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US RE47,741 E1Granted
Antibacterial aminoglycoside analogs
AssigneeAchaogen, Inc.
InventorsPaola Dozzo, Adam Aaron Goldblum, James Bradley Aggen, Martin Sheringham Linsell
Life of this patent
Estimating the term…
Abstract
Compounds having antibacterial activity are disclosed. The compounds have the following structure (I): including stereoisomers, pharmaceutically acceptable salts and prodrugs thereof, wherein Q1, Q2, Q3, R11 and R12 are as defined herein. Methods associated with preparation and use of such compounds, as well as pharmaceutical compositions comprising such compounds, are also disclosed.
Claims22
A compound having the following structure (I):
- or a stereoisomer or pharmaceutically acceptable salt thereof,
- wherein:
- Q1 is alkyl optionally substituted with hydroxyl or amino,
- Q2 is hydrogen, optionally substituted alkyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, —C(═NH)NR7R8,
- Q3 is hydrogen, optionally substituted alkyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, —C(═NH)NR7R8,
- each R4, R5, R7, R8 and R11 is, independently, hydrogen or C1-C6 alkyl optionally substituted with one or more halogen, hydroxyl or amino;
- each R6 is, independently, hydrogen, halogen, hydroxyl, amino or C1-C6 alkyl;
- or R4 and R5 together with the atoms to which they are attached can form a heterocyclic ring having from 4 to 6 ring atoms, or R5 and one R6 together with the atoms to which they are attached can form a heterocyclic ring having from 3 to 6 ring atoms, or R4 and one R6 together with the atoms to which they are attached can form a carbocyclic ring having from 3 to 6 ring atoms, or R7 and R8 together with the atom to which they are attached can form a heterocyclic ring having from 3 to 6 ring atoms;
- each R9 and R12 is, independently, hydrogen, hydroxyl, amino or C1-C6 alkyl optionally substituted with one or more halogen, hydroxyl or amino;
- each R10 is, independently, hydrogen, halogen, hydroxyl, amino or C1-C6 alkyl;
- or R9 and one R10 together with the atoms to which they are attached can form a heterocyclic ring having from 3 to 6 ring atoms;
- and
- each n is, independently, an integer from 0 to 4, and
- wherein (i) at least one of Q2 and Q3 is other than hydrogen, and (ii) Q1 is not ethyl or —C(═O)CH3.
11 more elements
A compound having the following structure (I):
- or a stereoisomer or pharmaceutically acceptable salt thereof,
- wherein:
- Q1 is
- Q2 is hydrogen, optionally substituted alkyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, —C(═NH)NR7R8,
- Q3 is hydrogen, optionally substituted alkyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, —C(═NH)NR7R8,
- each R4, R5, R7, R8 and R11 is, independently, hydrogen or C1-C6 alkyl optionally substituted with one or more halogen, hydroxyl or amino;
- each R6 is, independently, hydrogen, halogen, hydroxyl, amino or C1-C6 alkyl;
- or R4 and R5 together with the atoms to which they are attached can form a heterocyclic ring having from 4 to 6 ring atoms, or R5 and one R6 together with the atoms to which they are attached can form a heterocyclic ring having from 3 to 6 ring atoms, or R4 and one R6 together with the atoms to which they are attached can form a carbocyclic ring having from 3 to 6 ring atoms, or R7 and R8 together with the atom to which they are attached can form a heterocyclic ring having from 3 to 6 ring atoms;
- each R9 and R12 is, independently, hydrogen, hydroxyl, amino or C1-C6 alkyl optionally substituted with one or more halogen, hydroxyl or amino;
- each R10 is, independently, hydrogen, halogen, hydroxyl, amino or C1-C6 alkyl;
- or R9 and one R10 together with the atoms to which they are attached can form a heterocyclic ring having from 3 to 6 ring atoms;
- and
- each n is, independently, an integer from 0 to 4, and
- wherein (i) at least one of Q2 and Q3 is other than hydrogen, and (ii) for Q1, R5 and one R6 together with the atoms to which they are attached form a heterocyclic ring having 3 ring atoms, or R4 and one R6 together with the atoms to which they are attached form a carbocyclic ring having 3 ring atoms, or R9 and one R10 together with the atoms to which they are attached form a heterocyclic ring having 3 ring atoms.
11 more elements
Dependencies are inferred from the claim text.