Patent ID: 6340683
Filing Date: 2002-01-22
Classification: A61P,C07D

Abstract:
A compound having the structure: wherein R1 is F; Cl; Br; I; NR3R4 or heteroaryl, wherein the heteroaryl may be substituted with one or more of F, Cl, Br, I, â€”CN, â€”NO2, â€”NR5R6, â€”SO2R5, â€”(CH2)nC(Y)R7, â€”(CH2)nYR5, â€”(CH2)nC(Y)NR5R6, â€”(CH2)nNR5C(Y)R5, â€”(CH2)nCO2Râ€”(CH2)nSO2NR5R6, a straight chained or branched C1-C7 alkyl, monofluoroalkyl, polyfluoroalkyl, aminoalkyl, C2-C7 alkenyl or C2-C7 alkynyl, or C3-C7 cycloalkyl or a cycloalkenyl; wherein R2 is NR3R4; wherein R3 is independently H; â€”(CH2)uYR5; â€”(CH2)tC(Y)NR5R6; â€”(CH2)uNR5C(Y)R5; â€”(CH2)tC(Y)R7; â€”(CH2)tCO2R5; â€”(CH2)uNR5R6; â€”(CH2)uCN; â€”C(Y)R5; â€”C(Y)NR5R6; â€”CO2R5; straight chained or branched C1-C7 alkyl, C2-C7 alkenyl, or C2-C7 alkynyl; C3-C7 cycloalkyl or cycloalkenyl; phenyl; C1-C6 phenylalkyl; C1-C6, heteroarylalkyl; wherein the phenyl, C1-C6 phenylalkyl, or C1-C6 heteroarylalkyl may be substituted with one or more of F, Cl, Br, I, â€”CN, â€”NO2, â€”NR5R6, â€”SO2R5, â€”(CH2)nC(Y)R7, â€”(CH2)nYR5, â€”(CH2)nC(Y)NR5R6, â€”(CH2)nNR5C(Y)R5, â€”(CH2)nCO2R5, â€”(CH2)nSO2NR5R6, a straight chained or branched C1-C7 alkyl, monofluoroalkyl, polyfluoroalkyl, aminoalkyl, C2-C7 alkenyl or C2-C7 alkynyl, or a C3-C7 cycloalkyl or cycloalkenyl; wherein R4 is independently â€”(CH2)uYR5; â€”(CH2)tC(Y)NR5R6; â€”(CH2)uNR5C(Y)R5; â€”(CH2)tC(Y)R7; â€”(CH2)tCO2R5; â€”(CH2)uNR5R6; â€”(CH2)nCN; straight chained or branched C1-C7 alkyl; straight chained or branched C2-C7 alkenyl or C2-C7 alkynyl; C3-C7 cycloalkyl or cycloalkenyl; phenyl; or C1-C6 phenylalkyl; wherein the phenyl or C1-C6 phenylalkyl may be substituted with one or more of F, Cl, Br, I, â€”CN, â€”NO2, â€”NR5R6, â€”SO2R5, â€”(CH2)nC(Y)R7, â€”(CH2)nYR5, â€”(CH2)nC(Y)NR5R6, â€”(CH2)nNR5C(Y)R5, â€”(CH2)nCO2R5, â€”(CH2)nSO2NR5R6, a straight chained or branched C1-C7 alkyl, monofluoroalkyl, polyfluoroalkyl, aminoalkyl, C2-C7 alkenyl or C2-C7 alkynyl, or a C3-C7 cycloalkyl or cycloalkenyl; or R3 and R4 taken together with the nitrogen atom to which they are attached are 1-azetidinyl, 1-pyrrolidinyl, 1-piperidinyl, or 1H-azepanyl, wherein the 1-azetidinyl, 1-pyrrolidinyl, 1-piperidinyl, or 1H-azepanyl is substituted with one or more of F, â€”CN, â€”(CH2)nYR5R6, â€”SO2R5, â€”(CH2)nC(Y)R7, â€”(CH2)nYR5, â€”(CH2)nC(Y)NR5R6, â€”(CH2)nNR5C(Y)R5, â€”(CH2)nCO2R5, a straight chained or branched C1-C7 alkyl, monofluoroalkyl, polyfluoroalkyl, aminoalkyl, a C2-C7 alkenyl or C2-C7 alkynyl, a C3-C7 cycloalkyl or