Flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
G01N-033/543
G01N-033/50
A61K-008/55
A61K-047/22
A61K-008/49
A61K-047/24
C07C-233/65
C07C-235/54
C07C-275/30
C07C-275/34
C07D-307/84
C07D-317/68
G01N-033/566
G01N-033/74
A23L-002/56
C07D-405/12
C07F-009/655
A23L-027/00
A23L-027/20
출원번호
US-0509761
(2014-10-08)
등록번호
US-10060909
(2018-08-28)
발명자
/ 주소
Tachdjian, Catherine
Patron, Andrew P.
Adamski-Werner, Sara L.
Bakir, Farid
Chen, Qing
Darmohusodo, Vincent
Hobson, Stephen Terrence
Li, Xiaodong
Qi, Ming
Rogers, Daniel H.
Rinnova, Marketa
Servant, Guy
Tang, Xiao-Qing
Zoller, Mark
Wallace, David
Xing, Amy
Gubernator, Klaus
출원인 / 주소
Senomyx, Inc.
대리인 / 주소
Knobbe Martens Olson & Bear LLP
인용정보
피인용 횟수 :
0인용 특허 :
90
초록▼
The present invention relates to the discovery that certain non-naturally occurring, non-peptide amide compounds and amide derivatives, such as oxalamides, ureas, and acrylamides, are useful flavor or taste modifiers, such as a flavoring or flavoring agents and flavor or taste enhancer, more particu
The present invention relates to the discovery that certain non-naturally occurring, non-peptide amide compounds and amide derivatives, such as oxalamides, ureas, and acrylamides, are useful flavor or taste modifiers, such as a flavoring or flavoring agents and flavor or taste enhancer, more particularly, savory (the “umami” taste of monosodium glutamate) or sweet taste modifiers,—savory or sweet flavoring agents and savory or sweet flavor enhancers, for food, beverages, and other comestible or orally administered medicinal products or compositions.
대표청구항▼
1. An amide compound having the following formula: or a comestibly acceptable salt thereof; whereinA is phenyl;m is 1 or 2;each R1′ is independently selected from alkyl, alkoxy, alkoxy-alkyl, hydroxyalkyl, CN, CO2H, CO2R6, CHO, COR6, SR6, fluoro, chloro, cycloalkyl, cycloalkenyl, heterocycle, aryl,
1. An amide compound having the following formula: or a comestibly acceptable salt thereof; whereinA is phenyl;m is 1 or 2;each R1′ is independently selected from alkyl, alkoxy, alkoxy-alkyl, hydroxyalkyl, CN, CO2H, CO2R6, CHO, COR6, SR6, fluoro, chloro, cycloalkyl, cycloalkenyl, heterocycle, aryl, haloalkoxy, and heteroaryl;R6 is C1-C6 alkyl;i) R2 is a C3-C10 branched alkyl or cycloalkyl optionally substituted with one to four substituents each independently selected from alkoxy, alkoxy-alkyl, hydroxyalkyl, OH, NH2, NHR6, N(R6)2, CN, CO2H, CO2R6, CHO, COR6, SH, SR6, halogen, alkenyl, cycloalkyl, cycloalkenyl, aryl, haloalkyl, haloalkoxy, and heteroaryl; and R6 is C1-C6 alkyl; orii) R2 is a 1-(1,2,3,4) tetrahydronapthalene ring or an 2,3-dihydro-1H-indene ring having the following formula: wherein n is 1, 2, or 3, and each R2′ can be bonded to either the aromatic or non-aromatic ring and is independently selected from hydrogen, fluoro, chloro, NH2, NHCH3, N(CH3)2, CO2CH3, SCH3, SEt, methyl, ethyl, isopropyl, vinyl, trifluoromethyl, methoxy, ethoxy, isopropoxy, and trifluoromethoxy groups,wherein the amide compound has a molecular weight of 500 grams per mole or less. 2. The amide compound of claim 1, wherein m is 1. 