JP5021169B2 - 好中球依存性炎症性疾患の治療におけるキラルアリールケトン - Google Patents
好中球依存性炎症性疾患の治療におけるキラルアリールケトン Download PDFInfo
- Publication number
- JP5021169B2 JP5021169B2 JP2004558041A JP2004558041A JP5021169B2 JP 5021169 B2 JP5021169 B2 JP 5021169B2 JP 2004558041 A JP2004558041 A JP 2004558041A JP 2004558041 A JP2004558041 A JP 2004558041A JP 5021169 B2 JP5021169 B2 JP 5021169B2
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- Prior art keywords
- phenyl
- pharmaceutical composition
- formula
- isobutyl
- residue
- Prior art date
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- Expired - Fee Related
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/18—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by doubly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/24—Sulfones; Sulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/562—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
- C07C45/676—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton by elimination of carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/213—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/213—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C49/215—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4056—Esters of arylalkanephosphonic acids
- C07F9/4059—Compounds containing the structure (RY)2P(=X)-(CH2)n-C(=O)-(CH2)m-Ar, (X, Y = O, S, Se; n>=1, m>=0)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biochemistry (AREA)
- Dermatology (AREA)
- Urology & Nephrology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Pulmonology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
- Indole Compounds (AREA)
- Pyridine Compounds (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02027453.6 | 2002-12-10 | ||
| EP02027453 | 2002-12-10 | ||
| PCT/EP2003/013946 WO2004052830A1 (en) | 2002-12-10 | 2003-12-09 | Chiral arylketones in the treatement of neutrophil-dependent inflammatory deseases |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006509022A JP2006509022A (ja) | 2006-03-16 |
| JP2006509022A5 JP2006509022A5 (https=) | 2007-03-01 |
| JP5021169B2 true JP5021169B2 (ja) | 2012-09-05 |
Family
ID=32479711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004558041A Expired - Fee Related JP5021169B2 (ja) | 2002-12-10 | 2003-12-09 | 好中球依存性炎症性疾患の治療におけるキラルアリールケトン |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US20060247297A1 (https=) |
| EP (1) | EP1581474B1 (https=) |
| JP (1) | JP5021169B2 (https=) |
| CN (1) | CN100383110C (https=) |
| AT (1) | ATE406343T1 (https=) |
| AU (1) | AU2003289993B8 (https=) |
| CA (1) | CA2507765C (https=) |
| CY (1) | CY1108596T1 (https=) |
| DE (1) | DE60323264D1 (https=) |
| DK (1) | DK1581474T3 (https=) |
| ES (1) | ES2312834T3 (https=) |
| NO (1) | NO332223B1 (https=) |
| PT (1) | PT1581474E (https=) |
| RU (1) | RU2345759C2 (https=) |
| SI (1) | SI1581474T1 (https=) |
| WO (1) | WO2004052830A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2421213C1 (ru) * | 2010-02-24 | 2011-06-20 | Новосибирский институт органической химии им. Н.Н. Ворожцова Сибирского отделения Российской академии наук (НИОХ СО РАН) | Применение 2-гидрокси-3-метил-6-(1-метилэтенил)циклогекс-3-енона в качестве анальгезирующего средства |
| CN109928868A (zh) * | 2019-03-22 | 2019-06-25 | 河北科技大学 | 1,3-双(2,5-二甲基苯基)丙-2-酮的合成方法及其应用 |
| CN115894198B (zh) * | 2022-11-04 | 2024-05-17 | 浙江永太科技股份有限公司 | Qulipta的关键中间体1-(2,3,6-三氟苯基)丙烷-2-酮的制备方法 |
