Esters of 3-demethylthiocolchicine and n-acyl analogs
AssigneeThe United States of America as represented by the Department of Health and Human Services
InventorArnold Brossi
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Abstract
The present invention relates to esters of 3-demethylthiocolchicine and N-acyl analogs thereof having the following formula: ##STR1## wherein R is O-CO-alkyl, O-CO-CH.sub.2 Oalkyl, O-CO-Phenyl, O-COOalkyl; the alkyl group having from 1 to 4 carbon atoms and the Ac group representing acetyl and its higher homologs, benzoyl, alkoxyacetyl, or haloacetyl. The invention further relates to processes for preparing these ester compounds, pharmaceutical compositions thereof and methods for treating diseases such as gout, Mediterranean fever and liver disorders.
Claims19
A compound of the formula ##STR4## wherein R is selected from the group consisting of O-CO-alkyl, O-CO-CH2-O-alkyl, O-CO-phenyl, and O-COOalkyl, the alkyl group having 1 to 4 carbon atoms, the Ac group being acetyl and its higher homologs, haloacetyl or alkoxyacetyl;
- or R is hydroxy and Ac is chosen from the group consisting of trifluoroacetyl and fluoroacetyl with the proviso that when R is O-CO-alkyl, Ac can only be acetyl, haloacetyl or alkoxyacetyl, and the alkyl in O-CO-alkyl cannot be methyl.
A method of inhibiting the formation of microtubules in mammals which comprises administering to a mammal a therapeutically effective amount of a compound of the formula ##STR5## wherein R is chosen from the group consisting of O-CO-alkyl, O-CO-CH.sub.2 -O-alkyl, O-CO-phenyl, and O-COO-alkyl, the alkyl group having 1 to 4 carbon atoms, the Ac group being acetyl and its higher homologs, benzoyl, haloacetyl or alkoxyacetyl;
- or R is hydroxy and Ac is chosen from the group consisting of butyryl, trifluoroacetyl or fluoroacetyl, with the proviso that if R is O-CO-CH.sub.3, then Ac cannot be acetyl.
Dependencies are inferred from the claim text.