AU2012295410B2 - Process for the manufacturing of sevoflurane - Google Patents
Process for the manufacturing of sevoflurane Download PDFInfo
- Publication number
- AU2012295410B2 AU2012295410B2 AU2012295410A AU2012295410A AU2012295410B2 AU 2012295410 B2 AU2012295410 B2 AU 2012295410B2 AU 2012295410 A AU2012295410 A AU 2012295410A AU 2012295410 A AU2012295410 A AU 2012295410A AU 2012295410 B2 AU2012295410 B2 AU 2012295410B2
- Authority
- AU
- Australia
- Prior art keywords
- sevoflurane
- reaction mixture
- initial reaction
- amine
- lower alkyl
- 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.)
- Ceased
Links
- DFEYYRMXOJXZRJ-UHFFFAOYSA-N sevoflurane Chemical compound FCOC(C(F)(F)F)C(F)(F)F DFEYYRMXOJXZRJ-UHFFFAOYSA-N 0.000 title claims abstract description 146
- 229960002078 sevoflurane Drugs 0.000 title claims abstract description 144
- 238000000034 method Methods 0.000 title claims abstract description 58
- 238000004519 manufacturing process Methods 0.000 title description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 148
- 239000011541 reaction mixture Substances 0.000 claims abstract description 65
- 239000002904 solvent Substances 0.000 claims abstract description 42
- 238000006243 chemical reaction Methods 0.000 claims abstract description 37
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 28
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims abstract description 27
- 230000000269 nucleophilic effect Effects 0.000 claims abstract description 26
- 230000000977 initiatory effect Effects 0.000 claims abstract description 4
- 150000001412 amines Chemical class 0.000 claims description 31
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical group CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 150000003512 tertiary amines Chemical class 0.000 claims description 17
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 15
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- 238000010992 reflux Methods 0.000 claims description 10
- -1 n-tributylamine Chemical compound 0.000 claims description 8
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 6
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 claims description 3
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000004508 fractional distillation Methods 0.000 claims description 3
- CLZGJKHEVKJLLS-UHFFFAOYSA-N n,n-diheptylheptan-1-amine Chemical compound CCCCCCCN(CCCCCCC)CCCCCCC CLZGJKHEVKJLLS-UHFFFAOYSA-N 0.000 claims description 3
- DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 claims description 3
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 claims description 3
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 claims description 3
- OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 claims description 3
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 claims description 3
- 125000005270 trialkylamine group Chemical group 0.000 claims description 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 3
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 claims description 3
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims 2
- 239000000047 product Substances 0.000 description 16
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 12
- 238000003682 fluorination reaction Methods 0.000 description 12
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 11
- 239000007795 chemical reaction product Substances 0.000 description 10
- 238000005406 washing Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- LDDQLRUQCUTJBB-UHFFFAOYSA-N ammonium fluoride Chemical class [NH4+].[F-] LDDQLRUQCUTJBB-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 229940043279 diisopropylamine Drugs 0.000 description 4