3. The amide compound of claim 1, wherein m is 2. 4. The amide compound of claim 3, wherein each R1′ is independently selected from fluoro, chloro, SCH3, SEt, methyl, ethyl, isopropyl, vinyl, methoxy, ethoxy, isopropoxy, and trifluoromethoxy. 5. The amide compound of claim 1, wherein R2 is a C3-C10 branched alkyl optionally substituted with one to four substituents independently selected from alkoxy, alkoxy-alkyl, haloalkyl, haloalkoxy, and CO2R6; and R6 is C1-C6 alkyl. 6. The amide compound of claim 5, wherein R2 is a C3-C10 branched alkyl optionally substituted with one or two substituents independently selected from hydroxy, fluoro, chloro, CO2CH3, SCH3, SEt, methyl, ethyl, isopropyl, trifluoromethyl, methoxy, ethoxy, isopropoxy, and trifluoromethoxy. 7. The amide compound of claim 1, wherein R2 is a cycloalkyl ring having 3 to 10 ring carbon atoms optionally substituted with one to four substituents independently selected from alkyl, alkoxy, alkoxy-alkyl, hydroxyalkyl, haloalkyl, haloalkoxy, and halogen. 8. The amide compound of claim 7, wherein R2 is a cycloalkyl ring having 5 to 8 ring carbon atoms optionally substituted with one to four substituents independently selected from methyl, ethyl, isopropyl, trifluoromethyl, methoxy, ethoxy, isopropoxy, and trifluoromethoxy. 9. The amide compound of claim 1, wherein A is a phenyl ring;m is 2;each R1′ is independently selected from fluoro, chloro, SCH3, SEt, methyl, ethyl, isopropyl, vinyl, methoxy, ethoxy, isopropoxy, and trifluoromethoxy; andR2 is a C3-C10 branched alkyl optionally substituted with one or two substituents independently selected from fluoro, chloro, CO2CH3, SCH3, SEt, methyl, ethyl, isopropyl, trifluoromethyl, methoxy, ethoxy, isopropoxy, and trifluoromethoxy; or a cycloalkyl ring having 5 to 8 ring carbon atoms optionally substituted with one to four substituents independently selected from fluoro, chloro, CO2CH3, SCH3, SEt, methyl, ethyl, isopropyl, trifluoromethyl, methoxy, ethoxy, isopropoxy, and trifluoromethoxy. 10. The amide compound of claim 1, wherein R2 is a 1-(1,2,3,4)tetrahydronapthalene ring or an 2,3-dihydro-1H-indene ring having the following formula: wherein each R2′ can be bonded to either the aromatic or non-aromatic ring and is independently selected from hydrogen, fluoro, chloro, CO2CH3, SCH3, SEt, methyl, ethyl, isopropyl, vinyl, trifluoromethyl, methoxy, ethoxy, isopropoxy, and trifluoromethoxy groups. 11. The amide compound of claim 10, wherein R2 has the following formula: wherein each R2′ are independently selected from the group consisting of hydrogen, fluoro, chloro, COOCH3, SCH3, SEt, methyl, ethyl, isopropyl, vinyl, trifluoromethyl, methoxy, ethoxy, isopropoxy, and trifluoromethoxy. 12. An amide compound having the following formula: or a comestibly acceptable salt thereof; wherein(R1′)m-A is wherein m is 1, 2, or 3, and each R1′ is independently selected from fluoro, chloro, NH2, NHCH3, N(CH3)2, CO2CH3, SCH3, SEt, methyl, ethyl, isopropyl, vinyl, methoxy, ethoxy, isopropoxy, and trifluoromethoxy;i) R2 is a C3-C10 branched alkyl or cycloalkyl optionally substituted with one to four substituents each independently selected from alkoxy, alkoxy-alkyl, hydroxyalkyl, NH2, NHR6, N(R6)2, CN, CO2H, CO2R6, CHO, COR6, SH, SR6, halogen, alkenyl, cycloalkyl, cycloalkenyl, aryl, and heteroaryl and R6 is C1-C6 alkyl, orii) R2 is a 1-(1,2,3,4) tetrahydronapthalene ring or an 2,3-dihydro-1H-indene ring having the following formula: wherein n is 1, 2, or 3, and each R2′ can be bonded to either the aromatic or non-aromatic ring and is independently selected from hydrogen, fluoro, chloro, NH2, NHCH3, N(CH3)2, CO2CH3, SCH3, SEt, methyl, ethyl, isopropyl, vinyl, trifluoromethyl, methoxy, ethoxy, isopropoxy, and trifluoromethoxy groups,wherein the amide compound has a molecular weight of 500 grams per mole or less. 13. The amide compound of claim 1, wherein A is phenyl; R2 is a C3-C10 branched alkyl substituted with one to four substituents each independently selected from alkoxy, alkoxy-alkyl, CO2R6, COR6, and halogen. 14. An amide compound selected from the group consisting of (R)-methyl 2-(3-chloro-4-methoxybenzamido)-4-methylpentanoate,4-methoxy-3-methyl-N-(5-methylhexan-3-yl)benzamide,N-(heptan-4-yl)-2-methylbenzo[d][1,3]dioxole-5-carboxamide,(S)-methyl 4-methyl-2-(4-methyl-3-(methylthio)benzamido)pentanoate,4-methoxy-3-methyl-N-(2-methylheptan-4-yl)benzamide,N-(heptan-4-yl)-6-methylbenzo[d][1,3]dioxole-5-carboxamide,3,4-dimethyl-N-(2-methylhexan-3-yl)benzamide,(R)-methyl 4-methyl-2-(5-methylbenzofuran-2-carboxamido)pentanoate,N-(hexan-3-yl)-4-methoxy-3-methylbenzamide,N-(heptan-4-yl)-3-methyl-4-(methylthio)benzamide,N-(hexan-3-yl)-3-methyl-4-(methylthio)benzamide,methyl 2-(3-chloro-4-methoxybenzamido)hexanoate,3,4-dimethyl-N-(2-methylheptan-4-yl)benzamide,N-(hexan-3-yl)-3,4-dimethylbenzamide,N-(heptan-4-yl)-3,4-dimethylbenzamide,(R)-methyl 4-methyl-2-(4-(methylthio)benzamido)pentanoate,4-ethoxy-N-(heptan-4-yl)-3-methylbenzamide,3,4-dimethyl-N-(5-methylhexan-3-yl)benzamide,(R)-methyl 4-methyl-2-(4-vinylbenzamido)pentanoate,4-methoxy-3-methyl-N-(2-methylhexan-3-yl)benzamide,N-(heptan-4-yl)benzo[d][1,3]dioxole-5-carboxamide,(R)-methyl 2-(benzo[d][1,3]dioxole-6-carboxamido)-4-methylpentanoate,(R)-N-(1-methoxy-4-methylpentan-2-yl)-3,4-dimethylbenzamide,(R)-methyl-2-(2,3-dimethylfuran-5-carboxamido)-4-methylpentanoate,4-Methoxy-N-(1-methoxymethyl-3-methyl-butyl)-3-methyl-benzamide,3-chloro-2-hydroxy-N-(2-methyl-1,2,3,4-tetrahydronaphthalen-1-yl)benzamide,3-chloro-2-hydroxy-N-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)benzamide,(R)-3-chloro-2-hydroxy-N-(1,2,3,4-tetrahydronaphthalen-1-yl)benzamide,3-chloro-2-hydroxy-N-(5-hydroxy-1,2,3,4-tetrahydronaphthalen-1-yl)benzamide,3-chloro-2-hydroxy-N-(4-methyl-1,2,3,4-tetrahydronaphthalen-1-yl)benzamide,3-chloro-2-hydroxy-N-(6-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)benzamide,3-chloro-2-hydroxy-N-(1,2,3,4-tetrahydronaphthalen-1-yl)benzamide,2,3-dihydroxy-N-(2-methyl-1,2,3,4-tetrahydronaphthalen-1-yl)benzamide,2-hydroxy-N-(2-methyl-1,2,3,4-tetrahydronaphthalen-1-yl)benzamide,2,3-dihydroxy-N-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)benzamide,(S)-2,6-dimethyl-N-(1,2,3,4-tetrahydronaphthalen-1-yl)benzamide,N-(5,7-dimethyl-1,2,3,4-tetrahydronaphthalen-1-yl)-3-methylisoxazole-4-carboxamide,3-methyl-N-(2-methyl-1,2,3,4-tetrahydronaphthalen-1-yl)isoxazole-4-carboxamide,3-methyl-N-(4-methyl-1,2,3,4-tetrahydronaphthalen-1-yl)isoxazole-4-carboxamide,N-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)-3-methylisoxazole-4-carboxamide,(R)-5-bromo-N-(1,2,3,4-tetrahydronaphthalen-1-yl)nicotinamide,(R)-3-methyl-N-(1,2,3,4-tetrahydronaphthalen-1-yl)isoxazole-4-carboxamide,(S)-5-bromo-N-(1,2,3,4-tetrahydronaphthalen-1-yl)nicotinamide,(R)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)furan-3-carboxamide,(R)-5-methyl-N-(1,2,3,4-tetrahydronaphthalen-1-yl)isoxazole-4-carboxamide,(R)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)furan-3-carboxamide,3-methyl-N-(1,2,3,4-tetrahydronaphthalen-l-yl)isoxazole-4-carboxamide,N-(3,3-dimethylbutan-2-yl)-2,3,5,6-tetrafluoro-4-methylbenzamide,2,3,5,6-tetrafluoro-4-methyl-N-(3-methylbutan-2-yl)benzamide,2,3,5,6-tetrafluoro-4-methyl-N-(2-methylcyclohexyl)benzamide,N-(2-methylcyclohexyl)-3-(trifluoromethoxy)benzamide,3-chloro-5-fluoro-N-(2-methylcyclohexyl)benzamide,(R)-N-(3,3-dimethylbutan-2-yl)-2,3,5,6-tetrafluoro-4-methylbenzamide,4-fluoro-N-(2-methylcyclohexyl)-3-(trifluoromethyl)benzamide,(S)-2,3,5,6-tetrafluoro-4-methyl-N-(3-methylbutan-2-yl)benzamide,2,5-dichloro-N-(2-methylcyclohexyl)benzamide,3,5-dichloro-2,6-dimethoxy-N-(2-methylcyclohexyl)benzamide, and2,6-dimethyl-N-(2-methylcyclohexyl)benzamide, or a comestibly acceptable salt thereof. 15. An ingestible composition comprising at least a savory flavor modulating amount of at least one compound of claim 1, or a comestibly acceptable salt thereof. 16. The ingestible composition of claim 15, wherein the amide compound is present in a concentration from about 0.01 ppm to about 30 ppm. 17. The ingestible composition of claim 15, wherein the amide compound is present in a concentration from about 0.05 ppm to about 15 ppm. 18. The ingestible composition of claim 15, wherein the amide compound is present in a concentration from about 0.1 ppm to about 5 ppm. 19. The ingestible composition of claim 15, wherein the amide compound is present in a concentration from about 0.1 ppm to about 3 ppm. 20. A method for modulating the taste of an ingestible composition comprising: combining the ingestible composition with at least a savory flavor modulating amount of a compound of claim 1, or a comestibly acceptable salt thereof, so as to form a taste modified ingestible composition. 