Process for preparing polyol-based esters of acyl-capped hydroxy carboxylic acids
The invention relates to a method for producing polyol esters, especially polyglycerol esters, of acyl-capped or acyl-blocked 3-hydroxybutyric acid as well as the products thus obtained and to their functionalized (e. g. esterified) derivatives, as well as to the various uses and applications of these products.
1 . A polyglycerol ester of an acetoacetyl-capped 3-hydroxybutyric acid according to general formula (IIIb″)
R 6 O—CH 2 —CH(OR 6 )—CH 2 —[O—CH 2 —CH(OR 6 )—CH 2 ] p —OR 6 (IIb″)
wherein, in the general formula (IIIb″),
the variable p represents an integer from 1 to 4,
the radical R 6 , each independently of one another, identical or different, represents: hydrogen
or a radical CH 3 -CH(OR 2 )-CH 2 -C(O)-, wherein the radical R 2 represents a radical CH 3 -C(O)-CH 2 -C(O)- or a radical R 4 , wherein the radical R 4 represents a radical of the type linear or branched, saturated or mono-or polyunsaturated (C 1 -C 33 -alkyl)-C(O)-, however, with the proviso that at least one radical R 6 does not represent hydrogen, and with the proviso that at least one radical R 6 represents a radical CH 3 -CH(OR 2 )-CH 2 -C(O)-.
2 . The polyglycerol ester of an acetoacetyl-capped 3-hydroxybutyric acid according to claim 1 ,
wherein the polyglycerol ester of an acetoacetyl-capped 3-hydroxybutyric acid corresponds to general formula (IIIc″)
R 6 O—CH 2 —CH(OR 6 )—CH 2 —O—CH 2 —CH(OR 6 )—CH 2 —OR 6 (IIIc″)
wherein, in the general formula (IIIc”), the radical R 6 , each independently of one another, identical or different, represents: hydrogen or a radical CH 3 -CH(OR 2 )-CH 2 -C(O)-, wherein the radical R 2 represents a radical CH 3 -C(O)-CH 2 -C(O)-or a radical R 4 , wherein the radical R 4 represents a radical of the type linear or branched, saturated or mono-or polyunsaturated (C 1 -C 33 -alkyl)-C(O)-, however, with the proviso that at least one radical R 6 does not represent hydrogen, and with the proviso that at least one radical R 6 represents a radical CH 3 -CH(OR 2 )-CH 2 -C(O)-.
3 . A mixture comprising at least two different polyglycerol esters of an acetoacetyl-capped of 3-hydroxybutyric acid according to claim 1 .
4 . A pharmaceutical composition comprising at least one polyglycerol ester of an acetoacetyl-capped 3-hydroxybutyric acid according to claim 1 .
5 . The pharmaceutical composition according to claim 4 ,
wherein the pharmaceutical composition is a drug or medicament.
6 . A method for treating a human or an animal suffering from a disease of the human or animal body,
wherein the method comprises the administration of an efficient amount of at least one polyglycerol ester of an acetoacetyl-capped 3-hydroxybutyric acid according to claim 1 .
7 . The method of claim 6 ,
wherein the disease is selected among diseases associated with a disorder of the energy metabolism or diseases associated with a disorder of the keto-body metabolism.
8 . The method of claim 6 ,
wherein the disease is selected among craniocerebral trauma, stroke, hypoxia, cardiovascular diseases, myocardial infarction, refeeding syndrome, anorexia, epilepsy, neurodegenerative diseases, dementia, Alzheimer's disease, Parkinson's disease, multiple sclerosis and amyotrophic lateral sclerosis, fat metabolic diseases, glucose transporter defect (GLUT1 defect), VL-FAOD and mitochondriopathies, mitochondrial thiolase defect, Huntington's disease, cancers, T-cell lymphomas, astrocytomas and glioblastomas, HIV, rheumatic diseases, rheumatoid arthritis and arthritis urica, diseases of the gastrointestinal tract, chronic inflammatory bowel diseases, ulcerative colitis and Crohn's disease, lyosomal storage diseases, sphingolipidosis, Niemann-Pick disease, diabetes mellitus and effects or side-effects of chemotherapy.
9 . A food or a food product comprising at least one polyglycerol ester of an acetoacetyl-capped 3-hydroxybutyric acid according to claim 1 .