Alcoholic beverage substitutes

Abstract

Alcoholic beverage-substitutes such as a beer-substitute, a wine-substitute, a cider-substitute, an alcopop-substitute or a spirit-substitute beverage, comprising a base liquid (e.g., a base beverage) and a 2-aminoindan derivative such as defined by Formula I in the specification are disclosed.

1 - 48 . (canceled) 
     
     
         49 . An alcoholic beverage-substitute comprising a base liquid and a compound of Formula I or a physiologically acceptable salt thereof: 
       
         
           
           
               
               
           
         
         wherein:
 each of R 1  and R 2  is independently H, (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkynyl, (C 3 -C 8 )cycloalkyl, aryl, heteroaryl, heteroalicyclic, —O(C 1 -C 8 )alkyl, —OH, —OSO 2 CF 3 , —OSO 2 —(C 1 -C 8 )alkyl, —SOR 5 , —CO 2 R 5 , —CONR 5 R 6 , —COR 5 , —CF 3 , CN, —SR 5 , —SO 2 NR 5 R 6 , —SO 2 R 5 , —OCO—(C 1 -C 8 )alkyl, —NCO—(C 1 -C 8 )alkyl, —CH 2 O—(C 1 -C 8 )alkyl, —(C 1 -C 6 )alkyl-OH, —NHSO 2 R 5 , or halogen, or R 1  and R 2  together with two or more of the phenyl carbon atoms form a —X 1 —(CR 5 R 6 ) m- —X 2 — ring, wherein each of X 1  and X 2  is independently C, O, NH, or S; 
 m is 1, 2, 3, or 4; 
 each of R 3  and R 4  is independently H, (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkynyl, (C 3 -C 8 ) cycloalkyl, or —(CH 2 ) p -thienyl, wherein p is 1, 2, 3, or 4, or R 3  and R4 are joined together to form a heterocylic ring containing the nitrogen atom to which they are attached; and 
 each of R 5  and R 6  is independently H, (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 3 -C 8 )cycloalkyl or aryl; and 
 wherein:
 the alcoholic beverage-substitute is a beer-substitute, and the beer-substitute comprises the compound of Formula I in an amount within a range of from 0.20 mg/ml to 0.70 mg/ml; or 
 the alcoholic beverage-substitute is an alcopop-substitute, and the alcopop-substitute comprises the compound of Formula I in an amount within a range of from 0.25 to 0.60 mg/ml. 
 
 
       
     
     
         50 . The alcoholic beverage-substitute according to  claim 49 , wherein at least one of R 3  and R 4  is H. 
     
     
         51 . The alcoholic beverage-substitute according to  claim 49 , wherein each of R 1  and R 2  is H, —OCH 3 , or —OSO 2 CF 3 , or R 1  and R 2  together with two or more of the phenyl carbon atom form a —O(CH 2 ) m O— ring, wherein m is 1 or 2. 
     
     
         52 . The alcoholic beverage-substitute according to  claim 49 , wherein the compound is:
 5-methoxy-2-aminoindan;   5,6-dimethoxy-2-aminoindan;   5-methoxy-2-(N-propylamino)indan;   5,6-dimethoxy-2-(N-propylamino)indan;   5,6-dimethoxy-2-(di-N-butylamino)indan;   5-(trifluoromethylsulfonyloxy)-2-(N-propylamino)indan;   5,6-(di-trifluoromethylsulfonyloxy)-2-(N-propylamino)indan;   5,6-dimethoxy-2(pyrrolidino)indan;   5-(trifluoromethylsulfonyloxy)-6-hydroxy-2-(di-N-propylamino)indan;   5-(triluuoromethylsulfonyloxy)-6-acetoxy-2-(di-N-propylarnino)indan;   5-trifluromethansulfonyloxy-6-methoxy-2-(di-N-propylamino)indan;   5,6-ethylenedioxy-2-(di-N-propylamino)indan;   5,6-methylenedioxy-2-(di-N-propylamino)indan; or a physiologically acceptable salt thereof.   
     
