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Therapeutical polyanhydride compounds for drug delivery

A technology of polymers and compounds, applied in drug combination, drug delivery, active ingredients of artificially synthesized polymeric materials, etc., can solve problems such as difficult processing, lower glass transition temperature, high melting temperature, etc.

Inactive Publication Date: 2005-07-20
RUTGERS THE STATE UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these compounds exhibit high melting and glass transition temperatures and reduced solubility, thus making them difficult to process

Method used

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  • Therapeutical polyanhydride compounds for drug delivery
  • Therapeutical polyanhydride compounds for drug delivery
  • Therapeutical polyanhydride compounds for drug delivery

Examples

Experimental program
Comparison scheme
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Embodiment 1

[0132] The synthesis of embodiment 1 amoxicillin polymer

[0133] Scheme 1 shows the attachment of amoxicillin in the polyanhydrides of the present invention. The carboxylic acid groups of low molecular weight drug molecules are preferably protected by acetylation. The protected drug molecule is then exposed to the chlorinated form of the linker of formula (IV), wherein n is 8. The amino group from the drug molecule replaces the chlorine group of the diacid chloride formula (IV) and passes through the amino group of the drug molecule and the linker (R 2 ) combined. Subsequent exposure of the attached drug to heat and / or vacuum removes the protecting group, thus creating a polymeric drug delivery system.

[0134] plan 1

[0135]

Embodiment 2

[0136] The synthesis of embodiment 2 cephalexin polymer

[0137] Cefalexin polymer was prepared as shown in Scheme 2. First the carboxylic acid group of the cephalexin is protected, for example with a benzyl group. The drug is then linked to sebacoyl chloride (formula (IV), where n is 8). After this linkage, the protecting groups are removed to generate carboxylic acids, which are then acetylated to generate monomers. This monomer is melt polymerized.

[0138] Scenario 2

[0139]

Embodiment 3

[0141] Other polymeric drug delivery systems that can be prepared in this way via the polyanhydride linkers of formula (I) of the present invention include, but are not necessarily limited to, carbidopa delivery systems, levodopa delivery systems, and amtenac delivery systems . Homopolymers of carbidopa and levodopa drug delivery systems are depicted in formulas (V) and (VI), respectively.

[0142]

[0143] Although these structures depict homopolymers, copolymers of these drugs can also be routinely prepared based on the teachings provided herein. In addition, polymeric drug delivery systems comprising polyanhydrides of formula (I) and other drugs satisfying the structural requirements, i.e., one carboxylic acid group, at least one amino group, thiol, Alcohol or phenolic groups and have a molecular weight of about 1000 Daltons or less.

[0144]The above-identified polymers, compounds and / or compositions comprising a bioactive agent or compound, or drug molecule of the in...

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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 drug to a host via the polymeric drug delivery systems. Medical implants based on the polymeric drug delivery system of the invention are also provided.

Description

Background of the invention [0001] Polymers comprising aromatic or aliphatic anhydrides have been extensively studied in the past for a variety of applications. For example, fibers comprising aliphatic polyanhydrides were produced for the textile industry in the 1930's. In the mid-1950's, aromatic polyanhydrides with improved film and fiber forming properties were prepared. Recently, attempts have been made to synthesize polyanhydrides with greater thermal and hydrolytic stability and sustained drug release properties. [0002] US Patents 4,757,128 and 4,997,904 disclose the preparation of polyanhydrides with improved sustained drug release properties from pure, isolated prepolymers of dibasic acids and acetic acid. However, these biocompatible and biodegradable aromatic polyanhydrides have free radicals or aliphatic linkages resulting in compounds with slow degradation times and relatively insoluble degradation products unless incorporated with more hydrophilic monomers ( ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K9/00A61K9/16A61K47/48A61L27/18A61L27/34A61L27/54A61L29/06A61L29/08A61L29/16A61L31/06A61L31/10A61L31/16
CPCA61K47/48207A61L2300/41A61L31/16A61L27/18A61L29/16A61L29/085A61L29/06A61L2300/604A61L27/54A61K9/0021A61L27/34A61K9/0024A61L31/10A61K9/1641A61K47/48192A61L31/06A61K47/59A61K47/595A61P25/16A61P31/04C08L73/02A61K47/50A61K31/74A61K47/30A61K47/34
Inventor K·E·尤里赫
Owner RUTGERS THE STATE UNIV