Derivatives of a-21978c cyclic peptides

Details Derivatives of a-21978c cyclic peptides Derivatives of a-21978c cyclic peptides

C - Chemistry, Metallurgy

07

K

530/7.08

C07K 7/64 (2006.01) A61K 35/00 (2006.01) C07K 7/08 (2006.01) C07K 7/50 (2006.01) C07K 7/58 (2006.01) C07K 7/62 (2006.01) C07K 11/02 (2006.01) C12P 21/04 (2006.01)

Patent

CA 1216579

Abstract of the Invention This invention relates to A-21978C cyclic peptide derivatives of the formula Image in which R, R1 and R2 are, independently, hydrogen, C4-Cl4-alkyl, optionally substituted C2-C19-alkanoyl, C5-C19-alkenoyl or an amino-protecting group, R3, R4 and R5 are all hydrogen, or (i) R3 and R1; and/or (ii) R4 and R, and/or (iii) R5 and R2, taken together may represent a C4-C14 alkylidene group, provided that 1) at least one of R, R1 or R2 must be other than hydrogen or an amino-protecting group, 2) at least one of R1 or R2 must be hydrogen or an amino-protecting group, 3) the R, R1 and R2 groups must together contain at least four carbon atoms, and 4) when R1 and R2 are both selected from hydrogen or an amino-protecting group, R cannot be 8-methyldecanoyl, 10-methylundecanoyl, 10-methyldodecanoyl, the specific C10-alkanoyl group of A-21978C factor C0 or the specific C12-alkanoyl groups of A-21978C factors C4 and C5; and the pharmaceutically- acceptable salts thereof. This invention also relates to the production of these useful antibiotics and intermediates to useful antibiotics. This process includes acylating or alkylating the A-21978C nucleus or a protected derivative thereof, with the desired acylating agent or an activated derivative thereof, or in the case of the alkylated derivatives, preparing the appropriate Schiff base followed by reduction of the imine bond, and optionally, if desired, removing any protecting group present in the product of the reactions.

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