US 11,981,687 B2
Methods of preparing cytotoxic benzodiazepine derivatives
Baudouin Gérard, Belmont, MA (US); Richard A. Silva, Needham, MA (US); Michael Louis Miller, Framingham, MA (US); and Manami Shizuka, Belmont, MA (US)
Assigned to IMMUNOGEN, INC., Waltham, MA (US)
Filed by IMMUNOGEN, INC., Waltham, MA (US)
Filed on Jun. 15, 2022, as Appl. No. 17/841,026.
Application 17/841,026 is a continuation of application No. 17/077,688, filed on Oct. 22, 2020, granted, now 11,390,633.
Application 17/077,688 is a continuation of application No. 16/442,718, filed on Jun. 17, 2019, granted, now 10,844,078, issued on Nov. 24, 2020.
Application 16/442,718 is a continuation of application No. 15/878,991, filed on Jan. 24, 2018, granted, now 10,385,071, issued on Aug. 20, 2019.
Claims priority of provisional application 62/450,270, filed on Jan. 25, 2017.
Prior Publication US 2023/0039161 A1, Feb. 9, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 207/452 (2006.01); C07C 205/19 (2006.01); C07D 487/04 (2006.01); C07D 519/00 (2006.01); C07D 519/04 (2006.01)
CPC C07D 519/00 (2013.01) [C07C 205/19 (2013.01); C07D 207/452 (2013.01); C07D 487/04 (2013.01); C07D 519/04 (2013.01)] 23 Claims
 
1. A method of preparing a compound of formula (Xa):

OG Complex Work Unit Chemistry
or a salt thereof, comprising reacting the compound of formula (IX):

OG Complex Work Unit Chemistry
or a salt thereof, with a carboxylic acid deprotecting agent, wherein P1 is a carboxylic acid protecting group.