Preparation and studies of the co-crystals of meloxicam with carboxylic acids

Myz, S. A.; Шахтшнейдер, Т. П.; Tumanov, Nikolay; Boldyreva, Elena V.

doi:10.1007/s11172-012-0248-6

Cited by 22 publications

(32 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For example, if liquids that do not dissolve any reactant component still exhibit an effect on co-grinding, one can obviously exclude transition to a solution phase reaction. 60 Following this methodology, a series of solvents were tested for the a-glycine + b-malonic acid system, Fig. 18.…”

Section: Liquid Assisted Grindingmentioning

confidence: 99%

Advances in elucidating mechanochemical complexities via implementation of a simple organic system

et al. 2014

View full text Add to dashboard Cite

Mechanochemistry is becoming increasingly popular amongst both the academic and industrial communities as an alternative method for inducing physical and chemical reactions. Despite its rapidly expanding application, little is understood of its mechanisms, greatly limiting its capacity. In the present work the application of specialty devices allowed submission of the simple organic system, α-glycine + β-malonic acid, to isolated shearing and impact treatment. In doing so, unique products were observed to result from each of these major mechanical actions; shear inducing formation of the known salt, glycinium semi-malonate (GSM), and impact yielding formation of a novel phase. Correlation of these isolated treatments with a more common ball mill indicated two unique regions within the milling jar, each characterised by varying ratios of shear and impact, leading to different products being observed. It is widely accepted that, particularly when considering organic systems, mechanical treatment often acts by inducing increases in local temperature, leading to volatilisation or melting. A combination of DSC and TGA were used to investigate the role of temperature on the system in question. Invariably, heating induced formation of GSM, with evidence supporting a eutectic melt, rather than a gas-phase reaction. Shear heating alone is unable to describe formation of the novel phase obtained through impact treatment. By considering the formation and character of mechanically produced tablets, a model is described that may account for formation of this novel phase. This system and methodology for mechanochemical study offers intriguing opportunities for continued study of this widely used and exciting field.

show abstract

Section: Liquid Assisted Grindingmentioning

confidence: 99%

Advances in elucidating mechanochemical complexities via implementation of a simple organic system

et al. 2014

View full text Add to dashboard Cite

show abstract

“…Coformers are typically chosen from among the dicarboxylic acids due to their favourable molecular shape and the presence of functional groups capable of forming multiple hydrogen bonds, combined with their affordability and availability. Meloxicam (MXM), 4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide, belongs to the oxicam family of APIs and is commonly used in the treatment of rheumatoid arthritis (Myz et al, 2012;Weyna et al 2012). MXM is known to cocrystallize with numerous aliphatic and aromatic dicarboxylic acids under various conditions (temperature, pressure, solvents).…”

Section: Chemical Contextmentioning

confidence: 99%

“…Two polycrystalline samples were obtained by dry and slurry (with acetone) grinding of 1:2 molar mixture of reactants (0.035g, 0.1mmol MXM; 0.023g, 0.2mmol ACA). The 2:1 ratio would correspond to the target stoichiometry and is usually used for obtaining other MXM co-crystals with aliphatic dicarboxylic acids (Myz et al, 2012;Weyna et al 2012). However, to obtain MXM-ACA 2:1 co-crystals we used a 1:2 MXM:ACA ratio because ACA is highly hygroscopic and converts to its monohydrate form on grinding, not participating then in the co-crystallization.…”

Section: Synthesis and Crystallizationmentioning

confidence: 99%

Crystal structure of a 2:1 co-crystal of meloxicam with acetylendicarboxylic acid

Tantardini¹,

Arkhipov²,

Cherkashina³

et al. 2016

Acta Cryst E

View full text Add to dashboard Cite

show abstract

“…Crystallisation is traditionally used to purify compounds and to crystallise components selectively as 35 pure phases from multicomponent mixtures, be they solutions or melts 20-24 . In such cases, the multicomponent crystals can be obtained under non-equilibrium conditions only, such as rapid precipitation by anti-solvents, spray-drying, or by co-grinding 5,[29][30][31][32][33][34][35][36] . to co-crystallise several components in one solid phase, one needs to know the thermodynamics and kinetics of the process [25][26][27][28] .…”

Section: Introductionmentioning

confidence: 99%

“…In other cases, the target multicomponent crystal is thermodynamically 45 stable, but the components as solid phases differ so much in melting temperatures or in solubilities, that it is very difficult to find a practical method of co-crystallising them into a single phase. Attempts are also known in which phase diagrams are applied to predict the result of co-grinding component mixtures 43,44 , although it was shown in several papers that the products of cogrinding, more often than not, correspond to non-equilibrium 60 conditions 33,[45][46][47][48] . For example, detailed studies of the solubility curves for all components make it possible to get co-crystals by crystallisation from multicomponent solutions even if the solubilities of components differ significantly 26,27,37 .…”

Section: Introductionmentioning

confidence: 99%

Bis(paracetamol) pyridine – a new elusive paracetamol solvate: from modeling the phase diagram to successful single-crystal growth and structure–property relations

et al. 2015

View full text Add to dashboard Cite

Multi-component crystals -salts, co-crystals, or solvates -are usually designed based on the analysis of complementarity of functional groups and intermolecular interactions of the components. However, no crystal design can do without a practical method of crystal growth. Not all compounds that should be 10 expected to exist based on the "synthon approach" can be prepared in real experiments. This paper aims to illustrate that, in addition to the synthon approach, it is equally important to take into account phase diagrams when searching for practical methods of crystallising multi-component crystals, either as single crystals or as fine particles. Here, we describe the crystallization of bis(paracetamol) pyridine solvate from a glass-like metastable phase produced by quench-freezing of the paracetamol-pyridine solution 15 with subsequent low-temperature annealing. These procedures must be carried out strictly within the boundaries of the two-phase region "solid solvate + liquor", which was found only as a result of modelling the phase diagram. The crystal structure was solved by single-crystal X-ray diffraction and compared with co-crystals of paracetamol found in Cambridge Structural Database. The structureforming role of the intermolecular interactions and their characteristics were studied by variable-20 temperature experiments over the range of 100-275 K. This was compared with the structures of pure paracetamol polymorphs and other solvates and co-crystals at ambient and non-ambient conditions.

show abstract

Preparation and studies of the co-crystals of meloxicam with carboxylic acids

Cited by 22 publications

References 32 publications

Advances in elucidating mechanochemical complexities via implementation of a simple organic system

Advances in elucidating mechanochemical complexities via implementation of a simple organic system

Crystal structure of a 2:1 co-crystal of meloxicam with acetylendicarboxylic acid

Bis(paracetamol) pyridine – a new elusive paracetamol solvate: from modeling the phase diagram to successful single-crystal growth and structure–property relations

Contact Info

Product

Resources

About