US20100166700A1 - Acryloyloxyethylphosphorylcholine Containing Polymer Conjugates and Their Preparation - Google Patents

Acryloyloxyethylphosphorylcholine Containing Polymer Conjugates and Their Preparation Download PDF

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Publication number
US20100166700A1
US20100166700A1 US12/281,071 US28107107A US2010166700A1 US 20100166700 A1 US20100166700 A1 US 20100166700A1 US 28107107 A US28107107 A US 28107107A US 2010166700 A1 US2010166700 A1 US 2010166700A1
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Prior art keywords
alkyl
group
phenyl
biologically active
cycloalkyl
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US12/281,071
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Stephen A. Charles
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Kodiak Sciences Inc
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Oligasis LLC
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Priority to US12/281,071 priority Critical patent/US20100166700A1/en
Assigned to OLIGASIS CORPORATION reassignment OLIGASIS CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CHARLES, STEPHEN A.
Publication of US20100166700A1 publication Critical patent/US20100166700A1/en
Assigned to OLIGASIS, LLC reassignment OLIGASIS, LLC MERGER (SEE DOCUMENT FOR DETAILS). Assignors: OLIGASIS CORPORATION
Abandoned legal-status Critical Current

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    • 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
    • A61K47/58—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 by reactions only involving carbon-to-carbon unsaturated bonds, e.g. poly[meth]acrylate, polyacrylamide, polystyrene, polyvinylpyrrolidone, polyvinylalcohol or polystyrene sulfonic acid resin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/06—Drugs for disorders of the endocrine system of the anterior pituitary hormones, e.g. TSH, ACTH, FSH, LH, PRL, GH
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/06—Antianaemics
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
    • C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent

Definitions

  • bioactive agents For some biologically active agents a degree of success has been achieved in developing suitable formulations of bioactive agents by conjugating the agents to water soluble polymers.
  • the conjugation of biologically active agents to water soluble polymers is generally viewed as providing a variety of benefits for the delivery of biologically active agents, and in particular, proteins and peptides.
  • PEG polyethylene glycol
  • a reduction in immunogenicity or antigenicity, increased half-life, increased solubility, decreased clearance by the kidney and decreased enzymatic degradation have been attributed to conjugates of a variety of water soluble polymers and bioactive agents, including PEG conjugates.
  • isomers refer to certain compounds of the present invention which possess asymmetric carbon atoms (optical centers) or double bonds; the racemates, diastereomers, geometric isomers and individual isomers (e.g., separate enantiomers). All of these are encompassed by the term “isomers” within the scope of the present invention.
  • “Patient” or “subject in need thereof” refers to a living organism suffering from or prone to a condition that can be prevented or treated by administration of a pharmaceutical composition as provided herein.
  • Non-limiting examples include humans, other mammals and other non-mammalian animals.
  • therapeutic antibodies that may serve as biologically active agents include, but are not limited, to HERCEPTINTM (Trastuzumab) (Genentech, CA) which is a humanized anti-HER2 monoclonal antibody for the treatment of patients with metastatic breast cancer; REOPROTM (abciximab) (Centocor) which is an anti-glycoprotein IIb/IIIa receptor on the platelets for the prevention of clot formation; ZENAPAXTM (daclizumab) (Roche Pharmaceuticals, Switzerland) which is an immunosuppressive, humanized anti-CD25 monoclonal antibody for the prevention of acute renal allograft rejection; PANOREXTM which is a murine anti-17-IA cell surface antigen IgG2a antibody (Glaxo Wellcome/Centocor); BEC2 which is a murine anti-idiotype (GD3 epitope) IgG antibody (ImClone System); IMC-C225 which is a chimeric anti-EGFR I
  • Conjugates of the invention and compositions (e.g., pharmaceutical compositions) containing conjugates of the invention can be used to treat a variety of conditions.
  • the invention contemplates that the conjugates of the invention (e.g., phosphorylcholine containing polymer conjugated to a biologically active agent) and compositions containing the conjugates of the invention can be employed to treat such conditions and that such conjugates provide for an enhanced treatment therapy relative to the same biologically active agent not coupled to a phosphorylcholine containing polymer.
  • the molar ratio of that zwitterionic monomer to the total amount of comonomers is in the range 1:50 to 50:1; in other embodiments, the ratio is in the range of about 1:10 to about 10:1, and in still other embodiments the ratio is in the range of about 1:5 to 1:1.
  • Star architectures may also be prepared employing compounds bearing multiple halogens on a single carbon atom (e.g., trichloromethanol, or 2,2,2-trichloroethanol etc.) or cyclic molecules bearing multiple halogens (e.g., tri- or tetrabromocycloalkanes such as tribromocyclohexanol or tetrabromocyclohexanol).
  • compounds having star architecture have 3 polymer arms and in other embodiments they have 4 polymer arms.
  • the use of one or more ligands to solubilize transition metal catalyst is desirable.
  • Suitable ligands are usefully used in combination with a variety of transition metal catalysts including where copper chloride or bromide, or ruthenium chloride transition metal salts are part of the catalyst.
  • the choice of a ligand affects the function of catalyst as ligands not only aid in solubilizing transition metal catalysts in organic reaction media, but also adjust their redox potential. Selection of a ligand is also based upon the solubility and separability of the catalyst from the product mixture. Where polymerization is to be carried out in a liquid phase soluble ligands/catalyst are generally desirable although immobilized catalysts may be employed.
  • the resulting reaction mixture was analyzed on a Shodex KW-803 size exclusion column using a Beckman Coulter System Gold or Agilent 1100 series HPLC system at 280 nm with a flow rate of 1 mL/min. (after 24 hours, FIG. 5 (7: conjugate; 8: EPO; 9: buffer); after 48 hours, FIG. 6 (10: conjugate; 11: EPO; 12: buffer); and after 72 hours, FIG. 7 (13: conjugate; 14: EPO; 15: buffer)).
  • Taxol which bears two hydroxyl groups is be conjugated to the homopolymers bearing a free reactive carboxyl group prepared in Example 21, part 2a of 1,000, 2,000, 5,000, 10,000, 20,000 or 40,000 Daltons.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Epidemiology (AREA)
  • Diabetes (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Hematology (AREA)
  • Endocrinology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
US12/281,071 2006-02-28 2007-02-28 Acryloyloxyethylphosphorylcholine Containing Polymer Conjugates and Their Preparation Abandoned US20100166700A1 (en)

