IP Library › Granted Patent US 12,414,997

Granted Patent B2

US 12,414,997 · App. 17/047,279 · Granted Sep 16, 2025

Brush prodrugs and uses thereof

Inventors: Jeremiah A. Johnson (Boston, MA); Farrukh Vohidov (Arlington, MA)

Assignee: Massachusetts Institute of Technology

A61K47/59 A61K31/138 A61K31/167 A61K31/282 A61K31/404 A61K31/44 A61K31/475 A61K31/502 A61K31/519 A61K31/573 A61K38/212 A61K47/545 C07F15/0046 C08G61/08 C08G2261/136 C08G2261/1426 C08G2261/143 C08G2261/1432 C08G2261/418

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Quick Facts

Patent No.: US 12,414,997
App. No.: 17/047,279
Granted: Sep 16, 2025
Kind: B2

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Abstract

The present disclosure provides, in some aspects, macromonomers of Formula (I), and salts thereof; methods of preparing the macromonomers, and salts thereof; Brush prodrugs (polymers); methods of preparing the Brush prodrugs; compounds of Formula (II); conjugates of Formula (III), and salts thereof; pharmaceutical compositions comprising a Brush prodrug, or a conjugate or a salt thereof; kits comprising: a macromonomer or a salt thereof, a Brush prodrug, a compound, a conjugate or a salt thereof, or a pharmaceutical composition; methods of using the Brush prodrugs, or conjugates or salts thereof; and uses of the Brush prodrugs, and conjugates or salts thereof. These chemical entities may be useful in delivering pharmaceutical agents to a subject or cell.

Claims (128)

1. A macromonomer of Formula (I):

or a salt thereof, wherein:

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

a is an integer from 1 to 20, inclusive;

each instance of —Y—Z— is

each instance of M is independently hydrogen or a pharmaceutical 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; and

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 W is independently a single bond, —O—, —S—, or —NR E —;

each instance of R E is independently hydrogen, substituted or unsubstituted, C 1-6 alkyl, or a nitrogen protecting group;

each instance of W′ is independently —O—, —S—, or —NR J —;

each instance of R′ is independently hydrogen, substituted or unsubstituted, C 1-6 alkyl, or a nitrogen protecting group;

each instance of R K and R L is independently hydrogen, halogen, substituted or unsubstituted, C 1-6 alkyl, substituted or unsubstituted, C 2-6 alkenyl, substituted or unsubstituted, C 2-6 alkynyl, substituted or unsubstituted, 3- to 7-membered, monocyclic carbocyclyl, substituted or unsubstituted, 3- to 7-membered, monocyclic heterocyclyl, substituted or unsubstituted phenyl, substituted or unsubstituted, 5- or 6-membered, monocyclic heteroaryl, —OR a , —N(R a ) 2 , —SR a , —CN, —SCN, —C(═NR a )R a , —C(═NR a )OR a , —C(═NR a )N(R a ) 2 , —C(═O)R a , —C(═O)OR a , —C(═O)N(R a ) 2 , —NO 2 , —NR a C(═O)R a , —NR a C(═O)OR a , —NR a C(═O)N(R a ) 2 , —OC(═O)R a , —OC(═O)OR a , or —OC(═O)N(R a ) 2 ;

each instance of R a is independently hydrogen, substituted or unsubstituted, C 1-6 alkyl, substituted or unsubstituted, C 2-6 alkenyl, substituted or unsubstituted, C 2-6 alkynyl, substituted or unsubstituted, 3- to 7-membered, monocyclic carbocyclyl, substituted or unsubstituted, 3- to 7-membered, monocyclic heterocyclyl, substituted or unsubstituted phenyl, substituted or unsubstituted, 5- or 6-membered, monocyclic heteroaryl, an oxygen protecting group when attached to an oxygen atom, a sulfur protecting group when attached to a sulfur atom, or a nitrogen protecting group when attached to a nitrogen atom; or two instances of R a attached to the same nitrogen atom are joined to form substituted or unsubstituted, 3- to 7-membered, monocyclic heterocyclyl, or substituted or unsubstituted, 5- or 6-membered, monocyclic heteroaryl;

each instance of T is independently a single bond, substituted or unsubstituted, C 1-20 alkylene, substituted or unsubstituted, C 2-20 alkenylene, substituted or unsubstituted, C 2-20 alkynylene, substituted or unsubstituted, C 2-20 heteroalkylene, substituted or unsubstituted, C 2-20 heteroalkenylene, or substituted or unsubstituted, C 2-20 heteroalkynylene, wherein:

