CA2353930A1 - Purification of echinocandin cyclopeptide compounds - Google Patents
Purification of echinocandin cyclopeptide compounds Download PDFInfo
- Publication number
- CA2353930A1 CA2353930A1 CA002353930A CA2353930A CA2353930A1 CA 2353930 A1 CA2353930 A1 CA 2353930A1 CA 002353930 A CA002353930 A CA 002353930A CA 2353930 A CA2353930 A CA 2353930A CA 2353930 A1 CA2353930 A1 CA 2353930A1
- Authority
- CA
- Canada
- Prior art keywords
- acetic acid
- product
- group
- echinocandin
- mixture
- 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.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 33
- 238000000746 purification Methods 0.000 title description 15
- 108010049047 Echinocandins Proteins 0.000 title description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 136
- 238000000034 method Methods 0.000 claims abstract description 57
- 230000008569 process Effects 0.000 claims abstract description 35
- 238000000855 fermentation Methods 0.000 claims abstract description 27
- 230000004151 fermentation Effects 0.000 claims abstract description 27
- 239000000047 product Substances 0.000 claims abstract description 23
- 239000000203 mixture Substances 0.000 claims abstract description 20
- 239000006227 byproduct Substances 0.000 claims abstract description 18
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 14
- 108010069514 Cyclic Peptides Proteins 0.000 claims abstract description 12
- 102000001189 Cyclic Peptides Human genes 0.000 claims abstract description 12
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
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- 239000011347 resin Substances 0.000 claims description 18
- 125000003277 amino group Chemical group 0.000 claims description 16
- 239000011148 porous material Substances 0.000 claims description 13
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 11
- 239000002245 particle Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
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- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical group C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 claims description 3
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 claims description 3
- 229910000342 sodium bisulfate Inorganic materials 0.000 claims description 3
- UJTTUOLQLCQZEA-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-(4-hydroxybutyl)carbamate Chemical compound C1=CC=C2C(COC(=O)NCCCCO)C3=CC=CC=C3C2=C1 UJTTUOLQLCQZEA-UHFFFAOYSA-N 0.000 claims description 2
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- 238000010828 elution Methods 0.000 description 32
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- -1 Sporiofungin A Chemical compound 0.000 description 18
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- 239000000243 solution Substances 0.000 description 12
- 238000004007 reversed phase HPLC Methods 0.000 description 9
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- 239000010452 phosphate Substances 0.000 description 5
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
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- 238000011084 recovery Methods 0.000 description 4
- 230000000717 retained effect Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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- 230000000144 pharmacologic effect Effects 0.000 description 1
- DQXPFAADCTZLNL-FXDJFZINSA-N pneumocandin B0 Chemical compound C1([C@H](O)[C@@H](O)[C@H]2C(=O)N[C@H](C(=O)N3CC[C@H](O)[C@H]3C(=O)N[C@H](O)[C@H](O)C[C@@H](C(N[C@H](C(=O)N3C[C@H](O)C[C@H]3C(=O)N2)[C@@H](C)O)=O)NC(=O)CCCCCCCC[C@@H](C)C[C@@H](C)CC)[C@H](O)CC(N)=O)=CC=C(O)C=C1 DQXPFAADCTZLNL-FXDJFZINSA-N 0.000 description 1
