Immunological adjuvant compounds compositions and methods of use thereof

A compound of the formula 2:

• wherein:
• R1 is selected from the group consisting of
• (a) C(O);
• (b) C(O)-C1-14 alkyl-C(O), wherein said C1-14 alkyl is optionally substituted with hydroxy, C1-5 alkoxy, C1-5 alkylenedioxy, C105 alkylamino, or C1-5-alkyl-aryl, wherein said aryl moiety of said C1-5-alkyl-aryl is optionally substituted with C1-5 alkoxy, C1-5 alkyl amino, C1-5 alkoxy-amino, C1-5 alkylamino-C1-5 alkoxy, —O—C1-5 alkylamino-C1-5 alkoxy, —O—C1-5 alkylamino-C(O)-C1-5 alkyl C(O)OH, —O—C1-5 alkylamino-C(O)-C1-5 alkyl-C(O)-C1-5 alkyl;
• (c) C2 to C15 straight or branched chain alkyl optionally substituted with hydroxy or alkoxy;
• and
• (d) —C(O)-C6-12 arylene-C(O)- wherein said arylene is optionally substituted with hydroxy, halogen, nitro or amino;
• a and b are independently 0, 1, 2, 3 or 4
• d, d′, d″, e, e′ and e″ are independently an integer from 1 or 4;
• X1, X2, Y1 and Y2 are independently selected from the group consisting of a null, oxygen, NH and N(C(O)C1-4 alkyl), and N(C1-4 alkyl)2;
• W1 and W2 are independently selected from the group consisting of carbonyl, methylene, sulfone and sulfoxide;
• R2 and R5 are independently selected from the group consisting of:
• (a) C2 to C20 straight chain or branched chain alkyl which is optionally substituted with oxo, hyroxy or alkoxy,
• (b) C2 to C20 straight chain or branched chain alkenyl or dialkenyul which is optionally substituted with oxo, hydroxy or alkoxy;
• (c) C2 to C20 straight chain or branched chain alkoxy which is optionally substituted with oxo, hydroxy or alkoxy;
• (d) —NH-C2 to C20 straight chain or branched chain alkyl, wherein said alkyl group is optionally substituted with oxo, hydroxy or alkoxy;
• and
• (e)
• wherein Z is selected from the group consisting of O and NH, and M and N are independently selected from the group consisting of C2 to C20 straight chain or branched chain alkyl, alkenyl, alkoxy, acyloxy, alkylamino, and acylamino;
• R3 and R6 are independently selected from the group consisting of C2 to C20 straight chain or branched chain alkyl or alkenyl optionally substituted with oxo or fluoro;
• R4 and R7 are independently selected from the group consisting of C(O)C2 to C20 straight chain or branched chain alkyl or alkenyl;
• C2 to C20 straight chain or branched chain alkyl;
• C2 to C20 straight chain or branched chain alkoxy;
• C2 to C20 straight chain or branched chain alkenyl;
• wherein said alkyl, alkenyl or alkoxy groups can be independently and optionally substituted with hydroxy, fluoro or C1 to C5 alkoxy;
• G1, G2, G3 and G4 are independently selected from the group consisting of oxygen, methylene, amino, thiol, —NHC(O)—, and —N(C(O)C1-4 alkyl)-;
• or G2R4 or G4R7 may together be a hydrogen atom or hydroxyl;
• a′ and b′ are independently 2, 3, 4, 5, 6, 7, and 8, preferably 2;
• Z1 is selected from the group consisting of —OP(O)(OH)2, —P(O)(OH)2, —OP(O)(OR8)(OH) where R8 is a C1-C4 alkyl chain, —OS(O)2OH, —S(O)2OH, —CO2H, —OB(OH)2, —OH, —CH3, —NH2, —NR93 where R9 is a C1-C4 alkyl chain;
• Z2 is selected from the group consisting of —OP(O)(OH)2, —P(O)(OH)2, —OP(O)(OR10)(OH) where R10 is a C1-C4 alkyl chain, -OS(O)2OH, —S(O)2OH, —CO2H, —OB(OH)2, —OH, —CH3, —NH2, —NR11, where R11 is a C1-C4 alkyl chain;
• or a pharmaceutically acceptable salt thereof.