ZA200610418B - Novel oxabispidine compounds and their use in the treatment of cardiac arrhythmias - Google Patents
Novel oxabispidine compounds and their use in the treatment of cardiac arrhythmias Download PDFInfo
- Publication number
- ZA200610418B ZA200610418B ZA200610418A ZA200610418A ZA200610418B ZA 200610418 B ZA200610418 B ZA 200610418B ZA 200610418 A ZA200610418 A ZA 200610418A ZA 200610418 A ZA200610418 A ZA 200610418A ZA 200610418 B ZA200610418 B ZA 200610418B
- Authority
- ZA
- South Africa
- Prior art keywords
- ethyl
- diazabicyclo
- oxa
- cyano
- alkyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 142
- 206010003119 arrhythmia Diseases 0.000 title claims description 16
- 238000011282 treatment Methods 0.000 title claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 183
- 125000001424 substituent group Chemical group 0.000 claims description 93
- 125000005843 halogen group Chemical group 0.000 claims description 87
- 125000002947 alkylene group Chemical group 0.000 claims description 68
- 125000003118 aryl group Chemical group 0.000 claims description 61
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 51
- 229910052799 carbon Inorganic materials 0.000 claims description 45
- -1 N-[2-(7-benzyl-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)ethyl]-4- cyanobenzenesulfonamide Chemical compound 0.000 claims description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 40
- 125000003545 alkoxy group Chemical group 0.000 claims description 37
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 35
- 125000003107 substituted aryl group Chemical group 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 125000004076 pyridyl group Chemical group 0.000 claims description 19
- 125000004104 aryloxy group Chemical group 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 230000006793 arrhythmia Effects 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 239000011593 sulfur Chemical group 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000002015 acyclic group Chemical group 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- NHPQGZOBHSVTAQ-IBGZPJMESA-N (2s)-n-(3,5-dimethylphenyl)-1-(4-methoxyphenyl)sulfonylpyrrolidine-2-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1[C@H](C(=O)NC=2C=C(C)C=C(C)C=2)CCC1 NHPQGZOBHSVTAQ-IBGZPJMESA-N 0.000 claims description 2
- 206010047281 Ventricular arrhythmia Diseases 0.000 claims description 2
- 230000001746 atrial effect Effects 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 39
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 18
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 229940124530 sulfonamide Drugs 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 238000011321 prophylaxis Methods 0.000 claims 3
- 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
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 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
- WNISDSGJYBZINT-UHFFFAOYSA-N 1-(3-chlorophenyl)-n-[2-[7-[3-(4-cyanophenoxy)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]methanesulfonamide Chemical compound ClC1=CC=CC(CS(=O)(=O)NCCN2CC3CN(CCCOC=4C=CC(=CC=4)C#N)CC(O3)C2)=C1 WNISDSGJYBZINT-UHFFFAOYSA-N 0.000 claims 1
- XKJIILGQYGIMMK-UHFFFAOYSA-N 2-cyano-n-[2-[3-[(4-cyanophenyl)methyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]benzenesulfonamide Chemical compound C=1C=CC=C(C#N)C=1S(=O)(=O)NCCN(CC(C1)O2)CC2CN1CC1=CC=C(C#N)C=C1 XKJIILGQYGIMMK-UHFFFAOYSA-N 0.000 claims 1
