[Compounds with anti-gastric secretion and antiulcer activity. V. Derivatives of 3,3,4a,6,7,11b-hexahydro-2H,5H-benzo [1,4]cyclohep[1,2-b][1,4]-oxazine and related products].
A series of hexahydrobenzo[3,4]cyclohept[1,2-b][1,4]oxazines, with different substituents at the benzene and oxazine rings and nitrogen atom, was synthetized. The diastereomers and enantiomers of the unsubstituted compound and the related derivatives hexahydrobenzo[5,6] and exahydrobenzo[6,7]cyclohept[1,2-b][1,4]oxazine, hexahydro[1]benzoxepine and hexahydro[1]benzothiepin[5,4-b][1,4]oxazine, octahydrobenzo[3,4]cyclohept[1,2-b][1,4]diazine were also prepared. Some of these compounds inhibited at low doses gastric secretion in pylorus-ligated rats and antagonized ulcers in pylorus-ligated rats plus acetylsalicylic acid and in cold+restraint-stressed rats. When the most active compounds were tested on cats with Heidenhain pouch, they induced unwanted side effects that ruled out further development of these chemical series.
M
M
Bianchi
A
A
Butti
U
U
Pfeiffer
S
S
Rossi
F
F
Barzaghi
V
V
Marcaria
A
A
Nencioni
D000818:Animals; D000897:Anti-Ulcer Agents / Q000138:chemical synthesis* / Q000633:toxicity; D055598:Chemical Phenomena; D002621:Chemistry; D005260:Female; D005753:Gastric Mucosa / Q000187:drug effects / Q000378:metabolism; D008297:Male; D051379:Mice; D010078:Oxazines / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D051381:Rats
D000897:Anti-Ulcer Agents; D010078:Oxazines
Composti ad attività antisecretiva gastrica ed antiulcera. Nota V. Derivati di 3,4,4a,6,7,11b-esaidro-2H, 5H-benzo[1,4]cicloept-[1,2-b][1,4]ossazine e prodotti correlati.