JP4987719B2 - ポリエチレングリコール化合物と製造方法 - Google Patents
ポリエチレングリコール化合物と製造方法 Download PDFInfo
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- JP4987719B2 JP4987719B2 JP2007533676A JP2007533676A JP4987719B2 JP 4987719 B2 JP4987719 B2 JP 4987719B2 JP 2007533676 A JP2007533676 A JP 2007533676A JP 2007533676 A JP2007533676 A JP 2007533676A JP 4987719 B2 JP4987719 B2 JP 4987719B2
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- Prior art keywords
- polyethylene glycol
- reaction mixture
- compound
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- alcohol
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- 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
- C08G65/26—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 from cyclic ethers and other compounds
- C08G65/2603—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 from cyclic ethers and other compounds the other compounds containing oxygen
-
- 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
Description
本発明は、狭い分子量分布と低いジオール不純物のコンタミネーションと共に(例えば、40,000を超えるようなmPEG分子量が)以前に得られたものよりも高い分子量を有する置換ポリエチレングリコール化合物である。本発明はまた、それらの物質を製造する方法でもある。
4O)nYは実験に基づいた式であり、Yは水素とアルカリ金属の混合物であり、Yがアルカリ金属のとき、化合物が解離する。
以下の表1は、上記実施例に概略したシステムを用いた各種反応の処方(recipe)をあげたものである(バッチ4046は上記実施例である。)次の表2は表1の各種バッチに対する分析結果をあげたものである。
Claims (15)
- 式 RO(C2H4O)nY
を有する置換ポリエチレングリコール化合物の調製方法であって、ここでRはC1-7炭化水素基を表し、nは600から2000の範囲のC2H4O基の平均モル数を表し、Yは水素またはアルカリ金属を表し、該置換ポリエチレングリコール化合物は1から1.1の範囲において数平均分子量に対する重量平均分子量の比を有し、該置換ポリエチレングリコール化合物の重量平均分子量および数平均分子量がゲル透過クロマトグラフィーにより決定され、
(a)式R(OCH 2 CH 2 ) 0-20 OH(式中、RはC1-7炭化水素基を表す)により表されるアルコール、該アルコールのアルコキシド、およびポリエーテル溶媒を含む反応混合物を形成する工程であって、反応混合物が80℃から140℃の範囲の温度にあり、反応混合物の水分濃度が重量で10ppm未満であり、該アルコールに対する該アルコールのアルコキシドのモル比が0.01から100の範囲にある工程;および
(b)酸化エチレンと該反応混合物とを接触させ、酸化エチレンが反応して置換ポリエチレングリコール化合物を形成する工程
を含む方法。 - 該ポリエーテル溶媒がビス(2-メトキシエチル)エーテルである、請求項1記載の方法。
- 該アルコールがジエチレングリコールモノメチルエーテルである、請求項1記載の方法。
- 該アルコールがジエチレングリコールモノメチルエーテルである、請求項2記載の方法。
- 該反応混合物の温度が90℃から110℃の範囲にある、請求項4記載の方法。
- 工程(b)の終点での該反応混合物中における該置換ポリエチレングリコール化合物の濃度が該反応混合物の20から80重量%である、請求項4記載の方法。
- 工程(b)の終点での該反応混合物中における該置換ポリエチレングリコール化合物の濃度が反応混合物の40から60重量%である、請求項4記載の方法。
- 工程(b)の終点での該反応混合物がまた、ポリエチレングリコールを含み、ポリエチレングリコールの量がポリエチレングリコールと置換ポリエチレン化合物の合計モル数の10モル%未満のポリエチレングリコール量であり、液体クロマトグラフィーによりポリエチレングリコール量が決定される、請求項4記載の方法。
- 工程(b)の終点での該反応混合物がまた、ポリエチレングリコールを含み、ポリエチレングリコールの量がポリエチレングリコールと該置換ポリエチレン化合物の合計モル数の5モル%未満のポリエチレングリコール量であり、液体クロマトグラフィーにより該ポリエチレングリコール量が決定される、請求項4記載の方法。
- 工程(b)の終点での該反応混合物がまた、ポリエチレングリコールを含み、ポリエチレングリコールの量がポリエチレングリコールと該置換ポリエチレン化合物の合計モル数の2加1/2モル%未満のポリエチレングリコール量であり、液体クロマトグラフィーによりポリエチレングリコール量が決定される、請求項4記載の方法。
- 工程(b)の後、Yが水素であるように、該反応混合物に酸を添加する工程をさらに含む、請求項1記載の方法。
- 工程(b)の後、該反応混合物を非極性溶媒と混合し、置換ポリエチレングリコール化合物を沈殿させる工程をさらに含む、請求項1記載の方法。
- 工程(b)の後、該反応混合物を、非極性溶媒と酸とからなる反応混合物と混合し、Yが水素である該置換ポリエチレングリコール化合物を沈殿させる工程をさらに含む、請求項1記載の方法。
- nが少なくとも700である、請求項1記載の方法。
- 該アルコールがポリエーテルアルコールである、請求項1記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/952,198 | 2004-09-28 | ||
US10/952,198 US7199193B2 (en) | 2004-09-28 | 2004-09-28 | Polyethylene glycol compounds and process of making |
PCT/US2005/034251 WO2006036825A1 (en) | 2004-09-28 | 2005-09-27 | Polyethylene glycol compounds and process for making |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2008514763A JP2008514763A (ja) | 2008-05-08 |
JP2008514763A5 JP2008514763A5 (ja) | 2012-02-23 |
JP4987719B2 true JP4987719B2 (ja) | 2012-07-25 |
