Isosorbide derivatives and their use as flavor modifiers, tastants, and taste enhancers

• US 8,420,145 B2
• Filed: 03/03/2009
• Issued: 04/16/2013
• Est. Priority Date: 03/03/2008
• Status: Active Grant

• Current Assignee: Senomyx Inc (DSM-Firmenich AG)
• Original Assignee: Senomyx Inc (DSM-Firmenich AG)
• Inventors: Tachdjian, Catherine, Karanewsky, Donald S., Adamski-Werner, Sara L., Yamamoto, Jeffrey M., Servant, Guy
• Primary Examiner(s): SHTERENGARTS, SAMANTHA L
• Application Number:
  US12/396,917
• Publication Number:
  US 20090220662A1
• Time in Patent Office: 1,505 Days
• Field of Search: 426/536, 546/268.4, 548/200, 548/248, 548/256, 548/526, 549/60, 549/464
• US Class Current: 426/536
• CPC Class Codes: A23L 2/60 Sweeteners
• CPC Class Codes: A23L 27/205 Heterocyclic compounds
• CPC Class Codes: A23L 27/2052 having oxygen or sulfur as the only hetero atoms
• CPC Class Codes: C07D 493/04 Ortho-condensed systems

Abstract

The present invention provides isosorbide derivatives having the formula shown below and certain subgenera or species thereof, as flavor or taste modifiers, particularly, savory (“umami”) taste modifiers, savory flavoring agents and savory flavor enhancers in foods, beverages, and other comestible compositions,

Claims

1. A compound having structural formula (I)

2. The compound of claim 1, wherein Y is alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, carbocyclyl, or substituted carbocyclyl.

3. The compound of claim 1, wherein:

A is monocyclic five-membered heteroaryl selected from the group consisting of pyrrolyl, furanyl, thiofuranyl, oxazoloyl, isoxazolyl, thiazolyl, and triazole;

Y is alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkylnyl, heteroalkyl, substituted heteroalkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, arylalkenyl, substituted arylalkenyl,heterocyclyl, substituted heterocyclyl, carbocyclyl, substituted carbocyclyl, heteroarylalkyl, or substituted heteroarylalkyl;

X is —

O—

, —

S—

, —

S(O)—

, —

S(O)₂—

, —

C(R³R⁴)—

, —

C(O)—

, —

C(S)—

, —

C(═

NR³)—

, —

C(O)O—

, —

N(R³)—

, —

OC(O)—

, —

N(R³)C(O)—

, —

C(O)N(R³)—

, —

C(═

N—

OR³)—

, —

C(═

NR³)—

NR⁴—

, —

N(R³)C(═

NR⁴)—

, —

N(R³)C(S)—

, —

C(S)—

N(R³)—

, —

N(R³)S(O)₂—

, —

S(O)₂—

N(R³)—

, —

N(R³)C(═

NR⁴)O—

, —

C(═

NR⁴)O—

N(R³)—

, —

N(R³)—

C(═

NR⁴)—

N(⁵)—

, —

N(R³)N(R⁴)C(O)O—

, —

N(R³)C(O)O—

, —

N(R³)C(O)N(R⁴)—

, —

NR³—

C(O)—

C(O)—

NR⁴—

, —

C(O)—

C(O)—

NR⁴—

, —

P(O)(OR³)—

, or —

P(O)(R³)—

;

Z is alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkylnyl, heteroalkyl, substituted heteroalkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, arylalkenyl, substituted arylalkenyl, heteroaryl, substituted heteroaryl, heterocyclyl, substituted heterocyclyl, carbocyclyl, substituted carbocyclyl, heteroarylalkyl, or substituted heteroarylalkyl; and

R³, R⁴, and R⁵ are each independently hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkylnyl, heteroalkyl, substituted heteroalkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, arylalkenyl, substituted arylalkenyl, heteroaryl, substituted heteroaryl, heterocyclyl, substituted heterocyclyl, heteroarylalkyl, substituted heteroarylalkyl, carbocyclyl, or substituted carbocyclyl.

6. A composition comprising a compound having structural formula (I) of claim 1,

or the salt, solvate, ester, or N-oxide thereof;

and a carrier.

7. The composition of claim 6, which comprises an ingestible composition.

8. A method for modulating the savory taste of a composition comprising combining the composition with at least one compound of formula (I) according to claim 1.

9. A food or beverage product comprising a compound of formula (I) according to claim 1.

4. A compound having structural formula (Ia):

5. A compound having a structural formula selected from the group consisting of

10. A compound of the following structural formula (I):

11. The compound of claim 10, wherein Z is carbocyclyl or substituted carbocyclyl.

12. A ingestible composition comprising a compound of formula (I) of claim 10, or the salt, solvate, ester, or N-oxide thereof.

13. The ingestible composition of claim 12, which is a food or beverage.

14. A method for modulating the savory taste of a composition comprising combining the composition with at least one compound of formula (I) according to claim 10.