Process for the production of ramoplanin-like amide derivatives

Chemistry: natural resins or derivatives; peptides or proteins; – Peptides of 3 to 100 amino acid residues – Peptides containing saccharide radicals – e.g. – bleomycins – etc.

Reexamination Certificate

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C530S317000, C514S023000, C514S009100

Reexamination Certificate

active

10505881

ABSTRACT:
The invention regards a process for the production of ramoplanin-like derivatives of formula (I): RAMO-NC—CO—R (I), wherein the radical R represents a hydrocarbon radical and the portion RAMO-NH— represents deacylated ramoplanin, any of its factors or ramoplanose. The compound of Formula (I) are obtained by reacting a carboxylic acid R—COOH with deacylated ramoplanin, any of its factors or ramoplanose protected on the ornitine amino groups. New compounds wherein the hydrocarbon radical R is different form those characaterizing the ramoplanin and ramoplanose natural products and their tetrahydro-derivatives are calimed. The new compounds have the same or better antinfective activity, lower haemolytic effect and better tolerability profile than ramoplanin.

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patent: 6720305 (2004-04-01), Parenti et al.
patent: 318 680 (1989-06-01), None
Boger DL, “Vancomycin, Teicoplanin, and Ramoplanin: Synthetic and Mechanistic Studies” 2001, Medicinal Research Reviews, vol. 21(5), pp. 356-381.
Jiang et al., “Total Synthesis of the Ramoplanin A2 and Ramoplanose Aglycon” Jan. 2003, J. Am. Chem. Soc., vol. 125, pp. 1877-1887.
Degradation, and synthesis of semi synthetic analogs, of the natural antibiotic Ramoplanin, Anno Accademico 2000-2001, pp. 2-66.

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