Process for the preparation of ribonucleotide reductase inhibitors
AssigneeHoeschst Marion Roussel, Inc.
InventorsJames R. McCarthy, Donald P. Matthews, Jeffrey S. Sabol, James R. McConnell, Richard E. Donaldson, Robert Duquid
Life of this patent
Estimating the term…
Abstract
The present invention is directed toward a novel process of preparing 2'-exocyclic vinylfluoride derivatives of cytidine analogues for use as ribonucleotide reductase inhibitors. The novel process of the present invention utilizes a cytidine derivative as the required starting material and provides the ribonucleotide reductase inhibitor in a more efficient five step reaction sequence. The present invention further provides the ribonucleotide reductase inhibitor in a four step reaction sequence and results in an overall yield of greater than 35%.
Claims3
A compound of the formula ##STR40## wherein V is oxy or methylene
- R.sub.4 is C.sub.2 -C.sub.7 alkyl or C.sub.5 -C.sub.7 cycloalkyl and A.sub.B is a radical of the formula ##STR41## wherein Y is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy and B is a suitable nitrogen blocking group of the formula CR.sub.1 NR.sub.2 R.sub.3 wherein R.sub.1 is a hydrogen or C.sub.1 -C.sub.4 alkyl and R.sub.2 and R.sub.3 are independently C.sub.1 -C.sub.4 alkyl.
A compound of the formula ##STR42## wherein V is oxy or methylene
- R.sub.4 is C.sub.2 -C.sub.7 alkyl or C.sub.5 -C.sub.7 cycloalkyl and
- A.sub.B is a radical of the formula ##STR43## wherein Y is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy and B is a suitable nitrogen blocking group of the formula CR.sub.1 NR.sub.2 R.sub.3 wherein R.sub.1 is a hydrogen or C.sub.1 -C.sub.4 alkyl and R.sub.2 and R.sub.3 are independently C.sub.1 -C.sub.4 alkyl.
A compound of the formula ##STR44## which is (E)-2'-deoxy-2'-(fluoromethylene)cytidine monohydrate.
Dependencies are inferred from the claim text.