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Durch die Einwirkung von Anilinen auf 3, 6-Dichlorpyridazin wurden verschiedenartige 3-Chlor-6-anilinopyridazine dargestellt. Die letzteren lieferten durch Einwirkung von Natrium-Benzylalkoholat 3-Benzyloxy-6-anilinopyridazine, die durch Zersetzung mit Salzsaure in 6-Anilino-3 (2H)-pyridazinone ubergefuhrt wurden. Die so erhaltene 6-Anilino-3 (2H)-pyridazinone lieferten beim Einwirkenlassen von Methyljodid 2-Methyl-6-anilino-3 (2H)-pyridazinone. 3-Chlor-6-anilinopyridazine ergaben bei der katalytischen Hydrierung mit Palladium-Kohle 3-Anilinopyridazine. Ferner wurden einige 3-Alkoxy-6-benzylaminopyridazine hergestellt.

8-Oxo-7, 8-dihydropyrido[2, 3-d]pyridazine-5-carboxylic acid, 7-phenyl-8-oxo-7, 8-dihydropyrido[2, 3-d]pyridazine-5-carboxylic acid, and their esters, amides and hydrazides were prepared. Alkaline hydrolysis of 7-phenyl-8-oxo-7, 8-dihydroprido[2, 3-d]pyridazine-5-carboxylates gave phenylhydrazone of 3-formylpicolinic acid and good yields of 3-(2-carbamoyl)pyridylglyoxylates. Reaction of quinolinic anhydride with 2 molar equivalents of phenylhydrazine in acetic acid gave the cyclized phenylhydrazide, and its structure, 5-hydroxy-7-phenylpyrido[2, 3-d]pyridazin-8(7H)-one, was determined by its chlorination followed by catalytic hydrogenation to give 7-phenyl-1, 2, 3, 4-tetrahydropyrido[2, 3-d]pyridazin-8(7H)-one. 6, 7-Diphenylpyrido[2, 3-d]pyridazine-5, 8(6H, 7H)-dione was also prepared.

Durch Einwirkung von sekundaren Aminen auf 2-Chlormethylchinolin wurden 2-Aminomethylchinolin-derivate erhalten. Die letzteren wurden in Gegenwart von Raney-Nickel unter Druck katalytisch reduziert. Die so erhaltenen 2-Aminomethyl-1, 2, 3, 4-tetrahydrochinoline lieferten durch Einwirkung von Benzylchlorid bzw. p-Chlor-benzylchlorid 1-Benzyl-2-aminomethyl-1, 2, 3, 4-tetrahydrochinoline.

17β-(2-alkylamino-(or 2-arylamino- or 2-N, N-alkylarylamino-)-4-thiazolyl) androst-4-en-3-one derivatives were prepared from Reichstein's compound S 21-iodide, cortisone 21-iodide and desoxycorticosterone 21-iodide or corresponding 21-mesylate with N-alkylthiourea, N-arylthiourea or N, N-alkylarylthiourea respectively. Some of these compounds were found to have a digitalis-like properties (cardiac glucoside properties) as a result of pharmacological test.

Bei der Einwirkung von Benzylchlorid auf Maleinsaurehydrazid wurden mono- und dibenzylierte Verbindungen hergestellt. In diesem Zusammenhang wurden verschiedene Benzylderivate des Maleinsaurehydrazides hergestellt. Die Konstitution der oben erhaltenen Benzylderivate wurde vermittels UV-Spektren untergesucht.

The infrared absorption spectra of eleven 1-p-tolylthio-3-alkylureas and the corresponding sulfonyl compounds were recorded. Comparison of the thio and sulfonyl derivatives is made with respect to the influence exerted by the S or SO2 group on their respective frequencies due to phenyl and ureido groups. The variations of the absorption positions depend on the electronic nature of each groups. The nature of the alkyl group has relatively little effect on the position of these bands.

The preparation of a number of 4-benzamido-, 4-nicotinamido-, and 4-isonicotinamido-2, 6-dialkoxypyrimidines was described. Some of these new compounds showed strong antibacterial activities in vitro, and the structure-activity relationship was discussed.

Nous avons effectue le synthese des(alcoxy-2-pyrimidyl-4)-N1-sulfanilamides. La condensation des amino-4-alcoxy-2-pyrimidines avec le chlorure de p-nitro-benzenesulfonyle est tres difficile, surtout la (methoxy-2-pyrimidyl-4)-N1-sulfanilamide n'est pas obtenue par cette methode, donc elle a ete preparee par l'autre methode et possede l'activite antibacterienne intense.

