Bone cement compositions

• US 20060270750A1
• Filed: 04/05/2004
• Published: 11/30/2006
• Est. Priority Date: 04/04/2003
• Status: Abandoned Application

• Current Assignee: TA Contrast AB
• Original Assignee: TA Contrast AB
• Inventors: Klaveness, Jo, Brudeli, Bjarne, Almen, Torsten
• Application Number:
  US10/552,069
• Publication Number:
  US 20060270750A1
• Time in Patent Office: Days
• US Class Current: 523/113
• CPC Class Codes: A61L 24/001 Use of materials characterised by their function or physical properties
• CPC Class Codes: A61L 24/06 obtained by reactions only involving carbon-to-carbon unsaturated bonds A61L24/043, A61L24/046 take precedence
• CPC Class Codes: A61L 2430/02 for reconstruction of bones; weight-bearing implants
• CPC Class Codes: A61L 27/50 Materials characterised by their function or physical properties , e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials

Abstract

The present invention provides a bone cement comprising in admixture a monomer-containing liquid portion and a particulate polymer portion, wherein at least one of the portions comprises a dissolved nonpolymerizable organoiodine compound.

Claims

1. A bone cement comprising in admixture a monomer-containing liquid portion and a particulate polymer portion, wherein at least one of said portions comprises a dissolved non-polymerizable organoiodine compound.

6. The bone cement as claimed in claim 1, wherein said cement additionally comprises an antibiotic compound.

7. The bone cement as claimed in claim 6, wherein said antibiotic compound is selected from the group consisting of gentamicin, colistin, erythromycin, clindamicin, penicillins, norfloxacin and chloramphenicol.

8. The bone cement as claimed in claim 6, wherein said antibiotic compound is present in the form of a lipophilic ester.

9. The bone cement as claimed in claim 1, wherein the concentration of the organoiodine compound within the polymer particle portion differs by less than 50% compared to the concentration of the organoiodine within the polymer which is prepared in situ from the monomer during use.

10. The bone cement as claimed in claim 6, wherein the concentration of the antibiotic compound within the polymer particle portion differs by less than 50% compared to the concentration of the organoiodine within the polymer prepared in situ from the monomer during use.

11. The bone cement as claimed in claim 10, wherein the concentration of the antibiotic compound within the polymer particles portion differs by less than 10% compared to the concentration of the organoiodine within the polymer prepared in situ from the monomer during use.

12. The bone cement as claimed in claim 1, wherein said organoiodine compound is a cross-linking agent and is present in an amount of up to 2% wt of the composition.

13. The bone cement as claimed in claim 1, wherein the liquid portion additionally comprises at least one of hydroquinone, growth hormone, BMP or vitamins.

14. The bone cement as claimed in claim 1, wherein said liquid portion is present in a range of from 25 to 45% wt of cement.

15. The bone cement as claimed in claim 1, wherein said polymer portion additionally comprises at least one of hydroquinone, growth hormone, BMP or vitamins.

16. The bone cement as claimed in claim 1, wherein said polymer particles of said polymer portion have a mode particle size of from 1 to 200 μ

m.

17. The bone cement as claimed in claim 1, wherein said polymer particles of said polymer portions are polydisperse.

40. A method of affixing a joint prosthesis comprising inserting said prosthesis and a bone cement into a bone cavity, said cement is a cement as claimed in claim 1.

42. The bone cement as claimed in claim 9, wherein the concentration of the organoiodine compound within the polymer particles portion differs by less than 10% compared to the concentration of the organoiodine within the polymer prepared in situ from the monomer during use.

2. A bone cement comprising in admixture a monomer-containing liquid portion and a particulate polymer portion, wherein said liquid portion comprises a polymerizable organoiodine compound and said particulate polymer has a polymeric structure comprising covalently bonded residues of a polymerizable organoiodine compound.

3. A bone cement comprising in admixture a monomer-containing liquid portion and a particulate polymer portion, wherein said liquid portion comprises a polymerizable organoiodine compound and/or said particulate polymer has a polymeric structure comprising covalently bonded residues of a polymerizable organoiodine compound, wherein said polymerizable organoiodine compound comprises an organoiodine moiety covalently bonded via an amide bond, but not an ester bond, to a polymerizable moiety.

4. A bone cement having a chemically homogenized distribution of all components therein.

5. The bone cement as claimed in claim 4, wherein said cement comprises an X-ray contrast agent.

18. A bone cement kit comprising a monomer-containing liquid portion and separate therefrom a particulate polymer portion, wherein at least one of said portions comprises a dissolved non-polymerizable organoiodine compound, said kit optionally further comprises instructions for the preparation of a bone cement therewith.

