CA2259603A1 - Use of polymeric compositions for reducing or eliminating post-surgical adhesion formation - Google Patents
Use of polymeric compositions for reducing or eliminating post-surgical adhesion formationInfo
- Publication number
- CA2259603A1 CA2259603A1 CA002259603A CA2259603A CA2259603A1 CA 2259603 A1 CA2259603 A1 CA 2259603A1 CA 002259603 A CA002259603 A CA 002259603A CA 2259603 A CA2259603 A CA 2259603A CA 2259603 A1 CA2259603 A1 CA 2259603A1
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- ethylene oxide
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/44—Polyester-amides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/74—Synthetic polymeric materials
- A61K31/765—Polymers containing oxygen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/74—Synthetic polymeric materials
- A61K31/765—Polymers containing oxygen
- A61K31/77—Polymers containing oxygen of oxiranes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/74—Synthetic polymeric materials
- A61K31/785—Polymers containing nitrogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/04—Macromolecular materials
- A61L31/06—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P41/00—Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
- C08G63/08—Lactones or lactides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/664—Polyesters containing oxygen in the form of ether groups derived from hydroxy carboxylic acids
Abstract
The present invention relates to a method for reducing adhesions associated with post-operative surgery. The present method comprises administering or affixing a polymeric composition preferably comprising chain extended, coupled or crosslinked polyester/poly(oxyalkylene) ABA triblocks or AB diblocks having favourable EO/LA ratios to a site in the body which has been subjected to trauma, e.g. by surgery, excision or inflammatory disease. In the present invention, the polymeric material provides a barrier to prevent or reduce the extent of adhesions forming.
Claims (92)
1. A method for reducing or preventing adhesions in a patient comprising exposing tissue which has been subjected to tissue damage and is at risk for the formation of adhesions to a prepolymerized polymeric composition comprising chain extended, coupled or crosslinked poly(ester)/poly(oxyalkylene) ABA triblocks or AB diblocks, where A is a polyester unit and B is a polyoxyalkylene polymer unit, said polymeric composition having an EO/LA ratio falling within the range of about 0.1 to about 100.
2. The method according to claim 1 wherein said polyester unit is derived from the polymerization of monomers selected from the group consisting of lactic acid, lactide, glycolic acid, glycolide, .beta.-propiolactone, .epsilon.-caprolactone, .delta.-glutarolactone, .delta.-valerolactone, .beta.-butyrolactone, pivalolactone, .alpha.,.alpha.-diethylpropiolactone, ethylene carbonate, trimethylene carbonate, .gamma.-butyrolactone, p-dioxanone, 1,4-dioxepan-2-one, 3-methyl-1,4-dioxane-2,5-dione,
3,3,-dimethyl-1-4-dioxane-2,5-dione, cyclic esters of .alpha.-hydroxybutyric acid, .alpha.-hydroxyvaleric acid, .alpha.-hydroxyisovaleric acid, .alpha.-hydroxycaproic acid, .alpha.-hydroxy-.alpha.-ethylbutyric acid, .alpha.-hydroxyisocaproic acid, .alpha.-hydroxy-.alpha.-methyl valeric acid, .alpha.-hydroxyheptanoic acid, .alpha.-hydroxystearic acid, .alpha.-hydroxylignoceric acid, salicylic acid and mixtures, thereof.
3. The method according to claim 1 wherein said polyester comprises poly(aliphatic hydroxy carboxylic acid).
3. The method according to claim 1 wherein said polyester comprises poly(aliphatic hydroxy carboxylic acid).
4. The method according to claim 1 wherein said polyester comprises poly(aliphatic .alpha.-hydroxy carboxylic acid).
5. The method according to claim 1 wherein said polyester is obtained from polymerization of an aliphatic hydroxycarboxylic acid or ester selected from the group consisting of L-lactic acid, D,L-lactic acid, glycolic acid, L-lactide, D,L-lactide, glycolide or mixtures thereof.
6. The method according to claim 1 wherein said poly(oxyalkylene) polymer is comprised of poly(ethylene oxide).
7. The method according to claim 1 wherein said poly(oxyalkylene) polymer is comprised of a poly(ethylene oxide) homopolymer or poly(ethylene oxide)-co-poly(propylene oxide) block copolymer.
8. The method according to claim 1 wherein said polyester comprises units of an aliphatic hydroxycarboxylic acid or the corresponding cyclic dimeric ester selected from the group consisting of L-lactic acid, D,L-lactic acid, glycolic acid, L-lactide, D,L-lactide, glycolide or mixtures and said poly(oxyalkylene) polymer is comprised of a poly(ethylene oxide) homopolymer or poly(ethylene oxide)-co-poly(propylene oxide) block copolymers.
9. The method according to claim 5 wherein said A block is between about 1 and 400 carboxylic acid units in size and said B block is varies in size from about 100 Da to about 200,000 Da.
10. The method according to claim 7 wherein said A block comprises carboxylic acid units derived from L-lactide or D,L-lactide and said B block is comprised of poly(ethylene oxide).
11. The method according to claim 7 wherein said A block is approximately 6 to 30 carboxylic acid units in length and said B block is comprised of poly(ethylene oxide) having a molecular weight of between about 1,500 and 10,000 Da.
12. The method according to claim 1 wherein said composition is in the form of apreformed structure such as a film, rod, tube, bead, foam or ring or a dispersion, suspension, gel, liquid, spray or viscous solution.
