O-alkyl macrolide and azalide derivatives and regioselective...

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

Reexamination Certificate

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C536S007200, C536S018600

Reexamination Certificate

active

07435805

ABSTRACT:
The present disclosure relates to new 11-O-alkyl macrolides and azalides and pharmaceutically acceptable salts and solvates thereof, and to pharmaceutical compositions thereof. The disclosure also relates to a process for the preparation of 11-O-alkyl macrolides and azalides by regioselective 11-O-alkylation of macrolides and azalides having a vicinal diol system, using diazoalkanes in the presence of transition-metal halides or boric acid as catalysts. In another aspect, the disclosure relates to uses of the 11-O-alkyl macrolides and azalides as antibacterial agents or intermediates for the synthesis of other antibacterial agents.

REFERENCES:
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patent: 6593360 (2003-07-01), Lazarevski et al.
patent: 0 080 819 (1983-06-01), None
patent: 0 467 331 (1992-01-01), None
patent: WO-99/20639 (1999-04-01), None
Evtushenko, Evgeny V., “Regioselective methylation of methyl glycopyranosides with diazomethane in the presence of transition-metal chlorides and of boric acid”, Carbohydrate Research, vol. 316, pp. 187-200 (1999).
Bertho, Gildas, et al., “Solution confirmation of methylated macrolide antibiotics roxithromycin and erythromycin using NMR and molecular modelling. Ribosome-bound conformation determined by TRNOE and formation of cytochrome P450-metabolite complex”, International Journal of Biological Macromolecules, vol. 22, pp. 103-127 (1998).
Waddell, Sherman T., et al., “Synthesis and antibacterial activity of O-methyl derivatives of azalide antibiotics: I. 4″, 11 and 12-OMe derivatives via direct methylation”, Bioorganic & Medicinal Chemistry Letters, vol. 8, No. 5, Mar. 3, 1998, pp. 549-554.
Morimoto Shigeo, et al., “Chemical modifications of erythromycins. II. Synthesis and antibacterial activity of o-alkyl derivatives of erythromycin A”, Journal of Antibiotics, Japan Antibiotics Research Association, vol. 43, pp. 286-294 (1990.).

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