RU2005105568A - Производные альдегида полиэтиленгликоля - Google Patents
Производные альдегида полиэтиленгликоля Download PDFInfo
- Publication number
- RU2005105568A RU2005105568A RU2005105568/04A RU2005105568A RU2005105568A RU 2005105568 A RU2005105568 A RU 2005105568A RU 2005105568/04 A RU2005105568/04 A RU 2005105568/04A RU 2005105568 A RU2005105568 A RU 2005105568A RU 2005105568 A RU2005105568 A RU 2005105568A
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- RU
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- Prior art keywords
- formula
- compound
- polyethylene glycol
- hydrolysis
- blocking group
- Prior art date
Links
- 239000002202 Polyethylene glycol Substances 0.000 title claims 7
- 229920001223 polyethylene glycol Polymers 0.000 title claims 7
- -1 GLYCOL DERIVATIVES ALDEHYDE Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 32
- WGCNASOHLSPBMP-UHFFFAOYSA-N Glycolaldehyde Chemical compound OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 10
- 238000000034 method Methods 0.000 claims 9
- 230000000903 blocking effect Effects 0.000 claims 6
- 230000007062 hydrolysis Effects 0.000 claims 5
- 238000006460 hydrolysis reaction Methods 0.000 claims 5
- 125000003275 alpha amino acid group Chemical group 0.000 claims 3
- 230000015572 biosynthetic process Effects 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims 1
- HAXFWIACAGNFHA-UHFFFAOYSA-N aldrithiol Chemical compound C=1C=CC=NC=1SSC1=CC=CC=N1 HAXFWIACAGNFHA-UHFFFAOYSA-N 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 239000010802 sludge Substances 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- 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
- C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
- C08G65/324—Polymers modified by chemical after-treatment with inorganic 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
- C08G65/26—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
- C08G65/2615—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 the other compounds containing carboxylic acid, ester or anhydride groups
-
- 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
- C08G65/2618—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 nitrogen
- C08G65/2621—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 nitrogen containing amine groups
- C08G65/2624—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 nitrogen containing amine groups containing aliphatic amine groups
-
- 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
-
- 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
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Polyethers (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Hydrogenated Pyridines (AREA)
- Saccharide Compounds (AREA)
Claims (22)
1. Соединение формулы (I):
R1-(CH2CH2O)n-CH2CH2-X-Y-NH-(CH2)p-CHO (I)
где
R1 означает блокирующую группу,
X означает О или NH,
Y выбирают из группы, включающей
Z означает боковую цепь аминокислоты,
m равно от 1 до 17,
n равно от 10 до 10000, а
р равно от 1 до 3.
2. Соединение по п.1, где R1 выбирают из группы, включающей галоген, эпоксид, имид малеиновой кислоты, орто-пиридилдисульфид, тозилат, изоцианат, гидразингидрат, цианургалогенид, N-сукцинимидилокси, сульфо-N-сукцинимидилокси, 1-бензотриазолилокси, 1-имидазолилокси, пара-нитрофенилокси, и
3. Соединение по п.1 формулы (III):
4. Соединение по п.1 формулы (IV):
5. Соединение по п.1 формулы (V):
6. Соединение по п.1 формулы (VI):
7. Соединение формулы (II):
где R1 означает блокирующую группу,
m равно от 1 до 17,
n равно от 10 до 10000, а
р равно от 1 до 3.
8. Соединение по п.7, где р равно 3.
9. Соединение по п.7, где р равно 3, R1 означает метокси, m равно 1, а n равно от 100 до 750.
10. Соединение формулы (VIII):
где m равно от 1 до 17,
n равно от 10 до 10000, а
р равно от 1 до 3.
11. Соединение формулы (IX):
R1-(СН2-СН2-O)n-СН2-СН2-Х-Y-NH-(СН2)р-СН-(ОСН2-СН3)2 (IX)
где
R1 означает блокирующую группу,
Х означает О или NH,
Y выбирают из группы, включающей
Z означает боковую цепь аминокислоты,
m равно от 1 до 17,
n равно от 10 до 10000, а
р равно от 1 до 3.
12. Соединение формулы (X):
где R1 означает блокирующую группу,
m равно от 1 до 17,
n равно от 10 до 10000, а
р равно от 1 до 3.
