Bioabsorbable Surgical Composition

• US 20100092533A1
• Filed: 10/02/2009
• Published: 04/15/2010
• Est. Priority Date: 10/15/2008
• Status: Abandoned Application

• Current Assignee: Covidien LP (Medtronic Plc)
• Original Assignee: Covidien LP (Medtronic Plc)
• Inventors: Hadba, Ahmad, Stopek, Joshua
• Application Number:
  US12/572,358
• Publication Number:
  US 20100092533A1
• Time in Patent Office: Days
• US Class Current: 424/422
• CPC Class Codes: A61L 24/0042 Materials resorbable by the body
• CPC Class Codes: A61L 24/04 containing macromolecular materials
• CPC Class Codes: A61L 27/14 Macromolecular materials
• CPC Class Codes: A61L 27/58 Materials at least partially resorbable by the body
• 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 18/40 High-molecular-weight compounds C08G18/2805 takes precedence

Abstract

Bioabsorbable macromer compositions are provided including a polymeric component possessing a hydroxamate segment and a polymer segment. The polymeric component can be used by itself, or in some embodiments, combined with a second component, to form a macromer composition of the present disclosure. The resulting bioabsorbable macromer composition can be employed as an adhesive or sealant for medical/surgical uses.

Claims

1. A bioabsorbable macromer composition of the formula selected from the group consisting of

R₁-[A]_v-R₂

and

R₂-[A]_v-R₁-[A]_v-R₂

wherein R₁ comprises a hydroxamate segment, R₂ comprises a polymer segment selected from the group consisting of polysaccharides and polyols, A is a bioabsorbable group, and v is a number from about 1 to about 20.

2. A bioabsorbable macromer composition of the formula selected from the group consisting of

R₁-[A]_v-R₂—

R₃

and

R₃—

R₂-[A]_v-R₁-[A]_v-R₂—

R₃

wherein R₁ comprises a hydroxamate segment, R₂ comprises a polymer selected from the group consisting of polysaccharides and polyols, R₃ comprises a functional group selected from the group consisting of isocyanates, succinimides, aldehydes, and combinations thereof, A is a bioabsorbable group, and v is a number from about 1 to about 20.

3. A bioabsorbable macromer composition comprising:

a first polymeric component of the formula

R₃—

R₂-[A]_v-R₁-[A]_v-R₂—

R₃

wherein R₁ comprises a hydroxamate segment, R₂ comprises a polymer selected from the group consisting of polysaccharides and polyols, R₃ comprises a functional group selected from the group consisting of isocyanates, succinimides, aldehydes, and combinations thereof, A is a bioabsorbable group, and v is a number from about 1 to about 20; and

a second component possessing at least one group reactive with the functional component of the polymeric component.

4. A bioabsorbable macromer composition as in claim 3, wherein R₂ comprises a polyol selected from the group consisting of polyethylene oxide, polyethylene glycol, polypropylene glycol, polyethylene oxide-polypropylene oxide copolymers, polyethylene glycol-adipate, polyethylene glycol-polypropylene glycol copolymers, and combinations thereof.

5. A bioabsorbable macromer composition as in claim 3, wherein R₂ comprises polyethylene glycol.

6. A bioabsorbable macromer composition as in claim 3, wherein R₂ comprises a polysaccharide selected from the group consisting of sorbitol, mannitol, sucrose, dextran, cyclodextrin, and combinations thereof.

7. A bioabsorbable macromer composition as in claim 3, wherein the bioabsorbable group is selected from the group consisting of lactic acid, glycolic acid, 1,4-dioxane-2-one, 1,3-dioxane-2-one, succinnic acid, adipic acid, sebacic acid, malonic acid, glutaric acid, azelaic acid, ethyl dichlorophosphate, sebacic acid anhydride, azelaic acid anhydride, and combinations thereof.

8. A bioabsorbable macromer composition as in claim 3, wherein the bioabsorbable group is selected from the group consisting of lactide, glycolide, E-caprolactone, p-dioxanone, trimethylene carbonate, and combinations thereof.

