Back to results
US 12,390,528 B2Granted
Conjugated lipomers and uses thereof
AssigneeMassachusetts Institute of Technology
InventorsJames E. Dahlman, Avraham D. Schroeder, Daniel Griffith Anderson, Robert S. Langer, Christopher G. Levins
Life of this patent
Estimating the term…
Abstract
The present invention provides inventive conjugated polyethyleneimine (PEI) polymers and conjugated aza-macrocycles (collectively referred to herein as “conjugated lipomers” or “lipomers”) containing one or more groups of the formula (iii): wherein R3 and R4 are as defined herein. Also provided are compositions comprising the inventive conjugated lipomers, and methods of preparation and use.
Claims20
A conjugated lipomer of the Formula (II):
- or salt thereof;
- wherein:
- each instance of L1 is independently formula:
- provided that at least one L1 is formula (ii) and at least one L1 is formula (iii);
- n is an integer between 3 and 45, inclusive;
- each instance of R2 is independently hydrogen;
- acyl;
- silyl;
- sulfonyl;
- an amino protecting group;
- substituted or unsubstituted alkyl;
- substituted or unsubstituted alkenyl;
- substituted or unsubstituted alkynyl;
- substituted or unsubstituted heteroalkyl;
- substituted or unsubstituted heteroalkenyl;
- substituted or unsubstituted heteroalkynyl;
- substituted or unsubstituted carbocyclyl;
- substituted or unsubstituted heterocyclyl;
- substituted or unsubstituted aryl;
- substituted or unsubstituted heteroaryl;
- a substituted or unsubstituted polyethyleneimine;
- or a group of the formula (iii′):
- or the two R2 groups are joined to form a substituted or unsubstituted heterocyclyl;
- each instance of R3 is —C13H27;
- each instance of R4 is independently hydrogen, acyl;
- silyl;
- a hydroxyl protecting group;
- substituted or unsubstituted alkyl;
- substituted or unsubstituted alkenyl;
- substituted or unsubstituted alkynyl;
- substituted or unsubstituted heteroalkyl;
- substituted or unsubstituted heteroalkenyl;
- substituted or unsubstituted heteroalkynyl;
- substituted or unsubstituted carbocyclyl;
- substituted or unsubstituted heterocyclyl;
- substituted or unsubstituted aryl;
- or substituted or unsubstituted heteroaryl;
- A is —N(R5)2, wherein each instance of R5 is hydrogen;
- and
- Z is hydrogen;
- acyl;
- silyl;
- sulfonyl;
- an amino protecting group;
- substituted or unsubstituted alkyl;
- substituted or unsubstituted alkenyl;
- substituted or unsubstituted alkynyl;
- substituted or unsubstituted heteroalkyl;
- substituted or unsubstituted heteroalkenyl;
- substituted or unsubstituted heteroalkynyl;
- substituted or unsubstituted carbocyclyl;
- substituted or unsubstituted heterocyclyl;
- substituted or unsubstituted aryl;
- substituted or unsubstituted heteroaryl, or a group of the formula (iii′):
- or Z and the nitrogen atom to which it is attached form a substituted or unsubstituted heterocyclyl group.
52 more elements
A conjugated lipomer, or salt thereof, prepared by contacting a compound of Formula (I):
- or salt thereof, with one or more different epoxides of the formula (xii):
- wherein:
- n is an integer between 3 and 45, inclusive;
- each instance of R1 is independently selected from hydrogen or a group of the formula (ii′):
- A is —N(R5)2, wherein each instance of R5 is hydrogen;
- Z is hydrogen;
- acyl;
- silyl;
- sulfonyl;
- an amino protecting group;
- substituted or unsubstituted alkyl;
- substituted or unsubstituted alkenyl;
- substituted or unsubstituted alkynyl;
- substituted or unsubstituted heteroalkyl;
- substituted or unsubstituted heteroalkenyl;
- substituted or unsubstituted heteroalkynyl;
- substituted or unsubstituted carbocyclyl;
- substituted or unsubstituted heterocyclyl;
- substituted or unsubstituted aryl;
- or substituted or unsubstituted heteroaryl;
- or Z and the nitrogen atom to which it is attached form a substituted or unsubstituted heterocyclyl group;
- each instance of R2 is independently hydrogen;
- acyl;
- silyl;
- sulfonyl;
- an amino protecting group;
- substituted or unsubstituted alkyl;
- substituted or unsubstituted alkenyl;
- substituted or unsubstituted alkynyl;
- substituted or unsubstituted heteroalkyl;
- substituted or unsubstituted heteroalkenyl;
- substituted or unsubstituted heteroalkynyl;
- substituted or unsubstituted carbocyclyl;
- substituted or unsubstituted heterocyclyl;
- substituted or unsubstituted aryl;
- substituted or unsubstituted heteroaryl;
- a substituted or unsubstituted polyethyleneimine;
- or a group of the formula (iii′):
- or the two R2 groups are joined to form a substituted or unsubstituted heterocyclyl;
- each instance of R3 is —C13H27;
- each instance of R4 is independently hydrogen, acyl;
- silyl;
- a hydroxyl protecting group;
- substituted or unsubstituted alkyl;
- substituted or unsubstituted alkenyl;
- substituted or unsubstituted alkynyl;
- substituted or unsubstituted heteroalkyl;
- substituted or unsubstituted heteroalkenyl;
- substituted or unsubstituted heteroalkynyl;
- substituted or unsubstituted carbocyclyl;
- substituted or unsubstituted heterocyclyl;
- substituted or unsubstituted aryl;
- or substituted or unsubstituted heteroaryl;
- provided that the number average molar mass (Mn) of the compound of Formula (I) does not exceed 2000 g/mol (about 2 kDa).
51 more elements
Dependencies are inferred from the claim text.