WO1997029741A1 - Polymeric quaternary ammonium compounds and their use as ophthalmic antimicrobials - Google Patents
Polymeric quaternary ammonium compounds and their use as ophthalmic antimicrobials Download PDFInfo
- Publication number
- WO1997029741A1 WO1997029741A1 PCT/US1996/001975 US9601975W WO9729741A1 WO 1997029741 A1 WO1997029741 A1 WO 1997029741A1 US 9601975 W US9601975 W US 9601975W WO 9729741 A1 WO9729741 A1 WO 9729741A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- quaternary ammonium
- polymeric quaternary
- ammonium compound
- present
- concentration
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/74—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C215/90—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with quaternised amino groups bound to the carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/62—Quaternary ammonium compounds
- C07C211/63—Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
Definitions
- the present invention relates generally to a class of antimicrobials useful in pharmaceutical and cosmetic products.
- the present invention relates to polymeric quaternary ammonium compounds which are useful as disinfectants and preservatives for ophthalmic, pharmaceutical and contact lens care products.
- DuPont Patent discloses linear polymeric quaternary ammonium compounds and methods for their preparation.
- the method of the DuPont Patent may be generically described as a condensation reaction between a lower alkyl dihalide and a difunctional ditertiary amine.
- Contemplated uses for the compounds of the DuPont Patent include their use in photographic processing, to treat leather, as mold inhibitors and pesticides, and as modifying agents. There is no mention of use of these compounds as disinfectants or preservatives in pharmaceutical products.
- disinfectants and/or preservatives shall be collectively referred to as “antimicrobials” and compounds having disinfecting and or preserving efficacy shall be referred to as compounds having "antimicrobial activity.”
- antiimicrobials compounds having disinfecting and or preserving efficacy
- compounds having "antimicrobial activity” compounds having "antimicrobial activity”
- polymeric quaternary ammonium compounds or “polymers” shall hereinafter refer to polymeric quaternary ammonium compounds and their pharmaceutically acceptable salts, and the terms shall be used interchangeably throughout this specification.
- polymeric quaternary ammonium compounds of generic relationship to those disclosed in the DuPont Patent and the Green, et al. patents, are particularly suitable for use in ophthalmic compositions as antimicrobials.
- the polymers of the present invention are unique in at least two respects: 1) it has been discovered that optimum performance for the indicated utility is achieved only for a narrow range of molecular size, i.e., length of the polymer; and 2) the polymers of the present invention are characterized by a terminal end group R, which is -N(CH 3 ) 2 .
- the ophthalmic compositions of the present invention comprise the polymers of the present invention. These compositions include: contact lens care products, such as chemical disinfecting and storage solutions and preserved saline solutions; and other types of ophthalmic compositions, such as artificial tears and topical pharmaceutical preparations.
- Preferred polymers of the present invention are those of Structure (I), below:
- W N(CH 3 ) 2 or OH
- X is a pliarmaceutically acceptable anion, preferably a halide, particularly chloride; and n is an integer from 16 to 32, preferably from 20 to 24.
- the polymers of the present invention can be made and purified by utilizing the methods of the DuPont Patent or the Green, et al. patents to synthesize a polymeric mixture, then to separate the desired molecular weight fraction by chromatographic methods, by using dialysis membranes, by trituration, by a combination of these methods or by some other means.
- the polymers of the present invention may be used as antimicrobials in ophthalmic compositions, particularly as disinfectants in contact lens care products and as preservatives in other types of ophthalmic compositions, such as artificial tears or topical pharmaceutical preparations.
- the polymers of the present invention will be present in the compositions at a concentration between about 0.00001 and 1.0 percent by weight (wt%). If used as a disinfectant, the polymers are preferably present at a concentration of between about 0.0005 and 0.5 wt%; if use as a preservative, the polymers are present at a concentration between about 0.00005 and 0.05 wt%. It is preferred that the polymers are present at a concentration of between 0.001 and 0.05 wt% if used as a disinfectant and between 0.0001 and 0.01 wt% if used as a preservative.
- the ophthalmic compositions of the present invention may additionally contain other components, for example, ophthalmically acceptable buffers, tonicity agents, surfactants and therapeutic agents.
