CA2416336A1 - Multivalent neuraminidase inhibitor conjugates - Google Patents
Multivalent neuraminidase inhibitor conjugates Download PDFInfo
- Publication number
- CA2416336A1 CA2416336A1 CA002416336A CA2416336A CA2416336A1 CA 2416336 A1 CA2416336 A1 CA 2416336A1 CA 002416336 A CA002416336 A CA 002416336A CA 2416336 A CA2416336 A CA 2416336A CA 2416336 A1 CA2416336 A1 CA 2416336A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- formula
- group
- compound according
- neuraminidase
- 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
- 239000002911 sialidase inhibitor Substances 0.000 title description 8
- 229940123424 Neuraminidase inhibitor Drugs 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 314
- 238000000034 method Methods 0.000 claims abstract description 80
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- 108010006232 Neuraminidase Proteins 0.000 claims abstract description 51
- 238000002360 preparation method Methods 0.000 claims abstract description 28
- 238000011282 treatment Methods 0.000 claims abstract description 25
- 241000712461 unidentified influenza virus Species 0.000 claims abstract description 21
- 125000005647 linker group Chemical group 0.000 claims abstract description 18
- 230000008569 process Effects 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 238000011321 prophylaxis Methods 0.000 claims abstract description 12
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- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
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- 125000006850 spacer group Chemical group 0.000 claims abstract description 7
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 30
- -1 -COLG Chemical group 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 28
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- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 claims description 3
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- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims description 2
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- PGSADBUBUOPOJS-UHFFFAOYSA-N neutral red Chemical compound Cl.C1=C(C)C(N)=CC2=NC3=CC(N(C)C)=CC=C3N=C21 PGSADBUBUOPOJS-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
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- 230000002285 radioactive effect Effects 0.000 description 1
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- 230000035945 sensitivity Effects 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
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- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
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- DIORMHZUUKOISG-UHFFFAOYSA-N sulfoformic acid Chemical compound OC(=O)S(O)(=O)=O DIORMHZUUKOISG-UHFFFAOYSA-N 0.000 description 1
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- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
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- 229960001124 trientine Drugs 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/351—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom not condensed with another ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
-
- 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
- A61P31/12—Antivirals
-
- 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
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring 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
