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WO1997049385B1 - Methods and compositions for enhancing the bioadhesive properties of polymers using organic excipients - Google Patents

Methods and compositions for enhancing the bioadhesive properties of polymers using organic excipients

Info

Publication number
WO1997049385B1
WO1997049385B1 PCT/US1997/010256 US9710256W WO9749385B1 WO 1997049385 B1 WO1997049385 B1 WO 1997049385B1 US 9710256 W US9710256 W US 9710256W WO 9749385 B1 WO9749385 B1 WO 9749385B1
Authority
WO
WIPO (PCT)
Prior art keywords
microsphere
polymer
composition
anhydride
polymers
Prior art date
Application number
PCT/US1997/010256
Other languages
French (fr)
Other versions
WO1997049385A1 (en
Filing date
Publication date
Priority claimed from US08/670,326 external-priority patent/US5955096A/en
Application filed filed Critical
Priority to EP97929973A priority Critical patent/EP0912166B1/en
Priority to JP10503153A priority patent/JP2000513355A/en
Priority to AT97929973T priority patent/ATE230978T1/en
Priority to DE69718470T priority patent/DE69718470T2/en
Publication of WO1997049385A1 publication Critical patent/WO1997049385A1/en
Publication of WO1997049385B1 publication Critical patent/WO1997049385B1/en

Links

Abstract

Methods and compositions are provided for enhancing the bioadhesive properties of polymers used in drug delivery systems. The bioadhesive properties of a polymer are enhanced by incorporating an anhydride oligomer into the polymer to enhance the ability of the polymer to adhere to a tissue surface such as a mucosal membrane. Anhydride oligomers which enhance the bioadhesive properties of a polymer include oligomers synthesized from dicarboxylic acid monomers, preferably those found in Krebs glycolysis cycle, especially fumaric acid. The oligomers can be incorporated within a wide range of polymers including proteins, polysaccharides and synthetic biocompatible polymers. In one embodiment, anhydride oligomers can be incorporated within polymers used to form or coat drug delivery systems, such as microspheres, which contain a drug or diagnostic agent. The oligomers can either be solubilized and blended with the polymer before manufacture or else used as a coating with polymers over existing systems. The polymers, for example in the form of microspheres, have improved ability to adhere to mucosal membranes, and thus can be used to deliver a drug or diagnostic agent via any of a range of mucosal membrane surfaces including those of the gastrointestinal, respiratory, excretory and reproductive tracts.

