# US 10,441,533 B2 · Ophthalmic compositions comprising polyether substituted polymers

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- Number: US 10,441,533 B2
- Document ID: US10441533B2
- Status: Granted
- Kind: B2
- Application number: 15/811,760
- Filed: 2017-11-14
- Published: 2018-03-08
- Granted: 2019-10-15
- Earliest claimed: 2004-11-22
- Assignees: Johnson & Johnson Vision Care, Inc.
- Applicants: Johnson & Johnson Vision Care, Inc.
- Inventors: Frank Molock; Kathrine Osborn Lorenz; Shivkumar Mahadevan
- Web page: https://patentgrep.com/patent/US10441533B2

## CPC

- A61K 9/0048: {Eye, e.g. artificial tears}
- A61K 31/765: Polymers containing oxygen
- A61K 31/78: of acrylic acid or derivatives thereof
- A61P 27/04: Artificial tears; Irrigation solutions
- C11D 3/0078: {Compositions for cleaning contact lenses, spectacles or lenses}
- G02B 1/041: {Lenses}
- G02B 1/043: {Contact lenses}
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS

## Abstract

The present invention relates to ophthalmic solutions and devices comprising at least one water soluble polymer having a molecular weight of at least about 500,000 Daltons and comprising linear or branched polyether pendant groups having a molecular weight of at least about 300.

## Claims

### Claim 1

An ophthalmic device comprising at least one water soluble polymer having a molecular weight of at least about 500,000 Daltons and comprising linear or branched polyether pendant groups having a molecular weight of at least about 300, wherein the polyether pendant groups provide a hydrophilic, brush or comb-like structure to the water soluble polymer.

### Claim 2 (depends on 1)

The device of claim 1 where said polyether pendant groups are derived from monomers of the Formula I
A-[(CZpHq)y—O]n—CHm—X3-m
wherein n is 7 or greater; Z is a C1-C6 substituted or unsubstituted alkyl group, q is 0, 1 or 2 and p is 2-q, y is 2 to 4, m is 1 or 2; A is any free radical polymerizable group and X is a substituent independently selected from the group consisting of H, hydroxyl, unsubstituted straight or branched alkyl groups, substituted straight or branched alkyl groups, substituted and un substituted amines, substituted and un substituted amides, mercaptans, ethers and esters.

### Claim 3 (depends on 2)

The device of claim 2 wherein X is selected from substituted or unsubstituted straight or branched C1-16 alkyl groups.

### Claim 4 (depends on 3)

The device of claim 3 wherein X is selected from is selected from substituted or unsubstituted straight or branched C1-12 alkyl groups.

### Claim 5 (depends on 3)

The device of claim 3 wherein said alkyl group is substituted with a group selected from the group consisting of carboxylic acids, esters, acyl halides, amines, amides, ketones, aldehydes, halides, sulfides, mercaptans, quartenary ammonium salts and combinations thereof.

### Claim 6 (depends on 3)

The device of claim 3 wherein n is an integer of between 7 to 50.

### Claim 7 (depends on 3)

The device of claim 3 wherein n is an integer of between 7 to 40.

### Claim 8 (depends on 1)

The device of claim 1 wherein said polymer comprises at least about 20% of backbone units have a pendant group bound thereto.

### Claim 9 (depends on 1)

The device of claim 1 wherein said polymer comprises at least about 30% of backbone units have a pendant group bound thereto.

### Claim 10 (depends on 2)

The device of claim 2 wherein at least about 20% of said pendant groups are polyether pendant groups of Formula I.

### Claim 11 (depends on 2)

The device of claim 2 wherein at least about 60% of said pendant groups are polyether pendant groups of Formula I.

### Claim 12 (depends on 2)

The device of claim 2 wherein at least about 75% of said pendant groups are polyether pendant groups of Formula I.

### Claim 13 (depends on 1)

The device of claim 1 wherein said pendant groups further comprise at least one second pendant group selected from the group consisting of silicones, sugars, carbohydrates, polyethers, amides, lactams, sulfonic acids, sulfonates, amines, hydroxyls, ethers, esters, aldehydes, ketones, amino acids, methacrylated long chain hydrocarbons, polymerizable ionic compounds, reactive latent compounds which may be converted to ionic groups after the water soluble polymer is polymerized and combinations thereof.

### Claim 14 (depends on 1)

The device of claim 1 wherein said pendant groups further comprise at least one second pendant group selected from the group consisting of amides, lactams, glycosylated materials, polymerizable ionic compounds and combinations thereof.

