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United States Patent (19) 11 Patent Number: 5,723,500 Stringer Et Al

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United States Patent (19) 11 Patent Number: 5,723,500 Stringer Et Al IIIUS005723500A United States Patent (19) 11 Patent Number: 5,723,500 Stringer et al. (45) Date of Patent: Mar. 3, 1998 54 ANTIPLAQUE ORAL COMPOSITION AND 553142 8/1974 Switzerland. METHOD 9210992 7/1992 WTPO 75 Inventors: Orum D. Stringer, Yardley, Pa.; John OTHER PUBLICATIONS C. Brahms. Trenton, N.J.; Malathy Subramanian, Branchburg, N.J.; Chemical Abstracts vol. 93, No. 17. Oct. 27, 1980. Ernest E. Kelly. New Brunswick, N.J. (Abstract No. 162715-Japan Kokai 55 016 802-Ajino moto). 73) Assignee: Colgate-Palmolive Company, New York, N.Y. Primary Examiner-Marianne M. Cintins Assistant Examiner-Dwayne C. Jones 21) Appl. No.: 649,389 Attorney, Agent, or Firm-Henry S. Goldfine 22) Filed: May 17, 1996 57 ABSTRACT (51) Int. Cl. ............... A01N31/08: A61K 31/05 An oral antiplaque composition and treatment of teeth (52 U.S. Cl. .......................... 514/736: 514/734; 514/731; therewith wherein the essential antiplaque agent is a sub 424/49 stantially water insoluble noncationic antibacterial phenol 58 Field of Search .................................. 514/731, 734, containing, relative to the hydroxyl group, an alkyl or 514/736: 424/49 cycloalkyl group, preferably tert-butyl (t-butyl), in 2-position, and substituents in one or both of the 4- and (56) References Cited 5-positions, one of which may be phenyl or 2',3' and/or 4 U.S. PATENT DOCUMENTS substituted alkyl or cycloalkyl phenyl, preferably 4'-t-butyl phenyl or a phenanthrene containing a hydroxyl substituent 3.300,051 3/1974 Barnhart et al. ........................ 424/346 in the 2- or 3-position and alkyl or cycloalkyl, preferably 4,321,257 3/1982 Sipos ............. ... 424/80 t-butyl, substituents in the other of the 2- and 3-positions and 5,188,821 2/1993 Gaffar et al. ... 424/52 in at least one of the other rings. Novel antibacterial alky 5,487,893 1/1996 Vachy ................................... 424/195. lated phenols are also described. FOREIGN PATENT DOCUMENTS 2128026 10/1972 France. 46 Claims, No Drawings 5,723.500 1. 2 orally acceptable vehicle and an effective antiplaque amount ANTIPLAQUE ORAL COMPOSITION AND of at least one substantially water insoluble noncationic METHOD monohydroxy AA having one of the following formulae: BACKGROUND OF THE INVENTION Field of the Invention This invention relates to antibacterial antiplaque oral compositions and also to compositions containing a novel essential antiplaque component comprising a substantially water insoluble, noncationic antibacterial alkylated phenol O compound more fully described below and to a selected group of such compounds which are considered novel. Dental plaque is a soft deposit which forms on teeth as opposed to calculus which is a hard calcified deposit on teeth. Unlike calculus, plaque may form on any part of the 15 tooth surface, particularly including at the gingival margin. Hence, beside being unsightly, it is implicated in the occurence of gingivitis. Accordingly, it is highly desirable to include antimicro bial (antibacterial) agents which have been known to reduce plaque in oral compositions. The cationic antibacterial materials such as chlorhexidine, benzthonium chloride and cetyl pyridinium chloride have been the subject of greatest investigation as antibacterial 25 antiplaque agents. However, they are generally not effective when used with anionic materials. Noncationic antibacterial wherein R' is (1) a C-sn-alkyl, optionally partially or fully materials, on the other hand, can be compatible with anionic substituted with C-6 cycloalkyls or C-side chain alkyls, or components in an oral composition. (2) a C-8 cycloalkyl, optionally partially or fully substituted However, oral compositions typically are mixtures of 30 with C-7 side chain alkyls or C. cycloalkyls; numerous components and even such typically neutral mate the Bring and R of formula I are interchangeably rials as humectants can affect performance of such compo substituted in the 4 and 5 positions of the A ring of formula sitions. I. and R is H or R'; and Halogenated hydroxydiphenyl ethers such as triclosan (1) R' and Rare interchangeably substituted in the 4' and have been very effectively employed in oral compositions as 35 5' positions of the Bring of formula I, R is R' and R is H or R'; or antibacterial antiplaque agents. However, it is desirable to be (2) in the Bring, R in the 5'-position is H. R. in the 4' able to provide non-halogenated agents which are highly position is R. Ris independently H or R' in the 2' and/or effective and possibly even more effective than triclosan. 