Compounds and compositions for delivering active agents

1. A compound of the formula

or a salt thereof, wherein:

R 1 is —OH or —OCH 3 ;

R 2 , R 3 , R 4 , R 5 are independently selected from hydrogen, halogen, —OH, —OCH 3 , C 1 –C 4 alkyl, —NH 2 , —NH(CH 3 ), —N(CH 3 ) 2 , or —NO 2 ;

m is 0, 1, 3 or 4;

R 6 is a phenyl substituted with —O—R 7 —COOH at the ortho, meta, or para position;

R 6 is optionally substituted with one or more members selected from halogen, —OH, —OCH 3 , C 1 –C 4 alkyl, —NH 2 , NH(CH 3 ), —N(CH 3 ) 2 , and —NO 2 ; and

R 7 is C 2 –C 12 n-alkylene,

wherein m is 0 when R 1 is —OCH 3 .

2. A compound of the formula

or a salt thereof, wherein:

R 1 is —OH;

R 2 , R 3 , R 4 , and R 5 are independently selected from hydrogen, halogen, —OH, —OCH 3 , C 1 –C 4 alkyl, —NH 2 , —NH(CH 3 ), —N(CH 3 ) 2 , or —NO 2 ;

m is an integer ranging from 0 to 4;

R 6 is a phenyl substituted with —O—R 7 —COOH at the ortho, meta, or para position;

R 6 is optionally substituted with one or more members selected from halogen, —OH, —OCH 3 , C 1 –C 4 alkyl, —NH 2 , NH(CH 3 ), —N(CH 3 ) 2 , and —NO 2 ; and

R 7 is C 2 –C 12 n-alkylene.

3. The compound of claim 1 wherein said compound is:

or a salt thereof.

4. The compound of claim 3 wherein said compound is the disodium salt of compound 1.

5. A composition comprising:

(A) an active agent; and

(B) a compound as defined in claim 1 .

6. A composition comprising:

(A) an active agent; and

(B) a compound as defined in claim 3 .

7. A composition comprising:

(A) an active agent; and

(B) a compound as defined in claim 4 .

8. The composition of claim 5 , wherein the active agent is selected from the group consisting of a biologically active agent, a chemically active agent, and a combination thereof.

9. The composition of claim 8 , wherein the biologically active agent comprises at least one protein, polypeptide, peptide, hormone, polysaccharide, mucopolysaccharide, carbohydrate, or lipid.

10. The composition of claim 9 , wherein the biologically active agent is selected from the group consisting of: growth hormones, interferons, interleukin, insulin, heparin, calcitonin, erythropoietin, 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, parathyroid hormone, fragments of parathyroid hormone, antimicrobials, anti-fungal agents, vitamins, and analogs, fragments, mimetics and polyethylene glycol (PEG)-modified derivatives of these compounds, and any combination thereof.

11. The composition of claim 10 , wherein the biologically active agent comprises insulin, unfractionated heparin, low molecular weight heparin, very low molecular weight heparin, ultra low molecular weight heparin, calcitonin, PTH, EPO, hGH or combinations thereof.

12. The composition of claim 11 , wherein the biologically active agent comprises insulin.

13. A dosage unit form comprising:

(A) the composition of claim 5 ; 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.

14. The dosage unit form of claim 13 , wherein the active agent is selected from the group consisting of a biologically active agent, a chemically active agent, and a combination thereof.

15. The dosage unit form of claim 14 , wherein the biologically active agent comprises at least one protein, polypeptide, peptide, hormone, polysaccharide, mucopolysaccharide, carbohydrate, or lipid.

16. The dosage unit form of claim 15 , wherein the biologically active agent is selected from the group consisting of: growth hormones, interferons, interleukin, insulin, heparin, calcitonin, erythropoietin, 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, parathyroid hormone, fragments of parathyroid hormone, antimicrobials, anti-fungal agents, vitamins, and analogs, fragments, mimetics and polyethylene glycol (PEG)-modified derivatives of these compounds, and any combination thereof.

17. The dosage unit form of claim 15 , wherein the biologically active agent comprises insulin, unfractionated heparin, low molecular weight heparin, very low molecular weight heparin, ultra low molecular weight heparin, calcitonin, PTH, EPO, hGH, or combinations thereof.

18. The dosage unit form of claim 17 , wherein the active agent comprises insulin.

19. The dosage unit form of claim 13 , wherein the dosage unit form is a tablet, a capsule, a powder, or a liquid.

20. The dosage unit form of claim 13 , wherein dosing unit form comprises a dosing vehicle and dosing vehicle is selected from the group consisting of water, 25% aqueous propylene glycol, phosphate buffer, 1,2-propane diol, ethanol, and any combination thereof.

21. A method for administering a biologically-active agent to an animal in need of the agent, the method comprising administering to the animal the composition of claim 5 .

22. A method for administering a biologically-active agent to an animal in need of the agent, the method comprising administering to the animal via the pulmonary route the composition of claim 7 .

23. 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.

24. The compound of claim 1 wherein said compound is:

or a salt thereof.

25. The compound of claim 1 wherein said compound is:

or a salt thereof.

26. The compound of claim 1 wherein said compound is:

or a salt thereof.

27. The compound of claim 1 wherein said compound is:

or a salt thereof.

28. The compound of claim 1 wherein said compound is:

or a salt thereof.

29. The compound of claim 1 wherein said compound is:

or a salt thereof.

30. The compound of claim 1 wherein said compound is:

or a salt thereof.

31. The compound of claim 1 wherein said compound is:

or a salt thereof.

32. A compound of the formula:

or a salt thereof.

33. The compound of claim 1 wherein m is 0.

34. The compound of claim 1 , wherein R 7 is C 3 –C 9 n-alkylene.

35. The compound of claim 34 , wherein R 7 is C 3 –C 7 n-alkylene.

36. The compound of claim 1 , wherein R 6 is substituted with a chlorine at the para position to the O—R 7 —COOH substituent.

37. The compound of claim 2 , wherein m is 1–4.