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US 2006/0148863 A1Published application
Substituted 1,2,4-oxadiazoles, compositions and methods of use
AssigneePTC Therapeutics, Inc.
InventorsGary Karp, Seongwoo Hwang, Guangming Chen, Neil Almstead, Young-Choon Moon
Life of this patent
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Abstract
Novel 1,2,4-oxadiazole benzoic acid compounds, methods of using and pharmaceutical compositions comprising an 1,2,4-oxadiazole benzoic acid derivative are disclosed. The methods include methods of treating or preventing a disease ameliorated by modulation of premature translation termination or nonsense-mediated mRNA decay, or ameliorating one or more symptoms associated therewith.
Claims19
A compound of the formula:
- or a pharmaceutically acceptable salt, solvate or stereoisomer thereof, wherein:
- Z is substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocycle;
- R1 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, —(CH2CH2O)nR6 or any biohydrolyzable group;
- R2, R3, R4, R5 and R6 are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl;
- substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, alkoxy, aryloxy, heteroaryloxy, halogen, CF3, OCF3, OCHF2, CN, COOH, COOR7, SO2R7, NO2, NH2, or N(R7)2;
- each occurrence of R7 is independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl;
- substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, alkoxy, aryloxy, heteroaryloxy, halogen or CF3;
- n is an integer from 1 to 7;
- with the proviso that when R1, R2, R3, R4, and R5 are each hydrogen, Z is not 3-(4-pyridinyl)propyl, or 2-(4-piperidinyl) ethyl.
6 more elements
A compound selected from the group consisting of:
- 3-[5-(2-Chloro-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-benzoic acid;
- 3-(5-Benzo[1,3]dioxol-5-yl-[1,2,4]oxadiazol-3-yl)-benzoic acid;
- 3-[5-(3-Methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-benzoic acid;
- 3-(5-Benzo[b]thiophen-2-yl-[1,2,4]oxadiazol-3-yl)-benzoic acid;
- 3-(5-Thiophen-2-yl-[1,2,4]oxadiazol-3-yl)-benzoic acid;
- 3-[5-(2,5-Dimethyl-furan-3-yl)-[1,2,4]oxadiazol-3-yl]-benzoic acid;
- 3-[5-(4-Pyrrol-1-yl-phenyl)-[1,2,4]oxadiazol-3-yl]-benzoic acid;
- 3-(5-Benzo[1,2,5]oxadiazol-5-yl-[1,2,4]oxadiazol-3-yl)-benzoic acid;
- 3-[5-(6-Chloro-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-benzoic acid;
- 3-(5-Furan-2-yl-[1,2,4]oxadiazol-3-yl)-benzoic acid;
- 3-(5-Pyridin-3-yl-[1,2,4]oxadiazol-3-yl)-benzoic acid;
- 3-(5-Pyridin-4-yl-[1,2,4]oxadiazol-3-yl)-benzoic acid;
- 3-[5-(1-Acetyl-piperidin-4-yl)-[1,2,4]oxadiazol-3-yl]-benzoic acid;
- 3-(5-Isoxazol-5-yl-[1,2,4]oxadiazol-3-yl)-benzoic acid;
- 3-{5-[3-(2-Chloro-6-fluoro-phenyl)-5-methyl-isoxazol-4-yl]-[1,2,4]oxadiazol-3-yl}-benzoic acid;
- 3-[5-(6-Chloro-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-benzoic acid;
- 3-[5-(2-Methylsulfanyl-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-benzoic acid;
- 3-[5-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-[1,2,4]oxadiazol-3-yl]-benzoic acid;
- 3-{5-[3-(2-Chloro-phenyl)-5-methyl-isoxazol-4-yl]-[1,2,4]oxadiazol-3-yl}-benzoic acid;
- 3-[5-(6-Pyrrolidin-1-yl-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-benzoic acid;
- 3-[5-(6-Morpholin-4-yl-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-benzoic acid;
- 3-[5-(3,4,5,6-Tetrahydro-2H-[1,2′]bipyridinyl-5′-yl)-[1,2,4]oxadiazol-3-yl]-benzoic acid;
- or a pharmaceutically acceptable salt, hydrate, solvate, or stereoisomer thereof.
20 more elements
Dependencies are inferred from the claim text.