Dehydroandrosterone analogs including an anti-inflammatory pharmacore and methods of use
This invention provides novel compounds comprising the following anti-inflammatory pharmacore: wherein X, R 1 and R 2 are defined herein. Also provided are pharmaceutical compositions, kits and articles of manufacture comprising such compounds, methods and intermediates useful for making the compounds, and methods of using the compounds and compositions.
1. A compound of the formula:
wherein:
R 1 and R 2 are each independently:
alkyl (C≦12) , alkenyl (C≦12) , or a substituted version of either of these groups; or
R 1 and R 2 are taken together and are alkanediyl (C≦12) or alkenediyl (C≦12) ; and
R 20 , R 21 , and R 22 are each independently:
hydrogen, hydroxy, halo, oxo, or amino; or
alkyl (C≦12) , alkenyl (C≦12) , alkoxy (C≦12) , acyl-oxy (C≦12) , alkylsilyl-oxy (C≦12) , or a substituted version of any of these groups;
or a pharmaceutically acceptable salt, tautomer, acetal, or ketal thereof.
2. The compound of claim 1 , further defined as:
wherein R 20 , R 21 , and R 22 are each independently:
hydrogen, hydroxy, halo, oxo, or amino, ; or
alkyl (C≦12) , alkenyl (C≦12) , alkoxy (C≦12) , acyl-oxy (C≦12) , alkylsilyl-oxy (C≦12) , or a substituted version of any of these groups;
or a pharmaceutically acceptable salt, tautomer, acetal or ketal thereof.
3. The compound of claim 1 , further defined by the formula:
or a pharmaceutically acceptable salt or tautomer thereof.
4. The compound of claim 1 , further defined by the formula:
or a pharmaceutically acceptable salt or tautomer thereof.
5. The compound of claim 1 , further defined by the formula:
or a pharmaceutically acceptable salt or tautomer thereof.
6. The compound of claim 1 , further defined by the formula:
or a pharmaceutically acceptable salt or tautomer thereof.
7. The compound of claim 1 , further defined by the formula:
or a pharmaceutically acceptable salt or tautomer thereof.
8. The compound of claim 1 , further defined by the formula:
or a pharmaceutically acceptable salt or tautomer thereof.
9. The compound of claim 1 , further defined by the formula:
or a pharmaceutically acceptable salt or tautomer thereof.
10. The compound of claim 1 , further defined by the formula:
or a pharmaceutically acceptable salt or tautomer thereof.
11. The compound of claim 1 , further defined by the formula:
or a pharmaceutically acceptable salt or tautomer thereof.