     
         53 . The alcoholic beverage-substitute according to  claim 49 , wherein the beer-substitute comprises ethanol in an amount that is more than 0.01% by volume but less than 0.50% by volume. 
     
     
         54 . The alcoholic beverage-substitute according to  claim 49 , wherein the alcopop-substitute comprises ethanol in an amount that is more than 0.01% by volume but less than 1.00% by volume. 
     
     
         55 . An alcoholic beverage-substitute comprising a base liquid and a compound, wherein the base liquid is a fruit juice, fruit syrup, concentrate or nectar from fruits jello, vegetable juice, agave, a carbonated beverage, a caffeinated beverage, a specialized flavor formulation emulating the taste of existing wines and spirits, a non-alcoholic cocktail, malt beer, a dealcoholized cider, a dealcoholized wine, a dealcoholized beer, a dealcoholized spirit, tonic water or water, and wherein the compound is:
 5-methoxy-2-aminoindan;   5,6-dimethoxy-2-aminoindan;   5-methoxy-2-(N-propylamino)indan;   5,6-dimethoxy-2-(N-propylamino)indan;   5,6-dimethoxy-2-(di-N-butylamino)indan;   5-(trifluoromethylsulfonyloxy)-2-(N-propylamino)indan;   5,6-(di-trifluoromethylsulfonyloxy)-2-(N-propylamino)indan;   5,6-dimethoxy-2(pyrrolidino)indan;   5-(trifluoromethylsulfonyloxy)-6-hydroxy-2-(di-N-propylamino)indan;   5-(triluuoromethylsulfonyloxy)-6-acetoxy-2-(di-N-propylarnino)indan;   5-trifluromethansulfonyloxy-6-methoxy-2-(di-N-propylamino)indan;   5,6-ethylenedioxy-2-(di-N-propylamino)indan;   5,6-methylenedioxy-2-(di-N-propylamino)indan; or a physiologically acceptable salt thereof.   
     
     
         56 . An alcoholic beverage-substitute, wherein the alcoholic beverage-substitute is a wine-substitute comprising a base liquid and a compound, wherein the compound is:
 5-methoxy-2-aminoindan;   5,6-dimethoxy-2-aminoindan;   5-methoxy-2-(N-propylamino)indan;   5,6-dimethoxy-2-(N-propylamino)indan;   5,6-dimethoxy-2-(di-N-butylamino)indan;   5-(trifluoromethylsulfonyloxy)-2-(N-propylamino)indan;   5,6-(di-trifluoromethylsulfonyloxy)-2-(N-propylamino)indan;   5,6-dimethoxy-2(pyrrolidino)indan;   5-(trifluoromethylsulfonyloxy)-6-hydroxy-2-(di-N-propylamino)indan;   5-(triluuoromethylsulfonyloxy)-6-acetoxy-2-(di-N-propylarnino)indan;   5-trifluromethansulfonyloxy-6-methoxy-2-(di-N-propylamino)indan;   5,6-ethylenedioxy-2-(di-N-propylamino)indan;   5,6-methylenedioxy-2-(di-N-propylamino)indan; or a physiologically acceptable salt thereof; and
 wherein an amount of the compound is within a range of from 0.50 mg/ml to 1.25 mg/ml. 
   
     
     
         57 . The alcoholic beverage-substitute according to  claim 56 , wherein the wine-substitute comprises ethanol in an amount that is more than 0.01% by volume but less than 5.0% by volume. 
     
