AU2004208873B2 - Methods for producing quinazoline alkaloids - Google Patents
Methods for producing quinazoline alkaloids Download PDFInfo
- Publication number
- AU2004208873B2 AU2004208873B2 AU2004208873A AU2004208873A AU2004208873B2 AU 2004208873 B2 AU2004208873 B2 AU 2004208873B2 AU 2004208873 A AU2004208873 A AU 2004208873A AU 2004208873 A AU2004208873 A AU 2004208873A AU 2004208873 B2 AU2004208873 B2 AU 2004208873B2
- Authority
- AU
- Australia
- Prior art keywords
- compound
- iii
- process according
- salt
- production
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 63
- 229930002339 quinazoline alkaloid Natural products 0.000 title 1
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 62
- 230000008569 process Effects 0.000 claims description 48
- 238000004519 manufacturing process Methods 0.000 claims description 25
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 22
- 150000003839 salts Chemical group 0.000 claims description 22
- 238000002425 crystallisation Methods 0.000 claims description 20
- 239000011541 reaction mixture Substances 0.000 claims description 18
- 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
- 239000013078 crystal Substances 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 11
- 238000006722 reduction reaction Methods 0.000 claims description 11
- 239000011701 zinc Substances 0.000 claims description 9
- 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
- 238000010438 heat treatment Methods 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 239000012458 free base Substances 0.000 claims description 4
- 230000008014 freezing Effects 0.000 claims description 4
- 238000007710 freezing Methods 0.000 claims description 4
- 239000012670 alkaline solution Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- VARHXCYGZKSOOO-UHFFFAOYSA-N Deoxyvasicinone Natural products C1=CC=C2C(=O)N(CCC3)C3=NC2=C1 VARHXCYGZKSOOO-UHFFFAOYSA-N 0.000 description 58
- 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
- 239000000047 product Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- TXJUTRJFNRYTHH-UHFFFAOYSA-N 1h-3,1-benzoxazine-2,4-dione Chemical compound C1=CC=C2C(=O)OC(=O)NC2=C1 TXJUTRJFNRYTHH-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000007858 starting material Substances 0.000 description 6
- 125000003790 chinazolinyl group Chemical group 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000003786 synthesis reaction 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
- 238000006214 Clemmensen reduction reaction Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
- 229910000669 Chrome steel Inorganic materials 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 239000012047 saturated solution Substances 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- YIICVSCAKJMMDJ-UHFFFAOYSA-N L-vasicine Natural products C1=CC=C2N=C3C(O)CCN3CC2=C1 YIICVSCAKJMMDJ-UHFFFAOYSA-N 0.000 description 2
- YIICVSCAKJMMDJ-SNVBAGLBSA-N Peganine Chemical compound C1=CC=C2N=C3[C@H](O)CCN3CC2=C1 YIICVSCAKJMMDJ-SNVBAGLBSA-N 0.000 description 2
- YIICVSCAKJMMDJ-JTQLQIEISA-N Peganine Natural products C1=CC=C2N=C3[C@@H](O)CCN3CC2=C1 YIICVSCAKJMMDJ-JTQLQIEISA-N 0.000 description 2
- 240000005523 Peganum harmala Species 0.000 description 2
- 235000005126 Peganum harmala Nutrition 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 206010013663 drug dependence Diseases 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000013067 intermediate product Substances 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
- 239000002904 solvent Substances 0.000 description 2
- 208000011117 substance-related disease Diseases 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-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
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 102000010909 Monoamine Oxidase Human genes 0.000 description 1
- 108010062431 Monoamine oxidase Proteins 0.000 description 1
- 206010057852 Nicotine dependence Diseases 0.000 description 1
- 241000183024 Populus tremula Species 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 208000025569 Tobacco Use disease Diseases 0.000 description 1
- 241000159213 Zygophyllaceae Species 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000008901 benefit Effects 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
- 238000006757 chemical reactions by type Methods 0.000 description 1
- 239000000544 cholinesterase inhibitor Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940035564 duration Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification 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
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 230000002194 synthesizing effect Effects 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10304141A DE10304141B4 (de) | 2003-02-03 | 2003-02-03 | Verfahren zur Herstellung von Chinazolin-Alkaloiden |
| DE10304141.9 | 2003-02-03 | ||
| PCT/EP2004/000485 WO2004069836A1 (de) | 2003-02-03 | 2004-01-22 | Verfahren zur herstellung von chinazolin-alkaloiden |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2004208873A1 AU2004208873A1 (en) | 2004-08-19 |
| AU2004208873B2 true AU2004208873B2 (en) | 2009-12-17 |
Family
ID=32747532
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2004208873A Ceased AU2004208873B2 (en) | 2003-02-03 | 2004-01-22 | Methods for producing quinazoline alkaloids |
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 |
Family Cites Families (7)
| 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 |
| JP3180464B2 (ja) * | 1991-08-30 | 2001-06-25 | 新日本理化株式会社 | ジアセタール化合物の製造方法 |
| DE19530606A1 (de) * | 1995-08-21 | 1997-02-27 | Basf Ag | 1-(Pyridyl)-pyrazole |
| JP3958452B2 (ja) * | 1997-10-31 | 2007-08-15 | 大日精化工業株式会社 | 新規化学発光試薬及びその製造方法 |
| 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
Non-Patent Citations (3)
| Title |
|---|
| Jen et al. J. Med. Chem. 1973, 16(6), 633-637 * |
| Spath et al. Chemische Berichte 1935, 2221-2226 * |
| Yadav et al. Tetrahetron Lett. 2002, 43, 1905-1907 * |
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 |
| 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 |
| JP2006516578A (ja) | 2006-07-06 |
| 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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