ZA200105825B - Method for preparing an aza-macrolide with 4" (R) NH2. - Google Patents
Method for preparing an aza-macrolide with 4" (R) NH2. Download PDFInfo
- Publication number
- ZA200105825B ZA200105825B ZA200105825A ZA200105825A ZA200105825B ZA 200105825 B ZA200105825 B ZA 200105825B ZA 200105825 A ZA200105825 A ZA 200105825A ZA 200105825 A ZA200105825 A ZA 200105825A ZA 200105825 B ZA200105825 B ZA 200105825B
- Authority
- ZA
- South Africa
- Prior art keywords
- general formula
- compound
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- substituted
- process according
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 28
- 239000003120 macrolide antibiotic agent Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 67
- 230000008569 process Effects 0.000 claims abstract description 25
- 230000000269 nucleophilic effect Effects 0.000 claims abstract description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- 230000000707 stereoselective effect Effects 0.000 claims abstract description 9
- 238000006073 displacement reaction Methods 0.000 claims abstract description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 150000001540 azides Chemical class 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- GMRIOAVKKGNMMV-UHFFFAOYSA-N tetrabutylazanium;azide Chemical group [N-]=[N+]=[N-].CCCC[N+](CCCC)(CCCC)CCCC GMRIOAVKKGNMMV-UHFFFAOYSA-N 0.000 claims description 6
- OALSNYDESGVYDZ-UHFFFAOYSA-N tetraoctylazanium;azide Chemical compound [N-]=[N+]=[N-].CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC OALSNYDESGVYDZ-UHFFFAOYSA-N 0.000 claims description 6
- 230000004913 activation Effects 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 230000009467 reduction Effects 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- -1 sulphonimides Chemical class 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 238000011065 in-situ storage Methods 0.000 claims description 3
- 239000012038 nucleophile Substances 0.000 claims description 3
- 230000003213 activating effect Effects 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 239000003849 aromatic solvent Substances 0.000 claims description 2
- MBOBEQIPNVBHFP-UHFFFAOYSA-N azidophosphane Chemical compound PN=[N+]=[N-] MBOBEQIPNVBHFP-UHFFFAOYSA-N 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 150000002429 hydrazines Chemical class 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 150000003949 imides Chemical class 0.000 claims description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 2
- 150000003456 sulfonamides Chemical class 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical group OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 2
- 101100087393 Caenorhabditis elegans ran-2 gene Proteins 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 abstract description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 229960003276 erythromycin Drugs 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 4
- 229930006677 Erythromycin A Natural products 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 4
- AJSDVNKVGFVAQU-BIIVOSGPSA-N cladinose Chemical group O=CC[C@@](C)(OC)[C@@H](O)[C@H](C)O AJSDVNKVGFVAQU-BIIVOSGPSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical group 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000006237 Beckmann rearrangement reaction Methods 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 101100167365 Caenorhabditis elegans cha-1 gene Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 101100113485 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) chs-3 gene Proteins 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- DSQCNXSPLHDLED-UHFFFAOYSA-M methanesulfonate;tetrabutylphosphanium Chemical compound CS([O-])(=O)=O.CCCC[P+](CCCC)(CCCC)CCCC DSQCNXSPLHDLED-UHFFFAOYSA-M 0.000 description 1
- QWYMUVSVJFMERY-UHFFFAOYSA-M methanesulfonate;tetraoctylazanium Chemical compound CS([O-])(=O)=O.CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC QWYMUVSVJFMERY-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
