CA2294711A1 - Novel polymeric compositions - Google Patents
Novel polymeric compositions Download PDFInfo
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- CA2294711A1 CA2294711A1 CA002294711A CA2294711A CA2294711A1 CA 2294711 A1 CA2294711 A1 CA 2294711A1 CA 002294711 A CA002294711 A CA 002294711A CA 2294711 A CA2294711 A CA 2294711A CA 2294711 A1 CA2294711 A1 CA 2294711A1
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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
- 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
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- 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
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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
- 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 novel bioabsorbable polymeric compositions based upon AB polyester polyether or related diblocks and triblocks. Compositions according to the present invention may be used in medical applications, for example, for reducing or preventing adhesion formation subsequent to medical procedures such as surgery, for producing surgical articles including stents and grafts, as coatings, sealants, lubricants, as transient barriers in the body, for materials which control the release of bioactive agents in the body, for wound and bum dressings and producing biodegradable articles, among numerous others.
Claims (30)
1. A polymeric composition comprising coupled AB diblocks, where A is a polyester unit 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 and B is derived from a hydroxyl, amine or carboxylic terminated compound end-capped with a non-reactive group, said hydroxyl, amine or carboxyl terminated compound initiating the polymerization of said monomers to form said polyester unit, said AB diblock being further reacted with one or more coupling agents or crosslinking agents to produce di-diblocks, multi-blocks, star-like polymers and comb-like polymers.
2. The composition according to claim 1 wherein said non-reactive group is an alkyl, aryl, aralkyl, substituted alkyl, substituted aryl, substituted aralkyl, a protecting group or a -C=C- containing group.
3. The composition according to claim 2 wherein said non-reactive group is a alkyl group.
4. The composition according to claim 1 wherein said coupling agent is a compound according to the structure:
where R' is a C2 to C12, preferably a C2 to C8 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 or p-phenylene.
where R' is a C2 to C12, preferably a C2 to C8 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 or p-phenylene.
5. The composition accoding to claim 4 wherein said diblock is reacted with a crosslinking agent to produce a star polymer.
6. The composition according to claim 1 wherein said polyester comprises poly(hydroxy carboxylic acid).
7. The composition 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, caprolactone or mixtures thereof.
8. The composition according to claim 1 wherein said composition further includes a bioactive agent.
9. A composition according to the structure:
where a is a positive integer, X is a C1-C8 alkylene group, R1 is H or CH3, and Z is derived from a monofunctional monomeric or polymeric compound end-capped with an amine or hydroxyl group or is derived from a compound end-capped with an amine or hydroxyl group which also contains a blocking group or a -C=C-group, said compound being selected from an alkyl amine or alcohol, an aryl amine or alcohol, an aralkyl amine or alcohol or a substituted alkyl amine or alcohol, a substituted aryl amine or alcohol or a substituted aralkyl amine or alcohol.
where a is a positive integer, X is a C1-C8 alkylene group, R1 is H or CH3, and Z is derived from a monofunctional monomeric or polymeric compound end-capped with an amine or hydroxyl group or is derived from a compound end-capped with an amine or hydroxyl group which also contains a blocking group or a -C=C-group, said compound being selected from an alkyl amine or alcohol, an aryl amine or alcohol, an aralkyl amine or alcohol or a substituted alkyl amine or alcohol, a substituted aryl amine or alcohol or a substituted aralkyl amine or alcohol.
10. The composition according to claim 9 wherein Z is represented by the structure M-(O-R-)m-Y
where m is a positive integer, Y is O or NH, R is a C2 to C10 alkylene group and M is a non-reactive group or a group containing a blocking group or a -C=C-groups.
where m is a positive integer, Y is O or NH, R is a C2 to C10 alkylene group and M is a non-reactive group or a group containing a blocking group or a -C=C-groups.
11. The composition according to claim 10, wherein M is selected from a C1 to alkyl group, an aryl group, an aralkyl group or a substituted C1 to C12 alkyl group, aryl group, aralkyl group, a blocking group or a C=C containing group.
12. The composition according to claim 10 wherein X is a C1 alkylene group.
13. The composition according to claim 10 wherein R1 is H when X is a C2-C8 alkylene group.
14. The composition according to claim 10 wherein said compound is a substituted or unsubstituted C1 to C12 alkyl amine or alcohol.
