Antiseptic polymethylmethacrylate bone cement

Patent metadata

Field	Value
Publication number	US-10322207-B2
Application number	US-201715637456-A
Country	US
Kind code	B2
Filing date	Jun 29, 2017
Priority date	Jul 4, 2016
Publication date	Jun 18, 2019
Grant date	Jun 18, 2019

Abstract

An antiseptic composition for use as bone cement, in particular an antiseptic polymethylmethacrylate bone cement. The composition can be cured and comprises a pharmacologically tolerable salt of a monoperoxy dicarboxylic acid, whereby the salt of the monoperoxy dicarboxylic acid can be dissolved from the composition in the presence of water. Preferably, the salt of the monoperoxy dicarboxylic acid in the composition is used in the form of a powder, whereby the powder has a mean particle size of not more than 250 μm. Preferably, the salt of the monoperoxy dicarboxylic acid, in solution at room temperature, is not degraded within 5 min by the catalase enzyme.

First claim

The invention claimed is:

1. A composition for use as a bone cement, the composition comprising a curable, pharmacologically tolerable mixture of a polymerizable monomer and a pharmacologically tolerable salt of a monoperoxy dicarboxylic acid, wherein the salt of the monoperoxy dicarboxylic acid can be dissolved from the composition in the presence of water.

2. Composition according to claim 1 , wherein the composition is an antiseptic bone cement.

3. Composition according to claim 1 , wherein the composition is an antiseptic polymethylmethacrylate bone cement.

4. Composition according to claim 1 , wherein the salt of the monoperoxy dicarboxylic acid is in alkaline earth salt or an alkali salt.

5. Composition according to claim 4 , wherein the alkaline earth salt is a magnesium salt.

6. Composition according to claim 1 , wherein the salt of the monoperoxy dicarboxylic acid is not soluble in methylmethacrylate at room temperature.

7. Composition according to claim 1 , wherein the salt of the monoperoxy dicarboxylic acid in the composition is used in the form of a powder, whereby the powder has a mean particle size of not more than 250 μm.

8. Composition according to claim 1 , wherein the salt of the monoperoxy dicarboxylic acid is not degraded within 5 min by the catalase enzyme in aqueous solution at room temperature.

9. Composition according to claim 1 , which contains 0.5% by weight to 6.0% by weight of the salt of the monoperoxy dicarboxylic acid, relative to the total amount of the composition.

10. Composition according to claim 1 , wherein the monoperoxy dicarboxylic acid is selected from at least one element of the group of monoperoxy phthalic acid, monoperoxy glutaric acid, monoperoxy succinic acid, and monoperoxy cyclohexyldicarboxylic acid.

11. Composition according to claim 10 , wherein the monoperoxy dicarboxylic acid is monoperoxy phthalic acid.

12. Composition according to claim 10 , wherein the composition comprises the magnesium salt of monoperoxy phthalic acid.

13. Composition according to claim 1 , wherein the composition comprises at least one monomer for radical polymerisation and at least one organic polymer, whereby the polymer is soluble in said monomer.

14. Composition according to claim 13 , wherein the organic polymer is selected from poly(alkyl-2-acrylic acid alkylester), poly(aryl-2-acrylic acid alkylester), poly(arylalkyl-2-acrylic acid alkylester), each independently having 1 to 20 C atoms in the alkyl group, each independently having 6 to 14 C atoms in the aryl group, each independently having 6 to 14 C atoms in the arylalkyl group, and each independently having 1 to 10 C atoms in the alkylester group or a mixture comprising at least two of said polymers.

15. Composition according to claim 13 , wherein the organic polymer is selected from the group of poly(methacrylic acid methylester), poly(methacrylic acid ethylester), poly(methylmethacrylic acid propylester), poly(methacrylic acid isopropylester), poly(methylmethacrylate-co-methylacrylate), poly(styrene-co-methylmethacrylate), copolymers of monomers making up said polymers, and a mixture of at least two of said polymers.

16. Composition according to claim 13 , wherein the monomer is selected from at least one 2-alkyl-acrylic acid alkylester, 2-aryl-acrylic acid alkylester, 2-arylalkyl-acrylic acid alkylester, each independently having 1 to 20 C atoms in the alkyl group, each independently having 6 to 14 C atoms in the aryl group, each independently having 6 to 14 C atoms in the arylalkyl group, and each independently having 1 to 10 C atoms in the alkylester group or a mixture comprising at least two of said monomers.

17. Composition according to claim 13 , wherein the organic polymer comprises at least one poly(methacrylic acid methylester) (PMMA), or a poly(methacrylic acid methylester-co-polymer), and methacrylic acid methylester (MMA) as monomer.

18. Kit 1 , comprising a paste A and a paste B, whereby
(a) paste A contains:
(a1) at least one monomer for radical polymerisation;
(a2) at least one organic polymer that is soluble in (a1);
(a3) optionally, at least one polymerisation inhibitor; and
(a4) at least one component of a redox initiator system;
(b) paste B contains:
(b1) at least one monomer for radical polymerisation;
(b2) at least one organic polymer that is soluble in (b1); and
(b3) at least one polymerisation accelerator;
and whereby at least one of the pastes A or B contains, as component (a5) or (b4), a pharmacologically tolerable salt of a monoperoxy dicarboxylic acid.

19. Kit comprising a powder component C and a liquid monomer component D, whereby
(c) powder component C contains:
(c1) at least one powdered poly(meth)acrylate;
(c2) at least one powdered radiopaquer;
(c3) at least one polymerisation initiator;
(d) monomer component D contains:
(d1) at least one monomer for radical polymerisation;
(d2) optionally, at least one polymerisation inhibitor;
(d3) optionally, at least one organic polymer that is soluble in (d1); and
(d4) at least one polymerisation accelerator;
and whereby powder component C contains, as component (c4), a pharmacologically tolerable salt of a monoperoxy dicarboxylic acid.

20. Curable bone cement, obtained by polymerisation of a composition according to claim 1 .

21. Cured bone cement, obtained by polymerisation of a composition according to claim 1 , whereby the cured bone cement comprises a content of the pharmacologically tolerable salt of the monoperoxy dicarboxylic acid of 0.5% by weight to 6% by weight, relative to the total composition.

22. Cured bone cement according to claim 21 , wherein the salt of the monoperoxy dicarboxylic acid is dissolved from the composition in the presence of water during the curing and the monoperoxy dicarboxylic acid is not degraded within 5 min by the catalase enzyme.

23. Form body, obtained by polymerisation of a composition according to claim 1 .

24. Method of using a composition according to claim 1 as implant, as antiseptic implant, as revision implant, for mechanical fixation of primary total articular endoprostheses, for mechanical fixation of revision total articular endoprostheses, for augmentation of osteoporotic bone tissue, for vertebroplasty, kyphoplasty, and augmentation of drill holes in osteoporotic bone tissue, for filling bone cavities, for femuroplasty, for the manufacture of spacers, for mechanical fixation of articular endoprostheses, for covering skull defects or for the production of carrier materials for local antibiotics therapy or as carrier material for local release of pharmaceutically active substances.

Assignees

• Heraeus Medical Gmbh

Inventors

• Vogt Sebastian
• Calderón Ortiz Lorena

Classifications

• C08F212/08

  Styrene · CPC title

• A61K33/40

  Peroxides · CPC title

• A61L24/0015

  Medicaments; Biocides · CPC title

• A61L2300/212

  Peroxy acids, peracids · CPC title

• C08K5/14

  Peroxides · CPC title