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ID=35432615
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JP2007533676A Expired - Fee Related JP4987719B2 (ja) | 2004-09-28 | 2005-09-27 | ポリエチレングリコール化合物と製造方法 |
Country Status (8)
Country | Link |
---|---|
US (2) | US7199193B2 (ja) |
EP (1) | EP1797131B1 (ja) |
JP (1) | JP4987719B2 (ja) |
KR (1) | KR101279664B1 (ja) |
CN (1) | CN101031604B (ja) |
AT (1) | ATE552286T1 (ja) |
ES (1) | ES2384979T3 (ja) |
WO (1) | WO2006036825A1 (ja) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2896643A1 (en) | 2014-01-16 | 2015-07-22 | Shin-Etsu Chemical Co., Ltd. | Method for producing polyalkylene glycol derivative having amino group at end, with narrow molecular weight distribution |
KR20160067752A (ko) | 2014-12-04 | 2016-06-14 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 말단에 아미노기를 갖는 폴리알킬렌글리콜 유도체의 제조 방법 |
US9708350B2 (en) | 2014-12-04 | 2017-07-18 | Shin-Etsu Chemical Co., Ltd. | Method for producing polyalkylene glycol derivative having amino group at end, polymerization initiator for use in the same, and alcohol compound as raw material for the polymerization initiator |
US10377775B2 (en) | 2014-12-04 | 2019-08-13 | Shin-Etsu Chemical Co., Ltd. | Method for producing polyalkylene glycol derivative having amino group at end |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102004059489C5 (de) † | 2004-12-10 | 2011-12-08 | Clariant Produkte (Deutschland) Gmbh | Verfahren zur Herstellung von reinen alpha-Alkoxy-omega-hydroxy-Polyalkylenglykolen |
CN101679625B (zh) * | 2007-05-29 | 2013-06-26 | 栗村化学株式会社 | 链末端官能化的甲氧基聚乙二醇及其金属纳米颗粒 |
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 |
US8569444B2 (en) | 2008-11-11 | 2013-10-29 | Nof Corporation | Polyalkylene glycol derivative and process for producing same |
JP5713274B2 (ja) * | 2009-03-31 | 2015-05-07 | 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 |
JP5569787B2 (ja) * | 2009-03-31 | 2014-08-13 | 日油株式会社 | 高分子量ポリエチレングリコール化合物の精製方法 |
ES2379571T3 (es) * | 2009-06-18 | 2012-04-27 | Basf Se | Procedimiento para la obtención de óxidos de monohidroxipolialquileno |
WO2013157486A1 (ja) * | 2012-04-18 | 2013-10-24 | 旭硝子株式会社 | ポリエーテル類の製造方法 |
US9315549B2 (en) | 2013-01-28 | 2016-04-19 | New York University | Treatment methods using atoxic neurotoxin derivatives |
CA2969463A1 (en) | 2014-12-09 | 2016-06-16 | New York University | Clostridial neurotoxin fusion proteins, propeptide fusions, their expression, and use |
CN110832008A (zh) * | 2017-08-17 | 2020-02-21 | 沙特基础工业全球技术有限公司 | 制备聚氧乙烯的脂肪酸单酯的方法、由其制备的酯及其用途 |
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US4911926A (en) | 1988-11-16 | 1990-03-27 | Mediventures Inc. | Method and composition for reducing postsurgical adhesions |
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 |
JP3050228B2 (ja) * | 1998-03-24 | 2000-06-12 | 日本油脂株式会社 | オキシラン誘導体及びその製造方法 |
DE69929311T2 (de) | 1998-03-24 | 2006-09-07 | Nof Corp. | Oximanderivate und verfahren zu ihrer herstellung |
DE10121807A1 (de) * | 2001-05-04 | 2002-11-07 | Bayer Ag | Verfahren zur Herstellung von Polyetherpolyolen |
PT1656410E (pt) | 2003-07-22 | 2010-06-11 | Nektar Therapeutics | Processo para preparação de polímeros funcionalizados a partir de álcoois poliméricos |
-
2004
- 2004-09-28 US US10/952,198 patent/US7199193B2/en not_active Expired - Fee Related
-
2005
