CA2417388A1 - Therapeutic polyanhydride compounds for drug delivery - Google Patents

Therapeutic polyanhydride compounds for drug delivery Download PDF

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CA2417388A1
CA2417388A1 CA002417388A CA2417388A CA2417388A1 CA 2417388 A1 CA2417388 A1 CA 2417388A1 CA 002417388 A CA002417388 A CA 002417388A CA 2417388 A CA2417388 A CA 2417388A CA 2417388 A1 CA2417388 A1 CA 2417388A1
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polymer
acid
carbon atoms
biologically active
active compound
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CA2417388C (en
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Kathryn E. Uhrich
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Rutgers State University of New Jersey
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Rutgers, The State University
Kathryn E. Uhrich
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    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
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Abstract

Polyanhydrides which link low molecular weight drugs containing a carboxylic acid group and an amine, thiol, alcohol or phenol group within their structu re into polymeric drug delivery systems are provided. Also provided are methods of producing polymeric drug delivery systems via these polyanhydride linkers as well as methods of administering low molecular weight drugs to a host via the polymeric drug delivery systems.

Claims (37)

1. A polymer comprising a backbone, wherein the backbone comprises an anhydride linkage, and wherein the backbone comprises one or more groups that will yield a biologically active compound upon hydrolysis of the polymer; provided that the biologically active compound is not an ortho-hydroxy aryl carboxylic acid.
2. The polymer of claim 1 which comprises one or more units of formula (I) in the backbone:
-C(=O)R1-X-R2-X-R1-C(=O)-O- (I) wherein each R1 is group that will provide a biologically active compound upon hydrolysis of the polymer; provided that the biologically active compound is not an ortho-hydroxy aryl carboxylic acid each X is independently an amide linkage, a thioester linkage, or an ester linkage; and R2is a linking group.
3. The polymer of claims 1 or 2, wherein the biologically active compound is a non-steroidal anti-inflammatory drug, an anti-bacterial drug, an anti-fungal drug, an anti-cancer drug, an anti-thrombotic drug or an immunosuppressive drug.
4. The polymer of claims 1 or 2, wherein the biologically active compound is 3-amino-4-hydroxybutyric acid, 6-diazo-5-oxo-L-norleucine, aceclofenac, acediasulfone, alminoprofen, amfenac, amoxicillin, amphotericin B, ampicillin, apalcillin, apicycline, aspoxicillin, azaserine, aztreonam, bambermycin(s), biapenem, bromfenac, bucillamine, bumadizon, candicidin(s), carbenicillin, carprofen, carumonam, carzinophillin A, cefadroxil, cefamandole, cefatrizine, cefbuperazone, cefclidin, cefdinir, cefditoren, cefepime, cefetamet, cefixime, cefmenoxime, cefminox, cefodizime, cefonicid, cefoperazone, ceforanide, cefotaxime, cefotetan, cefotiam, cefozopran, cefpimizole, cefpiramide, cefpirome, cefprozil, cefroxadine, ceftazidime, cefteram, ceftibuten, ceftriaxone, cefuzonam, cephalexin, cephaloglycin, cephalosporin C, cephradine, ciprofloxacin, clinafloxacin, cyclacillin, denopterin, diclofenac, edatrexate, eflornithine, enfenamic acid, enoxacin, epicillin, etodolac, flomoxef, flufenamic acid, grepafloxacin, hetacillin, imipenem, lomefloxacin, lucensomycin, lymecycline, meclofenamic acid, mefenamic acid, melphalan, meropenem, methotrexate, moxalactam, mupirocin, mycophenolic acid, mycophenolic acid, nadifloxacin, natamycin, niflumic acid, norfloxacin, nystatin, oxaceprol, panipenem, pazufloxacin, penicillin N, pipemidic acid, podophyllinic acid 2-ethylhydrazide, procodazole, pteropterin, quinacillin, ritipenem, romurtide, S-adenosylmethionine, salazosulfadimidine, sparfloxacin, streptonigrin, succisulfone, sulfachrysoidine, sulfaloxic acid, teicoplanin, temafloxacin, temocillin, ticarcillin, tigemonam, tolfenamic acid, (N-((5-(((1,4-Dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl)methylamino)-2-thienyl)carbonyl)-L-glutamic acid), tosufloxacin, trovafloxacin, ubenimex or vancomycin.
