WO2001049696A1 - N,o-amidomalonate platinum complexes - Google Patents

N,o-amidomalonate platinum complexes Download PDF

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Publication number
WO2001049696A1
WO2001049696A1 PCT/US2001/000284 US0100284W WO0149696A1 WO 2001049696 A1 WO2001049696 A1 WO 2001049696A1 US 0100284 W US0100284 W US 0100284W WO 0149696 A1 WO0149696 A1 WO 0149696A1
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WO
WIPO (PCT)
Prior art keywords
platinum
polymer
chelate
composition
amidomalonate
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.)
Ceased
Application number
PCT/US2001/000284
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English (en)
French (fr)
Inventor
Donald R. Stewart
John R. Rice
John V. St. John
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Abeona Therapeutics Inc
Original Assignee
Access Pharmaceuticals Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Access Pharmaceuticals Inc filed Critical Access Pharmaceuticals Inc
Priority to AU27621/01A priority Critical patent/AU2762101A/en
Priority to EP01901752A priority patent/EP1254145A1/en
Priority to CA2396702A priority patent/CA2396702C/en
Priority to JP2001550236A priority patent/JP5025062B2/ja
Publication of WO2001049696A1 publication Critical patent/WO2001049696A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0086Platinum compounds
    • C07F15/0093Platinum compounds without a metal-carbon linkage
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50Medicinal 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
    • A61K47/51Medicinal 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
    • A61K47/56Medicinal 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
    • A61K47/58Medicinal 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 by reactions only involving carbon-to-carbon unsaturated bonds, e.g. poly[meth]acrylate, polyacrylamide, polystyrene, polyvinylpyrrolidone, polyvinylalcohol or polystyrene sulfonic acid resin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • A61P35/04Antineoplastic agents specific for metastasis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Definitions

  • platinum complexes might be achieved by targeting of platinum complexes to tumor cells.
  • Conventional small molecule platinum complexes such as cisplatin, carboplatin, and oxaliplatin are not specifically targeted to tumor cells, and following intravenous administration, they can diffuse into normal cells as readily as they diffuse into tumor cells. Also, their doses are rapidly cleared. At 3 hour post injection 90% of plasma platinum from cisplatin is irreversibly protein bound (Physican's. Desk Ref. 1997). For cisplatin and carboplatin 25% and 65%o, respectively, of the dose is renally secreted within 12 h (DeVita et al. 1993). Improvements in therapeutic index might be possible if platinum complexes are more readily delivered to tumors and/or more readily taken up by tumor cells than normal cells.
  • 195 Pt has a practical sensitivity limit of ⁇ bout > 10 mM platinum.
  • Examples of the chemical shifts for cis-diammine platinum(II) complexes include: -2168 ppm for cisplatin, -1723 for carboplatin, -1584 ppm for diaqua, -1841 ppm for monoaqua-monochloro, -1732 ppm for O,O-aminomalonate, -2156 ppm for N,O- aminomalonate, and -2020 ppm forN,O-chelate of N-acetylglycine (Appleton 1990; Gibson 1990; Appleton 2000). Corresponding DACH-Pt complexes appear further upfield.
  • Figure 3B shows the structure of an N,O-Pt chelate of amidomalonate-cis- diamineplatinum(II).
  • Y ONp lower molecular weight polymers with narrower polydispersities are formed. Without ONp groups or added p-nitrophenol much higher molecular weight poly(HPMA) polymers are found.
  • the 351 kDa material came from a reaction without any ONp esters and without any added p-nitrophenol.
  • When p-nitrophenol is added to polymerization without ONp esters smaller HPMA polymers are obtained with narrower and more uniform molecular weight distributions.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Oncology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Polyamides (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
PCT/US2001/000284 2000-01-04 2001-01-04 N,o-amidomalonate platinum complexes Ceased WO2001049696A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
AU27621/01A AU2762101A (en) 2000-01-04 2001-01-04 N,o-amidomalonate platinum complexes
EP01901752A EP1254145A1 (en) 2000-01-04 2001-01-04 N,o-amidomalonate platinum complexes
CA2396702A CA2396702C (en) 2000-01-04 2001-01-04 N,o-amidomalonate platinum complexes
JP2001550236A JP5025062B2 (ja) 2000-01-04 2001-01-04 N,o−アミドマロネート白金錯体

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US17443500P 2000-01-04 2000-01-04
US60/174,435 2000-01-04

Publications (1)

Publication Number Publication Date
WO2001049696A1 true WO2001049696A1 (en) 2001-07-12

Family

ID=22636134

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2001/000284 Ceased WO2001049696A1 (en) 2000-01-04 2001-01-04 N,o-amidomalonate platinum complexes

Country Status (8)

