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US 7,683,097 B2Granted
Topoisomerase inhibitors
AssigneePropharmacon, Inc.
InventorsMartin A. Murphy, John Robert Schullek, John S. Ward, Gary C. Look, Brian Siesel
Life of this patent
Estimating the term…
Abstract
The present invention provides compounds that are effective against inhibiting topoisomerase (i.e., topoisomerase I and/or topoisomerase II). These compounds are used for treating cell-proliferative disorders. In some instances, these compounds have anticancer activity, e.g., against multi-drug resistant cancers.
Claims5
A compound of formula
- or a pharmaceutically acceptable salt thereof,
- wherein R1 is a member selected from the group consisting of hydrogen, (C1-C8)alkyl, (C1-C8)heteroalkyl, (C3-C8)heterocycloalkyl(C1-C8)alkyl and aryl(C1-C8)alkyl;
- R2 is a member selected from the group consisting of
- Z is a bond;
- and
- R3 is a member selected from the group consisting of hydrogen, halogen, alkyl, alkoxy, hydroxy, halo(C1-C6)alkyl, heteroalkyl, —NO2, —CN, —CH2CN, —SR9, —O—S(O)R9, —S(O)2R9, and —S(O)R9, wherein R9 is a member selected from the group consisting of (C1-C4)alkyl, amino and alkylamino.
3 more elements
A compound of formula
- or a pharmaceutically acceptable salt thereof,
- wherein R1 is a member selected from the group consisting of hydrogen, (C1-C8)alkyl, (C1-C8)heteroalkyl, (C3-C8)heterocycloalkyl(C1-C8)alkyl and aryl(C1-C8)alkyl;
- R2 has the formula:
- wherein
- X7 is N, O, or S and when X7 is S or O, either R21 or R24 is absent;
- g is an integer from 1-6;
- R21, R22, R23 and R24 are each independently a member selected from the group consisting of hydrogen, halogen, halo(C1-C6)alkyl, (C1-C6)alkyl, (C3-C6)cycloalkyl, aryl, heteroaryl, aryl(C1-C6)alkyl and —C(O)2R25;
- wherein R25 is hydrogen;
- alternatively, when X7 is N then R21 and R24 taken together with X7 join to form a 4-to 7-membered ring containing 0-3 heteroatoms, wherein said 4-to 7-membered ring is optionally substituted with 1-3 substituents selected from the group consisting of (C1-C6)alkyl, (C1-C6)acyl, aryl, heteroaryl, hydroxy, alkoxy, amino and alkylamino;
- alternatively, R23 and R24 taken together with the atoms to which they are attached join to form a 4- to 7-membered ring containing 0-3 heteroatoms, wherein said 4- to 7-membered ring is optionally substituted with 1-3 substitutents selected from the group consisting of (C1-C6)alkyl, (C1-C6)heteroalkyl, hydroxy and C(O)2R26, wherein R26 is hydrogen or (C1-C4)alkyl;
- Z is a bond;
- and
- R3 is a member selected from the group consisting of hydrogen, halogen, alkyl, alkoxy, hydroxy, halo(C1-C6)alkyl, heteroalkyl, —NO2, —CN, —CH2CN, —SR9, —O—S(O)R9, —S(O)2R9, and —S(O)R9, wherein R9 is a member selected from the group consisting of (C1-C4)alkyl, amino and alkylamino.
10 more elements
A compound selected from group consisting of:
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (2-methoxy-pyrimidin-5-yl)-amide,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid pyrazin-2-ylamide,
- 6-Chloro-3″-carboxamido-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-methoxy-pyridin-3-yl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-methoxy-pyridin-3-yl)-amide,
- 6-Chloro-3″-hydroxy-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-methoxy-pyridin -3-yl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-chloro-pyridin-3-yl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-fluoro-pyridin-3-yl)-amide,
- 6-Chloro-[1,1′;4′, 1″]terphenyl-3-carboxylic acid (6-methyl-pyridin-3-yl)-amide,
- 6-Chloro-3″-hydroxymethyl-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-methoxy-pyridin-3-yl)-amide,
- 6-Chloro-4″-hydroxy-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-methoxy-pyridin-3-yl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid p-tolylamide,
- 6-Chloro-4″-hydroxymethyl-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-methoxy-pyridin-3-yl)-amide,
- 6-Chloro-3″-methanesulfonyl-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-methoxy-pyridin-3-yl)-amide,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid [1,2,4]triazin-3-ylamide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (2-pyrrolidin-1-yl-ethyl)-amide,
- 5-Fluoro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-methoxy-pyridin-3-yl)-amide,
- 6-Methyl-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-methoxy-pyridin-3-yl)-amide,
- 6″-Chloro-2′-fluoro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid pyridin-3-ylamide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (2-pyridin-3-yl-2-pyrrolidin-1-yl -ethyl)-amide,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid (4,5-dihydro-thiazol-2-yl)-amide,
- 6″-Chloro-4-dimethylaminomethyl-[1,1′;4′,1″]terphenyl-3″-carboxylic acid (6-methoxy-pyridin-3-yl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (2-diethylamino-ethyl)-amide,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid (6-piperazin-1-yl-pyridin-3-yl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid pyrimidin-4-ylamide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid 3-aminomethyl-benzylamide,
- 4-Methyl-piperazine-1-carboxylic acid 2-chloro-5-(6-methoxy-pyridin-3-ylcarbamoyl)-[1,1′;4′,1″]terphenyl-4″-yl ester,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (piperidin-4-ylmethyl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-hydroxymethyl-pyridin-3-yl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid piperidin-4-ylamide,
- 6-Chloro-[1,1 ′;4′,1″]terphenyl-3-carboxylic acid (6-methylsulfanyl-pyridin-3-yl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid [6-(4-methyl-piperazin-1-yl)-pyridin-3-yl]-amide,
- 6-Methyl-[1,1′;4′,1″]terphenyl-3-carboxylic acid (5-chloro-pyridin-2-yl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (5-phenyl-[1,3,4]oxadiazol-2-yl)-amide,
- 6-Chloro-3″-dimethylaminomethyl-[1,1′;4′,1″]terphenyl-3-carboxylic acid (4-methoxy-phenyl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (2-dimethylamino-ethyl)-pyridin-3-yl-amide,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid (6-methanesulfonyl-benzothiazol-2-yl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (tetrahydro-furan-2-ylmethyl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-yl)-(3-dimethylamino-pyrrolidin-1-y-1)-methanone,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid [3-(2-methyl-[1,3]dioxolan-2-yl)-phenyl]-amide,
- 4″-Benzyloxy-6-chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-methoxy-pyridin-3-yl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid pyridin-3-ylamide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (furan-2-ylmethyl)-amide,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid quinolin-6-ylamide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (3-fluoro-4-methoxy-phenyl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid [6-(2-dimethylamino-ethylsulfanyl)-pyridin-3-yl]-amide,
- 2-Chloro-5-(6-methoxy-pyridin-3-ylcarbamoyl)-[1,1′;4′,1″]terphenyl-3″-carboxylic acid,
- 4″-Aminomethyl-6-chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-methoxy-pyridin-3-yl)-amide,
- 6-Chloro-3″-formyl-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-methoxy-pyridin-3-yl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid methyl-(2-pyridin-2-yl-ethyl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (2-methylsulfanyl-pyrimidin-5-yl)-amide,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid (5-chloro-pyrimidin-2-yl)-amide,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid (4-ethoxy-phenyl)-amide,