cycloalkenyl, or phenyl or heteroaryl; wherein if â€”(CH2)nNR5R6, â€”(CH2)nYR5, or â€”(CH2)nNR5C(Y)R5 are in the 2-position, then n is not 0; wherein the phenyl or heteroaryl may be substituted with one or more of F, Cl, Br, I, â€”CN, â€”NO2, â€”NR5R6, â€”SO2R5, â€”(CH2)nC(Y)R7, â€”(CH2)nYR5, â€”(CH2)nC(Y)NR5R6, â€”(CH2)nNR5C(Y)R5, â€”(CH2)nCO2R5, â€”(CH2)nSO2NR5R6, a straight chained or branched C1-C7 alkyl, monofluoroalkyl, polyfluoroalkyl, aminoalkyl, a C2-C7 alkenyl or C2-C7 alkynyl, or a C3-C7 cycloalkyl or cycloalkenyl; or R3 and R4 taken together with the nitrogen atom to which they are attached are morpholinyl, thiomorpholinyl, [1,4]oxazepanyl, [1,4]thiazepanyl, piperazinyl, or [1,4]diazepanyl, wherein the morpholinyl, thiomorpholinyl, [1,4]oxazepanyl, [1,4]thiazepanyl, piperazinyl, or [1,4]diazepanyl is substituted with one or more straight chained or branched C1-C7 alkyl or C1-C7 phenylalkyl; and wherein the nitrogen atom of the piperazinyl or [1,4]diazepanyl ring is substituted with â€”(CH2)uYR5; â€”(CH2)tC(Y)NR5R6; â€”(CH2)uNR5C(Y)R5; â€”(CH2)tC(Y)R7; â€”(CH2)tCO2R5; â€”(CH2)uNR5R6; â€”(CH2)uCN; â€”C(Y)R5; â€”C(Y)NR5R6; â€”CO2R5; straight chained or branched C1-C7 alkyl, C2-C7 alkenyl, or C2-C7 alkynyl; or C3-C7 cycloalkyl or cycloalkenyl; phenyl, C1-C6 phenylalkyl; or C1-C6 heteroarylalkyl; wherein the phenyl, C1-C6 phenylalkyl; or C1-C6 heteroarylalkyl may be substituted with one or more of F, Cl, Br, I, â€”CN, â€”NO2, â€”NR5R6, â€”SO2R5, â€”(CH2)nC(Y)R7, â€”(CH2)nYR5, â€”(CH2)nC(Y)NR5R6, â€”(CH2)nNR5C(Y)R5, â€”(CH2)nCO2R5, â€”(CH2)nSO2NR5R6, a straight chained or branched C1-C7 alkyl, monofluoroalkyl, polyfluoroalkyl, aminoalkyl, C2-C7 alkenyl or C2-C7 alkynyl, or a C3-C7 cycloalkyl or cycloalkenyl; wherein each of R5, R6, and R7 is independently H; or straight chained or branched C1-C7 alkyl; wherein each n independently is an integer from 0 to 6 inclusive; wherein each t independently is an integer from 1 to 4 inclusive; wherein each u independently is an integer from 2 to 4 inclusive; wherein Y is O or S; wherein R8 is â€ƒprovided that if R8 contains a piperidinyl group and m is O, then the compound is not an &agr;-aminal-containing compound; wherein each of R9 and R10 is independently H; straight chained or branched C1-C4 alkyl; wherein R11 is wherein R12 is H; wherein R13 is independently H; â€”(CH2)uYR5; â€”(CH2)tC(Y)NR5R6; â€”(CH2)uNR5C(Y)R5; â€”(CH2)tC(Y)R7; â€”(CH2)tCO2R5; â€”(CH2)uNR5R6; â€”(CH2)uCN; â€”C(Y)R5; â€”C(Y)NR5R6; â€”CO2R5; straight chained or branched C1-C7 