JP2008502678A5 - - Google Patents
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- JP2008502678A5 JP2008502678A5 JP2007516430A JP2007516430A JP2008502678A5 JP 2008502678 A5 JP2008502678 A5 JP 2008502678A5 JP 2007516430 A JP2007516430 A JP 2007516430A JP 2007516430 A JP2007516430 A JP 2007516430A JP 2008502678 A5 JP2008502678 A5 JP 2008502678A5
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- JP
- Japan
- Prior art keywords
- ethyl
- oxa
- diazabicyclo
- cyano
- compound
- 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.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims 125
- 125000000217 alkyl group Chemical group 0.000 claims 83
- 125000001424 substituent group Chemical group 0.000 claims 39
- 125000005843 halogen group Chemical group 0.000 claims 34
- 229910052799 carbon Inorganic materials 0.000 claims 31
- 125000002947 alkylene group Chemical group 0.000 claims 29
- 125000003118 aryl group Chemical group 0.000 claims 29
- 229910052739 hydrogen Inorganic materials 0.000 claims 28
- -1 4-cyanophenoxy Chemical group 0.000 claims 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims 22
- 238000006243 chemical reaction Methods 0.000 claims 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 15
- 229910052757 nitrogen Inorganic materials 0.000 claims 13
- 125000003107 substituted aryl group Chemical group 0.000 claims 13
- 125000003545 alkoxy group Chemical group 0.000 claims 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- 206010003119 arrhythmia Diseases 0.000 claims 6
- 230000006793 arrhythmia Effects 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims 6
- 125000004076 pyridyl group Chemical group 0.000 claims 6
- 238000000034 method Methods 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 238000011282 treatment Methods 0.000 claims 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 125000004104 aryloxy group Chemical group 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 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 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims 2
- 239000012321 sodium triacetoxyborohydride Substances 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 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
- 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
- YSEUGKIDEPJNDB-UHFFFAOYSA-N 4-cyano-n-[2-[7-[2-(2-fluorophenyl)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=CC=C1F YSEUGKIDEPJNDB-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
- PJAWWAHOIPODIN-UHFFFAOYSA-N 4-cyano-n-[2-[7-[2-(3-fluorophenyl)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=CC(F)=C1 PJAWWAHOIPODIN-UHFFFAOYSA-N 0.000 claims 1
- SVOUIFYZIRHHHY-UHFFFAOYSA-N 4-cyano-n-[2-[7-[2-(4-fluorophenyl)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=C1 SVOUIFYZIRHHHY-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
- ZZDAXXDPCZOEER-UHFFFAOYSA-N 4-cyano-n-[2-[7-[3-(4-fluorophenoxy)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=C1 ZZDAXXDPCZOEER-UHFFFAOYSA-N 0.000 claims 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 1
- XETZHZZXWRLZBZ-UHFFFAOYSA-N 5-chloro-n-[2-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-1,3-dimethylpyrazole-4-sulfonamide Chemical compound CC1=NN(C)C(Cl)=C1S(=O)(=O)NCCN1CC(O2)CN(CCOC=3C=CC(=CC=3)C#N)CC2C1 XETZHZZXWRLZBZ-UHFFFAOYSA-N 0.000 claims 1
- KWOVTHWLRKOCTM-UHFFFAOYSA-N 5-chloro-n-[2-[7-[3-(4-cyanophenoxy)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]-1,3-dimethylpyrazole-4-sulfonamide Chemical compound CC1=NN(C)C(Cl)=C1S(=O)(=O)NCCN1CC(O2)CN(CCCOC=3C=CC(=CC=3)C#N)CC2C1 KWOVTHWLRKOCTM-UHFFFAOYSA-N 0.000 claims 1
- 206010003130 Arrhythmia supraventricular Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 claims 1
- 206010047281 Ventricular arrhythmia Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 230000001746 atrial effect Effects 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 229940079593 drug Drugs 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
- 230000002140 halogenating effect Effects 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 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
- FSQOJADNTXFIDT-UHFFFAOYSA-N n-[2-[3-[2-(4-cyano-2-fluorophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-2,3-dihydro-1-benzofuran-5-sulfonamide Chemical compound FC1=CC(C#N)=CC=C1OCCN1CC(O2)CN(CCNS(=O)(=O)C=3C=C4CCOC4=CC=3)CC2C1 FSQOJADNTXFIDT-UHFFFAOYSA-N 0.000 claims 1
- JPEMHHZKMYYQAE-UHFFFAOYSA-N n-[2-[3-[2-(4-cyano-2-fluorophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-2,4-difluoro-n-methylbenzenesulfonamide Chemical compound C=1C=C(F)C=C(F)C=1S(=O)(=O)N(C)CCN(CC(C1)O2)CC2CN1CCOC1=CC=C(C#N)C=C1F JPEMHHZKMYYQAE-UHFFFAOYSA-N 0.000 claims 1
- WHHAVRYQXRZQQH-UHFFFAOYSA-N n-[2-[3-[2-(4-cyano-2-fluorophenoxy)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)F)CC2C1 WHHAVRYQXRZQQH-UHFFFAOYSA-N 0.000 claims 1
- VLXAEAXVQDCEEW-UHFFFAOYSA-N n-[2-[3-[2-(4-cyano-2-fluorophenoxy)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)F)CC2C1 VLXAEAXVQDCEEW-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
- WULDWQZLRKAERS-UHFFFAOYSA-N n-[2-[3-[2-(4-cyano-2-fluorophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-n-methyl-2,3-dihydro-1-benzofuran-5-sulfonamide Chemical compound C=1C=C2OCCC2=CC=1S(=O)(=O)N(C)CCN(CC(C1)O2)CC2CN1CCOC1=CC=C(C#N)C=C1F WULDWQZLRKAERS-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
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| 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 |
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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 |
| SE9903759D0 (sv) * | 1999-10-18 | 1999-10-18 | Astra Ab | Pharmaceutically active compounds |
| AR030756A1 (es) | 2000-10-02 | 2003-09-03 | Astrazeneca Ab | Compuesto de oxabispidina util en el tratamiento de arritmias cardiacas |
| 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
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