGOLJPRPDF-UHFFFAOYSA-N 2,6-dichloro-n-[4-chloro-3-[2-(diethylamino)ethoxy]phenyl]-4-(trifluoromethoxy)benzenesulfonamide Chemical compound C1=C(Cl)C(OCCN(CC)CC)=CC(NS(=O)(=O)C=2C(=CC(OC(F)(F)F)=CC=2Cl)Cl)=C1 YSXHWGOLJPRPDF-UHFFFAOYSA-N 0.000 claims description 4
- UIZHOFJFIOCYLH-UHFFFAOYSA-N 2,6-dichloro-n-[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]-4-(trifluoromethyl)benzenesulfonamide Chemical compound C1=C(Cl)C(OCCN(C)C)=CC(NS(=O)(=O)C=2C(=CC(=CC=2Cl)C(F)(F)F)Cl)=C1 UIZHOFJFIOCYLH-UHFFFAOYSA-N 0.000 claims description 4
- IXDSFPBNCXOJPU-UHFFFAOYSA-N 2-chloro-n-[4-chloro-3-[2-(diethylamino)ethoxy]phenyl]-4,5-dimethoxybenzenesulfonamide Chemical compound C1=C(Cl)C(OCCN(CC)CC)=CC(NS(=O)(=O)C=2C(=CC(OC)=C(OC)C=2)Cl)=C1 IXDSFPBNCXOJPU-UHFFFAOYSA-N 0.000 claims description 4
- RBBKQTCUTJVFMU-UHFFFAOYSA-N 2-chloro-n-[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]-4,5-dimethoxybenzenesulfonamide Chemical compound C1=C(OC)C(OC)=CC(Cl)=C1S(=O)(=O)NC1=CC=C(Cl)C(OCCN(C)C)=C1 RBBKQTCUTJVFMU-UHFFFAOYSA-N 0.000 claims description 4
- FBDNNDQEJFJXMT-UHFFFAOYSA-N 3,4-dibromo-n-[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]benzenesulfonamide Chemical compound C1=C(Cl)C(OCCN(C)C)=CC(NS(=O)(=O)C=2C=C(Br)C(Br)=CC=2)=C1 FBDNNDQEJFJXMT-UHFFFAOYSA-N 0.000 claims description 4
- RRCCVANXQVZDQV-UHFFFAOYSA-N 3-bromo-5-chloro-n-[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]thiophene-2-sulfonamide Chemical compound C1=C(Cl)C(OCCN(C)C)=CC(NS(=O)(=O)C2=C(C=C(Cl)S2)Br)=C1 RRCCVANXQVZDQV-UHFFFAOYSA-N 0.000 claims description 4
- JDLBUPJYYDKUGR-UHFFFAOYSA-N 4,5-dibromo-n-[4-chloro-3-[2-(diethylamino)ethoxy]phenyl]thiophene-2-sulfonamide Chemical compound C1=C(Cl)C(OCCN(CC)CC)=CC(NS(=O)(=O)C=2SC(Br)=C(Br)C=2)=C1 JDLBUPJYYDKUGR-UHFFFAOYSA-N 0.000 claims description 4
- RILUDCIFCROZJR-UHFFFAOYSA-N 4,5-dibromo-n-[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]thiophene-2-sulfonamide Chemical compound C1=C(Cl)C(OCCN(C)C)=CC(NS(=O)(=O)C=2SC(Br)=C(Br)C=2)=C1 RILUDCIFCROZJR-UHFFFAOYSA-N 0.000 claims description 4
- HFQJPPUMFYTOFU-UHFFFAOYSA-N 4,5-dichloro-n-[3-[2-(dimethylamino)ethoxy]-4-iodophenyl]thiophene-2-sulfonamide Chemical compound C1=C(I)C(OCCN(C)C)=CC(NS(=O)(=O)C=2SC(Cl)=C(Cl)C=2)=C1 HFQJPPUMFYTOFU-UHFFFAOYSA-N 0.000 claims description 4
- GIMUZKRVACFTNP-UHFFFAOYSA-N 4-bromo-5-chloro-n-[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]thiophene-2-sulfonamide Chemical compound C1=C(Cl)C(OCCN(C)C)=CC(NS(=O)(=O)C=2SC(Cl)=C(Br)C=2)=C1 GIMUZKRVACFTNP-UHFFFAOYSA-N 0.000 claims description 4
- QWNCSOFIJZPQFI-UHFFFAOYSA-N 4-bromo-n-[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]-2,6-dimethylbenzenesulfonamide Chemical compound C1=C(Cl)C(OCCN(C)C)=CC(NS(=O)(=O)C=2C(=CC(Br)=CC=2C)C)=C1 QWNCSOFIJZPQFI-UHFFFAOYSA-N 0.000 claims description 4
