MXPA06014692A - Nuevos compuestos de oxabispidina y su uso en el tratamiento de arritmias cardiacas. - Google Patents
Nuevos compuestos de oxabispidina y su uso en el tratamiento de arritmias cardiacas.Info
- Publication number
- MXPA06014692A MXPA06014692A MXPA06014692A MXPA06014692A MXPA06014692A MX PA06014692 A MXPA06014692 A MX PA06014692A MX PA06014692 A MXPA06014692 A MX PA06014692A MX PA06014692 A MXPA06014692 A MX PA06014692A MX PA06014692 A MXPA06014692 A MX PA06014692A
- Authority
- MX
- Mexico
- Prior art keywords
- ethyl
- oxa
- cyano
- diazabicyclo
- formula
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 386
- 206010003119 arrhythmia Diseases 0.000 title claims abstract description 26
- 238000011282 treatment Methods 0.000 title claims abstract description 19
- 230000006793 arrhythmia Effects 0.000 claims abstract description 16
- 238000011321 prophylaxis Methods 0.000 claims abstract description 8
- 230000001746 atrial effect Effects 0.000 claims abstract description 6
- 206010047281 Ventricular arrhythmia Diseases 0.000 claims abstract description 5
- 206010003130 Arrhythmia supraventricular Diseases 0.000 claims abstract description 4
- -1 4-cyanophenoxy Chemical group 0.000 claims description 346
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 241
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 135
- 125000000217 alkyl group Chemical group 0.000 claims description 128
- 125000001424 substituent group Chemical group 0.000 claims description 123
- 125000005843 halogen group Chemical group 0.000 claims description 107
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 101
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 99
- 125000002947 alkylene group Chemical group 0.000 claims description 67
- 125000003118 aryl group Chemical group 0.000 claims description 65
- 239000002904 solvent Substances 0.000 claims description 63
- 239000000203 mixture Substances 0.000 claims description 62
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 56
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 55
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 53
- 238000002360 preparation method Methods 0.000 claims description 49
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 44
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 claims description 40
- 229910052799 carbon Inorganic materials 0.000 claims description 38
- 229910052757 nitrogen Inorganic materials 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 229920006395 saturated elastomer Polymers 0.000 claims description 27
- 125000003107 substituted aryl group Chemical group 0.000 claims description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 22
- 125000004076 pyridyl group Chemical group 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
- 125000002619 bicyclic group Chemical group 0.000 claims description 17
- 239000001301 oxygen Substances 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 13
- 125000004104 aryloxy group Chemical group 0.000 claims description 13
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 13
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 12
- 241001139947 Mida Species 0.000 claims description 12
- 101100070530 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) het-6 gene Proteins 0.000 claims description 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 11
- 239000011593 sulfur Substances 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 9
- SJMCLWCCNYAWRQ-UHFFFAOYSA-N propane-2-sulfonamide Chemical compound CC(C)S(N)(=O)=O SJMCLWCCNYAWRQ-UHFFFAOYSA-N 0.000 claims description 9
- 230000009467 reduction Effects 0.000 claims description 9
- 229940124530 sulfonamide Drugs 0.000 claims description 9
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 8
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 8
- 101100515517 Arabidopsis thaliana XI-I gene Proteins 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 6
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 239000003638 chemical reducing agent Substances 0.000 claims description 6
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 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 description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 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 description 5
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 5
- 239000012321 sodium triacetoxyborohydride Substances 0.000 claims description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 4
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000002015 acyclic group Chemical group 0.000 claims description 4
- OVIZSQRQYWEGON-UHFFFAOYSA-N butane-1-sulfonamide Chemical compound CCCCS(N)(=O)=O OVIZSQRQYWEGON-UHFFFAOYSA-N 0.000 claims description 4
- 238000010511 deprotection reaction Methods 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims description 3
- PCBZRNYXXCIELG-WYFCWLEVSA-N COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 Chemical compound COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 PCBZRNYXXCIELG-WYFCWLEVSA-N 0.000 claims description 3
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 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 description 3
- 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 description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- 125000000980 1H-indol-3-ylmethyl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C(C([H])([H])[*])C2=C1[H] 0.000 claims description 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 claims description 2
- WRWYGOVGIGCDLE-UHFFFAOYSA-N [O]c1ccccc1F Chemical group [O]c1ccccc1F WRWYGOVGIGCDLE-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 239000000306 component Substances 0.000 claims 1
- ZCRZCMUDOWDGOB-UHFFFAOYSA-N ethanesulfonimidic acid Chemical compound CCS(N)(=O)=O ZCRZCMUDOWDGOB-UHFFFAOYSA-N 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 238000004519 manufacturing process Methods 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
- DISKQMLINWSDKG-UHFFFAOYSA-N n-[2-[7-[2-(4-chlorophenyl)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]-4-cyano-n-methylbenzenesulfonamide Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)N(C)CCN(CC(C1)O2)CC2CN1CCC1=CC=C(Cl)C=C1 DISKQMLINWSDKG-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
- 102200160920 rs35304565 Human genes 0.000 claims 1
- 102220084927 rs778740017 Human genes 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 245
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- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011534 wash buffer Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 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)
- 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 |
| PCT/SE2005/000891 WO2005123748A1 (en) | 2004-06-15 | 2005-06-13 | Novel oxabispidine compounds and their use in the treatment of cardiac arrhythmias |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA06014692A true MXPA06014692A (es) | 2007-02-12 |
Family
ID=32710059
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA06014692A MXPA06014692A (es) | 2004-06-15 | 2005-06-13 | Nuevos compuestos de oxabispidina y su uso en el tratamiento de arritmias cardiacas. |
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 |
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 |
| 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
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 |
| 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 |
| RU2379311C9 (ru) | 2010-05-27 |
| 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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA | Abandonment or withdrawal |