CA2705367C - Method for converting trans-cis nepetalactone to cis-trans nepetalactone using molecular sieves - Google Patents
Method for converting trans-cis nepetalactone to cis-trans nepetalactone using molecular sieves Download PDFInfo
- Publication number
- CA2705367C CA2705367C CA2705367A CA2705367A CA2705367C CA 2705367 C CA2705367 C CA 2705367C CA 2705367 A CA2705367 A CA 2705367A CA 2705367 A CA2705367 A CA 2705367A CA 2705367 C CA2705367 C CA 2705367C
- Authority
- CA
- Canada
- Prior art keywords
- trans
- nepetalactone
- cis
- mixture
- catmint oil
- 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
Links
- 239000002808 molecular sieve Substances 0.000 title claims abstract description 92
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 title claims abstract description 91
- ZDKZHVNKFOXMND-VDAHYXPESA-N trans-cis-Nepetalactone Natural products O=C1OC=C(C)[C@@H]2[C@@H]1[C@H](C)CC2 ZDKZHVNKFOXMND-VDAHYXPESA-N 0.000 title claims abstract description 70
- ZDKZHVNKFOXMND-NBEYISGCSA-N cis-trans-nepetalactone Chemical compound O=C1OC=C(C)[C@@H]2[C@H]1[C@@H](C)CC2 ZDKZHVNKFOXMND-NBEYISGCSA-N 0.000 title claims abstract description 55
- ZDKZHVNKFOXMND-ZQARSLAVSA-N trans-cis-nepetalactone Chemical compound O=C1OC=C(C)[C@@H]2[C@@H]1[C@@H](C)CC2 ZDKZHVNKFOXMND-ZQARSLAVSA-N 0.000 title claims abstract description 53
- 238000000034 method Methods 0.000 title claims abstract description 46
- ZDKZHVNKFOXMND-FTLITQJKSA-N cis-trans-Nepetalactone Natural products O=C1OC=C(C)[C@@H]2[C@H]1[C@H](C)CC2 ZDKZHVNKFOXMND-FTLITQJKSA-N 0.000 title claims abstract description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000010438 heat treatment Methods 0.000 claims abstract description 11
- 240000009215 Nepeta cataria Species 0.000 claims description 59
- 235000010679 Nepeta cataria Nutrition 0.000 claims description 57
- 239000000203 mixture Substances 0.000 claims description 50
- -1 trans-cis nepetalactone compound Chemical class 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 16
- LSRNBGXEEKNZHN-UHFFFAOYSA-N Dihydronepetalactone Chemical compound O=C1OCC(C)C2C1C(C)CC2 LSRNBGXEEKNZHN-UHFFFAOYSA-N 0.000 claims description 12
- 241001529733 Nepeta Species 0.000 claims description 3
- 239000003921 oil Substances 0.000 description 54
- 230000000694 effects Effects 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- ZDKZHVNKFOXMND-UHFFFAOYSA-N cis-Nepetalactone Natural products O=C1OC=C(C)C2C1C(C)CC2 ZDKZHVNKFOXMND-UHFFFAOYSA-N 0.000 description 13
- 150000001768 cations Chemical class 0.000 description 11
- 239000011324 bead Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 9
- 239000010457 zeolite Substances 0.000 description 9
- 229910021536 Zeolite Inorganic materials 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 238000003860 storage Methods 0.000 description 7
- PLWVFYKDQKCFIY-UHFFFAOYSA-N (+)-Nepetalic acid Natural products O=C1OC(O)C(C)C2C1C(C)CC2 PLWVFYKDQKCFIY-UHFFFAOYSA-N 0.000 description 6
- RGTMAXSVLBZNEL-RBXMUDONSA-N (1r,2s,5r)-2-methyl-5-[(2r)-1-oxopropan-2-yl]cyclopentane-1-carboxylic acid Chemical compound O=C[C@H](C)[C@H]1CC[C@H](C)[C@H]1C(O)=O RGTMAXSVLBZNEL-RBXMUDONSA-N 0.000 description 6
- RGTMAXSVLBZNEL-UHFFFAOYSA-N Nepetalic acid Natural products O=CC(C)C1CCC(C)C1C(O)=O RGTMAXSVLBZNEL-UHFFFAOYSA-N 0.000 description 6
- 230000004913 activation Effects 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000011148 porous material Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 101100055523 Caenorhabditis elegans amt-2 gene Proteins 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000000638 solvent extraction Methods 0.000 description 3
- 238000001256 steam distillation Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 101100065719 Drosophila melanogaster Ets98B gene Proteins 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910000323 aluminium silicate Inorganic materials 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- ZDKZHVNKFOXMND-XVYDVKMFSA-N cis-cis-nepetalactone Chemical compound O=C1OC=C(C)[C@H]2[C@@H]1[C@@H](C)CC2 ZDKZHVNKFOXMND-XVYDVKMFSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229910052680 mordenite Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- NZTAYUZDCFZKGA-UHFFFAOYSA-N 2-methyl-5-propan-2-ylcyclopentane-1-carboxylic acid Chemical compound CC(C)C1CCC(C)C1C(O)=O NZTAYUZDCFZKGA-UHFFFAOYSA-N 0.000 description 1
- 241000269350 Anura Species 0.000 description 1
- 101100065718 Caenorhabditis elegans ets-4 gene Proteins 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GNKTZDSRQHMHLZ-UHFFFAOYSA-N [Si].[Si].[Si].[Ti].[Ti].[Ti].[Ti].[Ti] Chemical compound [Si].[Si].[Si].[Ti].[Ti].[Ti].[Ti].[Ti] GNKTZDSRQHMHLZ-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 229910001657 ferrierite group Inorganic materials 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 238000000194 supercritical-fluid extraction Methods 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/94—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Seasonings (AREA)
- Pyrane Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US99011707P | 2007-11-26 | 2007-11-26 | |
| US60/990,117 | 2007-11-26 | ||
| PCT/US2008/084795 WO2009070641A1 (en) | 2007-11-26 | 2008-11-26 | Method for converting trans-cis nepetalactone to cis-trans nepetalactone using molecular sieves |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2705367A1 CA2705367A1 (en) | 2009-06-04 |
| CA2705367C true CA2705367C (en) | 2016-05-31 |
Family
ID=40364434
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2705367A Expired - Fee Related CA2705367C (en) | 2007-11-26 | 2008-11-26 | Method for converting trans-cis nepetalactone to cis-trans nepetalactone using molecular sieves |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8802870B2 (https=) |
| EP (1) | EP2217586B1 (https=) |
| JP (1) | JP5377508B2 (https=) |
| KR (1) | KR101577472B1 (https=) |
| CN (1) | CN101874027B (https=) |
| CA (1) | CA2705367C (https=) |
| ES (1) | ES2442010T3 (https=) |
| MX (1) | MX2010005706A (https=) |
| WO (1) | WO2009070641A1 (https=) |
| ZA (1) | ZA201003220B (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7547793B2 (en) * | 2003-03-19 | 2009-06-16 | E.I. Du Pont De Nemours And Company | Method for making insect repellent composition |
| WO2007133683A2 (en) * | 2006-05-10 | 2007-11-22 | E. I. Du Pont De Nemours And Company | Formulated tick and insect repellent compositions |
