Erythromycin a 11,12-carbonate 9-oxime derivatives

Claim 2

A compound of the formula I, ##STR7## a pharmaceutically acceptable ester thereof or a pharmaceutically acceptable acid addition salt thereof wherein R 1 is unsubstituted or substituted oxime of the formula II ═N O--R.sup.B TM II wherein R B is hydrogen, unsubstituted or substituted alkyl of 1 to 6 carbon atoms, unsubstituted or substituted alkenyl of 2 to 6 carbon atoms, unsubstituted or substituted alkynyl of 2 to 6 carbon atoms, unsubstituted or substituted cycloalkyl of 3 to 7 carbon atoms, unsubstituted or substituted aryl, unsubstituted or substituted cycloalkyl alkyl of 3 to 7 carbon atoms in the cycloalkyl moiety and 1 to 6 carbon atoms in the alkyl moiety, unsubstituted or substituted arylalkyl of 1 to 6 carbon atoms in the alkyl moiety, unsubstituted or substituted alkylcycloalkyl of 1 to 6 carbon atoms in the alkyl moiety and 3 to 7 carbon atoms in the cycloalkyl moiety or unsubstituted or substituted alkylaryl of 1 to 6 carbon atoms in the alkyl moiety wherein the aryl moiety is phenyl or naphthyl and wherein the substituents are selected from the group consisting of heterocyclyl, amino, mono-, di- or tri- alkyl amino of 1 to 6 carbon atoms in the alkyl moiety, alkanoyl amino of 1 to 6 carbon atoms in the alkyl moiety, hydroxy, alkoxy of 1 to 6 carbon atoms, alkoxyalkoxy of 1 to 6 carbon atoms in each alkoxy moiety, alkenyloxy of 2 to 6 carbon atoms, alkynyloxy of 2 to 6 carbon atoms, aryloxy wherein aryl is as above defined, aralkyloxy wherein the aryl moiety is as above defined and the alkyl moiety is of 1 to 6 carbon atoms, mercapto, alkylthio of 1 to 6 carbon atoms, alkenylthio of 2 to 6 carbon atoms, alkynylthio of 2 to 6 carbon atoms, arylthio wherein aryl is as above defined, aralkylthio wherein the aryl moiety is above defined and the alkyl moiety is of 1 to 6 carbon atoms, heterocyclylthio, sulphamoyl, carbamoyl, amidino, guanidino, nitro, oxo, formyl, chloro, bromo, fluoro, cyano, thiocyanato, carboxy, a carboxyl salt, a carboxyl ester, alkanoyloxy of 1 to 6 carbon atoms, acyl, arylcarbonyloxy wherein aryl is as above defined, and heterocyclylcarbonyloxy, or R B is acyl; or R 1 is imino; R 3 is hydrogen or alkyl of 1 to 6 carbon atoms unsubstituted or substituted by heterocyclyl, amino, mono-, di- or tri- alkyl amino of 1 to 6 carbon atoms in each alkyl moiety, alkanoyl amino of 1 to 6 carbon atoms in the alkyl moiety, hydroxy, alkoxy of 1 to 6 carbon atoms, alkoxyalkoxy of 1 to 6 carbon atoms in each alkoxy moiety, alkenyloxy of 2 to 6 carbon atoms, alkynyloxy of 2 to 6 carbon atoms, aryloxy wherein aryl is as above defined, aralkyloxy wherein the aryl moiety is as above defined and the