15. A composition according to the chemical structure:
where a is a positive integer, Z is derived from an amine- or hydroxyl-containing monofunctional monomeric or polymeric compound end-capped with an amine or hydroxyl group or is derived from a compound endcapped with an amine or hydroxyl group which also contains a blocking group or a -C=C-group, said amine- or alcohol-containing compound being selected from an alkyl amine or alcohol, an aryl amine or alcohol, an aralkyl amine or alcohol or a substituted alkyl amine or alcohol, a substituted aryl amine or alcohol, or a substituted aralkyl amine or alcohol, X is a C1-C8 alkylene 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, an oligoester or polyester, or a polyoxyalkylene chain-containing group, and R1 is H or CH3.
where a is a positive integer, Z is derived from an amine- or hydroxyl-containing monofunctional monomeric or polymeric compound end-capped with an amine or hydroxyl group or is derived from a compound endcapped with an amine or hydroxyl group which also contains a blocking group or a -C=C-group, said amine- or alcohol-containing compound being selected from an alkyl amine or alcohol, an aryl amine or alcohol, an aralkyl amine or alcohol or a substituted alkyl amine or alcohol, a substituted aryl amine or alcohol, or a substituted aralkyl amine or alcohol, X is a C1-C8 alkylene 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, an oligoester or polyester, or a polyoxyalkylene chain-containing group, and R1 is H or CH3.
16. The composition according to claim 15 wherein Z is represented by the structure M-(O-R-)m -Y
where m is a positive integer, Y is O or NH, R is a C2 to C10 alkylene group, and M is a non-reactive group or a group containing a blocking group or a -C=C-group.
where m is a positive integer, Y is O or NH, R is a C2 to C10 alkylene group, and M is a non-reactive group or a group containing a blocking group or a -C=C-group.
17. The composition according to claim 16 wherein M 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 blocking group or a C=C containing group.
18. The composition according too claim 17 wherein M is methyl or ethyl.
19. The composition according to claim 15 wherein said poly(oxyalkylene) chain containing group is poly(ethylene oxide), poly(ethylene oxide)-co-poly(propylene oxide) or a poly(ethylene oxide) rich chain.
20. The composition according to claim 15 where R1 is H when X is a C2-C8 alkylene group.
21. The composition according to claim 15 wherein X is a C1 alkylene group.
22. The composition according to claim 15 wherein said amine- or alcohol-containing compound is a substituted or unsubstituted C1 to C12 alkyl amine or alcohol.
23. A polymeric composition according to the chemical structure:
where a is a positive integer, Z is derived from an amine- or hydroxyl-containing monofunctional monomeric or polymeric compound end-capped with an amine or hydroxyl group or is derived from a compound end-capped with an amine or hydroxyl group which also contains a blocking group or a -C=C-group, said amine- or alcohol-containing compound being selected from an alkyl amine or alcohol, an aryl amine or alcohol, an aralkyl amine or alcohol or a substituted alkyl amine or alcohol, a substituted aryl amine or alcohol, or a substituted aralkyl amine or alcohol, X is a C1-C8 alkylene 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 or p-phenylene or a poly(ethylene oxide) containing or poly(ethylene oxide) rich chain and R1 is H or CH3
where a is a positive integer, Z is derived from an amine- or hydroxyl-containing monofunctional monomeric or polymeric compound end-capped with an amine or hydroxyl group or is derived from a compound end-capped with an amine or hydroxyl group which also contains a blocking group or a -C=C-group, said amine- or alcohol-containing compound being selected from an alkyl amine or alcohol, an aryl amine or alcohol, an aralkyl amine or alcohol or a substituted alkyl amine or alcohol, a substituted aryl amine or alcohol, or a substituted aralkyl amine or alcohol, X is a C1-C8 alkylene 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 or p-phenylene or a poly(ethylene oxide) containing or poly(ethylene oxide) rich chain and R1 is H or CH3
24. The composition according to claim 23 wherein Z is represented by the structure M-(O-R-)m-Y- where m is a positive integer, Y is O or NH, R is a C2 to C10 alkylene group, and M is a non-reactive group or a group containing a blocking group or a -C=C-group.
25. The composition according to claim 24 wherein M 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 blocking group or a C=C containing group.
26. The composition according to claim 25 wherein M is methyl or ethyl.
27. The composition according to claim 24 where R1 is H when X is a C2-C8 alkylene group.
28. The composition according to claim 24 wherein X is a C1 alkylene group.
29. The composition according to claim 24 wherein said amine- or alcohol-containing compound is a substituted or unsubstituted C1 to C12 alkyl amine or alcohol.
