NOVEL CAMP PDE-III INHIBITORS - IMIDAZO[4,5-B]PYRIDIN-2(3H)-ONES AND THIAZOLO[4,5-B]PYRIDIN-2(3H)-ONES AND THEIR ANALOGS

被引：30

作者：

SINGH, B ^{[1
]}

BACON, ER ^{[1
]}

ROBINSON, S ^{[1
]}

FRITZ, RK ^{[1
]}

LESHER, GY ^{[1
]}

KUMAR, V ^{[1
]}

DORITY, JA ^{[1
]}

REUMAN, M ^{[1
]}

KUO, GH ^{[1
]}

EISSENSTAT, MA ^{[1
]}

PAGANI, ED ^{[1
]}

BODE, DC ^{[1
]}

BENTLEY, RG ^{[1
]}

CONNELL, MJ ^{[1
]}

HAMEL, LT ^{[1
]}

SILVER, PJ ^{[1
]}

机构：

[1] STERLING WINTHROP,DEPT VASC & BIOCHEM PHARMACOL,DIV PHARMACEUT RES,COLLEGEVILLE,PA 19426

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 1994年 / 37卷 / 02期

关键词：

D O I：

10.1021/jm00028a007

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The transformation of milrinone to 1,3-dihydro-5-methyl-6-(4-pyridinyl)-2H-imidazo[4,5-b]pyridin-2-one (13a), 5-methyl-6-(4-pyridinyl)thiazolo[4,5-b]pyridin-2(3H)-one (51), and 7-methyl-6-(4-pyridinyl)-1,8-naphthyridin-2(vl)-one (22) resulted in very potent cAMP PDE III inhibitors with in vitro activity in the nanomolar range. 1,3-Dihydro-2H-imidazo[4,5-b]pyridin-2-ones 13 were prepared from 2-aminopyridine-3-carboxylic acids (7, 10) via Curtius rearrangement. 1,8-Naphthyridin-2(1H)-one 22 and the corresponding 3,4-dihydro derivative 28 were prepared from 5-bromo-2-methyl[3,4'-bipyridin]-6-amine (21) and 5-bromo-2-methyl[3,4-bipyridin]-6(1H)-on (24), respectively, via Heck reaction. Thiazolo[4,5-b] pyridin-2(3H)-ones 35 were prepared from 6-bromo[3,4'-bipyridin]-8-amines 30 and 32 via a four-step sequence. Treatment of 6-amino-2-methyl[3,4'-bipyridine]-5-thiol (59) with ethyl bromoacetate and ethyl bromodifluoroacetate gave pyridothiazinones 60 and 61, respectiveiy.

引用

页码：248 / 254

页数：7

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