Inhibitors of farnesyl protein transferase

C - Chemistry – Metallurgy – 07 – K

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C07K 5/083 (2006.01) A61K 31/16 (2006.01) A61K 31/40 (2006.01) A61K 31/47 (2006.01) A61K 38/05 (2006.01) A61K 38/06 (2006.01) C07C 323/30 (2006.01) C07D 207/12 (2006.01) C07D 217/26 (2006.01) C07D 401/12 (2006.01) C07K 5/062 (2006.01) A61K 38/00 (2006.01)

Patent

CA 2155448

Inhibition of farnesyl transferase, which is an enzyme involved in ras oncogene expression, is effected by compounds of the formula Image their enantiomers, diastereomers, and pharmaceutically acceptable salts, prodrugs, and solvates, wherein: G is Image , Image , Image or Image ; when G is Image or Image , it is optionally substituted, at any available position or positions, with halo, alkyl or substituted alkyl having 1 to 20 carbon atoms, alkoxy, or a combination of these groups; G1 is Image optionally substituted, at any of the available position or positions on the ring, with halo, alkyl or substituted alkyl having 1 to 20 carbon atoms, alkoxy, aryl, aralkyl, hydroxy, alkanoyl, alkanoyloxy, amino, alkylamino, dialkylamino, alkanoylamino, thiol, alkylthio, alkylthiono, alkylsulfonyl, sulfonamido, nitro, cyano, carboxy, carbamyl, N-hydroxycarbamyl, N-alkylcarbamyl, N-dialkylcarbamyl, alkoxycarbonyl, phenyl, substituted phenyl, or a combination of these groups; G2 is Image , Image or -NR6-CH(Q1)-; J, K and L are each, independently, N, NR7, O, S or CR6 with the provisos that only one of the groups J, K and L can be O or S, and at least one of the groups J or L must be N, NR7, O or S to form a fused five-membered heteroring; the bond between J and K or K and L may also form one side of a phenyl ring fused to the fused five-membered heteroring; Q is is alkyl, cycloalkyl, substituted alkyl, aryl, pyrrolyl, furyl, thiophenyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl, pyrrolidyl or pyridyl; Q1, A1 and A2 are each, independently, H, alkyl, substituted alkyl, phenyl or substituted phenyl; G3 is R8, -C(O)OR8, -C(O)NR8R9, -C(O)N(R10)OR8, -C(O)NHSO2R11 or -CH2OR8; X is -SH, -OH or -NHR12; X1 is -NR13-, -CH2- or -CH(NHR14)-; Y and Z are each, independently, -CH2- or -C(O)-; R1 - R14 are each, independently, H or alkyl having 1 to 20 carbon atoms; R3 may also be substituted alkyl or cycloalkyl; R4, R5 and R11 may also be aryl or aralkyl; R7, R8, R9 and R10 may also be aralkyl; and R12, R13 and R14 may also be substituted alkyl or aralkyl; m is 0 or an integer from 1 to 2; q is 0 or an integer from 1 to 3; t is an integer from 1 to 2; and the dotted line represents an optional double bond.

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