Alkyd-lactone copolymers for medical applications

1. A composition, comprising: a synthetic, biodegradable, biocompatible polymer comprising the reaction product of a polybasic acid or derivative thereof, a monoglyceride and a lactone monomer.

2. The composition of claim 1 wherein said polybasic acid or derivative thereof is selected from the group consisting of succinic acid, succinic anhydride, malic acid, tartaric acid, citric acid, diglycolic acid, diglycolic anhydride, glutaric acid, glutaric anhydride, adipic acid, pimelic acid, suberic acid, sebacic acid, fumaric acid, maleic acid, maleic anhydride, mixed anhydrides, esters, activated esters and acid halides.

3. The composition of claim 1 wherein said monoglyceride is selected from the group consisting of monostearoyl glycerol, monopalmitoyl glycerol, monomyrisitoyl glycerol, monocaproyl glycerol, monodecanoyl glycerol, monolauroyl glycerol, monolinoleoyl glycerol and monooleoyl glycerol.

4. The composition of claim 3 wherein said polybasic acid derivative is succinic anhydride.

5. The composition of claim 3 wherein said polybasic acid is succinic acid.

6. The composition of claim 1 wherein said lactone monomer is selected from the group consisting of glycolide, d-lactide, 1-lactide, meso-lactide, epsilon-caprolactone, para-dioxanone, trimethylene carbonate, 1,4 dioxepan-2-one, and 1,5 dioxepan-2-one.

7. The composition of claim 1 wherein said polymer is branched.

8. The composition of claim 1 wherein said polymer comprises the reaction product of said monoglyceride, said lactone monomer, and at least two of said polybasic acids or derivatives thereof selected from the group consisting of succinic acid, succinic anhydride, malic acid, tartaric acid, citric acid, diglycolic acid and diglycolic anhydride.

9. The composition of claim 1 wherein said polymer comprises the reaction product of said polybasic acid or derivative thereof, said lactone monomer, and at least two monoglycerides selected from the group consisting of monostearoyl glycerol, monopalmitoyl glycerol, monomyrisitoyl glycerol, monocaproyl glycerol, monodecanoyl glycerol, monolauroyl glycerol, monolinoleoyl glycerol and monooleoyl glycerol.

10. The composition of claim 1 wherein said polymer comprises the reaction product of said monoglyceride, said polybasic acid or derivative thereof, and at least two lactone monomers selected from the group consisting of glycolide, d-lactide, l-lactide, meso-lactide, epsilon-caprolactone, para-dioxanone, trimethylene carbonate, 1,4 dioxepan-2-one, and 1,5 dioxepan-2-one.

11. The composition of claim 1 wherein said polymer further comprises an end-capping moiety selected from the group consisting of alkyls, alkenyls, alkynyls, acrylates, methacrylates, amines, isocyanates and isothiocyanates.

12. The composition of claim 1 , further comprising an effective amount of a bioactive agent.

13. The composition of claim 12 wherein said bioactive agent is selected from the group consisting of antiinfectives, analgesics, anorexics, antihelmintics, antiarthritics, antiasthmatics, anticonvulsants, antidepressants, antidiuretics, antidiarrheals, antihistamines, antiinflammatory agents, antimigraine preparations, antinauseants, antineoplastics, antiparkinsonism drugs, antipruritics, antipsychotics, antipyretics, antispasmodics, anticholinergics, sympathomimetics, xanthine derivatives, calcium channel blockers, beta-blockers, antiarrhythmics, antihypertensives, diuretics, vasodilators, central nervous system stimulants, decongestants, hormones, steroids, hypnotics, immunosuppressives, muscle relaxants, parasympatholytics, psychostimulants, sedatives, tranquilizers, naturally derived or genetically engineered proteins, growth factors, polysaccharides, glycoproteins, or lipoproteins, oligonucleotides, antibodies, antigens, cholinergics, chemotherapeutics, hemostatics, clot dissolving agents, radioactive agents and cystostatics.

