ZA200109800B - New bispidine compounds useful in the treatment of cardiac arrhythmias. - Google Patents
New bispidine compounds useful in the treatment of cardiac arrhythmias. Download PDFInfo
- Publication number
- ZA200109800B ZA200109800B ZA200109800A ZA200109800A ZA200109800B ZA 200109800 B ZA200109800 B ZA 200109800B ZA 200109800 A ZA200109800 A ZA 200109800A ZA 200109800 A ZA200109800 A ZA 200109800A ZA 200109800 B ZA200109800 B ZA 200109800B
- Authority
- ZA
- South Africa
- Prior art keywords
- compound
- formula
- alkyl
- represent
- compounds
- Prior art date
Links
- 206010003119 arrhythmia Diseases 0.000 title claims description 16
- 238000011282 treatment Methods 0.000 title claims description 12
- PTPQJKANBKHDPM-UHFFFAOYSA-N 3,7-diazabicyclo[3.3.1]nonane Chemical class C1NCC2CNCC1C2 PTPQJKANBKHDPM-UHFFFAOYSA-N 0.000 title claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 211
- 125000000217 alkyl group Chemical group 0.000 claims description 92
- 229910052799 carbon Inorganic materials 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- 238000006243 chemical reaction Methods 0.000 claims description 39
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000002947 alkylene group Chemical group 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 230000009467 reduction Effects 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- -1 substituted Chemical class 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- 230000006793 arrhythmia Effects 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 229910052717 sulfur Chemical group 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000011593 sulfur Chemical group 0.000 claims description 7
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 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 5
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 claims description 2
- 206010047281 Ventricular arrhythmia Diseases 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 230000001746 atrial effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 238000011321 prophylaxis Methods 0.000 claims 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 238000009472 formulation Methods 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- 239000003960 organic solvent Substances 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
- 239000003638 chemical reducing agent Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003416 antiarrhythmic agent Substances 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 125000005233 alkylalcohol group Chemical group 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- ICGLPKIVTVWCFT-UHFFFAOYSA-N 4-methylbenzenesulfonohydrazide Chemical compound CC1=CC=C(S(=O)(=O)NN)C=C1 ICGLPKIVTVWCFT-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 230000000747 cardiac effect Effects 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000002336 repolarization Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
- DLNAKYFPFYUBDR-UHFFFAOYSA-N (4-aminophenyl)-(7-benzyl-3,7-diazabicyclo[3.3.1]nonan-3-yl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)N1CC(CN(CC=2C=CC=CC=2)C2)CC2C1 DLNAKYFPFYUBDR-UHFFFAOYSA-N 0.000 description 1
- FTABKDGWKNKXQJ-UHFFFAOYSA-N (4-chlorophenyl)-(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=C(Cl)C=C1 FTABKDGWKNKXQJ-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N Azide Chemical compound [N-]=[N+]=[N-] IVRMZWNICZWHMI-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
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-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
- 125000002015 acyclic group Chemical group 0.000 description 1
- 230000003288 anthiarrhythmic effect 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
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=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
