ZA200703957B - Method for the preparation of sevoflurane - Google Patents
Method for the preparation of sevoflurane Download PDFInfo
- Publication number
- ZA200703957B ZA200703957B ZA200703957A ZA200703957A ZA200703957B ZA 200703957 B ZA200703957 B ZA 200703957B ZA 200703957 A ZA200703957 A ZA 200703957A ZA 200703957 A ZA200703957 A ZA 200703957A ZA 200703957 B ZA200703957 B ZA 200703957B
- Authority
- ZA
- South Africa
- Prior art keywords
- choch
- reaction
- sevoflurane
- potassium fluoride
- water
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 36
- DFEYYRMXOJXZRJ-UHFFFAOYSA-N sevoflurane Chemical compound FCOC(C(F)(F)F)C(F)(F)F DFEYYRMXOJXZRJ-UHFFFAOYSA-N 0.000 title claims description 30
- 229960002078 sevoflurane Drugs 0.000 title claims description 30
- 238000002360 preparation method Methods 0.000 title claims description 9
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 107
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 84
- 238000006243 chemical reaction Methods 0.000 claims description 78
- 239000011698 potassium fluoride Substances 0.000 claims description 56
- 235000003270 potassium fluoride Nutrition 0.000 claims description 52
- 239000000203 mixture Substances 0.000 claims description 37
- 239000003444 phase transfer catalyst Substances 0.000 claims description 23
- 230000007062 hydrolysis Effects 0.000 claims description 20
- 238000006460 hydrolysis reaction Methods 0.000 claims description 20
- 239000000460 chlorine Substances 0.000 claims description 18
- 239000011541 reaction mixture Substances 0.000 claims description 16
- VBKNTGMWIPUCRF-UHFFFAOYSA-M potassium;fluoride;hydrofluoride Chemical compound F.[F-].[K+] VBKNTGMWIPUCRF-UHFFFAOYSA-M 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 150000003983 crown ethers Chemical group 0.000 claims description 4
- 239000002608 ionic liquid Chemical group 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 150000004714 phosphonium salts Chemical group 0.000 claims description 4
- 229920000151 polyglycol Chemical group 0.000 claims description 4
- 239000010695 polyglycol Chemical group 0.000 claims description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 2
- DHZKUVDKQZJAMV-UHFFFAOYSA-M potassium;fluoride;hydrate Chemical compound O.[F-].[K+] DHZKUVDKQZJAMV-UHFFFAOYSA-M 0.000 claims 3
- 239000000047 product Substances 0.000 description 82
- 238000010533 azeotropic distillation Methods 0.000 description 24
- 238000003682 fluorination reaction Methods 0.000 description 24
- 238000003756 stirring Methods 0.000 description 23
- 238000004817 gas chromatography Methods 0.000 description 22
- 101001019134 Ilyobacter polytropus (strain ATCC 51220 / DSM 2926 / LMG 16218 / CuHBu1) Homoserine O-acetyltransferase 1 Proteins 0.000 description 20
- 150000003839 salts Chemical class 0.000 description 20
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical class ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 7
- 239000000376 reactant Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- -1 KHF Chemical class 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001348 alkyl chlorides Chemical class 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 239000006184 cosolvent Substances 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 150000004673 fluoride salts Chemical class 0.000 description 2
- 239000012025 fluorinating agent Substances 0.000 description 2
- 239000003983 inhalation anesthetic agent Substances 0.000 description 2
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- IPILPUZVTYHGIL-UHFFFAOYSA-M tributyl(methyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](C)(CCCC)CCCC IPILPUZVTYHGIL-UHFFFAOYSA-M 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical class CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 150000001349 alkyl fluorides Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- NYDMUQVQXHFCQF-UHFFFAOYSA-L benzyl(triethyl)azanium dichloride Chemical compound [Cl-].[Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1.CC[N+](CC)(CC)CC1=CC=CC=C1 NYDMUQVQXHFCQF-UHFFFAOYSA-L 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000005661 deetherification reaction Methods 0.000 description 1
- YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 150000005218 dimethyl ethers Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000004812 organic fluorine compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- JHMDMBVWHYMAPJ-UHFFFAOYSA-M tributyl(pentan-2-yl)azanium;chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)C(C)CCC JHMDMBVWHYMAPJ-UHFFFAOYSA-M 0.000 description 1
- 238000005406 washing Methods 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
-
- 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
-
- 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
- C07C43/13—Saturated ethers containing hydroxy or O-metal groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Anesthesiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62870704P | 2004-11-17 | 2004-11-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200703957B true ZA200703957B (en) | 2008-07-30 |
Family
ID=36407760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200703957A ZA200703957B (en) | 2004-11-17 | 2007-05-16 | Method for the preparation of sevoflurane |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US8058482B2 (es) |
| EP (2) | EP2481721A3 (es) |
| JP (1) | JP4875626B2 (es) |
| KR (1) | KR101249315B1 (es) |
| CN (1) | CN101065346B (es) |
| AP (1) | AP2350A (es) |
| AU (1) | AU2005306472B2 (es) |
| BR (1) | BRPI0517854A (es) |
| CA (1) | CA2587672C (es) |
| EA (1) | EA200701073A1 (es) |
| ES (1) | ES2402145T3 (es) |
| HK (1) | HK1114602A1 (es) |
| HU (1) | HUP0700487A2 (es) |
| IL (1) | IL183176A (es) |
| IN (1) | IN2014DN04060A (es) |
| MX (1) | MX2007005899A (es) |
| NZ (1) | NZ555172A (es) |
| PL (2) | PL383328A1 (es) |
| TR (1) | TR200703377T1 (es) |
| WO (1) | WO2006055748A2 (es) |
| ZA (1) | ZA200703957B (es) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6332223B1 (en) | 2000-04-05 | 2001-12-25 | Gray Matter Holdings, Llc | Apparatus and method for making an ear warmer having interior seams |
| US6735784B2 (en) | 2002-01-28 | 2004-05-18 | 180S, Inc. | Apparatus and method for making an ear warmer and an ear warmer frame |
| US7650649B2 (en) | 2003-08-12 | 2010-01-26 | 180S, Inc. | Ear warmer having an external frame |
| US7212645B2 (en) | 2003-08-12 | 2007-05-01 | 180S, Inc. | Ear warmer with a speaker system |
| EP2066609B1 (en) * | 2006-09-29 | 2016-01-06 | Cristália Produtos Químicos Farmacêuticos Ltda. | Process for the preparation of fluoromethyl 2,2,2-trifluoro-1-(trifluoromethyl) ethyl ether |
| WO2008091909A2 (en) | 2007-01-22 | 2008-07-31 | 180S, Inc. | Ear protection device |
| JP5163064B2 (ja) * | 2007-11-13 | 2013-03-13 | ダイキン工業株式会社 | 新規カルボン酸エステル、その用途及びその製造方法 |
| CN101659603B (zh) * | 2008-08-27 | 2014-05-07 | 中化蓝天集团有限公司 | 一种制备氟甲基-1,1,1,3,3,3-六氟异丙基醚的方法 |
| CN102199076B (zh) * | 2010-03-25 | 2014-05-14 | 上海源力生物技术有限公司 | 制备七氟烷的方法 |
| FR2975990B1 (fr) * | 2011-06-01 | 2013-05-24 | Rhodia Operations | Procede de preparation d'un compose organique fluore |
| US8729313B2 (en) * | 2011-08-15 | 2014-05-20 | Baxter International Inc. | Process for the manufacturing of sevoflurane |
| RU2479566C1 (ru) * | 2012-01-11 | 2013-04-20 | Общество с ограниченной ответственностью "Пермская химическая компания" | Способ получения севофлурана |
| CN103934020B (zh) * | 2013-01-22 | 2016-03-30 | 福建海西联合药业有限公司 | 八取代的双胍盐作为氟甲基六氟异丙基醚的合成催化剂的应用及催化合成方法 |
| US8907146B2 (en) * | 2013-02-04 | 2014-12-09 | Honeywell International Inc. | Process for the preparation of 1-chloro-3,3,3-trifluoropropene using a phase transfer catalyst |
| TW201609651A (zh) | 2013-11-12 | 2016-03-16 | 陶氏農業科學公司 | 用於氟化化合物之過程（一） |
| BR102014028164A2 (pt) | 2013-11-12 | 2015-09-08 | Dow Agrosciences Llc | processo para fluoração de compostos |
