RU2379311C9 - Новые оксабиспидиновые соединения и их применение в лечении сердечных аритмий - Google Patents
Новые оксабиспидиновые соединения и их применение в лечении сердечных аритмий Download PDFInfo
- Publication number
- RU2379311C9 RU2379311C9 RU2006145202/04A RU2006145202A RU2379311C9 RU 2379311 C9 RU2379311 C9 RU 2379311C9 RU 2006145202/04 A RU2006145202/04 A RU 2006145202/04A RU 2006145202 A RU2006145202 A RU 2006145202A RU 2379311 C9 RU2379311 C9 RU 2379311C9
- Authority
- RU
- Russia
- Prior art keywords
- ethyl
- oxa
- diazabicyclo
- cyano
- benzenesulfonamide
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract 49
- 206010003119 arrhythmia Diseases 0.000 title abstract 3
- -1 3,5-dimethylisoxazolyl Chemical group 0.000 claims abstract 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 22
- 229910052799 carbon Inorganic materials 0.000 claims abstract 10
- 125000005843 halogen group Chemical group 0.000 claims abstract 10
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract 9
- 150000002367 halogens Chemical class 0.000 claims abstract 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 3
- 125000005842 heteroatom Chemical group 0.000 claims abstract 3
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract 3
- 239000001301 oxygen Substances 0.000 claims abstract 3
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 3
- 150000003839 salts Chemical class 0.000 claims abstract 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims abstract 2
- 230000000694 effects Effects 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 39
- 125000001424 substituent group Chemical group 0.000 claims 37
- 125000002947 alkylene group Chemical group 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims 1
- LJNALGCCKPAENZ-UHFFFAOYSA-N 4-cyano-n-[2-[3-[(4-cyano-2-fluorophenyl)methyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-n-methylbenzenesulfonamide Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)N(C)CCN(CC(C1)O2)CC2CN1CC1=CC=C(C#N)C=C1F LJNALGCCKPAENZ-UHFFFAOYSA-N 0.000 claims 1
- NTQVIPLTMGDUNR-UHFFFAOYSA-N 4-cyano-n-[2-[3-[(4-cyanophenyl)methyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-n-methylbenzenesulfonamide Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)N(C)CCN(CC(C1)O2)CC2CN1CC1=CC=C(C#N)C=C1 NTQVIPLTMGDUNR-UHFFFAOYSA-N 0.000 claims 1
- ZELRGNLVCKCIDB-UHFFFAOYSA-N 4-cyano-n-[2-[3-[(4-fluorophenyl)methyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-n-methylbenzenesulfonamide Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)N(C)CCN(CC(C1)O2)CC2CN1CC1=CC=C(F)C=C1 ZELRGNLVCKCIDB-UHFFFAOYSA-N 0.000 claims 1
- KVCKGSVFJOBICN-UHFFFAOYSA-N 4-cyano-n-[2-[3-[2-(2,6-difluorophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-n-methylbenzenesulfonamide Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)N(C)CCN(CC(C1)O2)CC2CN1CCOC1=C(F)C=CC=C1F KVCKGSVFJOBICN-UHFFFAOYSA-N 0.000 claims 1
- BFMAWDMCMBCWFS-UHFFFAOYSA-N 4-cyano-n-[2-[3-[2-(2-fluorophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-n-methylbenzenesulfonamide Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)N(C)CCN(CC(C1)O2)CC2CN1CCOC1=CC=CC=C1F BFMAWDMCMBCWFS-UHFFFAOYSA-N 0.000 claims 1
- CWQJEYCQFHDOBZ-UHFFFAOYSA-N 4-cyano-n-[2-[7-[2-(2,4-difluorophenyl)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]-n-methylbenzenesulfonamide Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)N(C)CCN(CC(C1)O2)CC2CN1CCC1=CC=C(F)C=C1F CWQJEYCQFHDOBZ-UHFFFAOYSA-N 0.000 claims 1
- JCVUUGGGIYOZFN-UHFFFAOYSA-N 4-cyano-n-[2-[7-[2-(3,4-difluorophenyl)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]-n-methylbenzenesulfonamide Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)N(C)CCN(CC(C1)O2)CC2CN1CCC1=CC=C(F)C(F)=C1 JCVUUGGGIYOZFN-UHFFFAOYSA-N 0.000 claims 1
