UA81919C2 - Производные бензимидазола, способ их получения и применение этих соединений в производстве разных медикаментов, и фармацевтическая композиция, содержащая такие соединения - Google Patents
Производные бензимидазола, способ их получения и применение этих соединений в производстве разных медикаментов, и фармацевтическая композиция, содержащая такие соединения Download PDFInfo
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- UA81919C2 UA81919C2 UAA200502658A UA2005002658A UA81919C2 UA 81919 C2 UA81919 C2 UA 81919C2 UA A200502658 A UAA200502658 A UA A200502658A UA 2005002658 A UA2005002658 A UA 2005002658A UA 81919 C2 UA81919 C2 UA 81919C2
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- Prior art keywords
- alkyl
- group
- substituted
- methyl
- bis
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 145
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 title claims description 21
- 239000003814 drug Substances 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title description 2
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title 1
- 208000002193 Pain Diseases 0.000 claims abstract description 33
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- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- -1 cyano, acetoxymethyl Chemical group 0.000 claims description 126
- 125000000217 alkyl group Chemical group 0.000 claims description 106
- 125000003118 aryl group Chemical group 0.000 claims description 40
- 125000001424 substituent group Chemical group 0.000 claims description 35
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 150000002367 halogens Chemical class 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 27
- 125000004429 atom Chemical group 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
- 241000605059 Bacteroidetes Species 0.000 claims description 11
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 241001465754 Metazoa Species 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
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- 125000005549 heteroarylene group Chemical group 0.000 claims description 7
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- 239000011734 sodium Substances 0.000 claims description 6
- 208000024827 Alzheimer disease Diseases 0.000 claims description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 229910052796 boron Inorganic materials 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 201000011510 cancer Diseases 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
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- 206010052779 Transplant rejections Diseases 0.000 claims description 3
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
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- 125000006224 2-tetrahydrofuranylmethyl group Chemical group [H]C([H])(*)C1([H])OC([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000005466 alkylenyl group Chemical group 0.000 claims 1
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- 238000003818 flash chromatography Methods 0.000 description 19
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 19
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- 239000002904 solvent Substances 0.000 description 19
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 230000000694 effects Effects 0.000 description 17
- 239000003480 eluent Substances 0.000 description 17
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
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- 239000012267 brine Substances 0.000 description 15
