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US 11,981,687 B2Granted
Methods of preparing cytotoxic benzodiazepine derivatives
AssigneeImmunoGen, Inc.
InventorsBaudouin Gérard, Richard A. Silva, Michael Louis Miller, Manami Shizuka
Life of this patent
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Abstract
The invention provides novel methods for preparing indolinobenzodiazepine dimer compounds and their synthetic precursors.
Claims23
A method of preparing a compound of formula (Xa):
- or a salt thereof, comprising reacting the compound of formula (IX):
- or a salt thereof, with a carboxylic acid deprotecting agent, wherein P1 is a carboxylic acid protecting group.
A method of preparing a compound of formula (IX):
- or a salt thereof, comprising reacting a compound of formula (VIII):
- or a salt thereof, with a compound of formula (c):
- or a salt thereof, wherein E1 is —OH, halide or —C(═O)E1 is an activated ester;
- and P1 is a carboxylic acid protecting group.
1 more element
A method of preparing a compound of formula (Xa):
- or a salt thereof, comprising the steps of:
- 1) reacting a compound of formula (VIII):
- or a salt thereof, with a compound of formula (c):
- or a salt thereof, to form a compound of formula (IX):
- and
- 2) reacting the compound of formula (IX) with a carboxylic acid deprotecting agent, wherein E1 is —OH, halide or —C(═O)E1 is an activated ester;
- and P1 is a carboxylic acid protecting group.
4 more elements
Dependencies are inferred from the claim text.