Polymeric compositions

• US 7,879,356 B2
• Filed: 03/13/2001
• Issued: 02/01/2011
• Est. Priority Date: 07/11/1997
• Status: Expired due to Fees

• Current Assignee: Yissum Research Development Company of the Hebrew University of Jerusalem Ltd. (Hebrew University of Jerusalem)
• Original Assignee: Synthemed, Inc. (Pathfinder Cell Therapy, Inc.)
• Inventors: Cohn, Daniel, Levi, Avraham, Stern, Theodor
• Primary Examiner(s): Richter; Johann R
• Assistant Examiner(s): FISHER, ABIGAIL L
• Application Number:
  US09/804,745
• Publication Number:
  US 20010009662A1
• Time in Patent Office: 3,612 Days
• Field of Search: 514/772.1, 514/772.3, 525/408, 525/450, 424/486
• US Class Current: 424/486
• CPC Class Codes: A61L 31/06 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds A61L31/041 takes precedence
• CPC Class Codes: A61P 17/02 for treating wounds, ulcers, burns, scars, keloids, or the like
• CPC Class Codes: A61P 31/18 for HIV
• CPC Class Codes: A61P 41/00 Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
• CPC Class Codes: C08G 63/08 Lactones or lactides
• CPC Class Codes: C08G 63/664 derived from hydroxy carboxylic acids
• CPC Class Codes: C08G 69/44 Polyester-amides
• CPC Class Codes: C08L 67/04 Polyesters derived from hydroxycarboxylic acids, e.g. lactones C08L67/06 takes precedence
• CPC Class Codes: C08L 77/12 Polyester-amides

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 burn dressings and producing biodegradable articles, among numerous others.

Claims

1. A biodegradable or bioerodible polymeric composition consisting essentially of hydrophilically crosslinked 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, β

-propiolactone, ε

-caprolactone, δ

-glutarolactone, δ

-valerolactone, β

-butyrolactone, pivalolactone, α

,α

-diethylpropiolactone, ethylene carbonate, trimethylene carbonate, γ

-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 α

-hydroxybutyric acid, α

-hydroxyvaleric acid, α

-hydroxyisovaleric acid, α

-hydroxycaproic acid, α

-hydroxy-α

-ethylbutyric acid, α

-hydroxyisocaproic acid, α

-hydroxy-α

-methyl valeric acid, α

-hydroxyheptanoic acid, α

-hydroxystearic acid, α

-hydroxylignoceric acid, salicylic acid and mixtures, thereof and B is a polyoxyalkylene polymer which is end-capped with a non-reactive group, said AB diblock being further reacted with one or more water soluble or water dispersible crosslinking agents to produce crosslinked diblock polymers wherein said crosslinking agents comprise (poly)ethylene oxide chains or (poly)ethylene oxide-co-(poly)propylene oxide chains.

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 C₁-C₁₂ alkyl group.

4. The composition according to claim 1 wherein said polyester comprises poly(hydroxy carboxylic acid).

5. 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.

6. The composition according to claim 2 wherein said non-reactive group is an optionally substituted alkyl group.

7. The composition according to claim 6 wherein said non-reactive group is a methyl group.

8. The composition according to claim 7 wherein said polyoxyalkylene polymer is a polyethyleneoxide polymer.

9. The composition according to claim 1 wherein A is a polyester unit derived from the polymerization of lactide monomers.

10. The composition according to claim 2 wherein A is a polyester unit derived from the polymerization of lactide monomers.

11. The composition according to claim 3 wherein A is a polyester unit derived from the polymerization of lactide monomers.

12. The composition according to claim 6 wherein A is a polyester with derived from the polymerization of lactide monomers.

13. The composition according to claim 7 wherein A is a polyester unit derived from the polymerization of lactide monomers.

14. The composition according to claim 8 wherein A is a polyester unit derived from the polymerization of lactide monomers.

15. The composition according to claim 9 wherein said polyoxyalkylene polymer is a polyethyleneoxide polymer.

16. The composition according to claim 10 wherein said polyoxyalkylene polymer is a polyethyleneoxide polymer.

17. The composition according to claim 11 wherein said polyoxyalkylene polymer is a polyethyleneoxide polymer.

18. The composition according to claim 12 wherein said polyoxyalkylene polymer is a polyethyleneoxide polymer.

19. The composition according to claim 13 wherein said polyoxyalkylene polymer is a polyethyleneoxide polymer.