19. A bone cement kit comprising a monomer-containing liquid portion and separate therefrom a particulate polymer portion, wherein said liquid portion comprises a polymerizable organoiodine compound and said particulate polymer has a polymer structure comprising covalently bonded residues of a polymerizable organoiodine compound, said kit optionally further comprises instructions for the preparation of a bone cement therewith.

20. A bone cement kit comprising a monomer-containing liquid portion and separate therefrom a particulate polymer portion, wherein said liquid portion comprises a polymerizable organoiodine compound and/or said particulate polymer has a polymer structure comprising covalently bonded residues of a polymerizable organoiodine compound, wherein said polymerizable organoiodine compound comprises an organoiodine moiety covalently bonded via an amide bond, but not an ester bond, to a polymerizable moiety.

21. A bone cement kit providing a bone cement comprising a chemically homogeneous distribution of all components within the final bone cement.

22. The bone cement kit as claimed in claim 21, wherein said cement comprises an X-ray contrast agent.

23. The bone cement kit as claimed in claim 21, wherein said cement additionally comprises an antibiotic agent.

24. An organoiodine compound of formula IV

wherein each R⁶ group which may be the same or different, is an acyloxyalkylcarbonylamino, N-(acyloxyalkyl carbonyl)acyloxyalkylamino, N-acyloxyalkylcarbonyl-N-alkyl-amino, acyloxyalkylaminocarbonyl, bis(acyloxyalkyl)aminocarbonyl, N-acyloxyalkyl-N-alkylaminocarbonyl, alkoxyalkylaminocarbonyl, N-alkylalkoxyalkylaminocarbonyl, bis(alkoxyalkyl)aminocarbonyl, alkoxyalkylcarbonylamino, N-alkylalkoxyalkylcarbonylamino or N-alkoxyalkylcarbonylalkoxyalkylamino group or a triiodophenyl group attached via a 1 to 10 atom bridge optionally substituted by an acyloxyalkyl, acyloxyalkylcarbonyl, acyloxyalkylamino, acyloxyalkylcarbonylamino, acyloxyalkylaminocarbonyl, alkoxyalkyl, alkoxyalkylcarbonyl, alkoxyalkylamino, alkoxyalkylcarbonylamino, or alkoxyalkylaminocarbonyl group or by a polymerizable group, or one or two R⁶ groups is/are a polymerizable group, optionally attached via a 1 to 10 atom bridge;

or where one R⁶ group is a polymerizable group, and one or both of the remaining R⁶ groups is an alkylamino, bisalkylamino, alkylcarbonylamino, N-alkyl-alkylcarbonylamino, alkylaminocarbonyl or bis-alkyl-aminocarbonyl group.

25. The organoiodine compound as claimed in claim 24, wherein each R⁶ group is a triiodophenyl group attached via a 1 to 10 atom bridge composed of bridging atoms selected from O, N and C.

36. The method for preparing an organoiodine compound as claimed in claim 24, wherein said compound is prepared from triiodophenyl carboxylic acids and amines.

37. The method as claimed in claim 36, additionally comprising a polymerization initiator.

38. The method as claimed in claim 37, wherein said polymerization initiator is selected from the group consisting of N,N-dimethylp-toluidine, N,N-dimethylaminobenzyl alcohol (DMOH) and N,N-dimethylaminobenzyl oleate (DMAO).

39. The method as claimed in claim 37, wherein said polymerization initiator is present in an amount up to 2% wt of the composition.

26. A method of producing a bone cement comprising admixing a liquid monomer portion and a particulate polymer portion, wherein admixture of said portions is effected under helium.

27. A method for preparing a particulate polymer of a bone cement, wherein polymer particles are formed by emulsion polymerization.

28. The method as claimed in claim 27, wherein said emulsion is oil-in-water.

29. The method as claimed in claim 27, wherein the emulsion has an aqueous phase additionally comprising an emulsifier.

32. The method as claimed in claim 27, wherein polymerization is effected at a temperature in the range of from 50 to 100°

C.

33. The method as claimed in claim 32, wherein polymerization is effected at a temperature in the range of from 70 to 80°

C.

34. The method as claimed in claim 27, additionally comprising a polymerization initiator.

35. The method as claimed in claim 34, wherein said polymerization initiator is selected from the group consisting of benzyl peroxide (BPO), 2,2′

-azo-bis-isobutlyronitrile (AIBN) and t-butyl peroxybenzoate.

30. A method of producing polymer particles by emulsion polymerization wherein salts are added to the aqueous phase.

31. A method of producing polymer particles by emulsion polymerization, wherein the pH is adjusted by the addition of acids, bases or by the use of buffers.

41. Bone cement characterized in that the mechanical properties regarding the ultimate tensile strength and ultimate strain are greater than 10% higher than Palacos®

bone.