- XLXMBBXTRYEUDF-UHFFFAOYSA-N 4-bromo-n-[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]-2-methylbenzenesulfonamide Chemical compound C1=C(Cl)C(OCCN(C)C)=CC(NS(=O)(=O)C=2C(=CC(Br)=CC=2)C)=C1 XLXMBBXTRYEUDF-UHFFFAOYSA-N 0.000 claims description 4
- PUFGLWFLHAGLJF-UHFFFAOYSA-N 4-bromo-n-[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]-3-methoxybenzenesulfonamide Chemical compound C1=C(Br)C(OC)=CC(S(=O)(=O)NC=2C=C(OCCN(C)C)C(Cl)=CC=2)=C1 PUFGLWFLHAGLJF-UHFFFAOYSA-N 0.000 claims description 4
- LBSIAWBAFOKZAO-UHFFFAOYSA-N 4-chloro-n-[3-[2-(dimethylamino)ethoxy]-4-iodophenyl]-2,1,3-benzoxadiazole-7-sulfonamide Chemical compound C1=C(I)C(OCCN(C)C)=CC(NS(=O)(=O)C=2C3=NON=C3C(Cl)=CC=2)=C1 LBSIAWBAFOKZAO-UHFFFAOYSA-N 0.000 claims description 4
- WVBWLSQBSSJGBM-UHFFFAOYSA-N 4-chloro-n-[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]-3-nitrobenzenesulfonamide Chemical compound C1=C(Cl)C(OCCN(C)C)=CC(NS(=O)(=O)C=2C=C(C(Cl)=CC=2)[N+]([O-])=O)=C1 WVBWLSQBSSJGBM-UHFFFAOYSA-N 0.000 claims description 4
- WTMVUZMFFWMTOF-UHFFFAOYSA-N 5-bromo-6-chloro-n-[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]pyridine-3-sulfonamide Chemical compound C1=C(Cl)C(OCCN(C)C)=CC(NS(=O)(=O)C=2C=C(Br)C(Cl)=NC=2)=C1 WTMVUZMFFWMTOF-UHFFFAOYSA-N 0.000 claims description 4
- PZHBDXXBLJSGBN-UHFFFAOYSA-N 5-chloro-n-[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]-4-nitrothiophene-2-sulfonamide Chemical compound C1=C(Cl)C(OCCN(C)C)=CC(NS(=O)(=O)C=2SC(Cl)=C(C=2)[N+]([O-])=O)=C1 PZHBDXXBLJSGBN-UHFFFAOYSA-N 0.000 claims description 4
- WJVIXIBJHLTUIG-UHFFFAOYSA-N 5-chloro-n-[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]naphthalene-1-sulfonamide Chemical compound C1=C(Cl)C(OCCN(C)C)=CC(NS(=O)(=O)C=2C3=CC=CC(Cl)=C3C=CC=2)=C1 WJVIXIBJHLTUIG-UHFFFAOYSA-N 0.000 claims description 4
- 206010002383 Angina Pectoris Diseases 0.000 claims description 4
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
- 206010012335 Dependence Diseases 0.000 claims description 4
- 206010019280 Heart failures Diseases 0.000 claims description 4
- 208000007920 Neurogenic Inflammation Diseases 0.000 claims description 4
- 208000006011 Stroke Diseases 0.000 claims description 4
- 230000036506 anxiety Effects 0.000 claims description 4
- 206010003119 arrhythmia Diseases 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 230000002503 metabolic effect Effects 0.000 claims description 4
- XSGKINSQQVSAJW-UHFFFAOYSA-N n-[3-[2-(dimethylamino)ethoxy]-4-iodophenyl]-3-methoxybenzenesulfonamide Chemical compound COC1=CC=CC(S(=O)(=O)NC=2C=C(OCCN(C)C)C(I)=CC=2)=C1 XSGKINSQQVSAJW-UHFFFAOYSA-N 0.000 claims description 4
