Patent ID: 6486167
Filing Date: 2002-11-26
Classification: A61P,C07D

Abstract:
A compound of formula I: whereinR1, R2 and R3 are each individually hydrogen, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C1-C6)alkoxy, nitro, hydroxy, NRgRh, COORk, ORm, or halo; or R1 and R2 taken together are methylenedioxy and R3 is hydrogen, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C1-C6)alkoxy, nitro, hydroxy, NRgRh, COORK, ORm, or halo; or R2 and R3 taken together are methylenedioxy and R1 is hydrogen, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C1-C6)alkoxy, nitro, hydroxy, NRgRh, COORk, ORm, or halo; R4 is oxy, (C1-C6)alkyl, or is absent; R5 is hydrogen, hydroxy, or (C1-C6)alkyl; R6, R7 and R8 are each individually hydrogen, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C1-C6)alkoxy, nitro, hydroxy, NRgRh, COORk, ORm, or halo; or R6 and R7 taken together are methylenedioxy and R8 is hydrogen, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C1-C6)alkoxy, nitro, hydroxy, NRgRh, COORk, ORm, or halo; or R7 and R8 taken together are methylenedioxy and R6 is hydrogen, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C1-C6)alkoxy, nitro, hydroxy, NRgRh, C(&boxH;O)Rk, COORk, ORm, or halo; each bond represented by â€”â€”â€”â€”â€” is individually present or absent; X is C(Ra)(Rb) or NRc; Y is C(Rd)(Re) or NRf; if present, Ra and Rb are each independently hydrogen or (C1-C6)alkyl if the bond between the 11- and 12-positions represented by â€”â€”â€”â€”â€” is absent; or Ra is hydrogen or (C1-C6)alkyl and Ra is absent if the bond between the 11- and 12-positions represented by â€”â€”â€”â€”â€” is present; if present, Rc and Rf are each independently hydrogen or (C1-C6)alkyl if the bond between the 11- and 12-positions represented by â€”â€”â€”â€”â€” is absent; or Rc and Rf are each independently (C1-C6)alkyl or absent if the bond between the 11- and 12-positions represented by â€”â€”â€”â€”â€” is present; if present, Rd and Re are each independently hydrogen or (C1-C6)alkyl if the bond between the 11- and 12-positions represented by â€”â€”â€”â€”â€” is absent; or Rd is hydrogen or (C1-C6)alkyl and Re is absent if the bond between the 11- and 12-positions represented by â€”â€”â€”â€”â€” is present; each Rg and Rh is independently hydrogen, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C1-C6)alkoxy, (C1-C6)alkanoyl, aryl, aryl(C1-C6)alkyl, aryloxy, or aryl(C1-C6)alkoxy; or Rg and Rh together with the nitrogen to which they are attached are pyrrolidino, piperidino, morpholino, or thiomorpholino; each Rk is independently hydrogen, or (C1-C6)alkyl; and each Rm is independently (C1-C6)alkanoyl, aryl, or aryl(C1-C6)alkyl; wherein any (C1-C6)alkyl, (C3-C6)cycloalkyl, or (C1-C6)alkoxy of R1, R2, R3, R6, R7, R8, or Rk is optionally substituted on carbon with 1, 2, or 3 substituents independently selected from hydroxy, halo, NRnRp, (C3-C6)cycloalkyl, or (C1-C6)alkoxy; wherein each Rn and Rp is independently hydrogen, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C1-C6)alkoxy, or (C1-C6)alkanoyl; or Rn and Rp together with the nitrogen to which they are attached are pyrrolidino, piperidino, morpholino, or thiomorpholino; wherein any aryl is optionally be substituted with 1, 2, or 3 substituents independently selected from hydroxy, halo, nitro, trifluoromethyl, trifluoromethoxy, carboxy, amino, (C1-C6)alkyl, (C3-C6)cycloalkyl, and (C1-C6)alkoxy; provided that at least one of R2 and R8 is hydrogen, methyl, nitro, hydroxy, amino, fluoro or chloro; or at least one of R2 and R8 forms part of a methylenedioxy; and provided that R1-R3 and R6-R8 are not all hydrogen; provided the compound is not 9-methylbenzo[i]phenanthridine; 1-chloro-2-methoxybenzo[i]phenanthridine; 2-methoxybenzo[i]phenanthridine; 2,3-methylenedioxy-8,9-methylenedioxybenzo[i]phenanthridine; 5,8-dimethylbenzo[i]phenanthridine; 2-methoxy-5-methylbenzo[i]phenanthridine; 2-methoxy-5,8-dimethyl benzo[i]phenanthridine; 5,6-dihydro-9-methylbenzo[i]phenanthridine; or 1-chloro-2-methoxy-5,6-dihydrobenzo[i]phenanthridine; or a pharmaceutically acceptable salt thereof.