30. A polymeric composition according to the chemical structure:
where a is a positive integer, Z is derived from an amine- or hydroxyl-containing monofunctional monomeric or polymeric compound end-capped with an amine or hydroxyl group or is derived from a compound end-capped with an amine or hydroxyl group which also contains a blocking group or a -C=C-group, said amine- or alcohol-containing compound being selected from an alkyl amine or alcohol, an aryl amine or alcohol, an aralkyl amine or alcohol or a substituted alkyl amine or alcohol, a substituted aryl amine or alcohol, or a substituted aralkyl amine or alcohol, X is a C1-C8 alkylene 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, R"' is selected from or derived from the group consisting of a diol, which generates urethane groups upon reaction with a diisocyanate, a diamine, which generates urea groups upon reaction with a diisocyanate, or a dicarboxylic acid which generates amide groups upon reaction with a diisocyanate, said diol being selected from the group consisting of C2 to C24 diols, a poly(oxyalkylene) diol compound of the structure -(O-R)m -O- where R is a C2 to C10 alkylene group and m is a positive integer, poly(oxyalkylene)-rich diols, OH-terminated polyesters, oligoesters or an ACA triblock, wherein in said ACA triblock, A is a polyester unit and C is selected from the group consisting of a diol and a diamine, said diamine being selected from the group consisting of C2 to C24 diamines, amino acids, oligopeptides, proteins, enzymes, growth hormones, said dicarboxylic acid being selected from the group consisting of C0 to C24 dicarboxylic acids, COOH-terminated polycaprolactone, and COOH-terminated polyesters or oligoesters, and R1 is H
or CH3.
33. The composition according to claim 32 wherein Z is represented by the structure M-(O-R-)m -Y- where m is a positive integer, Y is O or NH, R is a C2 to C10 alkylene group, and M is a non-reactive group or a group containing a blocking group or a -C=C-group.
34. The composition according to claim 33 wherein M 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 blocking group or a C=C containing group.
35. The composition according to claim 34 wherein M is methyl or ethyl.
36. The composition according to claim 32 where R1 is H when X is a C2-C8 alkylene group.
37. The composition according to claim 32 wherein X is a C1 alkylene group.
38. The composition according to claim 32 wherein said amine- or alcohol-containing compound is a substituted or unsubstituted C1 to C12 alkyl amine or alcohol.
39. The composition according to claim 32 wherein said diol is a C2 to C12 diol.
40. The composition according to claim 32 wherein R is ethylene or propylene.
41. The composition according to claim 32 wherein said diamine is a C2 to C12 diamine.
42. The composition according to claim 32 wherein said diamine is lysine or polylysine.
43. The composition according to claim 32 wherein said dicarboxylic acid is a C2 to C12 dicarboxylic acid.
44. The composition according to claim 32 wherein said dicarboxylic acid is a COOH-terminated polyester.
45. A composition comprising a polymer of the chemical structure:
where a is a positive integer, Z is derived from an amine- or hydroxyl-containing monofunctional monomeric or polymeric compound end-capped with an amine or hydroxyl group or is derived from a compound end-capped with an amine or hydroxyl group which also contains a blocking group or a -C=C-group, said amine- or alcohol-containing compound being selected from an alkyl amine or alcohol. an aryl amine or alcohol, an aralkyl amine or alcohol or a substituted alkyl amine or alcohol, a substituted aryl amine or alcohol, or a substituted aralkyl amine or alcohol, X is a C1-C8 alkylene group 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, a carboxyl-terminated oligoester or polyester, or a polyoxyalkylene chain-containing group preferably comprised of poly(ethylene oxide), poly(ethylene oxide)-co-poly(propylene oxide) or a poly(ethylene oxide) rich chain, and R2 is selected from or derived from the group consisting of a diol, which generates urethane groups upon reaction with a diisocyanate, a diamine, which generates urea groups upon reaction with a diisocyanate or a dicarboxylic acid which generates amide groups upon reaction with a diisocyanate, said diol preferably being selected from the group consisting of C2 to C24 diols, poly(oxyalkylene) diols of the structure -(O-R)m -O- where R
is a C2 to C10 alkylene group and m is a positive integer, poly(oxyalkylene)-rich diols, OH-terminated polyesters, oligoesters or ACA triblocks, wherein in said ACA triblock, A is a polyester unit and C is selected from the group consisting of poly(ethylene oxide), poly(ethylene oxide)-co-poly(propylene oxde), a poly(ethylene oxide) rich chain, a diol and a diamine, said diamine being selected from the group consisting of C2 to C24 diamines, amino acids, and oligopeptides, proteins, enzymes and growth hormones, said dicarboxylic acid being selected from the group consisting of C0 to C24 dicarboxylic acids and COOH-terminated polyesters or oligoesters.
46. The composition according to claim 45 wherein Z is represented by the structure M-(O-R-)m -Y- where m is a positive integer, Y is O or NH, R is a C2 to C10 alkylene group, and M is a non-reactive group or a group containing a blocking group or a -C=C-group.
47. The composition according to claim 46 wherein M 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 blocking group or a C=C containing group.
48. The composition according to claim 47 wherein M is methyl or ethyl.
49. The composition according to claim 45 where R1 is H when X is a C2-C8 alkylene group.
50. The composition according to claim 45 wherein X is a C1 alkylene group.
51. The composition according to claim 45 wherein said amine- or alcohol-containing compound is a substituted or unsubstituted C1 to C12 alkyl amine or alcohol.