- JWWYVNFEGBCQDQ-UHFFFAOYSA-N 2-cyano-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=C(C#N)C=1S(=O)(=O)NCCN(CC(C1)O2)CC2CN1CCOC1=CC=C(C#N)C=C1 JWWYVNFEGBCQDQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- OOHRBUYYIXNIEX-UHFFFAOYSA-N 3-cyano-n-[2-[3-[(4-cyanophenyl)methyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]benzenesulfonamide Chemical compound C=1C=CC(C#N)=CC=1S(=O)(=O)NCCN(CC(C1)O2)CC2CN1CC1=CC=C(C#N)C=C1 OOHRBUYYIXNIEX-UHFFFAOYSA-N 0.000 claims 1
- UBHAKYHYEIJSOR-UHFFFAOYSA-N 3-cyano-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=C(C=CC=3)C#N)CC2C1 UBHAKYHYEIJSOR-UHFFFAOYSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- GONSDAIMSPSEFA-UHFFFAOYSA-N 4-cyano-n-[2-[3-(1h-indol-3-ylmethyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]benzenesulfonamide Chemical compound C1C(O2)CN(CC=3C4=CC=CC=C4NC=3)CC2CN1CCNS(=O)(=O)C1=CC=C(C#N)C=C1 GONSDAIMSPSEFA-UHFFFAOYSA-N 0.000 claims 1
- SZKKSZMTQHGTGE-UHFFFAOYSA-N 4-cyano-n-[2-[3-[(1-methylindol-3-yl)methyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]benzenesulfonamide Chemical compound C12=CC=CC=C2N(C)C=C1CN(CC(C1)O2)CC2CN1CCNS(=O)(=O)C1=CC=C(C#N)C=C1 SZKKSZMTQHGTGE-UHFFFAOYSA-N 0.000 claims 1
- KQWTVYKRYOXSIC-UHFFFAOYSA-N 4-cyano-n-[2-[3-[(2-cyanophenyl)methyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]benzenesulfonamide Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)NCCN(CC(C1)O2)CC2CN1CC1=CC=CC=C1C#N KQWTVYKRYOXSIC-UHFFFAOYSA-N 0.000 claims 1
- PCKDXYZUAWJFCD-UHFFFAOYSA-N 4-cyano-n-[2-[3-[(3,5-dimethyl-1,2-oxazol-4-yl)methyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]benzenesulfonamide Chemical compound CC1=NOC(C)=C1CN1CC(O2)CN(CCNS(=O)(=O)C=3C=CC(=CC=3)C#N)CC2C1 PCKDXYZUAWJFCD-UHFFFAOYSA-N 0.000 claims 1
- AXQFGWUGUCVEGW-UHFFFAOYSA-N 4-cyano-n-[2-[3-[(4-fluorophenyl)methyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]benzenesulfonamide Chemical compound C1=CC(F)=CC=C1CN1CC(O2)CN(CCNS(=O)(=O)C=3C=CC(=CC=3)C#N)CC2C1 AXQFGWUGUCVEGW-UHFFFAOYSA-N 0.000 claims 1
- BZLVWGJGWNHXRQ-UHFFFAOYSA-N 4-cyano-n-[2-[3-[(5-fluoro-1h-indol-3-yl)methyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]benzenesulfonamide Chemical compound C12=CC(F)=CC=C2NC=C1CN(CC(C1)O2)CC2CN1CCNS(=O)(=O)C1=CC=C(C#N)C=C1 BZLVWGJGWNHXRQ-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
- VIEBEGODSKYRJC-UHFFFAOYSA-N 4-cyano-n-[2-[3-[2-(2,6-difluorophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]benzenesulfonamide Chemical compound FC1=CC=CC(F)=C1OCCN1CC(O2)CN(CCNS(=O)(=O)C=3C=CC(=CC=3)C#N)CC2C1 VIEBEGODSKYRJC-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
- CAHAVAXRPUUEHH-UHFFFAOYSA-N 4-cyano-n-[2-[3-[2-(2-fluorophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]benzenesulfonamide Chemical compound FC1=CC=CC=C1OCCN1CC(O2)CN(CCNS(=O)(=O)C=3C=CC(=CC=3)C#N)CC2C1 CAHAVAXRPUUEHH-UHFFFAOYSA-N 0.000 claims 1
- GHARGDUDBWXSSD-UHFFFAOYSA-N 4-cyano-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)C#N)CC2C1 GHARGDUDBWXSSD-UHFFFAOYSA-N 0.000 claims 1
- AZGMGXKJNFPTTM-UHFFFAOYSA-N 4-cyano-n-[2-[3-[2-(4-fluorophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]benzenesulfonamide Chemical compound C1=CC(F)=CC=C1OCCN1CC(O2)CN(CCNS(=O)(=O)C=3C=CC(=CC=3)C#N)CC2C1 AZGMGXKJNFPTTM-UHFFFAOYSA-N 0.000 claims 1
