Immunologically active dipeptidyl 2-amino-1,2-dideoxy...

C - Chemistry – Metallurgy – 07 – H

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260/8, 530/9

C07H 5/04 (2006.01) C07D 309/14 (2006.01) C07K 9/00 (2006.01)

Patent

CA 1173430

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 or different and are each independently hydrogen or acyl of the formula: Image where X is -O-, -S-,-CH2-, or Image ; R9, R10 and R12 may be the same or different and are each independently hydrogen; C1-20 alkyl;C2-20 alkenyl; C1-20 alkylcar- bonyloxy; amino; phenyl; benzyl; C1-20 alkoxy- methyl; or C1-20alkylamido; R11 is hydrogen; C1-30 alkyl; C2-30 alkenyl; C1-30 alkoxy; phenyl; C1-20 alkylsulfonyl; or cholesteryl; and m is 0-90; and n is 0 or 1 provided that when n is 0, R11 may additionally be 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 heterocycle option- ally substituted with C1-20alkylcarbonyl; R5 is hydrogen; or R5 R6 together is -CH2-CH2-CH2; R6 is hydrogen; C1-7 alkyl; hydroxymethyl; mercapto- methyl: 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 hydrogen or C1-3 alkyl; when R2 is C1-10 alkyl the stereochemistry at asym- metric center I can be either ? or ?; when R6 is not hydrogen the stereochemistry at at asymmetric center II is ?: the stereochemistry at asymmetric center III is ?.

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