Polyethylene oxide-containing quaternary ammunium polymers and pharmaceutical compositions containing an antimicrobial amount of same

• US 5,536,494 A
• Filed: 10/04/1994
• Issued: 07/16/1996
• Est. Priority Date: 10/04/1994
• Status: Expired due to Fees

• Current Assignee: Alcon Manufacturing Limited (Alcon Incorporated)
• Original Assignee: Alcon Laboratories Incorporated (Alcon Incorporated)
• Inventors: Park, Joonsup
• Primary Examiner(s): Kulkosky, Peter F.
• Application Number:
  US08/318,022
• Time in Patent Office: 651 Days
• Field of Search: 424/78.04, 528/422
• US Class Current: 424/78.04
• CPC Class Codes: A01N 33/12 Quaternary ammonium compounds
• CPC Class Codes: A61L 12/145 Polymeric quaternary ammonium compounds
• CPC Class Codes: C08G 65/33303 containing amino group

Abstract

PEO-containing quaternary ammonium compounds have good broad spectrum antimicrobial activity. These compounds are useful in pharmaceutical compositions as preservatives and in contact lens care compositions as preservatives and/or disinfectants.

Claims

1. A pharmaceutical composition comprising an antimicrobially-effective amount of a polymer having a single repeating unit of the formula ##STR3## wherein R=polyethylene oxide of molecular weight from 80-2,000;

CH₂ -phenyl-CH₂ ;

or 2-butenyl;

PEO=polyethylene oxide of molecular weight from 80-2,000;

X=halogen, acetate, or sulfate; and

n=5-100;

and a pharmaceutically acceptable carrier therefor.

2. The composition of claim 1, wherein the polymer is present at a concentration from about 0.1 to about 0.0001 wt %.

3. The composition of claim 2, wherein the polymer is present at a concentration from about 0.05 to about 0.0005 wt %.

4. The composition of claim 3, wherein the polymer is present at a concentration of about 0.001 wt %.

5. The composition of claim 1 wherein R=polyethylene oxide of molecular weight from 80-2,000.

6. The composition of claim 1 wherein R=CH₂ -phenyl-CH₂.

7. The composition of claim 1 wherein R=2-butenyl.

8. The composition of claim 1 wherein PEO=polyethylene oxide of molecular weight from 80-1000;

X=Cl; and

n=10-70.

9. The composition of claim 8 wherein R=2-butenyl;

PEO=polyethylene oxide of molecular weight from 80-500; and

n=20-40.

10. The composition of claim 1, wherein the polymer has a number average molecular weight, based on NMR spectroscopy, of at least 5,000, has end groups independently selected from the group consisting of N(CH₃)₂ and OCH₂ CH₂ Cl, and wherein

PEO=polyethylene oxide of molecular weight 400;

X=Cl; and

n=10-70.

11. The composition of claim 10, wherein R=2-butenyl;

and n=20-40.

12. A method of disinfecting a contact lens, comprising contacting, for a time sufficient to disinfect the lens, the contact lens to a composition comprising a disinfecting amount of a polymer having a single repeating unit of the formula ##STR4## wherein R=polyethylene oxide of molecular weight from 80-2,000;

CH₂ -phenyl-CH₂ ;

or 2-butenyl;

PEO=polyethylene oxide of molecular weight from 80-2,000;

X=halogen, acetate, or sulfate; and

n=5-100;

and a pharmaceutically acceptable carrier therefor.

13. The method of claim 12, wherein the compound of formula I is present at a concentration from about 0.1 to about 0.0001 wt %.

14. The method of claim 13, wherein the compound of formula I is present at a concentration from about 0.05 to about 0.0005 wt. %.

15. The method of claim 14, wherein the compound of formula I is present at a concentration of about 0.001 wt %.

16. The method of claim 12 wherein R=polyethylene oxide of molecular weight from 80-2,000.

17. The method of claim 12 wherein R=CH₂ -phenyl-CH₂.

18. The method of claim 12 wherein R=2-butenyl.

19. The method of claim 12 wherein PEO=polyethylene oxide of molecular weight from 80-1000;

X=Cl; and

n=10-70.

20. The method of claim 19 wherein R=2-butenyl;

PEO=polyethylene oxide of molecular weight from 80-500; and

n=20-40.

21. The method of claim 12, wherein the polymer has a number average molecular weight, based on NMR spectroscopy, of at least 5,000, has end groups independently selected from the group consisting of N(CH₃)₂ and OCH₂ CH₂ Cl, and wherein

PEO=polyethylene oxide of molecular weight 400;

X=Cl; and

n=10-70.

22. The method of claim 21, wherein R=2-butenyl;

and n=20-40.

23. A polymer comprising a single repeating unit of the formula ##STR5## wherein R=polyethylene oxide of molecular weight from 80-2,000;

CH₂ -phenyl-CH₂ ;

or 2-butenyl;

PEO=polyethylene oxide of molecular weight from 80-2,000;

X=halogen, acetate, or sulfate; and

n=5-100.