US 12,258,609 B2
Method for producing glycerides of hydroxycarboxylic acids
Dirk Lochmann, Witten (DE); Sebastian Reyer, Witten (DE); and Michael Stehr, Witten (DE)
Assigned to KetoLipix Therapeutics GmbH, (DE)
Appl. No. 17/379,083
Filed by KetoLipix Therapeutics GmbH, Hamburg (DE)
PCT Filed Jan. 23, 2019, PCT No. PCT/EP2019/051539
§ 371(c)(1), (2) Date Jul. 19, 2021,
PCT Pub. No. WO2020/147978, PCT Pub. Date Jul. 23, 2020.
Claims priority of application No. PCT/EP2019/051116 (WO), filed on Jan. 17, 2019.
Prior Publication US 2023/0151395 A1, May 18, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. C12P 7/625 (2022.01); A23L 33/12 (2016.01); A61K 31/22 (2006.01); A61K 31/225 (2006.01); A61P 3/04 (2006.01); C07C 67/08 (2006.01); C12P 7/62 (2022.01)
CPC C12P 7/625 (2013.01) [A23L 33/12 (2016.08); A61K 31/22 (2013.01); A61K 31/225 (2013.01); A61P 3/04 (2018.01); C07C 67/08 (2013.01); C12P 7/62 (2013.01)] 16 Claims
 
1. A method for producing a mixture of mono-, di- and triglycerides of 3-hydroxybutyruic acid of the general formula (III):
CH2(OR2)—CH(OR3)—CH(OR4)  (III),
comprising reacting at least one compound of the general formula (I):
CH3—CH(OH)—CH2—C(O)OR1  (I),
with glycerol,
wherein:
the reaction is carried out in the presence of an enzyme as catalyst;
the reaction is carried out in the absence of any solvent;
R1 is selected from the group consisting of H or C1-C4 alkyl;
R2, R3 and R4, each independently of one another, is selected from H or a radical of formula CH3—CH(OH)—CH2—C(O)—, provided that at least one of R2, R3 and R4, is not H; and
the mixture comprises monoglycerides of 3-hydroxybutyric acid (3-BHB-MG), diglycerides of 3-hydroxybutyric acid (3-BHB-DG) and triglycerides of 3-hydroxybutyric acid (3-BHB-TG), in a weight ratio of 3-BHB-MG/3-BHB-DG/3-BHB-TG in the range of 10-80/10-70/0.1-20.