Illudin analogs useful as antitumor agents

Details Illudin analogs useful as antitumor agents Illudin analogs useful as antitumor agents

C - Chemistry, Metallurgy

07

C

C07C 323/58 (2006.01) A61K 31/095 (2006.01) A61K 31/122 (2006.01) A61K 31/197 (2006.01) A61K 31/215 (2006.01) A61K 31/265 (2006.01) A61K 31/335 (2006.01) A61K 31/4164 (2006.01) A61P 35/00 (2006.01) C07C 49/737 (2006.01) C07C 49/753 (2006.01) C07C 49/757 (2006.01) C07C 69/96 (2006.01) C07C 205/45 (2006.01) C07C 323/20 (2006.01) C07C 323/22 (2006.01) C07C 323/52 (2006.01) C07D 233/60 (2006.01) C07D 317/72 (2006.01) C07D 319/08 (2006.01)

Patent

CA 2260926

The present invention provides illudin analogs of general formula (I) where R1 is (CH2)n-X-Y or H; n is 0 to 4; X is O or S or N or absent; and Y is an optionally substituted (C1-C8)alkyl, (C6-C10)aryl, (C6-C10)aryl(C1-C4)alkyl or cyclo(C3- C6)alkyl optionally comprising one or more heteroatoms; a monosaccharide, an amino acid residue, or H when n is 2-4; R2 is absent; or R1 and R2 together comprise a 5-- 7-membered cyclic ring; R3 is (C1-C4)alkyl or H; R4 is H, SCH2CO2(C1- C4)alkyl, O-(C5-C12)aryl or -S-(C5-C12)aryl; R5 is H, OH or absent; R6 is (C1-C4)alkyl or absent; R7 is OH or OSi((C1-C4)alkyl)3; or R6 and R7 together are ethylenedioxy; R8 is optionally substituted (C1-C4)alkyl; and the bonds represented by ----- are individually present or absent. The invention further provides dimers comprising analogs for formula (I).

Analogues d'illudine de formule générale (I) dans laquelle R1 est (CH2)n-X-Y ou H; n est 0 à 4; X est O ou S ou N ou absent; et Y est (C1-C8)alkyle éventuellement substitué, (C6-C10)aryle, (C6-C10)aryl(C1-C4)alkyle ou cyclo(C3-C6)alkyle comprenant éventuellement un ou plusieurs hétéroatomes; un monosaccharide, un reste d'acide aminé ou H lorsque n est 2 à 4; R2 est absent; ou R1 et R2 ensemble comprennent un noyau cyclique ayant 5 à 7 éléments; R3 est (C1-C4)alkyle ou H; R4 est H, SCH2CO2(C1-C4)alkyle, O-(C5-C12)aryle ou -S-(C5-C12)aryle; R5 est H, OH ou absent; R6 est (C1-C4)alkyle ou absent; R7 est OH ou OSi((C1-C4)alkyle)3; ou R6 et R7 ensemble sont éthylènedioxy; R8 est (C1-C4)alkyle éventuellement substitué; et les liaisons représentées par ----- sont individuellement présentes ou absentes. La présente invention concerne en outre des dimères comportant des analogues de formule (I).

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