KR20090082421A - 고상 초강산 촉매의 존재하의 에스터화에 의한 수크로스-6-에스터의 제조 방법 - Google Patents
고상 초강산 촉매의 존재하의 에스터화에 의한 수크로스-6-에스터의 제조 방법Info
- Publication number
- KR20090082421A KR20090082421A KR1020097010473A KR20097010473A KR20090082421A KR 20090082421 A KR20090082421 A KR 20090082421A KR 1020097010473 A KR1020097010473 A KR 1020097010473A KR 20097010473 A KR20097010473 A KR 20097010473A KR 20090082421 A KR20090082421 A KR 20090082421A
- Authority
- KR
- South Korea
- Prior art keywords
- ester
- sucrose
- tio
- solid
- sucralose
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 42
- 239000003930 superacid Substances 0.000 title claims abstract description 33
- 239000003054 catalyst Substances 0.000 title claims abstract description 30
- 239000007787 solid Substances 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims description 7
- 238000005886 esterification reaction Methods 0.000 title claims description 6
- 230000032050 esterification Effects 0.000 title claims description 5
- 229930006000 Sucrose Natural products 0.000 claims abstract description 33
- 239000005720 sucrose Substances 0.000 claims abstract description 33
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims abstract description 31
- 229910010413 TiO 2 Inorganic materials 0.000 claims abstract description 26
- 235000019408 sucralose Nutrition 0.000 claims abstract description 26
- 239000004376 Sucralose Substances 0.000 claims abstract description 25
- BAQAVOSOZGMPRM-QBMZZYIRSA-N sucralose Chemical compound O[C@@H]1[C@@H](O)[C@@H](Cl)[C@@H](CO)O[C@@H]1O[C@@]1(CCl)[C@@H](O)[C@H](O)[C@@H](CCl)O1 BAQAVOSOZGMPRM-QBMZZYIRSA-N 0.000 claims abstract description 24
- 229910018072 Al 2 O 3 Inorganic materials 0.000 claims abstract description 23
- 150000002148 esters Chemical group 0.000 claims abstract description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 59
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- 239000003960 organic solvent Substances 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 15
- 238000005660 chlorination reaction Methods 0.000 claims description 12
- 239000007790 solid phase Substances 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
- 239000000706 filtrate Substances 0.000 claims description 4
- DCKVFVYPWDKYDN-UHFFFAOYSA-L oxygen(2-);titanium(4+);sulfate Chemical compound [O-2].[Ti+4].[O-]S([O-])(=O)=O DCKVFVYPWDKYDN-UHFFFAOYSA-L 0.000 claims description 4
- 229910000348 titanium sulfate Inorganic materials 0.000 claims description 4
- 238000001354 calcination Methods 0.000 claims description 3
- 230000002194 synthesizing effect Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000001308 synthesis method Methods 0.000 claims description 2
- 238000010189 synthetic method Methods 0.000 claims description 2
- 239000012320 chlorinating reagent Substances 0.000 claims 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims 2
- 229910052719 titanium Inorganic materials 0.000 claims 2
- 239000010936 titanium Substances 0.000 claims 2
- HDUMBHAAKGUHAR-UHFFFAOYSA-J titanium(4+);disulfate Chemical compound [Ti+4].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O HDUMBHAAKGUHAR-UHFFFAOYSA-J 0.000 claims 2
- 239000011701 zinc Substances 0.000 claims 2
- 229910052725 zinc Inorganic materials 0.000 claims 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims 1
- QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- -1 sucralose ester Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 21
- 238000006243 chemical reaction Methods 0.000 abstract description 16
- FACOTAQCKSDLDE-YKEUTPDRSA-N [(2R,3R,4R,5R,6R)-6-[(2R,3S,4S,5S)-2,5-bis(chloromethyl)-3,4-dihydroxyoxolan-2-yl]oxy-3-chloro-4,5-dihydroxyoxan-2-yl]methyl acetate Chemical compound O[C@@H]1[C@@H](O)[C@@H](Cl)[C@@H](COC(=O)C)O[C@@H]1O[C@@]1(CCl)[C@@H](O)[C@H](O)[C@@H](CCl)O1 FACOTAQCKSDLDE-YKEUTPDRSA-N 0.000 abstract description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract description 6
- 238000000746 purification Methods 0.000 abstract description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 20
- 235000019439 ethyl acetate Nutrition 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 9
- 239000006188 syrup Substances 0.000 description 9
- 235000020357 syrup Nutrition 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 206010013911 Dysgeusia Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910001867 inorganic solvent Inorganic materials 0.000 description 1
- 239000003049 inorganic solvent Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- BAQAVOSOZGMPRM-UHFFFAOYSA-N sucralose Chemical compound OC1C(O)C(Cl)C(CO)OC1OC1(CCl)C(O)C(O)C(CCl)O1 BAQAVOSOZGMPRM-UHFFFAOYSA-N 0.000 description 1
- 125000000185 sucrose group Chemical group 0.000 description 1
- 235000021092 sugar substitutes Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K13/00—Sugars not otherwise provided for in this class
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Health & Medical Sciences (AREA)
- Saccharide Compounds (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/552,813 | 2006-10-25 | ||
| US11/552,813 US20080103295A1 (en) | 2006-10-25 | 2006-10-25 | Process for the preparation of sucrose-6-ester by esterification in the presence of solid superacid catalyst |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20090082421A true KR20090082421A (ko) | 2009-07-30 |
Family
ID=39325403
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020097010473A Withdrawn KR20090082421A (ko) | 2006-10-25 | 2007-10-24 | 고상 초강산 촉매의 존재하의 에스터화에 의한 수크로스-6-에스터의 제조 방법 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20080103295A1 (enExample) |
| EP (1) | EP2097432A4 (enExample) |
| JP (1) | JP2010508286A (enExample) |
| KR (1) | KR20090082421A (enExample) |
| CN (1) | CN101558076A (enExample) |
| AU (1) | AU2007308948A1 (enExample) |
| BR (1) | BRPI0718058A2 (enExample) |
| CA (1) | CA2667366A1 (enExample) |
| MX (1) | MX2009004356A (enExample) |
| RU (1) | RU2009119517A (enExample) |
| TW (1) | TW200833707A (enExample) |
| WO (1) | WO2008052077A2 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8258291B2 (en) * | 2006-10-25 | 2012-09-04 | Mamtek International Limited | Process for the preparation of sucralose by the chlorination of sugar with triphosgene (BTC) |
| US8149122B2 (en) * | 2008-03-05 | 2012-04-03 | Metropolitan Industries, Inc. | Liquid level detection system with floating RFID tag |
| US20100022765A1 (en) * | 2008-07-23 | 2010-01-28 | David Losan Ho | Methods for extracting and purifying sucralose intermediate |
| US7862744B2 (en) * | 2008-07-23 | 2011-01-04 | Mamtek International Limited | Methods and systems for preparing materials for sucralose production |