- JHQBXOVSJXGIRC-UHFFFAOYSA-N 4-cyano-n-[2-[7-[2-[4-(difluoromethoxy)phenyl]ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]-n-methylbenzenesulfonamide Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)N(C)CCN(CC(C1)O2)CC2CN1CCC1=CC=C(OC(F)F)C=C1 JHQBXOVSJXGIRC-UHFFFAOYSA-N 0.000 claims 1
- XXUBZTCWKJTBSM-UHFFFAOYSA-N 4-cyano-n-[2-[7-[3-(2,4-difluorophenoxy)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]-n-methylbenzenesulfonamide Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)N(C)CCN(CC(C1)O2)CC2CN1CCCOC1=CC=C(F)C=C1F XXUBZTCWKJTBSM-UHFFFAOYSA-N 0.000 claims 1
- OLKDMBCMQTXGQZ-UHFFFAOYSA-N C(#N)C1=CC(=C(OCCN2CC3CN(CC(C2)O3)CCNC(O)=O)C=C1)F.C(C)(C)(C)OC(C)(C)C Chemical compound C(#N)C1=CC(=C(OCCN2CC3CN(CC(C2)O3)CCNC(O)=O)C=C1)F.C(C)(C)(C)OC(C)(C)C OLKDMBCMQTXGQZ-UHFFFAOYSA-N 0.000 claims 1
- 101001047090 Homo sapiens Potassium voltage-gated channel subfamily H member 2 Proteins 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- IZSJGOHJUONAPF-UHFFFAOYSA-N n-[2-(3-benzyl-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl)ethyl]-4-cyano-n-methylbenzenesulfonamide Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)N(C)CCN(CC(C1)O2)CC2CN1CC1=CC=CC=C1 IZSJGOHJUONAPF-UHFFFAOYSA-N 0.000 claims 1
- WRYJODWAZQEDTO-UHFFFAOYSA-N n-[2-(3-benzyl-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl)ethyl]-4-fluorobenzenesulfonamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)NCCN1CC(O2)CN(CC=3C=CC=CC=3)CC2C1 WRYJODWAZQEDTO-UHFFFAOYSA-N 0.000 claims 1
- NBVCPDKXRPINAQ-UHFFFAOYSA-N n-[2-[3-(1,2-benzoxazol-3-ylmethyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-4-cyanobenzenesulfonamide Chemical compound C1C(O2)CN(CC=3C4=CC=CC=C4ON=3)CC2CN1CCNS(=O)(=O)C1=CC=C(C#N)C=C1 NBVCPDKXRPINAQ-UHFFFAOYSA-N 0.000 claims 1
- UWJWFBNYVTWXCN-UHFFFAOYSA-N n-[2-[3-(1,3-benzoxazol-2-ylmethyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-4-cyanobenzenesulfonamide Chemical compound C1C(O2)CN(CC=3OC4=CC=CC=C4N=3)CC2CN1CCNS(=O)(=O)C1=CC=C(C#N)C=C1 UWJWFBNYVTWXCN-UHFFFAOYSA-N 0.000 claims 1
- JKYRVIXUFLUELO-UHFFFAOYSA-N n-[2-[3-(1-benzofuran-3-ylmethyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-4-cyanobenzenesulfonamide Chemical compound C1C(O2)CN(CC=3C4=CC=CC=C4OC=3)CC2CN1CCNS(=O)(=O)C1=CC=C(C#N)C=C1 JKYRVIXUFLUELO-UHFFFAOYSA-N 0.000 claims 1
- VVCAFZDPOWQEGJ-BSSNWTCHSA-N n-[2-[3-[(2s)-3-(4-cyanophenoxy)-2-hydroxypropyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-1-phenylmethanesulfonamide Chemical compound C([C@@H](O)CN1CC2CN(CCNS(=O)(=O)CC=3C=CC=CC=3)CC(O2)C1)OC1=CC=C(C#N)C=C1 VVCAFZDPOWQEGJ-BSSNWTCHSA-N 0.000 claims 1
- SXIUZAIGXHEFLZ-PELRDEGISA-N n-[2-[3-[(2s)-3-(4-cyanophenoxy)-2-hydroxypropyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]propane-2-sulfonamide Chemical compound C([C@@H](O)CN1CC2CN(CC(C1)O2)CCNS(=O)(=O)C(C)C)OC1=CC=C(C#N)C=C1 SXIUZAIGXHEFLZ-PELRDEGISA-N 0.000 claims 1
- OOPOYODXWVTCHK-UHFFFAOYSA-N n-[2-[3-[(4-cyanophenyl)methyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-1-phenylmethanesulfonamide Chemical compound C1C(O2)CN(CC=3C=CC(=CC=3)C#N)CC2CN1CCNS(=O)(=O)CC1=CC=CC=C1 OOPOYODXWVTCHK-UHFFFAOYSA-N 0.000 claims 1
- NSAYJESLSNBXFB-UHFFFAOYSA-N n-[2-[3-[(4-cyanophenyl)methyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-3,5-dimethyl-1,2-oxazole-4-sulfonamide Chemical compound CC1=NOC(C)=C1S(=O)(=O)NCCN1CC(O2)CN(CC=3C=CC(=CC=3)C#N)CC2C1 NSAYJESLSNBXFB-UHFFFAOYSA-N 0.000 claims 1
- NIECGVKIKWVLNN-UHFFFAOYSA-N n-[2-[3-[(4-cyanophenyl)methyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-4-fluorobenzenesulfonamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)NCCN1CC(O2)CN(CC=3C=CC(=CC=3)C#N)CC2C1 NIECGVKIKWVLNN-UHFFFAOYSA-N 0.000 claims 1
