[Synthesis of new pyrido-(3',2':4,5)-thieno-(3,2-d)-1,2,3-triazine derivatives as antianaphylactics].

Some new pyrido[3',2':4,5]thieno[3,2-d]1,2,3-triazine-4(3H)-ones (C) were synthesized from 2-thioxo-1,2-dihydro-3-carbonitriles (A) via the 3-amino-thieno[2,3-b]pyridine-2-carboxamides (B). Substances of structure A were converted to 3-amino-thieno[2,3-b]pyridine-2-carbonitriles (G) which yielded the desired 4-amino substituted compounds I via the tricyclic 4-chloro-pyrido[3',2':4:5]thieno[3,2-d]1,2,3-triazines (H) by the reaction with N-nucleophiles. Some of the investigated compounds showed a respectable antianaphylactic activity.

[Synthesis of thieno(2,3-b)pyridines with oxalamidic acid or an oxalamidic alkylester residues and of 4-alkoxy-pyrido(3',2':4,5)thieno(3,2-d)pyridine-2-carboxylic acid derivates].

N-(2-Alkoxycarbonyl-thieno[2,3-b]pyrid-3-yl)oxalamide acid alkylester B were synthesized by the reaction of 3-amino-2-carboxylic esters A with oxalic acid diethylester in presence of sodium alkoxides. The 3-amino-2-cyano-thieno[2,3-b]pyridines C yielded under the same conditions via the N-(2-cyano-thieno[2,3-b]pyrid-3-yl)oxalamidic acid alkylesters D/1-D/4 the 4-alkoxy-pyrido[3',2':4,5]thieno[3,2-d]pyrimidine-2-carboxylic acid alkylesters E/1-E/8. The compounds D/1, D/2 and E/1-E/5 were hydrolyzed to give the corresponding carboxylic acids.

[Synthesis of furo(2,3-b)pyridine amidines with antianaphylactic activity].

The synthesis of furo[2,3-b]pyridine formamidines (D/1-D/11, F) was realized by the reaction of the 3-amino-furo[2,3-b]pyridines C/1-C/11 and E, substituted in position 2 with a carbonyl moiety with dimethylformamide/phosphoroxide chloride or with N-formyl-piperidine or N-formyl-morpholine and phosphoroxide chloride. The acetamidines H were yielded from 4-oxo-4H-3-methyl-pyrido[3',2':4,5]furo[3,2-d]1,3-oxazines with aminoethanol. The 4-oxo-4H-3-amino-3,4-dihydro-pyrido[3',2':4,5]furo[3,2-d]pyrimidines K and M reacted with dimethylformamide/phosphoroxide chloride to give the tricyclic formamidines L and K.

[Synthesis of N-(2-carboxy-thieno(2,3-b)pyridin-3-yl)-formamidines corresponding alkyl esters with antianaphylactic activity].

A lot of N-(2-carboxy-thieno[2,3-b]pyridin-3-yl)formamidines especially in form of their amine salts--were synthesized by reaction of 3-amino-thieno[2,3-b]pyridine-2-carboxylic acids with dimethylformamide/phosphoroxide chloride or by reaction of 4-oxo-4H-pyrido[3',2':4,5]thieno[3,2-d]1,3- oxazines with amines. Carboxylic acid alkylesters of this structure were yielded from 3-amino-thieno[2,3-b]pyridine-2-carbonic acid alkylesters by reaction with dimethylformamide/phosphoroxide chloride or with N-formyl-piperidine or N-formyl-morpholine and phosphoroxide chloride. The compounds showed antianaphylactic activity.

[Synthesis of N-(2-carboxy-thieno(2,3-b)pyridin-3-yl)-amidines by the reaction with 4-oxo-4H-pyrido(3',2':4,5)-thieno(3,2-d)-1,3-oxazines with secondary cycloaliphatic amines].

4-Oxo-4H-pyrido[3',2':4,5]thieno[3,2-d]1,3-oxazines react with secondary cycloaliphatic amines to give besides the expected bisamides the amine salts of N-(2-carboxy-thieno[2,3-b]pyridine-3-yl)amidines. These compounds showed inhibitory activity against different lipoxygenases, but a small chemical stability.