55309-05-2Relevant academic research and scientific papers
Influence of metabolism on the activity of a new anti-fertility agent, 2-(3-ethoxyphenyl)-5,6-dihydro-s-triazolo [5,1-a]isoquinoline (DL 204-IT), in the rat and the hamster
Assandri,Perazzi,Martinelli,Ferrari,Ripamonti,Tuan,Galliani
, p. 2104 - 2111 (2007/10/02)
The activity of a new non-hormonal anti-fertility agent, 2-(3-ethoxyphenyl)-5,6-dihydro-s-triazolo[5,1-a]isoquinoline (DL 204-IT), effective in terminating pregnancy after i.m. or s.c. treatment, was tested after single and multiple oral doses given to rats and hamsters. Although the compound was absorbed well from the gastro-intestinal tract and the plasma levels of the radioactivity administered were rather high and sustained, the oral activity was by two orders of magnitude lower than the parenteral one. The plasma profile of the metabolites found after both p.o. and i.m. administration indicates that the compound is rapidly metabolized. Seven metabolites (I-VII) were isolated from the urine of pregnant rats and fully characterized by MS, IR and NMR spectroscopy. They are 2-(3-hydroxyphenyl)-5,6-dihydro-s-triazolo[5,1-a]isoquinoline (I); 2-(3,4-dihydroxyphenyl)-5,6-dihydro-s-triazolo-[5,1-a]isoquinoline (II); 2-(3-hydroxyphenyl)-5,6-dihydro-6β-hydroxy-s-triazolo[5,1-a]isoquinoline (III); metabolite I-sulphate ester (IV); metabolite III-3-sulphate ester (V); metabolite 1-β-D-glucuronide (VI) and metabolite II 3-β-D-glucuronide (VII). Metabolite I was shown to be from 1/10 (rat) to 1/30 (hamster) as active as the parent compound, while metabolites II and III were completely inactive. The very low oral activity of DL 204-IT seems to be due mainly to its rapid biotransformation.
2-Substituted phenyl-s-triazolo[5,1-a] isoquinoline compounds
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, (2008/06/13)
A new process for preparing s-triazolo[5,1-a]-isoquinoline derivatives of the formula STR1 wherein A represents the group --CH2 --CH2 -- or --CH=CH--; R is selected from hydrogen, amino, lower alkylamino, di-lower alkylamino, acylamino, diacylamino, ureido, thioureido, carbethoxythioureido, benzoylthioureido, sulfhydryl, lower alkyl, trifluoromethyl, phenyl, substituted phenyl, pyridyl, methylpyridyl and dimethylpyridyl; and R1 and R2 each independently represents hydrogen or lower alkoxy, by condensation of a 2-amino-3,4-dihydro-1(2H)-isoquinolinone with an imidolyl, cyanamide, cyanic or thiocyanic derivative. New compounds of the formula I wherein A represents the group --CH2 --CH2 -- or --CH=CH--, R has the same meaning as above with the exclusion of hydrogen, methyl, phenyl, and trifluoromethyl, R1 and R2 have the same meaning as above, with the proviso that when A represents the group --CH=CH--, R cannot be tolyl or pyridyl. The new compounds and some of the intermediates of the process are active as antiinflammatories, CNS depressants and anti-fertility agents.
2-Substituted phenyl-5-triazols [5,1-a] isoquinoline compounds
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, (2008/06/13)
A new process for preparing s-triazolo[5,1-a]-isoquinoline derivatives of the formula STR1 wherein A represents the group --CH2 --CH2 -- or --CH=CH--; R is selected from hydrogen, amino, lower alkylamino, di-lower alkylamino, acylamino, diacylamino, ureido, thioureido, carbethoxythioureido, benzoylthioureido, sulfhydryl, lower alkyl, trifluoromethyl, phenyl, substituted phenyl, pyridyl, methylpyridyl and dimethylpyridyl; and R1 and R2 each independently represents hydrogen or lower alkoxy; by condensation of a 2-amino-3,4-dihydro-1(2H)-isoquinolinone with an imidolyl, cyanamide, cyanic or thiocyanic derivative. New compounds of the formula I wherein A represents the group --CH2 --CH2 -- or --CH=CH--, R has the same meaning as above with the exclusion of hydrogen, methyl, phenyl, and trifluoromethyl, R1 and R2 have the same meaning as above, with the proviso that when A represents the group --CH=CH--, R cannot be tolyl or pyridyl. The new compounds and some of the intermediates of the process are active as antiinflammatories, CNS depressants and anti-fertility agents.
