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US 9,957,296 B2Granted
Triazole macrocycle systems
AssigneeAileron Therapeutics, Inc.
InventorHuw M. Nash
Life of this patent
Estimating the term…
Abstract
The present invention provides novel peptidomimetic macrocycles and methods for their preparation and use, as well as amino acid analogs and macrocycle-forming linkers, and kits useful in their production.
Claims8
A method of synthesizing a peptidomimetic macrocycle, the method comprising:
- (a) synthesizing a peptide that incorporates:
- (i) an alkyne moiety;
- and
- (ii) an amino acid moiety of the formula:
- wherein:
- R2 is alkyl, alkenyl, alkynyl, arylalkyl, cycloalkylalkyl, heteroalkyl, or heterocycloalkyl, each of which is unsubstituted or substituted with halo-, or —H;
- each Q and T is independently selected from the group consisting of alkylene, cycloalkylene, heterocycloalkylene, arylene, heteroarylene and [—R4—K—R4—]n, each of which is unsubstituted or substituted with R5;
- each K is independently O, S, SO, SO2, CO, CO2, or CONR3;
- each R3 is independently alkyl, alkenyl, alkynyl, arylalkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, cycloalkylalkyl, cycloaryl, or heterocycloaryl, each of which is unsubstituted or substituted with R5, or —H;
- each R4 is independently alkylene, alkenylene, alkynylene, heteroalkylene, cycloalkylene, heterocycloalkylene, arylene, or heteroarylene;
- each R5 is independently halogen, alkyl, —OR6, —N(R6)2, —SR6, —SORE, —SO2R6, —CO2R6, a fluorescent moiety, a radioisotope or a therapeutic agent;
- each R6 is independently —H, alkyl, alkenyl, alkynyl, arylalkyl, cycloalkylalkyl, heterocycloalkyl, a fluorescent moiety, a radioisotope or a therapeutic agent;
- R8 is —H, alkyl, alkenyl, alkynyl, arylalkyl, cycloalkylalkyl, heteroalkyl, or heterocycloalkyl;
- R10 and R11 are independently —H or any protecting group suitable for peptide synthesis;
- g and h are each independently an integer from 0 to 5;
- n is an integer from 1 to 5;
- and
- (b) macrocyclizing the peptide,
- wherein the peptidomimetic macrocycle comprises an additional macrocycle.
16 more elements
Dependencies are inferred from the claim text.