13. The method according to claim 1 wherein said composition further includes a bioactive agent.
14. The method according to claim 1 wherein said composition is chain extended or coupled with a diisocyanate of the general formula:
where R' is a C2 to C12 alkylene group, a cycloalkyl or cycloalkyl-containing group, an aryl or aryl-containing group, 4,4'-diphenylmethane, toluene, naphthalene, 4,4'-dieyelohexylmethane, eyelohexyl, 3,3'-dimethylphenyl, 3,3'-dimethyl-diphenylmethane, 4,6'-xylylene, 3,5,5-trimethylcyclohexyl, 2,2,4-trimethylhexamethylene, p-phenylene or a poly(ethylene oxide) containing or poly(ethylene oxide) rich chain.
where R' is a C2 to C12 alkylene group, a cycloalkyl or cycloalkyl-containing group, an aryl or aryl-containing group, 4,4'-diphenylmethane, toluene, naphthalene, 4,4'-dieyelohexylmethane, eyelohexyl, 3,3'-dimethylphenyl, 3,3'-dimethyl-diphenylmethane, 4,6'-xylylene, 3,5,5-trimethylcyclohexyl, 2,2,4-trimethylhexamethylene, p-phenylene or a poly(ethylene oxide) containing or poly(ethylene oxide) rich chain.
15. The method according to claim 1 wherein said composition is chain extended or coupled with a compound of the general formula:
where R'' is a C0 to C12 alkylene group or a hydroxyl or carboxylic acid substituted alkylene group, alkene, a cycloalkyl, hydroxyl or carboxylic acid containing cycloalkyl or cycloalkyl-containing group, an aryl or aryl-containing group or a polyoxyalkylene chain-containing group comprised of poly(ethylene oxide), poly(ethylene oxide)-co-poly(propylene oxide) or poly(ethylene oxide) rich ehains and L is hydroxyl, a halide selected from Cl, I or Br or an ester group.
where R'' is a C0 to C12 alkylene group or a hydroxyl or carboxylic acid substituted alkylene group, alkene, a cycloalkyl, hydroxyl or carboxylic acid containing cycloalkyl or cycloalkyl-containing group, an aryl or aryl-containing group or a polyoxyalkylene chain-containing group comprised of poly(ethylene oxide), poly(ethylene oxide)-co-poly(propylene oxide) or poly(ethylene oxide) rich ehains and L is hydroxyl, a halide selected from Cl, I or Br or an ester group.
16. The method according to claim 15 wherein said poly(oxyalkylene) comprises poly(ethylene oxide).
17. The method according to claim 14 wherein said poly(oxyalkylene) comprises poly(ethylene oxide).
18. The method according to claim 1 wherein said composition comprises AB diblocks.
19. The method according to claim 18 wherein said AB diblock is end-capped with a non-reactive group.
20. The method according to claim 19 wherein said unreactive group is selected from the group consisting of alkyl, aryl, aralkyl, a substituted alkyl, aryl, aralkyl and a protecting group.
21. The method according to claim 1 wherein said composition comprises ABA triblocks.
22. The method according to claim 1 wherein said composition is crosslinked.
23. The method according to claim 2 wherein said composition is crosslinked.
24. A method for reducing or preventing adhesions in a patient comprising exposing tissue which has been subjected to tissue damage and is at risk for the formation of adhesions to a polymeric composition comprising polymers of the chemical structure:
where m, a and b are positive integers, R is an ethylene group and/or propylene group with the proviso that R is not exclusively a propylene group when R' contains an absence of poly(ethylene oxide), R' is a C2 to C12 alkylene group, a cycloalkyl or cycloalkyl-containing group, an aryl or aryl-containing group, 4,4'-diphenylmethane, toluene, naphthalene, 4,4'-dicyclohexylmethane, cyclohexyl, 3,3'-dimethylphenyl, 3,3'-dimethyl-diphenylmethane, 4,6'-xylylene, 3,5,5-trimethylcyclohexyl, 2,2,4-trimethylhexamethylene, p-phenylene, or a poly(ethylene oxide) containing or poly(ethylene oxide) rich chain and R1 is H or CH3.
where m, a and b are positive integers, R is an ethylene group and/or propylene group with the proviso that R is not exclusively a propylene group when R' contains an absence of poly(ethylene oxide), R' is a C2 to C12 alkylene group, a cycloalkyl or cycloalkyl-containing group, an aryl or aryl-containing group, 4,4'-diphenylmethane, toluene, naphthalene, 4,4'-dicyclohexylmethane, cyclohexyl, 3,3'-dimethylphenyl, 3,3'-dimethyl-diphenylmethane, 4,6'-xylylene, 3,5,5-trimethylcyclohexyl, 2,2,4-trimethylhexamethylene, p-phenylene, or a poly(ethylene oxide) containing or poly(ethylene oxide) rich chain and R1 is H or CH3.
25. The method according to claim 24 wherein R1 is CH3.
26. The method according to claim 24 wherein m is 4 to about 5,000, R1 is CH3 and R is an ethylene group.
27. The method according to claim 24 wherein m is about 30 to about 230, R1 is CH3 and R is an ethylene group.
28. The method according to claim 24 wherein R' is a C6 alkylene group.
29. The method according to claim 24 wherein said composition is in the form of a preformed structure such as a film, rod, tube, bead, foam, ring or a viscous liquid, dispersion, suspension, viscous solution, spray or gel.
