EP1682096A1 - Procede permettant de preparer des compositions de clopidogrel - Google Patents
Procede permettant de preparer des compositions de clopidogrelInfo
- Publication number
- EP1682096A1 EP1682096A1 EP04797570A EP04797570A EP1682096A1 EP 1682096 A1 EP1682096 A1 EP 1682096A1 EP 04797570 A EP04797570 A EP 04797570A EP 04797570 A EP04797570 A EP 04797570A EP 1682096 A1 EP1682096 A1 EP 1682096A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- clopidogrel
- granules
- particles
- aggregates
- composition
- 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.)
- Withdrawn
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/2027—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
-
- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
- A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2059—Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2806—Coating materials
- A61K9/2833—Organic macromolecular compounds
- A61K9/286—Polysaccharides, e.g. gums; Cyclodextrin
- A61K9/2866—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
Definitions
- This invention relates to pharmaceutical compositions comprising clopidogrel and to processes for preparing such compositions.
- Clopidogrel is a known anti-thrombotic agent which inhibits platelet aggregation. See Merck Index, 12 th Edition, entry 2457. Clopidogrel is administered currently in the form of the biphosphate salt as a film-coated tablet.
- clopidogrel salts are known to exhibit difficulties in formulation.
- the present applicants have found that clopidogrel in base or salt form, e.g. as mesylate or hydrochloride, is problematic to formulate for example as a tablet, and attribute this principally to hygroscopicity.
- clopidogrel tablets suffer from degradation on storage.
- this invention provides a composition suitable for oral administration comprising clopidogrel in base or pharmaceutically acceptable salt form which composition comprises a polymer coating.
- the polymer coating may comprise a polyvinyl acetate or a polyvinyl alcohol.
- clopidogrel when in salt form clopidogrel may be selected from mesylate, hydroiodide, hydrobromide and hydrochloride.
- this invention provides a composition suitable for oral administration comprising clopidogrel in base or pharmaceutically acceptable salt form which composition comprises a hydrophobic component.
- Suitable hydrophobic components include hydrogenated vegetable oils.
- the hydrophobic component-containing compositions of this invention may comprise a polymer coating, e.g. a polyvinyl acetate or a polyvinyl alcohol.
- a polymer coating e.g. a polyvinyl acetate or a polyvinyl alcohol.
- the hydrophobic component when present, is not coated.
- this invention provides clopidogrel in form of coated particles, granules or agglomerates.
- this invention provides a composition suitable for oral administration comprising clopidogrel in base or pharmaceutically acceptable salt form wherein the clopidogrel is in the form of coated particles, granules or agglomerates.
- this invention provides a composition suitable for oral administration comprising clopidogrel in pharmaceutically acceptable salt form which composition comprises
- a polymer coating selected from a polyvinyl acetate or a polyvinyl alcohol
- hydrophobic component comprising a hydrogenated vegetable oil, wherein the salt is selected from mesylate, hydrobromide, hydroiodide and hydrochloride, and wherein the clopidogrel is in the form of coated particles, granules or agglomerates.
- the particle-, granule- or agglomerate-coating may comprise a hydrophobic polymer, e.g. a polyvinyl acetate or a polyvinyl alcohol, a hydrogenated vegetable oil or a cyclodextrin.
- a hydrophobic polymer e.g. a polyvinyl acetate or a polyvinyl alcohol, a hydrogenated vegetable oil or a cyclodextrin.
- Preferred polymer coatings employed in the compositions of this invention are selected from celluose acetate, polymethacrylates for example Eudragit E or Eudragit NE 30 D, and ethylcellulose.
- Suitable vegetable oils include hydrogenated cottonseed oil e.g. those available commercially as Lubritab or Sterotex; hydrogenated palm oil, e.g. available as Softisan 154 or Dynasan P60; hydrogenated soyabean oil such as that available as Sterotex HM.
- the hydrophobic component may be selected from cetyl alcohol, cetostearyl alcohol, cholesterol, gyceryl monostearate, glyceryl monooleate, glyceryl palmitostearate and stearic acid.
- the cyclodextrin may comprise an alpha-, beta- or gamma-cyclodextrin.
