JP2008511729A - 高純度高分子量メトキシポリエチレングリコール（ｍｐｅｇ） - Google Patents
高純度高分子量メトキシポリエチレングリコール（ｍｐｅｇ） Download PDFInfo
- Publication number
- JP2008511729A JP2008511729A JP2007530186A JP2007530186A JP2008511729A JP 2008511729 A JP2008511729 A JP 2008511729A JP 2007530186 A JP2007530186 A JP 2007530186A JP 2007530186 A JP2007530186 A JP 2007530186A JP 2008511729 A JP2008511729 A JP 2008511729A
- Authority
- JP
- Japan
- Prior art keywords
- ethylene glycol
- monomethoxypoly
- molecular weight
- polymer
- mpeg
- 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.)
- Pending
Links
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims description 62
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title 1
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 45
- 238000000034 method Methods 0.000 claims abstract description 27
- 150000002009 diols Chemical class 0.000 claims abstract description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000000203 mixture Substances 0.000 claims abstract description 13
- 229920000642 polymer Polymers 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 238000000108 ultra-filtration Methods 0.000 claims description 11
- 239000000243 solution Substances 0.000 claims description 10
- 238000000926 separation method Methods 0.000 claims description 9
- 239000012528 membrane Substances 0.000 claims description 8
- 239000011347 resin Substances 0.000 claims description 8
- 229920005989 resin Polymers 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 239000003586 protic polar solvent Substances 0.000 claims description 6
- 238000001694 spray drying Methods 0.000 claims description 6
- 238000002336 sorption--desorption measurement Methods 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 238000004587 chromatography analysis Methods 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 238000001556 precipitation Methods 0.000 claims description 4
- 238000002955 isolation Methods 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000011148 porous material Substances 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical group ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 238000004811 liquid chromatography Methods 0.000 claims 2
- VPGHVKMBMPDAJD-UHFFFAOYSA-N 2,3-dinitrobenzoyl chloride Chemical group [O-][N+](=O)C1=CC=CC(C(Cl)=O)=C1[N+]([O-])=O VPGHVKMBMPDAJD-UHFFFAOYSA-N 0.000 claims 1
- 238000009614 chemical analysis method Methods 0.000 claims 1
- 229920001427 mPEG Polymers 0.000 abstract description 50
- 238000006116 polymerization reaction Methods 0.000 abstract description 6
- 229920002125 Sokalan® Polymers 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 239000004584 polyacrylic acid Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000012466 permeate Substances 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000000975 bioactive effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- -1 methyltrityl Chemical group 0.000 description 3
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- GHUBZYXDFSBGLI-UHFFFAOYSA-N 1-[[(2,3-dimethoxyphenyl)-diphenylmethoxy]-diphenylmethyl]-2,3-dimethoxybenzene Chemical compound COC1=CC=CC(C(OC(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C(=C(OC)C=CC=2)OC)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1OC GHUBZYXDFSBGLI-UHFFFAOYSA-N 0.000 description 1
