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Details for Patent: 7,005,141

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Details for Patent: 7,005,141

Title:Oral drug delivery compositions and methods
Abstract: The present invention relates to an oral drug delivery system, and in particular to modified amino acids and modified amino acid derivatives for use as a delivery system of sensitive agents such as bioactive peptides. The modified amino acids and derivatives can form non-covalent mixtures with active biological agents and in an alternate embodiment can releasably carry active agents. Modified amino acids can also form drug containing microspheres. These mixtures are suitable for oral administration of biologically active agents to animals. Methods for the preparation of such amino acids are also disclosed.
Inventor(s): Milstein; Sam J. (Larchmont, NY), Barantsevitch; Evgueni N. (New Rochelle, NY), Sarubbi; Donald J. (Bronxville, NY), Leone-Bay; Andrea (Ridgefield, CT), Paton; Duncan R. (Purdys, NY)
Assignee: Emisphere Technologies Inc. (Tarrytown, NY)
Filing Date:Aug 20, 2002
Application Number:10/225,104
Claims:1. A composition comprising: (A) at least one biologically-active agent; and (B) a compound having the formula: Ar--Y--(R.sup.1).sub.n--OH wherein: Ar is a substituted or unsubstituted phenyl; Y is ##STR00010## R.sup.1 has the formula ##STR00011## wherein: R.sup.3 is C.sub.1 to C.sub.24 alkyl; R.sup.4 is hydrogen, C.sub.1 to C.sub.4 alkyl, or C.sub.1 to C.sub.4 alkenyl; and n is equal to 1.

2. The composition of claim 1, wherein said biologically-active agent is selected from the group consisting of a peptide, a polysaccharide, a mucopolysaccharide, a carbohydrate, a lipid or any combination thereof.

3. The composition of claim 2, wherein said biologically-active agent is a peptide.

4. The composition of claim 2, wherein said biologically-active agent is a polysaccharide.

5. The composition of claim 2, wherein said biologically-active agent is a mucopolysaccharide.

6. The composition of 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, low molecular weight heparin, calcitonin, erythropoietin, atrial naturetic factor, an antigen, a monoclonal antibody, somatostatin, adrenocorticotropin, gonadotropin releasing hormone, oxytocin, vasopressin, cromolyn sodium, vancomycin, desferrioxamine, or any combination thereof.

7. The composition of claim 6, wherein said biologically-active agent is human growth hormone.

8. The composition of claim 6, wherein said biologically-active agent is interferon.

9. The composition of claim 6, wherein said biologically-active agent is insulin.

10. The composition of claim 6, wherein said biologically-active agent is heparin.

11. The composition of claim 6, wherein said biologically-active agent is low molecular weight heparin.

12. The composition of claim 6, wherein said biologically-active agent is calcitonin.

13. The composition of claim 6, wherein said biologically-active agent is erythropoietin.

14. The composition of claim 6, wherein said biologically-active agent is an antigen.

15. The composition of claim 6, wherein said biologically-active agent is cromolyn sodium.

16. A dosage unit form comprising (A) the composition of claim 1; and (B) (a) an excipient (b) a diluent, (c) a disintegrant, (d) a lubricant, (e) a plasticizer, (f) a colorant, (g) a dosing vehicle, or (h) any combination thereof.

17. The dosage unit form of claim 16, comprising a tablet, a capsule, or a liquid.

18. The dosage unit form of claim 17, wherein said biologically-active agent is selected from the group consisting of a peptide, a polysaccharide, a mucopolysaccharide, a carbohydrate, a lipid or any combination thereof.

19. The dosage unit form of claim 18, wherein said biologically-active agent is a peptide.

20. The dosage unit form of claim 18, wherein said biologically-active agent is a polysaccharide.

21. The dosage unit form of claim 18, wherein said biologically-active agent is a mucopolysaccharide.

22. The dosage unit form of claim 17, 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, low molecular weight heparin, calcitonin, erythropoietin, atrial naturetic factor, an antigen, a monoclonal antibody, somatostatin, adrenocorticotropin, gonadotropin releasing hormone, oxytocin, vasopressin, cromolyn sodium, vancomycin, desferrioxamine, or any combination thereof.

23. The dosage unit form of claim 22, wherein said biologically-active agent is human growth hormone.

24. The dosage unit form of claim 22, wherein said biologically-active agent is interferon.

25. The dosage unit form of claim 22, wherein said biologically-active agent is insulin.

26. The dosage unit form of claim 22, wherein said biologically-active agent is heparin.

27. The dosage unit form of claim 22, wherein said biologically-active agent is low molecular weight heparin.

28. The dosage unit form of claim 22, wherein said biologically-active agent is calcitonin.

29. The dosage unit form of claim 22, wherein said biologically-active agent is erythropoietin.

30. The dosage unit form of claim 22, wherein said biologically-active agent is an antigen.

31. The dosage unit form of claim 22, wherein said biologically-active agent is cromolyn sodium.

32. A method for preparing a composition, said method comprising mixing: (A) at least one biologically-active agent; and (B) a compound having the formula: Ar--Y--(R.sup.1).sub.n--OH wherein: Ar is a substituted or unsubstituted phenyl; Y is ##STR00012## R.sup.1 has the formula ##STR00013## wherein: R.sup.3 is C.sub.1 to C.sub.24 alkyl, (C.sub.1 to C.sub.10 alkyl) phenyl, or phenyl (C.sub.1 to C.sub.10 alkyl); R.sup.4 is hydrogen, C.sub.1 to C.sub.4 alkyl, or C.sub.1 to C.sub.4 alkenyl; and n is equal to 1.

33. The method of claim 32, wherein said biologically-active agent is selected from the group consisting of a peptide, a polysaccharide, a mucopolysaccharide, a carbohydrate, a lipid or any combination thereof.

34. The method of claim 33, wherein said biologically-active agent is a peptide.

35. The method of claim 33, wherein said biologically-active agent is a polysaccharide.

36. The method of claim 33, wherein said biologically-active agent is a mucopolysaccharide.

37. The method of claim 32, 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, low molecular weight heparin, calcitonin, erythropoietin, atrial naturetic factor, an antigen, a monoclonal antibody, somatostatin, adrenocorticotropin, gonadotropin releasing hormone, oxytocin, vasopressin, cromolyn sodium, vancomycin, desferrioxamine, or any combination thereof.

38. The method of claim 37, wherein said biologically-active agent is human growth hormone.

39. The method of claim 37, wherein said biologically-active agent is interferon.

40. The method of claim 37, wherein said biologically-active agent is insulin.

41. The method of claim 37, wherein said biologically-active agent is heparin.

42. The method of claim 37, wherein said biologically-active agent is low molecular weight heparin.

43. The method of claim 37, wherein said biologically-active agent is calcitonin.

44. The method of claim 37, wherein said biologically-active agent is erythropoietin.

45. The method of claim 37, wherein said biologically-active agent is an antigen.

46. The method of claim 37, wherein said biologically-active agent is cromolyn sodium.
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