9,3",4"-Triacyl ester of the antibiotic SF-837 M1 substance and the production thereof

Claim 2

A 9,3",4"-tri-alkanoyl SF-837 M 1 substance of the formula (II): ##STR11##wherein R 1 and R 4 are each acetyl or propionyl and R 3 is acetyl, propionyl, n-butyryl, isobutyryl or isovaleryl.

Claim 3

A 9,3",4"-tri-alkanoyl SF-837 M 1 substance as claimed in claim 1 which is of the formula (II'): ##STR12##wherein R 5 is acetyl or propionyl, R 6 is acetyl, propionyl, isobutyryl or isovaleryl, and R 7 is acetyl or propionyl, provided that when R 5 is acetyl, R 6 is acetyl or propionyl, provided that when R 5 and R 7 are each acetyl, R 6 is propionyl, provided that when R 5 is acetyl and R 7 is propionyl, R 6 is acetyl, propionyl, isobutyryl or isovaleryl, and provided that when R 5 is propionyl, R 6 is acetyl or propionyl and R 7 is propionyl.

Claim 4

A 9,3",4"-tri-alkanoyl SF-837 M 1 substance as claimed in claim 1, which is selected from the consisting of 9,4"-di-acetyl-3"-propionyl SF-837 M 1 substance; 9,3"-di-acetyl-4"-propionyl SF-837 M 1 substance; 9-acetyl-4"-isobutyryl-3"-propionyl SF-837 M 1 substance; 9-acetyl-4"-isovaleryl-3"-propionyl SF-837 M 1 substance; 9,3"-dipropionyl-4"-acetyl SF-837 M 1 substance; 9-acetyl-3",4"-dipropionyl SF-837 M 1 substance and 9,3",4"-tripropionyl SF-837 M 1 substance.

Claim 5

A 9,3",4"-tri-alkanoyl SF-837 M 1 substance as claimed in claim 1, which is 9,3"-di-acetyl-4"-propionyl SF-837 M 1 substance.

Claim 6

A 9,2',3",4"-tetra-alkanoyl SF-837 M 1 substance of the formula (III): ##STR13##wherein R 1 and R 4 are each acetyl or propionyl, R 2 is acetyl or propionyl, and R 3 is acetyl, propionyl, n-butyryl, isobutyryl or isovaleryl.

Claim 7

A 9,2',3",4"-tetra-alkanoyl SF-837 M 1 substance of the formula (III): ##STR13##wherein R 1 and R 4 are each acetyl or propionyl, R 2 is acetyl or propionyl, and R 3 is acetyl, propionyl, n-butyryl, isobutyryl or isovaleryl.

Claim 8

A 9,18,2',3",4"-penta-alkanoyl SF-837 M 1 substance of the formula (IV): ##STR14##wherein R 1 and R 4 are each acetyl or propionyl, R 2 is acetyl or propionyl, and R 3 is acetyl, propionyl, n-butyryl, isobutyryl or isovaleryl.

Claim 9

A 9,18,2',3",4"-penta-alkanoyl SF-837 M 1 substance of the formula (IV): ##STR14##wherein R 1 and R 4 are each acetyl or propionyl, R 2 is acetyl or propionyl, and R 3 is acetyl, propionyl, n-butyryl, isobutyryl or isovaleryl.

Claim 10

A pharmaceutical composition suitable for use in treating bacterial infections in a living animal, comprising a therapeutically effective amount of a compound selected from the group consisting of 9,3",4"-tri-alkanoyl SF-837 M 1 substance of the formula (II) as claimed in claim 1 (and/or), a pharmaceutically acceptable salt thereof and a mixture of said substance and said salt of the 9,3",4"-tri-alkanoyl SF-837 M 1 substance, in combination with a pharmaceutically acceptable carrier.

Claim 11

A process for the production of a 9,3",4"-tri-alkanoyl SF-837 M 1 substance of the formula (IT) as defined in claim 1, which comprises the step (i) of acylating an initial material selected from the group consisting of SF-837 substance, 9,2',4"-tri-acetyl SF-837 M 1 substance, 9,2'-di-acetyl SF-837 substance, 9-propionyl SF-837 substance and 9,2'-dipropionyl SF-837 substance of the formula (V) ##STR15##wherein R 1 ' and R 2 ' are each a hydrogen atom and R 3 ' is propionyl; or R 1 ', R 2 ' and R 3 ' are each acetyl; or R 1 ' and R 2 ' are each acetyl and R 3 ' is propionyl; or R 1 ' and R 3 ' are each propionyl and R 2 ' is a hydrogen atom; or R 1 ', R 2 ' and R 3 ' are each propionyl, with an alkanoic acid anhydride of the formula (VI): r.sub.3 --o--r.sub.3 (vi) wherein R 3 is acetyl, propionyl, n-butyryl, isobutyryl or isovaleryl group at a temperature of 50° to 120° C and in the presence of an organic base selected from pyridine, quinoline, α-picoline, diethylaniline, N-ethylmorpholine and triethylamine for a sufficient time to produce a 9,2',3",4"-tetra-alkanoyl SF-837 M 1 substance of the formula (III): ##STR16##wherein R 1 , R 2 and R 4 are each acetyl or propionyl and R 3 is as defined above in the formula (VI), provided that R 4 is the same as R 3 ' initially present at the 4"-position of the initial material employed, or a 9,18,2',3",4"-penta-alkanoyl SF-837 M 1 substance of the formula (IV): ##STR17##wherein R 1 , R 2 and R 4 are each acetyl or propionyl and R 3 is a defined above in the formula (VI), provided that R 4 is the same a R 3 ' initially present at the 4"-position of the initial material employed, or a mixture of these substances, with concurrent and intermolecular shifting of the alkanoyl group from the 4"-position to the 3"-position, and the step (ii) of hydrolyzing partially and selectively the 9,2',3",4"-tetra-alkanoyl SF-837 M 1 substance of the formula (III) or the 9,18,2',3",4"-penta-alkanoyl SF-837 M 1 substance or a mixture of these substances in an aqueous alkanol or an aqueous acetone at a temperature of from ambient temperature to the refluxing temperature of the aqueous alkanol or aqueous acetone employed, to produce the desired 9,3",4"-tri-alkanoyl SF-837 M 1 substance of the formula (II) as defined in claim 1.