- TVNUOQNXBCYGKJ-UHFFFAOYSA-N n-[4-chloro-3-[2-(diethylamino)ethoxy]phenyl]-3,4-dimethoxybenzenesulfonamide Chemical compound C1=C(Cl)C(OCCN(CC)CC)=CC(NS(=O)(=O)C=2C=C(OC)C(OC)=CC=2)=C1 TVNUOQNXBCYGKJ-UHFFFAOYSA-N 0.000 claims description 4
- CULCVHMNCFNHME-UHFFFAOYSA-N n-[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]-2-nitro-4-(trifluoromethyl)benzenesulfonamide Chemical compound C1=C(Cl)C(OCCN(C)C)=CC(NS(=O)(=O)C=2C(=CC(=CC=2)C(F)(F)F)[N+]([O-])=O)=C1 CULCVHMNCFNHME-UHFFFAOYSA-N 0.000 claims description 4
- AYJWCCMSXOCCPH-UHFFFAOYSA-N n-[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]-3,4-dimethoxybenzenesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C(OCCN(C)C)=C1 AYJWCCMSXOCCPH-UHFFFAOYSA-N 0.000 claims description 4
- VZYVVEDVDUDCNC-UHFFFAOYSA-N n-[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]-4,5-dimethoxy-2-methylbenzenesulfonamide Chemical compound C1=C(OC)C(OC)=CC(C)=C1S(=O)(=O)NC1=CC=C(Cl)C(OCCN(C)C)=C1 VZYVVEDVDUDCNC-UHFFFAOYSA-N 0.000 claims description 4
- FLVLRGQZTZSYFW-UHFFFAOYSA-N n-[4-chloro-3-[3-(dimethylamino)propyl]phenyl]-3,4-dimethoxybenzenesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C(CCCN(C)C)=C1 FLVLRGQZTZSYFW-UHFFFAOYSA-N 0.000 claims description 4
- 230000002232 neuromuscular Effects 0.000 claims description 4
- 208000037803 restenosis Diseases 0.000 claims description 4
- 201000000980 schizophrenia Diseases 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- SMJKGFIZGMZZPJ-UHFFFAOYSA-N 2-bromo-n-[4-chloro-3-[2-(diethylamino)ethoxy]phenyl]-4,5-dimethoxybenzenesulfonamide Chemical compound C1=C(Cl)C(OCCN(CC)CC)=CC(NS(=O)(=O)C=2C(=CC(OC)=C(OC)C=2)Br)=C1 SMJKGFIZGMZZPJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- KQKFDZULFRFMIT-UHFFFAOYSA-N 2,3-dichloro-n-[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]benzenesulfonamide Chemical compound C1=C(Cl)C(OCCN(C)C)=CC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)Cl)=C1 KQKFDZULFRFMIT-UHFFFAOYSA-N 0.000 claims description 2
- ZYJADJQNSILTOD-UHFFFAOYSA-N 2,4-dichloro-n-[3-[2-(dimethylamino)ethoxy]-4-iodophenyl]-6-methylbenzenesulfonamide Chemical compound C1=C(I)C(OCCN(C)C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2C)Cl)=C1 ZYJADJQNSILTOD-UHFFFAOYSA-N 0.000 claims description 2
- NKTGNKIOIBOEJE-UHFFFAOYSA-N 2,5-dichloro-n-[3-[2-(dimethylamino)ethoxy]-4-iodophenyl]thiophene-3-sulfonamide Chemical compound C1=C(I)C(OCCN(C)C)=CC(NS(=O)(=O)C2=C(SC(Cl)=C2)Cl)=C1 NKTGNKIOIBOEJE-UHFFFAOYSA-N 0.000 claims description 2
- LYPWYMVZIVYJOF-UHFFFAOYSA-N 2-bromo-n-[4-chloro-3-[2-(methylamino)ethoxy]phenyl]-4,5-dimethoxybenzenesulfonamide Chemical compound C1=C(Cl)C(OCCNC)=CC(NS(=O)(=O)C=2C(=CC(OC)=C(OC)C=2)Br)=C1 LYPWYMVZIVYJOF-UHFFFAOYSA-N 0.000 claims description 2
