JP4875626B2 - セボフルランの調製のための方法 - Google Patents
セボフルランの調製のための方法 Download PDFInfo
- Publication number
- JP4875626B2 JP4875626B2 JP2007543255A JP2007543255A JP4875626B2 JP 4875626 B2 JP4875626 B2 JP 4875626B2 JP 2007543255 A JP2007543255 A JP 2007543255A JP 2007543255 A JP2007543255 A JP 2007543255A JP 4875626 B2 JP4875626 B2 JP 4875626B2
- Authority
- JP
- Japan
- Prior art keywords
- choch
- product
- water
- reaction
- mol
- 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.)
- Expired - Fee Related
Links
- DFEYYRMXOJXZRJ-UHFFFAOYSA-N sevoflurane Chemical compound FCOC(C(F)(F)F)C(F)(F)F DFEYYRMXOJXZRJ-UHFFFAOYSA-N 0.000 title claims description 84
- 238000000034 method Methods 0.000 title claims description 34
- 229960002078 sevoflurane Drugs 0.000 title claims description 27
- 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 145
- 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 claims description 128
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 125
- 238000006243 chemical reaction Methods 0.000 claims description 106
- 239000011698 potassium fluoride Substances 0.000 claims description 74
- 235000003270 potassium fluoride Nutrition 0.000 claims description 71
- 239000000203 mixture Substances 0.000 claims description 60
- 239000003444 phase transfer catalyst Substances 0.000 claims description 22
- 230000007062 hydrolysis Effects 0.000 claims description 19
- 238000006460 hydrolysis reaction Methods 0.000 claims description 19
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 17
- 239000011541 reaction mixture Substances 0.000 claims description 17
- ASZZHBXPMOVHCU-UHFFFAOYSA-N 3,9-diazaspiro[5.5]undecane-2,4-dione Chemical compound C1C(=O)NC(=O)CC11CCNCC1 ASZZHBXPMOVHCU-UHFFFAOYSA-N 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 claims description 6
- 150000003983 crown ethers Chemical group 0.000 claims description 5
- 150000004714 phosphonium salts Chemical group 0.000 claims description 5
- 239000000460 chlorine Substances 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
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 4
- MFIUDWFSVDFDDY-UHFFFAOYSA-M butyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCC)C1=CC=CC=C1 MFIUDWFSVDFDDY-UHFFFAOYSA-M 0.000 claims description 3
- 239000006184 cosolvent Substances 0.000 claims description 3
- YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- JHMDMBVWHYMAPJ-UHFFFAOYSA-M tributyl(pentan-2-yl)azanium;chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)C(C)CCC JHMDMBVWHYMAPJ-UHFFFAOYSA-M 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 150000003990 18-crown-6 derivatives Chemical group 0.000 claims 2
- SGWCNDDOFLBOQV-UHFFFAOYSA-N oxidanium;fluoride Chemical compound O.F SGWCNDDOFLBOQV-UHFFFAOYSA-N 0.000 claims 2
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- DHZKUVDKQZJAMV-UHFFFAOYSA-M potassium;fluoride;hydrate Chemical compound O.[F-].[K+] DHZKUVDKQZJAMV-UHFFFAOYSA-M 0.000 claims 1
- 239000000047 product Substances 0.000 description 165
- 238000004817 gas chromatography Methods 0.000 description 50
- 150000003839 salts Chemical class 0.000 description 40
- 238000003756 stirring Methods 0.000 description 35
- 238000010533 azeotropic distillation Methods 0.000 description 34
- 101001019134 Ilyobacter polytropus (strain ATCC 51220 / DSM 2926 / LMG 16218 / CuHBu1) Homoserine O-acetyltransferase 1 Proteins 0.000 description 32
- 238000003682 fluorination reaction Methods 0.000 description 24
- 238000004821 distillation Methods 0.000 description 16
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical class ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 9
- PJAIMBYNTXNOCN-UHFFFAOYSA-N 3,6-dibromo-1h-indole Chemical compound BrC1=CC=C2C(Br)=CNC2=C1 PJAIMBYNTXNOCN-UHFFFAOYSA-N 0.000 description 7
- 239000000376 reactant Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000000746 purification Methods 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
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000003795 chemical substances by application 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
- -1 fluoride ions Chemical class 0.000 description 3
- 239000008187 granular material Substances 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
- 239000000243 solution Substances 0.000 description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
- IPILPUZVTYHGIL-UHFFFAOYSA-M tributyl(methyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](C)(CCCC)CCCC IPILPUZVTYHGIL-UHFFFAOYSA-M 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 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
- 238000004587 chromatography analysis Methods 0.000 description 2
- 150000004673 fluoride salts Chemical class 0.000 description 2
