| Antibacterial 5,5'-disubstituted 3,3'-dialkoxy-2,2'-dihydroxy-1,1'-biphenyl compounds and related methods -> Monitor Keywords |
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Antibacterial 5,5'-disubstituted 3,3'-dialkoxy-2,2'-dihydroxy-1,1'-biphenyl compounds and related methodsRelated Patent Categories: Drug, Bio-affecting And Body Treating Compositions, Chewing Gum TypeAntibacterial 5,5'-disubstituted 3,3'-dialkoxy-2,2'-dihydroxy-1,1'-biphenyl compounds and related methods description/claimsThe Patent Description & Claims data below is from USPTO Patent Application 20060233722, Antibacterial 5,5'-disubstituted 3,3'-dialkoxy-2,2'-dihydroxy-1,1'-biphenyl compounds and related methods. Brief Patent Description - Full Patent Description - Patent Application Claims
CROSS REFERENCE TO RELATED APPLICATION [0001] This application claims priority to U.S. Provisional Patent Application Ser. No. 60/662,992, filed Mar. 18, 2005, the contents of which are incorporated herein by reference. BACKGROUND OF THE INVENTION [0002] A number of disease conditions are associated with the action of bacteria in the oral cavity. Dental plaque is a soft deposit that forms on the surface of the teeth as a by-product of bacterial growth. Gingivitis, an inflammation or infection of the gums and alveolar bones, is generally believed to be caused by plaque causing bacteria and the toxins formed as by-products from the bacteria. In addition, plaque provides a locus for calculus or tartar formation. Periodontitis is generally believed to occur where unremoved plaque hardens into calculus (tartar), which affects the periodontal ligaments. As plaque and tartar continue to build up, the gums begin to recede, which can lead to continued infection and potentially the loss of teeth. [0003] To prevent or treat these diseased conditions, antibacterial agents are incorporated into oral care compositions such as toothpaste and mouthwashes or rinses. Application of antibacterial compositions in the oral cavity tends to retard plaque formation and related oral infections. [0004] The antiplaque efficacy of antibacterial compounds in a dentifrice composition depends on a number of factors, including the presence of other ingredients that may interfere with its action. For example, certain cationic antibacterial compounds and certain nonionic antibacterial compounds lose their effectiveness when formulated with certain anionic surfactants or other anionic active ingredients, such as tartar control phosphates. In many instances, it is preferred to use antibacterial compounds that do not show the adverse interactions with such anionic components. [0005] Some substituted phenols and biphenols are known to have antimicrobial properties. Natural products such as eugenol (4-allyl-2-methoxyphenol) have been used in oral care as a pulp capping agent and root canal sealer. It is generally recognized as safe by the FDA. A dimer of eugenol, dehydrodieugenol, is reported to be less cytotoxic and have greater anti-inflammatory activity than eugenol. There is an ongoing need to find biphenol compounds with acceptable combinations of antibacterial activity and safety. BRIEF SUMMARY OF THE INVENTION [0006] The invention provides an antiplaque oral composition that includes an orally acceptable carrier, and an antibacterially effective amount of a compound of structure (I): In the structure, R.sup.1 and R.sup.2 are independently selected from a lower C.sub.1-4 alkyl group and R.sup.3 and R.sup.4 are independently an alkenyl or alkyl group having from 1 to 20 carbon atoms. [0007] Also included in the invention are toothpastes or tooth gels that include at least one humectant; at least one abrasive compound; and an antibacterially effective amount of the compound represented by structure of formula (I): In (I), R.sup.1 and R.sup.2 are independently selected from a lower C.sub.1-4 alkyl group and R.sup.3 and R.sup.4 are independently an alkenyl or alkyl group having from 1 to 20 carbon atoms. [0008] Also provided are methods of inhibiting bacterial growth in the oral cavity of an animal by application of the compound of formula (I). DETAILED DESCRIPTION OF THE INVENTION [0009] A class of 5,5'-disubstituted 3,3'-dialkoxy-2,2'-dihydroxy-1,1'-biphenyl compounds exhibits inhibitory action against a variety of bacteria commonly found in the oral cavity. The compounds are used as antiplaque and/or antibacterial components of dentifrices and other oral compositions. The invention provides various oral compositions containing the compounds and an orally acceptable carrier. In various embodiments, antibacterial and antiplaque oral compositions are provided in the form of a toothpaste