NZ534708A - Polyalkylene glycol with moiety for conjugating biologically active compound - Google Patents
Polyalkylene glycol with moiety for conjugating biologically active compoundInfo
- Publication number
- NZ534708A NZ534708A NZ534708A NZ53470803A NZ534708A NZ 534708 A NZ534708 A NZ 534708A NZ 534708 A NZ534708 A NZ 534708A NZ 53470803 A NZ53470803 A NZ 53470803A NZ 534708 A NZ534708 A NZ 534708A
- Authority
- NZ
- New Zealand
- Prior art keywords
- alkyl
- group
- substituted
- saturated
- formula
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 242
- 229920001515 polyalkylene glycol Polymers 0.000 title claims abstract description 145
- 230000001268 conjugating effect Effects 0.000 title description 3
- 238000011282 treatment Methods 0.000 claims abstract description 27
- 208000036142 Viral infection Diseases 0.000 claims abstract description 23
- 230000009385 viral infection Effects 0.000 claims abstract description 23
- 208000005176 Hepatitis C Diseases 0.000 claims abstract description 14
- 201000006417 multiple sclerosis Diseases 0.000 claims abstract description 8
- -1 cyano, nitro, azido, sulfhydryl Chemical group 0.000 claims description 464
- 229920006395 saturated elastomer Polymers 0.000 claims description 295
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 240
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 190
- 125000001072 heteroaryl group Chemical group 0.000 claims description 188
- 239000000203 mixture Substances 0.000 claims description 182
- 150000001412 amines Chemical class 0.000 claims description 178
- 125000003118 aryl group Chemical group 0.000 claims description 176
- 150000002148 esters Chemical group 0.000 claims description 170
- 229910052736 halogen Inorganic materials 0.000 claims description 167
- 150000002367 halogens Chemical group 0.000 claims description 167
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 142
- 150000001299 aldehydes Chemical class 0.000 claims description 142
- 229920000642 polymer Polymers 0.000 claims description 137
- 229910052739 hydrogen Inorganic materials 0.000 claims description 135
- 239000001257 hydrogen Substances 0.000 claims description 135
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims description 133
- 125000000217 alkyl group Chemical group 0.000 claims description 130
- 239000002243 precursor Substances 0.000 claims description 113
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 111
- 125000001424 substituent group Chemical group 0.000 claims description 107
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 103
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 98
- 125000000623 heterocyclic group Chemical group 0.000 claims description 98
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 98
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical group [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 97
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 96
- 150000007942 carboxylates Chemical group 0.000 claims description 96
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical group [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 95
- 125000002252 acyl group Chemical group 0.000 claims description 95
- 125000003545 alkoxy group Chemical group 0.000 claims description 95
- 125000004414 alkyl thio group Chemical group 0.000 claims description 95
- 125000003368 amide group Chemical group 0.000 claims description 95
- 150000001409 amidines Chemical group 0.000 claims description 95
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 95
- 150000007970 thio esters Chemical group 0.000 claims description 95
- DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical group CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 claims description 95
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 95
- 150000002466 imines Chemical group 0.000 claims description 94
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 94