- (3-Amino-pyrrolidin-1-yl)-(6-chloro-[1,1′;4′,1″]terphenyl-3-yl)-methanone,
- [1,1′;4′,1″]terphenyl-3″-carboxylic acid (2-pyrrolidin-1-yl-ethyl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid [3-(2-morpholin-4-yl-acetylamino)-phenyl]-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid [4-(2-morpholin-4-yl-acetylamino)-phenyl]-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid [1-(2-bromo-acetyl)-piperidin-4-ylmethyl]-amide,
- 6″-Chloro-[1,1′;4′,1 ″]terphenyl-3″-carboxylic acid (3-methyl-isoxazol-5-yl)-amide,
- 6-Chloro-[1,1′;4′,1 ″]terphenyl-3-carboxylic acid (5-bromo-pyridin-2-yl)-amide,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid (6-morpholin-4-yl-pyridin-3-yl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-dimethylaminomethyl-pyridin-3-yl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-trifluoromethyl-pyridin-3-yl)-amide,
- 6-Fluoro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-methoxy-pyridin-3-yl)-amide,
- 6″-Chloro-2′-fluoro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid (2-pyrrolidin-1-yl-ethyl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (2-dimethylamino-ethyl)-amide,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid (3-methoxy-phenyl)-amide,
- [1-(6-Chloro-[1,1′;4′,1″]terphenyl-3-carbonyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (5-methyl-isoxazol-3-yl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-ethenesulfinyl-pyridin-3-yl)-amide,
- 6-Chloro-2″-dimethylaminomethyl-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-methoxy-pyridin-3-yl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (1-carbamimidoyl-piperidin-4-yl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (2-cyano-ethyl)-amide,
- 6″-Chloro-2′-fluoro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid pyrazin-2-ylamide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (2-pyridin-3-yl-ethyl)-amide,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid (4-cyano-phenyl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid [2-(1H-imidazol-4-yl)-ethyl]-pyrrolidin-2-ylmethyl-amide,
- [1-(6-Chloro-[1,1′;4′,1″]terphenyl-3-carbonyl)-piperidin-4-ylmethyl]-carbamic acid tert-butyl ester,
- 6-Methoxy-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-methoxy-pyridin-3-yl)-amide,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid (6-dimethylamino-pyridin-3-yl)-amide,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid quinolin-8-ylamide,
- 6″-Chloro-2′-fluoro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid (piperidin-4-ylmethyl)-amide,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid (3-acetyl-phenyl)-amide,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid benzo[1,3]dioxol-5-ylamide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (3,4,5-trimethoxy-phenyl)-amide,
- 6-Chloro-4″-methanesulfonyl-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-methoxy-pyridin-3-yl)-amide,
- (6-Chloro-[1,1′;4′,1″]terphenyl3-yl)-[1,4]diazepan-1-yl-methanone,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid pyridin-4-ylamide,
- 6-Hydroxy-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-methoxy-pyridin-3-yl)-amide,
- (3-{[(6-Chloro-[1,1′;4′,1″]terphenyl-3-carbonyl)-amino]-methyl}-benzyl)-carbamic acid tert-butyl ester,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid [4-(acetyl-methyl-amino)-phenyl]-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (2-methanesulfonyl-pyrimidin-5-yl)-amide,
- 6-Chloro-3″,4″,5″-methanesulfonyl-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-methoxy-pyridin-3-yl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-methanesulfinyl-pyridin-3-yl)-amide,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid cyclopentylamide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid {2-[4-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-ethyl}-amide,
- (6-Chloro-[1,1′;4′,1″]terphenyl-3-yl)-(3-pyridin-4-yl-pyrrolidin-1-y-1)-methanone,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (pyridin-4-ylmethyl)-amide,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid (3-phenyl-[1,2,4]thiadiazol-5-yl)-amide,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid (5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-amide,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid (4-methanesulfonyl-phenyl)-amide,
- (6-Chloro-[1,1′;4′,1″]terphenyl-3-yl)-piperazin-1-yl-methanone,