14. The composition of claim 1 comprising a microdispersion, said microdispersion comprising a solid polymer phase dispersed in a liquid polymer phase, wherein one of said solid polymer and said liquid polymer comprise the reaction product of a polybasic acid or derivative thereof, a monoglyceride, and a lactone monomer; wherein said solid polymer has a melting point between about 25° C. and about 70° C., and wherein said liquid polymer has a melting point below about 25° C.

15. The composition of claim 13 wherein said polybasic acid or derivative thereof is selected from the group consisting of succinic acid, succinic anhydride, malic acid, tartaric acid, citric acid, diglycolic acid, diglycolic anhydride, glutaric acid, glutaric anhydride, adipic acid, pimelic acid, suberic acid, sebacic acid, fumaric acid, maleic acid, maleic anhydride, mixed anhydrides, esters, activated esters and acid halides.

16. The composition of claim 14 wherein said monoglyceride is selected from the group consisting of monostearoyl glycerol, monopalmitoyl glycerol, monomyrisitoyl glycerol, monocaproyl glycerol, monodecanoyl glycerol, monolauroyl glycerol, monolinoleoyl glycerol and monooleoyl glycerol.

17. The composition of claim 15 wherein said polybasic acid derivative is succinic anhydride.

18. The composition of claim 15 wherein said polybasic acid is succinic acid.

19. The composition of claim 13 wherein said lactone monomer is selected from the group consisting of glycolide, d-lactide, l-lactide, meso-lactide, epsilon-caprolactone, para-dioxanone, trimethylene carbonate, 1,4 dioxepan-2-one, and 1,5 dioxepan-2-one.

20. The composition of claim 13 further comprising an effective amount of a bioactive agent.

21. The composition of claim 13 wherein both said solid polymer and said liquid polymer comprise the reaction product of a polybasic acid or derivative thereof, a monoglyceride, and a lactone monomer.

22. A medical device comprising a coating, said coating comprising: a synthetic, biodegradable, biocompatible polymer comprising the reaction product of a polybasic acid or derivative thereof, a monoglyceride, and a lactone monomer.

23. The medical device of claim 22 wherein said polybasic acid or derivative thereof is selected from the group consisting of succinic acid, succinic anhydride, malic acid, tartaric acid, citric acid, diglycolic acid, diglycolic anhydride, glutaric acid, glutaric anhydride, adipic acid, pimelic acid, suberic acid, sebacic acid, fumaric acid, maleic acid, maleic anhydride, mixed anhydrides, esters, activated esters and acid halides.

24. The medical device of claim 22 wherein said monoglyceride is selected from the group consisting of monostearoyl glycerol, monopalmitoyl glycerol, monomyrisitoyl glycerol, monocaproyl glycerol, monodecanoyl glycerol, monolauroyl glycerol, monolinoleoyl glycerol and monooleoyl glycerol.

25. The medical device of claim 24 wherein said polybasic acid derivative is succinic anhydride.

26. The medical device of claim 24 wherein said polybasic acid is succinic acid.

27. The medical device of claim 22 wherein said lactone monomer is selected from the group consisting of glycolide, d-lactide, l-lactide, meso-lactide, epsilon-caprolactone, para-dioxanone, trimethylene carbonate, 1,4 dioxepan-2-one, and 1,5 dioxepan-2-one.

28. The medical device of claim 22 wherein said polymer is branched.

29. The medical device of claim 22 wherein said polymer comprises the reaction product of said monoglyceride, said lactone monomer, and at least two of said polybasic acids or derivatives thereof selected from the group consisting of succinic acid, succinic anhydride, malic acid, tartaric acid, citric acid, diglycolic acid and diglycolic anhydride.

