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United States Patent (19) 11 Patent Number: 4,828,822 Miihlemann Et Al

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United States Patent (19) 11 Patent Number: 4,828,822 Miihlemann Et Al United States Patent (19) 11 Patent Number: 4,828,822 Miihlemann et al. (45) Date of Patent: May 9, 1989 (54) PROCESS FOR STABILIZING AQUEOUS S. Ebell, "Karies und Zuckeraustauschstoffe', Emah COMPOSITIONS CONTAINING T N SALTS rungsclorschung Hett, 1978, pp. 171-174. 75) Inventors: Hans R. Miihlemann, Zollikon; Hans H. R. Muhlemann, "Zuckerfreie, Zahnschonende und Schmid, Muttenz, both of Nicht-Kariogene Bonbons und Sussigkeiten'. Switzerland 88, Scand J. Dent. Res., 193-200 (1980), “Effect of Mouthrinses With Tin(II), Fluoride, Lanthanum Chlo 73) Assignee: GABA International AG, Basel, ride, Sodium Fluoride and Chlorohexidine on the Switzerland Amount of Lipoteichoic Acid Formed in Plaque'. (21) Appl. No.: 109,830 Substitution of Sucrose by Lycasin in Candy, Roslagen Study, Frostell et al., Acta Odontol. Scand., 1974, 32(4), 22 Filed: Oct. 16, 1987 235-54 (Eng), 71769m, CA 82-71769. Chemical Abstract, 80-128408h, Effect of Mouth Related U.S. Application Data Rinses with Sucrose, Glucose, Fructose, Lactose, Sor 63 Continuation-in-part of Ser. No. 363,013, Mar. 29, bitol, and Lycasin on the pH of Dental Plaque. 1982, abandoned, which is a continuation of Ser. No. Chemical Abstracts, 93-106820c, Effect of Inorganic 192,874, Oct. 1, 1980, abandoned. Ions and Surface Active Organic Compounds on the (30) Foreign Application Priority Data Adherence of Oral Streptococci. Oct. 2, 1979 GB United Kingdom ................. 7934159 Chemical Abstract, 93:43218q, Relation of Amylase to Starch and Lycasin Metabolism in Human Dental Jan. 24, 1980 GB United Kingdom ................. 8002433 Plaque in Vitro. Feb. 1, 1980 GB United Kingdom ................. 8003525 Fed. Reg. 17,245(1974). 51 Int. Cl." ......................... A61K 7/16; A61K 7/18; Chemical Abstract, 93:143814Z, Effect of Mouthrinses A61K 7/22 with Tin (II), Fluoride, Lanthanum Chloride, Sodium 52 U.S. C. ......................................... 424/52; 424/54 Fluoride, and Chlorhexidine on the Amount of Lipotei 58 Field of Search .................................... 424/52, 54 choic Acid Formed in Plaque. (56) References Cited Chemical Abstract, 93-143813y, Effect on low pH and Fluoride Levels Upon Growth and Sugar Catabolism U.S. PATENT DOCUMENTS by Plaque Bacteria. 3,083,143 3/1963 Schmid et al. Chemical Abstract, 163957s, Mouthwash Compositions 3,105,013 9/1963 Saul et al. Containing Maltitol. 3,277,118 10/1966 Schmid et al. 3,282,792 11/1966 Fiscella . Chemical Abstract, 91:90089s, Effects of 3 Months Fre 3,413,326 11/1968 Schmid . quent Consumption of Hydrogenated Starch Hydroly 3,445,567 5/1969 Muhler . zate (Lycasin), Maltitol, Sorbitol and Xylitol on Human 3,544,678 12/1970 Griebstein . Dental Plaque. 3,914,406 10/1975 Yankell . Chemical Abstract, 91:54724m, Acid Production from 3,932,604 1/1976 Barth . Sucrose Substitutes in Human Dental Plaque. 3,970,747 7/1976 Barth. 4,088,752 5/1978 Muhlemann et al. Chemical Abstract, 89:19588.6m, Acid Production from 4,117,109 9/1978 Stookey . Swedish Lycasin (Candy Quality) and French Lycasin 4,157,386 6/1979 La Rochelle. (80/55), in Human Dental Plaques. 4,279,888 7/1981 Suganuma et al. Chemical Abstract, 93:184332j, Lycasin Hydrogenated 4,308,252 12/1981 Tomaich et al. Hydrolyzates. 4,308,253 12/1981 Schmid et al. Chemical Abstracts, 91:Spalte 417v, An In Vivo Study of the Effects of Fluoride (Stannous Fluoride 0.4%, FOREIGN PATENT DOCUMENTS APF 1.23%, and Neutral Sodium Fluride 0.05%) on 9698.62 6/1975 Canada. Levels of Organisms Resembling Actnomyces, Gingi 865272 4/1961 United Kingdom . 869257 5/1962 United Kingdom . val Inflamation and Plaque Accumulation. 1003595 9/1965 United Kingdom . Chemical Abstract, 91-73170u, Technological Prob 1066795 4/1967 United Kingdom. lems in the Incorporation of Hydrogenated Glucose 1067352 5/1967 United Kingdom. Syrups and L-Sorbose. 1194885 6/1970 United Kingdom. Chemical Abstracts, 88-47350w, Acid Production from 1249742 10/1971 United Kingdom. Lycasin, Maltitol, Sorbitol and Xylitol by Oral Strepto 1272454 4/1972 United Kingdom. cocci and Lactobacilli. 1381826 1/1975 United Kingdom. Chemical Abstracts, 81-54360h, Topical Fluoride Prep 1475899 6/1977 United Kingdom. arations for Reducing Incidence of Dental Caries. 2007974A 10/1978 United Kingdom. Chemical Abstract, 76-57450v, Effects of Sucrose, OTHER PUBLICATIONS Starch, and a Hydrogenated Starch Derivateive on Dental Caries in the Rat. Chemical Abstract, 108480, Toxicological Aspects of Chemical Abstract, 75-74793f, Effects of Consumption Stannous Fluoride after Ingestion as a Clear, of Hydrogenated Saccharides and Sucrose on the Blood Precipitate-Free Solution Compared to Sodium Fluo Sugar Concentration. ride. Chemical Abstract, 92-35405n, Contribution of Maltitol 4,828,822 Page 2 and Lycasin to Experimental Enamel Demineralization lysis of the tin salts by the addition of certain cationic in the Human Mouth. surfactant diamine salts. The additive fully preserves, or Topical Fluoride Preparations for Reducing Incidence even potentiates, the inhibiting action of tin salts on of Dental Caries Notice of Status, 63-Pharmaceuticals, plaque formation an dental caries. The formulations Robert Doerge, 54360h. advantageously also contain a non-ionic, water-soluble Primary Examiner-Shep K. Rose addition product of ethylene oxide which further in Attorney, Agent, or Firm-Finnegan, Henderson, proves the stability. Farabow, Garrett & Dunner 57 ABSTRACT Formulations for oral care and dental care, which con tain tin (II) salts and water, are stabilized against hydro 6 Claims, No Drawings 4,828,822 1. 