Country Link
US (1) US6692734B2 (enExample)
EP (1) EP1254145A1 (enExample)
JP (2) JP5025062B2 (enExample)
KR (1) KR100729015B1 (enExample)
AU (1) AU2762101A (enExample)
CA (1) CA2396702C (enExample)
WO (1) WO2001049696A1 (enExample)
ZA (1) ZA200205358B (enExample)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014168956A1 (en) 2013-04-10 2014-10-16 Mimedx Group, Inc. Ndga polymers and metal complexes thereof
WO2015035446A1 (en) * 2013-09-10 2015-03-19 Starpharma Pty Ltd Macromolecules of dendrimer-platinum conjugates
US10159744B2 (en) 2012-11-19 2018-12-25 Mimedx Group, Inc. Cross-linked collagen comprising metallic anticancer agents
US11118016B2 (en) 2018-07-19 2021-09-14 Starpharma Pty Ltd. Therapeutic dendrimer
US12071517B2 (en) 2018-07-19 2024-08-27 Starpharma Pty Ltd. Therapeutic dendrimer

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7166733B2 (en) * 2000-01-04 2007-01-23 Access Pharmaceuticals, Inc. O,O'-Amidomalonate and N,O-Amidomalonate platinum complexes
US7138520B2 (en) * 2003-01-13 2006-11-21 Massachusetts Institute Of Technology Coordination complexes having tethered therapeutic agents and/or targeting moieties, and methods of making and using the same
US7754684B2 (en) * 2003-06-11 2010-07-13 Access Pharmaceuticals, Inc. Macromolecular platinum chelates
RU2472812C2 (ru) 2005-12-05 2013-01-20 НИТТО ДЕНКО КОРПОРЭЙШН (Джэпэн/Джэпэн) Конъюгаты полиглутамат-аминокислота и способы
DK2155254T3 (da) * 2007-05-09 2013-03-04 Nitto Denko Corp Med platinlægemidler konjugerede polymere
PL2209814T3 (pl) * 2007-11-13 2017-08-31 Bio-Technology General (Israel) Ltd. Proces sterylizacji przez filtrację z rozcieńczaniem dla lepkosprężystych biopolimerów
KR101705077B1 (ko) * 2008-10-07 2017-02-09 렉산 파마슈티컬스, 인코포레이티드 Hpma-도세탁셀 또는 젬시타빈 컨쥬게이트 및 이의 용도
JP5281358B2 (ja) * 2008-10-27 2013-09-04 学校法人常翔学園 高分子、経上皮吸収促進剤、及び医薬用製剤
EP2488207A4 (en) 2009-10-13 2015-06-10 Rexahn Pharmaceuticals Inc POLYMERIC ANTIBODY RELEASE SYSTEMS
JP5684056B2 (ja) 2010-08-16 2015-03-11 株式会社マキタ 手持ち工具
KR20180019536A (ko) 2015-06-24 2018-02-26 니폰 가야꾸 가부시끼가이샤 신규한 백금(ⅳ) 착물
WO2017047497A1 (ja) 2015-09-14 2017-03-23 日本化薬株式会社 6配位白金錯体の高分子結合体
EP3706801A4 (en) * 2017-11-08 2022-04-06 L.E.A.F Holdings Group LLC PLATINUM COMPLEXES AND USES THEREOF
CN113018311A (zh) * 2019-12-25 2021-06-25 沈阳药科大学 顺铂配合物以及顺铂配合物脂质体的制备方法
CN117105797B (zh) * 2023-08-25 2025-09-23 湖南科技大学 一种谷氨酸铂配合物及其制备方法和应用

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10159744B2 (en) 2012-11-19 2018-12-25 Mimedx Group, Inc. Cross-linked collagen comprising metallic anticancer agents
WO2014168956A1 (en) 2013-04-10 2014-10-16 Mimedx Group, Inc. Ndga polymers and metal complexes thereof
JP2016519708A (ja) * 2013-04-10 2016-07-07 ミメディクス グループ インコーポレイテッド Ndgaポリマーおよびその金属錯体
EP2983653A4 (en) * 2013-04-10 2016-12-21 Mimedx Group Inc NDGA POLYMERS AND METAL COMPLEXES THEREOF
US10335433B2 (en) 2013-04-10 2019-07-02 Mimedx Group, Inc. NDGA polymers and metal complexes thereof
WO2015035446A1 (en) * 2013-09-10 2015-03-19 Starpharma Pty Ltd Macromolecules of dendrimer-platinum conjugates
US11118016B2 (en) 2018-07-19 2021-09-14 Starpharma Pty Ltd. Therapeutic dendrimer
US11970583B2 (en) 2018-07-19 2024-04-30 Starpharma Pty Ltd. Therapeutic dendrimer
US12071517B2 (en) 2018-07-19 2024-08-27 Starpharma Pty Ltd. Therapeutic dendrimer

Also Published As

Publication number Publication date
AU2762101A (en) 2001-07-16
ZA200205358B (en) 2003-08-20
JP5025062B2 (ja) 2012-09-12
EP1254145A1 (en) 2002-11-06
JP2003530317A (ja) 2003-10-14
KR20020082208A (ko) 2002-10-30
KR100729015B1 (ko) 2007-06-14
US6692734B2 (en) 2004-02-17
JP2011137046A (ja) 2011-07-14
CA2396702C (en) 2010-03-23
CA2396702A1 (en) 2001-07-12
US20010038830A1 (en) 2001-11-08

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