WO2001036510A2 - Use of poly(diallylamine) polymers - Google Patents
Use of poly(diallylamine) polymers Download PDFInfo
- Publication number
- WO2001036510A2 WO2001036510A2 PCT/GB2000/004308 GB0004308W WO0136510A2 WO 2001036510 A2 WO2001036510 A2 WO 2001036510A2 GB 0004308 W GB0004308 W GB 0004308W WO 0136510 A2 WO0136510 A2 WO 0136510A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polymer
- diallylamine
- poly
- formula
- group
- 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.)
- Ceased
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0605—Polycondensates containing five-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0611—Polycondensates containing five-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only one nitrogen atom in the ring, e.g. polypyrroles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
-
- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P41/00—Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
Definitions
- amide is generally understood to refer to a group of formula C(0)NR a R b where R a and R b are hydrogen or an optionally substituted hydrocarbyl group.
- sulphonamide correspondingly relates to groups of formula S(0)2NR a R b .
- An electron withdrawing group or groups may be used in compounds of formula I to activate one or more of the double bonds in preparation for polymerisation. The nature of each electron withdrawing group will depend upon its position in relation to the double bond it is required to activate, as well as the nature of any other functional groups within the compound.
- R 6 will comprise a bridging group for example as is known in polymer chemistry. It may include straight or branched chain alkyl groups, optionally substituted or interposed with functional groups or siloxane groups such as alkyl siloxanes.
- the length of the bridging group will affect the properties of the polymeric material derived from the monomer. This can be used to design polymers with properties which are best suited to the application. For instance when the bridging group comprises relatively long chains, (for example with in excess of 6 repeat units, for example from 6-20 repeat units), the polymer will have pliable plastic properties. Alternatively, when the bridging group is relatively short, (e.g. less than 6 repeat units) the material will be more brittle.
- the poly (diallylamine) polymer used in the various aspects of the present invention may be a homopolymer, or a copolymer derived from a mixture of a monomer of formula I or la with another monomer. Many such other monomers are known in the art; they may themselves include diallylamine compounds.
- R 25 , R 26 , R 27 and R 28 are each independently selected from hydrogen or hydrocarbyl groups such as alkyl and in particular methyl; the compound optionally contains a metal ion such as magnesium or zinc, within the macrocyclic heterocyclic unit; and
- Particularly preferred polymers for use in the various aspects of the present invention are those derived from the monomers prepared in accordance with the experimental examples below.
- Compounds of formula I are suitably prepared by conventional methods, for example by reacting a compound of formula VIII:
- a further advantage is their versatility, allowing a wide range of desired physicochemical properties to be built into the polymers formed from them.
- either amorphous or ordered systems can be prepared depending upon the polymerisation conditions used. Copolymerisation can also be used to affect the physical properties of the end product.
- Systems can be prepared which mimic conventional polymers, or which involve donor/acceptor systems.
- the polymers can be produced in a range of physical forms, including films and coatings, using heat or radiation curing techniques if desired.
- Ir vmax (thin film): 3321 (s), 3086, 2934, 1620, 1551, 1420, 1358, 1234, 1136, 1060, 994, 927, 756, 665, 560 cm "1 .
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Polymers & Plastics (AREA)
- Nanotechnology (AREA)
- Medical Informatics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biophysics (AREA)
- Biotechnology (AREA)
- General Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Surgery (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Gastroenterology & Hepatology (AREA)
- Diabetes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002391539A CA2391539C (en) | 1999-11-17 | 2000-11-10 | Use of poly(diallylamine) polymers |
| AT00974674T ATE287911T1 (de) | 1999-11-17 | 2000-11-10 | Verwendung von poly(diallylamin) polymeren |
| DE60017805T DE60017805T2 (de) | 1999-11-17 | 2000-11-10 | Verwendung von poly(diallylamin) polymeren |
| JP2001538997A JP2003514935A (ja) | 1999-11-17 | 2000-11-10 | ポリ(ジアリルアミン)ポリマー類の使用 |
| EP00974674A EP1265942B1 (en) | 1999-11-17 | 2000-11-10 | Use of poly(diallylamine) polymers |
| AU12893/01A AU772653B2 (en) | 1999-11-17 | 2000-11-10 | Use of poly(diallylamine) polymers |
| US10/130,246 US7767229B1 (en) | 1999-11-17 | 2000-11-10 | Use of poly diallyamine polymers |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9927088.6 | 1999-11-17 | ||
| GBGB9927088.6A GB9927088D0 (en) | 1999-11-17 | 1999-11-17 | Use of poly(diallylamine) polymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2001036510A2 true WO2001036510A2 (en) | 2001-05-25 |
| WO2001036510A3 WO2001036510A3 (en) | 2002-09-12 |
Family
ID=10864611
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/GB2000/004308 Ceased WO2001036510A2 (en) | 1999-11-17 | 2000-11-10 | Use of poly(diallylamine) polymers |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7767229B1 (enExample) |
| EP (1) | EP1265942B1 (enExample) |
| JP (1) | JP2003514935A (enExample) |
| AT (1) | ATE287911T1 (enExample) |
| AU (1) | AU772653B2 (enExample) |
| CA (1) | CA2391539C (enExample) |
| DE (1) | DE60017805T2 (enExample) |
| GB (1) | GB9927088D0 (enExample) |
| WO (1) | WO2001036510A2 (enExample) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008001102A1 (en) | 2006-06-30 | 2008-01-03 | Novel Polymer Solutions Limited | Method of producing a polymeric material, polymer, monomeric compound and method of preparing a monomeric compound |
| WO2007110621A3 (en) * | 2006-03-25 | 2008-02-28 | Ionic Polymer Solutions Ltd | Quaternary ammonium compounds and their uses |
| WO2012017233A1 (en) | 2010-08-02 | 2012-02-09 | Novel Polymer Solutions Limited | Methods of coating a low surface energy substrate |
| WO2012017237A1 (en) | 2010-08-02 | 2012-02-09 | Novel Polymer Solutions Limited | Composite articles and methods of producing same |
| WO2012017235A1 (en) | 2010-08-02 | 2012-02-09 | Novel Polymer Solutions Limited | Covered floors and methods of adhering flooring to a floor |
| WO2012131375A2 (en) | 2011-03-31 | 2012-10-04 | Novel Polymer Solutions Limited | Window frames, structural elements for a roofed construction and methods of assembling same |
| WO2013038192A1 (en) | 2011-09-13 | 2013-03-21 | Novel Polymer Solutions Limited | Mineral processing using a polymeric material that includes a moiety which selectively binds to a mineral |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102010002141A1 (de) | 2010-02-19 | 2011-08-25 | Momentive Performance Materials GmbH, 51373 | Integrale Bestrahlungseinheit |
| JP5889321B2 (ja) | 2010-11-04 | 2016-03-22 | アルビレオ アクチエボラグ | 肝疾患の処置用のibat阻害剤 |
| US9925696B2 (en) | 2011-08-18 | 2018-03-27 | Momentive Performance Materials Gmbh | Irradiation and molding unit |
| JP2015523926A (ja) | 2012-06-11 | 2015-08-20 | モーメンテイブ・パーフオーマンス・マテリアルズ・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | プラスチック複合成形体の製造方法 |
| HRP20171590T1 (hr) | 2013-06-05 | 2017-12-29 | Tricida Inc. | Polimeri koji vežu protone za oralnu primjenu |
| JP6751020B2 (ja) | 2014-06-25 | 2020-09-02 | Eaファーマ株式会社 | 固形製剤及びその着色防止又は着色低減方法 |
| PL3229816T3 (pl) | 2014-12-10 | 2020-09-21 | Tricida Inc. | Polimery wiążące protony do podawania doustnego |
| US10786529B2 (en) | 2016-02-09 | 2020-09-29 | Albireo Ab | Oral cholestyramine formulation and use thereof |
| US10441604B2 (en) | 2016-02-09 | 2019-10-15 | Albireo Ab | Cholestyramine pellets and methods for preparation thereof |
| US10441605B2 (en) | 2016-02-09 | 2019-10-15 | Albireo Ab | Oral cholestyramine formulation and use thereof |
| EP3452028A4 (en) | 2016-05-06 | 2020-04-15 | Tricida Inc. | COMPOSITIONS AND METHOD FOR TREATING ACID-BASED DISORDERS |
| EP3664781A1 (en) | 2017-08-09 | 2020-06-17 | Albireo AB | Cholestyramine granules, oral cholestyramine formulations and use thereof |
| US10934380B1 (en) | 2017-09-25 | 2021-03-02 | Tricida, Inc. | Crosslinked poly(allylamine) polymer pharmaceutical compositions |
| AU2018360867B2 (en) | 2017-11-03 | 2024-12-12 | Tricida, Inc. | Compositions for and method of treating acid-base disorders |
| US10793534B2 (en) | 2018-06-05 | 2020-10-06 | Albireo Ab | Benzothia(di)azepine compounds and their use as bile acid modulators |
| EP3802504B1 (en) | 2018-06-05 | 2023-01-18 | Albireo AB | Benzothia(di)azepine compounds and their use as bile acid modulators |
| US11801226B2 (en) | 2018-06-20 | 2023-10-31 | Albireo Ab | Pharmaceutical formulation of odevixibat |
| WO2019245448A1 (en) | 2018-06-20 | 2019-12-26 | Albireo Ab | Crystal modifications of odevixibat |
| US11549878B2 (en) | 2018-08-09 | 2023-01-10 | Albireo Ab | In vitro method for determining the adsorbing capacity of an insoluble adsorbant |
| US10722457B2 (en) | 2018-08-09 | 2020-07-28 | Albireo Ab | Oral cholestyramine formulation and use thereof |
| US11007142B2 (en) | 2018-08-09 | 2021-05-18 | Albireo Ab | Oral cholestyramine formulation and use thereof |
| US10941127B2 (en) | 2019-02-06 | 2021-03-09 | Albireo Ab | Benzothiadiazepine compounds and their use as bile acid modulators |
| RS63899B1 (sr) | 2019-02-06 | 2023-02-28 | Albireo Ab | Benzotiadiazepinska jedinjenja i njihova upotreba kao modulatora žučnih kiselina |
| US10975045B2 (en) | 2019-02-06 | 2021-04-13 | Aibireo AB | Benzothiazepine compounds and their use as bile acid modulators |
| US11014898B1 (en) | 2020-12-04 | 2021-05-25 | Albireo Ab | Benzothiazepine compounds and their use as bile acid modulators |
| EP4069361B1 (en) | 2019-12-04 | 2024-01-03 | Albireo AB | Benzothia(di)azepine compounds and their use as bile acid modulators |
| CN114761018B (zh) | 2019-12-04 | 2025-12-02 | 阿尔比里奥公司 | 苯并硫杂二氮杂环庚三烯化合物及其作为胆汁酸调节剂的用途 |
| MX2022006731A (es) | 2019-12-04 | 2022-06-09 | Albireo Ab | Compuestos de benzoti(di)azepina y su uso como moduladores del acido biliar. |
| EP4069359B1 (en) | 2019-12-04 | 2024-01-03 | Albireo AB | Benzothia(di)azepine compounds and their use as bile acid modulators |
| EP4188541B1 (en) | 2020-08-03 | 2024-12-25 | Albireo AB | Benzothia(di)azepine compounds and their use as bile acid modulators |
| JP2023549226A (ja) | 2020-11-12 | 2023-11-22 | アルビレオ エービー | 進行性家族性肝内胆汁うっ滞症(pfic)を処置するためのオデビキシバット |
| KR20230117393A (ko) | 2020-12-04 | 2023-08-08 | 알비레오 에이비 | 벤조티아(디)아제핀 화합물 및 담즙산 조절제로서의용도 |
| TW202313579A (zh) | 2021-06-03 | 2023-04-01 | 瑞典商艾爾比瑞歐公司 | 苯并噻(二)氮呯(benzothia(di)azepine)化合物及其作為膽酸調節劑之用途 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE520401A (enExample) * | 1952-06-03 | |||
| US3957699A (en) * | 1973-06-12 | 1976-05-18 | Ici Australia Limited | Process for polymerizing allylamines employing a redox initiator consisting of Fe++ or Ti+++ with H2 O2, hydroxyl amine, or hydroperoxides to form insoluble crosslinked polymers |
| US4121986A (en) * | 1975-05-07 | 1978-10-24 | Ici Australia Limited | Process for the polymerization of polyallylamines in the presence of a mineral acid solution |
| JPS5747302A (en) * | 1980-09-03 | 1982-03-18 | Mitsubishi Petrochem Co Ltd | Preparation of crosslinkable electrolytic polymer |
| JPS62257481A (ja) * | 1986-04-30 | 1987-11-10 | 三洋化成工業株式会社 | 染料固着剤 |
