CA2559888A1 - 2-(amino-substituted)-4-aryl pyramidines and related compounds useful for treating inflammatory diseases - Google Patents
2-(amino-substituted)-4-aryl pyramidines and related compounds useful for treating inflammatory diseases Download PDFInfo
- Publication number
- CA2559888A1 CA2559888A1 CA002559888A CA2559888A CA2559888A1 CA 2559888 A1 CA2559888 A1 CA 2559888A1 CA 002559888 A CA002559888 A CA 002559888A CA 2559888 A CA2559888 A CA 2559888A CA 2559888 A1 CA2559888 A1 CA 2559888A1
- Authority
- CA
- Canada
- Prior art keywords
- 4alkyl
- optionally substituted
- heteroaryl
- phenyl
- halo
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 title claims description 327
- 208000027866 inflammatory disease Diseases 0.000 title claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 65
- 102000001892 Protein Kinase C-theta Human genes 0.000 claims abstract description 30
- 108010015499 Protein Kinase C-theta Proteins 0.000 claims abstract description 30
- 230000002757 inflammatory effect Effects 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 615
- -1 1H-benzimidazol-1-yl Chemical group 0.000 claims description 119
- 125000005843 halogen group Chemical group 0.000 claims description 116
- 125000001072 heteroaryl group Chemical group 0.000 claims description 116
- 125000001931 aliphatic group Chemical group 0.000 claims description 106
- 125000000217 alkyl group Chemical group 0.000 claims description 96
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 80
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 73
- 229910052757 nitrogen Inorganic materials 0.000 claims description 72
- 125000003118 aryl group Chemical group 0.000 claims description 55
- 229910052739 hydrogen Inorganic materials 0.000 claims description 53
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 45
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
- 229910052760 oxygen Inorganic materials 0.000 claims description 38
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 34
- 125000004076 pyridyl group Chemical group 0.000 claims description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 125000003386 piperidinyl group Chemical group 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 31
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- 125000005842 heteroatom Chemical group 0.000 claims description 26
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- 238000012360 testing method Methods 0.000 description 1
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- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
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- 230000000699 topical effect Effects 0.000 description 1
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- 208000035408 type 1 diabetes mellitus 1 Diseases 0.000 description 1
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- 210000002700 urine Anatomy 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
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- 229910052720 vanadium Inorganic materials 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
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- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
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- 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
- A61P11/06—Antiasthmatics
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
- C07D401/10—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 aromatic 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
- C07D403/10—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 aromatic rings
