Compounds, Compositions, And Methods For Reducing Or Eliminating Bitter Taste

A composition comprising a compound according to a formula selected from the group consisting of:

• (a) Formula (I):
• or a comestibly or biologically acceptable salt or derivative thereof, or an enantiomer or diastereomer thereof,
• wherein, as valence and stability permit:
• R1 is absent or is selected from the group consisting of hydroxyl, C1-6alkoxy, and C1-6acyloxy;
• R2 is selected from the group consisting of hydrogen, C1-6alkyl, C2-6alkenyl, and C2-6alkynyl;
• R3 is selected from the group consisting of hydrogen and C1-6alkoxy;
• R4 is selected from the group consisting of hydroxyl, C1-6alkoxy, and C1-16acyloxy;
• or R3 and R4 together form ═O;
• wherein any of R1, R2, R3, and R4, independently, is optionally substituted with 1-3 substituents selected from the group consisting of C1-10alkyl, C1-10haloalkyl, halo, hydroxyl, carboxyl, C1-10alkoxycarbonyl, C2-10alkenyloxycarbonyl, C2-10alkynyloxycarbonyl, C1-10acyl, C1-10acylamino, C1-10acyloxy, C1-10carbonate, C1-10alkoxy, phenyloxy, phosphoryl, phosphate, phosphonate, phosphinate, amino, diC1-10alkylamino, monoC1-10alkylamino, C1-13amido, C1-10imino, C1-10carbamate, C1-10urea, cyano, nitro, azido, sulfhydryl, C1-10alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, C3-7carbocyclyl, C3-7carbocyclyl-C1-6alkyl, C1-6heterocyclyl, C1-6heterocyclyl-C1-6alkyl, phenyl, phenyl-C1-6alkyl, C1-5heteroaryl, and C1-5heteroaryl-C1-6alkyl;
• and wherein heterocyclic or heteroaromatic rings, independently for each occurrence, comprise 1-4 heteroatoms selected from N, O, and S;
• and
• m is 0-2;
• n is 0-2;
• p is 0-2;
• t is 0-2;
• wherein C1 and C6 in Formula (I) optionally are bonded together to form a 6-membered ring;
• and
• wherein all dotted bonds indicate optional carbon-carbon double bonds;
• wherein the composition is edible and capable of reducing bitter taste of a bitter tastant;
• (b) Formula (V):
• or a comestibly or biologically acceptable salt or derivative thereof, or an enantiomer or diastereomer thereof,
• wherein, as valence and stability permit:
• R1, independently for each occurrence, is selected from the group consisting of halo, hydroxyl, C1-6alkyl, C1-6haloalkyl, C2-6alkenyl, C2-6alkynyl, and C1-6alkoxy;
• R2 is selected from the group consisting of hydrogen, halo, hydroxyl, C1-6alkyl, C1-6haloalkyl, C2-6alkenyl, C2-6alkynyl, C2-6alkoxy, C1-6acyloxy optionally substituted by hydroxyl, amino, mono- or disubstituted C1-6alkyl amino, or carboxyl;
• R3 is selected from the group consisting of hydrogen, hydroxyl, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, and C1-6alkoxy;
• R4 is selected from the group consisting of hydrogen, hydroxyl, C1-21alkyl, C2-21alkenyl, C2-21alkynyl, and C1-6alkoxy, wherein R4 is optionally substituted by one or more occurrences of hydroxyl or acetyloxy;
• R5 is selected from the group consisting of hydrogen, hydroxyl, C1-21alkyl, C2-21alkenyl, C2-21alkynyl, and C2-6alkoxy, wherein R5 is optionally substituted by one or more occurrences of hydroxyl or acetyloxy;
• or R4 and R5 together form ═O;
