Self assembling diketopiperazine drug delivery system
First Claim
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1. A microparticulate system for drug delivery comprising:
- diketopiperazine microparticles incorporating a biologically active agent selected from the group consisting of proteins, peptides, polysaccharides, lipids, lipopolysaccharides, nucleic acids and other biologically active organic molecules,wherein the microparticles are stable at a first defined pH due to association and precipitation of the diketopiperazines and unstable at a second defined pH due to dissociation of the diketopiperazines.
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Abstract
Drug delivery systems have been developed based on the formation of diketopiperazine (or analogs) microparticles. In the preferred embodiment the microparticle is stable at low pH and disintegrates at physiological pH, and is particularly useful for oral drug delivery. In the most preferred embodiment the microparticles are formed in the presence of the drug to be delivered, for example, insulin or heparin. The diketopiperazine synthetic intermediates are preferably formed by cyclodimerization to form diketopiperazine derivatives at elevated conditions under dehydrating conditions, then precipitated with drug to be incorporated into microparticles.
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Citations
20 Claims
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1. A microparticulate system for drug delivery comprising:
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diketopiperazine microparticles incorporating a biologically active agent selected from the group consisting of proteins, peptides, polysaccharides, lipids, lipopolysaccharides, nucleic acids and other biologically active organic molecules, wherein the microparticles are stable at a first defined pH due to association and precipitation of the diketopiperazines and unstable at a second defined pH due to dissociation of the diketopiperazines. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8)
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9. A method for making a microparticulate system for drug delivery comprising
forming diketopiperazines in a solution with a first defined pH at which the diketopiperazines are soluble, adding to the diketopiperazine solution a biologically active agent selected from the group consisting of proteins, peptides, polysaccharides, lipids, lipopolysaccharides, nucleic acids and other biologically active organic molecules, imaging agents, and cell specific targeting agents, in a solution having a second defined pH precipitating the diketopiperazines to form microparticles of the diketopiperazines containing the biologically active agent.
- 14. A method for administering a biologically active agent to a patient comprising providing the agent selected from the group consisting of proteins, peptides, polysaccharides, lipids, lipopolysaccharides, nucleic acids and other biologically active organic molecules, imaging agents, and cell specific targeting agents, in combination with microparticles formed of diketopiperazines, wherein the microparticles are stable at a first defined pH due to association and precipitation of the diketopiperazines and unstable at a second defined pH due to dissociation of the diketopiperazines.
Specification