Phenyl amine carboxylic acid compounds and compositions for delivering active agents

1. A compound selected from the group consisting of

Cpd #

R 1

R 2

R 3

R 4

R 5

R 6

R 7

R 8

1

H

H

H

H

COOH

(CH 2 ) 7

bond

H

2

H

H

H

H

C(O)NH 2

(CH 2 ) 7

bond

H

3

H

H

H

H

C(O)CH 3

(CH 2 ) 7

bond

H

4

H

H

H

H

C(O)NH 2

CH 2

Para-Ph

H

5

H

H

H

H

NO 2

(CH 2 ) 7

bond

H

and salts thereof.

2. A composition comprising:

(A) an active agent; and

(B) at least one compound having the formula

Cpd #

R 1

R 2

R 3

R 4

R 5

R 6

R 7

R 8

1

H

H

H

H

COOH

(CH 2 ) 7

bond

H

2

H

H

H

H

C(O)NH 2

(CH 2 ) 7

bond

H

3

H

H

H

H

C(O)CH 3

(CH 2 ) 7

bond

H

4

H

H

H

H

C(O)NH 2

CH 2

Para-Ph

H

5

H

H

H

H

NO 2

(CH 2 ) 7

bond

H

or a salt 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, small polar organic molecules, 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, recombinant human growth hormones, 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-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, bisphosphonates, alendronate, tiludronate, etidronate, clodronate, pamidronate, olpadronate, incadronate, parathyroid hormone, fragments of parathyroid hormone, antimicrobials, daptomycin, anti-fungal agents, vitamins; analogs, fragments, mimetics and polyethylene glycol-modified derivatives of these compounds, and any combination thereof.

6. The composition of claim 5 , wherein the biologically active agent comprises insulin, unfractionated heparin, low molecular weight heparin, very low molecular weight heparin, ultra low molecular weight heparin, calcitonin, parathyroid hormone, erythropoietin, daptomycin, human growth hormones, analogs, fragments, mimetics or polyethylene glycol-modified derivatives of these compounds; or any combination thereof.

7. The composition of claim 6 , wherein the biologically active agent comprises 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 wherein the biologically active agent comprises at least one protein, polypeptide, peptide, hormone, polysaccharide, mucopolysaccharide, small polar organic molecules, carbohydrate, or lipid.

11. The dosage unit form of claim 9 , wherein the biologically active agent is selected from the group consisting of:

growth hormones, human growth hormones, recombinant human growth hormones, 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-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, bisphosphonates, alendronate, tiludronate, etidronate, clodronate, pamidronate, olpadronate, incadronate, parathyroid hormone, parathyroid hormone, fragments of parathyroid hormone, antimicrobials, daptomycin, anti-fungal agents, vitamins, analogs, fragments, mimetics and polyethylene glycol-modified derivatives of these compounds, and any combination thereof.

12. The dosage unit form of claim 11 , wherein the biologically active agent comprises insulin, unfractionated heparin, low molecular weight heparin, very low molecular weight heparin, ultra low molecular weight heparin, calcitonin, parathyroid hormone, erythropoietin, human growth hormones, analogs, fragments, mimetics or polyethylene glycol-modified derivatives of these compounds; or any combination thereof.

13. The dosage unit form of claim 12 , wherein the active agent comprises calcitonin.

14. The dosage unit form of claim 9 , wherein the dosage unit form comprises a tablet, a capsule, a powder, or a liquid.

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) at least one compound as claimed in claim 1 ; and

(C) optionally, a dosing vehicle.