Sweet flavor modifier

Patent metadata

Field	Value
Publication number	US-9695162-B2
Application number	US-201615290691-A
Country	US
Kind code	B2
Filing date	Oct 11, 2016
Priority date	Feb 19, 2013
Publication date	Jul 4, 2017
Grant date	Jul 4, 2017

Abstract

The present invention includes compounds having structural formula (Ia):

or salts or solvates thereof. These compounds are useful as sweet flavor modifiers. The present invention also includes compositions comprising the present compounds and methods of enhancing the sweet taste of compositions.

First claim

We claim:

1. An ingestible composition comprising
a compound represented by structural Formula (Ia):

or a salt or solvate thereof; wherein,
R 1 and R 2 are independently C1 to C2 alkyl; or alternatively, R 1 and R 2 , together with the carbon atom to which they are attached, form a C3 to C6 cycloalkyl;
n is 0, 1, or 2; and
R 3 is halo, cyano, hydroxyl, amine, substituted amine, alkoxy, substituted alkoxy, aryloxy, substituted aryloxy, acyl, sulfonamide, ester, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, substituted heteroarylalkyl, carbocyclyl, substituted carbocyclyl, heterocyclyl, or substituted heterocyclyl,
wherein the substituents of a moiety indicated as substituted are selected from the group consisting of —R a , halo, —OR b , —SR b , —NR c R c , trihalomethyl, —CF 3 , —CN, —OCN, —SCN, —NO, —NO 2 , —N 3 , —S(O) 2 R b , —S(O) 2 OR b , —OS(O) 2 R b , —OS(O) 2 OR b , —P(O)(OR b )(OR b ), —C(O)R b , —C(S)R b , —C(NR b )R b , —C(O)OR b , —C(S)OR b , —C(O)NR c R c , —C(NR b )NR c R c , —OC(O)R b , —OC(S)R b , —OC(O)OR b , —OC(S)OR b , —NR b C(O)R b , —NR b C(S)R b , —NR b C(O)OR b , —NR b C(S)OR b , —NR b C(O)NR c R c , —NR b C(NR b )R b and —NR b C(NR b )NR c R c , where R a is selected from the group consisting of alkyl, cycloalkyl, cycloheteroalkyl, aryl, arylalkyl, heteroaryl and heteroarylalkyl; each R b is independently hydrogen or R a ; and each R c is independently R b or alternatively, the two R c s may be taken together with the nitrogen atom to which they are bonded form a 4-, 5-, 6- or 7-membered cycloheteroalkyl which may optionally include from 1 to 4 of the same or different additional heteroatoms selected from the group consisting of O (oxygen), N (nitrogen) and S (sulfur); and
an ingestibly acceptable excipient.

2. The ingestible composition of claim 1 , wherein R 1 and R 2 are both methyl, or ethyl.

3. The ingestible composition of claim 1 , wherein R 1 and R 2 , together with the carbon atom to which they are attached, form cyclopropyl, cyclobutyl, or cyclohexyl.

4. The ingestible composition of claim 1 , wherein the compound is represented by structural Formula (Ib):

or a salt or solvate thereof; wherein,
R 1 and R 2 are both methyl, or ethyl; or alternatively, R 1 and R 2 , together with the carbon atom to which they are attached, form cyclopropyl, cyclobutyl, or cyclohexyl.

5. The ingestible composition of claim 1 , wherein when a group is indicated as substituted the substituent is one or more selected from the group consisting of —R a , halo, —OR b , —NR c R c , —CN, —S(O) 2 R b , and —C(O)NR c R c , where R a is selected from the group consisting of alkyl, cycloalkyl, cycloheteroalkyl, aryl, arylalkyl, heteroaryl and heteroarylalkyl; each R b is independently hydrogen or R a ; and each R c is independently R b or alternatively, the two R c s may be taken together with the nitrogen atom to which they are bonded form a 4-, 5-, 6- or 7-membered cycloheteroalkyl which may optionally include from 1 to 4 of the same or different additional heteroatoms selected from the group consisting of O (oxygen), N (nitrogen) and S (sulfur).

6. The ingestible composition of claim 1 , further comprising one or more sweeteners.

7. The ingestible composition of claim 6 , wherein the sweetener is selected from the group consisting of sucrose, fructose, glucose, galactose, mannose, lactose, tagatose, maltose, high fructose corn syrup, D-tryptophan, glycine, erythritol, isomalt, lactitol, mannitol, sorbitol, xylitol, maltodextrin, maltitol, isomalt, hydrogenated glucose syrup (HGS), hydrogenated starch hydrolyzate (HSH), stevioside, rebaudioside A, other sweet Stevia-based glycosides, carrelame, other guanidine-based sweeteners, saccharin, acesulfame-K, cyclamate, sucralose, alitame, mogroside, neotame, aspartame, other aspartame derivatives, and combinations thereof.

8. The ingestible composition of claim 1 , which is in form of a food or beverage product, a pharmaceutical composition, a nutritional product, a dietary supplement, over-the-counter medication, or oral care product.

9. The ingestible composition of claim 8 , wherein the food or beverage product is for human or animal consumption.

10. The ingestible composition of claim 8 , wherein the food or beverage product is selected from the group consisting of the Soup category; the Dried Processed Food category; the Beverage category; the Ready Meal category; the Canned or Preserved Food category; the Frozen Processed Food category; the Chilled Processed Food category; the Snack Food category; the Baked Goods category; the Confectionary category; the Dairy Product category; the Ice Cream category; the Meal Replacement category; the Pasta and Noodle category; the Sauces, Dressings, Condiments category; the Baby Food category; the Spreads category; sweet coatings, frostings, or glazes; and combinations thereof.

11. An ingestible composition comprising a compound selected from the group consisting of

or a salt or solvate thereof; and
an ingestibly acceptable excipient.

12. The ingestible composition of claim 11 , wherein the compound is selected from the group consisting of

or a salt or solvate thereof.

13. The ingestibl

Assignees

• Senomyx Inc

Inventors

• Adamski-Werner Sara
• Darmohusodo Vincent
• Tachdjian Catherine
• Karanewsky Donald
• Petrovic Goran
• Kimmich Rachel
• Fotsing Joseph R

Classifications

• A61P27/00

  Drugs for disorders of the senses · CPC title

• C07D417/12 Primary

  linked by a chain containing hetero atoms as chain links · CPC title

• A23L27/2056

  having at least two different hetero atoms, at least one being a nitrogen atom · CPC title

• C07D471/04

  Ortho-condensed systems · CPC title

• A23L33/15

  Vitamins · CPC title