109882-25-9

Usage

Uses

Impurity of Bendamustine (B132500), an anticancer drug.

Upstream product

• 186581-53-3 diazomethane 
• 16506-27-7 bendamustine 
• 1221157-11-4 4-(5-amino-1-methyl-1H-benzoimidazol-2-yl)butyric acid methyl ester hydrochloride 
• 79-11-8 chloroacetic acid 
• 1221157-09-0 4-(2,4-dinitrophenylcarbamoyl)butyric acid methyl ester 
• 1221157-10-3 4-[(2,4-dinitrophenyl)methylcarbamoyl]butyric acid methyl ester 
• 1501-26-4 methyl 4-(chlorocarbonyl)butyrate 
• 97-02-9 2,4-Dinitroanilin 
• 67-56-1 methanol 
• 3543-75-7 bendamustine hydrochloride 
• 1221157-20-5 4-(5-amino-1-methyl-1H-benzoimidazol-2-yl)-butyric acid methyl ester 
• 109882-31-7 4-{5-[bis-(2-hydroxyethyl)amino]-1-methyl-1H-benzoimidazol-2-yl}-butanoic acid methyl ester 

Downstream Products

• 3543-75-7 bendamustine hydrochloride 

Relevant academic research and scientific papers

Improved continuous flow processing: Benzimidazole ring formation via catalytic hydrogenation of an aromatic nitro compound

In the development of a new route to bendamustine hydrochloride, the API in Treanda, the key benzimidazole intermediate 5 was generated via catalytic heterogeneous hydrogenation of an aromatic nitro compound using a batch reactor. Because of safety concer

BENDAMUSTINE DERIVATIVES AND METHODS OF USING SAME

The present invention is directed to bendamustine esters and bendamustine amides and their use for the treatment of cancer: (I) wherein R1 is C6-C24alkyl or polyethylene glycol; and (II) wherein R2 is C1-C24alkylene; and R3 is-COOC1-3alkyl; or R2-R3 is C1-C24alkyl; or a pharmaceutically acceptable salt form thereof.

Process for the preparation of bendamustine hydrochloride and related compounds

The present invention relates to a process for preparing bendamustine hydrochloride, derivatives and related compounds thereof.

Discovery of a novel, efficient, and scalable route to bendamustine hydrochloride: The API in Treanda

Process Research and Development activities leading to a new and efficient route to bendamustine hydrochloride, 1, the active ingredient in Treanda, a treatment for blood cancers, are disclosed. Two key features of this new process include a one-pot hydrogenation/dehydration sequence to construct the benzimidazole moiety and a novel reductive alkylation using chloroacetic acid and borane to install the bischloroethyl side chain. The number of synthetic steps has been significantly reduced to five from the eight in the current commercial process. The overall yield has been improved from 12% to 45%. Additionally, this new route eliminates chloroform, ethylene oxide, and sodium sulfide. Scale-up of the new route has been successfully demonstrated to prepare kilogram quantities of bendamustine hydrochloride.

PROCESSES FOR THE PREPARATION OF BENDAMUSTINE

New methods for the preparation of bendamustine, and the pharmaceutical salts thereof, are described. Novel compounds useful for the preparation of bendamustine are also described.