Isosorbide derivatives and their use as flavor modifiers, tastants, and taste enhancers

A compound of formula (Ib):

• or a salt, solvate, ester, or N-oxide thereof, wherein
• M is O or S;
• and
• W and Z are each independently alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkylnyl, alkoxy, alkylamine, 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.

A composition comprising 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(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)NR2—R6, —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), or —P(O)R1R2;
• X is —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)—, 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;
• and
• 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 heteroarylalkyl.