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US 8,541,590 B2Granted
Proteasome inhibitors and processes for their preparation, purification and use
AssigneeCephalon, Inc.
InventorRenee Caroline Roemmele
Life of this patent
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Abstract
The invention provides boronic esters of Formula I wherein R1, R2, R3, and R4 are as described herein, and methods for the preparation and purification thereof.
Claims15
A boronic ester of Formula I
- wherein
- R1 is 2-(6-phenyl)pyridinyl, R2 is (1R)-1-hydroxyethyl, and R3 and R4 are H;
- R1 is 2-(6-phenyl)pyridinyl, R2 is (1R)-1-hydroxyethyl, and R3 and R4 are methyl;
- or
- R1 is 2-pyrazinyl, R2 is benzyl, and R3 and R4 are H.
2 more elements
A process for purifying a boronic acid of Formula IA
- wherein
- R1 is 2-(6-phenyl)pyridinyl and R2 is (1R)-1-hydroxyethyl, or R1 is 2-pyrazinyl and R2 is benzyl;
- comprising the steps of:
- (a) converting the boronic acid of Formula IA into a boronic ester of Formula VII
- (b) crystallizing the boronic ester of Formula VII from solution;
- (c) isolating the crystallized boronic ester of Formula VII from the solution;
- and
- (d) converting the isolated boronic ester of Formula VII back into the boronic acid of Formula IA.
5 more elements
A process for preparing a boronic acid of Formula IA
- wherein
- R1 is 2-(6-phenyl)pyridinyl and R2 is (1R)-1-hydroxyethyl, or R1 is 2-pyrazinyl and R2 is benzyl;
- comprising the steps of:
- (a) preparing a boronic ester of Formula V
- wherein
- R1 is 2-(6-phenyl)pyridinyl, R2 is (1R)-1-hydroxyethyl, and R3 and R4 are H;
- R1 is 2-(6-phenyl)pyridinyl, R2 is (1R)-1-hydroxyethyl, and R3 and R4 are methyl;
- or
- R1 is 2-pyrazinyl, R2 is benzyl, and R3 and R4 are H;
- (b) crystallizing a boronic ester of Formula I from a solution of the boronic ester of Formula V
- (c) converting the boronic ester of Formula I into the boronic acid of Formula IA.
8 more elements
Dependencies are inferred from the claim text.