Detail of "62929-91-3"

CAS Number:
62929-91-3
Name:
2(1H)-Quinolinone,8-hydroxy-5-[(1R,2S)-1-hydroxy-2-[(1-methylethyl)amino]butyl]-, hydrochloride(1:1), rel-
Molecular Structure:
Formula:
C16H22 N2 O3 . Cl H
Molecular Weight:
326.86
Synonyms:
2(1H)-Quinolinone,8-hydroxy-5-[(1R,2S)-1-hydroxy-2-[(1-methylethyl)amino]butyl]-,monohydrochloride, rel- (9CI); 2(1H)-Quinolinone,8-hydroxy-5-[1-hydroxy-2-[(1-methylethyl)amino]butyl]-, monohydrochloride,(R*,S*)-(?à)-; 2(1H)-Quinolinone,8-hydroxy-5-[1-hydroxy-2-[(1-methylethyl)amino]butyl]-, monohydrochloride,(R*,S*)-; Meptin; OPC 2009; Procaterol hydrochloride
Safety:
Poison by subcutaneous, intravenous, and intraperitoneal routes. Moderately toxic by ingestion. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits toxic fumes of NO_x and HCl. Details

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Isomers of erythro-5-(1-hydroxy-2-isopropylaminobutyl)-8-hydroxycarbostyril, a new bronchodilator: Isomers of erythro-5-(1-hydroxy-2-isopropylaminobutyl)-8-hydroxycarbostyril, a new bronchodilator. Yoshizaki, Shiro; Manabe, Yoshiaki; Tamada, Shigeharu; Nakagawa, Kazuyuki; Tei, Seiso (Dep. Pharmacol., Otsuka Pharm. Co., Ltd., Tokushima, Japan). J. Med. Chem., 20(8), 1103-4 (English) 1977. CODEN: JMCMAR. DOCUMENT TYPE: Journal CA Section: 1 (Pharmacodynamics) Section cross-reference(s): 27 Racemic erythro-5-[1-hydroxy-2-(isopropylaminobutyl]-8-hydroxycarbostyril-HCl (rac-erythro-I-HCl) [62929-91-3] was O-benzylated, and resolved by crystn. of dibenzoyltartrate salts, followed by debenzylation to give (-)-erythro-I-HCl [62910-94-5] and (+)-erythro-I-HCl [62910-95-6]. Inversion of the O-benzylated erythro isomers was achieved by N-acetylation, replacement of OH by Cl, alk. hydrolysis, and dibenzylation to give rac-threo-I-HCl [62910-96-7], (-)-threo-I-HCl [62910-97-8], and (+)-threo-I-HCl [62910-98-9]. In tests in anesthetized dogs for inhibition of histamine-induced bronchospasm ad increase in heart rate, rac- ad (-)-erythro-I had potent and .beta.2-selective bronchodilator activities, while the other isomers had weak .beta.-adrenoceptor stimulant activities. Structure-activity relations are discussed.