Biocompatible surgical compositions

• US 8,790,488 B2
• Filed: 01/02/2013
• Issued: 07/29/2014
• Est. Priority Date: 12/08/2005
• Status: Expired due to Fees

• Current Assignee: Covidien LP (Medtronic Plc)
• Original Assignee: Covidien LP (Medtronic Plc)
• Inventors: Hadba, Ahmad R., Belcheva, Nadya
• Primary Examiner(s): Leonard, Michael L
• Application Number:
  US13/732,699
• Publication Number:
  US 20130138148A1
• Time in Patent Office: 573 Days
• Field of Search: 528/44, 528/59, 528/77, 528/85, 528/61, 528/62, 528/64, 156/331.4, 156/331.7, 524/589, 524/590, 524/591
• US Class Current: 156/331.7
• CPC Class Codes: A61B 17/0057 Implements for plugging an opening in the wall of a hollow or tubular organ, e.g. for sealing a vessel puncture or closing a cardiac septal defect sutures A61B17/04; closing rectum or urethra near body surface A61F2/0009
• CPC Class Codes: A61L 24/04 containing macromolecular materials
• CPC Class Codes: C08G 18/10 Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
• CPC Class Codes: C08G 18/283 Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
• CPC Class Codes: C08G 18/3203 Polyhydroxy compounds
• CPC Class Codes: C08G 18/3206 aliphatic
• CPC Class Codes: C08G 18/3278 containing at least three hydroxy groups
• CPC Class Codes: C08G 18/3281 containing three hydroxy groups
• CPC Class Codes: C08G 18/4277 Caprolactone and/or substituted caprolactone
• CPC Class Codes: C08G 18/4615 containing nitrogen
• CPC Class Codes: C08G 18/4887 containing carboxylic ester groups derived from carboxylic acids other than acids of higher fatty oils or other than resin acids
• CPC Class Codes: C08G 18/73 acyclic
• CPC Class Codes: C08G 2190/00 Compositions for sealing or packing joints
• CPC Class Codes: C08G 2230/00 Compositions for preparing biodegradable polymers
• CPC Class Codes: C08L 77/04 Polyamides derived from alpha-amino carboxylic acids C08L77/10 takes precedence
• CPC Class Codes: C09J 175/04 Polyurethanes
• CPC Class Codes: C09J 177/00 Adhesives based on polyamides obtained by reactions forming a carboxylic amide link in the main chain based on polyhydrazides C09J179/06; based on polyamide-imides C09J179/08; Adhesives based on derivatives of such polymers

Abstract

Biocompatible macromer compositions are provided including an isocyanate-functional polyalkylene oxide combined with at least one multi-functional isocyanate as a first component, and a multi-amino functional compound possessing multiple primary amines as a second component. The isocyanate-functional polyalkylene oxide has pendant polyalkylene oxide groups. The resulting biocompatible macromer composition can be employed as an adhesive or sealant for medical/surgical uses.

Claims

1. A biocompatible surgical adhesive comprising:

an isocyanate-functional methoxy polyethylene glycol combined with at least one multi-functional isocyanate; and

at least one diamine,

wherein the isocyanate-functional methoxy polyethylene glycol includes degradable linkages and has pendant polyalkylene oxide groups, and

wherein the biocompatible surgical adhesive further comprises an enzyme which increases the degradation rate of the degradable linkages.

2. The biocompatible surgical adhesive as in claim 1, wherein the at least one multi-functional isocyanate is selected from the group consisting of diisocyanates, triisocyanates and combinations thereof.

3. The biocompatible surgical adhesive as in claim 1, wherein the at least one multi-functional isocyanate is a diisocyanate selected from the group consisting of toluene diisocyanate, xylylene diisocyanate, bisphenylene diisocyanate, 4,4′

-oxybis(phenyl isocyanate), lysine diisocyanate, 2,4,6-trimethyl-1,3-phenylene diisocyanate, naphthylene diisocyanate, diphenylmethane diisocyanate, trimethylene diisocyanate, tetramethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, ethylethylene diisocyanate, trimethylhexane diisocyanate, heptanemethylene diisocyanate, butane diisocyanate, and combinations thereof.

4. The biocompatible surgical adhesive as in claim 1, wherein the at least one multi-functional isocyanate is a triisocyanate selected from the group consisting of triphenylmethane triisocyanate, tris(isocyanatophenyl) thiophosphate, lysine ester triisocyanate, 1,6,11-undecane triisocyanate, 1,3,6-hexamethylene triisocyanate, 1,8-diisocyanato-4-isocyanatomethyloctane, bicycloheptane triisocyanate, and combinations thereof.

5. The biocompatible surgical adhesive as in claim 1, wherein the diamine is selected from the group consisting of ethylene diamine, hexamethylene diamine, N,N′

-bis(3-aminopropyl)-1,2-ethane diamine, N-(3-aminopropyl)-1,3-propane diamine, N-(2-aminoethyl)-1,3 propane diamine, N-(3-aminopropyl)-1,4-butane diamine, N,N′

-bis(3-aminopropyl)-1,4-butane diamine, cyclohexane diamine, isomers of cyclohexane diamine, toluene diamine, phenylene diamine, and isophorone diamine.

6. The biocompatible surgical adhesive as in claim 1, wherein the isocyanate-functional methoxy polyethylene glycol combined with the at least one multi-functional isocyanate are present in an amount from about 50% to about 99% by weight of the biocompatible surgical adhesive, and the diamine is present in an amount from about 1% to about 50% by weight of the biocompatible surgical adhesive.

7. The biocompatible surgical adhesive as in claim 1, wherein the isocyanate-functional methoxy polyethylene glycol combined with the at least one multi-functional isocyanate are present in an amount from about 5% to about 45% by weight of the biocompatible surgical adhesive, and the diamine is present in an amount from about 55% to about 95% by weight of the biocompatible surgical adhesive.

8. The biocompatible surgical adhesive as in claim 1, wherein the biocompatible surgical adhesive includes a biologically active agent.

9. The biocompatible surgical adhesive as in claim 1, wherein the biocompatible surgical adhesive includes a medicinal agent.

10. A method for closing a wound comprising:

applying the biocompatible surgical adhesive of claim 1 to said wound; and

allowing the biocompatible surgical adhesive to set thereby closing said wound.

11. The method of claim 10, wherein the wound is a surgical incision.

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

applying the biocompatible surgical adhesive of claim 1 to said void; and

allowing the biocompatible surgical adhesive to set thereby filling said void.

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

applying the biocompatible surgical adhesive of claim 1 to said device, said surface or both;

bringing the device, biocompatible surgical adhesive and surface into contact with each other; and

allowing the biocompatible surgical adhesive to set thereby adhering the device and surface to each other.

14. The method of claim 13 wherein said medical device is an implant.