NZ523540A - New bispidine compounds and their use in the treatment of cardiac arrhythmias - Google Patents
New bispidine compounds and their use in the treatment of cardiac arrhythmiasInfo
- Publication number
- NZ523540A NZ523540A NZ523540A NZ52354001A NZ523540A NZ 523540 A NZ523540 A NZ 523540A NZ 523540 A NZ523540 A NZ 523540A NZ 52354001 A NZ52354001 A NZ 52354001A NZ 523540 A NZ523540 A NZ 523540A
- Authority
- NZ
- New Zealand
- Prior art keywords
- formula
- compound
- alkyl
- optionally substituted
- represent
- Prior art date
Links
- 238000011282 treatment Methods 0.000 title claims abstract description 17
- 206010003119 arrhythmia Diseases 0.000 title claims description 24
- PTPQJKANBKHDPM-UHFFFAOYSA-N 3,7-diazabicyclo[3.3.1]nonane Chemical class C1NCC2CNCC1C2 PTPQJKANBKHDPM-UHFFFAOYSA-N 0.000 title claims description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 392
- 238000000034 method Methods 0.000 claims abstract description 38
- 230000008569 process Effects 0.000 claims abstract description 7
- 238000011321 prophylaxis Methods 0.000 claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims description 241
- 125000002947 alkylene group Chemical group 0.000 claims description 84
- 125000003118 aryl group Chemical group 0.000 claims description 80
- 238000006243 chemical reaction Methods 0.000 claims description 78
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 75
- -1 -OH Chemical group 0.000 claims description 68
- 125000001424 substituent group Chemical group 0.000 claims description 66
- 125000005843 halogen group Chemical group 0.000 claims description 58
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 52
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 239000012634 fragment Substances 0.000 claims description 29
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
- 101100095563 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) SEO1 gene Proteins 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 20
- 230000009467 reduction Effects 0.000 claims description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 14
- 230000006793 arrhythmia Effects 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 238000005481 NMR spectroscopy Methods 0.000 claims description 11
- 150000001721 carbon Chemical group 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 10
- 101100070530 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) het-6 gene Chemical group 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 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 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 239000007800 oxidant agent Substances 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- 101000983970 Conus catus Alpha-conotoxin CIB Proteins 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000002671 adjuvant Substances 0.000 claims description 4
- 230000001746 atrial effect Effects 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 229910052717 sulfur Chemical group 0.000 claims description 4
- 239000011593 sulfur Chemical group 0.000 claims description 4
- IVRMZWNICZWHMI-UHFFFAOYSA-N Azide Chemical compound [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims description 3
- 206010047281 Ventricular arrhythmia Diseases 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 238000010511 deprotection reaction Methods 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 2
- 238000004809 thin layer chromatography Methods 0.000 claims description 2
- 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 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 238000004949 mass spectrometry Methods 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 229940037201 oris Drugs 0.000 claims 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 219
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 34
- 239000000203 mixture Substances 0.000 description 34
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000003960 organic solvent Substances 0.000 description 24
- 239000002904 solvent Substances 0.000 description 23
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- 238000010992 reflux Methods 0.000 description 19
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 17
- 238000012360 testing method Methods 0.000 description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
- 239000002585 base Substances 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- 229910000027 potassium carbonate Inorganic materials 0.000 description 13
- 229910001868 water Inorganic materials 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 235000019439 ethyl acetate Nutrition 0.000 description 12
- 238000002474 experimental method Methods 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 125000006239 protecting group Chemical group 0.000 description 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
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- 239000003054 catalyst Substances 0.000 description 9
- 210000004027 cell Anatomy 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
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- 239000000243 solution Substances 0.000 description 9
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- 125000004429 atom Chemical group 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 8
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 8
