# US 7,744,910 B2 · Compounds and compositions for delivering active agents > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 7,744,910 B2 - Document ID: US7744910B2 - Status: Granted - Kind: B2 - Application number: 11/531,602 - Filed: 2006-09-13 - Published: 2007-01-11 - Granted: 2010-06-29 - Earliest claimed: 1998-08-07 - Assignees: Emisphere Technologies, Inc. - Inventors: David Gschneidner; Andrea Leone-Bay; Eric Wang; Lynn Errigo; Koc-Kan Ho; Jeffrey Bruce Press; Nai Fang Wang; Pingwah Tang - Web page: https://patentgrep.com/patent/US7744910B2 ## CPC - C07C 233/83: of an acyclic saturated carbon skeleton - A61K 9/0014: {Skin, i.e. galenical aspects of topical compositions (non-active ingredients are additionally classified in A61K47/00; A61K9/0009, A61K9/0021, A61K9/7015, A61K9/7023 take precedence; cosmetic preparations A61K8/00, A61Q; preparations for wound dressings or bandages A61L26/00)} - A61K 9/0019: {Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner (non-active ingredients are additionally classified in A61K47/00)} - A61K 9/0031: {Rectum, anus} - A61K 47/18: Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids - A61P 5/06: of the anterior pituitary hormones, e.g. TSH, ACTH, FSH, LH, PRL, GH - A61P 5/18: of the parathyroid hormones - A61P 7/02: Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors - A61P 19/10: for osteoporosis - C07C 233/51: having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings - C07C 235/24: having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring - C07C 235/34: having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms - C07C 235/60: having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms - C07C 235/64: having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring - C07C 235/74: of a saturated carbon skeleton - C07C 271/28: to a carbon atom of a non-condensed six-membered aromatic ring - C07C 271/54: to carbon atoms of hydrocarbon radicals substituted by carboxyl groups - C07C 271/58: with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring - C07C 275/42: being further substituted by carboxyl groups - C07C 309/59: Nitrogen analogues of carboxyl groups - C07C 317/44: having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton - C07D 239/91: with aryl or aralkyl radicals attached in position 2 or 3 - C07D 239/94: Nitrogen atoms - C07D 239/96: Two oxygen atoms - C07D 265/26: Two oxygen atoms, e.g. isatoic anhydride - C07D 311/18: substituted otherwise than in position 3 or 7 - C07D 317/68: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen - A61K 38/00: Medicinal preparations containing peptides (peptides containing beta-lactam rings A61K31/00; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, A61K31/00; ergot alkaloids of the cyclic peptide type A61K31/48; containing macromolecular compounds having statistically distributed amino acid units A61K31/74; medicinal preparations containing antigens or antibodies A61K39/00; medicinal preparations characterised by the non-active ingredients, e.g. peptides as drug carriers, A61K47/00) - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) - A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) ## Abstract Compounds and compositions for the delivery of active agents are provided. Methods of administration and preparation are provided as well. ## Claims ### Claim 1 A compound represented by the formula: or a pharmaceutically acceptable salt thereof. ### Claim 2 (depends on 1) The compound of claim 1 wherein the pharmaceutically acceptable salt is sodium salt. ### Claim 3 (depends on 1) A composition comprising: (A) at least one biologically active agent; and (B) the compound of claim 1. ### Claim 4 (depends on 3) The compound of claim 3 wherein the pharmaceutically acceptable salt is sodium salt. ### Claim 5 (depends on 3) The composition of defined in claim 3, wherein said biologically active agent comprises at least one protein, polypeptide, peptide, hormone, polysaccharide, mucopolysaccharide, carbohydrate, or lipid. ### Claim 6 (depends on 5) The composition of claim 5, wherein said biologically active agent comprises a protein, polypeptide or peptide. ### Claim 7 (depends on 5) The composition of claim 5, wherein said biologically active agent comprises a mucopolysaccharide. ### Claim 8 (depends on 3) The composition of