52. The composition according to claim 45 wherein said diol is a C2 to C12 diol.
53. The composition according to claim 45 wherein R is ethylene or propylene.
54. The composition according to claim 45 wherein said diamine is a C2 to C12 diamine.
55. The composition according to claim 45 wherein said diamine is lysine or polylysine.
56. The composition according to claim 45 wherein said dicarboxylic acid is a C2 to C12 dicarboxylic acid.
57. The composition according to claim 45 wherein said dicarboxylic acid is a COOH-terminated polyester.
58. A polymer composition of the chemical structure:
where a is a positive integer, Z is derived from an amine- or hydroxyl-containing monofunctional monomeric or polymeric compound end-capped with an amine or hydroxyl group or is derived from a compound end-capped with an amine or hydroxyl group which also contains a blocking group or a -C=C-group, said amine- or alcohol-containing compound being selected from an alkyl amine or alcohol, an aryl amine or alcohol, an aralkyl amine or alcohol or a substituted alkyl amine or alcohol, a substituted aryl amine or alcohol, or a substituted aralkyl amine or alcohol, X is a C1-C8 alkylene 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, R"' is selected from or derived from the group consisting of a diol, which generates urethane groups upon reaction with a diisocyanate, a diamine, which generates urea groups upon reaction with a diisocyanate, or a dicarboxyiic acid which generates amide groups upon reaction with a diisocyanate, said diol being selected from the group consisting of Cz to C24 diols, a poly(oxyalkylene) diol compound of the structure -(O-R)," -O- where R is a C, to C,o alkylene group and m is a positive integer, poly(oxyalkylene)-rich diols, OH-terminated polyesters, oligoesters or an ACA triblock, wherein in said ACA triblock, A is a polyester unit and C is selected from the group consisting of a diol and a diamine, said diamine being selected from the group consisting of Cz to C,4 diamines, amino acids, oligopeptides, proteins, enzymes, growth hormones, said dicarboxylic acid being selected from the group consisting of Co to Cz4 dicarboxylic acids, COOH-terminated polycaprolactone, and COON-terminated polyesters or oligoesters, and R, is 1-1 or CH3 .
59. The composition according to claim 57 wherein Z is represented by the structure M-(O-R-)m -Y- where m is a positive integer, Y is O or NH, R is a CZ to C,o alkylene group, and M is a non-reactive group or a group containing a blocking group or a -C=C-group.
60. The composition according to claim 58 wherein M is a C, to C,2 alkyl group, an aryl group, an aralkyl group or a substituted C, to C,, alkyl group, an aryl group, an aralkyl group, a blocking group or a C=C containing group.
61. The composition according to claim 60 wherein M is methyl or ethyl.
62. The composition according to claim 57 where R, is H when X is a Cz-C8 alkylene group.
63. The composition according to claim 57 wherein X is a C, alkylene group.
64. The composition according to claim 57 wherein said amine- or alcohol-containing compound is a substituted or unsubstituted C, to C,2 alkyl amine or alcohol.
65. The composition according to claim 57 wherein said diol is a C2 to C12 diol.
66. The composition according to claim 57 wherein R is ethylene or propylene.
67. The composition according to claim 57 wherein said diamine is a C2 to C12 diamine.
68. The composition according to claim 57 wherein said diamine is lysine or polylysine.
69. The composition according to claim 57 wherein said dicarboxylic acid is a C2 to C12 dicarboxylic acid.
70. The composition according to claim 57 wherein said dicarboxylic acid is a COOH-terminated polyester.
71. A composition of the chemical structure:
where a is a positive integer, Z is derived from an amine- or hydroxyl-containing monofunctional monomeric or polymeric compound end-capped with an amine or hydroxyl group or is derived from a compound end-capped with an amine or hydroxyl group which also contains a blocking group or a -C=C-group, said amine- or alcohol-containing compound being selected from an alkyl amine or alcohol, an aryl amine or alcohol, an aralkyl amine or alcohol or a substituted alkyl amine or alcohol, a substituted aryl amine or alcohol, or a substituted aralkyl amine or alcohol, X is a C1-C8 alkylene 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, R"' is selected from or derived from the group consisting of a diol, which generates urethane groups upon reaction with a diisocyanate, a diamine, which generates urea groups upon reaction with a diisocyanate, or a dicarboxylic acid which generates amide groups upon reaction with a diisocyanate, said diol being selected from the group consisting of C2 to C24 diols, a poly(oxyalkylene) diol compound of the structure -(O-R)m -O- where R is a C2 to C10 alkylene group and m is a positive integer, poly(oxyalkylene)-rich diols, OH-terminated polyesters, oligoesters or an ACA triblock, wherein in said ACA triblock, A is a polyester unit and C is selected from the group consisting of a diol and a diamine, said diamine being selected from the group consisting of C2 to C24 diamines, amino acids, oligopeptides, proteins, enzymes, growth hormones, said dicarboxylic acid being selected from the group consisting of C0 to C24 dicarboxylic acids, COOH-terminated polycaprolactone, and COOH-terminated polyesters or oligoesters, and R1 is H
or CH3.
