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Claims for Patent: 7,276,534

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Claims for Patent: 7,276,534

Title:Carbon-substituted diketopiperazine delivery systems
Abstract: Compositions useful in the delivery of active agents are provided. These delivery compositions include (a) an active agent; and (b) a carrier of at least one mono-C-substituted or di-C-substituted diketopiperazine. Methods for preparing these compositions and administering these compositions are also provided.
Inventor(s): Milstein; Sam J. (Larchmont, NY)
Assignee: Emisphere Technologies, Inc. (Tarrytown, NY)
Application Number:11/061,590
Patent Claims: 1. A composition comprising (a) a biologically active agent; and (b) at least one diketopiperazine having the formula: ##STR00005## wherein R and R.sup.1 are C.sub.1-C.sub.24 alkyl having a functional group selected from halogen, oxygen, sulfur or nitrogen; R and R.sup.1 optionally interrupted with O, N, or S; R and R.sup.1 are optionally substituted with C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 alkenyl or CO.sub.2R.sup.2 or any combination thereof; and R.sup.2 is hydrogen, C.sub.1-C.sub.4 alkyl, or C.sub.1-C.sub.4 alkenyl.

2. The composition as defined in claim 1, further comprising a microsphere.

3. The composition as defined in claim 2, wherein said microsphere comprises a microcapsule.

4. The composition as defined in claim 2, wherein said microsphere has a diameter of less than about 10 .mu.m.

5. The composition as defined in claim 1, wherein said biologically active agent is selected from the group consisting of human growth hormone, bovine growth hormone, growth hormone-releasing hormone, an interferon, interleukin-I, interleukin-II, insulin, heparin, calcitonin, erythropoietin, atrial naturetic factor, a monoclonal antibody, somatostatin, adrenocorticotropin, gonadotropin releasing hormone, oxytocin, vasopressin, vancomycin, or any combination of any of the foregoing.

6. The composition as defined in claim 1, wherein said biologically active agent is selected from the group consisting of an interferon, interleukin-I, interleukin-II, insulin, heparin, calcitonin, oxytocin, vasopressin, vancomycin, or any combination of any of the foregoing.

7. The composition as defined in claim 1, wherein said diketopiperazine is derived from lysine.

8. The composition as defined in claim 1, wherein R and R.sup.1 are substituted with CO.sub.2R.sup.2 and R.sup.2 is H.

9. The composition as defined in claim 1, wherein Rand R.sup.1 are substituted with a C.sub.1-C.sub.4 alkenyl group.

10. The composition as defined in claim 8, wherein R and R.sup.1 are substituted with a C.sub.1-C.sub.4 alkenyl group.

11. The composition as defined in claim 1, wherein R and R.sup.1 are interrupted by nitrogen.

12. The composition as defined in claim 8, wherein R and R.sup.1 are interrupted by nitrogen.

13. The composition as defined in claim 1, wherein the functional group is oxygen.

14. The composition as defined in any of claims 1-4 or 7-13, wherein the biologically active agent is insulin.

15. A method of administering insulin to a subject in need thereof comprising administering to the subject the composition of claim 14.
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