Ophthalmic Compositions Comprising a Branched, Glycerol Monoalkyl Compound and a Fatty Acid Monoester

• US 20070286767A1
• Filed: 03/26/2007
• Published: 12/13/2007
• Est. Priority Date: 06/08/2006
• Status: Active Grant

• Current Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Original Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Inventors: Salamone, Joseph C., Burke, Susan E., Phillips, Eric, Zhao, Fang, Barniak, Vicki
• Granted Patent: US 7,670,997 B2
• Time in Patent Office: Days
• US Class Current: 422/28
• CPC Class Codes: A61K 9/0048 Eye, e.g. artificial tears
• CPC Class Codes: A61L 12/141 Biguanides, e.g. chlorhexidine
• CPC Class Codes: A61L 12/142 Polymeric biguanides
• CPC Class Codes: A61L 12/143 Quaternary ammonium compounds
• CPC Class Codes: A61L 12/145 Polymeric quaternary ammonium compounds
• CPC Class Codes: C11D 1/667 Neutral esters, e.g. sorbitan esters
• CPC Class Codes: C11D 3/0026 Low foaming or foam regulating compositions
• CPC Class Codes: C11D 3/0078 Compositions for cleaning contact lenses, spectacles or lenses
• CPC Class Codes: C11D 3/2068 Ethers
• CPC Class Codes: C11D 3/2093 Esters; Carbonates
• CPC Class Codes: C11D 3/30 Amines; Substituted amines ; Quaternized amines
• CPC Class Codes: C11D 3/3427 containing thiol, mercapto or sulfide groups, e.g. thioethers or mercaptales
• CPC Class Codes: C11D 3/48 Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
• CPC Class Codes: Y10S 134/901 Contact lens

Abstract

An aqueous ophthalmic composition comprising a branched, glycerol monoalkyl compound and a fatty acid monoester. The fatty acid monoester comprises an aliphatic fatty acid portion having six to fourteen carbon atoms and an aliphatic hydroxyl portion. The composition will also have an osmolality in a range from 200 mOsmol/kg to 400 mOsmol/kg. The invention is also directed to a method of inhibiting the formation of foam in an aqueous ophthalmic composition that includes a surfactant as well as to a method of enhancing the biocidal efficacy of an aqueous ophthalmic composition containing a fatty acid monoester.

Claims

1. An aqueous ophthalmic composition comprising:

a branched, glycerol monoalkyl compound; and

a fatty acid monoester, wherein the fatty acid monoester comprises an aliphatic fatty acid portion having six to fourteen carbon atoms and an aliphatic hydroxyl portion;

said composition having an osmolality in a range from 200 mOsmol/kg to 400 mOsmol/kg.

2. The composition of claim 1 wherein the branched, glycerol monoalkyl compound is selected from a branched, glycerol monoalkyl ether, a branched, glycerol monoalkyl amine or a branched, glycerol monoalkyl sulfide, or any mixture thereof, and is present in a total amount from 0.05 ppm to 1,000 ppm.

3. The composition of claim 2 wherein the aliphatic fatty acid portion is a straight chain, saturated or unsaturated hydrocarbon with eight to ten carbons, or a branched chain, saturated or unsaturated hydrocarbon with eight to ten carbons.

4. The composition of claim 3 wherein the aliphatic hydroxyl portion is selected from propylene glycol, polyethylene glycol, polypropylene glycol, glycerol, linear polyol and cyclic polyol.

5. The composition of claim 3 wherein the aliphatic hydroxyl portion is glycerol.

6. The composition of claim 1 wherein the branched, glycerol monoalkyl compound is 3-[(2-ethylhexyl)oxy]-1,2-propanediol, 3-[(2-ethylhexyl)amino]-1,2-propanediol, 3-[(2-ethylhexyl)thiol]-1,2-propanediol or any mixture thereof.

7. The composition of claim 1 further comprising a cationic antimicrobial component selected from the group consisting of poly[dimethylimino-2-butene-1,4-diyl]chloride, α

-[4-tris(2-hydroxyethyl)ammonium chloride-2-butenyl]poly[1-dimethyl ammonium chloride-2-butenyl]-ω

-tris(2-hydroxyethyl)ammonium chloride, myristamidopropyl dimethylamine, benzalkonium halides, alexidine and salts thereof, salts of chlorhexidine, hexamethylene biguanides and salts thereof and their polymers, and mixtures thereof.

