CA2450949A1 - Methods and compositions for polyene antibiotics with reduced toxicity - Google Patents

Methods and compositions for polyene antibiotics with reduced toxicity Download PDF

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Publication number
CA2450949A1
CA2450949A1 CA002450949A CA2450949A CA2450949A1 CA 2450949 A1 CA2450949 A1 CA 2450949A1 CA 002450949 A CA002450949 A CA 002450949A CA 2450949 A CA2450949 A CA 2450949A CA 2450949 A1 CA2450949 A1 CA 2450949A1
Authority
CA
Canada
Prior art keywords
carbon atoms
desirably
polyene
amphotericin
core
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.)
Granted
Application number
CA002450949A
Other languages
French (fr)
Other versions
CA2450949C (en
Inventor
John Samuel
Afsaneh Lavasanifar
Glen S. Kwon
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.)
Wisconsin Alumni Research Foundation
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of CA2450949A1 publication Critical patent/CA2450949A1/en
Application granted granted Critical
Publication of CA2450949C publication Critical patent/CA2450949C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
    • A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • A61K31/138—Aryloxyalkylamines, e.g. propranolol, tamoxifen, phenoxybenzamine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00—Medicinal preparations containing inorganic active ingredients
    • A61K33/24—Heavy metals; Compounds thereof
    • A61K33/243—Platinum; Compounds thereof
    • 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
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics

Abstract

Provided are methods and compositions for reducing the toxicity of certain hydrophobic therapeutic agents, especially polyene antibiotics, in particular, Amphotericin B (AmB), and therapeutics such as paclitaxel, tamoxifen, an acylated prodrug or an acylated cis-platin, by incorporating these agents within micelles comprising an amphiphilic block-forming copolymer. Where the polyene is amphotericin B, desirably the spacer is an alkyl molecule of about 2 to about 8 carbon atoms, desirably 6 carbon atoms, and the core is an N-alkyl molecule of about 8 to about 28 carbon atoms, desirably 12 to 22 carbon atoms, advantageously, 12 to 18 carbon atoms, and as specifically embodied, 18 carbon atoms (stearate moiety). For the formulation of a larger polyene, the spacer and core are proportionately larger than those for amphotericin B. As specifically exemplified herein, the polymer backbone is a PEO of about 270 units with about 10-30 core-forming PLAA subunits, and advantageously about 14-24. Desirably the stearate moiety has a substitution level on the copolymer from about 35 percent to about 70 percent.
CA002450949A 2001-06-28 2002-06-28 Methods and compositions for polyene antibiotics with reduced toxicity Expired - Lifetime CA2450949C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US30210901P 2001-06-28 2001-06-28
US60/302,109 2001-06-28
PCT/US2002/020827 WO2003002096A1 (en) 2001-06-28 2002-06-28 Methods and compositions for polyene antibiotics with reduced toxicity

Publications (2)

Publication Number Publication Date
CA2450949A1 true CA2450949A1 (en) 2003-01-09
CA2450949C CA2450949C (en) 2009-04-28

Family

ID=23166294

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002450949A Expired - Lifetime CA2450949C (en) 2001-06-28 2002-06-28 Methods and compositions for polyene antibiotics with reduced toxicity

Country Status (3)