Claims

AMENDED CLAIMS
[received by the International Bureau on 20 January 1998 (20.01.98); original claims 1 , 20 and 27 amended; original claims 5, 8, 30 and 33 cancelled; remaining claims unchanged (5 pages)]
1. A method for improving the bioadhesiveness of a polymer, the method comprising incorporating an anhydride oligomer in the polymer in an amount effective to enhance the ability of the polymer to adhere to a mucosal membrane, wherein the anhydride oligomer includes twenty or fewer diacid units linked by anhydride linkages or has a molecular weight of 5000 Daltons or less.
2. The method of claim 1 wherein the anhydride oligomer is associated with the polymer by ionic or covalent bonds.
3. The method of claim 1 wherein the anhydride oligomer comprises dicarboxylic acid monomers selected from the group consisting of fumaric, maleic, succinic, adipic, sebacic and carboxyphenolic acids.
4. The method of claim 1 wherein the anhydride oligomer comprises dicarboxylic acid monomers selected from the group consisting of bis(p-carboxyphenoxy)methane, bis(p-carboxyphenoxy)propane, and bis(ρ-carboxyphenoxy)hexane, phthalic acid, isophthalic acid, terephthalic acid, azeleic acid, pimelic acid, itaconic acid, cyclohexane dicarboxylic acid, 1 ,4 phenylene dipropionic acid and 1 , 10-dodecanedioic acid.
6. The method of claim 1 wherein the polymer is in the form of a microsphere, and wherein the method comprises improving the bioadhesiveness of the microsphere by incoφorating the anhydride oligomer in the polymer during formation of the microsphere, thereby to enhance the ability of the microsphere to adhere to a mucosal membrane.
7. The method of claim 6 wherein the anhydride oligomer is in the form of a fine dispersion of particles on at least the surface of the microsphere.
9. The method of claim 6 wherein the polymer incoφorating the anhydride oligomer is coated onto the surface of a microsphere formed of a different material.
10. The method of claim 1 wherein the polymer is selected from the group consisting of proteins and polysaccharides. 11. The method of claim 1 wherein the polymer is selected from the group consisting of polyamides, polycarbonates, polyalkylenes, polyaryalkylenes, polyalkylene glycols, polyalkylene oxides, polyalkylene terephthalates, polyvinyl polymers, polyphosphazenes, polyacrylamides, polysiloxanes, polyurethanes, polymers of acrylic and methacrylic acid, celluloses, poly anhydrides, polyesters, poly(hydroxy acids), and blends and copolymers thereof.
12. The method of claim 6 wherein the microsphere further comprises a therapeutic or diagnostic agent.
13. The method of claim 12 wherein the diagnostic agent is selected from the group consisting of gases, gas evolving agents and radio-opaque compounds.
14. The method of claim 1 wherein the polymer defines or coats a drug delivery device containing a therapeutic agent.
15. The method of claim 1 wherein the polymer defines or coats a surgical implant device.
16. The method of claim 1 wherein the microsphere has a diameter greater than or equal to 10 microns.
17. The method of claim 1 wherein the microsphere has a diameter between 2 and 5 microns.
18. The method of claim 1 wherein the microsphere has a diameter of less than 2 microns.
19. The method of claim 1 wherein the microsphere has a diameter less than 1 micron.
20. A method for delivering a therapeutic or diagnostic agent to a patient comprising administering to a mucosal membrane of the patient in a pharmaceutically acceptable carrier the therapeutic or diagnostic agent within a microsphere, wherein the surface of the microsphere comprises a polymer having an anhydride oligomer incorporated therein which improves the adhesion of the polymer to the mucosal membrane, and wherein the anhydride oligomer includes twenty or fewer diacid units linked by anhydride linkages or has a molecular weight of 5000 Daltons or less.
21. The method of claim 20 wherein the microsphere is administered by a route selected from the group consisting of nasal, vaginal, rectal and oral administration.
22. The method of claim 20 comprising administering the agent within the microsphere to a mucosal membrane selected from the group consisting of gastrointestinal, respiratory, excretory and reproductive mucous membranes.
23. The method of claim 20 wherein the microsphere has a diameter greater than or equal to 10 microns.
24. The method of claim 20 wherein the microsphere has a diameter of between and 5 microns.
25. The method of claim 20 wherein the microsphere has a diameter less than 2 microns.
26. The method of claim 20 wherein the microsphere has a diameter less than 1 micron.
27. A composition comprising a polymer incoφorating an anhydride oligomer in an amount effective to improve adhesion of the polymer to a mucosal membrane, wherein the anhydride oligomer includes twenty or fewer diacid units linked by anhydride linkages or has a molecular weight of 5000 Daltons or less.
28. The composition of claim 27 wherein the anhydride oligomer is associated with the polymer by ionic interactions or covalent bonds.
29. The composition of claim 27 wherein the anhydride oligomer comprises dicarboxylic acid monomers selected from the group consisting of fumaric, maleic, succinic, adipic, sebacic and carboxyphenolic acids.
31. The composition of claim 27 wherein the polymer is in the form of a microsphere. 32. The composition of claim 31 wherein the anhydride oligomer is in the form of a fine dispersion of particles on at least the surface of the microsphere.
34. The composition of claim 31 wherein the polymer incoφorating the anhydride oligomer is coated onto the surface of a microsphere formed of a different material.
35. The composition of claim 27 wherein the polymer is selected from the group consisting of proteins and polysaccharides.
36. The composition of claim 27 wherein the polymer is selected from the group consisting of polyamides, polycarbonates, polyalkylenes, polyaryalkylenes, polyalkylene glycols, polyalkylene oxides, polyalkylene terephthalates, polyvinyl polymers, polyphosphazenes, polyacrylamides, polysiloxanes, polyurethanes, polymers of acrylic and methacrylic acid, celluloses, polyanhydrides, polyesters, poly(hydroxy acids), and blends and copolymers thereof.
37. The composition of claim 31 wherein the microsphere further comprises a therapeutic or diagnostic agent.
38. The composition of claim 37 wherein the diagnostic agent is selected from the group consisting of gases, gas evolving agents and radio-opaque compounds.
39. The composition of claim 27 wherein the polymer defines or coats a drug delivery device containing a therapeutic agent.
40. The composition of claim 31 wherein the microsphere has a diameter greater than or equal to 10 microns.
41. The composition of claim 31 wherein the microsphere has a diameter of between 2 to 5 microns.
42. The composition of claim 31 wherein the microsphere has a diameter less than 2 microns.
43. The composition of claim 31 wherein the microsphere has a diameter less than 1 micron.
44. A method of forming a bioadhesive microsphere, the method comprising forming the microsphere of anhydride oligomers having a molecular weight of 5000 Daltons or less.
45. The method of claim 44 wherein the microsphere further comprises a therapeutic or diagnostic agent.
PCT/US1997/010256 1996-06-25 1997-06-12 Methods and compositions for enhancing the bioadhesive properties of polymers using organic excipients WO1997049385A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP97929973A EP0912166B1 (en) 1996-06-25 1997-06-12 Methods and compositions for enhancing the bioadhesive properties of polymers using organic excipients
JP10503153A JP2000513355A (en) 1996-06-25 1997-06-12 Methods and compositions for enhancing the bioadhesive properties of polymers using organic excipients
AT97929973T ATE230978T1 (en) 1996-06-25 1997-06-12 METHOD AND PREPARATIONS FOR IMPROVING THE BIOADHESIVE PROPERTIES OF POLYMERS USING ORGANIC EXCIPIENTS
DE69718470T DE69718470T2 (en) 1996-06-25 1997-06-12 METHOD AND PREPARATIONS FOR IMPROVING THE BIOADHESIVE PROPERTIES OF POLYMERS USING ORGANIC EXCIPIENTS

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US670,326 1996-06-25
US08/670,326 US5955096A (en) 1996-06-25 1996-06-25 Methods and compositions for enhancing the bioadhesive properties of polymers using organic excipients

Publications (2)

Publication Number Publication Date
WO1997049385A1 WO1997049385A1 (en) 1997-12-31
WO1997049385B1 true WO1997049385B1 (en) 1998-02-26

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Country Status (6)

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US (3) US5955096A (en)
EP (1) EP0912166B1 (en)
JP (1) JP2000513355A (en)
AT (1) ATE230978T1 (en)
DE (1) DE69718470T2 (en)
WO (1) WO1997049385A1 (en)

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