30. The medical device of claim 22 wherein said polymer comprises the reaction product of said polybasic acid or derivative thereof, said lactone monomer, and at least two monoglycerides selected from the group consisting of monostearoyl glycerol, monopalmitoyl glycerol, monomyrisitoyl glycerol, monocaproyl, glycerol, monodecanoyl glycerol, monolauroyl glycerol, monolinoleoyl glycerol and monooleoyl glycerol.

31. The medical device of claim 22 wherein said polymer comprises the reaction product of said monoglyceride, said polybasic acid or derivative thereof, and at least two lactone monomers selected from the group consisting of glycolide, d-lactide, l-lactide, meso-lactide, epsilon-caprolactone, para-dioxanone, trimethylene carbonate, 1,4 dioxepan-2-one, and 1,5 dioxepan-2-one.

32. The medical device of claim 22 wherein said polymer further comprises an end-capping moiety selected from the group consisting of alkyls, alkenyls, alkynyls, acrylates, methacrylates, amines, isocyanates and isothiocyanates.

33. The medical device of claim 22 , further comprising an effective amount of a bioactive agent.

34. The medical device of claim 22 further comprising an aliphatic polyester prepared from the group of monomers selected from the group consisting of glycolide, L-lactide, D-lactide, meso-lactide, rac-lactide, ε-caprolactone, trimethylene carbonate, p-dioxanone, 1,4-dioxanone, 1,4-dioxepan-2-one, 1,5-dioxepan-2-one and substituted derivatives thereof.

35. A synthetic polymer comprising the reaction product of:

a polybasic acid or derivative thereof;

a monoglyceride; and

a lactone monomer.

36. The polymer of claim 35 wherein said polybasic acid or derivative thereof is selected from the group consisting of succinic acid, succinic anhydride, malic acid, tartaric acid, citric acid, diglycolic acid, diglycolic anhydride, glutaric acid, glutaric anhydride, adipic acid, pimelic acid, suberic acid, sebacic acid, fumaric acid, maleic acid, maleic anhydride, mixed anhydrides, esters, activated esters and acid halides.

37. The polymer of claim 35 wherein said monoglyceride is selected from the group consisting of monostearoyl glycerol, monopalmitoyl glycerol, monomyrisitoyl glycerol, monocaproyl glycerol, monodecanoyl glycerol, monolauroyl glycerol, monolinoleoyl glycerol and monooleoyl glycerol.

38. The polymer of claim 37 wherein said polybasic acid derivative is succinic anhydride.

39. The polymer of claim 37 wherein said polybasic acid is succinic acid.

40. The polymer of claim 35 wherein said lactone monomer is selected from the group consisting of glycolide, d-lactide, l-lactide, meso-lactide, epsilon-caprolactone, para-dioxanone, trimethylene carbonate, 1,4 dioxepan-2-one, and 1,5 dioxepan-2-one.

41. The polymer of claim 35 wherein said polymer is branched.

42. The polymer of claim 35 wherein said polymer comprises the reaction product of said monoglyceride, said lactone monomer, and at least two of said polybasic acids or derivatives thereof selected from the group consisting of succinic acid, succinic anhydride, malic acid, tartaric acid, citric acid, diglycolic acid and diglycolic anhydride.

43. The polymer of claim 35 wherein said polymer comprises the reaction product of said polybasic acid or derivative thereof, said lactone monomer, and at least two monoglycerides selected from the group consisting of monostearoyl glycerol, monopalmitoyl glycerol, monomyrisitoyl glycerol, monocaproyl glycerol, monodecanoyl glycerol, monolauroyl glycerol, monolinoleoyl glycerol and monooleoyl glycerol.

44. The polymer of claim 35 wherein said polymer comprises the reaction product of said monoglyceride, said polybasic acid or derivative thereof, and at least two lactone monomers selected from the group consisting of glycolide, d-lactide, l-lactide, meso-lactide, epsilon-caprolactone, para-dioxanone, trimethylene carbonate, 1,4 dioxepan-2-one, and 1,5 dioxepan-2-one.