Benzodiazepinone compounds and methods of treatment using same
AssigneeThe Regents of the University of Michigan
InventorsGary D. Glick, Alexander Ross Hurd, Chad Alan Van Huis
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Abstract
The invention provides 1,4-benzodiazepinone compounds, pharmaceutical compositions, and methods of treating autoimmune disorders, chronic inflammatory disorders, and hyperproliferative disorders. For example, the 1,4-benzodiazepinone compounds and pharmaceutical compositions are contemplated to be useful for treating rheumatoid arthritis, graft-versus-host disease, inflammatory bowel disease, and the like.
Claims27
A compound represented by Formula I:
- including a pharmaceutically acceptable salt thereof, wherein:
- X1 is Cl or F;
- X2 is hydrogen, halogen, hydroxyl, methoxy, ethoxy, methyl, or ethyl;
- R1 is hydrogen, C1-C3 alkyl, hydroxyethyl, or hydroxypropyl;
- R2 is
- R3 and R4 are independently hydrogen, C1-C5 alkyl, or Z;
- provided that both R3 and R4 are not hydrogen, and provided that both R3 and R4 are not Z;
- R5 represents independently for each occurrence halogen, trifluoromethyl, or C1-C5 alkyl;
- R6 represents independently for each occurrence hydrogen or C1-C5 alkyl;
- Z is C1-C4alkylene-CO2R6, C1-C4alkylene-C(O)N(R6)2, or C1-C4alkyl substituted with —OR6;
- n is 1 or 2;
- and
- the stereochemical configuration at a stereocenter in a compound represented by Formula I is R, S, or a mixture thereof.
(canceled)
(canceled)
(canceled)
A compound represented by Formula II:
- including a pharmaceutically acceptable salt thereof, wherein:
- X is hydrogen, halogen, hydroxyl, methoxy, ethoxy, methyl, or ethyl;
- R1 is hydrogen, C1-C3 alkyl, hydroxyethyl, or hydroxypropyl;
- R2 is
- R3 represents independently for each occurrence halogen, trifluoromethyl, or C1-C5 alkyl;
- n is 1 or 2;
- and
- the stereochemical configuration at a stereocenter in a compound represented by Formula II is R, S, or a mixture thereof.
19-25. (canceled)
A compound represented by Formula III:
- including a pharmaceutically acceptable salt thereof, wherein:
- X1 is Cl, F, or CF3;
- X2 is hydrogen, halogen, hydroxyl, methoxy, ethoxy, methyl, or ethyl;
- R1 is hydrogen, C1-C3 alkyl, hydroxyethyl, or hydroxypropyl;
- R2 represents independently for each occurrence halogen, trifluoromethyl, or C1-C3 alkyl;
- R3 represents independently for each occurrence C1-C3 alkyl, C1-C4alkylene-CO2R5, or C1-C4alkylene-C(O)N(R5)2;
- R4 is hydrogen or halogen;
- R5 represents independently for each occurrence hydrogen or C1-C5 alkyl;
- m and n are independently 1 or 2;
- and
- the stereochemical configuration at a stereocenter in a compound represented by Formula III is R, S, or a mixture thereof.
27-39. (canceled)
43-44. (canceled)
(canceled)
Dependencies are inferred from the claim text.