Substituted naphthyridine derivatives as inhibitors of macrophage migration inhibitory factor and their use in the treatment of human diseases
AssigneeAvanir Pharmaceuticals
InventorsJagadish Sircar, Sunil K.C., Wenbin Ying, Timothy Davis
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Abstract
Inhibitors of MIF having a naphthyridine backbone are provided which have utility in the treatment of a variety of disorders, including the treatment of pathological conditions associated with MIF activity. The inhibitors of MIF have the following structures: including stereoisomers, prodrugs and pharmaceutically acceptable salts thereof, wherein n, R, R1, R2, X, Y and Z are as defined herein. Compositions containing an inhibitor of MIF in combination with a pharmaceutically acceptable carrier are also provided, as well as methods for use of the same.
Claims13
A compound having a structure:
- or a stereoisomer or a pharmaceutically acceptable salt thereof, wherein:
- R is selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, acylalkyl, substituted acylalkyl, heterocycle, substituted heterocycle, —(CH2)mC(═O)Ar, and —(CH2)mNR4R5;
- R1 is selected from the group consisting of —CN, —NO, —NO2, —C(═O)R3, —C(═O)OH, —NHC(═O)R3, —C(═O)OR3, —C(═O)NR4R5, —NR3C(═O)R3, —SO2NR4R5, —NR3SO2R3, —NHSO2R3, —S(O)mR3, —(CH2)mNR4R5, and —(CH2)mC(═O)Ar;
- R3 is independently selected from the group consisting of alkyl, substituted alkyl, alkenyl, substituted alkenyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, acylalkyl, substituted acylalkyl, heterocycle, substituted heterocycle;
- R4 and R5 are independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, acylalkyl, substituted acylalkyl, heterocycle, and substituted heterocycle, or R4 and R5 taken together comprise heterocycle or substituted heterocycle;
- X is selected from the group consisting of hydrogen, halogen, —F, —Cl, —CN, —NO, —NO2, —OCF3, —CF3, —NHSO2R3, —C(═O)R3, —C(═O)OR3, —C(═O)NR4R5, —NR3C(═O)R3, —NR3SO2R3, —S(O)mR3, —R3, —OR3, —SR3, —C(═O)OH, —NHC(═O)R3, and —NR4R5;
- Y is selected from the group consisting of hydrogen, halogen, —F, —Cl, —CN, —NO, —NO2, —OCF3, —CF3, —NHSO2R3, —C(═O)R3, —C(═O)OR3, —C(═O)NR4R5, —NR3C(═O)R3, —NR3SO2R3, —S(O)mR3, —R3, —OR3, —SR3, —C(═O)OH, —NHC(═O)R3, and —NR4R5;
- Z is selected from the group consisting of hydrogen, halogen, —F, —Cl, —CN, —NO, —NO2, —OCF3, —CF3, —NHSO2R3, —C(═O)R3, —C(═O)OR3, —C(═O)NR4R5, —NR3C(═O)R3, —NR3SO2R3, —S(O)mR3, —R3, —OR3, —SR3, —C(═O)OH, —NHC(═O)R3, and —NR4R5;
- Ar is selected from the group consisting of aryl and substituted aryl;
- m is independently 0, 1, 2, 3, or 4;
- and
- n is 0, 1, or 2.
A compound having a structure:
A compound having a structure:
Dependencies are inferred from the claim text.