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/02—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving viable microorganisms
- C12Q1/04—Determining presence or kind of microorganism; Use of selective media for testing antibiotics or bacteriocides; Compositions containing a chemical indicator therefor
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Virology (AREA)
- Zoology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Wood Science & Technology (AREA)
- Animal Behavior & Ethology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Microbiology (AREA)
- Communicable Diseases (AREA)
- Analytical Chemistry (AREA)
- Biophysics (AREA)
- Toxicology (AREA)
- Biotechnology (AREA)
- Immunology (AREA)
- Genetics & Genomics (AREA)
- Oncology (AREA)
- Physics & Mathematics (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPR0010 | 2000-09-08 | ||
| AUPR0010A AUPR001000A0 (en) | 2000-09-08 | 2000-09-08 | Novel chemical compounds and their use |
| PCT/AU2001/001128 WO2002020514A1 (en) | 2000-09-08 | 2001-09-07 | Multivalent neuraminidase inhibitor conjugates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2416336A1 true CA2416336A1 (en) | 2002-03-14 |
Family
ID=3824061
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002416336A Abandoned CA2416336A1 (en) | 2000-09-08 | 2001-09-07 | Multivalent neuraminidase inhibitor conjugates |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7205333B2 (https=) |
| EP (1) | EP1315719A4 (https=) |
| JP (1) | JP5095066B2 (https=) |
| KR (1) | KR20030046406A (https=) |
| AU (3) | AUPR001000A0 (https=) |
| BR (1) | BR0113755A (https=) |
| CA (1) | CA2416336A1 (https=) |
| MX (1) | MXPA03002022A (https=) |
| WO (1) | WO2002020514A1 (https=) |
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| WO2002092555A1 (en) * | 2001-05-11 | 2002-11-21 | Sankyo Company, Limited | Sialic acid derivatives |
| EP1423385B1 (en) * | 2001-09-07 | 2008-07-02 | Biota Scientific Management Pty. Ltd. | Intermediates for preparing neuraminidase inhibitor conjugates |
| CN1285591C (zh) | 2001-11-09 | 2006-11-22 | 百奥塔科学管理有限公司 | 二聚化合物及其作为抗病毒剂的应用 |
| AU2002340635B2 (en) * | 2001-11-09 | 2008-03-13 | Biota Scientific Management Pty Ltd | Dimeric compounds and their use as anti-viral agents |
| AU2002336823B2 (en) * | 2001-11-09 | 2008-03-20 | Biota Scientific Management Pty Ltd | Dimeric compounds and their use as anti-viral agents |
| AUPR879601A0 (en) * | 2001-11-09 | 2001-12-06 | Biota Scientific Management Pty Ltd | Novel chemical compounds and their use |
| AUPR879401A0 (en) | 2001-11-09 | 2001-12-06 | Biota Scientific Management Pty Ltd | Novel chemical compounds and their use |
| AUPR879701A0 (en) * | 2001-11-09 | 2001-12-06 | Biota Scientific Management Pty Ltd | Novel chemical compounds and their use |
| AUPR879501A0 (en) | 2001-11-09 | 2001-12-06 | Biota Scientific Management Pty Ltd | Novel chemical compounds and their use |
| AU2002340632B2 (en) * | 2001-11-09 | 2008-03-20 | Biota Scientific Management Pty Ltd | Dimeric compounds and their use as anti-viral agents |
| CN1930304B (zh) * | 2003-11-21 | 2016-01-06 | Anp技术公司 | 不对称支化的聚合物缀合物和微阵列检测 |
| EP1808428B1 (en) | 2006-01-16 | 2010-12-22 | Research Institute of Petroleum Industry (RIPI) | Descaling solutions comprising EDDH |
| US7875747B2 (en) * | 2006-10-10 | 2011-01-25 | Afton Chemical Corporation | Branched succinimide dispersant compounds and methods of making the compounds |
| US7960139B2 (en) | 2007-03-23 | 2011-06-14 | Academia Sinica | Alkynyl sugar analogs for the labeling and visualization of glycoconjugates in cells |