- compositions of this invention herein described may be administered in form of a tablet, sachet, or hard or soft gelatine capsule. Coated tablets are preferred.
- the clopidogrel may be present in an amount of up to 50% by weight, for example 10 to 45%, e.g. 20 to 40%, e.g. 25 to 35% by weight, based on the total weight of the composition.
- compositions of this invention may include:
- Lactose DCL 11 is a suitable grade in the compositions of this invention.
- microcrystalline cellulose in an amount when present of up to 40% by weight, for example 5 to 35%, e.g. 8 to 25%, e.g. 10 to 20% by weight based on the total weight of the composition.
- Avicel PH 112 is an appropriate grade for use in the compositions of this invention.
- Starch 1500 LM is an appropriate grade for use in the compositions of this invention;
- the hydrogenated vegetable oil when present in an amount of up to about 15% by weight, e.g. 1 to 10%, e.g. 2 to 7% by weight, based on the weight of the composition.
- oils are commercially available for example under the trade mark Sterotex;
- the polymer coating when present, in an amount of up to about 10 % by weight, e.g. 2 to 8%, e.g. 4 to 6 % by weight, based on the weight of the composition.
- Such coatings are available commercially for example under the trade mark Opadry AMB;
- a filler in an amount when present of up to 80% by weight, for example 5 to 75%, e.g. 10 to 65%, e.g. 15 to 50% by weight based on the total weight of the composition.
- Mannitol and xylitol are examples of suitable fillers in compositions of this invention.
- Other components may include titanium dioxide, a hydroxypropyl methylcellulose, a hydroxyl propylcellulose and a propylene glycol.
- compositions of this invention are more straightforward to formulate than hitherto known compositions.
- the applicants have found that processability of the components in forming, e.g. tablets, is easier than for known processes for making solid clopidogrel compositions.
- compositions of this invention are storage-stable. Thus no or negligible degradation is observed on storage at ambient conditions over periods of days, weeks and months.
- the clopidogrel employed in the compositions and processes of this invention may be in racemate form, in form of a partially- or wholly-enriched diastereomer.
- the clopidogrel may be in form of a pure or substantially pure diastereomer, e.g. > 90% e.g. 93%, 94%, 95% or > 95%, e.g. 96%, 97% or greater diastereomer as determined using known methods.
- this invention provides a process for preparing tablets comprising clopidogrel in base or pharmaceutically acceptable salt form which process comprises a) compacting the clopidrogrel with anhydrous or substantially anhydrous components so as to form aggregates, b) breaking down the aggregates so as to form granules or particles, c) optionally mixing the granules or particles with at least one further component, and d) compacting or compressing the granules or particles thus formed into tablets.
- Compaction may be carried out for example using a roller compactor.
- the desiccant e.g. anhydrous silica
- the aggregates or granules may be mixed with the aggregates or granules. This improves stability and flow of the processed mixture.
- a hydrophobic lubricant e.g. hydrogenated vegetable oil, may be added. This provides improved stability over that observed using conventional lubricants.
- the process may be carried out in a low- or ultra-low humidity environment.
- step a) may be milled to granules or particles by screening through a comminuting mill, for example an oscillating granulator, quadrocomill or hammer mill.
- step b) serves to break the aggregates down in size.
- process step b) may be carried out so as to form granules with a small or negligible proportion of particles.
- the output from step b) may amount to 80% or more granules by weight in a granule/particle mixture, e.g. 85%, 90%, 95% or greater e.g. 98%, 99% or 100% granules.
- the solvent medium may comprise an aqueous or organic solvent or mixture of organic solvents.
- an aqueous medium when employed, this may containing up to 100% by weight water, e.g. 5 to 80%, e.g. 10 to 60% by weight.
- the thus coated or encapsulated particles or granules may be further processed, for example into tablets using compaction or compression.
- Coating of the clopidogrel particles may be achieved using a fiuidised bed, e.g. a Wurster, or by water-in-oil or oil-in-water phase separation or coacervation encapsulation methods.
- coating of the clopidogrel granules or particles may be carried out after process step b) or step c) if present and before step d).