| BRPI0719458A2 (pt) * | 2006-12-21 | 2014-02-04 | Du Pont | "Processos para a obtenção de óleo de girataria" |
| WO2008079253A1 (en) | 2006-12-21 | 2008-07-03 | E. I. Du Pont De Nemours And Company | Hydrogenation of catmint oil |
| CN101563334B (zh) * | 2006-12-21 | 2012-08-22 | 纳幕尔杜邦公司 | 通过氢化荆芥内酯制备二氢荆芥内酯 |
| US8558015B2 (en) * | 2006-12-21 | 2013-10-15 | E I Du Pont De Nemours And Company | Solvent addition and removal in the hydrogenation of catmint oil |
| US9521844B2 (en) | 2006-12-21 | 2016-12-20 | E I Du Pont De Nemours And Company | Solvent addition and removal in the hydrogenation of catmint oil |
| KR101577472B1 (ko) | 2007-11-26 | 2015-12-14 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 분자체를 사용하여 트랜스-시스 네페타락톤을 시스-트랜스 네페타락톤으로 변환하는 방법 |
| PH12012500935A1 (en) | 2009-11-11 | 2012-11-26 | Du Pont | Method for the enhanced recovery of catmint oil |
| EP2762873A4 (en) | 2011-09-26 | 2015-05-20 | Toto Ltd | METHOD FOR SPECIFIC DETECTION OF A TEST SUBSTANCE |
| JP6107466B2 (ja) | 2012-06-28 | 2017-04-05 | セントラル硝子株式会社 | トランス−１，３，３，３−テトラフルオロプロペンの精製方法 |
| CN103012338B (zh) * | 2012-12-07 | 2014-10-08 | 南京中医药大学 | 一种荆芥内酯对溴苯甲酸酯及其制备工艺和用途 |
| CN114324645B (zh) * | 2021-12-24 | 2023-10-24 | 广州白云山汉方现代药业有限公司 | 一种快速鉴别藏荆芥药材的方法 |
| US12378213B1 (en) | 2024-08-13 | 2025-08-05 | William Allen Boulanger | Process for the hydrogenation of catnip oil |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4496467A (en) * | 1983-02-23 | 1985-01-29 | International Flavors & Fragrances Inc. | Insect repellent, pheremonal, animal repellent diagnostic and/or aroma augmenting or enhancing compositions and articles containing at least a major proportion of poly(epsilon caprolactone)homopolymers, and having imbedded therein one or more functional |
| US4686093A (en) * | 1984-04-13 | 1987-08-11 | Union Carbide Corporation | Molecular sieve compositions with aluminum, phosphorus and at least two other elements |
| CA1241628A (en) | 1984-04-13 | 1988-09-06 | Brent M.T. Lok | Molecular sieve compositions |
| CA1241943A (en) | 1984-04-13 | 1988-09-13 | Brent M.T. Lok | Molecular sieve compositions |
| EP0159624B1 (en) | 1984-04-13 | 1991-12-18 | Uop | Molecular sieve compositions |
| CN1011220B (zh) * | 1984-04-13 | 1991-01-16 | 联合碳化公司 | 分子筛的制备方法 |
| US4869896A (en) * | 1984-05-30 | 1989-09-26 | Angus Chemical Company | Potentiated insect repellent composition and method |
| US5072063A (en) * | 1990-01-09 | 1991-12-10 | Dowelanco | Process for rearranging allylic geminal dihalogen compounds |
| EP0938460B1 (en) * | 1996-11-13 | 2004-01-28 | Chevron Phillips Chemical Company LP | Process for olefin isomerization |
| US6524605B1 (en) * | 1999-08-06 | 2003-02-25 | Iowa State University Research Foundation, Inc. | Biorational repellents obtained from terpenoids for use against arthropods |
| US6673756B2 (en) * | 2000-09-20 | 2004-01-06 | Symrise Gmbh & Co. Kg | Multiphase soaps |
| US6462015B1 (en) * | 2000-11-10 | 2002-10-08 | International Flavors & Fragrances Inc. | Bicyclic lactones, perfumery uses thereof, processes for preparing same and intermediates therefor |
