CN100475837C - Branched polyglycol-amino acid oligopeptide and active derivative and medicinal composition thereof - Google Patents
Branched polyglycol-amino acid oligopeptide and active derivative and medicinal composition thereof Download PDFInfo
- Publication number
- CN100475837C CN100475837C CNB2004100480166A CN200410048016A CN100475837C CN 100475837 C CN100475837 C CN 100475837C CN B2004100480166 A CNB2004100480166 A CN B2004100480166A CN 200410048016 A CN200410048016 A CN 200410048016A CN 100475837 C CN100475837 C CN 100475837C
- Authority
- CN
- China
- Prior art keywords
- polyoxyethylene glycol
- amino acid
- compound
- group
- oligopeptides
- 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.)
- Expired - Lifetime
Links
- 108010038807 Oligopeptides Proteins 0.000 title claims abstract description 58
- 102000015636 Oligopeptides Human genes 0.000 title claims abstract description 58
- 239000000203 mixture Substances 0.000 title claims description 13
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- 229930012538 Paclitaxel Natural products 0.000 claims abstract description 17
- 229960001592 paclitaxel Drugs 0.000 claims abstract description 17
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims abstract description 15
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 claims abstract description 12
- -1 polyoxyethylene Polymers 0.000 claims description 134
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 118
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 92
- 229940024606 amino acid Drugs 0.000 claims description 62
- 229940079593 drug Drugs 0.000 claims description 52
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 45
- 239000000126 substance Substances 0.000 claims description 42
- 239000000243 solution Substances 0.000 claims description 39
- 235000001014 amino acid Nutrition 0.000 claims description 36
- 150000001413 amino acids Chemical class 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 36
- 229960002989 glutamic acid Drugs 0.000 claims description 31
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 30
- 239000004471 Glycine Substances 0.000 claims description 27
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- 239000000499 gel Substances 0.000 claims description 23
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 20
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 18
- 102000004860 Dipeptidases Human genes 0.000 claims description 16
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 7
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- VRPJIFMKZZEXLR-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid Chemical compound CC(C)(C)OC(=O)NCC(O)=O VRPJIFMKZZEXLR-UHFFFAOYSA-N 0.000 description 1
- KWVPFECTOKLOBL-KTKRTIGZSA-N 2-[(z)-octadec-9-enoxy]ethanol Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCO KWVPFECTOKLOBL-KTKRTIGZSA-N 0.000 description 1
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- XEHFSYYAGCUKEN-UHFFFAOYSA-N Dihydroscopoletin Natural products C1CC(=O)OC2=C1C=C(OC)C(O)=C2 XEHFSYYAGCUKEN-UHFFFAOYSA-N 0.000 description 1
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- 229910021529 ammonia Inorganic materials 0.000 description 1
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- 150000004676 glycans Chemical class 0.000 description 1
- 125000003827 glycol group Chemical group 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6903—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being semi-solid, e.g. an ointment, a gel, a hydrogel or a solidifying gel
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/59—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes
- A61K47/60—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes the organic macromolecular compound being a polyoxyalkylene oligomer, polymer or dendrimer, e.g. PEG, PPG, PEO or polyglycerol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P41/00—Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
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- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Medicinal Preparation (AREA)
Abstract
Description
Claims (27)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