13. Соединение формулы (XI):
m равно от 1 до 17,
n равно от 10 до 10000, а
р равно от 1 до 3.
14. Способ получения альдегида полиэтиленгликоля, включающий гидролиз соединения формулы (IX):
R1-(CH2-CH2-O)n-CH2CH2-X-Y-NH-(CH2)p-CH-(OCH2-CH3)2 (IX)
с образованием альдегида полиэтиленгликоля формулы (I):
R1-(CH2CH2O)n-CH2CH2-X-Y-NH-(CH2)p-CHO (I)
где R1 означает блокирующую группу,
Х означает О или NH,
Y выбирают из группы, включающей
Z означает боковую цепь аминокислоты,
m равно от 1 до 17,
n равно от 10 до 10000, а
р равно от 1 до 3.
15. Способ получения альдегида полиэтиленгликоля, включающий гидролиз соединения формулы (X):
с образованием альдегида полиэтиленгликоля формулы (II):
где R1 означает блокирующую группу,
m равно от 1 до 17,
n равно от 10 до 10000, а
р равно от 1 до 3.
16. Способ по п.15, где соединение формулы (X) получают при взаимодействии соединения формулы (XII)
R1-(CH2-CH2-O)n-CH2CH2-O-(CH2)m-COOH (XII)
с соединением формулы (XIII)
Н2N-(СН2)р-СН-(ОСН2-СН3)2 (XIII).
17. Способ по п.16, где соединение формулы (XII) получают при гидролизе соединения формулы (XIV)
R1-O-(CH2-CH2-O)n-CH2CH2-O-(CH2)m-COOR3 (XIV)
где R3 означает разветвленный или неразветвленный С1-С4алкил.
18. Способ по п.17, где соединение формулы (XIV) получают при взаимодействии соединения формулы (XV)
R1-(CH2-CH2-O)n-CH2CH2-OH (XV)
с соединением формулы (XVI)
R2-(СН2)m-COORз (XVI)
где R2 означает галоген.
19. Способ получения альдегида полиэтиленгликоля, включающий гидролиз соединения формулы (XVII)
с образованием полиэтиленгликоля формулы (VIII)
где m равно от 1 до 17,
n равно от 10 до 10000, а
р равно от 1 до 3.
20. Способ по п.19, где соединение формулы (VIII) получают при взаимодействии соединения формулы (XVIII):
НООС-(СН2)m-O-СН2СН2-(СН2-СН2-O)n-СН2СН2-O-(СН2)m-СООН (XVIII)
с соединением формулы (XIX):
Н2N-(СН2)р-СН-(ОСН2-СН3)2 (XIX).
21. Способ по п.20, где соединение формулы (XVIII) получают при гидролизе соединения формулы (XX):
R3ООС-(СН2)m-СН2СН2-O-(СН2-СН2-O)n-СН2СН2-O-(СН2)m-COOR3(ХХ)
где R3 означает разветвленный ил неразветвленный С1-С4алкил.
22. Способ по п.21, где соединение формулы (XX) получают при взаимодействии соединения формулы (XXI)
НО-СН2СН2-(СН2-СН2-O)n-СН2СН2-ОН (XXI)
с соединением формулы (XVI):
R2-(CH2)m-COOR3 (XVI)
где R2 означает галоген.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39819602P | 2002-07-24 | 2002-07-24 | |
| US60/398,196 | 2002-07-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2005105568A true RU2005105568A (ru) | 2005-10-20 |
| RU2288212C2 RU2288212C2 (ru) | 2006-11-27 |
Family
ID=31495721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2005105568/04A RU2288212C2 (ru) | 2002-07-24 | 2003-07-16 | Производные альдегида полиэтиленгликоля |
Country Status (28)
| Country | Link |
|---|---|
| US (2) | US7273909B2 (ru) |
| EP (1) | EP1539857B1 (ru) |
| JP (1) | JP4071238B2 (ru) |
| KR (1) | KR100615753B1 (ru) |
| CN (1) | CN1671769B (ru) |
| AR (1) | AR040607A1 (ru) |
| AT (1) | ATE344289T1 (ru) |
| AU (1) | AU2003250971B2 (ru) |
| BR (1) | BR0312863B1 (ru) |
| CA (1) | CA2493221C (ru) |
| DE (1) | DE60309482T2 (ru) |
| DK (1) | DK1539857T3 (ru) |
| ES (1) | ES2274277T3 (ru) |
