IP Library Granted Patent US 8,877,922
Granted Patent B2
US 8,877,922 · App. 14/096,531 · Granted Nov 4, 2014

Sweet flavor modifier

Inventors: Catherine Tachdjian (San Diego, CA); Donald Karanewsky (Escondido, CA); Sara Werner (San Diego, CA); Vincent Darmohusodo (Encinitas, CA); Jeff Yamamoto (San Diego, CA)
Assignee: Senomyx, Inc.
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Quick Facts
Patent No.
US 8,877,922
App. No.
14/096,531
Granted
Nov 4, 2014
Kind
B2
Abstract

The present invention includes compounds having structural formula (I): 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.

Claims (42)

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, 2, or 3;

X is a covalent bond or —NR 1 —;

R 1 is hydrogen or C1 to C6 alkyl;

Y is alkyl, substituted alkyl, heteroalkyl, substituted heteroalkyl, 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, heteroalkyl, halo, hydroxyl, alkoxy, amino, alkylamino, cyano, nitro, haloalkyl, carboxylic acid, amide, ester, acyl, thiol, alkylthio, and sulfonamide,

wherein the substituents are selected from the group consisting of —R a , halo, —O, ═O, —OR b , —SR b , —S − , ═S, —NR c R c , ═NR b , ═N—OR b , —CF 3 , —CN, —OCN, —SCN, —S(O) 2 R b , —S(O) 2 NR b , —S(O) 2 O − , —S(O) 2 OR b , —OS(O) 2 R b , —OS(O) 2 O − , —OS(O) 2 OR b , —C(O)R b , —C(S)R b , —C(NR b )R b , —C(O)O − , —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)O − , —OC(O)OR b , —OC(S)OR b , —NR b C(O)R b , —NR b C(S)R b , —NR b C(O)O − , —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, heteroalkyl, cycloheteroalkyl, aryl, arylalkyl, heteroaryl and heteroarylalkyl; each R b is independently hydrogen or R a ; and each R e 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, N and S.

2. The compound of claim 1 , wherein X is NH.

3. The compound of claim 1 , wherein X is a covalent bond.

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

wherein,

Y is alkyl, substituted alkyl, heteroalkyl, substituted heteroalkyl, carbocyclyl, substituted carbocyclyl, heterocyclyl, substituted heterocyclyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, aralkyl, substituted aralkyl, heteroarylalkyl, or substituted heteroarylalkyl.

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

wherein,

Y is alkyl, substituted alkyl, heteroalkyl, substituted heteroalkyl, carbocyclyl, substituted carbocyclyl, heterocyclyl, substituted heterocyclyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, aralkyl, substituted aralkyl, heteroarylalkyl, or substituted heteroarylalkyl.

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

wherein,

Y is alkyl, substituted alkyl, heteroalkyl, substituted heteroalkyl, carbocyclyl, substituted carbocyclyl, heterocyclyl, substituted heterocyclyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, aralkyl, substituted aralkyl, heteroarylalkyl, or substituted heteroarylalkyl.

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

wherein,

Y is alkyl, substituted alkyl, heteroalkyl, substituted heteroalkyl, carbocyclyl, substituted carbocyclyl, heterocyclyl, substituted heterocyclyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, aralkyl, substituted aralkyl, heteroarylalkyl, or substituted heteroarylalkyl.

8. The compound of claim 4 , wherein Y is —(C1 to C3 alkylene)-aryl or —(C1 to C3 alkylene)-substituted aryl.

9. The compound of claim 4 , wherein Y is —(C1 to C3 alkylene)-heteroaryl or —(C1 to C3 alkylene)-substituted heteroaryl.

10. The compound of claim 5 , wherein Y is C1 to C12 alkyl, substituted C1 to C12 alkyl, five or six-membered heteroaryl, substituted five or six-membered heteroaryl, —(C1 to C3 alkylene)-(five or six-membered heteroaryl), or —(C1 to C3 alkylene)-(substituted five or six-membered heteroaryl).

