Method for producing polygylcerol esters of polycarboxylic acids esterified with oxobutanol

A method for producing polyglycerol esters of polycarboxylic acids esterified with oxobutanol,

• wherein the following reactants (i), (ii) and (iii) are reacted with one another:
• (i) at least one oxobutanol of the general formula (I)
• CH3—CH(OH)—CH2—C(O)OR1 (I)
• wherein, in the general formula (I), the radical R1 is selected among C1-C5-alkyl and hydroxy-C3-C5-alkyl,
• (ii) at least one polycarboxylic acid (II) selected among the polycarboxylic acid (II) in its free form and in the form of its salts, esters and anhydrides,
• (iii) at least one polyglycerol (III);
• wherein the method is carried out as one of a one-step method and a method comprising several steps, and
• wherein the method is carried out in the absence of any solvent;
• wherein, when the polycarboxylic acid (II) is used in the form of a free acid, water is formed simultaneously during the reaction, wherein the water is continuously withdrawn from the reaction;
• wherein, when the polycarboxylic acid (II) is used in the form of an anhydride, the corresponding free polycarboxylic acid (II) and water are formed, wherein the resulting free polycarboxylic acid (II) is further reacted or, after the reaction has taken place, is removed and recycled and wherein the water is continuously withdrawn from the reaction;
• wherein, when the polycarboxylic acid (II) is used in the form of an ester, the corresponding ester alcohol and water are formed, wherein the resulting ester alcohol and water are continuously withdrawn from the reaction;
• so that, as a reaction product (IV), one or more polyglycerol esters of polycarboxylic acids esterified with oxobutanol are obtained.

A polyglycerol ester of polycarboxylic acids esterified with oxobutanol,

• wherein the polyglycerol ester of polycarboxylic acids esterified with oxobutanol corresponds to the general formula (IVa)
• R4O—CH2—CH(OR4)—CH2—[O—CH2—CH(OR4)—CH2]p—OR4 (IVa)
• wherein, in the general formula (IVa), the radical R4, independently of one another, represents:
• hydrogen;
• a radical R1—O—C(O)—CH2—CH(CH3)—O—(O)C—X—C(O)—,
• wherein the radical R1 is selected among C1-C5-alkyl and hydroxy-C3-C5-alkyl, and
• wherein X represents a saturated or unsaturated organic radical comprising 1 to 10 carbon atoms, which may be mono- or polysubstituted with one or more of the following radicals:
• hydroxyl, carboxyl, —O—C(O)—CH2—CH(OH)—CH3 and —C(O)—O—CH(CH3)—CH2—C(O)OR1 with R1 as defined hereinbefore;
• a radical H3C—CH(OH)—CH2—C(O)—;
• a radical HOOC—X—C(O)— with X as defined hereinbefore;
• however, with the proviso that at least one radical R4 represents a radical R1—O—C(O)—CH2—CH(CH3)—O—(O)C—X—C(O)— as defined hereinbefore;
• and
• wherein, in the general formula (IVa), the variable p represents an integer from 1 to 6.

A pharmaceutical composition comprising at least one polyglycerol ester of polycarboxylic acids esterified with oxobutanol,

• wherein the polyglycerol ester of polycarboxylic acids esterified with oxobutanol corresponds to the general formula (IVa)
• R4O—CH2—CH(OR4)—CH2—[O—CH2—CH(OR4)—CH2]p—OR4 (IVa)
• wherein, in the general formula (IVa), the radical R4, independently of one another, represents:
• hydrogen;
• a radical R1—O—C(O)—CH2—CH(CH3)—O—(O)C—X—C(O)—,
• wherein the radical R1 is selected among C1-C5-alkyl and hydroxy-C3-C5-alkyl, and
• wherein X represents a saturated or unsaturated organic radical comprising 1 to 10 carbon atoms, which may be mono- or polysubstituted with one or more of the following radicals:
• hydroxyl, carboxyl, —O—C(O)—CH2—CH(OH)—CH3 and —C(O)—O—CH(CH3)—CH2—C(O)OR1 with R1 as defined hereinbefore;
• a radical H3C—CH(OH)—CH2—C(O)—;
• a radical HOOC—X—C(O)— with X as defined hereinbefore;
• however, with the proviso that at least one radical R4 represents a radical R1—O—C(O)—CH2—CH(CH3)—O—(O)C—X—C(O)— as defined hereinbefore;
• and
• wherein, in the general formula (IVa), the variable p represents an integer from 1 to 6.

A method of treating a human or an animal suffering from a disease of the human or animal body,

• wherein the method comprises the step of administering to said human or animal a therapeutically efficient amount of at least one polyglycerol ester of polycarboxylic acids esterified with oxobutanol,
• wherein the polyglycerol ester of polycarboxylic acids esterified with oxobutanol corresponds to the general formula (IVa)
• R4O—CH2—CH(OR4)—CH2—[O—CH2—CH(OR4)—CH2]p—OR4 (IVa)
• wherein, in the general formula (IVa), the radical R*, independently of one another, represents:
• hydrogen;
• a radical R1—O—C(O)—CH2—CH(CH3)—O—(O)C—X—C(O)—,
• wherein the radical R1 is selected among C1-C5-alkyl and hydroxy-C3-C5-alkyl, and
• wherein X represents a saturated or unsaturated organic radical comprising 1 to 10 carbon atoms, which may be mono- or polysubstituted with one or more of the following radicals:
• hydroxyl, carboxyl, —O—C(O)—CH2—CH(OH)—CH3 and —C(O)—O—CH(CH3)—CH2—C(O)OR1 with R1 as defined hereinbefore;
• a radical H3C—CH(OH)—CH2—C(O)—;
• a radical HOOC—X—C(O)— with X as defined hereinbefore;
• however, with the proviso that at least one radical R4 represents a radical R1—O—C(O)—CH2—CH(CH3)—O—(O)C—X—C(O)— as defined hereinbefore;
• and
• wherein, in the general formula (IVa), the variable p represents an integer from 1 to 6.

A food product comprising at least one polyglycerol ester of polycarboxylic acids esterified with oxobutanol,

• wherein the polyglycerol ester of polycarboxylic acids esterified with oxobutanol corresponds to the general formula (IVa)
• R4O—CH2—CH(OR4)—CH2—[O—CH2—CH(OR4)—CH2]p—OR4 (IVa)
• wherein, in the general formula (IVa), the radical R4, independently of one another, represents:
• hydrogen;
• a radical R1—O—C(O)—CH2—CH(CH3)—O—(O)C—X—C(O)—,
• wherein the radical R1 is selected among C1-C5-alkyl and hydroxy-C3-C5-alkyl, and
• wherein X represents a saturated or unsaturated organic radical comprising 1 to 10 carbon atoms, which may be mono- or polysubstituted with one or more of the following radicals:
• hydroxyl, carboxyl, —O—C(O)—CH2—CH(OH)—CH3 and —C(O)—O—CH(CH3)—CH2—C(O)OR1 with R1 as defined hereinbefore;
• a radical H3C—CH(OH)—CH2—C(O)—;
• a radical HOOC—X—C(O)— with X as defined hereinbefore;
• however, with the proviso that at least one radical R4 represents a radical R1—O—C(O)—CH2—CH(CH3)—O—(O)C—X—C(O)— as defined hereinbefore;
• and
• wherein, in the general formula (IVa), the variable p represents an integer from 1 to 6.