Sweet flavor modifier

Patent metadata

Field	Value
Publication number	US-9745293-B2
Application number	US-201715460103-A
Country	US
Kind code	B2
Filing date	Mar 15, 2017
Priority date	Aug 6, 2012
Publication date	Aug 29, 2017
Grant date	Aug 29, 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 modulating the sweet taste of compositions.

First claim

What is claims is:

1. A compound having structural Formula (Ia):

or a salt or solvate thereof;
wherein
m is 4, and n is 0; or m is 3, and n is 1; or m and n are both 2;
q is 0, 1, or 2;
X is a covalent bond;
Y is alkyl, substituted alkyl, carbocyclyl, substituted carbocyclyl, heterocyclyl, substituted heterocyclyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, aralkyl, substituted aralkyl, heteroarylalkyl, or substituted heteroarylalkyl; and
each R 2 is independently selected from the group consisting of alkyl, halo, hydroxyl, alkoxy, and haloalkyl,
wherein the substituents of a moiety indicated as substituted are selected from the group consisting of —R a , halo, ═O, —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).

2. The compound of claim 1 , which is represented by structural Formula (Ib):

or a salt or solvate thereof.

3. The compound of claim 1 , which is represented by structural Formula (Id):

or a salt or solvate thereof.

4. The compound of claim 1 , which is selected from the group consisting of

or a salt or solvate thereof.

5. The compound of claim 1 , which is

or a salt or solvate thereof.

6. The compound of claim 1 , which is selected from the group consisting of

or a salt or solvate thereof.

7. The compound of claim 1 , which is selected from the group consisting of

or a salt or solvate thereof.

8. The compound of claim 1 , wherein Y is alkyl, carbocyclyl, heterocyclyl, aryl, heteroaryl, aralkyl, or heteroarylalkyl.

9. The compound of claim 1 , wherein the substituents of a moiety indicated as substituted are selected from the group consisting of —R a , halo, —OR b , —SR b , trihalomethyl, —CF 3 , —CN, —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 , —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 , and —NR b C(NR b )R b , 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 .

10. The compound of claim 1 , wherein the substituents of a moiety indicated as substituted are selected from the group consisting of —R a , halo, trihalomethyl, —CF 3 , —CN, where R a is selected from the group consisting of alkyl, cycloalkyl, cycloheteroalkyl, aryl, arylalkyl, heteroaryl and heteroarylalkyl.

11. A compound having structural Formula (Ia):

or a salt or solvate thereof;
wherein
m is 4, and n is 0; or m is 3, and n is 1; or m and n are both 2;
q is 0, 1, or 2;
X is a covalent bond or —NR 1 —;
R 1 is hydrogen or C1 to C6 alkyl;
Y is carbocyclyl, substituted carbocyclyl, heterocyclyl, substituted heterocyclyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, aralkyl, substituted aralkyl, heteroarylalkyl, or substituted heteroarylalkyl; and
each R 2 is independently selected from the group consisting of alkyl, halo, hydroxyl, alkoxy, and haloalkyl,
wherein the substituents of a moiety indicated as substituted are selected from the group consisting of —R a , halo, ═O, —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).

12. The compound of claim 11 , wherein Y is carbocyclyl, heterocyclyl, aryl, heteroaryl, aralkyl, or heteroarylalkyl.

13. The compound of claim 11 , wherein X is a covalent bond.

14. The compound of claim 11 , wherein the compound is represented by structural Formula (Ib):

or a salt or solvate thereof.

15. The compound of claim 11 , wherein the compound is represented by structural Formula (Ic):

or a salt or solvate thereof.

16. The compound of claim 11 , wherein the compound is represented by structural Formula (Id):

Assignees

• Senomyx Inc

Inventors

• Tachdjian Catherine
• Karanewsky Donald
• Werner Sara
• Darmohusodo Vincent
• Yamamoto Jeff

Classifications

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• A61P1/02

  Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis · CPC title

• C07D417/12 Primary

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

• A23L2/60

  Sweeteners · CPC title

• A23L29/35

  Degradation products of starch, e.g. hydrolysates, dextrins; Enzymatically modified starches · CPC title