Antibacterial 5,5'-disubstituted 3,3'-dialkoxy-2,2'-dihydroxy-1,1'-biphenyl compounds and related methods

Abstract

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 1 and R 2 are independently selected from a lower C 1-4 alkyl group and R 3 and R 4 are independently an alkenyl or alkyl group having from 1 to 20 carbon atoms. 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 the structure of formula (I). Also provided are methods of inhibiting bacterial growth in the oral cavity of an animal by application of the compound of formula (I).

1 . An antiplaque oral composition comprising 
 an orally acceptable carrier; and    an antibacterially effective amount of a compound of structure (I)                          wherein R 1  and R 2  are independently a lower C 1-4  alkyl group and R 3  and R 4  are independently an alkenyl or alkyl group having from 1 to 20 carbon atoms.    
   
   
       2 . The composition of  claim 1 , wherein structure (I) is dehydrodieugenol.  
   
   
       3 . The composition of  claim 1 , wherein R 3  and R 4  are not both 2-propenyl when R 1  and R 2  are both methyl.  
   
   
       4 . The composition of  claim 1 , comprising 0.001% to 10% by weight of the compound of formula (I).  
   
   
       5 . The composition of  claim 1 , wherein the carrier is a liquid carrier.  
   
   
       6 . The composition of  claim 1 , wherein the carrier is a powder carrier.  
   
   
       7 . The composition of  claim 1 , wherein the carrier dissolves upon contact with an oral environment.  
   
   
       8 . The composition of  claim 1  in a form selected from a paste, a gel, a powder, a mouth rinse, a lozenge, a chewing gum, and an edible strip.  
   
   
       9 . The composition of  claim 1 , wherein R 1  and R 2  independently are methyl.  
   
   
       10 . The composition of  claim 1 , wherein R 3  and R 4  independently are alkyl.  
   
   
       11 . The composition of  claim 1 , wherein R 3  and R 4  independently have 1 to 8 carbon atoms.  
   
   
       12 . The composition of  claim 1 , wherein R 3  and R 4  independently have 4 to 8 carbon atoms.  
   
   
       13 . A toothpaste or gel composition comprising 
 at least one humectant;    at least one abrasive compound; and    an antibacterially effective amount of                          wherein R 1  and R 2  are independently a lower C 1-4  alkyl group and R 3  and R 4  are independently an alkenyl or alkyl group having from 1 to 20 carbon atoms.    
   
   
       14 . The composition of  claim 13 , wherein the compound of structure (I) is dehydrodieugenol.  
   
   
       15 . The composition of  claim 13 , wherein R 3  and R 4  are not both 2-propenyl when R 1  and R 2  are both methyl.  
   
   
       16 . The composition of  claim 13 , further comprising an antitartar effective amount of an anticalculus agent comprising at least one phosphate compound.  
   
   
       17 . The composition of  claim 13 , wherein the anticalculus agent comprises tetrasodium pyrophosphate and trisodium polyphosphate.  
   
   
       18 . The composition of  claim 17 , wherein the anticalculus agent comprises a synthetic anionic polycarboxylate.  
   
   
       19 . The composition of  claim 18 , wherein the synthetic anionic polycarboxylate comprises a maleic anhydride copolymer with methyl vinyl ether.  
   
   
       20 . The composition of  claim 13 , comprising 
 0.01-5% by weight of a compound of structure (I);                          1-70% by weight or at least one humectant;    1-70% by weight of an abrasive compound;    0.5-2.5% by weight of tetrasodium pyrophosphate (TSPP); and    1-10% by weight of sodium tripolyphosphates (STPP).    
   
   
       21 . The composition of  claim 20 , wherein the weight radio of TSPP:STPP is about 1:7.  
   
   
       22 . The composition of  claim 20 , further comprising an anionic polycarboxylate.  
   
   
       23 . The composition of  claim 22 , wherein the ratio of TSPP:STPP:polycarboxylate is about 1:7:1.  
   
   
       24 . A method for inhibiting bacterial growth in the oral cavity of an animal, comprising applying to the oral surfaces of the subject animal an antibacterial composition comprising a compound of structure (I)  
     
       
         
         
             
             
         
       
     
     wherein R 1  and R 2  are independently a lower C 1-4  alkyl group and R 3  and R 4  are independently an alkenyl or alkyl group having from 1 to 20 carbon atoms.  
   
   
       25 . The method of  claim 24 , wherein the compound of structure (I) is dehydrodieugenol.  
   
   
       26 . The method of  claim 24 , wherein R 3  and R 4  are not both 2-propenyl when R 1  and R 2  are both methyl.  
   
   
       27 . The method of  claim 24 , wherein application comprises brushing the teeth.  
   
   
       28 . The method of  claim 24 , wherein applying comprises rinsing the oral surfaces with the composition, wherein the composition is in the form of a mouth rinse.  
   
   
       29 . The method of  claim 24 , wherein the antibacterial composition is a toothpaste or gel.  
   
   
       30 . The method of  claim 24 , wherein the antibacterial composition is a mouth rinse.  
   
   
       31 . The method of  claim 24 , wherein the animal is selected from mammals, an equine species, a feline species, a canine species, and a human.