| KR102597093B1 (ko) * | 2023-06-07 | 2023-11-03 | 옙바이오 주식회사 | 줄기세포 노화 억제 신규 화합물 및 이의 약학적 용도 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL267501A (https=) * | 1960-07-26 | |||
| US3591350A (en) * | 1968-06-17 | 1971-07-06 | M & T Chemicals Inc | Novel plating process |
| SE385883B (sv) * | 1972-04-10 | 1976-07-26 | Ciba Geigy Ag | Forfarande for framstellning av nya pyridinkarbonsyraestrar |
| JPS5842851B2 (ja) | 1976-03-05 | 1983-09-22 | 三井東圧化学株式会社 | 2−(4′−アルキルフエニル)プロピオン酸の製造方法 |
| US4151172A (en) | 1977-08-11 | 1979-04-24 | E. R. Squibb & Sons, Inc. | Phosphonoacyl prolines and related compounds |
| JPS5697249A (en) | 1979-12-30 | 1981-08-05 | Ota Seiyaku Kk | Preparation of 2-arylalkane acid |
| JP2782359B2 (ja) | 1989-06-22 | 1998-07-30 | 日本石油化学株式会社 | 2―(4―イソブチルフエニル)―2―ブテン |
| AU644281B2 (en) | 1991-04-24 | 1993-12-02 | Sumitomo Pharmaceuticals Company, Limited | Novel thiazole derivatives |
| JPH05286902A (ja) * | 1992-04-10 | 1993-11-02 | Sumitomo Pharmaceut Co Ltd | α−クロロ−β−ケトエステル誘導体の製造方法 |
| IT1303249B1 (it) * | 1998-10-23 | 2000-11-06 | Dompe Spa | Alcune n-(2-aril-propionil)-solfonammidi e preparazionifarmaceutiche che le contengono. |
| IT1317826B1 (it) * | 2000-02-11 | 2003-07-15 | Dompe Spa | Ammidi, utili nell'inibizione della chemiotassi dei neutrofiliindotta da il-8. |
-
2003
- 2003-12-09 DK DK03782344T patent/DK1581474T3/da active
- 2003-12-09 AU AU2003289993A patent/AU2003289993B8/en not_active Ceased
- 2003-12-09 CA CA2507765A patent/CA2507765C/en not_active Expired - Fee Related
- 2003-12-09 ES ES03782344T patent/ES2312834T3/es not_active Expired - Lifetime
- 2003-12-09 EP EP03782344A patent/EP1581474B1/en not_active Expired - Lifetime
- 2003-12-09 WO PCT/EP2003/013946 patent/WO2004052830A1/en not_active Ceased
- 2003-12-09 CN CNB200380107685XA patent/CN100383110C/zh not_active Expired - Fee Related
- 2003-12-09 SI SI200331435T patent/SI1581474T1/sl unknown
- 2003-12-09 AT AT03782344T patent/ATE406343T1/de active
- 2003-12-09 JP JP2004558041A patent/JP5021169B2/ja not_active Expired - Fee Related
- 2003-12-09 RU RU2005121554/04A patent/RU2345759C2/ru not_active IP Right Cessation
- 2003-12-09 US US10/537,824 patent/US20060247297A1/en not_active Abandoned
- 2003-12-09 PT PT03782344T patent/PT1581474E/pt unknown
- 2003-12-09 DE DE60323264T patent/DE60323264D1/de not_active Expired - Lifetime
-
2005
- 2005-06-23 NO NO20053086A patent/NO332223B1/no not_active IP Right Cessation
-
2008
- 2008-11-26 CY CY20081101364T patent/CY1108596T1/el unknown
- 2008-12-03 US US12/327,767 patent/US9328057B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ATE406343T1 (de) | 2008-09-15 |
| US20090203652A1 (en) | 2009-08-13 |
| ES2312834T3 (es) | 2009-03-01 |
| EP1581474B1 (en) | 2008-08-27 |
| HK1085721A1 (zh) | 2006-09-01 |
| AU2003289993A1 (en) | 2004-06-30 |
| DK1581474T3 (da) | 2008-12-08 |
| PT1581474E (pt) | 2008-12-09 |
| RU2345759C2 (ru) | 2009-02-10 |
| AU2003289993B2 (en) | 2008-04-24 |
| CN1732145A (zh) | 2006-02-08 |
| RU2005121554A (ru) | 2006-01-20 |
| EP1581474A1 (en) | 2005-10-05 |
| CA2507765A1 (en) | 2004-06-24 |
| JP2006509022A (ja) | 2006-03-16 |
| WO2004052830A1 (en) | 2004-06-24 |
| NO332223B1 (no) | 2012-07-30 |
| NO20053086L (no) | 2005-06-23 |
| CA2507765C (en) | 2012-03-20 |
| US20060247297A1 (en) | 2006-11-02 |
| US9328057B2 (en) | 2016-05-03 |
| AU2003289993B8 (en) | 2008-05-08 |
| DE60323264D1 (de) | 2008-10-09 |
| CN100383110C (zh) | 2008-04-23 |
| SI1581474T1 (sl) | 2009-02-28 |
| CY1108596T1 (el) | 2014-04-09 |
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