72. The composition according to claim 71 wherein Z is represented by the structure M-(O-R-)m -Y- where m is a positive integer, Y is O or NH, R is a C2 to C10 alkylene group, and M is a non-reactive group or a group containing a blocking group or a -C=C-group.
73. The composition according to claim 72 wherein M 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 blocking group or a C=C containing group.
74. The composition according to claim 73 wherein M is methyl or ethyl.
75. The composition according to claim 71 where R1 is H when X is a C2-C8 alkylene group.
76. The composition according to claim 71 wherein X is a C1 alkylene group.
77. The composition according to claim 71 wherein said amine- or alcohol-containing compound is a substituted or unsubstituted C1 to C12 alkyl amine or alcohol.
78. The composition according to claim 71 wherein said diol is a C2 to C12 diol.
79. The composition according to claim 71 wherein R is ethylene or propylene.
80. The composition according to claim 71 wherein said diamine is a C2 to C12 diamine.
81. The composition according to claim 71 wherein said diamine is lysine or polylysine.
82. The composition according to claim 71 wherein said dicarboxylic acid is a C2 to C12 dicarboxylic acid.
83. The composition according to claim 71 wherein said dicarboxylic acid is a COOH-terminated polyester.
84. 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, R3 is an ethylene or propylene group with the proviso that R3 is not exclusively a propylene group when R2 and R3 contain an absence of poly(ethylene oxide), R1 is a hydrogen or methyl group, R2 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, R3 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 ACA triblock, wherein A is a polyester unit and C 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 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.
85. The composition according to claim 84 wherein said diol is selected from the group consisting of ethylene glycol, butanediol, OH-terminated polycaprolactone, poly(propylene glycol), OH-terminated polyester or oligoesters, 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, tartaric acid, COOH-terminated polycaprolactone, and COOH-terminated polyesters or oligoesters.
86. The composition according to claim 85 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 contains a blocking group or a -C=C- group.
87. The composition according to claim 86 where M is methyl or ethyl.
88. 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 the polymer composition according to claim 84.
where a is a positive integer, Z is derived from an amine- or hydroxyl-containing monofunctional monomeric or polymeric compound end-capped with an amine or hydroxyl group or is derived from a compound end-capped with an amine or hydroxyl group which also contains a blocking group or a -C=C-group, said amine- or alcohol-containing compound being selected from an alkyl amine or alcohol, an aryl amine or alcohol, an aralkyl amine or alcohol or a substituted alkyl amine or alcohol, a substituted aryl amine or alcohol, or a substituted aralkyl amine or alcohol, X is a C1-C8 alkylene 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, R"' is selected from or derived from the group consisting of a diol, which generates urethane groups upon reaction with a diisocyanate, a diamine, which generates urea groups upon reaction with a diisocyanate, or a dicarboxylic acid which generates amide groups upon reaction with a diisocyanate, said diol being selected from the group consisting of C2 to C24 diols, a poly(oxyalkylene) diol compound of the structure -(O-R)m -O- where R is a C2 to C10 alkylene group and m is a positive integer, poly(oxyalkylene)-rich diols, OH-terminated polyesters, oligoesters or an ACA triblock, wherein in said ACA triblock, A is a polyester unit and C is selected from the group consisting of a diol and a diamine, said diamine being selected from the group consisting of C2 to C24 diamines, amino acids, oligopeptides, proteins, enzymes, growth hormones, said dicarboxylic acid being selected from the group consisting of C0 to C24 dicarboxylic acids, COOH-terminated polycaprolactone, and COOH-terminated polyesters or oligoesters, and R1 is H
or CH3.
33. The composition according to claim 32 wherein Z is represented by the structure M-(O-R-)m -Y- where m is a positive integer, Y is O or NH, R is a C2 to C10 alkylene group, and M is a non-reactive group or a group containing a blocking group or a -C=C-group.
34. The composition according to claim 33 wherein M 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 blocking group or a C=C containing group.
35. The composition according to claim 34 wherein M is methyl or ethyl.
36. The composition according to claim 32 where R1 is H when X is a C2-C8 alkylene group.
37. The composition according to claim 32 wherein X is a C1 alkylene group.
38. The composition according to claim 32 wherein said amine- or alcohol-containing compound is a substituted or unsubstituted C1 to C12 alkyl amine or alcohol.