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CNB2004100480166A CN100475837C (en) | 2004-06-11 | 2004-06-11 | Branched polyglycol-amino acid oligopeptide and active derivative and medicinal composition thereof |
PCT/CN2005/000834 WO2005121181A1 (en) | 2004-06-11 | 2005-06-10 | Multi-drop tree branching polyethylene glycol-oligopeptides and active derivates and pharmaceutical compounds there of |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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CNB2004100480166A CN100475837C (en) | 2004-06-11 | 2004-06-11 | Branched polyglycol-amino acid oligopeptide and active derivative and medicinal composition thereof |
Publications (2)
Publication Number | Publication Date |
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CN1706865A CN1706865A (en) | 2005-12-14 |
CN100475837C true CN100475837C (en) | 2009-04-08 |
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CNB2004100480166A Expired - Lifetime CN100475837C (en) | 2004-06-11 | 2004-06-11 | Branched polyglycol-amino acid oligopeptide and active derivative and medicinal composition thereof |
Country Status (2)
Country | Link |
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CN (1) | CN100475837C (en) |
WO (1) | WO2005121181A1 (en) |
Families Citing this family (36)
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US9492400B2 (en) | 2004-11-04 | 2016-11-15 | Massachusetts Institute Of Technology | Coated controlled release polymer particles as efficient oral delivery vehicles for biopharmaceuticals |
ATE432955T1 (en) | 2005-12-05 | 2009-06-15 | Nitto Denko Corp | POLYGLUTAMAT-AMINO ACID CONJUGATES AND METHODS |
AU2006321912B2 (en) * | 2005-12-06 | 2012-07-12 | Covidien Lp | Carbodiimide crosslinking of functionalized polethylene glycols |
WO2007070682A2 (en) | 2005-12-15 | 2007-06-21 | Massachusetts Institute Of Technology | System for screening particles |
US8367113B2 (en) | 2006-05-15 | 2013-02-05 | Massachusetts Institute Of Technology | Polymers for functional particles |
WO2007150030A2 (en) | 2006-06-23 | 2007-12-27 | Massachusetts Institute Of Technology | Microfluidic synthesis of organic nanoparticles |
CN101168594B (en) * | 2006-10-24 | 2011-07-27 | 北京键凯科技有限公司 | Polyglycol active derivative with oligopeptide as framework, preparation method thereof and conjugate of with pharmaceutical molecule |
US9217129B2 (en) | 2007-02-09 | 2015-12-22 | Massachusetts Institute Of Technology | Oscillating cell culture bioreactor |
WO2008124632A1 (en) | 2007-04-04 | 2008-10-16 | Massachusetts Institute Of Technology | Amphiphilic compound assisted nanoparticles for targeted delivery |
MX350501B (en) | 2007-10-12 | 2017-09-07 | Massachusetts Inst Technology | Vaccine nanotechnology. |
US8277812B2 (en) | 2008-10-12 | 2012-10-02 | Massachusetts Institute Of Technology | Immunonanotherapeutics that provide IgG humoral response without T-cell antigen |
US8591905B2 (en) | 2008-10-12 | 2013-11-26 | The Brigham And Women's Hospital, Inc. | Nicotine immunonanotherapeutics |
US8343497B2 (en) | 2008-10-12 | 2013-01-01 | The Brigham And Women's Hospital, Inc. | Targeting of antigen presenting cells with immunonanotherapeutics |
US8343498B2 (en) | 2008-10-12 | 2013-01-01 | Massachusetts Institute Of Technology | Adjuvant incorporation in immunonanotherapeutics |
ITRM20080551A1 (en) * | 2008-10-15 | 2010-04-16 | Univ Catania | AMPHIFYL DERIVATIVES OF POLYOSSIETHYLENE GLYCOL (PEG), PREPARATION PROCEDURE AND THEIR USE IN THE PREPARATION OF PHARMACEUTICAL SYSTEMS. |
CN101724144A (en) * | 2008-11-03 | 2010-06-09 | 北京键凯科技有限公司 | Novel multi-arm polyethylene glycol, preparation method and application thereof |
CN102108119A (en) * | 2009-12-25 | 2011-06-29 | 天津键凯科技有限公司 | Multi-arm polyethylene glycol derivative, combination thereof with medicine, and gel |
CN102266566B (en) * | 2010-06-03 | 2013-06-12 | 中国人民解放军军事医学科学院毒物药物研究所 | Magnetic compound, and preparation method and purpose thereof |
US20140228279A1 (en) * | 2011-10-03 | 2014-08-14 | Nanyang Technological University | Cationic peptidopolysaccharides with excellent broad- spectrum antimicrobial activities and high selectivity |
