Use of cyclohexanol derivatives as antimicrobial active compounds

Abstract

The present invention relates to the use of at least one cyclohexanol derivative of the formula (I) and/or (II) as antimicrobial active compound or as anti-acne, antidandruff, antiperspirant or deodorant active compound, to preparations comprising these compounds, and to specific cyclohexanol derivatives and to a process for the preparation thereof.

The invention claimed is: 
     
       1. A method for achieving an antimicrobial effect in a host in need thereof, comprising administering to a host in need thereof an effective amount of at least one compound of the formula I and/or II 
       
         
           
           
               
               
           
         
         in which R1, R2, R3, R4 and R5 stand, independently of one another, for a radical selected from
 H, OH, OCOCH 3 , O—(CH 2 —CH 2 —O) n —CH 2 —CH 2 —OH, where n=0 to 20, 
 straight-chain or branched alkyl or alkoxy group having 1 to 20 C atoms, where at least one of the radicals R1, R2, R3, R4 and R5 stands for OH, OCOCH 3  or O—(CH 2 —CH 2 —O) n —CH 2 —CH 2 —OH, where n=0 to 20, 
 
         and in which R6 and R7 stand, independently of one another, for a radical selected from
 H, 
 (CH 2 —CH 2 —O) n —CH 2 —CH 2 —OH, where n=0 to 20, 
 straight-chain or branched alkyl group having 1 to 20 C atoms, 
 straight-chain or branched alkenyl or alkynyl group having 2 to 20 C atoms and one or more double or triple bonds, 
 where the alkyl, alkenyl or alkynyl group may also contain one or more saturated or unsaturated C 3 - to C 12 -cycloalkyl groups, 
 
       
       with the proviso the following compound is excluded: 
       
         
           
           
               
               
           
         
       
     
     
       2. The method according to  claim 1  comprising administering in the form of cosmetic or pharmaceutical formulations, medicinal products or foods. 
     
     
       3. The method according to  claim 2  comprising administering in the form of a dental or oral care product. 
     
     
       4. The method according to  claim 1 , wherein the radicals R1, R2, R3, R4 and R5 stand, independently of one another, for H or OH, where 1, 2 or 3 of the radicals R1, R2, R3, R4 and R5 stand for OH. 
     
     
       5. The method according to  claim 4 , wherein the compound of the formula I and II is a compound of formula Ia, Ib, IIa and IIb 
       
         
           
           
               
               
           
         
         in which R6 and R7 stand, independently of one another, for
 H, 
 (CH 2 —CH 2 —O) n —CH 2 —CH 2 —OH, where n=0 to 20, 
 straight-chain or branched alkyl group having 1 to 20 C atoms, 
 straight-chain or branched alkenyl or alkynyl group having 2 to 20 C atoms and one or more double or triple bonds, 
 
         where the alkyl, alkenyl or alkynyl group may also contain one or more saturated or unsaturated C 3 - to C 12 -cycloalkyl groups. 
       
     
     
       6. The method according to  claim 1 , wherein the radicals R6 and R7 stand for
 H, 
 CH 2 —CH 2 —OH, 
 straight-chain or branched alkyl group having 1 to 10 C atoms, 
 which may also contain a saturated or unsaturated C 6 -cycloalkyl group. 
 
     
     
       7. The method according to  claim 6 , wherein the compound of the formula I is a compound selected from formulae I-1 to I-10 and I-12 to I-28 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
       8. A method for achieving an antimicrobial effect in a subject, comprising administering to a subject in need thereof an anti-acne, antidandruff, antiperspirant or deodorant formulation containing an effective amount of at least one compound of the formula I and/or II 
       
         
           
           
               
