RU2003128953A - Деградация эпотилонов - Google Patents
Деградация эпотилонов Download PDFInfo
- Publication number
- RU2003128953A RU2003128953A RU2003128953/04A RU2003128953A RU2003128953A RU 2003128953 A RU2003128953 A RU 2003128953A RU 2003128953/04 A RU2003128953/04 A RU 2003128953/04A RU 2003128953 A RU2003128953 A RU 2003128953A RU 2003128953 A RU2003128953 A RU 2003128953A
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- RU
- Russia
- Prior art keywords
- formula
- compound
- scheme
- epothilone
- iii
- Prior art date
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- 230000015556 catabolic process Effects 0.000 title claims 2
- 238000006731 degradation reaction Methods 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims abstract 31
- 238000000034 method Methods 0.000 claims abstract 13
- 229930013356 epothilone Natural products 0.000 claims abstract 4
- 150000003883 epothilone derivatives Chemical class 0.000 claims abstract 4
- BEFZAMRWPCMWFJ-JRBBLYSQSA-N Epothilone C Natural products O=C1[C@H](C)[C@@H](O)[C@@H](C)CCC/C=C\C[C@@H](/C(=C\c2nc(C)sc2)/C)OC(=O)C[C@H](O)C1(C)C BEFZAMRWPCMWFJ-JRBBLYSQSA-N 0.000 claims 4
- XOZIUKBZLSUILX-SDMHVBBESA-N Epothilone D Natural products O=C1[C@H](C)[C@@H](O)[C@@H](C)CCC/C(/C)=C/C[C@@H](/C(=C\c2nc(C)sc2)/C)OC(=O)C[C@H](O)C1(C)C XOZIUKBZLSUILX-SDMHVBBESA-N 0.000 claims 4
- BEFZAMRWPCMWFJ-UHFFFAOYSA-N desoxyepothilone A Natural products O1C(=O)CC(O)C(C)(C)C(=O)C(C)C(O)C(C)CCCC=CCC1C(C)=CC1=CSC(C)=N1 BEFZAMRWPCMWFJ-UHFFFAOYSA-N 0.000 claims 4
- XOZIUKBZLSUILX-UHFFFAOYSA-N desoxyepothilone B Natural products O1C(=O)CC(O)C(C)(C)C(=O)C(C)C(O)C(C)CCCC(C)=CCC1C(C)=CC1=CSC(C)=N1 XOZIUKBZLSUILX-UHFFFAOYSA-N 0.000 claims 4
- BEFZAMRWPCMWFJ-QJKGZULSSA-N epothilone C Chemical compound O1C(=O)C[C@H](O)C(C)(C)C(=O)[C@H](C)[C@@H](O)[C@@H](C)CCC\C=C/C[C@H]1C(\C)=C\C1=CSC(C)=N1 BEFZAMRWPCMWFJ-QJKGZULSSA-N 0.000 claims 4
- XOZIUKBZLSUILX-GIQCAXHBSA-N epothilone D Chemical compound O1C(=O)C[C@H](O)C(C)(C)C(=O)[C@H](C)[C@@H](O)[C@@H](C)CCC\C(C)=C/C[C@H]1C(\C)=C\C1=CSC(C)=N1 XOZIUKBZLSUILX-GIQCAXHBSA-N 0.000 claims 4
- 239000003054 catalyst Substances 0.000 claims 3
- 238000003776 cleavage reaction Methods 0.000 claims 3
- 230000007017 scission Effects 0.000 claims 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 2
- 239000005977 Ethylene Substances 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 238000005865 alkene metathesis reaction Methods 0.000 claims 2
- 125000004185 ester group Chemical group 0.000 claims 2
- 230000007062 hydrolysis Effects 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 0.000 claims 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims 1
- 108090000371 Esterases Proteins 0.000 claims 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000000855 fermentation Methods 0.000 claims 1
- 230000004151 fermentation Effects 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000000686 lactone group Chemical group 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 238000005649 metathesis reaction Methods 0.000 claims 1
- 229910052750 molybdenum Inorganic materials 0.000 claims 1
- 239000011733 molybdenum Substances 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- -1 p-methoxybenzyl Chemical group 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 229910052707 ruthenium Inorganic materials 0.000 claims 1
- 125000004665 trialkylsilyl group Chemical group 0.000 claims 1
- PNPBGYBHLCEVMK-UHFFFAOYSA-N benzylidene(dichloro)ruthenium;tricyclohexylphosphanium Chemical compound Cl[Ru](Cl)=CC1=CC=CC=C1.C1CCCCC1[PH+](C1CCCCC1)C1CCCCC1.C1CCCCC1[PH+](C1CCCCC1)C1CCCCC1 PNPBGYBHLCEVMK-UHFFFAOYSA-N 0.000 abstract 1
- 239000011984 grubbs catalyst Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/14—Nitrogen or oxygen as hetero atom and at least one other diverse hetero ring atom in the same ring
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
- C12P17/181—Heterocyclic compounds containing oxygen atoms as the only ring heteroatoms in the condensed system, e.g. Salinomycin, Septamycin
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/62—Carboxylic acid esters
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
- Y10T436/141111—Diverse hetero atoms in same or different rings [e.g., alkaloids, opiates, etc.]
