US 12,077,606 B2
Cyclic peptide analogs and conjugates thereof
Ippei Usui, San Diego, CA (US); Bryan Junn Lee, San Diego, CA (US); Steven Bruce Cohen, San Diego, CA (US); Venkat Rami Reddy Macherla, San Diego, CA (US); Jacob Neal Beverage, La Jolla, CA (US); Chung-Mao Pan, San Diego, CA (US); Farhana Barmare, San Diego, CA (US); and Eduardo Esquenazi, La Jolla, CA (US)
Assigned to Sirenas LLC, San Diego, CA (US)
Filed by Sirenas LLC, San Diego, CA (US)
Filed on Dec. 22, 2021, as Appl. No. 17/560,105.
Application 17/560,105 is a division of application No. 16/330,049, granted, now 11,254,705, previously published as PCT/US2017/049764, filed on Aug. 31, 2017.
Claims priority of provisional application 62/383,330, filed on Sep. 2, 2016.
Prior Publication US 2022/0227808 A1, Jul. 21, 2022
Int. Cl. C07K 11/02 (2006.01); A61K 38/08 (2019.01); A61K 47/68 (2017.01); A61P 35/00 (2006.01); C07K 7/06 (2006.01); C07K 16/32 (2006.01); A61K 38/00 (2006.01); C07K 16/00 (2006.01)
CPC C07K 7/06 (2013.01) [A61K 38/08 (2013.01); A61K 47/6811 (2017.08); A61K 47/6855 (2017.08); A61K 47/6889 (2017.08); A61P 35/00 (2018.01); C07K 16/32 (2013.01); A61K 38/00 (2013.01); C07K 16/00 (2013.01); C07K 2319/00 (2013.01)] 41 Claims
 
1. A compound of Formula (III):

OG Complex Work Unit Chemistry
or a salt thereof, wherein
R1, R2, R3, R8a, R8b, R9, R10, R11, R12, R13, and R14 are each independently H, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted cycloalkenyl;
R4 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted heterocyclyl;
R5 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl, halo, or perhaloalkyl;
R6 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl, halo, or perhaloalkyl;
R7 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted heterocyclyl;
R15 is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, or substituted or unsubstituted alkyl;
n is 0, 1, or 2;
X1 is —N(Rd)— or —O—;
X2 is O or S;
Y1 and Y2 are each independently —N(Rd)—, —O—, or —S—;
Y3 is —N(R4)—, —O—, —S—, or substituted or unsubstituted heterocycloalkyl;
Y4ª is —O—, —NRb—, or —S—;
each Rb and Rd is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted cycloalkenyl;
W is (CH2)m—Z—(CH2)p;
Z is substituted or unsubstituted alkyl, substituted or unsubstituted substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or (CH2CH2O)q;
m, and p are each independently an integer from 0-12;
q is an integer from 1-12;
a, b, c, and d are each independently 0, 1, or 2;
each L1 is independently

OG Complex Work Unit Chemistry
wherein a1 is 0, 1, or 2, and each Rx is unsubstituted or substituted alkyl;
each L2 is independently

OG Complex Work Unit Chemistry
wherein b1 is an integer from 0 to 12;
each L3 is independently

OG Complex Work Unit Chemistry
wherein each AA is an amino acid, c1 is an integer from 0-12, and c2 is an integer from 0-10;
each L4 is independently

OG Complex Work Unit Chemistry
wherein d1 is an integer from 0-12, and d2 is an integer from 0-30; and
Fn is selected from the group consisting of
H, unsubstituted or substituted alkyl,

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
wherein e1, e2, and e3 are each independently an integer from 0-12, and Re is H or alkyl.