JP2009510253A5 - - Google Patents
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- JP2009510253A5 JP2009510253A5 JP2008534615A JP2008534615A JP2009510253A5 JP 2009510253 A5 JP2009510253 A5 JP 2009510253A5 JP 2008534615 A JP2008534615 A JP 2008534615A JP 2008534615 A JP2008534615 A JP 2008534615A JP 2009510253 A5 JP2009510253 A5 JP 2009510253A5
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- JP
- Japan
- Prior art keywords
- group
- polymer
- salt
- substituted
- acid
- 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
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- 238000000034 method Methods 0.000 claims 33
- 229920000642 polymer Polymers 0.000 claims 14
- -1 amine salt Chemical class 0.000 claims 9
- 150000001412 amines Chemical group 0.000 claims 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
- 230000000890 antigenic effect Effects 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 4
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 229910052700 potassium Inorganic materials 0.000 claims 3
- 239000011591 potassium Substances 0.000 claims 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- PXACTUVBBMDKRW-UHFFFAOYSA-M 4-bromobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-M 0.000 claims 2
- SPXOTSHWBDUUMT-UHFFFAOYSA-M 4-nitrobenzenesulfonate Chemical compound [O-][N+](=O)C1=CC=C(S([O-])(=O)=O)C=C1 SPXOTSHWBDUUMT-UHFFFAOYSA-M 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- 239000002202 Polyethylene glycol Substances 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 claims 2
- 125000004405 heteroalkoxy group Chemical group 0.000 claims 2
- 229910003002 lithium salt Inorganic materials 0.000 claims 2
- 159000000002 lithium salts Chemical class 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 229920001223 polyethylene glycol Polymers 0.000 claims 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- IUIPEIAZMKNLSP-UHFFFAOYSA-N CC(C)(C)N(C(=O)O)C(=O)OC Chemical compound CC(C)(C)N(C(=O)O)C(=O)OC IUIPEIAZMKNLSP-UHFFFAOYSA-N 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 229960005215 dichloroacetic acid Drugs 0.000 claims 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 229920001451 polypropylene glycol Polymers 0.000 claims 1
- 229920013730 reactive polymer Polymers 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- XKXIQBVKMABYQJ-UHFFFAOYSA-M tert-butyl carbonate Chemical compound CC(C)(C)OC([O-])=O XKXIQBVKMABYQJ-UHFFFAOYSA-M 0.000 claims 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/242,656 US7601798B2 (en) | 2005-10-04 | 2005-10-04 | Methods of preparing polymers having terminal amine groups using protected amine salts |
| PCT/US2006/038562 WO2007044319A2 (en) | 2005-10-04 | 2006-09-29 | Methods of preparing polymers having terminal amine groups using protected amine salts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009510253A JP2009510253A (ja) | 2009-03-12 |
| JP2009510253A5 true JP2009510253A5 (https=) | 2009-11-05 |
Family
ID=37902700
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008534615A Pending JP2009510253A (ja) | 2005-10-04 | 2006-09-29 | 保護されたアミン塩を用いて、末端アミン基を有するポリマーを調製する方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US7601798B2 (https=) |
| EP (1) | EP1931313A4 (https=) |
| JP (1) | JP2009510253A (https=) |
| KR (1) | KR20080056267A (https=) |
| CN (1) | CN101321516A (https=) |
| AU (1) | AU2006302585A1 (https=) |
| CA (1) | CA2623542A1 (https=) |
| IL (1) | IL190415A0 (https=) |
| TW (1) | TW200718730A (https=) |
| WO (1) | WO2007044319A2 (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1913036B1 (en) * | 2005-07-20 | 2013-03-06 | Bridgestone Corporation | Amine functionalized polymers |
