发明名称 Anti-infective compounds
摘要 The present invention relates to small molecule compounds and their use in the treatment of bacterial infections, in particular Tuberculosis.
申请公布号 US8865734(B2) 申请公布日期 2014.10.21
申请号 US201113634165 申请日期 2011.03.18
申请人 Institut Pasteur Korea;Institut National de la Sante et de la Rech 发明人 No Zaesung;Kim Jaeseung;Brodin Priscille;Seo Min Jung;Kim Young Mi;Cechetto Jonathan;Jeon Heekyoung;Genovesio Auguste;Lee Saeyeon;Kang Sunhee;Ewann Fanny Anne;Nam Ji Youn;Christophe Thierry;Fenistein Denis Philippe Cedric;Heo Jamung;Jiyeon Jang
分类号 C07D401/04;A61K31/437 主分类号 C07D401/04
代理机构 Saliwanchik, Lloyd & Eisenschenk 代理人 Saliwanchik, Lloyd & Eisenschenk
主权项 1. A compound having the general formula Ia:wherein m is 0, 1, 2, 3 or 4; n is 0, 1, 2, or 3; X, Y and Z are CH; R1 is, at each occurrence, independently selected from the group consisting of hydrogen, halogen, C1-C10 alkyl, C1-C3 haloalkyl, C3-C7 cycloalkyl, hydroxyl, oxo, —OR4, —C(O)OR4, —C(O)R4, —C(O)N(R4)2, —CN, —NO2, —NH2, —N(R4)2, —OR4HetA, —OR4N(R4)2, —C(O)N(R4)R4HetA, —C(O)N(R4)HetA, —C(O)HetA, —C(O)N(R4)R4S(O)2R4; —S(O)2N(R4)2, —S(O)2R4, —N(R4)C(O)R4SR4, —N(R4)R4S(O)2R4, —N(R4)S(O)2R4, —C(S)R4, aryl, benzyl, and heterocyclyl, any of which is optionally substituted; R2 is, at each occurrence, independently selected from the group consisting of hydrogen, halogen, C1-C10 alkyl, C3-C10 cycloalkyl, C2-C10 alkenyl, C3-C10 cycloalkenyl, C2-C10 alkynyl, C1-C10 haloalkyl, —OH, —OR5, C1-C10 alkoxy, C3-C10 cycloalkoxy, C3-C15 cycloalkylalkoxy, C3-C15 cycloalkylalkyl, —CN, —NO2, —NH2, —N(R5)2, —C(O)R5, —C(O)OR5, —C(O)N(R5)2, —SR5, —S(O)R5, —S(O)2R5, —S(O)2N(R5)2, aryl, benzyl, heteroaryl, and heterocyclyl, any of which is optionally substituted; R3 is, at each occurrence, independently selected from the group consisting of hydrogen, halogen, C1-C10 alkyl, C3-C10 cycloalkyl, hydroxyl, —OR6, —CN, —NO2, —NH2, —N(R6)C(O)R6, —C(O)R6, —C(O)OR6, —C(O)N(R6)2, —S(O)R6, —S(O)2R6, —S(O)2N(R6)2, aryl, benzyl, heteroaryl, heterocyclyl, any of which is optionally substituted, or two groups of R3 are connected to each other to make a five or six membered cyclic or heterocyclic ring, any of which is optionally substituted; R4 is, at each occurrence, independently selected from the group consisting of hydrogen, C1-C10 alkyl, C3-C10 cycloalkyl, C2-C10 alkenyl, C3-C10 cycloalkenyl, C2-C10 alkynyl, C1-C10 haloalkyl, —C(O)R7, —R7(R7)C(O)R7, —C(O)OR7, —R7(R7)C(O)OR7, —C(O)N(R7)2, —R7(R7)C(O)N(R7)2, —S(O)R7, —S(O)2R7, —S(O)2N(R7)2, aryl, benzyl, heteroaryl, and heterocyclyl, any of which is optionally substituted; and R5, R6 and R7 are, at each occurrence, independently selected from the group consisting of hydrogen, C1-C10 alkyl, C3-C10 cycloalkyl, C2-C10 alkenyl, C3-C10 cycloalkenyl, C2-C10 alkynyl, C1-C10 haloalkyl, aryl, benzyl, heteroaryl, and heterocyclyl, any of which is optionally substituted; and pharmaceutically acceptable salts thereof, and wherein the compound has a formula selected from the following formulae 5, 8, 13, 14, 17, 18, 20, 21, 23-43, 46, 48, 50, 51, 53, 59, 68, 69, 74, 79, 80, 89-91, 142, 143, 161, 196, 211-213, 219, 221, 222, 239-247, 264, 313-329 and 331: 