optionally one or more carbons in each instance of the substituted or unsubstituted, C 1-20 alkylene, substituted or unsubstituted, C 2-20 alkenylene, substituted or unsubstituted, C 2-20 alkynylene, substituted or unsubstituted, C 2-20 heteroalkylene, substituted or unsubstituted, C 2-20 heteroalkenylene, and substituted or unsubstituted, C 2-20 heteroalkynylene are independently replaced with substituted or unsubstituted carbocyclylene, substituted or unsubstituted heterocyclylene, substituted or unsubstituted arylene, or substituted or unsubstituted heteroarylene; and

optionally one or more heteroatoms in each instance of the substituted or unsubstituted, C 2-20 heteroalkylene, substituted or unsubstituted, C 2-20 heteroalkenylene, and substituted or unsubstituted, C 2-20 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; and

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.

2. A method of preparing a macromonomer of claim 1 , or a salt thereof, comprising coupling a compound of the formula:

or a salt thereof, with a compound of the formula: HOR C or HN(R D ) 2 , or a salt thereof.

3. A polymer prepared by polymerizing one or more types of macromonomers of claim 1 , or a salt thereof, in the presence of a metathesis catalyst.

4. A method of preparing a polymer of claim 3 comprising polymerizing a macromonomer of Formula (I):

or a salt thereof, in the presence of a metathesis catalyst, wherein:

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

a is an integer from 1 to 20, inclusive;

each instance of —Y—Z— is

each instance of M is independently hydrogen or a pharmaceutical agent;

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

each instance of W is independently a single bond, —O—, —S—, or —NR E —;

each instance of R E is independently hydrogen, substituted or unsubstituted, C 1-6 alkyl, or a nitrogen protecting group;

each instance of W′ is independently —O—, —S—, or —NR J —;

each instance of R′ is independently hydrogen, substituted or unsubstituted, C 1-6 alkyl, or a nitrogen protecting group;

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; and

X is —OR C or —N(R D ) 2 , wherein:

5. A method of preparing a polymer of claim 3 comprising polymerizing a first macromonomer of Formula (I):

or a salt thereof, and a second macromonomer of Formula (I), or a salt thereof, in the presence of a metathesis catalyst, wherein at least one instance of M of the first macromonomer is different from at least one instance of M of the second macromonomer, and wherein:

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

a is an integer from 1 to 20, inclusive;

each instance of —Y—Z— is

each instance of M is independently hydrogen or a pharmaceutical agent;

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

each instance of W is independently a single bond, —O—, —S—, or —NR E —;

each instance of R E is independently hydrogen, substituted or unsubstituted, C 1-6 alkyl, or a nitrogen protecting group;

each instance of W′ is independently —O—, —S—, or —NR J —;

each instance of R J is independently hydrogen, substituted or unsubstituted, C 1-6 alkyl, or a nitrogen protecting group;

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; and

X is —OR C or —N(R D ) 2 , wherein:

6. A pharmaceutical composition comprising a polymer of claim 3 and optionally a pharmaceutically acceptable excipient.

7. A kit comprising:

a macromonomer of claim 1 , or a salt thereof; and

instructions for using the macromonomer, or a salt thereof.

8. A method of delivering a pharmaceutical agent to a subject in need thereof comprising administering to the subject in need thereof a polymer of claim 3 .

9. A method of delivering a pharmaceutical agent to a cell comprising contacting the cell with a polymer of claim 3 .

10. A method of treating a disease in a subject in need thereof comprising administering to or implanting in the subject in need thereof a therapeutically effective amount of:

a polymer of claim 3 ;

wherein at least one instance of M is a therapeutic agent.

11. A method of preventing a disease in a subject in need thereof comprising administering to or implanting in the subject in need thereof a prophylactically effective amount of:

a polymer of claim 3 ;

wherein at least one instance of M is a prophylactic agent.

12. A method of diagnosing a disease in a subject comprising administering to or implanting in the subject a diagnostically effective amount of:

a polymer of claim 3 ;

wherein at least one instance of M is a diagnostic agent.

13. A kit comprising:

a polymer of claim 3 ; and

instructions for using the polymer.

