Patent ID: 6809099
Filing Date: 2004-10-26
Classification: A61P,C07D

Abstract:
A compound having the structure (I): wherein:m is 0, 2, 3, 4, or 5; R1 is â€”NRARB wherein RA and RB are independently hydrogen, â€”(C&boxH;O)RC, â€”NHRC, â€”(SO2)RC, â€”ORC, or an aliphatic, heteroaliphatic, aryl, or heteroaryl moiety, or RA and RB, when taken together form an heteroaryl or cycloheteroaliphatic moiety, wherein each occurrence of RC is independently hydrogen, â€”ORD, â€”SRD, â€”NHRD, â€”(C&boxH;O)RD, or an aliphatic, heteroaliphatic, aryl, or heteroaryl moiety, wherein each occurrence of RD is independently hydrogen, or an aliphatic, heteroaliphatic, aryl, heteroaryl, acyl, alkoxy, aryloxy, alkylthio, arylthio, heteroaryloxy, or heteroarylthio moiety; wherein R2 is hydrogen, â€”ORE, &boxH;O, â€”C(&boxH;O)RE, â€”CO2RE, â€”CN, â€”SCN, halogen, â€”SRE, â€”SORE, â€”SO2RE, â€”NO2, â€”N(RE)2, â€”NHC(O)RE, or an aliphatic, heteroaliphatic, aryl, or heteroaryl moiety, wherein each occurrence of RE is independently hydrogen, or an aliphatic, heteroaliphatic, aryl, heteroaryl, acyl, alkoxy, aryloxy, alkylthio, arylthio, heteroaryloxy, or heteroarylthio moiety; wherein R3 is hydrogen, â€”COORF, â€”CORF, â€”CN, or an aliphatic, heteroaliphatic, aryl, or heteroaryl moiety, wherein each occurrence of RF is independently hydrogen, or an aliphatic, heteroaliphatic, aryl, heteroaryl, alkoxy, aryloxy, alkylthio, arylthio, heteroaryloxy, or heteroarylthio moiety; wherein:the foregoing aliphatic or heteroaliphatic moieties in R1, R2 and R3 may independently be unsubstituted or substituted with one or more substitutents independently selected from aliphatic, heteroaliphatic, aryl, heteroaryl, alkylaryl, alkylheteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylthio, arylthio, heteroarylthio, F, Cl, Br, I, â€”OH, â€”NO2, â€”CN, â€”SCN, â€”CF3, â€”CHCF3, â€”CHCl2, â€”CH2OH, â€”CH2CH2OH, â€”CH2NH2, â€”CH2SO2CH3, â€”C(O)Rx, â€”CO2(Rx), â€”CON(Rx)2, â€”OC(O)Rx, â€”OCO2Rx, â€”OCON(Rx)2, â€”S(O)2Rx, or â€”B(ORx)2 wherein each occurrence of Rx independently is aliphatic, heteroaliphatic, aryl, heteroaryl, alkylaryl, or alkylheteroaryl where each of the foregoing aliphatic and heteroaliphatic moiety is unsubstituted; and each of the foregoing aryl, heteroaryl, or cycloheteroaliphatic moieties in R1, R2 and R3 may independently be unsubstituted or substituted with one, two or three substitutents independently selected from aliphatic, heteroaliphatic, aryl, heteroaryl, alkylaryl, alkylheteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylthio, arylthio, heteroarylthio, F, Cl, Br, I, â€”OH, â€”NO2, â€”CN, â€”SCN, â€”CF3, â€”CHCF3, â€”CHCl2, â€”CH2OH, â€”CH2CH2OH, â€”CH2NH2, â€”CH2SO2CH3, â€”C(O)Rx, â€”CO2(Rx), â€”CON(Rx)2, â€”OC(O)Rx, â€”OCO2Rx, â€”OCON(Rx)2, â€”N(Rx)2, â€”S(O)2Rx, â€”NRx(CO)Rx, or â€”B(ORx)2 wherein each occurrence of Rx independently is aliphatic, heteroaliphatic, aryl, heteroaryl, alkylaryl, or alkylheteroaryl where each of the foregoing aliphatic, heteroaliphatic, aryl, heteroaryl, alkylaryl, alkylheteroaryl, aryloxy, heteroaryloxy, arylthio, and heteroarylthio moiety is unsubstituted; wherein R4 and R6 are each independently hydrogen, or