- MTOMMXOKVBBTOQ-UHFFFAOYSA-N 2-chloro-n-[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]-4-(trifluoromethyl)benzenesulfonamide Chemical compound C1=C(Cl)C(OCCN(C)C)=CC(NS(=O)(=O)C=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 MTOMMXOKVBBTOQ-UHFFFAOYSA-N 0.000 claims description 2
- YBASKKYIBQNQIH-UHFFFAOYSA-N 3,5-dichloro-n-[3-[2-(dimethylamino)ethoxy]-4-iodophenyl]benzenesulfonamide Chemical compound C1=C(I)C(OCCN(C)C)=CC(NS(=O)(=O)C=2C=C(Cl)C=C(Cl)C=2)=C1 YBASKKYIBQNQIH-UHFFFAOYSA-N 0.000 claims description 2
- JBPGHZQBBJNBPD-UHFFFAOYSA-N 3-chloro-n-[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]-4-fluorobenzenesulfonamide Chemical compound C1=C(Cl)C(OCCN(C)C)=CC(NS(=O)(=O)C=2C=C(Cl)C(F)=CC=2)=C1 JBPGHZQBBJNBPD-UHFFFAOYSA-N 0.000 claims description 2
- KODQFFPVWNXLEN-UHFFFAOYSA-N 3-chloro-n-[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]-4-methylbenzenesulfonamide Chemical compound C1=C(Cl)C(OCCN(C)C)=CC(NS(=O)(=O)C=2C=C(Cl)C(C)=CC=2)=C1 KODQFFPVWNXLEN-UHFFFAOYSA-N 0.000 claims description 2
- CDTLYRXJWAYZSP-UHFFFAOYSA-N 4,5-dichloro-n-[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]thiophene-2-sulfonamide Chemical compound C1=C(Cl)C(OCCN(C)C)=CC(NS(=O)(=O)C=2SC(Cl)=C(Cl)C=2)=C1 CDTLYRXJWAYZSP-UHFFFAOYSA-N 0.000 claims description 2
- JJLDDNFUIRHGFZ-UHFFFAOYSA-N 4-bromo-n-[3-[2-(dimethylamino)ethoxy]-4-iodophenyl]benzenesulfonamide Chemical compound C1=C(I)C(OCCN(C)C)=CC(NS(=O)(=O)C=2C=CC(Br)=CC=2)=C1 JJLDDNFUIRHGFZ-UHFFFAOYSA-N 0.000 claims description 2
- VZIOIBSOJBIYEF-UHFFFAOYSA-N 4-bromo-n-[4-chloro-3-[2-(diethylamino)ethoxy]phenyl]-2,6-dimethylbenzenesulfonamide Chemical compound C1=C(Cl)C(OCCN(CC)CC)=CC(NS(=O)(=O)C=2C(=CC(Br)=CC=2C)C)=C1 VZIOIBSOJBIYEF-UHFFFAOYSA-N 0.000 claims description 2
- COFSMASMXHNWDQ-UHFFFAOYSA-N 4-bromo-n-[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]-2-ethylbenzenesulfonamide Chemical compound CCC1=CC(Br)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C(OCCN(C)C)=C1 COFSMASMXHNWDQ-UHFFFAOYSA-N 0.000 claims description 2
- RSQDXXXDMMHJGV-UHFFFAOYSA-N 4-bromo-n-[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]benzenesulfonamide Chemical compound C1=C(Cl)C(OCCN(C)C)=CC(NS(=O)(=O)C=2C=CC(Br)=CC=2)=C1 RSQDXXXDMMHJGV-UHFFFAOYSA-N 0.000 claims description 2
- PIDBLANPVQAXGL-UHFFFAOYSA-N 4-chloro-n-[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]-2,5-dimethylbenzenesulfonamide Chemical compound C1=C(Cl)C(OCCN(C)C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(C)C=2)C)=C1 PIDBLANPVQAXGL-UHFFFAOYSA-N 0.000 claims description 2
- SWDNLAHAXXBJFA-UHFFFAOYSA-N 4-chloro-n-[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]naphthalene-2-sulfonamide Chemical compound C1=C(Cl)C(OCCN(C)C)=CC(NS(=O)(=O)C=2C=C3C=CC=CC3=C(Cl)C=2)=C1 SWDNLAHAXXBJFA-UHFFFAOYSA-N 0.000 claims description 2
