The effect of solution environment and the electrostatic factor on the crystallisation of desmotropes of irbesartan

The experimental conditions necessary for stabilising irbesartan (IBS) tautomers in solution and selectively obtaining the desmotropic crystal forms are presented herein. 1H and 2H tautomers were stabilized in specific solution conditions and the 2H-tetrazole imidazole interaction was confirmed by s...

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Bibliographic Details
Published in:RSC advances 2019-02, Vol.9 (9), p.5244-525
Main Authors: Araya-Sibaja, Andrea M, Urgellés, Mariola, Vásquez-Castro, Felipe, Vargas-Huertas, Felipe, Vega-Baudrit, José Roberto, Guillén-Girón, Teodolito, Navarro-Hoyos, Mirtha, Cuffini, Silvia L
Format: Article
Language:English
Subjects:
Chemistry
Crystallization
Imidazole
NMR
Nuclear magnetic resonance
Tautomers
Tetrazoles
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Summary:The experimental conditions necessary for stabilising irbesartan (IBS) tautomers in solution and selectively obtaining the desmotropic crystal forms are presented herein. 1H and 2H tautomers were stabilized in specific solution conditions and the 2H-tetrazole imidazole interaction was confirmed by solution-state NMR. The results showed that highly polar and polarisable solvents (higher values of the electrostatic factor (EF)) lead to the crystallisation of IBS form B. Furthermore, the variations of pH in methanol, in turn, determined the crystallisation of desmotropes A and/or B. The experimental conditions necessary for stabilising irbesartan (IBS) tautomers in solution and selectively obtaining the desmotropic crystal forms are presented herein.
ISSN:2046-2069
2046-2069
DOI:10.1039/c8ra10146a