CA2183292A1 - Improved method of preparing polyalkylene oxide carboxylic acids - Google Patents

Improved method of preparing polyalkylene oxide carboxylic acids

Info

Publication number
CA2183292A1
CA2183292A1 CA2183292A CA2183292A CA2183292A1 CA 2183292 A1 CA2183292 A1 CA 2183292A1 CA 2183292 A CA2183292 A CA 2183292A CA 2183292 A CA2183292 A CA 2183292A CA 2183292 A1 CA2183292 A1 CA 2183292A1
Authority
CA
Canada
Prior art keywords
carboxylic acids
polyalkylene oxide
improved method
oxide carboxylic
preparing polyalkylene
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
CA2183292A
Other languages
French (fr)
Other versions
CA2183292C (en
Inventor
Anthony J. Martinez
Richard B. Greenwald
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.)
Enzon Pharmaceuticals Inc
Original Assignee
Enzon 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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=27170183&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CA2183292(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority to US08/440,732 priority Critical patent/US5605976A/en
Priority to US08/696,198 priority patent/US5681567A/en
Priority to CA002183292A priority patent/CA2183292C/en
Priority to DK96202288.5T priority patent/DK0824126T4/en
Priority to EP96202288A priority patent/EP0824126B2/en
Priority to AT96202288T priority patent/ATE243723T1/en
Priority to ES96202288T priority patent/ES2202409T3/en
Application filed by Enzon Inc filed Critical Enzon Inc
Priority to DE69628827T priority patent/DE69628827T3/en
Priority to US08/883,150 priority patent/US5756593A/en
Publication of CA2183292A1 publication Critical patent/CA2183292A1/en
Publication of CA2183292C publication Critical patent/CA2183292C/en
Application granted granted Critical
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/338—Polymers modified by chemical after-treatment with inorganic and organic compounds
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
    • C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
    • C08G65/3322—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof acyclic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
    • C08G65/33396—Polymers modified by chemical after-treatment with organic compounds containing nitrogen having oxygen in addition to nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/337—Polymers modified by chemical after-treatment with organic compounds containing other elements

Abstract

The present invention is directed to methods of preparing high punt polyalkylene oxide carboxylic acids. The methods include reacting a polyalkylene oxide such as polyethylene glycol with a t-butyl haloacetate in the presence of a base followed by treatment with an acid such as trifluoroacetic acid. The resultant polymer carboxylic acids are of sufficient purity so that expensive and time consuming purification steps required for pharmaceutical grade polymers are avoided.
CA002183292A 1995-05-15 1996-08-14 Improved method of preparing polyalkylene oxide carboxylic acids Expired - Fee Related CA2183292C (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
US08/440,732 US5605976A (en) 1995-05-15 1995-05-15 Method of preparing polyalkylene oxide carboxylic acids
US08/696,198 US5681567A (en) 1995-05-15 1996-08-13 Method of preparing polyalkylene oxide carboxylic acids
DK96202288.5T DK0824126T4 (en) 1995-05-15 1996-08-14 Preparation of carboxylic acid-containing polyethers and biologically active substances
EP96202288A EP0824126B2 (en) 1995-05-15 1996-08-14 Preparation of carboxylic acid-containing polyether and biologically active substances derived thereof
AT96202288T ATE243723T1 (en) 1995-05-15 1996-08-14 PRODUCTION OF POLYETHERS THAT CONTAIN CARBOXYL GROUPS AND BIOLOGICALLY ACTIVE SUBSTANCES
ES96202288T ES2202409T3 (en) 1995-05-15 1996-08-14 POLYETER PREPARATION WITH CONTENT IN CARBOXILIC ACID AND DERIVED BIOLOGICALLY ACTIVE SUBSTANCES.
CA002183292A CA2183292C (en) 1995-05-15 1996-08-14 Improved method of preparing polyalkylene oxide carboxylic acids
DE69628827T DE69628827T3 (en) 1995-05-15 1996-08-14 Preparation of polyethers containing carboxyl groups and biologically active substances
US08/883,150 US5756593A (en) 1995-05-15 1997-06-27 Method of preparing polyalkyene oxide carboxylic acids

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US08/440,732 US5605976A (en) 1995-05-15 1995-05-15 Method of preparing polyalkylene oxide carboxylic acids
EP96202288A EP0824126B2 (en) 1995-05-15 1996-08-14 Preparation of carboxylic acid-containing polyether and biologically active substances derived thereof
CA002183292A CA2183292C (en) 1995-05-15 1996-08-14 Improved method of preparing polyalkylene oxide carboxylic acids

Publications (2)

Publication Number Publication Date
CA2183292A1 true CA2183292A1 (en) 1998-02-15
CA2183292C CA2183292C (en) 2001-01-30

Family

ID=27170183

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002183292A Expired - Fee Related CA2183292C (en) 1995-05-15 1996-08-14 Improved method of preparing polyalkylene oxide carboxylic acids

Country Status (7)

Country Link
US (2) US5605976A (en)
EP (1) EP0824126B2 (en)
AT (1) ATE243723T1 (en)
CA (1) CA2183292C (en)
DE (1) DE69628827T3 (en)
DK (1) DK0824126T4 (en)
ES (1) ES2202409T3 (en)

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