JP2006516578A - キナゾリンアルカロイドの製造方法 - Google Patents
キナゾリンアルカロイドの製造方法 Download PDFInfo
- Publication number
- JP2006516578A JP2006516578A JP2006501573A JP2006501573A JP2006516578A JP 2006516578 A JP2006516578 A JP 2006516578A JP 2006501573 A JP2006501573 A JP 2006501573A JP 2006501573 A JP2006501573 A JP 2006501573A JP 2006516578 A JP2006516578 A JP 2006516578A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- iii
- salt
- process according
- hours
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 18
- 229930002339 quinazoline alkaloid Natural products 0.000 title description 4
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 65
- 238000000034 method Methods 0.000 claims abstract description 59
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims abstract description 23
- 150000003839 salts Chemical group 0.000 claims abstract description 19
- 238000006722 reduction reaction Methods 0.000 claims abstract description 17
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 238000002425 crystallisation Methods 0.000 claims description 22
- 230000008025 crystallization Effects 0.000 claims description 21
- 239000011541 reaction mixture Substances 0.000 claims description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 239000013078 crystal Substances 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 9
- 239000011701 zinc Substances 0.000 claims description 8
- 229910052725 zinc Inorganic materials 0.000 claims description 8
- 229960000583 acetic acid Drugs 0.000 claims description 7
- 239000012362 glacial acetic acid Substances 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- 239000012458 free base Substances 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 239000012670 alkaline solution Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- VARHXCYGZKSOOO-UHFFFAOYSA-N Deoxyvasicinone Natural products C1=CC=C2C(=O)N(CCC3)C3=NC2=C1 VARHXCYGZKSOOO-UHFFFAOYSA-N 0.000 description 60
- WUFQLZTXIWKION-UHFFFAOYSA-N Deoxypeganine Chemical compound C1C2=CC=CC=C2N=C2N1CCC2 WUFQLZTXIWKION-UHFFFAOYSA-N 0.000 description 42
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- KTCXMTWSISEJFZ-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-pyrrolo[2,1-b]quinazolin-10-ium;chloride Chemical compound Cl.C1C2=CC=CC=C2N=C2N1CCC2 KTCXMTWSISEJFZ-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 150000003246 quinazolines Chemical class 0.000 description 3
- 239000012047 saturated solution Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- YIICVSCAKJMMDJ-JTQLQIEISA-N (3s)-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-3-ol Chemical compound C1=CC=C2N=C3[C@@H](O)CCN3CC2=C1 YIICVSCAKJMMDJ-JTQLQIEISA-N 0.000 description 1
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical compound NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 description 1
- SYLRFDTUTMLVNM-UHFFFAOYSA-N 4-phenoxybutanoyl chloride Chemical compound ClC(=O)CCCOC1=CC=CC=C1 SYLRFDTUTMLVNM-UHFFFAOYSA-N 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 241000256186 Anopheles <genus> Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229910000669 Chrome steel Inorganic materials 0.000 description 1
- KLHYPYAETJWSBK-UHFFFAOYSA-J Cl[Zn](Cl)(Cl)Cl Chemical class Cl[Zn](Cl)(Cl)Cl KLHYPYAETJWSBK-UHFFFAOYSA-J 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 229940123685 Monoamine oxidase inhibitor Drugs 0.000 description 1
- 206010057852 Nicotine dependence Diseases 0.000 description 1
- 240000005523 Peganum harmala Species 0.000 description 1