3' positions, and n is 2; and Phenol and alkyl substituted phenols are well known and Rin formula III is independently H or R' in the 5, 6, 7 widely used antimicrobials. Thymol (2-isopropyl-5- and/or 8 positions and m is 4. methylphenol) is an active antimicrobial agent in commer We have further found that in the vast majority of cial mouthrinse formulations, but its anti-microbial activity instances, highly and unexpectedly superior antimicrobial is considered relatively low and possibly insufficient, its activity is supplied by AA's of one of the above formulae activity for example being only a small fraction of the 45 containing t-butyl (tert-butyl) as at least one and preferably activity of triclosan. Hitherto, alternatives to triclosan hav two (or even or more) of the R' and R' values. ing substantially greater antiplaque activity than thymol or This invention is at least in part based on our further than monoalkyl phenols and optimally comparable to or findings that: even greater then the activity of triclosan have not been 1. tert-butyl (t-butyl) substitution at the ortho position of available. 50 an unsubstituted phenol can enhance its antimicrobial effect It is an object of this invention to provide an antiplaque by a factor of 10. oral composition with substantial antiplaque effectiveness 2. tert-butyl substitution of the pendant phenyl group of a containing noncationic phenolic oral antibacterial antiplaque phenylphenol (formula I), e.g., substitution of 2-tert-butyl agents (AA) as alternatives to triclosan. Another object is to 5-phenyl phenol to give 2-tert-butyl-5-(4'-tert-butylphenyl) provide alkyl phenolic AA's which, except for the single OH 55 phenol likewise enhances the activity of the resultant by an group, are entirely hydrocarbon and which have oral anti additional factor of 10. microbial activities up to 100 or more times the activity of Thus, for instance, 3-phenyl phenol (3-hydroxybiphenyl) thymol, for instance up to as much as or exceeding the has an activity slightly less than that of thymol vs. A. activity of triclosan. A further object is to provide such AA's viscoscus, a common constituent of human dental plaque. which are. or can be expected to be. found in nature, e.g. On the other hand, 2-tert-butyl-5-phenyl phenol (3-hydroxy plant material, etc. Still another object is to provide novel 4-tert-butylbiphenyl) has an observed activity 50 times AA's. Other objects and advantages will appear as the greater than thymol and 2-tert-butyl-5-(4'-tert-butylphenyl) description proceeds. phenol (3-hydroxy-4,4'-di-tert-butylbiphenyl) has an observed activity greater than 100 times that of thymol. SUMMARY OF THE INVENTION 65 As described herein other alkyl phenol AA's also provide In accordance with some of its aspects, this invention enhanced antibacterial effectiveness for prevention or reduc relates to an oral antiplaque composition comprising an tion of plaque formation. 5,723.500 3 4 By way of further example, phenols of the type -continued OH (6) OH (1) C(CH3)3 C C(CH3)3 C(CH3)3 10 2-t-butyl-5-(4'-t-butyl-phenyl)phenol and OH (7) C(CH3)3 2-t-butyl-4-(4'-t-butylphenyl)phenol 15 OH (2) CCH3)3 O C CH3CH C C(CH3)3 2-t-butyl-3-hydroxy-10, 10-dimethyl-9,10 dihydrophenanthrene R10 can have an activity level in the range 100x thymol. This is 2-t-butyl-4-R0-phenol the activity level of triclosan. wherein R0 = phenyl 25 The above AA compounds (1)-(7) fall within the scope of the AA agents of formulas I and, DI and it will be understood and that related compounds active as AA agents can be employed containing indicated variations invalues, numbers OH (3) and positions of R" and R. R. as for example: 30 2-methyl-5-(4'-cyclopropylphenyl)phenol 2-octyl-5-(4'-cyclohexylphenyl)phenol 2-cyclohexyl-5-(4-isopropylphenyl)phenol 2.4-diisopropyl-5-phenylphenol 2,4-dicyclopropyl-5-phenylphenol 35 2,4-dimethyl-5-phenylphenol 2-t-butyl-5(4'-isopropylphenyl)phenol 2-t-butyl-4-(4'-cyclohexylphenyl)phenol 2-t-butyl-4-(1,1-dimethyloctyl)5-phenylphenol 2-t-butyl-5-phenylphenol 2-(1-cyclopropylbutyl)-4-t-butyl-5-phenylphenol 2-isopropyl-4-phenylphenol 2-cyclobutyl-4-phenylphenol can to have an activity level at least 10x that of thymol. 2-ethyl-4-phenylphenol 2-isooctyl-5-phenylphenol 2-cyclopropyl-5-phenylphenol Phenols of the type: 45 2-methyl-5-phenylphenol 2-(1-t-butylhexyl)-5-phenylphenol OH (4) 2-t-butyl-3-hydroxy-10, 10-di-t-butyl-9,10 dihydrophenanthrene 2-(1,1-dimethylpropyl-3-hydroxy-10.10-di-cyclohexyl-9. C C(CH3)3 SO 10-dihydrophenanthrene While 2-tert-butyl-5-phenyl phenol (3-hydroxy-4-tert butylbiphenyl) is known, it's use as an antimicrobial is not O C(CH3)3 believed to have been reported in the literature. The same applies to a number of other compounds of any of the above 24,di-t-butyl-5-phenylphenol 55 formulae, for instance formula I. As described below, a number of the AA's are also novel.
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