Halogen labeled compounds including estradiol derivatives, their synthetic intermediates and the syntheses thereof
US4659517A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Oct 22, 1984 |
| Grant date | Apr 21, 1987 |
| Priority date | — |
| Expiry date | Oct 22, 2004 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07J31/006
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
A method of preparation of halogen labeled organic compounds is described. In particular, estradiol derivatives labeled by halogen substitution at C-16 are synthesized according to the present invention. A triflate intermediate is prepared from which either 16-alpha-halo-substituted-17-beta-estradiols or 16-beta-halo-substituted-17-beta-estradiols can be rapidly formed as desired. In particular, the preparation of 16-alpha-.sup.123 I-17-beta-estradiol and 16-beta-.sup.123 I-17-beta-estradiol are shown and are synthesized from a 17-beta-estradiol-16-beta-triflate. Both 16-alpha-.sup.123 I- and 16-beta-.sup.123 I-17-beta-estradiol made according to the present invention are shown to have a high specific activity. The method of synthesis is sufficiently rapid so that the relatively short half-life of .sup.123 I is readily accommodated. The high stereospecificity of each step of the reaction sequence in preparing the labeled estradiols provides for highly efficient syntheses and little waste of radio-label.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.