MITOGLITAZONE

MITOGLITAZONE

MSDC-0160; CAY 10415; 146062-49-9

5-(4-(2-(5-cthylpyridin-2-yl)- 2-oxoethoxy)benzyl)-1,3 -thiazolidiiie-2,4-dione of Formula (I)

BACKGROUND

Thiazolidinedione analogs either prevent or ameliorate an insulin resistance state, which occurs genetically or is induced by dietary means. 5-(4-(2-(5-Ethylpyridin-2-yl)-2- oxoethoxy)benzyl)-l,3-thiazolidine-2,4-dione of Formula (I) (Mitoglitazonc) is an antidiabetic thiazolidinedione being evaluated for the treatment of non-insulin-dependent diabetes mellitus. Non-insulin-dependent diabetes mellitus (NIDDM) is a metabolic disease characterized by a reduction in the response of the peripheral target tissue to insulin and the inability of pancreatic insulin reserves to overcome the reduced response. Improvement of insulin sensitivity of the target tissue not only reduces the consequences of the disease but actually aids in the prevention of NIDDM.

The synthesis of Mitoglitazone has been reported (J. Med. Chem. , 1966, 39, 5053- 5063; Org. Pro. Res. & Dev. (OPRD), 2002, 6, 721-728 and U.S. PaL No. 5,441,971).

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http://pubs.acs.org/doi/abs/10.1021/op025549s

An efficient six-step synthesis has been developed for the preparation of the thiazolidinedione analogue PNU-91325 (3) from the commercially available olefin 12. This process involves a novel epoxide ring opening with a deactivated phenol under phase-transfer conditions. Significant improvements were made in the oxidation of a secondary alcohol to the ketone and the 1,4-reduction of an enone from a previous process. Overall, this route allows for the preparation of PNU-91325 in 25% yield.

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US5,441,971

http://www.google.com/patents/US5441971

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WILL BE UPDATED