DE602005005953T2 - Verfahren zur herstellung von carboxyalkylinulin - Google Patents
Verfahren zur herstellung von carboxyalkylinulin Download PDFInfo
- Publication number
- DE602005005953T2 DE602005005953T2 DE602005005953T DE602005005953T DE602005005953T2 DE 602005005953 T2 DE602005005953 T2 DE 602005005953T2 DE 602005005953 T DE602005005953 T DE 602005005953T DE 602005005953 T DE602005005953 T DE 602005005953T DE 602005005953 T2 DE602005005953 T2 DE 602005005953T2
- Authority
- DE
- Germany
- Prior art keywords
- inulin
- slurry
- reaction
- range
- temperature
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims description 11
- 229920001202 Inulin Polymers 0.000 claims abstract description 53
- JYJIGFIDKWBXDU-MNNPPOADSA-N inulin Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@]1(OC[C@]2(OC[C@]3(OC[C@]4(OC[C@]5(OC[C@]6(OC[C@]7(OC[C@]8(OC[C@]9(OC[C@]%10(OC[C@]%11(OC[C@]%12(OC[C@]%13(OC[C@]%14(OC[C@]%15(OC[C@]%16(OC[C@]%17(OC[C@]%18(OC[C@]%19(OC[C@]%20(OC[C@]%21(OC[C@]%22(OC[C@]%23(OC[C@]%24(OC[C@]%25(OC[C@]%26(OC[C@]%27(OC[C@]%28(OC[C@]%29(OC[C@]%30(OC[C@]%31(OC[C@]%32(OC[C@]%33(OC[C@]%34(OC[C@]%35(OC[C@]%36(O[C@@H]%37[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O%37)O)[C@H]([C@H](O)[C@@H](CO)O%36)O)[C@H]([C@H](O)[C@@H](CO)O%35)O)[C@H]([C@H](O)[C@@H](CO)O%34)O)[C@H]([C@H](O)[C@@H](CO)O%33)O)[C@H]([C@H](O)[C@@H](CO)O%32)O)[C@H]([C@H](O)[C@@H](CO)O%31)O)[C@H]([C@H](O)[C@@H](CO)O%30)O)[C@H]([C@H](O)[C@@H](CO)O%29)O)[C@H]([C@H](O)[C@@H](CO)O%28)O)[C@H]([C@H](O)[C@@H](CO)O%27)O)[C@H]([C@H](O)[C@@H](CO)O%26)O)[C@H]([C@H](O)[C@@H](CO)O%25)O)[C@H]([C@H](O)[C@@H](CO)O%24)O)[C@H]([C@H](O)[C@@H](CO)O%23)O)[C@H]([C@H](O)[C@@H](CO)O%22)O)[C@H]([C@H](O)[C@@H](CO)O%21)O)[C@H]([C@H](O)[C@@H](CO)O%20)O)[C@H]([C@H](O)[C@@H](CO)O%19)O)[C@H]([C@H](O)[C@@H](CO)O%18)O)[C@H]([C@H](O)[C@@H](CO)O%17)O)[C@H]([C@H](O)[C@@H](CO)O%16)O)[C@H]([C@H](O)[C@@H](CO)O%15)O)[C@H]([C@H](O)[C@@H](CO)O%14)O)[C@H]([C@H](O)[C@@H](CO)O%13)O)[C@H]([C@H](O)[C@@H](CO)O%12)O)[C@H]([C@H](O)[C@@H](CO)O%11)O)[C@H]([C@H](O)[C@@H](CO)O%10)O)[C@H]([C@H](O)[C@@H](CO)O9)O)[C@H]([C@H](O)[C@@H](CO)O8)O)[C@H]([C@H](O)[C@@H](CO)O7)O)[C@H]([C@H](O)[C@@H](CO)O6)O)[C@H]([C@H](O)[C@@H](CO)O5)O)[C@H]([C@H](O)[C@@H](CO)O4)O)[C@H]([C@H](O)[C@@H](CO)O3)O)[C@H]([C@H](O)[C@@H](CO)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 JYJIGFIDKWBXDU-MNNPPOADSA-N 0.000 claims abstract description 49
- 229940029339 inulin Drugs 0.000 claims abstract description 49
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- 239000002609 medium Substances 0.000 claims abstract description 9
- 239000012736 aqueous medium Substances 0.000 claims abstract description 7
- 238000010438 heat treatment Methods 0.000 claims abstract description 3
- 239000002002 slurry Substances 0.000 claims description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- 239000011541 reaction mixture Substances 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 10
- 239000003153 chemical reaction reagent Substances 0.000 claims description 10
- -1 haloalkyl carboxylate Chemical class 0.000 claims description 10
- 150000002772 monosaccharides Chemical group 0.000 claims description 8
- 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 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims 1
- BJHIKXHVCXFQLS-UYFOZJQFSA-N fructose group Chemical group OCC(=O)[C@@H](O)[C@H](O)[C@H](O)CO BJHIKXHVCXFQLS-UYFOZJQFSA-N 0.000 claims 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 abstract description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract description 5
