US 12,263,357 B2
Antibody-pyrrolobenzodiazepine derivative conjugate which binds caludin-6 and claudin-9
Narihiro Toda, Tokyo (JP); Yusuke Ota, Tokyo (JP); Fuminao Doi, Tokyo (JP); Masaki Meguro, Tokyo (JP); Ichiro Hayakawa, Tokyo (JP); Shinji Ashida, Tokyo (JP); Takeshi Masuda, Tokyo (JP); Takashi Nakada, Tokyo (JP); Mitsuhiro Iwamoto, Tokyo (JP); Naoya Harada, Tokyo (JP); Tomoko Terauchi, Tokyo (JP); Daisuke Okajima, Tokyo (JP); Kensuke Nakamura, Tokyo (JP); Hiroaki Uchida, Tokyo (JP); and Hirofumi Hamada, Tokyo (JP)
Assigned to DAIICHI SANKYO COMPANY, LIMITED, Tokyo (JP)
Filed by DAIICHI SANKYO COMPANY, LIMITED, Tokyo (JP)
Filed on Apr. 8, 2024, as Appl. No. 18/629,444.
Application 17/714,032 is a division of application No. 17/543,697, filed on Dec. 6, 2021, granted, now 11,583,590.
Application 18/629,444 is a continuation of application No. 17/714,032, filed on Apr. 5, 2022.
Application 17/543,697 is a continuation of application No. 16/651,501, granted, now 11,628,223, previously published as PCT/JP2018/036252, filed on Sep. 28, 2018.
Claims priority of application No. 2017-190713 (JP), filed on Sep. 29, 2017.
Prior Publication US 2024/0299573 A1, Sep. 12, 2024
This patent is subject to a terminal disclaimer.
Int. Cl. A61P 35/00 (2006.01); A61K 47/68 (2017.01); C07D 487/04 (2006.01); C07K 16/30 (2006.01)
CPC C07D 487/04 (2013.01) [A61K 47/6803 (2017.08); A61K 47/68035 (2023.08); A61P 35/00 (2018.01); C07K 16/30 (2013.01)] 17 Claims
 
1. An antibody-drug conjugate selected from the group consisting of:

OG Complex Work Unit Chemistry
wherein
m2 represents an integer of 1;
Ab represents an antibody comprising a heavy chain comprising a CDRH1 consisting of an amino acid sequence represented by SEQ ID NO: 9, a CDRH2 consisting of an amino acid sequence represented by SEQ ID NO: 10, and a CDRH3 consisting of an amino acid sequence represented by SEQ ID NO: 11 and a light chain comprising a CDRL1 consisting of an amino acid sequence represented by SEQ ID NO: 5, a CDRL2 consisting of an amino acid sequence represented by SEQ ID NO: 6, and a CDRL3 consisting of an amino acid sequence represented by SEQ ID NO: 7; and
N297 glycan represents N297-(Fuc)MSG1 having a structure of:

OG Complex Work Unit Chemistry
wherein
each wavy line represents bonding to Asn297 of the antibody,
L(PEG) represents —NH—CH2CH2—(O—CH2CH2)3—*, wherein the amino group at the left end is bound via an amide bond to carboxylic acid at the 2-position of a sialic acid at the non-reducing terminal in the 1-3 branched chains of β-Man in the N297 glycan, and each asterisk represents bonding to a nitrogen atom at the 1- or 3-position of the triazole ring in the corresponding structural formula.