ZA200501053B - Salt of morphine-6-glucuronide - Google Patents
Salt of morphine-6-glucuronide Download PDFInfo
- Publication number
- ZA200501053B ZA200501053B ZA2005/01053A ZA200501053A ZA200501053B ZA 200501053 B ZA200501053 B ZA 200501053B ZA 2005/01053 A ZA2005/01053 A ZA 2005/01053A ZA 200501053 A ZA200501053 A ZA 200501053A ZA 200501053 B ZA200501053 B ZA 200501053B
- Authority
- ZA
- South Africa
- Prior art keywords
- hbr
- morphine
- treatment
- salt
- glucuronide
- Prior art date
Links
- GNJCUHZOSOYIEC-GAROZEBRSA-N Morphine-6-glucuronide Chemical compound O([C@H]1C=C[C@H]2[C@H]3CC=4C5=C(C(=CC=4)O)O[C@@H]1[C@]52CCN3C)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O GNJCUHZOSOYIEC-GAROZEBRSA-N 0.000 title abstract description 12
- 150000003839 salts Chemical class 0.000 title description 35
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims abstract description 88
- 238000000034 method Methods 0.000 claims abstract description 17
- 239000003814 drug Substances 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- 239000003960 organic solvent Substances 0.000 claims description 7
- 208000000059 Dyspnea Diseases 0.000 claims description 6
- 206010013975 Dyspnoeas Diseases 0.000 claims description 6
- 208000002193 Pain Diseases 0.000 claims description 5
- 201000011510 cancer Diseases 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 230000001154 acute effect Effects 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 208000017667 Chronic Disease Diseases 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 230000000202 analgesic effect Effects 0.000 abstract description 4
- 201000010099 disease Diseases 0.000 abstract description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 2
- 239000002585 base Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 20
- 238000003860 storage Methods 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 12
- 238000003556 assay Methods 0.000 description 11
- 230000015556 catabolic process Effects 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 229910019142 PO4 Inorganic materials 0.000 description 9
- 238000006731 degradation reaction Methods 0.000 description 9
- 229960004592 isopropanol Drugs 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 9
- 239000010452 phosphate Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 8
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 229910021653 sulphate ion Inorganic materials 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 239000007857 degradation product Substances 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 5
- 239000013078 crystal Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical class O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 239000008380 degradant Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 230000003211 malignant effect Effects 0.000 description 2
- 229960005181 morphine Drugs 0.000 description 2
- 239000013558 reference substance Substances 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 238000002798 spectrophotometry method Methods 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- IBRSSZOHCGUTHI-UHFFFAOYSA-N 2-chloropyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1Cl IBRSSZOHCGUTHI-UHFFFAOYSA-N 0.000 description 1
- IJJWOSAXNHWBPR-HUBLWGQQSA-N 5-[(3as,4s,6ar)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-n-(6-hydrazinyl-6-oxohexyl)pentanamide Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)NCCCCCC(=O)NN)SC[C@@H]21 IJJWOSAXNHWBPR-HUBLWGQQSA-N 0.000 description 1
- 241000408896 Alenia Species 0.000 description 1
- 241001116389 Aloe Species 0.000 description 1
- 241000005672 Baia Species 0.000 description 1
- 101100479031 Caenorhabditis elegans aars-2 gene Proteins 0.000 description 1
- 101000916289 Ctenocephalides felis Salivary antigen 1 Proteins 0.000 description 1