- 150000007942 carboxylates Chemical class 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 229920002670 Fructan Polymers 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- ZFTFOHBYVDOAMH-XNOIKFDKSA-N (2r,3s,4s,5r)-5-[[(2r,3s,4s,5r)-5-[[(2r,3s,4s,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-2-(hydroxymethyl)oxolan-2-yl]oxymethyl]-2-(hydroxymethyl)oxolane-2,3,4-triol Chemical class O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@@H]1[C@@H](O)[C@H](O)[C@](CO)(OC[C@@H]2[C@H]([C@H](O)[C@@](O)(CO)O2)O)O1 ZFTFOHBYVDOAMH-XNOIKFDKSA-N 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 5
- 239000008186 active pharmaceutical agent Substances 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241001136792 Alle Species 0.000 description 1
- RKWGIWYCVPQPMF-UHFFFAOYSA-N Chloropropamide Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 RKWGIWYCVPQPMF-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 102000004877 Insulin Human genes 0.000 description 1
- 108090001061 Insulin Proteins 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229940125396 insulin Drugs 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005374 membrane filtration Methods 0.000 description 1
- 238000001728 nano-filtration Methods 0.000 description 1
- 150000002482 oligosaccharides Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0051—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Fructofuranans, e.g. beta-2,6-D-fructofuranan, i.e. levan; Derivatives thereof
- C08B37/0054—Inulin, i.e. beta-2,1-D-fructofuranan; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04075280 | 2004-01-30 | ||
| EP04075280A EP1559727A1 (en) | 2004-01-30 | 2004-01-30 | Method for the manufacture of carboxyalkylinulin |
| PCT/BE2005/000011 WO2005073256A1 (en) | 2004-01-30 | 2005-01-28 | Method for the manufacture of carboxyalkylinulin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE602005005953D1 DE602005005953D1 (de) | 2008-05-21 |
| DE602005005953T2 true DE602005005953T2 (de) | 2009-09-10 |
Family
ID=34639450
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE602005005953T Expired - Lifetime DE602005005953T2 (de) | 2004-01-30 | 2005-01-28 | Verfahren zur herstellung von carboxyalkylinulin |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7728124B2 (https=) |
| EP (2) | EP1559727A1 (https=) |
| JP (1) | JP5019513B2 (https=) |
| CN (1) | CN1914230B (https=) |
| AT (1) | ATE391731T1 (https=) |
| AU (1) | AU2005209336B2 (https=) |
| CA (1) | CA2555205C (https=) |
| DE (1) | DE602005005953T2 (https=) |
| ES (1) | ES2307140T3 (https=) |
| RU (1) | RU2373223C2 (https=) |
| WO (1) | WO2005073256A1 (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2388308A1 (en) | 2010-05-19 | 2011-11-23 | Dequest AG | Cleaning composition with improved stain removal |
| US8883711B2 (en) | 2010-05-19 | 2014-11-11 | Italmatch Chemicals Spa | Cleaning composition with improved stain removal |
| WO2013087665A2 (en) * | 2011-12-12 | 2013-06-20 | Dequest Ag | Cosmetic composition for skin or hair care |
| EP2626373A1 (en) | 2012-02-08 | 2013-08-14 | Dequest AG | Method for the manufacture of concentrated aqueous solutions of alkali metal salt of carboxymethyl fructan |
| CN104231117B (zh) * | 2014-09-22 | 2016-08-10 | 忻州师范学院 | 一种离子液体促进下制备羧甲基菊粉的方法 |
| CN107674100A (zh) * | 2017-09-28 | 2018-02-09 | 中国科学院烟台海岸带研究所 | 一种菊粉短链脂肪酸酯的制备方法 |
