US 7,247,634 B2 · Rifamycin derivatives effective against drug-resistant microbes

Abstract

Rifamycin derivatives having antimicrobial activities, including activities against drug-resistant microorganisms are claimed in this invention. The inventive rifamycin derivatives are uniquely designed in that they have a rifamycin moiety covalently linked to a linker group through the C-3 carbon of the rifamycin moiety and the linker is, in turn covalently linked to a therapeutic moiety or antibacterial agent/pharmacophore. The therapeutic moiety can be a quinolone, an oxazolidinone, a macrolide, an aminoglycoside, a tetracycline core or a structure/pharmacophore associated with an antibacterial agent.

Claims53

Dependent claims

A rifamycin compound having a structural formula I or II:

wherein,
A is a quinolone or its pharmacophore, covalently coupled to a linker group “X”;
X is a linker group that is covalently coupled to both rifamycin moiety at C-3 position and “A”, wherein “X” is selected from one or a combination of 1 to 3 of the following structural elements:
a) —(C1-C6)alkylene,
b) —(C1-C6)alkenylene,
c) —(C1-C6)alkynylene,
d) —(C3-C8)cycloalkylene,
e) —O—,
f) —C(H)═N—, provided the group was not directly attached to the C-3 position of the rifamycin moiety,
g) —C(═O)—,
h) —C(═N—O—R13)—, wherein R13 represents hydrogen, (C1-C6)alkyl, or substituted (C1-C6)alkyl,
i) —S(O)n—, wherein n is a number between 0 and 2,
j) —N(R14)—, wherein R14 represents hydrogen, (C1-C6)alkyl, or substituted (C1-C6)alkyl, and
k) arylene,
wherein, the carbon or nitrogen atoms of the linker group “X” can be substituted by 1 to 3 substituents selected from (C1-C6)alkyl, substituted (C1-C6)alkyl, amino, (C1-C6)alkylamino, di(C1-C6)alkylamino, hydroxyl, and (C1-C6)alkoxy;
R1 is hydrogen, or acetyl,
or a pharmaceutically acceptable salt of the structural formula I or II.

14 more elements

Dependencies are inferred from the claim text.

Rifamycin derivatives effective against drug-resistant microbes

Life of this patent

Rifamycin derivatives effective against drug-resistant microbes

Life of this patent

Abstract

Claims53