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1. (WO2016092547) ALCOHOLIC BEVERAGE SUBSTITUTES
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WHAT IS CLAIMED IS:

1. An alcoholic beverage-substitute comprising a base liquid and a compound represented by Formula I:


Formula I

wherein:

each of Ri and R2 is independently selected from the group consisting of H, (Q-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C3-C8)cycloalkyl, aryl, heteroaryl, heteroalicyclic, -0(Ci-C8)alkyl, OH, -OS02CF3, -OS02-(Ci-C8)alkyl, -SOR5, -C02R5, -CONR5R6, -COR5, -CF3, CN, -SR5, -S02NR5R6, -S02R5, -OCO-(Ci-C8)alkyl, -NCO-(Ci-C8)alkyl, -CH20-(Ci-C8)alkyl, -(Ci-C6)alkyl-OH, -NHS02R5, and halogen, or, alternatively, Ri and R2 together with two or more of the phenyl carbon atoms form a -Xi-(CR5R6)m-- 2- ring, wherein each of Xi and X2 is independently selected from C, O, NH or S and m is 1, 2, 3, or 4;

each of R3 and R4 is independently selected from the group consisting of H, (Ci-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C3-C8) cycloalkyl, and -(CH2)p-thienyl, wherein p is 1, 2, 3, or 4, or alternatively, R3 and R4 are joined together to form a heterocylic ring (heteroalicyclic or heteroaryl) containing the nitrogen atom to which they are attached; and

each of R5 and R6 is independently selected from the group consisting of H, (Ci-C8)alkyl, (C2-C8)alkenyl, (C3-C8)cycloalkyl and aryl;

or a physiologically acceptable salt thereof.

2. The alcoholic beverage-substitute according to claim 1, wherein:

each of Ri and R2 is independently selected from the group consisting of H, (Ci-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C3-C8)cycloalkyl, aryl, -OCH3, OH, -OS02CF3, -OS02CH3, -SOR5, -C02R5, -CONR5R6, -COR5, -CF3, -CN, -SR5, -

SO2NR5R6, -SO2R5, -CH2-OH, halogen, phthalimidyl, thiophenyl, pyrrolyl, pyrrolinyl, and oxazolyl, or, alternatively, Ri and R2 together with two or more of the phenyl carbon atoms form a -0(CH2)mO- ring, wherein m is 1 or 2;

R3 and R4 are joined together to form a heterocylic ring containing 4 to 8 carbon atoms with the nitrogen atom to which they are attached; and

each of R5 and R6 is independently selected from the group consisting of H, ( -C8) alkyl, (C2-C8) alkenyl, and (C3-C8) cycloalkyl.

3. The alcoholic beverage-substitute according to claim 1, wherein at least one of R3 and R4 is H.

4. The alcoholic beverage-substitute according to any one of claims 1 to 3, wherein each of Ri and R2 is H, -OCH3, or -OS02CF3, or Ri and R2 together with two or more of the phenyl carbon atom form a -0(CH2)mO- ring, wherein m is 1 or 2.

5. The alcoholic beverage-substitute according to claim 1 or 3, wherein R3 or R4 is propyl.

6. The alcoholic beverage-substitute according to any one of claims 1 to 5, wherein said compound is selected from:

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; and

5,6-methylenedioxy-2-(di-N-propylamino)indan.

7. The alcoholic beverage-substitute according to any one of claims 1 to 6, wherein said base liquid is a beverage selected from fruit juice, fruit syrup, concentrate or nectar from fruits jello, vegetable juice, a plant material such as agave, a carbonated beverage such as cola, a caffeinated beverage, a specialized flavor formulation emulating the taste of existing wines and spirits, a non-alcoholic cocktail ("mocktails"), malt beer, a dealcoholized cider, a dealcoholized wine, a dealcoholized beer, a dealcoholized spirit, tonic water and water.

8. The alcoholic beverage-substitute according to any one of claims 1 to 7, being selected from a beer-substitute, a wine-substitute, a cider-substitute, a spirit-substitute and alcopop substitute beverage.

9. The alcoholic beverage-substitute according to any one of claims 1 to 7 being a beer-substitute.

10. The alcoholic beverage-substitute according to claim 9, wherein said a beer-substitute is selected from an ale-substitute, a stout-substitute, a porter-substitute, and a lager-substitute.

11. The alcoholic beverage-substitute according to claim 9 or 10, wherein said beer-substitute comprises said compound represented by Formula I in an amount that imparts to the beverage the psychotropic effect, palatability and the pleasures of drinking provided by an alcoholic beer containing 4.8-10 % alcohol by volume.