- 235000005126 Peganum harmala Nutrition 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 208000025569 Tobacco Use disease Diseases 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000000544 cholinesterase inhibitor Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 206010013663 drug dependence Diseases 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000002899 monoamine oxidase inhibitor Substances 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- -1 phenoxyl group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Addiction (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10304141A DE10304141B4 (de) | 2003-02-03 | 2003-02-03 | Verfahren zur Herstellung von Chinazolin-Alkaloiden |
| PCT/EP2004/000485 WO2004069836A1 (de) | 2003-02-03 | 2004-01-22 | Verfahren zur herstellung von chinazolin-alkaloiden |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006516578A true JP2006516578A (ja) | 2006-07-06 |
| JP2006516578A5 JP2006516578A5 (https=) | 2007-02-08 |
Family
ID=32747532
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006501573A Pending JP2006516578A (ja) | 2003-02-03 | 2004-01-22 | キナゾリンアルカロイドの製造方法 |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US7495096B2 (https=) |
| EP (1) | EP1590351B1 (https=) |
| JP (1) | JP2006516578A (https=) |
| KR (1) | KR20050096165A (https=) |
| CN (1) | CN100558727C (https=) |
| AR (1) | AR042946A1 (https=) |
| AT (1) | ATE407135T1 (https=) |
| AU (1) | AU2004208873B2 (https=) |
| BR (1) | BRPI0407012A (https=) |
| CA (1) | CA2514945A1 (https=) |
| DE (2) | DE10304141B4 (https=) |
| DK (1) | DK1590351T3 (https=) |
| EA (1) | EA009047B1 (https=) |
| ES (1) | ES2314366T3 (https=) |
| MX (1) | MXPA05008179A (https=) |
| MY (1) | MY141734A (https=) |
| NO (1) | NO20053689L (https=) |
| NZ (1) | NZ541101A (https=) |
| PL (1) | PL378406A1 (https=) |
| PT (1) | PT1590351E (https=) |
| SI (1) | SI1590351T1 (https=) |
| TW (1) | TW200418811A (https=) |
| UA (1) | UA81287C2 (https=) |
| WO (1) | WO2004069836A1 (https=) |
| ZA (1) | ZA200505160B (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004048927A1 (de) * | 2004-10-06 | 2006-04-20 | Lts Lohmann Therapie-Systeme Ag | Pharmazeutische Kombination enthaltend Desoxypeganin und Cyp2D6 Inhibitoren |
| EP3661502A4 (en) | 2017-08-03 | 2020-12-02 | Galectin Sciences, LLC | COMPOUNDS FOR THE PREVENTION AND TREATMENT OF MEDICAL CONDITIONS AND THEIR USES |
| KR102728780B1 (ko) * | 2021-11-30 | 2024-11-08 | 이화여자대학교 산학협력단 | 데옥시바시시논을 유효성분으로 포함하는 미백용 조성물 및 상기 데옥시바시시논 제조방법 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH069644A (ja) * | 1991-08-30 | 1994-01-18 | New Japan Chem Co Ltd | ジアセタール化合物の製造方法 |
| JPH11246853A (ja) * | 1997-10-31 | 1999-09-14 | Dainichiseika Color & Chem Mfg Co Ltd | 新規化学発光試薬及びその製造方法 |
| JPH11511155A (ja) * | 1995-08-21 | 1999-09-28 | ビーエーエスエフ アクチェンゲゼルシャフト | １−（ピリジル）ピラゾール |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU605614A1 (ru) * | 1971-10-20 | 1978-05-05 | Ордена Трудового Красного Знамени Институт Химии Растительных Веществ Ан Узбекской Сср | Антихолинэстеразное средство |
| DE19906975B4 (de) | 1999-02-19 | 2004-04-15 | Lts Lohmann Therapie-Systeme Ag | Arzneiform zur Behandlung von Alzheimer'scher Demenz |
| DE19906979B4 (de) | 1999-02-19 | 2004-07-08 | Lts Lohmann Therapie-Systeme Ag | Verwendung von Desoxypeganin zur Behandlung der Nikotinabhängigkeit |
| DE19906978B4 (de) | 1999-02-19 | 2004-07-08 | Lts Lohmann Therapie-Systeme Ag | Pharmazeutische Zusammensetzung enthaltend Desoxypeganin zur Behandlung der Drogenabhängigkeit |
-
2003
- 2003-02-03 DE DE10304141A patent/DE10304141B4/de not_active Expired - Fee Related
-
2004
- 2004-01-22 DK DK04704202T patent/DK1590351T3/da active
