Ring E-modified analogues of(-)-podophyllotoxin and etoposide and a method for their synthesis
US6051721A · kind A · utility
Assignee
Inventor
Key dates
| Filing date | Oct 2, 1997 |
| Grant date | Apr 18, 2000 |
| Priority date | — |
| Expiry date | Oct 2, 2017 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07H17/04
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
A process of preparing ring E-modified analogues of (-)-podophyllotoxin as potential new chemotherapeutic agents. The process generates corresponding analogues of (-)-podophyllotoxin, itself, and allows new molecular interactions in the southern hemisphere (ring E) of the molecule. A method of preparing enantiomerically enriched compounds of the formula (I) and (II): ##STR1## wherein R is: ##STR2## wherein X, X', Y, Y' and Z are ring E substituents and R.sup.1 is one of a)-e) below. PA1 a) --OH, PA1 b) an ether or glycoside, PA1 c) a substituted or unsubstituted amine or aniline, PA1 d) a C.sub.2 -C.sub.8 alkenyl group, preferably --CH.sub.2 CH.dbd.CH.sub.2, PA1 e) a C.sub.1 -C.sub.8 alcohol, preferably --CH.sub.2 CH.sub.2 CH.sub.2 OH. The process produces enantiomerically enriched compounds which do not occur naturally and are not readily available from (-)-podophyllotoxin.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.