PREPARATION OF TRIAZOLO[1,5-C]PYRIMIDINES AS POTENTIAL ANTIASTHMA AGENTS

被引：95

作者：

MEDWID, JB

PAUL, R

BAKER, JS

BROCKMAN, JA

DU, MT

HALLETT, WA

HANIFIN, JW

HARDY, RA

TARRANT, ME

TORLEY, LW

WRENN, S

机构：

[1] Medical Research Division, American Cyanamid Company, Lederle Laboratories

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 1990年 / 33卷 / 04期

关键词：

D O I：

10.1021/jm00166a023

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

With the use of the human basophil histamine release assay, 5-ary1-2-amino[1,2,4]triazolo[1,5-c]pyrimidines were found to be active as mediator release inhibitors. These compounds were prepared by reacting arylamidines with sodium ethyl formylacetate or with ethyl propiolate to give pyrimidinones. Treatment with phosphorus oxychloride gave a chloropyrimidine, which was converted to a hydrazinopyrimidine with hydrazine. Cyclization, using cyanogen bromide, gave the triazolo[1,5-c]pyrimidines, after a Dimroth rearrangement. Following a structure-activity evaluation, the 5-[3-(trifluoromethyl)phenyl]-2-amino (8-10), 5-(3-bromophenyl)-2-amino (8-13), 5-[3-(difluoromethoxy)-phenyl]-2-amino (8-11), and 5-(4-pyridinyl)-2-amino (6-7) compounds were found to have the best activity. They were chosen for further pharmacological and toxicological study. © 1990, American Chemical Society. All rights reserved.

引用

页码：1230 / 1241

页数：12

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