- ISRXMEYARGEVIU-UHFFFAOYSA-N n-methyl-n-propan-2-ylpropan-2-amine Chemical compound CC(C)N(C)C(C)C ISRXMEYARGEVIU-UHFFFAOYSA-N 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 238000010189 synthetic method Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229920006362 Teflon® Polymers 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- 229910000792 Monel Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000004673 fluoride salts Chemical class 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- HHYFUCXZHKDNPT-UHFFFAOYSA-N 2-(chloromethoxy)-1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)C(C(F)(F)F)OCCl HHYFUCXZHKDNPT-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 238000002695 general anesthesia Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000003983 inhalation anesthetic agent Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/38—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/40—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation
- C07C41/42—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/12—Saturated ethers containing halogen
- C07C43/123—Saturated ethers containing halogen both carbon chains are substituted by halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/210,272 US8729313B2 (en) | 2011-08-15 | 2011-08-15 | Process for the manufacturing of sevoflurane |
| US13/210,272 | 2011-08-15 | ||
| PCT/US2012/049558 WO2013025377A1 (en) | 2011-08-15 | 2012-08-03 | Process for the manufacturing of sevoflurane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2012295410A1 AU2012295410A1 (en) | 2013-05-02 |
| AU2012295410B2 true AU2012295410B2 (en) | 2014-10-30 |
Family
ID=46924518
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2012295410A Ceased AU2012295410B2 (en) | 2011-08-15 | 2012-08-03 | Process for the manufacturing of sevoflurane |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8729313B2 (OSRAM) |
| EP (1) | EP2744772B1 (OSRAM) |
| JP (1) | JP5926802B2 (OSRAM) |
| CN (1) | CN103635451B (OSRAM) |
| AU (1) | AU2012295410B2 (OSRAM) |
| BR (1) | BR112013033851A2 (OSRAM) |
| MX (1) | MX353760B (OSRAM) |
| PL (1) | PL2744772T3 (OSRAM) |
| WO (1) | WO2013025377A1 (OSRAM) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9102604B1 (en) * | 2010-02-15 | 2015-08-11 | Baxter International Inc. | Methods for cleaning distilling columns |
| MX2018010079A (es) | 2016-02-23 | 2019-01-21 | Sagetech Medical Equipment Ltd | Mejoras para la elaboracion y reelaboracion de agentes anestesicos volatiles usando fluidos supercriticos. |
| US10035745B1 (en) | 2016-07-30 | 2018-07-31 | Baxter International Inc. | Methods of purifying crude sevoflurane |
| JP6299905B1 (ja) * | 2017-02-06 | 2018-03-28 | セントラル硝子株式会社 | セボフルランの製造方法 |
| CN108689808B (zh) * | 2017-04-06 | 2021-11-16 | 江苏恒瑞医药股份有限公司 | 一种氯甲基六氟异丙醚的制备方法 |
| CN114671742A (zh) * | 2020-12-24 | 2022-06-28 | 鲁南制药集团股份有限公司 | 一种七氟烷的制备方法 |
| CN113943214B (zh) * | 2021-11-11 | 2023-12-19 | 福建海西联合药业有限公司 | 一种运用于七氟烷生产的工艺 |
| CN119661328B (zh) * | 2024-12-13 | 2025-07-08 | 河北一品制药股份有限公司 | 一种七氟烷的清洁生产工艺 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5886239A (en) * | 1997-11-21 | 1999-03-23 | Baxter International Inc. | Method of preparing monofluoromethyl ethers |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3476860A (en) | 1966-12-08 | 1969-11-04 | Air Reduction | Halomethyl fluoroisopropyl ethers as anesthetic agents |
| US3527814A (en) | 1968-03-08 | 1970-09-08 | Air Reduction | Halomethyl fluoroisopropyl ethers |
