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Ophthalmic composition with hyaluronic acid

Inactive Publication Date: 2008-12-18
BAUSCH & LOMB INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The invention is about an eye drop solution that contains a special polymer and hyaluronic acid. The polymer has certain groups that make it effective at cleaning and disinfecting contact lenses. The solution can be used to clean, disinfect, or package contact lenses.

Problems solved by technology

However, as with any antimicrobial component there remains a tradeoff between the concentration of the antimicrobial component in the solution and the comfort experienced by the patient.

Method used

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  • Ophthalmic composition with hyaluronic acid
  • Ophthalmic composition with hyaluronic acid
  • Ophthalmic composition with hyaluronic acid

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0115]PHMB (Cosmocil CG®, 6.0 g, 3.3 mmol), hexamethylene bis(cyanoguanido) (HMBDA) (0.9 g, 3.6 mmol) and concentrated hydrochloric acid (360 μL) are added to a reaction flask and heated to 100° C. until most of the liquid dissipates from the flask. The temperature of the reaction mixture is then heated to 155° C. for four hours. The reaction is allowed to cool overnight to room temperature over a flow of nitrogen. The resulting solids are dissolved in 50 mL of distilled water and solution purified by dialysis (100 MWCO tubing) overnight. The purified product is freeze dried, 4.81 g.

example 2

[0116]PHMB (Cosmocil®CQ, 6.0 g, 3.3 mmol), hexamethylene bis(cyanoguanido) (HMBDA) (1.8 g, 7.2 mmol) and concentrated hydrochloric acid (720 μL) are added to a reaction flask and heated to 100° C. until most of the liquid dissipates from the flask. The temperature of the reaction mixture is then heated to 155° C. for four hours. The reaction is allowed to cool overnight to room temperature over a flow of nitrogen. The resulting solids are dissolved in 60 mL of distilled water and the solution purified by dialysis (100 MWCO tubing) overnight. The purified product is freeze dried, 5.3 g.

[0117]Examples 1 and 2 were analyzed by 13C NMR (see, below) to determine the molar concentration of terminal end groups. The 13C NMR data for Examples 1 and 2 along with commercial samples of PHMB are summarized in Table 5.

TABLE 5terminal groupsin-chainMnMn(mol %)(mol %)Example(GPC)(NMR)amineCGGGGGCosmocil ®1568141930.231.738.091.78.3CQCosmocil ®1695138320.829.949.389.610.41001139212768.425.965.789.41...

examples 3a to 3c

[0118]For each of the preparations, PHMB (Cosmocil®100, 6.0 g, 3.3 mmol) (Cosmocil®100 is a solid form of PHMB), hexamethylene bis(cyanoguanido) (HMBDA) (1.8 g, 7.2 mmol) and concentrated hydrochloric acid (720 μL) are added to a reaction flask and heated to 100° C. until most of the liquid dissipates from the flask. The temperature of the reaction mixture is then heated to 155° C. for four hours. The reaction is allowed to cool overnight to room temperature over a flow of nitrogen. The resulting solids are dissolved in 60 mL of distilled water and the solution purified by dialysis (100 MWCO tubing) overnight. The purified product is then freeze dried overnight.

[0119]The 13C NMR data for Examples 3A to 3C are summarized in Table 6.

TABLE 6terminal groupsin-chainMnMn(mol %)(mol %)Example(GPC)(NMR)amineCGGGGG3A180814669.520.070.586.913.13B175814607.523.069.587.912.13C1751144911.520.068.587.212.8

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Abstract

An ophthalmic composition comprising a polymeric biguanide composition having less than 18 mol % of terminal amine groups and 55 mol % or greater of terminal guanidine groups as measured by 13C NMR, and 0.005 w / v % to 0.04 w / v % hyaluronic acid. Alternatively, the ophthalmic composition comprises a polymeric biguanide composition comprising less than 18 mol % of terminal amine groups and 40 mol % or greater of terminal cyanoguanidino groups as measured by 13C NMR, and 0.005 w / v % to 0.04 w / v % hyaluronic acid. The compositions can be used for cleaning, disinfecting or packaging a contact lens.

Description

[0001]This application claims priority to U.S. provisional application No. 60 / 943,620 filed Jun. 13, 2007 under 35 U.S.C. §119(e).[0002]The present invention relates to an ophthalmic composition with hyaluronic acid and a biguanide, and to a method of cleaning, disinfecting or packaging contact lenses with the composition.BACKGROUND OF THE INVENTION [0003]Biguanides, including polymeric biguanides, as a class are known to have antimicrobial activity. Poly(hexamethylene biguanide) also known as PHMB or PAPB has been used as an antimicrobial component in many applications including topical disinfectants and as a preservative in health care products. PHMB is commonly represented by the following formula, though it is known to exist as a complex mixture of polymeric biguanides with various terminal groups including guanidine (not shown).The value n represents the number of repeating units of the biguanide polymer. GB 1434040 describes the use of PHMB and several other biguanide structur...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K31/785C11D3/37A01P1/00
CPCA61L12/142C11D1/90C11D1/92C11D3/0078C11D3/222C11D3/227C11D3/3723C11D3/48A61P27/02
Inventor BURKE, SUSAN E.VENKATESH, SRINIHEILER, DAVID J.
Owner BAUSCH & LOMB INC