US 12,152,039 B2
Compounds and methods of their manufacturing
Jacob Westman, Järlåsa (SE); and Catarina Malmberg, Uppsala (SE)
Assigned to DICOT PHARMA AB, Uppsala (SE)
Filed by DICOT PHARMA AB, Uppsala (SE)
Filed on Oct. 27, 2023, as Appl. No. 18/496,043.
Application 18/496,043 is a continuation of application No. 18/469,860, filed on Sep. 19, 2023.
Claims priority of application No. 2251130-7 (SE), filed on Sep. 30, 2022.
Prior Publication US 2024/0124481 A1, Apr. 18, 2024
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 493/18 (2006.01)
CPC C07D 493/18 (2013.01) 15 Claims
 
1. A method of producing a therapeutically active limonoid from a compound of Formula Ia or Formula Tb, or both,

OG Complex Work Unit Chemistry
wherein R1 is a straight, branched or cyclic alkyl group with 1 to 6 carbon atoms that is unsubstituted or substituted with OH or a halogen, said method comprising
(i) providing a composition comprising:
the compound Formula Ia, or Formula Ib, or both,

OG Complex Work Unit Chemistry
wherein
R1 is as defined above,
R2 and R3 independently are selected from straight, branched or cyclic, substituted or unsubstituted alkyl groups with 1 to 6 carbons or from a nicotinyl group; and/or
providing an extract composition from Entandrophragma caudatum, comprising at least the compound of Formula IIa, wherein
a) R2 and R3 independently are selected from straight or branched alkyl groups with 1 to 6 carbon atoms or a nicotinyl group; and
b) R1 is methyl;
(ii) subjecting the extract composition and/or optionally the composition from step (i) to one or more distillations and to an introduction of a solvent comprising an aliphatic alkanol;
(iii) performing an alkanolysis reaction by, in the presence of the aliphatic alcohol, adding an aliphatic metal alkoxide to start the reaction, and subsequently an acid to stop the alkanolysis reaction, thereby obtaining the compound or Formula Ia, or Formula Ib, or both.