- NNOHXABAQAGKRZ-UHFFFAOYSA-N 3,5-dinitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC(C(Cl)=O)=CC([N+]([O-])=O)=C1 NNOHXABAQAGKRZ-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 238000003109 Karl Fischer titration Methods 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000001268 conjugating effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012465 retentate Substances 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/30—Post-polymerisation treatment, e.g. recovery, purification, drying
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Polyethers (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/932,629 US20060045866A1 (en) | 2004-09-01 | 2004-09-01 | Novel high purity and high molecular weight mPEG alcohol compositions |
| PCT/US2005/030518 WO2006028745A1 (en) | 2004-09-01 | 2005-08-25 | High purity, high molecular weight methoxy-polyethylenglycols (mpeg) |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008511729A true JP2008511729A (ja) | 2008-04-17 |
| JP2008511729A5 JP2008511729A5 (enExample) | 2008-10-23 |
Family
ID=35355094
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007530186A Pending JP2008511729A (ja) | 2004-09-01 | 2005-08-25 | 高純度高分子量メトキシポリエチレングリコール（ｍｐｅｇ） |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US20060045866A1 (enExample) |
| EP (1) | EP1789473A1 (enExample) |
| JP (1) | JP2008511729A (enExample) |
| KR (1) | KR20070058549A (enExample) |
| CN (1) | CN101068850B (enExample) |
| WO (1) | WO2006028745A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010114073A1 (ja) * | 2009-03-31 | 2010-10-07 | 日油株式会社 | 高分子量ポリオキシアルキレン誘導体の精製方法 |
| JP2010254981A (ja) * | 2009-03-31 | 2010-11-11 | Nof Corp | 高分子量ポリエチレングリコール化合物の精製方法 |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2592904C (en) * | 2004-12-30 | 2015-04-07 | 3M Innovative Properties Company | Chiral fused [1,2]imidazo[4,5-c] ring compounds |
| WO2008101311A1 (en) * | 2007-02-22 | 2008-08-28 | Biovectra Inc. | Process for purification of water soluble polymers |
| KR100922113B1 (ko) * | 2007-12-29 | 2009-10-16 | 아이디비켐(주) | 고순도의 벤질옥시폴리에틸렌글리콜 및 그의 유도체의제조방법 |
| JP5001184B2 (ja) * | 2008-01-29 | 2012-08-15 | 三洋化成工業株式会社 | ポリオキシアルキレンエーテル組成物の製造法 |
| TWI451876B (zh) | 2008-06-13 | 2014-09-11 | Lilly Co Eli | 聚乙二醇化之離脯胰島素化合物 |
| ATE545673T1 (de) | 2009-06-18 | 2012-03-15 | Basf Se | Verfahren zur herstellung von monohydroxypolyalkylenoxiden |
| JP2013530271A (ja) | 2010-05-21 | 2013-07-25 | ゼフィロス インコーポレイテッド | 構造材料の塗布方法 |
| GB201207481D0 (en) | 2012-04-26 | 2012-06-13 | Zephyros Inc | Applying flowable materials to synthetic substrates |
| CN107321128B (zh) * | 2017-05-31 | 2020-11-03 | 南京威尔药业集团股份有限公司 | 一种用于生产高纯单甲氧基聚乙二醇的反应系统 |
| US10988489B2 (en) * | 2018-11-27 | 2021-04-27 | Clark Atlanta University | Organoboranes useful as electrolytes for lithium batteries |
| CN112724396A (zh) * | 2020-12-28 | 2021-04-30 | 苏州欣影生物医药技术有限公司 | 一种提高聚乙二醇类衍生物分子量分布的纯化方法 |
| CN114636773B (zh) * | 2022-05-23 | 2022-08-23 | 广东国标医药科技有限公司 | 一种药用辅料中聚乙二醇单甲醚2000的含量测定方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2983763A (en) * | 1956-04-12 | 1961-05-09 | Jefferson Chem Co Inc | Decolorizing the product of reacting an alkylene oxide with a hydroxylcontaining organic compound in the presence of an alkaline reacting catalyst |
| US3974127A (en) * | 1973-09-17 | 1976-08-10 | E. I. Du Pont De Nemours And Company | Alkylene oxide condensates of tetramethylpiperidine alcohols or glycols |
| US4911926A (en) * | 1988-11-16 | 1990-03-27 | Mediventures Inc. | Method and composition for reducing postsurgical adhesions |
