Synthesis of 3-methyl-substituted pyrazolotriazolopyrimidin-4-one and pyrazolothiazolopyrimidin-4-one derivatives

As a part of a research on anti-inflammatory analgesic compounds 3-methyl substituted pyrazolotria-zolopyrimidin-4-one and pyrazolothiazolopyrimidin-4-one derivatives were prepared by previously reported procedures. None of the compounds showed improved activity when compared with the previously reported unsubstituted analogs.

[1]  M. Santagati,et al.  Synthesis and NK-2 antagonist effect of 1,6-diphenyl-pyrazolo [3,4-d]-thiazolo[3,2-a]4H-pyrimidin-4-one , 1996 .

[2]  S. Guccione,et al.  Potential of alkyl orthoformates as alkylating agents of non‐electron rich nitrogen heterocycles , 1995 .

[3]  S. Guccione,et al.  Pyrimido[5,4-b]indole derivatives. 1. A new class of potent and selective alpha 1 adrenoceptor ligands. , 1991, Journal of medicinal chemistry.

[4]  Toshio Hayashi,et al.  Reactions of α-Cyano-β-methoxy-β-alkylacrylic Esters with Hydrazine and Hydroxylamine , 1969 .

[5]  H. Beyer,et al.  Über Thiazole, XXIX. Mitteil.: Über die Kondensationsprodukte von Thiosemicarbazid mit α- Chloracetessigester und eine neuartige Ringverengung des 2-Amino-5- methyl-6-carbäthoxy −1.3.4-thiodiazins zum 3-Methyl-4- carbäthoxy-5-amino-pyrazol , 1956 .

[6]  I. B. Douglass,et al.  The Preparation and Hydrolysis of Mono- and Disubstituted Benzoylthioureas1 , 1934 .

[7]  S. Guccione,et al.  Unforeseen alkylating effect of triethylorthoformate in the synthesis of pyrazolotriazolopyrimidine derivative , 1995 .

[8]  G. Ambrosini,et al.  Pyrimido[5,4-b]benzofuran and pyrimido[5,4-b]benzothiophene derivatives Ligands for α1-and 5HT1A-receptors , 1993 .

[9]  S. Guccione,et al.  Pyrazolothiazolopyrimidine derivatives as a novel class of anti-inflammatory or antinociceptive agents: synthesis, structural characterization and pharmacological evaluation , 1993 .

[10]  S. Guccione,et al.  Synthesis and pharmacological properties of pyrazolotriazolopyrimidine derivatives , 1992 .

[11]  R. Pech,et al.  Über neue Pyrazolverbindungen. IV Darstellung und Cyclisierungsverhalten einiger akzeptorsubstituierter N‐(Pyrazol‐3‐yl)‐thioharnstoffe , 1991 .

[12]  C. T. Adams,et al.  Dehydrogenation and coupling reactions in the presence of iodine and molten salt hydrogen iodide acceptors , 1977 .