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical group [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims description 93
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 92
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 91
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 91
- AWIJRPNMLHPLNC-UHFFFAOYSA-N methanethioic s-acid Chemical group SC=O AWIJRPNMLHPLNC-UHFFFAOYSA-N 0.000 claims description 84
- 150000002431 hydrogen Chemical class 0.000 claims description 74
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 71
- CYWHLOXWVAWMFO-UHFFFAOYSA-N 3-sulfanyl-1h-pyridine-2-thione Chemical compound SC1=CC=CN=C1S CYWHLOXWVAWMFO-UHFFFAOYSA-N 0.000 claims description 71
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 71
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 71
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 71
- 150000001241 acetals Chemical class 0.000 claims description 71
- 125000003342 alkenyl group Chemical group 0.000 claims description 71
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 claims description 71
- 150000002118 epoxides Chemical class 0.000 claims description 71
- PGLTVOMIXTUURA-UHFFFAOYSA-N iodoacetamide Chemical compound NC(=O)CI PGLTVOMIXTUURA-UHFFFAOYSA-N 0.000 claims description 71
- 239000012948 isocyanate Substances 0.000 claims description 71
- 150000002513 isocyanates Chemical class 0.000 claims description 71
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- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 71
- 150000003457 sulfones Chemical class 0.000 claims description 71
- 150000003573 thiols Chemical class 0.000 claims description 71
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 71
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 70
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 70
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 70
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 68
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 64
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 62
- 229940015043 glyoxal Drugs 0.000 claims description 62
- 229920001223 polyethylene glycol Polymers 0.000 claims description 62
- 125000005647 linker group Chemical group 0.000 claims description 56
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 55
- 229910052760 oxygen Inorganic materials 0.000 claims description 54
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 52
- 229910052717 sulfur Inorganic materials 0.000 claims description 52
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 51
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 49
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 33
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
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- 102000003996 Interferon-beta Human genes 0.000 claims description 18
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- 125000003277 amino group Chemical group 0.000 claims description 11
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- 125000003275 alpha amino acid group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
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- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 5
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
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- IWUCXVSUMQZMFG-RGDLXGNYSA-N 1-[(2s,3s,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide Chemical compound N1=C(C(=O)N)N=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 IWUCXVSUMQZMFG-RGDLXGNYSA-N 0.000 claims 9
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| US20150246097A9 (en) * | 2002-01-18 | 2015-09-03 | Biogen Idec Ma Inc. | Polyalkylene Polymer Compounds and Uses Thereof |
| GEP20064024B (en) * | 2002-01-18 | 2007-01-10 | Biogen Idec Inc | Polyalkylene glycol comprising a radical for conjugation of biologically active compound |