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- 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
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Steroid Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9900459A FR2788524B1 (fr) | 1999-01-18 | 1999-01-18 | Procede utile pour transformer la fonction 4"(s)-oh du motif cladinose d'un aza macrolide en 4"(r)-nh2 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200105825B true ZA200105825B (en) | 2002-05-08 |
Family
ID=9540950
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200105825A ZA200105825B (en) | 1999-01-18 | 2001-07-16 | Method for preparing an aza-macrolide with 4" (R) NH2. |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | USRE40040E1 (de) |
| EP (1) | EP1144428B1 (de) |
| JP (1) | JP2003505340A (de) |
| AT (1) | ATE279426T1 (de) |
| AU (1) | AU768838B2 (de) |
| BR (1) | BRPI0007593B8 (de) |
| CA (1) | CA2359967C (de) |
| DE (1) | DE60014849T2 (de) |
| DK (1) | DK1144428T3 (de) |
| ES (1) | ES2232414T3 (de) |
| FR (1) | FR2788524B1 (de) |
| NZ (1) | NZ513025A (de) |
| PT (1) | PT1144428E (de) |
| WO (1) | WO2000042056A1 (de) |
| ZA (1) | ZA200105825B (de) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55151598A (en) * | 1979-05-11 | 1980-11-26 | Taisho Pharmaceut Co Ltd | Erythromycin a derivative and its preparation |
| CA2064634C (en) * | 1991-04-04 | 1998-08-04 | James V. Heck | 9-deoxo-8a-aza-8a-homoerythromycin a derivatives modified at the 4"- and8a-positions |
| EP0549040A1 (de) * | 1991-12-20 | 1993-06-30 | Merck & Co. Inc. | Verfahren zur Herstellung von 4"-Derivaten von 9-Deoxo-8a-Aza-8a-Alkyl-8a-Homoerythromycin A |
| ES2203635T3 (es) * | 1994-04-27 | 2004-04-16 | Novartis Ag | Nucleosidos y oligonucleotidos con grupos 2'-eter. |
| GB9806029D0 (en) * | 1998-03-20 | 1998-05-20 | Merck & Co Inc | 8a-Azalides as veterinary antimicrobial agents |
| JP2003512290A (ja) * | 1997-09-10 | 2003-04-02 | メルク エンド カムパニー インコーポレーテッド | 家畜抗菌剤としての８ａ−アザライド |
-
1999
- 1999-01-18 FR FR9900459A patent/FR2788524B1/fr not_active Expired - Lifetime
-
2000
- 2000-01-17 AU AU19870/00A patent/AU768838B2/en not_active Expired
- 2000-01-17 JP JP2000593623A patent/JP2003505340A/ja active Pending
- 2000-01-17 PT PT00900224T patent/PT1144428E/pt unknown
- 2000-01-17 EP EP00900224A patent/EP1144428B1/de not_active Expired - Lifetime
- 2000-01-17 BR BRPI0007593A patent/BRPI0007593B8/pt not_active IP Right Cessation
- 2000-01-17 ES ES00900224T patent/ES2232414T3/es not_active Expired - Lifetime
- 2000-01-17 DE DE60014849T patent/DE60014849T2/de not_active Expired - Lifetime
- 2000-01-17 DK DK00900224T patent/DK1144428T3/da active
- 2000-01-17 WO PCT/FR2000/000089 patent/WO2000042056A1/fr active IP Right Grant
- 2000-01-17 NZ NZ513025A patent/NZ513025A/en not_active IP Right Cessation
- 2000-01-17 CA CA2359967A patent/CA2359967C/en not_active Expired - Lifetime
- 2000-01-17 AT AT00900224T patent/ATE279426T1/de active
-
2001
- 2001-07-16 ZA ZA200105825A patent/ZA200105825B/en unknown
-
2005
- 2005-09-09 US US11/223,912 patent/USRE40040E1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1144428B1 (de) | 2004-10-13 |
| DE60014849T2 (de) | 2006-03-09 |
| NZ513025A (en) | 2003-11-28 |
| BR0007593B1 (pt) | 2014-01-28 |
| DE60014849D1 (de) | 2004-11-18 |
| PT1144428E (pt) | 2005-02-28 |
| FR2788524A1 (fr) | 2000-07-21 |
| ATE279426T1 (de) | 2004-10-15 |
| AU1987000A (en) | 2000-08-01 |
| CA2359967C (en) | 2011-08-30 |
| WO2000042056A1 (fr) | 2000-07-20 |
| AU768838B2 (en) | 2004-01-08 |
| DK1144428T3 (da) | 2005-02-14 |
| JP2003505340A (ja) | 2003-02-12 |
| USRE40040E1 (en) | 2008-01-29 |
| FR2788524B1 (fr) | 2002-04-26 |
| EP1144428A1 (de) | 2001-10-17 |
| CA2359967A1 (en) | 2000-07-20 |
| ES2232414T3 (es) | 2005-06-01 |
| BR0007593A (pt) | 2001-11-06 |
| BRPI0007593B8 (pt) | 2021-05-25 |
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