or gel, a tooth powder, a mouthwash or mouth rinse, a lozenge, chewing gum, an edible strip, and the like. The antibacterial compounds may be conveniently synthesized using novel coupling reaction steps, although any method of synthesis known or to be developed in the art can be used. [0010] The invention provides disubstituted 2,4'-diphenols and derivatives represented by the structure: exclusive of dehydrodieugenol. R.sup.1 and R.sup.2 are independently a lower C.sub.1-4 alkyl group and R.sup.3 and R.sup.4 are independently an alkenyl or alkyl group having from 1 to 20 carbon atoms, with the proviso that R.sup.3 and R.sup.4 are not both 2-propenyl when R.sup.1 and R.sup.2 are both CH.sub.3. Preferably, R contains 1 to 8 carbon atoms. In various embodiments, R has 4 to 8 carbon atoms. [0011] Antiplaque oral compositions are provided that contain an orally acceptable carrier and an antibacterial effective amount of at least one compound of structure (I). In various embodiments, the compositions contain from about 0.001% to about 10% by weight of (I). Without limitation, the orally acceptable carrier is a liquid carrier; a powder carrier; or a carrier that dissolves upon contact with saliva and other components of an oral environment. In other embodiments, the carrier can comprise a gum base. The oral compositions are provided variously in the form of a toothpaste or gel, a tooth powder, a mouthwash or mouth rinse, a lozenge, chewing gum, and an edible strip. Other forms of the composition include without limitation a liquid suitable for painting a dental surface, a wafer, a wipe or towelette, an implant, a dental floss, and forms that are edible or chewable by a small mammal, such as a dog or cat. [0012] In other embodiments, the invention provides toothpaste or gel compositions that contain at least one humectant, at least one abrasive material, and an antibacterial effective amount of at least one compound of structure (I). In various embodiments, the toothpaste or gel compositions further comprise an anticalculus agent such as a phosphate compound, alternatively combined with synthetic anionic polycarboxylates. In an exemplary embodiment, the toothpaste or gel composition comprises [0013] 0.001-5% by weight of compound (I); [0014] 1-70% by weight humectant; [0015] 1-70% by weight abrasive compounds; [0016] 0.5-2.5% by weight tetrasodium pyrophosphate (TSPP); and [0017] 1-10% by weight sodium tripolyphosphate (STPP). [0018] In other embodiments, the invention provides a method for inhibiting bacterial growth in the oral cavity of a subject animal, human or non-human, comprising applying to the oral surfaces of the subject animal an antibacterial composition comprising at least one compound of structure (I). In various embodiments, the method involves brushing the teeth and rinsing with compositions containing compound (I). As above, the method can be practiced by applying the antibacterial composition in a wide variety of forms such as toothpastes, tooth gels, tooth powder, mouth rinse, mouthwash, paint on gels, dissolvable or edible strips, chewing gum, lozenges, and the like. In various embodiments, treatment of oral surfaces with antibacterial compositions containing the compound of formula (I) may lead to reduction or elimination of plaque, to prevention or treatment of gingivitis, to amelioration of oral malodor, and prevention of periodontal disease. [0019] In various embodiments, the antibacterial compounds are selected from a class of 5,5'-disubstituted-3,3'-dimethoxy-2,2'-dihydroxy-1,1'-biphenyls, represented by the structure: where R.sup.3 and R.sup.4 independently represent an alkenyl or alkyl group of 1 to 20 carbon atoms. For example, dehydrodieugenol is the compound where R.sup.3 and R.sup.4 are 2-propenyl. In various embodiments, the antibacterial compounds are selected from structures (I) and (II) excluding dehydrodieugenol. Structure (II) corresponds to structure (I) where R.sup.1 and R.sup.2 are both methyl. [0020] In some embodiments of structures (I) and II, both R.sup.3 and R.sup.4 are alkyl groups. In other embodiments, both R.sup.3 and R.sup.4 are alkenyl groups. In yet other embodiments, one of the groups R.sup.3 and R.sup.4 is an alkyl group and the other is an alkenyl group. In various embodiments, the groups R.sup.3 and R.sup.4 are the same. In various embodiments, oral compositions containing compounds (I) and/or (II) exhibit antibacterial efficacy comparable to compositions containing triclosan. Continue reading about Antibacterial 5,5'-disubstituted 3,3'-dialkoxy-2,2'-dihydroxy-1,1'-biphenyl compounds and related methods... 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