IP Library Patent Application 14731224
Patent Application
App. No. 14/731,224

SWEET FLAVOR MODIFIER

Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US None
App. No.
14/731,224
Abstract

The present invention includes compounds having structural formula (I), or pharmaceutically acceptable salts, solvate, and/or ester 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 ingestible compositions. Furthermore, the present invention provides methods for preparing the compounds.

Claims (54)

1 . A compound having a structural Formula (II) or (II′),

or a tautomer, salt, and/or solvate thereof, wherein:

A is —OR 1 , —NR 1 C(O)R 2 , —NHOR 1 , —NR 1 R 2 , —NR 1 CO 2 R 2 , —NR 1 C(O)NR 2 R 3 , —NR 1 C(S)NR 2 R 3 or —NR 1 C(═NH)NR 2 R 3 ;

B is hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, acyl, substituted acyl, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, substituted heteroarylalkyl, —CN, —OR 4 , —S(O) a R 4 , —NR 4 R 5 , —C(O)NR 4 R 5 , —CO 2 R 4 , —NR 4 CO 2 R 5 , —NR 4 C(O)NR 5 R 6 , —NR 4 C(S)NR 5 R 6 , —NR 4 C(═NH)NR 5 R 6 , —SO 2 NR 4 R 5 , —NR 4 SO 2 R 5 , —NR 4 SO 2 NR 5 R 6 , —B(OR 4 )(OR 5 ), —P(O)(OR 4 )(OR 5 ), or —P(O)(R 4 )(OR 5 );

C is —OR 7 , —S(O) b R 7 , SO 3 R 7 , —C(O)NR 7 R 8 , —CO 2 R 7 , —NR 7 CO 2 R 8 , —NR 7 C(O)NR 8 R 9 , —NR 7 C(═NH)NR 8 R 9 , —SO 2 NR 7 R 8 , —NR 7 SO 2 R 8 , —NR 7 SO 2 NR 8 R 9 , —B(OR 7 )(OR 8 ), —P(O)(OR 7 )(OR 8 ), —P(O)(R 7 )(OR 8 ), or heteroaryl;

Y forms a single bond with either W or Z and a double bond with the other of W or Z;

W is —C(R 10 )—, —S—, —N—, —N(R 11 )—, or —O—;

Y is —C(R 12 )— or —N—;

Z is —C(R 13 )—, —S—, —N—, —N(R 14 )—, or —O—;

R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are independently hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, acyl, substituted acyl, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl or substituted heteroarylalkyl; or alternatively, R 1 and R 2 , R 2 and R 3 , R 4 and R 5 , R 5 and R 6 , R 7 and R 8 , or R 8 and R 9 , together with the atoms to which they are bonded, form a cycloheteroalkyl or substituted cycloheteroalkyl ring.

R 10 is hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, acyl, substituted acyl, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, substituted heteroarylalkyl, halo, —CN, —OR 15 , —S(O) c R 15 , —NR 15 R 16 , —C(O)NR 15 R 16 , —CO 2 R 15 , —SO 2 NR 15 R 16 , —NR 15 SO 2 R 16 , —P(O)(OR 15 )(OR 16 ) or —P(O)(R 15 )(OR 16 );

R 12 is hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, acyl, substituted acyl, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, substituted heteroarylalkyl, halo, —CN, —OR 17 , —S(O) d R 17 , —OC(O)R 17 , —NR 17 R 18 , —C(O)NR 17 R 18 , —CO 2 R 17 , —SO 2 NR 17 R 18 , —NR 17 SO 2 R 18 , —P(O)(OR 17 )(OR 18 ) or —P(O)(R 17 )(OR 18 );

R 13 is hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, acyl, substituted acyl, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, substituted heteroarylalkyl, halo, —CN, —OR 19 , —S(O) e R 19 , —OC(O)R 19 , —NR 19 R 20 , —C(O)NR 19 R 20 , C(O)R 19 , —CO 2 R 19 , —SO 2 NR 19 R 20 , —NR 19 SO 2 R 20 , —P(O)(OR 19 )(OR 20 ) or —P(O)(R 19 )(OR 20 ); or alternatively R 10 and R 12 , or R 12 and R 13 , together with the atoms to which they are attached, form a cycloalkyl, substituted cycloalkyl, cycloheteroalkyl or substituted cycloheteroalkyl ring;

a, b, c, d and e are independently 0, 1, or 2;

