Thiazolidinedione analogues
First Claim
Patent Images
1. A method of treating a metabolic inflammation mediated disease comprising administering to a patient a pharmaceutical composition including a compound of formula I:
- or a pharmaceutically acceptable salt thereof, wherein;
R1 is hydrogen or an optionally substituted aliphatic;
R2 is hydrogen, halo, hydroxy, oxo, or optionally substituted aliphatic;
R3 is hydrogen, halo, or optionally substituted aliphatic; and
Ring A is a phenyl or a monocyclic heteroaryl having 1-3 heteroatoms selected from N, O, or S, either of which is substituted with —
CH2—
R1 at any chemically feasible position on ring A.
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Abstract
The present invention relates to thiazolidinedione analogues that are useful for treating metabolic inflammation mediated diseases such as diabetes.
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Citations
26 Claims
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1. A method of treating a metabolic inflammation mediated disease comprising administering to a patient a pharmaceutical composition including a compound of formula I:
-
or a pharmaceutically acceptable salt thereof, wherein; R1 is hydrogen or an optionally substituted aliphatic; R2 is hydrogen, halo, hydroxy, oxo, or optionally substituted aliphatic; R3 is hydrogen, halo, or optionally substituted aliphatic; and Ring A is a phenyl or a monocyclic heteroaryl having 1-3 heteroatoms selected from N, O, or S, either of which is substituted with —
CH2—
R1 at any chemically feasible position on ring A.- View Dependent Claims (6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22)
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2. A method of treating a metabolic inflammation mediated disease comprising administering to a patient a pharmaceutical composition including a compound of formula III:
-
or a pharmaceutically acceptable salt thereof, wherein; R1 is hydrogen or an optionally substituted aliphatic; R2 is hydrogen, hydroxyl, or aliphatic optionally substituted with hydroxy; R3 is hydrogen, halo, or optionally substituted aliphatic; and Ring A is a monocyclic heteroaryl having 1-3 heteroatoms selected from N, O, or S that is substituted with —
CH2—
R1 at any chemically feasible position on ring A.
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3. A method of treating a metabolic inflammation mediated disease comprising administering to a patient a pharmaceutical composition including a compound of formula IV:
-
or a pharmaceutically acceptable salt thereof, wherein; R1 is hydrogen or an optionally substituted aliphatic; R2 is hydrogen, hydroxyl, or aliphatic optionally substituted with hydroxy; and R3 is hydrogen, halo, or optionally substituted aliphatic.
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4. A method of treating a metabolic inflammation mediated disease comprising administering to a patient a pharmaceutical composition including a compound of formula V:
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or a pharmaceutically acceptable salt thereof, wherein; R1 is hydrogen or an optionally substituted aliphatic; R2 is hydrogen, hydroxyl, or aliphatic optionally substituted with hydroxy; and R3 is hydrogen, halo, or optionally substituted aliphatic.
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5. A method of treating a metabolic inflammation mediated disease comprising administering to a patient a pharmaceutical composition including a compound of formula VI:
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or a pharmaceutically acceptable salt thereof, wherein; R1 is hydrogen or an optionally substituted aliphatic; R2 is hydrogen, hydroxyl, or aliphatic optionally substituted with hydroxy; and R3 is hydrogen, halo, or optionally substituted aliphatic.
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23. A method of treating a metabolic inflammation mediated disease comprising administering to a patient a pharmaceutical composition including a compound selected from
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24. A method of treating or reducing the severity of inflammatory disease comprising administering metformin and a compound of formula I
or a pharmaceutically acceptable salt thereof, wherein: -
R1 is hydrogen or an optionally substituted aliphatic; R2 is hydrogen, halo, hydroxy, oxo, or optionally substituted aliphatic; R3 is hydrogen, halo, or optionally substituted aliphatic; and Ring A is a phenyl or a monocyclic heteroaryl having 1-3 heteroatoms selected from N, O, or S, either of which is substituted with —
CH2—
R1 at any chemically feasible position on ring A.
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25. A method of treating or reducing the severity of a disease in a patient, wherein said disease is selected from dyslipidemia, central obesity, rheumatoid arthritis, lupus, myasthenia gravis, vasculitis, multiple schlerosis, Chronic Obstructive Pulmonary Disease (COPD), inflammatory bowel disease, nonalcoholic fatty liver disease (NAFLD), nonalcoholic steatohepatitis (NASH), acute allergic reactions, transplant rejection, Alzheimer'"'"'s disease, Parkinson'"'"'s disease, and multiple sclerosis, wherein said method comprises the step of contacting said patient with a compound of formula I:
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or a pharmaceutically acceptable salt thereof, wherein; R1 is hydrogen or an optionally substituted aliphatic; R2 is hydrogen, halo, hydroxy, oxo, or optionally substituted aliphatic; R3 is hydrogen, halo, or optionally substituted aliphatic; and Ring A is a phenyl or a monocyclic heteroaryl having 1-3 heteroatoms selected from N, O, or S, either of which is substituted with —
CH2—
R1 at any chemically feasible position on ring A.
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26. A pharmaceutical composition useful for treating metabolic mediated disease comprising metformin and a compound of formula I:
-
or a pharmaceutically acceptable salt thereof, wherein; R1 is hydrogen or an optionally substituted aliphatic; R2 is hydrogen, halo, hydroxy, oxo, or optionally substituted aliphatic; R3 is hydrogen, halo, or optionally substituted aliphatic; and Ring A is a phenyl or a monocyclic heteroaryl having 1-3 heteroatoms selected from N, O, or S, either of which is substituted with —
CH2—
R1 at any chemically feasible position on ring A.
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Specification