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US 2025/0144032 A1Published application
Poly(beta-amino ester) microparticles for micronutrient fortification
AssigneeMassachusetts Institute of Technology
InventorsRobert S. Langer, Ana Jaklenec, Ruiqing Xiao, Linzixuan Zhang
Life of this patent
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Abstract
Provided herein are compounds, such as compounds of Formulae (I) and (III), and compositions, methods, uses, and kits thereof. The compounds provided herein are poly(β-amino esters) useful for delivery of agents, such as vitamins and minerals, for the treatment and/or prevention of various diseases and conditions (e.g., micronutrient deficiency).
Claims87
A compound of Formula (I):
- or a pharmaceutically acceptable salt, stereoisomer, or isotopically labeled derivative thereof, wherein:
- L is a heterocycle comprising at least one oxygen atom;
- each Z is independently of Formula (i), (ii), (iii), or (iv):
- linker A is branched or unbranched, optionally substituted, cyclic or acyclic aliphatic;
- branched or unbranched, optionally substituted, cyclic or acyclic heteroaliphatic;
- optionally substituted arylene;
- or optionally substituted heteroarylene;
- R1 and R2 are each independently hydrogen;
- branched or unbranched, optionally substituted, cyclic or acyclic aliphatic;
- branched or unbranched, optionally substituted, cyclic or acyclic heteroaliphatic;
- branched or unbranched, optionally substituted, cyclic or acyclic acyl;
- optionally substituted aryl;
- optionally substituted heteroaryl;
- or a nitrogen protecting group;
- or
- one or both R1 or R2 are each optionally independently joined to linker A together with the intervening atoms to form a linker comprising one or more N-containing heterocycles;
- or
- R1 and R2 are joined together with the intervening atoms to form a N-containing heterocycle;
- R3 is branched or unbranched, optionally substituted, cyclic or acyclic aliphatic;
- branched or unbranched, optionally substituted, cyclic or acyclic heteroaliphatic;
- branched or unbranched, optionally substituted, cyclic or acyclic acyl;
- optionally substituted aryl;
- optionally substituted heteroaryl;
- or a nitrogen protecting group;
- linker B is branched or unbranched, optionally substituted, cyclic or acyclic aliphatic;
- branched or unbranched, optionally substituted, cyclic or acyclic heteroaliphatic;
- optionally substituted arylene;
- or optionally substituted heteroarylene;
- R4 is hydrogen, branched or unbranched, optionally substituted, cyclic or acyclic aliphatic;
- branched or unbranched, optionally substituted, cyclic or acyclic heteroaliphatic;
- branched or unbranched, optionally substituted, cyclic or acyclic acyl;
- optionally substituted aryl;
- optionally substituted heteroaryl;
- or a nitrogen protecting group;
- or
- R4 is joined to linker B together with the intervening atoms to form a linker comprising a N-containing heterocycle;
- and
- m, n, and p are each independently an integer between 1 and 10,000.
35 more elements
A compound of Formula (III):
- or a pharmaceutically acceptable salt, stereoisomer, or isotopically labeled derivative thereof, wherein:
- L is a heterocycle comprising at least one oxygen atom;
- each Z is independently of Formula (i), (ii), (iii), or (iv):
- linker A is branched or unbranched, optionally substituted, cyclic or acyclic aliphatic;
- branched or unbranched, optionally substituted, cyclic or acyclic heteroaliphatic;
- optionally substituted arylene;
- or optionally substituted heteroarylene;
- R1 and R2 are each independently hydrogen;
- branched or unbranched, optionally substituted, cyclic or acyclic aliphatic;
- branched or unbranched, optionally substituted, cyclic or acyclic heteroaliphatic;
- branched or unbranched, optionally substituted, cyclic or acyclic acyl;
- optionally substituted aryl;
- optionally substituted heteroaryl;
- or a nitrogen protecting group;
- or
- one or both R1 or R2 are each optionally independently joined to linker A together with the intervening atoms to form a linker comprising one or more N-containing heterocycles;
- or
- R1 and R2 are joined together with the intervening atoms to form a N-containing heterocycle;
- R3 is branched or unbranched, optionally substituted, cyclic or acyclic aliphatic;
- branched or unbranched, optionally substituted, cyclic or acyclic heteroaliphatic;
- branched or unbranched, optionally substituted, cyclic or acyclic acyl;
- optionally substituted aryl;
- optionally substituted heteroaryl;
- or a nitrogen protecting group;
- linker B is branched or unbranched, optionally substituted, cyclic or acyclic aliphatic;
- branched or unbranched, optionally substituted, cyclic or acyclic heteroaliphatic;
- optionally substituted arylene;
- or optionally substituted heteroarylene;
- R4 is hydrogen, branched or unbranched, optionally substituted, cyclic or acyclic aliphatic;
- branched or unbranched, optionally substituted, cyclic or acyclic heteroaliphatic;
- branched or unbranched, optionally substituted, cyclic or acyclic acyl;
- optionally substituted aryl;
- optionally substituted heteroaryl;
- or a nitrogen protecting group;
- or
- R4 is joined to linker B together with the intervening atoms to form a linker comprising a N-containing heterocycle;
- m, n, and p are each independently an integer between 1 and 10,000;
- each instance of RA is independently —ORC, —SRC, —N(RC)2, —ZRC, or
- each instance of RB is independently
- and
- each instance of RC is independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted heteroalkyl, optionally substituted heteroalkenyl, optionally substituted heteroalkynyl, optionally substituted carbocyclyl, optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl, an oxygen protecting group when attached to an oxygen atom, a sulfur protecting group when attached to a sulfur atom, a nitrogen protecting group when attached to a nitrogen atom, or two instances of RC attached to the same intervening atom are joined together with the intervening atom to form optionally substituted heterocyclyl or optionally substituted heteroaryl.