- 101001047083 Gallus gallus Calcium-activated potassium channel subunit alpha-1 Proteins 0.000 description 1
- 238000010268 HPLC based assay Methods 0.000 description 1
- 238000003109 Karl Fischer titration Methods 0.000 description 1
- -1 Morphine-6-glucuronide sulphate salt Chemical class 0.000 description 1
- 208000001294 Nociceptive Pain Diseases 0.000 description 1
- 108010049358 Oncogene Protein p65(gag-jun) Proteins 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 208000004550 Postoperative Pain Diseases 0.000 description 1
- JXVIIQLNUPXOII-UHFFFAOYSA-N Siduron Chemical compound CC1CCCCC1NC(=O)NC1=CC=CC=C1 JXVIIQLNUPXOII-UHFFFAOYSA-N 0.000 description 1
- LGDAGYXJBDILKZ-UHFFFAOYSA-N [2-methyl-1,1-dioxo-3-(pyridin-2-ylcarbamoyl)-1$l^{6},2-benzothiazin-4-yl] 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 LGDAGYXJBDILKZ-UHFFFAOYSA-N 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 235000011399 aloe vera Nutrition 0.000 description 1
- 238000012863 analytical testing Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000012505 colouration Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 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 description 1
- 238000002474 experimental method Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229930182480 glucuronide Natural products 0.000 description 1
- 150000008134 glucuronides Chemical class 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 238000000097 high energy electron diffraction Methods 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- GRVOTVYEFDAHCL-RTSZDRIGSA-N morphine sulfate pentahydrate Chemical compound O.O.O.O.O.OS(O)(=O)=O.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O GRVOTVYEFDAHCL-RTSZDRIGSA-N 0.000 description 1
- 208000004296 neuralgia Diseases 0.000 description 1
- 208000021722 neuropathic pain Diseases 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000004686 pentahydrates Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000002636 symptomatic treatment Methods 0.000 description 1
- 235000012976 tarts Nutrition 0.000 description 1
- 238000012956 testing procedure Methods 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 230000000007 visual effect Effects 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Epidemiology (AREA)
- Neurosurgery (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0218811.8A GB0218811D0 (en) | 2002-08-14 | 2002-08-14 | Salts of morphine-6-glucuronide |
| PCT/GB2003/003562 WO2004016633A1 (en) | 2002-08-14 | 2003-08-14 | Salt of morphine-6-glucuronide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200501053B true ZA200501053B (en) | 2005-10-26 |
Family
ID=9942230
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA2005/01053A ZA200501053B (en) | 2002-08-14 | 2005-02-04 | Salt of morphine-6-glucuronide |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US20060166900A1 (enExample) |
| EP (1) | EP1537132B1 (enExample) |
| JP (1) | JP4727990B2 (enExample) |
| KR (1) | KR101077501B1 (enExample) |
| AT (1) | ATE315041T1 (enExample) |
| AU (1) | AU2003255790B2 (enExample) |
| CA (1) | CA2494812C (enExample) |
| DE (1) | DE60303149T2 (enExample) |
| DK (1) | DK1537132T3 (enExample) |
| EA (1) | EA008212B1 (enExample) |
| ES (1) | ES2256790T3 (enExample) |
| GB (1) | GB0218811D0 (enExample) |
| IL (1) | IL166596A0 (enExample) |
| NO (1) | NO20051261L (enExample) |
| PL (1) | PL211031B1 (enExample) |
| WO (1) | WO2004016633A1 (enExample) |
| ZA (1) | ZA200501053B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2578626C (en) | 2005-06-27 | 2011-07-19 | Biovail Laboratories International S.R.L. | Modified-release formulations of a bupropion salt |
| FR2939437B1 (fr) * | 2008-12-10 | 2010-12-17 | Sanofi Aventis | Derives de morphine-6-glucuronide, leur preparation et leur application en therapeutique |
