JP5479466B2 - 匂い物質として適するイソロンギホラニル誘導体 - Google Patents
匂い物質として適するイソロンギホラニル誘導体 Download PDFInfo
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- JP5479466B2 JP5479466B2 JP2011515052A JP2011515052A JP5479466B2 JP 5479466 B2 JP5479466 B2 JP 5479466B2 JP 2011515052 A JP2011515052 A JP 2011515052A JP 2011515052 A JP2011515052 A JP 2011515052A JP 5479466 B2 JP5479466 B2 JP 5479466B2
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- Prior art keywords
- tetradecane
- formula
- compound
- tetracyclo
- oxa
- 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.)
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- 239000003205 fragrance Substances 0.000 title claims abstract description 27
- 239000000203 mixture Substances 0.000 claims abstract description 29
- 150000001875 compounds Chemical class 0.000 claims description 48
- ZKLCERPSLCNFLX-UHFFFAOYSA-N C1CC2COC34CCC(C3)CC4C2C1 Chemical compound C1CC2COC34CCC(C3)CC4C2C1 ZKLCERPSLCNFLX-UHFFFAOYSA-N 0.000 claims description 34
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000000796 flavoring agent Substances 0.000 claims description 2
- 235000019634 flavors Nutrition 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 239000002304 perfume Substances 0.000 abstract description 7
- BGHCVCJVXZWKCC-NJFSPNSNSA-N tetradecane Chemical class CCCCCCCCCCCCC[14CH3] BGHCVCJVXZWKCC-NJFSPNSNSA-N 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 23
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
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- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 8
- 238000003818 flash chromatography Methods 0.000 description 8
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- QFUGDIRAXMEYHK-UHFFFAOYSA-N 2,2,7,7-tetramethyltricyclo[6.2.1.01.6]undec-4-en-5-yl acetate Chemical compound CC1(C)C2C(OC(=O)C)=CCC(C)(C)C32CC1CC3 QFUGDIRAXMEYHK-UHFFFAOYSA-N 0.000 description 3
- JEHCMNSAMPRFFY-UHFFFAOYSA-N 2,2,8,8-tetramethyl-octahydro-1h-2,4a-methanonapthalene-10-diol Chemical compound OC1C(O)CC(C)(C)C2(C3)C1C(C)(C)C3CC2 JEHCMNSAMPRFFY-UHFFFAOYSA-N 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 3
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
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- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
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- 244000179970 Monarda didyma Species 0.000 description 2
- 235000010672 Monarda didyma Nutrition 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
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- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- HQKQRXZEXPXXIG-VJOHVRBBSA-N chembl2333940 Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@H]1[C@@](OC(C)=O)(C)CC2 HQKQRXZEXPXXIG-VJOHVRBBSA-N 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
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- 150000002170 ethers Chemical class 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
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- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 description 2
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- 239000001939 cymbopogon martini roxb. stapf. oil Substances 0.000 description 1
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- YWFYGWQCHRDJSZ-UHFFFAOYSA-N dodecan-5-yl acetate Chemical compound CCCCCCCC(OC(C)=O)CCCC YWFYGWQCHRDJSZ-UHFFFAOYSA-N 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229940043259 farnesol Drugs 0.000 description 1
