Compounds, compositions, and methods for reducing or eliminating bitter taste

Patent metadata

Field	Value
Publication number	US-9408407-B2
Application number	US-201414480853-A
Country	US
Kind code	B2
Filing date	Sep 9, 2014
Priority date	Apr 15, 2010
Publication date	Aug 9, 2016
Grant date	Aug 9, 2016

Abstract

The present invention provides edible compositions comprising a compound of the present invention, food products comprising such edible compositions and methods of preparing such food products. The present invention also provides methods of reducing the amount of NaCl in a food product, methods of reducing the sodium intake in a diet, and methods of reducing bitter taste in a food product.

First claim

We claim:

1. A composition comprising: i) a bitter tastant selected from the group consisting of KCl and potassium lactate; and ii) a compound according to a formula selected from the group consisting of:
(a) Formula (V):

or a comestibly or biologically acceptable salt or derivative thereof, or an enantiomer or diastereomer thereof,
wherein, as valence and stability permit:
R 1 , independently for each occurrence, is selected from the group consisting of halo, hydroxyl, C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, and C 1-6 alkoxy;
R 2 is selected from the group consisting of hydrogen, halo, hydroxyl, C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 alkoxy, C 1-6 acyloxy optionally substituted by hydroxyl, amino, mono- or disubstituted C 1-6 alkyl amino, or carboxyl;
R 3 is selected from the group consisting of hydrogen, hydroxyl, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, and C 1-6 alkoxy;
R 4 is selected from the group consisting of hydrogen, hydroxyl, C 1-21 alkyl, C 2-21 alkenyl, C 2-21 alkynyl, and C 1-6 alkoxy, wherein R 4 is optionally substituted by one or more occurrences of hydroxyl or acetyloxy;
R 5 is selected from the group consisting of hydrogen, hydroxyl, C 1-21 alkyl, C 2-21 alkenyl, C 2-21 alkynyl, and C 1-6 alkoxy, wherein R 5 is optionally substituted by one or more occurrences of hydroxyl or acetyloxy;
or R 4 and R 5 together form ═O;
wherein any of R 1 , R 2 , R 3 , R 4 , and R 5 , independently and independently for each occurrence, is optionally substituted with 1-3 substituents selected from the group consisting of C 1-10 alkyl, C 1-10 haloalkyl, halo, hydroxyl, carboxyl, C 1-10 alkoxycarbonyl, C 2-10 alkenyloxycarbonyl, C 2-10 alkynyloxycarbonyl, C 1-10 acyl, C 1-10 acylamino, C 1-10 acyloxy, C 1-10 carbonate, C 1-10 alkoxy, phenyloxy, phosphoryl, phosphate, phosphonate, phosphinate, amino, diC 1-10 alkylamino, monoC 1-10 alkylamino, C 1-13 amido, C 1-10 imino, C 1-10 carbamate, C 1-10 urea, cyano, nitro, azido, sulfhydryl, C 1-10 alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, C 3-7 carbocyclyl, C 3-7 carbocyclyl-C 1-6 alkyl, C 1-6 heterocyclyl, C 1-6 heterocyclyl-C 1-6 alkyl, phenyl, phenyl-C 1-6 alkyl, C 1-5 heteroaryl, and C 1-5 heteroaryl-C 1-6 alkyl; and wherein heterocyclic or heteroaromatic rings, independently for each occurrence, comprise 1-4 heteroatoms selected from N, O, and S; and
n is 0-3;
(b) Formula (XI):

or a comestibly or biologically acceptable salt or derivative thereof, or an enantiomer or diastereomer thereof,
wherein, as valence and stability permit:
the bond with a dotted line optionally represents a single or double bond,
R 1 , R 2 , R 3 , R 6 , and R 7 are independently selected from the group consisting of hydrogen, C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl;
wherein each of R 1 , R 2 , R 3 , R 6 , and R 7 may be optionally independently substituted with one or more substituents selected from the group consisting of halo, —OH, ═O, —SH, ═S, —NH 2 , —CO 2 H, —O(C 1-10 alkyl), —O(C 2-10 alkenyl), —O(C 2-10 alkynyl), —S(C 1-10 alkyl), —S(C 2-10 alkenyl), —S(C 2-10 alkynyl), —NH(C 1-10 alkyl), —NH(C 2-10 alkenyl), —NH(C 2-10 alkynyl), —N(C 1-10 alkyl) 2 , —N(C 2-10 alkenyl) 2 , and —N(C 2-10 alkynyl) 2 ;