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 7
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
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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
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- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 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
- 238000010998 test method Methods 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 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
- A61P9/06—Antiarrhythmics
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0002603A SE0002603D0 (sv) | 2000-07-07 | 2000-07-07 | New compounds |
| SE0002788A SE0002788D0 (sv) | 2000-07-27 | 2000-07-27 | New compounds |
| PCT/SE2001/001544 WO2002004446A1 (en) | 2000-07-07 | 2001-07-04 | New bispidine compounds and their use in the treatment of cardiac arrhythmias |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ523540A true NZ523540A (en) | 2004-07-30 |
Family
ID=26655177
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ523540A NZ523540A (en) | 2000-07-07 | 2001-07-04 | New bispidine compounds and their use in the treatment of cardiac arrhythmias |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP1301510A1 (cs) |
| JP (1) | JP2004502772A (cs) |
| KR (1) | KR20030014426A (cs) |
| CN (1) | CN1440407A (cs) |
| AR (1) | AR030302A1 (cs) |
| AU (1) | AU2001271161A1 (cs) |
| BR (1) | BR0112267A (cs) |
| CA (1) | CA2412848A1 (cs) |
| CZ (1) | CZ200332A3 (cs) |
| EE (1) | EE200300013A (cs) |
| HU (1) | HUP0301304A2 (cs) |
| IL (1) | IL153485A0 (cs) |
| IS (1) | IS6660A (cs) |
| MX (1) | MXPA02012942A (cs) |
| NO (1) | NO20030057L (cs) |
| NZ (1) | NZ523540A (cs) |
| PL (1) | PL360474A1 (cs) |
| RU (1) | RU2002134450A (cs) |
| SK (1) | SK42003A3 (cs) |
| WO (1) | WO2002004446A1 (cs) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004103991A1 (en) * | 2003-05-20 | 2004-12-02 | 'chemical Diversity Research Institute', Ltd. | 2-substituted piperidines, focused library and a pharmaceutical compound |
| US7399765B2 (en) | 2003-09-19 | 2008-07-15 | Abbott Laboratories | Substituted diazabicycloalkane derivatives |
| SE0302775D0 (sv) * | 2003-10-20 | 2003-10-20 | Astrazeneca Ab | Chemical compound and assay |
| RU2472793C1 (ru) * | 2011-07-20 | 2013-01-20 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Московский государственный университет тонких химических технологий имени М.В. Ломоносова" (МИТХТ им.М.В.Ломоносова) | 1,5-бис[(трет-бутиламино)метил]-n,n'-ди-трет-бутилбиспидин-9-она и способ его получения |
| CN116444556A (zh) * | 2023-03-24 | 2023-07-18 | 苏州威迈芯材半导体有限公司 | 一种有机硅中间体4-苯甲腈基氧烷基三烷氧基硅烷的制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| DE4402933A1 (de) * | 1994-02-01 | 1995-08-03 | Kali Chemie Pharma Gmbh | Neue 3-Benzoyl-3,7-diazabicyclo[3,3,1] nonan-Verbindungen enthaltende Arzneimittel |
| SE9704709D0 (sv) * | 1997-12-17 | 1997-12-17 | Astra Ab | Pharmaceutically active compounds |
| SE9902271D0 (sv) * | 1999-06-16 | 1999-06-16 | Astra Ab | Pharmaceutically active compounds |
| SE9902268D0 (sv) * | 1999-06-16 | 1999-06-16 | Astra Ab | Pharmaceutically active compounds |
| SE9902269D0 (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 |
-
2001
- 2001-06-28 AR ARP010103085A patent/AR030302A1/es not_active Application Discontinuation
- 2001-07-04 EE EEP200300013A patent/EE200300013A/xx unknown
- 2001-07-04 MX MXPA02012942A patent/MXPA02012942A/es unknown
- 2001-07-04 CZ CZ200332A patent/CZ200332A3/cs unknown
- 2001-07-04 SK SK4-2003A patent/SK42003A3/sk unknown
- 2001-07-04 BR BR0112267-3A patent/BR0112267A/pt not_active IP Right Cessation
- 2001-07-04 KR KR10-2003-7000248A patent/KR20030014426A/ko not_active Withdrawn
- 2001-07-04 NZ NZ523540A patent/NZ523540A/en unknown
- 2001-07-04 JP JP2002509311A patent/JP2004502772A/ja active Pending
- 2001-07-04 EP EP01950132A patent/EP1301510A1/en not_active Withdrawn
- 2001-07-04 CN CN01812475A patent/CN1440407A/zh active Pending
- 2001-07-04 CA CA002412848A patent/CA2412848A1/en not_active Abandoned
- 2001-07-04 AU AU2001271161A patent/AU2001271161A1/en not_active Abandoned
- 2001-07-04 HU HU0301304A patent/HUP0301304A2/hu unknown
- 2001-07-04 PL PL36047401A patent/PL360474A1/xx not_active Application Discontinuation
- 2001-07-04 IL IL15348501A patent/IL153485A0/xx unknown
- 2001-07-04 RU RU2002134450/04A patent/RU2002134450A/ru not_active Application Discontinuation
- 2001-07-04 WO PCT/SE2001/001544 patent/WO2002004446A1/en not_active Ceased
-
2002
- 2002-12-19 IS IS6660A patent/IS6660A/is unknown
-
2003
- 2003-01-06 NO NO20030057A patent/NO20030057L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| KR20030014426A (ko) | 2003-02-17 |
| WO2002004446A1 (en) | 2002-01-17 |
| CA2412848A1 (en) | 2002-01-17 |
| EE200300013A (et) | 2004-10-15 |
| JP2004502772A (ja) | 2004-01-29 |
| AU2001271161A1 (en) | 2002-01-21 |
| CZ200332A3 (cs) | 2003-04-16 |
| HUP0301304A2 (hu) | 2003-08-28 |
| IL153485A0 (en) | 2003-07-06 |
| NO20030057D0 (no) | 2003-01-06 |
| MXPA02012942A (es) | 2003-10-06 |
| EP1301510A1 (en) | 2003-04-16 |
| BR0112267A (pt) | 2003-05-20 |
| PL360474A1 (en) | 2004-09-06 |
| CN1440407A (zh) | 2003-09-03 |
| SK42003A3 (en) | 2003-07-01 |
| AR030302A1 (es) | 2003-08-20 |
| RU2002134450A (ru) | 2004-07-10 |
| IS6660A (is) | 2002-12-19 |
| NO20030057L (no) | 2003-01-31 |
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