Sweet flavor modifier

Patent metadata

Field	Value
Publication number	US-9475803-B2
Application number	US-201414768167-A
Country	US
Kind code	B2
Filing date	Feb 19, 2014
Priority date	Feb 19, 2013
Publication date	Oct 25, 2016
Grant date	Oct 25, 2016

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. 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, ═O, —OR b , —SR b , ═S, —NR c R c , ═NR b , ═N—OR b , trihalomethyl, —CF 3 , —CN, —OCN, —SCN, —NO, —NO 2 , ═N 2 , —N 3 , —S(O) 2 R b , —S(O) 2 NR 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).

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

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

4. The compound of claim 1 , which 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;
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.

5. A compound selected from the group consisting of

or a salt or solvate thereof.

6. The compound 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, ═O, —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).

7. The compound of claim 5 , which is selected from the group consisting of

or a salt or solvate thereof.

8. The compound of claim 5 , which is selected from the group consisting of

or a salt or solvate thereof.

9. The compound of claim 5 , which is selected from the group consisting of

or a salt or solvate thereof.

10. The compound of claim 5 , which is selected from the group consisting of

or a salt or solvate thereof.

11. The compound of claim 5 , which is selected from the group consisting of

or a salt or solvate thereof.

12. The compound of claim 5 , which is selected from the group consisting of

Assignees

• Senomyx Inc

Inventors

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

Classifications

• A61P27/00

  Drugs for disorders of the senses · CPC title

• A23L27/2056

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

• C07D417/12 Primary

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

• A23L33/15

  Vitamins · CPC title

• C07D498/04

  Ortho-condensed systems · CPC title