CA2449769C - S-omeprazole (esomeprazole) inclusion complex with cyclodextrins - Google Patents
S-omeprazole (esomeprazole) inclusion complex with cyclodextrins Download PDFInfo
- Publication number
- CA2449769C CA2449769C CA2449769A CA2449769A CA2449769C CA 2449769 C CA2449769 C CA 2449769C CA 2449769 A CA2449769 A CA 2449769A CA 2449769 A CA2449769 A CA 2449769A CA 2449769 C CA2449769 C CA 2449769C
- Authority
- CA
- Canada
- Prior art keywords
- omeprazole
- cyclodextrin
- inclusion complex
- solution
- complex
- 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.)
- Expired - Fee Related
Links
- 229960000381 omeprazole Drugs 0.000 title claims abstract description 46
- 229920000858 Cyclodextrin Polymers 0.000 title claims abstract description 36
- 229940097362 cyclodextrins Drugs 0.000 title description 4
- SUBDBMMJDZJVOS-DEOSSOPVSA-N esomeprazole Chemical compound C([S@](=O)C1=NC2=CC=C(C=C2N1)OC)C1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-DEOSSOPVSA-N 0.000 title description 2
- 229960004770 esomeprazole Drugs 0.000 title description 2
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000000243 solution Substances 0.000 claims abstract description 16
- 239000007864 aqueous solution Substances 0.000 claims abstract description 13
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000012670 alkaline solution Substances 0.000 claims description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 4
- 239000004327 boric acid Substances 0.000 claims description 4
- 238000002955 isolation Methods 0.000 claims 2
- 230000001376 precipitating effect Effects 0.000 claims 2
- 208000017189 Gastrointestinal inflammatory disease Diseases 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- 238000007865 diluting Methods 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 210000004211 gastric acid Anatomy 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- -1 benzimidazole compound Chemical class 0.000 abstract description 10
- 230000003287 optical effect Effects 0.000 abstract description 9
- 239000011149 active material Substances 0.000 abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 description 11
- 150000001556 benzimidazoles Chemical class 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 229960003174 lansoprazole Drugs 0.000 description 3
- 229960004157 rabeprazole Drugs 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 150000004684 trihydrates Chemical class 0.000 description 3
- IQPSEEYGBUAQFF-SANMLTNESA-N 6-(difluoromethoxy)-2-[(s)-(3,4-dimethoxypyridin-2-yl)methylsulfinyl]-1h-benzimidazole Chemical class COC1=CC=NC(C[S@](=O)C=2NC3=CC=C(OC(F)F)C=C3N=2)=C1OC IQPSEEYGBUAQFF-SANMLTNESA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000003019 stabilising effect Effects 0.000 description 2
- SUBDBMMJDZJVOS-XMMPIXPASA-N (R)-omeprazole Chemical compound C([S@@](=O)C=1NC2=CC=C(C=C2N=1)OC)C1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-XMMPIXPASA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- IQPSEEYGBUAQFF-UHFFFAOYSA-N Pantoprazole Chemical compound COC1=CC=NC(CS(=O)C=2NC3=CC=C(OC(F)F)C=C3N=2)=C1OC IQPSEEYGBUAQFF-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000003699 antiulcer agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000027119 gastric acid secretion Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- MJIHNNLFOKEZEW-UHFFFAOYSA-N lansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1 MJIHNNLFOKEZEW-UHFFFAOYSA-N 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229960005019 pantoprazole Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- YREYEVIYCVEVJK-UHFFFAOYSA-N rabeprazole Chemical compound COCCCOC1=CC=NC(CS(=O)C=2NC3=CC=CC=C3N=2)=C1C YREYEVIYCVEVJK-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- 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