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Microbiology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Silicon Polymers (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (11)
1. Способ деградации эпотилона С или эпотилона D, где эпотилон С или эпотилон D подвергают олефиновому метатезу в присутствии этилена и затем, необязательно, гидролизу сложноэфирных групп (схема I).
2. Способ по п.1, где эпотилон С или D является продуктом ферментации.
3. Способ получения эпотилона формулы 9
где
(i) эпотилон формулы 2а (схемы I и II), превращается в соединение формулы 3а (схема II),
(ii) соединение формулы 3а взаимодействует с соединением формулы 6, которое было получено в результате взаимодействия соединения формулы 4 с соединением формулы 5 (схема II); с образованием соединения формулы 7 (схема II),
(iii) соединение формулы 7 взаимодействует в присутствии катализатора Грубба с получением соединения формулы 8а (схема II),
(iv) соединение формулы 8а превращается в соединение формулы 8b (схема II) и
(v) соединение формулы 8b превращается в соединение формулы 9 (схема II).
4. Способ по п.3, где на стадии (i) вначале защищают свободные гидроксильные группы и затем проводят гидролиз сложноэфирных групп.
5. Способ по п.3, где на стадии (iv) удаление защитных групп проводят в кислой среде, предпочтительно, с использованием трифторуксусной кислоты.
6. Способ получения соединения формулы 3b
где
(i) проводят расщепление лактонной группы эпотилона С или эпотилона D,
(ii) продукт расщепления формулы 10 (схема III), необязательно, подвергают этерификации диазометаном и
3,7-гидроксильные группы необязательно защищают, получая соединение формулы 11 (схема III), и
(iii) соединение формулы 11 подвергают олефиновому метатезу и
3,7-гидроксильные группы, необязательно, защищают, получая соединение формулы 3b (схема III).
7. Способ по п.6, где на стадии (i) расщепление проводят эстеразой печени свиньи, или после защиты 3,7-гидроксильных групп, водным основанием.
8. Способ по п.6, где на стадии (iii) в качестве олефина используют этилен и/или в качестве катализатора метатеза используют рутениевый или молибденовый катализатор.
9. Способ по п.3 или 6, где 3,7-гидроксильные группы защищают триалкилсилилом или п-метоксибензилом.
10. Способ по п.6, где соединение формулы 3b далее обрабатывают в соответствии со стадиями от (ii) до (v) п.3.
