Compounds and compositions for delivering active agents

1. A compound selected from the group consisting of:

and salts thereof.

2. A composition comprising:

(A) an active agent; and

(B) a compound selected from the group consisting of

and salts thereof, and mixtures thereof.

3. The composition of claim 2 , wherein the active agent is selected from the group consisting of a biologically active agent, a chemically active agent, and a combination thereof.

4. The composition of claim 3 , wherein the biologically active agent comprises at least one protein, polypeptide, peptide, hormone, polysaccharide, mucopolysaccharide, carbohydrate, or lipid.

5. The composition of claim 3 , wherein the biologically active agent is selected from the group consisting of:

growth hormones, human growth hormones (hGH), recombinant human growth hormones (rhGH), bovine growth hormones, porcine growth hormones, growth hormone-releasing hormones, interferons, α-interferon, β-interferon, γ-interferon, interleukin- 1, interleukin-2, insulin, porcine insulin, bovine insulin, human insulin, human recombinant insulin, insulin-like growth factor (IGF), IGF-1, heparin, unfractionated heparin, heparinoids, dermatans, chondroitins, low molecular weight heparin, very low molecular weight heparin, ultra low molecular weight heparin, calcitonin, salmon calcitonin, eel calcitonin, human calcitonin; erythropoietin (EPO), atrial naturetic factor, antigens, monoclonal antibodies, somatostatin, protease inhibitors, adrenocorticotropin, gonadotropin releasing hormone, oxytocin, leutinizing-hormone-releasing-hormone, follicle stimulating hormone, glucocerebrosidase, thrombopoietin, filgrastim, prostaglandins, cyclosporin, vasopressin, cromolyn sodium, sodium chromoglycate, disodium chromoglycate, vancomycin, desferrioxamine (DFO), parathyroid hormone (PTH), fragments of PTH, antimicrobials, anti-fungal agents, vitamins; analogs, fragments, mimetics and polyethylene glycol (PEG)-modified derivatives of these compounds; and any combination thereof.

6. The composition of claim 3 , wherein the biologically active agent comprises salmon calcitonin, heparin, low molecular weight heparin, hGH or combinations thereof.

7. The composition of claim 3 , wherein the biologically active agent comprises salmon calcitonin.

8. A dosage unit form comprising:

(A) the composition of claim 2 ; 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.

9. The dosage unit form of claim 8 , wherein the active agent is selected from the group consisting of a biologically active agent, a chemically active agent, and a combination thereof.

10. The dosage unit form of claim 9 , wherein the biologically active agent comprises at least one protein, polypeptide, peptide, hormone, polysaccharide, mucopolysaccharide, carbohydrate, or lipid.

11. The dosage unit form of claim 10 , wherein the biologically active agent is selected from the group consisting of: growth hormones, human growth hormones (hGH), recombinant human growth hormones (rhGH), bovine growth hormones, porcine growth hormones, growth hormone-releasing hormones, interferons, α-interferon, β-interferon, γ-interferon, interleukin-1, interleukin-2, insulin, porcine insulin, bovine insulin, human insulin, human recombinant insulin, insulin-like growth factor(JGF), IGF-1, heparin, unfractionated heparin, hepannoids, dermatans, chondroitins, low molecular weight heparin, very low molecular weight heparin, ultra low molecular weight heparin, calcitonin, salmon calcitonin, eel calcitonin, human calcitonin; erythropoietin (EPO), atrial naturetic factor, antigens, monoclonal antibodies, somatostatin, protease inhibitors, adrenocorticotropin, gonadotropin releasing hormone, oxytocin, leutinizing-hormone-releasing-hormone, follicle stimulating hormone, glucocerebrosidase, thrombopoietin, filgrastim, prostaglandins, cyclosporin, vasopressin, cromolyn sodium, sodium chromoglycate, disodium chromoglycate, vancomycin, desferrioxamine (DFO), parathyroid hormone (PTH), fragments of PTH, antimicrobials, anti-fungal agents, vitamins; analogs, fragments, mimetics and polyethylene glycol (PEG)-modified derivatives of these compounds; and any combination thereof.

12. The dosage unit form of claim 10 , wherein the biologically active agent comprises salmon calcitonin.

13. The dosage unit form of claim 8 , wherein the dosage unit form is in the form of a tablet, a capsule, a particle, a powder, a sachet, or a liquid.

14. The dosage unit form of claim 8 , wherein the dosing vehicle is a liquid selected from the group consisting of water, aqueous propylene glycol, phosphate buffer, 1,2-propane diol, ethanol, and any combination thereof.

15. A method for administering an active agent to an animal in need of the agent, the method comprising administering orally to the animal the composition of claim 2 .

16. A method for preparing a composition comprising mixing:

(A) at least one active agent;

(B) the compound of claim 1 ; and

(C) optionally, a dosing vehicle.

