ZA200109796B - 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
- ZA200109796B ZA200109796B ZA200109796A ZA200109796A ZA200109796B ZA 200109796 B ZA200109796 B ZA 200109796B ZA 200109796 A ZA200109796 A ZA 200109796A ZA 200109796 A ZA200109796 A ZA 200109796A ZA 200109796 B ZA200109796 B ZA 200109796B
- Authority
- ZA
- South Africa
- Prior art keywords
- compound
- formula
- alkyl
- group
- represent
- Prior art date
Links
- 206010003119 arrhythmia Diseases 0.000 title claims description 15
- 238000011282 treatment Methods 0.000 title claims description 13
- PTPQJKANBKHDPM-UHFFFAOYSA-N 3,7-diazabicyclo[3.3.1]nonane Chemical class C1NCC2CNCC1C2 PTPQJKANBKHDPM-UHFFFAOYSA-N 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 119
- 125000000217 alkyl group Chemical group 0.000 claims description 112
- 229910052799 carbon Inorganic materials 0.000 claims description 41
- 125000002947 alkylene group Chemical group 0.000 claims description 36
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 125000001424 substituent group Chemical group 0.000 claims description 26
- 125000004122 cyclic group Chemical group 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000002015 acyclic group Chemical group 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 13
- -1 linear or branched C Chemical group 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 230000006793 arrhythmia Effects 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 229910052717 sulfur Chemical group 0.000 claims description 5
- 239000011593 sulfur Chemical group 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 206010047281 Ventricular arrhythmia Diseases 0.000 claims description 2
- 230000001746 atrial effect Effects 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 238000011321 prophylaxis Methods 0.000 claims 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 4
- 125000003107 substituted aryl group Chemical group 0.000 claims 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 claims 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- 230000029936 alkylation Effects 0.000 claims 2
- 238000005804 alkylation reaction Methods 0.000 claims 2
- 238000009472 formulation Methods 0.000 claims 2
- 150000007524 organic acids Chemical class 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 108091008716 AR-B Proteins 0.000 claims 1
- 229910019567 Re Re Inorganic materials 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 239000003416 antiarrhythmic agent Substances 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 230000000747 cardiac effect Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 150000001204 N-oxides Chemical class 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
- 125000000842 isoxazolyl 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
- 125000004193 piperazinyl group Chemical group 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 230000002336 repolarization Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 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
- DLNAKYFPFYUBDR-HDICACEKSA-N (4-aminophenyl)-[(1s,5r)-7-benzyl-3,7-diazabicyclo[3.3.1]nonan-3-yl]methanone Chemical compound C1=CC(N)=CC=C1C(=O)N1C[C@@H](CN(CC=2C=CC=CC=2)C2)C[C@@H]2C1 DLNAKYFPFYUBDR-HDICACEKSA-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
- BKXNECYZQMFRLG-UHFFFAOYSA-N (4-imidazol-1-ylphenyl)-(7-propan-2-yl-3,7-diazabicyclo[3.3.1]nonan-3-yl)methanone Chemical compound C1N(C(C)C)CC(C2)CC1CN2C(=O)C(C=C1)=CC=C1N1C=CN=C1 BKXNECYZQMFRLG-UHFFFAOYSA-N 0.000 description 1
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 230000036982 action potential Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 229950005516 ambasilide Drugs 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
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants 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
- 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
- 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
- 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
- 238000009509 drug development Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000002541 furyl 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
- 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
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 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
- 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
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 239000012453 solvate Substances 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
