US 12,410,262 B2
Peptide conjugates of cytotoxins as therapeutics
Daniel Richard Marshall, New Haven, CT (US); Johanna Marie Csengery, New Fairfield, CT (US); Robert John Maguire, New Haven, CT (US); and Robert A. Volkmann, Mystic, CT (US)
Assigned to Cybrexa 2, Inc., New Haven, CT (US)
Filed by Cybrexa 2, Inc., New Haven, CT (US)
Filed on Feb. 27, 2023, as Appl. No. 18/174,981.
Application 18/174,981 is a continuation of application No. 16/925,094, filed on Jul. 9, 2020, granted, now 11,634,508.
Claims priority of provisional application 63/040,859, filed on Jun. 18, 2020.
Claims priority of provisional application 62/872,643, filed on Jul. 10, 2019.
Prior Publication US 2024/0010755 A1, Jan. 11, 2024
This patent is subject to a terminal disclaimer.
Int. Cl. A61P 35/00 (2006.01); A61K 31/4745 (2006.01); A61K 38/00 (2006.01); C07D 491/147 (2006.01); C07D 491/16 (2006.01); C07D 491/22 (2006.01); C07K 14/00 (2006.01); C07K 19/00 (2006.01)
CPC C07K 19/00 (2013.01) [A61K 31/4745 (2013.01); A61P 35/00 (2018.01); C07D 491/147 (2013.01); C07D 491/16 (2013.01); C07D 491/22 (2013.01); C07K 14/00 (2013.01); A61K 38/00 (2013.01); C07K 2319/00 (2013.01)] 19 Claims
 
1. A method of treating cancer in a patient in need thereof, comprising administering to the patient a therapeutically effective amount of a compound of Formula (I):
R8-Q-R7  (I)
or a pharmaceutically acceptable salt thereof, wherein:
R7 is a peptide;
R8 is:

OG Complex Work Unit Chemistry
Q is:

OG Complex Work Unit Chemistry
R1 and R3 together with the carbon atoms to which they are attached form a C3-14 cycloalkyl group or 4-14 membered heterocycloalkyl group, each optionally substituted with 1, 2, or 3 substituents independently selected from C1-4 alkyl, halo, CN, NO2, ORa1, SRa1, C(O)Rb1, C(O)NRc1Rd1, C(O)ORa1, OC(O)Rb1, OC(O)NRc1Rd1, NRc1Rd1, NRc1C(O)Rb1, NRc1C(O)ORa1, and NRc1C(O)NRc1Rd1;
R2 and R4 are each independently selected from H, C1-4 alkyl, C1-4 alkenyl, C6-10 aryl, C3-10 cycloalkyl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, halo, CN, NO2, ORa1, SRa1, C(O)Rb1, C(O)NRc1Rd1, C(O)ORa1, OC(O)Rb1, OC(O)NRc1Rd1, NRc1Rd1, NRc1C(O)Rb1, NRc1C(O)ORa1, and NRc1C(O)NRc1Rd1, wherein said C1-4 alkyl, C1-4 alkenyl, C6-10 aryl, C3-10 cycloalkyl, 5-10 membered heteroaryl, and 4-10 membered heterocycloalkyl, are each optionally substituted with 1, 2, or 3 substituents independently selected from halo, CN, NO2, ORa1, SRa1, C(O)Rb1, C(O)NRc1Rd1, C(O)ORa1, OC(O)Rb1, OC(O)NRc1Rd1, NRc1Rd1, NRc1C(O)Rb1, NRc1C(O)ORa1, and NRc1C(O)NRc1Rd1, and
Ra1, Rb1, Rc1, and Rd1 are each independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 haloalkyl, OH, CN, NO2, and CO2CH3; wherein said C1-6 alkyl and C2-6 alkenyl are each optionally substituted with OH, CN, NO2, or CO2CH3.