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Dermatology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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| Application Number | Priority Date | Filing Date | Title |
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| US53489804P | 2004-01-08 | 2004-01-08 | |
| US60/534,898 | 2004-01-08 | ||
| PCT/US2005/000663 WO2005066139A2 (en) | 2004-01-08 | 2005-01-10 | 2-(amino-substituted)-4-aryl pyramidines and related compounds useful for treating inflammatory diseases |
Publications (1)
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| CA2559888A1 true CA2559888A1 (en) | 2005-07-21 |
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Family Applications (1)
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|---|---|---|---|
| CA002559888A Abandoned CA2559888A1 (en) | 2004-01-08 | 2005-01-10 | 2-(amino-substituted)-4-aryl pyramidines and related compounds useful for treating inflammatory diseases |
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| CY (1) | CY1109529T1 (enExample) |
| DE (1) | DE602005015677D1 (enExample) |
| DK (1) | DK1701944T3 (enExample) |
| ES (1) | ES2330863T3 (enExample) |
| HR (1) | HRP20090572T1 (enExample) |
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| RS (1) | RS51091B (enExample) |
| SI (1) | SI1701944T1 (enExample) |
| TW (1) | TW200533357A (enExample) |
| WO (1) | WO2005066139A2 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
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| TW200533357A (en) * | 2004-01-08 | 2005-10-16 | Millennium Pharm Inc | 2-(amino-substituted)-4-aryl pyrimidines and related compounds useful for treating inflammatory diseases |
| CN1989131A (zh) * | 2004-03-30 | 2007-06-27 | 希龙公司 | 取代的噻吩衍生物用作抗癌药 |
| GB0428250D0 (en) * | 2004-12-23 | 2005-01-26 | Novartis Ag | Organic compounds |
| US20080318929A1 (en) * | 2005-12-21 | 2008-12-25 | Barbosa Antonio J M | Pyrimidine Derivatives Useful as Inhibitors of Pkc-Theta |
| CA2644643C (en) * | 2006-03-22 | 2015-05-19 | Janssen Pharmaceutica N.V. | Inhibitors of the interaction between mdm2 and p53 |
| DK2430921T3 (en) * | 2007-04-03 | 2017-10-16 | Du Pont | SUBSTITUTED BENZEN FUNGICIDES |
| MX2010004740A (es) | 2007-10-30 | 2010-05-27 | Genentech Inc | Purificacion de anticuerpos por cromatografia de intercambio cationico. |
| WO2009107391A1 (ja) | 2008-02-27 | 2009-09-03 | 武田薬品工業株式会社 | ６員芳香環含有化合物 |
| EP2169665B1 (en) | 2008-09-25 | 2018-05-02 | LG Electronics Inc. | A method and an apparatus for processing a signal |
| WO2011083483A2 (en) * | 2010-01-11 | 2011-07-14 | Healor Ltd. | Method for treatment of inflammatory disease and disorder |
| CA2800936A1 (en) * | 2010-07-02 | 2012-01-05 | Ventana Medical Systems, Inc. | Hapten conjugates for target detection |
| ES2543050T3 (es) | 2011-02-28 | 2015-08-14 | Array Biopharma, Inc. | Inhibidores de serina/treonina quinasa |
| EP2739618B1 (en) | 2011-08-04 | 2015-09-16 | Array Biopharma, Inc. | Quinazoline compounds as serine/threonine kinase inhibitors |
| AR090220A1 (es) | 2012-03-01 | 2014-10-29 | Array Biopharma Inc | Inhibidores de serina/treonina cinasa |
| SMT201800608T1 (it) | 2012-04-24 | 2019-01-11 | Vertex Pharma | Inibitori di dna-pk |
| MX369989B (es) | 2012-08-27 | 2019-11-27 | Array Biopharma Inc | Inhibidores de serina/treonina cinasa para el tratamiento de enfermedades hiperproliferativas. |
| AU2014244555B2 (en) | 2013-03-12 | 2018-06-28 | Vertex Pharmaceuticals Incorporated | DNA-PK inhibitors |
| ES2851724T3 (es) | 2013-09-18 | 2021-09-08 | Epiaxis Therapeutics Pty Ltd | Modulación de células madre |
| HUE041877T2 (hu) | 2013-10-17 | 2019-06-28 | Vertex Pharma | (S)-N-Metil-8-(1-((2'-metil-[4,5'-bipirimidin]-6-il)amino)propán-2-il)kinolin-4-karboxamid kokristályai és deuterált származékai DNS-PK inhibitorokként |
