US 6,472,384 B1 · Antimicrobial compounds

Abstract

The present invention relates to ester, ether and N-alkylcarbamoyl derivatives of compound (Ia) and pharmaceutically acceptable salts thereof. These compounds exhibit excellent antibacterial activity and are useful for the treatment or prevention of bacterial infections. (wherein R1 is a hydrogen atom or a methyl group; R2a is a hydrogen atom, a protecting group for a hydroxy group, or a methyl group; R3 is a hydrogen atom or a protecting group for a hydroxy group; R4a is a hydrogen atom, a hydroxy group or a protected hydroxy group; R5 is a hydrogen atom or a protecting group for a hydroxy group; and X is a methylene group or a sulfur atom). The invention also includes compounds which are related to the aforeidentified compounds.

Claims93

Dependent claims

A compound of formula (I) or a pharmaceutically acceptable salt thereof:

wherein:
R1 is a methyl group, R2 is a methyl group, R4 is a hydroxy group, and X is a methylene group;
R1 is a methyl group, R2 is a hydrogen atom, R4 is a hydroxy group, and X is a methylene group;
R1 is a methyl group, R2 is a methyl group, R4 is a hydrogen atom, and X is a methylene group;
R1 is a hydrogen atom, R2 is a hydrogen atom, R4 is a hydroxy group, and X is a methylene group;
or
R1 is a methyl group, R2 is a methyl group, R4 is a hydroxy group, and X is a sulfur atom.

4 more elements

A pharmaceutically acceptable ester, ether, or an N-carbamoyl selected from the group consisting of an N-alkylcarbamoyl, an N-alkenylcarbamoyl and an N-alkynylcarbamoyl of a compound of formula (Ia), or a pharmaceutically acceptable salt thereof:

wherein:
R1 is a hydrogen atom or a methyl group;
R2a is a hydrogen atom, a protecting group for a hydroxy group, or a methyl group;
R3 is a hydrogen atom or a protecting group for a hydroxy group;
R4a is a hydrogen atom, a hydroxy group or a protected hydroxy group;
R5 is a hydrogen atom or a protecting group for a hydroxy group;
and
X is a methylene group or a sulfur atom,
PROVIDED THAT:
when
X is a sulfur atom,
R1 is a methyl group, R2a is a methyl group, and R4a is a hydroxy group or a protected hydroxy group;
when
X is a methylene group, R1 is a methyl group, and R2a is a hydrogen atom,
R4a is a hydroxy group or a protected hydroxy group;
or
when
X is a methylene group, and R1 is a hydrogen atom,
R2a is a methyl group, and R4a is a hydroxy group or a protected hydroxy group;
AND THAT:
when X is a methylene group, R1 is a hydrogen atom, R2a is a methyl group, and R3 is a hydrogen atom or a phenoxythiocarbonyl group, R4a may not be a hydroxy group when R1 is a hydrogen atom, and R4a and R5 may not together represent an oxyalkylene group;
AND THAT the compound wherein X is a methylene group, R1 is a hydrogen atom, R2a is a methyl group, R3 is a pivaloyl group, R4a is an acetoxy group and R5 is an acetyl group is excluded.

19 more elements

A compound of formula (Ib) selected from the compound group consisting of the following compounds, or a pharmaceutically acceptable salt thereof.