-
- 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
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/716—Glucans
- A61K31/724—Cyclodextrins
-
- 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
- A61K47/6951—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 using cyclodextrin
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Nanotechnology (AREA)
- General Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Medical Informatics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biophysics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0113792.6 | 2001-06-06 | ||
| GB0113792A GB2376231A (en) | 2001-06-06 | 2001-06-06 | Benzimidazole-cyclodextrin inclusion complex |
| PCT/GB2002/002542 WO2002098423A1 (en) | 2001-06-06 | 2002-06-06 | S-omeprazole (esomeprazole) inclusion complex with cyclodextrins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2449769A1 CA2449769A1 (en) | 2002-12-12 |
| CA2449769C true CA2449769C (en) | 2010-12-14 |
Family
ID=9916040
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2449769A Expired - Fee Related CA2449769C (en) | 2001-06-06 | 2002-06-06 | S-omeprazole (esomeprazole) inclusion complex with cyclodextrins |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US20040147481A1 (enExample) |
| EP (1) | EP1401442B1 (enExample) |
| JP (1) | JP2004536810A (enExample) |
| AT (1) | ATE282412T1 (enExample) |
| AU (1) | AU2002344386B2 (enExample) |
| CA (1) | CA2449769C (enExample) |
| DE (1) | DE60201995T2 (enExample) |
| ES (1) | ES2232780T3 (enExample) |
| GB (1) | GB2376231A (enExample) |
| LT (1) | LT5182B (enExample) |
| LV (1) | LV13154B (enExample) |
| NZ (1) | NZ529956A (enExample) |
| PL (1) | PL366940A1 (enExample) |
| PT (1) | PT1401442E (enExample) |
| RU (1) | RU2313343C2 (enExample) |
| WO (1) | WO2002098423A1 (enExample) |
| ZA (1) | ZA200309841B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1707217A1 (en) | 2004-12-17 | 2006-10-04 | Wacker Chemie AG | Process for preparing an alpha lipoic acid/cyclodextrin complex and product prepared |
| US20060229277A1 (en) * | 2005-04-08 | 2006-10-12 | Orbus Pharma, Inc. | Stabilized pharmaceutical compositions comprising an HMG-CoA reductase inhibitor |
| SI1973896T1 (sl) * | 2005-12-28 | 2009-08-31 | Union Quimico Farma | Postopek priprave (S) - enantiomere omeprazola |
| KR20070069567A (ko) * | 2005-12-28 | 2007-07-03 | 에스케이케미칼주식회사 | 저장안정성이 우수한 ｓ-오메프라졸 함유 포접 복합체 및이의 제조방법 |
| WO2009040825A1 (en) | 2007-09-25 | 2009-04-02 | Hetero Drugs Limited | A process for preparation of enantiomerically pure esomeprazole |
| WO2010097583A1 (en) * | 2009-02-24 | 2010-09-02 | Cipla Limited | Esomeprazole potassium polymorph and its preparation |
| CN104277030B (zh) * | 2013-07-03 | 2016-04-20 | 湖南理工学院 | 一种反应萃取分离泮托拉唑对映体的方法 |
| CN103768028A (zh) * | 2014-01-15 | 2014-05-07 | 山东新时代药业有限公司 | 一种注射用埃索美拉唑钠无菌冻干粉末及其制备工艺 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3427787A1 (de) * | 1984-07-27 | 1986-01-30 | Byk Gulden Lomberg Chemische Fabrik Gmbh, 7750 Konstanz | Wirkstoffkomplexe von 5-methoxy-2((4-methoxy-3,5-dimethyl-2-pyridyl) methylsulfinyl)-1h-benzimidazol mit cyclodextrinen, deren herstellung und arzneimittel |
| TW224049B (enExample) * | 1991-12-31 | 1994-05-21 | Sunkyong Ind Ltd | |