21. The method of claim 20, wherein the amide compound is present in the modified ingestible composition at a concentration from about 0.01 ppm to about 30 ppm. 22. The method of claim 20, wherein the amide compound is present in the modified ingestible composition in a concentration from about 0.05 ppm to about 15 ppm. 23. The method of claim 20, wherein the amide compound is present in the modified ingestible composition in a concentration from about 0.1 ppm to about 5 ppm. 24. The method of claim 20, wherein the amide compound is present in the modified ingestible composition in a concentration from about 0.1 ppm to about 3 ppm. 25. The amide compound of claim 14, which selected from the group consisting of (R)-methyl 2-(3-chloro-4-methoxybenzamido)-4-methylpentanoate,4-methoxy-3-methyl-N-(5-methylhexan-3-yl)benzamide,N-(heptan-4-yl)-2-methylbenzo[d][1,3]dioxole-5-carboxamide,(S)-methyl 4-methyl-2-(4-methyl-3-(methylthio)benzamido)pentanoate,4-methoxy-3-methyl-N-(2-methylheptan-4-yl)benzamide,N-(heptan-4-yl)-6-methylbenzo[d][1,3]dioxole-5-carboxamide,3,4-dimethyl-N-(2-methylhexan-3-yl)benzamide,(R)-methyl 4-methyl-2-(5-methylbenzofuran-2-carboxamido)pentanoate, and(R)-N-(1-methoxy-4-methylpentan-2-yl)-3,4-dimethylbenzamide, or a comestibly acceptable salt thereof. 26. The amide compound of claim 14, which selected from the group consisting of N-(hexan-3-yl)-4-methoxy-3-methylbenzamide,N-(heptan-4-yl)-3-methyl-4-(methylthio)benzamide,N-(hexan-3-yl)-3-methyl-4-(methylthio)benzamide,methyl 2-(3-chloro-4-methoxybenzamido)hexanoate,3,4-dimethyl-N-(2-methylheptan-4-yl)benzamide,N-(hexan-3-yl)-3,4-dimethylbenzamide,N-(heptan-4-yl)-3,4-dimethylbenzamide,(R)-methyl 4-methyl-2-(4-(methylthio)benzamido)pentanoate,4-ethoxy-N-(heptan-4-yl)-3-methylbenzamide,3,4-dimethyl-N-(5-methylhexan-3-yl)benzamide, and(R)-N-(1-methoxy-4-methylpentan-2-yl)-3,4-dimethylbenzamide, or a comestibly acceptable salt thereof. 27. The amide compound of claim 14, which selected from the group consisting of (R)-methyl 4-methyl-2-(4-vinylbenzamido)pentanoate,4-methoxy-3-methyl-N-(2-methylhexan-3-yl)benzamide,N-(heptan-4-yl)benzo[d][1,3]dioxole-5-carboxamide,(R)-methyl 2-(benzo[d][1,3]dioxole-6-carboxamido)-4-methylpentanoate,(R)-N-(1-methoxy-4-methylpentan-2-yl)-3,4-dimethylbenzamide,(R)-methyl-2-(2,3-dimethylfuran-5-carboxamido)-4-methylpentanoate, and4-Methoxy-N-(1-methoxymethyl-3-methyl-butyl)-3-methyl-benzamide, or a comestibly acceptable salt thereof. 28. The amide compound of claim 14, which selected from the group consisting of (R)-N-(1-methoxy-4-methylpentan-2-yl)-3,4-dimethylbenzamide,3-chloro-2-hydroxy-N-(2-methyl-1,2,3,4-tetrahydronaphthalen-1-yl)benzamide,3-chloro-2-hydroxy-N-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)benzamide,(R)-3-chloro-2-hydroxy-N-(1,2,3,4-tetrahydronaphthalen-1-yl)benzamide,3-chloro-2-hydroxy-N-(5-hydroxy-1,2,3,4-tetrahydronaphthalen-1-yl)benzamide,3-chloro-2-hydroxy-N-(4-methyl-1,2,3,4-tetrahydronaphthalen-1-yl)benzamide,3-chloro-2-hydroxy-N-(6-