12. The alcoholic beverage-substitute according to claim 11, wherein said beer-substitute comprises said compound represented by Formula I in an amount within a range selected from 0.20 mg/ml to 0.70 mg/ml, 0.20 to 0.68 mg/ml, 0.25 to 0.68 mg/ml, 0.28 to 0.66 mg/1, 0.30 to 0.66 mg/ml, 0.28 to 0.65 mg/ml, 0.28 to 0.60 mg/ml 0.30 to 0.60 mg/ml, 0.30 to 0.58 mg/ml, 0.30 to 0.55 mg/ml, 0.30 to 0.50 mg/ml, 0.30 to

0.48 mg/ml, 0.30 to 0.45 mg/ml, 0.30 to 0.42 mg/ml, 0.30 to 0.40 mg/ml, 0.30 to 0.38 mg/ml or 0.31 to 0.36 mg/ml.

13. The alcoholic beverage-substitute according to claim 12, wherein said beer-substitute comprises 0.31 mg/ml to 0.33 mg/ml of said compound.

14. The alcoholic beverage-substitute according to any one of claims 9 to 13, wherein said beer-substitute comprises ethanol in an amount that is more than 0.01 % by volume but less than 0.50 %, less than 0.25 %, less than 0.2 %, less than 0.15 %, less than 0.10 %, or less than 0.05 % by volume.

15. The alcoholic beverage-substitute according to any one of claims 1 to 7, being a wine-substitute.

16. The alcoholic beverage-substitute of claim 15, wherein said wine-substitute is selected from a dry red wine-substitute, a dry white wine- substitute, a semi-dry red wine-substitute, a semi-dry white wine-substitute, a rose wine-substitute, a dessert wine-substitute, a Port wine-substitute, a Champagne-substitute, a sparkling wine-substitute and vermouth-substitute.

17. The alcoholic beverage-substitute according to claim 15 or 16, comprising said compound represented by Formula I in amount that imparts to the beverage the psychotropic effect, palatability and the pleasures of drinking provided by an alcoholic wine containing 10-14 % alcohol by volume.

18. The alcoholic beverage-substitute beverage according to claim 17, comprising said compound represented by Formula I in an amount within a range selected from 0.50 mg/ml to 1.25 mg/ml, 0.55 to 1.25 mg/ml, 0.55 to 1.20 mg/ml, 0.60 to 1.20 mg/1, 0.65 to 1.20 mg/ml, 0.70 to 1.20 mg/ml, 0.70 to 1.10 mg/ml, 0.75 to 1.10 mg/ml, 0.75 to 1.00 mg/ml, 0.78 to 1.00 mg/ml, 0.80 to 1.00 mg/ml, 0.80 to 1.05 mg/ml, 0.80 to 0.98 mg/ml or 0.80 to 0.95 mg/ml.

19. The alcoholic beverage-substitute beverage according to claim 18, comprising 0.79 mg/ml to 0.95 mg/ml of said compound.

20. The alcoholic beverage-substitute according to any one of claims 15 to 19, wherein said wine- substitute comprises ethanol in an amount that is more than 0.01 % by volume but less than 5.0 %, less than 4.0 %, less than 3.0 %, less than 2.5 %, less than 2.0 %, less than 1.5 %, less than 1.0 %, less than 0.5 %, less than 0.25 %, less than 0.2 %, less than 0.15 %, less than 0.10 %, or less than 0.05 % by volume.

21. The alcoholic beverage substitute according to claim 8, being a spirit-substitute.

22. The alcoholic beverage substitute according to claim 21, wherein said spirit-substitute is selected from a brandy-substitute, a liquor-substitute, saki-substitute, Ouzo-substitute, an arrack-substitute, a rum-substitute, a vodka-substitute, a tequila-substitute, a schnapps-substitute, a whiskey-substitute, a gin-substitute, a cordial-substitute, Cachaca-substitute and a slivovitz-substitute.

23. The alcoholic beverage-substitute according to claim 21 or 22, comprising said compound represented by Formula I in amount that imparts to the beverage the psychotropic effect, palatability and the pleasures of drinking provided by an alcoholic spirit containing 30-40 % alcohol by volume.

24. The alcoholic beverage-substituted beverage according to claim 23, comprising said compound represented by Formula I in an amount within a range selected from 1.90 mg/ml to 2.97 mg/ml, 1.90 mg/ml to 2.64 mg/ml 1.90 mg/ml to 2.60 mg/ml, 1.90 to 2.55 mg/ml, 1.95 to 2.55 mg/ml, 1.95 to 2.50 mg/ml, 1.95 to 2.40 mg/ml, 1.95 to 2.30 mg/ml, 1.96 to 2.35 mg/1, 1.96 to 2.30 mg/ml, 1.96 to 2.28 mg/ml, 1.96 to 2.25 mg/ml, 1.96 to 2.20 mg/ml, 1.98 to 2.28 mg/ml, 1.98 to 2.25 mg/ml, or 1.98 to 2.20 mg/ml.

