Carbon analogs of penicillin
US4361514A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Feb 17, 1981 |
| Grant date | Nov 30, 1982 |
| Priority date | — |
| Expiry date | Feb 17, 2001 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07F9/5407
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
In accordance with this invention, it has been found that carbon and oxygen analogs of 6.beta.-aminopenicillanic acid and biologically active derivatives thereof can be formed from esters of 6-oxopenicillanic acid. For example, 6.beta.-phenoxyacetoxypenicillanic acid--an oxygen analog of penicillin V and 6.beta.-phenoxyacetylmethylpenicillanic acid--a carbon analog of penicillin V, may be formed from an ester of 6-oxopenicillanate. The ester of 6-oxopenicillanic acid is formed by a diiospropyl carbodiimide/dimethyl sulfoxide oxidation of the corresponding ester of 6.alpha.-hydroxypenicillanic acid. The oxygen analogs are formed by reducing the ester of 6-oxopenicillanic acid to the corresponding 6.beta.-hydroxypenicillanate and then forming the desired analog by acylation. The carbon analogs are formed by a Wittig reaction of the ester of 6-oxopenicillanic acid with a suitable acylmethylenetriphenylphosphorane followed by saturation of the newly formed double bond and removal of the protective ester group.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.