ES2295937T3 - Analogos de 9,10-alfa,alfa-oh-taxano y procedimientos para su produccion. - Google Patents
Analogos de 9,10-alfa,alfa-oh-taxano y procedimientos para su produccion. Download PDFInfo
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- ES2295937T3 ES2295937T3 ES04789167T ES04789167T ES2295937T3 ES 2295937 T3 ES2295937 T3 ES 2295937T3 ES 04789167 T ES04789167 T ES 04789167T ES 04789167 T ES04789167 T ES 04789167T ES 2295937 T3 ES2295937 T3 ES 2295937T3
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- 208000016691 refractory malignant neoplasm Diseases 0.000 claims 1
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 20
- 125000000217 alkyl group Chemical group 0.000 abstract description 17
- 125000003118 aryl group Chemical group 0.000 abstract description 15
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 4
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 93
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- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 10
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- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 10
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- TYLVGQKNNUHXIP-MHHARFCSSA-N 10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)C=4C=CC=CC=4)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 TYLVGQKNNUHXIP-MHHARFCSSA-N 0.000 description 7
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- NNHYAHOTXLASEA-UHFFFAOYSA-N 1-(dimethoxymethyl)-4-methoxybenzene Chemical compound COC(OC)C1=CC=C(OC)C=C1 NNHYAHOTXLASEA-UHFFFAOYSA-N 0.000 description 3
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- 239000011549 crystallization solution Substances 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 1
- CETVQRFGPOGIQJ-UHFFFAOYSA-N lithium;hexane Chemical compound [Li+].CCCCC[CH2-] CETVQRFGPOGIQJ-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002633 protecting effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000011894 semi-preparative HPLC Methods 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000008259 solid foam Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 1
- 125000005607 tigloyl group Chemical group 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
Classifications
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50668003P | 2003-09-25 | 2003-09-25 | |
| US506680P | 2003-09-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2295937T3 true ES2295937T3 (es) | 2008-04-16 |
Family
ID=34393186
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES04789167T Expired - Lifetime ES2295937T3 (es) | 2003-09-25 | 2004-09-27 | Analogos de 9,10-alfa,alfa-oh-taxano y procedimientos para su produccion. |
Country Status (14)
| Country | Link |
|---|---|
| US (8) | US7745650B2 (OSRAM) |
| EP (2) | EP1785416A3 (OSRAM) |
| JP (5) | JP4874102B2 (OSRAM) |
| CN (1) | CN1886400A (OSRAM) |
| AT (1) | ATE377593T1 (OSRAM) |
| AU (1) | AU2004275881A1 (OSRAM) |
| CA (1) | CA2539975C (OSRAM) |
| DE (1) | DE602004009943T2 (OSRAM) |
| DK (1) | DK1664033T3 (OSRAM) |
| ES (1) | ES2295937T3 (OSRAM) |
| HR (1) | HRP20080057T3 (OSRAM) |
| PL (1) | PL1664033T3 (OSRAM) |
| PT (1) | PT1664033E (OSRAM) |
| WO (1) | WO2005030150A2 (OSRAM) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL1664033T3 (pl) * | 2003-09-25 | 2008-04-30 | Tapestry Pharmaceuticals Inc | Analogi 9,10-alfa, alfa-OH-taksanu i sposoby ich wytwarzania |
| JP2008536479A (ja) | 2005-02-11 | 2008-09-11 | ユニバーシティ オブ サザン カリフォルニア | ジスルフィド架橋を有するタンパク質の発現法 |
| MX2008008120A (es) * | 2005-12-21 | 2008-09-24 | Tapestry Pharmaceuticals Inc | Nuevos compuestos y metodos para formar taxanos y uso de los mismos. |
| CA2634746A1 (en) * | 2005-12-21 | 2007-07-05 | Tapestry Pharmaceuticals, Inc. | Processes for taxane derivatives and intermediates useful therein |
| RU2008142363A (ru) * | 2006-03-27 | 2010-05-10 | Тэпистри Фармасьютикалз, Инк. (Us) | Конвергентный способ синтеза таксановых производных |
| EP2029156A4 (en) * | 2006-05-01 | 2010-07-21 | Univ Southern California | COMBINATION THERAPY FOR CANCER TREATMENT |