| FR2686088B1 (fr) * | 1992-01-10 | 1995-06-23 | Atochem Elf Sa | Procede de fabrication de polycondensats multisequences, en etoile ou en reseaux par couplage a l'aide de di- ou multi-aldehydes, et polycondensats ainsi obtenus. |
| FR2689895A1 (fr) * | 1992-04-10 | 1993-10-15 | Chryso | Procédé de préparation d'amines polyoxyalkylées. |
| US5348569A (en) * | 1993-06-30 | 1994-09-20 | Praxair Technology, Inc. | Modified poly(phenylene oxide) based membranes for enhanced fluid separation |
| US5308881A (en) * | 1993-10-25 | 1994-05-03 | The Celotex Corporation | Surfactant for polyisocyanurate foams made with alternative blowing agents |
| US5605976A (en) * | 1995-05-15 | 1997-02-25 | Enzon, Inc. | Method of preparing polyalkylene oxide carboxylic acids |
| US5752991A (en) * | 1995-12-29 | 1998-05-19 | Chevron Chemical Company | Very long chain alkylphenyl polyoxyalkylene amines and fuel compositions containing the same |
| US6280745B1 (en) * | 1997-12-23 | 2001-08-28 | Alliance Pharmaceutical Corp. | Methods and compositions for the delivery of pharmaceutical agents and/or the prevention of adhesions |
| WO1998029459A1 (en) * | 1996-12-27 | 1998-07-09 | Kao Corporation | Method for the purification of ionic polymers |
| US6323322B1 (en) * | 1997-04-30 | 2001-11-27 | Enzon, Inc. | Single-chain antigen-binding proteins capable of glycosylation, production and uses thereof |
| KR100358276B1 (ko) * | 1998-03-24 | 2002-10-25 | 닛폰 유시 가부시키가이샤 | 옥시란 유도체 및 이의 제조방법 |
| US6642422B2 (en) * | 1998-06-17 | 2003-11-04 | Nof Corporation | Polyoxyalkylene monoalkyl ether, process for producing the same, polymerizable polyoxyalkylene monoalky ether derivative, polymer of said derivative and dispersant comprising said polymer |
| TW593427B (en) * | 2000-12-18 | 2004-06-21 | Nektar Therapeutics Al Corp | Synthesis of high molecular weight non-peptidic polymer derivatives |
| MXPA06001000A (es) * | 2003-07-22 | 2006-05-15 | Nektar Therapeutics Al Corp | Metodo para preparar polimeros funcionalizados a partir de alcoholes polimericos. |
-
2004
- 2004-09-01 US US10/932,629 patent/US20060045866A1/en not_active Abandoned
-
2005
- 2005-08-25 CN CN2005800346808A patent/CN101068850B/zh not_active Expired - Fee Related
- 2005-08-25 WO PCT/US2005/030518 patent/WO2006028745A1/en not_active Ceased
- 2005-08-25 JP JP2007530186A patent/JP2008511729A/ja active Pending
- 2005-08-25 EP EP05792760A patent/EP1789473A1/en not_active Withdrawn
- 2005-08-25 KR KR1020077007148A patent/KR20070058549A/ko not_active Ceased
-
2009
- 2009-10-22 US US12/603,708 patent/US20100041160A1/en not_active Abandoned
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010114073A1 (ja) * | 2009-03-31 | 2010-10-07 | 日油株式会社 | 高分子量ポリオキシアルキレン誘導体の精製方法 |
| JP2010254978A (ja) * | 2009-03-31 | 2010-11-11 | Nof Corp | 高分子量ポリオキシアルキレン誘導体の精製方法 |
| JP2010254981A (ja) * | 2009-03-31 | 2010-11-11 | Nof Corp | 高分子量ポリエチレングリコール化合物の精製方法 |
| US8097692B2 (en) | 2009-03-31 | 2012-01-17 | Nof Corporation | Purification method of high-molecular-weight polyoxyalkylene derivative |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20070058549A (ko) | 2007-06-08 |
| US20100041160A1 (en) | 2010-02-18 |
| EP1789473A1 (en) | 2007-05-30 |
| WO2006028745A1 (en) | 2006-03-16 |
| CN101068850A (zh) | 2007-11-07 |
| US20060045866A1 (en) | 2006-03-02 |
| CN101068850B (zh) | 2011-09-28 |
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