Pradimic acids, amides, and pradimicin derivatives
AssigneeBristol-Myers Squibb Company
InventorsSatsuki Okuyama, Takaaki Okita, Hajime Kamachi
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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.
Claims11
A compound of the formula ##STR23## wherein R.sup.1 is hydrogen or a group of the formula ##STR24## 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, .beta.-D-xylosyl, or a hydroxy protecting group;
- or an acid addition salt thereof.
A compound having the formula ##STR26## wherein 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, .beta.-D-xylosyl, or a hydroxy protecting group;
- R.sup.5 is hydrogen, R.sup.7 is carboxy, R.sup.6 is trifluoromethyl, benzyl, aminomethyl, 4-aminobutyl, 3-guanidinylpropyl, ethylcarbomoylthiomethyl, 1-hydroxyethyl, fluoromethyl, 2-amino-2-carboxyethyldithiomethyl, carboxymethyl, or 4-imidazolylmethyl, with the proviso that the amino acid moiety has the D-configuration, or R.sup.6 is hydroxy methyl with the proviso that the amino acid moiety has the L-configuration;
- or R.sup.5 and R.sup.6 are both hydrogen and R.sup.7 is 5-tetrazolyl;
- or a pharmaceutically acceptable salt thereof.
Dependencies are inferred from the claim text.