Conformational considerations in the design of dual antagonists of platelet-activating factor (PAF) and histamine

Kaminski, James J.; Carruthers, Nicholas I.; Wong, Shing-Chun; Chan, Tze‐Ming; Billah, M. Motassim; Tozzi, Salvatore; McPhail, Andrew T.

doi:10.1016/s0968-0896(99)00075-9

Cited by 14 publications

(6 citation statements)

References 8 publications

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“…3. The powder X-ray diffraction pattern of LOR raw material shows main peaks at 6.4, 12.7, 15.1, 19.6, 21.2, 23.8, and 30.5° of 2θ angle, and this diffraction pattern is consistent with the crystal structure of LOR with BEQGIN reference code [25]. The FUM raw material has main peaks of powder X-ray diffraction at 18.6, 22.8, 24.5, 25.9, 28.9, and 29.5° 2θ angle, and the diffraction pattern conform to form α of FUM with FUMAAC reference code [26].…”

Section: Characterization By Powder X-ray Diffraction Methodssupporting

confidence: 68%

The Preparation and Solubility of Loratadine-Fumaric Acid Binary Mixture

Alatas

Aprilliana

Sopyan

2016

Asian J Pharm Clin Res

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Objective: Loratadine (LOR) is a biopharmaceutics classification system Class II drug that has low solubility and high permeability, so its absorption rate is determined by the dissolution rate. The aim of this study was to prepare an LOR-fumaric acid (LOR-FUM) binary mixture and to investigate its influence on the solubility and dissolution rate of LOR.Methods: LOR-FUM binary mixture was prepared by the wet grinding method in an equimolar ratio by the addition of two drops of methanol. Characterization of LOR-FUM binary mixture was conducted by the construction of the phase solubility, powder X-ray diffractometry, Fourier transforms infrared spectroscopy, and polarizing microscopy methods. Solubility test was performed in water at room temperature, whereas the in vitro dissolution test was performed in the pH 1.2, 4.5, and 6.8 buffer solutions. Results:The phase solubility curve of LOR in FUM solution is similar to type B S . The powder X-ray diffraction results show the crystallinity of LOR was changed become more amorphous indicating the salt formation. Fourier transforms infrared spectroscopy (FTIR) spectra of LOR-FUM binary mixture showed the vibration peaks of an imine group on the pyridine ring of LOR and carbonyl group on the FUM are not detected. On the other hand, the polarizing microscope images showed the crystal habit of LOR-FUM binary mixture after recrystallized from methanol contrast to crystal habit of its pure components. The solubility in water of LOR-FUM binary mixture was higher than pure LOR. Amount of LOR released from LOR-FUM binary mixture in pH 4.5 and 6.8 buffer solutions was faster than from pure LOR. Conclusion:A binary mixture of LOR and FUM may improve the solubility and dissolution rate of LOR.

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Section: Characterization By Powder X-ray Diffraction Methodssupporting

confidence: 68%

The Preparation and Solubility of Loratadine-Fumaric Acid Binary Mixture

Alatas

Aprilliana

Sopyan

2016

Asian J Pharm Clin Res

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“…Indexing results confirmed that loratadine is monoclinic with space group C 2/ c and unit-cell parameters after Pawley refinement: a = 28.302(18) Å, b = 4.996(3) Å, c = 29.154(19) Å, β = 109.158(2)°, unit-cell volume V = 3894.25 Å 3 , and Z = 8 (Table I). A comparison of unit-cell parameters from powder data and single-crystal data (Kaminski et al , 1999) displays a significantly consistency, and the deviations of the two methods were between 0.011 and 0.155%. All lines were indexed and are consistent with the C 2/ c space group.…”

Section: Resultsmentioning

confidence: 97%

“…The single crystallographic data of loratadine [ a = 28.299(3) Å, b = 4.993(1) Å, c = 29.137(3) Å, β = 109.189(9)°, unit-cell volume V = 3888.20 Å 3 , Z = 8, and space group C 2/ c ] was obtained by Kaminski et al (1999). To date, the detailed X-ray powder diffraction data for loratadine have not been reported.…”

Section: Introductionmentioning

confidence: 99%

X-ray powder diffraction data for loratadine (C₂₂H₂₃ClN₂0₂)

et al. 2014

Powder Diffr.

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“…1 Examples of these compounds include loratadine ( 1 , H 1 histamine antagonist), 2 SCH 66336 ( 2 , anti-cancer agent), 3 and MK-2461 ( 3 , anti-cancer agent). 4 The cycloheptabenzopyridine ring system has been previously prepared by intramolecular cyclizations of carboxylic acids, 5 nitriles, 6 alcohols, 7 ketones, 8 and by other routes. 9 For acid-promoted reactions of carboxylic acids, the cyclization requires extreme conditions (i.e., polyphosphoric acid, 200°C).…”

Section: Introductionmentioning

confidence: 99%

Cyclizations of phenylethyl-substituted pyridinecarboxaldehydes

Naredla

Klumpp

2013

Tetrahedron

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Several phenylethyl-substituted pyridinecarboxaldehydes were prepared from 2-bromo-3-pyridinecarboxaldehyde and these substances are found to undergo cyclization reactions in acidic media. In the absence of added nucleophile, acid promoted cyclization and oxidation (MnO2) provides an efficient route to 10,11-dihydro-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-ones. Arene nucleophiles may also be added to the acidic mixture to provide good yields of triarylmethane products. Mechanisms are proposed involving dicationic superelectrophilic intermediates.

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Conformational considerations in the design of dual antagonists of platelet-activating factor (PAF) and histamine

Cited by 14 publications

References 8 publications

The Preparation and Solubility of Loratadine-Fumaric Acid Binary Mixture

The Preparation and Solubility of Loratadine-Fumaric Acid Binary Mixture

X-ray powder diffraction data for loratadine (C₂₂H₂₃ClN₂0₂)

Cyclizations of phenylethyl-substituted pyridinecarboxaldehydes

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Conformational considerations in the design of dual antagonists of platelet-activating factor (PAF) and histamine

Cited by 14 publications

References 8 publications

The Preparation and Solubility of Loratadine-Fumaric Acid Binary Mixture

The Preparation and Solubility of Loratadine-Fumaric Acid Binary Mixture

X-ray powder diffraction data for loratadine (C22H23ClN202)

Cyclizations of phenylethyl-substituted pyridinecarboxaldehydes

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X-ray powder diffraction data for loratadine (C₂₂H₂₃ClN₂0₂)