Country Link
US (1) US6939561B2 (en)
CA (1) CA2450949C (en)
WO (1) WO2003002096A1 (en)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003082303A1 (en) * 2002-03-29 2003-10-09 Wisconsin Alumni Research Foundation Polymeric micelle formulations of hydrophobic compounds and methods
FR2840614B1 (en) 2002-06-07 2004-08-27 Flamel Tech Sa POLYAMINOACIDS FUNCTIONALIZED BY ALPHA-TOCOPHEROL AND THEIR PARTICULARLY THERAPEUTIC APPLICATIONS
FR2855521B1 (en) 2003-05-28 2005-08-05 Flamel Tech Sa POLYAMINOACIDES FUNCTIONALIZED BY AT LEAST ONE YDROPHOBIC GROUP AND THEIR PARTICULARLY THERAPEUTIC APPLICATIONS.
CA2603987A1 (en) 2005-04-12 2006-10-19 Wisconsin Alumni Research Foundation Micelle composition of polymer and passenger drug
ITMI20060494A1 (en) * 2006-03-17 2007-09-18 Sifi Spa PHARMACEUTICAL COMPOSITION OF OPHTHALMIC CONTAINING AMPHIFILE COPOLYMERS OF POLYASPARTAMIDE
WO2008106129A2 (en) * 2007-02-26 2008-09-04 Wisconsin Alumni Research Foundation Polymeric micelles for combination drug delivery
EP2155165A1 (en) * 2007-04-20 2010-02-24 BioCure, Inc. Drug delivery vehicle containing vesicles in a hydrogel base
ITRM20070327A1 (en) * 2007-06-11 2008-12-12 Univ Palermo COLLOIDAL VECTORS WITH POLYAMINOACIDIC STRUCTURE FOR THE ORAL RELEASE OF PEPTIDES AND PROTEINS AND ITS RELATED PRODUCTION METHOD.
US20100210575A1 (en) * 2007-06-29 2010-08-19 Wisconsin Alumni Research Foundation Structuring effect of cholesterol in peg-phospholipid micelles, drug delivery of amphotericin b, and combination antifungals
US20090232762A1 (en) * 2008-03-11 2009-09-17 May Pang Xiong Compositions for delivery of therapeutic agents
US8697098B2 (en) * 2011-02-25 2014-04-15 South Dakota State University Polymer conjugated protein micelles
WO2010068432A1 (en) * 2008-11-25 2010-06-17 Ecole Polytechnique Federale De Lausanne (Epfl) Block copolymers and uses thereof
KR101721281B1 (en) 2009-09-25 2017-04-10 위스콘신 얼럼나이 리서어치 화운데이션 Micelle encapsulation of therapeutical agents
EP2371823A1 (en) 2010-04-01 2011-10-05 Bayer CropScience AG Cyclopropyl-substituted phenylsulfonylamino(thio)carbonyltriazolinones, their production and use as herbicides and plant growth regulators
JP2014518842A (en) 2011-02-25 2014-08-07 サウス ダコタ ステート ユニバーシティー Polymer conjugate protein micelle
TWI454450B (en) 2012-11-02 2014-10-01 Ind Tech Res Inst Organic compound and organic electroluminescence device employing the same
US10711106B2 (en) 2013-07-25 2020-07-14 The University Of Chicago High aspect ratio nanofibril materials

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5059591B1 (en) 1983-05-26 2000-04-25 Liposome Co Inc Drug preparations of reduced toxicity
PT78628B (en) 1984-05-02 1986-06-18 Liposome Co Inc Pharmaceutical composition with reduced toxicity
KR940003548U (en) 1992-08-14 1994-02-21 김형술 Laundry dryer
US5686110A (en) 1994-06-02 1997-11-11 Enzon, Inc. Water soluble complex of an alkyl or olefinic end capped polyalkylene oxide and a water insoluble substance
US5885613A (en) 1994-09-30 1999-03-23 The University Of British Columbia Bilayer stabilizing components and their use in forming programmable fusogenic liposomes
US5925720A (en) 1995-04-19 1999-07-20 Kazunori Kataoka Heterotelechelic block copolymers and process for producing the same
CA2229068A1 (en) 1995-08-10 1997-02-20 Masao Kato Block polymer having functional groups on its both ends
US6217886B1 (en) * 1997-07-14 2001-04-17 The Board Of Trustees Of The University Of Illinois Materials and methods for making improved micelle compositions
EP1315777B1 (en) * 2000-09-06 2007-10-31 AP Pharma, Inc. Degradable polyacetal polymers

Also Published As

Publication number Publication date
US6939561B2 (en) 2005-09-06
CA2450949C (en) 2009-04-28
US20030086964A1 (en) 2003-05-08
WO2003002096A1 (en) 2003-01-09

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Effective date: 20220628