US 12,377,153 B2
Poly(beta-thioester) polymers and polymeric nanoparticles
Robert Langer, Newton, MA (US); Carlo Traverso, Newton, MA (US); Ameya Kirtane, Somerville, MA (US); Daniel Reker, Somerville, MA (US); Lewis Scott Jones, Cambridge, MA (US); Hyunjoon Kim, Cambridge, MA (US); and Netra Rajesh, Cambridge, MA (US)
Assigned to MASSACHUSETTS INSTITUTE OF TECHNOLOGY, Cambridge, MA (US); and THE BRIGHAM AND WOMEN'S HOSPITAL, INC., Boston, MA (US)
Appl. No. 17/597,974
Filed by MASSACHUSETTS INSTITUTE OF TECHNOLOGY, Cambridge, MA (US); and THE BRIGHAM AND WOMEN'S HOSPITAL, INC., Boston, MA (US)
PCT Filed Jul. 31, 2020, PCT No. PCT/US2020/044551
§ 371(c)(1), (2) Date Jan. 31, 2022,
PCT Pub. No. WO2021/022185, PCT Pub. Date Feb. 4, 2021.
Claims priority of provisional application 62/881,755, filed on Aug. 1, 2019.
Prior Publication US 2022/0175938 A1, Jun. 9, 2022
Int. Cl. A61K 47/58 (2017.01); C08F 222/10 (2006.01); C08F 228/02 (2006.01); B82Y 20/00 (2011.01)
CPC A61K 47/58 (2017.08) [C08F 222/102 (2020.02); C08F 228/02 (2013.01); B82Y 20/00 (2013.01)] 3 Claims
 
1. A method of modulating the immune system, comprising administering to a subject a polymer of Formula (I):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein,
R1 is

OG Complex Work Unit Chemistry
Y1 is C1-3 alkyl, (C1-6 alkyl)-NHC(═O), C═O, 5 to 10-membered heteroaryl, or absent, wherein heteroaryl is optionally substituted, independently for each occurrence, one, two, or three times with C1-3 alkyl, C1-3 alkoxy, C1-3 haloalkyl, halogen, or 6 to 10-membered aryl;
Y2 is C1-6 alkyl, 6 to 10-membered aryl, biphenyl, 5 to 10-membered heteroaryl, (CH2CH2O)pCH2CH2, C═N—(C1-6 alkyl)-N═C, O, S, or SO2, wherein the alkyl, aryl, biphenyl, and heteroaryl are optionally substituted, independently for each occurrence, one, two, or three times with C1-6 alkyl, C1-6 alkoxy, C1-6 haloalkyl, (C0-3 alkyl)-OH, NH2, NH(C1-6 alkyl), N(C1-6 alkyl)2, halogen, or carboxylic acid;
R2 is C1-6 alkyl, 6 to 10-membered aryl, O, or

OG Complex Work Unit Chemistry
Z1 is C1-6 alkyl or 6 to 10-membered aryl;
Z2 is O, O(C═O)O, or absent;
Z3 is 6 to 10-membered aryl, 5 to 10-membered heteroaryl, or absent;
Z4 is C1-6 alkyl, 5 to 15-membered cycloalkyl, 5 to 15-membered heterocyclyl, 6 to 14-membered aryl, 5 to 15-membered heteroaryl, or (C═O)O-(6 to 10-membered aryl)-O(C═O), each of which are optionally substituted, independently for each occurrence, one, two, or three times with C1-3 alkyl, C1-3 haloalkyl, or halogen;
n is 25-250;
p is 1, 2, 3, or 4; and
wherein R1, R2, Y1, Y2, Z1, Z2, Z3, and Z4 are each, independently, the same for every occurrence in the polymer.