Pyrrolo[2,1- c ][1,4]benzodiazepine compounds and processes...

Details Pyrrolo[2,1- c ][1,4]benzodiazepine compounds and processes... Pyrrolo[2,1- c ][1,4]benzodiazepine compounds and processes...

2007-12-25

2007-12-25

Kifle, Bruck (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

C540S496000

Reexamination Certificate

active

11367223

ABSTRACT:
The present invention provides novel pyrrolo [2,1-c][1,4]benzodiazepine compounds. This invention also provides a process for the preparation of novel pyrrolo[2,1-c][1,4]benzodiazepine compounds. These novel pyrrolo [2,1-c][1,4]benzodiazepine compounds are useful as antitumor agents. It also provides a process for the preparation of 7-methoxy-8-{n-[4-(2-oxo-2H-4-chromenyl)piperazino]alkyl}-oxy-(11aS)-1,2,3,11a-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one and 7-methoxy-8-{n-[4-(7-alkoxy-8-methyl-2-oxo-2H-4-chromenyl)piperazino]alkyl}-oxy-(11aS)-1,2,3,11a-5H-pyrrolo[2,1-c][1,4]. benzodiazepine-5-one with aliphatic chain length variations for these compounds.

REFERENCES:
Gregson et al. (2001) Design, synethesis, and evaluation of a novel pyrrolobenzodiazepine DNA-interactive agent with highly efficient cross-linking ability and potent cytotoxicity. J. Med. Chem. 44:737-748.
Hurley et al. (1977) Pyrrolo(1,4)benzodiazepine antitumor antibiotics in vitro interaction of anthramycin, sibiromycin and tomaymycin with DNA using specifically radiolabelled molecules. Biochimica et Biophysica Acta. 475:521-535.
Kaplan et al. (1981) Anthramycin binding to deoxyribonucleic acid-mitomycin C complexes. Evidence for drug-induced deoxyribonucleic acid conformational change and cooperativity in mitromycin C binding. American Chemical Society. 20:7572-7582.
Kohn et al. (1970) Reaction of anthramycin with deoxyribonucleic acid. J. Mol. Biol. 51:551-571.
Thurston et al. (1996) Synthesis of sequence-selective C8-linked pyrrolo[2,1-c][1,4]benzodiazepine DNA interstrand cross-linking agents. J. Org. Chem. 61:8141-8147.

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