- DFQUSLQYURJBIT-KGPSKUFKSA-N pneumocandin ao Chemical compound C1([C@H](O)[C@@H](O)[C@H]2C(=O)N[C@H](C(=O)N3C[C@H](C)[C@H](O)[C@H]3C(=O)N[C@H](O)[C@H](O)C[C@@H](C(N[C@H](C(=O)N3C[C@H](O)C[C@H]3C(=O)N2)[C@@H](C)O)=O)NC(=O)CCCCCCCC[C@@H](C)C[C@@H](C)CC)[C@H](O)CC(N)=O)=CC=C(O)C=C1 DFQUSLQYURJBIT-KGPSKUFKSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011045 prefiltration Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 239000013014 purified material Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- OGNAOIGAPPSUMG-UHFFFAOYSA-N spiro[2.2]pentane Chemical compound C1CC11CC1 OGNAOIGAPPSUMG-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 239000010891 toxic waste Substances 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/50—Cyclic peptides containing at least one abnormal peptide link
- C07K7/54—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring
- C07K7/56—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring the cyclisation not occurring through 2,4-diamino-butanoic acid
-
- 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
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11152498P | 1998-12-09 | 1998-12-09 | |
| US60/111,524 | 1998-12-09 | ||
| PCT/US1999/029008 WO2000034315A2 (en) | 1998-12-09 | 1999-12-08 | Purification of echinocandin cyclopeptide compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2353930A1 true CA2353930A1 (en) | 2000-06-15 |
Family
ID=22339024
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002353930A Abandoned CA2353930A1 (en) | 1998-12-09 | 1999-12-08 | Purification of echinocandin cyclopeptide compounds |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6506726B1 (enExample) |
| EP (1) | EP1137663B1 (enExample) |
| JP (1) | JP2003511345A (enExample) |
| KR (1) | KR20010101151A (enExample) |
| CN (1) | CN1337968A (enExample) |
| AT (1) | ATE338059T1 (enExample) |
| AU (1) | AU766091B2 (enExample) |
| BR (1) | BR9916101A (enExample) |
| CA (1) | CA2353930A1 (enExample) |
| DE (1) | DE69933046T2 (enExample) |
| DK (1) | DK1137663T3 (enExample) |
| ES (1) | ES2272096T3 (enExample) |
| IL (1) | IL143563A0 (enExample) |
| PT (1) | PT1137663E (enExample) |
| RU (1) | RU2001118849A (enExample) |
| WO (1) | WO2000034315A2 (enExample) |
| ZA (1) | ZA200104621B (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6743777B1 (en) * | 1992-03-19 | 2004-06-01 | Eli Lilly And Company | Cyclic peptide antifungal agents and process for preparation thereof |
| ATE294571T1 (de) * | 1999-03-03 | 2005-05-15 | Lilly Co Eli | Echinocandin pharmazeutische zusammensetzungen |
| BR0009248A (pt) | 1999-03-03 | 2001-11-20 | Lilly Co Eli | Formação e troca de ânion de sais de amÈnioequinocandina cristalinos |
| KR20020003864A (ko) * | 1999-03-03 | 2002-01-15 | 피터 지. 스트링거 | 에키노칸딘/탄수화물 착물 |
| AU771727B2 (en) | 1999-03-03 | 2004-04-01 | Eli Lilly And Company | Processes for making pharmaceutical oral ECB formulations and compositions |
| US6991800B2 (en) * | 2002-06-13 | 2006-01-31 | Vicuron Pharmaceuticals Inc. | Antifungal parenteral products |
| EP1778301A2 (en) * | 2004-06-29 | 2007-05-02 | Reliance Life Sciences Pvt., Ltd. | Process for improvement of virus-safe biological fluids |
| DE102004060750A1 (de) | 2004-12-15 | 2006-07-13 | Sanofi-Aventis Deutschland Gmbh | Verfahren zur Deacylierung von Lipopeptiden |
| TW200826957A (en) * | 2006-10-16 | 2008-07-01 | Teva Gyogyszergyar Zartkoruen Mukodo Reszvenytarsasag | Purification processes for echinocandin-type compounds |
| US9394340B2 (en) | 2009-03-24 | 2016-07-19 | Cadila Healthcare Limited | Purification process for lipopeptides |
| CN102219832B (zh) * | 2010-04-15 | 2013-08-21 | 上海天伟生物制药有限公司 | 一种氮杂环六肽或其盐的纯化方法 |
| CN102336817B (zh) * | 2010-07-16 | 2016-06-15 | 浙江震元制药有限公司 | 棘球白素b母核的分离方法 |
| CN102432674B (zh) * | 2010-09-29 | 2014-01-22 | 上海天伟生物制药有限公司 | 一种环脂肽化合物或其盐的纯化方法 |
