Pyrazoloanthrone and derivatives thereof as JNK inhibitors and compositions and methods related thereto
AssigneeSignal Pharmaceuticals, LLC
InventorsBrydon L. Bennett, Shripad S. Bhagwat, Anthony M. Manning, Brion W. Murray, Eoin C. O'Leary, Yoshitaka Satoh
Life of this patent
Estimating the term…
Abstract
Compounds having activity as selective inhibitors of JNK are disclosed The compounds of this invention are pyrazoloanthrone and derivatives thereof having the following structure: wherein R1 and R2 are as defined herein. Such compounds have utility in the treatment of a wide range of conditions that are responsive to JNK inhibition. Thus, methods of treating such conditions are also disclosed, as are pharmaceutical compositions containing one or more compounds of the above compounds.
Claims19
A compound having the structure:
- or a pharmaceutically acceptable salt thereof,
- wherein
- R1 and R2 are optional substituents that are the same or different and independently represent trifluoromethyl, sulfonyl, aryl, arylalkyloxy, arylalkyl, cycloalkylalkyloxy, cycloalkyloxy, alkoxyalkoxy, aminoalkoxy, mono- or di-alkylaminoalkoxy, or a group represented by formula (a), (b), (c) or (d):
- R3 and R4 are the same or different and independently represent cycloalkyl, aryl, arylalkyl, cycloalkylalkyl, aryloxyalkyl, alkoxyalkyl, alkoxyamino, or alkoxy(mono- or di-alkylamino);
- and
- R5 represents hydrogen, alkyl, cycloalkyl, carbocyclic aromatic, heterocyclic aromatic, arylalkyl, cycloalkylalkyl, alkoxy, amino, mono- or di-alkylamino, arylamino, arylalkylamino, cycloalkylamino or cycloalkylalkylamino, with the proviso that carbocyclic aromatic is not phenyl;
- and with the proviso that at least R1 or R2 is present.
A compound having one of the following structures:
- or a pharmaceutically acceptable salt thereof,
- wherein
- R1 represents trifluoromethyl, sulfonyl, carboxyl, alkoxycarbonyl, aryl, arylalkyloxy, arylalkyl, cycloalkylalkyloxy, cycloalkyloxy, alkoxyalkoxy, aminoalkoxy, mono- or di-alkylaminoalkoxy, or a group represented by formula (a), (b), (c) or (d):
- when R1 is present, R3 and R4 are the same or different and independently represent alkyl, cycloalkyl, aryl, arylalkyl, cycloalkylalkyl, aryloxyalkyl, alkoxyalkyl, alkoxyamino, or alkoxy(mono- or di-alkylamino);
- when R1 is present, R5 represents hydrogen, alkyl, cycloalkyl, aryl, arylalkyl, cycloalkylalkyl, alkoxy, amino, mono- or di-alkylamino, arylamino, arylalkylamino, cycloalkylamino or cycloalkylalkylamino;
- R2 represents trifluoromethyl, sulfonyl, aryl, arylalkyloxy, arylalkyl, cycloalkylalkyloxy, cycloalkyloxy, alkoxyalkyl, alkoxyalkoxy, aminoalkoxy, mono- or di-alkylaminoalkoxy, or a group represented by formula (a), (b), (c) or (d):
- when R2 is present, R3 and R4 are the same or different and independently represent cycloalkyl, aryl, arylalkyl, cycloalkylalkyl, aryloxyalkyl, alkoxyalkyl, alkoxyamino, or alkoxy(mono- or di-alkylamino);
- and
- when R2 is present, R5 represents hydrogen, alkyl, cycloalkyl, carbocyclic aromatic, heterocyclic aromatic, arylalkyl, cycloalkylalkyl, alkoxy, amino, mono- or di-alkylamino, arylamino, arylalkylamino, cycloalkylamino or cycloalkylalkylamino with the proviso that carbocyclic aromatic is not phenyl.
A pharmaceutical composition comprising a compound having the structure:
- or a pharmaceutically acceptable salt thereof, a pharmaceutically acceptable carrier or a pharmaceutically acceptable diluent and a dispersing agent, a surface active agent, a binder or a lubricant.
A compound having the structure:
- or a pharmaceutically acceptable salt thereof,
- wherein
- R1 and R2 are optional substituents that are the same or different and independently represent, trifluoromethyl, sulfonyl, carboxyl, alkoxycarbonyl, aryl, arylalkyloxy, arylalkyl, cycloalkylalkyloxy, cycloalkyloxy, alkoxyalkyl, alkoxyalkoxy, aminoalkoxy, mono- or di-alkylaminoalkoxy, or a group represented by formula (a), (b), (c) or (d):
- R3 and R4 are the same or different and independently represent alkyl, cycloalkyl, aryl, arylalkyl, cycloalkylalkyl, aryloxyalkyl, alkoxyalkyl, alkoxyamino, or alkoxy(mono- or di-alkylamino);
- and
- R5 represents hydrogen, alkyl, cycloalkyl, aryl, arylalkyl, cycloalkylalkyl, alkoxy, amino, mono- or di-alkylamino, arylamino, arylalkylamino, cycloalkylamino or cycloalkylalkylamino;
- and with the proviso that at least one of R1 or R2 is present.
A solid pharmaceutical composition selected from a pill, capsule or tablet, comprising a compound having the structure:
- or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier or a pharmaceutically acceptable diluent.
Dependencies are inferred from the claim text.