- 239000012025 fluorinating agent Substances 0.000 description 2
- 239000007789 gas Substances 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
- 238000006467 substitution reaction Methods 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
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- GDXHBFHOEYVPED-UHFFFAOYSA-N 1-(2-butoxyethoxy)butane Chemical compound CCCCOCCOCCCC GDXHBFHOEYVPED-UHFFFAOYSA-N 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000007513 acids Chemical class 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
- 229940035674 anesthetics Drugs 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000009286 beneficial effect Effects 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
- 150000001804 chlorine Chemical class 0.000 description 1
- 238000005661 deetherification reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 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
- 239000003193 general anesthetic agent Substances 0.000 description 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical compound NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 description 1
- 125000005843 halogen group Chemical class 0.000 description 1
- 239000003983 inhalation anesthetic agent Substances 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 239000002609 medium Substances 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
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 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
- 238000001179 sorption measurement Methods 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
- 230000009466 transformation Effects 0.000 description 1
- 238000010792 warming 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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62870704P | 2004-11-17 | 2004-11-17 | |
| US60/628,707 | 2004-11-17 | ||
| PCT/US2005/041752 WO2006055748A2 (en) | 2004-11-17 | 2005-11-17 | Method for the preparation of sevoflurane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008520698A JP2008520698A (ja) | 2008-06-19 |
| JP4875626B2 true JP4875626B2 (ja) | 2012-02-15 |
Family
ID=36407760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007543255A Expired - Fee Related JP4875626B2 (ja) | 2004-11-17 | 2005-11-17 | セボフルランの調製のための方法 |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US8058482B2 (enExample) |
| EP (2) | EP1812368B1 (enExample) |
| JP (1) | JP4875626B2 (enExample) |
| KR (1) | KR101249315B1 (enExample) |
| CN (1) | CN101065346B (enExample) |
| AP (1) | AP2350A (enExample) |
| AU (1) | AU2005306472B2 (enExample) |
| BR (1) | BRPI0517854A (enExample) |
| CA (1) | CA2587672C (enExample) |
| EA (1) | EA200701073A1 (enExample) |
| ES (1) | ES2402145T3 (enExample) |
| HU (1) | HUP0700487A2 (enExample) |
| IL (1) | IL183176A (enExample) |
| IN (1) | IN2014DN04060A (enExample) |
| MX (1) | MX2007005899A (enExample) |
| NZ (1) | NZ555172A (enExample) |
| PL (2) | PL1812368T3 (enExample) |
| TR (1) | TR200703377T1 (enExample) |
| WO (1) | WO2006055748A2 (enExample) |
| ZA (1) | ZA200703957B (enExample) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8325961B2 (en) | 2003-08-12 | 2012-12-04 | 180S, Inc. | Ear warmer with a speaker system |
| US8438666B2 (en) | 2000-04-05 | 2013-05-14 | 180S, Inc. | Ear warmer with adjustability |
| US8443466B2 (en) | 2007-01-22 | 2013-05-21 | 180S, Inc. | Ear protection device |
| US8713714B2 (en) | 2002-01-28 | 2014-05-06 | 180S, Inc. | Apparatus and method for making an ear warmer and an ear warmer frame |
| US9259355B2 (en) | 2003-08-12 | 2016-02-16 | 180S, Inc. | Ear warmer with fabric member |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5021745B2 (ja) * | 2006-09-29 | 2012-09-12 | クリスタリア プロデュトス キミコス ファーマシューティコス リミターダ | フルオロメチル２，２，２−トリフロオロ−１−（トリフルオロメチル）エチルエーテルの製造方法 |
| 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 |
| BR102014028164A2 (pt) * | 2013-11-12 | 2015-09-08 | Dow Agrosciences Llc | processo para fluoração de compostos |
| TW201609652A (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（三） |
| 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） |
| ES2743155T3 (es) * | 2013-11-18 | 2020-02-18 | Basf Coatings Gmbh | Composición acuosa de revestimiento para el revestimiento por laca de electro-inmersión de sustratos eléctricamente conductores que contienen bismuto, tanto presente en forma disuelta, como también en forma no disuelta |
| 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 |
| 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 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0641026A (ja) * | 1992-03-21 | 1994-02-15 | Hoechst Ag | ３，５−ジフルオロアニリンの製造方法 |
| JPH06228042A (ja) * | 1992-11-04 | 1994-08-16 | Hoechst Ag | フッ化ベンジル及びその製造方法 |