alkyl moiety is of 1 to 6 carbon atoms, mercapto, alkylthio of 1 to 6 carbon atoms, alkenylthio of 2 to 6 carbon atoms, alkynylthio of 2 to 6 carbon atoms, arylthio wherein aryl is as above defined, aralkylthio wherein the aryl moiety is above defined and the alkyl moiety is of 1 to 6 carbon atoms, heterocyclylthio, sulphamoyl, carbamoyl, amidino, guanidino, nitro, oxo, formyl, chloro, bromo, fluoro, cyano, thiocyanato, carboxy, a carboxyl salt, a carboxyl ester, alkanoyloxy of 1 to 6 carbon atoms, acyl, arylcarbonyloxy wherein aryl is as above defined, and heterocyclylcarbonyloxy; R 7 is hydrogen or methyl; one of R 8 and R 9 is hydrogen, hydroxy, alkoxy of 1 to 6 carbon atoms, alkanoyloxy of 1 to 6 carbon atoms, amino or R A --SO 2 --O--wherein R A is unsubstituted or substituted alkyl of 1 to 6 carbon atoms, unsubstituted or substituted alkenyl of 2 to 6 carbon atoms, unsubstituted or substituted aryl wherein aryl is as above defined, unsubstituted or substituted aralkyl wherein aryl is as above defined and the alkyl moiety is of 1 to 6 carbon atoms, unsubstituted or substituted aryloxyalkyl of 1 to 6 carbon atoms in the alkyl moiety wherein aryl is as above defined and wherein the substituent is selected from the group consisting of heterocyclyl, amino, mono-, di- or tri- alkyl amino of 1 to 6 carbon atoms in each alkyl moiety, alkanoyl amino of 1 to 6 carbon atoms in the alkyl moiety, hydroxy, alkoxy of 1 to 6 carbon atoms, alkoxyalkoxy of 1 to 6 carbon atoms in each alkoxy moiety, alkenyloxy of 2 to 6 carbon atoms, alkynyloxy of 2 to 6 carbon atoms, aryloxy as above defined, aralkyloxy wherein the aryl moiety is as above defined and the alkyl moiety is of 1 to 6 carbon atoms, mercapto, alkylthio of 1 to 6 carbon atoms, alkenylthio of 2 to 6 carbon atoms, alkynylthio of 2 to 6 carbon atoms, arylthio wherein aryl is as above defined, aralkylthio wherein the aryl moiety is above defined and the alkyl moiety is of 1 to 6 carbon atoms, heterocyclylthio, sulphamoyl, carbamoyl, amidino, guanidino, nitro, oxo, formyl, chloro, bromo, fluoro, cyano, thiocyanato, carboxy, a carboxyl salt, a carboxyl ester, alkanoyloxy of 1 to 6 carbon atoms, acyl, arylcarbonyloxy wherein aryl is as above defined, and heterocyclylcarbonyloxy; or R A it R G --CH 2 --CH 2 --SO 2 --O-- wherein R G is amino, carbamoyl, sulphamoyl, ureido, thioureido, alkoxy of 1 to 6 carbon atoms, alkylthio of 1 to 6 carbon atoms, aryloxy wherein the aryl moiety is as above defined, arylthio wherein the aryl moiety is as above defined, or benzyloxy, and the other of R 8 and R 9 is hydrogen, or R 8 and R 9 together are oxo, oxime, or substituted oxime of the formula II ═N O--R.sup.B II wherein R B is as above defined.