CN103083680B (en) * | 2011-11-07 | 2014-12-24 | 北京键凯科技有限公司 | Polyethylene glycol (PEG)-amino acid oligopeptide-irinotecan combo and its medicinal composition |
WO2014114262A1 (en) * | 2013-01-28 | 2014-07-31 | 天津键凯科技有限公司 | Water soluble polymer-amino acid oligopeptide-medicine combination, preparation method therefore, and use thereof |
US9700633B2 (en) | 2013-01-28 | 2017-07-11 | Jenkem Technology Co., Ltd., Tianjin Branch | Conjugates of water soluble polymer-amino acid oligopeptide-drug, preparation method and use thereof |
CN104448295B (en) * | 2013-12-02 | 2018-01-23 | 北京键凯科技股份有限公司 | The rapamycin derivative of polyethylene glycol multijaw oligopeptides bonding |
CN105017522A (en) * | 2015-07-20 | 2015-11-04 | 湖南华腾制药有限公司 | Polyethylene glycol-modified unnatural amino acid preparation method |
CN106928454B (en) * | 2015-12-30 | 2021-07-20 | 北京大学 | Polyamino acid compound |
CN107469089B (en) * | 2016-06-07 | 2022-01-07 | 北京键凯科技股份有限公司 | PEG connector and aglucon drug conjugate |
CN108264538B (en) * | 2017-01-04 | 2023-08-29 | 辽宁药联制药有限公司 | Solid Phase Synthesis Method of Aspartic Acid Condensate |
CN108659227B (en) * | 2017-03-30 | 2020-11-06 | 北京键凯科技股份有限公司 | Preparation method of Y-type branched hydrophilic polymer carboxylic acid derivative |
WO2018177055A1 (en) * | 2017-03-30 | 2018-10-04 | 北京键凯科技股份有限公司 | Method for preparing y-branched hydrophilic polymer carboxylic acid derivative |
CN108003342A (en) * | 2018-02-02 | 2018-05-08 | 中国科学院长春应用化学研究所 | Polyaminoacid, its preparation method and load medicinal gel |
EP3778705A4 (en) * | 2018-03-29 | 2022-01-05 | NOF Corporation | Degradable polyethylene glycol derivative |
CN109897179B (en) * | 2019-04-02 | 2021-08-17 | 中国科学院长春应用化学研究所 | Multi-arm polyethylene glycol-poly (L-glutamate) block copolymer, and preparation method and application thereof |
WO2021060439A1 (en) * | 2019-09-26 | 2021-04-01 | 日油株式会社 | Heterobifunctional monodispersed polyethylene glycol having peptide linker |
CN112251484B (en) * | 2020-10-26 | 2022-05-24 | 江南大学 | Method for preparing glycine oligopeptide-polyethylene glycol copolymer under catalysis of lipase |
CN115975182A (en) * | 2023-01-10 | 2023-04-18 | 深圳市乐土生物医药有限公司 | Amino acid copolymer and application thereof |
CN116178733B (en) * | 2023-03-03 | 2023-08-01 | 浙江博美生物技术有限公司 | Branched monodisperse PEG derivative based on trifunctional amino acid, preparation method and application |
Citations (1)
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CN1381512A (en) * | 2002-01-15 | 2002-11-27 | 泛亚生物技术有限公司 | Multi-arm fork type functional polyethylene glycol preparation method and its application in medicine |
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EP1251530A3 (en) * | 2001-04-16 | 2004-12-29 | Shipley Company LLC | Dielectric laminate for a capacitor |
CN100475269C (en) * | 2002-03-05 | 2009-04-08 | 北京键凯科技有限公司 | Binding agent of hydrophilic polymer-glutamic acid oligopeptide and medicinal molecular, composition containing said binding agent and use thereof |
CN1254496C (en) * | 2002-05-30 | 2006-05-03 | 中国科学院过程工程研究所 | Method of preparing branched polyethylene glycol |
-
2004
- 2004-06-11 CN CNB2004100480166A patent/CN100475837C/en not_active Expired - Lifetime
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2005
- 2005-06-10 WO PCT/CN2005/000834 patent/WO2005121181A1/en active Application Filing
Patent Citations (1)
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CN1381512A (en) * | 2002-01-15 | 2002-11-27 | 泛亚生物技术有限公司 | Multi-arm fork type functional polyethylene glycol preparation method and its application in medicine |
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CN1706865A (en) | 2005-12-14 |
WO2005121181A1 (en) | 2005-12-22 |
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Effective date of registration: 20161223 Address after: 124000 Liaoning Province, Panjin city Shuangtaizi District Park Street, South and West No. 2111020090140248 Patentee after: Liaoning Kai Kai Technology Co.,Ltd. Address before: 100085 Haidian District, Beijing on the road to information on the international science and Technology Park, building C, floor four, layer Patentee before: JENKEM TECHNOLOGY Co.,Ltd. (BEIJING) |
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Granted publication date: 20090408 |