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Therapeutic polyanhydride compounds for drug delivery

a technology of polyanhydride compounds and drug delivery, applied in the direction of drugs, prostheses, immunological disorders, etc., can solve the problems of slow degradation time, relatively insoluble degradation products, difficult processing, etc., and achieve the effect of improving solubility and processability

Inactive Publication Date: 2005-03-10
RUTGERS THE STATE UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention provides a new type of polymer that can be used to make drug delivery systems. These polymers have the advantage of being biodegradable and can be easily solubilized. The polymers have specific units that will release a therapeutically active compound when they are exposed to water. The polymers can be used to link low molecular weight drugs containing carboxylic acid groups and amine, thiol, alcohol, or phenol groups. The resulting drug delivery systems can be used to treat diseases in animals and plants. The invention also provides a method for making the polymer and using it for medical therapy. The polymer can be made using specific processes and intermediates.

Problems solved by technology

However, these biocompatible and biodegradable aromatic polyanhydrides have radical or aliphatic bonds resulting in compounds with slow degradation times as well as relatively insoluble degradation products unless incorporated into a copolymer containing a more hydrophilic monomer, such as sebacic acid.
However, these compounds exhibit high melt and glass transition temperatures and decreased solubility, thus making them difficult to process.

Method used

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  • Therapeutic polyanhydride compounds for drug delivery
  • Therapeutic polyanhydride compounds for drug delivery
  • Therapeutic polyanhydride compounds for drug delivery

Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis of Amoxicillin Polymer

The linkage of amoxicillin in a polyanhydride of the present invention is shown in the scheme 1. The carboxylic acid group of the low molecular weight drug molecule is protected, preferably via acetylation. The protected drug molecules are then exposed to a chlorinated form of the linker of formula (IV), wherein n is 8. The amine groups from the drug molecules displace the chlorine groups of the diacyl halide Formula (IV) and bind to the linker(R2) via the amine, groups of the drug molecules. The linked drug is exposed to heat and / or vacuum to remove the protecting groups, thereby resulting in a polymeric drug delivery system.

example 2

Synthesis of Cephalexin Polymer

A cephalexin polymer is prepared as depicted in scheme 2. The carboxylic acid group of cephalexin is first protected, for example with a benzylic group. The drug is then linked to sebacoyl chloride (formula (IV) where n is 8). Following this linkage, the protecting groups are removed to produce carboxylic acids which are then acetylated to produce monomer. The monomer is polymerized as a melt.

example 3

Other polymeric drug delivery systems can be prepared in accordance with this method via the polyanhydride linker of Formula (I) of the present invention include, but are certainly not limited to, a carbidopa delivery system, a levodopa delivery system and an amtenac delivery system. Homopolymers of the carbidopa and levodopa drug delivery systems are depicted in Formulas (V) and (VI), respectively

While these structures depict homopolymers, copolymers of such drugs can also be prepared routinely based upon the teachings provided herein. Further, polymeric drug delivery systems comprising the polyanhydride of Formula (I) and other drugs meeting the structural requirements, namely one carboxylic acid group, at least one amine, thiol, alcohol or phenol group, and having a molecular weight of approximately 1000 daltons or less can also be routinely prepared via the disclosed methods.

Activity

The ability of a polymer of the invention to produce a given therapeutic effect can be de...

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Abstract

Polyanhydrides which link low molecular weight drugs containing a carboxylic acid group and an amine, thiol, alcohol or phenol group within their structure into polymeric drug delivery systems are provided. Also provided are methods of producing polymeric drug delivery systems via these polyanhydride linkers as well as methods of administering low molecular weight drugs to a host via the polymeric drug delivery systems.

Description

BACKGROUND OF THE INVENTION Polymers comprising aromatic or aliphatic anhydrides have been studied extensively over the years for a variety of uses. For example, in the 1930s fibers comprising aliphatic polyanhydrides were prepared for use in the textile industry. In the mid 1950s, aromatic polyanhydrides were prepared with improved film and fiber forming properties. More recently, attempts have been made to synthesize polyanhydrides with greater thermal and hydrolytic stability and sustained drug release properties. U.S. Pat. Nos. 4,757,128 and 4,997,904 disclose the preparation of polyanhydrides with improved sustained drug release properties from pure, isolated prepolymers of diacids and acetic acid. However, these biocompatible and biodegradable aromatic polyanhydrides have radical or aliphatic bonds resulting in compounds with slow degradation times as well as relatively insoluble degradation products unless incorporated into a copolymer containing a more hydrophilic monomer,...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K8/368A61K8/85A61K9/20A61K31/198A61K31/43A61K31/545A61K31/765A61K47/48A61L27/18A61P25/16A61P31/04A61Q19/00C08G67/04C08L73/02
CPCA61K8/368A61K8/85C08L73/02C08G67/04A61Q19/08A61Q19/00A61Q5/006A61L2300/416A61L2300/41A61K9/2031A61K31/765A61K47/48023A61K47/481A61K47/48115A61K47/48192A61K47/48207A61L17/005A61L17/10A61L27/18A61L27/34A61L27/54A61L27/58A61L31/06A61L31/10A61L31/148A61L31/16A61L2300/406A61K47/54A61K47/55A61K47/552A61K47/59A61K47/595A61P25/16A61P29/00A61P31/04A61P31/10A61P35/00A61P37/06A61P7/02
Inventor UHRICH, KATHRYN E.
Owner RUTGERS THE STATE UNIV
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