2-Methyl-N-(pyridin-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (5) N-Benzyl-2-methylimidazo[1,2-a]pyridine-3-carboxamide (8) 2-Methyl-N-(pyridin-3-ylmethyl)imidazo[1,2-a]pyridine-3-carboxamide (13) 2-Methyl-N-(pyridin-4-ylmethyl)imidazo[1,2-a]pyridine-3-carboxamide (14) N-((1H-Indo)-5-yl)methyl)-2-methylimidazo[1,2-a]pyridine-3-carboxamide (17) N—(Cyclohexylmethyl)-2-methylimidazo[1,2-a]pyridine-3-carboxamide (18) 2-Methyl-N-(piperidin-4-ylmethyl)imidazo[1,2-a]pyridine-3-carboxamide (20) 2-Methyl-N-phenethylimidazo[1,2-a]pyridine-3-carboxamide (21) 2-Methyl-N-(2-phenoxyethyl)imidazo[1,2-a]pyridine-3-carboxamide (23) N-(2-(Benzyloxy)ethyl)-2-methylimidazo[1,2-a]pyridine-3-carboxamide (24) (S)-Methyl 2-(2-methylimidazo[1,2-a]pyridine-3-carboxamido)-3-phenylpropanoate (25) N-(2-Methylimidazo[1,2-a]pyridin-3-yl)-2-phenylacetamide (26) N-Benzyl-8-chloro-2-methylimidazo[1,2-a]pyridine-3-carboxamide (27) N-Benzyl-7-chloro-2-methylimidazo[1,2-a]pyridine-3-carboxamide (28) N-Benzyl-6-chloro-2-methylimidazo[1,2-a]pyridine-3-carboxamide (29) N-Benzyl-2,8-dimethylimidazo[1,2-a]pyridine-3-carboxamide (30) N-Benzyl-2,7-dimethylimidazo[1,2-a]pyridine-3-carboxamide (31) N-Benzyl-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxamide (32) N-Benzyl-2,5-dimethylimidazo[1,2-a]pyridine-3-carboxamide (33) N-Benzyl-6-fluoro-2-methylimidazo[1,2-a]pyridine-3-carboxamide (34) N-Benzyl-7-cyano-2-methylimidazo[1,2-a]pyridine-3-carboxamide (35) N-Benzyl-6-cyano-2-methylimidazo[1,2-a]pyridine-3-carboxamide (36) N-Benzyl-2-methyl-7-phenylimidazo[1,2-a]pyridine-3-carboxamide (37) N-Benzyl-2-methyl-6-phenylimidazo[1,2-a]pyridine-3-carboxamide (38) N-Benzyl-8-fluoro-2-methylimidazo[1,2-a]pyridine-3-carboxamide (39) N-Benzyl-2-methyl-8-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxamide (40) N-Benzyl-8-methoxy-2-methylimidazo[1,2-a]pyridine-3-carboxamide (41) N-Benzyl-8-cyano-2-methylimidazo[1,2-a]pyridine-3-carboxamide (42) N-Benzyl-8-hydroxy-2-methylimidazo[1,2-a]pyridine-3-carboxamide (43) N-Benzyl-2-ethylimidazo[1,2-a]pyridine-3-carboxamide (46) N-Benzyl-2-propylimidazo[1,2-a]pyridine-3-carboxamide (48) N-Benzyl-2-cyclopropylimidazo[1,2-a]pyridine-3-carboxamide (50) N-Benzyl-2-isopropylimidazo[1,2-a]pyridine-3-carboxamide (51) N-Benzyl-2-phenylimidazo[1,2-a]pyridine-3-carboxamide (53) 2-Ethyl-N-(4-(trifluoromethoxy)benzyl)imidazo[1,2-a]pyridine-3-carboxamide (59) 2-Ethyl-7-methyl-N-(4-morpholinobenzyl)imidazo[1,2-a]pyridine-3-carboxamide (68) 2-Ethyl-7-methyl-N-(naphthalen-2-ylmethyl)imidazo[1,2-a]pyridine-3-carboxamide (69) 6-Chloro-2-methyl-N-(4-morpholinobenzyl)imidazo[1,2-a]pyridine-3-carboxamide (74) 6-Chloro-2-ethyl-N-(4-(piperidin-1-yl)benzyl)imidazo[1,2-a]pyridine-3-carboxamide (79) 6-Chloro-2-ethyl-N-(naphthalen-2-ylmethyl)imidazo[1,2-a]pyridine-3-carboxamide (80) 7-Chloro-2-ethyl-N-(4-morpholinobenzyl)imidazo[1,2-a]pyridine-3-carboxamide (89) 7-Chloro-2-ethyl-N-(4-(piperidin-1-yl)benzyl)imidazo[1,2-a]pyridine-3-carboxamide (90) 7-Chloro-2-ethyl-N-(naphthalen-2-ylmethyl)imidazo[1,2-a]pyridine-3-carboxamide (91) N-(7-Chloro-2-ethylimidazo[1,2-a]pyridin-3-yl)biphenyl-4-carboxamide (142) 2-(Biphenyl-4-yl)-N-(7-chloro-2-ethylimidazo[1,2-a]pyridin-3-yl)acetamide (143) [1,1′-Biphenyl]-4-ylmethyl 