Substituted bicyclic fused ring compounds as indoleamine-2,3-dioxygenase inhibitors

A compound selected from one of the following formulae:

• wherein:
• each of X1 and X2 is C;
• X7 is selected from C and N;
• each of R1 and R2 is H;
• each of R3 and R5 is H;
• R4 is an organic group selected from halogen, an unsubstituted C1-C6 alkyl group, a C1-C6 alkyl group substituted with 1-3 halogens, a C3-C6 cycloalkyl group, a C1-C6 alkoxy group, and a nitrile group;
• R31 is selected from:
• H;
• a substituted or unsubstituted linear or branched carbonyl group selected from —(CO)Me, —(CO)Et, —(CO)Pr, —(CO)iPr, —(CO)nBu, —(CO)iBu, —(CO)tBu, —(C O)Ph, —(CO)CH2Ph, —(CO)CH2OH, —(CO)CH2OCH3, —(CO)CH2NH2, —(CO)CH2N HMe, —(CO)CH2NMe2, —(CO)-cyclopropyl, —(CO)-1,3-epoxypropan-2-yl, —(CO)N H2, —(CO)NHMe, —(CO)NMe2, —(CO)NHEt, —(CO)NEt2, —(CO)-pyrollidine-N-yl, —( CO)-morpholine-N-yl, —(CO)-piperazine-N-yl, —(CO)—N-methyl-piperazine-N-yl, —(CO)NHCH2CH2OH, —(CO)NHCH2CH2OMe, —(CO)NHCH2CH2NH2, —(CO)NHCH2CH2NHMe, and —(CO)NHCH2CH2NMe2;
• a substituted or unsubstituted sulphonyl group selected from —SO2Me, —SO2Et, —SO2Pr, —SO2iPr, —SO2Ph, —SO2-(2,3 or 4)-F-Ph, —SO2-cyclopropyl, —SO2CH2CH2OCH3, —SO2NH2, —SO2NHMe, —SO2NMe2, —SO2NHEt, —SO2NEt2, —SO2-pyrrolidine-N-yl, —SO2-morpholine-N-yl, —SO2NHCH2OMe, and —SO2NHCH2CH2OMe;
• —NH—C(O)—C1-4alkyl;
• —NH—SO2—C1-4alkyl;
• a substituted or unsubstituted phenyl group selected from P-, 2-F-Ph-, 3-F-Ph-, 4-F-Ph-, 2-Cl-Ph-, 3-Cl-Ph-, 4-Cl-Ph-, 2-Br-Ph-, 3-Br-Ph-, 4-Br-Ph-, 2-I-Ph-, 3-I-Ph, 4-I-Ph-, 2,(3,4,5 or 6)-F2-Ph-, 2,(3,4,5 or 6)-Cl2-Ph-, 2,(3,4,5 or 6)-Br2-Ph-, 2,(3,4,5 or 6)-I2-Ph-, 2,(3,4,5 or 6)-Me2-Ph-, 2,(3,4,5 or 6)-Et2-Ph-, 2,(3,4,5 or 6)-Pr2-Ph-, 2,(3,4,5 or 6)-Bu2-Ph-, 2,(3,4,5 or 6)-(CN)2-Ph-, 2,(3,4,5 or 6)-(NO2)2-Ph-, 2,(3,4,5 or 6)-(NH2)2-Ph-, 2,(3,4,5 or 6)-(MeO)2-Ph-, 2,(3,4,5 or 6)-(CF3)2-PH-, 3, (4 or 5)-F2-Ph-, 3,(4 or 5)-Cl2-Ph-, 3,(4 or 5)-Br2-Ph-, 3,(4 or 5)-I2-Ph-, 3,(4 or 5)-Me2-Ph-, 3,(4 or 5)-Et2-Ph-, 3,(4 or 5)-Pr2-Ph-, 3,(4 or 5)-Bu2-Ph-, 3,(4 or 5)-(CN)2-Ph-, 3,(4 or 5)-(NO2)2-Ph-, 3,(4 or 5)-(NH2)2-Ph-, 3,(4 or 5)-(MeO)2-Ph-, 3,(4 or 5)-(CF3)2-Ph-, 2-Me-Ph-, 3-Me-Ph-, 4-Me-Ph-, 2-Et-Ph-, 3-Et-Ph-, 4-Et-Ph-, 2-Pr-Ph-, 3-Pr-Ph-, 4-Pr-Ph-, 2-Bu-Ph-, 3-Bu-Ph-, 4-Bu-Ph-, 2-(CN)-Ph-, 3-(CN)-Ph-, 4-(CN)-Ph-, 2-(NO2)-Ph-, 3-(NO2)-Ph-, 4-(NO2)-Ph-, 2-(NH2)-Ph-, 3-(NH2)-Ph-, 4-(NH2)-Ph-, 2-MeO-Ph-, 3-MeO-Ph-, 4-MeO-Ph-, 2-(NH2—CO)-Ph-, 3-(NH2—CO)-Ph-, 4-(NH2—CO)-Ph-, 2-CF3-Ph-, 3-CF3-Ph-, 4-CF3-Ph-, 2-CF3O-Ph-, 3-CF3O-Ph-, and 4-CF3O-Ph-;
