ISOSORBIDE DERIVATIVES AND THEIR USE AS FLAVOR MODIFIERS, TASTANTS, AND TASTE ENHANCERSThe 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,A compound having structural formula (I) or the salt, solvate, ester, or N-oxide thereof, wherein:A is aryl, heteroaryl, or a covalent bond;Y is 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, heterocyclylalkyl, substituted heterocyclylalkyl, carbocyclyl, substituted carbocyclyl, acyl, halo, -CN, -NO2, -OR1, -S(O)R1, -S(O)2R1, -OC(O)R1, -N(R^C(O)R2, -NR1R2, -C(O)NR1R2, -C(O)OR1, -S(O)2NR1R2, -COR1, -N(R1)-C(=N-OR2)R6, -N(R^C(S)NR2R6, -C(=N-0R1)R2, -C(=NR!)-NR2R6, -N(R1)C(=NR2)NR6R7, -N(R!)C(S)R2, -N(R^-C(O)-C(O)R2, -C(S)-NR1R2, -N(R1)C(=NR2)OR6, -C(=NR1)O-NR2R6, -N(R1)N(R2)C(O)OR6, , -N(R^C(O)OR2, -N(R^C(O)NR2R6, -N(R^-C(O)-C(O)-NR2R6, -C(O)-C(O)-NR1R2, -P(O)(OR1XOR2), -P(O)(OR1XR2), or -P(O)R1R2;X is -0-, -S-, -S(O)-, -S(O)2-, -C(R3R4)-, -C(O)-, -C(S)-, -C(=NR3)-, -C(O)O-, -N(R3)-, -OC(O)-, -N(R3)C(0)-, -C(O)N(R3)-, -N(R3)-C(=N-OR4)-, -C(=N-0R3)-, -C(=NR3)-NR4-, -N(R3)C(S)N(R4)-R5, -N(R3)C(O)N(R4)-R5, -N(R3)C(=NR4)-, -N(R3)C(S)-, -N(R3)-C(0)-C(0)-, -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(R5)-, -N(R3)N(R4)C(O)O-, -N(R3)C(0)0-, -N(R3)C(O)N(R4)-, -N(R3)-C(0)-C(0)- 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, heteroarylalkyl, substituted heteroarylalkyl, heterocyclylalkyl, substituted heterocyclylalkyl, carbocyclyl, or substituted carbocyclyl; R1, R2, R3, R4, R5, R6, and R7 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, carbocyclyl, substituted carbocyclyl, heteroarylalkyl, or substituted hetero arylalkyl; and with the following provisos:(a) when A is triazole or tetrazole; then -X-Z is not -O-alkyl, -O-acyl, or sulfonamido;(b) when A is tetrazole, and Z is cyclohexyl; then X is not -NH-C(O)-, -NH-C(O)-NH-; and(c) when A is a covalent bond, then Y is not hydrogen.
이소소르비드 유도체 및 향미 개선제, 미각 촉진제 및 맛 향상제로서의 그의 용도본 발명은 식품, 음료 및 다른 식용 조성물에서 향미 또는 맛 개선제, 특히 감칠맛 ('우마미') 맛 개선제, 감칠맛 향미제 및 감칠맛 향미 향상제로서, 하기 식을 갖는 이소소르비드 유도체 및 그의 특정 아속 (subgenus) 또는 종 (species)을 제공한다.구조식 (I)을 가지는 화합물 또는 그의 염, 용매 화합물, 에스테르 또는 N-옥사이드 화합물:상기 식에서,A는 아릴, 헤테로아릴 또는 공유 결합이고;Y는 수소, 알킬, 치환된 알킬, 알케닐, 치환된 알케닐, 알키닐, 치환된 알키닐, 헤테로알킬, 치환된 헤테로알킬, 아릴, 치환된 아릴, 아릴알킬, 치환된 아릴알킬, 아릴알케닐, 치환된 아릴알케닐, 헤테로아릴, 치환된 헤테로아릴, 헤테로사이클릴, 치환된 헤테로사이클릴, 헤테로아릴알킬, 치환된 헤테로아릴알킬, 헤테로사이클릴알킬, 치환된 헤테로사이클릴알킬, 카보사이클릴, 치환된 카보사이클릴, 아실, 할로, -CN, -NO2, -OR1, -S(O)R1, -S(O)2R1, -OC(O)R1, -N(R1)C(O)R2, -NR1R2, -C(O)NR1R2, -C(O)OR1, -S(O)2NR1R2, -COR1, -N(R1)S(O)2R2, -SR1, -C(R1R2R6), -C(S)-R1, -C(=NR2)-R1, -N(R1)-C(=N-OR2)R6, -N(R1)C(S)NR2R6, -C(=N-OR1)R2, -C(=NR1)-NR2R6, -N(R1)C(=NR2)NR6R7, -N(R1)C(S)R2, -N(R1)-C(O)-C(O)R2, -C(S)-NR1R2, -N(R1)C(=NR2)OR6, -C(=NR1)O-NR2R6, -N(R1)N(R2)C(O)OR6, -N(R1)C(O)OR2, -N(R1)C(O)NR2R6, -N(R1)-C(O)-C(O)-NR2R6, -C(O)-C(O)-NR1R2, -P(O)(OR1)(OR2), -P(O)(OR1)(R2) 또는 -P(O)R1R2이며;X는 -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)-, -N(R3)-C(=N-OR4)-, -C(=N-OR3)-, -C(=NR3)-NR4-, -N(R3)C(S)N(R4)-R5, -N(R3)C(O)N(R4)-R5, -N(R3)C(=NR4)-, -N(R3)C(S)-, -N(R3)-C(O)-C(O)-, -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(R5)-, -N(R3)N(R4)C(O)O-, -N(R3)C(O)O-, -N(R3)C(O)N(R4)-, -N(R3)-C(O)-C(O)-NR4-, -C(O)-C(O)-NR4-, -P(O)(OR3)- 또는 -P(O)R3-이고;Z는 알킬, 치환된 알킬, 알케닐, 치환된 알케닐, 알키닐, 치환된 알키닐, 헤테로알킬, 치환된 헤테로알킬, 아릴, 치환된 아릴, 아릴알킬, 치환된 아릴알킬, 아릴알케닐, 치환된 아릴알케닐, 헤테로아릴, 치환된 헤테로아릴, 헤테로사이클릴, 치환된 헤테로사이클릴, 헤테로아릴알킬, 치환된 헤테로아릴알킬, 헤테로사이클릴알킬, 치환된 헤테로사이클릴알킬, 카보사이클릴 또는 치환된 카보사이클릴이며;R1, R2, R3, R4, R5, R6 및 R7은 각각 독립적으로 수소, 알킬, 치환된 알킬, 알케닐, 치환된 알케닐, 알키닐, 치환된 알키닐, 헤테로알킬, 치환된 헤테로알킬, 아릴, 치환된 아릴, 아릴알킬, 치환된 아릴알킬, 아릴알케닐, 치환된 아릴알케닐, 헤테로아릴, 치환된 헤테로아릴, 헤테로사이클릴, 치환된 헤테로사이클릴, 카보사이클릴, 치환된 카보사이클릴, 헤테로아릴알킬 또는 치환된 헤테로아릴알킬이고;단,(a) A가 트리아졸 또는 테트라졸이면 -X-Z는 -O-알킬, -O-아실 또는 술폰아미도가 아니며;(b) A가 테트라졸이고 Z가 사이클로헥실이면 X는 -NH-C(O)-, -NH-C(O)-NH가 아니고;(c) A가 공유 결합이면 Y는 수소가 아니다.