2019
DOI: 10.1021/acs.cgd.9b01299
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Selective Synthesis of a Salt and a Cocrystal of the Ethionamide–Salicylic Acid System

Abstract: Herein is presented a rare example of salt/ cocrystal polymorphism involving the adduct between ethionamide (ETH) and salicylic acid (SAL). Both the salt and cocrystal forms have the same stoichiometry and composition and are both stable at room temperature. The synthetic procedure was successfully optimized in order to selectively obtain both polymorphs. The two adducts' structures were thoroughly investigated by means of singlecrystal X-ray diffraction, solid-state NMR spectroscopy, and density functional th… Show more

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Cited by 60 publications
(39 citation statements)
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“…In all cases, endothermic DSC peaks, corresponding to lower melting points than for pure ETN, are observed. This behavior is recurrent for ETN as all the adducts reported in literature are characterized by lower melting points [ 16 , 25 , 26 , 27 ].…”
Section: Resultsmentioning
confidence: 82%
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“…In all cases, endothermic DSC peaks, corresponding to lower melting points than for pure ETN, are observed. This behavior is recurrent for ETN as all the adducts reported in literature are characterized by lower melting points [ 16 , 25 , 26 , 27 ].…”
Section: Resultsmentioning
confidence: 82%
“…The latter, in particular, are more and more commonly pursued as an alternative to salts in the quest for performance enhancement of APIs, because cocrystallization offers greater opportunities than salification: (i) it is viable for molecules that do not display any ionizable moiety; (ii) the possible coformers (i.e., molecules selected to cocrystallize with the API) are more numerous than the possible counterions; (iii) cocrystallization can significantly improve the solubility of the APIs without altering their permeability. As of today, many pharmaceutical cocrystals have been successfully prepared and reported in the literature [ 7 , 16 , 17 , 18 , 19 , 20 ].…”
Section: Introductionmentioning
confidence: 99%
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“…The accuracy of the NH bond length measurements can be improved by using a phase modulated saturation pulse to more reliably saturate the 14 N spins. [24][25] 1 H{ 14 N} FS RESPDOR was also performed on the ammonium 1 H signal of hist at 17.2 ppm to confirm the accuracy of the NH distance measurements (Figure S11). Using 1 H{ 14 N} FS RESPDOR rNH = 1.10 Å was determined, in good agreement with the value of rNH = 1.09 Å measured by Levitt and co-workers with 15 N{ 1 H} symmetry-based recoupling, separated local field (SLF) experiments on 15 N-enriched hist.…”
Section: Resultsmentioning
confidence: 96%
“…[24] However, experiment times on the order of 6-10 hours have been reported to record 1 H{ 14 N} RESPDOR dipolar dephasing curves of amino acids [24] and multicomponent APIs. [25] 1 H{ 14 N} FS RESPDOR allowed complete dipolar dephasing curves to be obtained in only 20 minutes each for 1 and 2 (Figure 4D, Figures S9 and S10). 1 H{ 14 N} RESPDOR curves for 1 and 2 were calculated with the SIMPSON simulation program for a 1 H-14 N-14 N spin system.…”
Section: Resultsmentioning
confidence: 99%