30. The method according to claim 24 wherein a and b are the same integer.
31. The method according to claim 24 wherein said polymeric composition includes a bioactive agent.
32. The method according to claim 24 wherein said poly(oxyalkylene) is poly(ethylene oxide).
33. A method for reducing or preventing adhesions in a patient comprising exposing tissue which has been subjected to tissue damage and is at risk for the formation of adhesions to a polymeric composition comprising polymers of the chemical structure:
where m, x and y are positive integers, R is an ethylene or propylene group with the proviso that R is not exclusively a propylene group when R'' contains an absence of poly(ethylene oxide), R1 is a hydrogen or methyl group, R'' is a C 0 to C12 alkylene group or a hydroxyl or carboxylic acid substituted alkyl group, a cycloalkyl, a hydroxyl-containing cycloalkyl, or cycloalkyl-containing group, an aryl or aryl-containing group, or a polyoxyalkylene chain-containing group comprised of poly(ethylene oxide), poly(ethylene oxide)-co-poly(propylene oxide) or a poly(ethylene oxide) rich chain.
where m, x and y are positive integers, R is an ethylene or propylene group with the proviso that R is not exclusively a propylene group when R'' contains an absence of poly(ethylene oxide), R1 is a hydrogen or methyl group, R'' is a C 0 to C12 alkylene group or a hydroxyl or carboxylic acid substituted alkyl group, a cycloalkyl, a hydroxyl-containing cycloalkyl, or cycloalkyl-containing group, an aryl or aryl-containing group, or a polyoxyalkylene chain-containing group comprised of poly(ethylene oxide), poly(ethylene oxide)-co-poly(propylene oxide) or a poly(ethylene oxide) rich chain.
34. The method according to claim 33 wherein R1 is CH3.
35. The method according to claim 33 wherein m is 4 to about 5,000, R1 is CH3 and R is an ethylene group.
36. The method according to claim 33 wherein m is about 30 to about 230, R1 is CH3 and R is an ethylene group.
37. The method according to claim 33 wherein R' is a C6 alkylene group.
38. The method according to claim 33 wherein said composition is in the form of a prerolmed structure such as a film, rod, tube, bead, foam or ring or a viscous liquid, gel, dispersion, suspension, spray or viscous solution.
39. The method according to claim 33 wherein said composition includes a bioactive agent.
40. A method for reducing or preventing adhesions in a patient comprising exposing tissue which has been subjected to tissue damage and is at risk for the formation of adhesions to a prepolymerized polymeric composition comprising polymers of the chemical structure:
where j, k and m are positive integers, R is an ethylene or propylene group with the proviso that R is not exclusively a propylene group when R' and R''' contain an absence of poly(ethylene oxide), R' is a C2 to C12 alkylene group, a cycloalkyl or cycloalkyl-containing group, an aryl or aryl-containing group, 4,4'-diphenylmethane, toluene, naphthalene, 4,4'-dicyclohexylmethane, cyclohexyl, 3,3'-dimethylphenyl, 3,3'-dimethyl-diphenylmethane, 4,6'-xylylene, 3,5,5-trimethylcyclohexyl, 2,2,4-trimethylhexamethylene, p-phenylene, or a poly(ethylene oxide) containing or poly(ethylene oxide) rich chain, R''' is selected from the group consisting of poly(ethylene oxide), poly(ethylene oxide)-co-poly(propylene oxide), a poly(ethylene oxide)-rich chain, a diol, a diamine, a dicarboxylic acid and an ABA triblock wherein A is a polyester unit and B is selected from the group consisting of poly(ethylene oxide), poly(ethylene oxide)-co-poly(propylene oxide), a poly(ethylene oxide)-rich chain, a diol, a diamine, and a dicarboxylic acid and R1 is H or CH3, said polymeric composition having an EO/LA ratio which falls within the range of about 0.1 to about 100.
where j, k and m are positive integers, R is an ethylene or propylene group with the proviso that R is not exclusively a propylene group when R' and R''' contain an absence of poly(ethylene oxide), R' is a C2 to C12 alkylene group, a cycloalkyl or cycloalkyl-containing group, an aryl or aryl-containing group, 4,4'-diphenylmethane, toluene, naphthalene, 4,4'-dicyclohexylmethane, cyclohexyl, 3,3'-dimethylphenyl, 3,3'-dimethyl-diphenylmethane, 4,6'-xylylene, 3,5,5-trimethylcyclohexyl, 2,2,4-trimethylhexamethylene, p-phenylene, or a poly(ethylene oxide) containing or poly(ethylene oxide) rich chain, R''' is selected from the group consisting of poly(ethylene oxide), poly(ethylene oxide)-co-poly(propylene oxide), a poly(ethylene oxide)-rich chain, a diol, a diamine, a dicarboxylic acid and an ABA triblock wherein A is a polyester unit and B is selected from the group consisting of poly(ethylene oxide), poly(ethylene oxide)-co-poly(propylene oxide), a poly(ethylene oxide)-rich chain, a diol, a diamine, and a dicarboxylic acid and R1 is H or CH3, said polymeric composition having an EO/LA ratio which falls within the range of about 0.1 to about 100.
41. The method according to claim 40 wherein said diol is selected from the group consisting of ethylene glycol, butanediol, OH-terminated polycaprolactone, poly(propylene glycol), OH-terminated polyester or oligoesters, tartaric acid, said diamine is selected from the group consisting of ethylene diamine, hexamethylene diamine, amino acids, and oligopeptides and said dicarboxylic acid is selected from the group consisting of succinic acid, sebacic acid, adipic acid, malic acid, oxalic acid, maleic acid, fumaric acid, COOH-terminated polycaprolactone, and COOH-terminated polyesters or oligoesters.
