JP2009523191A5 - - Google Patents
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- Publication number
- JP2009523191A5 JP2009523191A5 JP2008550324A JP2008550324A JP2009523191A5 JP 2009523191 A5 JP2009523191 A5 JP 2009523191A5 JP 2008550324 A JP2008550324 A JP 2008550324A JP 2008550324 A JP2008550324 A JP 2008550324A JP 2009523191 A5 JP2009523191 A5 JP 2009523191A5
- Authority
- JP
- Japan
- Prior art keywords
- polyalkylene oxide
- acid
- alkyl
- solvent system
- haloacetate
- 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
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 15
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims 21
- 239000002904 solvent Substances 0.000 claims 5
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- 239000002202 Polyethylene glycol Substances 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 229920001223 polyethylene glycol Polymers 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 239000011630 iodine Chemical group 0.000 claims 1
- 229910052740 iodine Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000005259 measurement Methods 0.000 claims 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims 1
- 229910000104 sodium hydride Inorganic materials 0.000 claims 1
- 239000012312 sodium hydride Substances 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical group CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 claims 1
- KUYMVWXKHQSIAS-UHFFFAOYSA-N tert-butyl 2-chloroacetate Chemical compound CC(C)(C)OC(=O)CCl KUYMVWXKHQSIAS-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/328,662 | 2006-01-10 | ||
| US11/328,662 US7989554B2 (en) | 2006-01-10 | 2006-01-10 | Reacting polyalkylene oxide with base, tertiary alkyl haloacetate, then acid to prepare polyalkylene oxide carboxylic acid |
| PCT/US2006/049706 WO2007081596A2 (en) | 2006-01-10 | 2006-12-28 | High efficiency method of preparing polyalkylene oxide carboxylic acids |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009523191A JP2009523191A (ja) | 2009-06-18 |
| JP2009523191A5 true JP2009523191A5 (https=) | 2012-06-21 |
| JP5199125B2 JP5199125B2 (ja) | 2013-05-15 |
Family
ID=38256821
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008550324A Expired - Fee Related JP5199125B2 (ja) | 2006-01-10 | 2006-12-28 | ポリアルキレンオキシド・カルボン酸の高効率製法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7989554B2 (https=) |
| EP (1) | EP1976896B1 (https=) |
| JP (1) | JP5199125B2 (https=) |
| KR (1) | KR20080083064A (https=) |
| CN (1) | CN101356203A (https=) |
| AT (1) | ATE512994T1 (https=) |
| AU (1) | AU2006335041A1 (https=) |
| CA (1) | CA2636280A1 (https=) |
| IL (1) | IL192409A0 (https=) |
| TW (1) | TW200732374A (https=) |
| WO (1) | WO2007081596A2 (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7671067B2 (en) * | 2006-02-09 | 2010-03-02 | Enzon Pharmaceuticals, Inc. | Treatment of non-hodgkin's lymphomas with multi-arm polymeric conjugates of 7-ethyl-10-hydroxycamtothecin |
| US7462627B2 (en) * | 2006-02-09 | 2008-12-09 | Enzon Pharmaceuticals, Inc. | Multi-arm polymeric conjugates of 7-ethyl-10-hydroxycamptothecin for treatment of breast, colorectal, pancreatic, ovarian and lung cancers |
| US20090156629A1 (en) * | 2006-06-09 | 2009-06-18 | Enzon Pharmaceuticals, Inc. | Indenoisoquinoline-releasable polymer conjugates |
| WO2008098178A2 (en) * | 2007-02-09 | 2008-08-14 | Enzon Pharmaceuticals, Inc. | Treatment of resistant or refractory cancers with multi-arm polymeric conjugates of 7-ethyl-10-hydroxycamptothecin |
| EP2147122B1 (en) * | 2007-04-20 | 2014-07-16 | Sigma-Tau Rare Diseases S.A. | Enzymatic anticancer therapy |
| HUE027603T2 (en) * | 2007-04-20 | 2016-10-28 | Sigma-Tau Rare Disease Ltd | Stable, recombinant adenosine deaminase |
| TW200922624A (en) * | 2007-07-11 | 2009-06-01 | Enzon Pharmaceuticals Inc | Polymeric drug delivery system containing a multi-substituted aromatic moiety |
| TW201010732A (en) * | 2008-08-29 | 2010-03-16 | Enzon Pharmaceuticals Inc | Method of treating RAS associated cancer |
| CA2738807A1 (en) * | 2008-10-21 | 2010-04-29 | Enzon Pharmaceuticals, Inc. | Treatment of neuroblastoma with multi-arm polymeric conjugates of 7-ethyl-10-hydroxycamptothecin |
| ES2753391T3 (es) | 2014-10-14 | 2020-04-08 | Halozyme Inc | Composiciones de adenosina desaminasa 2 (ADA2), variantes de la misma y métodos de uso de las mismas |
| US20240400945A1 (en) * | 2021-10-13 | 2024-12-05 | Basf Se | Compositions comprising polymers, polymers, and their use |
Family Cites Families (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4179337A (en) | 1973-07-20 | 1979-12-18 | Davis Frank F | Non-immunogenic polypeptides |
| US4315074A (en) | 1978-05-19 | 1982-02-09 | Pierce Chemical Company | Molecular transformation procedure |
| JPS57206622A (en) | 1981-06-10 | 1982-12-18 | Ajinomoto Co Inc | Blood substitute |
| JPS59204172A (ja) | 1983-04-28 | 1984-11-19 | Kowa Co | アセメタシンの製造法 |
| JPS60156395A (ja) | 1984-01-17 | 1985-08-16 | Mihama Hisaharu | 修飾リパーゼ |
| DE3675588D1 (de) | 1985-06-19 | 1990-12-20 | Ajinomoto Kk | Haemoglobin, das an ein poly(alkenylenoxid) gebunden ist. |
| US4760176A (en) | 1985-12-20 | 1988-07-26 | Borg-Warner Chemicals, Inc. | Aminocarboxylic acid-terminated polyoxy-alkylenes and process for the preparation thereof |
| US4814098A (en) | 1986-09-06 | 1989-03-21 | Bellex Corporation | Magnetic material-physiologically active substance conjugate |
| US5080891A (en) | 1987-08-03 | 1992-01-14 | Ddi Pharmaceuticals, Inc. | Conjugates of superoxide dismutase coupled to high molecular weight polyalkylene glycols |
| US5006333A (en) | 1987-08-03 | 1991-04-09 | Ddi Pharmaceuticals, Inc. | Conjugates of superoxide dismutase coupled to high molecular weight polyalkylene glycols |
| US4925968A (en) | 1987-12-23 | 1990-05-15 | American Home Products Corporation | N-acyl-N-naphthoylglycines as aldose reductase inhibitors |
| US5122614A (en) | 1989-04-19 | 1992-06-16 | Enzon, Inc. | Active carbonates of polyalkylene oxides for modification of polypeptides |
| US5453517A (en) | 1992-02-25 | 1995-09-26 | Molecular Probes, Inc. | Reactive derivatives of bapta used to make ion-selective chelators |
| US5122514A (en) | 1990-04-23 | 1992-06-16 | Abbott Laboratories | Psoriasis treatment |
| US5244910A (en) | 1990-08-15 | 1993-09-14 | Abbott Laboratories | Renin inhibitors |
| JP3051145B2 (ja) | 1990-08-28 | 2000-06-12 | 住友製薬株式会社 | 新規なポリエチレングリコール誘導体修飾ペプチド |
| US5545698A (en) | 1990-08-31 | 1996-08-13 | University Of Minnesota | Polyethylene glycol derivatives for solid-phase applications |
| US5145992A (en) | 1991-05-06 | 1992-09-08 | G. D. Searle & Co. | Process and preparation of α-alkoxy acetic acids and their salts |