8. The composition of claim 1 further comprising a cationic antimicrobial component selected from the group consisting of poly(hexamethylene biguanide) or PHMB-CG*, which is present from 0.01 ppm to 3 ppm, α

-[4-tris(2-hydroxyethyl)ammonium chloride-2-butenyl]poly[1-dimethylammonium chloride-2-butenyl]-ω

-tris(2-hydroxyethyl)ammonium chloride, which is present from 1 ppm to 100 ppm, and any mixture thereof.

9. The composition of claim 3 further comprising dexpanthenol, sorbitol or any mixture thereof.

10. The composition of claim 3 further comprising 2-amino-2-methyl-1,3-propanediol, and glycolic acid, asparatic acid or a mixture thereof, wherein a molar ratio of the total glycolic acid, asparatic acid or mixture thereof to AMPD is from 1:

20 to 1.3;

1.

11. The use of the ophthalmic composition of claim 1 in an eye care or a contact lens care product selected from the group consisting of eye drops, contact lens preservative solution, contact lens cleaning solution, and contact lens multi-purpose solution.

12. The use of the ophthalmic composition of claim 1 as a contact lens multi-purpose solution to disinfect a soft contact lens.

13. A method of inhibiting the formation of foam in an aqueous ophthalmic composition comprising a surfactant, the method comprising adding a branched, glycerol monoalkyl compound to the composition in an amount from 0.05 ppm to 30.0 ppm to inhibit the formation of foam or to destabilize foam in the composition, the composition having an osmolality in a range from 200 mOsmol/kg to 400 mOsmol/kg.

14. The method of claim 13 wherein the branched, glycerol monoalkyl compound is selected from a branched, glycerol monoalkyl ether, a branched, glycerol monoalkyl amine or a branched, glycerol monoalkyl sulfide, or any mixture thereof

15. The method of claim 13 wherein the ophthalmic composition further comprises a cationic antimicrobial component selected from the group consisting of poly[dimethylimino-2-butene-1,4-diyl]chloride, α

-[4-tris(2-hydroxyethyl)ammonium chloride-2-butenyl]poly[1-dimethylammonium chloride-2-butenyl]-ω

-tris(2-hydroxyethyl)ammonium chloride, myristamidopropyl dimethylamine, benzalkonium halides, alexidine and salts thereof, salts of chlorhexidine, hexamethylene biguanides and salts thereof and their polymers, and mixtures thereof.

16. The method of claim 13 wherein the ophthalmic composition further comprises a cationic antimicrobial component selected from the group consisting of poly(hexamethylene biguanide), which is present from 0.01 ppm to 3 ppm, α

-[4-tris(2-hydroxyethyl)ammonium chloride-2-butenyl]poly[1-dimethylammonium chloride-2-butenyl]-ω

-tris(2-hydroxyethyl)ammonium chloride, which is present from 1 ppm to 100 ppm, and any mixture thereof.

17. A method of enhancing the biocidal efficacy of an aqueous ophthalmic composition containing a fatty acid monoester, the method comprising adding a branched, glycerol monoalkyl compound to the composition, wherein the wherein the fatty acid monoester comprises an aliphatic fatty acid portion having six to fourteen carbon atoms and an aliphatic hydroxyl portion, and the composition has an osmolality in a range from 200 mOsmol/kg to 400 mOsmol/kg.

18. The method of claim 17 further comprising adding one or more cationic antimicrobial components selected from the group consisting of poly[dimethylimino-2-butene-1,4-diyl]chloride, α

-[4-tris(2-hydroxyethyl)ammonium chloride-2-butenyl]poly[1-dimethylammonium chloride-2-butenyl]-ω

-tris(2-hydroxyethyl) ammonium chloride, myristamidopropyl dimethylamine, benzalkonium halides, alexidine and salts thereof, salts of chlorhexidine and hexamethylene biguanides and salts thereof and their polymers, to the composition, wherein the cationic antimicrobial component is added in an effective amount to provide a contact lens multipurpose solution to disinfect soft silicon lenses.

19. The method of claim 17 wherein the one or more cationic antimicrobial components are selected from the group consisting of poly(hexamethylene biguanide) or PHMB-CG*, which is present from 0.01 ppm to 3 ppm, and α

-[4-tris(2-hydroxyethyl)ammonium chloride-2-butenyl]poly[1-dimethylammonium chloride-2-butenyl]-ω

-tris(2-hydroxyethyl)ammonium chloride, which is present from 1 ppm to 100 ppm.

20. The method of claim 17 wherein the branched, glycerol monoalkyl compound is selected from a branched, glycerol monoalkyl ether, a branched, glycerol monoalkyl amine, a branched, glycerol monoalkyl sulfide, or any mixture thereof, and is present in a total amount from 0.05 ppm to 1,000 ppm.