CA2255070C - Novel compounds having antiviral activity - Google Patents
Novel compounds having antiviral activity Download PDFInfo
- Publication number
- CA2255070C CA2255070C CA002255070A CA2255070A CA2255070C CA 2255070 C CA2255070 C CA 2255070C CA 002255070 A CA002255070 A CA 002255070A CA 2255070 A CA2255070 A CA 2255070A CA 2255070 C CA2255070 C CA 2255070C
- Authority
- CA
- Canada
- 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.)
- Expired - Fee Related
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 225
- 230000000840 anti-viral effect Effects 0.000 title abstract description 19
- 239000002253 acid Substances 0.000 claims abstract description 64
- 150000003839 salts Chemical class 0.000 claims abstract description 47
- 150000002632 lipids Chemical class 0.000 claims abstract description 42
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 14
- 150000002148 esters Chemical class 0.000 claims abstract description 14
- 150000001408 amides Chemical class 0.000 claims abstract description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000011734 sodium Substances 0.000 claims description 91
- 229910052708 sodium Inorganic materials 0.000 claims description 90
- 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 50
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 241000700605 Viruses Species 0.000 claims description 44
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 34
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- 125000004429 atom Chemical group 0.000 claims description 29
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- 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 10
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- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 229940040102 levulinic acid Drugs 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229960003194 meglumine Drugs 0.000 description 1
- NGYIMTKLQULBOO-UHFFFAOYSA-L mercury dibromide Chemical compound Br[Hg]Br NGYIMTKLQULBOO-UHFFFAOYSA-L 0.000 description 1
- FQGYCXFLEQVDJQ-UHFFFAOYSA-N mercury dicyanide Chemical compound N#C[Hg]C#N FQGYCXFLEQVDJQ-UHFFFAOYSA-N 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- WVJKHCGMRZGIJH-UHFFFAOYSA-N methanetriamine Chemical compound NC(N)N WVJKHCGMRZGIJH-UHFFFAOYSA-N 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical compound CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QSQGNBGEHSFMAA-UHFFFAOYSA-N octane-1,2,3-triol Chemical compound CCCCCC(O)C(O)CO QSQGNBGEHSFMAA-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000002482 oligosaccharides Chemical group 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- XYKIUTSFQGXHOW-UHFFFAOYSA-N propan-2-one;toluene Chemical compound CC(C)=O.CC1=CC=CC=C1 XYKIUTSFQGXHOW-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- 235000011088 sodium lactate Nutrition 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 235000019722 synbiotics Nutrition 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 150000003569 thioglycosides Chemical class 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 241001430294 unidentified retrovirus Species 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 210000003501 vero cell Anatomy 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000012873 virucide Substances 0.000 description 1
- 239000002545 virucidic Substances 0.000 description 1
- 229960002555 zidovudine Drugs 0.000 description 1
Classifications
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (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 |
|---|---|
| CA2255070A1 CA2255070A1 (en) | 1997-11-20 |
| CA2255070C true CA2255070C (en) | 2006-08-15 |
Family
ID=14825732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002255070A Expired - Fee Related CA2255070C (en) | 1996-05-16 | 1997-05-16 | Novel compounds having antiviral activity |
Country Status (8)
| Country | Link |
|---|---|
| US (3) | US6337390B1 (enExample) |
| EP (1) | EP0957107B1 (enExample) |
