Patent ID: 6521660
Filing Date: 2003-02-18
Classification: C07C,C07D,C07F

Abstract:
A taxane derivative having the formula whereinX1 is â€”OX6, â€”SX7, or â€”NX8X9; X2 is hydrogen, alkyl, alkenyl, alkynyl, aryl, or heteroaryl; X3 is alkyl; X4 is hydrogen; X5 is â€”COX10, â€”COOX10, â€”COSX10, â€”CONX8X10, or â€”SO2X11; X6 is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, or hydroxy protecting group; X7 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, or sulfhydryl protecting group; X8 is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, or heterosubstituted alkyl, alkenyl, alkynyl, aryl or heteroaryl; X9 is an amino protecting group; X10 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, or heterosubstituted alkyl, alkenyl alkynyl, aryl or heteroaryl; X11 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, â€”OX10, or â€”NX8X14; X14 is hydrogen, alkyl, alkenyl, alkynyl, aryl, or heteroaryl; R1 is hydrogen, hydroxy, protected hydroxy or together with R14 forms a carbonate; R2 is hydrogen, hydroxy, â€”OCOR31 together with R2a forms an oxo; R2a is hydrogen or taken together with R2 forms an oxo or; 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, â€”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, protected 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, alkyl, alkenyl, alkynyl, aryl, or heteroaryl, hydroxy, protected hydroxy or together with R6a forms an oxo; R6a is hydrogen, alkyl, alkenyl, alkynyl, aryl, or heteroaryl, hydroxy, protected hydroxy or together with R6 forms an oxo; R7 is hydrogen or together with R7a forms an oxo, R7a is hydrogen, halogen, protected hydroxy, â€”OR28, or together with R7 forms an oxo; R9 is hydrogen or together with R9a forms an oxo, R9a is hydrogen, hydroxy, protected hydroxy, acyloxy, or together with R9 forms an oxo; R10 is hydrogen or together with R10a forms an oxo, R10a is hydrogen, â€”OCOR29, hydroxy, or protected hydroxy, or together with R10 forms an oxo; R14 is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, hydroxy, protected hydroxy or together with R1 forms a carbonate; R14a is hydrogen, alkyl, alkenyl, alkynyl, aryl, or heteroaryl; R28 is hydrogen, acyl, or hydroxy protecting group; R29, R30, and R31 are independently hydrogen, alkyl, alkenyl, alkynyl, monocyclic aryl or monocyclic heteroaryl; and the taxane has a structure which differs from that of taxol or docetaxel with respect to the C13 side chain and at least one other substituent.