| US5877192A (en) * | 1993-05-28 | 1999-03-02 | Astra Aktiebolag | Method for the treatment of gastric acid-related diseases and production of medication using (-) enantiomer of omeprazole |
| SE9301830D0 (sv) * | 1993-05-28 | 1993-05-28 | Ab Astra | New compounds |
| SE504459C2 (sv) * | 1994-07-15 | 1997-02-17 | Astra Ab | Förfarande för framställning av substituerade sulfoxider |
| JPH0948730A (ja) * | 1995-06-02 | 1997-02-18 | Takeda Chem Ind Ltd | 水溶性の改善されたベンズイミダゾール系抗潰瘍剤含有安定組成物 |
| AU5780696A (en) * | 1995-06-02 | 1996-12-18 | Takeda Chemical Industries Ltd. | Stabilized composition comprising an antiulcerative benzimid azole |
| SE510666C2 (sv) | 1996-12-20 | 1999-06-14 | Astra Ab | Nya Kristallmodifikationer |
| JP4608031B2 (ja) * | 1997-03-13 | 2011-01-05 | ヘキサル アーゲー | アミノ酸／シクロデキストリン混合物による酸感受性ベンズイミダゾール類の安定化 |
| PT1018340E (pt) * | 1999-01-06 | 2003-12-31 | Tecnimede Sociedade Tecnico Medicinal Sa | Complexos de inclusao de sais de aminoacidos de derivados do benzimidazol com ciclodextrinas, sua preparacao e formulacoes farmaceuticas que os contem |
| KR100712039B1 (ko) * | 1999-08-26 | 2007-04-27 | 에이에이아이파머 인코포레이티드 | 알콕시로 치환된 벤즈이미다졸 화합물, 상기 화합물을포함하는 약학적 제제, 및 상기 화합물의 이용방법 |
| US6262085B1 (en) * | 1999-08-26 | 2001-07-17 | Robert R. Whittle | Alkoxy substituted Benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same |
| SE9903831D0 (sv) * | 1999-10-22 | 1999-10-22 | Astra Ab | Formulation of substituted benzimidazoles |
-
2001
- 2001-06-06 GB GB0113792A patent/GB2376231A/en not_active Withdrawn
-
2002
- 2002-06-06 AT AT02776528T patent/ATE282412T1/de not_active IP Right Cessation
- 2002-06-06 EP EP02776528A patent/EP1401442B1/en not_active Expired - Lifetime
- 2002-06-06 ES ES02776528T patent/ES2232780T3/es not_active Expired - Lifetime
- 2002-06-06 WO PCT/GB2002/002542 patent/WO2002098423A1/en not_active Ceased
- 2002-06-06 RU RU2003137221/15A patent/RU2313343C2/ru not_active IP Right Cessation
- 2002-06-06 AU AU2002344386A patent/AU2002344386B2/en not_active Ceased
- 2002-06-06 US US10/479,658 patent/US20040147481A1/en not_active Abandoned
- 2002-06-06 DE DE60201995T patent/DE60201995T2/de not_active Expired - Lifetime
- 2002-06-06 PL PL02366940A patent/PL366940A1/xx not_active Application Discontinuation
- 2002-06-06 NZ NZ529956A patent/NZ529956A/en unknown
- 2002-06-06 CA CA2449769A patent/CA2449769C/en not_active Expired - Fee Related
- 2002-06-06 PT PT02776528T patent/PT1401442E/pt unknown
- 2002-06-06 JP JP2003501462A patent/JP2004536810A/ja active Pending
-
2003
- 2003-12-03 LT LT2003100A patent/LT5182B/lt not_active IP Right Cessation
- 2003-12-19 ZA ZA200309841A patent/ZA200309841B/en unknown
-
2004
- 2004-01-06 LV LVP-04-01A patent/LV13154B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1401442A1 (en) | 2004-03-31 |
| JP2004536810A (ja) | 2004-12-09 |
| RU2003137221A (ru) | 2005-06-10 |
| RU2313343C2 (ru) | 2007-12-27 |
| DE60201995T2 (de) | 2005-11-24 |
| ES2232780T3 (es) | 2005-06-01 |
| HK1064602A1 (en) | 2005-02-04 |
| PL366940A1 (en) | 2005-02-07 |
| LT2003100A (en) | 2004-09-27 |
| ATE282412T1 (de) | 2004-12-15 |
| US20040147481A1 (en) | 2004-07-29 |
| ZA200309841B (en) | 2005-03-14 |
| LT5182B (lt) | 2004-12-27 |
| GB0113792D0 (en) | 2001-07-25 |
| AU2002344386B2 (en) | 2006-11-30 |
| PT1401442E (pt) | 2005-02-28 |
| GB2376231A (en) | 2002-12-11 |
| EP1401442B1 (en) | 2004-11-17 |
| CA2449769A1 (en) | 2002-12-12 |
| DE60201995D1 (de) | 2004-12-23 |
| WO2002098423A1 (en) | 2002-12-12 |
| LV13154B (en) | 2004-07-20 |
| NZ529956A (en) | 2005-07-29 |
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