Pradimic acids, amides, and novel pradimicin derivatives

Details Pradimic acids, amides, and novel pradimicin derivatives Pradimic acids, amides, and novel pradimicin derivatives

1994-08-03

1995-05-09

Lilling, Herbert J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 64, 536 168, 536 172, 536 181, A61K 3170, C07H 1524

Patent

active

054140730

ABSTRACT:
The present invention relates to intermediates, pradimic acids and pradimic acid amides of the formula (II) ##STR1## wherein R is OH or NH.sub.2 ; R.sup.1 is hydrogen or a group of the formula ##STR2## with the proviso that when R is OH, R.sup.1 is not hydrogen; Y is OH or NR.sup.2 R.sup.3 ; R.sup.2 is hydrogen or methyl; R.sup.3 is hydrogen, C.sub.1-5 alkyl, or an amino protecting group; R.sup.4 is hydrogen, hydroxy protecting group, or .beta.-D-xylosyl. The invention relates also to novel processes for the preparation of pradimic acids and pradimic acid amides, as well as novel pradimicin derivatives prepared therefrom.

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Y., Sawada et al., "Pradimicins M, N, O and P, New Diydrobenzonaphthacenequinones Produced by Blocked Mutatns of Actinomadura Hibisca P157-2", The Journal of Antibiotics, vol. 46, No. 11, pp. 1367-1374, Nov. 1, 1990.
S. Okuyama et al., "Synthesis and Antifungal Activities of Alanine-Exchanged Analogs of Pradimicin A", The Journal of Antibiotics, vol. 46, No. 3, pp. 500-506, Mar. 1, 1993.
S. Okuyama et al., "Synthesis of 4'-N-Cbz-Pradimic Acid From Pradimicin A", Chemical and Pharmaceutical Bulletin, vol. 41, No. 1, pp. 223-225, Jan. 1, 1993.
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