R 11 and R 14 are independently hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, acyl, substituted acyl, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl or substituted heteroarylalkyl; and

R 15 , R 16 , R 17 , R 18 , R 19 , and R 20 are independently hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, acyl, substituted acyl, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl or substituted heteroarylalkyl; or alternatively R 15 and R 16 , R 17 and R 18 , or R 19 and R 20 , together with the atoms to which they are attached, form a cycloheteroalkyl or substituted cycloheteroalkyl ring; and

with the following provisos:

(a) when W is —O— or —S— or —NR 11 —, then Z is —C(R 13 )— or —N—;

(b) when Z is —O— or —S— or —NR 14 —, then W is —C(R 10 )— or —N—; and

(c) when W is —C(R 10 )— or —N—, then Z cannot be —C(R 13 )— or —N—.

2 . The compound of claim 1 having a structural Formula (IIa) or (IIa′),

or a tautomer, salt, and/or solvate, wherein,

W is —C(R 10 )—, or —N—;

Y is —C(R 12 )— or —N—; and

Z is —S—, —N(R 14 )—, or —O—.

3 . The compound of claim 1 having a structural Formula (IIb) or (IIb′),

or a tautomer, salt, and/or solvate, wherein,

W is —S—, —N(R 11 )—, or —O—;

Y is —C(R 12 )— or —N—; and

Z is —C(R 13 )—, or —N—.

4 . The compound of claim 3 having the structure

or a tautomer, salt and/or solvate thereof.

5 . An ingestible composition comprising

a compound of claim 1 ; and

an ingestibly acceptable excipient.

6 . The ingestible composition of claim 5 , 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, corn syrup (including high fructose corm 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 5 , which has an increased sweet taste as compared to the ingestible composition not containing the compound of claim 1 , as judged by a majority of a panel of at least eight human taste testers.

9 . The ingestible composition of claim 5 , 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.

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

11 . The ingestible composition of claim 5 , 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.

12 . A method of enhancing the sweet taste of an ingestible composition comprising contacting the ingestible composition thereof with a compound of claim 1 to form a modified ingestible composition.

13 . A sweet enhancing composition, comprising a compound of claim 1 in an amount effective to provide sweetening in combination with a first amount of sweetener, wherein the sweetening is more than the sweetening provided by the first amount of sweetener without the compound.

14 . An ingestible composition comprising the sweet enhancing composition of claim 13 .

15 . The ingestible composition of claim 14 , 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.

16 . A flavoring concentrate formulation comprising

i) as flavor modifying ingredient, a compound of claim 1 ;

ii) a carrier; and

iii) optionally at least one adjuvant.

17 . The flavoring concentrate formulation of claim 16 , wherein the at least one adjuvant comprises one or more flavoring agents.

18 . The flavoring concentrate formulation of claim 16 , wherein the at least one adjuvant comprises one or more sweeteners.

19 . The flavoring concentrate formulation of claim 16 , wherein the at least one adjuvant comprises one or more ingredients selected from the group consisting of a emulsifier, a stabilizer, an antimicrobial preservative, an antioxidant, vitamins, minerals, fats, starches, protein concentrates and isolates, salts, a freezing point depressant, nucleating agent, and combinations thereof.

20 . The flavoring concentrate formulation of claim 16 , which is in a form selected from the group consisting of liquid, solid, semi-solid, foamy material, paste, gel, cream, lotion, and combinations thereof.

21 . The flavoring concentrate formulation of claim 16 , wherein the compound of claim 1 is in a concentration that is at least 2 times of the concentration in a ready-to-use composition.

Assignments (1)
MERGER Recorded Nov 6, 2020
From: SENOMYX, INC.
To: FIRMENICH INCORPORATED
Reel/Frame 054305/0053 →