Co-crystal of (R,R)-1,2-cyclohexanediol with (R,R)-tartaric acid, a key structure in resolution of the (±)-trans-diol by supercritical extraction, and the related ternary phase system

Thorey, Paul; Bombicz, Petra; Szilágyi, Imre Miklós; Molnar, Peter; Bánsághi, György; Székely, Edit; Simándi, Béla; Pa̋rkányi, László; Pokol, György; Madarász, János

doi:10.1016/j.tca.2009.09.001

Cited by 29 publications

(25 citation statements)

References 33 publications

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“…Cocrystallization typically relies on strong intermolecular interactions, such as hydrogen and halogen bonding, which are more universal. Cocrystallization has been explored by us and others in the context of chiral resolution to target several racemic drug systems . On the basis of these methods, and drawing a parallelism to CIDT, we set out to go beyond chiral resolution, targeting a cocrystallization‐induced spontaneous deracemization (CoISD) process.…”

Section: Methodsmentioning

confidence: 99%

“…Cocrystallization has been explored by us and others in the context of chiral resolution to target several racemic drug systems. [22][23][24][25] On the basis of these methods, and drawing a parallelism to CIDT, we set out to go beyond chiral resolution, targeting a cocrystallization-induced spontaneous deracemization (CoISD) process. The industrially friendly thermodynamic process developed in this study is applicable to all compounds, whether they form salts or not, and to both conglomerate-and racemic-compound-forming systems, thereby making it a general process, in contrast to all other crystallization-based deracemization processes.…”

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confidence: 99%

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Cocrystallization‐Induced Spontaneous Deracemization: A General Thermodynamic Approach to Deracemization

et al. 2020

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Processes leading to enantiomerically pure compounds are of utmost importance, in particular for the pharmaceutical industry. Starting from a racemic mixture, crystallization‐induced diastereomeric transformation allows in theory for 100 % transformation of the desired enantiomer. However, this method has the inherent limiting requirement for the organic compound to form a salt. Herein, this limitation is lifted by introducing cocrystallization in the context of thermodynamic deracemization, with the process applied to a model chiral fungicide. We report a new general single thermodynamic deracemization process based on cocrystallization for the deracemization of (R,S)‐4,4‐dimethyl‐1‐(4‐fluorophenyl)‐2‐(1H‐1,2,4‐triazol‐1‐yl)pentan‐3‐one. This study demonstrates the feasibility of this novel approach and paves the way to further development of such processes.

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Section: Methodsmentioning

confidence: 99%

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confidence: 99%

Cocrystallization‐Induced Spontaneous Deracemization: A General Thermodynamic Approach to Deracemization

et al. 2020

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“…Therefore thermal analysis is a common part of characterizing compounds with biological activity [20,21,22,23,24,25]. Thermoanalytical methods provide important information on the thermal stability, polymorphic forms or structural changes [26,27,28], and purity of potential new drugs [29,30,31,32]. In continuation of our earlier work on synthesis, physical and chemical characterization of iron(II) complexes with amine ligands [33] in this paper Pt(II) coordination compounds with different amine ligands are described.…”

Section: Introductionmentioning

confidence: 93%

Synthesis, physico-chemical characterization and bacteriostatic study of Pt complexes with substituted amine ligands

Holló

Szilágyi

Várhelyi

et al. 2016

J Therm Anal Calorim

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Three complexes of general formula PtCl 2 R 2 were synthesized, where R is the amine ligand with aromatic substituents. Coordination compounds [Pt(an) 2 Cl 2 ] (1), [Pt(pa) 2 Cl 2 ] (2) and [Pt(aph) 2 Cl 2 ] (3), where an is 2-aminonaphtalene, pa is 2-pyrimidinamine and aph is 4-anilinophenol, were characterized by on-line coupled TG/DTA-MS, powder XRD and spectroscopic techniques (FTIR, ESI-MS and NMR), and tested against selected Gram(+) and Gram(-) bacteria. The thermal data show that all three compounds contain lattice or absorbed water, and the stability of the anhydrous compounds in nitrogen decreases in the order 2 > 1 > 3. Above 200 °C, the complexes loose characteristic fragments of their ligands. The spectroscopic data are in accordance with the thermal properties of the samples and prove their composition. The compounds are more effective inhibitors of Gram(+) than Gram(−) bacteria.

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“…However, such a complex structure determines the superior physicochemical properties of ternary eutectic composition than the binary one, which also efficiently reduces the drug side effects. 22 − 24 Therefore, it is particularly essential to acquire the related information about the micromolecular structural changes during the formation process of such ternary eutectics and/or co-crystals.…”

Section: Introductionmentioning

confidence: 99%

Vibrational Spectroscopic Investigation into Novel Ternary Eutectic Formed between Pyrazinamide, Fumaric Acid, and Isoniazid

et al. 2020

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To improve the efficacy of anti-tuberculosis (anti-TB) therapy, drug–drug co-crystallization stands for an alternative approach to settle the tuberculosis problem. Directly co-crystallizing two typical parent anti-TB drugs (pyrazinamide, PZA and isoniazid, INH) into a single binary co-crystal could not be obtained successfully. Multicomponent eutectic are highly effective and useful for enhancing the dissolution rate, bioavailability, and physical stability of the poorly water-soluble active pharmaceutical ingredient (API) drugs, when the attempts of forming a binary co-crystal have failed. Therefore, the ternary eutectic composition conception was proposed in this study, in which fumaric acid (FA) was chosen as the molecule to connect two first-line anti-tubercular drugs. First of all, three starting materials (including PZA, INH, and FA) were grinded at a 1:1:1 molar ratio, the eutectic composition was investigated through vibrational spectroscopic techniques, including terahertz time-domain spectroscopy (THz-TDS) and Raman spectroscopy. Additionally, the density functional theory (DFT) was utilized to simulate the optimized structures and vibrational modes of two possible theoretical eutectic composition forms. The THz absorption spectrum of the theoretical form I shows much more consistency with the experimental results than that of form II. Raman spectra also help to characterize the differences in vibrational modes between the eutectic composition and the starting parent compounds. The results provide us with both structural information and intermolecular hydrogen bonding interactions within specific multicomponent eutectic composition formulations based on Raman and terahertz vibrational spectroscopic techniques in combination with theoretical calculations.

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Co-crystal of (R,R)-1,2-cyclohexanediol with (R,R)-tartaric acid, a key structure in resolution of the (±)-trans-diol by supercritical extraction, and the related ternary phase system

Cited by 29 publications

References 33 publications

Cocrystallization‐Induced Spontaneous Deracemization: A General Thermodynamic Approach to Deracemization

Cocrystallization‐Induced Spontaneous Deracemization: A General Thermodynamic Approach to Deracemization

Synthesis, physico-chemical characterization and bacteriostatic study of Pt complexes with substituted amine ligands

Vibrational Spectroscopic Investigation into Novel Ternary Eutectic Formed between Pyrazinamide, Fumaric Acid, and Isoniazid

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