5. The polymer of claim 3, wherein the anti-bacterial compound is acediasulfone, amfenac, amoxicillin, ampicillin, apalcillin, apicycline, aspoxicillin, aztreonam, bambermycin(s), biapenem, carbenicillin, carumonam, cefadroxil, cefamandole, cefatrizine, cefbuperazone, cefclidin, cefdinir, cefditoren, cefepime, cefetamet, cefixime, cefmenoxime, cefminox, cefodizime, cefonicid, cefoperazone, ceforanide, cefotaxime, cefotetan, cefotiam, cefozopran, cefpimizole, cefpiramide, cefpirome, cefprozil, cefroxadine, ceftazidime, cefteram, ceftibuten, ceftriaxone, cefuzonam, cephalexin, cephaloglycin, cephalosporin C, cephradine, ciprofloxacin, clinafloxacin, cyclacillin, enoxacin, epicillin, flomoxef, grepafloxacin, hetacillin, imipenem, lomefloxacin, lymecycline, meropenem, moxalactam, mupirocin, nadifloxacin, norfloxacin, panipenem, pazufloxacin, penicillin N, pipemidic acid, quinacillin, ritipenem, salazosulfadimidine, sparfloxacin, succisulfone, sulfachrysoidine, sulfaloxic acid, teicoplanin, temafloxacin, temocillin, ticarcillin, tigemonam, tosufloxacin, trovafloxacin, or vancomycin.
6. The polymer of claim 3, wherein the anti-fungal compound is amphotericin B, azaserine, candicidin(s), lucensomycin, natamycin or nystatin.
7. The polymer of claim 3, wherein the anti-cancer compound is 6-diazo-5-oxo-L-norleucine, azaserine, carzinophillin A, denopterin, edatrexate, eflornithine, melphalan, methotrexate, mycophenolic acid, podophyllinic acid 2-ethylhydrazide, pteropterin, streptonigrin, (N-((5-(((1,4-Dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl)methylamino)-2-thienyl)carbonyl)-L-glutamic acid), or, ubenimex.
8. The polymer of claim 3, wherein the immunosuppressive compound is bucillamine, mycophenolic acid, procodazole, romurtide or ubenimex.
9. The polymer of claim 3, wherein the non-steroidal anti-inflammatory compound is 3-amino-4-hydroxybutyric acid, aceclofenac, alminoprofen, bromfenac, bumadizon, carprofen, diclofenac, enfenamic acid, etodolac, flufenamic acid, meclofenamic acid, mefenamic acid, niflumic acid, oxaceprol, S-adenosylmethionine or tolfenamic acid.
10. The polymer of claim 4, wherein the biologically active compound is amoxicillin or cephalexin.
11. The polymer of claim 4, wherein the biologically active compound is carbidopa, or levodopa.
12. The polymer of claim 2 which is a polymer of formula (II) or(III) as illustrated herein above.
13. The polymer of claim 2, wherein R is a divalent, branched or unbranched, saturated or unsaturated, hydrocarbon chain, having from 1 to 25 carbon atoms, wherein one or more (e.g. 1, 2, 3, or 4) of the carbon atoms is optionally replaced by (-O-) or (-NR-), and wherein the chain is optionally substituted on carbon with one or more (e.g. 1, 2, 3, or 4) substituents selected from the group consisting of (C1-C6)alkoxy, (C3-C6)cycloalkyl, (C1-C6)alkanoyl, (C1-C6)alkanoyloxy, (C1-C6)alkoxycarbonyl, (C1-C6)alkylthio, azido, cyano, nitro, halo, hydroxy, oxo, carboxy, aryl, aryloxy, heteroaryl, and heteroaryloxy.
14. The polymer of claim 2, wherein R2 is a divalent, branched or unbranched, saturated or unsaturated, hydrocarbon chain, having from 1 to 25 carbon atoms, wherein the chain is optionally substituted on carbon with one or more (e.g. 1, 2, 3, or 4) substituents selected from the group consisting of (C1-C6)alkoxy, (C3-C6)cycloalkyl, (C1-C6)alkanoyl, (C1-C6)alkanoyloxy, (C1-C6)alkoxycarbonyl, (C1-C6)alkylthio, azido, cyano, nitro, halo, hydroxy, oxo, carboxy, aryl, aryloxy, heteroaryl, and heteroaryloxy.
15. The polymer of claim 2, wherein R2 is a peptide.