Claim 3

A compound according to claim 1 which is selected from the group consisting of erythromycin A 11,12-carbonate 9-oxime; erythromycin A 11,12-carbonate 9-methoxime; 6-O-methylerythromycin A 11,12-carbonate 9-methoxime; 6-O-methylerythromycin A 11,12-carbonate 9-ethoxime; 6-O-methylerythromycin A 11,12-carbonate 9-oxime; 6-O-methylerythromycin A 11,12-carbonate 9-(2-methoxyethoxymethyl)oxime; 6-O-methylerythromycin A 11,12-carbonate 9-methoxymethyloxime; erythromycin A 11,12-carbonate 9- ethoxime; erythromycin A 11,12-carbonate 9-isopropyloxime; erythromycin A 11,12-carbonate 9-carbamoylmethyloxime; erythromycin A 11,12-carbonate 9-methoxymethyloxime; erythromycin A 11,12-carbonate 9-(2-methoxyethoxymethyl)oxime; erythromycin A 11,12 -carbonate 9-(2-hydroxyethyl)oxime; erythromycin A 11,12-carbonate 9-(2-keto-1-pyrrolodinylmethyl)oxime; erythromycin A 11,12-carbonate-9-prop-2-enyloxime; erythromycin A 11,12-carbonate-9-n-propyloxime; erythromycin A 11,12-carbonate-9-ethoxymethyloxime; erythromycin A 11,12-carbonate-9-(2-dimethylaminoethyl)oxime; erythromycin A 11,12-carbonate-9-methylthiomethoxime; erythromycin A 11,12-carbonate-9-cyclopentyloxime; erythromycin A 11,12-carbonate-9-(2-methylprop-2-enyl)-oxime; erythromycin A 11,12-carbonate-9-(2-methylpropyl)oxime; erythromycin A 11,12-carbonate-9-(2-oxopropyl)oxime; erythromycin A 11,12-carbonate-9-dimethyl-carbamoylmethoxime; erythromycin A 11,12-carbonate-9-(2-methoxyethyl)oxime; erythromycin A 11,12-carbonate-9-methoxycarbonylmethyloxime; erythromycin A 11,12-carbonate-9-(2-pyridyl)methyloxime; erythromycin A 11,12-carbonate 9-isopropyloxime, a pharmaceutically acceptable ester thereof and a pharmaceutically acceptable acid addition salt thereof.

Claim 4

A pharmaceutical composition useful for treating bacterial infections in humans and animals which comprises an antibacterially effective amount of the compound of the formula I, ##STR8## a pharmaceutically acceptable ester thereof or a pharmaceutically acceptable acid addition salt thereof wherein R 1 is unsubstituted or substituted oxime of the formula II ═N O--R.sup.B II wherein R B is hydrogen, unsubstituted or substituted alkyl of 1 to 6 carbon atoms, unsubstituted or substituted alkenyl of 2 to 6 carbon atoms, unsubstituted or substituted alkynyl of 2 to 6 carbon atoms, unsubstituted or substituted cycloalkyl of 3 to 7 carbon atoms, unsubstituted or substituted aryl, unsubstituted or substituted cycloalkyl alkyl of 3 to 7 carbon atoms in the cycloalkyl moiety and 1 to 6 carbon atoms in the alkyl moiety, unsubstituted or substituted arylalkyl of 1 to 6 carbon atoms in the alkyl moiety, unsubstituted or substituted alkylcycloalkyl of 1 to 6 carbon atoms in the alkyl moiety and 3 to 7 carbon atoms in the cycloalkyl moiety or unsubstituted or substituted alkylaryl of 1 to 6 carbon atoms in the alkyl moiety wherein the aryl moiety is phenyl or naphthyl and wherein the substituents are selected from the group consisting of heterocyclyl, amino, mono-, di- or tri- alkyl amino of 1 to 6 carbon atoms in each alkyl moiety, alkanoyl amino of 1 to 6 carbon atoms in the alkyl moiety hydroxy, alkoxy of 1 to 6 carbon atoms, alkoxyalkoxy of 1 to 6 carbon atoms in each alkoxy moiety, alkenyloxy of 2 to 6 carbon atoms, alkynyloxy of 2 to 6 carbon atoms, aryloxy wherein aryl is as above defined, aralkyloxy wherein the aryl moiety is as above defined and the alkyl moiety is of 1 to 6 carbon atoms, mercapto, alkylthio of 1 to 6 carbon atoms, alkenylthio of 2 to 6 carbon atoms, alkynylthio of 2 to 6 carbon atoms, arylthio wherein aryl is as above defined, aralkylthio wherein the aryl moiety is above defined and