- Example 1 The procedure described in the synthesis of Example 1 was employed using 2.16 g
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/117,839 US6051611A (en) | 1991-11-08 | 1996-02-14 | Polymeric quaternary ammonium compounds and their use as ophthalmic antimicrobias |
AU49808/96A AU712908B2 (en) | 1996-02-14 | 1996-02-14 | Polymeric quaternary ammonium compounds and their use as ophthalmic antimicrobials |
EP96906426A EP0880351A4 (en) | 1996-02-14 | 1996-02-14 | Polymeric quaternary ammonium compounds and their use as ophthalmic antimicrobials |
PCT/US1996/001975 WO1997029741A1 (en) | 1996-02-14 | 1996-02-14 | Polymeric quaternary ammonium compounds and their use as ophthalmic antimicrobials |
JP09529296A JP2000505486A (en) | 1996-02-14 | 1996-02-14 | Polymeric quaternary ammonium compounds and their use as ophthalmic antimicrobial agents |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/US1996/001975 WO1997029741A1 (en) | 1996-02-14 | 1996-02-14 | Polymeric quaternary ammonium compounds and their use as ophthalmic antimicrobials |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1997029741A1 true WO1997029741A1 (en) | 1997-08-21 |
Family
ID=22254716
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1996/001975 WO1997029741A1 (en) | 1991-11-08 | 1996-02-14 | Polymeric quaternary ammonium compounds and their use as ophthalmic antimicrobials |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP0880351A4 (en) |
JP (1) | JP2000505486A (en) |
AU (1) | AU712908B2 (en) |
WO (1) | WO1997029741A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106561631A (en) * | 2016-10-13 | 2017-04-19 | 刘鹏飞 | Saliva preservation solution, and preparation method and application thereof |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3874870A (en) * | 1973-12-18 | 1975-04-01 | Mill Master Onyx Corp | Microbiocidal polymeric quarternary ammonium compounds |
US4025653A (en) * | 1975-04-07 | 1977-05-24 | Millmaster Onyx Corporation | Microbiocidal polymeric quaternary ammonium compounds |
US4089977A (en) * | 1976-11-24 | 1978-05-16 | Kewanee Industries | Polymeric anti-microbial agent |
US4407791A (en) * | 1981-09-28 | 1983-10-04 | Alcon Laboratories, Inc. | Ophthalmic solutions |
US4444750A (en) * | 1980-11-17 | 1984-04-24 | Millmaster Onyx Group, Inc. | Method of conditioning hair |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4525346A (en) * | 1981-09-28 | 1985-06-25 | Alcon Laboratories, Inc. | Aqueous antimicrobial ophthalmic solutions |
CA2009118C (en) * | 1989-02-21 | 1996-02-27 | Mary F. Mowrey-Mckee | Method and composition for cleaning and disinfecting contact lenses |
CA2041871C (en) * | 1990-05-09 | 2000-07-11 | Ruth A. Rosenthal | Contact lens cleaning and disinfecting with combinations of polymeric quaternary ammonium compounds and enzymes |
CA2125060C (en) * | 1993-07-02 | 1999-03-30 | Henry P. Dabrowski | Ophthalmic solution for artificial tears |
US5603929A (en) * | 1994-11-16 | 1997-02-18 | Alcon Laboratories, Inc. | Preserved ophthalmic drug compositions containing polymeric quaternary ammonium compounds |
-
1996
- 1996-02-14 EP EP96906426A patent/EP0880351A4/en not_active Withdrawn
- 1996-02-14 AU AU49808/96A patent/AU712908B2/en not_active Ceased
- 1996-02-14 WO PCT/US1996/001975 patent/WO1997029741A1/en not_active Application Discontinuation
- 1996-02-14 JP JP09529296A patent/JP2000505486A/en not_active Abandoned
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3874870A (en) * | 1973-12-18 | 1975-04-01 | Mill Master Onyx Corp | Microbiocidal polymeric quarternary ammonium compounds |
US4025653A (en) * | 1975-04-07 | 1977-05-24 | Millmaster Onyx Corporation | Microbiocidal polymeric quaternary ammonium compounds |
US4089977A (en) * | 1976-11-24 | 1978-05-16 | Kewanee Industries | Polymeric anti-microbial agent |
US4444750A (en) * | 1980-11-17 | 1984-04-24 | Millmaster Onyx Group, Inc. | Method of conditioning hair |
US4407791A (en) * | 1981-09-28 | 1983-10-04 | Alcon Laboratories, Inc. | Ophthalmic solutions |
Non-Patent Citations (1)
Title |
---|
See also references of EP0880351A4 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106561631A (en) * | 2016-10-13 | 2017-04-19 | 刘鹏飞 | Saliva preservation solution, and preparation method and application thereof |
Also Published As
Publication number | Publication date |
---|---|
EP0880351A4 (en) | 2003-01-08 |
JP2000505486A (en) | 2000-05-09 |
EP0880351A1 (en) | 1998-12-02 |
AU4980896A (en) | 1997-09-02 |
AU712908B2 (en) | 1999-11-18 |
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