| EP3561032A1 (en) | 2018-04-27 | 2019-10-30 | The Procter & Gamble Company | Antimicrobial hard surface cleaners comprising alkylpyrrolidones |
| EP4234668A3 (en) | 2018-04-27 | 2023-10-04 | The Procter & Gamble Company | Hard surface cleaners comprising carboxylated fructan |
| EP3561031B1 (en) | 2018-04-27 | 2025-06-04 | The Procter & Gamble Company | Alkaline hard surface cleaners comprising alkylpyrrolidones |
| JP7637622B2 (ja) * | 2019-08-01 | 2025-02-28 | 株式会社ダイセル | 多孔質セルロース及びその製造方法 |
| EP4484535A1 (en) | 2023-06-28 | 2025-01-01 | The Procter & Gamble Company | Hard surface cleaners comprising carboxylated fructan |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3303153A1 (de) * | 1983-01-31 | 1984-08-02 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur herstellung von hochsubstituierten carboxyalkylcellulosen und deren mischethern |
| JPH03287595A (ja) * | 1990-04-04 | 1991-12-18 | Kao Corp | カルボキシアルキル化グリコシド及びその製造方法 |
| DE4101910A1 (de) * | 1991-01-23 | 1992-07-30 | Laevosan Gmbh & Co Kg | Verfahren zur herstellung eines pyrogenfreien gut wasserloeslichen fructans sowie ein nierendiagnostikum, das ein solches fructan enthaelt |
| NL9302163A (nl) * | 1993-12-10 | 1995-07-03 | Univ Delft Tech | Gecarboxymethyleerde oligo- en polysacchariden als kristallisatie inhibitors. |
| EP0879249B1 (en) * | 1996-02-09 | 2001-09-05 | Coöperatie Cosun U.A. | Modified inulin |
| EP0930317A1 (en) * | 1998-01-21 | 1999-07-21 | Tiense Suikerraffinaderij N.V. (Raffinerie Tirlemontoise S.A.) | Process for the manufacture of chicory inulin, hydrolysates and derivatives of inulin, and improved chicory inulin products, hydrolysates and derivatives |
| NL1008371C2 (nl) * | 1998-02-20 | 1999-08-24 | Cooperatie Cosun U A | Werkwijze voor het bestrijden van aanslag in het suikerproces. |
-
2004
- 2004-01-30 EP EP04075280A patent/EP1559727A1/en not_active Withdrawn
-
2005
- 2005-01-28 DE DE602005005953T patent/DE602005005953T2/de not_active Expired - Lifetime
- 2005-01-28 EP EP05700220A patent/EP1713831B1/en not_active Expired - Lifetime
- 2005-01-28 AT AT05700220T patent/ATE391731T1/de active
- 2005-01-28 CN CN2005800037274A patent/CN1914230B/zh not_active Expired - Lifetime
- 2005-01-28 US US10/587,878 patent/US7728124B2/en active Active
- 2005-01-28 CA CA2555205A patent/CA2555205C/en not_active Expired - Lifetime
- 2005-01-28 RU RU2006130010/04A patent/RU2373223C2/ru active
- 2005-01-28 WO PCT/BE2005/000011 patent/WO2005073256A1/en not_active Ceased
- 2005-01-28 AU AU2005209336A patent/AU2005209336B2/en not_active Expired
- 2005-01-28 JP JP2006549794A patent/JP5019513B2/ja not_active Expired - Lifetime
- 2005-01-28 ES ES05700220T patent/ES2307140T3/es not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| AU2005209336A1 (en) | 2005-08-11 |
| JP2007532698A (ja) | 2007-11-15 |
| ES2307140T3 (es) | 2008-11-16 |
| ATE391731T1 (de) | 2008-04-15 |
| US20070225483A1 (en) | 2007-09-27 |
| US7728124B2 (en) | 2010-06-01 |
| EP1713831B1 (en) | 2008-04-09 |
| RU2373223C2 (ru) | 2009-11-20 |
| CA2555205C (en) | 2012-09-18 |
| CA2555205A1 (en) | 2005-08-11 |
| EP1713831A1 (en) | 2006-10-25 |
| JP5019513B2 (ja) | 2012-09-05 |
| AU2005209336B2 (en) | 2011-08-25 |
| DE602005005953D1 (de) | 2008-05-21 |
| CN1914230B (zh) | 2010-05-26 |
| EP1559727A1 (en) | 2005-08-03 |
| RU2006130010A (ru) | 2008-03-10 |
| WO2005073256A1 (en) | 2005-08-11 |
| CN1914230A (zh) | 2007-02-14 |
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