| BR0314172A (pt) | 2002-09-09 | 2005-07-26 | Nektar Therapeutics Al Corp | Polìmero solúvel em água, composição, forma de hidrato ou acetal, composto,composição, usos do composto e do conjugado, e, processo para preparar o conjugado |
| US8129330B2 (en) | 2002-09-30 | 2012-03-06 | Mountain View Pharmaceuticals, Inc. | Polymer conjugates with decreased antigenicity, methods of preparation and uses thereof |
| US20040136952A1 (en) * | 2002-12-26 | 2004-07-15 | Mountain View Pharmaceuticals, Inc. | Polymer conjugates of cytokines, chemokines, growth factors, polypeptide hormones and antagonists thereof with preserved receptor-binding activity |
| JP5207590B2 (ja) | 2002-12-26 | 2013-06-12 | マウンテン ビュー ファーマシューティカルズ，インコーポレイテッド | 増強された生物学的能力を有するインターフェロン−βのポリマー結合体 |
| CN100343304C (zh) | 2002-12-31 | 2007-10-17 | 尼克塔治疗亚拉巴马公司 | 水解稳定的马来酰亚胺封端的聚合物 |
| US7432331B2 (en) | 2002-12-31 | 2008-10-07 | Nektar Therapeutics Al, Corporation | Hydrolytically stable maleimide-terminated polymers |
| WO2005000268A2 (en) | 2003-06-26 | 2005-01-06 | Control Delivery Systems, Inc. | Bioerodible sustained release drug delivery systems |
| EP1635875B8 (en) | 2003-06-26 | 2008-12-24 | pSivida Inc | In-situ gelling drug delivery system |
| EP1758583A2 (en) * | 2004-05-31 | 2007-03-07 | Ranbaxy Laboratories Limited | Arylpiperazine derivatives useful as adrenergic receptor antagonists |
| US7851565B2 (en) | 2004-12-21 | 2010-12-14 | Nektar Therapeutics | Stabilized polymeric thiol reagents |
| WO2006130553A2 (en) * | 2005-06-02 | 2006-12-07 | Schering Corporation | Hcv protease inhibitors |
| US8268935B2 (en) * | 2005-07-08 | 2012-09-18 | Elan Pharmaceuticals, Inc. | Preparation of polymer conjugates of therapeutic, agricultural, and food additive compounds |
| WO2007137260A2 (en) * | 2006-05-22 | 2007-11-29 | Elan Pharmaceuticals, Inc. | Preparation of polymer conjugates of vla-4 antagonists via a mitsunobu' s reaction |
| WO2008066816A2 (en) * | 2006-11-28 | 2008-06-05 | The Board Of Trustees Of The University Of Illinois | Derivatization or ligaton of peptides |
| CA2693645A1 (en) * | 2007-07-11 | 2009-01-15 | Enzon Pharmaceuticals, Inc. | Polymeric drug delivery systems containing an aromatic allylic acid |
| CA2693616A1 (en) * | 2007-07-11 | 2009-01-15 | Enzon Pharmaceuticals, Inc. | Polymeric drug delivery system containing a multi-substituted aromatic moiety |
| CL2008002399A1 (es) * | 2007-08-16 | 2009-01-02 | Pharmaessentia Corp | Conjugado sustancialmente puro que posee una porcion polimerica, una porcion proteica (interferon alfa 2b) y un ligante alifatico de 1 a 10 atomos de carbono, util en el tratamiento de las hepatitis b o c. |
| AU2009255994B2 (en) * | 2008-06-05 | 2014-07-17 | Bristol-Myers Squibb Company | Use of pegylated Type III Interferons for the treatment of hepatitis C |
| BRPI0911722B1 (pt) * | 2008-07-31 | 2022-09-13 | Pharmaessentia Corp | Conjugado de peptídeo-polímero |
| GB0823309D0 (en) * | 2008-12-19 | 2009-01-28 | Univ Bath | Functionalising reagents and their uses |
| CN102428512A (zh) | 2009-06-02 | 2012-04-25 | 松下电器产业株式会社 | 下混装置、编码装置以及其方法 |
| UA109646C2 (uk) * | 2009-12-10 | 2015-09-25 | Терапевтичне застосування кон'югатів білка з полімером | |
| US20130225789A1 (en) * | 2012-02-29 | 2013-08-29 | Yi Sun | Polyethylene Glycol Having Hetero Multiple Functional Groups |
| US8993614B2 (en) | 2012-03-15 | 2015-03-31 | F. Hoffmann-La Roche Ag | Substituted pyrrolidine-2-carboxamides |
| KR101475630B1 (ko) * | 2013-05-31 | 2014-12-22 | 동국대학교 산학협력단 | 포도근 추출물 또는 이의 분획물을 유효성분으로 포함하는 c형 간염의 예방 또는 치료용 조성물 |
| WO2016013911A1 (ko) * | 2014-07-24 | 2016-01-28 | 에이비온 주식회사 | 페길화된 인터페론 -베타 변이체 |
| EP3782652A1 (en) | 2014-08-19 | 2021-02-24 | Biogen MA Inc. | Pegylation method |
| GB201419108D0 (en) | 2014-10-27 | 2014-12-10 | Glythera Ltd | Materials and methods relating to linkers for use in antibody drug conjugates |
| EA037151B1 (ru) | 2014-11-06 | 2021-02-11 | Фармаэссентия Корпорейшн | Способ лечения с использованием пегилированного интерферона |
| EP3421442B1 (en) * | 2017-06-28 | 2020-08-05 | Construction Research & Technology GmbH | Dispersant for inorganic particles |
