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 excipientsInfo
- 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
Links
- 229920000642 polymer Polymers 0.000 title claims abstract 36
- 238000000034 method Methods 0.000 title claims abstract 31
- 239000000203 mixture Substances 0.000 title claims abstract 19
- 239000000227 bioadhesive Substances 0.000 title claims abstract 5
- 230000002708 enhancing effect Effects 0.000 title abstract 2
- 239000008012 organic excipient Substances 0.000 title 1
- 239000004005 microsphere Substances 0.000 claims abstract 32
- 150000008064 anhydrides Chemical class 0.000 claims abstract 23
- 229940039227 diagnostic agent Drugs 0.000 claims abstract 9
- 239000000032 diagnostic agent Substances 0.000 claims abstract 9
- 239000003814 drug Substances 0.000 claims abstract 9
- 239000012528 membrane Substances 0.000 claims abstract 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract 4
- 238000012377 drug delivery Methods 0.000 claims abstract 4
- 239000000178 monomer Substances 0.000 claims abstract 4
- 150000004676 glycans Chemical class 0.000 claims abstract 3
- 229920001282 polysaccharide Polymers 0.000 claims abstract 3
- 239000005017 polysaccharide Substances 0.000 claims abstract 3
- 102000004169 proteins and genes Human genes 0.000 claims abstract 3
- 108090000623 proteins and genes Proteins 0.000 claims abstract 3
- 230000002496 gastric effect Effects 0.000 claims abstract 2
- 230000000241 respiratory effect Effects 0.000 claims abstract 2
- 229940124597 therapeutic agent Drugs 0.000 claims 7
- 210000004379 membrane Anatomy 0.000 claims 6
- -1 polyaryalkylenes Polymers 0.000 claims 6
- 230000001225 therapeutic effect Effects 0.000 claims 5
- 239000007789 gas Substances 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 2
- 229920001283 Polyalkylene terephthalate Polymers 0.000 claims 2
- 239000004952 Polyamide Substances 0.000 claims 2
- 229920002732 Polyanhydride Polymers 0.000 claims 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims 2
- 150000007513 acids Chemical class 0.000 claims 2
- 229920002678 cellulose Polymers 0.000 claims 2
- 235000010980 cellulose Nutrition 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 229920001577 copolymer Polymers 0.000 claims 2
- 239000006185 dispersion Substances 0.000 claims 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims 2
- 239000000463 material Substances 0.000 claims 2
- 239000002245 particle Substances 0.000 claims 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 claims 2
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims 2
- 229920002627 poly(phosphazenes) Polymers 0.000 claims 2
- 229920002401 polyacrylamide Polymers 0.000 claims 2
- 229920001281 polyalkylene Polymers 0.000 claims 2
- 229920001515 polyalkylene glycol Polymers 0.000 claims 2
- 229920002647 polyamide Polymers 0.000 claims 2
- 229920000515 polycarbonate Polymers 0.000 claims 2
- 239000004417 polycarbonate Substances 0.000 claims 2
- 229920000728 polyester Polymers 0.000 claims 2
- 229920001296 polysiloxane Polymers 0.000 claims 2
- 229920002635 polyurethane Polymers 0.000 claims 2
- 239000004814 polyurethane Substances 0.000 claims 2
- 229920002554 vinyl polymer Polymers 0.000 claims 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims 1
- DFOCUWFSRVQSNI-UHFFFAOYSA-N 3-[4-(2-carboxyethyl)phenyl]propanoic acid Chemical compound OC(=O)CCC1=CC=C(CCC(O)=O)C=C1 DFOCUWFSRVQSNI-UHFFFAOYSA-N 0.000 claims 1
- ITEKDBLBCIMYAT-UHFFFAOYSA-N 4-[(4-carboxyphenoxy)methoxy]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OCOC1=CC=C(C(O)=O)C=C1 ITEKDBLBCIMYAT-UHFFFAOYSA-N 0.000 claims 1
- LFPLRGMCQXEYDO-UHFFFAOYSA-N 4-[1-(4-carboxyphenoxy)propoxy]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1OC(CC)OC1=CC=C(C(O)=O)C=C1 LFPLRGMCQXEYDO-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000007943 implant Substances 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims 1
- 210000004400 mucous membrane Anatomy 0.000 claims 1
- 230000001850 reproductive effect Effects 0.000 claims 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 abstract 2
- 229940079593 drug Drugs 0.000 abstract 2
- 229920000249 biocompatible polymer Polymers 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 239000001530 fumaric acid Substances 0.000 abstract 1
- 230000034659 glycolysis Effects 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 210000005000 reproductive tract Anatomy 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 1
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.
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 |
Family
ID=24689975
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1997/010256 WO1997049385A1 (en) | 1996-06-25 | 1997-06-12 | Methods and compositions for enhancing the bioadhesive properties of polymers using organic excipients |
Country Status (6)
| Country | Link |
|---|---|
| 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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|---|---|---|---|---|
| US9108070B2 (en) | 2006-09-13 | 2015-08-18 | Polymerix Corporation | Active agents and their oligomers and polymers |
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