39. The composition according to claim 32 wherein said diol is a C2 to C12 diol.
40. The composition according to claim 32 wherein R is ethylene or propylene.
41. The composition according to claim 32 wherein said diamine is a C2 to C12 diamine.
42. The composition according to claim 32 wherein said diamine is lysine or polylysine.
43. The composition according to claim 32 wherein said dicarboxylic acid is a C2 to C12 dicarboxylic acid.
44. The composition according to claim 32 wherein said dicarboxylic acid is a COOH-terminated polyester.
45. A composition comprising a polymer of the chemical structure:
where a is a positive integer, Z is derived from an amine- or hydroxyl-containing monofunctional monomeric or polymeric compound end-capped with an amine or hydroxyl group or is derived from a compound end-capped with an amine or hydroxyl group which also contains a blocking group or a -C=C-group, said amine- or alcohol-containing compound being selected from an alkyl amine or alcohol. an aryl amine or alcohol, an aralkyl amine or alcohol or a substituted alkyl amine or alcohol, a substituted aryl amine or alcohol, or a substituted aralkyl amine or alcohol, X is a C1-C8 alkylene group 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, a carboxyl-terminated oligoester or polyester, or a polyoxyalkylene chain-containing group preferably comprised of poly(ethylene oxide), poly(ethylene oxide)-co-poly(propylene oxide) or a poly(ethylene oxide) rich chain, and R2 is selected from or derived from the group consisting of a diol, which generates urethane groups upon reaction with a diisocyanate, a diamine, which generates urea groups upon reaction with a diisocyanate or a dicarboxylic acid which generates amide groups upon reaction with a diisocyanate, said diol preferably being selected from the group consisting of C2 to C24 diols, poly(oxyalkylene) diols of the structure -(O-R)m -O- where R
is a C2 to C10 alkylene group and m is a positive integer, poly(oxyalkylene)-rich diols, OH-terminated polyesters, oligoesters or ACA triblocks, wherein in said ACA triblock, A is a polyester unit and C is selected from the group consisting of poly(ethylene oxide), poly(ethylene oxide)-co-poly(propylene oxde), a poly(ethylene oxide) rich chain, a diol and a diamine, said diamine being selected from the group consisting of C2 to C24 diamines, amino acids, and oligopeptides, proteins, enzymes and growth hormones, said dicarboxylic acid being selected from the group consisting of C0 to C24 dicarboxylic acids and COOH-terminated polyesters or oligoesters.
46. The composition according to claim 45 wherein Z is represented by the structure M-(O-R-)m -Y- where m is a positive integer, Y is O or NH, R is a C2 to C10 alkylene group, and M is a non-reactive group or a group containing a blocking group or a -C=C-group.
47. The composition according to claim 46 wherein M 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 blocking group or a C=C containing group.
48. The composition according to claim 47 wherein M is methyl or ethyl.
49. The composition according to claim 45 where R1 is H when X is a C2-C8 alkylene group.
50. The composition according to claim 45 wherein X is a C1 alkylene group.
51. The composition according to claim 45 wherein said amine- or alcohol-containing compound is a substituted or unsubstituted C1 to C12 alkyl amine or alcohol.
52. The composition according to claim 45 wherein said diol is a C2 to C12 diol.
53. The composition according to claim 45 wherein R is ethylene or propylene.
54. The composition according to claim 45 wherein said diamine is a C2 to C12 diamine.
55. The composition according to claim 45 wherein said diamine is lysine or polylysine.
56. The composition according to claim 45 wherein said dicarboxylic acid is a C2 to C12 dicarboxylic acid.
57. The composition according to claim 45 wherein said dicarboxylic acid is a COOH-terminated polyester.
58. A polymer composition of the chemical structure:
where a is a positive integer, Z is derived from an amine- or hydroxyl-containing monofunctional monomeric or polymeric compound end-capped with an amine or hydroxyl group or is derived from a compound end-capped with an amine or hydroxyl group which also contains a blocking group or a -C=C-group, said amine- or alcohol-containing compound being selected from an alkyl amine or alcohol, an aryl amine or alcohol, an aralkyl amine or alcohol or a substituted alkyl amine or alcohol, a substituted aryl amine or alcohol, or a substituted aralkyl amine or alcohol, X is a C1-C8 alkylene 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, R"' is selected from or derived from the group consisting of a diol, which generates urethane groups upon reaction with a diisocyanate, a diamine, which generates urea groups upon reaction with a diisocyanate, or a dicarboxyiic acid which generates amide groups upon reaction with a diisocyanate, said diol being selected from the group consisting of Cz to C24 diols, a poly(oxyalkylene) diol compound of the structure -(O-R)," -O- where R is a C, to C,o alkylene group and m is a positive integer, poly(oxyalkylene)-rich diols, OH-terminated polyesters, oligoesters or an ACA triblock, wherein in said ACA triblock, A is a polyester unit and C is selected from the group consisting of a diol and a diamine, said diamine being selected from the group consisting of Cz to C,4 diamines, amino acids, oligopeptides, proteins, enzymes, growth hormones, said dicarboxylic acid being selected from the group consisting of Co to Cz4 dicarboxylic acids, COOH-terminated polycaprolactone, and COON-terminated polyesters or oligoesters, and R, is 1-1 or CH3 .
