CA2702344C - Analogues of glycolipids useful as immunoadjuvants - Google Patents
Analogues of glycolipids useful as immunoadjuvants Download PDFInfo
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- CA2702344C CA2702344C CA2702344A CA2702344A CA2702344C CA 2702344 C CA2702344 C CA 2702344C CA 2702344 A CA2702344 A CA 2702344A CA 2702344 A CA2702344 A CA 2702344A CA 2702344 C CA2702344 C CA 2702344C
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- 229930186217 Glycolipid Natural products 0.000 title description 9
- 230000001571 immunoadjuvant effect Effects 0.000 title description 3
- 239000000568 immunological adjuvant Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 80
- 239000000427 antigen Substances 0.000 claims abstract description 62
- 108091007433 antigens Proteins 0.000 claims abstract description 61
- 102000036639 antigens Human genes 0.000 claims abstract description 61
- 238000000034 method Methods 0.000 claims abstract description 35
- 230000028993 immune response Effects 0.000 claims abstract description 16
- 239000000203 mixture Substances 0.000 claims description 76
- 125000000217 alkyl group Chemical group 0.000 claims description 53
- 125000003118 aryl group Chemical group 0.000 claims description 40
- 125000005842 heteroatom Chemical group 0.000 claims description 25
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 125000006239 protecting group Chemical group 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 125000001853 C4-C20 hydrocarbyl group Chemical group 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 230000001580 bacterial effect Effects 0.000 claims description 3
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- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 4
- VQFKFAKEUMHBLV-BYSUZVQFSA-N 1-O-(alpha-D-galactosyl)-N-hexacosanoylphytosphingosine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@H]([C@H](O)[C@H](O)CCCCCCCCCCCCCC)CO[C@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O VQFKFAKEUMHBLV-BYSUZVQFSA-N 0.000 abstract description 26
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- 101150041968 CDC13 gene Proteins 0.000 description 22
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- 125000003342 alkenyl group Chemical group 0.000 description 20
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 241000699670 Mus sp. Species 0.000 description 14
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 description 14
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- 235000011152 sodium sulphate Nutrition 0.000 description 10
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 10
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- 238000006243 chemical reaction Methods 0.000 description 9
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- 125000005647 linker group Chemical group 0.000 description 9
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- 229910052757 nitrogen Inorganic materials 0.000 description 8
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- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 7
- 241000699666 Mus <mouse, genus> Species 0.000 description 7
- 229910019142 PO4 Inorganic materials 0.000 description 7
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 7
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- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 7
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 7
- 230000000091 immunopotentiator Effects 0.000 description 7
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
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- 238000003556 assay Methods 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
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- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
- XMHIUKTWLZUKEX-UHFFFAOYSA-N hexacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O XMHIUKTWLZUKEX-UHFFFAOYSA-N 0.000 description 6
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- NNISLDGFPWIBDF-MPRBLYSKSA-N alpha-D-Gal-(1->3)-beta-D-Gal-(1->4)-D-GlcNAc Chemical compound O[C@@H]1[C@@H](NC(=O)C)C(O)O[C@H](CO)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)[C@@H](O)[C@@H](CO)O1 NNISLDGFPWIBDF-MPRBLYSKSA-N 0.000 description 5
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- 230000028327 secretion Effects 0.000 description 1
- 239000012679 serum free medium Substances 0.000 description 1
- 229940069764 shark liver oil Drugs 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
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229940084106 spermaceti Drugs 0.000 description 1
- 239000012177 spermaceti Substances 0.000 description 1
- WWUZIQQURGPMPG-KRWOKUGFSA-N sphingosine Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO WWUZIQQURGPMPG-KRWOKUGFSA-N 0.000 description 1
- 150000003410 sphingosines Chemical class 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000010186 staining Methods 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
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000008362 succinate buffer Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 235000020238 sunflower seed Nutrition 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Substances C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 241000712461 unidentified influenza virus Species 0.000 description 1