2 effective mouth rinse is produced P.E. Norris, J. Amer. PROCESS FOR STABILIZING AOUEOUS Pharm. Ass. 20 (1959), 86). Fresh rinsing solutions can COMPOSITIONS CONTAINING TIN SALTS also be prepared, immediately prior to use, from SnF2 tablets or by dilution of highly concentrated and more The invention relates to a process for stabilizing oral 5 stable 20% strength SnF2 solutions I.L. Shannon and compositions for the prophylaxis and combating of colleagues, J. Southern Calif. State Dent. Ass. 33 plaque formation and of dental caries, which composi (1965), 520). tions contain one or more tin (II) salts in a water con Long-lasting stability has been achieved by incorpo taining medium, and whose stability over a lengthy rating tin(II) fluoride into anhydrous glycerol I.L. period is ensured through stabilisation of the tin salt(s). 10 Shannon, Caries Res. 3 (1969), 339. The term oral compositions in particular embraces Aqueous solutions of tin(II) fluoride containing tooth-pastes, dental gels, mouthwashes, mouth sprays, added sodium fluoride, glycerol or tartaric acid at ap rinsing tablets, prophylaxis pastes, solutions for local propriate concentrations can, for a limited period of application, and the like. time, be kept in a clear, precipitate-free and esthetically The tin(II) ions have a plaque-inhibiting action; this 15 acceptable condition at room temperature and at an action has been demonstrated in dogs, for local applica elevated temperature. However, the concentration of tion, and in man, for the use of mouthwashes containing tritratable tin(II) ions proves to be greatly reduced by SnF2. It has also been found that mouthwashes contain the additives J.K. Lim, loc. cit. and J. Dent. Res. 50 ing SnF2at a concentration corresponding to 780 and (1971), 531. 3,100 ppm of Snt t reduce the formation of acid from 20 Viewed overall, the numerous attempts to stabilise sucrose in the bacterial deposits. SnF2 is generally the aqueous solutions of tin(II) fluoride have only pro recognised by scientific circles as an agent for combat duced a small partial success, namely through the prep ing dental caries, and is an effective constituent of car aration of mouthwashes immediately prior to use ies-inhibiting preparations. Anon, Federal Register 39 (1974), 17245). On the other The metabolic effects of low Snf2 concentrations in 25 hand, in conventional formulations for the care of the counteracting plaque are in the main attributable to the mouth and the teeth, which formulations are required to antibacterial action of the tin(II) ions, which probably withstand, without damage, at least a certain period of cause changes in the cell membranes of the bacteria. It storage, the problem has hitherto remained unsolved. has also been found that the reduction in plaque under Further attempts to stabilize oral aqueous composi the action of tin(II) ions is accompanied by a regression 30 tions containing a stannous salt comprise adding an of gingivitis. orally acceptable acid such that the pH of the composi In practical respects, however, it is an important tion is in the range of from 2 to 4, i.e. the composition is disadvantage that tin(II) salts, inter alia tin(II) fluoride, in substantially acidic state (GB 2,007,974, Y. Ochiai et rapidly decompose in oral preparations diluted with al.), or adding as a complexing agent hydroxyethylni water; this is true in particular for the low concentration 35 trilodiacetic acid, m-hydroxybenzoic acid, 1,2,3- ranges and at the pH values acceptable in the mouth propanetricarboxylic acid or itaconic acid (U.S. Pat. (pH from about 4.5 to 9.0), such as are encountered in No. 3,544,678, W.J. Griebstein). As further complexing mouthwashes, rinsing solutions, toothpastes and other agents of the same kind, hydroxyl substituted aliphatic formulations for the care of the mouth and of the teeth. di- and tri-carboxylic acids like malic acid and citric Freshly prepared solutions of tin(II) fluoride or of tin acid also may be used for stabilisation of Snf2 in aque (II) chloride and an alkali metal fluoride show opales ous compositions (U.S. Pat. No. 3,282,792, A.J. Fis cence and turbidity within from one to 10 minutes. cella). When the solutions are left to stand, white precipitates It has now been found, surprisingly, that the addition subsequently form, and these progressively increase in of certain water-soluble organic diamine salts to aque amount over a period of 3 to 7 days Accepted Dental 45 ous media which contain tin(II) fluoride, other tin(II) Therapeutics, 36th edition, Amer.
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