# US 10,500,139 B2 · Formulations and materials with cationic polymers

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- Number: US 10,500,139 B2
- Document ID: US10500139B2
- Status: Granted
- Kind: B2
- Application number: 14/908,911
- Filed: 2014-07-31
- Published: 2016-06-30
- Granted: 2019-12-10
- Earliest claimed: 2013-08-02
- Assignees: UCL Business PLC
- Applicants: Ucl Business Ltd
- Inventors: Anne Margaret Young
- Web page: https://patentgrep.com/patent/US10500139B2

## CPC

- A61K 6/891: Compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- A61K 6/69: Medicaments
- A61K 6/836: Glass
- A61K 6/838: Phosphorus compounds, e.g. apatite
- A61K 6/887: Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- A61L 24/0084: {containing fillers of phosphorus-containing inorganic compounds, e.g. apatite}
- A61L 27/10: Ceramics or glasses
- A61L 27/12: Phosphorus-containing materials, e.g. apatite
- A61L 27/16: obtained by reactions only involving carbon-to-carbon unsaturated bonds
- A61L 27/18: obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- A61L 27/26: Mixtures of macromolecular compounds
- A61L 27/46: with phosphorus-containing inorganic fillers
- A61L 27/48: with macromolecular fillers
- A61L 27/54: Biologically active materials, e.g. therapeutic substances {(A61L27/227 takes precedence)}
- A61L 2300/404: Biocides, antimicrobial agents, antiseptic agents
- A61L 2430/02: for reconstruction of bones; weight-bearing implants
- A61L 2430/12: for dental implants or prostheses
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K)

## Abstract

This invention provides fluid formulations and materials produced therefrom for repairing dental and bone defects, processes for the production of the fluid formulations and materials, and to uses of these formulations and materials. In particular, the invention provides the use cationic polymers such as polylysine in these formulations and materials, and the advantageous properties derived therefrom which include mechanical and antibacterial properties.

## Claims

### Claim 1

A process for production of a material which is a composite or a compomer, the process comprising the steps of:
i) providing a fluid formulation comprising:
(1) a fluid phase containing no water comprising at least one base monomeric or oligomeric hydrophobic compound capable of polymerisation and optionally cross-linking, which comprises a polymerisable methacrylate moiety,
(2) a filler which comprises:
(a) a reactive component comprising at least one calcium-containing compound, and
(b) a glass powder or silane-treated glass powder, and
(c) a cationic polymer, which is polylysine, present in the filler as solid particles; and
ii) covalently polymerising and optionally cross-linking said base monomeric or oligomeric compound via the methacrylate moiety, thereby forming a solid polymer matrix comprising the particles of cationic polymer.

### Claim 2 (depends on 1)

The process of claim 1, wherein the at least one base monomeric or oligomeric compound capable of polymerization is selected from urethane dimethacrylate (UDMA) and bisphenol A glycidyl methacrylate (BISGMA).

### Claim 3 (depends on 1)

The process of claim 1, wherein the formulation further comprises one or more of the following additives: a polymerisation initiator and/or hydroxyquinone.

### Claim 4 (depends on 1)

The process of claim 1, wherein the filler comprises an active agent selected from one or more of an antibacterial agent, chlorhexidine, cetyl pyridinium chloride, thymol, an antibiotic, gentamicin, tetracycline, oxycycline or minocycline.

### Claim 5 (depends on 4)

The process of claim 4, wherein the filler comprises between about 2 and 10 wt % chlorhexidine.

### Claim 6 (depends on 1)

The process of claim 1, wherein the method further comprises causing or allowing the calcium-containing compound in said filler to react with water absorbed into the polymer matrix to produce a solid filler material comprising the cationic polymer which is dispersed throughout the material.

### Claim 7 (depends on 1)

The process of claim 1 wherein the calcium-containing compound is selected from the group consisting of: α tricalcium phosphate (TCP), β tricalcium phosphate (TCP), di calcium phosphate, dicalcium phosphate dihydrate (brushite), calcium dihydrogen phosphate, monocalcium phosphate monohydrate (MCPM), tetracalcium phosphate, α calcium pyrophosphate, β calcium pyrophosphate and γ calcium pyrophosphate.

### Claim 8 (depends on 1)

The process of claim 1, wherein the reactive component is a mixture of β-TCP and MCPM, optionally in a 1:1 molar ratio, or a mixture of tristrontium phosphate and MCPM, optionally in a 1:1 molar ratio.

### Claim 9 (depends on 1)

The process of claim 1, wherein the filler is present and comprises about 5 to 25 wt % glass fibres.

### Claim 10 (depends on 1)

The process of claim 1, wherein the formulation comprises a polymerisation activator selected from N-tolylglycine glycidyl methacrylate (NTGGMA) or dimethyl paratoluidine (DMPT).

### Claim 11 (depends on 1)

The process of claim 1, wherein the filler comprises about 0.1-20 wt % polylysine and about 0-10 wt % chlorhexidine.

### Claim 12 (depends on 1)

The process of claim 1, wherein the fluid phase comprises a diluent monomer.

### Claim 13 (depends on 12)

The process of claim 12, wherein the diluent monomer is selected from: polypropylene glycol dimethacrylate (PPGDMA), and triethylene glycol dimethacrylate (TEGDMA).

### Claim 14 (depends on 1)

The process of claim 1, wherein the fluid phase comprises an adhesive monomer selected from the list consisting of: 4-methacryloxyethyl trimellitic anhydride (4-META); Pyromellitic Dimethacrylate (PMDM) and Methylmethacrylate, hydroxyethylmethacrylate (HEMA), present at 2-10 wt %.

### Claim 15 (depends on 14)

The process of claim 14, wherein the fluid phase comprises 4-methacryloxyethyl trimellitic anhydride (4-META).

### Claim 16 (depends on 13)

The process of claim 13, wherein fluid phase comprises Urethane Dimethacrylate (UDMA) and Polypropylene Glycol Dimethacrylate (PPGDMA).

### Claim 17 (depends on 7)

The process of claim 7, wherein the calcium-containing compound is Monocalcium Phosphate Monohydrate (MCPM).

### Claim 18 (depends on 1)

The process of claim 1, wherein the filler comprises about 0.5-10 wt % polylysine.

### Claim 19 (depends on 1)

A method of tooth or bone repair, or of fixation of a dental or surgical implant into a cavity or location, which method comprises performing the process of claim 1, wherein:
(i) the fluid formulation is introduced into the site of the tooth or bone damage or the cavity or location;
(ii) polymerising and/or cross-linking said base monomeric or oligomeric compound is performed by curing said formulation to form a material which is adhered to the damaged tooth or bone or the cavity or location.

### Claim 20 (depends on 19)

The method according to claim 19, wherein:
(i) the cationic polymer promotes water sorption of the material;
(ii) the cationic polymer promotes formation of a bone or dentine-like layer on the material, and re-adsorbs on this layer;
(iii) the material comprises an active agent and the cationic polymer promotes release of the active agent;
(iv) the cationic polymer enhances conversion of the polymerising and/or cross-linking compound to a polymer matrix; or
(v) any combination thereof.