- 239000012646 vaccine adjuvant Substances 0.000 description 1
- 229940124931 vaccine adjuvant Drugs 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229940118696 vibrio cholerae Drugs 0.000 description 1
- 210000002845 virion Anatomy 0.000 description 1
- 239000010698 whale oil Substances 0.000 description 1
- 241000228158 x Triticosecale Species 0.000 description 1
- 229940051021 yellow-fever virus Drugs 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 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
- C07H15/26—Acyclic or carbocyclic radicals, substituted by 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
- A61P31/04—Antibacterial agents
-
- 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
- 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
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- 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
- C07H15/18—Acyclic radicals, substituted by carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biochemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Immunology (AREA)
- Oncology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Virology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Saccharide Compounds (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US97978507P | 2007-10-12 | 2007-10-12 | |
| US60/979,785 | 2007-10-12 | ||
| PCT/IB2008/003263 WO2009060305A2 (en) | 2007-10-12 | 2008-10-10 | Analogues of glycolipids useful as immunoadjuvants |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2702344A1 CA2702344A1 (en) | 2009-05-14 |
| CA2702344C true CA2702344C (en) | 2016-09-27 |
Family
ID=40626266
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2702344A Active CA2702344C (en) | 2007-10-12 | 2008-10-10 | Analogues of glycolipids useful as immunoadjuvants |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8697659B2 (enExample) |
| EP (1) | EP2483287B1 (enExample) |
| JP (1) | JP5416125B2 (enExample) |
| CN (1) | CN102066394B (enExample) |
| AU (1) | AU2008326138B2 (enExample) |
| CA (1) | CA2702344C (enExample) |
| ES (1) | ES2574825T3 (enExample) |
| WO (1) | WO2009060305A2 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5640079B2 (ja) | 2009-05-18 | 2014-12-10 | シグモイド・ファーマ・リミテッドＳｉｇｍｏｉｄ Ｐｈａｒｍａ Ｌｉｍｉｔｅｄ | 油滴含有組成物 |
| CN102573802A (zh) * | 2009-08-12 | 2012-07-11 | 希格默伊德药业有限公司 | 包含聚合物基质和油相的免疫调节组合物 |
| AU2013237497B2 (en) * | 2012-03-19 | 2016-05-12 | Max-Planck-Gesellschaft Zur Forderung Der Wissenschaften E.V. | Carbohydrate-glycolipid conjugate vaccines |
| GB201212010D0 (en) | 2012-07-05 | 2012-08-22 | Sigmoid Pharma Ltd | Formulations |
| PT3215127T (pt) | 2014-11-07 | 2021-02-10 | Sublimity Therapeutics Ltd | Composições que compreendem ciclosporina |
| WO2022256467A1 (en) * | 2021-06-02 | 2022-12-08 | The Charlotte Mecklenburg Hospital Authority D/B/A Atrium Health | Compositions and methods comprising deoxy-pentitols |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW261533B (enExample) * | 1992-07-16 | 1995-11-01 | Kirin Brewery | |
| EP1437358B1 (en) | 2001-08-16 | 2006-10-18 | Daiichi Asubio Pharma Co., Ltd. | Novel glycolipid and remedial agent for autoimmune disease containing the same as active ingredient |
| GB0314682D0 (en) * | 2003-06-24 | 2003-07-30 | Isis Innovation | Materials and methods relating to the modulation of T cell response to soluble antigen |
| EP1784196B1 (en) | 2004-08-27 | 2016-12-21 | Albert Einstein College Of Medicine Of Yeshiva University | Ceramide derivatives as modulators of immunity and autoimmunity |
| US7923013B2 (en) * | 2004-12-28 | 2011-04-12 | The Rockefeller University | Glycolipids and analogues thereof as antigens for NKT cells |
| EP1776963A1 (en) | 2005-10-19 | 2007-04-25 | Gbf-Gesellschaft Für Biotechnologische Forschung Mbh | Hexosylceramides as adjuvants and their uses in pharmaceutical compositions |
-
2008
- 2008-10-10 CA CA2702344A patent/CA2702344C/en active Active
- 2008-10-10 EP EP08848559.4A patent/EP2483287B1/en active Active
- 2008-10-10 WO PCT/IB2008/003263 patent/WO2009060305A2/en not_active Ceased
- 2008-10-10 CN CN200880119643.0A patent/CN102066394B/zh not_active Expired - Fee Related
- 2008-10-10 ES ES08848559.4T patent/ES2574825T3/es active Active
- 2008-10-10 JP JP2010528504A patent/JP5416125B2/ja not_active Expired - Fee Related
- 2008-10-10 AU AU2008326138A patent/AU2008326138B2/en not_active Ceased
- 2008-10-10 US US12/734,140 patent/US8697659B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN102066394A (zh) | 2011-05-18 |
| JP5416125B2 (ja) | 2014-02-12 |
| US8697659B2 (en) | 2014-04-15 |
| EP2483287B1 (en) | 2016-03-16 |
| WO2009060305A2 (en) | 2009-05-14 |
| CN102066394B (zh) | 2015-04-01 |
| US20110033485A1 (en) | 2011-02-10 |
| CA2702344A1 (en) | 2009-05-14 |
| AU2008326138B2 (en) | 2013-10-17 |
| ES2574825T3 (es) | 2016-06-22 |
| WO2009060305A3 (en) | 2013-05-23 |
| EP2483287A2 (en) | 2012-08-08 |
| AU2008326138A1 (en) | 2009-05-14 |
| JP2011510910A (ja) | 2011-04-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20130930 |