# US 8,771,725 B2 · Poly(urea-urethane) compositions useful as topical medicaments and methods of using the same

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- Number: US 8,771,725 B2
- Document ID: US8771725B2
- Status: Granted
- Kind: B2
- Application number: 12/244,272
- Filed: 2008-10-02
- Published: 2009-04-16
- Granted: 2014-07-08
- Earliest claimed: 2007-10-12
- Assignees: Chesson Laboratory Associates, Inc.
- Applicants: Jerry Chesson; Timothy J. Romack; Lance L. Swick; David R. Terry
- Inventors: Jerry Chesson; Timothy J. Romack; Lance L. Swick; David R. Terry
- Web page: https://patentgrep.com/patent/US8771725B2

## CPC

- A61K 31/785: Polymers containing nitrogen
- A61K 8/87: Polyurethanes
- A61K 9/0014: {Skin, i.e. galenical aspects of topical compositions (non-active ingredients are additionally classified in A61K47/00; A61K9/0009, A61K9/0021, A61K9/7015, A61K9/7023 take precedence; cosmetic preparations A61K8/00, A61Q; preparations for wound dressings or bandages A61L26/00)}
- A61K 9/7015: {Drug-containing film-forming compositions, e.g. spray-on}
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61K 47/08: containing oxygen, {e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides}
- A61K 47/10: Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
- A61K 47/18: Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
- A61K 47/22: Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
- A61K 47/26: Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
- A61L 26/0019: {obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds}
- A61L 26/0052: {Mixtures of macromolecular compounds}
- A61P 17/00: Drugs for dermatological disorders
- A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61Q 19/00: Preparations for care of the skin
- A61K 9/7069: {obtained otherwise than by reactions only involving carbon to carbon unsaturated bonds, e.g. polysiloxane, polyesters, polyurethane, polyethylene oxide}
- C08L 75/00: Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

The present invention provides a method of treating a skin ailment including administering to a subject in need thereof, a therapeutically effective amount of a composition including (i) a primary diamine; (ii) a secondary aromatic diamine; (iii) a polyisocyanate; and (iv) optionally, a polyol. The present invention also provides a method of forming a skin bandage.

## Claims

### Claim 1

A method of treating a skin ailment comprising administering to a subject in need thereof, a therapeutically effective amount of a composition comprising topically applying the composition comprising
(i) a primary polyamine;
(ii) a secondary aromatic polyamine;
(iii) a polyisocyanate; and
(iv) optionally, a polyol,
wherein the skin ailment comprises at least one of the ailments selected from the group consisting of psoriasis, bites or stings, burns, sores, hemorrhoids, anal sphincter muscle tears, and cuts and scrapes; and
wherein the composition further comprises an antibacterial, antifungal and/or antiviral medicament, and
wherein at least one of the primary polyamine, the secondary aromatic polyamine and the polyol reacts with the polyisocyanate to form a poly(urea-urethane) prepolymer.

### Claim 2 (depends on 1)

The method of claim 1, wherein the primary polyamine comprises a polyether.

### Claim 3 (depends on 1)

The method of claim 1, wherein the primary polyamine comprises polyoxypropylenediamine.

### Claim 4 (depends on 1)

The method of claim 1, wherein the secondary aromatic polyamine comprises N,N-dialkylaminodiphenylmethane or bis(sec-butylamino)diphenylmethane.

### Claim 5 (depends on 1)

The method of claim 1, wherein the polyisocyanate comprises at least one of diphenymethanediisocyanate (MDI), a modified form of monomeric MDI, MDI containing resin, aliphatic diisocyanates, aromatic diisocyanates, alicyclic diisocyanates, ethylene diisocyanate, ethylidene diisocyanate, propylene diisocyanate, butylene diisocyanate, cyclopentylene-1,3-diisocyanate, cyclohexylene-1,4,diisocyanate, cyclohexylene-1,2-diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 4,4′-diphenylmethane diisocyanate, 2,2-diphenylpropane-4,4′-diisocyanate, p-phenylene diisocyanate, m-phenylene diisocyanate, xylylene diisocyanate, 1,4-naphthylene diisocyanate, 1,5-naphthylene diisocyanate, diphenyl-4,4′-diisocyanate, azobenzene-4,4′diisocyanate, diphenylsulfone-4,4′ diisocyanate, dichlorohexamethylene diisocyanate, tetramethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, 1-chlorobenzene-2,4-diisocyanate, furfurylidene diisocyanate and triphenylmethane triisocyanate.

### Claim 6 (depends on 5)

The method of claim 5, wherein the polyisocyanate comprises MDI, a modified form of monomeric MDI and/or a MDI containing resin.

### Claim 7 (depends on 1)

The method of claim 1, wherein the polyisocyanate comprises a carbodiimide modified MDI.

### Claim 8 (depends on 1)

The method of claim 1, wherein the polyol comprises at least one of ethylene glycol, propylene glycol, 1,3-butylene glycol, 1,4-butylene glycol, 2,3-butylene glycol, a propylene oxide adduct of trimethylol propane, polyethylene glycol 200, polyethylene glycol 400 and polyethylene glycol 600.

### Claim 9 (depends on 8)

The method of claim 8, wherein the polyol comprises at least one of ethylene glycol, propylene glycol and a propylene oxide adduct of trimethylol propane.

### Claim 10 (depends on 1)

The method of claim 1, wherein composition further comprises a non-aqueous solvent selected from the group consisting of acetone, methyl ethyl ketone, methylisobutylketone, N-methylcyclohexanone, acetaldehyde, propionaldehyde, butyraldehyde, isobutyraldehyde, methyl acetate, ethyl acetate, butyl acetate, and methyl propyl acetate.

### Claim 11 (depends on 10)

The method of claim 10, wherein the volume ratio of the primary diamine in the composition ranges from about 3.6% to about 12.2% v/v, based on the total volume of the composition.

### Claim 12 (depends on 3)

The method of claim 3, wherein the ratio of the primary diamine and secondary aromatic diamine to the polyisocyanate in the composition is from about 2.8:1 to about 3.8:1 by volume.

### Claim 13 (depends on 1)

The method of claim 1, wherein the composition further comprises a colorant and/or pigment.

### Claim 14 (depends on 1)

The method of claim 1, wherein the skin ailment is psoriasis.

### Claim 15 (depends on 1)

The method of claim 1, wherein the skin ailment is bites or stings.

### Claim 16 (depends on 1)

The method of claim 1, wherein the skin ailment is burns.

### Claim 17 (depends on 1)

The method of claim 1, wherein the skin ailment is sores.

### Claim 18 (depends on 1)

The method of claim 1, wherein the skin ailment is hemorrhoids.

### Claim 19 (depends on 1)

The method of claim 1, wherein the skin ailment is anal sphincter muscle tears.

### Claim 20 (depends on 1)

The method of claim 1, wherein the skin ailment is cuts and scrapes.