- UPVJFSQQJZKWHC-UHFFFAOYSA-N 4-cyano-n-[2-[3-[[4-(difluoromethoxy)phenyl]methyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]benzenesulfonamide Chemical compound C1=CC(OC(F)F)=CC=C1CN1CC(O2)CN(CCNS(=O)(=O)C=3C=CC(=CC=3)C#N)CC2C1 UPVJFSQQJZKWHC-UHFFFAOYSA-N 0.000 claims 1
- MVGKZMNFBNXXML-UHFFFAOYSA-N 4-cyano-n-[2-[7-(2-phenylethyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]benzenesulfonamide Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)NCCN(CC(C1)O2)CC2CN1CCC1=CC=CC=C1 MVGKZMNFBNXXML-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
- JZQFSZBHCNSVBL-UHFFFAOYSA-N 4-cyano-n-[2-[7-[2-(2,4-difluorophenyl)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]benzenesulfonamide Chemical compound FC1=CC(F)=CC=C1CCN1CC(O2)CN(CCNS(=O)(=O)C=3C=CC(=CC=3)C#N)CC2C1 JZQFSZBHCNSVBL-UHFFFAOYSA-N 0.000 claims 1
- QTDOWORSRNKJFY-UHFFFAOYSA-N 4-cyano-n-[2-[7-[2-(3,4-difluorophenyl)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]benzenesulfonamide Chemical compound C1=C(F)C(F)=CC=C1CCN1CC(O2)CN(CCNS(=O)(=O)C=3C=CC(=CC=3)C#N)CC2C1 QTDOWORSRNKJFY-UHFFFAOYSA-N 0.000 claims 1
- WFIDWCOYFTXMAY-UHFFFAOYSA-N 4-cyano-n-[2-[7-[2-(4-fluorophenyl)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]benzenesulfonamide Chemical compound C1=CC(F)=CC=C1CCN1CC(O2)CN(CCNS(=O)(=O)C=3C=CC(=CC=3)C#N)CC2C1 WFIDWCOYFTXMAY-UHFFFAOYSA-N 0.000 claims 1
- ATYHFRVGVJBBJI-UHFFFAOYSA-N 4-cyano-n-[2-[7-[2-[4-(difluoromethoxy)phenyl]ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]benzenesulfonamide Chemical compound C1=CC(OC(F)F)=CC=C1CCN1CC(O2)CN(CCNS(=O)(=O)C=3C=CC(=CC=3)C#N)CC2C1 ATYHFRVGVJBBJI-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
- KAVQVUCYJDNFRD-UHFFFAOYSA-N 4-cyano-n-[2-[7-[3-(2,4-difluorophenoxy)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]benzenesulfonamide Chemical compound FC1=CC(F)=CC=C1OCCCN1CC(O2)CN(CCNS(=O)(=O)C=3C=CC(=CC=3)C#N)CC2C1 KAVQVUCYJDNFRD-UHFFFAOYSA-N 0.000 claims 1
- PCQBJKLSSMQWRQ-UHFFFAOYSA-N 4-cyano-n-[2-[7-[3-(2-fluorophenoxy)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]benzenesulfonamide Chemical compound FC1=CC=CC=C1OCCCN1CC(O2)CN(CCNS(=O)(=O)C=3C=CC(=CC=3)C#N)CC2C1 PCQBJKLSSMQWRQ-UHFFFAOYSA-N 0.000 claims 1
- SBROHTKRPQYBCS-UHFFFAOYSA-N 4-cyano-n-[2-[7-[3-(3,4-difluorophenoxy)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]benzenesulfonamide Chemical compound C1=C(F)C(F)=CC=C1OCCCN1CC(O2)CN(CCNS(=O)(=O)C=3C=CC(=CC=3)C#N)CC2C1 SBROHTKRPQYBCS-UHFFFAOYSA-N 0.000 claims 1
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- NEZSJEOOLKCAFY-UHFFFAOYSA-N 4-cyano-n-[2-[7-[3-(4-cyano-2-fluorophenoxy)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]benzenesulfonamide Chemical compound FC1=CC(C#N)=CC=C1OCCCN1CC(O2)CN(CCNS(=O)(=O)C=3C=CC(=CC=3)C#N)CC2C1 NEZSJEOOLKCAFY-UHFFFAOYSA-N 0.000 claims 1
- RKQWDCHCELQJCM-UHFFFAOYSA-N 4-cyano-n-[2-[7-[3-(4-cyanophenoxy)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]benzenesulfonamide Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)NCCN(CC(C1)O2)CC2CN1CCCOC1=CC=C(C#N)C=C1 RKQWDCHCELQJCM-UHFFFAOYSA-N 0.000 claims 1
- SUCKYMCXAOSKOE-UHFFFAOYSA-N 4-cyano-n-[3-[3-[(4-cyanophenyl)methyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propyl]benzenesulfonamide Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)NCCCN(CC(C1)O2)CC2CN1CC1=CC=C(C#N)C=C1 SUCKYMCXAOSKOE-UHFFFAOYSA-N 0.000 claims 1
- FTRQFWIIXZGOBZ-UHFFFAOYSA-N 4-cyano-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)C#N)CC2C1 FTRQFWIIXZGOBZ-UHFFFAOYSA-N 0.000 claims 1
- NIFVNKXVUFLPEB-UHFFFAOYSA-N 4-cyano-n-[3-[3-[2-(4-fluorophenyl)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propyl]benzenesulfonamide Chemical compound C1=CC(F)=CC=C1CCN1CC(O2)CN(CCCNS(=O)(=O)C=3C=CC(=CC=3)C#N)CC2C1 NIFVNKXVUFLPEB-UHFFFAOYSA-N 0.000 claims 1
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- 125000004434 sulfur atom Chemical group 0.000 description 3
- 150000001204 N-oxides Chemical class 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000002336 repolarization Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- PTPQJKANBKHDPM-UHFFFAOYSA-N 3,7-diazabicyclo[3.3.1]nonane Chemical class C1NCC2CNCC1C2 PTPQJKANBKHDPM-UHFFFAOYSA-N 0.000 description 1
- SMSHIXOEBWOYJS-UHFFFAOYSA-N 5,6,7,8-tetrahydroquinazoline Chemical compound C1=NC=C2CCCCC2=N1 SMSHIXOEBWOYJS-UHFFFAOYSA-N 0.000 description 1
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- 208000018452 Torsade de pointes Diseases 0.000 description 1
- 208000002363 Torsades de Pointes Diseases 0.000 description 1
- 229940123445 Tricyclic antidepressant Drugs 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 230000036982 action potential Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004601 benzofurazanyl group Chemical group N1=C2C(=NO1)C(=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 208000006218 bradycardia Diseases 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 230000011128 cardiac conduction Effects 0.000 description 1
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 1
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 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)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0401539A SE0401539D0 (sv) | 2004-06-15 | 2004-06-15 | New compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200610418B true ZA200610418B (en) | 2008-07-30 |
Family
ID=32710059
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200610418A ZA200610418B (en) | 2004-06-15 | 2006-12-12 | Novel oxabispidine compounds and their use in the treatment of cardiac arrhythmias |
| ZA200710111A ZA200710111B (en) | 2004-06-15 | 2007-11-22 | New oxabispidine compounds for the treatment of cardiac arrhythmias |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200710111A ZA200710111B (en) | 2004-06-15 | 2007-11-22 | New oxabispidine compounds for the treatment of cardiac arrhythmias |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US7648985B2 (fr) |
| EP (1) | EP1765832B8 (fr) |
| JP (1) | JP2008502678A (fr) |
| KR (1) | KR20070039045A (fr) |
| CN (2) | CN101525339A (fr) |
| AR (1) | AR049823A1 (fr) |
| AU (2) | AU2005254924B2 (fr) |
| BR (1) | BRPI0512012A (fr) |
| CA (1) | CA2568895A1 (fr) |
| DK (1) | DK1765832T3 (fr) |
| ES (1) | ES2434043T3 (fr) |
| IL (1) | IL179560A0 (fr) |
| MX (1) | MXPA06014692A (fr) |
| NO (1) | NO20070148L (fr) |
| RU (1) | RU2379311C9 (fr) |
| SE (1) | SE0401539D0 (fr) |
| SG (1) | SG153822A1 (fr) |
| TW (1) | TW200612907A (fr) |
| UA (1) | UA85877C2 (fr) |
| UY (1) | UY28959A1 (fr) |
| WO (1) | WO2005123748A1 (fr) |
| ZA (2) | ZA200610418B (fr) |
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 |
| AR057064A1 (es) * | 2005-06-13 | 2007-11-14 | Astrazeneca Ab | Compuestos para el tratamiento de arritmias cardiacas, formulacion farmaceutica y preparacion del compuesto |
| TW200734342A (en) * | 2005-12-15 | 2007-09-16 | Astrazeneca Ab | New compounds for the treatment of cardiac arrhythmias |
