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US 7,598,292 B2Granted
4-((phenoxyalkyl)thio)-phenoxyacetic acids and analogs
AssigneeJanssen Pharmaceutica NV
InventorsGee-Hong Kuo, Rui Zhang, Aihua Wang, Alan R. DeAngelis
Life of this patent
Estimating the term…
Abstract
The invention features 4-((phenoxyalkyl)thio)-phenoxyacetic acids and analogs, compositions containing them, and methods of using them as PPAR delta modulators to treat or inhibit the progression of, for example, dyslipidemia.
Claims39
A compound of Formula (I):
- wherein
- X is selected from a covalent bond, S, and O;
- Y is S or O;
- Z is O or CH2, provided when Y is O, then Z is O;
- R1 and R2 are independently selected from H, C1-3 alkyl, C1-3 alkoxy, halo, and NRaRb wherein Ra and Rb are independently H or C1-3 alkyl;
- R3 and R4 are independently selected from H, halo, cyano, C1-5alkyl, hydroxy, C2-4 acyl, C1-4 alkoxy, and NRcRd wherein Rc and Rd are independently H or C1-3 alkyl, provided that R3 and R4 are not both H;
- R5 and R6 are independently selected from halo, phenyl, C1-9 alkyl, C1-8 alkoxy, C2-9 alkenyl, C2-9 alkenyloxy, C3-7 cycloalkyl, C3-7 cycloalkoxy, C3-7cycloalkyl-C1-7alkyl, C3-7cycloalkyl-C1-7alkoxy, C3-7cycloalkyloxy-C1-6-alkyl, and C3-7cycloalkyloxy-C1-7alkoxy, or
- R5 and R6 together form C1-9 alkylidenyl or C3-9 alkenylidenyl;
- or R5,
- R6 and the carbon atom to which they are attached together form C3-7 cycloalkyl;
- n is 0, 1 or 2;
- and
- m is 0, 1 or 2;
- or a pharmaceutically acceptable salt thereof.
11 more elements
A compound which is selected from:
- {2-Methyl-4-[2-(4-trifluoromethyl-phenoxymethyl )-allylsulfanyl]-phenoxy}-acetic acid;
- (2-Methyl-4-{2-[2-(4-trifluoromethyl-phenyl)-ethyl]-allylsulfanyl}-phenoxy)-acetic acid;
- {2-Methyl-4-[2-(4-trifluoromethoxy-phenoxymethyl)-allylsulfanyl]-phenoxy}-acetic acid;
- {2-Chloro-4-[2-(4-trifluoromethyl-phenoxymethyl )-allylsulfanyl]-phenoxy}-acetic acid;
- {2-Methyl-4-[3-methyl-2-(4-trifluoromethyl-phenoxymethyl)-but-2-enylsulfanyl]-phenoxy}-acetic acid;
- {4-[3,3-Difluoro-2-(4-trifluoromethyl-phenoxymethyl )-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;
- {3-Chloro-4-[2-(4-trifluoromethyl-phenoxymethyl)-allylsulfanyl]-phenyl}-acetic acid;
- {2-Methyl-4-[1-(4-trifluoromethyl-phenoxymethyl)-cyclopropylmethylsulfanyl]-phenoxy}-acetic acid;
- {2-Methyl-4-[2-propyl-2-(4-trifluoromethyl-phenoxymethyl)-pentylsulfanyl]-phenoxy}-acetic acid;
- {4-[2-(4-Chloro-phenoxymethyl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;
- {4-[2-(3,4-Dichloro-phenoxymethyl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;
- {4-[3-Cyano-2-(4-trifluoromethyl-phenoxymethyl )-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;
- {2-Methyl-4-[3-phenyl-2-(4-trifluoromethyl-phenoxymethyl)-allylsulfanyl]-phenoxy}-acetic acid;
- {2-Methyl-4-[3-naphthalen-1-yl-2-(4-trifluoromethyl-phenoxymethyl)-allylsulfanyl]-phenoxy}-acetic acid;
- {4-[2,2-Difluoro-3-(4-trifluoromethyl-phenoxy)-propylsulfanyl]-2-methyl-phenoxy}-acetic acid;
- {4-[2-(4-Chloro-3-trifluoromethyl-phenoxymethyl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;
- {4-[2-(4-Methoxy-phenoxymethyl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;
- {4-[2-(4-Dimethylamino-phenoxymethyl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;
- {2-Trifluoromethyl-4-[2-(4-trifluoromethyl-phenoxymethyl )-allylsulfanyl]-phenoxy}-acetic acid;
- {3-Chloro-4-[2-(4-trifluoromethyl-phenoxymethyl)-allylsulfanyl]-phenoxy}-acetic acid;
- {2-Methoxy-4-[2-(4-trifluoromethyl-phenoxymethyl)-allylsulfanyl]-phenoxy}-acetic acid;
- {2-Methyl-4-[3-(4-trifluoromethyl-phenoxy)-but-3-enylsulfanyl]-phenoxy}-acetic acid;
- {2-Methyl-4-[2-(4-trifluoromethyl-phenoxy)-allylsulfanyl]-phenoxy}-acetic acid;
- {4-[2-(4-tert-Butyl-phenoxymethyl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;
- {4-[2-(4-Isopropyl-phenoxymethyl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;
- {2-Chloro-4-[2-(3,4-dichloro-phenoxymethyl)-allylsulfanyl]-phenoxy}-acetic acid;
- {2-Chloro-4-[2-(4-trifluoromethoxy-phenoxymethyl)-allylsulfanyl]-phenoxy}-acetic acid;
- {4-[2,2-Dimethyl-3-(4-trifluoromethyl-phenoxy)-propylsulfanyl]-2-methyl-phenoxy}-acetic acid;
- {2-Chloro-4-[2,2-dimethyl-3-(4-trifluoromethyl-phenoxy)-propylsulfanyl]-phenoxy}-acetic acid;
- and
- {2-Chloro-4-[1-(4-trifluoromethyl-phenoxymethyl)-cyclopropylmethylsulfanyl]-phenoxy}-acetic acid;
- {3-Chloro-4-[2,2-dimethyl-3-(4-trifluoromethyl-phenoxy)-propylsulfanyl]-phenyl}-acetic acid;
- {3-Chloro-4-[2,2-dimethyl-3-(4-trifluoromethoxy-phenoxy)-propylsulfanyl]-phenyl}-acetic acid;
- and
- {3-Chloro-4-[3-methyl-2-(4-trifluoromethyl-phenoxymethyl)-but-2-enylsulfanyl]-phenyl}-acetic acid
- or a pharmaceutically acceptable salt thereof.
33 more elements
A compound which is {2-methyl-4-[2-(4-trifluoromethyl-phenoxymethyl)-allylsulfanyl]-phenoxy}-acetic acid or a pharmaceutically acceptable salt thereof.
Dependencies are inferred from the claim text.