| US10485772B2 (en) | 2014-08-25 | 2019-11-26 | EpiAxis Therapeutics Pty Ltd. | Compositions for modulating cancer stem cells and uses therefor |
| US11110108B2 (en) | 2016-09-27 | 2021-09-07 | Vertex Pharmaceuticals Incorporated | Method for treating cancer using a combination of DNA-damaging agents and DNA-PK inhibitors |
| EP4444423A1 (en) | 2021-12-06 | 2024-10-16 | Helmholtz-Zentrum Dresden - Rossendorf e.V. | 3-((3-([1,1'-biphenyl]-3-ylmethoxy)phenoxy)methyl)benzonitrile derivatives and the use thereof |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5698697A (en) | 1995-07-19 | 1997-12-16 | Mitsubishi Chemical Corporation | 2-cyanopiperazine and method of producing the same |
| AU1924699A (en) * | 1997-12-19 | 1999-07-12 | Smithkline Beecham Corporation | Compounds of heteroaryl substituted imidazole, their pharmaceutical compositionsand uses |
| KR20010041015A (ko) | 1998-02-17 | 2001-05-15 | 윌리엄 제이. 리플린 | 항바이러스성 피리미딘 유도체 |
| US7045519B2 (en) * | 1998-06-19 | 2006-05-16 | Chiron Corporation | Inhibitors of glycogen synthase kinase 3 |
| ATE274510T1 (de) * | 1998-06-19 | 2004-09-15 | Chiron Corp | Glycogen synthase kinase 3 inhibitoren |
| EE200100341A (et) * | 1998-12-24 | 2002-12-16 | Aventis Pharmaceuticals Products Inc. | Asendatud (aminoiminometüül- või aminometüül)bensoheteroarüülühendid, nende kasutamine ja farmatseutiline kompositsioon |
| US6492516B1 (en) * | 1999-05-14 | 2002-12-10 | Merck & Co., Inc. | Compounds having cytokine inhibitory activity |
| JP2003503354A (ja) | 1999-06-30 | 2003-01-28 | メルク エンド カムパニー インコーポレーテッド | Ｓｒｃキナーゼ阻害剤化合物 |
| AR032130A1 (es) * | 1999-08-13 | 2003-10-29 | Vertex Pharma | Un compuesto inhibidor de quinasas proteicas, una composicion farmaceutica que lo incluye, y un metodo para tratar afecciones con dicho compuesto |
| GB0003224D0 (en) * | 2000-02-11 | 2000-04-05 | Glaxo Group Ltd | Chemical compounds |
| US6869956B2 (en) | 2000-10-03 | 2005-03-22 | Bristol-Myers Squibb Company | Methods of treating inflammatory and immune diseases using inhibitors of IκB kinase (IKK) |
| AU1152702A (en) | 2000-10-12 | 2002-04-22 | Merck & Co Inc | Aza- and polyaza-naphthalenyl carboxamides useful as hiv integrase inhibitors |
| CA2441733A1 (en) * | 2001-03-29 | 2002-10-10 | Vertex Pharmaceuticals Incorporated | Inhibitors of c-jun n-terminal kinases (jnk) and other protein kinases |
| EP1389206B1 (en) * | 2001-04-13 | 2006-09-13 | Vertex Pharmaceuticals Incorporated | Inhibitors of c-jun n-terminal kinases (jnk) and other protein kinases |
| GB0112803D0 (en) | 2001-05-25 | 2001-07-18 | Glaxo Group Ltd | Pyrimidine derivatives |
| MXPA04004166A (es) * | 2001-11-07 | 2004-07-08 | Hoffmann La Roche | Aminopirimidinas y piridinas. |
| TWI319387B (en) * | 2002-04-05 | 2010-01-11 | Astrazeneca Ab | Benzamide derivatives |
| CA2489458A1 (en) * | 2002-06-14 | 2003-12-24 | Altana Pharma Ag | Substituted diaminopyrimidines |
| TW200510311A (en) | 2002-12-23 | 2005-03-16 | Millennium Pharm Inc | CCr8 inhibitors |
| EP1590334B1 (en) * | 2003-01-30 | 2009-08-19 | Boehringer Ingelheim Pharmaceuticals Inc. | 2,4-diaminopyrimidine derivatives useful as inhibitors of pkc-theta |
| AU2004229392A1 (en) * | 2003-04-09 | 2004-10-28 | Exelixis, Inc. | Tie-2 modulators and methods of use |
| AR044519A1 (es) * | 2003-05-02 | 2005-09-14 | Novartis Ag | Derivados de piridin-tiazol amina y de pirimidin-tiazol amina |
| US7459460B2 (en) * | 2003-05-28 | 2008-12-02 | Bristol-Myers Squibb Company | Trisubstituted heteroaromatic compounds as calcium sensing receptor modulators |
| TW200533357A (en) * | 2004-01-08 | 2005-10-16 | Millennium Pharm Inc | 2-(amino-substituted)-4-aryl pyrimidines and related compounds useful for treating inflammatory diseases |
