Phenoxy alkyl diethanolamine and diisopropanolamine compounds for delivering active agents
View Patent ↗The present invention relates to particular phenoxy alkyl diethanolamine and diisopropanolamine compounds for delivering biologically active agents to a target. These compounds are well suited for forming non-covalent mixtures with active agents for oral, intracolonic, pulmonary, and other routes of administration to animals.
1. A compound selected from
and salts thereof.
2. The compound of claim 1 , wherein the compound is
or a salt thereof.
3. The compound of claim 1 , wherein the compound is
or a salt thereof.
4. The compound of claim 1 , wherein the compound is
or a salt thereof.
5. The compound of claim 1 , wherein the compound is
or a salt thereof.
6. The compound of claim 1 , wherein the compound is
or a salt thereof.
7. A pharmaceutical composition comprising:
(A) a biologically active agent; and
(B) a compound of claim 1 .
8. The pharmaceutical composition of claim 7 , wherein the biologically active agent comprises at least one protein, polypeptide, peptide, hormone, polysaccharide, mucopolysaccharide, carbohydrate, or lipid, and any combination thereof.
9. The pharmaceutical composition of claim 7 , wherein the biologically active agent is selected from the group consisting of: triptans, BIBN-4096BS, growth hormones, human growth hormones recombinant human growth hormones (rhGH), bovine growth hormones, porcine growth hormones, growth hormone releasing hormones, growth hormone releasing factor, 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 (TGF), 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, thrombopoeitin, filgrastim, postaglandins, 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.
10. The pharmaceutical composition of claim 7 , wherein the biologically active agent comprises a triptan, insulin, BIBN-4096BS, calcitonin, parathyroid hormone, erythropoietin, growth hormones and any combination thereof.
11. A dosage unit form comprising:
(A) a pharmaceutical composition of claim 7 ; and
(B) at least one of
(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.
12. A method for administering a biologically active agent to an animal in need of the agent, the method comprising administering orally to the animal a pharmaceutical composition of claim 7 .
13. A method for preparing a composition comprising mixing:
(A) at least one biologically active agent;
(B) at least one compound of claim 1 ; and
(C) optionally, a dosing vehicle.
14. A compound selected from
and pharmaceutically acceptable salts thereof.
15. The pharmaceutical composition of claim 7 , wherein the biologically active agent is selected from the group consisting of: BIBN-4096BS, growth hormones, human growth hormones recombinant human growth hormones (rhGH), bovine growth hormones, porcine growth hormones, growth hormone releasing hormones, growth hormone releasing factor, 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, thrombopoeitin, filgrastim, postaglandins, 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.
16. The pharmaceutical composition of claim 7 , wherein the biologically active agent comprises insulin, BIBN-4096BS, calcitonin, parathyroid hormone, erythropoietin, growth hormones and any combination thereof.
17. A pharmaceutical composition comprising:
(A) a biologically active agent; and
(B) a compound of claim 14 ;
wherein the biologically active agent is selected the group consisting of: BIBN-4096BS, growth hormones, human growth hormones recombinant human growth hormones (rhGH), bovine growth hormones, porcine growth hormones, growth hormone releasing hormones, growth hormone releasing factor, 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, thrombopoeitin, filgrastim, postaglandins, 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.
18. The pharmaceutical composition of claim 17 , wherein the biologically active agent is selected from the group consisting of insulin, BIBN-4096BS, calcitonin, parathyroid hormone, erythropoietin, growth hormones and any combination thereof.
19. The compound of claim 14 , wherein the compound is
or a pharmaceutically acceptable salt thereof.
20. A pharmaceutical composition comprising:
(A) a biologically active agent; and
(B) the compound of claim 19 .
21. A method for administering a biologically active agent to an animal in need of the agent, the method comprising administering orally to the animal a pharmaceutical composition of claim 20 .