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US 10,723,766 B2Granted
Derivatives of gamma-amanitin
AssigneeHeidelberg Pharma Research GmbH
InventorsSusanne Werner-Simon, Christian Lutz, Christoph Müller, Werner Simon
Life of this patent
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Abstract
The invention relates to γ-amaninamide (1; x=0, 1 or 2), γ-amaninamidic acid (2; x=0, 1 or 2), and γ-amaninamidic hydroxamic acid (3; x=0, 1 or 2), novel derivatives of γ-amanitin (4), and methods and novel building blocks for the synthesis thereof.
Claims4
A method for synthesizing a compound of formula 6 (2S,3R,4S)—CH3—CH(OR1)—CH(CH3)—CH(NHR2)—C(═O)OR3, wherein R1 is C(═O)—R1′, wherein R1′ is alkyl, comprising the steps of (a) complexing the compound 5 (2S,3R,4S)-L-4-hydroxyisoleucine with copper or boron compounds;
- (b) acylation of the 4-hydroxy group of the resulting compound from step (a) with a compound R1′—C(═O)—X, wherein X is a leaving group;
- (c) cleavage of the metal complex resulting from step (b);
- (d) protection of the α-amino group with an R2 group, wherein the R2 group is an Fmoc group;
- and (e) protection of the carboxyl group with an R3 group, wherein the R3 group is a benzyl group or t-butyl group.
1 more element
Dependencies are inferred from the claim text.