an aliphatic, heteroaliphatic, aryl, heteroaryl, acyl, alkoxy, aryloxy, alkylthio, arylthio, heteroaryloxy, or heteroarylthio moiety where the foregoing aliphatic, heteroaliphatic, aryl, heteroaryl, aryloxy, arylthio, heteroaryloxy and heteroarylthio moieties in R4 and R6 are unsubstituted; wherein R5 and R7 are each independently hydrogen, â€”ORG, â€”C(&boxH;O)RG, â€”CO2RG, â€”CN, â€”SCN, halogen, â€”SRG, â€”SORG, â€”SO2RG, â€”NO2, â€”N(RG)2, â€”NHC(O)RG, or an aliphatic, heteroaliphatic, aryl or heteroaryl moiety, wherein each occurrence of Rg is independently hydrogen, or an aliphatic, heteroaliphatic, aryl, heteroaryl, acyl, alkoxy, aryloxy, alkylthio, arylthio, heteroaryloxy, or heteroarylthio moiety where the each of the foregoing aliphatic, heteroaliphatic, aryl, heteroaryl, aryloxy, arylthio, heteroaryloxy and heteroarylthio moiety in R5 and R6 is unsubstituted; wherein R8 is hydrogen, alkyl, â€”OH, &boxH;O, â€”CN, â€”SCN, halogen, â€”SH, alkoxy, thioalkyl, amino, or alkylamino; wherein X1, X2, X3 and X4 are each independently hydrogen, â€”ORH, &boxH;O, â€”C(&boxH;O)RH, â€”CO2RH, â€”CN, â€”SCN, halogen, â€”SRH, â€”SORH, â€”SO2RH, â€”NO2, â€”N(RH)2, â€”NHC(O)RH, or an aliphatic, heteroaliphatic, aryl, or heteroaryl moiety, wherein each occurrence of RH is independently hydrogen, or an aliphatic, heteroaliphatic, aryl, heteroaryl, acyl, alkoxy, aryloxy, alkylthio, arylthio, heteroaryloxy, or heteroarylthio moiety where each of the foregoing aliphatic, heteroaliphatic, aryl, heteroaryl, aryloxy, arylthio, heteroaryloxy and heteroarylthio moiety in X1, X2, X3 and X4 is unsubstituted; whereby if at least either X1 and X2 or X3 and X4 are doubly bonded to the 6-membered ring, then the dotted bonds in either or both of the 6-membered rings represent two single bonds and one double bond, and a quinone moiety is generated, or if at least either X1 and X2 or X3 and X4 are singly bonded to the 6-membered ring, then the dotted bonds in either or both of the 6-membered rings represent two double bonds and one single bond, and a hydroquinone moiety is generated; wherein:each of foregoing acyl, alkoxy, alkylthio, thioalkyl, or alkylamino contains unsubstituted cyclic, acyclic, branched or unbranched alkyl of 1 to 10 carbon atoms; each of the foregoing aliphatic moiety is cyclic, acyclic, branched or unbranched alkyl, alkenyl, or alkynyl containing 1 to 10 carbon atoms; each of the foregoing heteroaliphatic moiety is cyclic, acyclic, branched or unbranched alkyl, alkenyl, or alkynyl containing 1 to 10 carbon atoms and which further contains one or more oxygen, sulfur, nitrogen, phosphorus or silicon atoms in place of the carbon atoms; each of the foregoing cycloheteroaliphatic moiety is a cyclic heteroaliphatic; each of the foregoing aryl is monocyclic or bicyclic carbocyclic ring system having one or two aromatic ring; each of the foregoing heteroaryl is a cyclic aromatic radical having from five to ten ring atoms of which one ring atom is selected from S, O, and N; zero or two ring atoms are additional heteroatoms independently selected from S, O, and N; and the remaining ring atoms are carbon; and pharmaceutically acceptable salts thereof.