JP4099234B2 - 抗ウイルス活性を有する新規化合物 - Google Patents
抗ウイルス活性を有する新規化合物 Download PDFInfo
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- JP4099234B2 JP4099234B2 JP54074697A JP54074697A JP4099234B2 JP 4099234 B2 JP4099234 B2 JP 4099234B2 JP 54074697 A JP54074697 A JP 54074697A JP 54074697 A JP54074697 A JP 54074697A JP 4099234 B2 JP4099234 B2 JP 4099234B2
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- JP
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- Prior art keywords
- compound
- salt
- glycero
- galacto
- dideoxy
- 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.)
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 216
- 230000000840 anti-viral effect Effects 0.000 title description 16
- 239000002253 acid Substances 0.000 claims abstract description 60
- 150000003839 salts Chemical class 0.000 claims abstract description 51
- 150000002632 lipids Chemical class 0.000 claims abstract description 31
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 11
- 239000011734 sodium Substances 0.000 claims description 88
- 229910052708 sodium Inorganic materials 0.000 claims description 87
- 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 claims description 49
- 241000700605 Viruses Species 0.000 claims description 37
- -1 (docosyloxymethyl) propyl Chemical group 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 23
- 239000003814 drug Substances 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 230000000694 effects Effects 0.000 claims description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
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- 229930182475 S-glycoside Natural products 0.000 claims description 7
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- 150000001768 cations Chemical class 0.000 claims description 4
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
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- 230000003013 cytotoxicity Effects 0.000 abstract description 14
- 231100000135 cytotoxicity Toxicity 0.000 abstract description 14
- 229930182470 glycoside Natural products 0.000 abstract description 14
- 150000002338 glycosides Chemical class 0.000 abstract description 12
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 98
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 72
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 70
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- 238000007429 general method Methods 0.000 description 49
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- 238000000034 method Methods 0.000 description 40
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- 125000004429 atom Chemical group 0.000 description 26
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- 239000000243 solution Substances 0.000 description 21
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
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- BATGFXRKHSIQIS-UHFFFAOYSA-N 1-butoxydocosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCOCCCC BATGFXRKHSIQIS-UHFFFAOYSA-N 0.000 description 15
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- 239000002904 solvent Substances 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- 125000003473 lipid group Chemical group 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 125000001736 nosyl group Chemical group S(=O)(=O)(C1=CC=C([N+](=O)[O-])C=C1)* 0.000 description 12
- 235000000346 sugar Nutrition 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 241000725303 Human immunodeficiency virus Species 0.000 description 9
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- 238000012360 testing method Methods 0.000 description 9
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 150000004676 glycans Chemical class 0.000 description 8
- 229920001282 polysaccharide Polymers 0.000 description 8
- 239000005017 polysaccharide Substances 0.000 description 8
- 229940035024 thioglycerol Drugs 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 230000036436 anti-hiv Effects 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 125000003132 pyranosyl group Chemical group 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 239000006228 supernatant Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 6
- 150000002772 monosaccharides Chemical class 0.000 description 6