• wherein any of R1, R2, R3, R4, and R5, independently and independently for each occurrence, is optionally substituted with 1-3 substituents selected from the group consisting of C1-10alkyl, C1-10haloalkyl, halo, hydroxyl, carboxyl, C1-10alkoxycarbonyl, C2-10alkenyloxycarbonyl, C2-10alkynyloxycarbonyl, C1-10acyl, C1-10acylamino, C1-10acyloxy, C1-10carbonate, C1-10alkoxy, phenyloxy, phosphoryl, phosphate, phosphonate, phosphinate, amino, diC1-10alkylamino, monoC1-10alkylamino, C1-13amido, C1-10imino, C1-10carbamate, C1-10urea, cyano, nitro, azido, sulfhydryl, C1-10alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, C3-7carbocyclyl, C3-7carbocyclyl-C1-6alkyl, C1-6heterocyclyl, C1-6heterocyclyl-C1-6alkyl, phenyl, phenyl-C1-6alkyl, C1-5heteroaryl, and C1-5heteroaryl-C1-6alkyl;
• 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;
• wherein the composition is edible and capable of reducing bitter taste of a bitter tastant;
• (c) Formula (VIII):
• or a comestibly or biologically acceptable salt or derivative thereof, or an enantiomer or diastereomer thereof,
• wherein, as valence and stability permit:
• R1, independently for each occurrence, is selected from the group consisting of hydrogen, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, and C1-6acyl;
• R2 is selected from the group consisting of hydrogen, C1-6alkyl, C2-6alkenyl, and C2-6alkynyl;
• R3 is selected from the group consisting of hydrogen, C1-6alkyl, C2-6alkenyl, and C2-6alkynyl;
• or R2 and R3 together form ═O;
• R4 is selected from the group consisting of hydrogen, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C1-6acyl, and C6-10aryl-C1-6alkyl;
• wherein any of R1, R2, R3, and R4, independently and independently for each occurrence, is optionally substituted with 1-3 substituents selected from the group consisting of C1-10alkyl, C1-10haloalkyl, halo, hydroxyl, carboxyl, C1-10alkoxycarbonyl, C2-10alkenyloxycarbonyl, C2-10alkynyloxycarbonyl, C1-10acyl, C1-10acylamino, C1-10acyloxy, C1-10carbonate, C1-10alkoxy, phenyloxy, phosphoryl, phosphate, phosphonate, phosphinate, amino, diC1-10alkylamino, monoC1-10alkylamino, C1-13amido, C1-10imino, C1-10carbamate, C1-10urea, cyano, nitro, azido, sulfhydryl, C1-10alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, C3-7carbocyclyl, C3-7carbocyclyl-C1-6alkyl, C1-6heterocyclyl, C1-6heterocyclyl-C1-6alkyl, phenyl, phenyl-C1-6alkyl, C1-5heteroaryl, and C1-5heteroaryl-C1-6alkyl;
• 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;
• and
• wherein the composition is edible and capable of reducing bitter taste of a bitter tastant;
• (d) 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,
• R1, R2, R3, R6, and R7 are independently selected from the group consisting of hydrogen, C1-6alkyl, C2-6alkenyl, and C2-6alkynyl;
• wherein each of R1, R2, R3, R6, and R7 may be optionally independently substituted with one or more substituents selected from the group consisting of halo, —OH, ═O, —SH, ═S, —NH2, —CO2H, —O(C1-10alkyl), —O(C2-10alkenyl), —O(C2-10alkynyl), —S(C1-10alkyl), —S(C2-10alkenyl), —S(C2-10alkynyl), —NH(C1-10alkyl), —NH(C2-10alkenyl), —NH(C2-10alkynyl), —N(C1-10alkyl)2, —N(C2-10alkenyl)2, and —N(C2-10alkynyl)2;
• R4 is absent or selected from the group consisting of hydrogen, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C1-6acyl, C1-6acyloxy, C1-6alkylester, C1-6alkenylester, and C1-6alkynylester;
• wherein R4 may be optionally substituted with one or more substituents selected from the group consisting of halo, —OH, ═O, —SH, ═S, —NH2, —CO2H, —O(C1-10alkyl), —O(C2-10alkenyl), —O(C2-10alkynyl), —S(C1-10alkyl), —S(C2-10alkenyl), —S(C2-10alkynyl), —NH(C1-10alkyl), —NH(C2-10alkenyl), —NH(C2-10alkynyl), —N(C1-10alkyl)2, —N(C2-10alkenyl)2, —N(C2-10alkynyl)2, C1-10acyl, C1-10acyloxy, C1-10acylamino, C1-10acylthioxy, C1-10alkylester, C1-10alkenylester, C1-10alkynylester, C1-10alkylamide, C1-10alkenylamide, C1-10alkynylamide, C1-10alkylthioester, C1-10alkenylthioester, and C1-10alkynylthioester;
