Improved and Efficient Process for the Production of Highly Pure Iloperidone: A Psychotropic Agent

Solanki, Pavankumar V.; Uppelli, Sekhar Babu; Pandit, Bhushan S.; Mathad, Vijayavitthal T.

doi:10.1021/op400335p

Cited by 10 publications

(3 citation statements)

References 5 publications

(6 reference statements)

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“…[88,89] Second-generation atypical antipsychotics are the benzofused isoxazoles risperidone 20 (among the top-ten costliest drugs), [89] its metabolite paliperidone 21,i loperidone 22,a nd ocaperidone 23 (Figure 8). [90][91][92][93] Compounds 20, 21,a nd 23 represent as uccessful application of scaffold hopping. [94] They act principally as dopaminergic D 2 and serotonergic 5-HT 2A receptor antagonists (preferably to the latter) towardr epressing schizophrenia and bipolar disorder.…”

Section: Psychoactive Drugs (Psychotropics)mentioning

confidence: 99%

The Isoxazole Ring and Its N‐Oxide: A Privileged Core Structure in Neuropsychiatric Therapeutics

et al. 2017

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Mental disorders are neuropsychiatric conditions that are marked by unusual or irregular thinking, feelings, or behavior, and lead to distress and/or impaired functions. Major psychiatric conditions are depression, anxiety, and psychoses of various types. Their etiopathogeneses, of a primary or secondary origin, are associated with genetic and environmental factors. They are commonly treated with psychoactive drugs (also known as psychotropics), which target serotonin, dopamine, norepinephrine, glutamate, and nuclear receptors (NRs), including retinoic acid receptor-related orphan receptors (RORs) and other receptors in the central nervous system (CNS). Herein we present a diverse array of isoxazole derivatives, among which are some prominent marketed drugs. Some of the derivatives and forms, including N-oxides, are under either (pre)clinical evaluation or patent protection as new generation of psychotropics, and a few have effective blood-brain barrier (BBB) permeability. Various drug-like isoxazol(in)es and their structural features and efficiency, modified through scaffold hopping, are described and discussed in the context of treating neuropsychiatric conditions.

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Section: Psychoactive Drugs (Psychotropics)mentioning

confidence: 99%

The Isoxazole Ring and Its N‐Oxide: A Privileged Core Structure in Neuropsychiatric Therapeutics

et al. 2017

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“…However, these papers were restricted to the determination of Iloperidone and failed to discuss the details of processrelated impurities and degradation impurities formed under the stress conditions employed. Recently, we reported an efficient and industrial scale synthesis of Iloperidone [19] from our laboratory. During the synthesis of Iloperidone, we come across many process related impurities and some of them were captured in our prior report.…”

Section: Introductionmentioning

confidence: 99%

Development and Validation of RP-UPLC Method for the Determination of Iloperidone, Its Related Compounds and Degradation Products in Bulk and Dosage Form

Landge¹,

Jadhav²,

Vishwambar³

et al. 2014

AJAC

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A rapid, specific, sensitive, and precise reverse-phase UPLC method developed for the quantitative determination of an atypical antipsychotic drug Iloperidone and its eight potential impurities in drug substances and drug products is described in this report. Chromatographic separation was achieved on a Waters Acquity UPLC ® HSS C18 (2.1 mm × 100 mm, 1.8 micron) column thermostated at 35˚C with a short runtime of 10 min. Quantification is achieved with photodiode array detection at 225 nm over the concentration range of 0.03 -0.15 µg/mL. Forced degradation study was carried out under acidic, alkaline, oxidative, photolytic and thermal conditions to demonstrate the stability-indicating capability of the developed UPLC method. Comparison of system performance with conventional high-performance liquid chromatography is made with respect to analysis time, efficiency, and sensitivity. The method is validated according to the ICH guidelines and is applied successfully for the determination of Iloperidone in tablets.

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“…Iloperidone is an antipsychotic pharmaceutical bearing an aromatic methyl ketone functionality . We have demonstrated that the CF 3 analog of iloperidone 6q can be synthesized from 2q by simple S N 2 displacement of the chloride with a commercially available amine (Scheme ).…”

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Access to Aryl and Heteroaryl Trifluoromethyl Ketones from Aryl Bromides and Fluorosulfates with Stoichiometric CO

et al. 2020

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We report a sequential one-pot preparation of aromatic trifluoromethyl ketones starting from readily accessible aryl bromides and fluorosulfates, the latter easily prepared from the corresponding phenols. The methodology utilizes low pressure carbon monoxide generated ex situ from COgen to generate Weinreb amides as reactive intermediates that undergo monotrifluoromethylation affording the corresponding aromatic trifluoromethyl ketones (TFMKs) in good yields. The stoichiometric use of CO enables the possibility for accessing 13 C-isotopically labeled TFMK by switching to the use of 13 COgen.

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Improved and Efficient Process for the Production of Highly Pure Iloperidone: A Psychotropic Agent

Cited by 10 publications

References 5 publications

The Isoxazole Ring and Its N‐Oxide: A Privileged Core Structure in Neuropsychiatric Therapeutics

The Isoxazole Ring and Its N‐Oxide: A Privileged Core Structure in Neuropsychiatric Therapeutics

Development and Validation of RP-UPLC Method for the Determination of Iloperidone, Its Related Compounds and Degradation Products in Bulk and Dosage Form

Access to Aryl and Heteroaryl Trifluoromethyl Ketones from Aryl Bromides and Fluorosulfates with Stoichiometric CO

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