NO328559B1 - Taksanderivatkrystall og fremgangsmate for fremstilling derav, samt antitumormiddel som omfatter krystallet - Google Patents
Taksanderivatkrystall og fremgangsmate for fremstilling derav, samt antitumormiddel som omfatter krystallet Download PDFInfo
- Publication number
- NO328559B1 NO328559B1 NO20042723A NO20042723A NO328559B1 NO 328559 B1 NO328559 B1 NO 328559B1 NO 20042723 A NO20042723 A NO 20042723A NO 20042723 A NO20042723 A NO 20042723A NO 328559 B1 NO328559 B1 NO 328559B1
- Authority
- NO
- Norway
- Prior art keywords
- mixture
- crystal
- water
- crystals
- present
- Prior art date
Links
- 239000013078 crystal Substances 0.000 title claims abstract description 94
- 238000000034 method Methods 0.000 title claims abstract description 14
- 239000002246 antineoplastic agent Substances 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 9
- DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 title description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 54
- 239000000203 mixture Substances 0.000 claims abstract description 44
- 239000002904 solvent Substances 0.000 claims abstract description 26
- 238000002425 crystallisation Methods 0.000 claims abstract description 18
- 230000008025 crystallization Effects 0.000 claims abstract description 18
- 239000003960 organic solvent Substances 0.000 claims abstract description 16
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 57
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 45
- 239000003814 drug Substances 0.000 claims description 12
- 229940079593 drug Drugs 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 11
- 238000001035 drying Methods 0.000 claims description 5
- WCMBUDUPBVQEDN-VHSXEESVSA-N (2r,3s)-3-(3-fluoropyridin-2-yl)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H]([C@@H](O)C(O)=O)C1=NC=CC=C1F WCMBUDUPBVQEDN-VHSXEESVSA-N 0.000 abstract description 2
- 150000002576 ketones Chemical class 0.000 abstract description 2
- 150000002825 nitriles Chemical class 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 25
- 239000000126 substance Substances 0.000 description 17
- 238000003756 stirring Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000001914 filtration Methods 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 238000004455 differential thermal analysis Methods 0.000 description 4
- 238000002411 thermogravimetry Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 230000000259 anti-tumor effect Effects 0.000 description 3
- -1 fusion drips Substances 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 239000007884 disintegrant Substances 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 102000029749 Microtubule Human genes 0.000 description 1
- 108091022875 Microtubule Proteins 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 229930012538 Paclitaxel Natural products 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 229940084030 carboxymethylcellulose calcium Drugs 0.000 description 1
- 230000032823 cell division Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007951 isotonicity adjuster Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 210000001853 liver microsome Anatomy 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 210000004688 microtubule Anatomy 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 229960001592 paclitaxel Drugs 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 102000054765 polymorphisms of proteins Human genes 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
- 150000004579 taxol derivatives Chemical class 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- 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
- A61K31/443—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with oxygen as a ring hetero atom
-
- 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
- C07D493/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001363681 | 2001-11-29 | ||
| PCT/JP2002/012506 WO2003045953A1 (fr) | 2001-11-29 | 2002-11-29 | Cristaux de derive de taxane et procede de production associe |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO20042723L NO20042723L (no) | 2004-06-28 |
| NO328559B1 true NO328559B1 (no) | 2010-03-22 |
Family
ID=19173983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20042723A NO328559B1 (no) | 2001-11-29 | 2004-06-28 | Taksanderivatkrystall og fremgangsmate for fremstilling derav, samt antitumormiddel som omfatter krystallet |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US7410980B2 (ko) |
| EP (1) | EP1457492B1 (ko) |
| JP (1) | JP4310191B2 (ko) |
