Antibacterial therapeutics and prophylactics

a technology of antibacterial therapy and prophylactics, applied in the field of new molecules, compositions and formulations for the treatment of bacterial infections, can solve the problems of reducing the permeability or uptake of antibiotics, affecting and affecting the permeability of antibiotics, so as to minimize nephrotoxicity, ototoxicity and gastrointestinal side effects, the effect of improving the delivery of antibiotics

Inactive Publication Date: 2020-05-07
VYOME BIOSCI PVT +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The patent describes compounds that can be formulated into slow-release or controlled-release formulations. This helps to deliver the compound to the site of infection for a prolonged period of time at optimal concentration, reducing the risk of side effects caused by high drug concentration in the body. The invention also provides effective formulations with new antibiotics that can prevent biofilm formation and have significant antibacterial and anti-inflammatory effects.

Problems solved by technology

A serious challenge in today's global health scenario is the wide spread of drug resistant bacterial strains capable of evading even the most recently developed generation of antibiotics (Fait & Tor 2014, Perspect Medicin Chem 6: 25; Michael et al 2014, Front Public Health 2: 145.).
Some genes encode enzymes that are responsible for modifying or degrading the antibiotic while some result in mutation of the antibiotic target enzyme or metabolic process that hinders the interaction of the antibiotic with the target protein.
Other genetic elements may decrease the permeability or the uptake of the antibiotic.

Method used

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  • Antibacterial therapeutics and prophylactics
  • Antibacterial therapeutics and prophylactics
  • Antibacterial therapeutics and prophylactics

Examples

Experimental program
Comparison scheme
Effect test

example 2

of Compound 6

[0345]

2-Chloro-N-(5-nitrothiazol-2-yl)-acetamide (A)

[0346]To a stirred solution of 5-nitrothiazol-2-amine (2 g, 13.80 mmol) and triethylamine (2.85 ml, 20.60 mmol) in acetonitrile, chloroacetyl chloride (1.44 ml, 17.80 mmol) was added slowly at 0° C., and the reaction mixture was stirred at room temperature for four hours. Then solvent was evaporated at reduced pressure and extracted with ethyl acetate. The organic layer was washed with 1 N HCl, brine and finally dried over sodium sulphate to obtain the compound A which was directly used for next reaction without further purification (2.6 g, 85%). 1H NMR (CDCl3): δ 8.29 (s, 1H, ArH), 4.28 (s, 1H, CH2).

6-Fluoro-1-methyl-7-(4-(2-((5-nitrothiazol-2-yl)amino)-2-oxoethyl)piperazin-1-yl)-4-oxo-1H,4H-[1,3]-thiazeto[3,2-a]quinoline-3-carboxylic acid (6)

[0347]To a stirred solution of 6-fluoro-1-methyl-4-oxo-7-(piperazin-1-yl)-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid (1.70 g, 4.87 mmol) and triethylamine (1.33 ml, 9....

example 3

of Compound 10

[0348]

(5-Nitrofuran-2-yl)methanol (A)

[0349]To a solution 5-nitrofuran-2-carbaldehyde (794 mg, 5.63 mmol) in dry methanol (10 ml), sodium borohydride (320 mg, 8.44 mmol) was added in portions at 0° C. Then the reaction mixture was stirred at room temperature for another 1 h. After completion, the reaction mixture was acidified with 3 N HCl and extracted with ethyl acetate. Organic layer was washed with brine, dried over sodium sulphate and finally solvent evaporated under vacuum to obtain the compound A. This was directly used for the next step without further purification (670 mg, 83%).