Priority Applications (1)

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US12/281,071 US20100166700A1 (en) 2006-02-28 2007-02-28 Acryloyloxyethylphosphorylcholine Containing Polymer Conjugates and Their Preparation

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US77691606P 2006-02-28 2006-02-28
US12/281,071 US20100166700A1 (en) 2006-02-28 2007-02-28 Acryloyloxyethylphosphorylcholine Containing Polymer Conjugates and Their Preparation
PCT/US2007/005372 WO2007100902A2 (en) 2006-02-28 2007-02-28 Acryloyloxyethylphosphorylcholine containing polymer conjugates and their preparation

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US13/959,563 Active US8846021B2 (en) 2006-02-28 2013-08-05 Acryloyloxyethylphosphorylcholine containing polymer conjugates and their preparation
US14/456,875 Abandoned US20150050714A1 (en) 2006-02-28 2014-08-11 Acryloyloxyethylphosphorylcholine Containing Polymer Conjugates And Their Preparation
US16/424,265 Abandoned US20200000930A1 (en) 2006-02-28 2019-05-28 Acryloyloxyethylphosphorylcholine Containing Polymer Conjugates And Their Preparation
US17/553,605 Pending US20220096643A1 (en) 2006-02-28 2021-12-16 Acryloyloxyethylphosphorylcholine Containing Polymer Conjugates And Their Preparation

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US14/456,875 Abandoned US20150050714A1 (en) 2006-02-28 2014-08-11 Acryloyloxyethylphosphorylcholine Containing Polymer Conjugates And Their Preparation
US16/424,265 Abandoned US20200000930A1 (en) 2006-02-28 2019-05-28 Acryloyloxyethylphosphorylcholine Containing Polymer Conjugates And Their Preparation
US17/553,605 Pending US20220096643A1 (en) 2006-02-28 2021-12-16 Acryloyloxyethylphosphorylcholine Containing Polymer Conjugates And Their Preparation

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US (5) US20100166700A1 (de)
EP (2) EP3222142A1 (de)
JP (2) JP5528710B2 (de)
DK (1) DK1988910T3 (de)
ES (1) ES2657628T3 (de)
LT (1) LT1988910T (de)
PT (1) PT1988910T (de)
SI (1) SI1988910T1 (de)
WO (2) WO2007100902A2 (de)

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WO2015035342A2 (en) 2013-09-08 2015-03-12 Oligasis Llc Factor viii zwitterionic polymer conjugates
US9067988B2 (en) 2010-12-01 2015-06-30 Alderbio Holdings Llc Methods of preventing or treating pain using anti-NGF antibodies
US9078878B2 (en) 2010-12-01 2015-07-14 Alderbio Holdings Llc Anti-NGF antibodies that selectively inhibit the association of NGF with TrkA, without affecting the association of NGF with p75
US20150376271A1 (en) * 2014-06-28 2015-12-31 Oligasis, Llc Dual pdgf/vegf antagonists
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US10363290B2 (en) 2014-10-17 2019-07-30 Kodiak Sciences Inc. Butyrylcholinesterase zwitterionic polymer conjugates
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