US 2020/0369685 A1Published application

Boronic ester prodrugs and uses thereof

OwnerJeremiah A. Johnson, Paiman Ghoroghchian +4inventors

InventorsJeremiah A. Johnson, Paiman Ghoroghchian, Yivan Jiang, Hung Vanthanh Nguyen, Irene Ghobrial, Alexandre Detappe

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Abstract

Disclosed herein are compounds of Formula (I) or (II). The compounds include an agent (e.g., pharmaceutical agent, cosmetic agent, or nutraceutical agent) through a linker that includes a boronic ester moiety in the backbone of the linker. The compounds may be monomers. Also provided are polymers prepared by polymerizing the monomers. The polymers may be useful for delivering the agent to a subject, tissue, biological sample, or a cell. Also provided are methods of preparing the polymers, compositions and kits comprising the polymers, and methods of use (e.g., use in delivering the agent, treating a disease, preventing a disease, diagnosing a disease) involving the polymers or compositions. The structure of the boronic ester moiety may be fine tuned so that the properties related to delivery to a subject, biological sample, tissue, or cell may be fine tuned.

Claims32

Dependent claims

A compound of Formula (I) or (II):

or a salt thereof, wherein:
X is a reaction handle;
L1 is a substituted or unsubstituted linker, wherein the backbone of L1 comprises two or more atoms;
each instance of Y is independently —C(R1)2—;
each instance of R is independently absent, hydrogen, halogen, substituted or unsubstituted, C1-6 alkyl, substituted or unsubstituted, C2-6 alkenyl, substituted or unsubstituted, C2-6 alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, —ORa, —N(Ra)2, —SRa, —CN, —SCN, —C(═NRa)Ra, —C(═NRa)ORa, —C(═NRa)N(Ra)2, —C(═O)Ra, —C(═O)ORa, —C(═O)N(Ra)2, —NO2, —NRaC(═O)Ra, —NRaC(═O)ORa, —NRaC(═O)N(Ra)2, —OC(═O)Ra, —OC(═O)ORa, or —OC(═O)N(Ra)2, or two instances of R are joined to form substituted or unsubstituted carbocyclyl or substituted or unsubstituted heterocyclyl;
each instance of Ra is independently hydrogen, halogen, substituted or unsubstituted, C1-6 alkyl, substituted or unsubstituted, C2-6 alkenyl, substituted or unsubstituted, C2-6 alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, a nitrogen protecting group when attached to a nitrogen atom, an oxygen protecting group when attached to an oxygen atom, or a sulfur protecting group when attached to a sulfur atom, or two instances of Ra on a nitrogen atom are joined with the nitrogen atom to form substituted or unsubstituted heterocyclyl or substituted or unsubstituted heteroaryl;
each instance of L is independently a bond or a substituted or unsubstituted linker, wherein the atom in the backbone of L attached to Ring A or Ring C is carbon;
each instance of M is independently an agent;
each instance of m is independently an integer between 1 and 10, inclusive;
each instance of c is independently an integer between 1 and 2, inclusive;
and
d is an integer between 1 and 10, inclusive.

9 more elements

A polymer comprising one or more types of repeating units, wherein at least one type of the repeating units comprises a moiety of the formula:

wherein:
L1 is a substituted or unsubstituted linker, wherein the backbone of L1 comprises two or more atoms;
each instance of Y is independently —C(R1)2—;
each instance of R is independently absent, hydrogen, halogen, substituted or unsubstituted, C1-6 alkyl, substituted or unsubstituted, C2-6 alkenyl, substituted or unsubstituted, C2-6 alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, —ORa, —N(Ra)2, —SRa, —CN, —SCN, —C(═NRa)Ra, —C(═NRa)ORa, —C(═NRa)N(Ra)2, —C(═O)Ra, —C(═O)ORa, —C(═O)N(Ra)2, —NO2, —NRaC(═O)Ra, —NRaC(═O)ORa, —NRaC(═O)N(Ra)2, —OC(═O)Ra, —OC(═O)ORa, or —OC(═O)N(Ra)2, or two instances of R are joined to form substituted or unsubstituted carbocyclyl or substituted or unsubstituted heterocyclyl;
each instance of Ra is independently hydrogen, halogen, substituted or unsubstituted, C1-6 alkyl, substituted or unsubstituted, C2-6 alkenyl, substituted or unsubstituted, C2-6 alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, a nitrogen protecting group when attached to a nitrogen atom, an oxygen protecting group when attached to an oxygen atom, or a sulfur protecting group when attached to a sulfur atom, or two instances of Ra on a nitrogen atom are joined with the nitrogen atom to form substituted or unsubstituted heterocyclyl or substituted or unsubstituted heteroaryl;
each instance of L is independently a bond or a substituted or unsubstituted linker, wherein the atom in the backbone of L attached to Ring A or Ring C is carbon;
each instance of M is independently an agent;
each instance of m is independently an integer between 1 and 10, inclusive;
each instance of c is independently an integer between 1 and 2, inclusive;
and
d is an integer between 1 and 10, inclusive.

8 more elements

Dependencies are inferred from the claim text.

Facts

Application: 16/825,269Filed 20 Mar 2020
Priority: 20 May 2019
Published: 26 Nov 2020
Term ends: Not estimatedThe source records don’t support an estimate.

Classification10 codes

C07F 5/02
Compounds containing elements of Groups 3 or 13 of the Periodic Table: boron compounds
C07F 5/025
Boron compounds: boronic and borinic acid compounds
A61K 31/69
Medicinal preparations containing organic active ingredients: boron compounds
A61K 47/59
The modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule: obtained otherwise than by…