IP Library › Granted Patent US 12,186,396
Granted Patent B2
US 12,186,396 · App. 17/751,540 · Granted Jan 7, 2025

Branched multi-functional macromonomers and related polymers and uses thereof

Inventors: Jeremiah A. Johnson (Boston, MA); Nolan Gallagher (Cambridge, MA); Farrukh Vohidov (Cambridge, MA); Yivan Jiang (Revere, MA); Hung Vanthanh Nguyen (Braintree, MA)
Assignee: Massachusetts Institute of Technology
A61K47/18A61K47/34A61K47/595A61P35/00B01J31/2278C07D403/14C07D405/14C08G61/08C08G69/48C08G83/00C08L71/02G01N33/574B01J2523/821C08G2261/135C08G2261/136C08G2261/1414C08G2261/1424C08G2261/1426C08G2261/1432C08G2261/418C08G2261/76
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Quick Facts
Patent No.
US 12,186,396
App. No.
17/751,540
Granted
Jan 7, 2025
Kind
B2
Abstract

Disclosed are methods, compositions, reagents, systems, and kits to prepare and utilize branched multi-functional macromonomers, which contain a ring-opening metathesis polymerizable norbornene group, one or more reactive sites capable of undergoing click chemistry, and a terminal acyl group capable of undergoing a coupling reaction; branched multi-cargo macromonomers; and the corresponding polymers are disclosed herein. Various embodiments show that the macromonomers and polymers disclosed herein display unprecedented control of cargo loading of agents. These materials have the potential to be utilized for the treatment of diseases and conditions such as cancer and hypertension.

Claims (54)

1. A macromonomer of Formula (I):

or a salt thereof, wherein:

each instance of RA is independently hydrogen, halogen, or substituted or unsubstituted, C 1-6 alkyl;

a is an integer from 1 to 20, inclusive;

each instance of M is independently hydrogen or an agent;

each instance of m is independently an integer from 1 to 10, inclusive;

each instance of L is independently substituted or unsubstituted, C 1-200 alkylene, substituted or unsubstituted, C 2-200 alkenylene, substituted or unsubstituted, C 2-200 alkynylene, substituted or unsubstituted, C 2-200 heteroalkylene, substituted or unsubstituted, C 2-200 heteroalkenylene, or substituted or unsubstituted, C 2-200 heteroalkynylene, wherein:

optionally one or more carbons in each instance of the substituted or unsubstituted, C 1-200 alkylene, substituted or unsubstituted, C 2-200 alkenylene, substituted or unsubstituted, C 2-200 alkynylene, substituted or unsubstituted, C 2-200 heteroalkylene, substituted or unsubstituted, C 2-200 heteroalkenylene, and substituted or unsubstituted, C 2-200 heteroalkynylene are independently replaced with substituted or unsubstituted carbocyclylene, substituted or unsubstituted heterocyclylene, substituted or unsubstituted arylene, or substituted or unsubstituted heteroarylene;

optionally one or more heteroatoms in each instance of the substituted or unsubstituted, C 2-200 heteroalkylene, substituted or unsubstituted, C 2-200 heteroalkenylene, and substituted or unsubstituted, C 2-200 heteroalkynylene are independently replaced with substituted or unsubstituted carbocyclylene, substituted or unsubstituted heterocyclylene, substituted or unsubstituted arylene, or substituted or unsubstituted heteroarylene;

provided that when each instance of M is hydrogen, at least one instance of -L(M) m comprises a click-chemistry handle;

each instance of R B is independently hydrogen, halogen, or substituted or unsubstituted, C 1-6 alkyl;

each instance of b is independently an integer from 1 to 20, inclusive;

e is an integer from 1 to 10, inclusive;

X is —OR C or —N(R D ) 2 , wherein:

R C is hydrogen, substituted or unsubstituted, C 1-1000 alkyl, substituted or unsubstituted, C 2-1000 alkenyl, substituted or unsubstituted, C 2-1000 alkynyl, substituted or unsubstituted, C 1-1000 heteroalkyl, substituted or unsubstituted, C 2-1000 heteroalkenyl, substituted or unsubstituted, C 2-1000 heteroalkynyl, an oxygen protecting group, or a leaving group; and

each instance of R D is independently hydrogen, substituted or unsubstituted, C 1-1000 alkyl, substituted or unsubstituted, C 2-1000 alkenyl, substituted or unsubstituted, C 2-1000 alkynyl, substituted or unsubstituted, C 1-1000 heteroalkyl, substituted or unsubstituted, C 2-1000 heteroalkenyl,-substituted or unsubstituted, C 2-1000 heteroalkynyl, or a nitrogen protecting group, or two R D are taken together to form a substituted or unsubstituted heterocyclyl or substituted or unsubstituted heteroaryl moiety.

2. A macromonomer of Formula (II):

or a salt thereof, wherein:

each instance of RA is independently hydrogen, halogen, or substituted or unsubstituted, C 1-6 alkyl;

a is an integer from 1 to 20, inclusive;

each instance of M′ is independently an agent;

each instance of m′ is independently an integer from 2 to 10, inclusive;

each instance of L is independently substituted or unsubstituted, C 1-200 alkylene, substituted or unsubstituted, C 2-200 alkenylene, substituted or unsubstituted, C 2-200 alkynylene, substituted or unsubstituted, C 2-200 heteroalkylene, substituted or unsubstituted, C 2-200 heteroalkenylene, or substituted or unsubstituted, C 2-200 heteroalkynylene, wherein:

optionally one or more carbons in each instance of the substituted or unsubstituted, C 1-200 alkylene, substituted or unsubstituted, C 2-200 alkenylene, substituted or unsubstituted, C 2-200 alkynylene, substituted or unsubstituted, C 2-200 heteroalkylene, substituted or unsubstituted, C 2-200 heteroalkenylene, and substituted or unsubstituted, C 2-200 heteroalkynylene are independently replaced with substituted or unsubstituted carbocyclylene, substituted or unsubstituted heterocyclylene, substituted or unsubstituted arylene, or substituted or unsubstituted heteroarylene;

optionally one or more heteroatoms in each instance of the substituted or unsubstituted, C 2-200 heteroalkylene, substituted or unsubstituted, C 2-200 heteroalkenylene, and substituted or unsubstituted, C 2-200 heteroalkynylene are independently replaced with substituted or unsubstituted carbocyclylene, substituted or unsubstituted heterocyclylene, substituted or unsubstituted arylene, or substituted or unsubstituted heteroarylene;

each instance of R B is independently hydrogen, halogen, or substituted or unsubstituted, C 1-6 alkyl;

each instance of b is independently an integer from 1 to 20, inclusive;

e is an integer from 1 to 10, inclusive;

X is —OR C or —N(R D ) 2 , wherein:

R C is hydrogen, substituted or unsubstituted, C 1-1000 alkyl, substituted or unsubstituted, C 2-1000 alkenyl, substituted or unsubstituted, C 2-1000 alkynyl, substituted or unsubstituted, C 1-1000 heteroalkyl, substituted or unsubstituted, C 2-1000 heteroalkenyl, substituted or unsubstituted, C 2-1000 heteroalkynyl, an oxygen protecting group, or a leaving group;

each instance of R D is independently hydrogen, substituted or unsubstituted, C 1-1000 alkyl, substituted or unsubstituted, C 2-1000 alkenyl, substituted or unsubstituted, C 2-1000 alkynyl, substituted or unsubstituted, C 1-1000 heteroalkyl, substituted or unsubstituted, C 2-1000 heteroalkenyl, substituted or unsubstituted, C 2-1000 heteroalkynyl, or a nitrogen protecting group, or two R D are taken together to form a substituted or unsubstituted heterocyclyl or substituted or unsubstituted heteroaryl moiety; and

each instance of R1 is independently hydrogen, halogen, or substituted or unsubstituted, C 1-6 alkyl, or two R1 bonded to the same carbon are taken together to form an oxo group.