| EP2623611B1 (en) * | 2010-09-30 | 2016-07-13 | Shanghai Techwell Biopharmaceutical Co., Ltd | Method for purifying cyclic lipopeptide or salt thereof |
| CN102153616A (zh) * | 2010-12-27 | 2011-08-17 | 浙江海正药业股份有限公司 | 一种环己肽类化合物及其盐的分离纯化方法 |
| JP5809296B2 (ja) | 2011-03-03 | 2015-11-10 | シーチェイド ファーマシューティカルズ，インコーポレーテッド | 抗真菌薬及びそれらの使用 |
| HUE027806T2 (en) * | 2011-04-20 | 2016-11-28 | Xellia Pharmaceuticals Aps | A method for purifying micafungin |
| CN102952178B (zh) * | 2011-08-24 | 2016-04-27 | 华北制药集团新药研究开发有限责任公司 | 一种高纯度棘白霉素类化合物的制备方法 |
| KR102236462B1 (ko) | 2012-03-19 | 2021-04-08 | 시다라 세라퓨틱스, 인코포레이티드 | 에키노칸딘 계열의 화합물에 대한 투여 용법 |
| CN103483427A (zh) * | 2012-06-09 | 2014-01-01 | 浙江海正药业股份有限公司 | 一种棘白菌素类化合物的纯化方法 |
| CN103910783B (zh) * | 2014-04-23 | 2016-07-06 | 华北制药集团新药研究开发有限责任公司 | 一种高纯度棘白霉素b母核的制备方法 |
| EP3058958B1 (en) | 2015-02-23 | 2018-09-19 | Selectchemie AG | Anidulafungin composition |
| CN108883152A (zh) | 2016-01-08 | 2018-11-23 | 奇达拉治疗公司 | 防止和治疗肺孢子虫感染的方法 |
| ES2955711T3 (es) | 2016-03-16 | 2023-12-05 | Cidara Therapeutics Inc | Regímenes de dosificación para el tratamiento de infecciones fúngicas |
| CN106248857A (zh) * | 2016-07-15 | 2016-12-21 | 广西医科大学 | 利用薄层层析快速检测植物环肽的方法 |
| CA3069423C (en) | 2017-07-12 | 2025-04-15 | Napp Pharmaceutical Group Limited | Formulations for the treatment of fungal infections |
| CN119504952A (zh) * | 2024-11-15 | 2025-02-25 | 上海天伟生物制药有限公司 | 一种棘白菌素药物杂质化合物及其制备方法与应用 |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4293489A (en) | 1979-12-13 | 1981-10-06 | Eli Lilly And Company | Derivatives of A-30912A nucleus |
| US4293482A (en) | 1979-12-13 | 1981-10-06 | Eli Lilly And Company | A-30912A Nucleus |
| US4320052A (en) | 1979-12-13 | 1982-03-16 | Eli Lilly And Company | Derivatives of A-30912A nucleus |
| US4304716A (en) | 1979-12-13 | 1981-12-08 | Eli Lilly And Company | S 31794/F-1 Nucleus |
| US4874843A (en) | 1987-12-03 | 1989-10-17 | Eli Lilly And Company | Chromatographic purification process |
| EP0294990A3 (en) | 1987-06-10 | 1990-05-09 | Eli Lilly And Company | Chromatographic purification process |
| US5166135A (en) | 1988-09-12 | 1992-11-24 | Merck & Company, Inc. | Method for the control of pneumocystis carinii |
| DK173802B1 (da) | 1988-09-12 | 2001-11-05 | Merck & Co Inc | Præparat til behandling af Pneumocystis carinii infeksioner og anvendelse af et cyclohexapeptid til fremstilling af et lægemiddel mod Pneumocystis carinii infektioner |
| US5310726A (en) | 1990-03-19 | 1994-05-10 | Merck & Co., Inc. | Lipopeptide compounds |
| IL98349A (en) | 1990-06-07 | 1995-05-26 | Lilly Co Eli | Diphylase lipopeptide |
| IL98506A (en) | 1990-06-18 | 1996-09-12 | Fujisawa Pharmaceutical Co | Cyclic peptide antibiotics processes for the preparation thereof and pharmaceutical compositions containing them |
| US5965525A (en) | 1992-03-19 | 1999-10-12 | Eli Lilly And Company | Cyclic peptide antifungal agents |
| MY136593A (en) | 1992-03-19 | 2008-10-31 | Lilly Co Eli | Cyclic peptide antifungal agents and process for preparation thereof |
| US5541160A (en) | 1994-04-04 | 1996-07-30 | Merck & Co., Inc. | Antifungal and anti-pneumocystis compounds, compositions containing such compounds, and methods of use |
| US5646111A (en) | 1995-04-07 | 1997-07-08 | Eli Lilly And Company | Cyclic peptide antifungal Agents |
| US5786325A (en) | 1995-05-26 | 1998-07-28 | Eli Lilly And Company | Cyclic peptide antifungal agents and methods of making and using |
| US5652213A (en) | 1995-05-26 | 1997-07-29 | Eli Lilly And Company | Cyclic peptide antifungal agents |
| US5618787A (en) | 1995-05-26 | 1997-04-08 | Eli Lilly And Company | Cyclic peptide antifungal agents |
| US5629290A (en) | 1995-05-26 | 1997-05-13 | Eli Lilly And Company | Cyclic peptide antifungal agents |