59. The composition according to claim 57 wherein Z is represented by the structure M-(O-R-)m -Y- where m is a positive integer, Y is O or NH, R is a CZ to C,o alkylene group, and M is a non-reactive group or a group containing a blocking group or a -C=C-group.
60. The composition according to claim 58 wherein M is a C, to C,2 alkyl group, an aryl group, an aralkyl group or a substituted C, to C,, alkyl group, an aryl group, an aralkyl group, a blocking group or a C=C containing group.
61. The composition according to claim 60 wherein M is methyl or ethyl.
62. The composition according to claim 57 where R, is H when X is a Cz-C8 alkylene group.
63. The composition according to claim 57 wherein X is a C, alkylene group.
64. The composition according to claim 57 wherein said amine- or alcohol-containing compound is a substituted or unsubstituted C, to C,2 alkyl amine or alcohol.
65. The composition according to claim 57 wherein said diol is a C2 to C12 diol.
66. The composition according to claim 57 wherein R is ethylene or propylene.
67. The composition according to claim 57 wherein said diamine is a C2 to C12 diamine.
68. The composition according to claim 57 wherein said diamine is lysine or polylysine.
69. The composition according to claim 57 wherein said dicarboxylic acid is a C2 to C12 dicarboxylic acid.
70. The composition according to claim 57 wherein said dicarboxylic acid is a COOH-terminated polyester.
71. A composition of the chemical structure:
where a is a positive integer, Z is derived from an amine- or hydroxyl-containing monofunctional monomeric or polymeric compound end-capped with an amine or hydroxyl group or is derived from a compound end-capped with an amine or hydroxyl group which also contains a blocking group or a -C=C-group, said amine- or alcohol-containing compound being selected from an alkyl amine or alcohol, an aryl amine or alcohol, an aralkyl amine or alcohol or a substituted alkyl amine or alcohol, a substituted aryl amine or alcohol, or a substituted aralkyl amine or alcohol, X is a C1-C8 alkylene 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, R"' is selected from or derived from the group consisting of a diol, which generates urethane groups upon reaction with a diisocyanate, a diamine, which generates urea groups upon reaction with a diisocyanate, or a dicarboxylic acid which generates amide groups upon reaction with a diisocyanate, said diol being selected from the group consisting of C2 to C24 diols, a poly(oxyalkylene) diol compound of the structure -(O-R)m -O- where R is a C2 to C10 alkylene group and m is a positive integer, poly(oxyalkylene)-rich diols, OH-terminated polyesters, oligoesters or an ACA triblock, wherein in said ACA triblock, A is a polyester unit and C is selected from the group consisting of a diol and a diamine, said diamine being selected from the group consisting of C2 to C24 diamines, amino acids, oligopeptides, proteins, enzymes, growth hormones, said dicarboxylic acid being selected from the group consisting of C0 to C24 dicarboxylic acids, COOH-terminated polycaprolactone, and COOH-terminated polyesters or oligoesters, and R1 is H
or CH3.
72. The composition according to claim 71 wherein Z is represented by the structure M-(O-R-)m -Y- where m is a positive integer, Y is O or NH, R is a C2 to C10 alkylene group, and M is a non-reactive group or a group containing a blocking group or a -C=C-group.
73. The composition according to claim 72 wherein M 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 blocking group or a C=C containing group.
74. The composition according to claim 73 wherein M is methyl or ethyl.
75. The composition according to claim 71 where R1 is H when X is a C2-C8 alkylene group.
76. The composition according to claim 71 wherein X is a C1 alkylene group.
77. The composition according to claim 71 wherein said amine- or alcohol-containing compound is a substituted or unsubstituted C1 to C12 alkyl amine or alcohol.
78. The composition according to claim 71 wherein said diol is a C2 to C12 diol.
79. The composition according to claim 71 wherein R is ethylene or propylene.
80. The composition according to claim 71 wherein said diamine is a C2 to C12 diamine.
81. The composition according to claim 71 wherein said diamine is lysine or polylysine.
82. The composition according to claim 71 wherein said dicarboxylic acid is a C2 to C12 dicarboxylic acid.
83. The composition according to claim 71 wherein said dicarboxylic acid is a COOH-terminated polyester.
84. 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, R3 is an ethylene or propylene group with the proviso that R3 is not exclusively a propylene group when R2 and R3 contain an absence of poly(ethylene oxide), R1 is a hydrogen or methyl group, R2 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, R3 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 ACA triblock, wherein A is a polyester unit and C 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 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.