R 4 is absent or selected from the group consisting of hydrogen, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 acyl, C 1-6 acyloxy, C 1-6 alkylester, C 1-6 alkenylester, and C 1-6 alkynylester;
wherein R 4 may be optionally substituted with one or more substituents selected from the group consisting of halo, —OH, ═O, —SH, ═S, —NH 2 , —CO 2 H, —O(C 1-10 alkyl), —O(C 2-10 alkenyl), —O(C 2-10 alkynyl), —S(C 1-10 alkyl), —S(C 2-10 alkenyl), —S(C 2-10 alkynyl), —NH(C 1-10 aklyl), —NH(C 2-10 alkenyl), —NH(C 2-10 alkynyl), —N(C 1-10 alkyl) 2 , —N(C 2-10 alkenyl) 2 , —N(C 2-10 alkynyl) 2 , C 1-10 acyl, C 1-10 acyloxy, C 1-10 acylamino, C 1-10 acylthioxy, C 1-10 alkylester, C 1-10 alkenylester, C 1-10 alkynylester, C 1-10 alkylamide, C 1-10 alkenylamide, C 1-10 alkynylamide, C 1-10 alkylthioester, C 1-10 alkenylthioester, and C 1-10 alkynylthioester;

R 5 is absent or selected from the group consisting of hydrogen, C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl;
wherein R 5 may be optionally independently substituted with one or more substituents selected from the group consisting of halo, —OH, ═O, —SH, ═S, —NH 2 , —CO 2 H, —O(C 1-10 alkyl), —O(C 2-10 alkenyl), —O(C 2-10 alkynyl), —S(C 2-10 alkenyl), —S(C 2-10 alkynyl), —NH(C 2-10 alkenyl), —NH(C 2-10 alkynyl), —N(C 1-10 alkyl) 2 , —N(C 2-10 alkenyl) 2 , and —N(C 2-10 alkynyl) 2 ;

wherein R 6 and R 7 are optionally taken together to form ═O, ═S or ═C(R a ) 2 ;
wherein each R a is independently selected from the group consisting of hydrogen, C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl;

wherein when the bond with the dotted line represents a double bond and R 4 is present, X is selected from the group consisting of ═C(R a )— and ═N—;
wherein when the bond with the dotted line represents a double bond and R 4 is absent, X is selected from the group consisting of ═O and ═S; and
wherein when the bond with the dotted line represents a single bond, X is selected from the group consisting of —C(R a ) 2 —, —N(R a )—, —O—, and —S—;
provided that when the bond with the dotted line represents a double bond, R 5 is absent, and when the bond with the dotted line represents a single bond, R 4 is present; and
(c) Formula (XII):

or a comestibly or biologically acceptable salt or derivative thereof, or an enantiomer or diastereomer thereof,
wherein, as valence and stability permit:
the bond with a dotted line optionally represents a single or double bond,
R 1 and R 2 are independently selected from the group consisting of hydrogen, C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl;
wherein R 1 and R 2 may be optionally independently substituted with one or more substituents selected from the group consisting of halo, —OH, ═O, —SH, ═S, —NH 2 , —CO 2 H, —O(C 1-10 alkyl), —O(C 2-10 alkenyl), —O(C 2-10 alkynyl), —S(C 1-10 alkyl), —S(C 2-10 alkenyl), —S(C 2-10 alkynyl), —NH(C 1-10 alkyl), —NH(C 2-10 alkenyl), —NH(C 2-10 alkynyl), —N(C 1-10 alkyl) 2 , —N(C 2-10 alkenyl) 2 , and —N(C 2-10 alkynyl) 2 ;

R 3 and R 4 are independently selected from the group consisting of hydrogen, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 acyl, C 1-6 acyloxy, C 1-6 alkylester, C 1-6 alkenylester, and C 1-6 alkynylester;
wherein each of R 3 and R 4 may be optionally independently substituted with one or more substituents selected from the group consisting of halo, —OH, ═O, —SH, ═S, —NH 2 , —CO 2 H, —O(C 1-10 alkyl), —O(C 2-10 alkenyl), —O(C 2-10 alkynyl), —S(C 1-10 alkyl), —S(C 2-10 alkenyl), —S(C 2-10 alkynyl), NH(C 1-10 alkyl), NH(C 2-10 alkenyl), NH(C 2-10 alkynyl), N(C 1-10 alkyl) 2 , N(C 2-10 alkenyl) 2 , N(C 2-10 alkynyl) 2 , C 1-10 acyl, C 1-10 acyloxy, C 1-10 acylamino, C 1-10 acylthioxy, C 1-10 alkylester, C 1-10 alkenylester, C 1-10 alkynylester, C 1-10 alkylamide, C 1-10 alkenylamide, C 1-10 alkynylamide, C 1-10 alkylthioester, C 1-10 alkenylthioester, and C 1-10 alkynylthioester; and

X and Y are independently selected from the group consisting of a direct bond, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, N(R a ), —O—, —S—, ═O, and ═S, provided that when either X or Y is ═O or ═S, then R 3 an

Assignees

• Chromocell Corp
• Kraft Foods Group Brands Llc

Inventors

• Shekdar Kambiz
• Lavery Daniel
• Gunnet Joseph
• Langer Jessica
• Leland Jane V
• Hayashi David
• Brown Peter H
• Slade Louise
• Jones William P

Classifications

• A61K47/14

  Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters · CPC title

• A61K47/06

  Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite · CPC title

• C07D311/22

  with oxygen or sulfur atoms directly attached in position 4 · CPC title

• A61K47/10

  Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers · CPC title

• A23L27/2052

  having oxygen or sulfur as the only hetero atoms · CPC title