the alkyl moiety is of 1 to 6 carbon atoms, heterocyclylthio, sulphamoyl, carbamoyl, amidino, guanidino, nitro, oxo, formyl, chloro, bromo, fluoro, cyano, thiocyanato, carboxy, a carboxyl salt, a carboxyl ester, alkanoyloxy of 1 to 6 carbon atoms, acyl, arylcarbonyloxy wherein aryl is as above defined, and heterocyclylcarbonyloxy, or R B is acyl; or R 1 is imino; R 3 is hydrogen or alkyl of 1 to 6 carbon atoms unsubstituted or substituted by heterocyclyl, amino, mono-, di- or tri- alkyl amino of 1 to 6 carbon atoms in each alkyl moiety, alkanoyl amino of 1 to 6 carbon atoms in the alkyl moiety, hydroxy, alkoxy of 1 to 6 carbon atoms, alkoxyalkoxy of 1 to 6 carbon atoms in each alkoxy moiety, alkenyloxy of 2 to 6 carbon atoms, alkynyloxy of 2 to 6 carbon atoms, aryloxy wherein aryl is as above defined, aralkyloxy wherein the aryl moiety is as above defined and the alkyl moiety is of 1 to 6 carbon atoms, mercapto, alkylthio of 1 to 6 carbon atoms, alkenylthio of 2 to 6 carbon atoms, alkynylthio of 2 to 6 carbon atoms, arylthio wherein aryl is as above defined, aralkylthio wherein the aryl moiety is above defined and the alkyl moiety is of 1 to 6 carbon atoms, heterocyclylthio, sulphamoyl, carbamoyl, amidino, guanidino, nitro, oxo, formyl, chloro, bromo, fluoro, cyano, thiocyanato, carboxy, a carboxyl salt, a carboxyl ester, alkanoyloxy of 1 to 6 carbon atoms, acyl, arylcarbonyloxy wherein aryl is as above defined, and heterocyclylcarbonyloxy; R 7 is hydrogen or methyl; one of R 8 and R 9 is hydrogen, hydroxy, alkoxy of 1 to 6 carbon atoms, alkanoyloxy of 1 to 6 carbon atoms, amino or R A --SO 2 --O--wherein R A is unsubstituted or substituted alkyl of 1 to 6 carbon atoms, unsubstituted or substituted alkenyl of 2 to 6 carbon atoms, unsubstituted or substituted aryl wherein aryl is as above defined, unsubstituted or substituted aralkyl wherein aryl is as above defined and the alkyl moiety has 1 to 6 carbon atoms, unsubstituted or substituted aryloxyalkyl of 1 to 6 carbon atoms in the alkyl moiety wherein aryl is as above defined and wherein the substituent is selected from the group consisting of heterocyclyl, amino, mono-, di- or tri- alkyl amino of 1 to 6 carbon atoms in each alkyl moiety, alkanoyl amino of 1 to 6 carbon atoms in the alkyl moiety, hydroxy, alkoxy of 1 to 6 carbon atoms, alkoxyalkoxy of 1 to 6 carbon atoms in each alkoxy moiety, alkenyloxy of 2 to 6 carbon atoms, alkynyloxy of 2 to 6 carbon atoms, aryloxy wherein aryl is as above defined, aralkyloxy wherein the aryl moiety is as above defined and the alkyl moiety is of 1 to 6 carbon atoms, mercapto, alkylthio of 1 to 6 carbon atoms, alkenylthio of 2 to 6 carbon atoms, alkynylthio of 2 to 6 carbon atoms, arylthio wherein aryl is as above defined, aralkylthio wherein the aryl moiety is above defined and the alkyl moiety is of 1 to 6 carbon atoms, heterocyclylthio, sulphamoyl, carbamoyl, amidino, guanidino, nitro, oxo, formyl, chloro, bromo, fluoro, cyano, thiocyanato, carboxy, a carboxyl salt, a carboxyl ester, alkanoyloxy of 1 to 6 carbon atoms, acyl, arylcarbonyloxy wherein aryl is as above defined, and heterocyclylcarbonyloxy; or R A is R G --CH 2 --CH 2 --SO 2 --O--wherein R G is amino, carbamoyl, sulphamoyl, ureido, thioureido, alkoxy of 1 to 6 carbon atoms, alkylthio of 1 to 6 carbon atoms, aryloxy wherein the aryl moiety is as above defined, arylthio wherein the aryl moiety is as above defined, or benzyloxy, and the other of R 8 and R 9 is hydrogen, or R 8 and R 9 together are oxo, oxime, or substituted oxime or the formula II ═N O--R.sup.B II wherein R B is as above defined, in combination with a pharmaceutically acceptable carrier.