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 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)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9902268A SE9902268D0 (sv) | 1999-06-16 | 1999-06-16 | Pharmaceutically active compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200109796B true ZA200109796B (en) | 2003-02-28 |
Family
ID=20416100
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200109796A ZA200109796B (en) | 1999-06-16 | 2001-11-28 | New bispidine compounds useful in the treatment of cardiac arrhythmias. |
Country Status (24)
| Country | Link |
|---|---|
| EP (1) | EP1192157A1 (no) |
| JP (1) | JP2003502329A (no) |
| KR (1) | KR20020010713A (no) |
| CN (1) | CN1144805C (no) |
| AR (1) | AR024577A1 (no) |
| AU (1) | AU761576B2 (no) |
| BR (1) | BR0011660A (no) |
| CA (1) | CA2375841A1 (no) |
| CZ (1) | CZ20014495A3 (no) |
| EE (1) | EE200100675A (no) |
| HK (1) | HK1045520A1 (no) |
| HU (1) | HUP0203959A3 (no) |
| IL (1) | IL146754A0 (no) |
| IS (1) | IS6201A (no) |
| MX (1) | MXPA01012919A (no) |
| NO (1) | NO20016117L (no) |
| NZ (1) | NZ516013A (no) |
| PL (1) | PL354032A1 (no) |
| RU (1) | RU2250903C2 (no) |
| SE (1) | SE9902268D0 (no) |
| SK (1) | SK18272001A3 (no) |
| TR (1) | TR200103663T2 (no) |
| WO (1) | WO2000077000A1 (no) |
| ZA (1) | ZA200109796B (no) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| SE0101327D0 (sv) | 2001-04-12 | 2001-04-12 | Astrazeneca Ab | New crystalline forms |
| TWI499418B (zh) * | 2009-05-21 | 2015-09-11 | Nerviano Medical Sciences Srl | 異喹啉－１（２ｈ）－酮衍生物 |
| EP2729444B1 (de) * | 2011-07-08 | 2017-08-23 | Bayer Intellectual Property GmbH | Verfahren zur herstellung von 2-amino-5-cyano-n,3-dimethylbenzamid |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| SE9704709D0 (sv) * | 1997-12-17 | 1997-12-17 | Astra Ab | Pharmaceutically active compounds |
-
1999
- 1999-06-16 SE SE9902268A patent/SE9902268D0/xx unknown
-
2000
- 2000-06-15 EE EEP200100675A patent/EE200100675A/xx unknown
- 2000-06-15 WO PCT/SE2000/001254 patent/WO2000077000A1/en not_active Application Discontinuation
- 2000-06-15 IL IL14675400A patent/IL146754A0/xx unknown
- 2000-06-15 HU HU0203959A patent/HUP0203959A3/hu unknown
- 2000-06-15 BR BR0011660-2A patent/BR0011660A/pt not_active IP Right Cessation
- 2000-06-15 JP JP2001503858A patent/JP2003502329A/ja active Pending
- 2000-06-15 CA CA002375841A patent/CA2375841A1/en not_active Abandoned
- 2000-06-15 SK SK1827-2001A patent/SK18272001A3/sk unknown
- 2000-06-15 EP EP00946589A patent/EP1192157A1/en not_active Withdrawn
- 2000-06-15 KR KR1020017016168A patent/KR20020010713A/ko not_active Application Discontinuation
- 2000-06-15 CZ CZ20014495A patent/CZ20014495A3/cs unknown
- 2000-06-15 MX MXPA01012919A patent/MXPA01012919A/es unknown
- 2000-06-15 RU RU2001132563/04A patent/RU2250903C2/ru not_active IP Right Cessation
- 2000-06-15 CN CNB008116962A patent/CN1144805C/zh not_active Expired - Fee Related
- 2000-06-15 AU AU60324/00A patent/AU761576B2/en not_active Ceased
- 2000-06-15 TR TR2001/03663T patent/TR200103663T2/xx unknown
- 2000-06-15 NZ NZ516013A patent/NZ516013A/xx unknown
- 2000-06-15 PL PL00354032A patent/PL354032A1/xx not_active Application Discontinuation
- 2000-06-16 AR ARP000103015A patent/AR024577A1/es not_active Application Discontinuation
-
2001
- 2001-11-28 ZA ZA200109796A patent/ZA200109796B/en unknown
- 2001-12-14 NO NO20016117A patent/NO20016117L/no not_active Application Discontinuation
- 2001-12-14 IS IS6201A patent/IS6201A/is unknown
-
2002
- 2002-09-27 HK HK02107165.2A patent/HK1045520A1/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL146754A0 (en) | 2002-07-25 |
| BR0011660A (pt) | 2002-03-26 |
| SK18272001A3 (sk) | 2002-12-03 |
| WO2000077000A9 (en) | 2003-06-19 |
| HK1045520A1 (zh) | 2002-11-29 |
| PL354032A1 (en) | 2003-12-15 |
| RU2250903C2 (ru) | 2005-04-27 |
| TR200103663T2 (tr) | 2002-05-21 |
| AU761576B2 (en) | 2003-06-05 |
| CN1370167A (zh) | 2002-09-18 |
| HUP0203959A2 (hu) | 2003-03-28 |
| KR20020010713A (ko) | 2002-02-04 |
| AU6032400A (en) | 2001-01-02 |
| JP2003502329A (ja) | 2003-01-21 |
| CZ20014495A3 (cs) | 2002-05-15 |
| NZ516013A (en) | 2003-06-30 |
| AR024577A1 (es) | 2002-10-16 |
| EE200100675A (et) | 2003-02-17 |
| HUP0203959A3 (en) | 2003-04-28 |
| CN1144805C (zh) | 2004-04-07 |
| EP1192157A1 (en) | 2002-04-03 |
| IS6201A (is) | 2001-12-14 |
| WO2000077000A1 (en) | 2000-12-21 |
| SE9902268D0 (sv) | 1999-06-16 |
| NO20016117L (no) | 2002-02-15 |
| CA2375841A1 (en) | 2000-12-21 |
| NO20016117D0 (no) | 2001-12-14 |
| MXPA01012919A (es) | 2002-07-30 |
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