Edaravone cocrystals: synthesis, screening, and preliminary characterization

Veverka, Miroslav; Dubaj, Tibor; Gallovič, Ján; Švajdlenka, Emil; Meľuchová, Beáta; Jorı́k, Vladimı́r; Šimon, Peter

doi:10.1007/s00706-013-1029-0

Cited by 5 publications

(2 citation statements)

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“…The case study compound, PROPY, shows structural similarity to two other compounds, antipyrine and edaravone, which contain the same molecular skeleton (phenylpyrazole); however PROPY contains an isopropyl substituent which causes steric hindrance at the carbonyl (Figure ). A number of multicomponent systems − have been reported for antipyrine and edaravone, from which additional knowledge can be gained and can be used in the design and search for cocrystals of PROPY. An analysis of these systems indicates that most of the coformers feature CO 2 H donor groups.…”

Section: Resultsmentioning

confidence: 99%

Design of Cocrystals for Molecules with Limited Hydrogen Bonding Functionalities: Propyphenazone as a Model System

Mapp

Coles

Aitipamula

2016

Crystal Growth & Design

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ABSTRACT:We report eight new cocrystals with an analgesic drug, propyphenazone, which belongs to a family of compounds that possess limited or no hydrogen bonding functionality. Such molecules 2 present difficulties in predicting and selecting appropriate coformers for potential multicomponent systems, and current prediction methodologies are unsuitable due to their focus around hydrogen bonding. This study used a knowledge-based strategy to identify appropriate coformers as well as testing a wide variety of molecules to confirm the initial predictions. All new cocrystals were characterized using X-ray diffraction techniques as well as measuring their physiochemical properties. These included the thermal behavior, stability under slurry and accelerated conditions, solubility and dissolution rate and were compared with the parent propyphenazone. It was found that while the stability of most of the cocrystals and propyphenazone was comparable, a cocrystal with hydroquinone showed an increase in both the solubility and dissolution rate of propyphenazone.

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Section: Resultsmentioning

confidence: 99%

Design of Cocrystals for Molecules with Limited Hydrogen Bonding Functionalities: Propyphenazone as a Model System

Mapp

Coles

Aitipamula

2016

Crystal Growth & Design

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“…It has been reported that it can eliminate lipid peroxides and hydroxyl radicals. Edaravone was developed by Mitsubishi Tanabe Pharma Corporation and was approved to improve neurological symptoms, activities of daily living, and dysfunction caused by acute cerebral infarction in Japan, in 2001. − In 2017, the US Food and Drug Administration approved edaravone for the treatment of patients with amyotrophic lateral sclerosis (ALS), commonly known as Lou Gehrig’s disease. − Therefore, the demand for edaravone is increasing in the current market.…”

Section: Introductionmentioning

confidence: 99%

Scale-Up of a Continuous Manufacturing Process of Edaravone

Zhou

Hong

Mei

et al. 2021

Org. Process Res. Dev.

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Edaravone belongs to a class of brain-protective agents, which can scavenge free radicals. To reduce impurities and improve the yield, a continuous flow production process of edaravone was developed. The synthesis is continuously carried out in two steps. The throughput can reach 11.328 kg/day and the purity of the final product is 99.95%, which are in accordance with the needs of production. This is an efficient and quick production process suitable for industrial production.

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Electrochemical‐Induced C(sp³)−H Dehydrogenative Trimerization of Pyrazolones to Tripyrazolones

Yang

Yan

et al. 2021

Eur J Org Chem

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The electrochemical‐induced three‐component C(sp3)−H dehydrogenative trimerization of pyrazolones to tripyrazolones with hydrogen evolution has been accomplished under the metal‐ and external‐oxidant‐free conditions. This protocol provides an efficient and eco‐friendly method for the synthesis of tripyrazolones, which avoids the use of metals and stoichiometric chemical oxidants. A wide range of functional groups was tolerated to give selectively the desired products in high yields. Importantly, such an electrochemical‐oxidation‐induced dehydrogenative trimerization reaction could be easily scaled up with excellent efficiency.

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Edaravone cocrystals: synthesis, screening, and preliminary characterization

Cited by 5 publications

References 50 publications

Design of Cocrystals for Molecules with Limited Hydrogen Bonding Functionalities: Propyphenazone as a Model System

Design of Cocrystals for Molecules with Limited Hydrogen Bonding Functionalities: Propyphenazone as a Model System

Scale-Up of a Continuous Manufacturing Process of Edaravone

Electrochemical‐Induced C(sp³)−H Dehydrogenative Trimerization of Pyrazolones to Tripyrazolones

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Edaravone cocrystals: synthesis, screening, and preliminary characterization

Cited by 5 publications

References 50 publications

Design of Cocrystals for Molecules with Limited Hydrogen Bonding Functionalities: Propyphenazone as a Model System

Design of Cocrystals for Molecules with Limited Hydrogen Bonding Functionalities: Propyphenazone as a Model System

Scale-Up of a Continuous Manufacturing Process of Edaravone

Electrochemical‐Induced C(sp3)−H Dehydrogenative Trimerization of Pyrazolones to Tripyrazolones

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Electrochemical‐Induced C(sp³)−H Dehydrogenative Trimerization of Pyrazolones to Tripyrazolones