US 12,252,464 B2
Cationic sulfonamide amino lipids and amphiphilic zwitterionic amino lipids
Daniel J. Siegwart, Dallas, TX (US); and Jason B. Miller, Dallas, TX (US)
Assigned to The Board of Regents of The University of Texas System, Austin, TX (US)
Filed by The Board of Regents of The University of Texas System, Austin, TX (US)
Filed on May 10, 2023, as Appl. No. 18/315,446.
Application 16/744,118 is a division of application No. 15/597,049, filed on May 16, 2017, granted, now 10,562,849, issued on Feb. 18, 2020.
Application 18/315,446 is a continuation of application No. 17/399,774, filed on Aug. 11, 2021, granted, now 11,685,710.
Application 17/399,774 is a continuation of application No. 16/744,118, filed on Jan. 15, 2020, granted, now 11,542,229, issued on Jan. 3, 2023.
Claims priority of provisional application 62/337,196, filed on May 16, 2016.
Prior Publication US 2024/0174604 A1, May 30, 2024
This patent is subject to a terminal disclaimer.
Int. Cl. C07C 311/32 (2006.01); A61K 47/54 (2017.01); A61K 47/69 (2017.01); A61K 48/00 (2006.01); B82Y 5/00 (2011.01); C07C 229/06 (2006.01); C07C 309/14 (2006.01); C07F 9/09 (2006.01); C07F 9/10 (2006.01); C12N 15/11 (2006.01); C12N 15/113 (2010.01); C12N 15/88 (2006.01)
CPC C07C 311/32 (2013.01) [A61K 47/543 (2017.08); A61K 47/6911 (2017.08); A61K 48/0033 (2013.01); B82Y 5/00 (2013.01); C07C 229/06 (2013.01); C07C 309/14 (2013.01); C07F 9/091 (2013.01); C07F 9/106 (2013.01); C12N 15/11 (2013.01); C12N 15/111 (2013.01); C12N 15/113 (2013.01); C12N 15/88 (2013.01); C12N 2310/14 (2013.01); C12N 2310/20 (2017.05); C12N 2320/32 (2013.01)] 19 Claims
 
1. A pharmaceutical composition comprising:
(a) a polynucleotide;
(b) a lipid composition comprising a zwitterionic aminolipid comprising an alkylated phosphate anion having the structure:

OG Complex Work Unit Chemistry
wherein, * indicates a point of attachment of a quaternary ammonium cation to said alkylated phosphate anion, wherein said quaternary ammonium cation comprises the structure:

OG Complex Work Unit Chemistry
wherein, ** indicates a point of attachment of said quaternary ammonium cation to said alkylated phosphate anion;
R1 is a first lipid group; and
each R2 is independently H or a second lipid group.