| US11472894B2 (en) | 2018-07-23 | 2022-10-18 | Carnegie Mellon University | Enzyme-assisted ATRP procedures |
| US12053529B2 (en) | 2018-08-01 | 2024-08-06 | Carnegie Mellon University | Amino-reactive positively charged ATRP initiators that maintain their positive charge during synthesis of biomacro-initiators |
| CN109232898A (zh) * | 2018-08-02 | 2019-01-18 | 张玲 | 一种具有抗凝血功能的聚酰亚胺新材料的制备方法 |
| CN111534458B (zh) * | 2020-04-13 | 2022-01-14 | 浙江工业大学 | 无色杆菌tbc-1及其在降解1,3,6,8-四溴咔唑中的应用 |
| CN113716982B (zh) * | 2021-08-24 | 2022-05-06 | 重庆云瑞肥业有限公司 | 一种食品垃圾回收用发酵制肥装置 |
Family Cites Families (81)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3710795A (en) | 1970-09-29 | 1973-01-16 | Alza Corp | Drug-delivery device with stretched, rate-controlling membrane |
| US4179337A (en) | 1973-07-20 | 1979-12-18 | Davis Frank F | Non-immunogenic polypeptides |
| US4002531A (en) | 1976-01-22 | 1977-01-11 | Pierce Chemical Company | Modifying enzymes with polyethylene glycol and product produced thereby |
| DE3262575D1 (en) | 1981-12-23 | 1985-04-18 | Schering Corp | Stabilised interferon formulations and their preparation |
| WO1985003934A1 (fr) * | 1984-03-06 | 1985-09-12 | Takeda Chemical Industries, Ltd. | Proteine modifiee chimiquement et son procede de preparation |
| GB8334102D0 (en) | 1983-12-21 | 1984-02-01 | Searle & Co | Interferons with cysteine pattern |
| EP0154316B1 (en) | 1984-03-06 | 1989-09-13 | Takeda Chemical Industries, Ltd. | Chemically modified lymphokine and production thereof |
| DE3675588D1 (de) | 1985-06-19 | 1990-12-20 | Ajinomoto Kk | Haemoglobin, das an ein poly(alkenylenoxid) gebunden ist. |
| EP0229108B1 (en) | 1985-06-26 | 1990-12-27 | Cetus Corporation | Solubilization of proteins for pharmaceutical compositions using polymer conjugation |
| US4917888A (en) | 1985-06-26 | 1990-04-17 | Cetus Corporation | Solubilization of immunotoxins for pharmaceutical compositions using polymer conjugation |
| US4766106A (en) | 1985-06-26 | 1988-08-23 | Cetus Corporation | Solubilization of proteins for pharmaceutical compositions using polymer conjugation |
| JP2514950B2 (ja) | 1986-03-10 | 1996-07-10 | エフ・ホフマン―ラ ロシユ アーゲー | 化学修飾蛋白質，その製造法および中間体 |
| US4894226A (en) | 1986-11-14 | 1990-01-16 | Cetus Corporation | Solubilization of proteins for pharmaceutical compositions using polyproline conjugation |
| US5080891A (en) | 1987-08-03 | 1992-01-14 | Ddi Pharmaceuticals, Inc. | Conjugates of superoxide dismutase coupled to high molecular weight polyalkylene glycols |
| US5135919A (en) | 1988-01-19 | 1992-08-04 | Children's Medical Center Corporation | Method and a pharmaceutical composition for the inhibition of angiogenesis |
| US5116964A (en) | 1989-02-23 | 1992-05-26 | Genentech, Inc. | Hybrid immunoglobulins |
| US5286637A (en) * | 1989-08-07 | 1994-02-15 | Debiopharm, S.A. | Biologically active drug polymer derivatives and method for preparing same |
| US5252714A (en) * | 1990-11-28 | 1993-10-12 | The University Of Alabama In Huntsville | Preparation and use of polyethylene glycol propionaldehyde |
| US5595732A (en) | 1991-03-25 | 1997-01-21 | Hoffmann-La Roche Inc. | Polyethylene-protein conjugates |
| US5281698A (en) | 1991-07-23 | 1994-01-25 | Cetus Oncology Corporation | Preparation of an activated polymer ester for protein conjugation |
| WO1993012145A1 (en) | 1991-12-19 | 1993-06-24 | Baylor College Of Medicine | Pva or peg conjugates of peptides for epitope-specific immunosuppression |
| ZA933926B (en) | 1992-06-17 | 1994-01-03 | Amgen Inc | Polyoxymethylene-oxyethylene copolymers in conjuction with blomolecules |
| US5382657A (en) * | 1992-08-26 | 1995-01-17 | Hoffmann-La Roche Inc. | Peg-interferon conjugates |
| US5262564A (en) | 1992-10-30 | 1993-11-16 | Octamer, Inc. | Sulfinic acid adducts of organo nitroso compounds useful as retroviral inactivating agents anti-retroviral agents and anti-tumor agents |