- hydrophobic polymer may establish an effective moisture barrier around the particles or tablets.
- Typical dimensions observed using known methods of particles used in this invention range from 50 microns to 150 microns. 75% of the granules of this invention may be in the size range 100 microns to 500 microns, and 75% of the agglomerates of this invention may be in the size range 500 microns to 2000 microns.
- a preferred aspect of the invention is a clopidogrel composition as herein described in form of a coated particle, granule, agglomerate or tablet, wherein the coating is free of or substantially free of HPMC.
- Clopidogrel may be administered at a dose of lOmg, 25mg, 50mg, 60 mg, 75mg or lOOmg drug substance based on clopidogrel base, depending on the patient's body weight and other circumstances. This dose may be daily.
- the tablet weight When administered in tablet form, the tablet weight may be for example 50 mg, lOOmg, 150 mg, 200 mg or 300 mg in total.
- Clopidogrel base, mesylate and hydroiodide are sourced from the Torrent company.
- Clopidogrel hydrochloride may be prepared by processes analogous to those disclosed in published patent applications EP 0 281 459 and WO 98/51682.
- Clopidogrel hydrobromide may be prepared by passing HBr gas through an organic solution of clopidogrel base, e.g. in toluene, at ambient temperature.
- Clopidogrel hydrobromide salt precipitates and may be filtered and washed, e.g. with an organic solvent such as toluene.
- the wet cake of the salt may be dried under vacuum at elevated temperature, for example 50 to 80°C, e.g. 70 to 75°C, to provide clopidogrel HBr as an off-white solid.
- this invention provides a composition or process substantially as herein described with reference to the examples.
- this invention provides compositions produced using the processes of this invention.
- the compositions, e.g. tablets, produced by the processes of this invention may be free of or substantially free of HPMC.
- the components are mixed together, processed using dry roller compaction into aggregates, compacted to granules and formed into tablets. Processing takes place in a low-humidity environment. 1000 tablets are prepared and divided into 10 lots each of 100 tablets. All ten lots are stored at ambient conditions and inspected at daily intervals. No degradation is detected by visual inspection after 10 days. Negligible degradation is observed after two months.
- Example 1 is repeated using clopidogrel hydroiodide in place of the mesylate, using molar equivalent to 75 mg clopidogrel base. Stable tablets are produced.
- Example 1 is repeated using clopidogrel hydrochloride in place of the mesylate using molar equivalent to 75 mg clopidogrel base. Stable tablets are produced.
- the anhydrous components are mixed together, processed in analogous manner to that in Example 1 and formed into tablets.
- the tablets are coated using Opadry AMB.
- 1000 tablets are prepared and divided into 10 lots each of 100 tablets. All ten lots are stored at ambient conditions and inspected at daily intervals. No degradation is detected by visual inspection after 10 days. Negligible degradation isobserved after one month.
- Example 4 is repeated using clopidogrel hydroiodide in place of the mesylate.
- the molar equivalent to 75 mg clopidogrel base is used. Stable tablets are produced.
- Example 4 is repeated using clopidogrel hydrochloride (molar equivalent to 75 mg base) in place of the mesylate. Stable tablets are produced.
- compositions containing mannitol as a filler are prepared in the following Examples 7 and 9 to 12.
- Composition 7a is a:
- the clopidogrel salt is blended with mannitol, microcrystalline cellulose and part of the low substituted hydroxypropylcellulose.
- the blend is compacted using a Fitzpatrick Chilsonator roller compactor.
- the compacts are then milled into granules by screening through an oscillating granulator comminuting mill.
- the granules are blended with part of microcrystalline cellulose, low substituted hydroxypropylcellulose, mannitol, PEG 6000 and Sterotex.
- the blend is compressed into tablets using a Korsch rotary compressor.
- the tablets are then coated with Opadry AMB in a Hicoater perforated coating pan.
- compositions 7b and 7c An analogous procedure is used to prepare compositions 7b and 7c.
- compositions 9a to 9c are prepared in analogous manner to that for 7a.
- compositions 10a to 10c are prepared in analogous manner to that for 7a. Examples 1a to lie
- compositions 11a to lie are prepared in analogous manner to 7a above.