- QPXUUZXZTDCPDM-UHFFFAOYSA-N n-[2-[3-[2-(4-cyano-2-fluorophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-1-phenylmethanesulfonamide Chemical compound FC1=CC(C#N)=CC=C1OCCN1CC(O2)CN(CCNS(=O)(=O)CC=3C=CC=CC=3)CC2C1 QPXUUZXZTDCPDM-UHFFFAOYSA-N 0.000 claims 1
- TWZKRDAVVYGHAT-UHFFFAOYSA-N n-[2-[3-[2-(4-cyano-2-fluorophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-3-fluorobenzenesulfonamide Chemical compound FC1=CC=CC(S(=O)(=O)NCCN2CC3CN(CCOC=4C(=CC(=CC=4)C#N)F)CC(O3)C2)=C1 TWZKRDAVVYGHAT-UHFFFAOYSA-N 0.000 claims 1
- YQZCITIHBNXONZ-UHFFFAOYSA-N n-[2-[3-[2-(4-cyano-2-fluorophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-4-fluorobenzenesulfonamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)NCCN1CC(O2)CN(CCOC=3C(=CC(=CC=3)C#N)F)CC2C1 YQZCITIHBNXONZ-UHFFFAOYSA-N 0.000 claims 1
- UKTCTGYGCUERBN-UHFFFAOYSA-N n-[2-[3-[2-(4-cyano-2-fluorophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]benzenesulfonamide Chemical compound FC1=CC(C#N)=CC=C1OCCN1CC(O2)CN(CCNS(=O)(=O)C=3C=CC=CC=3)CC2C1 UKTCTGYGCUERBN-UHFFFAOYSA-N 0.000 claims 1
- WJXJSOGBWAHNMS-UHFFFAOYSA-N n-[2-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound CN1C=NC(S(=O)(=O)NCCN2CC3CN(CCOC=4C=CC(=CC=4)C#N)CC(O3)C2)=C1 WJXJSOGBWAHNMS-UHFFFAOYSA-N 0.000 claims 1
- UEQXFWJTIUWOKP-UHFFFAOYSA-N n-[2-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-1-phenylmethanesulfonamide Chemical compound C1C(O2)CN(CCOC=3C=CC(=CC=3)C#N)CC2CN1CCNS(=O)(=O)CC1=CC=CC=C1 UEQXFWJTIUWOKP-UHFFFAOYSA-N 0.000 claims 1
- QJZIEQUUKOHPKT-UHFFFAOYSA-N n-[2-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-2,3-dihydro-1-benzofuran-5-sulfonamide Chemical compound C=1C=C2OCCC2=CC=1S(=O)(=O)NCCN(CC(C1)O2)CC2CN1CCOC1=CC=C(C#N)C=C1 QJZIEQUUKOHPKT-UHFFFAOYSA-N 0.000 claims 1
- LJDGRKMMCUOYAA-UHFFFAOYSA-N n-[2-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-2,4-difluorobenzenesulfonamide Chemical compound FC1=CC(F)=CC=C1S(=O)(=O)NCCN1CC(O2)CN(CCOC=3C=CC(=CC=3)C#N)CC2C1 LJDGRKMMCUOYAA-UHFFFAOYSA-N 0.000 claims 1
- SCGHOSSLGPNTTM-UHFFFAOYSA-N n-[2-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-2-fluorobenzenesulfonamide Chemical compound FC1=CC=CC=C1S(=O)(=O)NCCN1CC(O2)CN(CCOC=3C=CC(=CC=3)C#N)CC2C1 SCGHOSSLGPNTTM-UHFFFAOYSA-N 0.000 claims 1
- XLPZOINVUSQMJC-UHFFFAOYSA-N n-[2-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-3,5-dimethyl-1,2-oxazole-4-sulfonamide Chemical compound CC1=NOC(C)=C1S(=O)(=O)NCCN1CC(O2)CN(CCOC=3C=CC(=CC=3)C#N)CC2C1 XLPZOINVUSQMJC-UHFFFAOYSA-N 0.000 claims 1
- VFNAHQAHRJJPPA-UHFFFAOYSA-N n-[2-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-3-fluorobenzenesulfonamide Chemical compound FC1=CC=CC(S(=O)(=O)NCCN2CC3CN(CCOC=4C=CC(=CC=4)C#N)CC(O3)C2)=C1 VFNAHQAHRJJPPA-UHFFFAOYSA-N 0.000 claims 1
- SYYICIIXCFHJDS-UHFFFAOYSA-N n-[2-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-4-fluorobenzenesulfonamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)NCCN1CC(O2)CN(CCOC=3C=CC(=CC=3)C#N)CC2C1 SYYICIIXCFHJDS-UHFFFAOYSA-N 0.000 claims 1
- HVJJFLMEITXIBQ-UHFFFAOYSA-N n-[2-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-4-methoxybenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NCCN1CC(O2)CN(CCOC=3C=CC(=CC=3)C#N)CC2C1 HVJJFLMEITXIBQ-UHFFFAOYSA-N 0.000 claims 1
- NJAKHOSWSSLROL-UHFFFAOYSA-N n-[2-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-n,3,5-trimethyl-1,2-oxazole-4-sulfonamide Chemical compound CC1=NOC(C)=C1S(=O)(=O)N(C)CCN(CC(C1)O2)CC2CN1CCOC1=CC=C(C#N)C=C1 NJAKHOSWSSLROL-UHFFFAOYSA-N 0.000 claims 1
- BZDRYXYPNHVSJP-UHFFFAOYSA-N n-[2-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NCCN(CC(C1)O2)CC2CN1CCOC1=CC=C(C#N)C=C1 BZDRYXYPNHVSJP-UHFFFAOYSA-N 0.000 claims 1