6-chloro-2-ethylimidazo[1,2-a]pyridine-3-carboxylate (161) 4-Phenoxybenzyl 6-chloro-2-ethylimidazo[1,2-a]pyridine-3-carboxylate (196) 6-Chloro-2-ethyl-N-(4-(pyrrolidin-1-yl)benzyl)imidazo[1,2-a]pyridine-3-carboxamide (211) 7-Chloro-2-ethyl-N-(4-(pyrrolidin-1-yl)benzyl)imidazo[1,2-a]pyridine-3-carboxamide (212) 7-Chloro-N-(4-(5,6-dihydropyridin-1(2H)-yl)benzyl)-2-ethylimidazo[1,2-a]pyridine-3-carboxamide (213) 2-ethyl-6-methyl-N-(4-morpholinobenzyl)imidazo[1,2-a]pyridine-3-carboxamide (219) N-(4-(Azepan-1-yl)benzyl)-6-chloro-2-ethylimidazo[1,2-a]pyridine-3-carboxamide (221) N-(4-(Azepan-1-yl)benzyl)-7-chloro-2-ethylimidazo[1,2-a]pyridine-3-carboxamide (222) 6-Chloro-2-ethyl-3-((4-(trifluoromethoxy)phenoxy)methyl)imidazo[1,2-a]pyridine (239) N-((6-Chloro-2-ethylimidazo[1,2-a]pyridin-3-yl)methyl)-4-(trifluoromethoxy)aniline (240) N-((6-Chloro-2-ethylimidazo[1,2-a]pyridin-3-yl)methyl)-4-(4-(4-fluorophenyl)piperazin-1-yl)aniline (241) N-((6-Chloro-2-ethylimidazo[1,2-a]pyridin-3-yl)methyl)-4-(4-fluorophenoxy)aniline (242) 5-(6-Chloro-2-ethylimidazo[1,2-a]pyridin-3-yl)-3-(4-(trifluoromethoxy)benzyl)-1,2,4-oxadiazole (243) 2-(7-Chloro-2-ethylimidazo[1,2-a]pyridin-3-yl)-5-((4-(4-(trifluoromethoxy)phenyl)piperazin-1-yl)methyl)-1,3,4-oxadiazole (244) 5-(6-Chloro-2-ethylimidazo[1,2-a]pyridin-3-yl)-3-(4-(4-fluorophenoxy)benzyl)-1,2,4-oxadiazole (245) 6-Chloro-N,2-diethylimidazo[1,2-a]pyridine-3-carboxamide (246) 6-Chloro-2-ethyl-N-isobutylimidazo[1,2-a]pyridine-3-carboxamide (247) 7-Chloro-2-ethyl-N-(4-(4-fluorophenoxy)benzyl)imidazo[1,2-a]pyridine-3-carboxamide (264) 2-Ethyl-6-fluoro-N-(4-morpholinobenzyl)imidazo[1,2-a]pyridine-3-carboxamide (313) 2-Ethyl-7-methoxy-N-(4-morpholinobenzyl)imidazo[1,2-a]pyridine-3-carboxamide (314) 6-Bromo-2-ethyl-N-(4-morpholinobenzyl)imidazo[1,2-a]pyridine-3-carboxamide (315) 2-Ethyl-6-fluoro-N-(4-morpholinobenzyl)imidazo[1,2-a]pyridine-3-carboxamide (316) 2-Ethyl-8-fluoro-N-(4-morpholinobenzyl)imidazo[1,2-a]pyridine-3-carboxamide (317) 2-Ethyl-8-methoxy-N-(4-morpholinobenzyl)imidazo[1,2-a]pyridine-3-carboxamide (318) 8-(Difluoromethoxy)-2-ethyl-N-(4-morpholinobenzyl)imidazo[1,2-a]pyridine-3-carboxamide (319) 8-Bromo-2-ethyl-N-(4-morpholinobenzyl)imidazo[1,2-a]pyridine-3-carboxamide (320) 2-Ethyl-N-(4-morpholinobenzyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxamide (321) 2-Ethyl-N-(4-morpholinobenzyl)-7-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxamide (322) 2-Ethyl-N-(4-morpholinobenzyl)-8-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxamide (323) 7-Bromo-2-ethyl-N-(4-morpholinobenzyl)imidazo[1,2-a]pyridine-3-carboxamide (324) 2-Ethyl-N-(4-morpholinobenzyl)-7-(pyridin-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (325) 2-Ethyl-N-(4-morpholinobenzyl)-7-(pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide (326) 2-Ethyl-N-(4-morpholinobenzyl)-8-(pyridin-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (327) 2-Ethyl-7-(4-methylpiperazin-1-yl)-N-(4-morpholinobenzyl)imidazo[1,2-a]pyridine-3-carboxamide (328) 2-Ethyl-7-(4-(4-fluorophenyl)piperazin-1-yl)-N-(4-morpholinobenzyl)imidazo[1,2-a]pyridine-3-carboxamide (329) 2-Ethyl-7-(4-(4-fluorobenzyl)piperazin-1-yl)-N-(4-morpholinobenzyl)imidazo[1,2-a]pyridine-3-carboxamide (331)
地址 Gyeonggi-Do KR