claim 3, wherein said biologically active agent is selected from the group consisting of: growth hormone, growth hormone-releasing hormones, interferons, interleukin-1, interleukin-2, insulin, insulin-like growth factor (IGF), heparin, 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, vancomycin, desferrioxamine (DFO), parathyroid hormone (PTH), antimicrobials, anti-fungal agents; analogs, fragments, mimetics and polyethylene glycol (PEG)-modified derivatives of these compounds; and any combination thereof. ### Claim 9 (depends on 8) The composition of claim 8, wherein said biologically active agent is selected from a growth hormone, interferon, insulin, heparin, cromolyn sodium, an antigen, an anti-microbial agent, calcitonin, parathyroid hormone, erythropoietin, and combinations thereof. ### Claim 10 (depends on 9) The composition of claim 9, wherein said growth hormone is selected from human growth hormones (hGH), recombinant human growth hormones (rhGH), bovine growth hormones, porcine growth hormones, or a combination thereof. ### Claim 11 (depends on 8) The composition of claim 8, wherein said biologically active agent is interferon. ### Claim 12 (depends on 8) The composition of claim 8, wherein said biologically active agent is insulin. ### Claim 13 (depends on 8) The composition of claim 8, wherein said insulin is selected from porcine insulin, bovine insulin, human insulin, and human recombinant insulin. ### Claim 14 (depends on 8) The composition of claim 8, wherein said biologically active agent is heparin. ### Claim 15 (depends on 14) The composition of claim 14, wherein said heparin is selected from low molecular weight heparin, very low molecular weight heparin, ultra low molecular weight heparin, heparinoids, dermatans, chondroitins, or a combination thereof. ### Claim 16 (depends on 15) The composition of claim 15, wherein said biologically active agent is low molecular weight heparin. ### Claim 17 (depends on 8) The composition of claim 8, wherein said biologically active agent is cromolyn sodium. ### Claim 18 (depends on 17) The composition of claim 17, wherein said cromolyn sodium is selected from sodium chromoglycate, disodium chromoglycate or a combination thereof. ### Claim 19 (depends on 8) The composition of claim 8, wherein said biologically active agent is an antigen. ### Claim 20 (depends on 8) The composition of claim 8, wherein said biologically active agent is an anti-microbial agent. ### Claim 21 (depends on 8) The composition of claim 8, wherein said biologically active agent is a calcitonin. ### Claim 22 (depends on 21) The composition of claim 21, wherein said calcitonin is selected from salmon calcitonin, eel calcitonin, human calcitonin or a combination thereof. ### Claim 23 (depends on 8) The composition of claim 8, wherein said biologically active agent is parathyroid hormone. ### Claim 24 (depends on 8) The composition of claim 8, wherein said biologically active agent is erythropoietin. ### Claim 25 (depends on 3) A dosage unit form comprising (A) a composition as defined in claim 3; 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. ### Claim 26 (depends on 25) The dosage unit form of claim 25 wherein the pharmaceutically acceptable salt is the sodium salt. ### Claim 27 (depends on 25) The dosage unit form of claim 25, comprising a powder. ### Claim 28 (depends on 25) The dosage unit form of claim 25 comprising a tablet. ### Claim 29 (depends on 25) The dosage unit form of claim 25 comprising a capsule. ### Claim 30 (depends on 25) The dosage unit form of claim 25 comprising a liquid. ### Claim 31 (depends on 25) The dosage unit form of claim 25, wherein said biologically active agent comprises at least one protein, polypeptide, peptide, hormone, polysaccharide, mucopolysaccharide, carbohydrate, or lipid. ### Claim 32 (depends on 31) The dosage unit form of claim 31, wherein said biologically active agent comprises a protein, polypeptide, or peptide. ### Claim 33 (depends on 31) The dosage unit form of claim 31, wherein said biologically active agent comprises a mucopolysaccharide. ### Claim 34 (depends on 25) The dosage unit form of claim 25, wherein said dosing vehicle is selected from the group consisting of water, 1,2-propane diol, ethanol, olive oil or any combination thereof. ### Claim 35 (depends on 25) The