Adhesive compositions for surgical use

• US 5,496,872 A
• Filed: 07/19/1994
• Issued: 03/05/1996
• Est. Priority Date: 07/21/1993
• Status: Expired due to Fees

• Current Assignee: Imedex
• Original Assignee: Imedex
• Inventors: Tayot, Jean-Louis, Tiollier, Je/ ro/ me, Soula, Ge/ rard, Constancis, Alain
• Primary Examiner(s): Michl, Paul R.
• Assistant Examiner(s): MERRIAM, ANDREW EDWIN
• Application Number:
  US08/277,069
• Time in Patent Office: 595 Days
• Field of Search: 523/111, 523/118, 524/606, 528/313, 528/318, 528/328, 514/626, 514/712, 602/50, 530/300
• US Class Current: 523/118
• CPC Class Codes: A61L 24/043 Mixtures of macromolecular materials
• CPC Class Codes: A61L 24/046 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds A61L24/043 takes precedence
• CPC Class Codes: A61L 27/18 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: A61L 27/26 Mixtures of macromolecular compounds
• CPC Class Codes: A61L 31/041 Mixtures of macromolecular compounds
• 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: C08L 81/04 Polysulfides

Abstract

The invention relates to an adhesive, biocompatible, biodegradable and non-toxic composition for surgical use, in particular for binding tissues, which composition is of the following general formula: ##STR1## in which: R is a hydrocarbon chain containing from 1 to 50 carbon atoms,

R₁ and R₂ are identical or different and are chosen from the following groups: ##STR2## R₃, R₄, R₅, R₆ and R₇ independently represent hydrogen or an aliphatic and/or alicyclic and/or aromatic group, ##STR3##

Claims

1. Adhesive, biocompatible, biodegradable and non-toxic composition for surgical use, in particular for binding biological tissues together or for binding a tissue and an implanted biomaterial, said composition being polymerizable and/or cross-linkable to form multidirectional networks, wherein the adhesive composition comprises at least an organic product containing at least two thiol functions and carboxylic functions, which may be protected or unprotected, and/or carbonyl functions, of the following general formula:

##STR26## in which;

x and y=1 or 2,

R is a hydrocarbon, chain containing from 1 to 50 carbon atoms, which is optionally substituted by a hydroxy, amino, acid or ester group, with the proviso that the radical --CO--R--CO-- is different from citric acid residue,

R₁ and R₂ are identical or different and are chosen from the following groups;

##STR27## wherein z=1 or 2, R₃, R₄, R₅, R₆ and R₇ independently represent hydrogen or an aliphatic and/or alicyclic and/or aromatic group, with the proviso that when said organic product comprises only two thiol functions, the composition includes also at least another organic product of the general formula (I) having at least three thiol functions.

2. Composition according to claim 1, wherein R₁ and R₂ represent --O--R₅.

3. Composition according to claim 1, wherein R₁ represents:

##STR28## and R₂ represents --O--R₅ or vice versa.

4. Composition according to claim 1, wherein R₁ and R₂ consist of the radical ##STR29##

5. Composition according to claim 1, wherein R is chosen such that the radical:

##STR30## in the formula (I) is a radical belonging to the class of the polycarboxylic, acid residues.

6. Composition according to claim 1, wherein R is composed of low-molecular-weight polylactic and/or polyglycolic and/or polyamino acid chains.

7. Composition according to claim 1, wherein it is provided in bioresorbable liquid solution, spray, gel or particle form or in the form of a bulk material.

8. Adhesive material according to claim 1, which comprises a combination of at least one of the products and/or polymers and/or crosslinked materials and/or compositions according to claim 1 with biological macromolecules, or synthetic or natural biodegradable polymers selected from the group consisting of:

polysaccharides;

proteins;

polyamine acids;

polyesters, polyortho esters, polyanhydrides, polyphosphazines;

and lipids and phospholipids.

9. Adhesive composition according to claim 8, wherein the polysaccharides are selected from the group consisting of starch, cellulose, chitosan, dextran, hyaluronic acid, chondroitin sulphate, and other mucopolysaccharides.

10. Adhesive composition according to claim 8, wherein the proteins are selected from the group consisting of collagen, gelatin, albumin and globulins.

11. Adhesive composition according to claim 8, wherein the polyesters are selected from the group consisting of lactic and glycolic polyesters.

12. Composition according to claim 1 wherein R is an alkylated chain containing 1 to 50 carbon atoms.

13. Compsotion according to claim 1 wherein R is an aliphatic chain of 1 to 10 carbon atoms.

14. Composition according to claim 1 wherein R₃, R₄, R₅, R₆, and R₇ independently represent a lower alkyl and/or an aromatic group.

15. Composition according to claim 1 wherein R₃, R₄, R₅ and R₆ and independently represent one of the following, groups:

##STR31## wherein 100 is an aromatic ring, at least one of R₃, R₄ and R₆ representing hydrogen or a --C(φ

)₃ group.

16. Composition according to claim 5 wherein the polycarboxylic acid residues are dicarboxylic acid residues,

17. Compositions according to claim 5 wherein R is selected from the following groups:

##STR32## with;

p≦

5,

q≧

5,

and finallly r≦

5.