119222-30-9

Upstream product

• 93416-62-7 5-amino-1-(2-fluorobenzyl)-1H-1,2,3-triazole-4-carboxamide 
• 62284-30-4 2-fluorobenzyl azide 

Downstream Products

• 119222-06-9 7-(N,N-dimethylamino)-3-(2-fluorobenzyl)-3H,1,2,3-triazolo-[4,5-d]pyrimidine 
• 119222-29-6 3-(2-fluorobenzyl)-7-chloro-1,2,3-triazolo[4,5-d]pyrimidine 

Relevant academic research and scientific papers

New amino derivatives of 1,2,3-triazolo[4,5-d]pyrimidines and their affinity towards A1 and A(2A) adenosine receptors

Starting from the appropriate azides (4-chlorobenzyl-, 2- thiophenemethyl-, 2-fluorobenzyl-, and 4-fluorobenzylazides) in which the variation of the substituent is at the basis of the four series of derivatives (a-d), the 7-aminosubstituted 1,2,3-triazolo[4,5-d]pyrimidines 4 were prepared by a well known synthetic route. The biological activity of compounds 4 was expected on the basis of the presence of particular substituents on N(7), and these substituents were introduced by the reaction of the 7 lactamic carbonyl function, present on precursors 3, with cycloalkyl-, aralkyl- and arylamines. Radioligand binding assays at bovine brain adenosine A1 and A(2A) receptors showed that some compounds possessed a high affinity and selectivity for the A1 receptor subtype. Furthermore, biological results indicated that the p-chlorobenzyl substituent lowered receptor binding, compared with the previously prepared benzyl and 2-chlorobenzyl derivatives, suggesting certain particular steric requirements of the lipophilic region which interacts with the benzyl substituent. The thiophenemethyl substituent conferred more activity than the benzyl one. The presence of a fluorine atom on the benzyl group determined a high affinity, especially when it was in the ortho position. Compounds 4c.1 (R = 2-fluorobenzyl, R' = cyclopentyl, Ki = 10.5 nM), 4c.2 (R = 2-fluorobenzyl, R' = cyclohexyl, Ki = 19.5 nM) and 4d.1 (R = 4- fluorobenzyl, R' = cyclopentyl, Ki = 26 nM) were the most active for A1 receptors.

3-benzyl-3H-1,2,3-triazolo[4,5-d]pyrimidines, compositions thereof, and method of treating epilepsy therewith

Tbe invention relates to 3H-1,2,3-triazolo[4,5-d]pyrimidine derivatives, especially substituted 3-benzyl-3H-1,2,3-triazolo[4,5-d]-pyrimidines of the general formula STR1 in which Ph represents a phenyl radical substituted by halogen, lower alkyl, trifluoromethyl and/or by cyano, R1 represents a free amino group or an amino group that is substituted aliphatically, cycloaliphatically, cycloaliphatically-aliphatically and/or by acyl, and R2 represents hydrogen, lower alkyl, a free amino group, or an amino group that is substituted aliphatically, cycloaliphaically, cycloaliphatically-aliphatically and/or by acyl, in free form or in form of a salt, with the proviso, that in a compound of formula I in free form, wherein R1 represents N,N-di-C1 -C6 -alkylamino in which the two N-C1 -C6 -alkyl groups may be the same or different, N-mono-C1 -C6 -alkylamino or amino, R2 is other than hydrogen and other than C1 - C6 -alkyl, if Ph represents a phenyl radical which is monosubstituted by halogen or by trifluoromethyl, and to compounds of formula I in free form wherein either Ph is o-fluorophenyl, R1 is N-mono-methylamino or amino, and R2 is hydrogen or methyl or wherein Ph is o-fluorophenyl, o-chlorophenyl or m-trifluoromethylphenyl, R1 is N,N-di-methylamino, and R2 is hydrogen or wherein Ph is m-fluorophenyl, p-fluorophenyl, o-chlorophenyl, o-trifluoromehylphenyl, m-trifluoromethylphenyl or p-trifluoromethylphenyl, R1 is N-mono-methylamino, and R2 is hydrogen. These compounds and salts can be used as pharmaceutical active ingredients and can be produced in a manner known per se.