JP2017501118A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2017501118A5 JP2017501118A5 JP2016528529A JP2016528529A JP2017501118A5 JP 2017501118 A5 JP2017501118 A5 JP 2017501118A5 JP 2016528529 A JP2016528529 A JP 2016528529A JP 2016528529 A JP2016528529 A JP 2016528529A JP 2017501118 A5 JP2017501118 A5 JP 2017501118A5
- Authority
- JP
- Japan
- Prior art keywords
- polyunsaturated
- container
- thioester
- mixing
- alcohol
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 claims 25
- 150000007970 thio esters Chemical class 0.000 claims 11
- 239000003963 antioxidant agent Substances 0.000 claims 10
- 230000003078 antioxidant effect Effects 0.000 claims 10
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 9
- -1 phosphine compound Chemical class 0.000 claims 8
- 150000001298 alcohols Chemical class 0.000 claims 7
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 6
- 150000003573 thiols Chemical class 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 5
- 238000004128 high performance liquid chromatography Methods 0.000 claims 5
- 150000002148 esters Chemical class 0.000 claims 4
- 125000005604 azodicarboxylate group Chemical group 0.000 claims 3
- 150000002430 hydrocarbons Chemical class 0.000 claims 3
- 150000002576 ketones Chemical class 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 claims 3
- UMZOWPPFHRRPDC-IIFHDYRKSA-N (2E,6Z,9Z,12Z,15Z)-octadeca-2,6,9,12,15-pentaen-1-ol Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/CC\C=C\CO UMZOWPPFHRRPDC-IIFHDYRKSA-N 0.000 claims 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims 2
- 125000006575 electron-withdrawing group Chemical group 0.000 claims 2
- DUYAAUVXQSMXQP-UHFFFAOYSA-N ethanethioic S-acid Chemical class CC(S)=O DUYAAUVXQSMXQP-UHFFFAOYSA-N 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical group CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 claims 2
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 claims 2
- 229960001295 tocopherol Drugs 0.000 claims 2
- 229930003799 tocopherol Natural products 0.000 claims 2
- 235000010384 tocopherol Nutrition 0.000 claims 2
- 239000011732 tocopherol Substances 0.000 claims 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
- ONZQYZKCUHFORE-UHFFFAOYSA-N 3-bromo-1,1,1-trifluoropropan-2-one Chemical compound FC(F)(F)C(=O)CBr ONZQYZKCUHFORE-UHFFFAOYSA-N 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 230000005595 deprotonation Effects 0.000 claims 1
- 238000010537 deprotonation reaction Methods 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 238000003818 flash chromatography Methods 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 125000000468 ketone group Chemical group 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 125000002640 tocopherol group Chemical group 0.000 claims 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1313238.6A GB201313238D0 (en) | 2013-07-24 | 2013-07-24 | Process for the preparation of a polyunsaturated ketone compound |
| GB1313238.6 | 2013-07-24 | ||
| PCT/EP2014/065853 WO2015011206A1 (en) | 2013-07-24 | 2014-07-23 | Process for the preparation of a polyunsaturated ketone compound |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017501118A JP2017501118A (ja) | 2017-01-12 |
| JP2017501118A5 true JP2017501118A5 (enExample) | 2018-03-15 |
| JP6563921B2 JP6563921B2 (ja) | 2019-08-21 |
Family
ID=49119228
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016528529A Expired - Fee Related JP6563921B2 (ja) | 2013-07-24 | 2014-07-23 | 多価不飽和ケトン化合物の製造方法 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US10093618B2 (enExample) |
| EP (2) | EP3398936A1 (enExample) |
| JP (1) | JP6563921B2 (enExample) |
| KR (1) | KR20160033781A (enExample) |
| CN (2) | CN108276317A (enExample) |
| CA (1) | CA2918950A1 (enExample) |
| ES (1) | ES2668322T3 (enExample) |
| GB (1) | GB201313238D0 (enExample) |
| HK (1) | HK1258174A1 (enExample) |
| IL (1) | IL243636B (enExample) |
| NO (1) | NO3024818T3 (enExample) |
| WO (1) | WO2015011206A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201501144D0 (en) | 2015-01-23 | 2015-03-11 | Avexxin As | Process for the preparation of a polyunsaturated ketone compound |