- Examples 12a and 12b clopidogrel HC1 tablets
- compositions are prepared in analogous manner to that in Example 7a above, with the omission of Opadry AMB coating in the formulation of Example 12b.
- the tablet composition of Example 12a exhibits enhanced stability over that of Example 12b.
- the process of this invention serves to provide more stable and robust clopidogrel compositions than hitherto known compositions. This allows economies such as elimination of more expensive packaging materials.
- the compositions are reproducible, straightforward and economic to manufacture.
- the invention provides more stable solid oral dosage forms of clopidogrel- mesylate, -hydroiodide and -hydrochloride.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB0325603.9A GB0325603D0 (en) | 2003-11-03 | 2003-11-03 | Organic compounds |
PCT/EP2004/012437 WO2005048992A1 (fr) | 2003-11-03 | 2004-11-03 | Procede permettant de preparer des compositions de clopidogrel |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1682096A1 true EP1682096A1 (fr) | 2006-07-26 |
Family
ID=29725839
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP04797570A Withdrawn EP1682096A1 (fr) | 2003-11-03 | 2004-11-03 | Procede permettant de preparer des compositions de clopidogrel |
Country Status (8)
Country | Link |
---|---|
EP (1) | EP1682096A1 (fr) |
JP (1) | JP2007527414A (fr) |
CN (1) | CN101848705A (fr) |
AU (1) | AU2004290511A1 (fr) |
BR (1) | BRPI0416109A (fr) |
CA (1) | CA2540965A1 (fr) |
GB (1) | GB0325603D0 (fr) |
WO (1) | WO2005048992A1 (fr) |
Families Citing this family (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005070464A2 (fr) * | 2004-01-21 | 2005-08-04 | Biofarma Ilac Sanayi Ve Ticaret A.S. | Formulation de comprimes de bisulfate de clopidogrel |
JP2007533746A (ja) | 2004-04-20 | 2007-11-22 | サノフイ−アベンテイス | クロピドグレル塩及びその多形型 |
ZA200608569B (en) * | 2004-04-20 | 2007-12-27 | Sanofi Aventis | Polymorphic forms of methyl (+)-(S)-alpha- (2-chlorophenyl)-6, 7-dinydrothieno[3,2-C] pyridine-5(4H) acetate hydrobromide, clopidrogel hydrobromide |
US20060223845A1 (en) * | 2005-02-24 | 2006-10-05 | Eran Turgeman | Clopidogrel base suitable for pharmaceutical formulation and preparation thereof |
DE202005013839U1 (de) * | 2005-09-01 | 2005-10-27 | Helm Ag | Pharmazeutische Formulierung für Salze monobasischer Säuren mit Clopidogrel |
WO2007054968A2 (fr) * | 2005-09-20 | 2007-05-18 | Torrent Pahrmaceuticals Limited | Compositions pharmaceutiques atypiques de mesylate de clopidogrel |
IS2385B (is) * | 2006-02-10 | 2008-07-15 | Actavis Group Hf. | Klópidógrel bísúlfat lyfjasamsetningar |
CZ298349B6 (cs) * | 2006-03-09 | 2007-09-05 | Zentiva, A. S | Farmaceutická kompozice clopidogrelu hydrogenbromidu |
US20100145053A1 (en) * | 2006-04-05 | 2010-06-10 | Cadila Healthcare Limited | Modified release clopidogrel formulation |
ES2342965T5 (es) | 2006-04-13 | 2013-04-03 | Acino Pharma Ag | Gliceridos parciales como lubricantes para composiciones farmacéuticas que contienen derviados de tieno(3,2-c)piridina |
