133783-64-9

Upstream product

• 461-82-5 4-(trifluoromethoxy)aniline 
• 98-59-9 p-toluenesulfonyl chloride 
• 133783-52-5 2-amino-2-[4-(trifluoromethoxy)phenyl]ethanol 

Downstream Products

• 133783-63-8 4-phenyl-1-[2-(4-trifluoromethoxyanilino)ethyl]-1,2,3,6-tetrahydropyridine 
• 139362-36-0 N-methyl-N-[2-(4-trifluoromethoxyanilino)ethyl]benzylamine 
• 139362-37-1 N-methyl-N-phenethyl-N'-(4-trifluoromethoxy-phenyl)-ethane-1,2-diamine 

Relevant academic research and scientific papers

Riluzole series. synthesis and in vivo 'antiglutamate' activity of 6- substituted-2-benzothiazolamines and 3-substituted-2-imino-benzothiazolines

Two series of analogues of riluzole, a blocker of excitatory amino acid mediated neurotransmission, have been synthesized: monosubstituted 2- benzothiazolamines and 3-substituted derivatives. Of all the compounds prepared in the first series, only 2-benzothiazolamines bearing alkyl, polyfluoroalkyl, or polyfluoroalkoxy substituents in the 6-position showed potent anticonvulsant activity against administration of glutamic acid in rats. The most active compounds displaying in vivo 'antiglutamate' activity were the 6-OCF3 (riluzole), 6-OCF2CF3, 6-CF3, and 6-CF2CF3 substituted derivatives with ED50 values between 2.5 and 3.2 mg/kg i.p. Among the second series of variously substituted benzothiazolines, compounds as active as riluzole or up to 3 times more potent were identified in two series: benzothiazolines bearing a β-dialkylaminoethyl moiety and compounds with an alkylthioalkyl chain and their corresponding sulfoxides and sulfones. The most potent derivatives were 2-imino-3-(2-methylthio)- and 2-imino-3-(2- methylsulfinyl)-ethyl-6-trifluoromethoxybenzothiazolines (61 and 64, ED50 = 1.0 and 1.1 mg/kg i.p., respectively). In addition, intraperitoneal administration of some of the best benzothiazolines protected mice from mortality produced by hypobaric hypoxia.

Benzothiazole derivatives and medicinal products containing them

STR1 Compounds of formula (I), in which R1 is a polyfluoralkoxy, R2 is a sulphur or nitrogen atom substituted by an alkyl radical or a sulfonyl or sulfinyl radical, R3 is a phenyl, benzoyl, --NR4 R5 or piperidinyl-4radical substituted in position 1 by a phenylalkyl radical, R4 is an alkyl radical, R5 is a phenylalkyl radical, n is equal to 1, 2 or 3, m is equal to 0, 1, 2 or 3. The present invention also relates to the salts of said compounds, processes for the preparation of the latter and drugs containing them.

2-imino-3-alkylbenzothiazoline derivatives bearing a heterocyclic substituent on the alkyl group, their preparation and medicinal products containing them.

Compounds of formula: STR1 in which R1 represents a substituted 1-piperazinyl, substituted 1,2,3,6-tetrahydro-1-pyridyl or substituted piperidino radical, R2 represents a polyfluoroalkoxy or a polyfluoroalkyl radical and n is equal to 2 or 3, the salts of these compounds with an acid, processes for preparing them and medicinal products containing them.