US 12,303,544 B2
Cytotoxic and anti-mitotic compounds, and methods of using the same
Geoffrey C. Winters, Vancouver (CA); Alexander Laurence Mandel, Vancouver (CA); James R. Rich, Vancouver (CA); Bradley John Hedberg, Vancouver (CA); Tom Han Hsiao Hsieh, Vancouver (CA); Elyse Marie Josée Bourque, L'Etang-du-Nord (CA); and John Babcook, Vancouver (CA)
Assigned to ZYMEWORKS BC INC., Vancouver (CA)
Filed by ZYMEWORKS BC INC., Vancouver (CA)
Filed on Feb. 21, 2023, as Appl. No. 18/112,402.
Application 18/112,402 is a continuation of application No. 16/273,045, filed on Feb. 11, 2019, granted, now 11,617,777.
Application 16/273,045 is a continuation of application No. 14/776,654, granted, now 10,201,614, issued on Feb. 12, 2019, previously published as PCT/US2014/029463, filed on Mar. 14, 2014.
Claims priority of provisional application 61/792,020, filed on Mar. 15, 2013.
Claims priority of provisional application 61/792,066, filed on Mar. 15, 2013.
Prior Publication US 2023/0390354 A1, Dec. 7, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 38/05 (2006.01); A61K 31/445 (2006.01); A61K 38/06 (2006.01); A61K 39/395 (2006.01); A61K 47/54 (2017.01); A61K 47/64 (2017.01); A61K 47/68 (2017.01); A61P 35/00 (2006.01); C07C 311/51 (2006.01); C07C 317/28 (2006.01); C07C 317/32 (2006.01); C07C 317/50 (2006.01); C07C 323/12 (2006.01); C07C 323/67 (2006.01); C07C 327/06 (2006.01); C07C 381/08 (2006.01); C07D 207/02 (2006.01); C07D 207/08 (2006.01); C07D 207/452 (2006.01); C07D 211/34 (2006.01); C07D 211/60 (2006.01); C07D 213/56 (2006.01); C07D 213/71 (2006.01); C07D 333/34 (2006.01); C07K 5/02 (2006.01); C07K 5/065 (2006.01); C07K 16/32 (2006.01); C07K 16/28 (2006.01)
CPC A61K 38/05 (2013.01) [A61K 31/445 (2013.01); A61K 38/06 (2013.01); A61K 39/3955 (2013.01); A61K 47/54 (2017.08); A61K 47/64 (2017.08); A61K 47/6415 (2017.08); A61K 47/6803 (2017.08); A61P 35/00 (2018.01); C07C 311/51 (2013.01); C07C 323/12 (2013.01); C07C 323/67 (2013.01); C07C 327/06 (2013.01); C07C 381/08 (2013.01); C07D 207/08 (2013.01); C07D 207/452 (2013.01); C07D 211/34 (2013.01); C07D 211/60 (2013.01); C07D 213/56 (2013.01); C07D 213/71 (2013.01); C07D 333/34 (2013.01); C07K 5/0205 (2013.01); C07K 5/06078 (2013.01); C07C 317/28 (2013.01); C07C 317/32 (2013.01); C07C 317/50 (2013.01); C07C 2601/02 (2017.05); C07C 2601/08 (2017.05); C07C 2601/14 (2017.05); C07K 16/2863 (2013.01); C07K 16/32 (2013.01); Y02A 50/30 (2018.01)] 24 Claims
 
1. An antibody-drug conjugate comprising a targeting moiety (T), a linker (L) and a drug moiety (D), wherein the targeting moiety (T) is an antibody or antigen-binding antibody fragment and the drug moiety (D) is a compound of Formula (Ib):

OG Complex Work Unit Chemistry
wherein:
R16 is selected from the group consisting of H and C1-6 alkyl;
R17 is selected from the group consisting of H and C1-6 alkyl;
R18 is C1-6 alkyl;
R26 is selected from the group consisting of optionally substituted alkyl and optionally substituted aryl, and
R27 is

OG Complex Work Unit Chemistry
and
wherein a C-terminus of the drug moiety (D) forms the point of attachment to the targeting moiety (T) via the linker (L).