| CN106117096B (zh) * | 2016-06-15 | 2018-01-19 | 苏州大学 | 一种非对称硫醚的合成方法 |
| CN106831511B (zh) * | 2017-01-24 | 2018-05-25 | 郯城博化化工科技有限公司 | 一种多元硫醇化合物的制备方法 |
| GB201807892D0 (en) | 2018-05-15 | 2018-06-27 | Avexxin As | Processes in the preparation of polyunsaturated ketone compounds |
| WO2025192727A1 (ja) * | 2024-03-15 | 2025-09-18 | 国立大学法人福井大学 | 硫黄含有ビニルエーテルの製造方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5024847A (en) * | 1989-09-18 | 1991-06-18 | Basf K&F Corporation | Sulfur containing acyclic terpenes |
| JPH0632773A (ja) | 1992-07-15 | 1994-02-08 | Sumitomo Seika Chem Co Ltd | ４，４’−チオビスベンゼンチオールの製造法 |
| CA2260859A1 (en) * | 1996-07-22 | 1998-01-29 | Monsanto Company | Thiol sulfone metalloprotease inhibitors |
| WO2002100991A2 (en) | 2001-06-13 | 2002-12-19 | Biorama 2000 S.R.L. | Mono-, di- and triglycerides or their mixtures containing trans-fatty acid residues and method of their formation |
| GB0202002D0 (en) | 2002-01-29 | 2002-03-13 | Leiv Eiriksson Nyotek A S | Use |
| CN101899063B (zh) * | 2002-12-11 | 2012-12-12 | 布里斯托尔-迈尔斯斯奎布公司 | 制备抗病毒药[1S-(1α,3α,4β)]-2-氨基-1,9-二氢-9-[4-羟基-3-(羟甲基)-2-亚甲环戊基]-6H-嘌呤-6-酮的方法 |
| EP2147910A1 (en) | 2008-07-15 | 2010-01-27 | Pronova BioPharma Norge AS | Novel lipid compounds |
| JP5349086B2 (ja) | 2009-03-05 | 2013-11-20 | 長谷川香料株式会社 | α，α−ジチオール化合物および香料組成物 |
| GB0909643D0 (en) | 2009-06-04 | 2009-07-22 | Avexxin As | Glomerulonephritis treatment |
| GB201014633D0 (en) | 2010-09-02 | 2010-10-13 | Avexxin As | Rheumatoid arthritis treatment |
| GB201221329D0 (en) | 2012-11-27 | 2013-01-09 | Avexxin As | Dermatitis treatment |
-
2013
- 2013-07-24 GB GBGB1313238.6A patent/GB201313238D0/en not_active Ceased
-
2014
- 2014-07-23 JP JP2016528529A patent/JP6563921B2/ja not_active Expired - Fee Related
- 2014-07-23 ES ES14742219.0T patent/ES2668322T3/es active Active
- 2014-07-23 CN CN201810252228.8A patent/CN108276317A/zh active Pending
- 2014-07-23 CN CN201480044978.6A patent/CN105492421B/zh not_active Expired - Fee Related
- 2014-07-23 US US14/907,147 patent/US10093618B2/en not_active Expired - Fee Related
- 2014-07-23 EP EP18164396.6A patent/EP3398936A1/en not_active Withdrawn
- 2014-07-23 WO PCT/EP2014/065853 patent/WO2015011206A1/en not_active Ceased
- 2014-07-23 EP EP14742219.0A patent/EP3024818B1/en not_active Not-in-force
- 2014-07-23 CA CA2918950A patent/CA2918950A1/en not_active Abandoned
- 2014-07-23 KR KR1020167004651A patent/KR20160033781A/ko not_active Ceased
- 2014-07-23 NO NO14742219A patent/NO3024818T3/no unknown
-
2016
- 2016-01-17 IL IL243636A patent/IL243636B/en active IP Right Grant
-
2019
- 2019-01-14 HK HK19100531.5A patent/HK1258174A1/zh unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2016520672A5 (enExample) | ||
| PH12014501863A1 (en) | Method for the preparationof triglycerides of medium-chain length fatty acids | |
| WO2014089385A3 (en) | Methods of synthesizing a prostacyclin analog | |
| JP2010530373A5 (enExample) | ||
| AR077526A1 (es) | Metodo para la sintesis de (1s,2r)- milnacipran | |
| JP2019194256A (ja) | カルボン酸エステルの製造方法 | |
| JP5822894B2 (ja) | ケト酸およびその誘導体の製造方法 | |
| US20150315136A1 (en) | Method for producing fluorinated organic compound and fluorinating reagent | |
| US10377706B2 (en) | Method for producing carboxylic acid thioester | |
| HK1247185A1 (zh) | 制备不饱和酮化合物的方法 | |
| CN105492421B (zh) | 用于制备多元不饱和酮化合物的方法 | |
| JP2015091940A (ja) | エイコサペンタエン酸及び／又はドコサヘキサエン酸含有組成物の製造方法 | |
| JP2013506705A5 (enExample) | ||
| CN103980172A (zh) | 一种1α,25-二羟基维生素D2的制备方法 | |
| AR094942A1 (es) | Métodos para preparar derivados de un ácido graso | |
| CN104326936B (zh) | 反式n-乙基-n-(2’-烷基苯基)-2-丁烯酰胺的合成方法 | |
| EP3732175A4 (en) | CATALYST COMPOSITION FOR THE PRODUCTION OF AN UNSATURATED CARBONIC ACID SALT AND ITS DERIVATIVES FROM CARBON DIOXIDE AND OLEFINE | |
| CN103980173A (zh) | 一种帕立骨化醇中间体的制备方法 | |
| BR112017007276A2 (pt) | preparação de éster de sorbato | |
| JP2015044990A5 (enExample) | ||
| US20200283387A1 (en) | Method for preparing methionine analogues | |
| JP2016037476A (ja) | スルホン酸ハロゲン化物を用いたアミド化方法及びエステル化方法 | |
| JP2017222582A (ja) | カルボン酸チオエステルの製造方法 | |
| MY157731A (en) | Aqueous surfactant solution and method for producing the same | |
| JP2007223984A5 (enExample) |