80272-23-7

Usage

InChI:InChI=1/C16H13FO/c1-10-2-7-13-14(9-16(18)15(13)8-10)11-3-5-12(17)6-4-11/h2-8,14H,9H2,1H3

Upstream product

• 460-00-4 1-Bromo-4-fluorobenzene 
• 80271-85-8 2-Cyano-3-(4-fluoro-phenyl)-3-p-tolyl-propionic acid ethyl ester 
• 18300-87-3 ethyl 2-cyano-3-p-tolylacrylate 
• 390-43-2 3-(4-fluoro-phenyl)-3-p-tolyl-propionic acid 

Downstream Products

• 344754-99-0 3-Chloro-1-(4-fluoro-phenyl)-5-methyl-indan 
• 85663-42-9 Lu 17-050 
• 80272-47-5 (1R,3R)-3-(4-Fluoro-phenyl)-6-methyl-indan-1-ol 

Relevant academic research and scientific papers

Indane derivatives, pharmaceutical compositions thereof and method of preparation

The present invention relates to novel 1-piperazino-3-phenyl-indane derivatives which have pronounced psychopharmacological activity such as neuroleptic activity, analgesic activity, antidepressant activity and, at the same time, a low degree of undesired side-effects, methods for the preparation of said indane derivatives, pharmaceutical compositions containing same, and methods for the treatment of psychic disorders, such as psychoses and depressions and pain, by administering a therapeutically active amount of one of said derivatives to a living animal body, including human beings.

Neuroleptic activity and dopamine-uptake inhibition in 1-piperazino-3-phenylindans

A series of 1-piperazino-3-phenylindans was synthesized and tested for neuroleptic and thymoleptic activity. Neuroleptic activity was found only in trans racemates and was associated with one of the enantiomers only. The potent and long-acting neuroleptic compound trans-4-[3-(4-fluorophenyl)-6-(trifluoromethyl)indan-1-yl]-1-piperazineeth anol (Lu 18-012, tefludazine) was developed by systematic variation of structural components. Thymoleptic activity was optimized, especially with respect to dopamine-uptake inhibition. No geometrical stereoselectivity was found with regard to dopamine-uptake inhibition, but a high enantioselectivity could be demonstrated for both cis and trans racemates. The most potent compounds were 1-piperazino-3-(3,4-dichlorophenyl)indans with IC50 values of about 2 nM for inhibition of dopamine uptake.