• R5 is absent or selected from the group consisting of hydrogen, C1-6alkyl, C2-6alkenyl, and C2-6alkynyl;
• wherein R5 may be optionally independently substituted with one or more substituents selected from the group consisting of halo, —OH, ═O, —SH, ═S, —NH2, —CO2H, —O(C1-10alkyl), —O(C2-10alkenyl), —O(C2-10alkynyl), —S(C1-10alkyl), —S(C2-10alkenyl), —S(C2-10alkynyl), —NH(C1-10alkyl), —NH(C2-10alkenyl), —NH(C2-10alkynyl), —N(C1-10alkyl)2, —N(C2-10alkenyl)2, and —N(C2-10alkynyl)2;
• wherein R6 and R7 are optionally taken together to form ═O, ═S or ═C(Ra)2;
• wherein each Ra is independently selected from the group consisting of hydrogen, C1-6alkyl, C2-6alkenyl, and C2-6alkynyl;
• wherein when the bond with the dotted line represents a double bond and R4 is present, X is selected from the group consisting of ═C(Ra)— and ═N—;
• wherein when the bond with the dotted line represents a double bond and R4 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(Ra)2—, —N(Ra)—, —O—, and —S—;
• provided that when the bond with the dotted line represents a double bond, R5 is absent, and when the bond with the dotted line represents a single bond, R4 is present;
• and
• wherein the composition is edible and capable of reducing bitter taste of a bitter tastant;
• and
• (e) 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,
• R1 and R2 are independently selected from the group consisting of hydrogen, C1-6alkyl, C2-6alkenyl, and C2-6alkynyl;
• wherein R1 and R2 may be optionally independently substituted with one or more substituents selected from the group consisting of halo, —OH, ═O, —SH, ═S, —NH2, —CO2H, —O(C1-10alkyl), —O(C2-10alkenyl), —O(C2-10alkynyl), —S(C1-10alkyl), —S(C2-10alkenyl), —S(C2-10alkynyl), —NH(C1-10alkyl), —NH(C2-10alkenyl), —NH(C2-10alkynyl), —N(C1-10alkyl)2, —N(C2-10alkenyl)2, and —N(C2-10alkynyl)2;
• R3 and R4 are independently selected from the group consisting of hydrogen, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C1-6acyl, C1-6acyloxy, C1-6alkylester, C1-6alkenylester, and C1-6alkynylester;
• wherein each of R3 and R4 may be optionally independently substituted with one or more substituents selected from the group consisting of halo, —OH, ═O, —SH, ═S, —NH2, —CO2H, —O(C1-10alkyl), —O(C2-10alkenyl), —O(C2-10alkynyl), —S(C1-10alkyl), —S(C2-10alkenyl), —S(C2-10alkynyl), NH(C1-10alkyl), NH(C2-10alkenyl), NH(C2-10alkynyl), N(C1-10alkyl)2, N(C2-10alkenyl)2, N(C2-10alkynyl)2, C1-10acyl, C1-10acyloxy, C1-10acylamino, C1-10acylthioxy, C1-10alkylester, C1-10alkenylester, C1-10alkynylester, C1-10alkylamide, C1-10alkenylamide, C1-10alkynylamide, C1-10alkylthioester, C1-10alkenylthioester, and C1-10alkynylthioester;
• and
• X and Y are independently selected from the group consisting of a direct bond, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, N(Ra), —O—, —S—, ═O, and ═S, provided that when either X or Y is ═O or ═S, then R3 and R4, respectively, are absent,
• wherein Ra is selected from the group consisting of hydrogen, C1-6alkyl, C2-6alkenyl, and C2-6alkynyl;
• and
• wherein the composition is edible and capable of reducing bitter taste of a bitter tastant.