Alogliptin and its benzoate salt. (24th May 2013)

• Record Type: Journal Article
• Authors: Gelbrich, Thomas; Kahlenberg, Volker; Griesser, Ulrich J.
• Is Part Of: Acta crystallographica. Volume 69:Part 6(2013:Jun.)
• Page Start: 674
• Page End: 678
• Publication Date: 2013-05-24
• Subjects: Crystallography -- Periodicals; Crystals -- Periodicals; 548.05
• DOI: 10.1107/S0108270113012560
• Languages: English
• ISSNs: 0108-2701

Abstract

<abstract abstract-type="main" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p>The crystal structure of the free base of the antidiabetic drug alogliptin [systematic name: 2‐({6‐[(3<italic>R</italic>)‐3‐aminopiperidin‐1‐yl]‐3‐methyl‐2, 4‐dioxo‐1, 2, 3, 4‐tetrahydropyrimidin‐1‐yl}methyl)benzonitrile], C₁₈H₂₁N₅O₂, displays a two‐dimensional N—H...O hydrogen‐bonded network. It contains two independent molecules, which have the same conformation but differ in their hydrogen‐bond connectivity. In the crystal structure of the benzoate salt (systematic name: (3<italic>R</italic>)‐1‐{3‐[(2‐cyanophenyl)methyl]‐1‐methyl‐2, 6‐dioxo‐1, 2, 3, 6‐tetrahydropyrimidin‐4‐yl}piperidin‐3‐aminium benzoate), C₁₈H₂₂N₅O₂⁺·C₇H₅O₂⁻, the NH₃⁺ group of the cation is engaged in three intermolecular N—H...O hydrogen bonds to yield a hydrogen‐bonded layer structure. The benzoate salt and the free base differ fundamentally in the conformations of their alogliptin moieties.</p> </abstract>