| KR (1) | KR100886805B1 (ko) |
| CN (1) | CN1295229C (ko) |
| AT (1) | ATE382624T1 (ko) |
| AU (1) | AU2002354126A1 (ko) |
| CA (1) | CA2468953C (ko) |
| DE (1) | DE60224440T2 (ko) |
| DK (1) | DK1457492T3 (ko) |
| ES (1) | ES2299612T3 (ko) |
| HK (1) | HK1065547A1 (ko) |
| MX (1) | MXPA04005192A (ko) |
| NO (1) | NO328559B1 (ko) |
| PT (1) | PT1457492E (ko) |
| RU (1) | RU2284328C2 (ko) |
| TW (1) | TWI333856B (ko) |
| WO (1) | WO2003045953A1 (ko) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2859996B1 (fr) * | 2003-09-19 | 2006-02-03 | Aventis Pharma Sa | Solvat acetonique du dimethoxy docetaxel et son procede de preparation |
| WO2005105807A1 (ja) * | 2004-04-30 | 2005-11-10 | Daiichi Pharmaceutical Co., Ltd. | 五環性タキサンの製造方法 |
| WO2007005829A2 (en) * | 2005-07-01 | 2007-01-11 | Nec Laboratories America, Inc. | Operating system-based memory compression for embedded systems |
| US8697892B2 (en) | 2010-06-30 | 2014-04-15 | Gfv, Llc | Taxane compounds, compositions and methods |
| US8785669B2 (en) | 2010-06-30 | 2014-07-22 | Gfv, Llc | Taxane compounds, compositions and methods |
| EP2447268A1 (en) * | 2010-10-29 | 2012-05-02 | INDENA S.p.A. | Crystalline form of 13-[(N-tert-butoxycarbonyl)-2'-O-hexanoyl-3-phenylisoserinyl]-10-deacetylbaccatin III |
| JP5909089B2 (ja) * | 2011-02-01 | 2016-04-26 | アークレイ株式会社 | 光学結晶、テラヘルツ波発生装置及び方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW480262B (en) | 1995-04-28 | 2002-03-21 | Daiichi Seiyaku Co | A taxol derivative having an antitumor activity and a pharmaceutical composition comprising the same |
| JP2000159757A (ja) | 1998-12-01 | 2000-06-13 | Dai Ichi Seiyaku Co Ltd | ７−デオキシタキソール誘導体の製造方法 |
| JP2002544269A (ja) * | 1999-05-17 | 2002-12-24 | ブリストル−マイヤーズ スクイブ カンパニー | パクリタキセルおよびパクリタキセル類似体の製造におけるシリルエーテルの切断のための新規反応条件 |
| US6677456B2 (en) | 1999-10-15 | 2004-01-13 | Daiichi Pharmaceutical Co., Ltd. | Pentacyclic taxan compound |
| MY125378A (en) | 1999-10-15 | 2006-07-31 | Daiichi Sankyo Co Ltd | Pentacyclic taxan compound |
| US7126003B2 (en) | 2001-03-07 | 2006-10-24 | Daiichi Pharmaceutical Co., Ltd. | Method for producing 2-azetidinone derivative |
-
2002
- 2002-11-29 EP EP02785977A patent/EP1457492B1/en not_active Expired - Lifetime
- 2002-11-29 TW TW091134817A patent/TWI333856B/zh not_active IP Right Cessation
- 2002-11-29 KR KR1020047008200A patent/KR100886805B1/ko not_active IP Right Cessation
- 2002-11-29 DE DE60224440T patent/DE60224440T2/de not_active Expired - Lifetime
- 2002-11-29 AU AU2002354126A patent/AU2002354126A1/en not_active Abandoned
- 2002-11-29 ES ES02785977T patent/ES2299612T3/es not_active Expired - Lifetime
- 2002-11-29 DK DK02785977T patent/DK1457492T3/da active
- 2002-11-29 JP JP2003547403A patent/JP4310191B2/ja not_active Expired - Fee Related
- 2002-11-29 CA CA2468953A patent/CA2468953C/en not_active Expired - Lifetime
- 2002-11-29 AT AT02785977T patent/ATE382624T1/de active
- 2002-11-29 CN CNB02823815XA patent/CN1295229C/zh not_active Expired - Fee Related
- 2002-11-29 RU RU2004119547/04A patent/RU2284328C2/ru active IP Right Revival
- 2002-11-29 PT PT02785977T patent/PT1457492E/pt unknown
- 2002-11-29 WO PCT/JP2002/012506 patent/WO2003045953A1/ja active IP Right Grant
- 2002-11-29 US US10/495,437 patent/US7410980B2/en not_active Expired - Lifetime
- 2002-11-29 MX MXPA04005192A patent/MXPA04005192A/es active IP Right Grant
-
2004
- 2004-06-28 NO NO20042723A patent/NO328559B1/no not_active IP Right Cessation
- 2004-10-28 HK HK04108450A patent/HK1065547A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE60224440D1 (de) | 2008-02-14 |
| DE60224440T2 (de) | 2009-01-02 |
| CN1295229C (zh) | 2007-01-17 |
| CN1596259A (zh) | 2005-03-16 |
| KR100886805B1 (ko) | 2009-03-05 |
| CA2468953C (en) | 2010-05-11 |
| KR20040081426A (ko) | 2004-09-21 |
| NO20042723L (no) | 2004-06-28 |
| US20050070579A1 (en) | 2005-03-31 |
| EP1457492A4 (en) | 2005-03-23 |
| DK1457492T3 (da) | 2008-05-13 |
| JP4310191B2 (ja) | 2009-08-05 |
| JPWO2003045953A1 (ja) | 2005-04-07 |
| HK1065547A1 (en) | 2005-02-25 |
| ES2299612T3 (es) | 2008-06-01 |
| AU2002354126A1 (en) | 2003-06-10 |
| MXPA04005192A (es) | 2005-02-22 |
| EP1457492B1 (en) | 2008-01-02 |
| ATE382624T1 (de) | 2008-01-15 |
| EP1457492A1 (en) | 2004-09-15 |
| WO2003045953A1 (fr) | 2003-06-05 |
| RU2004119547A (ru) | 2005-03-27 |
| CA2468953A1 (en) | 2003-06-05 |
| RU2284328C2 (ru) | 2006-09-27 |
| TW200301114A (en) | 2003-07-01 |
| US7410980B2 (en) | 2008-08-12 |
| PT1457492E (pt) | 2008-02-28 |
| TWI333856B (en) | 2010-12-01 |
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