Taro Pharmaceutical Industries Limited

Taro Pharmaceuticals U.s.a., Inc.

Martin Zarbov

Daniella Gutman

Shimon Chernyak

A method for producing a 6&#x3b1;-fluorinated corticosteroid or derivative thereof by reacting a 17-hydroxy-21-ester epoxide of Formula II with a stereoselective fluorinating agent to stereoselectively form a 21-ester-17-hydroxy 6&#x3b1;-fluorinated compound of Formula VII Rcan be OC(O)&#x2014;R; Rcan be C(O)&#x2014;R; Rcan be H or R. Each Rmay be the same or different and is independently selected from (C)alkyl, aryl and heteroaryl. The dashed line can be a single or a double bond. Rmay be, for example, acetyl; Rmay be, for example, alpha or beta methyl; Rmay be, for example, acetate or propionate, The stereoselective fluorinating agent used in the reaction may be, for example, a fluoropyridinium or fluoroquinuclidium compound, for example, Selectfluor&#xae;.

Method for the preparation of 6-&#x3b1; fluoro corticosteroids

A method for producing a 6&#x3b1;-fluorinated corticosteroid or derivative thereof by reacting a 17-hydroxy-21-ester epoxide of Formula II with a stereoselective fluorinating agent to stereoselectively form a 21-ester-17-hydroxy 6&#x3b1;-fluorinated compound of Formula VII Rcan be OC(O)&#x2014;R; Rcan be C(O)&#x2014;R; Rcan be H or R. Each Rmay be the same or different and is independently selected from (C)alkyl, aryl and heteroaryl. The dashed line can be a single or a double bond. Rmay be, for example, acetyl; Rmay be, for example, alpha or beta methyl; Rmay be, for example, acetate or propionate. The stereoselective fluorinating agent used in the reaction may be, for example, a fluoropyridinium or fluoroquinuclidium compound, for example, Selectfluor&#xae;.

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Kiriat Haim, Israel

Martin Zarbov