17. A composition comprising:

(A) an active agent; and

(B) a compound selected from the group consisting of compounds of the formula:

and salts thereof;

wherein:

R 1 –R 4 are independently H, —OH, halogen, C 1 –C 4 alkoxy, C 1 –C 4 alkyl, C 2 –C 4 alkenyl, C 2 –C 4 alkynyl, or aryl;

R 1 –R 4 are optionally substituted with halogen, -OH, C 1 –C 4 alkoxy, or C 1 –C 4 alkyl;

R 5 is a C 1 –C 4 alkylene optionally substituted with a C 1 –C 4 alkyl group;

R 7 is H, or C 1 –C 4 alkyl, or aryl; and

R 7 is optionally substituted with halogen or —OH, and mixtures thereof.

18. The composition of claim 17 , wherein the active agent comprises at least one protein, polypeptide, peptide, hormone, polysaccharide, mucopolysaccharide, carbohydrate, or lipid.

19. A compound of the formula:

or a salt thereof

wherein:

R 1 –R 4 are independently H, —OH, halogen, C 1 –C 4 alkoxy, C 1 –C 4 alkyl, C 2 –C 4 alkenyl, C 2 –C 4 alkynyl, or aryl;

R 1 –R 4 are optionally substituted with halogen, —OH, C 1 –C 4 alkoxy, or C 1 –C 4 alkyl;

R 5 is a C 1 –C 4 alkylene optionally substituted with a C 1 –C 4 alkyl group; and

R 7 is a hydroxy substituted aryl.

20. A composition comprising:

(A) an active agent; and

(B) a compound selected from the compounds of claim 19 and mixtures thereof.

21. The composition of claim 20 , wherein the active agent comprises at least one protein, polypeptide, peptide, hormone, polysaccharide, mucopolysaccharide, carbohydrate, or lipid.

22. A method of administering a growth hormone comprising orally administering a composition comprising:

(a) a growth hormone; and

(b) a compound of claim 1 .

23. A method of administering an interferon comprising orally administering a composition comprising:

(a) an interferon; and

(b) a compound of claim 1 .

24. A method of administering interleuken-1 comprising orally administering a composition comprising:

(a) interleuken-1; and

(b) a compound of claim 1 .

25. A method of administering interleuken-2 comprising orally administering a composition comprising:

(a) interleuken-2; and

(b) a compound of claim 1 .

26. A method of administering heparin comprising orally administering a composition comprising:

(a) heparin; and

(b) a compound of claim 1 .

27. A method of administering calcitonin comprising orally administering a composition comprising:

(a) calcitonin; and

(b) a compound of claim 1 .

28. A method of administering erythropoietin comprising orally administering a composition comprising:

(a) erythropoietin; and

(b) a compound of claim 1 .

29. A method of administering a monoclonal antibody comprising orally administering a composition comprising:

(a) a monoclonal antibody; and

(b) a compound of claim 1 .

30. A method of administering a somatostatin comprising orally administering a composition comprising:

(a) a somatostatin; and

(b) a compound of claim 1 .

31. A method of administering a protease inhibitor comprising orally administering a composition comprising:

(a) a protease inhibitor; and

(b) a compound of claim 1 .

32. A method of administering a ganadotropin releasing hormone comprising orally administering a composition comprising:

(a) a ganadotropin releasing hormone; and

(b) a compound of claim 1 .

33. A method of administering a leutinizing-hormone-releasing hormone comprising orally administering a composition comprising:

(a) a leutinizing-hormone-releasing hormone; and

(b) a compound of claim 1 .

34. A method of administering a follicle stimulating hormone comprising orally administering a composition comprising:

(a) a follicle stimulating hormone; and

(b) a compound of claim 1 .

35. A method of administering a bisphosphonate comprising orally administering a composition comprising:

(a) a bisphosphonate; and

(b) a compound of claim 1 .

36. The method of claim 35 , wherein the bisphosphonate is alendronate.

37. A method for administering an active agent to an animal in need of the agent, the method comprising orally administering to the animal a composition comprising the active agent and a compound of the formula:

or a salt thereof,

wherein:

R 1 –R 4 are independently H, —OH, halogen, C 1 –C 4 alkoxy, C 1 –C 4 alkyl, C 2 –C 4 alkenyl, C 2 –C 4 alkynyl, or aryl;

R 1 –R 4 are optionally substituted with halogen, —OH, C 1 –C 4 alkoxy, or C 1 –C 4 alkyl;

R 5 is a C 1 –C 4 alkylene optionally substituted with a C 1 –C 4 alkyl group;

R 7 is H or C 2 –C 4 alkyl; and

R 7 is optionally substituted with halogen or —OH.

38. The method of claim 37 , wherein the active agent comprises at least one protein, polypeptide, peptide, hormone, polysaccharide, mucopolysaccharide, carbohydrate, or lipid.