| WO2009032605A2 (en) * | 2007-08-27 | 2009-03-12 | Massachusetts Institute Of Technology | Bi-functional polymer-attached inhibitors of influenza virus |
| EP2296711A2 (en) * | 2008-05-29 | 2011-03-23 | MDRNA, Inc. | Multi-arm amines and uses thereof |
| JP5986745B2 (ja) | 2008-07-15 | 2016-09-06 | アカデミア シニカＡｃａｄｅｍｉａ Ｓｉｎｉｃａ | Ｐｔｆｅ様のアルミニウム・コート・ガラススライド上のグリカンアレイおよび関連する方法 |
| JP2012532894A (ja) * | 2009-07-16 | 2012-12-20 | グリフィス ユニバーシティ | 抗インフルエンザ薬 |
| US10087236B2 (en) | 2009-12-02 | 2018-10-02 | Academia Sinica | Methods for modifying human antibodies by glycan engineering |
| US11377485B2 (en) | 2009-12-02 | 2022-07-05 | Academia Sinica | Methods for modifying human antibodies by glycan engineering |
| US10338069B2 (en) | 2010-04-12 | 2019-07-02 | Academia Sinica | Glycan arrays for high throughput screening of viruses |
| US10130714B2 (en) | 2012-04-14 | 2018-11-20 | Academia Sinica | Enhanced anti-influenza agents conjugated with anti-inflammatory activity |
| WO2014031498A1 (en) | 2012-08-18 | 2014-02-27 | Academia Sinica | Cell-permeable probes for identification and imaging of sialidases |
| EP3013365B1 (en) | 2013-06-26 | 2019-06-05 | Academia Sinica | Rm2 antigens and use thereof |
| WO2014210564A1 (en) | 2013-06-27 | 2014-12-31 | Academia Sinica | Glycan conjugates and use thereof |
| US9782476B2 (en) | 2013-09-06 | 2017-10-10 | Academia Sinica | Human iNKT cell activation using glycolipids with altered glycosyl groups |
| CA2937123A1 (en) | 2014-01-16 | 2015-07-23 | Academia Sinica | Compositions and methods for treatment and detection of cancers |
| US10150818B2 (en) | 2014-01-16 | 2018-12-11 | Academia Sinica | Compositions and methods for treatment and detection of cancers |
| CN103819665B (zh) * | 2014-02-27 | 2015-10-28 | 中国科学院微生物研究所 | 四价扎那米韦及其制备方法与应用 |
| WO2015148915A1 (en) | 2014-03-27 | 2015-10-01 | Academia Sinica | Reactive labelling compounds and uses thereof |
| US10118969B2 (en) | 2014-05-27 | 2018-11-06 | Academia Sinica | Compositions and methods relating to universal glycoforms for enhanced antibody efficacy |
| CA2950423A1 (en) | 2014-05-27 | 2015-12-03 | Academia Sinica | Compositions and methods relating to universal glycoforms for enhanced antibody efficacy |
| KR20170003720A (ko) | 2014-05-27 | 2017-01-09 | 아카데미아 시니카 | 항-ｃｄ20 글리코항체 및 이의 용도 |
| KR102512592B1 (ko) | 2014-05-27 | 2023-03-21 | 아카데미아 시니카 | 항-ｈｅｒ2 글리코항체 및 이의 용도 |
| CN106714829A (zh) | 2014-05-28 | 2017-05-24 | 中央研究院 | 抗TNF‑α醣抗体及其用途 |
| CA2960712A1 (en) | 2014-09-08 | 2016-03-17 | Academia Sinica | Human inkt cell activation using glycolipids |
| US9975965B2 (en) | 2015-01-16 | 2018-05-22 | Academia Sinica | Compositions and methods for treatment and detection of cancers |
| US10495645B2 (en) | 2015-01-16 | 2019-12-03 | Academia Sinica | Cancer markers and methods of use thereof |
| AU2015378564A1 (en) | 2015-01-24 | 2017-07-13 | Academia Sinica | Novel glycan conjugates and methods of use thereof |
| ES2911027T3 (es) * | 2015-11-20 | 2022-05-17 | AusVir Therapeutics Pty Ltd | Compuestos para aplicaciones medicinales |
| WO2017156192A1 (en) | 2016-03-08 | 2017-09-14 | Academia Sinica | Methods for modular synthesis of n-glycans and arrays thereof |
| EP3500594A4 (en) | 2016-08-22 | 2020-03-11 | Cho Pharma Inc. | ANTIBODIES, BINDING FRAGMENTS AND METHOD FOR USE |
| TWI861205B (zh) * | 2019-09-06 | 2024-11-11 | 美商席達拉醫療有限公司 | 用於治療病毒感染之組合物及方法 |
Family Cites Families (15)