42. The method according to claim 40 wherein R1 is CH3.
43. The method according to claim 40 wherein m is 4 to about 5,000, R1 is CH3 and R is an ethylene group.
44. The method according to claim 40 wherein m is about 30 to about 230, R1 is CH3 and R is an ethylene group.
45. The method according to claim 40 wherein R' is a C6 alkylene group.
46. The method according to claim 40 wherein said composition is in the form of a preformed structure such as a film, rod, tube, bead, foam or ring or a viscous liquid, dispersion, suspension, viscous solution, spray or gel.
47. The method according to claim 40 wherein a and b are the same integer
48. The method according to claim 40 wherein said polymeric composition includes a bioactive agent.
49. The method according to claim 40 where R''' is poly(ethylene oxide) and has a molecular weight ranging from about 200 Da to about 10,000 Da.
50. The method according to claim 40 wherein R' is a C2 to C8 alkylene group.
51. A method for reducing or preventing adhesions in a patient comprising exposing tissue which has been subjected to tissue damage and is at risk for the formation of adhesions to a prepolymerized polymeric composition comprising chain extended, coupled or crosslinked ABA
triblocks or AB diblocks, where A is an aliphatic polyester and B is a compound selected from the group consisting of a diol, a diamine and a dicarboxylic acid, wherein said ABA triblock or AB
diblock is chain extended, coupled or crosslinked with an amount of at least one compound comprising poly(ethylene oxide) effective to provide an EO/LA ratio of said polymeric composition which falls within the range of about 0.1 to about 100.
triblocks or AB diblocks, where A is an aliphatic polyester and B is a compound selected from the group consisting of a diol, a diamine and a dicarboxylic acid, wherein said ABA triblock or AB
diblock is chain extended, coupled or crosslinked with an amount of at least one compound comprising poly(ethylene oxide) effective to provide an EO/LA ratio of said polymeric composition which falls within the range of about 0.1 to about 100.
52. The method according to claim 51 wherein said diol is selected from the group consisting of ethylene glycol, butanediol, OH-terminated polycaprolactone, poly(propylene glycol), OH-terminated polyester or oligoesters, tartaric acid, said diamine is selected from the group consisting of ethylene diamine, hexamethylene diamine, amino acids, and oligopeptides and said dicarboxylic acid is selected from the group consisting of succinic acid, sebacic acid, adipic acid, malic acid, oxalic acid, maleic acid, fumaric acid, COOH-terminated polycaprolactone, and COOH-terminated polyesters or oligoesters.
53. The method according to claim 51 wherein said polyester is derived from the polymerization of monomers selected from the group consisting of lactic acid, lactide, glycolic acid, glycolide, .beta.-propiolactone, .epsilon.-caprolactone, .delta.-glutarolactone, .delta.-valerolactone, .beta.-butyrolactone, pivalolactone, .alpha.,.alpha.-diethylpropiolactone, ethylene carbonate, trimethylene carbonate, .gamma.-butyrolactone, p-dioxanone, 1,4-dioxepan-2-one, 3-methyl-1,4-dioxane-2,5-dione, 3,3,-dimethyl-1-4-dioxane-2,5-dione, cyclic esters of .alpha.-hydroxybutyric acid, .alpha.-hydroxyvaleric acid, .alpha.-hydroxyisovaleric acid, .alpha.-hydroxycaproic acid, .alpha.-hydroxy-.alpha.-ethylbutyric acid, .alpha.-hydroxyisocaproic acid, .alpha.-hydroxy-.alpha.-methyl valeric acid, .alpha.-hydroxyheptanoic acid, .alpha.-hydroxystearic acid, .alpha.-hydroxylignoceric acid, salicylic acid and mixtures, thereof.
54. The method according to claim 51 wherein said polyester comprises poly(aliphatic hydroxy carboxylic acid).
55. The method according to claim 51 wherein said polyester comprises poly(aliphatic .alpha.-hydroxy carboxylic acid).
56. The method according to claim 51 wherein said polyester is obtained from polymerization of an aliphatic hydroxycarboxylic acid or ester selected from the group consisting of L-lactic acid, D,L-lactic acid, glycolic acid, L-lactide, D,L-lactide, glycolide or mixtures thereof.
57. The method according to claim 51 wherein said A block is between about 1 and 400 carboxylic acid units in size and said B block is varies in size from about 100 Da to about 200,000 Da.
58. The method according to claim 51 wherein said A block comprises carboxylic acid units derived from L-lactide or D,L-lactide and said B block is comprised of a diol.
59. The method according to claim 51 wherein said A block is approximately 6 to 30 carboxylic acid units in length and said B block is comprised of ethylene glycol or butane diol.
60. The method according to claim 51 wherein said composition is in the form of a preformed structure such as a film, rod, tube, bead, foam or ring or a dispersion, suspension, gel, liquid, spray or viscous solution.
61. The method according to claim 51 wherein said composition further includes a bioactive agent.
62. The method according to claim 51 wherein said composition is chain extended or coupled with a diisocyanate of the general formula:
where R' comprises a poly(oxyalkylene)-containing or poly(oxyethylene) rich chain.
where R' comprises a poly(oxyalkylene)-containing or poly(oxyethylene) rich chain.