14. The polymer of claim 3 , wherein each instance of R A and R B is hydrogen.

15. The polymer of claim 14 , wherein each instance of —Y—Z— is

16. The polymer of claim 15 , wherein each instance of L is independently substituted or unsubstituted, C 1-200 alkylene or substituted or unsubstituted, C 2-200 heteroalkylene, wherein one or more carbons in the C 1-200 alkylene or C 2-200 heteroalkylene are replaced with substituted or unsubstituted heteroarylene.

17. The polymer of claim 15 , wherein each instance of L is substituted or unsubstituted, C 3-30 alkylene.

18. The polymer of claim 16 , wherein each instance of W is a single bond.

19. The polymer of claim 18 , wherein each instance of R K is hydrogen, and each instance of R L is hydrogen.

20. The polymer of claim 19 , wherein each instance of T is independently a single bond, substituted or unsubstituted, C 1-20 alkylene, or substituted or unsubstituted, C 2-20 heteroalkylene, and each instance of M is a pharmaceutical agent.

21. The polymer of claim 20 , wherein X is —N(R D ) 2 .

22. The polymer of claim 21 , wherein each instance of R D is independently hydrogen or substituted or unsubstituted, C 1-1000 heteroalkyl, provided that at least one instance of R D is substituted or unsubstituted, C 50-1000 heteroalkyl.

23. The polymer of claim 3 , wherein the macromonomer is of the formula:

or a salt thereof.

24. The polymer of claim 3 , wherein the macromonomer is of the formula:

or a salt thereof.

25. The macromonomer of claim 1 , or a salt thereof, wherein the macromonomer is of the formula:

26. The macromonomer of claim 1 , or a salt thereof, wherein the macromonomer is of the formula:

27. The polymer of claim 21 , wherein X is

n is an integer from 40 to 100, inclusive; and R F is hydrogen or unsubstituted C 1-6 alkyl.

28. The polymer of claim 27 , wherein each instance of M is an anti-cancer agent.

29. The polymer of claim 28 , wherein each instance of m is independently 1, 2, or 3, and e is 1, 2, or 3.

30. The macromonomer of claim 1 , or a salt thereof, wherein each instance of R A and R B is hydrogen.

31. The macromonomer of claim 30 , or a salt thereof, wherein each instance of —Y—Z— is

32. The macromonomer of claim 31 , or a salt thereof, wherein each instance of L is independently substituted or unsubstituted, C 1-200 alkylene or substituted or unsubstituted, C 2-200 heteroalkylene, wherein one or more carbons in the C 1-200 alkylene or C 2-200 heteroalkylene are replaced with substituted or unsubstituted heteroarylene.

33. The macromonomer of claim 31 , or a salt thereof, wherein each instance of L is substituted or unsubstituted, C 3-30 alkylene.

34. The macromonomer of claim 32 , or a salt thereof, wherein each instance of W is a single bond.

35. The macromonomer of claim 34 , or a salt thereof, wherein each instance of R K is hydrogen, and each instance of R L is hydrogen.

36. The macromonomer of claim 35 , or a salt thereof, wherein each instance of T is independently a single bond, substituted or unsubstituted, C 1-20 alkylene, or substituted or unsubstituted, C 2-20 heteroalkylene, and each instance of M is a pharmaceutical agent.

37. The macromonomer of claim 36 , or a salt thereof, wherein X is —N(R D ) 2 .

38. The macromonomer of claim 37 , or a salt thereof, wherein each instance of R D is independently hydrogen or substituted or unsubstituted, C 1-1000 heteroalkyl, provided that at least one instance of R D is substituted or unsubstituted, C 50-1000 heteroalkyl.

39. The macromonomer of claim 37 , or a salt thereof, wherein X is

n is an integer from 40 to 100, inclusive; and R F is hydrogen or unsubstituted C 1-6 alkyl.

40. The macromonomer of claim 39 , or a salt thereof, wherein each instance of M is an anti-cancer agent.

41. The macromonomer of claim 40 , or a salt thereof, wherein each instance of m is independently 1, 2, or 3, and e is 1, 2, or 3.

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 9, 2021

From: JOHNSON, JEREMIAH A.; VOHIDOV, FARRUKH

To: MASSACHUSETTS INSTITUTE OF TECHNOLOGY

Reel/Frame 057425/0056 →

Continuity (3)

Provisional Application 62657715 · Apr 13, 2018

Related Publication 20210386861A1 · Dec 16, 2021

Related Publication 20220370628A9 · Nov 24, 2022

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