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)benzamide,3-chloro-2-hydroxy-N-(1,2,3,4-tetrahydronaphthalen-1-yl)benzamide,2,3-dihydroxy-N-(2-methyl-1,2,3,4-tetrahydronaphthalen-1-yl)benzamide,2-hydroxy-N-(2-methyl-1,2,3,4-tetrahydronaphthalen-1-yl)benzamide,2,3-dihydroxy-N-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)benzamide,(S)-2,6-dimethyl-N-(1,2,3,4-tetrahydronaphthalen-1-yl)benzamide,N-(5,7-dimethyl-1,2,3,4-tetrahydronaphthalen-1-yl)-3-methylisoxazole-4-carboxamide,3-methyl-N-(2-methyl-1,2,3,4-tetrahydronaphthalen-1-yl)isoxazole-4-carboxamide,3-methyl-N-(4-methyl-1,2,3,4-tetrahydronaphthalen-1-yl)isoxazole-4-carboxamide,N-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)-3-methylisoxazole-4-carboxamide,(R)-5-bromo-N-(1,2,3,4-tetrahydronaphthalen-1-yl)nicotinamide,(R)-3-methyl-N-(1,2,3,4-tetrahydronaphthalen-1-yl)isoxazole-4-carboxamide,(S)-5-bromo-N-(1,2,3,4-tetrahydronaphthalen-1-yl)nicotinamide,(R)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)furan-3-carboxamide,(R)-5-methyl-N-(1,2,3,4-tetrahydronaphthalen-1-yl)isoxazole-4-carboxamide,(R)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)furan-3-carboxamide, and3-methyl-N-(1,2,3,4-tetrahydronaphthalen-1-yl)isoxazole-4-carboxamide, or a comestibly acceptable salt thereof. 29. The amide compound of claim 14, which selected from the group consisting of (R)-N-(1-methoxy-4-methylpentan-2-yl)-3,4-dimethylbenzamide,N-(3,3-dimethylbutan-2-yl)-2,3,5,6-tetrafluoro-4-methylbenzamide,2,3,5,6-tetrafluoro-4-methyl-N-(3-methylbutan-2-yl)benzamide,2,3,5,6-tetrafluoro-4-methyl-N-(2-methylcyclohexyl)benzamide,N-(2-methylcyclohexyl)-3-(trifluoromethoxy)benzamide,3-chloro-5-fluoro-N-(2-methylcyclohexyl)benzamide,(R)-N-(3,3-dimethylbutan-2-yl)-2,3,5,6-tetrafluoro-4-methylbenzamide,4-fluoro-N-(2-methylcyclohexyl)-3-(trifluoromethyl)benzamide,(S)-2,3,5,6-tetrafluoro-4-methyl-N-(3-methylbutan-2-yl)benzamide,2,5-dichloro-N-(2-methylcyclohexyl)benzamide,3,5-dichloro-2,6-dimethoxy-N-(2-methylcyclohexyl)benzamide, and2,6-dimethyl-N-(2-methylcyclohexyl)benzamide, or a comestibly acceptable salt thereof. 30. The amide compound of claim 14, which selected from the group consisting of (R)-methyl 2-(3-chloro-4-methoxybenzamido)-4-methylpentanoate,(S)-methyl 4-methyl-2-(4-methyl-3-(methylthio)benzamido)pentanoate,(R)-methyl 4-methyl-2-(5-methylbenzofuran-2-carboxamido)pentanoate,methyl 2-(3-chloro-4-methoxybenzamido)hexanoate,(R)-methyl 4-methyl-2-(4-(methylthio)benzamido)pentanoate,(R)-methyl 4-methyl-2-(4-vinylbenzamido)pentanoate,(R)-N-(1-methoxy-4-methylpentan-2-yl)-3,4-dimethylbenzamide,(R)-methyl-2-(2,3-dimethylfuran-5-carboxamido)-4-methylpentanoate,4-Methoxy-N-(1-methoxymethyl-3-methyl-butyl)-3-methyl-benzamide, or a comestibly acceptable salt thereof. 31. The amide compound of claim 14, wherein the compound is (R)-N-(1-methoxy-4-methylpentan-2-yl)-3,4-dimethylbenzamide, or a comestibly acceptable salt thereof.
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