Claim 5

A pharmaceutical composition useful for treating bacterial infections in humans and animals which comprises an antibacterially effective amount of the compound of the formula I, ##STR8## a pharmaceutically acceptable ester thereof or a pharmaceutically acceptable acid addition salt thereof wherein R 1 is unsubstituted or substituted oxime of the formula II ═N O--R.sup.B II wherein R B is hydrogen, unsubstituted or substituted alkyl of 1 to 6 carbon atoms, unsubstituted or substituted alkenyl of 2 to 6 carbon atoms, unsubstituted or substituted alkynyl of 2 to 6 carbon atoms, unsubstituted or substituted cycloalkyl of 3 to 7 carbon atoms, unsubstituted or substituted aryl, unsubstituted or substituted cycloalkyl alkyl of 3 to 7 carbon atoms in the cycloalkyl moiety and 1 to 6 carbon atoms in the alkyl moiety, unsubstituted or substituted arylalkyl of 1 to 6 carbon atoms in the alkyl moiety, unsubstituted or substituted alkylcycloalkyl of 1 to 6 carbon atoms in the alkyl moiety and 3 to 7 carbon atoms in the cycloalkyl moiety or unsubstituted or substituted alkylaryl of 1 to 6 carbon atoms in the alkyl moiety wherein the aryl moiety is phenyl or naphthyl and wherein the substituents are selected from the group consisting of heterocyclyl, amino, mono-, di- or tri- alkyl amino of 1 to 6 carbon atoms in each alkyl moiety, alkanoyl amino of 1 to 6 carbon atoms in the alkyl moiety hydroxy, alkoxy of 1 to 6 carbon atoms, alkoxyalkoxy of 1 to 6 carbon atoms in each alkoxy moiety, alkenyloxy of 2 to 6 carbon atoms, alkynyloxy of 2 to 6 carbon atoms, aryloxy wherein aryl is as above defined, aralkyloxy wherein the aryl moiety is as above defined and the alkyl moiety is of 1 to 6 carbon atoms, mercapto, alkylthio of 1 to 6 carbon atoms, alkenylthio of 2 to 6 carbon atoms, alkynylthio of 2 to 6 carbon atoms, arylthio wherein aryl is as above defined, aralkylthio wherein the aryl moiety is above defined and the alkyl moiety is of 1 to 6 carbon atoms, heterocyclylthio, sulphamoyl, carbamoyl, amidino, guanidino, nitro, oxo, formyl, chloro, bromo, fluoro, cyano, thiocyanato, carboxy, a carboxyl salt, a carboxyl ester, alkanoyloxy of 1 to 6 carbon atoms, acyl, arylcarbonyloxy wherein aryl is as above defined, and heterocyclylcarbonyloxy, or R B is acyl; or R 1 is imino; R 3 is hydrogen or alkyl of 1 to 6 carbon atoms unsubstituted or substituted by heterocyclyl, amino, mono-, di- or tri- alkyl amino of 1 to 6 carbon atoms in each alkyl moiety, alkanoyl amino of 1 to 6 carbon atoms in the alkyl moiety, hydroxy, alkoxy of 1 to 6 carbon atoms, alkoxyalkoxy of 1 to 6 carbon atoms in each alkoxy moiety, alkenyloxy of 2 to 6 carbon atoms, alkynyloxy of 2 to 6 carbon atoms, aryloxy wherein aryl is as above defined, aralkyloxy wherein the aryl moiety is as above defined