Methods for closing suturable wounds by use of cyanoacrylate...

Drug – bio-affecting and body treating compositions – Solid synthetic organic polymer as designated organic active... – Monomer contains oxygen

Reexamination Certificate

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C424S078060

Reexamination Certificate

active

06214332

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention is directed to methods for closing opposed skin sections of suturable wounds by using polymerizable cyanoacrylate compositions comprising a compatible antimicrobial agent and, in particular, an iodine containing antimicrobial agent. These antimicrobial cyanoacrylate compositions provide for in situ formation of an antimicrobial polymeric cyanoacrylate film which film joins the separated skin sections of the suturable wound and, in a preferred embodiment, forms a covering over the closed wound.
2. References
The following publications, patent applications and patents are cited in this application as superscript numbers:
1 Barley, et al., International Patent Application Publication No. WO 93/25196, for Methods for Treating Non-Suturable Wounds by Use of Cyanoacrylate Adhesives, published Dec. 23, 1993
2 Barley, et al., Methods for Treating Suturable Wounds by Use of Sutures and Cyanoacrylate Adhesives, U.S. Pat. No. 5,254,132, issued Oct. 19, 1993
3 Greff, et al., U.S. Pat. No. 5,480,935, Cyanoacrylate Adhesive Compositions, issued Jan. 2, 1996
4 Beller, et al., Process for the Preparation of Iodine-Polyvinylpyrrolidone by Dry Mixing, U.S. Pat. No. 2,706,701, issued Apr. 19, 1955
5 Hosmer, Process of Stabilizing Polyvinylpyrrolidone, U.S. Pat. No. 2,826,532, issued Mar. 11, 1958
6 Siggin, Preparation of Iodine Polyvinylpyrrolidone Adducts, U.S. Pat. No. 2,900,305, issued Aug. 18, 1958
7 Joyner, et al., Plasticized Monomeric Adhesive Compositions and Articles Prepared Therefrom, U.S. Pat. Nos. 2,784,127, issued Mar. 5, 1957
8 Columbus, et al., Adhesive Cyanoacrylate Compositions with Reduced Adhesion to Skin, U.S. Pat. No. 4,444,933, issued Apr. 24, 1984
9 Leung, et al., Biocompatible Monomer and Polymer Compositions, U.S. Pat. No. 5,328,687, issued Jul. 12, 1994
10 Leplyanin, “Medical and Surgical Adhesive Composition and Process for Its Preparation”, International Application Publication No. WO 96/23532 published Aug. 8, 1996
11 Greff, et al., Cyanoacrylate Adhesive Compositions, U.S. Pat. No. 5,665,817, issued Sep. 9, 1997
12 Quinn, et al., A Randomized Trial Comparing Octylcyanoacrylate Tissue Adhesive and Sutures in the Management of Lacerations, J. Amer. Med. Assoc., (May 21, 1997) 277(19):1527-1530
All of the above patent applications and patents are herein incorporated by reference in their entirety to the same extent as if each individual publication, patent application or patent was specifically and individually indicated to be incorporated by reference in its entirety.
STATE OF THE ART
Polymerizable cyanoacrylate esters have been disclosed for a variety of topical uses on mammalian skin including use in covering small non-suturable superficial wounds on skin surfaces
1
as well as in closing suturable wounds.
2
Polymerizable cyanoacrylate esters suggested for such uses include cyanoacrylate esters of formula I:
wherein R is an alkyl or other suitable substituent. Such cyanoacrylate esters are disclosed in U.S. Pat. Nos. 3,527,224; 3,591,676; 3,667,472; 3,995,641; 4,035,334; and 4,650,826. Preferably, when applied to mammalian tissue, R is an alkyl group of from 1 to 10 carbon atoms and most often is butyl or octyl (e.g., n-butyl or n-octyl).
These compositions are liquid in nature and, upon contact with surface skin proteins and moisture, will polymerize and the resulting polymer bonds strongly to the skin. When a cyanoacrylate ester is applied over apposed skin sections of a suturable wound, subsequent polymerization will result in joining these apposed skin sections, and, hence, closure of the wound.
Cyanoacrylate ester compositions used for closing suturable wounds typically are formulated to contain a polymerization inhibitor to avoid premature polymerization of the formulation. Notwithstanding the benefits associated with the use of polymerizable cyanoacrylate ester compositions for application with suturable wounds, these compositions do not have a broad spectrum of antimicrobial activity including activity against microbial spores and, accordingly, cannot guarantee reductions in microbial populations on mammalian skin surface either under or adjacent the closed wound. Infection at the site of suturable wounds closed by conventional methods is, however, a significant health care concern. Accordingly, the use of polymerizable cyanoacrylate ester compositions for closing suturable wounds would be significantly augmented if these compositions were also widely antimicrobial.
Because polymerizable cyanoacrylate ester compositions alone are not sufficiently antimicrobial, incorporation of broad antimicrobial properties into the cyanoacrylate polymeric film necessitates, of course, that an antimicrobially effective amount of an antimicrobial agent be incorporated into the polymerizable cyanoacrylate ester composition and that sufficient amounts of this agent be released from the resulting polymeric cyanoacrylate film formed in situ on the patient's skin such that an antimicrobial effect is achieved. The incorporation of such an antimicrobial agent into the cyanoacrylate ester composition is problematic at best because several disparate criteria must be simultaneously met. First, the antimicrobial agent must be soluble or dispersible in the cyanoacrylate ester composition at the concentrations necessary to effect antimicrobial properties. Second, the antimicrobial agent employed must not cause premature polymerization of the cyanoacrylate ester composition. Third, the antimicrobial agent employed must not prevent in situ polymerization of the cyanoacrylate ester composition when applied to the skin. Fourth, the antimicrobial agent must be compatible with the intended use of the polymeric film by not inhibiting formation of a durable film. Finally, the impregnated antimicrobial agent must be released from the polymerized film in situ on the patient's skin in sufficient amounts to be antimicrobial.
Because of these disparate properties, many conventional antimicrobial agents are unsuitable for use in the polymerizable cyanoacrylate ester compositions used in the methods of this invention. However, in view of the clear benefits associated with the incorporation of an antimicrobial agent directly into these compositions, methods for closing suturable wounds using antimicrobial cyanoacrylate ester compositions would be particularly beneficial.
SUMMARY OF THE INVENTION
This invention is drawn to methods for closing opposed skin sections of suturable wounds by joining opposed skin sections together, applying an antimicrobial polymerizable cyanoacrylate ester composition to at least one surface of the opposed skin sections and subsequently polymerizing the cyanoacrylate ester in situ. In one embodiment, the opposed skin sections are brought together prior to application of the cyanoacrylate composition which is then applied over the closed sections. In another embodiment, the opposed skin sections are brought together after application of the cyanoacrylate to at least one surface of the opposed skin sections.
In particular, this invention is directed to methods for closing opposed skin sections of suturable wounds which methods utilize cyanoacrylate ester compositions comprising an antimicrobially effective amount of a compatible iodine containing antimicrobial agent. These compositions provide for in situ formation of an antimicrobial polymeric cyanoacrylate film which joins the opposed skin sections together. The specific antimicrobial agent employed is compatible with the cyanoacrylate ester composition insofar as the antimicrobial agent neither causes premature polymerization nor prevents polymerization of the monomer or reactive oligomer, rather a flexible and durable polymer film is formed in situ on mammalian skin by this composition. Moreover, in vitro assays evidence that the antimicrobial agent is released from the polymeric film in antimicrobially effective amounts thereby imparting antimicrobial properties to the polymeric film formed in situ.
The compatible iodine containing antimicro

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