Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Spiro condensed barbituric acid derivatives for use as antibacterial

A compound and pharmaceutical technology, applied in the field of substituted heterocycles, can solve problems such as weak antibacterial agents

Inactive Publication Date: 2010-03-31
ASTRAZENECA AB
View PDF0 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although cyclothiidine has potent activity against DNA gyrase, it is a weak antibacterial agent that only shows activity against some fungal strains (Nakada, N, 1993, Antimicrob. Agents Chemother. 37:2656-2661)

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
  • Spiro condensed barbituric acid derivatives for use as antibacterial
  • Spiro condensed barbituric acid derivatives for use as antibacterial
  • Spiro condensed barbituric acid derivatives for use as antibacterial

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[1229] (6aS, 7S, 9R)-rel-7,9-dimethyl-3-(1,3,4-thiadiazol-2-yl)-6a,7,9,10-tetrahydro -2'H, 5H-spiro[1,4-oxazino[4,3-a][1,8]naphthyridine-6,5'-pyrimidine]-2',4',6'(1' H,3′H)-trione

[1230] 2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-5-(1,3,4-thiadiazol-2-yl)pyridine-3-carbaldehyde (intermediate 114, 32 mg, 0.0107 mmol) and barbituric acid (16.4 mg, 0.0128 mmol) in anhydrous IPA (2 mL) were heated to 90° C. for 12 hours. The reaction mixture was cooled to room temperature and concentrated. The residue thus obtained was purified on a neutral aluminum column using a gradient of ethyl acetate / petroleum ether to give the product as a solid. MS(ES)MH + : 415.0, for C 18 h 18 N 6 o 4 S; 1 H NMR (400MHz, DMSO): δ1.0(d, 3H), 1.2(d, 3H), 2.8(m, 1H), 2.9(d, 1H), 3.6(m, 3H), 4.0(d, 1H ), 5.1 (dd, 1H), 7.8 (s, 1H), 8.6 (d, 1H), 9.5 (s, 1H), 11.7 (s, broad peak, 2H).

Embodiment 2

[1233] 3-Bromo-7,9-dimethyl-5,6a,7,8,9,10-hexahydro-1'H-spiro[pyrido[1,2-a][1,7]naphthyridine -6,5'-pyrimidine]-2',4',6'(3'H)-trione

[1234] Starting material: Intermediate 19.

[1235] MS(ES)MH + :407 for C 17 h 19 BrN 4 o 3 .

[1236] 1 H NMR (300 MHz, DMSO): 0.7 (2d, 3H), 0.9 (2d, 3H, 4:1 ratio), 1.0 (q, 1H), 1.4-1.8 (m, 3H), 2.7 (m, 1H), 2.8 and 2.9 (2d, 1H, 4:1 ratio), 3.2 (m, 1H), 3.4 (m, 1H), 3.6 (m, 1H), 3.9-4.1 (m, 1H), 7.1 (2s, 1H, 4:1 ratio), 7.9 (2s, 1H, 4:1 ratio), 11.5 (2s, 1H, 4:1 ratio), 11.7 (2s, 1H, 4:1 ratio).

Embodiment 3

[1238] (6aS,7S,9R)-rel-3-bromo-7,9-dimethyl-6a,7,9,10-tetrahydro-1′H,5H-spiro[[1,4]oxazine And[4,3-a][1,7]naphthyridine-6,5'-pyrimidine]-2',4',6'(3'H)-trione

[1239] Starting material: Intermediate 18.

[1240] MS(ES)MH + :409 for C 16 h 17 BrN 4 o 4 .

[1241] 1 H NMR (300MHz, DMSO): 0.95(d, 3H), 1.1(d, 3H), 2.7-3.0(m, 2H), 3.4-3.7(m, 4H), 4.1(d, 1H), 7.1(s , 1H), 8.0(s, 1H), 11.6(s, 1H), 11.8(s, 1H).

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

In one aspect, the present invention relates to compounds of Formula (I): to pharmaceutically acceptable salts thereof, to methods of using them to treat bacterial infections, and to method for theirpreparation.

Description

technical field [0001] The present invention relates to novel substituted heterocycles, their pharmaceutical compositions and methods of use. Furthermore, the present invention relates to therapeutic methods for treating bacterial infections. Background technique [0002] The continued development of antibiotic resistance that may render currently used antimicrobial agents ineffective against strains has been of serious concern to the international community of microbiology and infectious diseases. These conditions can result in considerable morbidity and mortality. In general, bacterial pathogens can be classified as Gram-positive or Gram-negative pathogens. Antibacterial compounds that have potent activity against both Gram-positive and Gram-negative pathogens are generally considered to have broad-spectrum activity. [0003] Gram-positive pathogens are of particular importance because the development of drug-resistant strains can be difficult to manage and eradicate on...

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
IPC IPC(8): C07D471/22C07D498/22A61K31/4545A61P31/04
CPCC07D498/22C07D471/22A61P31/04
Inventor G·S·巴萨拉布J·杜马斯P·希尔
Owner ASTRAZENECA AB
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com