• an aromatic heterocyclic group selected from pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, thiophen-2-yl, thiophen-3-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrimidin-6-yl, tetrazole-1yl, tetrazole-2-yl, tetrazole-3-yl, tetrazole-4-yl, tetrazole-5-yl, (1,3,4-oxadiazol)-2-yl, (1,3,4-oxadiazol)-5-yl, (1,3-thiazol)-2-yl, (1,3-thiazol)-4-yl, (1,3-thiazol)-5-yl, furan-2-yl, and furan-3-yl;
• and
• a substituted or unsubstituted saturated heterocyclic group selected from piperidin-3-yl, piperidin-4-yl, tetrahydrofuran-3-yl, tetrahydropyran-3-yl, and tetrahydropyran-4-yl;
• each R34 is independently selected from:
• H;
• a halogen;
• a nitrile group;
• a substituted or unsubstituted linear or branched C1-C6 alkyl group selected from Me, Et, Pr, i-Pr, n-Bu, i-Bu, t-Bu, pentyl and hexyl;
• a substituted or unsubstituted linear or branched C1-C6 alkyl-aryl group selected from —CH2Ph, —CH2(2,3 or 4)F-Ph, —CH2(2,3 or 4)Cl-Ph, —CH2(2,3 or 4)Br-Ph, —CH2(2,3 or 4)I-Ph, —CH2CH2Ph, —CH2CH2CH2Ph, —CH2CH2CH2CH2Ph, —CH2CH2CH2CH2CH2Ph, and —CH2CH2CH2CH2CH2CH2Ph;
• a substituted or unsubstituted linear or branched C1-C6 halogenated alkyl group selected from —CH2F, —CH2Cl, —CF3, —CCl3 —CBr3, —CI3, —CH2CF3, —CH2CCl3, —CH2CBr3, and —CH2CI3;
• an —NH2 group,
• a substituted or unsubstituted linear or branched primary, secondary or tertiary C1-C6 amine group selected from —NMeH, —NMe2, —NEtH, —NEtMe, —NEt2, —NPrH, —NPrMe, —NPrEt, —NPr2, —NBuH, —NBuMe, —NBuEt, —CH2—NH2, —CH2-NMeH, —CH2—NMe2, —CH2—NEtH, —CH2—NEtMe, —CH2—NEt2, —CH2—NPrH, —CH2—NPrMe, and —CH2—NPrEt;
• a substituted or unsubstituted amino-aryl group selected from —NH-Ph, —NH-(2,3 or 4)F-Ph, —NH-(2,3 or 4)Cl-Ph, —NH-(2,3 or 4)Br-Ph, —NH-(2,3 or 4)I-Ph, —NH-(2,3 or 4)Me-Ph, —NH-(2,3 or 4)Et-Ph, —NH-(2,3 or 4)Pr-Ph, —NH-(2,3 or 4)Bu-Ph, NH-(2,3 or 4)OMe-Ph, —NH-(2,3 or 4)OEt-Ph, —NH-(2,3 or 4)OPr-Ph, —NH-(2,3 or 4)OBu-Ph, —NH-2,(3,4,5 or 6)F2-Ph, —NH-2,(3,4,5 or 6)Cl2-Ph, —NH-2,(3,4,5 or 6)Br2-Ph, —NH-2,(3,4,5 or 6)I2-Ph, —NH-2,(3,4,5 or 6)Me2-Ph, —NH-2,(3,4,5 or 6)Et2-Ph, —NH-2,(3,4,5, or 6)Pr2-Ph, and —NH-2,(3,4,5 or 6)Bu2-Ph,
• a substituted or unsubstituted cyclic amine or amido group selected from pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, morpholin-2-yl, morpholin-3-yl, morpholin-4-yl, 2-keto-pyrrolidinyl, 3-keto-pyrrolidinyl, 2-keto-piperidinyl, 3-keto-piperidinyl, and 4-keto-piperidinyl;