| US4469898A (en) | 1979-12-26 | 1984-09-04 | Baxter Travenol Laboratories, Inc. | Method of synthesizing fluoromethylhexafluoroisopropyl ether |
| US4250334A (en) | 1979-12-26 | 1981-02-10 | Baxter Travenol Laboratories, Inc. | Method of synthesizing fluoromethylhexafluoroisopropyl ether |
| US5233098A (en) | 1990-05-30 | 1993-08-03 | Central Glass Company, Limited | Method for removing and recovering fluorinated alcohol from waste gas |
| JP2865554B2 (ja) | 1994-04-08 | 1999-03-08 | セントラル硝子株式会社 | フルオロメチル−１，１，１，３，３，３−ヘキサフルオロイソプロピルエーテルのガスクロマトグラフ分析 |
| GB9600072D0 (en) | 1996-01-04 | 1996-03-06 | Ici Plc | Process for the production of fluoromethylhexafluoroisopropylether |
| CN1074759C (zh) | 1996-02-21 | 2001-11-14 | 森陶硝子株式会社 | 氟甲基1,1,1,3,3,3－六氟异丙醚的生产方法 |
| US5969193A (en) | 1997-08-18 | 1999-10-19 | Medeva Pharmaceuticals Pa, Inc. | Method for the preparation of sevoflurane |
| US6100434A (en) * | 1999-03-26 | 2000-08-08 | Abbott Laboratories | Method for synthesizing sevoflurane and an intermediate thereof |
| US6469219B1 (en) | 2000-03-16 | 2002-10-22 | Halocarbon Products Corporation | Production of fluoromethyl 2,2,2-trifluoro-1-(trifluoromethyl)ethyl ether |
| GB0031310D0 (en) | 2000-12-21 | 2001-01-31 | Ici Plc | Process for the purification of fluoromethyl hexafluoroisopropyl ether |
| GB0031301D0 (en) | 2000-12-21 | 2001-01-31 | Ici Plc | Process for the production of fluoromethyl hexafluoroisopropyl ether |
| BRPI0406766B8 (pt) | 2003-01-14 | 2021-05-25 | Baxter Int | processo para a recuperação de 1,1,1,3,3,3-hexafluoroisopropanol a partir de corrente de rejeitos de síntese de sevoflurano |
| KR20060132685A (ko) | 2004-01-05 | 2006-12-21 | 할로카본 프로덕츠 코포레이션 | 제조 공정 중 및 최종 세보플란에서의 분석용크로마토그래피 방법 |
| EP1812368B1 (en) * | 2004-11-17 | 2012-12-26 | Piramal Critical Care, Inc. | Method for the preparation of sevoflurane |
| MX2009003354A (es) * | 2006-09-29 | 2009-04-14 | Cristalia Prod Quimicos Farm | Proceso para la preparacion de fluorometil 2,2,2,-trifluoro-1-(tri fluorometil) etil eter. |
| CN101337863B (zh) * | 2007-07-06 | 2012-04-25 | 江苏恒瑞医药股份有限公司 | 一种制备七氟烷的方法 |
| CN101314560B (zh) * | 2008-07-02 | 2011-06-15 | 鲁南制药集团股份有限公司 | 七氟烷的合成方法 |
-
2011
- 2011-08-15 US US13/210,272 patent/US8729313B2/en active Active
-
2012
- 2012-08-03 JP JP2014526059A patent/JP5926802B2/ja active Active
- 2012-08-03 CN CN201280032651.8A patent/CN103635451B/zh active Active
- 2012-08-03 WO PCT/US2012/049558 patent/WO2013025377A1/en not_active Ceased
- 2012-08-03 MX MX2014001828A patent/MX353760B/es active IP Right Grant
- 2012-08-03 AU AU2012295410A patent/AU2012295410B2/en not_active Ceased
- 2012-08-03 BR BR112013033851A patent/BR112013033851A2/pt not_active Application Discontinuation
- 2012-08-03 EP EP12762694.3A patent/EP2744772B1/en active Active
- 2012-08-03 PL PL12762694T patent/PL2744772T3/pl unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5886239A (en) * | 1997-11-21 | 1999-03-23 | Baxter International Inc. | Method of preparing monofluoromethyl ethers |
Also Published As
| Publication number | Publication date |
|---|---|
| MX2014001828A (es) | 2014-02-27 |
| US20130046117A1 (en) | 2013-02-21 |
| WO2013025377A1 (en) | 2013-02-21 |
| PL2744772T3 (pl) | 2015-11-30 |
| EP2744772A1 (en) | 2014-06-25 |
| US8729313B2 (en) | 2014-05-20 |
| BR112013033851A2 (pt) | 2017-02-07 |
| JP2014525409A (ja) | 2014-09-29 |
| JP5926802B2 (ja) | 2016-05-25 |
| MX353760B (es) | 2018-01-26 |
| EP2744772B1 (en) | 2015-07-01 |
| CN103635451A (zh) | 2014-03-12 |
| CN103635451B (zh) | 2016-08-24 |
| AU2012295410A1 (en) | 2013-05-02 |
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