1383982-64-6Relevant articles and documents
Process Development of a Suzuki Reaction Used in the Manufacture of Lanabecestat
Ashworth, Ian W.,Campbell, Andrew D.,Cherryman, Janette H.,Clark, Jemma,Crampton, Alex,Eden-Rump, Edward G. B.,Evans, Matthew,Jones, Martin F.,McKeever-Abbas, Sahar,Meadows, Rebecca E.,Skilling, Kathryn,Whittaker, David T. E.,Woodward, Robert L.,Inglesby, Phillip A.
, p. 1801 - 1808 (2018)
We developed a scalable Suzuki process for the synthesis of lanabecestat (+)-camsylate, an active pharmaceutical ingredient that was recently investigated in a Phase III clinical program for the treatment of early Alzheimer's disease. The evolution of this process culminated with the use of a stable and crystalline diethanolamine boronic ester that rapidly hydrolyses under the reaction conditions. Herein, we report that the liberated diethanolamine plays an important role in the catalytic process, with supporting evidence for an equilibrium between an unbound and bound palladium complex. Additionally, the diethanolamine acts as an internal scavenger during the crystallization of lanabecestat by increasing the solubility of the palladium species, obviating the need for a discrete scavenging step.
CAMSYLATE SALT
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, (2014/01/09)
A camsylate salt of (1r,1 'R,4R)- 4-methoxy-5"-methyl-6'-[5-(prop-1-yn-1-yl)pyridin-3-yl]-3'H-dispiro[cyclohexane-1,2'-inden-1'2'-imidazole]-4"-amine, pharmaceutical compositions containing the salt and therapeutic uses of the salt for treating Αβ-related pathologies such as Alzheimer's Disease, Down's syndrome, β-amyloid angiopathy and conditions such as dementia including dementia of mixed vascular and degenerative origin, pre-senile dementia, senile dementia and dementia associated with Parkinson's disease, progressive supranuclear palsy or cortical basal degeneration.