- 4-(6-Chloro-[1,1′;4′,1″]terphenyl-3-carbonyl)-piperazine-1-carboxamidine,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (3-chloro-4-methoxy-phenyl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-methyl-1-oxy-pyridin-3-yl)-amide,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid (2,2,2-trifluoro-ethyl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid pyridin-2-ylamide,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid (4-acetyl-phenyl)-amide,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid (3-methylsulfanyl-phenyl)-amide,
- 4-[(6-Chloro-[1,1′;4′,1″]terphenyl-3-carbonyl)-amino]-benzoic acid methyl ester,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-methoxy-pyrimidin-4-yl)-amide,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid (5-ethyl-[1,3,4]thiadiazol-2-yl)-amide,
- [(6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carbonyl)-phenyl-amino]-acetic acid ethyl ester,
- 4-Methyl-piperazine-1-carboxylic acid 5-(6-methoxy-pyridin-3-ylcarbamoyl)-[1,1′;4′,1″]terphenyl-2-yl ester,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (2-pyridin-3-yl-ethyl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-methoxy-1-oxy-pyridin-3-yl)-amide,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid benzo[1,2,5]thiadiazol-4-ylamide,
- (4-Aminomethyl-piperidin-1-yl)-(6-chloro-[1,1′;4′,1″]terphenyl-3-yl)-methanone,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-methanesulfonyl-pyridin-3-yl)-amide,
- Methanesulfonic acid 5-(6-methoxy-pyridin-3-ylcarbamoyl)-[1,1′;4′,1″]terphenyl-2-yl ester,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid (4-cyanomethyl-phenyl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-ethenesulfonyl-pyridin-3-yl)-amide,
- 1-(6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carbonyl)-piperidine-4-carboxylic acid ethyl ester,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (4-chloro-phenyl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (3,4-dichloro-phenyl)-amide,
- {(2-[(6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carbonyl)-amino]-thiazol-4-yl}-methoxyimino-acetic acid ethyl ester,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid (2-chloro-5-cyano-phenyl)-amide,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid (3-ethoxy-phenyl)-amide,
- 4-(6-Chloro-[1,1′;4′,1″]terphenyl-3-carbonyl)-[1,4]diazepane-1-carboxamidine,
- {2-[(6-Chloro-[1,1′;4′,1″]terphenyl-3-carbonyl)-amino]-ethyl }-trimethyl-ammonium,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid isoquinolin-5-ylamide,
- (6-Chloro-[1,1′;4′,1″]terphenyl-3-yl)-(2-pyridin-4-yl-pyrrolidin-1-yl)-methanone,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (pyridin-3-ylmethyl)-amide,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid (3,4-dimethyl-isoxazol-5-yl)-amide,
- 3-[(6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carbonyl)-amino]-pyrazine-2-carboxylic acid methyl ester,
- 6″-Chloro-[1,1′;4′,1 ″]terphenyl-3″-carboxylic acid (3,5-dimethoxy-phenyl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (4-chloro-phenyl)-methyl-amide,
- 4-[(6-Chloro-[1,1′;4′,1″]terphenyl-3-carbonyl)-amino]-piperidine-1-carboxylic acid tertbutyl ester,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (1 H-imidazol-4-ylmethyl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (5-methylsulfanyl-[1,3,4]thiadiazol-2-yl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (pyridin-2-ylmethyl)-amide,
- 2-(6-Chloro-[1,1′;4′,1″]terphenyl-3-carbonyl)-1,2,3,4-tetrahydro-iso-quinoline-3-carboxylic acid [2-(1H-imidazol-4-yl)-ethyl]-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid {5-amino-2-[2-(1H-imidazol-4-yl)-ethylcarbamoyl]-indan-2-yl }-amide,
- 2-(6-Chloro-[1,1′;4′,1″]terphenyl-3-carbonyl)-1,2,3,4-tetrahydro-iso-quinoline-3-carboxylic acid {2-cyclohexyl-1-[2-(1H-imidazol-4-yl)-ethylcarbamoyl]-ethyl }-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid [1,3,4]thiadiazol-2-ylamide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (2-pyridin-4-yl-ethyl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid {1-[2-(1H-imidazol-4-yl)-ethylcarbamoyl]-3-phenyl-propyl}-amide,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid (2-chloro-pyridin-3-yl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-chloro-pyridazin-3-yl)-amide,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid (4-methoxy-phenyl)-methyl-amide,
- 3-[(6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carbonyl)-amino]-benzoic acid ethyl ester,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (5-methyl-[1,3,4]thiadiazol-2-yl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (1-aza-bicyclo[2.2.2]oct-3-yl)-amide,
- (6-Chloro-[1,1′;4′,1″]terphenyl-3-yl)-(5-nitro-2,3-dihydro-indol-1-y-l)-methanone,
- 2-[(5″-Chloro-2′-fluoro-[1,1′;4′,1″]terphenyl-2″-carbonyl)-amino]-3-cyclohexyl-propionic acid,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid [2-(2,5-dioxo-pyrrolidin-1-yl)-phenyl]-amide,