| US5629289A (en) | 1995-07-25 | 1997-05-13 | Eli Lilly And Company | Cyclic peptide antifungal agents |
| EP0881907A4 (en) | 1996-02-01 | 2000-05-10 | Lilly Co Eli | FUNGICIDES IN THE FORM OF CYCLIC PEPTIDES |
| US5696084A (en) | 1996-08-16 | 1997-12-09 | Abbott Laboratories | Amino-lipopetide antifungal agents |
| CA2301184A1 (en) | 1997-08-04 | 1999-02-11 | Eli Lilly And Company | Cyclic peptide antifungal agents |
| EP0931834A3 (en) | 1997-12-23 | 2002-06-26 | Eli Lilly And Company | Echinocandin binding domain of 1,3-Beta-glucan synthase |
| US6323176B1 (en) | 1998-02-25 | 2001-11-27 | Eli Lilly And Company | Cyclic peptide antifungal agents |
| JP2002528388A (ja) | 1998-08-20 | 2002-09-03 | イーライ リリー アンド カンパニー | 環改変された環状ペプチドアナログ |
| EP1107982B1 (en) | 1998-08-28 | 2004-05-19 | Eli Lilly & Company | Reversible boron complexes of 1,2-(cis)-diol cyclic peptides |
| AU1517900A (en) | 1998-10-28 | 2000-05-15 | Eli Lilly And Company | Photochemical process for making 1-deoxy-2-keto derivatives |
| WO2000035945A1 (en) | 1998-12-16 | 2000-06-22 | Eli Lilly And Company | Cyclic peptide antifungal agents having a sugar substituent |
| JP2002535248A (ja) | 1998-12-16 | 2002-10-22 | イーライ リリー アンド カンパニー | 環式ペプチド抗真菌剤 |
| KR20020003864A (ko) | 1999-03-03 | 2002-01-15 | 피터 지. 스트링거 | 에키노칸딘/탄수화물 착물 |
| AU771727B2 (en) | 1999-03-03 | 2004-04-01 | Eli Lilly And Company | Processes for making pharmaceutical oral ECB formulations and compositions |
| ATE294571T1 (de) | 1999-03-03 | 2005-05-15 | Lilly Co Eli | Echinocandin pharmazeutische zusammensetzungen |
| BR0009248A (pt) | 1999-03-03 | 2001-11-20 | Lilly Co Eli | Formação e troca de ânion de sais de amÈnioequinocandina cristalinos |
-
1999
- 1999-12-08 IL IL14356399A patent/IL143563A0/xx unknown
- 1999-12-08 AU AU31132/00A patent/AU766091B2/en not_active Ceased
- 1999-12-08 US US09/857,924 patent/US6506726B1/en not_active Expired - Fee Related
- 1999-12-08 AT AT99965156T patent/ATE338059T1/de not_active IP Right Cessation
- 1999-12-08 BR BR9916101-0A patent/BR9916101A/pt not_active IP Right Cessation
- 1999-12-08 EP EP99965156A patent/EP1137663B1/en not_active Expired - Lifetime
- 1999-12-08 JP JP2000586757A patent/JP2003511345A/ja not_active Abandoned
- 1999-12-08 WO PCT/US1999/029008 patent/WO2000034315A2/en not_active Ceased
- 1999-12-08 DE DE69933046T patent/DE69933046T2/de not_active Expired - Fee Related
- 1999-12-08 CN CN99815515A patent/CN1337968A/zh active Pending
- 1999-12-08 DK DK99965156T patent/DK1137663T3/da active
- 1999-12-08 RU RU2001118849/04A patent/RU2001118849A/ru not_active Application Discontinuation
- 1999-12-08 PT PT99965156T patent/PT1137663E/pt unknown
- 1999-12-08 CA CA002353930A patent/CA2353930A1/en not_active Abandoned
- 1999-12-08 KR KR1020017007161A patent/KR20010101151A/ko not_active Withdrawn
- 1999-12-08 ES ES99965156T patent/ES2272096T3/es not_active Expired - Lifetime
-
2001
- 2001-06-06 ZA ZA200104621A patent/ZA200104621B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US6506726B1 (en) | 2003-01-14 |
| DK1137663T3 (da) | 2007-01-08 |
| DE69933046D1 (de) | 2006-10-12 |
| CN1337968A (zh) | 2002-02-27 |
| BR9916101A (pt) | 2002-06-04 |
| JP2003511345A (ja) | 2003-03-25 |
| EP1137663A2 (en) | 2001-10-04 |
| AU3113200A (en) | 2000-06-26 |
| AU766091B2 (en) | 2003-10-09 |
| ATE338059T1 (de) | 2006-09-15 |
| WO2000034315A8 (en) | 2000-10-26 |
| WO2000034315A3 (en) | 2000-12-28 |
| ES2272096T3 (es) | 2007-04-16 |
| PT1137663E (pt) | 2006-12-29 |
| EP1137663B1 (en) | 2006-08-30 |
| RU2001118849A (ru) | 2003-08-10 |
| IL143563A0 (en) | 2002-04-21 |
| DE69933046T2 (de) | 2007-09-13 |
| WO2000034315A2 (en) | 2000-06-15 |
| KR20010101151A (ko) | 2001-11-14 |
| ZA200104621B (en) | 2002-06-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |