1019113-44-0Relevant articles and documents
Asymmetric synthesis of a glucagon receptor antagonist via friedel-crafts alkylation of indole with chiral α-phenyl benzyl cation
Chung, John Y. L.,Steinhuebel, Dietrich,Krska, Shane W.,Hartner, Fred W.,Cai, Chaoxian,Rosen, Jonathan,Mancheno, Danny E.,Pei, Tao,Dimichele, Lisa,Ball, Richard G.,Chen, Cheng-Yi,Tan, Lushi,Alorati, Antony D.,Brewer, Sarah E.,Scott, Jeremy P.
, p. 1832 - 1845 (2013/01/15)
Development of a practical asymmetric synthesis of a glucagon receptor antagonist drug candidate for the treatment of type 2 diabetes is described. The antagonist consists of a 1,1,2,2-tetrasubstituted ethane core substituted with a propyl and three aryl groups including a fluoro-indole. The key steps to construct the ethane core and the two stereogenic centers involved a ketone arylation, an asymmetric hydrogenation via dynamic kinetic resolution, and an anti-selective Friedel-Crafts alkylation of a fluoro-indole with a chiral α-phenyl benzyl cation. We also developed two new efficient syntheses of the fluoro-indole, including an unusual Larock-type indole synthesis and a Sugasawa-heteroannulation route. The described convergent synthesis was used to prepare drug substance in 52% overall yield and 99% ee on multikilogram scales.
CRYSTALLINE POLYMORPHIC FORMS OF AN ANTIDIABETIC COMPOUND
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Page/Page column 7, (2010/08/04)
The present invention relates to polymorphic forms of a compound of formula A: This compound is useful as a glucagon receptor antagonist and serves as a pharmaceutically active ingredient for the treatment of type 2 diabetes and related conditions, such as hyperglycemia, obesity, dyslipidemia, and the metabolic syndrome. Hydrates, hemihydrates, anhydrates and similar polymorphic forms are included.
GLUCAGON RECEPTOR ANTAGONIST COMPOUNDS, COMPOSITIONS CONTAINING SUCH COMPOUNDS AND METHODS OF USE
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Page/Page column 38-39, (2010/04/06)
Glucagon receptor antagonist compounds are disclosed. The compounds are useful for treating type 2 diabetes and related conditions. Pharmaceutical compositions and methods of treatment are also included.
GLUCAGON RECEPTOR ANTAGONIST COMPOUNDS
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Page/Page column 35, (2010/08/05)
Glucagon receptor antagonist compounds are disclosed. The compounds are useful for treating type 2 diabetes and related conditions. Pharmaceutical compositions and methods of treatment are also included.
GLUCAGON RECEPTOR ANTAGONIST COMPOUNDS, COMPOSITIONS CONTAINING SUCH COMPOUNDS AND METHODS OF USE
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Page/Page column 34-35, (2010/08/09)
Glucagon receptor antagonist compounds are disclosed. The compounds are useful for treating type 2 diabetes and related conditions. Pharmaceutical compositions and methods of treatment are also included.
GLUCAGON RECEPTOR ANTAGONIST COMPOUNDS, COMPOSITIONS CONTAININ SUCH COMPOUNDS AND METHODS OF USE
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Page/Page column A, (2010/09/17)
Glucagon receptor antagonist compounds are disclosed. The compounds are useful for treating type 2 diabetes and related conditions. Pharmaceutical compositions and methods of treatment are also included.
Glucagon receptor antagonist compounds, compositions containing such compounds and methods of use
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Page/Page column 18, (2008/06/13)
Glucagon receptor antagonist compounds are disclosed. The compounds are useful for treating type 2 diabetes and related conditions. Pharmaceutical compositions and methods of treatment are also included.