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US 4,362,664 AGranted
Vinblastine oxazolidinedione disulfides and related compounds
AssigneeEli Lilly and Company
InventorsKoert Gerzon, Jean C. Miller
Life of this patent
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Abstract
Thioalkyl derivatives of vinblastine 3-spiro-5"-oxazolidine-2",4"-dione, mitotic inhibitors.
Claims6
A compound of the formula
- Q--CH.sub.2 --CH.sub.2 --S--S--CH.sub.2 --CH.sub.2 --Z
- wherein Q is a 3"-oxazolidindionyl radical of the formula:
- ##STR9## wherein R.sup.2 is CHO or CH.sub.3 ;
- one of R.sup.3 and R.sup.4 OH or H and the other is ethyl;
- and
- Z is Q, NCO or NH--CO.sub.2 --(C.sub.1 -C.sub.3)alkyl.
3 more elements
An oxazolidinedione of the formula:
- ##STR10## wherein one of R.sup.3 and R.sup.4 is OH or H and the other is ethyl;
- R.sup.2 is CH.sub.3 or CHO;
- R.sup.1 is OH or acetoxy and R is CH.sub.1 --CH.sub.2 --S--S--CH.sub.2 --CH.sub.2 --R.sup.9 wherein R.sup.9 is NCO or NH--CO--O--(C.sub.1 -C.sub.3)alkyl.
A process for preparing a compound of the structure
- Q--CH.sub.2 --CH.sub.2 --SH
- wherein Q is a 3"-oxazolidinedioxyl radical of the formula ##STR11## wherein R.sup.1 is OH or acetoxy;
- R.sup.2 is CH.sub.3 or CHO;
- and one of R.sup.3 and R.sup.4 is H or OH and the other is ethyl, which comprises reducing a compound of the formula Q--CH.sub.2 --CH.sub.2 --S--S--CH.sub.2 --CH.sub.2 --Z, wherein Z is Q, NCO or NH--CO.sub.2 --(C.sub.1 -C.sub.3)alkyl;
- and wherein R.sup.1 is acetoxy with zinc and acetic acid;
- and then, to produce a compound in which R.sup.1 is OH, subjecting the reduced compound to mild alkaline hydrolysis.
3 more elements
The process which comprises oxidizing a compound of the structure Q--CH.sub.2 --CH.sub.2 --S--H wherein Q is a 3"-oxazolidinedionyl radical of the formula ##STR12## wherein R.sup.2 is CH.sub.3 or CHO;
- R.sup.1 is OH or acetoxy and one of R.sup.3 and R.sup.4 is H or OH and the other is ethyl;
- with ferricyanide in hydrochloric acid.
Dependencies are inferred from the claim text.