### Claim 15 (depends on 1)

The device of claim 1 wherein said pendant groups further comprise at least one second pendant group selected from the group consisting lauryl methacrylate, butyl methacrylate, isopropyl methacrylate, methyl methacrylate, phenyl methacrylate, hydroxyethyl methacrylate, methacrylic acid, glycerol monomethacrylate, hydroxyethyl methacrylamide, 2-(-4-morpholinyl)ethyl methacrylate, morpholinyl methacrylamide, 2-(N,N-dimethylamino)ethyl methacrylate, dimethylacrylamide, N-vinyl pyrrolidone, N-vinyl-N-methylacetamide, styrene sulfonate, sodium 2- acrylamido-2-methyl-l-propanesulfonate, sulfopropylacrylamide and combinations thereof.

### Claim 16

An ophthalmic solution comprising at least one water soluble polymer having a molecular weight of at least about 500,000 Daltons and comprising linear or branched polyether pendant groups having a molecular weight of at least about 300, wherein the polyether pendant groups provide a hydrophilic, brush or comb-like structure to the water soluble polymer.

### Claim 17 (depends on 16)

The solution of claim 16 wherein said polyether pendant groups are derived from monomers of the Formula I
A-[(CZpHq)y—O]n—CHm—X3-m
wherein n is greater than 7; Z is a C1-C6 substituted or unsubstituted alkyl group, q is 0, 1 or 2 and p is 2-q, y is 2 to 4, m is 1 or 2; A is any free radical polymerizable group and X is a substituent independently selected from the group consisting of H, hydroxyl, unsubstituted straight or branched alkyl groups, substituted straight or branched alkyl groups, substituted and unsubstituted amines, substituted and unsubstituted amides, mercaptans, ethers and esters.

### Claim 18 (depends on 17)

The solution of claim 17 wherein X is selected from substituted or unsubstituted straight or branched C1-16 alkyl groups.

### Claim 19 (depends on 17)

The solution of claim 17 wherein X is selected from is selected from substituted or unsubstituted straight or branched C1-12 alkyl groups.

### Claim 20 (depends on 18)

The solution of claim 18 wherein said alkyl group is substituted with a group selected from the group consisting of carboxylic acids, esters, acyl halides, amines, amides, ketones, aldehydes, halides, sulfides, mercaptans, quartenary ammonium salts and combinations thereof.

### Claim 21 (depends on 17)

The solution of claim 17 wherein n is an integer of between 7 to 50.

### Claim 22 (depends on 16)

The solution of claim 16 wherein said polymer comprises at least about 20% of backbone units have a pendant group bound thereto.

### Claim 23 (depends on 16)

The solution of claim 16 wherein said pendant groups further comprise at least one second pendant group selected from the group consisting of amides, lactams, glycosylated materials, polymerizable ionic compounds and combinations thereof.

### Claim 24 (depends on 16)

The solution of claim 16 wherein said pendant groups further comprise at least one second pendant group selected from the group consisting lauryl methacrylate, butyl methacrylate, isopropyl methacrylate, methyl methacrylate, phenyl methacrylate, hydroxyethyl methacrylate, methacrylic acid, glycerol monomethacrylate, hydroxyethyl methacrylamide, 2-(-4-morpholinyl)ethyl methacrylate, morpholinyl methacrylamide, 2-(N,N-dimethylamino)ethyl methacrylate, dimethylacrylamide, N-vinyl pyrrolidone, N-vinyl-N-methylacetamide, styrene sulfonate, sodium 2- acrylamido-2-methyl-l-propanesulfonate, sulfopropylacrylamide and combinations thereof.

### Claim 25 (depends on 16)

The solution of claim 16, wherein said solution is a contact lens packing, storing or cleaning solution.

### Claim 26 (depends on 16)

The solution of claim 16, wherein said solution may be directly instilled into the eye.

### Claim 27 (depends on 18)

The solution of claim 18 further comprising additional components selected from the group consisting of tonicity adjusting agents, viscosity adjusting agents, antimicrobial agents, polyelectrolytes and mixtures thereof.

### Claim 28 (depends on 17)

The solution of claim 17 wherein at least about 20% of said pendant groups are polyether pendant groups of Formula I.

### Claim 29 (depends on 16)

The solution of claim 16 wherein said pendant groups further comprise at least one second pendant group selected from the group consisting of silicones, sugars, carbohydrates, polyethers, amides, lactams, sulfonic acids, sulfonates, amines, hydroxyls, ethers, esters, aldehydes, ketones, amino acids, methacrylated long chain hydrocarbons, polymerizable ionic compounds, reactive latent compounds which may be converted to ionic groups after the water soluble polymer is polymerized and combinations thereof.