(−)-huperzine A processes and related compositions and methods of treatment
The invention provides (1) processes for making substantially-pure (−) huperzine A and substantially-pure (−) huperzine A derivatives; (2) compositions useful in making substantially-pure (−) huperzine A and substantially-pure (−) huperzine A derivatives; and (3) methods of treating or preventing neurological disorders using substantially-pure (−) huperzine A and substantially-pure (−) huperzine A derivatives.
1. A compound according to the chemical structure:
wherein:
R 1 is a methyl group;
R 2 and R 5 are each independently selected from the group consisting of H and methyl;
R 3 at each occurrence is H or methyl;
R 4 is selected from the group consisting of H, OH, and Si(CH 3 ) 2 Ph;
R 6 is selected from the group consisting of —C(O)NH 2 or CN; and
R 7 is methyl; or
a pharmaceutically acceptable salt, enantiomer or diastereomer thereof.
2. The compound according to claim 1 wherein R 2 and R 5 are each H.
3. The compound according to claim 2 wherein R 4 is OH.
4. The compound according to claim 2 wherein R 4 is H.
5. The compound according to claim 2 wherein R 4 is Si(CH 3 ) 2 Ph.
6. A compound according to the chemical structure:
or
a pharmaceutically acceptable salt, enantiomer or diastereomer thereof.
7. The compound of claim 6 according to the chemical structure:
8. The compound of claim 6 according to the chemical structure:
9. The compound of claim 6 according to the chemical structure:
10. The compound of claim 6 according to the chemical structure: