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Design of poly(ester amides) for the control of agent-release from polymeric compositions

a polymer composition and agent-release technology, applied in the field of polymer matrices, can solve the problems of agents being released, creating adverse effects within the subject, and art has not yet developed a reliable control method

Inactive Publication Date: 2005-12-29
ABBOTT CARDIOVASCULAR
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Problems with PTCA include formation of intimal flaps or torn arterial linings, both of which can create another occlusion in the lumen of the coronary artery.
Moreover, thrombosis and restenosis may occur several months after the procedure and create a need for additional angioplasty or a surgical by-pass operation.
Local delivery of agents is often preferred over systemic delivery of agents, particularly where high systemic doses are necessary to achieve an effect at a particular site within a subject—high systemic doses of agents can often create adverse effects within the subject.
A disadvantage of this method is that the agents are released from the matrix through the blend and compete with one another for release.
Unfortunately, the art has not yet developed a reliable way to control the release of agents from a medical device or coating, yet such control can be important to obtaining the desired effects or reducing any adverse effects that may otherwise occur from administration of the agents.

Method used

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  • Design of poly(ester amides) for the control of agent-release from polymeric compositions
  • Design of poly(ester amides) for the control of agent-release from polymeric compositions
  • Design of poly(ester amides) for the control of agent-release from polymeric compositions

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0343] The PEA of formula (XVII) can be prepared according to the following procedure:

Method of Preparing of L-Leucine-ε-L-Lysine Benzyl Ester-2TosOH

[0344] L-leucine-ε-L-lysine HCl (New England Peptide, Inc.) (73.86 gm, 0.25 mole), p-toluenesulfonic acid (152.15 gm, 0.80 mole), benzyl alcohol (100.9 ml, 0.97 mole), and 200 ml of benzene is added to a 1 liter reaction flask equipped with a mechanical stirrer, Dean Stark trap, thermometer and argon inlet. The mixture is heated to 80° C. for 8 hours, and condensate is collected in the Dean Stark trap. The mixture is transferred to a 2 liter flask, and 1 liter of ethyl acetate is added to the mixture with stirring. The mixture is stored overnight at 4° C., and L-Leucine-E-L-Lysine Benzyl Ester-2TosOH and is isolated by filtration.

Method of Preparing co-poly-{[N,N′-sebacoyl-bis-(L-leucine)-1,6-hexylene diester]-[N,N′-sebacoyl-L-leucine-L-lysine mPEG amide]}

[0345] Dry triethylamine (61.6 ml, 0.44 mole) is added to a mixture of di-p-tol...

example 2

[0350] The copolymer represented by formula (XII) can be prepared in a manner analogous to the method used to prepare the copolymer represented by formula (XVII) by replacing the L-leucine-ε-L-lysine HCl with L-lysine HCl. While not intending to be bound by any theory or mechanism of action, a proposed reaction mechanism for the preparation of the PEA of formula (XII) according to one embodiment of the present invention is illustrated in FIG. 11b.

example 3

[0351] The PEA of formula (XV) can be prepared according to the following procedure:

Method of Preparing co-poly-{[N,N′-sebacoyl-bis-(L-leucine)-1,4-butylene diester]-[N,N′-sebacoyl-L-lysine-4-carboxy-TEMPO anhydride]}

[0352] Dry triethylamine (61.6 ml, 0.44 mole) is added to a mixture of a di-p-toluenesulfonic acid salt of bis-(L-leucine)-1,4-butylene diester (118.82 gm, 0.18 mole), a di-p-toluenesulfonic acid salt of L-lysine benzyl ester (11.603 gm, 0.02 mole), and di-p-nitrophenyl sebacinate (88.88 gm, 0.2 mole) in dry DMAC (110 ml). The mixture is stirred and heated at 80° C. for 12 hours, cooled to room temperature, diluted with ethanol (300 ml), and poured into water (1 liter).

[0353] The polymer is separated, washed with water, and dried under vacuum. A free carboxyl group can be generated by hydrogenolysis over a palladium catalyst. Ethanol (1200 ml) is combined with the polymer (100 gm) and a palladium on carbon catalyst in a 2 liter flask (Aldrich). Hydrogen is bubbled and...

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Abstract

The present invention generally encompasses a medical article, such as a medical device or coating comprising an agent or combination of agents, wherein the agent is distributed throughout a polymeric matrix. The polymeric matrix comprises an agent and a poly(ester amide) having a design that was preselected to provide a predetermined release rate of the combination of agents from the medical article.

Description

CROSS REFERENCE [0001] This application is a continuation-in-part of application Ser. No. 10 / 835,656, filed Apr. 30, 2004; a continuation-in-part of application Ser. No. 10 / 855,294, filed May 26, 2004; a continuation-in-part of application Ser. No. 11 / 115,631, filed Apr. 26, 2005; and a continuation-in-part of application Ser. No. 11 / 119,020, filed Apr. 29, 2005; each application of which is hereby incorporated herein by reference.BACKGROUND [0002] 1. Field of the Invention [0003] This invention is directed to the polymeric matrices that include poly(ester amides) to control the release profiles of agents from within these matrices. [0004] 2. Description of the State of the Art [0005] Biomaterial research scientists are striving to improve the compositions from which medical devices and coatings are produced. For example, the control of protein adsorption on an implant surface and the local administration of agents from an implant are areas of focus in biomaterials research. Uncontr...

Claims

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Application Information

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IPC IPC(8): A61L2/00A61L31/10A61L31/16
CPCA61L27/18A61L27/34A61L31/06A61L31/10A61L31/16A61L2300/604A61L2300/416C08L77/12A61P9/10
Inventor DESNOYER, JESSICA R.PACETTI, STEPHEN D.KLEINER, LOTHAR W.HOSSAINY, SYED F.A.CHEN, YUNG-MINGSTEWART, GORDONZHANG, GINA
Owner ABBOTT CARDIOVASCULAR
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