| JP (1) | JP4099234B2 (enExample) |
| AT (1) | ATE271560T1 (enExample) |
| AU (1) | AU737680C (enExample) |
| CA (1) | CA2255070C (enExample) |
| DE (1) | DE69729958T2 (enExample) |
| WO (1) | WO1997043296A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2255070C (en) * | 1996-05-16 | 2006-08-15 | Nissin Food Products Co., Ltd. | Novel compounds having antiviral activity |
| 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 |
| DE60007074T2 (de) | 1999-01-15 | 2004-09-16 | The Board Of Trustees For The University Of Illinois, Urbana | Sulfatierte phosphatidylinositole, ihre herstellung und verwendung |
| 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 |
| US8877917B2 (en) | 2007-04-23 | 2014-11-04 | Alnylam Pharmaceuticals, Inc. | Glycoconjugates of RNA interference agents |
| WO2009082607A2 (en) | 2007-12-04 | 2009-07-02 | Alnylam Pharmaceuticals, Inc. | Targeting lipids |
| AU2014277867B2 (en) * | 2007-12-04 | 2016-11-03 | Arbutus Biopharma Corporation | Targeting lipids |
| CA2708171C (en) | 2007-12-04 | 2018-02-27 | Alnylam Pharmaceuticals, Inc. | Folate conjugates |
| US8575123B2 (en) | 2008-04-11 | 2013-11-05 | Tekmira Pharmaceuticals Corporation | 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 |
| MY155507A (en) * | 2009-07-07 | 2015-10-30 | Adenovir Pharma Ab | Antiviral compounds |
| JOP20200092A1 (ar) | 2014-11-10 | 2017-06-16 | Alnylam Pharmaceuticals Inc | تركيبات iRNA لفيروس الكبد B (HBV) وطرق لاستخدامها |
| WO2017027980A1 (en) * | 2015-08-19 | 2017-02-23 | National Research Council Canada | Treatment and prevention of neisseria gonorrhoeae infection using cmp-activated nonulosonate analog compounds |
| US11324820B2 (en) | 2017-04-18 | 2022-05-10 | Alnylam Pharmaceuticals, Inc. | Methods for the treatment of subjects having a hepatitis b virus (HBV) infection |
| BR112021001613A2 (pt) | 2018-08-13 | 2021-05-04 | Alnylam Pharmaceuticals, Inc. | agentes de ácido ribonucleico de fita dupla, célula, composições farmacêuticas, métodos de inibição da expressão gênica, de inibição da replicação e de tratar um sujeito, métodos para reduzir o nível de um antígeno e para reduzir a carga viral e uso de um agente de dsrna |
| JP2024542305A (ja) * | 2021-10-14 | 2024-11-14 | アウルストーン・メディカル・リミテッド | Ｅｖｏｃプローブを合成するための方法 |
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 |
| CA2255070C (en) * | 1996-05-16 | 2006-08-15 | Nissin Food Products Co., Ltd. | Novel compounds having antiviral activity |
-
1997
- 1997-05-16 CA CA002255070A patent/CA2255070C/en not_active Expired - Fee Related
- 1997-05-16 AU AU27895/97A patent/AU737680C/en not_active Ceased
- 1997-05-16 EP EP97922075A patent/EP0957107B1/en not_active Expired - Lifetime
- 1997-05-16 JP JP54074697A patent/JP4099234B2/ja not_active Expired - Fee Related
- 1997-05-16 DE DE69729958T patent/DE69729958T2/de not_active Expired - Fee Related
- 1997-05-16 WO PCT/JP1997/001654 patent/WO1997043296A1/ja not_active Ceased
- 1997-05-16 AT AT97922075T patent/ATE271560T1/de not_active IP Right Cessation
- 1997-05-16 US US09/180,618 patent/US6337390B1/en not_active Expired - Fee Related
-
2001
- 2001-10-31 US US09/984,920 patent/US6541461B2/en not_active Expired - Fee Related
-
2002
- 2002-09-23 US US10/252,036 patent/US6835720B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US6541461B2 (en) | 2003-04-01 |
| US6337390B1 (en) | 2002-01-08 |
| DE69729958T2 (de) | 2005-07-28 |
| DE69729958D1 (de) | 2004-08-26 |
| EP0957107B1 (en) | 2004-07-21 |
| EP0957107A4 (enExample) | 1999-11-17 |
| US20020077472A1 (en) | 2002-06-20 |
| AU737680B2 (en) | 2001-08-30 |
| WO1997043296A1 (en) | 1997-11-20 |
| AU737680C (en) | 2002-05-02 |
| US20030073664A1 (en) | 2003-04-17 |
| ATE271560T1 (de) | 2004-08-15 |
| AU2789597A (en) | 1997-12-05 |
| CA2255070A1 (en) | 1997-11-20 |
| US6835720B2 (en) | 2004-12-28 |
| JP4099234B2 (ja) | 2008-06-11 |
| EP0957107A1 (en) | 1999-11-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |