[Synthesis of 3-cyano-6-methyl-4-pyridyl-2(1H)-pyridinethiones as well as 2-substituted 6-methyl-4-pyridyl-pyridine-3-carbonitriles and 3-carbonic acid amides, respectively, and testing their cardiovascular activity]. / Synthese von 3-Cyan-6-methyl-4-pyridyl-2(1H)-pyridinthionen sowie neuer in 2-Stellung substituierter 6-Methyl-4-pyridyl-pyridin-3-carbonitrile bzw. -3-carbonsäureamide und deren Prüfung auf kardiovaskuläre Wirksamkeit.

By the base catalyzed reaction of our previously described 3-cyano-6-methyl-4-pyridyl-2(1H)-pyridinethiones 1 and 2, respectively, with branched and unbranched, respectively, alkyl, aralkyl-, alkinyl-, hydroxyalkyl-, ethoxycarbonyl- and carbamoylalkylhalides the new in 2-position substituted 6-methyl-4-pyridyl-pyridine-3-carbonitriles 15-30 were formed. By means of oxidation of the 2-methylthio-substituted pyridine-3-carbonitriles 3 and 4 with potassium periodate and potassium permanganate in diluted acetic acid, respectively, the sulfinyl compounds 5 and 6, respectively, and the sulfonyl compounds 7 and 8, respectively, were prepared. By heating of 3 and 4, respectively, with concentrated sulphuric acid the 2-methylthio-pyridine-3-carboxamides 9 and 10 were obtained. The oxidation of these compounds with potassium periodate and potassium permanganate, respectively, had yield the pyridines 11 and 12, respectively, as well as 13 and 14, respectively.

[Synthesis of 3-substituted 6-methyl-4-pyridyl-2 (1H) pyridones and testing of their cardiovascular action]. / Synthese von 3-substituierten 6-Methyl-4-pyridyl-2(1H)-pyridonen und deren Prüfung auf kardiovaskuläre Wirksamkeit.

Reaction of our previously described and in 4- and 6-, respectively, position with 3- and 4-, respectively, substituted 3-cyan-2(1H)-pyridones 4 and 5 with concentrated sulphuric acid had yielded the 3-carbamoyl-pyridones 8 and 9. Hofmann reaction was followed and the 3-amino substituted pyridones 10 and 11 were formed. As by-products the 5-bromo substituted 3-amino-pyridones 12 and 13 were obtained. 4 and 5 were refluxed in the presence of diluted sulphuric acid to yield the decarboxylated pyridones 14 and 15. Cardiotonic Activity of the compounds 4-9 compared to amrinone (Cordemcura) was investigated.

[Synthesis of phenol-antigen conjugates by reacting N-hydroxysuccinimidic esters of hydroxybenzoic acids with human serum albumin and bovine gamma globulin]. / Synthese von Phenol-Antigen-Konjugaten durch Umsetzung von N-Hyroxysuccinimidestern von Hydroxybenzoesäuren mit Humanserumalbumin und Rindergammaglobulin.

Salicylic acid, beta-resorcylic acid and gentisic acid were acetylated and then reacted with N-hydroxysuccinimide according to the DDC procedure to give the corresponding activated esters. The reaction of these N-hydroxysuccinimidic esters with human serum albumin and bovine gamma globulin yielded modified proteins containing hydroxybenzoyl residues linked to amino groups, the mode of linkage being of the acid amide type.

[Suppressive effects of 5-bromuracile and 5-bromuracile-epsilon-aminocaproic acid on the humoral anti-sheep erythrocyte immune response of mice in vivo and in vitro (author's transl)]. / Suppressive Wirkungen von 5-Bromuracil und 5-Bromuracil-Aminocapronsäure auf die humorale Anti-Schaferythrozyten-Immunreaktion der Maus in vivo und in vitro.

4 x 30 mg/kg 5-bromuracile (5-BrU) - injected shortly after the antigen once per day - suppress the development of direct plaque forming cells (PFC) in the spleen of immunized mice on the 4th day of the primary reaction weakly. 5 higher doses epsilon-aminocapronic acid (ACA) were not immunosuppressive, but those of 5-BrU-ACA. The immunosuppression was of short time, 6 days later equal direct PFCs were found in the spleens of experimental and control groups. 5 x 150 mg/kg 5-BrU-ACA or ACA decreased the formation of indirect PFCs on the 10th day of immune response. In vivo 5-BrU and 5-BrU-ACA inhibited the development of non or specific stimulated spleen cells to direct PFCs only in partially cytotoxic concentrations of 5 times 10(-4) Mol.