NZ504909A - Bispidine derivatives useful as antiarrhythmic agents - Google Patents
Bispidine derivatives useful as antiarrhythmic agentsInfo
- Publication number
- NZ504909A NZ504909A NZ504909A NZ50490998A NZ504909A NZ 504909 A NZ504909 A NZ 504909A NZ 504909 A NZ504909 A NZ 504909A NZ 50490998 A NZ50490998 A NZ 50490998A NZ 504909 A NZ504909 A NZ 504909A
- Authority
- NZ
- New Zealand
- Prior art keywords
- compound
- formula
- mmol
- pct
- alkyl
- Prior art date
Links
- PTPQJKANBKHDPM-UHFFFAOYSA-N 3,7-diazabicyclo[3.3.1]nonane Chemical class C1NCC2CNCC1C2 PTPQJKANBKHDPM-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 239000003416 antiarrhythmic agent Substances 0.000 title description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 361
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 48
- 206010003119 arrhythmia Diseases 0.000 claims abstract description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 21
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 16
- 230000006793 arrhythmia Effects 0.000 claims abstract description 16
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 14
- 238000011282 treatment Methods 0.000 claims abstract description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000005037 alkyl phenyl group Chemical group 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 6
- 238000011321 prophylaxis Methods 0.000 claims abstract description 6
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 2
- 235000011468 Albizia julibrissin Nutrition 0.000 claims description 115
- 241001070944 Mimosa Species 0.000 claims description 115
- 238000000034 method Methods 0.000 claims description 104
- 238000006243 chemical reaction Methods 0.000 claims description 82
- 238000005481 NMR spectroscopy Methods 0.000 claims description 49
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 30
- -1 ammo Chemical group 0.000 claims description 25
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 24
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 11
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 11
- 230000009467 reduction Effects 0.000 claims description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 230000001746 atrial effect Effects 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 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 description 4
- 206010047281 Ventricular arrhythmia Diseases 0.000 claims description 3
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 claims 2
- BAWFJGJZGIEFAR-NNYOXOHSSA-N NAD zwitterion Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 BAWFJGJZGIEFAR-NNYOXOHSSA-N 0.000 claims 1
- ACFIXJIJDZMPPO-NNYOXOHSSA-N NADPH Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](OP(O)(O)=O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 ACFIXJIJDZMPPO-NNYOXOHSSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000004949 mass spectrometry Methods 0.000 claims 1
- 229950006238 nadide Drugs 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 238000004809 thin layer chromatography Methods 0.000 claims 1
- 101100240522 Caenorhabditis elegans nhr-18 gene Proteins 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 100
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 98
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 73
- 239000011541 reaction mixture Substances 0.000 description 60
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 52
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical class CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 52
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 45
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 38
- 238000004440 column chromatography Methods 0.000 description 38
- 239000000203 mixture Substances 0.000 description 37
- 101150041968 CDC13 gene Proteins 0.000 description 36
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 32