- 229930002886 farnesol Natural products 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- IFYYFLINQYPWGJ-VIFPVBQESA-N gamma-Decalactone Natural products CCCCCC[C@H]1CCC(=O)O1 IFYYFLINQYPWGJ-VIFPVBQESA-N 0.000 description 1
- PHXATPHONSXBIL-JTQLQIEISA-N gamma-Undecalactone Natural products CCCCCCC[C@H]1CCC(=O)O1 PHXATPHONSXBIL-JTQLQIEISA-N 0.000 description 1
- 229940020436 gamma-undecalactone Drugs 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229940113087 geraniol Drugs 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- UFLHIIWVXFIJGU-UHFFFAOYSA-N hex-3-en-1-ol Natural products CCC=CCCO UFLHIIWVXFIJGU-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 1
- 239000010656 jasmine oil Substances 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 239000000171 lavandula angustifolia l. flower oil Substances 0.000 description 1
- 229930007744 linalool Natural products 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 229940043353 maltol Drugs 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002088 nanocapsule Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 239000001931 piper nigrum l. white Substances 0.000 description 1
- 239000001738 pogostemon cablin oil Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 235000019719 rose oil Nutrition 0.000 description 1
- 239000010666 rose oil Substances 0.000 description 1
- 229930007790 rose oxide Natural products 0.000 description 1
- 239000010671 sandalwood oil Substances 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- GOZDTZWAMGHLDY-UHFFFAOYSA-L sodium picosulfate Chemical compound [Na+].[Na+].C1=CC(OS(=O)(=O)[O-])=CC=C1C(C=1N=CC=CC=1)C1=CC=C(OS([O-])(=O)=O)C=C1 GOZDTZWAMGHLDY-UHFFFAOYSA-L 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- LFSYLMRHJKGLDV-UHFFFAOYSA-N tetradecanolide Natural products O=C1CCCCCCCCCCCCCO1 LFSYLMRHJKGLDV-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
- 238000003420 transacetalization reaction Methods 0.000 description 1
- WENNKWXPAWNIOO-UHFFFAOYSA-N undecan-5-one Chemical compound CCCCCCC(=O)CCCC WENNKWXPAWNIOO-UHFFFAOYSA-N 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 239000002936 woody odorant Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/70—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with ring systems containing two or more relevant rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0812006.5 | 2008-07-01 | ||
| GBGB0812006.5A GB0812006D0 (en) | 2008-07-01 | 2008-07-01 | Organic compounds |
| PCT/CH2009/000223 WO2010000083A1 (en) | 2008-07-01 | 2009-06-29 | Isolongifolanyl-derivatives suitable as odorants |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011526252A JP2011526252A (ja) | 2011-10-06 |
| JP2011526252A5 JP2011526252A5 (enExample) | 2012-08-16 |
| JP5479466B2 true JP5479466B2 (ja) | 2014-04-23 |
Family
ID=39707816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011515052A Expired - Fee Related JP5479466B2 (ja) | 2008-07-01 | 2009-06-29 | 匂い物質として適するイソロンギホラニル誘導体 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8349890B2 (enExample) |
| EP (1) | EP2315758B1 (enExample) |
| JP (1) | JP5479466B2 (enExample) |
| CN (1) | CN102076676B (enExample) |
| AT (1) | ATE545640T1 (enExample) |
| BR (1) | BRPI0914935B1 (enExample) |
| ES (1) | ES2381931T3 (enExample) |
| GB (1) | GB0812006D0 (enExample) |
| MX (1) | MX2010013412A (enExample) |
| WO (1) | WO2010000083A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201006042D0 (en) * | 2010-04-12 | 2010-05-26 | Givaudan Sa | Improvements in or relating to organic compounds |