| US8133707B2 (en) * | 2006-01-17 | 2012-03-13 | Enzon Pharmaceuticals, Inc. | Methods of preparing activated polymers having alpha nitrogen groups |
| US20090156629A1 (en) * | 2006-06-09 | 2009-06-18 | Enzon Pharmaceuticals, Inc. | Indenoisoquinoline-releasable polymer conjugates |
| WO2008089185A2 (en) * | 2007-01-16 | 2008-07-24 | Enzon Pharmaceuticals, Inc. | Posaconazole polymer conjugates and methods of treatment using posaconazole and polymer conjugates thereof |
| HUE027603T2 (en) * | 2007-04-20 | 2016-10-28 | Sigma-Tau Rare Disease Ltd | Stable, recombinant adenosine deaminase |
| EP2147122B1 (en) * | 2007-04-20 | 2014-07-16 | Sigma-Tau Rare Diseases S.A. | Enzymatic anticancer therapy |
| TW200922624A (en) * | 2007-07-11 | 2009-06-01 | Enzon Pharmaceuticals Inc | Polymeric drug delivery system containing a multi-substituted aromatic moiety |
| 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 |
| CN114080232A (zh) | 2019-03-21 | 2022-02-22 | 科迪亚克生物科学公司 | 用于疫苗递送的细胞外囊泡 |
| WO2020191369A1 (en) | 2019-03-21 | 2020-09-24 | Codiak Biosciences, Inc. | Process for preparing extracellular vesicles |
| US20230366794A1 (en) | 2020-09-23 | 2023-11-16 | Codiak Biosciences, Inc. | Process for preparing extracellular vesicles |
| US20240241020A1 (en) | 2020-09-23 | 2024-07-18 | Lonza Sales Ag | Process for preparing extracellular vesicles |
| CN114409890A (zh) * | 2022-02-28 | 2022-04-29 | 中国科学院长春应用化学研究所 | 一种氨基功能化的聚乙二醇衍生物及其制备方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4179337A (en) | 1973-07-20 | 1979-12-18 | Davis Frank F | Non-immunogenic polypeptides |
| US5206344A (en) | 1985-06-26 | 1993-04-27 | Cetus Oncology Corporation | Interleukin-2 muteins and polymer conjugation thereof |
| US5643575A (en) * | 1993-10-27 | 1997-07-01 | Enzon, Inc. | Non-antigenic branched polymer conjugates |
| US6448369B1 (en) | 1997-11-06 | 2002-09-10 | Shearwater Corporation | Heterobifunctional poly(ethylene glycol) derivatives and methods for their preparation |
| US6824766B2 (en) * | 1998-04-17 | 2004-11-30 | Enzon, Inc. | Biodegradable high molecular weight polymeric linkers and their conjugates |
| KR20020022691A (ko) * | 1999-06-08 | 2002-03-27 | 와이즈먼 앤드루 | 아미노옥시기를 포함하는 원자가 플랫폼 분자 |
| US20030149307A1 (en) | 2001-10-24 | 2003-08-07 | Baxter International Inc. | Process for the preparation of polyethylene glycol bis amine |
| WO2004035657A1 (en) * | 2002-10-15 | 2004-04-29 | Baxter International Inc. | Process for the preparation of polyethylene glycol bis amine |
| US7332164B2 (en) * | 2003-03-21 | 2008-02-19 | Enzon Pharmaceuticals, Inc. | Heterobifunctional polymeric bioconjugates |
| KR100512483B1 (ko) | 2003-05-07 | 2005-09-05 | 선바이오(주) | 신규한 폴리에틸렌글리콜-말레이미드 유도체의 합성방법 |
| EP1688150A1 (en) * | 2005-02-08 | 2006-08-09 | Novo Nordisk A/S | Process for the preparation of alkoxyamine functionalised poly ethylene glycols |
-
2005
- 2005-10-04 US US11/242,656 patent/US7601798B2/en not_active Expired - Fee Related
-
2006
- 2006-09-29 WO PCT/US2006/038562 patent/WO2007044319A2/en not_active Ceased
- 2006-09-29 KR KR1020087010397A patent/KR20080056267A/ko not_active Withdrawn
- 2006-09-29 US US11/537,172 patent/US7569657B2/en not_active Expired - Fee Related
- 2006-09-29 JP JP2008534615A patent/JP2009510253A/ja active Pending
- 2006-09-29 AU AU2006302585A patent/AU2006302585A1/en not_active Abandoned
- 2006-09-29 CA CA002623542A patent/CA2623542A1/en not_active Abandoned
- 2006-09-29 EP EP06816091A patent/EP1931313A4/en not_active Withdrawn
- 2006-09-29 CN CNA2006800455829A patent/CN101321516A/zh active Pending
- 2006-10-02 TW TW095136519A patent/TW200718730A/zh unknown
-
2008
- 2008-03-25 IL IL190415A patent/IL190415A0/en unknown
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