63. The method according to claim 51 wherein said composition is chain extended or coupled with a compound of the general formula:
where R'' is a polyoxyalkylene chain comprised of poly(ethylene oxide), poly(ethylene oxide)-co-poly(propylene oxide) or is a poly(ethylene oxide) rich chain and L is hydroxyl, a halide selected from Cl, I or Br or an ester group.
where R'' is a polyoxyalkylene chain comprised of poly(ethylene oxide), poly(ethylene oxide)-co-poly(propylene oxide) or is a poly(ethylene oxide) rich chain and L is hydroxyl, a halide selected from Cl, I or Br or an ester group.
64. The method according to claim 63 wherein R'' is poly(ethylene oxide).
65. The method according to claim 51 wherein said composition is crosslinked.
66. The method according to claim 51 wherein said composition is crosslinked.
67. A composition for use in reducing or preventing adhesions in a patient comprising a polymer of the chemical structure:
where m and a are positive integers, R is an ethylene group or propylene group with the proviso that R is not exclusively a propylene group, M is a non-reactive group and R1 is H or CH3 said composition having an EO/LA ratio ranging from about 0.1 to about 100.
where m and a are positive integers, R is an ethylene group or propylene group with the proviso that R is not exclusively a propylene group, M is a non-reactive group and R1 is H or CH3 said composition having an EO/LA ratio ranging from about 0.1 to about 100.
68. The composition according to claim 67 wherein R1 is CH3.
69. The composition according to claim 67 wherein said non-reactive group is a C1 to C12 alkyl group, an aryl group, an aralkyl group or a substituted C1 to C12 alkyl group, aryl group, aralkyl group or a blocking group.
70. The composition according to claim 67 wherein m is 4 to about 5,000, R1 is CH3 and R is an ethylene group.
71. The composition according to claim 67 wherein m is about 30 to about 230, R1 is CH3 and R is an ethylene group.
72. The composition according to claim 67 wherein said polymeric composition includes a bioactive agent.
73. A composition for use in reducing or preventing adhesions in a patient comprising a polymer of the chemical structure:
where m and x are positive integers, R is an ethylene group or propylene group with the proviso that R is not exclusively a propylene group when R'' contains an absence of poly(ethylene oxide), M is a non-reactive group, R'' is a C0 to C12 alkylene group or a hydroxyl or carboxylic acid substituted alkyl group, a cycloalkyl, a hydroxyl-containing cycloalkyl, or cycloalkyl-containing group, an aryl or aryl-containing group, or a polyoxyalkylene chain-containing group comprised of poly(ethylene oxide), poly(ethylene oxide)-co-poly(propylene oxide) or a poly(ethylene oxide) rich chain, R1 is H or CH3 and M is a non-reactive group, said polymeric composition having an EO/LA ratio which falls within the range of about 0.1 to about 100.
where m and x are positive integers, R is an ethylene group or propylene group with the proviso that R is not exclusively a propylene group when R'' contains an absence of poly(ethylene oxide), M is a non-reactive group, R'' is a C0 to C12 alkylene group or a hydroxyl or carboxylic acid substituted alkyl group, a cycloalkyl, a hydroxyl-containing cycloalkyl, or cycloalkyl-containing group, an aryl or aryl-containing group, or a polyoxyalkylene chain-containing group comprised of poly(ethylene oxide), poly(ethylene oxide)-co-poly(propylene oxide) or a poly(ethylene oxide) rich chain, R1 is H or CH3 and M is a non-reactive group, said polymeric composition having an EO/LA ratio which falls within the range of about 0.1 to about 100.
74. The composition according to claim 73 wherein said non-reactive group is a C1 to C12 alkyl group, an aryl group, an aralkyl group or a substituted C1 to C12 alkyl group, an aryl group, an aralkyl group or a blocking group.
75. The composition according to claim 73 where M is methyl or ethyl.
76. A composition for use in reducing or preventing adhesions in a patient comprising a polymer of the chemical structure:
where m and a are positive integers, R is an ethylene group and/or propylene group with the proviso that R is not exclusively a propylene group when R' contains an absence of poly(ethylene oxide), M is a non-reactive group, R' is a C2 to C12 alkylene group, a cycloalkyl or cycloalkyl-containing group, an aryl or aryl-containing group, 4,4'-diphenylmethane, toluene, naphthalene, 4,4'-dicyclohexylmethane, cyclohexyl, 3,3'-dimethylphenyl, 3,3'-dimethyl-diphenylmethane, 4,6'-xylylene, 3,5,5-trimethylcyclohexyl, 2,2,4-trimethylhexamethylene, p-phenylene or a poly(ethylene oxide) containing or poly(ethylene oxide) rich chain and R1 is H or CH3, said polymeric composition having an EO/LA ratio which falls within the range of about 0.1 to about 100.
where m and a are positive integers, R is an ethylene group and/or propylene group with the proviso that R is not exclusively a propylene group when R' contains an absence of poly(ethylene oxide), M is a non-reactive group, R' is a C2 to C12 alkylene group, a cycloalkyl or cycloalkyl-containing group, an aryl or aryl-containing group, 4,4'-diphenylmethane, toluene, naphthalene, 4,4'-dicyclohexylmethane, cyclohexyl, 3,3'-dimethylphenyl, 3,3'-dimethyl-diphenylmethane, 4,6'-xylylene, 3,5,5-trimethylcyclohexyl, 2,2,4-trimethylhexamethylene, p-phenylene or a poly(ethylene oxide) containing or poly(ethylene oxide) rich chain and R1 is H or CH3, said polymeric composition having an EO/LA ratio which falls within the range of about 0.1 to about 100.
