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US 2003/0195365 A1Published application
CC-1065 analog synthesis
AssigneeImmunoGen, Inc.
InventorsRobert Yongxin Zhao, Ravi V.J. Chari
Life of this patent
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Abstract
Improved synthesis of seco(−)CBI (5-hydroxy-3-amino-1-[S]-(chloromethyl)-1,2-dihydro-3H-benz(e)indole): 1 and improved syntheses therefrom of a wide variety of CC-1065 analogs that comprise a cyclopropabenzidole (CBI) alkylating moiety, and which are collectively DC1 and its derivatives, for the synthesis of cell-targeted therapeutic agents.
Claims17
A process for preparing a compound of formula (I) or a salt thereof, comprising:
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- (a) providing a compound of formula (II), wherein R is a protecting group;
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- (b) performing halogenation, alkylation and ring-closure reactions upon compound (II) under suitable conditions to provide racemate (III);
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- (c) isolating the (−) isomer of racemate (III);
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- (d) removing said R protecting groups from the isolated (−) isomer of compound (III) under suitable conditions to produce compound (I):
5 more elements
The compound of formula (II):
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- wherein R is a protecting group selected from the group consisting of tert-butyloxycarbonyl, diphenyloxycarbonyl, fluorenylmethyl oxycarbonyl, 2,2,2-trichloroethyl oxycarbonyl, 2-trimethylsilylethyl oxycarbonyl, diisopropylmethyl oxycarbonyl, 1-adamantyl oxycarbonyl, vinyl oxycarbonyl, allyl oxycarbonyl, benzyl oxycarbonyl, methoxy benzyl oxycarbonyl, nitrobenzyl oxycarbonyl, cyclohexyl oxycarbonyl, cyclopentyl oxycarbonyl.
Dependencies are inferred from the claim text.