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/12—Radicals substituted by oxygen atoms
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Immunology (AREA)
- Psychology (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE0203070A SE0203070D0 (en) | 2002-10-16 | 2002-10-16 | Novel compounds |
PCT/SE2003/001604 WO2004035548A1 (en) | 2002-10-16 | 2003-10-15 | Novel compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
UA81919C2 true UA81919C2 (ru) | 2008-02-25 |
Family
ID=20289294
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
UAA200502658A UA81919C2 (ru) | 2002-10-16 | 2003-10-15 | Производные бензимидазола, способ их получения и применение этих соединений в производстве разных медикаментов, и фармацевтическая композиция, содержащая такие соединения |
Country Status (20)
Country | Link |
---|---|
US (1) | US7407968B2 (ru) |
EP (1) | EP1554254A1 (ru) |
JP (1) | JP2006505568A (ru) |
KR (1) | KR20050049551A (ru) |
CN (1) | CN100349874C (ru) |
AR (1) | AR041626A1 (ru) |
AU (1) | AU2003269775B2 (ru) |
BR (1) | BR0315320A (ru) |
CA (1) | CA2501418A1 (ru) |
IS (1) | IS7827A (ru) |
MX (1) | MXPA05003901A (ru) |
NO (1) | NO20052182L (ru) |
NZ (1) | NZ539079A (ru) |
PL (1) | PL376564A1 (ru) |
RU (1) | RU2323211C2 (ru) |
SE (1) | SE0203070D0 (ru) |
TW (1) | TWI285638B (ru) |
UA (1) | UA81919C2 (ru) |
WO (1) | WO2004035548A1 (ru) |
ZA (1) | ZA200502928B (ru) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE0101387D0 (sv) * | 2001-04-20 | 2001-04-20 | Astrazeneca Ab | Novel compounds |
SE0203070D0 (en) | 2002-10-16 | 2002-10-16 | Astrazeneca Ab | Novel compounds |
SE0301701D0 (sv) * | 2003-06-10 | 2003-06-10 | Astrazeneca Ab | Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof |
SE0301698D0 (sv) * | 2003-06-10 | 2003-06-10 | Astrazeneca Ab | Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof |
SE0301699D0 (sv) * | 2003-06-10 | 2003-06-10 | Astrazeneca Ab | Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof |
ES2318556T3 (es) * | 2004-11-02 | 2009-05-01 | Pfizer, Inc. | Derivados de sulfonil bencimidazol. |
WO2007091950A1 (en) * | 2006-02-07 | 2007-08-16 | Astrazeneca Ab | Benzimidazoles and imidazopyridines useful in the treatment of diseases or disorders associated with cannabinoid receptor 2 (cb2) such as pain |
PT2090570E (pt) | 2006-09-05 | 2011-12-29 | Kyowa Hakko Kirin Co Ltd | Derivado de imidazole |
EP2070927A4 (en) * | 2006-09-13 | 2010-10-13 | Kyowa Hakko Kirin Co Ltd | CONDENSED HETEROCYCLIC DERIVATIVE |
ES2439255T3 (es) * | 2007-06-21 | 2014-01-22 | Cara Therapeutics, Inc. | Imidazoheterociclos sustituidos |
WO2009025785A2 (en) * | 2007-08-21 | 2009-02-26 | Merck & Co., Inc. | Cb2 receptor ligands for the treatment of pain |
US8759535B2 (en) | 2010-02-18 | 2014-06-24 | High Point Pharmaceuticals, Llc | Substituted fused imidazole derivatives, pharmaceutical compositions, and methods of use thereof |
EP3263568B1 (en) | 2011-07-18 | 2021-08-25 | Merck Patent GmbH | Benzamides |
WO2014011949A2 (en) | 2012-07-13 | 2014-01-16 | The Cleveland Clinic Foundation | Neuroprotective cb2 receptor agonists |
WO2016089648A1 (en) | 2014-12-01 | 2016-06-09 | Vtv Therapeutics Llc | Bach 1 inhibitors in combination with nrf2 activators and pharmaceutical compositions thereof |
CN111658644B (zh) * | 2020-03-31 | 2021-05-14 | 中山大学 | 一种小分子stat3抑制剂wz-2-033及其在制备治疗乳腺癌和胃癌药物中的应用 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2945044A (en) * | 1957-07-12 | 1960-07-12 | Ciba Pharm Prod Inc | Certain 1-(diethyl-aminoethyl), 5-amino, 2-benzyl or substituted benzyl, benzimidazoles |
