Nitrogen-containing saturated heterocyclic compound

A technology of compound and heterocyclic group, applied in the direction of medical preparations containing active ingredients, drug combination, organic chemistry, etc., can solve problems that do not involve details of morpholine compounds, etc.

Active Publication Date: 2014-02-05
SHANGAI PHARMA GRP CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, no details about morpholine compounds are involved in this publication

Method used

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  • Nitrogen-containing saturated heterocyclic compound
  • Nitrogen-containing saturated heterocyclic compound
  • Nitrogen-containing saturated heterocyclic compound

Examples

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Embodiment ）

[0447] Specific examples (Examples) of synthesizing the objective compound [I] of the present invention by the methods exemplified above are shown below, but the present invention is not limited thereto.

Embodiment 1

[0450] (2R)-N-cyclopropyl-N-{1-[4-(3-methoxypropoxy)-1-benzofuran-6-yl]ethyl}morpholine-2-carboxamide[ Ex(1-1), Ex(1-2)]

[0451] [chemical formula 25]

[0452]

[0453] To (2R)-2-[(cyclopropyl{1-[4-(3-methoxypropoxy)-1-benzofuran-6-yl]ethyl}amino)carbonyl]morpholine-4 - To a solution of tert-butyl carboxylate (200mg) and 2,6-lutidine (0.142ml) in chloroform (4ml), add trimethylsilyl trifluoromethanesulfonate (0.180ml) under ice-cooling, in Stir at the same temperature for 30 minutes. Under ice-cooling, saturated aqueous sodium bicarbonate solution was added, followed by extraction with ethyl acetate. The organic phase was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (eluent: chloroform / methanol / ammonia = 200 / 2 / 1) to give (2R)-N-cyclopropyl-N-{(1R)-1 as a colorless oil -[4-(3-Methoxypropoxy)-1-benzofuran-6-yl]ethyl}morpholine-2-carboxamide [Ex(1-1)] (1...

Embodiment 2

[0456] (2R)-N-{(1R)-1-[3-chloro-1-(3-methoxypropoxy)-1H-indolyl-6-yl]ethyl}-N-cyclopropyl Piperazine-2-carboxamide[Ex(2-1)]

[0457] [chemical formula 26]

[0458]

[0459] To (2R)-2-{[{(1R)-1-[3-chloro-1-(3-methoxypropyl)-1H-indolyl-6-yl]ethyl}(cyclopropyl )amino]carbonyl}piperazine-1,4-dicarboxylic acid tert-dibutyl ester (44.0mg) and 2,6-lutidine (0.050ml) in dichloromethane (1.0ml) solution, under ice cooling Trimethylsilyl trifluoromethanesulfonate (0.051 ml) was added, followed by stirring at the same temperature for 1 hour. Under ice-cooling, saturated aqueous sodium bicarbonate solution and methanol (2.0 ml) were added, extracted with chloroform, the organic phase was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by NH-silica gel chromatography (eluent: ethyl acetate→ethyl acetate / methanol=5 / 1) to give (2R)-N-{(1R)-1-[ 3-Chloro-1-(3-methoxypropyl)-1H-indolyl-6-yl]ethyl}-N-cy...

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PUM

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Abstract

The present invention provides a nitrogen-containing saturated heterocyclic compound of the formula [I]: wherein R 1 is a cycloalkyl group and the like, R 22 is an optionally substituted aryl and the like, R is a lower alkyl and the like, T is a carbonyl group, Z is -O- and the like, and R 3 to R 6 are the same or different and a hydrogen atom and the like; or a pharmaceutically acceptable salt, that is useful as a renin inhibitor.

Description

technical field [0001] The present invention relates to a medicine, especially a nitrogen-containing saturated heterocyclic compound effective as a renin inhibitor or a pharmacologically acceptable salt thereof, as well as their use, preparation method and intermediate. Background technique [0002] The development of renin inhibitor drugs is expected as a drug for the prevention and treatment of hypertension, cardiac insufficiency, diabetic nephropathy, and the like, and for example, 3,4-substituted piperidine compounds are disclosed (Patent Document 1). However, no details about morpholine compounds are mentioned in this publication. In addition, although the morpholine compound is disclosed in International Publication No. 2008 / 153182, only the compound in which R in the formula I of the present invention is hydrogen is disclosed (Patent Document 2). [0003] prior art literature [0004] patent documents [0005] Patent Document 1: International Publication No. 06 / 069...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D265/30A61K31/4025A61K31/416A61K31/437A61K31/496A61K31/5375A61K31/5377A61P9/00A61P9/12A61P13/12C07D403/12C07D405/12C07D413/12C07D413/14C07D471/04
CPCC07D471/04C07D231/56C07D413/14C07D265/30C07D403/12C07D405/12C07D413/12A61P9/00A61P9/04A61P9/12A61P13/12A61K31/5377
Inventor 饭嶋彻须釜宽川口隆行沈竞康夏广新谢建树
Owner SHANGAI PHARMA GRP CO LTD
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