and the alkyl moiety is of 1 to 6 carbon atoms, mercapto, alkylthio of 1 to 6 carbon atoms, alkenylthio of 2 to 6 carbon atoms, alkynylthio of 2 to 6 carbon atoms, arylthio wherein aryl is as above defined, aralkylthio wherein the aryl moiety is above defined and the alkyl moiety is of 1 to 6 carbon atoms, heterocyclylthio, sulphamoyl, carbamoyl, amidino, guanidino, nitro, oxo, formyl, chloro, bromo, fluoro, cyano, thiocyanato, carboxy, a carboxyl salt, a carboxyl ester, alkanoyloxy of 1 to 6 carbon atoms, acyl, arylcarbonyloxy wherein aryl is as above defined, and heterocyclylcarbonyloxy; R 7 is hydrogen or methyl; one of R 8 and R 9 is hydrogen, hydroxy, alkoxy of 1 to 6 carbon atoms, alkanoyloxy of 1 to 6 carbon atoms, amino or R A --SO 2 --O--wherein R A is unsubstituted or substituted alkyl of 1 to 6 carbon atoms, unsubstituted or substituted alkenyl of 2 to 6 carbon atoms, unsubstituted or substituted aryl wherein aryl is as above defined, unsubstituted or substituted aralkyl wherein aryl is as above defined and the alkyl moiety has 1 to 6 carbon atoms, unsubstituted or substituted aryloxyalkyl of 1 to 6 carbon atoms in the alkyl moiety wherein aryl is as above defined and wherein the substituent is selected from the group consisting of heterocyclyl, amino, mono-, di- or tri- alkyl amino of 1 to 6 carbon atoms in each alkyl moiety, alkanoyl amino of 1 to 6 carbon atoms in the alkyl moiety, hydroxy, alkoxy of 1 to 6 carbon atoms, alkoxyalkoxy of 1 to 6 carbon atoms in each alkoxy moiety, alkenyloxy of 2 to 6 carbon atoms, alkynyloxy of 2 to 6 carbon atoms, aryloxy wherein aryl is as above defined, aralkyloxy wherein the aryl moiety is as above defined and the alkyl moiety is of 1 to 6 carbon atoms, mercapto, alkylthio of 1 to 6 carbon atoms, alkenylthio of 2 to 6 carbon atoms, alkynylthio of 2 to 6 carbon atoms, arylthio wherein aryl is as above defined, aralkylthio wherein the aryl moiety is above defined and the alkyl moiety is of 1 to 6 carbon atoms, heterocyclylthio, sulphamoyl, carbamoyl, amidino, guanidino, nitro, oxo, formyl, chloro, bromo, fluoro, cyano, thiocyanato, carboxy, a carboxyl salt, a carboxyl ester, alkanoyloxy of 1 to 6 carbon atoms, acyl, arylcarbonyloxy wherein aryl is as above defined, and heterocyclylcarbonyloxy; or R A is R G --CH 2 --CH 2 --SO 2 --O--wherein R G is amino, carbamoyl, sulphamoyl, ureido, thioureido, alkoxy of 1 to 6 carbon atoms, alkylthio of 1 to 6 carbon atoms, aryloxy wherein the aryl moiety is as above defined, arylthio wherein the aryl moiety is as above defined, or benzyloxy, and the other of R 8 and R 9 is hydrogen, or R 8 and R 9 together are oxo, oxime, or substituted oxime or the formula II ═N O--R.sup.B II wherein R B is as above defined, in combination with a pharmaceutically acceptable carrier.