2-(Bromomethyl)-5-nitrofuran (B)

[0350]To a stirred solution of A (928 mg, 6.50 mmol) in DCM (20 ml), phosphorus tribromide (0.80 ml, 8.40 mmol) was added slowly at 0° C., and reaction mixture was stirred at room temperature for one hour. On completion, the reaction mixture was poured into crushed ice, neutralized with sodium bicarbonate solution and extracted with DCM, which on evaporati...

example 4

of Compound 11

[0352]

5-Nitrofuran-2-carbonyl chloride (A)

[0353]To an ice cold solution of 5-nitrofuran-2-carboxylic acid (450 mg, 2.90 mmol) in DCM (10 ml) oxalyl chloride (2.50 L, 29 mmol) was added followed by addition of catalytic amount of DMF at 0° C., and the reaction mixture was allowed to stir for 3 h at room temperature. On completion, the solvent was evaporated under reduced pressure to obtain the acid chloride A with a quantitative yield (498 mg).

6-Fluoro-1-methyl-7-(4-(5-nitrofuran-2-carbonyl)piperazin-1-yl)-4-oxo-1H,4H-[1,3]thiazeto[3,2-a]-quinoline-3-carboxylic acid (11)

[0354]To a stirred solution of 6-fluoro-1-methyl-4-oxo-7-(piperazin-1-yl)-1H,4H-[1,3]thiazeto[3,2-al]quinoline-3-carboxylic acid (1.2 g, 3.44 mmol) in DMF, triethylamine (0.80 ml, 5.7 mmol) was added, followed by addition of A (500 mg, 2.80 mmol) in DMF at 0° C. Then reaction mixture was stirred at room temperature for 18 h. After completion of the reaction excess ethyl acetate was added into the reactio...

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PUM

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Abstract

The present disclosure relates generally to novel molecules, compositions, and formulations for treatment of bacterial infections in general and more specifically to bacterial infections with antibiotic resistant pathogens.

Description

RELATED APPLICATIONS[0001]This application claims benefit under one or more of 35 U.S.C. § 119(a)-119 (d) of Indian Patent Application No. 2298 / DEL / 2015, filed on Jul. 28, 2015, the content of which is incorporated herein by reference in its entirety.FIELD OF THE INVENTION[0002]The present disclosure relates generally to novel molecules, compositions, and formulations for treatment of bacterial infections in general and more specifically to bacterial infections with antibiotic resistant pathogens.BACKGROUND OF THE INVENTION[0003]A serious challenge in today's global health scenario is the wide spread of drug resistant bacterial strains capable of evading even the most recently developed generation of antibiotics (Fait & Tor 2014, Perspect Medicin Chem 6: 25; Michael et al 2014, Front Public Health 2: 145.). Bacteria adopt various strategies to acquire drug resistant phenotypes (Dever & Dermody 1991. Arch Intern Med 151: 886). The bacterial genetic elements provide a number of resist...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07D513/04C07D487/04C07D311/22C07C323/60C07D413/14C07C323/59C07D471/00C07D403/12C07D405/12C07D263/38C07D239/96C07D215/56C07D401/12C07D263/48C07D263/24A61K47/38A61K47/36A61K47/34A61K47/12A61K47/10A61K9/06A61K9/00A01N43/90A01N43/78A01N43/76A01N43/46A61P31/04C07D417/12C07D413/12C07D405/14
CPCA61P31/04A61K47/38C07D417/12A61K9/0019A01N43/76C07D405/14C07D311/22C07D239/96C07D403/12A61K47/36C07D215/56A01N43/46C07D413/14C07D263/24A61K9/06C07D487/04C07D263/48C07C323/60A61K47/34A61K9/0014A01N43/90C07D263/38A01N43/78C07D471/00C07D405/12A61K47/12A61K47/10C07D413/12C07D401/12C07C323/59C07D513/04A61K9/0053A61K31/4743A61P13/02A61P17/10
Inventor SENGUPTA, SHILADITYAGHOSH, SHAMIKGHOSH, SUMANASINHA, MAUSADHASIVAM, SURESHBHATTACHARYYA, ANAMIKAMAVUDURU, SIVA GANESHTANDON, NUPARKUMAR, DEEPAK
Owner VYOME BIOSCI PVT
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