| US20030235601A1 (en) * | 2002-03-20 | 2003-12-25 | Hallahan David L. | Insect repellent compounds |
| US7067677B2 (en) * | 2002-04-03 | 2006-06-27 | E. I. Du Pont De Nemours And Company | Production of dihydronepetalactone by hydrogenation of nepetalactone |
| WO2003086069A2 (en) * | 2002-04-08 | 2003-10-23 | Jodi Haenke | Materials and methods for controlling wood-boring insects |
| US7820145B2 (en) * | 2003-08-04 | 2010-10-26 | Foamix Ltd. | Oleaginous pharmaceutical and cosmetic foam |
| GB0409542D0 (en) * | 2004-04-29 | 2004-06-02 | Unilever Plc | Cosmetic compositions |
| US8748477B2 (en) * | 2004-11-03 | 2014-06-10 | E I Du Pont De Nemours And Company | Formulations containing insect repellent compounds |
| CN101316510A (zh) * | 2005-09-30 | 2008-12-03 | 纳幕尔杜邦公司 | 蒲勒酸昆虫驱避剂 |
| WO2007133683A2 (en) * | 2006-05-10 | 2007-11-22 | E. I. Du Pont De Nemours And Company | Formulated tick and insect repellent compositions |
| BRPI0719458A2 (pt) * | 2006-12-21 | 2014-02-04 | Du Pont | "Processos para a obtenção de óleo de girataria" |
| WO2008079253A1 (en) * | 2006-12-21 | 2008-07-03 | E. I. Du Pont De Nemours And Company | Hydrogenation of catmint oil |
| EP2129643A2 (en) * | 2006-12-21 | 2009-12-09 | E. I. Du Pont de Nemours and Company | Hydrogenation of caryophyllene |
| US8558015B2 (en) * | 2006-12-21 | 2013-10-15 | E I Du Pont De Nemours And Company | Solvent addition and removal in the hydrogenation of catmint oil |
| CN101563334B (zh) * | 2006-12-21 | 2012-08-22 | 纳幕尔杜邦公司 | 通过氢化荆芥内酯制备二氢荆芥内酯 |
| DE102007026049A1 (de) * | 2007-05-31 | 2008-12-04 | Beiersdorf Ag | Repellentien gegen Wespen |
| KR101577472B1 (ko) | 2007-11-26 | 2015-12-14 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 분자체를 사용하여 트랜스-시스 네페타락톤을 시스-트랜스 네페타락톤으로 변환하는 방법 |
-
2008
- 2008-11-26 KR KR1020107014060A patent/KR101577472B1/ko not_active Expired - Fee Related
- 2008-11-26 WO PCT/US2008/084795 patent/WO2009070641A1/en not_active Ceased
- 2008-11-26 MX MX2010005706A patent/MX2010005706A/es active IP Right Grant
- 2008-11-26 CN CN200880117731.7A patent/CN101874027B/zh not_active Expired - Fee Related
- 2008-11-26 ES ES08853740.2T patent/ES2442010T3/es active Active
- 2008-11-26 EP EP08853740.2A patent/EP2217586B1/en not_active Not-in-force
- 2008-11-26 CA CA2705367A patent/CA2705367C/en not_active Expired - Fee Related
- 2008-11-26 JP JP2010535122A patent/JP5377508B2/ja not_active Expired - Fee Related
- 2008-11-26 US US12/744,513 patent/US8802870B2/en not_active Expired - Fee Related
-
2010
- 2010-05-06 ZA ZA2010/03220A patent/ZA201003220B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN101874027A (zh) | 2010-10-27 |
| EP2217586B1 (en) | 2013-11-13 |
| MX2010005706A (es) | 2010-06-02 |
| JP2011504882A (ja) | 2011-02-17 |
| KR101577472B1 (ko) | 2015-12-14 |
| JP5377508B2 (ja) | 2013-12-25 |
| EP2217586A1 (en) | 2010-08-18 |
| KR20100099207A (ko) | 2010-09-10 |
| CN101874027B (zh) | 2014-08-20 |
| ZA201003220B (en) | 2011-08-31 |
| US20100261915A1 (en) | 2010-10-14 |
| US8802870B2 (en) | 2014-08-12 |
| CA2705367A1 (en) | 2009-06-04 |
| WO2009070641A1 (en) | 2009-06-04 |
| ES2442010T3 (es) | 2014-02-07 |
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