16263-52-8

Usage

Uses

Used in Pharmaceutical Industry:
3-Chloro-1,2-benzisoxazole is used as a reactant/reagent for the preparation of piperazine and piperidine cyclohexyl derivatives. These derivatives have potential applications in the treatment of psychoneurosis, a class of mental disorders that includes conditions such as anxiety, depression, and neurotic disorders. The compound's reactivity and structural features make it a valuable building block in the synthesis of various pharmaceutical compounds with therapeutic potential.

InChI:InChI=1/C7H4ClNO/c8-7-5-3-1-2-4-6(5)10-9-7/h1-4H

Upstream product

• 119841-74-6 N,2-dihydroxybenzenecarbonimidoyl chloride 
• 89-73-6 salicylhydroxamic acid 
• 21725-69-9 3-hydroxybenzisoxazole 
• 21725-69-9 1,2-benz-4-isooxazolin-3-one 

Downstream Products

• 16302-63-9 3-Chlor-5-nitro-1,2-benzisoxazol 
• 374554-40-2 N-(benzo[d]isoxazol-3-yl)benzene-1,3-diamine 
• 87691-89-2 4(1,2-benzisoxazol-3-yl)piperazine 
• 251655-36-4 benzo[d]isoxazol-3-yl-{4-[3,5-bis(trifluoromethyl)pyrazol-1-yl]phenyl}amine 
• 87692-13-5 4-<4-(1,2-benzisoxazol-3-yl)-1-piperazinyl>-1-(4-fluorophenyl)-1-butanone hydrochloride 

Relevant academic research and scientific papers

An efficient synthesis of oxazolines: Via a cascade reaction between azaoxyallyl cations and 1,2-benzisoxazoles

A formal [3 + 2] cycloaddition reaction between the C and O terminals of azaoxyallyl cations formed in situ and 1,2-benzisoxazoles has been realized. This one-pot cycloaddition method provided an effective and practical pathway to synthesize oxazoline in good yields under mild conditions. The title products exhibited unique fluorescence properties.

Synthesis of a bicyclic piperazine from l-aspartic acid and application of a fluoride-promoted SNAr coupling

The process development is reported of a pivotal C-N bond formation involving ((7R,9aS)-octahydro-1H-pyrido[1,2-a]pyrazin-7-yl)methanol (2) undergoing nucleophilic aromatic substitution with 3-chlorobenzo[d]isoxazole (3) to furnish ((7R,9aS)-2-(benzo[d]isoxazol-3-yl)octahydro-1H-pyrido[1,2-a] pyrazin-7-yl)methanol (4) as a key intermediate for a family of compounds (1). Essential to the success of the coupling is the use of fluoride in combination with a phase transfer catalyst. The development of an alternative route to bicyclic piperazine 2 that uses l-aspartic acid (20) as a starting material to avoid the need for a classical salt resolution is described.

PROLINE DERIVATIVES AND USE THEREOF AS DRUGS

The present invention aims at providing compounds having therapeutic effects due to a DPP-IV inhibitory action, and satisfactory as pharmaceutical products. The present inventors have found that derivatives having a substituent introduced into the γ-position of proline represented by the formula (I) wherein each symbol is as defined in the specification, have a potent DPP-IV inhibitory activity, and completed the present invention by increasing the stability.

Synthesis of an Optically Active Octahydro-2H-pyridopyrazine Based CNS Agent

A synthesis of an optically active octahydro-2H-pyridopyrazine is presented.The key sequence involved the equilibration of an optically active cis-aldehyde to give the thermodynamic transaldehyde that was trapped by nitromethane anion.

Synthesis and Biological Evaluation of 1-(1,2-Benzisothiazol-3-yl)- and (1,2-Benzisoxazol-3-yl)piperazine Derivatives as Potential Antipsychotic Agents

Members of the series of title compounds were tested for potential antipsychotic activity in relevant receptor binding assays and behavioral screens.Structure-activity relationships within the series are discussed.Compound 24 (BMY 13859-1), a (1,2-benzisothiazol-3-yl)piperazine derivative, was selected for further study because of its potent and selective profile in primary CNS tests.It was active in the Sidman avoidance paradigm and blocked amphetamine-induced stereotyped behavior in dogs for up to 7 h.The compound's lack of typical neuroleptic-like effects in therat catalepsy test and its failure to produce dopamine receptor supersensitivity following chronic administration indicate that it should not cause the movement disorders commonly associated with antipsychotic therapy.Although 24 has potent affinity for dopaminergic binding sites, its even greater affinity for serotonin receptors suggests that a serotonergic component may be relevant to its atypical profile.Compound 24 is currently undergoing clinical evaluation in schizophrenic patients.