Patent ID: 8084456

Claim:
A tubulin inhibitor of the formula I: wherein: R 1 is H, C 1-6 alkyl, C 1-6 alkylNR 5 R 6 , C 1-6 alkylNR 5 COR 6 , C 1-6 alkylNR 5 SO 2 R 6 , C 1-6 alkylCO 2 R 5 , C 1-6 alkylCONR 5 R 6 , where R 5 and R 6 are each independently H, C 1-4 alkyl, aryl, hetaryl, C 1-4 alkylaryl, C 1-4 alkylhetaryl or may be joined to form a 3-8 membered ring optionally containing an atom selected from O, S, NR 7 and R 7 is selected from H, C 1-4 alkyl; R 2 and R 3 are each independently halogen, C 1-4 alkyl, OH, OC 1-4 alkyl, CF 3 , OCF 3 , CN, C 1-4 alkylNR 8 R 9 , OC 1-4 alkylNR 8 R 9 , OCONR 8 R 9 , NR 8 R 9 , NR 8 COR 9 , NR 10 CONR 8 R 9 , NR 8 SO 2 R 9 , COOR 8 , CONR 8 R 9 ; wherein R 8 , R 9 and R 10 are each independently H, C 1-4 alkyl, C 1-4 alkyl cycloalkyl, or may be joined to form a 3-8 membered ring optionally containing an atom selected from O, S, NR 11 ; wherein R 11 is H, C 1-11 alkyl or CF 3 ; alternatively, R 2 and R 3 , when located on adjacent carbon atoms, may be joined to form the ring system where R 22 is H, C 1-4 alkyl, or CF 3 ; Q is C 1-4 alkylene; W is C 2-4 alkyl or C 2-6 alkenyl, where C 2-4 alkyl or C 2-6 alkenyl may be optionally substituted with C 1-4 alkyl, OH, OC 1-4 alkyl, NR 15 R 16 ; wherein R 15 , and R 16 are each independently H, C 1-4 alkyl, C 1-4 alkyl cycloalkyl, C 1-4 alkyl cyclohetalkyl, aryl, hetaryl, or may be joined to form a 3-8 membered ring optionally containing an atom selected from O, S, NR 17 wherein R 17 is H or C 1-4 alkyl; A is aryl, or hetaryl each optionally substituted with 0-3 substituents independently selected from halogen, C 1-4 alkyl, CF 3 , aryl, hetaryl, OCF 3 , OC 1-4 alkyl, OC 2-5 alkylNR 18 R 19 , Oaryl, Ohetaryl, CO 2 R 18 , CONR 18 R 19 , NR 18 R 19 , C 1-4 alkylNR 18 R 19 , NR 20 C 1-4 alkylNR 18 R 19 , NR 18 COR 19 , NR 20 CONR 18 R 19 , NR 18 SO 2 R 19 ; wherein R 18 , R 19 are each independently H, C 1-4 alkyl, C 1-4 alkyl cyclohetalkyl, aryl, hetaryl, C 1-4 alkyl aryl, C 1-4 alkyl hetaryl, or may be joined to form a 3-8 membered ring optionally containing an atom selected from O, S, NR 21 ; wherein R 20 and R 21 are independently H or C 1-4 alkyl; and Z is H or C 1-4 alkyl, or a tubulin inhibitor of the formula or pharmaceutically acceptable prodrugs, salts or stereoisomers thereof, wherein prodrugs are esters of a free carboxy or hydroxy group or amides of a free amino group.