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|---|---|---|---|---|
| CZ288492B6 (en) | 1990-04-24 | 2001-06-13 | Biota Scient Management | Derivatives of alpha-D-neuraminic acid, process of their preparation, their use and pharmaceutical preparations based thereon |
| GB9400206D0 (en) | 1994-01-07 | 1994-03-02 | Glaxo Group Ltd | Chemical compound |
| AUPM354694A0 (en) | 1994-01-27 | 1994-02-17 | Biota Scientific Management Pty Ltd | Chemical compounds |
| AUPM623994A0 (en) | 1994-06-15 | 1994-07-07 | Biomolecular Research Institute Limited | Antiviral dendrimers |
| BR9607098B8 (pt) | 1995-02-27 | 2014-11-18 | Gilead Sciences Inc | Composto e composição farmacêutica. |
| GB9516276D0 (en) | 1995-08-08 | 1995-10-11 | Biota Scient Management | Chemical compounds |
| CA2245680C (en) * | 1996-03-01 | 2005-09-27 | Biota Scientific Management Pty. Ltd. | Method of detection of influenza virus and compounds for use therein |
| EP0889041B1 (en) * | 1996-03-06 | 2002-07-24 | TSUMURA & CO. | Novel iridoid derivatives and neovascularization inhibitors containing the same as active ingredient |
| RO121027B1 (ro) | 1996-06-14 | 2006-11-30 | Biocryst Pharmaceuticals, Inc. | Compuşi ciclopentanici substituiţi, compoziţiifarmaceutice şi utilizarea acestora |
| AUPO104396A0 (en) | 1996-07-17 | 1996-08-08 | Biomolecular Research Institute Limited | Antiviral linear polymers |
| ATE211468T1 (de) | 1996-07-22 | 2002-01-15 | Sankyo Co | Neuraminsäuredervate, ihre herstellung und medizinische verwendung |
| CN1126752C (zh) | 1996-08-13 | 2003-11-05 | 三共株式会社 | 神经氨酸化合物 |
| NZ335368A (en) * | 1996-11-14 | 2001-08-31 | Biota Scient Management | Macromolecular compound with one or more neuraminidase binders, binds to the active site of influenza virus neuraminidase |
| CA2315262C (en) | 1997-12-17 | 2009-11-10 | Biocryst Pharmaceuticals, Inc. | Substituted cyclopentane and cyclopentene compounds useful as neuraminidase inhibitors |
| AUPP913999A0 (en) * | 1999-03-12 | 1999-04-01 | Biota Scientific Management Pty Ltd | Novel chemical compounds and their use |
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2000
- 2000-09-08 AU AUPR0010A patent/AUPR001000A0/en not_active Abandoned
-
2001
- 2001-09-07 AU AU2001285601A patent/AU2001285601B2/en not_active Ceased
- 2001-09-07 US US10/363,988 patent/US7205333B2/en not_active Expired - Fee Related
- 2001-09-07 WO PCT/AU2001/001128 patent/WO2002020514A1/en not_active Ceased
- 2001-09-07 JP JP2002525135A patent/JP5095066B2/ja not_active Expired - Fee Related
- 2001-09-07 AU AU8560101A patent/AU8560101A/xx active Pending
- 2001-09-07 MX MXPA03002022A patent/MXPA03002022A/es active IP Right Grant
- 2001-09-07 BR BR0113755-7A patent/BR0113755A/pt not_active IP Right Cessation
- 2001-09-07 EP EP01964755A patent/EP1315719A4/en not_active Withdrawn
- 2001-09-07 KR KR10-2003-7001793A patent/KR20030046406A/ko not_active Withdrawn
- 2001-09-07 CA CA002416336A patent/CA2416336A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AU2001285601B2 (en) | 2005-10-27 |
| JP5095066B2 (ja) | 2012-12-12 |
| AUPR001000A0 (en) | 2000-10-05 |
| WO2002020514A1 (en) | 2002-03-14 |
| US7205333B2 (en) | 2007-04-17 |
| EP1315719A1 (en) | 2003-06-04 |
| AU8560101A (en) | 2002-03-22 |
| EP1315719A4 (en) | 2005-07-20 |
| JP2004507564A (ja) | 2004-03-11 |
| KR20030046406A (ko) | 2003-06-12 |
| US20040058853A1 (en) | 2004-03-25 |
| BR0113755A (pt) | 2003-07-08 |
| MXPA03002022A (es) | 2004-05-04 |
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