C-20- and c-23-modified macrolide derivatives

Details C-20- and c-23-modified macrolide derivatives C-20- and c-23-modified macrolide derivatives

C - Chemistry, Metallurgy

07

H

260/230.35

C07H 17/08 (2006.01)

Patent

CA 1234807

- i - ABSTRACT OF THE DISCLOSURE Described herein are novel C-20 and C-23 modified derivatives of tylosin and tylosin-like macrolides having the following formula (I): Image (I) wherein R is hydrogen, halo, cyano, -OR4, -OAr, -SR5, azido, N-phthalimido, amino (substituted or unsubstituted), or (substituted or unsubstituted) amido, where: R4 is hydrogen, C1-C4 alkyl, cyclohexyl, or (optionally substituted) benzyl, phenethyl or phenoxy- ethyl; Ar is an aryl, heteroaryl, alkanoyl or aroyl group; and R5 is a C1-C4 alkyl, cyclohexyl, aryl or heteroaryl group; - ii - R1 is hydrogen, hydroxy, halo, -OAr, (where Ar is as defined above), -SR5 (where R5 is as defined above), -O-tetrahydrofuranyl, -O-tetrahydropyanyl, azido, N-phthalimido, (substituted or unsubstituted) amino, or (substituted or unsubstituted) amido, or an N-containing heterocyclic group; R2 is hydrogen, or an optionally substituted C1-C5 alkanoyl, benzoyl, phenylacetyl or phenyl- propionyl group, and R3 is hydrogen, hydroxy, or an optionally substituted C1-C5 alkanoyloxy, benzoyloxy, phenylacetoxy or phenylpropionyloxy group, or a mycarosyloxy group. These compounds are useful as antibiotics and/or as intermediates for preparing macrolide antibiotics.

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