- 2005-09-27 CN CN2005800328299A patent/CN101031604B/zh not_active Expired - Fee Related
- 2005-09-27 EP EP05798703A patent/EP1797131B1/en not_active Not-in-force
- 2005-09-27 WO PCT/US2005/034251 patent/WO2006036825A1/en active Application Filing
- 2005-09-27 ES ES05798703T patent/ES2384979T3/es active Active
- 2005-09-27 KR KR1020077006984A patent/KR101279664B1/ko active IP Right Grant
- 2005-09-27 JP JP2007533676A patent/JP4987719B2/ja not_active Expired - Fee Related
- 2005-09-27 AT AT05798703T patent/ATE552286T1/de active
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2007
- 2007-02-28 US US11/712,574 patent/US20070213479A1/en not_active Abandoned
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2896643A1 (en) | 2014-01-16 | 2015-07-22 | Shin-Etsu Chemical Co., Ltd. | Method for producing polyalkylene glycol derivative having amino group at end, with narrow molecular weight distribution |
US9187404B2 (en) | 2014-01-16 | 2015-11-17 | Shin-Etsu Chemical Co., Ltd. | Method for producing polyalkylene glycol derivative having amino group at end, with narrow molecular weight distribution |
KR20160067752A (ko) | 2014-12-04 | 2016-06-14 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 말단에 아미노기를 갖는 폴리알킬렌글리콜 유도체의 제조 방법 |
EP3064524A1 (en) | 2014-12-04 | 2016-09-07 | Shin-Etsu Chemical Co., Ltd. | Method for producing polyalkylene glycol derivative having amino group at end |
US9708350B2 (en) | 2014-12-04 | 2017-07-18 | Shin-Etsu Chemical Co., Ltd. | Method for producing polyalkylene glycol derivative having amino group at end, polymerization initiator for use in the same, and alcohol compound as raw material for the polymerization initiator |
EP3412700A1 (en) | 2014-12-04 | 2018-12-12 | Shin-Etsu Chemical Co., Ltd. | Compounds |
EP3412701A1 (en) | 2014-12-04 | 2018-12-12 | Shin-Etsu Chemical Co., Ltd. | Polyalkylene glycol product |
US10377775B2 (en) | 2014-12-04 | 2019-08-13 | Shin-Etsu Chemical Co., Ltd. | Method for producing polyalkylene glycol derivative having amino group at end |
US10472377B2 (en) | 2014-12-04 | 2019-11-12 | Shin-Etsu Chemical Co., Ltd. | Method for producing polyalkylene glycol derivative having amino group at end, polymerization initiator for use in the same, and alcohol compound as raw material for the polymerization initiator |
US10550136B2 (en) | 2014-12-04 | 2020-02-04 | Shin-Etsu Chemical Co., Ltd. | Method for producing polyalkylene glycol derivative having amino group at end |
US11066430B2 (en) | 2014-12-04 | 2021-07-20 | Shin-Etsu Chemical Co., Ltd. | Method for producing polyalkylene glycol derivative having amino group at end |
Also Published As
Publication number | Publication date |
---|---|
JP2008514763A (ja) | 2008-05-08 |
ES2384979T3 (es) | 2012-07-16 |
WO2006036825A1 (en) | 2006-04-06 |
EP1797131B1 (en) | 2012-04-04 |
KR20070058534A (ko) | 2007-06-08 |
US20070213479A1 (en) | 2007-09-13 |
CN101031604A (zh) | 2007-09-05 |
CN101031604B (zh) | 2010-08-11 |
EP1797131A1 (en) | 2007-06-20 |
KR101279664B1 (ko) | 2013-06-27 |
US7199193B2 (en) | 2007-04-03 |
US20060074200A1 (en) | 2006-04-06 |
ATE552286T1 (de) | 2012-04-15 |
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Free format text: JAPANESE INTERMEDIATE CODE: R250 |
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LAPS | Cancellation because of no payment of annual fees |