- YIRDXIKHDISCGJ-UHFFFAOYSA-N n-[2-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]methanesulfonamide Chemical compound C1C(O2)CN(CCNS(=O)(=O)C)CC2CN1CCOC1=CC=C(C#N)C=C1 YIRDXIKHDISCGJ-UHFFFAOYSA-N 0.000 claims 1
- RDVGEKCBSXYDFD-UHFFFAOYSA-N n-[2-[7-[2-(1,2-benzoxazol-3-yl)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]-4-cyanobenzenesulfonamide Chemical compound C1C(O2)CN(CCC=3C4=CC=CC=C4ON=3)CC2CN1CCNS(=O)(=O)C1=CC=C(C#N)C=C1 RDVGEKCBSXYDFD-UHFFFAOYSA-N 0.000 claims 1
- DNDXMBRTAVDSHQ-UHFFFAOYSA-N n-[2-[7-[2-(4-chlorophenyl)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]-4-cyanobenzenesulfonamide Chemical compound C1=CC(Cl)=CC=C1CCN1CC(O2)CN(CCNS(=O)(=O)C=3C=CC(=CC=3)C#N)CC2C1 DNDXMBRTAVDSHQ-UHFFFAOYSA-N 0.000 claims 1
- VDQXZTKNRVATNS-UHFFFAOYSA-N n-[2-[7-[2-(4-cyanophenyl)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]-4-fluorobenzenesulfonamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)NCCN1CC(O2)CN(CCC=3C=CC(=CC=3)C#N)CC2C1 VDQXZTKNRVATNS-UHFFFAOYSA-N 0.000 claims 1
- ARLMFAVDRJKWJK-UHFFFAOYSA-N n-[2-[7-[2-[3,4-bis(difluoromethoxy)phenyl]ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]-4-cyanobenzenesulfonamide Chemical compound C1=C(OC(F)F)C(OC(F)F)=CC=C1CCN1CC(O2)CN(CCNS(=O)(=O)C=3C=CC(=CC=3)C#N)CC2C1 ARLMFAVDRJKWJK-UHFFFAOYSA-N 0.000 claims 1
- MJAFQRMQGNRMGJ-UHFFFAOYSA-N n-[2-[7-[3-(4-cyanophenoxy)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]-1,1,1-trifluoromethanesulfonamide Chemical compound C1C(O2)CN(CCNS(=O)(=O)C(F)(F)F)CC2CN1CCCOC1=CC=C(C#N)C=C1 MJAFQRMQGNRMGJ-UHFFFAOYSA-N 0.000 claims 1
- IUXXPERGRRBARE-UHFFFAOYSA-N n-[2-[7-[3-(4-cyanophenoxy)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound CN1C=NC(S(=O)(=O)NCCN2CC3CN(CCCOC=4C=CC(=CC=4)C#N)CC(O3)C2)=C1 IUXXPERGRRBARE-UHFFFAOYSA-N 0.000 claims 1
- DNUFLAXTXJTMDL-UHFFFAOYSA-N n-[2-[7-[3-(4-cyanophenoxy)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]-1-phenylmethanesulfonamide Chemical compound C1C(O2)CN(CCCOC=3C=CC(=CC=3)C#N)CC2CN1CCNS(=O)(=O)CC1=CC=CC=C1 DNUFLAXTXJTMDL-UHFFFAOYSA-N 0.000 claims 1
- BSNKKGAUJBMSRR-UHFFFAOYSA-N n-[2-[7-[3-(4-cyanophenoxy)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]-2,3-dihydro-1-benzofuran-5-sulfonamide Chemical compound C=1C=C2OCCC2=CC=1S(=O)(=O)NCCN(CC(C1)O2)CC2CN1CCCOC1=CC=C(C#N)C=C1 BSNKKGAUJBMSRR-UHFFFAOYSA-N 0.000 claims 1
- JCVFLWGCPSULRX-UHFFFAOYSA-N n-[2-[7-[3-(4-cyanophenoxy)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]-2,4-difluorobenzenesulfonamide Chemical compound FC1=CC(F)=CC=C1S(=O)(=O)NCCN1CC(O2)CN(CCCOC=3C=CC(=CC=3)C#N)CC2C1 JCVFLWGCPSULRX-UHFFFAOYSA-N 0.000 claims 1
- RCOLTNQLHZQCOG-UHFFFAOYSA-N n-[2-[7-[3-(4-cyanophenoxy)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]-3,5-dimethyl-1,2-oxazole-4-sulfonamide Chemical compound CC1=NOC(C)=C1S(=O)(=O)NCCN1CC(O2)CN(CCCOC=3C=CC(=CC=3)C#N)CC2C1 RCOLTNQLHZQCOG-UHFFFAOYSA-N 0.000 claims 1
- YGOIDNLIRHQXJA-UHFFFAOYSA-N n-[2-[7-[3-(4-cyanophenoxy)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]-4-fluorobenzenesulfonamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)NCCN1CC(O2)CN(CCCOC=3C=CC(=CC=3)C#N)CC2C1 YGOIDNLIRHQXJA-UHFFFAOYSA-N 0.000 claims 1
- GIRGRYFWBVUPSE-UHFFFAOYSA-N n-[2-[7-[3-(4-cyanophenoxy)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]-4-methoxybenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NCCN1CC(O2)CN(CCCOC=3C=CC(=CC=3)C#N)CC2C1 GIRGRYFWBVUPSE-UHFFFAOYSA-N 0.000 claims 1
- DIJXFMJAYGGVBL-UHFFFAOYSA-N n-[2-[7-[3-(4-cyanophenoxy)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]-5-methyl-1,2-oxazole-4-sulfonamide Chemical compound O1N=CC(S(=O)(=O)NCCN2CC3CN(CCCOC=4C=CC(=CC=4)C#N)CC(O3)C2)=C1C DIJXFMJAYGGVBL-UHFFFAOYSA-N 0.000 claims 1
- KMKKIOSIKAOLFN-UHFFFAOYSA-N n-[2-[7-[3-(4-cyanophenoxy)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NCCN(CC(C1)O2)CC2CN1CCCOC1=CC=C(C#N)C=C1 KMKKIOSIKAOLFN-UHFFFAOYSA-N 0.000 claims 1
- KFWVYZRFXBKHPC-UHFFFAOYSA-N n-[2-[7-[3-(4-cyanophenoxy)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]butane-1-sulfonamide Chemical compound C1C(O2)CN(CCNS(=O)(=O)CCCC)CC2CN1CCCOC1=CC=C(C#N)C=C1 KFWVYZRFXBKHPC-UHFFFAOYSA-N 0.000 claims 1
- GPPYBJJOFGJFTI-UHFFFAOYSA-N n-[2-[7-[3-(4-cyanophenoxy)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]methanesulfonamide Chemical compound C1C(O2)CN(CCNS(=O)(=O)C)CC2CN1CCCOC1=CC=C(C#N)C=C1 GPPYBJJOFGJFTI-UHFFFAOYSA-N 0.000 claims 1
- QHCMTLXVYCXROC-UHFFFAOYSA-N n-[2-[7-[3-(4-cyanophenoxy)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]propane-2-sulfonamide Chemical compound C1C(O2)CN(CCNS(=O)(=O)C(C)C)CC2CN1CCCOC1=CC=C(C#N)C=C1 QHCMTLXVYCXROC-UHFFFAOYSA-N 0.000 claims 1
- YUVULFFHSSTSQF-UHFFFAOYSA-N n-[3-(3-benzyl-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl)propyl]-4-cyanobenzenesulfonamide Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)NCCCN(CC(C1)O2)CC2CN1CC1=CC=CC=C1 YUVULFFHSSTSQF-UHFFFAOYSA-N 0.000 claims 1
- WJGRCJUWVBJBSF-UHFFFAOYSA-N n-[3-[3-[(4-cyanophenyl)methyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propyl]-3,5-dimethyl-1,2-oxazole-4-sulfonamide Chemical compound CC1=NOC(C)=C1S(=O)(=O)NCCCN1CC(O2)CN(CC=3C=CC(=CC=3)C#N)CC2C1 WJGRCJUWVBJBSF-UHFFFAOYSA-N 0.000 claims 1
- NXPCUJBWHLGVQM-UHFFFAOYSA-N n-[3-[3-[2-(4-cyano-2-fluorophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propyl]-4-fluorobenzenesulfonamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)NCCCN1CC(O2)CN(CCOC=3C(=CC(=CC=3)C#N)F)CC2C1 NXPCUJBWHLGVQM-UHFFFAOYSA-N 0.000 claims 1
- JYSRPVPEAZBXHI-UHFFFAOYSA-N n-[3-[3-[2-(4-cyano-2-fluorophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propyl]benzenesulfonamide Chemical compound FC1=CC(C#N)=CC=C1OCCN1CC(O2)CN(CCCNS(=O)(=O)C=3C=CC=CC=3)CC2C1 JYSRPVPEAZBXHI-UHFFFAOYSA-N 0.000 claims 1
- JUCKTYLWIRLCNS-UHFFFAOYSA-N n-[3-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propyl]-1-phenylmethanesulfonamide Chemical compound C1C(O2)CN(CCOC=3C=CC(=CC=3)C#N)CC2CN1CCCNS(=O)(=O)CC1=CC=CC=C1 JUCKTYLWIRLCNS-UHFFFAOYSA-N 0.000 claims 1
- PHTHSLUOTRLEHT-UHFFFAOYSA-N n-[3-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propyl]-2,4-difluorobenzenesulfonamide Chemical compound FC1=CC(F)=CC=C1S(=O)(=O)NCCCN1CC(O2)CN(CCOC=3C=CC(=CC=3)C#N)CC2C1 PHTHSLUOTRLEHT-UHFFFAOYSA-N 0.000 claims 1
- XARWJLCINVAJSY-UHFFFAOYSA-N n-[3-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propyl]-2-fluorobenzenesulfonamide Chemical compound FC1=CC=CC=C1S(=O)(=O)NCCCN1CC(O2)CN(CCOC=3C=CC(=CC=3)C#N)CC2C1 XARWJLCINVAJSY-UHFFFAOYSA-N 0.000 claims 1
- FIJVLWXAIQSMQM-UHFFFAOYSA-N n-[3-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propyl]-3,5-dimethyl-1,2-oxazole-4-sulfonamide Chemical compound CC1=NOC(C)=C1S(=O)(=O)NCCCN1CC(O2)CN(CCOC=3C=CC(=CC=3)C#N)CC2C1 FIJVLWXAIQSMQM-UHFFFAOYSA-N 0.000 claims 1
- JDJNGXPUPXBSFP-UHFFFAOYSA-N n-[3-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propyl]-4-fluorobenzenesulfonamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)NCCCN1CC(O2)CN(CCOC=3C=CC(=CC=3)C#N)CC2C1 JDJNGXPUPXBSFP-UHFFFAOYSA-N 0.000 claims 1
- NEQXHQUCZHHDMW-UHFFFAOYSA-N n-[3-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propyl]benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NCCCN(CC(C1)O2)CC2CN1CCOC1=CC=C(C#N)C=C1 NEQXHQUCZHHDMW-UHFFFAOYSA-N 0.000 claims 1
- CIICAQIUYRLOEX-UHFFFAOYSA-N n-[3-[3-[3-(4-cyanophenoxy)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propyl]-1-phenylmethanesulfonamide Chemical compound C1C(O2)CN(CCCOC=3C=CC(=CC=3)C#N)CC2CN1CCCNS(=O)(=O)CC1=CC=CC=C1 CIICAQIUYRLOEX-UHFFFAOYSA-N 0.000 claims 1
- CFTVZSZBSXXYLF-UHFFFAOYSA-N n-[3-[3-[3-(4-cyanophenoxy)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propyl]-3,5-dimethyl-1,2-oxazole-4-sulfonamide Chemical compound CC1=NOC(C)=C1S(=O)(=O)NCCCN1CC(O2)CN(CCCOC=3C=CC(=CC=3)C#N)CC2C1 CFTVZSZBSXXYLF-UHFFFAOYSA-N 0.000 claims 1
- LJGZEPZXSCIXCI-UHFFFAOYSA-N n-[3-[3-[3-(4-cyanophenoxy)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propyl]benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NCCCN(CC(C1)O2)CC2CN1CCCOC1=CC=C(C#N)C=C1 LJGZEPZXSCIXCI-UHFFFAOYSA-N 0.000 claims 1
- PUSGCGICUDEJIT-UHFFFAOYSA-N n-[3-[3-[3-(4-cyanophenoxy)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propyl]propane-2-sulfonamide Chemical compound C1C(O2)CN(CCCNS(=O)(=O)C(C)C)CC2CN1CCCOC1=CC=C(C#N)C=C1 PUSGCGICUDEJIT-UHFFFAOYSA-N 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 12
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 206010047281 Ventricular arrhythmia Diseases 0.000 abstract 1
- 230000006793 arrhythmia Effects 0.000 abstract 1
- 230000000903 blocking effect Effects 0.000 abstract 1
- 230000000747 cardiac effect Effects 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/08—Bridged systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/438—The ring being spiro-condensed with carbocyclic or heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heart & Thoracic Surgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0401539A SE0401539D0 (sv) | 2004-06-15 | 2004-06-15 | New compounds |
| SE0401539-2 | 2004-06-15 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| RU2006145202A RU2006145202A (ru) | 2008-07-20 |
| RU2379311C2 RU2379311C2 (ru) | 2010-01-20 |
| RU2379311C9 true RU2379311C9 (ru) | 2010-05-27 |
Family
ID=32710059
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2006145202/04A RU2379311C9 (ru) | 2004-06-15 | 2005-06-13 | Новые оксабиспидиновые соединения и их применение в лечении сердечных аритмий |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US7648985B2 (https=) |
| EP (1) | EP1765832B8 (https=) |
| JP (1) | JP2008502678A (https=) |
| KR (1) | KR20070039045A (https=) |
| CN (2) | CN101525339A (https=) |
| AR (1) | AR049823A1 (https=) |
| AU (2) | AU2005254924B2 (https=) |
| BR (1) | BRPI0512012A (https=) |
| CA (1) | CA2568895A1 (https=) |
| DK (1) | DK1765832T3 (https=) |
| ES (1) | ES2434043T3 (https=) |
| IL (1) | IL179560A0 (https=) |
| MX (1) | MXPA06014692A (https=) |
| NO (1) | NO20070148L (https=) |
| RU (1) | RU2379311C9 (https=) |
| SE (1) | SE0401539D0 (https=) |
| SG (1) | SG153822A1 (https=) |
| TW (1) | TW200612907A (https=) |
| UA (1) | UA85877C2 (https=) |
| UY (1) | UY28959A1 (https=) |
| WO (1) | WO2005123748A1 (https=) |
| ZA (2) | ZA200610418B (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE0401539D0 (sv) | 2004-06-15 | 2004-06-15 | Astrazeneca Ab | New compounds |
| JP2008543750A (ja) | 2005-06-13 | 2008-12-04 | アストラゼネカ アクチボラグ | 心不整脈の処置用の新規オキサビスピジン化合物 |
| TW200734342A (en) * | 2005-12-15 | 2007-09-16 | Astrazeneca Ab | New compounds for the treatment of cardiac arrhythmias |
| JP2011524398A (ja) | 2008-06-16 | 2011-09-01 | エフ．ホフマン−ラ ロシュ アーゲー | オレキシニン受容体アンタゴニストとしてのヘテロ芳香族モノアミド |
| TW201004963A (en) * | 2008-07-03 | 2010-02-01 | Targacept Inc | Derivatives of oxabispidine as neuronal nicotinic acetylcholine receptor ligands |
| WO2010059119A1 (en) * | 2008-11-21 | 2010-05-27 | Astrazeneca Ab | A combination of tert -butyl (2-{7- [2- (4-cyano-2- f luorophenoxy) ethyl] -9-oxa-3, 7-diazabicyclo [3.3.1] non-3- yl } ethyl) carbamate and certain antiarrhythmic benzofurans |
| US10077420B2 (en) | 2014-12-02 | 2018-09-18 | Histogenics Corporation | Cell and tissue culture container |