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 239000002904 solvent Substances 0.000 description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 239000010410 layer Substances 0.000 description 26
- 239000007787 solid Substances 0.000 description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- 235000019439 ethyl acetate Nutrition 0.000 description 22
- 229910000027 potassium carbonate Inorganic materials 0.000 description 22
- 239000012044 organic layer Substances 0.000 description 21
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 20
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- 239000003921 oil Substances 0.000 description 17
- 235000019198 oils Nutrition 0.000 description 17
- 239000000706 filtrate Substances 0.000 description 16
- 238000012360 testing method Methods 0.000 description 16
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 15
- 230000000694 effects Effects 0.000 description 15
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 15
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- 230000015572 biosynthetic process Effects 0.000 description 13
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
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- DMUXSGAKEXSNGN-UHFFFAOYSA-N 2-ethyloctanoic acid Chemical compound CCCCCCC(CC)C(O)=O DMUXSGAKEXSNGN-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 8
- 239000002585 base Substances 0.000 description 8
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- 229910002027 silica gel Inorganic materials 0.000 description 8
- 239000012267 brine Substances 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- CVNOWLNNPYYEOH-UHFFFAOYSA-N 4-cyanophenol Chemical compound OC1=CC=C(C#N)C=C1 CVNOWLNNPYYEOH-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 125000005233 alkylalcohol group Chemical group 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 5
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- ICGLPKIVTVWCFT-UHFFFAOYSA-N 4-methylbenzenesulfonohydrazide Chemical compound CC1=CC=C(S(=O)(=O)NN)C=C1 ICGLPKIVTVWCFT-UHFFFAOYSA-N 0.000 description 4
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- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
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- UXOFXTUCXRNLFA-UHFFFAOYSA-N phenyl-(7-propan-2-yl-3,7-diazabicyclo[3.3.1]nonan-3-yl)methanone Chemical compound C1N(C(C)C)CC(C2)CC1CN2C(=O)C1=CC=CC=C1 UXOFXTUCXRNLFA-UHFFFAOYSA-N 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- ASUAYTHWZCLXAN-UHFFFAOYSA-N prenol Chemical compound CC(C)=CCO ASUAYTHWZCLXAN-UHFFFAOYSA-N 0.000 description 1
- CAEWJEXPFKNBQL-UHFFFAOYSA-N prop-2-enyl carbonochloridate Chemical compound ClC(=O)OCC=C CAEWJEXPFKNBQL-UHFFFAOYSA-N 0.000 description 1
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
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- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
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- CTIRHWCPXYGDGF-HDICACEKSA-N tedisamil Chemical compound [H][C@]12CN(CC3CC3)C[C@]([H])(CN(CC3CC3)C1)C21CCCC1 CTIRHWCPXYGDGF-HDICACEKSA-N 0.000 description 1
- 229960002926 tedisamil Drugs 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9704709A SE9704709D0 (sv) | 1997-12-17 | 1997-12-17 | Pharmaceutically active compounds |
| PCT/SE1998/002276 WO1999031100A1 (en) | 1997-12-17 | 1998-12-10 | Novel bispidine antiarrhythmic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ504909A true NZ504909A (en) | 2001-11-30 |
Family
ID=20409426
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ504909A NZ504909A (en) | 1997-12-17 | 1998-12-10 | Bispidine derivatives useful as antiarrhythmic agents |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US6291475B1 (enExample) |
| EP (1) | EP1047695B1 (enExample) |
| JP (1) | JP2002508375A (enExample) |
| KR (1) | KR20010024723A (enExample) |