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- PMCPYLGCPSNSLS-FOLVSLTJSA-N bisaramil Chemical compound CCN1C[C@@H]2CN(C)C[C@H](C1)[C@@H]2OC(=O)C1=CC=C(Cl)C=C1 PMCPYLGCPSNSLS-FOLVSLTJSA-N 0.000 description 1
- 229950007885 bisaramil Drugs 0.000 description 1
- 208000006218 bradycardia Diseases 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 230000011128 cardiac conduction Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000003016 chromanyl group Chemical group O1C(CCC2=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
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 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
- 125000000842 isoxazolyl group Chemical group 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
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 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
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 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
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 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
- 125000004076 pyridyl 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
- 150000003242 quaternary ammonium salts Chemical class 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 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
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- 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
- 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
- A61K31/439—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 the ring forming part of a bridged ring system, e.g. quinuclidine
-
- 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)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9902270A SE9902270D0 (sv) | 1999-06-16 | 1999-06-16 | Pharmaceutically active compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200109800B true ZA200109800B (en) | 2003-02-28 |
Family
ID=20416102
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200109800A ZA200109800B (en) | 1999-06-16 | 2001-11-28 | New bispidine compounds useful in the treatment of cardiac arrhythmias. |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US6887881B1 (es) |
| EP (1) | EP1192154B1 (es) |
| JP (1) | JP2003502328A (es) |
| KR (1) | KR20020010711A (es) |
| CN (1) | CN1187350C (es) |
| AR (1) | AR024393A1 (es) |
| AT (1) | ATE261965T1 (es) |
| AU (1) | AU762244B2 (es) |
| BR (1) | BR0011673A (es) |
| CA (1) | CA2384339A1 (es) |
| CZ (1) | CZ20014494A3 (es) |
| DE (1) | DE60009069T2 (es) |
| DK (1) | DK1192154T3 (es) |
| EE (1) | EE200100674A (es) |
| ES (1) | ES2216912T3 (es) |
| HK (1) | HK1045690A1 (es) |
| HU (1) | HUP0202929A3 (es) |
| IL (1) | IL146752A0 (es) |
| IS (1) | IS6199A (es) |
| MX (1) | MXPA01012925A (es) |
| NO (1) | NO20016127L (es) |
| NZ (1) | NZ516015A (es) |
| PL (1) | PL353794A1 (es) |
| PT (1) | PT1192154E (es) |
| SE (1) | SE9902270D0 (es) |
| SK (1) | SK18282001A3 (es) |
| TR (1) | TR200103659T2 (es) |
| WO (1) | WO2000076999A1 (es) |
| ZA (1) | ZA200109800B (es) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9903759D0 (sv) * | 1999-10-18 | 1999-10-18 | Astra Ab | Pharmaceutically active 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 |
| US20160214983A1 (en) | 2013-09-30 | 2016-07-28 | Council Of Scientific & Industrial Research | 3,7-diazabicyclo[3.3.1]nonane carboxamides as antithrombotic agents |
Family Cites Families (20)
| 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 |
| ATA237287A (de) | 1987-09-21 | 1993-02-15 | Vaillant Gmbh | Steuerung der temperatur des heizmediums einer umlaufheizung |
| 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 |
| DE4402931A1 (de) | 1994-02-01 | 1995-08-03 | Kali Chemie Pharma Gmbh | Neue 3-Phenylsulfonyl-3,7-diazabicyclo[3,3,1] nonan-Verbindungen enthaltende Arzneimittel |
| JP2000500454A (ja) | 1995-11-13 | 2000-01-18 | スミスクライン・ビーチャム・コーポレイション | 血液調節化合物 |
| SE9602263D0 (sv) * | 1996-06-07 | 1996-06-07 | Astra Ab | New amino acid derivatives |
| SE9704709D0 (sv) * | 1997-12-17 | 1997-12-17 | Astra Ab | Pharmaceutically active compounds |