11. Соединения формул 2, 2a, 3, 3a, 3b, 4, 5, 6, 7, 8, 8a, 8b, 9, 10 и 11, получаемые в соответствии со способом по одному или нескольким из предыдущих пунктов.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01104448.4 | 2001-02-27 | ||
| EP01104448 | 2001-02-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2003128953A true RU2003128953A (ru) | 2005-03-10 |
Family
ID=8176579
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2003128953/04A RU2003128953A (ru) | 2001-02-27 | 2002-02-27 | Деградация эпотилонов |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US7157595B2 (ru) |
| EP (2) | EP1364040B1 (ru) |
| JP (1) | JP2004522801A (ru) |
| KR (1) | KR20030084952A (ru) |
| CN (1) | CN1501980A (ru) |
| AT (2) | ATE325201T1 (ru) |
| BR (1) | BR0207675A (ru) |
| CA (1) | CA2437707A1 (ru) |
| CZ (1) | CZ20032291A3 (ru) |
| DE (2) | DE60213884T2 (ru) |
| HU (1) | HUP0303895A3 (ru) |
| IL (1) | IL157312A0 (ru) |
| MX (1) | MXPA03007466A (ru) |
| NO (1) | NO20033784D0 (ru) |
| NZ (2) | NZ527557A (ru) |
| PL (1) | PL362556A1 (ru) |
| RU (1) | RU2003128953A (ru) |
| WO (1) | WO2002072858A2 (ru) |
| ZA (1) | ZA200306034B (ru) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1386922B1 (en) * | 1996-12-03 | 2012-04-11 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereof, analogues and uses thereof |
| DE19826988A1 (de) * | 1998-06-18 | 1999-12-23 | Biotechnolog Forschung Gmbh | Epothilon-Nebenkomponenten |
| US20020058286A1 (en) * | 1999-02-24 | 2002-05-16 | Danishefsky Samuel J. | Synthesis of epothilones, intermediates thereto and analogues thereof |
| US7649006B2 (en) | 2002-08-23 | 2010-01-19 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto and analogues thereof |
| WO2004018478A2 (en) | 2002-08-23 | 2004-03-04 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto, analogues and uses thereof |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0057736B1 (en) | 1981-02-05 | 1986-11-20 | Phillips Petroleum Company | Olefin disproportionation process and catalyst |
| ES2218328T5 (es) | 1995-11-17 | 2011-11-11 | GESELLSCHAFT FüR BIOTECHNOLOGISCHE FORSCHUNG MBH (GBF) | Derivados de epotilón, su preparación y utilización. |
| EP0923583A1 (de) * | 1996-08-30 | 1999-06-23 | Novartis AG | Verfahren zur herstellung von epothilonen und zwischenprodukte innerhalb des verfahrens |
| US5969145A (en) * | 1996-08-30 | 1999-10-19 | Novartis Ag | Process for the production of epothilones and intermediate products within the process |
| HU229833B1 (en) | 1996-11-18 | 2014-09-29 | Biotechnolog Forschung Gmbh | Epothilone d production process, and its use as cytostatic as well as phytosanitary agents |
| US6441186B1 (en) * | 1996-12-13 | 2002-08-27 | The Scripps Research Institute | Epothilone analogs |
| US6380394B1 (en) * | 1996-12-13 | 2002-04-30 | The Scripps Research Institute | Epothilone analogs |
| ZA981575B (en) * | 1997-02-25 | 1998-09-08 | Biotechnolog Forschung Gmbh | Epothilones which are modified in the side chain |
| US6605599B1 (en) | 1997-07-08 | 2003-08-12 | Bristol-Myers Squibb Company | Epothilone derivatives |
| US6365749B1 (en) | 1997-12-04 | 2002-04-02 | Bristol-Myers Squibb Company | Process for the preparation of ring-opened epothilone intermediates which are useful for the preparation of epothilone analogs |
| US6498257B1 (en) | 1998-04-21 | 2002-12-24 | Bristol-Myers Squibb Company | 2,3-olefinic epothilone derivatives |