- (6″-Chloro-[1,1′;4′,1″]terphenyl-3″-yl)-(4-phenyl-piperazin-1-yl)-methanone,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid benzo[1,3]dioxol-5-yl-ethyl-amide,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid [4-(4-nitro-benzenesulfonyl)-phenyl]-amide,
- 4-[(6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carbonyl)-amino]-benzoic acid ethyl ester,
- {4-[(6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carbonyl)-amino]-phenyl }-acetic acid ethyl ester,
- 2-{2-[(6-Chloro-[1,1′;4′,1″]terphenyl-3-carbonyl)-amino]-4-phenyl-butyrylamino}-4-phenyl-butyric acid,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (3-amino-propyl)-amide,
- 2-[(5″-Chloro-2′-fluoro-[1,1′;4′,1″]terphenyl-2″-carbonyl)-amino]-4-phenyl-butyric acid,
- 3-(6-Chloro-[1,1′;4′,1″]terphenyl-3-carbonyl)-thiazolidine-4-carboxylic acid,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid (5-cyclopropyl-[1,3,4]thiadiazol-2-yl)-amide,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid (4-cyano-naphthalen-1-yl)-amide,
- 2-{2-[(6-Chloro-[1,1′;4′,1″]terphenyl-3-carbonyl)-amino]-4-phenyl-butyrylamino }-3-cyclohexyl-propionic acid,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid [2-(1H-imidazol-4-yl)-ethyl]-piperidin-4-ylmethyl-amide,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid (2-benzenesulfonyl-phenyl)-amide,
- 2-{[2-(6-Chloro-[1,1′;4,′,1″]terphenyl-3-carbonyl)-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl]-amino}-3-(1H-imidazol-4-yl)-propionic acid,
- 3-(6-Chloro-[1,1′;4′,1″]terphenyl-3-carbonyl)-thiazolidine-4-carboxylic acid,
- 2-{[2-(6-Chloro-[1,1′;4′,1″]terphenyl-3-carbonyl)-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl]-amino}-3-(1H-imidazol4-yl)-propionic acid,
- 6-Fluoro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-methoxy-pyridin-3-yl)-amide,
- (6″-Chloro-[1,1′;4′,1″]terphenyl-3″-yl)-(6-nitro-2,3-dihydro-indol-1-yl)-methanone,
- 8-(6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carbonyl)-4-methyl-5,6,7,8-tetrahydro-1-oxa-8-aza-anthracen-2-one,
- 1-(6-Chloro-[1,1′;4′,1″]terphenyl-3-carbonyl)-octahydro-indole-2-carboxylic acid,
- 4-[(6-Chloro-[1,1′;4′,1″]terphenyl-3-carbonyl)-amino]-tetrahydro-pyran4-carboxylic acid,
- 1-[(6-Chloro-[1,1′;4′,1″]terphenyl-3-carbonyl)-amino]-4-hydroxy-cyclohexanecarboxylic acid,
- 4-[(6-Chloro-[1,1′;4′,1″]terphenyl-3-carbonyl)-amino]-piperidine-4-carboxylic acid,
- 1-[(6-Chloro-[1,1′;4′,1″]terphenyl-3-carbonyl)-amino]-3-hydroxy-cyclopentanecarboxylic acid,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-hydroxymethyl-pyridin-3-yl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid N′-pyridin-2-yl-hydrazide,
- N′-(6-Chloro-[1,1′;4′,1 ″]terphenyl-3-carbonyl)-hydrazinecarboxylic acid 9H-fluoren-9-ylmethyl ester,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid hydrazide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid [1,2,4]triazol-1-ylamide,
- 2-{2-[(6-Chloro-[1,1′;4′,1″]terphenyl-3-carbonyl)-amino]-4-phenyl-butyrylamino}-3-cyclohexyl-propionic acid,
- 6′-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid (4-methoxy-phenyl)-amide,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (1-{2-cyclohexyl-1-[2-(1H-imidazol-4-yl)-ethylcarbamoyl]-ethylcarbamoyl }-3-phenyl-propyl)-amide,
- 2-{2-[(6-Chloro-[1,1′;4′,1″]terphenyl-3-carbonyl)-amino]-4-phenyl-butyrylamino }-3-(1H-imidazol-4-yl)-propionic acid,
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid [6-(4-methyl-piperazin-1-ylmethyl)-pyridin-3-yl]-amide,
- {2-[(6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carbonyl)-amino]-thiazol-4-yl}-acetic acid ethyl ester,
- 6″-Chloro-[1,1′;4′,1 ″]terphenyl-3″-carboxylic acid cyclopropylmethyl-amide,
- 6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carboxylic acid cyclopropylamide,
- 2-[(6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carbonyl)-amino]-indan-2-carboxylic acid,
- 2-[(6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carbonyl)-methyl-amino]-propionic acid,
- 1-[(6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carbonyl)-amino]-cyclopropanecarboxylic acid,
- 3-[(6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carbonyl)-amino]-propionic acid,
- {3-[(6-Chloro-[1,1 ′;4′,1″]terphenyl-3-carbonyl)-amino]-propyl}-carbamic acid tert-butyl ester,
- 4-{[(6-Chloro-[1,1′;4′,1″]terphenyl-3-carbonyl)-amino]-methyl}-piperidine-1-carboxylic acid tert-butyl ester,
- 2-(6″-Chloro-[1,1′;4′,1″]terphenyl-3″-carbonyl)-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid, and
- 6-Chloro-[1,1′;4′,1″]terphenyl-3-carboxylic acid (6-fluoro-pyridin-3-yl)-amide.
198 more elements
Dependencies are inferred from the claim text.