DK2310350T3 - PROCEDURE FOR THE PREPARATION OF ALKENONES - Google Patents
PROCEDURE FOR THE PREPARATION OF ALKENONES Download PDFInfo
- Publication number
- DK2310350T3 DK2310350T3 DK09772571.7T DK09772571T DK2310350T3 DK 2310350 T3 DK2310350 T3 DK 2310350T3 DK 09772571 T DK09772571 T DK 09772571T DK 2310350 T3 DK2310350 T3 DK 2310350T3
- Authority
- DK
- Denmark
- Prior art keywords
- carboxylic acid
- acid halide
- weight
- reaction medium
- alkenone
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 49
- 238000002360 preparation method Methods 0.000 title description 2
- 239000012429 reaction media Substances 0.000 claims description 56
- -1 carboxylic acid halide Chemical class 0.000 claims description 48
- 238000006243 chemical reaction Methods 0.000 claims description 48
- 239000007788 liquid Substances 0.000 claims description 40
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 28
- 239000002243 precursor Substances 0.000 claims description 26
- 238000004519 manufacturing process Methods 0.000 claims description 18
- 238000004821 distillation Methods 0.000 claims description 10
- PNQBEPDZQUOCNY-UHFFFAOYSA-N trifluoroacetyl chloride Chemical group FC(F)(F)C(Cl)=O PNQBEPDZQUOCNY-UHFFFAOYSA-N 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000012433 hydrogen halide Substances 0.000 claims description 5
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Chemical group 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 229960000834 vinyl ether Drugs 0.000 description 25
- YKYIFUROKBDHCY-UHFFFAOYSA-N 4-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical compound CCOC=CC(=O)C(F)(F)F YKYIFUROKBDHCY-UHFFFAOYSA-N 0.000 description 24
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 23
- 238000001149 thermolysis Methods 0.000 description 19
- 239000002904 solvent Substances 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- 238000004508 fractional distillation Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000919 ceramic Substances 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
- KURKJXZWCPWPFX-UHFFFAOYSA-N 2,2-difluoroacetyl chloride Chemical group FC(F)C(Cl)=O KURKJXZWCPWPFX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 229940052303 ethers for general anesthesia Drugs 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VKNLVLNOHCTKII-ONEGZZNKSA-N (e)-1,1,1-trichloro-4-ethoxybut-3-en-2-one Chemical compound CCO\C=C\C(=O)C(Cl)(Cl)Cl VKNLVLNOHCTKII-ONEGZZNKSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- DCEPGADSNJKOJK-UHFFFAOYSA-N 2,2,2-trifluoroacetyl fluoride Chemical group FC(=O)C(F)(F)F DCEPGADSNJKOJK-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- AZPWOLJQERBBBM-UHFFFAOYSA-N 2-chloro-2,2-difluoroacetyl chloride Chemical group FC(F)(Cl)C(Cl)=O AZPWOLJQERBBBM-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- GGKAAPYKPQEJOK-UHFFFAOYSA-N 3-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical compound CCOC(=C)C(=O)C(F)(F)F GGKAAPYKPQEJOK-UHFFFAOYSA-N 0.000 description 1
- GETLJJKPKIDEIZ-UHFFFAOYSA-N 4,4,4-trifluoro-3-oxobutanoyl fluoride Chemical group FC(=O)CC(=O)C(F)(F)F GETLJJKPKIDEIZ-UHFFFAOYSA-N 0.000 description 1
- MPYKDYSKCIRYRA-UHFFFAOYSA-N 4-chloro-4-ethoxy-1,1,1-trifluorobutan-2-one Chemical compound CCOC(Cl)CC(=O)C(F)(F)F MPYKDYSKCIRYRA-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229960004424 carbon dioxide Drugs 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical class ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/41—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrogenolysis or reduction of carboxylic groups or functional derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/85—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08159744 | 2008-07-04 | ||
| PCT/EP2009/058525 WO2010000871A2 (en) | 2008-07-04 | 2009-07-06 | Process for the manufacture of alkenones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2310350T3 true DK2310350T3 (en) | 2017-12-11 |
Family
ID=39941475
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK09772571.7T DK2310350T3 (en) | 2008-07-04 | 2009-07-06 | PROCEDURE FOR THE PREPARATION OF ALKENONES |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8519195B2 (https=) |
| EP (1) | EP2310350B1 (https=) |
| JP (1) | JP5587307B2 (https=) |
| KR (1) | KR101652539B1 (https=) |
| CN (1) | CN102112428B (https=) |
| CA (1) | CA2729362C (https=) |
| DK (1) | DK2310350T3 (https=) |
