A series of 2‐amino‐benzimidazoles with various substituents in position 1 and at the amino group has been prepared. The methods used are the displacement of chlorine by an amino group in the position 2 of the benzimidazole ring and the condensation of o‐phenylenediamines with carbodiimides or S‐methyl‐isothioureas.

AbstractThe synthesis of a series of 1‐aminoalkyl‐2‐benzyl‐benzimidazoles is described. Some of these compounds show strong analgesic activity.

AbstractThe synthesis of a series of phenyl‐[1‐aminoalkyl‐benzimidazolyl‐(2)]‐acetic esters and amides is described. Some of the derivatives prepared show pronounced analgesic activity.

The products of the condensation of o-phenylenediamine with ethyl acetoacetate were re-investigated. Depending on the reaction conditions, 2-methylbenzimidazole (II), 2-isopropenyl-benzimidazole-2-one (VI) and 4,7-dihydro-5-methyl-1H-2,3-benzo-1,4-diazepin-7-one (IV) were obtained. 2-Acetonylbenzimidazole, which had erroneously been described in the literature, could not be isolated from the above mentioned reaction; it was prepared by condensing o-phenylenediamine with the ketal of ethyl acetoacetate followed by hydrolysis of the ketal group. The investigation was extended to the reaction of o-phenylenediamine with 2-carbethoxycyclohexanone and 2-carbethoxycyclopentanone as well as with N-substituted 3-carbethoxy-4-piperidones.

AbstractThe synthesis of a series of 1‐aminoalkyl‐2‐benzyl‐nitro‐benzimidazoles is described. Many of the 5‐nitro‐benzimidazoles prepared show strong analgesic activity. 1‐(β‐Diethylamino‐ethyl)‐2‐(p‐ethoxy‐benzyl)‐5‐nitro‐benzimidazole (XXXVIII) is 1000 times as potent as morphine and therefore the most active analgesic known until now.

AbstractThe reaction of o‐phenylenediamine with α‐phenyl‐ and γ‐phenyl‐acetoacetic ester has been investigated. The former yields mainly 1‐β‐methylstyryl‐benzimidazole‐2‐one (IX), the latter affords 4,7‐dihydro‐5‐benzyl‐1H‐2,3‐benzo‐1,4‐diazepin‐7‐one (XVI). The structures of these products have been elucidated.

The synthesis and pharmacological activity of basically substituted dibenzothiazepines are described. They possess interesting antihistamine and antiserotonine activity. By varying the substituents in the benzene nuclei, and by a suitable choice the basic side chains, the specifity and activity of some derivatives could be increased considerably, especially with the dibenzothiazepinones.

AbstractA new synthesis of γ‐carbolines is described. Starting from 2‐lithium l‐alkyl‐indoles, reaction with an a‐dialkylaminoketone yields 2‐indolylethanolamines, which are aminomethylated with formaldehyde and dimethylamine in the 3‐position of the indole nucleus. The dimethylaminomethyl nitrogen of this gramine derivative may be selectively quaternized with methyl iodide and the quaternary gramine derivative cyclized to N(b)‐quaternized 1‐hydroxy‐1,2,3,4‐tetrahydro‐γ‐carboline derivatives by hcating. Thc latter products may be aromatized at higher temperatures to quaternary γ‐carboline derivatives. The generality of thc new method is verified by numerous examples.

AbstractThe detoxification of a‐phenyl‐a‐ethyl‐glutarimide («Doriden») in the animal organism occurs principally by coupling with glucuronic acid. The products of the glucuronic acid coupling were isolated from the urine and were found to be pharmacologically inactive. The main components of the glucuronic mixture were isolated as crystalline derivatives; their structure was established by degradation and synthesis of the aglucone residue.

AbstractWith a view to investigate the biological degradation of „Doriden”︁ some glutarimides have been synthesized which are presumptive intermediate products.

AbstractThe synthesis of 1 H‐4‐phenyl‐pyrido‐[1, 2‐c]‐pyrimido‐1,3(2 H)‐ dione (VI) by condensation of phenyl‐pyridyl‐(2)‐acetamide (I) with diethyl carbonate and sodium ethoxide, as well as the preparation of some of its derivatives, is described.

The syntheses of 1-(β-dialkylamino-ethyl)-2-benzyl-5-nitro-benzimidazoles, a new series of powerful analgesics, are described.

AbstractDurch Umsetzung von [Pyridyl‐(2)‐methyl]‐lithium rnit Oestron und Dehydro‐epi‐O‐acetyl‐androsteron konnten die entsprechenden 17 β‐Hydroxy‐17 α‐picolyl‐Steroide erhalten werden. Die Lithium‐ Verbindung von 2‐Athyl‐pyridin, 1‐[Pyridyl‐(2′)]‐äthyl‐lithium, reagiert mit Dehydro‐epi‐O‐acetyl‐androsteron unter Bildung von zwei C‐20‐isomeren 17 β‐Hydroxy‐20‐pyridyl‐pregnenen. Die Hydrierung dieser Verbindungen wird ebenfalls beschrieben.