| FR2939796B1 (fr) * | 2008-12-11 | 2010-12-17 | Sanofi Aventis | Derives bicycliques de morphine-6-glucuronide, leur preparation et leur application en therapeutique |
| CN107028968B (zh) * | 2016-02-03 | 2020-12-04 | 江苏恒瑞医药股份有限公司 | 一种含有葡萄糖醛酸吗啡或其可药用盐的药物组合物 |
| CA3041308A1 (en) | 2016-10-21 | 2018-04-26 | Somniferum Labs LLC | Method, system and apparatus for controlled delivery of opioid and other medications |
| CN110054656B (zh) * | 2019-05-28 | 2021-02-02 | 宜昌人福药业有限责任公司 | 一种10-羰基/羟基吗啡-6-葡萄糖苷酸的合成方法 |
| CN113831373B (zh) * | 2020-06-23 | 2023-05-16 | 宜昌人福药业有限责任公司 | 一种吗啡-6-葡萄糖苷酸脱水物杂质的合成方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4908389A (en) * | 1986-08-27 | 1990-03-13 | Warner-Lambert Company | Penetration enhancement system |
| FR2680786B1 (fr) * | 1991-09-04 | 1995-03-10 | Irepa | Procede de synthese de glucuronides d'epoxy-4,5 morphinanes. |
| DE4403709A1 (de) * | 1994-02-07 | 1995-08-10 | Lohmann Therapie Syst Lts | Pharmazeutische Zusammensetzung zur systemischen transdermalen Verabreichung mit dem Wirkstoff Morphin-6-glucuronid |
| US5460826A (en) * | 1994-06-27 | 1995-10-24 | Alza Corporation | Morphine therapy |
| WO1997021416A2 (es) * | 1995-11-29 | 1997-06-19 | Rolabo Sl | Glicoconjugados de substancias opiaceas |
| IL134787A (en) * | 1997-09-25 | 2007-05-15 | Lohmann Therapie Syst Lts | Acid addition salts of morphine alkaloids, their preparation and pharmaceutical compositions containing them for trandermal and transmucosal application |
| US6740641B2 (en) * | 2001-07-27 | 2004-05-25 | Euro-Celtique, S.A. | Sugar derivatives of hydromorphone, dihydromorphine and dihydromorphine, compositions thereof and uses for treating or preventing pain |
-
2002
- 2002-08-14 GB GBGB0218811.8A patent/GB0218811D0/en not_active Ceased
-
2003
- 2003-08-14 KR KR1020057002442A patent/KR101077501B1/ko not_active Expired - Fee Related
- 2003-08-14 PL PL373553A patent/PL211031B1/pl unknown
- 2003-08-14 EP EP03787894A patent/EP1537132B1/en not_active Expired - Lifetime
- 2003-08-14 WO PCT/GB2003/003562 patent/WO2004016633A1/en not_active Ceased
- 2003-08-14 AU AU2003255790A patent/AU2003255790B2/en not_active Ceased
- 2003-08-14 CA CA2494812A patent/CA2494812C/en not_active Expired - Fee Related
- 2003-08-14 DK DK03787894T patent/DK1537132T3/da active
- 2003-08-14 DE DE60303149T patent/DE60303149T2/de not_active Expired - Lifetime
- 2003-08-14 AT AT03787894T patent/ATE315041T1/de active
- 2003-08-14 ES ES03787894T patent/ES2256790T3/es not_active Expired - Lifetime
- 2003-08-14 JP JP2004528672A patent/JP4727990B2/ja not_active Expired - Fee Related
- 2003-08-14 EA EA200500175A patent/EA008212B1/ru not_active IP Right Cessation
- 2003-08-14 US US10/524,149 patent/US20060166900A1/en not_active Abandoned
-
2005
- 2005-01-31 IL IL16659605A patent/IL166596A0/xx not_active IP Right Cessation
- 2005-02-04 ZA ZA2005/01053A patent/ZA200501053B/en unknown
- 2005-03-11 NO NO20051261A patent/NO20051261L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003255790B2 (en) | 2010-05-27 |
| JP2006500360A (ja) | 2006-01-05 |
| CA2494812C (en) | 2011-03-08 |
| PL373553A1 (en) | 2005-09-05 |
| EP1537132A1 (en) | 2005-06-08 |
| CA2494812A1 (en) | 2004-02-26 |
| PL211031B1 (pl) | 2012-04-30 |
| DE60303149T2 (de) | 2006-09-28 |
| KR20050055710A (ko) | 2005-06-13 |
| EA200500175A1 (ru) | 2005-08-25 |
| ES2256790T3 (es) | 2006-07-16 |
| DE60303149D1 (de) | 2006-03-30 |
| KR101077501B1 (ko) | 2011-10-28 |
| US20060166900A1 (en) | 2006-07-27 |
| ATE315041T1 (de) | 2006-02-15 |
| NO20051261L (no) | 2005-03-11 |
| JP4727990B2 (ja) | 2011-07-20 |
| AU2003255790A1 (en) | 2004-03-03 |
| EP1537132B1 (en) | 2006-01-04 |
| GB0218811D0 (en) | 2002-09-18 |
| EA008212B1 (ru) | 2007-04-27 |
| WO2004016633A1 (en) | 2004-02-26 |
| DK1537132T3 (da) | 2006-05-08 |
| IL166596A0 (en) | 2006-01-15 |
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