- 2004-01-22 DE DE502004007980T patent/DE502004007980D1/de not_active Expired - Lifetime
- 2004-01-22 EA EA200501135A patent/EA009047B1/ru not_active IP Right Cessation
- 2004-01-22 AT AT04704202T patent/ATE407135T1/de active
- 2004-01-22 KR KR1020057013954A patent/KR20050096165A/ko not_active Ceased
- 2004-01-22 AU AU2004208873A patent/AU2004208873B2/en not_active Ceased
- 2004-01-22 WO PCT/EP2004/000485 patent/WO2004069836A1/de not_active Ceased
- 2004-01-22 US US10/544,265 patent/US7495096B2/en not_active Expired - Fee Related
- 2004-01-22 CN CNB2004800034182A patent/CN100558727C/zh not_active Expired - Fee Related
- 2004-01-22 ES ES04704202T patent/ES2314366T3/es not_active Expired - Lifetime
- 2004-01-22 NZ NZ541101A patent/NZ541101A/en not_active IP Right Cessation
- 2004-01-22 PL PL378406A patent/PL378406A1/pl not_active Application Discontinuation
- 2004-01-22 BR BR0407012-7A patent/BRPI0407012A/pt not_active Application Discontinuation
- 2004-01-22 JP JP2006501573A patent/JP2006516578A/ja active Pending
- 2004-01-22 EP EP04704202A patent/EP1590351B1/de not_active Expired - Lifetime
- 2004-01-22 CA CA002514945A patent/CA2514945A1/en not_active Abandoned
- 2004-01-22 MX MXPA05008179A patent/MXPA05008179A/es active IP Right Grant
- 2004-01-22 SI SI200430943T patent/SI1590351T1/sl unknown
- 2004-01-22 UA UAA200507716A patent/UA81287C2/uk unknown
- 2004-01-22 PT PT04704202T patent/PT1590351E/pt unknown
- 2004-01-28 AR ARP040100246A patent/AR042946A1/es unknown
- 2004-01-30 MY MYPI20040294A patent/MY141734A/en unknown
- 2004-02-02 TW TW093102290A patent/TW200418811A/zh unknown
-
2005
- 2005-06-24 ZA ZA200505160A patent/ZA200505160B/en unknown
- 2005-07-29 NO NO20053689A patent/NO20053689L/no not_active Application Discontinuation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH069644A (ja) * | 1991-08-30 | 1994-01-18 | New Japan Chem Co Ltd | ジアセタール化合物の製造方法 |
| JPH11511155A (ja) * | 1995-08-21 | 1999-09-28 | ビーエーエスエフ アクチェンゲゼルシャフト | １−（ピリジル）ピラゾール |
| JPH11246853A (ja) * | 1997-10-31 | 1999-09-14 | Dainichiseika Color & Chem Mfg Co Ltd | 新規化学発光試薬及びその製造方法 |
Non-Patent Citations (4)
| Title |
|---|
| JPN5006000891, ＳＰＡＴＨ， Ｅ． ｅｔ ａｌ．, Ｃｈｅｍ． Ｂｅｒ．, 1935, ｐ．２２２１−６ * |
| JPN6010034591, ＪＥＮ， Ｔ． ｅｔ ａｌ．, Ｊ． Ｍｅｄ． Ｃｈｅｍ．, 1973, Ｖｏｌ．１６， Ｎｏ．６, ｐ．６３３−７ * |
| JPN6010034592, 浅原照三ほか, 溶剤ハンドブック, 1976, ｐ．７４９−５０ * |
| JPN6010034593, ＭＯＲＲＩＳ， Ｒ．Ｃ． ｅｔ ａｌ．, Ｊ． Ａｍ． Ｃｈｅｍ． Ｓｏｃ．, 1935, Ｖｏｌ．５７, ｐ．９５１−４ * |
Also Published As
| Publication number | Publication date |
|---|---|
| PL378406A1 (pl) | 2006-04-03 |
| EA009047B1 (ru) | 2007-10-26 |
| MXPA05008179A (es) | 2006-02-17 |
| MY141734A (en) | 2010-06-15 |
| AU2004208873B2 (en) | 2009-12-17 |
| HK1075898A1 (zh) | 2005-12-30 |
| DE502004007980D1 (de) | 2008-10-16 |
| ZA200505160B (en) | 2007-01-31 |
| CA2514945A1 (en) | 2004-08-19 |
| US7495096B2 (en) | 2009-02-24 |
| KR20050096165A (ko) | 2005-10-05 |
| UA81287C2 (en) | 2007-12-25 |
| EP1590351B1 (de) | 2008-09-03 |
| EA200501135A1 (ru) | 2006-02-24 |
| ES2314366T3 (es) | 2009-03-16 |
| AU2004208873A1 (en) | 2004-08-19 |
| WO2004069836A1 (de) | 2004-08-19 |
| US20060084669A1 (en) | 2006-04-20 |
| BRPI0407012A (pt) | 2006-01-10 |
| DK1590351T3 (da) | 2008-12-15 |
| PT1590351E (pt) | 2008-11-21 |
| DE10304141B4 (de) | 2006-03-09 |
| CN100558727C (zh) | 2009-11-11 |
| AR042946A1 (es) | 2005-07-06 |
| TW200418811A (en) | 2004-10-01 |
| DE10304141A1 (de) | 2004-08-26 |
| EP1590351A1 (de) | 2005-11-02 |
| NZ541101A (en) | 2009-03-31 |
| SI1590351T1 (sl) | 2009-02-28 |
| ATE407135T1 (de) | 2008-09-15 |
| NO20053689L (no) | 2005-07-29 |
| CN1745084A (zh) | 2006-03-08 |
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