9. A bioabsorbable macromer composition as in claim 3, wherein v is a number from about 2 to about 6.

10. A bioabsorbable macromer composition as in claim 3, wherein the hydroxamate segment comprises at least one hydroxamate of the formula

wherein R₅ is selected from the group consisting of vinyl groups, hydroxyl alkyl acrylate groups, hydroxy alkyl methacrylate groups, alkyl groups, alkoxy groups, alkenyl groups, acrylamides, methacrylamides, polymers, and combinations thereof, and R₆ is selected from the group consisting of hydrogen, alkyl groups, alkoxy groups, alkenyl groups, and combinations thereof.

11. A bioabsorbable macromer composition as in claim 3, wherein the isocyanate is selected from the group consisting of 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, 2,2′

-diphenylmethane diisocyanate, 2,4′

-diphenylmethane diisocyanate, 4,4′

-diphenylmethane diisocyanate, diphenyldimethylmethane diisocyanate, dibenzyl diisocyanate, naphthylene diisocyanate, phenylene diisocyanate, xylylene diisocyanate, 4,4′

-oxybis(phenyl isocyanate), tetramethylxylylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, lysine diisocyanate, 2-methylpentane-1,5-diisocyanate, 3-methylpentane-1,5-diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, isophorone diisocyanate, cyclohexane diisocyanate, hydrogenated xylylene diisocyanate, hydrogenated diphenylmethane diisocyanate, hydrogenated trimethylxylylene diisocyanate, 2,4,6-trimethyl 1,3-phenylene diisocyanate, and combinations thereof.

12. A bioabsorbable macromer composition as in claim 11, wherein the second component possesses at least one isocyanate-reactive group selected from the group consisting of at least one hydroxy group, at least one amine group, at least one sulfhydryl group, and combinations thereof.

13. A bioabsorbable macromer composition as in claim 12, wherein the second component possessing at least one hydroxy group is selected from the group consisting of water, polyether-based polyols, polycaprolactone-based polyols, polyhydric alcohols, disaccharides, and combinations thereof.

14. A bioabsorbable macromer composition as in claim 12, wherein the second component possessing at least one amine group is selected from the group consisting of bis(3-aminopropyl)amine, spermine, polyetheramines, trilysine, polylysine, polyarginine, albumin, ethylenediamine, N-ethylethylenediamine, N,N′

-diethylethylenediamine, butane-1,4-diamine, pentane-1,5-diamine, hexane-1,6-diamine, phenylene diamine, ethanolamine, N-ethylethanolamine, triethylenediamine, N-methylmorpholine, pentamethyl diethylenetriamine, dimethylcyclohexylamine, tetramethylethylenediamine, 1-methyl-4-dimethylaminoethyl-piperazine, 3-methoxy-N-dimethyl-propylamine, N-ethylmorpholine, diethylethanolamine, N-cocomorpholine, N,N-dimethyl-N′

,N′

-dimethylisopropyl-propylene diamine, N,N-diethyl-3-diethyl aminopropylamine, dimethyl-benzyl amine, and combinations thereof.

15. A bioabsorbable macromer composition as in claim 12, wherein the second component possessing at least one amine group comprises a diamine of the formula

NH₂—

R₄—

NH₂

wherein R₄ comprises a polymer selected from the group consisting of polysaccharides, polyols, and combinations thereof.

16. A bioabsorbable macromer composition as in claim 12, wherein the second component possessing at least one sulfhydryl group is selected from the group consisting of thiolated gelatin, thiolated collagen, PEG-thiols, pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), trimethylolpropane tris(2-mercaptoacetate), trimethylolpropane tris(2-mercaptopropionate), and combinations thereof.

17. A method for closing a wound comprising:

applying the bioabsorbable macromer composition of claim 3 to the wound; and

allowing the bioabsorbable macromer composition to set thereby closing the wound.

18. The method of claim 17 wherein the wound is a surgical incision.

19. A method for filling a void in animal tissue comprising:

applying the bioabsorbable macromer composition of claim 3 to the void; and

allowing the bioabsorbable macromer composition to set thereby filling the void.

20. A method for adhering a medical device to a surface of animal tissue comprising the steps of:

applying the bioabsorbable macromer composition of claim 3 to the device, the surface or both;

bringing the device, bioabsorbable macromer composition and surface into contact with each other; and

allowing the bioabsorbable macromer composition to set thereby adhering the device and surface to each other.

21. The method of claim 20, wherein said medical device is an implant.