dosage unit form of claim 25, wherein said biologically active agent is selected from the group consisting of: growth hormone, growth hormone-releasing hormones, interferons, interleukin-1, interleukin-2, insulin, insulin-like growth factor (IGF), heparin, 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, vancomycin, desferrioxamine (DFO), parathyroid hormone (PTH), antimicrobials, anti-fungal agents; analogs, fragments, mimetics and polyethylene glycol (PEG)-modified derivatives of these compounds; and any combination thereof. ### Claim 36 (depends on 35) The dosage unit form of claim 35, wherein said biologically active agent is selected from a growth hormone, interferon, insulin, heparin, cromolyn sodium, an antigen, an anti-microbial agent, calcitonin, parathyroid hormone, erythropoietin, and combinations thereof. ### Claim 37 (depends on 35) The dosage unit form of claim 35, wherein said growth hormone is selected from human growth hormones (hGH), recombinant human growth hormones (rhGH), bovine growth hormones, porcine growth hormones, or a combination thereof. ### Claim 38 (depends on 35) The dosage unit form of claim 35, wherein said biologically active agent is interferon. ### Claim 39 (depends on 35) The dosage unit form of claim 35, wherein said biologically active agent is insulin. ### Claim 40 (depends on 39) The dosage unit form of claim 39, wherein said insulin is selected from porcine insulin, bovine insulin, human insulin, and human recombinant insulin. ### Claim 41 (depends on 35) The dosage unit form of claim 35, wherein said biologically active agent is heparin. ### Claim 42 (depends on 41) The composition of claim 41, wherein said heparin is selected from low molecular weight heparin, very low molecular weight heparin, ultra low molecular weight heparin, heparinoids, dermatans, chondroitins, or a combination thereof. ### Claim 43 (depends on 42) The dosage unit form of claim 42, wherein said biologically active agent is low molecular weight heparin. ### Claim 44 (depends on 35) The dosage unit form of claim 35, wherein said biologically active agent is cromolyn sodium. ### Claim 45 (depends on 44) The dosage unit form of claim 44, wherein said cromolyn sodium is selected from sodium chromoglycate, disodium chromoglycate or a combination thereof. ### Claim 46 (depends on 35) The dosage unit form of claim 35, wherein said biologically active agent is an antigen. ### Claim 47 (depends on 35) The dosage unit form of claim 35, wherein said biologically active agent is an anti-microbial agent. ### Claim 48 (depends on 35) The dosage unit form of claim 35, wherein said biologically active agent is calcitonin. ### Claim 49 (depends on 35) The dosage unit form of claim 35, wherein said calcitonin is selected from salmon calcitonin, eel calcitonin, human calcitonin or a combination thereof. ### Claim 50 (depends on 35) The dosage unit form of claim 35, wherein said biologically active agent is parathyroid hormone. ### Claim 51 (depends on 35) The dosage unit form of claim 35, wherein said biologically active agent is erythropoietin. ### Claim 52 (depends on 3) A method for administering a biologically active agent to an animal, said method comprising administering to said animal the composition of claim 3. ### Claim 53 (depends on 52) The method of claim 52 wherein the pharmaceutically acceptable salt is the sodium salt. ### Claim 54 (depends on 52) The method of claim 52, wherein said biologically active agent is administered by a route selected from: oral, intranasal, sublingual, intraduodenal, subcutaneous, buccal, intracolonic, rectal, vaginal, mucosal, pulmonary, transdermal, intradermal, parenteral, intravenous, intramuscular and intraocular. ### Claim 55 (depends on 52) The method of claim 52, wherein said biologically active agent is administered by the oral route. ### Claim 56 (depends on 52) The method of claim 52, wherein said biologically active agent comprises at least one protein, polypeptide, peptide, hormone, polysaccharide, mucopolysaccharide, carbohydrate, or lipid. ### Claim 57 (depends on 56) The method of claim 56, wherein said biologically active agent comprises a protein, polypeptide, or peptide. ### Claim 58 (depends on 56) The method of claim 56, wherein said biologically active agent comprises a mucopolysaccharide. ### Claim 