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 1165315

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 repre- sented by the general formula: Image wherein R1, which can be singly or multiply substituted in the 2, 3, 4, 5, 6, 7, 8 or 9 position of the ring 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, cycloalkyl and substituted cyclo- alkyl, substituted oxygen, substituted 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 thereof; wherein R2, which can be singly substituted in any position of the ring not already substituted by R1, is: -?-X and X is the amino function of 7(R)-hydroxy-methyl l-thio- .alpha.-lincosaminide, 7(S)-hydroxy-methyl l-thio-.alpha.-lincosaminide, 7(S)-halo-methyl l-thio-.alpha.-lincosaminide, 7(R)-halo-methyl l-thio-.alpha.-lincosaminide, 7(S)-methoxy-methyl l-thio-.alpha.-linco- saminide, 7-deoxy-7(S)-(methylthio)-methyl l-thio-.alpha.-linco- saminide, 7-deoxy-7(S)-(2-hydroxyethylthio)-methyl l-thio- .alpha.-lincosaminide or 7-deoxy-7(S)-(3-hydroxypropylthio)-methyl l-thio-.alpha.-lincosaminide; wherein R3 is hydrogen, methyl 7 ethyl or C2H5OH; and wherein n is an integer of from 1 to 4.

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