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European Patent Office Europäisches Patentamt *EP001021204B1* (19) European Patent Office Office européen des brevets (11) EP 1 021 204 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.7: A61K 47/32, A61L 25/00 of the grant of the patent: 28.12.2005 Bulletin 2005/52 (86) International application number: PCT/US1998/020091 (21) Application number: 98949505.6 (87) International publication number: (22) Date of filing: 25.09.1998 WO 1999/015210 (01.04.1999 Gazette 1999/13) (54) BIOADHESIVE COMPOSITIONS AND METHODS FOR TOPICAL ADMINISTRATION OF ACTIVE AGENTS BIOLOGISCHE KLEBER UND VERFAHREN ZUR TOPISCHEN VERABREICHUNG VON WIRKSTOFFEN COMPOSITIONS BIOADHESIVES ET METHODES D’ADMINISTRATION LOCALE D’AGENTS ACTIFS (84) Designated Contracting States: • HOUZE, David AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU Miami, FL 33186 (US) MC NL PT SE • KANIOS, David Miami, FL 33196 (US) (30) Priority: 26.09.1997 US 61155 P (74) Representative: Isenbruck, Günter (43) Date of publication of application: Isenbruck, Bösl, Hörschler, Wichmann, Huhn 26.07.2000 Bulletin 2000/30 Patentanwälte Theodor-Heuss-Anlage 12 (73) Proprietor: NOVEN PHARMACEUTICALS, INC. 68165 Mannheim (DE) Miami, FL 33186 (US) (56) References cited: (72) Inventors: FR-A- 2 532 546 GB-A- 1 050 070 • MANTELLE, Juan GB-A- 2 046 773 US-A- 4 593 053 Miami, FL 33176 (US) US-A- 5 656 286 Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 1 021 204 B1 Printed by Jouve, 75001 PARIS (FR) EP 1 021 204 B1 Description 1. Background of the Invention 5 [0001] This invention relates generally to bioadhesive compositions and methods for the topical administration of active agents to a mammal. More particularly, this invention relates to compositions capable of being used in wet or moist environments, especially on mucous membranes, for a prolonged period of time. There is no limitation on the_type of drug that can be used in the present invention, provided that it can be topically administered. Thus, the active agent includes both drugs that are topically applied for local effects and those which can be administered topically for systemic 10 effects. 2. Description of Related Art [0002] Mucous membranes such as the mucosa of the buccal cavity have several physical attributes, such as a rich 15 blood supply, that makes it a desirable site for topical administration of active agents for systemic delivery. Transmucosal delivery of active agents further avoids first-pass metabolism by the liver as well as poor uptake or inactivation via the gastro-intestinal pathway. Examples of such agents include steroids such as estrogens, progestins and related com- pounds; androgens and anabolic steroids; non-steroidal anti-inflammatory agents such as ketoprofen; diclofenac; pro- pranolol; thyroid hormones; pH sensitive peptides and small proteins such as insulin and ACTH; physostigmine; sco- 20 polamine; verapamil; and gallopamil. [0003] Moreover, it is often desirable or necessary to deliver pharmaceutical agents locally, such as to alleviate pain in the buccal cavity. [0004] Buccal and/or mucosal delivery compositions, devices and methods re disclosed, for example, in U.S. Patent No. 3,972,995 to Tsuk, et al., U.S. Patent No. 4,755,396 to Hsiao et al., U.S. Patent No. 4,764,378 to Keith et al., U. 25 S. Patent No. 4,740,365 to Yukimatsu et al., U.S. Patent No. 4,889,720 to Konishi et al., U.S. Patent 5,047,244 to Sanvordeker et al., and RE 33,093 to Schiraldi et al. [0005] The use of bioadhesives in the administration of active agents to mucous membranes has been known for some time. The most commonly used bioadhesive compositions have "non-finite" (i.e., spreading substances which do not retain their form) and liquid or semi-liquid carriers such as pastes, gels, lotions, emulsions, creams, sprays, 30 drops or ointments. Increasing use has been recently made of "finite" carriers (i.e., non-spreading substances which retain their form) such as films, dressings and bandages, or which start as finite then dissolve such as lozenges and tablets. Such compositions and devices have been less than satisfactory in achieving controlled release of such agents, and in maintaining adhesion (i.e., simply staying in place) or efficacy for prolonged periods of time. Moreover, they often leave unacceptable tacky residues upon removal. 35 [0006] It is disclosed in U.S. Patent No. 5,446,070 to Mantelle, that concentrations of substantially dissolved anes- thetic agents and other drugs as high as 50% by weight can be achieved in a system containing a bioadhesive carrier in which the adhesion of the carrier is not hindered. However, a need exists to increase the amount of time such compositions can be maintained at the site of administration in order to achieve maximum prolongation of therapeutic effects, both systemically and locally. 40 [0007] French Patent No. 2,532,546 relates to a paste for protecting the skin, including (i) at least one hydrocolloid, insolubilized carboxymethylcellulose and/or another superabsorbent product derived from hydrocolloids, and a poly- vinylpyrrolidone as thickeners, (ii) demineralized water as a binder, (iii) an oil, (iv) a stearate and (v) a crosslinked and insolubilized polyvinylpyrrolidone. The French Patent No. 2,532,546 refers to compositions which require demineralized water as part of the paste, and all the examples of the French patent No. 2,532,546 contain over 20 parts by weight 45 water. [0008] The Great Britain Patent No. 2,046,773 relates to a gelatinous tacky article produced by heating together (a) at least one polyhydric alcohol and (b) a naturally occurring high molecular weight polysaccharide gums, other than Karaya, and copolymer resins of a vinyl ether and an organic acid anhydride or its corresponding free acid to promote chemical reaction there between. The Great Britain Patent No. 2,046,773 discloses the incorporation of an antimicrobial 50 agent to prevent bacterial growth in the adhesive and not to produce a desired effect when applied topically over the duration of the intended use. [0009] The Great Britain Patent No. 1,050,070 is concerned with sealing rings for use with surgical drainage pouches. According to one aspect of the invention, there is provided a sealing ring for use with a post-surgical drainage pouch adapted to receive drainage from the stoma of a patient, wherein the ring is formed from an oleaginous nonevaporative 55 carrier having a medicament therein of a sufficient quantity to produce a semisolid gelatinous ring, said ring having an opening to permit said ring to surround the stoma thereby to form a seal between the skin of a patient and the drainage pouch. [0010] U.S. Patent No. 4,593,053 relates to a skin-compatible, pressure sensitive, solid, adhesive gel or hydrogel 2 EP 1 021 204 B1 composition which includes from 25 to 50 weight percent polyvinyl pyrolidone (PVP, 2 to 5 weight percent polyvinyl alcohol (PVA), about 5 to about 40 weight percent humectant, about 3 to about 50 weight percent water, and about 0 to about 50 weight percent of an ionic species. U.S. Patent No. 4,593,053 refers to compositions which require dem- ineralized water as part of the composition, and all the examples of the U.S. Patent No. 4,593,053 contain over 22 5 parts by weight water. The U.S. Patent No. 4,593,053 teaches that the water is advantageously maintained in the composition at such high level to provide suitable adhesiveness, tack, cohesive strength, and skin-compatibility. (Col. 3, lines 1-5). [0011] U.S. Patent No. 5,656,286 relates to a pressure-sensitive adhesive composition for a transdermal drug de- livery system which includes a blend of at least two polymers, or at least one polymer and a soluble polyvinylpyrrolidone, 10 in combination with a drug. The drug is delivered from the pressure-sensitive adhesive composition and through dermis when the pressure-sensitive adhesive composition is in contact with human skin. [0012] A successful bioadhesive device for topical administration of active agents for prolonged periods of time needs to satisfy a number of physical characteristics. For instance, the release liner should be easily peelable from the bio- adhesive portion, yet the latter must be both sufficiently adhesive and cohesive to maintain close or intimate contact 15 with the site of application for prolonged periods of time, typically between 1 to 2 hours, and up to even 24 hours with certain active agents. The bioadhesive composition must further retain the active agent at an appropriate rate for sustained or controlled delivery under the conditions prevailing in wet and moist environments associated with mucosa. In addition, the bioadhesive composition must be non-toxic, not cause chemical irritation and, must be easily removable with minimal mechanical irritation or damage to the application site. 20 [0013] In this regard, compositions according to the present invention are capable of adhering for prolonged periods of time, such as, for example, greater than 1 hour, preferably 2 hours, more preferably 4 hours, even more preferably greater than 8 hours, up to even 24 hours, to moist tissue such as mucosa and thus the desired therapeutic effects are ensured by the high degree of adhesion
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