CA2520450A1 - Polymeric modifiers that improve the bioavailability of protein drugs and pharmaceutical compositions thereof - Google Patents

Polymeric modifiers that improve the bioavailability of protein drugs and pharmaceutical compositions thereof Download PDF

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Publication number
CA2520450A1
CA2520450A1 CA002520450A CA2520450A CA2520450A1 CA 2520450 A1 CA2520450 A1 CA 2520450A1 CA 002520450 A CA002520450 A CA 002520450A CA 2520450 A CA2520450 A CA 2520450A CA 2520450 A1 CA2520450 A1 CA 2520450A1
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CA
Canada
Prior art keywords
copolymer
optionally substituted
complex
formula
bioavailability
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
CA002520450A
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French (fr)
Other versions
CA2520450C (en
Inventor
Yuji Kasuya
Masashi Honma
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.)
Sankyo Co Ltd
Original Assignee
Sankyo Company Limited
Yuji Kasuya
Masashi Honma
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 Sankyo Company Limited, Yuji Kasuya, Masashi Honma filed Critical Sankyo Company Limited
Publication of CA2520450A1 publication Critical patent/CA2520450A1/en
Application granted granted Critical
Publication of CA2520450C publication Critical patent/CA2520450C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • 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
    • C08F216/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
    • C08F216/12—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
    • C08F216/14—Monomers containing only one unsaturated aliphatic radical
    • C08F216/16—Monomers containing no hetero atoms other than the ether oxygen
    • C08F216/18—Acyclic compounds
    • C08F216/20—Monomers containing three or more carbon atoms in the unsaturated aliphatic radical
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/02—Polyalkylene oxides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • A61K38/177—Receptors; Cell surface antigens; Cell surface determinants
    • 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
    • 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
    • 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
    • A61P19/00—Drugs for skeletal disorders
    • 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
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/04—Anhydrides, e.g. cyclic anhydrides
    • C08F222/06—Maleic anhydride
    • 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
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
    • C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
    • 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
    • C08F216/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
    • C08F216/12—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
    • C08F216/14—Monomers containing only one unsaturated aliphatic radical
    • C08F216/1416—Monomers containing oxygen in addition to the ether oxygen, e.g. allyl glycidyl ether
    • C08F216/1425—Monomers containing side chains of polyether groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2203/00—Applications
    • C08L2203/02—Applications for biomedical use

Abstract

A copolymer or a pharmacologically acceptable salt thereof is provided, which contains, as constitutional units, (a) one or more structural units of formula (I): wherein m is an integer of from 3 to 100, Alk represents alkylene, and R1 and R2 are the same or different and each represents hydrogen or optionally substituted alkyl, and (b) one or more structural units of formula (II):
wherein R3 represents hydroxyl, optionally substituted alkoxy, optionally substituted aryloxy, or a group represented by the formula -NR4R5, wherein R4 and R5 are the same or different and each represents hydrogen or optionally substituted alkyl. There is further provided a pharmaceutical composition comprising said copolymer, a protein modifier comprising said copolymer, a complex of said copolymer with a protein, a method of preventing or treating diseases using said complex, use of said complex in the manufacture of a medicament for preventing or treating diseases and methods for the synthesis of said copolymers and said complexes.
CA002520450A 2003-03-24 2004-03-24 Polymeric modifiers that improve the bioavailability of protein drugs and pharmaceutical compositions thereof Expired - Fee Related CA2520450C (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
JP2003-080389 2003-03-24
JP2003080389 2003-03-24
JP2003355853 2003-10-16
JP2003-355853 2003-10-16
JP2003426598 2003-12-24
JP2003-426598 2003-12-24
PCT/JP2004/004134 WO2004085500A1 (en) 2003-03-24 2004-03-24 Polymeric modifiers and pharmaceutical compositions

Publications (2)

Publication Number Publication Date
CA2520450A1 true CA2520450A1 (en) 2004-10-07
CA2520450C CA2520450C (en) 2009-11-03

Family

ID=33101948

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002520450A Expired - Fee Related CA2520450C (en) 2003-03-24 2004-03-24 Polymeric modifiers that improve the bioavailability of protein drugs and pharmaceutical compositions thereof

Country Status (23)

Country Link
US (1) US7811556B2 (en)
EP (1) EP1611173B1 (en)
KR (1) KR20050118201A (en)
AR (1) AR043917A1 (en)
AT (1) ATE388173T1 (en)
AU (1) AU2004223964B2 (en)
BR (1) BRPI0408526A (en)
CA (1) CA2520450C (en)
CL (1) CL2004000633A1 (en)
DE (1) DE602004012241T2 (en)
DK (1) DK1611173T3 (en)
ES (1) ES2301978T3 (en)
HK (1) HK1078598A1 (en)
IL (1) IL170489A (en)
MX (1) MXPA05010289A (en)
NZ (1) NZ542352A (en)
PA (1) PA8598701A1 (en)
PE (1) PE20041067A1 (en)
PL (1) PL1611173T3 (en)
PT (1) PT1611173E (en)
SI (1) SI1611173T1 (en)
TW (1) TWI293882B (en)
WO (1) WO2004085500A1 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2090599A1 (en) * 2008-02-13 2009-08-19 Construction Research and Technology GmbH Copolymer with polyether side chains and dicarbonic acid derivative building blocks

