Methods of preparing substituted tetracyclines with transition metal-based chemistries
US7067681B2 · kind B2 · utility
Assignee
Inventors
Key dates
| Filing date | Jul 9, 2003 |
| Grant date | Jun 27, 2006 |
| Priority date | — |
| Expiry date | Sep 23, 2023 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07C2603/46
- WIPO fieldPharmaceuticals
- WIPO sectorChemistry
Abstract
The present invention relates to novel chemistries which allow for heretofore unobtainable substituted tetracycline compounds which exhibit significant antibacterial activity. The methods disclosed herein utilize reactive tetracycline-based precursor compounds, reactive organic substituent precursors and transition metal catalysts under conditions such that a tetracycline compound substituted with the desired organic substituent is formed. In one embodiment of the invention, a substituted tetracycline compound may be prepared by combining a reactive tetracycline-based precursor compound such as an arene tetracycline diazonium salt, and a reactive organic substituent precursor, e.g., alkenes, substituted alkenes, vinyl monomers, aromatics and heteroaromatics, in the presence of a transition metal catalyst, such as palladium chloride, under conditions such that a tetracycline compound substituted with the organic substituent is formed. Such compounds may optionally act as intermediates for making other compounds, e.g., hydrogenation of unsaturated groups on the substituent.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.