- ZBPXFYJXSAROMG-UHFFFAOYSA-N 4-chloro-n-[[5-[[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]sulfamoyl]thiophen-2-yl]methyl]benzamide Chemical compound C1=C(Cl)C(OCCN(C)C)=CC(NS(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)=C1 ZBPXFYJXSAROMG-UHFFFAOYSA-N 0.000 claims description 2
- GLTHQYZTNQJITA-UHFFFAOYSA-N 5-bromo-n-[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]thiophene-2-sulfonamide Chemical compound C1=C(Cl)C(OCCN(C)C)=CC(NS(=O)(=O)C=2SC(Br)=CC=2)=C1 GLTHQYZTNQJITA-UHFFFAOYSA-N 0.000 claims description 2
- MZDBZBQDHGJUCJ-UHFFFAOYSA-N 5-chloro-n-[3-[2-(dimethylamino)ethoxy]-4-iodophenyl]-3-methyl-1-benzothiophene-2-sulfonamide Chemical compound C1=C(I)C(OCCN(C)C)=CC(NS(=O)(=O)C2=C(C3=CC(Cl)=CC=C3S2)C)=C1 MZDBZBQDHGJUCJ-UHFFFAOYSA-N 0.000 claims description 2
- ISHMGHRAHJHLEB-UHFFFAOYSA-N 5-chloro-n-[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]naphthalene-2-sulfonamide Chemical compound C1=C(Cl)C(OCCN(C)C)=CC(NS(=O)(=O)C=2C=C3C=CC=C(Cl)C3=CC=2)=C1 ISHMGHRAHJHLEB-UHFFFAOYSA-N 0.000 claims description 2
- LHDIONLRCHORNV-UHFFFAOYSA-N 5-chloro-n-[4-chloro-3-[2-(dimethylamino)ethoxy]phenyl]thiophene-2-sulfonamide Chemical compound C1=C(Cl)C(OCCN(C)C)=CC(NS(=O)(=O)C=2SC(Cl)=CC=2)=C1 LHDIONLRCHORNV-UHFFFAOYSA-N 0.000 claims description 2
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 230000000747 cardiac effect Effects 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
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- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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- 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
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Abstract
La présente invention concerne des sulfonamides, des compositions pharmaceutiques contenant ceux-ci et leur utilisation en tant qu'antagonistes de l'urotensine II.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17280799P | 1999-12-21 | 1999-12-21 | |
| US60/172,807 | 1999-12-21 | ||
| PCT/US2000/034574 WO2001045694A1 (fr) | 1999-12-21 | 2000-12-19 | Antagonistes des recepteurs de l'urotensine ii |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2394603A1 true CA2394603A1 (fr) | 2001-06-28 |
Family
ID=22629329
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002394603A Abandoned CA2394603A1 (fr) | 1999-12-21 | 2000-12-19 | Antagonistes des recepteurs de l'urotensine ii |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP1248607A4 (fr) |
| JP (1) | JP2003518057A (fr) |
| AU (1) | AU2441801A (fr) |
| CA (1) | CA2394603A1 (fr) |
| WO (1) | WO2001045694A1 (fr) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2001271018A1 (en) * | 2000-07-04 | 2002-01-14 | Takeda Chemical Industries Ltd. | Gpr14 antagonist |
| EP1331010A4 (fr) * | 2000-08-25 | 2008-08-06 | Takeda Pharmaceutical | Agents prophylactiques et remedes contre des maladies du systeme nerveux central |
