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The acid–base chemistry of a drug substance plays a key role in the development of a new drug. The acid–base chemistry will:

 

 

In addition, the acid-base chemistry can also be used to predict the extent of receptor binding and hypothesize the mode of action.


4-Anilino-3-quinolinecarbonitrile compounds show inhibitory activity against a range of enzymes which have been implicated in a number of diseases, and several of these compounds have found therapeutic application. One such drug is Bosutinib (SKI-606), a treatment for chronic myelogenous leukemia.

To investigate the acid-base chemistry of this compound a collaborative project was initiated with Sirius Scientific, employing a combination of potentiometric, UV spectrophotometric and NMR spectroscopic pH titrimetric methodology. These studies reveled Bosutinib:



Macroscopic protonation Scheme

Microscopic protonation Scheme

These studies have been published in the literature and greatly assisted in obtaining the marketing authorisation for Bositinib (Bosulif).  


ACID-BASE CHEMISTRY OF 4-ANILINO-3-QUINOLINECARBONITRILE COMPOUNDS