| US4759923A (en) * | 1987-06-25 | 1988-07-26 | Hercules Incorporated | Process for lowering serum cholesterol using poly(diallylmethylamine) derivatives |
| JPH021358A (ja) * | 1988-03-01 | 1990-01-05 | Sanyo Chem Ind Ltd | インクジェット記録紙用薬剤 |
| US6203785B1 (en) * | 1996-12-30 | 2001-03-20 | Geltex Pharmaceuticals, Inc. | Poly(diallylamine)-based bile acid sequestrants |
| US5985938A (en) * | 1997-11-05 | 1999-11-16 | Geltex Pharmaceuticals, Inc. | Method for reducing oxalate |
| US6083497A (en) * | 1997-11-05 | 2000-07-04 | Geltex Pharmaceuticals, Inc. | Method for treating hypercholesterolemia with unsubstituted polydiallylamine polymers |
| US6726905B1 (en) | 1997-11-05 | 2004-04-27 | Genzyme Corporation | Poly (diallylamines)-based phosphate binders |
| SG105450A1 (en) * | 1998-07-02 | 2004-08-27 | Nat Starch Chem Invest | Allylated amide compounds and die attach adhesives prepared therefrom |
| SG85658A1 (en) * | 1998-07-02 | 2002-01-15 | Nat Starch Chem Invest | Package encapsulants prepared from allylated amide compounds |
| GB9816167D0 (en) * | 1998-07-25 | 1998-09-23 | Secr Defence | Polymer production |
| GB9816171D0 (en) * | 1998-07-25 | 1998-09-23 | Secr Defence | Monomers and network polymers obtained therefrom |
-
1999
- 1999-11-17 GB GBGB9927088.6A patent/GB9927088D0/en not_active Ceased
-
2000
- 2000-11-10 EP EP00974674A patent/EP1265942B1/en not_active Expired - Lifetime
- 2000-11-10 WO PCT/GB2000/004308 patent/WO2001036510A2/en not_active Ceased
- 2000-11-10 AU AU12893/01A patent/AU772653B2/en not_active Ceased
- 2000-11-10 DE DE60017805T patent/DE60017805T2/de not_active Expired - Lifetime
- 2000-11-10 JP JP2001538997A patent/JP2003514935A/ja active Pending
- 2000-11-10 AT AT00974674T patent/ATE287911T1/de not_active IP Right Cessation
- 2000-11-10 US US10/130,246 patent/US7767229B1/en not_active Expired - Fee Related
- 2000-11-10 CA CA002391539A patent/CA2391539C/en not_active Expired - Fee Related
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007110621A3 (en) * | 2006-03-25 | 2008-02-28 | Ionic Polymer Solutions Ltd | Quaternary ammonium compounds and their uses |
| WO2008001102A1 (en) | 2006-06-30 | 2008-01-03 | Novel Polymer Solutions Limited | Method of producing a polymeric material, polymer, monomeric compound and method of preparing a monomeric compound |
| KR101381367B1 (ko) | 2006-06-30 | 2014-04-04 | 노벨 폴리머 솔루션스 리미티드 | 폴리머 물질을 생성하는 방법, 폴리머, 모노머 화합물 및 모노머 화합물을 제조하는 방법 |
| WO2012017233A1 (en) | 2010-08-02 | 2012-02-09 | Novel Polymer Solutions Limited | Methods of coating a low surface energy substrate |
| WO2012017237A1 (en) | 2010-08-02 | 2012-02-09 | Novel Polymer Solutions Limited | Composite articles and methods of producing same |
| WO2012017235A1 (en) | 2010-08-02 | 2012-02-09 | Novel Polymer Solutions Limited | Covered floors and methods of adhering flooring to a floor |
| WO2012131375A2 (en) | 2011-03-31 | 2012-10-04 | Novel Polymer Solutions Limited | Window frames, structural elements for a roofed construction and methods of assembling same |
| WO2013038192A1 (en) | 2011-09-13 | 2013-03-21 | Novel Polymer Solutions Limited | Mineral processing using a polymeric material that includes a moiety which selectively binds to a mineral |
| US10603676B2 (en) | 2011-09-13 | 2020-03-31 | Cidra Minerals Processing Inc. | Mineral processing |
| US11654443B2 (en) | 2011-09-13 | 2023-05-23 | Cidra Minerals Processing Inc. | Mineral processing |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE287911T1 (de) | 2005-02-15 |
| JP2003514935A (ja) | 2003-04-22 |
| GB9927088D0 (en) | 2000-01-12 |
| DE60017805D1 (de) | 2005-03-03 |
| EP1265942B1 (en) | 2005-01-26 |
| AU772653B2 (en) | 2004-05-06 |
| CA2391539C (en) | 2009-08-11 |
| AU1289301A (en) | 2001-05-30 |
| EP1265942A2 (en) | 2002-12-18 |
| WO2001036510A3 (en) | 2002-09-12 |
| DE60017805T2 (de) | 2006-01-12 |
| CA2391539A1 (en) | 2001-05-25 |
| US7767229B1 (en) | 2010-08-03 |
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