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Halogenated quinazolinyl nitrofurans as antibacterial agents

Inactive Publication Date: 2006-09-13
ULYSSES PHARMA PROD INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantages of nitrofurantoin are that it does not have good efficacy (i.e. requires relatively high doses to exert its antibacterial activity) and it does not have broad-spectrum antibacterial activity, which limits the application of this compound in the treatment of bacterial infections

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment I

[0053]

[0054] 6-Fluoro-2-methyl-4-(3H)quinazolinone (I)

[0055] 5-Fluoro-anthranilamide hydrochloride was prepared by adding 20 ml of concentrated hydrochloric acid (37% by weight) to a solution of 27.3 g of 5-fluoro-anthranilamide in 200 ml of methanol. The mixture was cooled in an ice bath to precipitate the hydrochloride, which was then collected and dried to give the product. A 17.4 g (0.1 mole) portion of the hydrochloride salt thus obtained was refluxed with 100 ml of acetic anhydride for 3 hours and the system was allowed to stabilize overnight. The mixture was then cooled in an ice bath and the solid collected by filtration on a Buchner funnel. The filter cake was slurried in 100 ml of water and warmed to facilitate dissolution and then 28% aqueous ammonia was added until the mixture was basic. After cooling, 6-fluoro-2-methyl-4-(3H)quinazolinone precipitated as a solid, which was then collected, washed with a little cold water and dried at 70°C to give the des...

Embodiment II

[0065] 6-fluoro-2-[2-(5-nitro-2-furyl)vinyl]-4-(m-hydroxyanilino)-quinazoline (VI)

[0066] Add 4.8 g (0.044 mole) m-aminophenol and 100 ml dimethylformamide to a new Erlenmeyer flask. The addition was stirred to dissolve the m-aminophenol and 6.5 g (0.02 mole) of 6-fluoro-2-[2-(5-nitro-2-furyl)vinyl]-4-chloroquinazoline (IV) was added. The reaction mixture was reacted as described in Example I to afford 6.5 g of crude product as a yellow solid which melted at 241-242°C with simultaneous decomposition. A 5.5 g sample was recrystallized from 40 ml dimethylformamide and 74 ml methanol was added to the warm solution, which was then cooled to recrystallize the purified product.

Embodiment III

[0068] 6-Fluoro-2-[2-(5-nitro-furyl)vinyl]-4-(o-hydroxyanilino)-quinazoline (VII)

[0069] To a 250 ml Erlenmeyer flask equipped with a magnetic stirrer and a heating oil bath was added 5.0 g (0.046 mole) of o-aminophenol and 100 ml of dimethylformamide. The addition was stirred to dissolve the o-aminophenol and 6.0 g (0.02 mole) of 6-fluoro-2-[2-(5-nitro-2-furyl)vinyl]-4-chloroquinazoline (IV) was added. The reaction mixture was reacted at 80-90° C. for 2 hours to form an organic precipitate; 100 ml of water was added to the warm mixture, then cooled and placed in a refrigerator overnight to crystallize. The solid was collected, washed with methanol and dried to give 7.5 g of a brown-tan solid. A solution of the product in 100 ml of dimethylformamide was treated with charcoal and filtered. To the warmed filtrate was added a first 75ml portion of methanol wood followed by a further 25ml portion. Cooling and scraping gave 5.5 g of the purified product as orange crystals.

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PUM

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Abstract

The present invention includes novel compounds of the formula (I) wherein X is absent or trans or cis CHCH, R1 is (C1-C10) alkyl unsubstituted or substituted by one to three hydroxy, (C1-C10) alkenyl unsubstituted or substituted by one to three hydroxy, (C1-C10) alkynyl unsubstituted or substituted by one to three hydroxy, or aryl unsubstituted or substituted by one to three hydroxy; R2 is hydrogen, alkyl or aryl; R3 and R4 are, independently of each other, H, halogen, or a solubilizing group, with the proviso that at least one of R3 and R4 is halogen; and pharmaceutically acceptable salts thereof. The invention also includes pharmaceutically acceptable formulations of said compounds which exhibit antibiotic activity against a wide spectrum of microorganisms including organisms which are resistant to multiple antibiotic families and are useful as antibacterial agents for treatment or prophylaxis of bacterial infections, or their use as antiseptics, agents for sterilization or disinfection.

Description

[0001] Cross References to Related Applications [0002] This application claims the benefit of United States Provisional Patent Application filed August 8, 2003, which is incorporated herein by reference. field of invention [0003] The present invention relates to a new nitrofuran antibiotic and its use in treating or preventing human or animal bacterial infection or its use as antiseptic, bactericide or disinfectant. These compounds exhibit antibiotic activity against a broad spectrum of microorganisms, including organisms of the multi-resistant antibiotic family. Background of the invention [0004] The following summary of the background art of the present invention is provided only to facilitate the understanding of the present invention, but neither this summary nor any references cited therein are admitted as prior art to the present invention. [0005] Control of bacterial infections in hospitals or in acquired immune populations is made extremely difficult by the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/04C07D405/06C07D405/14C07D413/14C07D417/14A61K31/395A01N43/54
CPCC07D405/06A01N43/54A61P31/02A61P31/04
Owner ULYSSES PHARMA PROD INC
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