alkyl; C1-C7 alkyl substituted with one or more F or Cl; C3-C7 cycloalkyl-C1-C7 alkyl; straight chained or branched C2-C7 alkenyl, or alkynyl; or C3-C7 cycloalkyl or cycloalkenyl; phenyl or C1-C6 phenylalkyl; wherein the phenyl or C1-C6 phenylalkyl may be substituted with one or more of F, Cl, â€”CN, â€”NO2, â€”NR5R6, â€”SO2R5, â€”(CH2)nC(Y)R7, â€”(CH2)nYR5, â€”(CH2)nC(Y)NR5R6, â€”(CH2)nNR5C(Y)R5, â€”(CH2)nCO2R5, â€”(CH2)nSO2NR5R6, a straight chained or branched C1-C7 alkyl, monofluoroalkyl, polyfluoroalkyl, aminoalkyl, a C2-C7 alkenyl or C2-C7 alkynyl, or a C3-C7 cycloalkyl or cycloalkenyl; or R12 and R13 together with the amide linkage to which they are attached are pyrrolidinonyl or piperidonyl; wherein R14 is H; straight chained or branched C1-C7 alkyl; F; or â€”(CH2)nOR5; wherein R15 is H, straight chained or branched C1-C7 alkyl, or F; wherein R16 is NR3R4, unsubstituted straight chained or branched C2-C7 alkyl, substituted straight chained or branched C1-C7 alkyl, wherein the C1-C7 alkyl may be substituted with one or more of F, Cl, â€”CN, â€”NR5R6, â€”SO2R5, â€”(CH2)nC(Y)R7, â€”(CH2)nYR5, â€”(CH2)nC(Y)NR5R6, â€”(CH2)nNR5C(Y)R5, â€”(CH2)nCO2R5, â€”(CH2)nOCF3, monofluoroalkyl, polyfluoroalkyl, or aminoalkyl, straight chained or branched C2-C7 alkenyl or C2-C7 alkynyl, or C3-C7 cycloalkyl or cycloalkenyl; phenyl, heteroaryl, or C1-C7 phenylalkyl, wherein the phenyl, heteroaryl, or C1-C7 phenylalkyl may be substituted with one or more of F, Cl, Br, I, â€”CN, â€”NO2, â€”NR5R6, â€”(CH2)nNR5C(Y)R5, â€”SO2R5, â€”(CH2)nC(Y)R7, â€”(CH2)nYR5, â€”(CH2)nC(Y)NR5R6, â€”(CH2)nCO2R5, â€”(CH2)nSO2NR5R6, ethylenedioxy, methylenedioxy, straight chained or branched C1-C7 alkyl, monofluoroalkyl, polyfluoroalkyl, or aminoalkyl, straight chained or branched C2-C7 alkenyl or alkynyl, or C3-C7 cycloalkyl or cycloalkenyl; quinolinyl, 1-naphthyl, 2-naphthyl, or 2,1,3-benzothiadiazolyl; with the provisos that when R1 is F, Cl, Br, or I, then R16 is 1-naphthyl; and when R1 and R2 are morpholinyl, then R16 is not NR3R4; wherein each m independently is an integer from 0 to 3 inclusive; wherein each s independently is an integer from 1 to 6 inclusive; wherein each p independently is an integer from 0 to 2 inclusive; wherein each q independently is an integer from 1 to 2 inclusive; wherein each r independently is an integer from 1 to 2 inclusive; wherein X is N or C; wherein heteroaryl is pyrazolyl, pyrrolyl, furanyl, pyridyl, imidazolyl, oxazolyl, pyrimidinyl, isoxazolyl, or thienyl; or a pharmaceutically acceptable salt thereof.