ZA200109800B - New bispidine compounds useful in the treatment of cardiac arrhythmias. - Google Patents

New bispidine compounds useful in the treatment of cardiac arrhythmias. Download PDF

Info

Publication number: ZA200109800B
Authority: ZA; South Africa
Prior art keywords: compound; formula; alkyl; represent; compounds
Prior art date: 1999-06-16

Application number

ZA200109800A

Other languages

English (en)

Inventor

Annika Bjoere

Torbjoern Halvarsson

Bertil Samuelsson

Magnus Bjoersne

Kurt-Juergen Hoffmann

Gert Strandlund

Original Assignee

Astrazeneca Ab

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1999-06-16

Filing date

2001-11-28

Publication date

2003-02-28

2001-11-28 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2003-02-28 Publication of ZA200109800B publication Critical patent/ZA200109800B/en

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)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Hydrogenated Pyridines (AREA)

ZA200109800A 1999-06-16 2001-11-28 New bispidine compounds useful in the treatment of cardiac arrhythmias. ZA200109800B (en)

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 (fr)
EP (1)	EP1192154B1 (fr)
JP (1)	JP2003502328A (fr)
KR (1)	KR20020010711A (fr)
CN (1)	CN1187350C (fr)
AR (1)	AR024393A1 (fr)
AT (1)	ATE261965T1 (fr)
AU (1)	AU762244B2 (fr)
BR (1)	BR0011673A (fr)
CA (1)	CA2384339A1 (fr)
CZ (1)	CZ20014494A3 (fr)
DE (1)	DE60009069T2 (fr)
DK (1)	DK1192154T3 (fr)
EE (1)	EE200100674A (fr)
ES (1)	ES2216912T3 (fr)
HK (1)	HK1045690A1 (fr)
HU (1)	HUP0202929A3 (fr)
IL (1)	IL146752A0 (fr)
IS (1)	IS6199A (fr)
MX (1)	MXPA01012925A (fr)
NO (1)	NO20016127L (fr)
NZ (1)	NZ516015A (fr)
PL (1)	PL353794A1 (fr)
PT (1)	PT1192154E (fr)
SE (1)	SE9902270D0 (fr)
SK (1)	SK18282001A3 (fr)
TR (1)	TR200103659T2 (fr)
WO (1)	WO2000076999A1 (fr)
ZA (1)	ZA200109800B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE9903759D0 (sv) *	1999-10-18	1999-10-18	Astra Ab	Pharmaceutically active compounds
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1999
- 1999-06-16 SE SE9902270A patent/SE9902270D0/xx unknown
2000
- 2000-06-15 KR KR1020017016165A patent/KR20020010711A/ko not_active Withdrawn
- 2000-06-15 PL PL00353794A patent/PL353794A1/xx not_active Application Discontinuation
- 2000-06-15 EP EP00944526A patent/EP1192154B1/fr not_active Expired - Lifetime
- 2000-06-15 AT AT00944526T patent/ATE261965T1/de not_active IP Right Cessation
- 2000-06-15 PT PT00944526T patent/PT1192154E/pt unknown
- 2000-06-15 EE EEP200100674A patent/EE200100674A/xx unknown
- 2000-06-15 BR BR0011673-4A patent/BR0011673A/pt not_active IP Right Cessation
- 2000-06-15 JP JP2001503857A patent/JP2003502328A/ja active Pending
- 2000-06-15 WO PCT/SE2000/001253 patent/WO2000076999A1/fr not_active Ceased
- 2000-06-15 HU HU0202929A patent/HUP0202929A3/hu unknown
- 2000-06-15 CA CA002384339A patent/CA2384339A1/fr not_active Abandoned
- 2000-06-15 NZ NZ516015A patent/NZ516015A/xx unknown
- 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 AU AU58611/00A patent/AU762244B2/en not_active Ceased
- 2000-06-15 SK SK1828-2001A patent/SK18282001A3/sk unknown
- 2000-06-15 DE DE60009069T patent/DE60009069T2/de not_active Expired - Fee Related
- 2000-06-15 CZ CZ20014494A patent/CZ20014494A3/cs unknown
- 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 TR TR2001/03659T patent/TR200103659T2/xx unknown
- 2000-06-15 HK HK02107115.3A patent/HK1045690A1/zh unknown
- 2000-06-15 ES ES00944526T patent/ES2216912T3/es not_active Expired - Lifetime
- 2000-06-15 DK DK00944526T patent/DK1192154T3/da active
- 2000-06-16 AR ARP000103017A patent/AR024393A1/es unknown
2001
- 2001-11-28 ZA ZA200109800A patent/ZA200109800B/en unknown
- 2001-12-14 NO NO20016127A patent/NO20016127L/no not_active Application Discontinuation
- 2001-12-14 IS IS6199A patent/IS6199A/is unknown

Also Published As

Publication number	Publication date
DK1192154T3 (da)	2004-06-28
KR20020010711A (ko)	2002-02-04
MXPA01012925A (es)	2002-07-30
JP2003502328A (ja)	2003-01-21
AU5861100A (en)	2001-01-02
US6887881B1 (en)	2005-05-03
SE9902270D0 (sv)	1999-06-16
HUP0202929A3 (en)	2003-04-28
IL146752A0 (en)	2002-07-25
WO2000076999A1 (fr)	2000-12-21
BR0011673A (pt)	2002-03-12
CN1187350C (zh)	2005-02-02
AR024393A1 (es)	2002-10-02
PL353794A1 (en)	2003-12-01
DE60009069T2 (de)	2004-10-14
NO20016127L (no)	2002-02-12
DE60009069D1 (de)	2004-04-22
AU762244B2 (en)	2003-06-19
SK18282001A3 (sk)	2002-12-03
IS6199A (is)	2001-12-14
NZ516015A (en)	2003-06-30
NO20016127D0 (no)	2001-12-14
EP1192154B1 (fr)	2004-03-17
CA2384339A1 (fr)	2000-12-21
ES2216912T3 (es)	2004-11-01
TR200103659T2 (tr)	2002-04-22
EE200100674A (et)	2003-02-17
PT1192154E (pt)	2004-07-30
HK1045690A1 (zh)	2002-12-06
HUP0202929A2 (hu)	2003-02-28
ATE261965T1 (de)	2004-04-15
EP1192154A1 (fr)	2002-04-03
CN1370164A (zh)	2002-09-18
CZ20014494A3 (cs)	2002-05-15

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