Immunologically active dipeptidyl 5-0, 6-0-acyl- 2-...

C - Chemistry – Metallurgy – 07 – K

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260/8, 530/9

C07K 9/00 (2006.01)

Patent

CA 1175804

ABSTRACT OF THE DISCLOSURE Immunologically active compounds of the formula: Image (I,) I II III wherein R1 is C1-7 alkyl, substituted C1-7 alkyl; phenyl; or substituted phenyl; R2 is hydrogen; or C1-10 alkyl; R3 and R4 may be the same ofd different and are each independiently acyl of the formula: Image where X is -O-, -S-, or Image ; R9, R10 and R12 may be the same of different and are each independently hydrogen; C1-20 alkyl; C1-20 alkylcarbonyloxy; amino; benzyl; C1-20 alkoxymethyl; or C1-20 alkylamido; r is 0 or 1; s is 0 or 1; and t is 0-20, provided that s may only be o when r and t are greater than 0, or when r is 0 and R11 is amino, phenyl, substituted phenyl, 1- adamantyl, or heterocycle selected from the group consisting of 2- or 3-furyl, 2- or 3-thienyl, 2- or 3-pyrrolidinyl, 2-, 3-, or 4-pyridyl, and 1-tetrazolyl, said hetero- cycle optionally substituted with C1-20 alkylcarbonyl; and R11 is hydrogen; C1-30 alkyl; C2-30 alkenyl: C1-30 alkoxy: phenyl; C1-20 alkylsulfonyl; or cholesteryl; and R4 may additionally be hydrogen; R5 is hydrogen; or R5-R6 together is -CH2-CH2-CH2: R6 is hydrogens C1-7 alkyl; hydroxymethyl; mercapto- nethyl; benzyl; or substituted benzyl; R7 and R8 may be the same or different and are each independently COOR or CONR'R", where R is hydrogen or C1-7 alkyl, and R' and R" are each independently hydrggen or C1-3 alkyl; when R2 is C1-10 alkyl, the steraochemistry at asym- metric center I can be either ? or ?; when R6 is not hydxoqen, the storeochemistry at asymmetric center II is ?; the atereochemistry at asymmetric center III is ?.

376750

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