| BR102014028162A2 (pt) | 2013-11-12 | 2015-09-08 | Dow Agrosciences Llc | processo para fluoração de compostos |
| JP6375385B2 (ja) * | 2013-11-18 | 2018-08-15 | ビーエーエスエフ コーティングス ゲゼルシャフト ミット ベシュレンクテル ハフツングＢＡＳＦ Ｃｏａｔｉｎｇｓ ＧｍｂＨ | 溶解と非溶解両方のビスマスを含む導電性基材のための水性ディップコーティング組成物 |
| TWI726900B (zh) | 2015-08-04 | 2021-05-11 | 美商陶氏農業科學公司 | 用於氟化化合物之過程 |
| 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 |
| CN108727166B (zh) * | 2017-04-17 | 2021-06-29 | 江苏恒瑞医药股份有限公司 | 一种氯甲基六氟异丙醚的精制方法 |
| CN107698430B (zh) * | 2017-11-01 | 2021-01-08 | 华东医药（西安）博华制药有限公司 | 一种七氟烷反应液的后处理方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3476860A (en) | 1966-12-08 | 1969-11-04 | Air Reduction | Halomethyl fluoroisopropyl ethers as anesthetic agents |
| US3683092A (en) | 1970-07-31 | 1972-08-08 | Baxter Laboratories Inc | Method of anesthesia |
| BR8402990A (pt) | 1983-06-23 | 1985-05-28 | Du Pont | Processo continuo para fluoretar haloalcanos |
| US4874901A (en) | 1988-05-06 | 1989-10-17 | Boc, Inc. | Process for the production of polyfluorinated ethers |
| JPH01301636A (ja) | 1988-05-31 | 1989-12-05 | Central Glass Co Ltd | １，２，２，２−テトラフルオロエチルジフルオロメチルエーテルの製造法 |
| US5294742A (en) * | 1992-03-21 | 1994-03-15 | Hoechst Atkiengesellschaft | Process for preparing 3,5-difluoroaniline |
| DE59310066D1 (de) * | 1992-11-04 | 2000-08-03 | Clariant Gmbh | Verfahren zur Herstellung fluorierter Benzile |
| JP3778298B2 (ja) * | 1995-01-13 | 2006-05-24 | ダイキン工業株式会社 | ヘキサフルオロプロペンの製造方法 |
| US5840703A (en) * | 1996-11-15 | 1998-11-24 | Corrigan; Patrick J. | Phase transfer catalyst for use in the synthesis of polyol fatty acid polyesters |
| GB9720483D0 (en) | 1997-09-26 | 1997-11-26 | Zeneca Resins Bv | Aqueous polymer dispersionsa |
| US6100434A (en) * | 1999-03-26 | 2000-08-08 | Abbott Laboratories | Method for synthesizing sevoflurane and an intermediate thereof |
| US6271422B1 (en) * | 2000-06-01 | 2001-08-07 | Abbott Laboratories | Method for fluoromethylation of alcohols via halogenative decarboxylation |
| US6846946B2 (en) * | 2002-02-15 | 2005-01-25 | Value Recovery, Inc. | Process for making organic products and improving the quality of non-product streams using phase transfer catalysis |
-
2005
- 2005-11-17 ES ES05824284T patent/ES2402145T3/es active Active
- 2005-11-17 EP EP12156826.5A patent/EP2481721A3/en not_active Withdrawn
- 2005-11-17 HU HU0700487A patent/HUP0700487A2/hu unknown
- 2005-11-17 AU AU2005306472A patent/AU2005306472B2/en not_active Ceased
- 2005-11-17 EP EP05824284A patent/EP1812368B1/en not_active Not-in-force
- 2005-11-17 CN CN2005800392651A patent/CN101065346B/zh not_active Expired - Fee Related
- 2005-11-17 CA CA2587672A patent/CA2587672C/en not_active Expired - Fee Related
- 2005-11-17 US US11/281,293 patent/US8058482B2/en not_active Expired - Fee Related
- 2005-11-17 WO PCT/US2005/041752 patent/WO2006055748A2/en active Application Filing
- 2005-11-17 PL PL383328A patent/PL383328A1/pl not_active Application Discontinuation
- 2005-11-17 PL PL05824284T patent/PL1812368T3/pl unknown
- 2005-11-17 EA EA200701073A patent/EA200701073A1/ru unknown
- 2005-11-17 JP JP2007543255A patent/JP4875626B2/ja not_active Expired - Fee Related
- 2005-11-17 NZ NZ555172A patent/NZ555172A/en not_active IP Right Cessation
- 2005-11-17 TR TR2007/03377T patent/TR200703377T1/xx unknown
- 2005-11-17 MX MX2007005899A patent/MX2007005899A/es active IP Right Grant
- 2005-11-17 AP AP2007003995A patent/AP2350A/xx active
- 2005-11-17 KR KR1020077013462A patent/KR101249315B1/ko active IP Right Grant
- 2005-11-17 BR BRPI0517854-1A patent/BRPI0517854A/pt not_active IP Right Cessation
- 2005-11-17 IN IN4060DEN2014 patent/IN2014DN04060A/en unknown
-
2007
- 2007-05-14 IL IL183176A patent/IL183176A/en active IP Right Grant
- 2007-05-16 ZA ZA200703957A patent/ZA200703957B/en unknown
-
2008
- 2008-04-24 HK HK08104567.7A patent/HK1114602A1/xx not_active IP Right Cessation
-
2011
- 2011-09-27 US US13/200,691 patent/US20120022296A1/en not_active Abandoned
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