               
           
         
         in which R1, R2, R3, R4 and R5 stand, independently of one another, for a radical selected from
 H, OH, OCOCH 3 , O—(CH 2 —CH 2 —O) n —CH 2 —CH 2 —OH, where n=0 to 20, 
 straight-chain or branched alkyl or alkoxy group having 1 to 20 C atoms, where at least one of the radicals R1, R2, R3, R4 and R5 stands for OH, OCOCH 3  or O—(CH 2 —CH 2 —O) n —CH 2 —CH 2 —OH, where n=0 to 20, 
 
         and in which R6 and R7 stand, independently of one another, for a radical selected from
 H, 
 (CH 2 —CH 2 —O) n —CH 2 —CH 2 —OH, where n=0 to 20, 
 straight-chain or branched alkyl group having 1 to 20 C atoms, 
 straight-chain or branched alkenyl or alkynyl group having 2 to 20 C atoms and one or more double or triple bonds, 
 
         where the alkyl, alkenyl or alkynyl group may also contain one or more saturated or unsaturated C 3 - to C 12 -cycloalkyl groups. 
       
     
     
       9. The method according to claim 1, wherein an effective amount of at least one compound of the formula I is administered to said host. 
     
     
       10. The method according to claim 9, wherein the radicals R1, R2, R3, R4 and R5 stand, independently of one another, for H or OH, where 1, 2 or 3 of the radicals R1, R2, R3, R4 and R5 stand for OH. 
     
     
       11. The method according to claim 10, wherein said compound of formula I is a compound of formula Ia or Ib: 
       
         
           
           
               
               
           
         
       
       in which R6 stands for
 H, 
 (CH 2 —CH 2 —O) n —CH 2 —CH 2 —OH, where n=0 to 20, 
 straight-chain or branched alkyl group having 1 to 20 C atoms, 
 straight-chain or branched alkenyl or alkynyl group having 2 to 20 C atoms and one or more double or triple bonds, 
 wherein the alkyl, alkenyl and alkynyl groups each optionally contain one or more saturated or unsaturated C 3 - to C 12 -cycloalkyl groups. 
 
     
     
       12. The method according to claim 11, wherein the R6 stands for
 H,   CH 2 —CH 2 —OH,   straight-chain or branched alkyl group having 1 to 10 C atoms, which optionally contains a saturated or unsaturated C 6 -cycloalkyl group.   
     
     
       13. The method according to claim 12, wherein the compound of the formula I is a compound selected from formulae I-15 to I-28 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       
        
       
     
     
       14. The method according to claim 13, wherein said compound of formula I is a compound of formula I-20. 
     
     
       15. The method according to claim 8, wherein an effective amount of at least one compound of the formula I is administered to said subject. 
     
     
       16. The method according to claim 15, wherein the radicals R1, R2, R3, R4 and R5 stand, independently of one another, for H or OH, where 1, 2 or 3 of the radicals R1, R2, R3, R4 and R5 stand for OH. 
     
     
       17. The method according to claim 16, wherein said compound of formula I is a compound of formula Ia or Ib: 
       
         
           
           
               
               
           
         
       
       in which R6 stands for
 H, 
 (CH 2 —CH 2 —O) n —CH 2 —CH 2 —OH, where n=0 to 20, 
 straight-chain or branched alkyl group having 1 to 20 C atoms, 
 straight-chain or branched alkenyl or alkynyl group having 2 to 20 C atoms and one or more double or triple bonds, 
 wherein the alkyl, alkenyl and alkynyl groups each optionally contain one or more saturated or unsaturated C 3 - to C 12 -cycloalkyl groups. 
 
     
     
       18. The method according to claim 17, wherein the R6 stands for
 H,   CH 2 —CH 2 —OH,   straight-chain or branched alkyl group having 1 to 10 C atoms, which optionally contains a saturated or unsaturated C 6 -cycloalkyl group.   
     
     
       19. The method according to claim 18, wherein the compound of the formula I is a compound selected from formulae I-15 to I-28 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       
        
       
     
     
       20. The method according to claim 18, wherein said compound of formula I is a compound of formula I-20.