77. The composition according to claim 66 wherein said non-reactive group is a C1 to C12 alkyl group, an aryl group, an aralkyl group or a substituted C1 to C12 alkyl group, an aryl group, an aralkyl group or a blocking group.
78. The composition according to claim 67 where M is methyl or ethyl.
79. A composition for use in reducing or preventing adhesions in a patient comprising a polymer of the chemical structure:
where m and k are positive integers, R is an ethylene or propylene group with the proviso that R is not exclusively a propylene group when R' and R''' contain an absence of poly(ethylene oxide), R' is a C2 to C12 alkylene group, a cycloalkyl or cycloalkyl-containing group, an aryl or aryl-containing group, 4,4'-diphenylmethane, toluene, naphthalene, 4,4'-dicyclohexylmethane, cyclohexyl, 3,3'-dimethylphenyl, 3,3'-dimethyl-diphenylmethane, 4,6'-xylylene, 3,5,5-trimethylcyclohexyl, 2,2,4-trimethylhexamethylene, p-phenylene or a poly(ethylene oxide) containing or poly(ethylene oxide) rich chain, R''' is selected from the group consisting of poly(ethylene oxide), poly(ethylene oxide)-co-poly(propylene oxide), a poly(ethylene oxide)-rich chain, a diol, a diamine, a dicarboxylic acid or an ABA triblock, wherein A is a polyester unit and B is selected from the group consisting of poly(ethylene oxide), poly(ethylene oxide)-co-poly(propylene oxide), a poly(ethylene oxide)-rich chain, a diol, a diamine, and a dicarboxylic acid, R1 is H or CH3 and M is a non-reactive group, said polymeric composition having an EO/LA ratio which falls within the range of about 0.1 to about 100.
where m and k are positive integers, R is an ethylene or propylene group with the proviso that R is not exclusively a propylene group when R' and R''' contain an absence of poly(ethylene oxide), R' is a C2 to C12 alkylene group, a cycloalkyl or cycloalkyl-containing group, an aryl or aryl-containing group, 4,4'-diphenylmethane, toluene, naphthalene, 4,4'-dicyclohexylmethane, cyclohexyl, 3,3'-dimethylphenyl, 3,3'-dimethyl-diphenylmethane, 4,6'-xylylene, 3,5,5-trimethylcyclohexyl, 2,2,4-trimethylhexamethylene, p-phenylene or a poly(ethylene oxide) containing or poly(ethylene oxide) rich chain, R''' is selected from the group consisting of poly(ethylene oxide), poly(ethylene oxide)-co-poly(propylene oxide), a poly(ethylene oxide)-rich chain, a diol, a diamine, a dicarboxylic acid or an ABA triblock, wherein A is a polyester unit and B is selected from the group consisting of poly(ethylene oxide), poly(ethylene oxide)-co-poly(propylene oxide), a poly(ethylene oxide)-rich chain, a diol, a diamine, and a dicarboxylic acid, R1 is H or CH3 and M is a non-reactive group, said polymeric composition having an EO/LA ratio which falls within the range of about 0.1 to about 100.
80. The method according to claim 79 wherein said diol is selected from the group consisting of ethylene glycol, butanediol, OH-terminated polycaprolactone, poly(propylene glycol), OH-terminated polyester or oligoesters, tartaric acid, said diamine is selected from the group consisting of ethylene diamine, hexamethylene diamine, amino acids, and oligopeptides and said dicarboxylic acid is selected from the group consisting of succinic acid, sebacic acid, adipic acid, malic acid, oxalic acid, maleic acid, fumaric acid, COOH-terminated polycaprolactone, and COOH-terminated polyesters or oligoesters.
81. The composition according to claim 79 wherein said non-reactive group is a C1 to C12 alkyl group, an aryl group, an aralkyl group or a substituted C1 to C12 alkyl group, an aryl group, an aralkyl group or a blocking group.
82. The composition according to claim 79 where M is methyl or ethyl.
83. A composition for use in reducing or preventing adhesions in a patient comprising a polymer of the chemical structure: .
where m and k are positive integers, R is an ethylene or propylene group with the proviso that R is not exclusively ethylene where R' contains an absence of poly(ethylene oxide), R' is a C2 to C12 alkylene group, a cycloalkyl or cycloalkyl-containing group, an aryl or aryl-containing group, 4,4'-diphenylmethane, toluene, naphthalene, 4,4'-dicyclohexylmethane, cyclohexyl, 3,3'-dimethylphenyl, 3,3'-dimethyl-diphenylmethane, 4,6'-xylylene, 3,5,5-trimethylcyclohexyl, 2,2,4-trimethylhexamethylene, p-phenylene or a poly(ethylene oxide) containing or poly(ethylene oxide) rich chain and K is any group derived from a compound which is unable to initiate ring opening polymerization of a starting lactone, said polymeric composition having an EO/LA ratio which falls within the range of about 0.1 to about 100.
where m and k are positive integers, R is an ethylene or propylene group with the proviso that R is not exclusively ethylene where R' contains an absence of poly(ethylene oxide), R' is a C2 to C12 alkylene group, a cycloalkyl or cycloalkyl-containing group, an aryl or aryl-containing group, 4,4'-diphenylmethane, toluene, naphthalene, 4,4'-dicyclohexylmethane, cyclohexyl, 3,3'-dimethylphenyl, 3,3'-dimethyl-diphenylmethane, 4,6'-xylylene, 3,5,5-trimethylcyclohexyl, 2,2,4-trimethylhexamethylene, p-phenylene or a poly(ethylene oxide) containing or poly(ethylene oxide) rich chain and K is any group derived from a compound which is unable to initiate ring opening polymerization of a starting lactone, said polymeric composition having an EO/LA ratio which falls within the range of about 0.1 to about 100.
