US 11,807,639 B1
Pyrrolo[3,4-b]quinoline compounds as antibacterial agents
Michelyne Haroun, Al-Ahsa (SA); and Christophe Tratrat, Al-Ahsa (SA)
Assigned to KING FAISAL UNIVERSITY, Al-Ahsa (SA)
Filed by KING FAISAL UNIVERSITY, Al-Ahsa (SA)
Filed on Mar. 23, 2023, as Appl. No. 18/125,449.
Int. Cl. C07D 471/04 (2006.01); A61P 31/04 (2006.01)
CPC C07D 471/04 (2013.01) [A61P 31/04 (2018.01)] 11 Claims
 
1. A compound having the formula I:

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt, ester, stereoisomer, or solvate thereof, wherein:
R1 is a C1-C6 alkyl or a C3-C6 cycloalkyl;
R2 is hydrogen or a halogen;
R3 is hydrogen, —OR6, —NH2, —NHR7, or —NR7R8;
R4 and R5, which may independently be the same or different, each represent:
1) a hydrogen atom,
2) a linear or branched C1-C6 polyhaloalkyl group,
3) —OR6,
4) —COR9,
5) —CH2NR7R8,
6) —CH2COR9, or
7) —CH2OR6;
each R6 may independently be the same or different and may each represent a hydrogen atom, an aryl group, a heteroaryl group, or a linear or branched C1-C6 polyhaloalkyl or a linear or branched C1-C6 alkyl group or a C3-C6 cycloalkyl group, each of which can be optionally substituted by a carboxylic acid group, by a group of formula —CONR7R8, or by a group of formula —NR7R8;
each R7 and R8, which may be the same or different, each represent hydrogen, a linear or branched C1-C6 alkyl group optionally substituted by one or more of a hydroxy group or an amino group (itself optionally substituted by one or two linear or branched C1-C6 alkyl groups), a C3-C8 cycloalkyl group, an aryl group optionally substituted by one or more of a C1-C6 alkyl group, a C1-C6 alkoxy group, or a halogen, or R7 and R8, taken together with the nitrogen atom to which they are attached, form a nitrogen-containing heterocycle ring which may be further substituted with a C1-C6 alkyl group; and
R9 represents:
1) a hydroxy group,
2) —OR6,
3) an amino group,
4) an amino group substituted by one or more aryl groups, heteroaryl groups, or linear or branched C1-C6 alkyl groups or C3-C8 cycloalkyl groups, each of which can be optionally substituted by a carboxylic acid group, by a group of formula —CONR7R8, or by a group of formula —NR7R8, wherein R7 and R8 may be the same or different,
5) a linear or branched C1-C6 alkyl group optionally substituted by a carboxylic acid group, or by a group of formula —CONR7R8 or —NR7R8, wherein R7 and R8 may be the same or different,
6) a C3-C8 cycloalkyl group:
7) a C1-C6 polyhalogen alkyl group; or
8) —OPO(OH)2.