3. A polymer prepared by polymerizing a macromonomer of claim 2 , or a salt thereof, in the presence of a metathesis catalyst.

4. A polymer prepared by polymerizing a macromonomer of claim 1 , or a salt thereof, in the presence of a metathesis catalyst.

5. A polymer prepared by subjecting to polymerization conditions a mixture comprising a solvent, a metathesis catalyst, and a macromonomer of claim 1 or a salt thereof.

6. The polymer of claim 5 , wherein e is 1.

7. The polymer of claim 6 , wherein each instance of RA is hydrogen, and each instance of R B is hydrogen.

8. The polymer of claim 7 , wherein a is 4, 5, or 6, and each instance of b is 2, 3, 4, 5, or 6.

9. The polymer of claim 8 , wherein each instance of m is 1.

10. The polymer of claim 5 , wherein X is —N(R D ) 2 .

11. The polymer of claim 9 , wherein X is —N(R D ) 2 .

12. The polymer of claim 5 , wherein each instance of R D is independently hydrogen or substituted or unsubstituted, C 1-1000 heteroalkyl.

13. The polymer of claim 11 , wherein each instance of R D is independently hydrogen or substituted or unsubstituted, C 1-1000 heteroalkyl.

14. The polymer of claim 5 , wherein each instance of R D is independently hydrogen or substituted or unsubstituted, C 50-1000 heteroalkyl.

15. The polymer of claim 11 , wherein each instance of R D is independently hydrogen or substituted or unsubstituted, C 50-1000 heteroalkyl.

16. The polymer of claim 5 , wherein each instance of L is independently substituted or unsubstituted, C 1-200 alkylene, or substituted or unsubstituted, C 2-200 heteroalkylene.

17. The polymer of claim 11 , wherein each instance of L is independently substituted or unsubstituted, C 1-200 alkylene, or substituted or unsubstituted, C 2-200 heteroalkylene.

18. The polymer of claim 5 , wherein each instance of L is substituted or unsubstituted, C 2-200 heteroalkylene, wherein one or more carbons and/or one or more heteroatoms of the substituted or unsubstituted, C 2-200 heteroalkylene are independently replaced with substituted or unsubstituted carbocyclylene, substituted or unsubstituted heterocyclylene, substituted or unsubstituted arylene, or substituted or unsubstituted heteroarylene.

19. The polymer of claim 11 , wherein each instance of L is substituted or unsubstituted, C 2-200 heteroalkylene, wherein one or more carbons and/or one or more heteroatoms of the substituted or unsubstituted, C 2-200 heteroalkylene are independently replaced with substituted or unsubstituted carbocyclylene, substituted or unsubstituted heterocyclylene, substituted or unsubstituted arylene, or substituted or unsubstituted heteroarylene.

20. The polymer of claim 13 , wherein each instance of L is substituted or unsubstituted, C 2-200 heteroalkylene, wherein one or more carbons and/or one or more heteroatoms of the substituted or unsubstituted, C 2-200 heteroalkylene are independently replaced with substituted or unsubstituted carbocyclylene, substituted or unsubstituted heterocyclylene, substituted or unsubstituted arylene, or substituted or unsubstituted heteroarylene.

21. The polymer of claim 11 , wherein M is a therapeutic agent.

22. The polymer of claim 13 , wherein M is a therapeutic agent.

23. The polymer of claim 20 , wherein M is a therapeutic agent.

24. The polymer of claim 23 , wherein the metathesis catalyst is a transition metal metathesis catalyst or Grubbs catalyst.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 31, 2022
From: JOHNSON, JEREMIAH A.; GALLAGHER, NOLAN; VOHIDOV, FARRUKH; JIANG, YIVAN; NGUYEN, HUNG VANTHANH
To: MASSACHUSETTS INSTITUTE OF TECHNOLOGY
Reel/Frame 060946/0261 →
Continuity (4)
Continuation 16898331 · Jun 10, 2020
Division 16024662 · Jun 29, 2018
Provisional Application 62528010 · Jun 30, 2017
Related Publication 20230068959A1 · Mar 2, 2023
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