84. The composition according to claim 83 wherein K is a C1 to C12 alkyl group, an aryl group, an aralkyl group or a substituted C1 to C12 alkyl group, an aryl group, an aralkyl group, a C=C- containing group.
85. The composition according to claim 83 where K is methyl or ethyl.
86. A composition for use in reducing or preventing adhesions in a patient comprising a polymer of the chemical structure:
where m and x are positive integers, is an ethylene or propylene group with the proviso that R is not exclusively a propylene group when R'' and R''' contain an absence of poly(ethylene oxide), R1 is a hydrogen or methyl group, R'' is a C0 to C12 alkylene group or a hydroxyl or carboxylic acid substituted alkyl group, a cycloalkyl, a hydroxyl-containing cycloalkyl, or cycloalkyl-containing group, an aryl or aryl-containing group, or a polyoxyalkylene chain-containing group comprised of poly(ethylene oxide), poly(ethylene oxide)-co-poly(propylene oxide) or a poly(ethylene oxide) rich chain, R''' is selected from the group consisting of poly(ethylene oxide), poly(ethylene oxide)-co-poly(propylene oxide), a poly(ethylene oxide)-rich chain, a diol, a diamine, a dicarboxylic acid and an ABA triblock, wherein A is a polyester unit and B is selected from the group consisting of poly(ethylene oxide), poly(ethylene oxide)-co-poly(propylene oxide), a poly(ethylene oxide)-rich chain, a diol, a diamine, and a dicarboxylic acid, R1 is H or CH3 and M is a non-reactive group, said polymeric composition having an EO/LA ratio which falls within the range of about 0.1 to about 100.
where m and x are positive integers, is an ethylene or propylene group with the proviso that R is not exclusively a propylene group when R'' and R''' contain an absence of poly(ethylene oxide), R1 is a hydrogen or methyl group, R'' is a C0 to C12 alkylene group or a hydroxyl or carboxylic acid substituted alkyl group, a cycloalkyl, a hydroxyl-containing cycloalkyl, or cycloalkyl-containing group, an aryl or aryl-containing group, or a polyoxyalkylene chain-containing group comprised of poly(ethylene oxide), poly(ethylene oxide)-co-poly(propylene oxide) or a poly(ethylene oxide) rich chain, R''' is selected from the group consisting of poly(ethylene oxide), poly(ethylene oxide)-co-poly(propylene oxide), a poly(ethylene oxide)-rich chain, a diol, a diamine, a dicarboxylic acid and an ABA triblock, wherein A is a polyester unit and B is selected from the group consisting of poly(ethylene oxide), poly(ethylene oxide)-co-poly(propylene oxide), a poly(ethylene oxide)-rich chain, a diol, a diamine, and a dicarboxylic acid, R1 is H or CH3 and M is a non-reactive group, said polymeric composition having an EO/LA ratio which falls within the range of about 0.1 to about 100.
87. The method according to claim 86 wherein said diol is selected from the group consisting of ethylene glycol, butanediol, OH-terminated polycaprolactone, poly(propylene glycol), OH-terminated polyester or oligoesters, tartaric acid, said diamine is selected from the group consisting of ethylene diamine, hexamethylene diamine, amino acids, and oligopeptides and said dicarboxylic acid is selected from the group consisting of succinic acid, sebacic acid, adipic acid, malic acid, oxalic acid, maleic acid, fumaric acid, COOH-terminated polycaprolactone, and COOH-terminated polyesters or oligoesters.
88. The composition according to claim 86 wherein said non-reactive group is a C1 to C12 alkyl group, an aryl group, an aralkyl group or a substituted C1 to C12 alkyl group, an aryl group, an aralkyl group or a blocking group.
89. The composition according to claim 86 where M is methyl or ethyl.
90. A composition for use in reducing or preventing adhesions in a patient comprising a polymer of the chemical structure:
where m and a are positive integers, R is an ethylene group and/or propylene group with the proviso that R is not exclusively a propylene group when R' contains an absence of poly(ethylene oxide), M is a non-reactive group, R' is a C2 to C12 alkylene group, a cycloalkyl or cycloalkyl-containing group, an aryl or aryl-containing group, 4,4'-diphenylmethane, toluene, naphthalene, 4,4'-dicyclohexylmethane, cyclohexyl, 3,3'-dimethylphenyl, 3,3'-dimethyl-diphenylmethane, 4,6'-xylylene, 3,5,5-trimethylcyclohexyl, 2,2,4-trimethylhexamethylene, p-phenylene or a poly(ethylene oxide) containing or poly(ethylene oxide) rich chain, M is a non-reactive group, R1 is H or CH3, said polymeric composition having an EO/LA ratio which falls within the range of about 0.1 to about 100.
where m and a are positive integers, R is an ethylene group and/or propylene group with the proviso that R is not exclusively a propylene group when R' contains an absence of poly(ethylene oxide), M is a non-reactive group, R' is a C2 to C12 alkylene group, a cycloalkyl or cycloalkyl-containing group, an aryl or aryl-containing group, 4,4'-diphenylmethane, toluene, naphthalene, 4,4'-dicyclohexylmethane, cyclohexyl, 3,3'-dimethylphenyl, 3,3'-dimethyl-diphenylmethane, 4,6'-xylylene, 3,5,5-trimethylcyclohexyl, 2,2,4-trimethylhexamethylene, p-phenylene or a poly(ethylene oxide) containing or poly(ethylene oxide) rich chain, M is a non-reactive group, R1 is H or CH3, said polymeric composition having an EO/LA ratio which falls within the range of about 0.1 to about 100.