a compound wherein R1 is a methyl group, R2 is a methyl group, R3a is a hydrogen atom, R4a is a hydroxy group, R5a is a hydrogen atom and X is a methylene group;
a compound wherein R1 is a methyl group, R2 is a hydrogen atom, R3a is a hydrogen atom, R4a is a hydroxy group, R5a is a hydrogen atom and X is a methylene group;
a compound wherein R1 is a methyl group, R2 is a methyl group, R3a is a hydrogen atom, R4a is a hydrogen atom, R5a is a hydrogen atom and X is a methylene group;
a compound wherein R1 is a methyl group, R2 is a methyl group, R3a is a decanoyl group, R4a is a hydroxy group, R5a is a hydrogen atom and X is a methylene group;
a compound wherein R1 is a methyl group, R2 is a methyl group, R3a is a lauroyl group, R4a is a hydroxy group, R5a is a hydrogen atom and X is a methylene group;
a compound wherein R1 is a methyl group, R2 is a methyl group, R3a is a myristoyl group, R4a is a hydroxy group, R5a is a hydrogen atom and X is a methylene group;
a compound wherein R1 is a methyl group, R2 is a methyl group, R3a is a pentadecanoyl group, R4a is a hydroxy group, R5a is a hydrogen atom and X is a methylene group;
a compound wherein R1 is a methyl group, R2 is a methyl group, R3a is a palmitoyl group, R4a is a hydroxy group, R5a is a hydrogen atom and X is a methylene group;
a compound wherein R1 is a hydrogen atom, R2 is a hydrogen atom, R3a is a hydrogen atom, R4a is a hydroxy group, R5a is a hydrogen atom and X is a methylene group;
a compound wherein R1 is a hydrogen atom, R2 is a methyl group, R3a is a decanoyl group, R4a is a hydroxy group, R5a is a hydrogen atom and X is a methylene group;
a compound wherein R1 is a hydrogen atom, R2 is a methyl group, R3a is a lauroyl group, R4a is a hydroxy group, R5a is a hydrogen atom and X is a methylene group;
a compound wherein R1 is a hydrogen atom, R2 is a methyl group, R3a is a myristoyl group, R4a is a hydroxy group, R5a is a hydrogen atom and X is a methylene group;
a compound wherein R1 is a hydrogen atom, R2 is a methyl group, R3a is a pentadecanoyl group, R4a is a hydroxy group, R5a is a hydrogen atom and X is a methylene group;
a compound wherein R1 is a hydrogen atom, R2 is a methyl group, R3a is a palmitoyl group, R4a is a hydroxy group, R5a is a hydrogen atom and X is a methylene group;
a compound wherein R1 is a methyl group, R2 is a methyl group, R3a is a hydrogen atom, R4a is a hydroxy group, R5a is a decanoyl group and X is a methylene group;
a compound wherein R1 is a methyl group, R2 is a methyl group, R3a is a hydrogen atom, R4a is a hydroxy group, R5a is a lauroyl group and X is a methylene group;
a compound wherein R1 is a methyl group, R2 is a methyl group, R3a is a hydrogen atom, R4a is a hydroxy group, R5a is a myristoyl group and X is a methylene group;
a compound wherein R1 is a methyl group, R2 is a methyl group, R3a is a hydrogen atom, R4a is a hydroxy group, R5a is a pentadecanoyl group and X is a methylene group;
a compound wherein R1 is a methyl group, R2 is a methyl group, R3a is a hydrogen atom, R4a is a hydroxy group, R5a is a palmitoyl group and X is a methylene group;
a compound wherein R1 is a hydrogen atom, R2 is a methyl group, R3a is a hydrogen atom, R4a is a hydroxy group, R5a is a decanoyl group and X is a methylene group;
a compound wherein R1 is a hydrogen atom, R2 is a methyl group, R3a is a hydrogen atom, R4a is a hydroxy group, R5a is a lauroyl group and X is a methylene group;
a compound wherein R1 is a hydrogen atom, R2 is a methyl group, R3a is a hydrogen atom, R4a is a hydroxy group, R5a is a myristoyl group and X is a methylene group;
a compound wherein R1 is a hydrogen atom, R2 is a methyl group, R3a is a hydrogen atom, R4a is a hydroxy group, R5a is a pentadecanoyl group and X is a methylene group;
a compound wherein R1 is a hydrogen atom, R2 is a methyl group, R3a is a hydrogen atom, R4a is a hydroxy group, R5a is a palmitoyl group and X is a methylene group;
a compound wherein R1 is a methyl group, R2 is a methyl group, R3a is a hexyloxycarbonyl group, R4a is a hydroxy group, R5a is a hydrogen atom and X is a methylene group;
a compound wherein R1 is a methyl group, R2 is a methyl group, R3a is a heptyloxycarbonyl group, R4a is a hydroxy group, R5a is a hydrogen atom and X is a methylene group;
a compound wherein R1 is a methyl group, R2 is a methyl group, R3a is an octyloxycarbonyl group, R4a is a hydroxy group, R5a is a hydrogen atom and X is a methylene group;
a compound wherein R1 is a methyl group, R2 is a methyl group, R3a is a nonyloxycarbonyl group, R4a is a hydroxy group, R5a is a hydrogen atom and X is a methylene group;
