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Details for Patent: 5,451,410

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Details for Patent: 5,451,410

Title: Modified amino acids for encapsulating active agents
Abstract:Modified amino acids and methods for their preparation and use as oral delivery systems for pharmaceutical agents are described. The modified amino acids are preparable by reacting single amino acids or mixtures of two or more kinds of amino acids with an amino modifying agent such as benzene sulfonyl chloride, benzoyl chloride, and hippuryl chloride. The modified amino acids form encapsulating microspheres in the presence of the active agent under sphere-forming conditions. Alternatively, the modified amino acids may be used as a carrier by simply mixing the amino acids with the active agent. The modified amino acids are particularly useful in delivering peptides, e.g. insulin or calmodulin, or other agents which are sensitive to the denaturing conditions of the gastrointestinal tract.
Inventor(s): Milstein; Sam J. (Larchmont, NY), Barantsetvich; Evgueni N. (New Rochelle, NY)
Assignee: Emisphere Technologies, Inc. (Hawthorne, NY)
Filing Date:Apr 22, 1993
Application Number:08/051,019
Claims:1. A composition comprising

(A) a biologically active agent; and

(B) carrier comprising at least one modified amino acid selected from the group consisting of

(i) an acylated amino acid;

(ii) a sulfonated amino acid; or

(iii) a combination of (i) and (ii).

2. A composition as defined in claim 1, wherein said acylated amino acid comprises an amino acid amide and said sulfonated amino acid comprises an amino acid sulfonamide.

3. A composition as defined in claim 1, wherein said carrier comprises a mixture of at least two of said modified amino acids.

4. The composition according to claim 1, wherein said modified amino acids are derived from reaction of an amino acid with an amino reactive modifying agent selected from the group consisting of benzene sulfonyl chloride, benzoyl chloride, hippuryl chloride, and amino acid carbodiimide.

5. The composition according to claim 1, wherein said biologically-active agent is selected from the group consisting of human growth hormone, bovine growth hormone, interferon, interleukin-II, insulin, calcitonin, erythropoietin, atrial naturetic factor, antigens, and monoclonal antibody.

6. The composition according to claim 1, wherein said biologically active agent comprises at least one protein.

7. The composition according to claim 6, wherein said protein comprises erythropoietin.

8. The composition according to claim 6, wherein said protein comprises interferon.

9. The composition according to claim 6, wherein said protein comprises calcitonin.

10. The composition according to claim 6, wherein said protein comprises insulin.

11. The composition according to claim 6, wherein said protein comprises atrial naturetic factor.

12. The composition according to claim 6, wherein said protein comprises interleukin II.

13. The composition according to claim 6, wherein said protein comprises human growth factor.

14. The composition according to claim 6, wherein said protein comprises bovine growth factor.

15. The composition according to claim 1, wherein said biologically active agent comprises at least one polysaccharide.

16. The composition according to claim 15, wherein said polysaccharide comprises heparin.

17. The composition according to claim 1, wherein said biologically active agent comprises an antigen.

18. The composition according to claim 1, wherein said biologically active agent comprises a monoclonal antibody.

19. A composition as defined in claim 1, wherein said composition comprises a microsphere.

20. A composition as defined in claim 1, wherein said microsphere comprises a microcapsule.

21. A composition as defined in claim 19, wherein said amino acid amide comprises a benzene amide of an amino acid and said amino acid sulfonamide comprises a benzene sulfonamide.
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