US 12,440,445 B2
Fusogenic compounds for delivery of biologically active molecules
Kwok Yin Tsang, Irvine, CA (US); Bharat Majeti, San Diego, CA (US); John Gaudette, Poway, CA (US); Roger Adami, Carlsbad, CA (US); Hao Bai, San Diego, CA (US); and Wenbin Ying, San Diego, CA (US)
Assigned to Nitto Denko Corporation, Osaka (JP)
Filed by Nitto Denko Corporation, Osaka (JP)
Filed on Apr. 5, 2022, as Appl. No. 17/658,078.
Application 17/658,078 is a division of application No. 16/182,571, filed on Nov. 6, 2018, granted, now 11,413,243.
Claims priority of provisional application 62/582,252, filed on Nov. 6, 2017.
Prior Publication US 2022/0233445 A1, Jul. 28, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 31/7105 (2006.01); A61K 9/1272 (2025.01); A61K 47/10 (2017.01); A61K 47/14 (2017.01); A61K 47/69 (2017.01); C07C 201/00 (2006.01); B82Y 5/00 (2011.01)
CPC A61K 9/1272 (2013.01) [A61K 31/7105 (2013.01); A61K 47/10 (2013.01); A61K 47/14 (2013.01); A61K 47/6911 (2017.08); C07C 201/00 (2013.01); B82Y 5/00 (2013.01)] 11 Claims
 
1. A fusogenic compound having Formula VII:

OG Complex Work Unit Chemistry
wherein each amphiphile has a structure represented by Formula VIII:

OG Complex Work Unit Chemistry
wherein R1 and R2 are:
R1 is CH2(CH2)nO(C═O)R4, CH2(CH2)nNH(C═O)R4, CH2(CH2)n(C═O)OR4, or CH2(CH2)n(C═O)NHR4;
R2 or CH2(CH2)mO(C═O)R5, CH2(CH2)mNH(C═O)R5, CH2(CH2)m(C═O)OR5, or CH2(CH2)m(C═O)NHR5;
wherein:
n and m are each independently from 1 to 2;
R4 and R5 are independently for each occurrence a C(12-20) alkyl group or a C(12-20) alkenyl group;
wherein each AAa is independently an amino acid of the following structure, and any stereoisomer thereof:

OG Complex Work Unit Chemistry
wherein the linker has a structure:

OG Complex Work Unit Chemistry
wherein Q1 is selected from the group consisting of branched or unbranched C(2-8)alkandiyl, branched or unbranched C(2-8)alkenediyl, branched or unbranched C(2-8)alkynediyl,

OG Complex Work Unit Chemistry
wherein Q2 is

OG Complex Work Unit Chemistry
wherein Q3 is

OG Complex Work Unit Chemistry
wherein X is selected from the group consisting of —O—, —S—, and —NH—;
n and p are independently for each occurrence 1 to 3;
m is independently 1 to 10; and
r and s are independently for each occurrence 1 to 5.