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Novel pyrrole derivatives

A drug and compound technology, applied in the field of new pyrrole derivatives, can solve disadvantages and other problems

Inactive Publication Date: 2016-03-30
UNIVERSITY OF LEICESTER
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Compounds that inhibit such properties are disadvantageous as drug candidates due to their potential non-specific binding to other cysteine-containing proteins in the body

Method used

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  • Novel pyrrole derivatives
  • Novel pyrrole derivatives
  • Novel pyrrole derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0100] Acronym

[0101] AcOH glacial acetic acid

[0102] aq.

[0103] Bn benzyl

[0104] Br wide

[0105] Boc tert-butoxycarbonyl

[0106] COPD chronic obstructive pulmonary disease

[0107] d doublet

[0108] DCM dichloromethane

[0109] DIPEAN, N-Diisopropylethylamine

[0110] DMAP4-dimethylaminopyridine

[0111] DMFN, N-Dimethylformamide

[0112] DMSO Dimethyl Sulfoxide

[0113] EDC1-ethyl-3-(3-dimethylaminopropyl)carbodiimide

[0114] EtOAc ethyl acetate

[0115] h hours (or hours)

[0116] HATUN,N,N′,N′-tetramethyl-O-(7-azobenzotriazol-1-yl)urea PF6

[0117] HPLC High Performance Liquid Chromatography

[0118] m multiplet

[0119] MeCN acetonitrile

[0120] MeOH Methanol

[0121] min minutes (or minutes)

[0122] NMR nuclear magnetic resonance

[0123] PBS Phosphate Buffered Saline

[0124] quin. quintet

[0125] RT room temperature

[0126] s unimodal

[0127] sat. Saturated

[0128] SAX solid supported strong cation exchange resin

[0129] sept. ...

Embodiment A1

[0149] Example A1: 3,4-Dihydroxy-1-(4-methoxyphenyl)-N 2 ,N 2 ,N 5 ,N 5 -Tetramethyl-1H-pyrrole-2,5-dicarboxamide (UL1-005)

[0150]

[0151] Step (i): Diethyl 2,2'-((4-methoxyphenyl)azanediyl)diacetate (1)

[0152] Ethyl 2-bromoacetate (146 mL, 1.30 mol) was added dropwise to a stirred solution of 4-methoxyaniline (75.0 g, 0.610 mol) and DIPEA (265 mL, 1.50 mol) in MeCN (300 mL). The reaction mixture was stirred at 60 °C for 16 h, then partitioned in 2M HCl (水溶液) (500 mL) and EtOAc (300 mL), the aqueous phase was extracted with EtOAc (300 mL), and the combined organics were sequentially extracted with 2M HCl (水溶液) (2×300mL), water (500mL) and brine (500mL), dried (MgSO 4 ), filtered and the solvent was removed in vacuo to give diethyl 2,2'-((4-methoxyphenyl)azanediyl)diacetate (1) (180 g, 100%) purple oil: m / z296(M+H) + (ES + ). 1 HNMR (400MHz, CDCl 3 )δ6.82-6.78(m,2H),6.64-6.59(m,2H),4.19(q,J=7.1Hz,4H),4.10(s,4H),3.74(s,3H),1.27(t , J=7.1Hz, 6H).

[0153] St...

Embodiment A2

[0163] Example A2: 3,4-dihydroxy-1-(4-methoxyphenyl)-N 2 ,N 2 ,N 5 ,N 5 - Alternative potential synthesis of tetramethyl-1H-pyrrole-2,5-dicarboxamide (UL1-005)

[0164]

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PUM

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Abstract

There are provided inter alia novel N-phenyl substituted pyrrole derivativesand theiruse in therapy, especially in the treatment of bacterial (e.g. pneumococcal) infections.

Description

technical field [0001] The present invention relates to compounds that are prodrugs of cytolysin inhibitors, and their use in therapy, including in pharmaceutical compositions, especially in the treatment of bacterial infections, such as pneumococcal infections. Background technique [0002] Streptococcus pneumoniae (pneumococcus) is one of the most threatening human pathogens, infecting more than 10 million people worldwide of all age groups, especially young children, the elderly and the immunocompromised. It is a major causative agent of severe and often fatal diseases such as pneumonia, bacteremia and meningitis. It is also the cause of other milder but debilitating diseases such as otitis media and keratitis. [0003] Even after decades of use of antibiotics and steroids as antibiotic adjuvants, the mortality and morbidity rates of pneumococcal disease remain high in developed countries and alarmingly high in developing countries. Although antibiotics kill pneumococci...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/36C07F9/09
CPCA61K31/496A61K31/675A61P31/04A61P43/00C07D207/36C07F9/572A61K45/06
Inventor 彼得·威廉·安德鲁马法尔达·皮雷斯·达马索马克·威廉·戴维斯弗里茨-弗里德尔·弗里克尔丹尼尔·哈姆扎西蒙·克里斯多夫·伊尔斯特拉娜·伦内恩
Owner UNIVERSITY OF LEICESTER