| CN117384037B (zh) * | 2023-12-13 | 2024-03-08 | 山东国邦药业有限公司 | 一种二氟乙酸乙酯的制备方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001028992A2 (en) * | 1999-10-18 | 2001-04-26 | Astrazeneca Ab | New oxabispidine compounds useful in the treatment of cardiac arrhythmias |
| WO2002028863A1 (en) * | 2000-10-02 | 2002-04-11 | Astrazeneca Ab | New oxabispidine compound useful in the treatment of cardiac arrhythmias |
Family Cites Families (28)
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| US3196154A (en) * | 1962-05-17 | 1965-07-20 | Sterling Drug Inc | 3-substituted-9-methyl-3, 9-diazabicyclo [3.3.1] nonanes |
| US3503939A (en) * | 1967-03-29 | 1970-03-31 | Du Pont | Polyamides from heterocyclic diamines |
| CH488048A (de) | 1969-06-12 | 1970-03-31 | Inventa Ag | Verfahren zur Herstellung von Polyesterfasern mit verbesserter Gummihaftung |
| DE2428792A1 (de) | 1974-06-14 | 1976-01-02 | Knoll Ag | Neue antiarrhythmika |
| JPS5772977A (en) | 1980-10-23 | 1982-05-07 | Dainippon Ink & Chem Inc | Fluorine-containing diepoxy compound and its preparation |
| DE3112055A1 (de) | 1981-03-27 | 1982-10-07 | Basf Ag, 6700 Ludwigshafen | Bispidinderivate, ihre herstellung und diese enthaltende arzneimittel |
| DE3234697A1 (de) | 1982-09-18 | 1984-03-22 | Kali-Chemie Pharma Gmbh, 3000 Hannover | Neue diazabicyclo-(3,3,1)-nonane |
| US4533713A (en) * | 1983-05-06 | 1985-08-06 | Minnesota Mining And Manufacturing Company | Fluoroaliphaticsulfonamides containing oxirane groups and/or N-β-hydroxyalkylene groups |
| PT88381B (pt) | 1987-09-09 | 1995-07-06 | Kali Chemie Pharma Gmbh | Processo para a preparacao de novos compostos 3,7-diazabiciclo{3,3,1} nonano, e de composicoes farmaceuticas que contem estes compostos |
| DE3732094A1 (de) | 1987-09-24 | 1989-04-06 | Basf Ag | Bispidinderivate als klasse iii-antiarrhythmika |
| US5140033A (en) * | 1989-04-03 | 1992-08-18 | Bayer Aktiengesellschaft | Antibacterial 5-alkylquinolonecarboxylic acids |
| US5110933A (en) | 1989-11-13 | 1992-05-05 | Board Of Regents Of Oklahoma State University | Salts of 3-azabicyclo[3.3.1]nonanes as antiarrhythmic agents, and precursors thereof |
| IL96507A0 (en) * | 1989-12-08 | 1991-08-16 | Merck & Co Inc | Nitrogen-containing spirocycles and pharmaceutical compositions containing them |
| FI100151B (fi) | 1992-09-04 | 1997-09-30 | Nokia Mobile Phones Ltd | Tehonsäästö matkaviestimessä |
| US5294621A (en) * | 1992-10-07 | 1994-03-15 | Ortho Pharmaceutical Corporation | Thieno tetrahydropyridines useful as class III antiarrhythmic agents |
| JPH06284071A (ja) | 1993-01-27 | 1994-10-07 | Casio Comput Co Ltd | 無線受信機 |
| US5468858A (en) | 1993-10-28 | 1995-11-21 | The Board Of Regents Of Oklahoma State University Physical Sciences | N-alkyl and n-acyl derivatives of 3,7-diazabicyclo-[3.3.1]nonanes and selected salts thereof as multi-class antiarrhythmic agents |
| FR2713081B1 (fr) | 1993-11-29 | 1996-01-12 | Celsa Lg | Filtre sanguin perfectionné à deux séries de pattes en pétales. |
| US5831099A (en) * | 1995-03-10 | 1998-11-03 | The United States Of America As Represented By The Secretary Of The Army | Compounds of 1,5-disubstituted-3,7 diaza bicyclo 3.3.0! octanes and products containing the same |
| SE9704709D0 (sv) | 1997-12-17 | 1997-12-17 | Astra Ab | Pharmaceutically active compounds |
| CZ20013608A3 (cs) | 1999-04-09 | 2002-05-15 | Astrazeneca Ab | Adamantanové deriváty |
| SE0101324D0 (sv) * | 2001-04-12 | 2001-04-12 | Astrazeneca Ab | New process |
| SE0101327D0 (sv) * | 2001-04-12 | 2001-04-12 | Astrazeneca Ab | New crystalline forms |
| SE0101323D0 (sv) | 2001-04-12 | 2001-04-12 | Astrazeneca Ab | New process |
| SE0201662D0 (sv) | 2002-05-31 | 2002-05-31 | Astrazeneca Ab | Pharmaceutical combination |