- 125000001117 oleyl 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])=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])[H] 0.000 description 6
- 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 6
- TTZAPPKPTGLRTD-UHFFFAOYSA-N 1-butoxyicosane Chemical compound CCCCCCCCCCCCCCCCCCCCOCCCC TTZAPPKPTGLRTD-UHFFFAOYSA-N 0.000 description 5
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- 239000000706 filtrate Substances 0.000 description 5
- ZHQXSNATWQNESB-UHFFFAOYSA-N 3-docosoxy-2-(docosoxymethyl)-2-methylpropan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCOCC(C)(CN)COCCCCCCCCCCCCCCCCCCCCCC ZHQXSNATWQNESB-UHFFFAOYSA-N 0.000 description 4
- LWCIBYRXSHRIAP-UHFFFAOYSA-N 3-phenylmethoxypropane-1,2-diol Chemical compound OCC(O)COCC1=CC=CC=C1 LWCIBYRXSHRIAP-UHFFFAOYSA-N 0.000 description 4
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
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- BQINXKOTJQCISL-GRCPKETISA-N keto-neuraminic acid Chemical compound OC(=O)C(=O)C[C@H](O)[C@@H](N)[C@@H](O)[C@H](O)[C@H](O)CO BQINXKOTJQCISL-GRCPKETISA-N 0.000 description 4
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 4
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
- C07H15/06—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical being a hydroxyalkyl group esterified by a fatty acid
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- 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
- A61P31/18—Antivirals for RNA viruses for HIV
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
- C07H15/10—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical containing unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/14—Acyclic radicals, not substituted by cyclic structures attached to a sulfur, selenium or tellurium atom of a saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
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- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
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- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
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- Veterinary Medicine (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12202596 | 1996-05-16 | ||
| JP8-122025 | 1996-05-16 | ||
| PCT/JP1997/001654 WO1997043296A1 (en) | 1996-05-16 | 1997-05-16 | Novel compounds having antiviral activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPWO1997043296A1 JPWO1997043296A1 (ja) | 1999-06-22 |
| JP4099234B2 true JP4099234B2 (ja) | 2008-06-11 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP54074697A Expired - Fee Related JP4099234B2 (ja) | 1996-05-16 | 1997-05-16 | 抗ウイルス活性を有する新規化合物 |
Country Status (8)
| Country | Link |
|---|---|
| US (3) | US6337390B1 (https=) |
| EP (1) | EP0957107B1 (https=) |
| JP (1) | JP4099234B2 (https=) |
| AT (1) | ATE271560T1 (https=) |
| AU (1) | AU737680C (https=) |
| CA (1) | CA2255070C (https=) |
| DE (1) | DE69729958T2 (https=) |
| WO (1) | WO1997043296A1 (https=) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69729958T2 (de) * | 1996-05-16 | 2005-07-28 | Nissin Food Products Co., Ltd | Verbindungen mit antiviraler aktivität |
| WO1999043689A1 (fr) * | 1998-02-27 | 1999-09-02 | Meiji Milk Products Co., Ltd. | Nouveaux derives de kdn et medicaments les contenant sous forme de principes actifs |
| CA2356306C (en) | 1999-01-15 | 2006-02-21 | The Board Of Trustees Of The University Of Illinois | Sulfated phosphatidylinositols, their preparation and use |
| WO2003049672A2 (en) * | 2001-10-30 | 2003-06-19 | Microbiotix, Inc. | Methods and compositions for treating flavivirus-mediated disease |
| JP2008074720A (ja) * | 2006-09-19 | 2008-04-03 | Noguchi Inst | Ｇｍ３糖鎖プローブ |
| CA2685127C (en) | 2007-04-23 | 2019-01-08 | Alnylam Pharmaceuticals, Inc. | Glycoconjugates of rna interference agents |
| AU2014277867B2 (en) * | 2007-12-04 | 2016-11-03 | Arbutus Biopharma Corporation | Targeting lipids |
| EP2231194B1 (en) | 2007-12-04 | 2017-02-22 | Alnylam Pharmaceuticals Inc. | Folate-irna conjugates |
| WO2009082607A2 (en) | 2007-12-04 | 2009-07-02 | Alnylam Pharmaceuticals, Inc. | Targeting lipids |
| WO2009126933A2 (en) | 2008-04-11 | 2009-10-15 | Alnylam Pharmaceuticals, Inc. | Site-specific delivery of nucleic acids by combining targeting ligands with endosomolytic components |
| JP5327839B2 (ja) * | 2008-06-09 | 2013-10-30 | 国立大学法人埼玉大学 | シアル酸誘導体の製造方法とインフルエンザウィルス阻害剤としての利用 |
