Derivatives of antibiotic AR-5 components

Compounds of the formulae:

• ##STR3## and the pharmaceutically acceptable salts thereof and esters thereof of acids selected from the group consisting of acetic, propionic, oxalic, valeric, oleic, palmitic, stearic, lauric, benzoic, lactic, para toluene sulfonic, methane sulfonic, citric, maleic, fumaric, tartaric, succinic, naphthalene sulfonic and adamantoic, wherein the wavy line indicates that the substituent may be in any of the possible stereochemical configurations;
• R is a member of a group consisting of hydrogen and hydroxyl;
• R' is a member of a group consisting of hydrogen and C.sub.2 -C.sub.18 alkanoyl, carbamoyl and thiocarbamoyl;
• M is a member of the group consisting of oxygen and H,OR';
• Q is a member of the group consisting of --NZ and --SZ' wherein --NZ is a member of the group consisting of amino, acylamino wherein the acyl group is an amionacid residue, C.sub.1 -C.sub.18 akylamino, C.sub.2 -C.sub.36 dialkylamino, hydroxy (C.sub.1 -C.sub.18)alkylamino, C.sub.1 -C.sub.18 alkylimino, or C.sub.7 -C.sub.18 aralkylimino, aminothiocarbonylamino(C.sub.1 -C.sub.18)alkyl, amidinyl, C.sub.1 -C.sub.18 alkylcarboxyamino, ureido, 4-ethyl-2,3-dioxopiperazinocarbonylamino, guanidino, C.sub.1 -C.sub.18, alkylguanidino and an aminoacid residue;
• --SZ' is a member of the group consisting of C.sub.1 -C.sub.18 alkylthio, thioxanthyl, including C.sub.1 -C.sub.18 alkyl, phenyl, phenyl substituted with a member of the group consisting of halogeno, trifluoromethyl, hydroxy and lower alkoxy, C.sub.7 -C.sub.18 aralkyl, thioxanthyl, C.sub.1 -C.sub.18 alkylamino(C.sub.1 -C.sub.18)alkylthio, phenylthio, halogenophenylthio, trifluoromethylphenylthio, hydroxyphenylthio, loweralkoxyphenylthio, C.sub.2 -C.sub.18 aralkylthio, heterocyclethio, heterocycle (C.sub.1 -C.sub.18) alkylthio, heterocycle (C.sub.7 -C.sub.18) aralkylthio, heterocyclephenylthio, heterocycle(halogeno) phenylthio, heterocycle(trifluoromethyl)phenylthio, heterocycle(hydroxy)phenylthio, heterocycle(loweralkoxy)phenylthio, (wherein the heterocycle contains at least one hetero atom selected from the group consisting of sulfur, nitrogen and oxygen), C.sub.1 -C.sub.18 alkylcarboxy(C.sub.1 -C.sub.18)alkylthio and sulfur containing amino acid residues, X is a member of the group consisting of hydrogen, OR'epi, mesyloxy, tosyloxy, trifluoromethanesulfonyloxy, halogeno, azido, amino, isocyanato, thiosiocyanato, C.sub.1 -C.sub.18 alkylimino, phenylimino, halogenophenylimino, trifluoromethylphenylimino, hydroxyphenylimino, loweralkoxyphenylimino, C.sub.7 -C.sub.18 aralkylimino, urethano, amidino, guanidino, C.sub.1 -C.sub.18 alkoxyamino, cyclicguanidino when Y is hydrogen;
• and Y in combination with X is oxygen.