Patent EP-1287006-B1 (EP)
Inventor: ACENA JOSE LUIS
IPC: C07C215/52
Filed: 2001-06-06
Granted: 2007-10-24
Abstract: New spisulosine derivatives of use in treating tumors are of the formula (I) wherein: each X is the same or different, and represents H, OH, OR', SH, SR', SOR', SO<SUB>2</SUB>R', NO<SUB>2</SUB>, NH<SUB>2</SUB>, NHR', N(R')<SUB>2</SUB>, CN, halogen, C(-O)H, C(-O)CH<SUB>3</SUB>, CO<SUB>2</SUB>H, CO<SUB>2</SUB>CH<SUB>3</SUB>, substituted or unsubstituted C<SUB>1</SUB>-C<SUB>18 </SUB>alkyl, substituted or unsubstituted C<SUB>2</SUB>-C<SUB>18 </SUB>alkenyl, substituted or unsubstituted C<SUB>2</SUB>-C<SUB>18 </SUB>alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaromatic, or two groups X may together form -O; Y is NR<SUB>1</SUB>, OR<SUB>1</SUB>, PR<SUB>1</SUB>, SR<SUB>1</SUB>, or halogen, wherein the number of substituents R<SUB>1 </SUB>is selected to suit the valency and each R<SUB>1 </SUB>is independently selected of H, OH, C(-O)R', P(-O)R'R'', substituted or unsubstituted C<SUB>1</SUB>-C<SUB>18 </SUB>alkyl, substituted or unsubstituted C<SUB>2</SUB>-C<SUB>18 </SUB>alkenyl, substituted or unsubstituted C<SUB>2</SUB>-C<SUB>18 </SUB>alkynyl, substituted or unsubstituted aryl, and wherein the dotted line indicates an optional double bond; each Z is the same different, and represents H, OH, OR', SH, SR', SOR', SO<SUB>2</SUB>R', NO<SUB>2</SUB>, NH<SUB>2</SUB>, NHR', N(R')<SUB>2</SUB>, NHC(O)R', CN, halogen, C(-O)H, C(-O)CH<SUB>3</SUB>, CO<SUB>2</SUB>H, CO<SUB>2</SUB>CH<SUB>3</SUB>, substituted or unsubstituted C<SUB>1</SUB>-C<SUB>18 </SUB>alkyl, substituted or unsubstituted C<SUB>2</SUB>-C<SUB>18 </SUB>alkenyl, substituted or unsubstituted C<SUB>2</SUB>-C<SUB>18 </SUB>alkenyl, substituted or unsubstituted C<SUB>2</SUB>-C<SUB>18 </SUB>alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaromatic, or two groups Z may together form -O; z is 0 to 25; y is to 0 to 20; R<SUB>2 </SUB>is H, C(-O)R', P(-O)R'R'', S(-O)R'R'', S(-O)<SUB>2</SUB>R', substituted or unsubstituted C<SUB>1</SUB>-C<SUB>18 </SUB>alkyl, substituted or unsubstituted C<SUB>2</SUB>-C<SUB>18 </SUB>Alkenyl, substituted or unsubstituted C<SUB>2</SUB>-C<SUB>18 </SUB>alkynyl, substituted or unsubstituted aryl; R<SUB>3 </SUB>is H, C(-O)R', P(-O)R'R'', S(-O)R'R'', S(-O)<SUB>2</SUB>R', substituted or unsubstituted C<SUB>1</SUB>-C<SUB>18 </SUB>alkyl, substituted or unsubstituted C<SUB>2</SUB>-C<SUB>18 </SUB>alkenyl, substituted or unsubstituted C<SUB>2</SUB>-C<SUB>18 </SUB>alkynyl, substituted or unsubstituted aryl; each of the R', R'' groups is independently selected from the group consisting of H, OH, NO<SUB>2</SUB>, NH<SUB>2</SUB>, SH, CN, halogen, -O, C(-O)H, C(-O)CH<SUB>3</SUB>, CO<SUB>2</SUB>H, CO<SUB>2</SUB><img id="CUSTOM-CHARACTER-00001" he="1.02mm" wi="0.68mm" file="US07138547-20061121-P00001.TIF" alt="custom character" img-content="character" img-format="tif"/><SUB>CH</SUB><img id="CUSTOM-CHARACTER-00002" he="1.02mm" wi="0.68mm" file="US07138547-20061121-P00001.TIF" alt="custom character" img-content="character" img-format="tif"/><SUB>3</SUB>, substituted or unsubstituted C<SUB>1</SUB>-C<SUB>18 </SUB>alkyl, substituted or unsubstituted C<SUB>1</SUB>-C<SUB>18 </SUB>alkoxy, substituted or unsubstituted C<SUB>2</SUB>-C<SUB>18 </SUB>alkenyl, substituted or unsubstituted C<SUB>2</SUB>-C<SUB>18 </SUB>alkynl, substituted or unsubstituted aryl; there may be one or more unsaturations in the hydrocarbon backbone defined by the chain (II) and salts thereof; with the exception of a C<SUB>16</SUB>-C<SUB>24 </SUB>2-amino-3-hydroxyalkane or a C<SUB>16</SUB>-C<SUB>24 </SUB>2-amino-3-hydroxyalkene