25. The alcoholic beverage-substituted according to claim 24, comprising 1.98 mg/ml to 2.20 mg/ml of said compound.

26. The alcoholic beverage-substitute according to any one of claims 21 to 25, wherein said spirit-substitute comprises ethanol in an amount that is more than 0.01 % but less than 15%, less than 14 %, less than 12 %, less than 11.0 %, less than 10.0 %, less than 9.0 %, less than 8.0 %, less than 7.0 %, less than 6.0 %, less than 4.50 %, less than 4.00 %, less than 3.50 %, less than 3.00 %, less than 2.50 %, less than 2.00 %, less than 1.50 %, less than 1.00 %, less than 0.50 %, less than 0.25 %, less than 0.2 %, less than 0.15 %, or less than 0.10 %, by volume.

27. The alcoholic beverage substitute according to any one of claims 1 to 7, being an alcopop-substitute.

28. The alcoholic beverage substitute according to claim 27, wherein said alcopop-substitute is selected from a beer cooler, a wine cooler and a spirit cooler.

29. The alcoholic beverage-substitute according to claim 27 or 28, comprising said compound represented by Formula I in amount that imparts to the beverage the psychotropic effect, palatability and the pleasures of drinking provided by an alcopop beverage containing 4.5-12.5 % alcohol by volume.

30. The alcoholic beverage-substituted beverage according to claim 29, comprising said compound represented by Formula I in an amount within a range selected from 0.25 to 0.60 mg/ml, 0.28 to 0.60 mg/1, 0.30 to 0.60 mg/ml, 0.28 to 0.58 mg/ml, 0.28 to 0.55 mg/ml 0.30 to 0.55 mg/ml, 0.30 to 0.50 mg/ml, 0.30 to 0.48 mg/ml, 0.30 to 0.45 mg/ml, 0.30 to 0.42 mg/ml, 0.30 to 0.40 mg/ml, 0.30 to 0.38 mg/ml or 0.31 to 0.36 mg/ml.

31. The alcoholic beverage-substituted according to claim 24, comprising 0.31 mg/ml to 0.33 mg/ml of said compound.

32. The alcoholic beverage-substitute according to any one of claims 27 to 31, wherein said alcopop-substitute comprises ethanol in an amount that is more than 0.01 % but less than 1.00 %, less than 0.70 %, less than 0.50 %, less than 0.25 %, less than 0.2 %, less than 0.15 %, less than 0.10 %, or less than 0.05 %, by volume.

33. A beer beverage comprising the beer substitute beverage according to any one of claims 9 to 14 and ethanol in an amount that is more than 0.5 % but less than 5.00 %, less than 4.50 %, less than 4.00 %, less than 3.50 %, less than 3.00 %, less than 2.50 %, less than 2.00 %, less than 1.50 %, or less than 1.00 %, by volume.

34. A wine beverage comprising the wine substitute beverage according to any one of claims 15 to 20 and ethanol in an amount that is more than 3.0 % but less than 7.5 %, less than 7.0 %, less than 6.5 %, less than 6.0 %, less than 5.0 %, less than 5.5 %, less than 5.0 %, less than 4.5 %, less than 4.0 %, or less than 3.5 %, by volume.

35. A spirit beverage comprising the spirit substitute beverage according to any one of claims 21 to 26 and ethanol in an amount that is more than 11.0 % but less than 20.0 %, less than 18.0 %, less than 16.0 %, less than 14.0 %, less than 15.0 %, less than 14.0 %, less than 13.5 %, less than 13.0 %, less than 12.5 %, or less than 12.0 %, by volume.

36. An alcopop beverage comprising the alcopop substitute beverage according to any one of claims 27 to 32, and ethanol in an amount that is more than 0.5 % but less than 5.00 %, less than 4.50 %, less than 4.00 %, less than 3.50 %, less than 3.00 %, less than 2.50 %, less than 2.00 %, less than 1.50 %, or less than 1.00 %, by volume.

37. A beverage comprising an alcohol-free base liquid and a compound represented by Formula I as defined herein in an amount that imparts to the beverage the psychotropic effect, palatability and the pleasures of drinking provided by an alcoholic beverage having alcohol in an amount of 2 % to 30 % by volume.