| AU2009259494A1 (en) | 2008-06-16 | 2009-12-23 | F. Hoffmann-La Roche Ag | Heteroaromatic monoamides as orexinin receptor antagonists |
| TW201004963A (en) * | 2008-07-03 | 2010-02-01 | Targacept Inc | Derivatives of oxabispidine as neuronal nicotinic acetylcholine receptor ligands |
| WO2010059119A1 (fr) * | 2008-11-21 | 2010-05-27 | Astrazeneca Ab | Combinaison de tert-butyl(2-{7-[2-(4-cyano-2-fluorophénoxy)éthyl]-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl}éthyl)carbamate et de certains benzofuranes antiarythmiques |
| 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 |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| NZ514477A (en) | 1999-04-09 | 2003-04-29 | Astrazeneca Ab | Adamantane derivatives |
| 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 |
| 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 |
| SE0101324D0 (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 |
| SE0401539D0 (sv) | 2004-06-15 | 2004-06-15 | Astrazeneca Ab | New compounds |
| SE0401540D0 (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 JP JP2007516430A patent/JP2008502678A/ja active Pending
- 2005-06-13 CN CN200910134138A patent/CN101525339A/zh active Pending
- 2005-06-13 US US11/570,451 patent/US7648985B2/en not_active Expired - Fee Related
- 2005-06-13 SG SG200904004-9A patent/SG153822A1/en unknown
- 2005-06-13 WO PCT/SE2005/000891 patent/WO2005123748A1/fr active Application Filing
- 2005-06-13 KR KR1020077000930A patent/KR20070039045A/ko active IP Right Grant
- 2005-06-13 CN CNA200580019259XA patent/CN1968956A/zh active Pending
- 2005-06-13 CA CA002568895A patent/CA2568895A1/fr not_active Abandoned
- 2005-06-13 DK DK05752679.0T patent/DK1765832T3/da active
- 2005-06-13 MX MXPA06014692A patent/MXPA06014692A/es not_active Application Discontinuation
- 2005-06-13 ES ES05752679T patent/ES2434043T3/es active Active
- 2005-06-13 RU RU2006145202/04A patent/RU2379311C9/ru not_active IP Right Cessation
- 2005-06-13 UA UAA200612695A patent/UA85877C2/uk unknown
- 2005-06-13 BR BRPI0512012-8A patent/BRPI0512012A/pt not_active IP Right Cessation
- 2005-06-13 EP EP05752679.0A patent/EP1765832B8/fr active Active
- 2005-06-13 AU AU2005254924A patent/AU2005254924B2/en not_active Ceased
- 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
Also Published As
| Publication number | Publication date |
|---|---|
| RU2379311C9 (ru) | 2010-05-27 |
| JP2008502678A (ja) | 2008-01-31 |
| RU2379311C2 (ru) | 2010-01-20 |
| KR20070039045A (ko) | 2007-04-11 |
| AU2005254924B2 (en) | 2009-08-27 |
| TW200612907A (en) | 2006-05-01 |
| WO2005123748A1 (fr) | 2005-12-29 |
| IL179560A0 (en) | 2007-05-15 |
| US20090270383A1 (en) | 2009-10-29 |
| AR049823A1 (es) | 2006-09-06 |
| UA85877C2 (uk) | 2009-03-10 |
| MXPA06014692A (es) | 2007-02-12 |
| ES2434043T3 (es) | 2013-12-13 |
| SG153822A1 (en) | 2009-07-29 |
| AU2005254924A1 (en) | 2005-12-29 |
| AU2009222548A1 (en) | 2009-10-22 |
| SE0401539D0 (sv) | 2004-06-15 |
| UY28959A1 (es) | 2006-01-31 |
| US20090005558A1 (en) | 2009-01-01 |
| EP1765832A1 (fr) | 2007-03-28 |
| EP1765832B8 (fr) | 2013-09-25 |
| US7648985B2 (en) | 2010-01-19 |
| CA2568895A1 (fr) | 2005-12-29 |
| NO20070148L (no) | 2007-01-09 |
| RU2006145202A (ru) | 2008-07-20 |
| BRPI0512012A (pt) | 2008-02-06 |
| CN1968956A (zh) | 2007-05-23 |
| CN101525339A (zh) | 2009-09-09 |
| DK1765832T3 (da) | 2013-10-21 |
| EP1765832B1 (fr) | 2013-08-14 |
| ZA200710111B (en) | 2009-08-26 |
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