Analogs of lincomycin and clindamycin

Details Analogs of lincomycin and clindamycin Analogs of lincomycin and clindamycin

C - Chemistry, Metallurgy

07

H

260/228

C07H 15/16 (2006.01)

Patent

CA 1164864

ABSTRACT OF THE DISCLOSURE Novel useful analogs of the well known antibiotics lincomycin and clindamycin. These analogs are prepared by condensing a cyclic acid with a sugar amine and are re!presented by the general formula: Image wherein A, B and E are nitrogen, CH3-N?, oxygen, sulfur or CR1R1; wherein R1, which can be singly or multiply attached to any ring carbon atom not already substituted by R2, is hydrogen, alkyl and substituted alkyl, wherein the alkyl portion is from 1 to 8 carbon atoms, and isomeric forms thereof, cyclo- alkyl and substituted cycloalkyl, substituted oxygen, sub- stituted nitrogen, halogen, phenyl and substituted phenyl or -(CH2)m-OH, -(CH2)m-NR4R5, and isomeric forms thereof, wherein m is an integer of from 1 to 8, and R4 and R5 are hydrogen or alkyl of from 1 to 8 carbon atoms and isomeric forms there- of; and wherein R2, which can be attached to any ring carbon, not already substituted by Rl, or nitrogen atom, is: -?-X and X is the amino function of 7(R)-hydroxy-methyl 1-thio-.alpha.- lincosaminide, 7(S)-hydroxy-methyl 1-thio-.alpha.-lincosaminide, 7(S)-halo-methyl 1-thio-.alpha.-lincosaminide, 7(R)-halo-methyl 1-thio-.alpha.-lincosaminide, 7(S)-methoxy-methyl 1-thio-.alpha.-linco- saminide, 7-deoxy-7(S)-(methylthio)-methyl 1-thio-.alpha.-linco- saminide, 7-deoxy-7(S)-(2-hydroxyethylthio)-methyl 1-thio-.alpha.- lincosaminide or 7-deoxy-7(S)-(3-hydroxypropylthio)-methyl 1-thio-.alpha.-lincosaminide.

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