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US 12,060,315 B2Granted
Production processes of S- and O-diacylated gamma-glutamyl-cysteamine prodrugs
AssigneeUniversity of Sunderland
InventorsRosaleen Joy Anderson, Lisa Frost, Neil Barnwell, Matthew Levick, Ivan Hales, Michael Dunn
Life of this patent
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Abstract
Methods are provided for the synthesis of a compound of formula (X). R2 is selected from —H, —C1-C4-alkyl, —C2-C4-alkenyl and C1-C4-aryl; R3 is selected from —C(O)H and —C(O)C1-C4-alkyl; and A is a pharmaceutically acceptable anion (e.g. a halide). Also provided are intermediate compounds formed during the synthesis.
Claims18
A method of forming a compound of formula (X), the method comprising reacting the compound of formula (III) with the compound of formula (V) to form the compound of formula (VI):
- and
- cleaving the R1-oxycarbonyl amide of the compound of formula (VI) with a strong acid of the formula HA to form the compound of formula (X):
- wherein
- R1 is —C(CH3)3;
- R2 is selected from —H, —C1-C4-alkyl, —C2-C4-alkenyl and C1-C4-alkyl-aryl;
- R3 is selected from —C(O)H and —C(O)C1-C4-alkyl;
- X is a halide;
- and
- A is a halide or other counterion of the strong acid,
- wherein reacting the compound of formula (III) with the compound of formula (V) is performed in the presence of a base having a pKa in water of less than 9.
7 more elements
Dependencies are inferred from the claim text.