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US 11,633,492 B2Granted
Process for the synthesis of linker-drug vc-seco-DUBA
AssigneeByondis B.V.
InventorsVladimir Janousek, Martin Kas
Life of this patent
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Abstract
The compound of formula (II) is an advantageous intermediate for improving the process of synthesizing the linker-drug vc-seco-DUBA, as well as for the overall process for preparing an antibody-drug conjugate comprising the vc-seco-DUBA linker-drug. The methods of making the compound of formula (II) can include recovery of the compound as a solid, such as via crystallization, in high yields and purity.
Claims16
A compound of formula (II):
A process for the synthesis of a compound of formula (II):
- which comprises reacting a compound of formula (III):
- with hydrogen chloride in 1,4-dioxane to form the compound of formula (II).
A process for the synthesis of vc-seco-DUBA of formula (I):
- which comprises:
- reacting a compound of formula (II):
- with a compound of formula (VII):
- to form vc-seco-DUBA of formula (I).
1 more element
A process for the synthesis of an antibody-drug conjugate of formula (VIII):
- wherein:
- Antibody is an antibody or an antigen-binding fragment thereof;
- and
- m is an average drug-to-antibody ratio of from 1 to 8;
- which comprises:
- (1) reacting a compound of formula (II):
- with a compound of formula (VII):
- to form vc-seco-DUBA of formula (I):
- (2) conjugating vc-seco-DUBA of formula (I) to an antibody, or an antigen-binding fragment thereof, to form an antibody-drug conjugate of formula (VIII).
6 more elements
Dependencies are inferred from the claim text.