ATE449597T1 (de) * | 2006-04-13 | 2009-12-15 | Rentschler Pharma Gmbh | Poloxamere als schmiermittel für pharmazeutische zusammensetzungen enthaltend thienoä3,2-cüpyridin-derivate |
WO2007128476A1 (fr) * | 2006-05-04 | 2007-11-15 | Sandoz Ag | Compositions pharmaceutiques contenant du chlorhydrate de clopidogrel |
KR20080055355A (ko) * | 2006-12-15 | 2008-06-19 | 에스케이케미칼주식회사 | 보관안정성이 우수한 클로피도그렐 함유 포접 복합체 |
KR20080055356A (ko) * | 2006-12-15 | 2008-06-19 | 에스케이케미칼주식회사 | 보관안정성이 우수한 클로피도그렐 함유 포접 복합체 |
EP1970054A3 (fr) | 2007-03-14 | 2009-06-03 | Ranbaxy Laboratories Limited | Comprimés de clopidogrel |
ES2408380T3 (es) * | 2007-04-20 | 2013-06-20 | Wockhardt Limited | Composiciones farmacéuticas de clopidogrel |
ES2376057T3 (es) * | 2008-02-26 | 2012-03-08 | Laboratorios Lesvi, S.L. | Formulaciones farmacéuticas que contienen clopidogrel. |
EP2107061A1 (fr) | 2008-04-02 | 2009-10-07 | Krka Tovarna Zdravil, D.D., Novo Mesto | Procédé de préparation de clopidogrel enrichi optiquement |
DE602008002820D1 (de) | 2008-04-25 | 2010-11-11 | Sandoz Ag | Hydrogensulfat von 2-Acetoxy-5-(a-cyclopropylcarbonyl-2-fluorbenzyl)-4,5,6,7-tetrahydrothienoÄ3,2-cÜpyridin und dessen Zubereitung |
SI2398468T1 (sl) | 2009-02-17 | 2017-03-31 | Krka, D.D., Novo Mesto | Farmacevtske sestave, ki obsegajo prasugrel ali njegove farmacevtsko sprejemljive kislinske adicijske soli in postopek za njihovo pripravo |
JP2013032289A (ja) * | 2009-10-28 | 2013-02-14 | Daiichi Sankyo Co Ltd | ワックス安定製剤 |
ES2363964B1 (es) | 2009-11-20 | 2012-08-22 | Gp Pharm, S.A. | Cápsulas de principios activos farmacéuticos y ésteres de ácidos grasos poliinsaturados. |
CN101766573B (zh) | 2010-02-05 | 2013-02-13 | 上海安必生制药技术有限公司 | 硫酸氢氯吡格雷固体制剂的制备工艺 |
CN101851247B (zh) * | 2010-06-04 | 2013-05-29 | 浙江华海药业股份有限公司 | 含有硫酸氢氯吡格雷晶体颗粒的组合物 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2363053C (fr) * | 2001-11-09 | 2011-01-25 | Bernard Charles Sherman | Formulation pour pastilles de bisulfate de clopidogrel |
EP1606231A1 (fr) * | 2003-02-03 | 2005-12-21 | Nadkarni, Sunil Sadanand | Procede de preparation de clopidogrel, ses sels et compositions pharmaceutiques |
-
2003
- 2003-11-03 GB GBGB0325603.9A patent/GB0325603D0/en not_active Ceased
-
2004
- 2004-11-03 BR BRPI0416109-2A patent/BRPI0416109A/pt not_active Application Discontinuation
- 2004-11-03 AU AU2004290511A patent/AU2004290511A1/en not_active Abandoned
- 2004-11-03 WO PCT/EP2004/012437 patent/WO2005048992A1/fr not_active Application Discontinuation
- 2004-11-03 EP EP04797570A patent/EP1682096A1/fr not_active Withdrawn
- 2004-11-03 JP JP2006537245A patent/JP2007527414A/ja not_active Withdrawn
- 2004-11-03 CN CN200480032288A patent/CN101848705A/zh active Pending
- 2004-11-03 CA CA002540965A patent/CA2540965A1/fr not_active Abandoned
Non-Patent Citations (1)
Title |
---|
See references of WO2005048992A1 * |
Also Published As
Publication number | Publication date |
---|---|
JP2007527414A (ja) | 2007-09-27 |
BRPI0416109A (pt) | 2007-01-02 |
GB0325603D0 (en) | 2003-12-10 |
CA2540965A1 (fr) | 2005-06-02 |
AU2004290511A1 (en) | 2005-06-02 |
WO2005048992A1 (fr) | 2005-06-02 |
CN101848705A (zh) | 2010-09-29 |
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