17β-(2-alkylamino-(or 2-arylamino-or 2-N, N-alkylarylamino-) thiazolyl) androst-4-en-3β, 17α-diol was prepared from corresponding 3-one with sodium boronhydride in dioxan or dioxane-methanol (1 : 1). 17β-(2-alkylamino-(or 2-arylamino-)-4-thiazolyl) androst-4-en-3β, 17α-diol 3-(hydrogen succinate) and O, N-bis(hydrogen succinate) were obtained from corresponding 3β, 17α-diol and 17α-ol-3-one with succinic anhydride. Some of this substance had a digitalis like properties.

By treating with secondary amines chloraceto-o-toluidide was converted to aminoaceto-o-toluidides, which were cyclized on heating with sodium amide to give 2-aminomethylindoles. N-Benzyl-N-(N, N-dimethylaminoaceto)-o-toluidide on treatment with sodium amide was converted to 1-benzyl-2-N, N-dimethylaminomethylindole. N-Benzyl-(or N-p-chlorobenzyl-) N-phenylhydrazine was treated with aminoacetones in the presence of a trace of acetic acid to convert the corresponding aminoacetone N-benzyl-(or N-p-chlorobenzyl-) N-phenylhydrazones. The indole cyclization of the latter gave 1-benzyl-2-methyl-3-aminoindoles. On treatment of aminoacetones with phenylhydrazine derivatives in ethyl alcohol, methylglyoxal diphenylhydrazone derivatives were obtained.

Durch die Einwirkung von phenacylbromiden auf 3-Amino-6-chlorpyridazin wurden verschiedenartige 2-Phenyl-6-chlorimidazo [1, 2-b] pyridazine hergestellt. Das Chloratom der letzteren wurde durch Einwirkung von Na-Alkoholaten, Dialkylaminen bzw. wasr. alkoholischem Kali gegen Alkoxyl-, Dialkylamino- bzw. Hydroxyl-gruppen ausgetaus ht.

N, N-Dialkyl 3-(substituted anilino) butyramides were prepared by condensing of N, N-dialkyl crotonamides or N, N-dialkyl 3-chlorobutyramides with substituted anilines. N, N-Dialkyl 3-(N'-benzyl-substituted anilino) butyramides were prepared from N, N-dialkyl 3-(substituted anilino) butyramides and benzyl chloride. Some of the compounds thus prepared have analgetic activities.

The methyl steroid-21-yl-β-D-glucopyranosiduronates were prepared by treatment of Reichstein's compound S, cortisone, hydrocortisone, prednisone and prednisolone with methyl 1-bromo-1-deoxy-2, 3, 4-tri-O-acetyl-α-D-glucopyranosiduronate. Treatment of these compounds with methanolic ammonia afforded the corresponding steroid-21-yl-β-D-glucopyranosiduronamide.

The synthesis of a number of sulfonamides having dialkylamino groups in the pyrimidine nucleus was described. Among these new compounds, N1-(6-chloro-2-dialkylamino-4-pyrimidyl)sulfanilamide were found to possess notable antibacterial activities.

The infrared absorption spectra of the two aminopyridazines were observed and compared with those of the three aminopyridines and aniline. The amino-form of the two aminopyridazines was confirmed, and at the same time the structural similarity of 4-aminopyridazine with 4-aminopyridine was shown by their infrared spectra. Similarly, the spectrum of 3-aminopyridazine was close to that of 2-aminopyridine. In addition, the correlation between the position and the nature of substituent was discussed.

The relation between the electronic structure and the local anesthetic activity of 2-diethylaminoacetanilide derivatives was investigated by a molecular orbital method and it was found that the stabilization energy due to the charge transfer complex formation between these compounds and thiamine has something to do with their local anesthetic activities.

N-Alkyl or N, N-dialkyl 3-(N'-acyl-, N'-alkyl- or N'-benzylsubstituted anilino)propionamide derivatives were prepared from corresponding N-alkyl or N, N-dialkyl 3-(substituted anilino) propionamides by treating with acid anhydride, alkylhalide, or formaldehyde, formic acid and benzyl chloride, respectively. N, N-Dialkyl 3-(substituted anilino) propylamines were also prepared by condensation of 3-(substituted anilino) propyl chlorides with secondary amines. N, N-Dialkyl 3-(N'-acyl-substituted anilino) propylamines were obtained by treatment of 3-(substituted anilino) propylamines with acid anhydrides. Some of these compounds were found to possess analgetic activities.