Solubility measurement and correlation of the form A of ibrutinib in organic solvents from 278.15 to 323.15 K

Chen, Zhenzhen; Zhai, Jinghuan; Liu, Xijian; Mao, Shimin; Zhang, Lijuan; Rohani, Sohrab; Lü, Jie

doi:10.1016/j.jct.2016.08.034

Cited by 27 publications

(12 citation statements)

References 23 publications

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“…The scanning wavenumber ranged from 500 to 4000 cm –1 . 38 PXRD was operated on a TD-3700 diffractometer with Cu Kα radiation (Tongda Instruments, Dandong, China). The step length from 3 to 80° was 0.05°, and the time per step was 5 s. 39 The thermal analyses by DSC and TGA were conducted on an HSC-4 differential scanning calorimeter (Henjiu Experimental Equipment, Bejing, China) and a WRT-12 thermogravimetric analyzer (Beiguang Hongyuan Instruments, Beijing, China), respectively.…”

Section: Experimental Sectionmentioning

confidence: 99%

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Direct Crystallization Resolution of Racemates Enhanced by Chiral Nanorods: Experimental, Statistical, and Quantum Mechanics/Molecular Dynamics Simulation Studies

Cao

Lou

et al. 2022

ACS Omega

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Three chiral nanorods of C 14 - l -Thea, C 14 - l -Phe, and C 14 - d -Phe were first synthesized and utilized as heterogeneous nucleants to enhance the resolution of racemic Asp via direct crystallization. Through the statistical analysis from 320 batches of nucleation experiments, we found that the apparent appearance diversity of two enantiomeric crystals of Asp existed in 80 homogeneous experiments without chiral nanorods. However, in 240 heterogeneous experiments with 4.0 wt % chiral nanorods of solute mass added, the appearance of those nuclei with the same chirality as the nanorods was apparently promoted, and that with the opposite chirality was totally inhibited. Under a supersaturation level of 1.08, the maximum ee of the initial nuclei was as high as 23.51%. When the cooling rate was 0.025 K/min, the ee of the product was up to 76.85% with a yield of 14.41%. Furthermore, the simulation results from quantum mechanics (QM) and molecular dynamics (MD) revealed that the higher chiral recognition ability of C 14 - l -Thea compared to C 14 - l -Phe that originated from the interaction difference between C 14 - l -Thea and Asp enantiomers was larger than that between C 14 - l -Phe and Asp enantiomers. Moreover, the constructed nanorods exhibited good stability and recyclability.

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Section: Experimental Sectionmentioning

confidence: 99%

“…The heating rate was 5.0 K per minute. 38 DLS was employed for the measurement of particle size distribution using a Zen 3690 nanosizer with an APD detector (Malvern Panalytical, Malvern, UK). A 4 mW helium–neon gas laser was used as the light source (633 nm).…”

Section: Experimental Sectionmentioning

confidence: 99%

Direct Crystallization Resolution of Racemates Enhanced by Chiral Nanorods: Experimental, Statistical, and Quantum Mechanics/Molecular Dynamics Simulation Studies

Cao

Lou

et al. 2022

ACS Omega

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“…Various thermodynamic models have been developed to correlate the experimental solubilities of solutes with calculated ones. The van’t Hoff model, Apelblat model, Buchowski–Ksiazczak model, and polynomial empirical models are commonly used solid–liquid equilibrium models to correlate the experimental solubilities with calculated ones and to investigate the impact of temperature on the molar fraction solubility of solutes. − Therefore, in this research work, the molar fraction solubilities of SAT in the above-mentioned monosolvents were measured from 293.2 to 313.2 K at 0.1 MPa atmospheric pressure (Figure ). Thus, the obtained solubility data of this study could be extremely useful in various fields such as purification, crystallization, separation, and formulation development of SAT in the pharmaceutical and chemical industries.…”

Section: Introductionmentioning

confidence: 99%

Thermodynamic Modeling and Solubility Study of Satranidazole in Different Monosolvents at Different Temperatures

Rathi¹,

Kale

Jouyban

2021

J. Chem. Eng. Data

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The solubility study of drugs in aqueous and organic solvents has practical importance in pharmaceutical industries. In this research work, the solubilities of satranidazole (SAT) were determined in 18 monosolvents, namely, methanol (MeOH), ethanol (EtOH), 1-propanol (1-PrOH), 2-propanol (2-PrOH), formamide, 1,4-dioxane, N,N-dimethyl formamide (DMF), N,N-dimethyl acetamide (DMA), dimethyl sulfoxide (DMSO), N-methyl-2-pyrrolidone (NMP), ethylene glycol (EG), propylene glycol (PG), 1,4-butanediol (BDOH), glycerin, polyethylene glycol-200 (PEG-200), PEG-400, PEG-600, and water, at five different temperatures (T = 293.2–313.2 K) and atmospheric pressure (p = 0.1 MPa). Experimental solubilities expressed in the molar fraction of SAT were correlated well with thermodynamic models including van’t Hoff model, Apelblat model, Buchowski–Ksiazczak model, and polynomial empirical model. The molar fraction solubility of SAT was recorded highest in NMP (7.963 × 10–2 at T = 293.2 K) followed by DMSO, formamide, DMF, DMA, PEG-600, PEG-400, PEG-200, 1,4-dioxane, PG, EG, BDOH, glycerin, MeOH, EtOH, 1-PrOH, 2-PrOH, and water as expected over the entire temperature range investigated.

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“… , According to the “heat of fusion rule” of the temperature and enthalpy of fusion of polymorphs, form I with a high melting point has a higher heat of fusion, indicating that form I is the stable phase, and forms I and II are monotropic systems. Solution crystallization is a traditional technology for the separation, purification, and engineering of the properties of crystalline compounds. − The solubilities of imidacloprid forms I and II are essential and crucial for the designing of the crystallization process. , Moreover, the difference in solubility between the two forms can provide the drive for solvent-mediated transformation from form II to form I . However, the solubility data of forms I and II published in the literature yet are relatively few.…”

Section: Introductionmentioning

confidence: 99%

“…9−12 The solubilities of imidacloprid forms I and II are essential and crucial for the designing of the crystallization process. 13,14 Moreover, the difference in solubility between the two forms can provide the drive for solvent-mediated transformation from form II to form I. 11 However, the solubility data of forms I and II published in the literature yet are relatively few.…”

Section: Introductionmentioning

confidence: 99%

Determination and Correlation of Solubility of Forms I and II of Imidacloprid in Seven Pure Solvents from 293.15 to 333.15 K

Wang

Shi

et al. 2020

J. Chem. Eng. Data

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The solubility of two forms of imidacloprid, forms I and II, in seven pure organic solvents was measured using the analytical gravimetric method. It was shown that the solubility of the two forms of imidacloprid increases as the temperature increases. Meanwhile, the solubility at a low temperature follows the order methyl acetate > ethyl acetate > n-butyl acetate > methanol > ethanol > n-propanol > n-butanol and the order at relatively high temperatures is methyl acetate > ethyl acetate > methanol > n-butyl acetate > ethanol > n-propanol > n-butanol. Differential scanning calorimetry and solubility data show that the two forms are monotropically related and form I is the stable phase. Besides, the experimental solubility of forms I and II in the seven pure solvents is well correlated by the modified Apelblat model and λh model, respectively.

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Solubility measurement and correlation of the form A of ibrutinib in organic solvents from 278.15 to 323.15 K

Cited by 27 publications

References 23 publications

Direct Crystallization Resolution of Racemates Enhanced by Chiral Nanorods: Experimental, Statistical, and Quantum Mechanics/Molecular Dynamics Simulation Studies

Direct Crystallization Resolution of Racemates Enhanced by Chiral Nanorods: Experimental, Statistical, and Quantum Mechanics/Molecular Dynamics Simulation Studies

Thermodynamic Modeling and Solubility Study of Satranidazole in Different Monosolvents at Different Temperatures

Determination and Correlation of Solubility of Forms I and II of Imidacloprid in Seven Pure Solvents from 293.15 to 333.15 K

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