• a substituted or unsubstituted cyclic C3-C8 alkyl group selected from cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl;
• —OH;
• a substituted or unsubstituted linear or branched C1-C6 alcohol group selected from —CH2OH, —CH2CH2OH, —CH2CH2CH2OH, —CH(CH3)CH2OH, —C(CH3)2OH, —CH2CH2CH2CH2OH, —CH(CH3)CH2CH2OH, —CH(CH3)CH(CH3)OH, —CH(CH2CH3)CH2OH, —C(CH3)2CH2OH, —CH2CH2CH2CH2CH2OH, and —CH2CH2CH2CH2CH2CH2OH;
• a substituted or unsubstituted linear or branched C1-C6 carboxylic acid group selected from —COOH, —CH2COOH, —CH2CH2COOH, —CH2CH2CH2COOH, —CH2CH2CH2CH2COOH, and —CH2CH2CH2CH2CH2COOH;
• a substituted or unsubstituted linear or branched carbonyl group selected from —(CO)Me, —(CO)Et, —(CO)Pr, —(CO)iPr, —(CO)nBu, —(CO)iBu, —(CO)tBu, —(C O)Ph, —(CO)CH2Ph, —(CO)CH2OH, —(CO)CH2OCH3, —(CO)CH2NH2, —(CO)CH2N HMe, —(CO)CH2NMe2, —(CO)-cyclopropyl, —(CO)-1,3-epoxypropan-2-yl;
• —(CO)N HMe, —(CO)NMe2, —(CO)NHEt, —(CO)NEt2, —(CO)-pyrollidine-N-yl, —(CO)-morph oline-N-yl, —(CO)-piperazine-N-yl, —(CO)-N-methyl-piperazine-N-yl, —(CO)NHC H2CH2OH, —(CO)NHCH2CH2OMe, —(CO)NHCH2CH2NH2, —(CO)NHCH2CH2NH Me, and —(CO)NHCH2CH2NMe2;
• a substituted or unsubstituted linear or branched C1-C6 carboxylic acid ester group selected from —COOMe, —COOEt, —COOPr, —COO-i-Pr, —COO-n-Bu, —COO-i-Bu, —COO-t-Bu, —CH2COOMe, —CH2CH2COOMe, —CH2CH2CH2COOMe, and —CH2CH2CH2CH2COOMe;
• a substituted or unsubstituted linear or branched C1-C6 amide group selected from —CO—NH2, —CO—NMeH, —CO—NMe2, —CO—NEtH, —CO—NEtMe, —CO—NEt2, —CO—NPrH, —CO—NPrMe, and —CO—NPrEt;
• a substituted or unsubstituted linear or branched C1-C7 amino carbonyl group selected from —NH—CO-Me, —NH—CO-Et, —NH—CO—Pr, —NH—CO-Bu, —NH—CO-pentyl, —NH—CO-hexyl, —NH—CO-Ph, —NMe-CO-Me, —NMe-CO-Et, —NMe-CO—Pr, —NMe-CO-Bu, —NMe-CO-pentyl, —NMe-CO-hexyl, and —NMe-CO-Ph;
• a substituted or unsubstituted linear or branched C1-C7 alkoxy or aryloxy group selected from —OMe, —OEt, —OPr, —O-i-Pr, —O-n-Bu, —O-i-Bu, —O-t-Bu, —O-pentyl, —O-hexyl, —OCH2F, —OCHF2, —OCF3, —O-Ph, —O—CH2-Ph, —O—CH2-(2,3 or 4)-F-Ph, —O—CH2-(2,3 or 4)-Cl-Ph, —CH2OMe, —CH2OEt, —CH2OPr, —CH2OBu, —CH2CH2OMe, —CH2CH2CH2OMe, —CH2CH2CH2CH2OMe, and —CH2CH2CH2CH2CH2OMe;
