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US 10,870,628 B2Granted
Formation of N-protected 3,6-bis-(4-aminobutyl)-2,5-diketopiperazine through a cyclic α-N-protected amino ester
AssigneeMannKind Corporation
InventorsJohn J. Freeman, Otto Phanstiel, William Elliot Bay, Kelly Sullivan Kraft
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Abstract
A method for the synthesis of N-protected 3,6-aminoalkyl-2,5-diketopiperazines is provided. The method includes obtaining a cyclic α-N protected active amino ester and adding it to a mixture of an amine catalyst in an organic solvent.
Claims20
A method for the synthesis of a compound according to Formula I:
- the method comprising adding a cyclic amino compound according to the following formula:
- to a catalyst in an organic solvent selected from THF, dioxane, and ethanol, and heating the mixture for a period of 2 to 6 hours,
- wherein the cyclic amino compound is added over a period of greater than one hour,
- wherein R is a C3 to C5 N-protected alkyl amine,
- wherein the protecting group (PG) is selected from the group consisting of amide forming protecting groups and carbamate forming protecting groups,
- wherein n is from 2-4, and
- wherein X is selected from C, P, and S.
4 more elements
A method for the synthesis of a diketopiperazine according to Formula II,
- the method comprising mixing a cyclic amino compound according to the following formula:
- with a catalyst in an organic solvent selected from THF, dioxane, and ethanol, and heating the mixture for a period of 2 to 6 hours, and removing the PG after formation of diketopiperazine,
- wherein R is a C4 N-protected alkyl amine,
- wherein the protecting group (PG) is selected from the group consisting of amide forming protecting groups and carbamate forming protecting groups, and
- wherein X is selected from C, P, and S.
2 more elements
Dependencies are inferred from the claim text.