11. The compound of claim 4 , wherein Y is C1 to C12 alkyl, substituted C1 to C12 alkyl, C1 to C12 heteroalkyl, or substituted C1 to C12 heteroalkyl.

12. The compound of claim 4 , wherein Y is three to seven-membered cycloalkyl, substituted three to seven-membered cycloalkyl, five to seven-membered heterocyclyl, or substituted five to seven-membered heterocyclyl.

13. The compound of claim 4 , wherein Y is phenyl or substituted phenyl.

14. The compound of claim 4 , wherein Y is an optionally substituted five or six-membered monocyclic heteroaryl, or an optionally substituted ten to twelve-membered bicyclic heteroaryl.

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

16. The compound of claim 7 , wherein Y is C1 to C12 alkyl, substituted C1 to C12 alkyl, five or six-membered heteroaryl, substituted five or six-membered heteroaryl, —(C1 to C3 alkylene)-(five or six-membered heteroaryl), or —(C1 to C3 alkylene)-(substituted five or six-membered heteroaryl).

17. The compound of claim 6 , wherein Y is C1 to C12 alkyl, substituted C1 to C12 alkyl, C1 to C12 heteroalkyl, or substituted C1 to C12 heteroalkyl.

18. The compound of claim 6 , wherein Y is three to seven-membered cycloalkyl, substituted three to seven-membered cycloalkyl, five to seven-membered heterocyclyl, or substituted five to seven-membered heterocyclyl.

19. The compound of claim 6 , wherein Y is phenyl or substituted phenyl.

20. The compound of claim 6 , wherein Y is an optionally substituted five or six-membered monocyclic heteroaryl, or an optionally substituted ten to twelve-membered bicyclic heteroaryl.

21. The compound of claim 6 , wherein Y is —(C1 to C3 alkylene)-aryl or —(C1 to C3 alkylene)-substituted aryl.

22. The compound of claim 6 , wherein Y is —(C1 to C3 alkylene)-heteroaryl or —(C1 to C3 alkylene)-substituted heteroaryl.

23. The compound of claim 1 , wherein the substituents are selected from the group consisting of —R a , halo, ═O, —OR b , —NR cR c , —NH 2 , —NH-alkyl, N-pyrrolidinyl, N-morpholinyl, —CF 3 , —CN, —OCN, —C(O)R b , —C(NR b )R b , —C(O)O − , —C(O)OR b , —C(O)NR c R c , —C(NR b )NR c R c , —OC(O)R b , —OC( O)O − , —OC(O)OR b , —NR b C(O)R b , —NR b C(O)O — , —NR b C(O)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, heteroalkyl, cycloheteroalkyl, aryl, arylalkyl, heteroaryl and heteroarylalkyl; each R b is independently hydrogen or Ra; and each R c is independently R b or alternatively, the two Res 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, N and S.

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

or a salt or solvate thereof.

Assignments (2)
CORRECTIVE ASSIGNMENT TO REMOVE THE APPLICATION NUMBER; 6179502 AND PCT NUMBER: US13053666 PREVIOUSLY RECORDED AT REEL: 033434 FRAME: 0347. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Oct 24, 2014
From: TACHDJIAN, CATHERINE; KARANEWSKY, DONALD S.; WERNER, SARA; YAMAMOTO, JEFF; DARMOHUSODO, VINCENT
To: SENOMYX, INC
Reel/Frame 034196/0708 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 31, 2014
From: TACHDJIAN, CATHERINE; KARANEWSKY, DONALD S; WERNER, SARA; YAMAMOTO, JEFF; DARMOHUSODO, VINCENT
To: SENOMYX, INC
Reel/Frame 033434/0347 →
Continuity (4)
Continuation PCTUS2013053666 · Aug 5, 2013
Provisional Application 61779502 · Mar 13, 2013
Provisional Application 61679912 · Aug 6, 2012
Related Publication 20140094453A1 · Apr 3, 2014