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Phosphate esters of gyrase and topoisomerase inhibitors

A compound, alkyl technology, applied in the direction of anti-inflammatory agents, chemical instruments and methods, non-central analgesics, etc.

Active Publication Date: 2014-04-02
SPARROW THERAPEUTICS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Such an inhibitor would be an attractive candidate for an antibiotic without a history of the resistance problems that plague other classes of antibiotics

Method used

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  • Phosphate esters of gyrase and topoisomerase inhibitors
  • Phosphate esters of gyrase and topoisomerase inhibitors
  • Phosphate esters of gyrase and topoisomerase inhibitors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach

[0052] It will be appreciated that various alternative embodiments of the compound or salt of formula (I) may be selected by requiring one or more of the alternative embodiments listed in (1) to (3) above. For example, further embodiments of the present invention can be obtained through the following combinations: (1)(a) and (3)(a); (1)(a) and (3)(b); (1)(a) and ( 3)(c); (1)(a) and (3)(d); (1)(b), (2)(a), and (3)(a); (1)(b), ( 2)(a), and (3)(b); (1)(b), (2)(a), and (3)(c); (1)(b), (2)(a), and (3)(d); (1)(b), (2)(b), and (3)(a); (1)(b), (2)(b), and (3)(b ); (1)(b), (2)(b), and (3)(c); (1)(b), (2)(b), and (3)(d); etc.

[0053] The prodrugs of the present invention are characterized by unexpectedly high water solubility. This solubility facilitates the administration of higher doses of the prodrug, resulting in greater drug loading per unit dose.

[0054] One embodiment of the invention relates to a method of controlling, treating or reducing the development, severity or effe...

specific Embodiment approach

[0141] In order that the present invention may be more fully understood, the following examples are set forth. These examples are for illustrative purposes only and should not be construed as limiting the scope of the invention in any way.

[0142] The following definitions describe terms and abbreviations used herein:

[0143] Acetyl

[0144] Butyl

[0145] Et ethyl

[0146] Ph phenyl

[0147] Me methyl

[0148] THF Tetrahydrofuran

[0149] DCM dichloromethane

[0150] CH 2 Cl 2 Dichloromethane

[0151] EtOAc ethyl acetate

[0152] CH 3 CN acetonitrile

[0153] EtOH ethanol

[0154] Et 2 O ether

[0155] MeOH Methanol

[0156] MTBE methyl tert-butyl ether

[0157] DMF N,N-Dimethylformamide

[0158] DMA N,N-Dimethylacetamide

[0159] DMSO Dimethyl Sulfoxide

[0160] HOAc acetic acid

[0161] TEA Triethylamine

[0162] TFA trifluoroacetic acid

[0163] TFAA Trifluoroacetic anhydride

[0164] Et 3 N triethylamine

[0165] DIPEA Diisopropylethylamine ...

preparation example 1

[0263] 2-(2-fluoro-6-nitrophenyl)-2,3-dihydrofuran (15A) and 2-(2-fluoro-6-nitrophenyl)-2,5-dihydrofuran (15B ) preparation.

[0264]

[0265] 2-Bromo-1-fluoro-3-nitro-benzene (14) (200.3 g, 98%, 892.3 mmol, Bosche F6657), 1,4-dioxane (981.5 mL, Sigma-Aldrich 360481 ) and 2, 3-Dihydrofuran (2) (341.1 mL, 99%, 4.462 mol, Aldrich 200018) was charged to the reaction flask, followed by N,N-diisopropylethylamine (155.4 mL, 892.3 mmol, Sigma-Aldrich 550043) and bromo(tri-tert-butylphosphine)palladium(I) dimer (6.936 g, 8.923 mmol, Johnson Matthey C4099). The mixture was stirred at reflux for 2 hours (HPLC showed 98% consumption of starting aryl bromide). It was cooled, the precipitate was removed by filtration, washed with EtOAc, and the filtrate was concentrated in vacuo to a dark reddish brown semi-solid oil. Dissolve the oil in CH 2 Cl 2 , via a silica filler with CH 2 Cl 2 Elution and concentration in vacuo gave a mixture of 15A and 15B as a dark amber oil (291.3 g). ...

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PUM

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Abstract

The present invention relates to phosphate esters of compounds that inhibit bacterial gyrase and / or Topoisomerase IV and pharmaceutical compositions thereof. These phosphate esters are useful for treating bacterial infections.

Description

[0001] Cross References to Related Applications [0002] This application claims the benefit under 35 U.S.C. §119 of U.S. Provisional Patent Application Serial No. 61 / 499,144, filed June 20, 2011; the entire contents of which are incorporated herein by reference. Background technique [0003] Bacterial resistance to antibiotics has long been recognized and is now recognized as a serious world health problem. Because of this resistance, some bacterial infections are difficult or even impossible to treat with antibiotics. This problem has become particularly acute with the recent development of multidrug resistance in certain bacterial strains, such as Streptococcus pneumoniae (SP), Mycobacterium tuberculosis and Enterococci. The emergence of vancomycin-resistant enterococci is particularly alarming because vancomycin, the only effective antibiotic previously used to treat this infection, has been considered a "last resort" drug for many infections. While many other drug-resis...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/14A61K31/506A61P31/00A61P1/00
CPCC07F9/65586C07B2200/05A61K45/06C07D405/14A61K31/688A61K31/685A61P1/00A61P1/02A61P9/00A61P11/00A61P13/00A61P15/00A61P17/00A61P19/00A61P27/02A61P27/16A61P29/00A61P31/00A61P31/04A61P35/00
Inventor Y·L·本纳尼P·S·查理弗森A·格里洛特A·勒迪尔安H·奥多德
Owner SPARROW THERAPEUTICS
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