Compounds and methods of their manufacturing
The present document is directed to methods for producing therapeutically active limonoids as well as new limonoid-type compounds.
1. A compound of Formula III
wherein R 1 is a straight branched or cyclic alkyl group with 1 to 6 carbon atoms that is unsubstituted or substituted.
2. The compound according to claim 1 , wherein R 1 is methyl.
3. The compound according to claim 1 , wherein the compound of formula III is obtained by reacting a compound of Formula Ia with a base, of sufficient strength to open the lactone ring, but not to hydrolyze the group R1 to form a carboxylic group, preferably the base is barium hydroxide octahydrate in methanol, to obtain the compound of Formula III
4. A compound of Formula IV
wherein R 1 is a straight, branched or cyclic alkyl group with 1 to 6 carbon atoms that is unsubstituted or substituted.
5. The compound according to claim 4 , wherein R 1 is methyl.
6. The compound according to claim 4 , wherein the compound of Formula IV is obtained by reacting a compound of Formula III with a selectively oxidizing agent, preferably Dess Martin periodinane, to obtain the compound of Formula IV.
7. A monohydrate salt of compound according to Formula V,
wherein R 1 is methyl,
wherein R2′ is a straight, branched or cyclic optionally substituted alkyl group
with 1 to 6 carbon atoms.
8. A compound according to Formula V,
wherein R 1 is a straight, branched or cyclic alkyl group with 1 to 6 carbon atoms that is unsubstituted or substituted with the proviso that R 1 is not hydrogen, methyl or ethyl,
wherein R2′ is a straight, branched or cyclic optionally substituted alkyl group with 1 to 6 carbon atoms.
9. The compound of claim 1 , wherein R 1 is a straight, branched or cyclic alkyl group with 1 to 6 carbon atoms that is unsubstituted.
10. The compound of claim 1 , wherein R 1 is a straight, branched or cyclic alkyl group with 1 to 6 carbon atoms that is substituted with —OH or a halogen.
11. The compound of claim 4 , wherein R 1 is a straight, branched or cyclic alkyl group with 1 to 6 carbon atoms that is unsubstituted.
12. The compound of claim 4 , wherein R 1 is a straight, branched or cyclic alkyl group with 1 to 6 carbon atoms that is substituted with —OH or a halogen.