US 7,256,187 B2 · Rifamycin C-11 oxime derivatives effective against drug-resistant microbes

Abstract

The invention relates to rifamycin derivatives having antimicrobial activities, including activities against drug-resistant microorganisms, specifically, the rifamycin derivatives having an oxime group at the C-11 position.

Claims45

Dependent claims

A compound of structural Formula I or Formula II:

or pharmaceutically acceptable salts thereof;
wherein:
L3 is any combination of 0 to 5 groups which independently are the same or different and are selected from —CR1R2—, —NR3—, —O—, —C(═O)—, —S(═O)0-2—, —C═N—, alkylene, alkenylene, and alkynylene;
X3 is —H, —OH, —NH2, —CO2H, halo, haloalkyl, —CN, alkyl, aryl, or -Q3;
L11 is any combination of 0 to 5 groups which independently are the same or different and are selected from —CR1R2—, —NR3—, —O—, —C(═O)—, —S(═O)0-2—, —C═N—, alkylene, alkenylene, and alkynylene;
X11 is —H, —OH, —NH2, —CO2H, halo, haloalkyl, —CN, alkyl, aryl, or -Q11;
Y is, when the compound is Formula I, ═O or ═NR4, and, when the compound is Formula II, —OH, —NHR4, —OR5, —OCH2CO2H, or —OCH2CONR6R7;
Z is —H or —COCH2R8, wherein R8 is —H, —OH, halo, —CN, —CO2H, —CONR9R10, —NR11R12, —OR13, —S(═O)0-2R14, or—Q25;
wherein R1 is —H, —OH, —SH, alkyl, cycloalkyl, aryl, alkoxy, alkylthio, alkylamino, or dialkylamino,
wherein R2, R3, R4, R5, R6, R7, R9, R10, R11, R12, R13, and R14 independently are the same or different and are H, alkyl, or aryl, and
where Q3, Q11, and Q25 independently are the same or different and are any of the structures:

8 more elements

Dependencies are inferred from the claim text.

Facts

Application

11/076,172Filed 9 Mar 2005 · us provisional application

Priority

10 Mar 2004

Published

US 2005/0203076 A115 Sep 2005

Granted

14 Aug 2007

Term ends

Not estimatedThe source records don’t support an estimate.

Classification12 codes

C07D 498/08
In which the condensed system contains two hetero rings: bridged systems
A61K 31/395
Heterocyclic compounds: having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
A61K 31/4427
Non condensed pyridines; Hydrogenated derivatives thereof: containing further heterocyclic ring systems
A61K 31/4525
Containing further heterocyclic ring systems: containing a five-membered ring with oxygen as a ring hetero atom

Rifamycin C-11 oxime derivatives effective against drug-resistant microbes

Life of this patent

Abstract

Claims45

Rifamycin C-11 oxime derivatives effective against drug-resistant microbes

Life of this patent

Abstract

Claims45