| SE9803517D0 (sv) * | 1998-10-15 | 1998-10-15 | Astra Ab | Pharmaceutical preparation |
| GB9823103D0 (en) * | 1998-10-23 | 1998-12-16 | Pfizer Ltd | Pharmaceutically active compounds |
| PL350907A1 (en) | 1999-04-09 | 2003-02-10 | Astrazeneca Ab | Adamantane derivatives |
| SE9901875D0 (sv) | 1999-05-25 | 1999-05-25 | Astra Pharma Prod | Novel compounds |
| SE9902271D0 (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 |
| SE9903759D0 (sv) * | 1999-10-18 | 1999-10-18 | Astra Ab | Pharmaceutically active compounds |
| SE0002603D0 (sv) * | 2000-07-07 | 2000-07-07 | Astrazeneca Ab | New compounds |
-
1999
- 1999-06-16 SE SE9902270A patent/SE9902270D0/xx unknown
-
2000
- 2000-06-15 EP EP00944526A patent/EP1192154B1/en not_active Expired - Lifetime
- 2000-06-15 CN CNB008116008A patent/CN1187350C/zh not_active Expired - Fee Related
- 2000-06-15 MX MXPA01012925A patent/MXPA01012925A/es unknown
- 2000-06-15 EE EEP200100674A patent/EE200100674A/xx unknown
- 2000-06-15 KR KR1020017016165A patent/KR20020010711A/ko not_active Application Discontinuation
- 2000-06-15 CZ CZ20014494A patent/CZ20014494A3/cs unknown
- 2000-06-15 PL PL00353794A patent/PL353794A1/xx not_active Application Discontinuation
- 2000-06-15 TR TR2001/03659T patent/TR200103659T2/xx unknown
- 2000-06-15 NZ NZ516015A patent/NZ516015A/xx unknown
- 2000-06-15 WO PCT/SE2000/001253 patent/WO2000076999A1/en not_active Application Discontinuation
- 2000-06-15 ES ES00944526T patent/ES2216912T3/es not_active Expired - Lifetime
- 2000-06-15 PT PT00944526T patent/PT1192154E/pt unknown
- 2000-06-15 DE DE60009069T patent/DE60009069T2/de not_active Expired - Fee Related
- 2000-06-15 AU AU58611/00A patent/AU762244B2/en not_active Ceased
- 2000-06-15 SK SK1828-2001A patent/SK18282001A3/sk unknown
- 2000-06-15 JP JP2001503857A patent/JP2003502328A/ja active Pending
- 2000-06-15 IL IL14675200A patent/IL146752A0/xx unknown
- 2000-06-15 US US09/623,709 patent/US6887881B1/en not_active Expired - Fee Related
- 2000-06-15 DK DK00944526T patent/DK1192154T3/da active
- 2000-06-15 BR BR0011673-4A patent/BR0011673A/pt not_active IP Right Cessation
- 2000-06-15 HU HU0202929A patent/HUP0202929A3/hu unknown
- 2000-06-15 CA CA002384339A patent/CA2384339A1/en not_active Abandoned
- 2000-06-15 AT AT00944526T patent/ATE261965T1/de not_active IP Right Cessation
- 2000-06-16 AR ARP000103017A patent/AR024393A1/es unknown
-
2001
- 2001-11-28 ZA ZA200109800A patent/ZA200109800B/en unknown
- 2001-12-14 IS IS6199A patent/IS6199A/is unknown
- 2001-12-14 NO NO20016127A patent/NO20016127L/no not_active Application Discontinuation
-
2002
- 2002-09-26 HK HK02107115.3A patent/HK1045690A1/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2000076999A1 (en) | 2000-12-21 |
| KR20020010711A (ko) | 2002-02-04 |
| NO20016127D0 (no) | 2001-12-14 |
| ES2216912T3 (es) | 2004-11-01 |
| US6887881B1 (en) | 2005-05-03 |
| NZ516015A (en) | 2003-06-30 |
| TR200103659T2 (tr) | 2002-04-22 |
| EP1192154B1 (en) | 2004-03-17 |
| HK1045690A1 (zh) | 2002-12-06 |
| AR024393A1 (es) | 2002-10-02 |
| SK18282001A3 (sk) | 2002-12-03 |
| AU5861100A (en) | 2001-01-02 |
| DE60009069T2 (de) | 2004-10-14 |
| CZ20014494A3 (cs) | 2002-05-15 |
| EP1192154A1 (en) | 2002-04-03 |
| CN1187350C (zh) | 2005-02-02 |
| PL353794A1 (en) | 2003-12-01 |
| DK1192154T3 (da) | 2004-06-28 |
| MXPA01012925A (es) | 2002-07-30 |
| EE200100674A (et) | 2003-02-17 |
| JP2003502328A (ja) | 2003-01-21 |
| BR0011673A (pt) | 2002-03-12 |
| HUP0202929A3 (en) | 2003-04-28 |
| CN1370164A (zh) | 2002-09-18 |
| SE9902270D0 (sv) | 1999-06-16 |
| DE60009069D1 (de) | 2004-04-22 |
| AU762244B2 (en) | 2003-06-19 |
| IS6199A (is) | 2001-12-14 |
| PT1192154E (pt) | 2004-07-30 |
| ATE261965T1 (de) | 2004-04-15 |
| HUP0202929A2 (hu) | 2003-02-28 |
| CA2384339A1 (en) | 2000-12-21 |
| IL146752A0 (en) | 2002-07-25 |
| NO20016127L (no) | 2002-02-12 |
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