| EP1379523B1 (fr) * | 2001-03-27 | 2005-07-27 | Actelion Pharmaceuticals Ltd. | Derives de 1,2,3,4-tetrahydro-isoquinoline en tant qu'antagonistes du recepteur de l'urotensine ii |
| JP2004529134A (ja) * | 2001-03-29 | 2004-09-24 | スミスクライン・ビーチャム・コーポレイション | ピロリジンスルホンアミド |
| US6849635B2 (en) * | 2001-05-07 | 2005-02-01 | Smithkline Beecham Corporation | Sulfonamides |
| EP1387679A4 (fr) * | 2001-05-07 | 2004-08-11 | Smithkline Beecham Corp | Sulfonamides |
| EP1385830A4 (fr) * | 2001-05-07 | 2005-08-17 | Smithkline Beecham Corp | Sulfonamides |
| WO2002089740A2 (fr) * | 2001-05-07 | 2002-11-14 | Smithkline Beecham Corporation | Sulfonamides |
| ES2254772T3 (es) | 2001-12-04 | 2006-06-16 | Actelion Pharmaceuticals Ltd. | 4-(piperidil-y pirrolidil-alquil-ureido)-quinoleinas como receptores antagonistas de urotensina ii. |
| AU2003252478A1 (en) * | 2002-07-10 | 2004-02-02 | Ono Pharmaceutical Co., Ltd. | Ccr4 antagonist and medicinal use thereof |
| ES2264003T3 (es) | 2002-10-07 | 2006-12-16 | Glaxo Group Limited | Derivados de sulfonamida como agentges antipsicoticos. |
| CA2540196C (fr) | 2003-09-26 | 2012-03-20 | Actelion Pharmaceuticals Ltd | Derives de pyridine et leur utilisation comme antagonistes de l'urotensine ii |
| AR051213A1 (es) | 2004-10-12 | 2006-12-27 | Actelion Pharmaceuticals Ltd | 1-(2-(4-bencil-4-hidroxi-piperidin-1-il)-etil)-3-(2-metil-quinolin-4-il)-urea como una sal sulfato cristalina |
| EP1976495A2 (fr) * | 2006-01-06 | 2008-10-08 | Aarhus Universitet | Composes agissant sur le transporteur de la serotonine |
| WO2010048332A2 (fr) * | 2008-10-22 | 2010-04-29 | Acucela, Inc. | Composés de traitement de maladies et troubles ophtalmiques |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4430757A1 (de) * | 1994-08-30 | 1996-03-07 | Boehringer Mannheim Gmbh | Neue 4-Aminopyridazine, Verfahren zu ihrer Herstellung sowie diese Verbindungen enthaltende Arzneimittel |
| DZ2376A1 (fr) * | 1996-12-19 | 2002-12-28 | Smithkline Beecham Plc | Dérivés de sulfonamides nouveaux procédé pour leurpréparation et compositions pharmaceutiques les c ontenant. |
-
2000
- 2000-12-19 AU AU24418/01A patent/AU2441801A/en not_active Abandoned
- 2000-12-19 CA CA002394603A patent/CA2394603A1/fr not_active Abandoned
- 2000-12-19 EP EP00988185A patent/EP1248607A4/fr not_active Withdrawn
- 2000-12-19 WO PCT/US2000/034574 patent/WO2001045694A1/fr not_active Ceased
- 2000-12-19 JP JP2001546633A patent/JP2003518057A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| EP1248607A1 (fr) | 2002-10-16 |
| AU2441801A (en) | 2001-07-03 |
| JP2003518057A (ja) | 2003-06-03 |
| WO2001045694A1 (fr) | 2001-06-28 |
| EP1248607A4 (fr) | 2004-10-06 |
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