A novel series of 6-methoxy-1H-benzotriazole-5-carboxamide derivatives with dual antiemetic and gastroprokinetic activities.
A novel series of 6-methoxy-1H-benzotriazole-5-carboxamide derivatives with a medium perhydroazacycle ring in the amine moiety were prepared, and their antiemetic and gastroprokinetic activities were evaluated. Among them, N-(1-ethylhexahydroazepin-3-yl)-, N-(1-ethyloctahydroazocin-3-yl)- and N-(1-ethyloctahydroazonin-3-yl)-6-methoxy-1H-benzotriazole-5-carbo xamides (24, 36, 37) showed a potent antiemetic activity (inhibition of apomorphine-induced emesis in dogs) along with gastroprokinetic activity (gastric emptying in rats).
Hirokawa
Y
Y
Discovery Research Laboratories I, Dainippon Pharmaceutical Co., Ltd., Osaka, Japan.
Yamazaki
H
H
Yoshida
N
N
Kato
S
S
D000818:Animals; D000932:Antiemetics / Q000737:chemistry / Q000494:pharmacology*; D001381:Azepines / Q000737:chemistry / Q000494:pharmacology*; D001392:Azocines / Q000737:chemistry / Q000494:pharmacology*; D004064:Digestive System / Q000187:drug effects; D004068:Digestive System Physiological Phenomena; D004285:Dogs; D005746:Gastric Emptying / Q000187:drug effects; D005765:Gastrointestinal Agents / Q000737:chemistry / Q000494:pharmacology*; D051381:Rats; D013329:Structure-Activity Relationship; D014230:Triazoles / Q000737:chemistry / Q000494:pharmacology*
D000932:Antiemetics; D001381:Azepines; D001392:Azocines; D005765:Gastrointestinal Agents; C116796:N-(1-ethylhexahydroazepin-3-yl)-6-methoxy-1H-benzotriazole-5-carboxamide; C116797:N-(1-ethyloctahydroazocin-3-yl)-6-methoxy-1H-benzotriazole-5-carboxamide; C116798:N-(1-ethyloctahydroazonin-3-yl)-6-methoxy-1H-benzotriazole-5-carboxamide; D014230:Triazoles