Concert Pharmaceuticals, Inc.

Can-fite Biopharma Ltd.

Vistagen Therapeutics, Inc.

Qaam Pharmaceuticals, LLC

Xuejun Karl Liu

Emerich Eisenreich

Steven A Weissman

Ramanaiah C Kanamarlapudi

Daniel Levin

Satish Puppali

Steven A Rich

Bingidimi Itute Mobele

Peter Leeming

Cameron Gibb

Pedro E HErnandez-Abad

Satish Goud Puppali

Paul Bruzinski

Pedro Hernandez-Abad

The invention relates to an overall enantio-specific synthesis of 4-chlorokynurenine compounds, in particular L-4-chlorokynurenine, with improved yields. Large-scale syntheses are disclosed. The invention also relates to novel intermediates in the synthesis of L-4-chlorokynurenine.

Synthesis of 4-chlorokynurenines and intermediates

Novel glycopyrronium fatty acid salts have been developed. Bi-phasic reaction conditions enable the desired counterion exchange reactions between glycopyrronium bromide and fatty acid salts of alkali metals and alkaline earth metals in methods to form glycopyrronium fatty acid salts. In preferred embodiments, an excess of the free fatty acid in the reaction mixture stabilizes the glycopyrronium fatty acid salt and reduces the formation of the impurity, Acid A. In some preferred embodiments, between 0.2 and 1.2 molar equivalent of excess free fatty acid is added to the reaction mixture. In another embodiment, approximately 1.2 molar equivalent of excess free fatty acid is added to the reaction mixture.

Glycopyrronium fatty acid salts and methods of making same

The present disclosure provides a method for the synthesis of IB-MECA. More specifically, the present disclosure provides a simple and high yield method for Good Manufacturing Production (GMP) of IB-MECA. The method involves the reaction of 6-halopurine-9-riboside with a diol protecting reagent; oxidation of the primary alcohol in the diol protected 6-halopurine-9-riboside with a diol protecting reagent; oxidation of the primary alcohol in the diol protected 6-halopurine; reaction of the diol protected 6-halopurine with a nucleophile (e.g. methylamine); substitution of the halogen group with iodobenzylamine and removal of the diol protecting group.

Process for the synthesis of IB-MECA

The present invention provides a convenient and efficient process for the preparation of enantiomerically enriched, deuterated secondary alcohols without reducing deuterium incorporation.

Process for preparing an enantiomerically enriched, deuterated secondary alcohol from a corresponding ketone without reducing deuterium incorporation

The present invention provides a process for the preparation of enantiomerically enriched, deuterated secondary alcohols of Formula 1-A by employing ketoreductases or carbonyl reductases without reducing deuterium incorporation. 

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Arcadia, CA, United States of America

Xuejun Karl Liu