FR1481049A (fr) | 1965-11-25 | 1967-05-19 | France Ministre Des Armees | Nouveaux dialkylaminoalkyl-1 p-alkoxyphényl alkyl-2 benzimidazoles 5-substitués |
CA2036307C (en) * | 1990-03-08 | 2002-07-09 | Susan Jean Ward | 3-arylcarbonyl-1-aminoalkyl-1h-indole-containing antiglaucoma compositions and method |
FR2741621B1 (fr) * | 1995-11-23 | 1998-02-13 | Sanofi Sa | Nouveaux derives de pyrazole, procede pour leur preparation et compositions pharmaceutiques en contenant |
FR2789079B3 (fr) | 1999-02-01 | 2001-03-02 | Sanofi Synthelabo | Derive d'acide pyrazolecarboxylique, sa preparation, les compositions pharmaceutiques en contenant |
AUPR118000A0 (en) * | 2000-11-02 | 2000-11-23 | Amrad Operations Pty. Limited | Therapeutic molecules and methods |
EP1363632B1 (en) | 2001-01-29 | 2010-08-25 | The University of Connecticut | Receptor selective cannabimimetic aminoalkylindoles |
SE0101387D0 (sv) * | 2001-04-20 | 2001-04-20 | Astrazeneca Ab | Novel compounds |
AU2002347022A1 (en) * | 2001-12-20 | 2003-07-09 | Novo Nordisk A/S | Benzimidazols and indols as glucagon receptor antagonists/inverse agonisten |
SE0203070D0 (en) | 2002-10-16 | 2002-10-16 | Astrazeneca Ab | Novel compounds |
-
2002
- 2002-10-16 SE SE0203070A patent/SE0203070D0/xx unknown
-
2003
- 2003-10-09 TW TW092128115A patent/TWI285638B/zh not_active IP Right Cessation
- 2003-10-15 EP EP03751705A patent/EP1554254A1/en not_active Withdrawn
- 2003-10-15 JP JP2004545139A patent/JP2006505568A/ja active Pending
- 2003-10-15 AR ARP030103753A patent/AR041626A1/es unknown
- 2003-10-15 BR BR0315320-7A patent/BR0315320A/pt not_active IP Right Cessation
- 2003-10-15 MX MXPA05003901A patent/MXPA05003901A/es not_active Application Discontinuation
- 2003-10-15 NZ NZ539079A patent/NZ539079A/en unknown
- 2003-10-15 PL PL376564A patent/PL376564A1/pl not_active Application Discontinuation
- 2003-10-15 WO PCT/SE2003/001604 patent/WO2004035548A1/en active IP Right Grant
- 2003-10-15 US US10/530,499 patent/US7407968B2/en not_active Expired - Fee Related
- 2003-10-15 AU AU2003269775A patent/AU2003269775B2/en not_active Ceased
- 2003-10-15 KR KR1020057006538A patent/KR20050049551A/ko not_active Application Discontinuation
- 2003-10-15 CN CNB2003801059214A patent/CN100349874C/zh not_active Expired - Fee Related
- 2003-10-15 CA CA002501418A patent/CA2501418A1/en not_active Abandoned
- 2003-10-15 RU RU2005109156/04A patent/RU2323211C2/ru not_active IP Right Cessation
- 2003-10-15 UA UAA200502658A patent/UA81919C2/ru unknown
-
2005
- 2005-04-11 ZA ZA200502928A patent/ZA200502928B/en unknown
- 2005-04-27 IS IS7827A patent/IS7827A/is unknown
- 2005-05-03 NO NO20052182A patent/NO20052182L/no not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
JP2006505568A (ja) | 2006-02-16 |
EP1554254A1 (en) | 2005-07-20 |
NO20052182L (no) | 2005-05-03 |
SE0203070D0 (en) | 2002-10-16 |
NZ539079A (en) | 2007-11-30 |
ZA200502928B (en) | 2006-02-22 |
MXPA05003901A (es) | 2005-06-22 |
RU2005109156A (ru) | 2006-01-20 |
CA2501418A1 (en) | 2004-04-29 |
US20070105893A1 (en) | 2007-05-10 |
PL376564A1 (pl) | 2006-01-09 |
AU2003269775A1 (en) | 2004-05-04 |
TW200410944A (en) | 2004-07-01 |
IS7827A (is) | 2005-04-27 |
CN100349874C (zh) | 2007-11-21 |
AR041626A1 (es) | 2005-05-26 |
CN1726194A (zh) | 2006-01-25 |
KR20050049551A (ko) | 2005-05-25 |
AU2003269775B2 (en) | 2007-05-03 |
BR0315320A (pt) | 2005-08-16 |
US7407968B2 (en) | 2008-08-05 |
TWI285638B (en) | 2007-08-21 |
WO2004035548A1 (en) | 2004-04-29 |
RU2323211C2 (ru) | 2008-04-27 |
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