Drug – bio-affecting and body treating compositions – Preparations characterized by special physical form – Biocides; animal or insect repellents or attractants
Reexamination Certificate
2000-06-01
2002-11-05
Page, Thurman K. (Department: 1615)
Drug, bio-affecting and body treating compositions
Preparations characterized by special physical form
Biocides; animal or insect repellents or attractants
C424S407000, C424S400000, C424S443000, C424S447000
Reexamination Certificate
active
06475502
ABSTRACT:
BACKGROUND OF THE INVENTION
Field of the Invention
This invention is directed to kits of parts comprising in a first container a cyanoacrylate prepolymer composition and in a second container a compatible antimicrobial agent. The kit may additionally contain an applicator means for applying the composition to mammalian skin. These kits provide for compositions useful in situ formation of antimicrobial polymeric cyanoacrylate films on mammalian skin which films are useful as wound dressings, wound bandages, surgical incise drapes, and the like.
References
The following publications, patent applications and patents are cited in this application as superscript numbers:
1
Hawkins, et al.,
Surgical Adhesive Compositions,
U.S. Pat. No. 3,591,676, issued Jul. 6, 1971
2
Halpern, et al.,
Adhesive for Living Tissue,
U.S. Pat. No. 3,667,472, issued Jun. 6, 1972
3
McIntire, et al.,
Process for the Preparation of Poly
(&agr;-
Cyanoacrylates
), U.S. Pat. No. 3,654,239, issued Apr. 4, 1972
4
Barley, et al.,
Methods for Treating Non
-
Suturable Wounds by Use of Cyanoacrylate Adhesives,
International Patent Application Publication No. WO 93/25196, published Dec. 23, 1993
5
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
6
Barley, et al.,
Methods for Reducing Skin Irritation From Artificial Devices by Use of Cyanoacrylate Adhesives,
U.S. Pat. No. 5,653,789, issued Aug. 5, 1997
7
Rabinowitz, et al.,
Method of Surgically Bonding Tissue Together,
U.S. Pat. No. 3,527,224, issued Sep. 8, 1970
8
Kronenthal, et al.,
Surgical Adhesives,
U.S. Pat. No. 3,995,641, issued Dec. 7, 1976
9
Davydov, et al.,
Medical Adhesive,
U.S. Pat. No. 4,035,334, issued Jul. 12, 1977
10
Waniczek, et al.,
Stabilized Cyanoacrylate Adhesives Containing Bis
-
Trialkylsilyl Esters of Sulfuric Acid,
U.S. Pat. No. 4,650,826, issued Mar. 17, 1987
11
Askill, et al., “
Methods for Draping Surgical Incision Sites
” U.S. Pat. No. 5,730,994, issued Mar. 24, 1998
12
Greff, et al.,
Cyanoacrylate Adhesive Compositions,
U.S. Pat. No. 5,480,935, issued Jan. 2, 1996
13
Hagen, et al., “
A Comparison of Two Skin Preps Used in Cardiac Surgical Procedures
”, AORN Journal, 62(3):393-402 (1995)
14
Ritter, et al., “
Retrospective Evaluation of an Iodophor
-
Incorporated Antimicrobial Plastic Adhesive Wound Drape
”, Clinical Orthopedics and Related Research, pp. 307-308 (1988)
15
Osuna, et al., “
Comparison of an Antimicrobial Adhesive Drape and Povidone
-
Iodine Preoperative Skin Preparation in Dogs
”, Veterinary Surgery, 21(6):458-462 (1992)
16
O'Sullivan, et al.,
High Viscosity Cyanoacrylate Adhesive Compositions, and Process for Their Preparation,
U.S. Pat. No. 4,038,345, issued Jul. 26, 1977
17
Beller, et al.,
Process for the Preparation of Iodine
-
Polyvinylpyrrolidone by Dry Mixing,
U.S. Pat. No. 2,706,701, issued Apr. 19, 1955
18
Hosmer,
Process of Stabilizing Polyvinylpyrrolidone,
U.S. Pat. No. 2,826,532, issued Mar. 11, 1958
19
Siggin,
Preparation of Iodine Polyvinylpyrrolidone Adducts,
U.S. Pat. No. 2,900,305, issued Aug. 18, 1958
20
Joyner, et al.,
Plasticized Monomeric Adhesive Compositions and Articles Prepared Therefrom,
U.S. Pat. Nos. 2,784,127, issued Mar. 5, 1957
21
Columbus, et al.,
Adhesive Cyanoacrylate Compositions with Reduced Adhesion to Skin,
U.S. Pat. No. 4,444,933, issued Apr. 24, 1984
22
Leung, et al.,
Biocompatible Monomer and Polymer Compositions,
U.S. Pat. No. 5,328,687, issued Jul. 12, 1994
23
Byram, et al.,
Use of Cyanoacrylate Adhesive Compositions to Inhibit Acute Radiation
-
Induced Skin Damage,
U.S. Pat. No. 5,554,365, issued Sep. 10, 1996.
24
Leplyanin, “
Medical and Surgical Adhesive Composition and Process for Its Preparation
”, International Application Publication No. WO 96/23532 published Aug. 8, 1996
25
Tighe, et al., “
Use of Cyanoacrylate Adhesives For Providing A Protective Barrier Film For The Skin
”, U.S. Pat. No. 5,580,565, issued on Dec. 3, 1996.
26
Cardarelli, et al., “
Film Forming Antimicrobial Material
”, U.S. Pat. No. 4,374,126, issued Feb. 15, 1983
27
Barnes, “
Biocidal Complex and Dressing Formed Therefrom
”, U.S. Pat. No. 5,051,256, issued Sep. 24, 1991
28
Dell, “
Film
-
Forming Composition Containing an Antimicrobial Agent and Methods
”, U.S. Pat. No. 4,542,012, issued Sep. 17, 1985
29
Brink, et al., “
Film
-
Forming Emulsion Containing Iodine and Methods of Use
”, U.S. Pat. No. 5,173,291, issued Dec. 22, 1992
30
Khan, et al., “
Preparation of a Skin Surface for a Surgical Procedure
”, U.S. Pat. No. 5,547,662, issued Aug. 20, 1996
31
Blum, et al.,
In vitro Determination of the Antimicrobial Properties of Two Cyanoacrylate Preparations,
J. Dent. Res., 54(3):500-503 (1975)
32
Greff et al., “
Cyanoacrylate Compositions Comprising an Antimicrobial Agent
”, U.S. Pat. No. 5,684,042, issued Nov. 4, 1997
33
Greff et al., “
Cyanoacrylate Compositions Comprising an Antimicrobial Agent
”, U.S. patent application No. 08/912,681, filed Aug. 18, 1997
34
Mixon, U.S. Pat. No. 5,069,907
35
Greff, et al.,
Methods for Sterilizing Cyanoacrylate Compositions,
U.S. Pat. No. 6,248,800 which issued on Jun. 19, 2001.
All of the above publications, 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
Cyanoacrylate esters have been disclosed for a variety of topical uses on mammalian skin including use as a replacement or adjunct for sutures or staples in closing the dermal layer of an incision after surgery.
1,2,5
Other disclosed topical uses include use as a hemostat
3
, use in covering small non-suturable wounds on skin surfaces
4
, use in inhibiting surface skin irritation arising from friction between the skin surface and artificial devices such as tapes, prosthetic devices, casts, etc.
6
and use in inhibiting acute radiation-induced skin damage.
23
Still another topical use of cyanoacrylate esters is its use in the in situ formation of a surgical incise drape.
11
In each case, when topically applied to mammalian skin, the cyanoacrylate rapidly polymerizes, typically within a minute, to form a coherent polymeric film which strongly adheres to the skin.
Cyanoacrylate esters suggested for such uses include the following structures:
wherein R is an alkyl or other suitable substituent. Such cyanoacrylate esters are disclosed in, for example, U.S. Pat. Nos. 3,527,224; 3,591,676; 3,667,472; 3,995,641; 4,035,334; and 4,650,826.
1,2,7-10
Cyanoacrylate ester compositions for topical skin application typically are formulated to contain both a plasticizer to enhance flexibility of the resulting polymeric film and a polymerization inhibitor to avoid premature polymerization of the composition. When employed topically on mammalian skin, Greff et al.
12
disclose that the cyanoacrylate composition preferably employs from about 50 to about 500 ppm sulfur dioxide as the polymerization inhibitor and from about 18-25 weight percent of a biocompatible plasticizer such as dioctyl phthalate.
Notwithstanding the beneficial properties associated with such cyanoacrylate ester compositions and their suitability for topical applications, these compositions do not possess a sufficient antimicrobial activity including activity against microbial spores
31
and, accordingly, cannot assure reductions in microbial populations on mammalian skin surface either under or adjacent to a polymeric cyanoacrylate film formed in situ on the skin.
Many of the uses of cyanoacrylate ester compositions enumerated above would, however, significantly benefit by additional antimicrobial property in the polymer film. For instance, covering small non-suturable wounds on skin surfaces with a polymeric cyanoacrylate film having antimicrobial activity would mitigate against possible wound infection. Likewise, when used as a surgical (incise) drape, such films
Askill Ian N.
Greff Richard J.
Lee Connie C.
Bennett Rachel M.
Burns Doane Swecker and Mathis LLP
Flowers Park Ltd.
Page Thurman K.
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