| PL2451822T3 (pl) * | 2009-07-07 | 2014-01-31 | Adenovir Pharma Ab | Nowe związki przeciwwirusowe użyteczne do leczenia epidemicznego zapalenia spojówek i rogówki (keratoconjonctivitis) lub do zapobiegania |
| TWI710633B (zh) | 2014-11-10 | 2020-11-21 | 美商阿尼拉製藥公司 | Ｂ型肝炎病毒（ＨＢＶ）ｉＲＮＡ組成物及其用途方法 |
| HK1257549A1 (zh) * | 2015-08-19 | 2019-10-25 | National Research Council Of Canada | 用 cmp 活化吡喃壬酮糖酸类似化合物治疗和预防奈瑟氏淋病球菌感染 |
| US11324820B2 (en) | 2017-04-18 | 2022-05-10 | Alnylam Pharmaceuticals, Inc. | Methods for the treatment of subjects having a hepatitis b virus (HBV) infection |
| CA3106701A1 (en) | 2018-08-13 | 2020-02-20 | Alnylam Pharmaceuticals, Inc. | Hepatitis b virus (hbv) dsrna agent compositions and methods of use thereof |
| EP4416163A1 (en) * | 2021-10-14 | 2024-08-21 | Owlstone Medical Limited | Method for the synthesis of evoc probes |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59164798A (ja) | 1983-03-09 | 1984-09-17 | Rikagaku Kenkyusho | シアル酸含有糖脂質誘導体 |
| JPH064671B2 (ja) | 1985-04-02 | 1994-01-19 | メクト株式会社 | シアル酸誘導体及びその製造方法 |
| JPS62212335A (ja) | 1986-03-14 | 1987-09-18 | Mitsui Toatsu Chem Inc | ２−アリ−ル−２−メチルプロピルエ−テル誘導体およびそれを有効成分として含有する殺虫剤 |
| JPS6345223A (ja) | 1986-04-04 | 1988-02-26 | Ueno Seiyaku Oyo Kenkyusho:Kk | ひと免疫不全ウイルス性疾患処置剤 |
| JPS63264493A (ja) | 1986-12-29 | 1988-11-01 | Mect Corp | 活性カルボニル基を持つシアル酸誘導体 |
| JPS6452794A (en) | 1987-05-29 | 1989-02-28 | Kanto Ishi Pharma Co Ltd | Sialic acid-containing thioglycerolipid derivative and production thereof |
| JPH01125394A (ja) | 1987-11-10 | 1989-05-17 | Mect Corp | シアロシルグリセロリピッド類及びその製造方法 |
| JPH02304025A (ja) | 1989-05-18 | 1990-12-17 | Tanabe Seiyaku Co Ltd | 抗レトロウィルス薬 |
| JPH0317020A (ja) * | 1989-06-14 | 1991-01-25 | Nippon Koutai Kenkyusho:Kk | 抗ｈｉｖ剤 |
| JPH03246297A (ja) | 1990-02-22 | 1991-11-01 | Nippon Koutai Kenkyusho:Kk | ガングリオシド誘導体及びこれを含有する抗ｈｉｖ剤 |
| JPH04136001A (ja) | 1990-09-27 | 1992-05-11 | Tanabe Seiyaku Co Ltd | β―シクロデキストリン・スルホンアミド誘導体のポリ硫酸エステル及びその製法 |
| ZA936452B (en) | 1992-09-02 | 1994-03-25 | Virostat Na N V | Sulphated glycoside |
| US5344417A (en) | 1992-09-11 | 1994-09-06 | Becton, Dickinson And Company | Universal fitting for inoculation receptacles |
| JPH06256373A (ja) | 1993-01-11 | 1994-09-13 | Dainippon Ink & Chem Inc | 硫酸化オリゴ糖配糖体アシル化物およびこれを有効成分とする抗ウイルス剤 |
| JP3062906B2 (ja) * | 1993-01-29 | 2000-07-12 | 丸金醤油株式会社 | Ｎ−アセチルノイラミン酸ホモポリマーの硫酸エステル |
| US5663151A (en) | 1994-03-04 | 1997-09-02 | Bristol-Myers Squibb Company | Sulfated α-glycolipid derivatives as cell adhesion inhibitors |
| JPH09183789A (ja) * | 1995-10-31 | 1997-07-15 | Sanwa Kagaku Kenkyusho Co Ltd | 新規な硫酸化及び燐酸化糖誘導体、その製法及び用途 |
| DE69729958T2 (de) * | 1996-05-16 | 2005-07-28 | Nissin Food Products Co., Ltd | Verbindungen mit antiviraler aktivität |
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1997
- 1997-05-16 DE DE69729958T patent/DE69729958T2/de not_active Expired - Fee Related
- 1997-05-16 US US09/180,618 patent/US6337390B1/en not_active Expired - Fee Related
- 1997-05-16 CA CA002255070A patent/CA2255070C/en not_active Expired - Fee Related
- 1997-05-16 EP EP97922075A patent/EP0957107B1/en not_active Expired - Lifetime
- 1997-05-16 AT AT97922075T patent/ATE271560T1/de not_active IP Right Cessation
- 1997-05-16 JP JP54074697A patent/JP4099234B2/ja not_active Expired - Fee Related
- 1997-05-16 AU AU27895/97A patent/AU737680C/en not_active Ceased
- 1997-05-16 WO PCT/JP1997/001654 patent/WO1997043296A1/ja not_active Ceased
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2001
- 2001-10-31 US US09/984,920 patent/US6541461B2/en not_active Expired - Fee Related
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2002
- 2002-09-23 US US10/252,036 patent/US6835720B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20030073664A1 (en) | 2003-04-17 |
| AU737680B2 (en) | 2001-08-30 |
| DE69729958T2 (de) | 2005-07-28 |
| ATE271560T1 (de) | 2004-08-15 |
| CA2255070A1 (en) | 1997-11-20 |
| CA2255070C (en) | 2006-08-15 |
| EP0957107A4 (https=) | 1999-11-17 |
| DE69729958D1 (de) | 2004-08-26 |
| EP0957107B1 (en) | 2004-07-21 |
| WO1997043296A1 (en) | 1997-11-20 |
| AU737680C (en) | 2002-05-02 |
| AU2789597A (en) | 1997-12-05 |
| US20020077472A1 (en) | 2002-06-20 |
| EP0957107A1 (en) | 1999-11-17 |
| US6541461B2 (en) | 2003-04-01 |
| US6835720B2 (en) | 2004-12-28 |
| US6337390B1 (en) | 2002-01-08 |
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