63463-50-3

Upstream product

• 63463-45-6 4-chloro-1-cyclopropylmethyl-piperidine 
• 63778-91-6 1-cyclopropylmethyl-4-piperidyl-magnesium chloride 
• 63418-31-5 3-trifluoro-methylthio-5H-dibenzo[a,d]cyclohepten-5-one 

Relevant academic research and scientific papers

Synthesis and stereospecific antipsychotic activity of (-) 1 cyclopropylmethyl 4 (3 trifluoromethylthio 5H dibenzo[a,d]cyclohepten 5 ylidene)piperidine

The synthesis and resolution of 3-iodocyproheptadine [(±)-5a] and a-cyclopropylmethyl-4-(3-iodo-5H-dibenzo-[a,d]cyclohepten-5-ylidene) piperidine [(±)-5b] are described. The resulting atropisomers undergo reaction with trifluoromethylthiocopper to give optically active products without extensive racemization. In this manner, optically pure (+)- and (-) 3-trifluoromethylthiocyproheptadine [(+)-6a and (-)-6a, respectively] and (+)- and (-)-1-cyclopropylmethyl-4-(3-trifluoromethylthio-5H-dibenzo[a,d]cyclohepten5-ylidene) piperidine [(+)-6b and (-)-6b, respectively] have been prepared. The influence of a chiral europium shift reagent on the proton and fluorine resonance signals as a diagnostic tool for the determination of the optical purities of these atropisomers is discussed. The four compounds, (+)-6a, (-)-6a,(+)-6b, and (-)-6b, were studied in squirrel monkeys for their ability to block conditioned avoidance responding. All of the antiavoidance activity was found to reside solely in the levorotatory compounds (-)-6a and (-)-6b. Further comparison of the enantiomers (-)-6b and (+)-6b showed that the ability to antagonize apomorphine-induced stereotyped behavior is confined to the levorotatory isomer (-)-6b while weak central anticholinergic activity resides solely in the dextrorotatory isomer (+)-6b. Neither (-)-6b nor (+)-6b has significant peripheral anticholinergic activity.

Method of traeting malaria with cyproheptadine derivatives

Various 3-substituted cyproheptadine derivatives are useful in the treatment of infection by Plasmodium falciparum and in the treatment of malaria either as compounds, pharmaceutically acceptable salts, or pharmaceutical composition ingredients in combina

Trifluoromethylthio (and sulfonyl) derivatives of cyproheptadine analogs

Cyproheptadine derivatives substituted with a trifluoromethylthio or trifluoromethylsulfonyl group in one of the benzo rings and having a hydroxyalkyl or cycloalkylalkyl group on the piperidine nitrogen are potent antipsychotic agents, with a low propensity to induce extrapyramidal side effects that are experienced with most major tranquilizers. The tranquilizing activity is predominantly in the levorotatory enantiomers, whereas the dextrorotatory enantiomers have anticholinergic activity. Each enantiomer is useful as a source of the other by racemization. The novel compounds are prepared by treatment of the corresponding iodo or bromo compound with bis(trifluoromethylthio)mercury and copper powder.