Some new derivatives of oleanolic acid were obtained, in which an atom of nitrogen was involved both in A and C ring and was an element of hydroxyimino or nitrile function, and also in heterocyclic ring (lactam system). In order to obtain these compounds, methyl 3- acethyloleanolate was subjected to a number of transformations which led to the derivatives 1 - 8 (oxidation, synthesis of oximes, Beckmann rearrangement, oxygen atom substitution, hydrolysis):

As it is known from our previous experiments [1, 2], the derivatives of oleanolic acid that contain seven-membered ring with a nitrogen atom are very good transdermal penetration promoters of therapeutic preparations. The effectiveness of these compounds is comparable to, and many a time more effective than that of N-dodecylcaprolactame, known as Azon^®, one of the most effective accelerator of transdermal transport. The element that is probably responsible for this activity of this compound is the lactam system, present in molecules of derivatives 1 - 8 as well. It is supposed that the azacompounds 5 and 6 will be one of the most active transdermal penetration enhancers obtained to the present time.

[1] L. Zaprutko, D. Partyka, B. Bednarczyk - Cwynar, "Synteza i zdolność do aktywowania transportu przezskórnego C-laktamowych pochodnych kwasu oleanolowego i erytrodiolu"; XLVII Zjazd Naukowy PTChem i SiTChem, Wrocław, 12 - 17 IX 2004, poster P - 069, Materiały Zjazdowe str. 138.

[2] L. Zaprutko, D. Partyka, B. Bednarczyk - Cwynar, "Triterpenoids. Part 21: Oleanolic Acid Derivatives as Percutaneous Transport Promoters"; Bioorg. Med. Chem. Lett. 2004, 14, 4723.

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