| WO2007143839A1 (en) * | 2006-06-12 | 2007-12-21 | 6570763 Canada Inc. | Semi-synthetic route for the preparation of paclitaxel, docetaxel and 10-deacetylbaccatin iii from 9-dihydro-13-acetylbaccatin iii |
| US7847111B2 (en) | 2006-06-19 | 2010-12-07 | Canada Inc. | Semi-synthetic route for the preparation of paclitaxel, docetaxel, and 10-deacetylbaccatin III from 9-dihydro-13-acetylbaccatin III |
| US11786504B2 (en) | 2006-09-28 | 2023-10-17 | Tapestry Pharmaceuticals, Inc. | Taxane analogs for the treatment of brain cancer |
| WO2008121476A1 (en) | 2007-03-28 | 2008-10-09 | Tapestry Pharmaceuticals, Inc. | Biologically active taxane analogs and methods of treatment by oral administration |
| US11873308B2 (en) | 2006-11-06 | 2024-01-16 | Tapestry Pharmaceuticals, Inc. | Biologically active taxane analogs and methods of treatment by oral administration |
| US20080207743A1 (en) * | 2007-02-28 | 2008-08-28 | Rodger Lamb | Biologically Active Taxane Analogs and Methods of Treatment |
| WO2008109360A1 (en) | 2007-02-28 | 2008-09-12 | Tapestry Pharmaceuticals, Inc | Taxane analogs for the treatment of brain cancer |
| US8802394B2 (en) | 2008-11-13 | 2014-08-12 | Radu O. Minea | Method of expressing proteins with disulfide bridges with enhanced yields and activity |
| US9227983B2 (en) | 2011-04-07 | 2016-01-05 | Arbor Therapeutics, LLC | Taxane and abeo-taxane analogs |
| SG10201602309VA (en) * | 2011-04-07 | 2016-05-30 | Arbor Therapeutics Llc | Taxane and abeo-taxane analogs |
| MX337464B (es) * | 2011-06-06 | 2016-03-07 | Arbor Therapeutics Llc | Profarmacos lipofilicos labiles al acido de los agentes quimioterapeuticos contra el cancer. |
| EP4096588B1 (en) | 2020-03-04 | 2024-08-21 | Aquedeon Medical, Inc. | Vascular and aortic graft connector deployment tool with telescoping sheath |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX9102128A (es) | 1990-11-23 | 1992-07-08 | Rhone Poulenc Rorer Sa | Derivados de taxano,procedimiento para su preparacion y composicion farmaceutica que los contiene |
| US6794523B2 (en) | 1991-09-23 | 2004-09-21 | Florida State University | Taxanes having t-butoxycarbonyl substituted side-chains and pharmaceutical compositions containing them |
| US5352806A (en) * | 1992-04-17 | 1994-10-04 | Abbott Laboratories | Taxol derivatives |
| FR2697019B1 (fr) * | 1992-10-15 | 1994-11-25 | Rhone Poulenc Rorer Sa | Nouveaux dérivés du taxane, leur préparation et les compositions pharmaceutiques qui les contiennent. |
| EP0668762B1 (en) * | 1992-11-13 | 2003-09-17 | Florida State University | Isobutenyl-substituted taxanes and their pharmaceutical compositions |
| EP0687260B1 (en) * | 1993-03-05 | 2003-02-19 | Florida State University | Process for the preparation of 9-desoxotaxanes |
| US6710191B2 (en) * | 1993-03-05 | 2004-03-23 | Florida State University | 9β-hydroxytetracyclic taxanes |
| ES2179070T3 (es) | 1993-03-05 | 2003-01-16 | Univ Florida State | Derivados del taxano c9 y composiciones farmaceuticas que las contienen. |
| DE69433355T2 (de) * | 1993-03-22 | 2004-05-27 | Florida State University, Tallahassee | Taxane ohne die c-9 oxo gruppe und diese enthaltende pharmazeutische präparate |
| FR2707293A1 (fr) | 1993-07-08 | 1995-01-13 | Rhone Poulenc Rorer Sa | Nouveaux taxoides, leur préparation et les compositions pharmaceutiques qui les contiennent. |
| FR2715846A1 (fr) * | 1994-02-07 | 1995-08-11 | Rhone Poulenc Rorer Sa | Nouvelle composition pharmceutique à base de taxoïdes. |
| IT1275936B1 (it) | 1995-03-17 | 1997-10-24 | Indena Spa | Derivati della 10-deacetilbaccatina iii e della 10-deacetil-14b- idrossibaccatina iii loro metodo di preparazione e formulazioni |
| US5635531A (en) * | 1996-07-08 | 1997-06-03 | Bristol-Myers Squibb Company | 3'-aminocarbonyloxy paclitaxels |
| US5739359A (en) * | 1997-01-24 | 1998-04-14 | Virginia Tech Intellectual Properties, Inc. | Methods for preparing 1-deoxy paclitaxels |
| US6048990A (en) * | 1998-05-01 | 2000-04-11 | Napro Biotherapeutics, Inc. | Method for selective acylation of C-2'-O-protected-10-hydroxy-taxol at the C-10 position |
| CO5280224A1 (es) * | 2000-02-02 | 2003-05-30 | Univ Florida State Res Found | Taxanos sustituidos con ester en c7, utiles como agentes antitumorales y composiciones farmaceuticas que los contienen |
