Multifunctional bioactive compounds

A compound of Formula I:

• wherein
• A is an immunoregulatory radical selected from the group consisting of Trp, Tyr, Phe and His;
• L1 and L2 are each independently a linker group selected from the group consisting of a single bond, —C(O)—, —C(O)NR2—, —NR2C(O)—, —NR2—, —C(O)—O—, —OC(O)—, —S—S—, SO2NR2—, NR2SO2, —S— and —O—;
• R2 is selected from the group consisting of H, C1-6alkyl, C1-6alkylencaryl, C(O)C1-6alkyl, C(O)aryl, SO2C1-6alkyl and SO2aryl;
• R5 is H or C1-6alkyl;
• * is the L or D configuration or mixtures thereof,
• m is an integer from 1 to 50;
• n is an integer from 0 to 50;
• and
• D is selected from the group consisting of H, C1-6alkyl, a side chain of an amino acid and a biologically active molecule,
• or a pharmaceutically acceptable salt, ester prodrug or amide prodrug thereof, provided that the compound is not:
• cyclo[Asp(TyrOBn)Asp(TyrOBn)];
• cyclo[Asp(TyrOH)Asp(TyrOH)];
• cyclo[Asp(PheOBn)Asp(PheOBn)];
• cyclo[Asp(PheOH)Asp(PheOH)];
• cyclo[Glu(PheOBn)Glu(PheOBn)];
• cyclo[Glu(PheOH)Glu(PheOH)];
• cyclo[Asp(PheOH)Arg];
• cyclo[Asp(PheNH2)Leu];
• or
• cyclo{Asp[PheN(Me)(Bn)]Phe}.

A compound of Formula II:

• wherein
• A is an immunoregulatory radical selected from the group consisting of Trp, Tyr, Phe, His, aryl and heteroaryl, where the aryl and heteroaryl groups are optionally substituted with 1 to 6 substituents independently selected from the group consisting of halo, OH, OC1-6alkoxy, C1-6alkyl, C2-6alkenyl, C2-6alkenyloxy, NH2, NH(C1-6alkyl), N(C1-6alkyl)(C1-6alkyl), CN, CF3, OCF3, NO2, C(O)C1-6alkyl, C(O)OC1-6alkyl, SO2C1-6alkyl, SO2NH2, SO2NHC1-6alkyl, phenyl and C1-6alkylenephenyl,
• and where heteroaryl is an aromatic carbocyclic ring containing from 5 to 10 carbon atoms, in which 1 to 4 carbon atoms have been replaced with a heteroatom selected from one or more of O, S and N—R1, where R1 is selected from the group consisting of H, C1-6alkyl, C1-6alkylenearyl, C(O)C1-6alkyl, C(O)aryl, SO2C1-6alkyl and SO2aryl when the N atom is sp3 hybridized, or is a lone pair of electrons when the N atom is sp2 hybridized;
• L1 is a linker group selected from the group consisting of —C(O)—, —C(O)NR2—, —NR2C(O)—, —NR2—, —C(O)—O—, —OC(O)—, —S—S—, —SO2NR2—, —NR2SO2, —S— and —O—;
• L2 is a linker group selected from the group consisting of a single bond, —C(O)—, —C(O)NR2—, —NR2C(O)—, —NR2—, —C(O)—O—, —OC(O)—, —S—S—, SO2NR2—, NR2SO2, —S— and —O—;
• R2 is selected from the group consisting of H, C1-6alkyl, C1-6alkylenearyl, C(O)C1-6alkyl, C(O)aryl, SO2C1-6alkyl and SO2aryl;
• R5 is H or C1-6alkyl;
• * is the L or D configuration or mixtures thereof,
• m is an integer from 1 to 50;
• n is an integer from 0 to 50;
• and
• D is a biologically active molecule,
• or a pharmaceutically acceptable salt, ester prodrug or amide prodrug thereof, provided that the compound is not:
• cyclo[Asp(TyrOBn)Asp(TyrOBn)];
• cyclo[Asp(TyrOH)Asp(TyrOH)];
• cyclo[Asp(PheOBn)Asp(PheOBn)];
• cyclo[Asp(PheOH)Asp(PheOH)];
• cyclo[Glu(PheOBn)Glu(PheOBn)];
• or
• cyclo[Glu(PheOH)Glu(PheOH)].