• a substituted or unsubstituted linear or branched aminoalkoxy group selected from —OCH2CH2NH2, —OCH2CH2NHMe, —OCH2CH2NMe2, —OCH2CH2NHEt, and —OCH2CH2NEt2;
• a substituted or unsubstituted sulphonyl group selected from —SO2Me, —SO2Et, —SO2Pr, —SO2iPr, —SO2Ph, —SO2-(2,3 or 4)-F-Ph, —SO2-cyclopropyl, —SO2CH2CH2OCH3, —SO2NH2, —SO2NHMe, —SO2NMe2, —SO2NHEt, —SO2NEt2, —SO2-pyrrolidine-N-yl, —SO2-morpholine-N-yl, —SO2NHCH2OMe, and —SO2NHCH2CH2OMe;
• a substituted or unsubstituted aminosulphonyl group selected from —NHSO2Me, —NHSO2Et, —NHSO2Pr, —NHSO2iPr, —NHSO2Ph, —NHSO2-(2,3 or 4)-F-Ph, —NHSO2-cyclopropyl, and —NHSO2CH2CH2OCH3;
• a substituted or unsubstituted aromatic group selected from Ph-, 2-F-Ph-, 3-F-Ph-, 4-F-Ph-, 2-Cl-Ph-, 3-Cl-Ph-, 4Cl-Ph-, 2-Br-Ph-, 3-Br-Ph-, 4-Br-Ph-, 2-I-Ph-, 3-I-Ph, 4-I-Ph-, 2,(3,4,5 or 6)-F2-Ph-, 2,(3,4,5 or 6)-Cl2-Ph-, 2,(3,4,5 or 6)-Br2-Ph-, 2,(3,4,5 or 6)-I2-Ph-, 2,(3,4,5 or 6)-Me2-Ph-, 2,(3,4,5 or 6)-Et2-Ph-, 2,(3,4,5 or 6) —Pr2-Ph-, 2,(3,4,5 or 6)-Bu2-Ph-, 2,(3,4,5 or 6)-(CN)2-Ph-, 2,(3,4,5 or 6)-(NO2)2-Ph-, 2,(3,4,5 or 6)-(NH2)2-Ph-, 2,(3,4,5 or 6)-(MeO)2-Ph-, 2,(3,4,5 or 6)-(CF3)2-Ph-, 3,(4 or 5)-F2-Ph-, 3,(4 or 5)-Cl2-Ph-, 3,(4 or 5)-Br2-Ph-, 3,(4 or 5)-I2-Ph-, 3,(4 or 5)-Me2-Ph-, 3,(4 or 5)-Et2-Ph-, 3,(4 or 5)-Pr2-Ph-, 3,(4 or 5)-Bu2-Ph-, 3,(4 or 5)-(CN)2-Ph-, 3,(4 or 5)-(NO2)2-Ph-, 3,(4 or 5)-(NH2)2-Ph-, 3,(4 or 5)-(MeO)2-Ph-, 3,(4 or 5)-(CF3)2-Ph-, 2-Me-Ph-, 3-Me-Ph-, 4-Me-Ph-, 2-Et-Ph-, 3-Et-Ph-, 4-Et-Ph-, 2-Pr-Ph-, 3-Pr-Ph-, 4-Pr-Ph-, 2-Bu-Ph-, 3-Bu-Ph-, 4-Bu-Ph-, 2-(CN)-Ph-, 3-(CN)-Ph-, 4-(CN)-Ph-, 2-(NO2)-Ph-, 3-(NO2)-Ph-, 4-(NO2)-Ph-, 2-(NH2)-Ph-, 3-(NH2)-Ph-, 4-(NH2)-Ph-, 2-MeO-Ph-, 3-MeO-Ph-, 4-MeO-Ph-, 2-(NH2—CO)-Ph-, 3-(NH2—CO)-Ph-, 4-(NH2—CO)-Ph-, 2-CF3-Ph-, 3-CF3-Ph-, 4-CF3-Ph-, 2-CF3O-Ph-, 3-CF3O-Ph-, and 4-CF3O-Ph-;
• and
• a substituted or unsubstituted saturated or unsaturated heterocyclic group selected from pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, thiophen-2-yl, thiophen-3-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrimidin-6-yl, tetrazole-1yl, tetrazole-2-yl, tetrazole-3-yl, tetrazole-4-yl, tetrazole-5-yl, (1,3,4-oxadiazol)-2-yl, (1,3,4-oxadiazol)-5-yl, (1,3-thiazol)-2-yl, (1,3-thiazol)-4-yl, (1,3-thiazol)-5-yl, furan-2-yl, furan-3-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydropyran-2-yl, tetrahydropyran-3-yl, and tetrahydropyran-4-yl;
• each R313 is independently selected from absent, H, —OH, halogen, and C1-6 alkyl;
• and L is absent.