| WO1993024476A1 (en) | 1992-06-04 | 1993-12-09 | Clover Consolidated, Limited | Water-soluble polymeric carriers for drug delivery |
| US5278303A (en) | 1992-06-12 | 1994-01-11 | University Of Toronto Innovations Foundation | Polymer-supported solution synthesis of oligosaccharides |
| CA2106141A1 (en) | 1992-09-28 | 1994-03-29 | Michael J. Betts | Antibiotic compounds |
| US5298643A (en) | 1992-12-22 | 1994-03-29 | Enzon, Inc. | Aryl imidate activated polyalkylene oxides |
| US5349001A (en) | 1993-01-19 | 1994-09-20 | Enzon, Inc. | Cyclic imide thione activated polyalkylene oxides |
| US5321095A (en) | 1993-02-02 | 1994-06-14 | Enzon, Inc. | Azlactone activated polyalkylene oxides |
| US5298410A (en) | 1993-02-25 | 1994-03-29 | Sterling Winthrop Inc. | Lyophilized formulation of polyethylene oxide modified proteins with increased shelf-life |
| US5436369A (en) | 1993-06-16 | 1995-07-25 | Bristol-Myers Squibb Company | Alicyclic phospholipase A2 inhibitors |
| US5430043A (en) | 1993-08-24 | 1995-07-04 | G. D. Searle & Co. | Platelet aggregation inhibitors |
| US5880131A (en) | 1993-10-20 | 1999-03-09 | Enzon, Inc. | High molecular weight polymer-based prodrugs |
| US5605976A (en) | 1995-05-15 | 1997-02-25 | Enzon, Inc. | Method of preparing polyalkylene oxide carboxylic acids |
| US5643575A (en) | 1993-10-27 | 1997-07-01 | Enzon, Inc. | Non-antigenic branched polymer conjugates |
| JP3407397B2 (ja) * | 1994-05-06 | 2003-05-19 | 日本油脂株式会社 | ポリオキシアルキレン誘導体および製造方法 |
| US5756593A (en) * | 1995-05-15 | 1998-05-26 | Enzon, Inc. | Method of preparing polyalkyene oxide carboxylic acids |
| US5847003A (en) | 1996-06-04 | 1998-12-08 | Avon Products, Inc. | Oxa acids and related compounds for treating skin conditions |
| JPH1087815A (ja) * | 1996-08-22 | 1998-04-07 | Enzon Inc | ポリアルキレンオキシドカルボン酸の改良製造方法 |
| US6153655A (en) | 1998-04-17 | 2000-11-28 | Enzon, Inc. | Terminally-branched polymeric linkers and polymeric conjugates containing the same |
| US6756037B2 (en) | 2000-03-31 | 2004-06-29 | Enzon, Inc. | Polymer conjugates of biologically active agents and extension moieties for facilitating conjugation of biologically active agents to polymeric terminal groups |
| DK1539857T3 (da) * | 2002-07-24 | 2007-03-12 | Hoffmann La Roche | Polyethylenglycol-aldehydderivater |
| JP3770246B2 (ja) * | 2003-04-11 | 2006-04-26 | 日本油脂株式会社 | ポリオキシアルキレン誘導体の製造方法 |
| US20050214250A1 (en) | 2003-11-06 | 2005-09-29 | Harris J M | Method of preparing carboxylic acid functionalized polymers |
-
2006
- 2006-01-10 US US11/328,662 patent/US7989554B2/en not_active Expired - Fee Related
- 2006-12-26 TW TW095148888A patent/TW200732374A/zh unknown
- 2006-12-28 AT AT06849274T patent/ATE512994T1/de not_active IP Right Cessation
- 2006-12-28 KR KR1020087019394A patent/KR20080083064A/ko not_active Withdrawn
- 2006-12-28 CN CNA2006800508510A patent/CN101356203A/zh active Pending
- 2006-12-28 JP JP2008550324A patent/JP5199125B2/ja not_active Expired - Fee Related
- 2006-12-28 AU AU2006335041A patent/AU2006335041A1/en not_active Abandoned
- 2006-12-28 WO PCT/US2006/049706 patent/WO2007081596A2/en not_active Ceased
- 2006-12-28 EP EP06849274A patent/EP1976896B1/en not_active Not-in-force
- 2006-12-28 CA CA002636280A patent/CA2636280A1/en not_active Abandoned
-
2008
- 2008-06-24 IL IL192409A patent/IL192409A0/en unknown
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