Journal of Medicinal Chemistry p. 559 - 586 (1985)
Update date:2022-08-02
Topics:
Nohara
Ishiguro
Ukawa
Sugihara
Maki
Sanno
5-Oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylic acids 23 and their tetrazole analogues 24 were synthesized from 4-oxo-4H-1-benzopyran-3-carbonitriles or 2-amino-4-oxo-4H-1-benzopyran-3-carboxaldehydes. When administered intravenously, they exhibited antiallergic activity in a reaginic PCA test in rats. In the carboxylic acid series, the activity was influenced by the substituents at the 2-position and increased substantially in the following order: Me, OMe < NH2 < OH, H < NHOMe. On the other hand, in the tetrazole series, 2-unsubsitituted derivatives showed the highest activity. Regardless of the kinds of substituents at positions 2 and 3, compounds bearing an alkyl group, especially an isopropyl group at the 7-position, were superior in activity to the corresponding unsubstituted compounds. Among these alkyl derivatives, 3-carboxylic acid derivatives, i.e., 23c (7-ethyl), 23g (2-amino-7-isopropyl), 23r [2-(methoxyamino)-7-isopropyl], and a 3-tetrazole derivative 24c (7-isopropyl), were 41-184 times as potent as disodium cromoglycate. They also exhibited remarkable activity when administered orally; clinical studies on 23g (AA-673) are in progress.
View Morewebsite:http://www.lonwinchem.com
Contact:Tel: 86-21-59858395
Address:No#966,Huaxu Road,Shanghai 201702,P.R.China
Dongtai Xinyuan Chemical Co., Ltd.
Contact:+86-21-56733000
Address:404F, 99Nong No.117 Zhongtan Rd. Shanghai
Zhangjiagang Golden Reach Fine Chemical Co.,LTD.
Contact:+86-512-6585 6968
Address:Changfu Road, Dongsha Chemical Industry Park, Zhangjiagang City, Jiangsu Province, China
MS( MAOSHENG )Chemical CO.,LTD
Contact:+86-519-82726678.82726378
Address:TAOXI INDUSTRY ZONE JINTAN
Suzhou Time-chem Technologies Co., Ltd.
Contact:0512-63983931/68086856
Address:No. 1326 of Binhe Road, New District, Suzhou, Jiangsu, P. R. China
Doi:10.1039/c5tc00350d
(2015)Doi:10.1002/ardp.200700013
(2007)Doi:10.1021/ja0737671
(2007)Doi:10.1021/om7006024
(2007)Doi:10.1021/jo00378a036
(1987)Doi:10.1002/anie.200504296
(2006)