Claim 6

A composition according to claim 3 wherein the compound is selected from the group consisting of erythromycin A 11,12-carbonate 9-oxime; erythromycin A 11,12-carbonate 9-methoxime; 6-O-methylerythromycin A 11,12-carbonate 9-methoxime; 6-O-methylerythromycin A 11,12-carbonate 9-ethoxime; 6O-methylerythromycin A 11,12-carbonate 9-oxime; 6-O-methylerythromycin A 11,12-carbonate 9-(2-methoxyethoxymethyl)oxime; 6-O-methylerythromycin A 11,12-carbonate 9-methoxymethyloxime; erythromycin A 11,12-carbonate 9-ethoxime; erythromycin A 11,12-carbonate 9-isopropyloxime; erythromycin A 11,12-carbonate 9-carbamoylmethyloxime; erythromycin A 11,12-carbonate 9-methoxymethyloxime; erythromycin A 11,12-carbonate 9-(2-methoxyethoxymethyl)oxime; erythromycin A 11,12-carbonate 9-(2-hydroxyethyl)oxime; erythromycin A 11,12-carbonate 9-(2-keto-1-pyrrolidinylmethyl)oxime; erythromycin A 11,12-carbonate-9-prop-2-enyloxime; erythromycin A 11,12-carbonate-9-n-propyloxime; erythromycin A 11,12-carbonate-9-ethoxymethyloxime; erythromycin A 11,12-carbonate-9-(2-dimethylaminoethyl)oxime; erythromycin A 11,12-carbonate-9-methylthiomethoxime; erythromycin A 11,12-carbonate-9-cyclopentyloxime; erythromycin A 11,12-carbonate-9-(2-methylprop-2-enyl)-oxime; erythromycin A 11,12-carbonate-9-(2-methylpropyl)oxime; erythromycin A 11,12-carbonate- 9-(2-oxopropyl)oxime; erythromycin A 11,12-carbonate-9-dimethylcarbamoylmethoxime; erythromycin A 11,12-carbonate-9-(2-methoxyethyl)oxime; erythromycin A 11,12-carbonate-9-methoxycarbonylmethyloxime; erythromycin A 11,12-carbonate-9-(2-pyridyl)methyloxime; erythromycin A 11,12-carbonate 9-isopropyloxime, a pharmaceutically acceptable ester thereof and a pharmaceutically acceptable acid addition salt thereof.

Claim 9

A method according to claim 5 wherein the compound is selected from the group consisting of erythromycin A 11,12-carbonate 9-oxime; erythromycin A 11,12-carbonate 9-methoxime; 6O-methylerythromycin A 11,12-carbonate 9-methoxime; 6O-methylerythromycin A 11,12-carbonate 9-ethoxime; 6O-methylerythromycin A 11,12-carbonate 9-oxime; 6-O-methylerythromycin A 11,12-carbonate 9-(2-methoxyethoxymethyl)oxime; 6-O-methylerythromycin A 11,12-carbonate 9-methoxymethyloxime; erythromycin A 11,12-carbonate 9-ethoxime; erythromycin A 11,12-carbonate 9-isopropyloxime; erythromycin A 11,12-carbonate 9-carbamoylmethyloxime; erythromycin A 11,12-carbonate 9-methoxymethyloxime; erythromycin A 11,12-carbonate 9-(2-methoxyethoxymethyl)oxime; erythromycin A 11,12-carbonate 9-(2-hydroxyethyl)oxime; erythromycin A 11,12-carbonate 9-(2-keto-1-pyrrolidinylmethyl)oxime; erythromycin A 11,12-carbonate-9-prop-2-enyloxime; erythromycin A 11,12-carbonate-9-n-propyloxime; erythromycin A 11,12-carbonate-9-ethoxymethyloxime; erythromycin A 11,12-carbonate-9-(2-dimethylaminoethyl)oxime; erythromycin A 11,12-carbonate-9-methylthiomethoxime; erythromycin A 11,12-carbonate-9-cyclopentyloxime; erythromycin A 11,12-carbonate-9-(2-methylprop-2-enyl)-oxime; erythromycin A 11,12-carbonate-9-(2-methylpropyl)oxime; erythromycin A 11,12-carbonate-9-(2-oxopropyl)oxime; erythromycin A 11,12-carbonate-9-dimethylcarbamoylmethoxime; erythromycin A 11,12-carbonate-9-(2-methoxyethyl)oxime; erythromycin A 11,12-carbonate-9-methoxycarbonylmethyloxime; erythromycin A 11,12-carbonate-9-(2-pyridyl)methyloxime; erythromycin A 11,12-carbonate 9-isopropyloxime, a pharmaceutically acceptable ester thereof and a pharmaceutically acceptable acid addition salt thereof.