C10 taxane derivatives and pharmaceutical compositions

Details C10 taxane derivatives and pharmaceutical compositions C10 taxane derivatives and pharmaceutical compositions

C - Chemistry, Metallurgy

07

D

C07D 409/12 (2006.01) A61K 31/337 (2006.01) A61K 31/381 (2006.01) C07D 305/14 (2006.01) C07D 405/12 (2006.01) C07D 407/12 (2006.01) C07F 7/18 (2006.01)

Patent

CA 2153805

Taxane derivatives substituted on the C10 position with novel substituents are disclosed. The novel compounds have utility as antileukemia and antitumor agents. The derivatives have the formula: (see formula III) wherein X1 is -OX6, or -SX7; X2 is hydrogen, alkyl, alkenyl, alkynyl, aryl, or heteroaryl; X3 and X4 are independently hydrogen, alkyl, alkenyl, alkynyl, or heteroaryl; X5 is -COX10, or -SO2X11; X6 is hydrogen, alkyl, alkenyl, alkynyl, aryl, or heteroaryl; X7 is alkyl, alkenyl, alkynyl, aryl, or heteroaryl; X8 is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, or substituted alkyl, alkenyl, alkynyl, aryl or heteroaryl, wherein the substituent is selected from nitrogen, oxygen, sulphur and halogen; X10 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, or heterosubstituted alkyl, alkenyl, alkynyl, aryl or heteroaryl; X11 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, -OX10, or -NX8X14; X14 is hydrogen, alkyl, alkenyl, alkynyl, aryl, or heteroaryl; R1 is hydrogen, hydroxy, or together with R14 forms a carbonate; R2 is hydrogen, hydroxy, -OCOR31, or together with R2a forms an oxo; R2a is hydrogen or together with R2 forms an oxo; R4 is hydrogen, together with R4a forms an oxo, oxirane or methylene, or together with R5a and the carbon atoms to which they are attached form an oxetane ring; R4a is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cyano, hydroxy, -OCOR30, or together with R4 forms an oxo, oxirane or methylene; R5 is hydrogen or together with R5a forms an oxo; R5a is hydrogen, hydroxy, acyloxy, together with R5 forms an oxo, or together with R4 and the carbon atoms to which they are attached form an oxetane ring; R6 is hydrogen; R6a is hydrogen, alkyl, alkenyl, alkynyl, aryl, or heteroaryl; R7 is hydrogen or together with R7a forms an oxo; R7a is hydroxy, or together with R7 forms an oxo; R9 together with R9a forms an oxo; R9a together with R9 forms an oxo; R10 is hydrogen or together with R10a forms an oxo; R10a is hydrogen or together with R10 forms an oxo; R14 is hydrogen, alkyl, alkenyl, alkynyl, aryl, or heteroaryl, hydroxy, or together with R1 forms a carbonate; R14a is hydrogen, alkyl, alkenyl, alkynyl, aryl, or heteroaryl; and R30 and R31 are independently hydrogen, alkyl, alkenyl, alkynyl, monocyclic aryl or monocyclic heteroaryl; provided, however, when R10 and R10a are hydrogen (a) R14 is other than hydrogen, (b) R4a is other than acetoxy, (c) R2 is other than benzoyloxy, (d) R1 is other than hydroxy, (e) X3 or X4 is cycloalkyl, alkenyl, or heteroaryl, or (f) X5 is -COX10 with X10 being heteroaryl.

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