| GT (1) | GT200300154A (ru) |
| HR (1) | HRP20050026A2 (ru) |
| IL (1) | IL165920A0 (ru) |
| JO (1) | JO2400B1 (ru) |
| MX (1) | MXPA05000799A (ru) |
| NO (1) | NO336974B1 (ru) |
| PA (1) | PA8577601A1 (ru) |
| PE (1) | PE20040703A1 (ru) |
| PL (1) | PL214871B1 (ru) |
| PT (1) | PT1539857E (ru) |
| RU (1) | RU2288212C2 (ru) |
| TW (1) | TWI276647B (ru) |
| UY (1) | UY27902A1 (ru) |
| WO (1) | WO2004013205A1 (ru) |
| ZA (1) | ZA200410296B (ru) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2497980C (en) | 2002-09-09 | 2011-06-21 | Nektar Therapeutics Al, Corporation | Method for preparing water-soluble polymer derivatives bearing a terminal carboxylic acid |
| AP2005003249A0 (en) | 2002-09-09 | 2005-03-31 | Nektar Therapeutics Al Corp | Water-soluble polymer alkanals. |
| US20050214250A1 (en) * | 2003-11-06 | 2005-09-29 | Harris J M | Method of preparing carboxylic acid functionalized polymers |
| US7989554B2 (en) * | 2006-01-10 | 2011-08-02 | Enzon Pharmaceuticals, Inc. | Reacting polyalkylene oxide with base, tertiary alkyl haloacetate, then acid to prepare polyalkylene oxide carboxylic acid |
| WO2008051383A2 (en) * | 2006-10-19 | 2008-05-02 | Amgen Inc. | Use of alcohol co-solvents to improve pegylation reaction yields |
| WO2008048079A1 (en) * | 2006-10-20 | 2008-04-24 | Postech Academy-Industry Foundation | Long acting formulation of biopharmaceutical |
| US8247493B2 (en) * | 2007-10-22 | 2012-08-21 | Postech Academy-Industry Foundation | Long acting formulation of biopharmaceutical |
| KR100967833B1 (ko) * | 2008-05-20 | 2010-07-05 | 아이디비켐(주) | 고순도의 폴리에틸렌글리콜 알데하이드 유도체의 제조방법 |
| EP2331139B1 (en) * | 2008-09-11 | 2019-04-17 | Nektar Therapeutics | Polymeric alpha-hydroxy aldehyde and ketone reagents and conjugation method |
| RU2439091C1 (ru) * | 2010-10-06 | 2012-01-10 | Общество С Ограниченной Ответственностью "Форт" (Ооо "Форт") | Производные полиэтиленгликоля, содержащие ароматическую диазогруппу |
| EP2592103A1 (en) | 2011-11-08 | 2013-05-15 | Adriacell S.p.A. | Polymer aldehyde derivatives |
| CA2916202C (en) * | 2013-06-24 | 2019-07-02 | Hanwha Chemical Corporation | Antibody-drug conjugate having improved stability and use thereof |
| TWI689310B (zh) * | 2014-07-11 | 2020-04-01 | 巨生生醫股份有限公司 | 治療鐵缺乏症之方法 |
| KR102247701B1 (ko) * | 2016-02-26 | 2021-05-03 | 한미정밀화학주식회사 | 폴리에틸렌글리콜 디알데히드 유도체의 제조방법 |
| CN109071419A (zh) | 2016-03-07 | 2018-12-21 | 韩美药品株式会社 | 聚乙二醇衍生物及其用途 |
| US11357861B2 (en) | 2017-09-29 | 2022-06-14 | Hanmi Pharm. Co., Ltd | Protein complex comprising non-peptidyl polymer-coupled fatty acid derivative compound as linker and preparation method therefor |
| WO2023111213A1 (en) | 2021-12-16 | 2023-06-22 | Rdp Pharma Ag | Cell penetrating polypeptides (cpps) and their use in human therapy |
| EP4480497A1 (en) | 2023-06-21 | 2024-12-25 | RDP Pharma AG | Bio-conjugates for oncology |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5252714A (en) * | 1990-11-28 | 1993-10-12 | The University Of Alabama In Huntsville | Preparation and use of polyethylene glycol propionaldehyde |
| US5770577A (en) * | 1994-11-14 | 1998-06-23 | Amgen Inc. | BDNF and NT-3 polypeptides selectively linked to polyethylene glycol |