| US5298410A (en) | 1993-02-25 | 1994-03-29 | Sterling Winthrop Inc. | Lyophilized formulation of polyethylene oxide modified proteins with increased shelf-life |
| US5359030A (en) | 1993-05-10 | 1994-10-25 | Protein Delivery, Inc. | Conjugation-stabilized polypeptide compositions, therapeutic delivery and diagnostic formulations comprising same, and method of making and using the same |
| US5681811A (en) | 1993-05-10 | 1997-10-28 | Protein Delivery, Inc. | Conjugation-stabilized therapeutic agent compositions, delivery and diagnostic formulations comprising same, and method of making and using the same |
| US5874075A (en) | 1993-10-06 | 1999-02-23 | Amgen Inc. | Stable protein: phospholipid compositions and methods |
| US5951974A (en) | 1993-11-10 | 1999-09-14 | Enzon, Inc. | Interferon polymer conjugates |
| HUT75533A (en) | 1993-11-10 | 1997-05-28 | Schering Corp | Improved interferon polymer conjugates |
| US5446090A (en) | 1993-11-12 | 1995-08-29 | Shearwater Polymers, Inc. | Isolatable, water soluble, and hydrolytically stable active sulfones of poly(ethylene glycol) and related polymers for modification of surfaces and molecules |
| US5639725A (en) | 1994-04-26 | 1997-06-17 | Children's Hospital Medical Center Corp. | Angiostatin protein |
| US5730990A (en) | 1994-06-24 | 1998-03-24 | Enzon, Inc. | Non-antigenic amine derived polymers and polymer conjugates |
| US5650234A (en) | 1994-09-09 | 1997-07-22 | Surface Engineering Technologies, Division Of Innerdyne, Inc. | Electrophilic polyethylene oxides for the modification of polysaccharides, polypeptides (proteins) and surfaces |
| US5824784A (en) | 1994-10-12 | 1998-10-20 | Amgen Inc. | N-terminally chemically modified protein compositions and methods |
| US5738846A (en) | 1994-11-10 | 1998-04-14 | Enzon, Inc. | Interferon polymer conjugates and process for preparing the same |
| WO1996017929A1 (en) | 1994-12-07 | 1996-06-13 | Novo Nordisk A/S | Polypeptide with reduced allergenicity |
| US5932462A (en) | 1995-01-10 | 1999-08-03 | Shearwater Polymers, Inc. | Multiarmed, monofunctional, polymer for coupling to molecules and surfaces |
| US5672662A (en) | 1995-07-07 | 1997-09-30 | Shearwater Polymers, Inc. | Poly(ethylene glycol) and related polymers monosubstituted with propionic or butanoic acids and functional derivatives thereof for biotechnical applications |
| SE9503380D0 (sv) * | 1995-09-29 | 1995-09-29 | Pharmacia Ab | Protein derivatives |
| AU730969B2 (en) * | 1995-10-19 | 2001-03-22 | University Of Washington | Discrete-length polyethylene glycols |
| US5702717A (en) | 1995-10-25 | 1997-12-30 | Macromed, Inc. | Thermosensitive biodegradable polymers based on poly(ether-ester)block copolymers |
| US5908621A (en) | 1995-11-02 | 1999-06-01 | Schering Corporation | Polyethylene glycol modified interferon therapy |
| US5747639A (en) | 1996-03-06 | 1998-05-05 | Amgen Boulder Inc. | Use of hydrophobic interaction chromatography to purify polyethylene glycols |
| AU5773798A (en) | 1997-01-29 | 1998-08-18 | Polymasc Pharmaceuticals Plc | Pegylation process |
| TR199902561T2 (xx) | 1997-03-05 | 2000-02-21 | Ribogene, Inc. | Hepatit C vir�s replikasyonunun se�ici bi�imde engelleyen maddelerin belirlenmesi i�in yeni tarama y�ntemleri |
| US5990237A (en) * | 1997-05-21 | 1999-11-23 | Shearwater Polymers, Inc. | Poly(ethylene glycol) aldehyde hydrates and related polymers and applications in modifying amines |
| US6448369B1 (en) | 1997-11-06 | 2002-09-10 | Shearwater Corporation | Heterobifunctional poly(ethylene glycol) derivatives and methods for their preparation |
| US7642323B2 (en) | 1997-11-06 | 2010-01-05 | Nektar Therapeutics | Heterobifunctional poly(ethylene glycol) derivatives and methods for their preparation |
| US6180095B1 (en) | 1997-12-17 | 2001-01-30 | Enzon, Inc. | Polymeric prodrugs of amino- and hydroxyl-containing bioactive agents |
| WO1999030727A1 (en) * | 1997-12-17 | 1999-06-24 | Enzon, Inc. | Polymeric prodrugs of amino- and hydroxyl-containing bioactive agents |
| US5985263A (en) | 1997-12-19 | 1999-11-16 | Enzon, Inc. | Substantially pure histidine-linked protein polymer conjugates |
| US5981709A (en) | 1997-12-19 | 1999-11-09 | Enzon, Inc. | α-interferon-polymer-conjugates having enhanced biological activity and methods of preparing the same |
| US5965119A (en) | 1997-12-30 | 1999-10-12 | Enzon, Inc. | Trialkyl-lock-facilitated polymeric prodrugs of amino-containing bioactive agents |
| JP4078032B2 (ja) * | 1998-03-12 | 2008-04-23 | ネクター セラピューティックス エイエル，コーポレイション | 近位の反応性基を持つポリ（エチレングリコール）誘導体 |
| SI1421956T1 (sl) | 1998-04-28 | 2007-10-31 | Serono Lab | Postopek za stopenjsko vezavo polietilenglikola (peg) na polipeptid |
| US6703381B1 (en) | 1998-08-14 | 2004-03-09 | Nobex Corporation | Methods for delivery therapeutic compounds across the blood-brain barrier |
| PL206536B1 (pl) | 1998-10-16 | 2010-08-31 | Biogen Idec Inc | Kompozycja, kompozycja farmaceutyczna glikozylowanego interferonu-beta-1a, zastosowanie kompozycji glikozylowanego interferonu-beta-1a, sposób in vitro przedłużania aktywności glikozylowanego interferonu-beta-1a |
| JP2003503367A (ja) * | 1999-06-11 | 2003-01-28 | シアウォーター・コーポレイション | キトサンとポリ（エチレングリコール）または関連ポリマーから得られるヒドロゲル |
| US7144574B2 (en) | 1999-08-27 | 2006-12-05 | Maxygen Aps | Interferon β variants and conjugates |
| KR20020034181A (ko) | 1999-08-27 | 2002-05-08 | 맥시겐 에이피에스 | 새로운 인터페론 베타-유사 분자 |
| US6531122B1 (en) * | 1999-08-27 | 2003-03-11 | Maxygen Aps | Interferon-β variants and conjugates |
| KR100653153B1 (ko) * | 1999-12-22 | 2006-12-01 | 넥타르 테라퓨틱스 에이엘, 코포레이션 | 수용성 중합체의 입체장애 유도체 |
| US6413507B1 (en) * | 1999-12-23 | 2002-07-02 | Shearwater Corporation | Hydrolytically degradable carbamate derivatives of poly (ethylene glycol) |
| US7052686B2 (en) * | 2000-09-29 | 2006-05-30 | Schering Corporation | Pegylated interleukin-10 |
| TW593427B (en) * | 2000-12-18 | 2004-06-21 | Nektar Therapeutics Al Corp | Synthesis of high molecular weight non-peptidic polymer derivatives |
| US7053150B2 (en) | 2000-12-18 | 2006-05-30 | Nektar Therapeutics Al, Corporation | Segmented polymers and their conjugates |
| EP1355936B1 (en) * | 2001-02-01 | 2007-06-27 | Biogen Idec MA Inc. | Polymer conjugates of neublastin and methods of using same |
| CA2469846A1 (en) | 2001-02-27 | 2002-09-26 | Maxygen Aps | New interferon beta-like molecules |
| US7009033B2 (en) | 2001-07-02 | 2006-03-07 | Polymer Source Inc. | Heterofunctional polyethylene glycol and polyethylene oxide, process for their manufacture |
| DK2939696T3 (en) * | 2001-10-18 | 2016-05-23 | Nektar Therapeutics | Polymer Conjugates of Opioid Antagonists |
| HUP0500997A2 (en) * | 2001-11-20 | 2007-11-28 | Pharmacia Corp | Chemically-modified human growth hormone conjugates |
| US6956135B2 (en) | 2001-12-11 | 2005-10-18 | Sun Bio, Inc. | Monofunctional polyethylene glycol aldehydes |
| US6916962B2 (en) | 2001-12-11 | 2005-07-12 | Sun Bio, Inc. | Monofunctional polyethylene glycol aldehydes |
| KR100488351B1 (ko) | 2001-12-11 | 2005-05-11 | 선바이오(주) | 신규한 폴리에틸렌글리콜-프로피온알데히드 유도체 |
| WO2003049699A2 (en) * | 2001-12-11 | 2003-06-19 | Sun Bio, Inc. | Novel monofunctional polyethylene glycol aldehydes |
| US7041855B2 (en) | 2001-12-11 | 2006-05-09 | Sun Bio, Inc. | Monofunctional polyethylene glycol aldehydes |
| GEP20064024B (en) * | 2002-01-18 | 2007-01-10 | Biogen Idec Inc | Polyalkylene glycol comprising a radical for conjugation of biologically active compound |
| BR0314172A (pt) | 2002-09-09 | 2005-07-26 | Nektar Therapeutics Al Corp | Polìmero solúvel em água, composição, forma de hidrato ou acetal, composto,composição, usos do composto e do conjugado, e, processo para preparar o conjugado |
| JP5207590B2 (ja) | 2002-12-26 | 2013-06-12 | マウンテン ビュー ファーマシューティカルズ，インコーポレイテッド | 増強された生物学的能力を有するインターフェロン−βのポリマー結合体 |
| US20110165122A1 (en) * | 2009-11-10 | 2011-07-07 | The Regents Of The University Of California | Method for targeted and sustained antiviral therapy |
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