91. The composition according to claim 90 wherein said non-reactive group is a C1 to C12 alkyl group, an aryl group, an aralkyl group or a substituted C1 to C12 alkyl group, an aryl group, an aralkyl group or a blocking group.
92. The composition according to claim 91 where M is methyl or ethyl.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/678,762 US5711958A (en) | 1996-07-11 | 1996-07-11 | Methods for reducing or eliminating post-surgical adhesion formation |
| US08/678,762 | 1996-07-11 | ||
| PCT/US1997/012168 WO1998002171A1 (en) | 1996-07-11 | 1997-07-11 | Methods and compositions for reducing or eliminating post-surgical adhesion formation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2259603A1 true CA2259603A1 (en) | 1998-01-22 |
| CA2259603C CA2259603C (en) | 2011-02-08 |
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ID=24724165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2259603A Expired - Fee Related CA2259603C (en) | 1996-07-11 | 1997-07-11 | Use of polymeric compositions for reducing or eliminating post-surgical adhesion formation |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US5711958A (en) |
| EP (1) | EP0939639B1 (en) |
| JP (1) | JP2000514457A (en) |
| KR (1) | KR20000023724A (en) |
| AT (1) | ATE330618T1 (en) |
| AU (1) | AU735698B2 (en) |
| BR (1) | BR9710243A (en) |
| CA (1) | CA2259603C (en) |
| DE (1) | DE69736186T2 (en) |
| ES (1) | ES2262182T3 (en) |
| WO (1) | WO1998002171A1 (en) |
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| US5278255A (en) * | 1990-08-17 | 1994-01-11 | The Dow Chemical Company | Unsaturated polyaminopolymer, derivatives thereof and processes for making |
| US5410016A (en) * | 1990-10-15 | 1995-04-25 | Board Of Regents, The University Of Texas System | Photopolymerizable biodegradable hydrogels as tissue contacting materials and controlled-release carriers |
| US5380536A (en) * | 1990-10-15 | 1995-01-10 | The Board Of Regents, The University Of Texas System | Biocompatible microcapsules |
| DE4111914A1 (en) * | 1991-04-12 | 1992-10-15 | Peter Neuenschwander | MATERIAL |
| US5314969A (en) * | 1992-05-11 | 1994-05-24 | Showa Highpolymer Co., Ltd. | Polyester sheet |
| FI92592C (en) * | 1992-10-16 | 1994-12-12 | Neste Oy | Process for the preparation of a lactic acid-based polyurethane |
| US5202413A (en) * | 1993-02-16 | 1993-04-13 | E. I. Du Pont De Nemours And Company | Alternating (ABA)N polylactide block copolymers |
| US5612052A (en) * | 1995-04-13 | 1997-03-18 | Poly-Med, Inc. | Hydrogel-forming, self-solvating absorbable polyester copolymers, and methods for use thereof |
-
1996
- 1996-07-11 US US08/678,762 patent/US5711958A/en not_active Expired - Lifetime
-
1997
- 1997-07-11 WO PCT/US1997/012168 patent/WO1998002171A1/en active IP Right Grant
- 1997-07-11 AT AT97934932T patent/ATE330618T1/en not_active IP Right Cessation
- 1997-07-11 CA CA2259603A patent/CA2259603C/en not_active Expired - Fee Related
- 1997-07-11 DE DE69736186T patent/DE69736186T2/en not_active Expired - Lifetime
- 1997-07-11 BR BR9710243-1A patent/BR9710243A/en not_active Application Discontinuation
- 1997-07-11 EP EP97934932A patent/EP0939639B1/en not_active Expired - Lifetime
- 1997-07-11 AU AU37984/97A patent/AU735698B2/en not_active Ceased
- 1997-07-11 JP JP10506210A patent/JP2000514457A/en not_active Ceased
- 1997-07-11 ES ES97934932T patent/ES2262182T3/en not_active Expired - Lifetime
- 1997-07-11 US US08/890,802 patent/US6136333A/en not_active Expired - Lifetime
-
1999
- 1999-01-11 KR KR1019997000185A patent/KR20000023724A/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0939639A4 (en) | 2002-03-13 |
| WO1998002171A1 (en) | 1998-01-22 |
| CA2259603C (en) | 2011-02-08 |
| AU735698B2 (en) | 2001-07-12 |
| US6136333A (en) | 2000-10-24 |
| ES2262182T3 (en) | 2006-11-16 |
| ATE330618T1 (en) | 2006-07-15 |
| EP0939639B1 (en) | 2006-06-21 |
| EP0939639A1 (en) | 1999-09-08 |
| DE69736186D1 (en) | 2006-08-03 |
| KR20000023724A (en) | 2000-04-25 |
| BR9710243A (en) | 2000-01-11 |
| US5711958A (en) | 1998-01-27 |
| DE69736186T2 (en) | 2007-05-03 |
| JP2000514457A (en) | 2000-10-31 |
| AU3798497A (en) | 1998-02-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20160711 |