59 (depends on 52) The method of claim 52, wherein said biologically active agent is selected from the group consisting of: growth hormone, growth hormone-releasing hormones, interferons, interleukin-1, interleukin-2, insulin, insulin-like growth factor (IGF), heparin, 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, vancomycin, desferrioxamine (DFO), parathyroid hormone (PTH), antimicrobials, anti-fungal agents; analogs, fragments, mimetics and polyethylene glycol (PEG)-modified derivatives of these compounds; and any combination thereof. ### Claim 60 (depends on 59) The method of claim 59, wherein said biologically active agent is selected from a growth hormone, interferon, insulin, heparin, cromolyn sodium, an antigen, an anti-microbial agent, calcitonin, parathyroid hormone, erythropoietin, and combinations thereof. ### Claim 61 (depends on 59) The method of claim 59, wherein said growth hormone is selected from human growth hormones (hGH), recombinant human growth hormones (rhGH), bovine growth hormones, porcine growth hormones, or a combination thereof. ### Claim 62 (depends on 59) The method of claim 59, wherein said biologically active agent is interferon. ### Claim 63 (depends on 59) The method of claim 59, wherein said biologically active agent is insulin. ### Claim 64 (depends on 63) The method of claim 63, wherein said insulin is selected from porcine insulin, bovine insulin, human insulin, and human recombinant insulin. ### Claim 65 (depends on 59) The method of claim 59, wherein said biologically active agent comprises heparin. ### Claim 66 (depends on 65) The method of claim 65, wherein said heparin is selected from low molecular weight heparin, very low molecular weight heparin, ultra low molecular weight heparin, heparinoids, dermatans, chondroitins, or a combination thereof. ### Claim 67 (depends on 66) The method of claim 66, wherein said biologically active agent is low molecular weight heparin. ### Claim 68 (depends on 59) The method of claim 59, wherein said biologically active agent is cromolyn sodium. ### Claim 69 (depends on 68) The method of claim 68, wherein said cromolyn sodium is sodium chromoglycate, disodium chromoglycate or a combination thereof. ### Claim 70 (depends on 59) The method of claim 59, wherein said biologically active agent is an antigen. ### Claim 71 (depends on 43) The method of claim 43, wherein said biologically active agent is an anti-microbial agent. ### Claim 72 (depends on 43) The method of claim 43, wherein said biologically active agent is calcitonin. ### Claim 73 (depends on 43) The method of claim 43, wherein said calcitonin is selected from salmon calcitonin, eel calcitonin, human calcitonin or a combination thereof. ### Claim 74 (depends on 43) The method of claim 43, wherein said biologically active agent is parathyroid hormone. ### Claim 75 (depends on 43) The method of claim 43, wherein said biologically active agent is erythropoietin. ### Claim 76 (depends on 1) A method for preparing a composition, said method comprising mixing: (A) at least one biologically active agent; (B) at least one compound as defined in claim 1; and (C) optionally, a dosing vehicle. ### Claim 77 (depends on 76) The method of claim 76 wherein the pharmaceutically acceptable salt is sodium salt. ### Claim 78 (depends on 76) The method of claim 76, wherein said biologically active agent comprises at least one protein, polypeptide, peptide, hormone, polysaccharide, mucopolysaccharide, carbohydrate, or lipid. ### Claim 79 (depends on 78) The method of claim 78, wherein said biologically active agent comprises a protein, polypeptide, or peptide. ### Claim 80 (depends on 78) The method of claim 78, wherein said biologically active agent comprises a mucopolysaccharide. ### Claim 81 (depends on 76) The method of claim 76, wherein said biologically active agent is selected from the group consisting of: growth hormone, growth hormone-releasing hormones, interferons, interleukin-1, interleukin-2, insulin, insulin-like growth factor (IGF), heparin, 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, vancomycin, desferrioxamine (DFO), parathyroid hormone (PTH), antimicrobials, anti-fungal agents; analogs, fragments, mimetics and polyethylene glycol (PEG)-modified derivatives of these compounds; and any combination thereof.