| ATE381328T1 (de) * | 2000-02-02 | 2008-01-15 | Univ Florida State Res Found | Heterosubstituierte taxan-c10-acetate als antitumormittel |
| US6825166B2 (en) | 2001-03-23 | 2004-11-30 | Tapestry Pharmaceuticals, Inc. | Molecular conjugates for use in treatment of cancer |
| CA2354471A1 (en) * | 2001-07-31 | 2003-01-31 | Florida State University Research Foundation, Inc. | C10 ester substituted taxanes |
| CA2470826A1 (en) | 2001-12-20 | 2003-07-03 | Bristol-Myers Squibb Company | Pharmaceutical compositions of orally active taxane derivatives having enhanced bioavailability |
| US6898834B1 (en) * | 2003-03-03 | 2005-05-31 | Westbridge Pty Ltd | Barrel stave reclaim |
| EP1894921A3 (en) | 2003-09-25 | 2008-03-12 | Tapestry Pharmaceuticals, Inc. | 9, 10-Alpha, Alpha-Oh-Taxane analogs and methods for production thereof |
| PL1664033T3 (pl) | 2003-09-25 | 2008-04-30 | Tapestry Pharmaceuticals Inc | Analogi 9,10-alfa, alfa-OH-taksanu i sposoby ich wytwarzania |
| WO2006124737A2 (en) | 2005-05-12 | 2006-11-23 | Tapestry Pharmaceuticals, Inc. | Molecular constructs suitable for targeted conjugates |
| CA2634746A1 (en) | 2005-12-21 | 2007-07-05 | Tapestry Pharmaceuticals, Inc. | Processes for taxane derivatives and intermediates useful therein |
| MX2008008120A (es) | 2005-12-21 | 2008-09-24 | Tapestry Pharmaceuticals Inc | Nuevos compuestos y metodos para formar taxanos y uso de los mismos. |
| RU2008142363A (ru) | 2006-03-27 | 2010-05-10 | Тэпистри Фармасьютикалз, Инк. (Us) | Конвергентный способ синтеза таксановых производных |
| WO2008121476A1 (en) | 2007-03-28 | 2008-10-09 | Tapestry Pharmaceuticals, Inc. | Biologically active taxane analogs and methods of treatment by oral administration |
| US20080207743A1 (en) | 2007-02-28 | 2008-08-28 | Rodger Lamb | Biologically Active Taxane Analogs and Methods of Treatment |
| WO2008109360A1 (en) | 2007-02-28 | 2008-09-12 | Tapestry Pharmaceuticals, Inc | Taxane analogs for the treatment of brain cancer |
-
2004
- 2004-09-27 PL PL04789167T patent/PL1664033T3/pl unknown
- 2004-09-27 EP EP06026009A patent/EP1785416A3/en not_active Withdrawn
- 2004-09-27 WO PCT/US2004/031816 patent/WO2005030150A2/en not_active Ceased
- 2004-09-27 US US10/951,555 patent/US7745650B2/en not_active Expired - Lifetime
- 2004-09-27 ES ES04789167T patent/ES2295937T3/es not_active Expired - Lifetime
- 2004-09-27 DK DK04789167T patent/DK1664033T3/da active
- 2004-09-27 HR HR20080057T patent/HRP20080057T3/xx unknown
- 2004-09-27 AU AU2004275881A patent/AU2004275881A1/en not_active Abandoned
- 2004-09-27 CA CA2539975A patent/CA2539975C/en not_active Expired - Lifetime
- 2004-09-27 CN CNA2004800346381A patent/CN1886400A/zh active Pending
- 2004-09-27 PT PT04789167T patent/PT1664033E/pt unknown
- 2004-09-27 DE DE602004009943T patent/DE602004009943T2/de not_active Expired - Fee Related
- 2004-09-27 JP JP2006528316A patent/JP4874102B2/ja not_active Expired - Lifetime
- 2004-09-27 AT AT04789167T patent/ATE377593T1/de not_active IP Right Cessation
- 2004-09-27 EP EP04789167A patent/EP1664033B1/en not_active Expired - Lifetime
-
2010
- 2010-06-02 US US12/792,427 patent/US7879904B2/en not_active Expired - Lifetime
- 2010-09-07 JP JP2010200399A patent/JP5525394B2/ja not_active Expired - Lifetime
- 2010-11-24 US US12/954,253 patent/US8962870B2/en active Active
-
2011
- 2011-04-08 JP JP2011086840A patent/JP5629632B2/ja not_active Expired - Lifetime
-
2014
- 2014-07-10 JP JP2014141964A patent/JP6106634B2/ja not_active Expired - Lifetime
-
2015
- 2015-01-23 US US14/604,147 patent/US9402824B2/en not_active Expired - Lifetime
-
2016
- 2016-07-12 JP JP2016137271A patent/JP6216417B2/ja not_active Expired - Lifetime
- 2016-07-27 US US15/220,975 patent/US9820962B2/en not_active Expired - Lifetime
-
2017
- 2017-10-09 US US15/728,049 patent/US10238621B2/en not_active Expired - Lifetime
-
2019
- 2019-01-14 US US16/247,425 patent/US10639293B2/en not_active Expired - Lifetime
-
2020
- 2020-04-15 US US16/849,879 patent/US20200237708A1/en not_active Abandoned
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