85. The composition according to claim 84 wherein said diol is selected from the group consisting of ethylene glycol, butanediol, OH-terminated polycaprolactone, poly(propylene glycol), OH-terminated polyester or oligoesters, 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, tartaric acid, COOH-terminated polycaprolactone, and COOH-terminated polyesters or oligoesters.
86. The composition according to claim 85 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 contains a blocking group or a -C=C- group.
87. The composition according to claim 86 where M is methyl or ethyl.
88. 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 the polymer composition according to claim 84.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/890,802 | 1997-07-11 | ||
| US08/890,802 US6136333A (en) | 1996-07-11 | 1997-07-11 | Methods and compositions for reducing or eliminating post-surgical adhesion formation |
| US09/006,664 | 1998-01-13 | ||
| US09/006,664 US6211249B1 (en) | 1997-07-11 | 1998-01-13 | Polyester polyether block copolymers |
| PCT/US1998/014128 WO1999002168A1 (en) | 1997-07-11 | 1998-07-08 | Novel polymeric compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2294711A1 true CA2294711A1 (en) | 1999-01-21 |
| CA2294711C CA2294711C (en) | 2010-09-14 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2294711A Expired - Fee Related CA2294711C (en) | 1997-07-11 | 1998-07-08 | Novel polymeric compositions |
Country Status (10)
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| US (2) | US6211249B1 (en) |
| EP (1) | EP1014998B1 (en) |
| JP (1) | JP2001509519A (en) |
| CN (1) | CN1267222A (en) |
| AT (1) | ATE250934T1 (en) |
| AU (1) | AU8294798A (en) |
| BR (1) | BR9811000A (en) |
| CA (1) | CA2294711C (en) |
| DE (1) | DE69818693T2 (en) |
| WO (1) | WO1999002168A1 (en) |
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| US5854382A (en) * | 1997-08-18 | 1998-12-29 | Meadox Medicals, Inc. | Bioresorbable compositions for implantable prostheses |
| US6818018B1 (en) * | 1998-08-14 | 2004-11-16 | Incept Llc | In situ polymerizable hydrogels |
| US6514534B1 (en) * | 1998-08-14 | 2003-02-04 | Incept Llc | Methods for forming regional tissue adherent barriers and drug delivery systems |
| US6743446B2 (en) * | 1999-12-15 | 2004-06-01 | The Ohio State University Research Foundation | Methods for stabilizing biologically active agents encapsulated in biodegradable controlled-release polymers |
-
1998
- 1998-01-13 US US09/006,664 patent/US6211249B1/en not_active Expired - Lifetime
- 1998-07-08 CA CA2294711A patent/CA2294711C/en not_active Expired - Fee Related
- 1998-07-08 AT AT98933260T patent/ATE250934T1/en not_active IP Right Cessation
- 1998-07-08 EP EP98933260A patent/EP1014998B1/en not_active Expired - Lifetime
- 1998-07-08 WO PCT/US1998/014128 patent/WO1999002168A1/en active IP Right Grant
- 1998-07-08 BR BR9811000-4A patent/BR9811000A/en not_active Application Discontinuation
- 1998-07-08 AU AU82947/98A patent/AU8294798A/en not_active Abandoned
- 1998-07-08 JP JP2000501759A patent/JP2001509519A/en active Pending
- 1998-07-08 DE DE69818693T patent/DE69818693T2/en not_active Expired - Lifetime
- 1998-07-08 CN CN98808245A patent/CN1267222A/en active Pending
-
2001
- 2001-03-13 US US09/804,745 patent/US7879356B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| BR9811000A (en) | 2000-09-19 |
| AU8294798A (en) | 1999-02-08 |
| EP1014998A1 (en) | 2000-07-05 |
| US20010009662A1 (en) | 2001-07-26 |
| EP1014998A4 (en) | 2000-10-25 |
| DE69818693T2 (en) | 2004-07-08 |
| US7879356B2 (en) | 2011-02-01 |
| CA2294711C (en) | 2010-09-14 |
| ATE250934T1 (en) | 2003-10-15 |
| US6211249B1 (en) | 2001-04-03 |
| WO1999002168A1 (en) | 1999-01-21 |
| JP2001509519A (en) | 2001-07-24 |
| EP1014998B1 (en) | 2003-10-01 |
| DE69818693D1 (en) | 2003-11-06 |
| CN1267222A (en) | 2000-09-20 |
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| EEER | Examination request | ||
| MKLA | Lapsed |
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