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1217005A (en) * 1916-05-08 1917-02-20 Judson D Mccarthy Photographic-printing frame.
DE3260845D1 (en) * 1981-01-16 1984-11-08 Nippon Catalytic Chem Ind Copolymer and method for manufacture thereof
JP2701295B2 (en) 1987-03-13 1998-01-21 日本油脂株式会社 Allyl ether-maleic anhydride copolymer
JP2621308B2 (en) 1987-03-13 1997-06-18 日本油脂株式会社 Allyl ether-maleic anhydride copolymer
JP2803265B2 (en) 1989-12-26 1998-09-24 日本油脂株式会社 Denatured polypeptide and use thereof
US5158622A (en) * 1991-02-12 1992-10-27 Betz Laboratories, Inc. Method and composition for treatment of aluminum
JP3271265B2 (en) * 1991-03-07 2002-04-02 日本油脂株式会社 Modified protease
JP3035675B2 (en) * 1991-08-21 2000-04-24 株式会社コーセー Modified superoxide dismutase
CA2080174A1 (en) * 1991-10-11 1993-04-12 John E. Hayes Polymer polyol dispersants from polymers containing anhydride groups
JP3106265B2 (en) 1992-05-26 2000-11-06 株式会社コーセー Modified lysozyme
US6004583A (en) * 1995-03-22 1999-12-21 Orex Pharmaceutical Development Corp. Protein-containing polymer composition for oral administration
US6369027B1 (en) 1995-12-22 2002-04-09 Amgen Inc. Osteoprotegerin
IT1293087B1 (en) 1997-07-10 1999-02-11 Isi Ist Sierovaccinogeno Ital MICROPARTICLES BASED ON HYBRID POLYMER MATERIALS FOR THE CONTROLLED RELEASE OF BIOLOGICALLY ACTIVE MOLECULES, PROCEDURE FOR THE
DE19834173A1 (en) * 1997-08-01 1999-02-04 Sueddeutsche Kalkstickstoff Copolymer based on unsaturated di:carboxylic acid derivatives and oxyalkylene glycol-alkenyl ether(s)
JPH11302199A (en) 1998-04-16 1999-11-02 Sankyo Co Ltd Drug carrier composed of graft copolymer
DE19847868C2 (en) * 1998-10-16 2003-09-25 Clariant Gmbh Explosives containing modified copolymers of polyisobutylene and maleic anhydride as emulsifiers
CN1338924A (en) * 1999-01-08 2002-03-06 艾米斯菲尔技术有限公司 Polymeric delivery agents and delivery agent compounds
ITTO20000942A1 (en) 2000-10-10 2001-01-10 Sergio Guzzoni PRICEDIMENT FOR THE MANAGEMENT OF MESSAGE INTERCHANGES BETWEEN CUSTOMER SUPPLIERS OF TELEPHONE SERVICES.
JP5109218B2 (en) 2001-09-28 2012-12-26 日油株式会社 Method for producing copolymer
JP2003105040A (en) 2001-09-28 2003-04-09 Nof Corp Method for manufacturing copolymer and its use

Also Published As

Publication number Publication date
SI1611173T1 (en) 2008-08-31
US20060062754A1 (en) 2006-03-23
KR20050118201A (en) 2005-12-15
DK1611173T3 (en) 2008-06-23
TWI293882B (en) 2008-03-01
MXPA05010289A (en) 2005-11-17
PE20041067A1 (en) 2005-01-22
EP1611173B1 (en) 2008-03-05
AU2004223964B2 (en) 2007-02-22
IL170489A (en) 2009-06-15
PL1611173T3 (en) 2008-08-29
ATE388173T1 (en) 2008-03-15
PA8598701A1 (en) 2005-02-04
DE602004012241D1 (en) 2008-04-17
CA2520450C (en) 2009-11-03
BRPI0408526A (en) 2006-03-07
US7811556B2 (en) 2010-10-12
NZ542352A (en) 2007-02-23
CL2004000633A1 (en) 2005-01-21
TW200501986A (en) 2005-01-16
ES2301978T3 (en) 2008-07-01
DE602004012241T2 (en) 2009-03-12
EP1611173A1 (en) 2006-01-04
WO2004085500A1 (en) 2004-10-07
AR043917A1 (en) 2005-08-17
PT1611173E (en) 2008-05-23
AU2004223964A1 (en) 2004-10-07
HK1078598A1 (en) 2006-03-17

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