| US6211412B1 (en) * | 1999-03-29 | 2001-04-03 | The University Of Kansas | Synthesis of epothilones |
| US6518421B1 (en) | 2000-03-20 | 2003-02-11 | Bristol-Myers Squibb Company | Process for the preparation of epothilone analogs |
| US6593115B2 (en) * | 2000-03-24 | 2003-07-15 | Bristol-Myers Squibb Co. | Preparation of epothilone intermediates |
-
2002
- 2002-02-27 DE DE60213884T patent/DE60213884T2/de not_active Expired - Lifetime
- 2002-02-27 DE DE60211124T patent/DE60211124T2/de not_active Expired - Lifetime
- 2002-02-27 IL IL15731202A patent/IL157312A0/xx unknown
- 2002-02-27 WO PCT/EP2002/002105 patent/WO2002072858A2/en active IP Right Grant
- 2002-02-27 MX MXPA03007466A patent/MXPA03007466A/es unknown
- 2002-02-27 EP EP02719946A patent/EP1364040B1/en not_active Expired - Lifetime
- 2002-02-27 PL PL02362556A patent/PL362556A1/xx not_active Application Discontinuation
- 2002-02-27 US US10/468,919 patent/US7157595B2/en not_active Expired - Lifetime
- 2002-02-27 EP EP04019590A patent/EP1564217B1/en not_active Expired - Lifetime
- 2002-02-27 KR KR10-2003-7011281A patent/KR20030084952A/ko not_active Application Discontinuation
- 2002-02-27 CA CA002437707A patent/CA2437707A1/en not_active Abandoned
- 2002-02-27 CZ CZ20032291A patent/CZ20032291A3/cs unknown
- 2002-02-27 HU HU0303895A patent/HUP0303895A3/hu unknown
- 2002-02-27 NZ NZ527557A patent/NZ527557A/en unknown
- 2002-02-27 RU RU2003128953/04A patent/RU2003128953A/ru not_active Application Discontinuation
- 2002-02-27 AT AT02719946T patent/ATE325201T1/de not_active IP Right Cessation
- 2002-02-27 AT AT04019590T patent/ATE335746T1/de not_active IP Right Cessation
- 2002-02-27 BR BR0207675-6A patent/BR0207675A/pt not_active IP Right Cessation
- 2002-02-27 NZ NZ539204A patent/NZ539204A/en unknown
- 2002-02-27 CN CNA028055349A patent/CN1501980A/zh active Pending
- 2002-02-27 JP JP2002571909A patent/JP2004522801A/ja not_active Withdrawn
-
2003
- 2003-08-05 ZA ZA200306034A patent/ZA200306034B/en unknown
- 2003-08-26 NO NO20033784A patent/NO20033784D0/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NZ527557A (en) | 2005-05-27 |
| DE60213884T2 (de) | 2007-02-22 |
| ATE325201T1 (de) | 2006-06-15 |
| DE60213884D1 (de) | 2006-09-21 |
| WO2002072858A2 (en) | 2002-09-19 |
| DE60211124T2 (de) | 2006-11-30 |
| DE60211124D1 (de) | 2006-06-08 |
| HUP0303895A3 (en) | 2007-06-28 |
| WO2002072858A3 (en) | 2002-12-19 |
| HUP0303895A2 (hu) | 2004-03-29 |
| JP2004522801A (ja) | 2004-07-29 |
| NO20033784L (no) | 2003-08-26 |
| EP1364040B1 (en) | 2006-05-03 |
| KR20030084952A (ko) | 2003-11-01 |
| CN1501980A (zh) | 2004-06-02 |
| NZ539204A (en) | 2005-12-23 |
| PL362556A1 (en) | 2004-11-02 |
| NO20033784D0 (no) | 2003-08-26 |
| ATE335746T1 (de) | 2006-09-15 |
| EP1564217A2 (en) | 2005-08-17 |
| CA2437707A1 (en) | 2002-09-19 |
| IL157312A0 (en) | 2004-02-19 |
| EP1364040A2 (en) | 2003-11-26 |
| EP1564217B1 (en) | 2006-08-09 |
| US20040092560A1 (en) | 2004-05-13 |
| BR0207675A (pt) | 2004-03-09 |
| ZA200306034B (en) | 2004-08-05 |
| CZ20032291A3 (cs) | 2004-02-18 |
| US7157595B2 (en) | 2007-01-02 |
| MXPA03007466A (es) | 2003-12-08 |
| EP1564217A3 (en) | 2005-08-31 |
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| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
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