Stem cell expansion and uses

1. A compound having the structure

wherein R 1 is hydroxy, an ester or an ether;

R 2 is hydroxy, an ester or an ether;

R 3 is halogen, hydroxy, an ester or an ether; and

one R 4 is —OH, an ester or an ether and the other R 4 is —H, optionally substituted alkyl, optionally substituted alkenyl or optionally substituted alkynyl.

2. The compound of claim 1 wherein R 4 in the β-configuration is —OH.

3. The compound of claim 2 wherein the R 4 in the α-configuration is —H.

4. The compound of claim 2 wherein the R 4 in the α-configuration is alkynyl.

5. The compound of claim 4 wherein alkynyl is ethynyl.

6. The compound of claim 1 wherein the compound has the structure

7. The compound of claim 6 wherein

R 1 and R 2 independently are hydroxy or an ester;

R 3 is —OH, an ester or halogen;

R 4 in the β-configuration is —OH or an ester and the R 4 in the α-configuration is —H or optionally substituted alkynyl.

8. The compound of claim 7 wherein optionally substituted alkynyl is ethynyl.

9. The compound of claim 1 wherein the compound is 3,7β,16α,17β-tetrahydroxy-androst-1,3,5(10)-triene, 3,17α-dihydroxy-7β-acetoxy-16α-fluoro-androst-1,3,5(10)-triene, 3,16α-dihydroxy-7β-acetoxy-16α-fluoro-androst-1,3,5(10)-triene or 3,16α,17β-trihydroxy-7β-methoxy-androst-1,3,5(10)-triene.

10. The compound of claim 1 wherein the compound is 3,7β,16α,17β-tetrahydroxy-androst-1,3,5(10)-triene.

11. The compound of claim 1 wherein the compound is 3,16α,17β-trihydroxy-7-acetoxy-androst-1,3,5(10),6-tetraene, 3,16α,17β-trihydroxy-7-methoxy-androst-1,3,5(10),6-tetraene, 3,17β-dihydroxy-7-acetoxy-16α-fluoro-androst-1,3,5(10),6-tetraene, 3,17β-dihydroxy-7-methoxy-16α-fluoro-androst-1,3,5(10),6-tetraene, 3,17β-dihydroxy-7,16α-diacetoxy-androst-1,3,5(10),6-tetraene or 3,17β-dihydroxy-7-methoxy-16α-acetoxy-androst-1,3,5(10),6-tetraene.

12. A compound having the structure

wherein the dotted lines are optional double bonds;

R 1 is —OH, an ester or an ether;

R 2 is —H, halogen, —OH, an ester or an ether;

R 3 independently or together are —H—OH, an ester, an ether, halogen or ═O;

wherein R 2 is —OH, an ester or an ether when both R 3 are —H or R 2 is halogen, —OH, an ester or an ether when one R 3 is halogen, —OH, an ester or an ether and the other R 3 is —H or C 1-6 alkyl, optionally substituted;

or one R 4 is hydroxy, an ester or an ether and the other R 4 is optionally substituted alkyl, optionally substituted alkenyl or optionally substituted alkynyl;

R 5 and R 6 independently are —H or optionally substituted alkyl.

13. The compound of claim 12 having the structure

14. The compound of claim 13 wherein the compound is 3β,16α,17β-trihydroxy-7-acetoxy-androst-5,7-diene, 3β,16α,17β-trihydroxy-7-methoxy-androst-5,7-diene, 3β,17β-dihydroxy-7-acetoxy-16α-fluoro-androst-5,7-diene, 3β,17β-dihydroxy-7-methoxy-16α-fluoro-androst-5,7-diene, 3β,17β-dihydroxy-7,16α-diacetoxy-androst-5,7-diene or 3β,17β-dihydroxy-7-methoxy, 16α-acetoxy-androst-5,7-diene.

15. The compound of claim 13 wherein the compound is 3β,17β-dihydroxy-7-acetoxy-androst-5,7-diene.

16. A pharmaceutical formulation comprising one or more excipients and a compound having the structure

wherein

R 1 is hydroxy, an ester or an ether;

R 2 is hydroxy, an ester or an ether;

R 3 is halogen, hydroxy, an ester or an ether; and

one R 4 is —OH, an ester or an ether and the other R 4 is —H, optionally substituted alkyl, optionally substituted alkenyl or optionally substituted alkynyl.

17. The pharmaceutical formulation of claim 16 wherein one R 4 in the β-configuration is —OH.

18. The pharmaceutical formulation of claim 17 wherein the other R 4 in the α-configuration is —H.

19. The pharmaceutical formulation of claim 17 wherein the other R 4 in the α-configuration is alkynyl.

20. The pharmaceutical formulation of claim 19 wherein alkynyl is ethynyl.

21. The pharmaceutical formulation of claim 16 wherein the pharmaceutical formulation has the structure

22. The pharmaceutical formulation of claim 21 wherein

R 1 and R 2 independently are hydroxy, an ester or an ether;

R 3 is —OH, an ester or halogen; and

one R 4 in the β-configuration is —OH or an ester and the other R 4 in the α-configuration is —H or optionally substituted alkynyl.

23. The pharmaceutical formulation of claim 22 wherein optionally substituted alkynyl is ethynyl.

24. The pharmaceutical formulation of claim 16 wherein the pharmaceutical formulation is 3,7β,16α,17β-tetrahydroxy-androst-1,3,5(10)-triene, 3,17α-dihydroxy-7β-acetoxy-16α-fluoro-androst-1,3,5(10)-triene, 3,16α-dihydroxy-7β-acetoxy-16α-fluoro-androst-1,3,5(10)-triene or 3,16α,17β-trihydroxy-7β-methoxy-androst-1,3,5(10)-triene.

25. The pharmaceutical formulation of claim 24 wherein the pharmaceutical formulation is 3,7β,16α,17β-tetrahydroxyandrost-1,3,5(10)-triene.

26. The pharmaceutical formulation of claim 1 wherein the pharmaceutical formulation is 3,16α,17β-trihydroxy-7-acetoxy-androst-1,3,5(10),6-tetraene, 3,16α,17β-trihydroxy-7-methoxy-androst-1,3,5(10),6-tetraene, 3,17β-dihydroxy-7-acetoxy-16α-fluoro-androst-1,3,5(10),6-tetraene, 3,17β-dihydroxy-7-methoxy-16α-fluoro-androst-1,3,5(10),6-tetraene, 3,17β-dihydroxy-7,16α-diacetoxy-androst-1,3,5(10),6-tetraene or 3,17β-dihydroxy-7-methoxy-16α-acetoxy-androst-1,3,5(10),6-tetraene.

27. The compound of claim 1 wherein the compound is purified or partially purified.

28. The compound of claim 6 wherein the compound is purified or partially purified.

29. The compound of claim 9 wherein the compound is purified or partially purified.