| RU2006135112A (ru) * | 2004-03-05 | 2008-04-10 | Чирон Корпорейшн (Us) | Тест-система in vitro для прогнозирования устойчивости пациента к терапевтическим средствам |
| CN1989131A (zh) * | 2004-03-30 | 2007-06-27 | 希龙公司 | 取代的噻吩衍生物用作抗癌药 |
| ES2505090T3 (es) * | 2004-05-07 | 2014-10-09 | Amgen Inc. | Derivados heterocíclicos nitrogenados como moduladores de proteína cinasas y su uso para el tratamiento de angiogénesis y cáncer |
| BRPI0511978A (pt) * | 2004-06-10 | 2008-01-22 | Irm Llc | compostos e composições como inibidores de proteìnas quinases |
| JP2008519034A (ja) * | 2004-11-03 | 2008-06-05 | バーテックス ファーマシューティカルズ インコーポレイテッド | イオンチャネル調節剤としてのピリミジン誘導体および使用方法 |
| TWI359810B (en) | 2004-11-04 | 2012-03-11 | Mitsubishi Tanabe Pharma Corp | Carboxylic acid derivative containing thiazole rin |
| MX2007007032A (es) * | 2004-12-17 | 2007-07-04 | Amgen Inc | Compuestos de aminopirimidina y metodos de uso. |
| US20060178388A1 (en) * | 2005-02-04 | 2006-08-10 | Wrobleski Stephen T | Phenyl-substituted pyrimidine compounds useful as kinase inhibitors |
| DE102005034821A1 (de) * | 2005-07-26 | 2007-02-08 | Fleissner Gmbh | Voluminöse Faserlaminate und ihre Herstellung |
| TWM293131U (en) * | 2006-01-10 | 2006-07-01 | Shuen Tai Prec Entpr Co Ltd | Handheld power hammer |
-
2005
- 2005-01-07 TW TW094100533A patent/TW200533357A/zh unknown
- 2005-01-10 DK DK05726205T patent/DK1701944T3/da active
- 2005-01-10 PT PT05726205T patent/PT1701944E/pt unknown
- 2005-01-10 ES ES05726205T patent/ES2330863T3/es not_active Expired - Lifetime
- 2005-01-10 SI SI200530816T patent/SI1701944T1/sl unknown
- 2005-01-10 AT AT05726205T patent/ATE437861T1/de active
- 2005-01-10 RS RSP-2009/0466A patent/RS51091B/sr unknown
- 2005-01-10 PL PL05726205T patent/PL1701944T3/pl unknown
- 2005-01-10 HR HR20090572T patent/HRP20090572T1/hr unknown
- 2005-01-10 EP EP09009692A patent/EP2123647A1/en not_active Withdrawn
- 2005-01-10 EP EP05726205A patent/EP1701944B1/en not_active Expired - Lifetime
- 2005-01-10 CA CA002559888A patent/CA2559888A1/en not_active Abandoned
- 2005-01-10 JP JP2006549475A patent/JP2007517895A/ja active Pending
- 2005-01-10 US US11/032,299 patent/US7732444B2/en not_active Expired - Fee Related
- 2005-01-10 DE DE602005015677T patent/DE602005015677D1/de not_active Expired - Lifetime
- 2005-01-10 WO PCT/US2005/000663 patent/WO2005066139A2/en not_active Ceased
- 2005-01-10 AR ARP050100080A patent/AR047185A1/es unknown
- 2005-01-10 AU AU2005204060A patent/AU2005204060A1/en not_active Abandoned
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2009
- 2009-10-27 CY CY20091101118T patent/CY1109529T1/el unknown
-
2010
- 2010-04-26 US US12/767,139 patent/US8268822B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US8268822B2 (en) | 2012-09-18 |
| AR047185A1 (es) | 2006-01-11 |
| WO2005066139A2 (en) | 2005-07-21 |
| DE602005015677D1 (de) | 2009-09-10 |
| EP1701944A2 (en) | 2006-09-20 |
| US20060040968A1 (en) | 2006-02-23 |
| US7732444B2 (en) | 2010-06-08 |
| PT1701944E (pt) | 2009-11-03 |
| ES2330863T3 (es) | 2009-12-16 |
| EP2123647A1 (en) | 2009-11-25 |
| ATE437861T1 (de) | 2009-08-15 |
| WO2005066139A3 (en) | 2005-10-13 |
| SI1701944T1 (sl) | 2010-03-31 |
| PL1701944T3 (pl) | 2010-01-29 |
| CY1109529T1 (el) | 2014-08-13 |
| US20110071134A1 (en) | 2011-03-24 |
| TW200533357A (en) | 2005-10-16 |
| RS51091B (sr) | 2010-10-31 |
| HRP20090572T1 (hr) | 2010-01-31 |
| AU2005204060A1 (en) | 2005-07-21 |
| EP1701944B1 (en) | 2009-07-29 |
| DK1701944T3 (da) | 2009-11-09 |
| JP2007517895A (ja) | 2007-07-05 |
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| FZDE | Discontinued |