| WO (1) | WO2010000871A2 (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106083710B (zh) | 2008-09-30 | 2021-03-12 | 索尔维公司 | 用于合成卤化的环状化合物的方法 |
| GB0903749D0 (en) * | 2009-03-04 | 2009-04-15 | Syngenta Participations Ag | Chemical process |
| ES2537676T3 (es) | 2009-07-06 | 2015-06-10 | Solvay Sa | Proceso para la fabricación de precursores halogenados de alquenonas en presencia de un disolvente |
| US8957254B2 (en) | 2009-07-06 | 2015-02-17 | Solvay Sa | Process for chemical synthesis from an alkenone made from a halogenated precursor |
| WO2012025548A1 (en) | 2010-08-27 | 2012-03-01 | Solvay Sa | Process for the preparation of alkenones |
| EP2607343A1 (en) * | 2011-12-22 | 2013-06-26 | Solvay Sa | Process for the manufacture of halogenated precursors of alkenones and of alkenones |
| IN2015DN00635A (https=) * | 2012-08-22 | 2015-06-26 | Solvay | |
| US10829456B2 (en) | 2016-01-28 | 2020-11-10 | Solvay Sa | Halogen substituted diketones, pyrazole compounds and processes for the manufacture of pyrazole compounds |
| EP3246313A1 (en) | 2016-05-19 | 2017-11-22 | Solvay Sa | Process for the manufacture of 2-substituted-5-(1-methylthio)alkylpyridines |
| JP2019524765A (ja) | 2016-08-02 | 2019-09-05 | ソルヴェイ（ソシエテ アノニム） | ピラゾールカルボン酸および誘導体の製造に有用なヒドラジニル化合物の製造、ヒドラジニル化合物ならびにその使用 |
| WO2019043238A1 (en) | 2017-09-04 | 2019-03-07 | Solvay Sa | PROCESS AND INTERMEDIARY FOR MANUFACTURING DIFLUOROACETYL CHLORIDE |
| EP3728198A1 (en) | 2017-12-22 | 2020-10-28 | Solvay Sa | Process for the manufacture of pyrazole carboxylic derivatives and precursors thereof |
| WO2019122204A1 (en) | 2017-12-22 | 2019-06-27 | Solvay Sa | Process for the manufacture of pyrazole compounds |
| KR20200103744A (ko) | 2017-12-22 | 2020-09-02 | 솔베이(소시에떼아노님) | 이미늄 화합물의 제조 방법 및 피라졸 유도체 제조에서의 이의 응용 |
| EP3632855A1 (en) | 2018-10-02 | 2020-04-08 | Solvay Sa | A method for providing aqueous compositions with reduced content of organic fluorinated compounds |
| CN112979443A (zh) * | 2019-12-13 | 2021-06-18 | 浙江蓝天环保高科技股份有限公司 | 一种三氟甲基丁烯酮类衍生物的连续制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0664805A1 (en) | 1992-10-13 | 1995-08-02 | Smithkline Beecham Plc | Heterocyclic -esters or -amides used as 5-ht 4? receptor antagonists |
| EP0744400B1 (en) | 1995-05-26 | 2002-09-11 | Ishihara Sangyo Kaisha, Ltd. | Process for producing 4-trifluoromethylnicotinic acid |
| EP1480934A2 (de) | 2002-02-08 | 2004-12-01 | Solvay Fluor und Derivate GmbH | Herstellung von alkenonen |
| DE10325715A1 (de) | 2003-06-06 | 2004-12-23 | Solvay Fluor Und Derivate Gmbh | Vereinfachte Herstellung von Alkenonen |
| MX2011000196A (es) | 2008-07-01 | 2011-03-24 | Dow Agrosciences Llc | Proceso mejorado para la preparacion de alquilpiridinas 2-trifluorometil-5-(1-sustituidas). |
| CN106083710B (zh) | 2008-09-30 | 2021-03-12 | 索尔维公司 | 用于合成卤化的环状化合物的方法 |
| GB0903749D0 (en) | 2009-03-04 | 2009-04-15 | Syngenta Participations Ag | Chemical process |
| CA2765487A1 (en) | 2009-07-06 | 2011-01-13 | Solvay Sa | Process for the manufacture of halogenated precursors of alkenones under specific conditions |
| ES2537676T3 (es) | 2009-07-06 | 2015-06-10 | Solvay Sa | Proceso para la fabricación de precursores halogenados de alquenonas en presencia de un disolvente |
| WO2011003860A1 (en) | 2009-07-06 | 2011-01-13 | Solvay Sa | Process for the manufacture of alkenones |
-
2009
- 2009-07-06 KR KR1020117002650A patent/KR101652539B1/ko active Active
- 2009-07-06 CN CN200980130639.9A patent/CN102112428B/zh active Active
- 2009-07-06 CA CA2729362A patent/CA2729362C/en not_active Expired - Fee Related
- 2009-07-06 EP EP09772571.7A patent/EP2310350B1/en active Active
- 2009-07-06 JP JP2011515483A patent/JP5587307B2/ja active Active
- 2009-07-06 WO PCT/EP2009/058525 patent/WO2010000871A2/en not_active Ceased
- 2009-07-06 US US12/999,673 patent/US8519195B2/en active Active
- 2009-07-06 DK DK09772571.7T patent/DK2310350T3/en active
Also Published As
| Publication number | Publication date |
|---|---|
| EP2310350A2 (en) | 2011-04-20 |
| CA2729362A1 (en) | 2010-01-07 |
| JP2011526605A (ja) | 2011-10-13 |
| WO2010000871A2 (en) | 2010-01-07 |
| KR101652539B1 (ko) | 2016-08-30 |
| JP5587307B2 (ja) | 2014-09-10 |
| US20110087052A1 (en) | 2011-04-14 |
| EP2310350B1 (en) | 2017-09-06 |
| US8519195B2 (en) | 2013-08-27 |
| CA2729362C (en) | 2016-09-27 |
| CN102112428A (zh) | 2011-06-29 |
| KR20110031217A (ko) | 2011-03-24 |
| WO2010000871A3 (en) | 2010-03-04 |
| CN102112428B (zh) | 2015-09-09 |
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