| GB0223712D0 (en) | 2002-10-14 | 2002-11-20 | Astrazeneca Ab | Chemical intermediate |
| SE0401540D0 (sv) * | 2004-06-15 | 2004-06-15 | Astrazeneca Ab | New compounds |
| SE0401539D0 (sv) | 2004-06-15 | 2004-06-15 | Astrazeneca Ab | New compounds |
-
2004
- 2004-06-15 SE SE0401539A patent/SE0401539D0/xx unknown
-
2005
- 2005-06-07 TW TW094118682A patent/TW200612907A/zh unknown
- 2005-06-13 KR KR1020077000930A patent/KR20070039045A/ko not_active Abandoned
- 2005-06-13 EP EP05752679.0A patent/EP1765832B8/en not_active Expired - Lifetime
- 2005-06-13 CN CN200910134138A patent/CN101525339A/zh active Pending
- 2005-06-13 AU AU2005254924A patent/AU2005254924B2/en not_active Ceased
- 2005-06-13 MX MXPA06014692A patent/MXPA06014692A/es not_active Application Discontinuation
- 2005-06-13 CN CNA200580019259XA patent/CN1968956A/zh active Pending
- 2005-06-13 CA CA002568895A patent/CA2568895A1/en not_active Abandoned
- 2005-06-13 RU RU2006145202/04A patent/RU2379311C9/ru not_active IP Right Cessation
- 2005-06-13 DK DK05752679.0T patent/DK1765832T3/da active
- 2005-06-13 BR BRPI0512012-8A patent/BRPI0512012A/pt not_active IP Right Cessation
- 2005-06-13 WO PCT/SE2005/000891 patent/WO2005123748A1/en not_active Ceased
- 2005-06-13 JP JP2007516430A patent/JP2008502678A/ja active Pending
- 2005-06-13 ES ES05752679T patent/ES2434043T3/es not_active Expired - Lifetime
- 2005-06-13 UA UAA200612695A patent/UA85877C2/uk unknown
- 2005-06-13 SG SG200904004-9A patent/SG153822A1/en unknown
- 2005-06-13 US US11/570,451 patent/US7648985B2/en not_active Expired - Fee Related
- 2005-06-14 UY UY28959A patent/UY28959A1/es unknown
- 2005-06-14 AR ARP050102431A patent/AR049823A1/es not_active Application Discontinuation
-
2006
- 2006-11-23 IL IL179560A patent/IL179560A0/en unknown
- 2006-12-12 ZA ZA200610418A patent/ZA200610418B/en unknown
-
2007
- 2007-01-09 NO NO20070148A patent/NO20070148L/no not_active Application Discontinuation
- 2007-11-22 ZA ZA200710111A patent/ZA200710111B/xx unknown
-
2009
- 2009-07-06 US US12/497,792 patent/US20090270383A1/en not_active Abandoned
- 2009-10-02 AU AU2009222548A patent/AU2009222548A1/en not_active Abandoned
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001028992A2 (en) * | 1999-10-18 | 2001-04-26 | Astrazeneca Ab | New oxabispidine compounds useful in the treatment of cardiac arrhythmias |
| WO2002028863A1 (en) * | 2000-10-02 | 2002-04-11 | Astrazeneca Ab | New oxabispidine compound useful in the treatment of cardiac arrhythmias |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2568895A1 (en) | 2005-12-29 |
| US7648985B2 (en) | 2010-01-19 |
| SE0401539D0 (sv) | 2004-06-15 |
| US20090005558A1 (en) | 2009-01-01 |
| AU2005254924B2 (en) | 2009-08-27 |
| EP1765832A1 (en) | 2007-03-28 |
| MXPA06014692A (es) | 2007-02-12 |
| CN101525339A (zh) | 2009-09-09 |
| US20090270383A1 (en) | 2009-10-29 |
| EP1765832B8 (en) | 2013-09-25 |
| SG153822A1 (en) | 2009-07-29 |
| TW200612907A (en) | 2006-05-01 |
| UY28959A1 (es) | 2006-01-31 |
| ES2434043T3 (es) | 2013-12-13 |
| NO20070148L (no) | 2007-01-09 |
| RU2006145202A (ru) | 2008-07-20 |
| BRPI0512012A (pt) | 2008-02-06 |
| WO2005123748A1 (en) | 2005-12-29 |
| AU2005254924A1 (en) | 2005-12-29 |
| DK1765832T3 (da) | 2013-10-21 |
| CN1968956A (zh) | 2007-05-23 |
| AU2009222548A1 (en) | 2009-10-22 |
| IL179560A0 (en) | 2007-05-15 |
| EP1765832B1 (en) | 2013-08-14 |
| JP2008502678A (ja) | 2008-01-31 |
| ZA200610418B (en) | 2008-07-30 |
| AR049823A1 (es) | 2006-09-06 |
| KR20070039045A (ko) | 2007-04-11 |
| RU2379311C2 (ru) | 2010-01-20 |
| ZA200710111B (en) | 2009-08-26 |
| UA85877C2 (uk) | 2009-03-10 |
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Effective date: 20110614 |