Unlock instant, AI-driven research and patent intelligence for your innovation.

Hydroxyquinoxalinecarboxamide derivative

A hydroxyl and alkyl technology, applied in the field of hydroxyquinoxaline formamide derivatives, can solve the problem that the structure of hydroxyquinoxaline is not disclosed or suggested

Inactive Publication Date: 2011-05-04
DAIICHI SANKYO CO LTD
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the hydroxyquinoxaline structure possessed by the compound of the present application as a partial structure thereof is not disclosed or suggested in these prior art documents

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Hydroxyquinoxalinecarboxamide derivative
  • Hydroxyquinoxalinecarboxamide derivative
  • Hydroxyquinoxalinecarboxamide derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0527]

[0528] N-{(1S)-2-[4-(4-chlorophenoxy)piperidin-1-yl]-1-methyl-2-oxoethyl}-3-hydroxyquinoxaline-2- Formamide

Embodiment 1-1

[0530] [(1S)-2-(4-Hydroxypiperidin-1-yl)-1-methyl-2-oxoethyl]carbamate tert-butyl ester

[0531] At 0°C, under nitrogen flow, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.30g, 12.0mmol) and 1-hydroxybenzotriazole- Hydrate (1.84 g, 12.0 mmol) was added to a dichloromethane solution of 4-hydroxypiperidine (1.00 g, 10.0 mmol) and N-(tert-butoxycarbonyl)-L-alanine (1.89 g, 10.0 mmol) (50ml) followed by further addition of triethylamine (1.21ml, 12.0mmol) and stirring at room temperature overnight. The reaction solution was diluted with dichloromethane, then washed successively with saturated aqueous sodium bicarbonate solution, saturated aqueous ammonium chloride solution, water and brine, and then the resulting organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated and the resulting residue was purified by medium pressure preparative liquid chromatography (manufacturer Biotage, Inc., NH, 40+M) to give [(1S)-2-(4-hydroxypiperid...

Embodiment 1-2

[0535] {(1S)-2-[4-(4-Chlorophenoxy)piperidin-1-yl]-1-methyl-2-oxoethyl}carbamate tert-butyl ester

[0536] A solution of diisopropyl azodicarboxylate (2.80 ml, 5.21 mmol) in 40% toluene was added to [(1S)-2-(4-hydroxypiperidin-1-yl)- 1-Methyl-2-oxoethyl] tert-butyl carbamate (1.29g, 4.74mmol), 4-chlorophenol (670mg, 5.21mmol) and triphenylphosphine (1.37g, 5.21mmol) in toluene ( 18ml), stirred overnight at 90°C. The reaction solution was concentrated and the resulting residue was purified by medium pressure preparative liquid chromatography (manufacturer Biotage, Inc., 40+M) to give {(1S)-2-[4-(4-chlorophenoxy) Piperidin-1-yl]-1-methyl-2-oxoethyl}carbamate tert-butyl ester (700 mg, yield 34%), light yellow amorphous substance.

[0537] 1 H-NMR (CDCl 3 , 400MHz) δ: 7.25 (2H, d, J = 9.0Hz), 6.85 (2H, d, J = 9.0Hz), 5.55 (1H, d, J = 7.8Hz), 4.65 (1H, m), 4.52 ( 1H, m), 3.88-3.36(4H, m), 2.01-1.76(4H, m), 1.44(9H, s), 1.31(3H, d, J=7.0Hz).

[0538] MS (ESI, m / z): 383 (M+H) ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

Disclosed is a novel hydroxyquinoxalinecarboxamide derivative which is useful for prevention and / or treatment of blood coagulation disorders. Specifically disclosed is a compound represent by formula (i) or a pharmacologically acceptable salt thereof. (i) In the formula, R1 and R2 independently represent a hydrogen atom, a halogen atom or the like; R3 represents a hydrogen atom or the like; R4 and R5 independently represent a hydrogen atom, a halogen atom, a C1-4 alkyl group or the like; R6 and R7 independently represent a hydrogen atom or a C1-4 alkyl group; X represents a C3-10 cycloalkyl group, C6-10 aryl group or 5-10 membered heterocyclic group, which may be substituted by a member selected from the substituent group alpha, or the like; Y represents -CO-, -O-, -NRa- or the like; and Ra represents a hydrogen atom, a C1-4 alkyl group or the like.

Description

technical field [0001] The present invention relates to hydroxyquinoxaline carboxamide derivatives and their pharmacologically acceptable salts, which can be used as medicines. More specifically, the present invention relates to hydroxyquinoxaline carboxamide derivatives, and pharmacologically acceptable salts thereof, which exhibit anticoagulant effects. Background technique [0002] In recent years, due to the development of medical care, the average life expectancy has become longer and the size of the elderly population has become larger. Additionally, the proportion of people suffering from cardiovascular disease has increased due to changes in eating habits and lifestyle. In particular, not only thrombotic diseases such as cerebral infarction, myocardial infarction or peripheral circulatory disturbance show high mortality, but severe life restriction caused by sequelae imposes a huge burden on patients. Inhibition of thrombus formation is important for the prevention...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12A61K31/498A61K31/501A61K31/506A61K31/5377A61P7/02A61P9/00C07D401/14C07D417/14
CPCC07D401/12C07D401/14C07D417/14A61P7/02A61P9/00
Inventor 本木佳代子川越敬一西中重行增田幸枝坂本笃信金子悟有田健横沟亚纪
Owner DAIICHI SANKYO CO LTD