| CH690143A5 (de) | 1995-01-27 | 2000-05-15 | Rieter Automotive Int Ag | Lambda/4-Schallabsorber. |
| 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 |
| US5990237A (en) | 1997-05-21 | 1999-11-23 | Shearwater Polymers, Inc. | Poly(ethylene glycol) aldehyde hydrates and related polymers and applications in modifying amines |
| AU1325400A (en) * | 1998-10-26 | 2000-05-15 | University Of Utah Research Foundation | Method for preparation of polyethylene glycol aldehyde derivatives |
| JO2291B1 (en) | 1999-07-02 | 2005-09-12 | اف . هوفمان لاروش ايه جي | Erythropoietin derivatives |
| KR100488351B1 (ko) | 2001-12-11 | 2005-05-11 | 선바이오(주) | 신규한 폴리에틸렌글리콜-프로피온알데히드 유도체 |
| EP1507755A4 (en) | 2001-12-11 | 2006-05-17 | Sun Bio Inc | NOVEL MONOFUNCTIONAL POLYETHYLENE GLYCOL ALDEHYDES |
-
2003
- 2003-07-16 KR KR1020057001223A patent/KR100615753B1/ko not_active Expired - Fee Related
- 2003-07-16 AU AU2003250971A patent/AU2003250971B2/en not_active Ceased
- 2003-07-16 PT PT03766194T patent/PT1539857E/pt unknown
- 2003-07-16 MX MXPA05000799A patent/MXPA05000799A/es active IP Right Grant
- 2003-07-16 EP EP03766194A patent/EP1539857B1/en not_active Expired - Lifetime
- 2003-07-16 WO PCT/EP2003/007734 patent/WO2004013205A1/en not_active Ceased
- 2003-07-16 DK DK03766194T patent/DK1539857T3/da active
- 2003-07-16 HR HR20050026A patent/HRP20050026A2/hr not_active Application Discontinuation
- 2003-07-16 BR BRPI0312863-6A patent/BR0312863B1/pt not_active IP Right Cessation
- 2003-07-16 JP JP2004525223A patent/JP4071238B2/ja not_active Expired - Fee Related
- 2003-07-16 ES ES03766194T patent/ES2274277T3/es not_active Expired - Lifetime
- 2003-07-16 CA CA002493221A patent/CA2493221C/en not_active Expired - Fee Related
- 2003-07-16 AT AT03766194T patent/ATE344289T1/de active
- 2003-07-16 PL PL375266A patent/PL214871B1/pl unknown
- 2003-07-16 DE DE60309482T patent/DE60309482T2/de not_active Expired - Lifetime
- 2003-07-16 RU RU2005105568/04A patent/RU2288212C2/ru not_active IP Right Cessation
- 2003-07-16 CN CN038176491A patent/CN1671769B/zh not_active Expired - Fee Related
- 2003-07-20 JO JO200383A patent/JO2400B1/en active
- 2003-07-21 AR AR20030102609A patent/AR040607A1/es not_active Application Discontinuation
- 2003-07-21 TW TW092119827A patent/TWI276647B/zh not_active IP Right Cessation
- 2003-07-21 US US10/623,978 patent/US7273909B2/en not_active Expired - Fee Related
- 2003-07-21 PE PE2003000727A patent/PE20040703A1/es not_active Application Discontinuation
- 2003-07-21 PA PA20038577601A patent/PA8577601A1/es unknown
- 2003-07-22 UY UY27902A patent/UY27902A1/es not_active Application Discontinuation
- 2003-07-23 GT GT200300154A patent/GT200300154A/es unknown
-
2004
- 2004-12-21 ZA ZA200410296A patent/ZA200410296B/en unknown
- 2004-12-22 IL IL16592004A patent/IL165920A0/xx not_active IP Right Cessation
-
2005
- 2005-01-03 NO NO20050019A patent/NO336974B1/no not_active IP Right Cessation
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2007
- 2007-03-14 US US11/724,009 patent/US20070167606A1/en not_active Abandoned
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