38. The beverage according to claim 37, wherein the amount of said compound represented by Formula I is in the rage selected from 0.20 mg/ml to 2.97 mg/ml, 0.20 mg/ml to 0.70 mg/ml, 0.28 to 0.65 mg/ml, 0.30 to 0.60 mg/ml, 0.30 to 0.55 mg/ml, 0.30 to 0.50 mg/ml, 0.30 to 0.45 mg/ml, 0.30 to 0.40 mg/ml, 0.31 to 0.36 mg/ml, 0.50 to 1.25 mg/ml, 0.55 to 1.20 mg/ml, 0.60 to 1.20 mg/ml, 0.70 to 1.20 mg/ml, 0.70 to 1.10 mg/ml, 0.75 to 1.00 mg/ml, 0.80 to 1.00 mg/ml, 0.80 to 1.05 mg/ml, 0.80 to 0.95 mg/ml, 1.25 to 1.90 mg/ml, 1.25 to 2.00 mg/ml, 1.90 to 2.97 mg/ml, 1.90 mg/ml to 2.60 mg/ml, 1.95 to 2.55 mg/ml, 1.95 to 2.50 mg/ml, 1.95 to 2.40 mg/ml, 1.96 to 2.30 mg/ml, 1.96 to 2.25 mg/ml, 1.96 to 2.20 mg/ml, 1.98 to 2.25 mg/ml, or 1.98 to 2.20 mg/ml.

39. The beverage according to claim 37 or 38, being selected from fruit juice, fruit syrup, concentrate or nectar from fruits, jello, vegetable juice, a plant material such as agave, a carbonated beverage such as cola, a caffeinated beverage, malt beer, tonic water and water.

40. A compound represented by Formula I:


Formula I

as described in any one of claims 1 to 6, for use in the manufacture of an alcoholic beverage substitute, or an alcoholic-like beverage.

41. Use of compound represented by Formula I:


Formula I

as described in any one of claims 1 to 6, for the preparation of an alcoholic beverage-substitute, or an alcoholic-like beverage.

42. The compound according to claim 40, or the use according to claim 41, wherein said alcoholic beverage substitute is selected from the group consisting of a beer-substitute, a wine-substitute, a spirit-substitute and an alcopop substitute.

43. The compound according to claim 40, or the use according to claim 41, wherein:

(i) said beer-substitute is as defined in any one of claims 9 to 14;

(ii) said wine-substitute is as defined in any one of claims 15 to 20;

(iii) said spirit-substitute is as defined in any one of claims 21 to 26;

(iv) said alcopop substitute is as defined in any one of claims 27 to 32; or

(v) said alcoholic-like beverage is as defined in any one of claims 37 to 39.

44. A process for the preparation of an alcoholic beverage substitute, the process comprising mixing a base liquid with a compound represented by Formula I in an amount that accounts for the psychotropic and palatability effects imparted by the alcoholic beverage.

45. The compound according to claim 40, or the use according to claim 41, or the process according to claim 44, wherein the amount of said compound represented by Formula I is in the rage selected from 0.20 mg/ml to 2.97 mg/ml, 0.20 mg/ml to 0.70 mg/ml, 0.28 to 0.65 mg/ml, 0.30 to 0.60 mg/ml, 0.30 to 0.55 mg/ml, 0.30 to 0.50 mg/ml, 0.30 to 0.45 mg/ml, 0.30 to 0.40 mg/ml, 0.31 to 0.36 mg/ml, 0.50 to 1.25 mg/ml, 0.55 to 1.20 mg/ml, 0.60 to 1.20 mg/ml, 0.70 to 1.20 mg/ml, 0.70 to 1.10 mg/ml, 0.75 to 1.00 mg/ml, 0.80 to 1.00 mg/ml, 0.80 to 1.05 mg/ml, 0.80 to 0.95 mg/ml, 1.25 to 1.90 mg/ml, 1.25 to 2.00 mg/ml, 1.90 to 2.97 mg/ml, 1.90 mg/ml to 2.60 mg/ml, 1.95 to 2.55 mg/ml, 1.95 to 2.50 mg/ml, 1.95 to 2.40 mg/ml, 1.96 to 2.30 mg/ml, 1.96 to 2.25 mg/ml, 1.96 to 2.20 mg/ml, 1.98 to 2.25 mg/ml, or 1.98 to 2.20 mg/ml.

46. The process according to claim 44, wherein:

(i) said alcoholic beverage substitute is beer- or cider-substitute, and the amount of said compound represented by Formula I is as defined in claim 12;

(ii) said alcoholic beverage substitute is a wine-substitute, and the amount of said compound represented by Formula I is as defined in claim 18;

(iii) said alcoholic beverage substitute is a spirit-substitute, and the amount of said compound represented by Formula I is as defined in claim 24; or

(iv) said alcoholic beverage substitute is an alcopop-substitute, and the amount of said compound represented by Formula I is as defined in claim 30.

47. The process according to claim 44, wherein said base liquid is a beverage as defined in claim 7.

48. The process according to any one of claims 44 to 47, further comprising adding to the base liquid at least one of a flavoring agent, a colorant, an odoriferous agent, C02, a viscosity modifying agent, a foaming agent, an antifoaming agent and a preservative.