Polyurethanes for osteoimplants

Patent metadata

Field	Value
Publication number	US-9789223-B2
Application number	US-201615144139-A
Country	US
Kind code	B2
Filing date	May 2, 2016
Priority date	Feb 4, 2003
Publication date	Oct 17, 2017
Grant date	Oct 17, 2017

Abstract

Biological-based polyurethanes and methods of making the same. The polyurethanes are formed by reacting a biodegradable polyisocyanate (such as lysine diisocyanate) with an optionally hydroxylated biomolecule to form polyurethane. The polymers formed may be combined with ceramic and/or bone particles to form a composite, which may be used as an osteoimplant.

First claim

What is claimed is:

1. A biodegradable polyurethane composite, comprising: a polyurethane matrix formed by reaction of a polyisocyanate with an optionally hydroxylated biomolecule to form a biodegradable polyurethane polymer; and a reinforcement embedded in the matrix, wherein the reinforcement comprises a material selected from the group consisting of bone and bone substitutes.

2. The polyurethane composite of claim 1 , wherein the reinforcement comprises a material selected from the group consisting of calcium carbonate, calcium sulfate, calcium phosphosilicate, sodium phosphate, calcium aluminate, calcium phosphate, calcium carbonate, hydroxyapatite, demineralized bone, mineralized bone, and combinations and modified forms of the above.

3. The polyurethane composite of claim 1 , wherein the biodegradable polyurethane polymer is cross-linked.

4. The polyurethane composite of claim 1 , wherein the polyisocyanate is a diisocyanate.

5. The polyurethane composite of claim 1 , wherein the polyisocyanate is selected from the group consisting of lysine diisocyanate, toluene diisocyanate, arginine diisocyanate, asparagine diisocyanate, glutamine diisocyanate, hexamethylene diisocyanate, hexane diisocyanate, methylene bis-p-phenyl diisocyanate, isocyanurate polyisocyanates, 1,4-butane diisocyanate, uretdione polyisocyanate, and aliphatic, alicyclic, and aromatic polyisocyanates.

6. The polyurethane composite of claim 1 , wherein the biomolecule is selected from the group consisting of phospholipids, fatty acids, cholesterols, polysaccharides, starches, and combinations and modified forms of the above.

7. The polyurethane composite of claim 1 , wherein the biomolecule is lecithin.

8. The polyurethane composite of claim 1 , further comprising polycaprolactone.

9. The polyurethane composite of claim 1 , further comprising one or more substances selected from a biomolecule, a bioactive agent, and a small molecule.

10. The polyurethane composite of claim 9 , wherein the substance is selected from the group consisting of lectins, growth factors, immunosuppressives, and chemoattractants.

11. The polyurethane composite of claim 1 , comprising at least 10 weight percent of the reinforcement.

12. The polyurethane composite of claim 1 , comprising at least 30 weight percent of the reinforcement.

13. The polyurethane composite of claim 1 , comprising at least 50 weight percent of the reinforcement.

14. The polyurethane composite of claim 1 , comprising at least 70 weight percent of the reinforcement.

15. The polyurethane composite of claim 1 , wherein the polyurethane composite has a wet compressive strength that exceeds the wet compressive strength of the polyurethane alone.

16. The polyurethane composite of claim 1 , wherein the polyurethane composite has a wet compressive strength of at least 3 MPa.

17. The polyurethane composite of claim 1 , wherein the polyurethane composite has a wet compressive strength of at least 10 MPa.

18. The polyurethane composite of claim 1 , wherein the polyurethane composite has a wet compressive strength of at least 50 MPa.

19. The polyurethane composite of claim 1 , wherein the polyurethane composite has a wet compressive strength of at least 75 MPa.

20. The polyurethane composite of claim 1 , wherein the polyurethane composite has a wet compressive strength of at least 100 MPa.

Assignees

• Warsaw Orthopedic Inc

Inventors

• Knaack David
• Winterbottom John
• Kaes David R
• Boyce Todd M
• Shimp Lawrence A

Classifications

• A61P19/08

  for bone diseases, e.g. rachitism, Paget's disease · CPC title

• A61L27/54

  Biologically active materials, e.g. therapeutic substances {(A61L27/227 takes precedence)} · CPC title

• C08G18/10

  Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step · CPC title

• A61L27/3608 Primary

  Bone, e.g. demineralised bone matrix [DBM], bone powder · CPC title

• C08G18/798

  containing urethdione groups · CPC title