| GB201021050D0 (en) * | 2010-12-13 | 2011-01-26 | Givaudan Sa | Moc compositions |
| WO2016058710A1 (en) * | 2014-10-14 | 2016-04-21 | Givaudan Sa | Malodor reducing compositions |
| CN104844515B (zh) * | 2015-03-30 | 2017-05-10 | 南京林业大学 | 异长叶烷基吡唑类化合物及其应用 |
| GB201512585D0 (en) | 2015-07-17 | 2015-08-26 | Givaudan Sa | Perfume compositions |
| CN105669559B (zh) * | 2016-01-12 | 2017-07-28 | 南京林业大学 | 蒎烷基吡唑类化合物及其合成方法与应用 |
| CN105669565B (zh) * | 2016-03-21 | 2017-07-11 | 南京林业大学 | 异长叶烷基嘧啶类化合物及其制备方法与应用 |
| WO2019141881A1 (en) * | 2019-03-13 | 2019-07-25 | Givaudan Sa | (3aS,4aR,5S,7aS,9R,9aR)-2,2,5,8,8,9a-hexamethyloctahydro-4H-4a,9-methanoazuleno[5,6-d][1,3]dioxole |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0374445A1 (fr) * | 1988-12-23 | 1990-06-27 | Firmenich Sa | Nouveaux composés cycliques oxygénés, leur utilisation à titre d'ingrédients parfumants, procédé pour leur préparation |
| DE4138732A1 (de) | 1991-11-19 | 1993-05-27 | Dragoco Gerberding Co Gmbh | Cyclische isolongifolanon-ketale, ihre herstellung und ihre verwendung |
| DE4406467A1 (de) * | 1994-02-23 | 1995-08-24 | Dragoco Gerberding Co Ag | Isolongifolanol-Derivate, ihre Herstellung und ihre Verwendung |
| DE19704484A1 (de) | 1997-02-06 | 1998-09-03 | Dragoco Gerberding Co Ag | Cyclische Cedren-Acetale, ihre Herstellung und ihre Verwendung |
| DE10038544A1 (de) * | 2000-08-03 | 2002-02-14 | Dragoco Gerberding Co Ag | Isolongifolenylether, ihre Herstellung und ihre Verwendung |
| US7115553B2 (en) | 2003-07-10 | 2006-10-03 | International Flavors & Fragrances Inc. | Acetonide fragrance compound |
| JP4662950B2 (ja) * | 2004-01-27 | 2011-03-30 | フイルメニツヒ ソシエテ アノニム | ウッディな香気を付与可能な香料成分 |
| GB0426376D0 (en) * | 2004-12-02 | 2005-01-05 | Givaudan Sa | Compounds |
| US7122513B2 (en) | 2004-12-09 | 2006-10-17 | International Flavor & Fragrance Inc. | Hexahydro-4H-indeno acetonide fragrance compound |
| JP5075828B2 (ja) * | 2005-09-14 | 2012-11-21 | ジボダン エス エー | 酸素含有三環式または四環式テルペノイド化合物 |
| US7579016B2 (en) * | 2007-07-13 | 2009-08-25 | The United States Of America As Represented By The Secretary Of Agriculture | Methods for repelling arthropods using isolongifolenone analogs |
-
2008
- 2008-07-01 GB GBGB0812006.5A patent/GB0812006D0/en not_active Ceased
-
2009
- 2009-06-29 ES ES09771890T patent/ES2381931T3/es active Active
- 2009-06-29 MX MX2010013412A patent/MX2010013412A/es active IP Right Grant
- 2009-06-29 EP EP09771890A patent/EP2315758B1/en not_active Not-in-force
- 2009-06-29 BR BRPI0914935-0A patent/BRPI0914935B1/pt not_active IP Right Cessation
- 2009-06-29 JP JP2011515052A patent/JP5479466B2/ja not_active Expired - Fee Related
- 2009-06-29 WO PCT/CH2009/000223 patent/WO2010000083A1/en not_active Ceased
- 2009-06-29 US US13/000,697 patent/US8349890B2/en not_active Expired - Fee Related
- 2009-06-29 AT AT09771890T patent/ATE545640T1/de active
- 2009-06-29 CN CN200980124748XA patent/CN102076676B/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP2315758A1 (en) | 2011-05-04 |
| MX2010013412A (es) | 2010-12-21 |
| JP2011526252A (ja) | 2011-10-06 |
| BRPI0914935B1 (pt) | 2017-07-18 |
| WO2010000083A1 (en) | 2010-01-07 |
| BRPI0914935A2 (pt) | 2015-08-11 |
| CN102076676B (zh) | 2013-12-04 |
| EP2315758B1 (en) | 2012-02-15 |
| CN102076676A (zh) | 2011-05-25 |
| GB0812006D0 (en) | 2008-08-06 |
| US8349890B2 (en) | 2013-01-08 |
| ES2381931T3 (es) | 2012-06-01 |
| ATE545640T1 (de) | 2012-03-15 |
| US20110104098A1 (en) | 2011-05-05 |
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