38 more elements
A method of preparing a compound comprising Formula (I), or a pharmaceutically acceptable salt, stereoisomer, or isotopically labeled derivative thereof, the method comprising reacting one or more compounds of Formula (II):
- or a salt, isotope, or stereoisomer thereof, with one or more compounds selected from
- or a salt, isotope, or stereoisomer thereof, wherein:
- L is a heterocycle comprising at least one oxygen atom;
- linker A is branched or unbranched, optionally substituted, cyclic or acyclic aliphatic;
- branched or unbranched, optionally substituted, cyclic or acyclic heteroaliphatic;
- optionally substituted arylene;
- or optionally substituted heteroarylene;
- R1 and R2 are each independently hydrogen;
- branched or unbranched, optionally substituted, cyclic or acyclic aliphatic;
- branched or unbranched, optionally substituted, cyclic or acyclic heteroaliphatic;
- branched or unbranched, optionally substituted, cyclic or acyclic acyl;
- optionally substituted aryl;
- optionally substituted heteroaryl;
- or a nitrogen protecting group;
- or
- one or both R1 or R2 are each optionally independently joined to linker A together with the intervening atoms to form a linker comprising one or more N-containing heterocycles;
- or
- R1 and R2 are joined together with the intervening atoms to form a N-containing heterocycle;
- R3 is branched or unbranched, optionally substituted, cyclic or acyclic aliphatic;
- branched or unbranched, optionally substituted, cyclic or acyclic heteroaliphatic;
- branched or unbranched, optionally substituted, cyclic or acyclic acyl;
- optionally substituted aryl;
- optionally substituted heteroaryl;
- or a nitrogen protecting group;
- linker B is branched or unbranched, optionally substituted, cyclic or acyclic aliphatic;
- branched or unbranched, optionally substituted, cyclic or acyclic heteroaliphatic;
- optionally substituted arylene;
- or optionally substituted heteroarylene;
- and
- R4 is hydrogen, branched or unbranched, optionally substituted, cyclic or acyclic aliphatic;
- branched or unbranched, optionally substituted, cyclic or acyclic heteroaliphatic;
- branched or unbranched, optionally substituted, cyclic or acyclic acyl;
- optionally substituted aryl;
- optionally substituted heteroaryl;
- or a nitrogen protecting group;
- or
- R4 is joined to linker B together with the intervening atoms to form a linker comprising a N-containing heterocycle.
34 more elements
A compound prepared by reacting one or more compounds of Formula (II):
- or a salt, isotope, or stereoisomer thereof, with one or more compounds selected from
- or a salt, isotope, or stereoisomer thereof, wherein:
- L is a heterocycle comprising at least one oxygen atom;
- linker A is branched or unbranched, optionally substituted, cyclic or acyclic aliphatic;
- branched or unbranched, optionally substituted, cyclic or acyclic heteroaliphatic;
- optionally substituted arylene;
- or optionally substituted heteroarylene;
- R1 and R2 are each independently hydrogen;
- branched or unbranched, optionally substituted, cyclic or acyclic aliphatic;
- branched or unbranched, optionally substituted, cyclic or acyclic heteroaliphatic;
- branched or unbranched, optionally substituted, cyclic or acyclic acyl;
- optionally substituted aryl;
- optionally substituted heteroaryl;
- or a nitrogen protecting group;
- or
- one or both R1 or R2 are each optionally independently joined to linker A together with the intervening atoms to form a linker comprising one or more N-containing heterocycles;
- or
- R1 and R2 are joined together with the intervening atoms to form a N-containing heterocycle;
- R3 is branched or unbranched, optionally substituted, cyclic or acyclic aliphatic;
- branched or unbranched, optionally substituted, cyclic or acyclic heteroaliphatic;
- branched or unbranched, optionally substituted, cyclic or acyclic acyl;
- optionally substituted aryl;
- optionally substituted heteroaryl;
- or a nitrogen protecting group;
- linker B is branched or unbranched, optionally substituted, cyclic or acyclic aliphatic;
- branched or unbranched, optionally substituted, cyclic or acyclic heteroaliphatic;
- optionally substituted arylene;
- or optionally substituted heteroarylene;
- and
- R4 is hydrogen, branched or unbranched, optionally substituted, cyclic or acyclic aliphatic;
- branched or unbranched, optionally substituted, cyclic or acyclic heteroaliphatic;
- branched or unbranched, optionally substituted, cyclic or acyclic acyl;
- optionally substituted aryl;
- optionally substituted heteroaryl;
- or a nitrogen protecting group;
- or
- R4 is joined to linker B together with the intervening atoms to form a linker comprising a N-containing heterocycle.
34 more elements
Dependencies are inferred from the claim text.