| CN (1) | CN1284956A (enExample) |
| AR (1) | AR017217A1 (enExample) |
| AT (1) | ATE261964T1 (enExample) |
| AU (1) | AU1795399A (enExample) |
| BR (1) | BR9813668A (enExample) |
| CA (1) | CA2314490A1 (enExample) |
| DE (1) | DE69822513T2 (enExample) |
| DK (1) | DK1047695T3 (enExample) |
| EE (1) | EE200000365A (enExample) |
| ES (1) | ES2216337T3 (enExample) |
| HU (1) | HUP0102307A3 (enExample) |
| ID (1) | ID24638A (enExample) |
| IL (1) | IL136374A0 (enExample) |
| IS (1) | IS5522A (enExample) |
| NO (1) | NO20003137L (enExample) |
| NZ (1) | NZ504909A (enExample) |
| PL (1) | PL341388A1 (enExample) |
| PT (1) | PT1047695E (enExample) |
| SE (1) | SE9704709D0 (enExample) |
| SI (1) | SI1047695T1 (enExample) |
| SK (1) | SK7812000A3 (enExample) |
| TR (1) | TR200001757T2 (enExample) |
| WO (1) | WO1999031100A1 (enExample) |
| ZA (1) | ZA9811130B (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9803517D0 (sv) * | 1998-10-15 | 1998-10-15 | Astra Ab | Pharmaceutical preparation |
| TWI229674B (en) | 1998-12-04 | 2005-03-21 | Astra Pharma Prod | Novel triazolo[4,5-d]pyrimidine compounds, pharmaceutical composition containing the same, their process for preparation and uses |
| SE9902269D0 (sv) * | 1999-06-16 | 1999-06-16 | Astra Ab | Pharmaceutically active compounds |
| US20040229900A1 (en) * | 1999-06-16 | 2004-11-18 | Astrazeneca Ab | Bispidine compounds useful in the treatment of cardiac arrythmias |
| SE9902271D0 (sv) * | 1999-06-16 | 1999-06-16 | Astra Ab | Pharmaceutically active compounds |
| SE9902270D0 (sv) * | 1999-06-16 | 1999-06-16 | Astra Ab | Pharmaceutically active compounds |
| US20050004113A1 (en) * | 1999-06-16 | 2005-01-06 | Astrazeneca Ab | New bispidine compounds useful in the treatment of cardiac arrhythmias |
| SE9902268D0 (sv) * | 1999-06-16 | 1999-06-16 | Astra Ab | Pharmaceutically active compounds |
| US7038054B1 (en) * | 1999-09-03 | 2006-05-02 | Pharmacopeia Drug Discovery, Inc. | Diazabicyclononane scaffold for combinatorial synthesis |
| SE9903759D0 (sv) * | 1999-10-18 | 1999-10-18 | Astra Ab | Pharmaceutically active compounds |
| EP1274710B1 (en) | 1999-12-14 | 2005-02-23 | NeuroSearch A/S | Novel heteroaryl-diazabicycloalkanes |
| SE9904765D0 (sv) | 1999-12-23 | 1999-12-23 | Astra Ab | Pharmaceutically-useful compounds |
| AR030302A1 (es) * | 2000-07-07 | 2003-08-20 | Astrazeneca Ab | Compuestos de bispidina, formulacion farmaceutica, uso para la fabricacion de medicamentos, proceso para la preparacion de estos compuestos y compuestos intermediarios |
| SE0002603D0 (sv) * | 2000-07-07 | 2000-07-07 | Astrazeneca Ab | New compounds |
| US6808924B1 (en) | 2000-07-11 | 2004-10-26 | Claudia Lanari | Mouse mammary tumor lines expressing estrogen and progesterone receptors |
| AR030756A1 (es) | 2000-10-02 | 2003-09-03 | Astrazeneca Ab | Compuesto de oxabispidina util en el tratamiento de arritmias cardiacas |
| SE0003795D0 (sv) | 2000-10-20 | 2000-10-20 | Astrazeneca Ab | Pharmaceutically useful compounds |
| SE0100326D0 (sv) | 2001-02-02 | 2001-02-02 | Astrazeneca Ab | New compounds |
| TWI259836B (en) * | 2001-04-12 | 2006-08-11 | Astrazeneca Ab | Modified release formulation suitable for antiarrhythmic compounds |
| SE0101329D0 (sv) * | 2001-04-12 | 2001-04-12 | Astrazeneca Ab | Pharmaceutical formulation |
| SE0101327D0 (sv) * | 2001-04-12 | 2001-04-12 | Astrazeneca Ab | New crystalline forms |
| SE0101324D0 (sv) * | 2001-04-12 | 2001-04-12 | Astrazeneca Ab | New process |
| DE60203007T2 (de) * | 2001-06-01 | 2005-07-07 | Neurosearch A/S | Heteroaryl-diazabicycloalkanderivaten als cns-modulatoren |
| TW200418468A (en) * | 2002-11-18 | 2004-10-01 | Solvay Pharm Gmbh | Liquid pharmaceutical formulations containing 3,7-diazabicyclo[3,3,1]nonane compounds and method of treatments relating to anti-arrhytmic events |
| US20050234091A1 (en) * | 2004-03-22 | 2005-10-20 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions and uses thereof |
| SE0401540D0 (sv) | 2004-06-15 | 2004-06-15 | Astrazeneca Ab | New compounds |
| 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 |
| CN102485725B (zh) * | 2010-12-02 | 2015-07-22 | 武汉药明康德新药开发有限公司 | 一种双氮杂环桥环类药物模板及其制备方法和应用 |
| WO2012172043A1 (en) | 2011-06-15 | 2012-12-20 | Laboratoire Biodim | Purine derivatives and their use as pharmaceuticals for prevention or treatment of bacterial infections |
| CN102875550B (zh) * | 2011-07-12 | 2016-01-06 | 常州合全药业有限公司 | 1,3,7-三取代-3,7-二氮杂双环[3,3,1]壬烷衍生物及制备方法 |
| CN104151277A (zh) * | 2014-06-30 | 2014-11-19 | 北京万全德众医药生物技术有限公司 | 盐酸决奈达隆一种氧化杂质的制备方法 |
| CN113683585B (zh) * | 2021-09-26 | 2023-07-11 | 齐鲁工业大学 | 一种含环氧基邻苯二甲腈单体的制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2428792A1 (de) | 1974-06-14 | 1976-01-02 | Knoll Ag | Neue antiarrhythmika |
| 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 |
| 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 |
| 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 |
| 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. |
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1997
- 1997-12-17 SE SE9704709A patent/SE9704709D0/xx unknown
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- 1998-12-10 CN CN98813573A patent/CN1284956A/zh active Pending
- 1998-12-10 EE EEP200000365A patent/EE200000365A/xx unknown
- 1998-12-10 PT PT98962796T patent/PT1047695E/pt unknown
- 1998-12-10 AT AT98962796T patent/ATE261964T1/de not_active IP Right Cessation
- 1998-12-10 DE DE69822513T patent/DE69822513T2/de not_active Expired - Fee Related
- 1998-12-10 EP EP98962796A patent/EP1047695B1/en not_active Expired - Lifetime
- 1998-12-10 DK DK98962796T patent/DK1047695T3/da active
- 1998-12-10 ID IDW20001081A patent/ID24638A/id unknown
- 1998-12-10 BR BR9813668-2A patent/BR9813668A/pt not_active IP Right Cessation
- 1998-12-10 CA CA002314490A patent/CA2314490A1/en not_active Abandoned
- 1998-12-10 SK SK781-2000A patent/SK7812000A3/sk unknown
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- 1998-12-10 JP JP2000539024A patent/JP2002508375A/ja active Pending
- 1998-12-10 PL PL98341388A patent/PL341388A1/xx unknown
- 1998-12-10 ES ES98962796T patent/ES2216337T3/es not_active Expired - Lifetime
- 1998-12-10 WO PCT/SE1998/002276 patent/WO1999031100A1/en not_active Ceased
- 1998-12-10 IL IL13637498A patent/IL136374A0/xx unknown
- 1998-12-10 US US09/214,756 patent/US6291475B1/en not_active Expired - Fee Related
- 1998-12-10 AU AU17953/99A patent/AU1795399A/en not_active Abandoned
- 1998-12-10 KR KR1020007006585A patent/KR20010024723A/ko not_active Withdrawn
- 1998-12-10 SI SI9830633T patent/SI1047695T1/xx unknown
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| US6291475B1 (en) | 2001-09-18 |
| NO20003137D0 (no) | 2000-06-16 |
| HUP0102307A2 (hu) | 2001-12-28 |
| PT1047695E (pt) | 2004-07-30 |
| SE9704709D0 (sv) | 1997-12-17 |
| AR017217A1 (es) | 2001-08-22 |
| CN1284956A (zh) | 2001-02-21 |
| WO1999031100A1 (en) | 1999-06-24 |
| AU1795399A (en) | 1999-07-05 |
| ID24638A (id) | 2000-07-27 |
| CA2314490A1 (en) | 1999-06-24 |
| ES2216337T3 (es) | 2004-10-16 |
| TR200001757T2 (tr) | 2000-09-21 |
| IL136374A0 (en) | 2001-06-14 |
| ATE261964T1 (de) | 2004-04-15 |
| EE200000365A (et) | 2001-10-15 |
| SK7812000A3 (en) | 2001-05-10 |
| SI1047695T1 (en) | 2004-08-31 |
| DE69822513D1 (de) | 2004-04-22 |
| HUP0102307A3 (en) | 2002-02-28 |
| DE69822513T2 (de) | 2005-03-10 |
| BR9813668A (pt) | 2000-10-17 |
| NO20003137L (no) | 2000-08-17 |
| EP1047695A1 (en) | 2000-11-02 |
| PL341388A1 (en) | 2001-04-09 |
| KR20010024723A (ko) | 2001-03-26 |
| ZA9811130B (en) | 1999-06-17 |
| EP1047695B1 (en) | 2004-03-17 |
| DK1047695T3 (da) | 2004-06-28 |
| JP2002508375A (ja) | 2002-03-19 |
| IS5522A (is) | 2000-06-02 |
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