16. The polymer of claim 2, wherein R2 is an amino acid.
17. The polymer of claim 2, wherein R2 is a divalent, branched or unbranched, saturated or unsaturated, hydrocarbon chain, having from 1 to 25 carbon atoms, wherein one or more (e.g. 1, 2, 3, or 4) of the carbon atoms is optionally replaced by (-O-) or (-NR-).
18. The polymer of claim 2, wherein R2 is a divalent, branched or unbranched, saturated or unsaturated, hydrocarbon chain, having from 3 to 15 carbon atoms, wherein one or more (e.g. 1, 2, 3, or 4) of the carbon atoms is optionally replaced by (-O-) or (-NR-), and wherein the chain is optionally substituted on carbon with one or more (e.g. 1, 2, 3, or 4) substituents selected from the group consisting of (C1-C6)alkoxy, (C3-C6)cycloalkyl, (C1-C6)alkanoyl, (C1-C6)alkanoyloxy, (C1-C6)alkoxycarbonyl, (C1-C6)alkylthio, azido, cyano, nitro, halo, hydroxy, oxo, carboxy, aryl, aryloxy, heteroaryl, and heteroaryloxy.
19. The polymer of claim 2, wherein R2 is a divalent, branched or unbranched, saturated or unsaturated, hydrocarbon chain, having from 3 to 15 carbon atoms, wherein one or more (e.g. 1, 2, 3, or 4) of the carbon atoms is optionally replaced by (-O-) or (-NR-).
20. The polymer of claim 2, wherein R2 is a divalent, branched or unbranched, saturated or unsaturated, hydrocarbon chain, having from 3 to 15 carbon atoms.
21. The polymer of claim 2, wherein R2 is a divalent, branched or unbranched, hydrocarbon chain, having from 3 to 15 carbon atoms.
22. The polymer of claim 2, wherein R2 is a divalent, branched or unbranched, hydrocarbon chain, having from 6 to 10 carbon atoms.
23. The polymer of claim 2, wherein R2 is a divalent hydrocarbon chain having 7, 8, or 9 carbon atoms.
24. The polymer of claim 2, wherein R2 is a divalent hydrocarbon chain having 8 carbon atoms.
25. The polymer of claim 1, further comprising another therapeutic agent dispersed in the matrix of the polymer.
26. The polymer of claim 1, further comprising another therapeutic agent appended to the polymer backbone.
27. A pharmaceutical composition comprising a polymer of claim 1 and a pharmaceutically acceptable carrier.
28. A therapeutic method for treating a disease in an animal comprising administering to an animal in need of such therapy, an effective amount of a polymer of claim 1.
29. A therapeutic method for producing an anti-bacterial effect in an animal comprising administering to an animal in need of such therapy, an effective amount of a polymer of claim 5.
30. A therapeutic method for producing an anti-fungal effect in an animal comprising administering to an animal in need of such therapy, an effective amount of a polymer of claim 6.
31. A therapeutic method for treating cancer comprising administering to an animal in need of such therapy, an effective amount of a polymer of claim 7.
32. A therapeutic method for producing an anti-inflammatory effect in an animal comprising administering to an animal in need of such therapy, an effective amount of a polymer of claim 9.
33. A method for producing a biocompatible and biodegradable polyester or polyamide which degrades into a biologically active compound comprising co-polymerizing a biologically active compound containing at least two alcohol or phenol groups or at least two amine groups with carboxylic acid groups or bis(acyl) chlorides.
34. A method of delivering a biologically active compound to a host comprising administering to the host a biocompatible and biodegradable polyester or polyamide of any one of claim 1.
35. The polymer as described in claim 1 for use in medical therapy.
36. The use of a polymer as described in claim 1 for the manufacture of a medicament useful for the treatment of a disease in a mammal, such as a human.
37
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US20050053577A1 (en) 2005-03-10
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WO2002009767A2 (en) 2002-02-07
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