     
         58 . An alcoholic beverage-substitute beverage, wherein the alcoholic beverage-substitute is a spirit-substitute, wherein the spirit-substitute comprises a base liquid and a compound, and wherein the compound is:
 5-methoxy-2-aminoindan;   5,6-dimethoxy-2-aminoindan;   5-methoxy-2-(N-propylamino)indan;   5,6-dimethoxy-2-(N-propylamino)indan;   5,6-dimethoxy-2-(di-N-butylamino)indan;   5-(trifluoromethylsulfonyloxy)-2-(N-propylamino)indan;   5,6-(di-trifluoromethylsulfonyloxy)-2-(N-propylamino)indan;   5,6-dimethoxy-2(pyrrolidino)indan;   5-(trifluoromethylsulfonyloxy)-6-hydroxy-2-(di-N-propylamino)indan;   5-(triluuoromethylsulfonyloxy)-6-acetoxy-2-(di-N-propylarnino)indan;   5-trifluromethansulfonyloxy-6-methoxy-2-(di-N-propylamino)indan;   5,6-ethylenedioxy-2-(di-N-propylamino)indan;   5,6-methylenedioxy-2-(di-N-propylamino)indan; or a physiologically acceptable salt thereof; and
 wherein an amount of the compound is within a range of from 1.90 mg/ml to 2.97 mg/ml. 
   
     
     
         59 . The alcoholic beverage-substitute according to  claim 58 , wherein the spirit-substitute comprises ethanol in an amount that is more than 0.01% by volume but less than 15% by volume. 
     
     
         60 . A process for the preparation of an alcoholic beverage substitute, the process comprising mixing a base liquid with a compound of Formula I or a physiologically acceptable salt thereof: 
       
         
           
           
               
               
           
         
         wherein:
 each of R 1  and R 2  is independently H, (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkynyl, (C 3 -C 8 )cycloalkyl, aryl, heteroaryl, heteroalicyclic, —O(C 1 -C 8 )alkyl, —OH, —OSO 2 CF 3 , —OSO 2 —(C 1 -C 8 )alkyl, —SOR 5 , —CO 2 R 5 , —CONR 5 R 6 , —COR 5 , —CF 3 , CN, —SR 5 , —SO 2 NR 5 R 6 , —SO 2 R 5 , —OCO—(C 1 -C 8 )alkyl, —NCO—(C 1 -C 8 )alkyl, —CH 2 O—(C 1 -C 8 )alkyl, —(C 1 -C 6 )alkyl-OH, —NHSO 2 R 5 , or halogen, or R 1  and R 2  together with two or more of the phenyl carbon atoms form a —X 1 —(CR 5 R 6 ) m- —X 2 — ring, wherein each of X 1  and X 2  is independently C, O, NH or S; 
 m is 1, 2, 3, or 4; 
 each of R 3  and R4 is independently H, (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkynyl, (C 3 -C 8 ) cycloalkyl, or —(CH 2 ) p -thienyl, wherein p is 1, 2, 3, or 4, or R 3  and R 4  are joined together to form a heterocylic ring containing the nitrogen atom to which they are attached; and 
 each of R 5  and R 6  is independently H, (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 3 -C 8 )cycloalkyl or aryl; and 
 wherein the amount of the compound of Formula I is in the range of from 0.20 mg/ml to 2.97 mg/ml. 
 
       
     
     
         61 . The process according to  claim 60 , wherein the compound of Formula I is:
 5-methoxy-2-aminoindan;   5,6-dimethoxy-2-aminoindan;   5-methoxy-2-(N-propylamino)indan;   5,6-dimethoxy-2-(N-propylamino)indan;   5,6-dimethoxy-2-(di-N-butylamino)indan;   5-(trifluoromethylsulfonyloxy)-2-(N-propylamino)indan;   5,6-(di-trifluoromethylsulfonyloxy)-2-(N-propylamino)indan;   5,6-dimethoxy-2(pyrrolidino)indan;   5-(trifluoromethylsulfonyloxy)-6-hydroxy-2-(di-N-propylamino)indan;   5-(triluuoromethylsulfonyloxy)-6-acetoxy-2-(di-N-propylarnino)indan;   5-trifluromethansulfonyloxy-6-methoxy-2-(di-N-propylamino)indan;   5,6-ethylenedioxy-2-(di-N-propylamino)indan;   5,6-methylenedioxy-2-(di-N-propylamino)indan; or a physiologically acceptable salt thereof.   
     
     
         62 . The alcoholic beverage-substitute according to  claim 49 , wherein the compound is 5-methoxy-2-aminoindan or a physiologically acceptable salt thereof.