Patent ID: 6518315
Filing Date: 2003-02-11
Classification: C07C,C07D

Abstract:
A compound of formula (I) or a pharmaceutically acceptable derivative thereof: whereR1 is H, OH, OC1-4alkyl, NO2 R2 is OH, OC1-4alkyl, OC&boxH;OC1-4alkyl or OC&boxH;OPh where the Ph can be optionally substituted by halogen, C1-3 alkyl or NO2; R1 and R2 along with the two carbon atoms of the phenyl ring to which they are attached can combine to form a 5 or 6 membered heterocyclic ring comprising 1 or 2 heteroatoms selected from O, S or N; R3 is C2-12alkyl, C2-12alkenyl or C2-12alkynyl each optionally substituted by one or more substituents selected from â€”OR, &boxH;O, nitro, halogen, â€”NRRâ€², â€”COOR or â€”CONRRâ€² where R and Râ€² are H or C1-4alkyl; R3 may be a linking group of a bis compound where R3 is C2-12alkylene, C2-12alkenylene or C2-12alkynylene each optionally substituted by one or more substituents selected from â€”OR, &boxH;O, nitro, halogen, â€”NRRâ€², â€”COOR or â€”CONRRâ€² where R and Râ€² are H or C1-4alkyl; R4 is H, CH3, OH or &boxH;O; when R4 is &boxH;O, then the carbon to which R4 is attached is not bonded to H; W is C(&boxH;O)â€”CH2, CH&boxH;CHâ€”, CH2CO, CH(OH)â€”CH2, C(CH3)(OH)CH2, CH2CH(OH), CH2C(CH3)OH, CO, CHOH, C(CH3)(OH), CH2, CH2CH2; X is â€”CHâ€”OH, C(CH3) OH, CH2, CH(CH3) or â€”C&boxH;O; Y is â€”CHâ€”OH, C(CH3)OH, CH2, CH(CH3) or â€”C&boxH;O; provided that one of W, X or Y has an OH group and provided that when (1) R1 is OC1-4alkyl, R2 is OH or OAcyl, W=CH2CH2 and X=C&boxH;O, R3 is C2-12 alkyl, R4 is H, then Y is not CHOH (gingerols); (2) R1 is OCH3, R2 is OH, W is CH2CH2, R3 is C5 or C7 alkyl, R4 is H and X=CHOH then Y is not CHOH (gingerdiol); (3) R1 is OCH3, R2 is OH, W is CH&boxH;CH, R3 is C2-12 alkyl, R4 is H and X is C&boxH;O, then Y is not CHOH (dehydrogingerols); (4) R1 is OCH3, R2 is OH, W=CH2CH2, X is CHOH, R4 is H and R3 is C5 alkyl then Y is not CH2 (reduced paradol); (5) R1 is OCH3, R2 is OH, W=CH2CH2, X is C=O, R4 is H then Y is not C(OH)CH3; (6) R1 is OC1-4 alkyl, R2 is OH or OAcyl, W=CH&boxH;CH and X=C&boxH;O, R3 is C2-9 alkyl, R4 is H, then Y is not CHOH; (7) R1=R2 is OH, W=CH&boxH;CH and X=C&boxH;O, R3 is C9 alkyl, R4 is H, then Y is not CHOH ([10]-nordehydrogingerols); (8) R1=R2 is OH, W=CH2CH2 and X=C&boxH;O, R3 is C2-12 alkyl, R4 is H, then Y is not CHOH (norgingerols); and (9) R1 is OC1-4 alkyl or OH, R2 is OH, W is CH2CH2, R3 is C2-12 alkyl, R4 is H and X is CHOH, then Y is not CHOH (gingerdiols or norgingerdiols).