Poly(nitrogen/amine) derivatives of a natural wax and ophthalmic compositions

• US 9,279,095 B2
• Filed: 01/23/2014
• Issued: 03/08/2016
• Est. Priority Date: 01/24/2013
• Status: Active Grant

• Current Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Original Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Inventors: Fridman, Krista, Xia, Erning, Liu, Xiaojun Michael
• Primary Examiner(s): FAY, ZOHREH A
• Application Number:
  US14/161,936
• Publication Number:
  US 20140206764A1
• Time in Patent Office: 775 Days
• US Class Current: 1/1
• CPC Class Codes: A61K 31/14 Quaternary ammonium compounds, e.g. edrophonium, choline betaines A61K31/205
• CPC Class Codes: A61K 31/785 Polymers containing nitrogen
• CPC Class Codes: A61K 35/644 Beeswax; Propolis; Royal jelly; Honey
• CPC Class Codes: A61K 36/00 Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines antigens from pollen A61K39/36
• CPC Class Codes: A61K 47/186 Quaternary ammonium compounds, e.g. benzalkonium chloride or cetrimide
• CPC Class Codes: A61K 47/44 Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin synthetic glycerides, e.g. medium-chain triglycerides, A61K47/14
• CPC Class Codes: A61K 9/0048 Eye, e.g. artificial tears
• CPC Class Codes: A61L 12/142 Polymeric biguanides
• CPC Class Codes: A61P 27/02 Ophthalmic agents
• CPC Class Codes: C08G 73/0206 Polyalkylene(poly)amines
• CPC Class Codes: C11C 3/04 by esterification of fats or fatty oils

Abstract

A poly(nitrogen/amine) derivative of a natural wax of formula I, and ophthalmic compositions and contact lens care solutions that contain the poly(nitrogen/amine) derivative of a natural wax of formula I. The invention is also directed to a method of treating a patient with dry eyes, the method comprising instructing a patient to administer one or more eye drops of the ophthalmic composition that includes a poly(nitrogen/amine) derivative of a natural wax of formula I.

Claims

1. An ophthalmic composition aqueous-based solution comprising 0.005 wt. % to 2.0 wt. % of a poly(nitrogen/amine) derivative of a natural wax of formula (I)

2. The composition of claim 1 wherein the natural wax is selected from the group consisting of beeswax, lanolin, PEG lanolin, jojoba and PEG jojoba.

3. The composition of claim 1 further comprising 0.002 w. % to 0.2 wt. % hyaluronic acid or 0.05 w. % to 0.3 wt. % hydroxypropyl guar.

4. The composition of claim 2 further comprising 0.002 w. % to 0.2 wt. % hyaluronic acid or 0.05 w. % to 0.3 wt. % hydroxypropyl guar.

5. The composition of claim 1 wherein the poly(nitrogen/amine) derivative of a natural wax is polyethyleneimine lanolin, the polyethyleneimine lanolin present from 0.005 wt. % to 0.3 wt. %.

6. The composition of claim 5 wherein the polyethyleneimine lanolin has a weight average molecular weight from 600 daltons to 6000 daltons.

7. The composition of claim 1 wherein the poly(nitrogen/amine) derivative of a natural wax is polyethyleneimine jojoba, the polyethyleneimine jojoba is present from 0.005 wt. % to 1.0 wt. %.

8. The composition of claim 7 wherein the polyethyleneimine jojoba has a weight average molecular weight from 600 daltons to 6000 daltons.

9. The composition of claim 1 wherein the composition further comprises a pharmaceutical agent.

10. The composition of claim 1 further comprising dexpanthenol, sorbitol, xylitol, glycolic acid, propylene glycol, 2-amino-2-methyl-1,3-propanediol, poly(ethyleneoxide-butyleneoxide) or any mixture thereof.

11. The composition of claim 1 further comprising one or more antimicrobial components selected from the group consisting poly(hexamethylene biguanide), which is present from 0.5 ppm to 1.5 ppm;

α

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

-tris(2-hydroxyethyl) ammonium chloride, which is present from 1 ppm to 10 ppm; and

alexidine, which is present from 1 ppm to 4 ppm.

12. The composition of claim 4 further comprising one or more antimicrobial components selected from the group consisting poly(hexamethylene biguanide), which is present from 0.5 ppm to 1.5 ppm;

α

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

-tris(2-hydroxyethyl) ammonium chloride, which is present from 1 ppm to 10 ppm; and

alexidine, which is present from 1 ppm to 4 ppm.

13. The composition of claim 1 further comprising 0.5 ppm to 1.5 ppm of poly(hexamethylene biguanide), or 1 ppm to 4 ppm alexidine,

wherein the poly(nitrogen/amine) derivative of a natural wax of formula (I) reduces an amount of the poly(hexamethylene biguanide), or alexidine, that is absorbed into a balafilcon A silicone hydrogel contact lens by at least 25% relative to an equivalent composition but in the absence of the derivatized natural wax, following a soak of the balafilcon A lens in the composition and the equivalent composition for six hours.

14. The composition of claim 13 further comprising α

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

-tris(2-hydroxyethyl) ammonium chloride, which is present from 1 ppm to 3 ppm.

18. The composition of claim 1, wherein the poly(nitrogen/amine) derivative of a natural wax of formula (I) is a branched poly(ethyleneimine) or linear poly(ethyleneimine) derivative of a natural wax.

19. The composition of claim 1, wherein the poly(nitrogen/amine) derivative of a natural wax of formula (I) is a branched poly(ethyleneimine) derivative of a natural wax.

20. The composition of claim 1, wherein the poly(nitrogen/amine) derivative of a natural wax of formula (I) is a linear poly(ethyleneimine) derivative of a natural wax.

15. A method of treating a patient with dry eyes, the method comprising instructing a patient to administer one or more eye drops of an ophthalmic composition aqueous-based solution comprising 0.005 wt. % to 2.0 wt. % of a poly(nitrogen/amine) derivative of a natural wax of formula I

16. The method of claim 15 wherein the natural wax is selected from the group consisting of beeswax, lanolin, PEG lanolin, jojoba and PEG jojoba.

17. The method of claim 15 wherein the patient wears contact lenses and the one or more drops are administered directly to the lenses positioned in the eye of the patient.