a compound wherein R1 is a methyl group, R2 is a methyl group, R3a is a decyloxycarbonyl group, R4a is a hydroxy group, R5a is a hydrogen atom and X is a methylene group;
a compound wherein R1 is a methyl group, R2 is a methyl group, R3a is an undecyloxycarbonyl group, R4a is a hydroxy group, R5a is a hydrogen atom and X is a methylene group;
a compound wherein R1 is a methyl group, R2 is a methyl group, R3a is a dodecyloxycarbonyl group, R4a is a hydroxy group, R5a is a hydrogen atom and X is a methylene group;
a compound wherein R1 is a methyl group, R2 is a methyl group, R3a is a hydrogen atom, R4a is a hydroxy group, R5a is a hexyloxycarbonyl group and X is a methylene group;
a compound wherein R1 is a methyl group, R2 is a methyl group, R3a is a hydrogen atom, R4a is a hydroxy group, R5a is a heptyloxycarbonyl group and X is a methylene group;
a compound wherein R1 is a methyl group, R2 is a methyl group, R3a is a hydrogen atom, R4a is a hydroxy group, R5a is an octyloxycarbonyl group and X is a methylene group;
a compound wherein R1 is a methyl group, R2 is a methyl group, R3a is a hydrogen atom, R4a is a hydroxy group, R5a is a nonyloxycarbonyl group and X is a methylene group;
a compound wherein R1 is a methyl group, R2 is a methyl group, R3a is a hydrogen atom, R4a is a hydroxy group, R5a is a decyloxycarbonyl group and X is a methylene group;
a compound wherein R1 is a methyl group, R2 is a methyl group, R3a is a hydrogen atom, R4a is a hydroxy group, R5a is an undecyloxycarbonyl group and X is a methylene group;
a compound wherein R1 is a methyl group, R2 is a methyl group, R3a is a hydrogen atom, R4a is a hydroxy group, R5a is a dodecyloxycarbonyl group and X is a methylene group;
a compound wherein R1 is a hydrogen atom, R2 is a methyl group, R3a is a hexyloxycarbonyl group, R4a is a hydroxy group, R5a is a hydrogen atom and X is a methylene group;
a compound wherein R1 is a hydrogen atom, R2 is a methyl group, R3a is a heptyloxycarbonyl group, R4a is a hydroxy group, R5a is a hydrogen atom and X is a methylene group;
a compound wherein R1 is a hydrogen atom, R2 is a methyl group, R3a is an octyloxycarbonyl group, R4a is a hydroxy group, R5a is a hydrogen atom and X is a methylene group;
a compound wherein R1 is a hydrogen atom, R2 is a methyl group, R3a is a nonyloxycarbonyl group, R4a is a hydroxy group, R5a is a hydrogen atom and X is a methylene group;
a compound wherein R1 is a hydrogen atom, R2 is a methyl group, R3a is a decyloxycarbonyl group, R4a is a hydroxy group, R5a is a hydrogen atom and X is a methylene group;
a compound wherein R1 is a hydrogen atom, R2 is a methyl group, R3a is an undecyloxycarbonyl group, R4a is a hydroxy group, R5a is a hydrogen atom and X is a methylene group;
a compound wherein R1 is a hydrogen atom, R2 is a methyl group, R3a is a dodecyloxycarbonyl group, R4a is a hydroxy group, R5a is a hydrogen atom and X is a methylene group;
a compound wherein R1 is a hydrogen atom, R2 is a methyl group, R3a is a hydrogen atom, R4a is a hydroxy group, R5a is a hexyloxycarbonyl group and X is a methylene group;
a compound wherein R1 is a hydrogen atom, R2 is a methyl group, R3a is a hydrogen atom, R4a is a hydroxy group, R5a is a heptyloxycarbonyl group and X is a methylene group;
a compound wherein R1 is a hydrogen atom, R2 is a methyl group, R3a is a hydrogen atom, R4a is a hydroxy group, R5a is an octyloxycarbonyl group and X is a methylene group;
a compound wherein R1 is a hydrogen atom, R2 is a methyl group, R3a is a hydrogen atom, R4a is a hydroxy group, R5a is a nonyloxycarbonyl group and X is a methylene group;
a compound wherein R1 is a hydrogen atom, R2 is a methyl group, R3a is a hydrogen atom, R4a is a hydroxy group, R5a is a decyloxycarbonyl group and X is a methylene group;
a compound wherein R1 is a hydrogen atom, R2 is a methyl group, R3a is a hydrogen atom, R4a is a hydroxy group, R5a is an undecyloxycarbonyl group and X is a methylene group;
a compound wherein R1 is a hydrogen atom, R2 is a methyl group, R3a is a hydrogen aton, R4a is a hydroxy group, R5a is a dodecyloxycarbonyl group and X is a methylene group;
a compound wherein R1 is a methyl group, R2 is a methyl group, R3a is a decyl group, R4a is a hydroxy group, R5a is a hydrogen atom and X is a methylene group;
and
a compound wherein R1 is a hydrogen atom, R2 is a methyl group, R3a is a decyl group, R4a is a hydroxy group, R5a is a hydrogen atom and X is a methylene group.

52 more elements

Dependencies are inferred from the claim text.

Antimicrobial compounds

Life of this patent

Antimicrobial compounds

Life of this patent

Abstract

Claims93