| JPH08193039A (ja) * | 1995-01-13 | 1996-07-30 | Daikin Ind Ltd | ヘキサフルオロプロペンの製造方法 |
| JP2002540179A (ja) * | 1999-03-26 | 2002-11-26 | アボット・ラボラトリーズ | セボフルランおよびその中間体を合成するための方法 |
| JP2004508293A (ja) * | 2000-06-01 | 2004-03-18 | アボット・ラボラトリーズ | ハロゲン化脱炭酸反応によるアルコールのフルオロメチル化法 |
Family Cites Families (8)
| 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 |
| 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 |
| 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 PL PL05824284T patent/PL1812368T3/pl unknown
- 2005-11-17 PL PL383328A patent/PL383328A1/pl not_active Application Discontinuation
- 2005-11-17 WO PCT/US2005/041752 patent/WO2006055748A2/en not_active Ceased
- 2005-11-17 EA EA200701073A patent/EA200701073A1/ru unknown
- 2005-11-17 US US11/281,293 patent/US8058482B2/en not_active Expired - Fee Related
- 2005-11-17 CA CA2587672A patent/CA2587672C/en not_active Expired - Fee Related
- 2005-11-17 TR TR2007/03377T patent/TR200703377T1/xx unknown
- 2005-11-17 NZ NZ555172A patent/NZ555172A/en not_active IP Right Cessation
- 2005-11-17 JP JP2007543255A patent/JP4875626B2/ja not_active Expired - Fee Related
- 2005-11-17 AP AP2007003995A patent/AP2350A/xx active
- 2005-11-17 MX MX2007005899A patent/MX2007005899A/es active IP Right Grant
- 2005-11-17 IN IN4060DEN2014 patent/IN2014DN04060A/en unknown
- 2005-11-17 AU AU2005306472A patent/AU2005306472B2/en not_active Ceased
- 2005-11-17 KR KR1020077013462A patent/KR101249315B1/ko not_active Expired - Fee Related
- 2005-11-17 ES ES05824284T patent/ES2402145T3/es not_active Expired - Lifetime
- 2005-11-17 BR BRPI0517854-1A patent/BRPI0517854A/pt not_active IP Right Cessation
- 2005-11-17 EP EP05824284A patent/EP1812368B1/en not_active Expired - Lifetime
- 2005-11-17 CN CN2005800392651A patent/CN101065346B/zh not_active Expired - Fee Related
- 2005-11-17 EP EP12156826.5A patent/EP2481721A3/en not_active Withdrawn
- 2005-11-17 HU HU0700487A patent/HUP0700487A2/hu unknown
-
2007
- 2007-05-14 IL IL183176A patent/IL183176A/en active IP Right Grant
- 2007-05-16 ZA ZA200703957A patent/ZA200703957B/en unknown
-
2011
- 2011-09-27 US US13/200,691 patent/US20120022296A1/en not_active Abandoned
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0641026A (ja) * | 1992-03-21 | 1994-02-15 | Hoechst Ag | ３，５−ジフルオロアニリンの製造方法 |
| JPH06228042A (ja) * | 1992-11-04 | 1994-08-16 | Hoechst Ag | フッ化ベンジル及びその製造方法 |
| JPH08193039A (ja) * | 1995-01-13 | 1996-07-30 | Daikin Ind Ltd | ヘキサフルオロプロペンの製造方法 |
| JP2002540179A (ja) * | 1999-03-26 | 2002-11-26 | アボット・ラボラトリーズ | セボフルランおよびその中間体を合成するための方法 |
| JP2004508293A (ja) * | 2000-06-01 | 2004-03-18 | アボット・ラボラトリーズ | ハロゲン化脱炭酸反応によるアルコールのフルオロメチル化法 |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8438666B2 (en) | 2000-04-05 | 2013-05-14 | 180S, Inc. | Ear warmer with adjustability |
| US8713714B2 (en) | 2002-01-28 | 2014-05-06 | 180S, Inc. | Apparatus and method for making an ear warmer and an ear warmer frame |
| US8325961B2 (en) | 2003-08-12 | 2012-12-04 | 180S, Inc. | Ear warmer with a speaker system |
| US9259355B2 (en) | 2003-08-12 | 2016-02-16 | 180S, Inc. | Ear warmer with fabric member |
| US10111781B2 (en) | 2003-08-12 | 2018-10-30 | 180S, Inc. | Ear warmer with a substantially continuous surface |
| US8443466B2 (en) | 2007-01-22 | 2013-05-21 | 180S, Inc. | Ear protection device |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4875626B2 (ja) | セボフルランの調製のための方法 | |
| ZA200703958B (en) | Process for production of 1,2,2,2-tetrafluoro ethyl difluoro methyl ether | |
| JP5021745B2 (ja) | フルオロメチル２，２，２−トリフロオロ−１−（トリフルオロメチル）エチルエーテルの製造方法 | |
| JP5244109B2 (ja) | クロロメチル２，２，２―トリフロオロ−１−（トリフルオロメチル）エチルエーテルの製造方法 | |
| RU2109725C1 (ru) | Способ очистки фторметил-1,1,1,3,3,3-гексафторизопропилового эфира | |
| CN101128412B (zh) | 氟化醚的合成 | |
| KR100285073B1 (ko) | 디플루오로메틸 메틸에테르의 기상클로린화반응 | |
| HK1114602B (zh) | 製備七氟烷的方法 | |
| JP6361786B2 (ja) | 有機化合物の精製方法 | |
| HK1169381A (en) | Product mixtures comprising sevoflurane, sevochlorane and sevochlorane hydrolysis products | |
| JP2001524482A (ja) | ハロゲン交換反応における改良された触媒作用 | |
| KR20020073207A (ko) | 1,3,5-트리클로로벤젠으로부터 3,5-디플루오로아닐린을제조하는 방법 | |
| JPH03181432A (ja) | フロラール水和物の精製方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20081117 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20110608 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20110906 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20110913 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110922 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20111026 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20111125 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20141202 Year of fee payment: 3 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 4875626 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |