JP2003511422A5 - - Google Patents
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- JP2003511422A5 JP2003511422A5 JP2001529753A JP2001529753A JP2003511422A5 JP 2003511422 A5 JP2003511422 A5 JP 2003511422A5 JP 2001529753 A JP2001529753 A JP 2001529753A JP 2001529753 A JP2001529753 A JP 2001529753A JP 2003511422 A5 JP2003511422 A5 JP 2003511422A5
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- JP
- Japan
- Prior art keywords
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- poly
- polymer
- alkyl
- substituted
- 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.)
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 68
- 238000000034 method Methods 0.000 description 56
- 125000000217 alkyl group Chemical group 0.000 description 54
- 229920000642 polymer Polymers 0.000 description 51
- 125000000524 functional group Chemical group 0.000 description 38
- 239000004305 biphenyl Substances 0.000 description 34
- 235000010290 biphenyl Nutrition 0.000 description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 34
- 239000000203 mixture Substances 0.000 description 19
- 229910052760 oxygen Inorganic materials 0.000 description 17
- 229910052717 sulfur Inorganic materials 0.000 description 17
- 229920001223 polyethylene glycol Polymers 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 12
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000006242 amine protecting group Chemical group 0.000 description 9
- 230000001588 bifunctional effect Effects 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 229920000547 conjugated polymer Polymers 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- 229920002521 macromolecule Polymers 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 230000000379 polymerizing effect Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 108090000765 processed proteins & peptides Proteins 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 3
- 229920001583 poly(oxyethylated polyols) Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- VBSYMODXUFYOLA-UHFFFAOYSA-N 5-phenylpenta-2,4-dienoyl chloride Chemical compound ClC(=O)C=CC=CC1=CC=CC=C1 VBSYMODXUFYOLA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical class OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 238000011210 chromatographic step Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 229920001584 poly(acrylomorpholines) Polymers 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- FEIQOMCWGDNMHM-KBXRYBNXSA-N (2e,4e)-5-phenylpenta-2,4-dienoic acid Chemical compound OC(=O)\C=C\C=C\C1=CC=CC=C1 FEIQOMCWGDNMHM-KBXRYBNXSA-N 0.000 description 1
- 108091034117 Oligonucleotide Proteins 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- -1 R1And R2Is H Chemical group 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- FEIQOMCWGDNMHM-UHFFFAOYSA-N cinnamylideneacetic acid Natural products OC(=O)C=CC=CC1=CC=CC=C1 FEIQOMCWGDNMHM-UHFFFAOYSA-N 0.000 description 1
- 230000001268 conjugating effect Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- YGGXZTQSGNFKPJ-UHFFFAOYSA-N methyl 2-naphthalen-1-ylacetate Chemical compound C1=CC=C2C(CC(=O)OC)=CC=CC2=C1 YGGXZTQSGNFKPJ-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 208000021596 pentasomy X Diseases 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US1999/023536 WO2001026692A1 (en) | 1999-10-08 | 1999-10-08 | Heterobifunctional poly(ethylene glycol) derivatives and methods for their preparation |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008033703A Division JP5150297B2 (ja) | 2008-02-14 | 2008-02-14 | ヘテロ二官能性ポリエチレングリコール誘導体およびその調製方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003511422A JP2003511422A (ja) | 2003-03-25 |
| JP2003511422A5 true JP2003511422A5 (enExample) | 2005-05-26 |
| JP4344110B2 JP4344110B2 (ja) | 2009-10-14 |
Family
ID=22273776
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001529753A Expired - Lifetime JP4344110B2 (ja) | 1999-10-08 | 1999-10-08 | ヘテロ二官能性ポリエチレングリコール誘導体およびその調製方法 |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP1455839B1 (enExample) |
| JP (1) | JP4344110B2 (enExample) |
| KR (1) | KR100499655B1 (enExample) |
| CN (1) | CN1284603C (enExample) |
| AU (1) | AU781336B2 (enExample) |
| BR (1) | BR9917517A (enExample) |
| CA (1) | CA2386762C (enExample) |
| CY (1) | CY1114128T1 (enExample) |
| DK (1) | DK1455839T3 (enExample) |
| ES (1) | ES2404685T3 (enExample) |
| HU (1) | HU228491B1 (enExample) |
| IL (2) | IL148890A0 (enExample) |
| MX (1) | MXPA02003540A (enExample) |
| NO (1) | NO331781B1 (enExample) |
| NZ (1) | NZ518143A (enExample) |
| PT (1) | PT1455839E (enExample) |
| WO (1) | WO2001026692A1 (enExample) |
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| KR100361933B1 (ko) | 1993-09-08 | 2003-02-14 | 라 졸라 파마슈티칼 컴파니 | 화학적으로정의된비중합성결합가플랫폼분자및그것의콘주게이트 |
| CA2414076A1 (en) | 2000-06-08 | 2001-12-13 | La Jolla Pharmaceutical Company | Multivalent platform molecules comprising high molecular weight polyethylene oxide |
| US6761824B2 (en) | 2000-08-17 | 2004-07-13 | Reeve Lorraine E | Process for the fractionation of polymers |
| US7118737B2 (en) | 2000-09-08 | 2006-10-10 | Amylin Pharmaceuticals, Inc. | Polymer-modified synthetic proteins |
| US7829074B2 (en) | 2001-10-18 | 2010-11-09 | Nektar Therapeutics | Hydroxypatite-targeting poly(ethylene glycol) and related polymers |
| 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 |
| US7550512B2 (en) | 2001-11-28 | 2009-06-23 | Keio University | Medical polymers and uses thereof |
| JP3493608B2 (ja) * | 2001-11-28 | 2004-02-03 | 学校法人慶應義塾 | 医用高分子及びその用途 |
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| US20040062748A1 (en) | 2002-09-30 | 2004-04-01 | Mountain View Pharmaceuticals, Inc. | Polymer conjugates with decreased antigenicity, methods of preparation and uses thereof |
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| AU2002353814A1 (en) * | 2002-10-15 | 2004-05-04 | Baxter Healthcare S.A. | Process for the preparation of polyethylene glycol bis amine |
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| US9040664B2 (en) | 2003-04-11 | 2015-05-26 | Antriabio, Inc. | Materials and methods for preparing protein-polymer conjugates |
| US8637650B2 (en) | 2003-11-05 | 2014-01-28 | Genovoxx Gmbh | Macromolecular nucleotide compounds and methods for using the same |
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| US7985783B2 (en) | 2006-09-21 | 2011-07-26 | The Regents Of The University Of California | Aldehyde tags, uses thereof in site-specific protein modification |
| BR112012002709A2 (pt) | 2009-08-05 | 2019-04-30 | Pieris Ag | formulações de liberação controlada de muteínas de lipocalina |
| WO2011050938A1 (de) | 2009-10-26 | 2011-05-05 | Genovoxx Gmbh | Konjugate von nukleotiden und methoden zu deren anwendung |
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| CN113583230A (zh) * | 2021-06-30 | 2021-11-02 | 苏州欣影生物医药技术有限公司 | 一种peg双胺选择性反应制备异双官能团的方法 |
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| CA2220339C (en) * | 1995-05-10 | 2009-10-13 | Kyowa Hakko Kogyo Co., Ltd. | Toxin conjugates having a spacer comprising polyalkylene glycol and peptide |
| 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 |
| US20020064546A1 (en) * | 1996-09-13 | 2002-05-30 | J. Milton Harris | Degradable poly(ethylene glycol) hydrogels with controlled half-life and precursors therefor |
| ES2211033T3 (es) * | 1998-01-07 | 2004-07-01 | Debio Recherche Pharmaceutique S.A. | Acrilatos de polietilenglicol heterobifuncionales degradables y geles y conjugados derivados de dichos acrilatos. |
| CA2323048C (en) * | 1998-03-12 | 2006-10-10 | Shearwater Polymers, Inc. | Poly(ethylene glycol) derivatives with proximal reactive groups |
-
1999
- 1999-10-08 MX MXPA02003540A patent/MXPA02003540A/es active IP Right Grant
- 1999-10-08 KR KR10-2002-7004507A patent/KR100499655B1/ko not_active Expired - Lifetime
- 1999-10-08 DK DK99951885.5T patent/DK1455839T3/da active
- 1999-10-08 AU AU64230/99A patent/AU781336B2/en not_active Expired
- 1999-10-08 WO PCT/US1999/023536 patent/WO2001026692A1/en not_active Ceased
- 1999-10-08 NZ NZ518143A patent/NZ518143A/en not_active IP Right Cessation
- 1999-10-08 CN CNB998169714A patent/CN1284603C/zh not_active Expired - Lifetime
- 1999-10-08 IL IL14889099A patent/IL148890A0/xx active IP Right Grant
- 1999-10-08 BR BR9917517-7A patent/BR9917517A/pt not_active Application Discontinuation
- 1999-10-08 JP JP2001529753A patent/JP4344110B2/ja not_active Expired - Lifetime
- 1999-10-08 EP EP99951885A patent/EP1455839B1/en not_active Expired - Lifetime
- 1999-10-08 PT PT99951885T patent/PT1455839E/pt unknown
- 1999-10-08 CA CA002386762A patent/CA2386762C/en not_active Expired - Lifetime
- 1999-10-08 HU HU0203149A patent/HU228491B1/hu unknown
- 1999-10-08 ES ES99951885T patent/ES2404685T3/es not_active Expired - Lifetime
-
2002
- 2002-03-26 IL IL148890A patent/IL148890A/en not_active IP Right Cessation
- 2002-04-02 NO NO20021555A patent/NO331781B1/no not_active IP Right Cessation
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2013
- 2013-04-23 CY CY20131100332T patent/CY1114128T1/el unknown
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