| SG190083A1 (en) | 2010-11-23 | 2013-06-28 | Lexington Pharmaceuticals Lab Llc | Low temperature chlorination of carbohydrates |
| WO2013056128A1 (en) | 2011-10-14 | 2013-04-18 | Lexington Pharmaceuticals Laboratories, Llc | Chlorination of carbohydrates and carbohydrate derivatives |
| CN106622302A (zh) * | 2016-11-29 | 2017-05-10 | 华东理工大学 | 一种制备高纯度烯烃的催化剂的制备方法 |
| CN112973166B (zh) * | 2019-12-17 | 2024-04-30 | 无锡弘鼎华化工设备有限公司 | 一种三氯蔗糖中和液溶剂的回收装置及方法 |
| CN111205340B (zh) * | 2020-02-18 | 2021-06-29 | 万华化学集团股份有限公司 | 一种蔗糖-6-乙酸酯的制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3072725A (en) * | 1960-11-14 | 1963-01-08 | Du Pont | Preparation of dimethylformamide |
| EP0043649B1 (en) * | 1980-07-08 | 1984-09-12 | TATE & LYLE PUBLIC LIMITED COMPANY | Process for the preparation of 4, 1',6'-trichloro-4,1',6'-trideoxygalactosucrose (tgs) |
| GB8818430D0 (en) * | 1988-08-03 | 1988-09-07 | Tate & Lyle Plc | Process |
| US4980463A (en) * | 1989-07-18 | 1990-12-25 | Noramco, Inc. | Sucrose-6-ester chlorination |
| CO4410190A1 (es) * | 1994-09-19 | 1997-01-09 | Lilly Co Eli | 3-[4-(2-AMINOETOXI)-BENZOIL]-2-ARIL-6-HIDROXIBENZO [b] TIOFENO CRISTALINO |
| US5498709A (en) * | 1994-10-17 | 1996-03-12 | Mcneil-Ppc, Inc. | Production of sucralose without intermediate isolation of crystalline sucralose-6-ester |
| US6998480B2 (en) * | 2002-03-08 | 2006-02-14 | Tate & Lyle Public Limited Company | Process for improving sucralose purity and yield |
| CN1176094C (zh) * | 2003-05-23 | 2004-11-17 | 广东省食品工业研究所 | 一种三氯蔗糖的合成方法 |
| US20060205936A1 (en) * | 2005-03-14 | 2006-09-14 | Sl Laboratories, Llc | Chlorination of Sucrose-6-esters |
| US8258291B2 (en) * | 2006-10-25 | 2012-09-04 | Mamtek International Limited | Process for the preparation of sucralose by the chlorination of sugar with triphosgene (BTC) |
-
2006
- 2006-10-25 US US11/552,813 patent/US20080103295A1/en not_active Abandoned
-
2007
- 2007-10-19 TW TW096139366A patent/TW200833707A/zh unknown
- 2007-10-24 EP EP07854399A patent/EP2097432A4/en not_active Withdrawn
- 2007-10-24 JP JP2009534842A patent/JP2010508286A/ja active Pending
- 2007-10-24 BR BRPI0718058-6A2A patent/BRPI0718058A2/pt not_active IP Right Cessation
- 2007-10-24 CA CA002667366A patent/CA2667366A1/en not_active Abandoned
- 2007-10-24 RU RU2009119517/04A patent/RU2009119517A/ru not_active Application Discontinuation
- 2007-10-24 KR KR1020097010473A patent/KR20090082421A/ko not_active Withdrawn
- 2007-10-24 MX MX2009004356A patent/MX2009004356A/es not_active Application Discontinuation
- 2007-10-24 AU AU2007308948A patent/AU2007308948A1/en not_active Abandoned
- 2007-10-24 WO PCT/US2007/082424 patent/WO2008052077A2/en not_active Ceased
- 2007-10-24 CN CNA2007800436663A patent/CN101558076A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CN101558076A (zh) | 2009-10-14 |
| WO2008052077A2 (en) | 2008-05-02 |
| EP2097432A2 (en) | 2009-09-09 |
| WO2008052077B1 (en) | 2008-09-18 |
| TW200833707A (en) | 2008-08-16 |
| CA2667366A1 (en) | 2008-05-02 |
| BRPI0718058A2 (pt) | 2013-11-05 |
| MX2009004356A (es) | 2009-08-27 |
| US20080103295A1 (en) | 2008-05-01 |
| RU2009119517A (ru) | 2010-11-27 |
| JP2010508286A (ja) | 2010-03-18 |
| AU2007308948A1 (en) | 2008-05-02 |
| WO2008052077A3 (en) | 2008-07-31 |
| EP2097432A4 (en) | 2012-06-13 |
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