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Deuterated secnidazole for use in the treatment of bacterial vaginosis and methods and uses thereof

A compound and hydrate technology, applied in antibacterial drugs, pharmaceutical formulations, organic active ingredients, etc., can solve problems such as slowing down the metabolic rate

Pending Publication Date: 2021-05-28
루핀인코포레이티드
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, incorporation of deuterium at a drug's metabolic site slows its rate of metabolism until another metabolite produced by attack at a carbon atom (which is not substituted by deuterium) becomes the dominant pathway due to metabolic switching
[0010] About Cytochrome P 450 Existing literature on deuterium substitution strategies applied to various pharmaceutical substances on enzymatic systems suggests that substantial primary deuterium KIE can occur

Method used

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  • Deuterated secnidazole for use in the treatment of bacterial vaginosis and methods and uses thereof
  • Deuterated secnidazole for use in the treatment of bacterial vaginosis and methods and uses thereof
  • Deuterated secnidazole for use in the treatment of bacterial vaginosis and methods and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0152] Embodiment 1: Deuteration is to human cytochrome P 450 Effect of isoforms on the metabolism of secnidazole

[0153] A study was conducted to determine the effect of deuterium on human cytochrome P 450 ("CYP") enzymes that affect the metabolism of secnidazole. The response of CYP enzymes expressed from cDNA to α,2-dimethyl-5-nitro-1H-imidazole-1-ethanol-d3 (“secnidazole-d3”) and α,2-dimethyl Metabolism of 5-nitro-1H-imidazole-1-ethanol-d6 (“secnidazole-d6”; see CAS No. 1346603-27-7) and obtained with non-deuterated secnidazole results for comparison.

[0154] Mix 600 μL containing enzyme protein in 100 mM potassium phosphate (pH 7.4), NADPH production system (1.3 mM NADP+, 3.3 mM glucose-6-phosphate, 0.4 U / mL glucose-6-phosphate dehydrogenase, 3.3 mM magnesium chloride) and 2 Reaction mixtures of each test substance (secnidazole, secnidazole-d3 or secnidazole-d6) at two concentrations (eg 1 μM and 10 μM) were incubated at 37°C. At two time points (0 and 120 min), th...

Embodiment 2

[0162] Embodiment 2: the composition of deuterated secnidazole particle

[0163] Deuterated secnidazole particles described below were prepared using deuterated secnidazole. The composition of the granules included a 1-gram dose of deuterated secnidazole.

[0164]

Embodiment 3

[0165] Example 3: Minimum Inhibitory Concentration ("MIC")

[0166] The MICs of the antimicrobials secnidazole (parent compound), secnidazole-D3, and secnidazole-D6 will be determined in combination with the following organisms: Lactobacillius crispatus; Atopobium vaginae; vaginal Gardnerella vaginalis; Megasphaera phylotype; Prevotella amnii; Prevotella timonensis; Prevotella bivia; MIC population distributions, MIC ranges, and MIC50 and MIC90 values ​​will also be determined.

[0167] The antimicrobial secnidazole ( parent compound), secnidazole-D3 and secnidazole-D6 agar dilution test. Biological isolates to be tested were collected from the female genital tract of women with and without bacterial vaginosis recovered between January 2013 and March 2015 in Pittsburgh, Pennsylvania. Older isolates were also included in the test.

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PUM

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Abstract

The present invention is related to deuterated secnidazole, a prodrug thereof, a hydrate thereof, a solvate thereof, a polymorph thereof, or a pharmaceutically acceptable salt thereof and its use for the treatment of bacterial vaginosis or trichomoniasis in a subject in need thereof. The present invention is also related to pharmaceutical compositions and methods and uses of treating bacterial vaginosis, trichomoniasis, amoebiasis, giardiasis, or a combination thereof.

Description

[0001] Cross References to Related Applications [0002] This PCT International Patent Application claims priority and priority to U.S. Provisional Application No. 62 / 727,159, filed September 5, 2018, which is hereby incorporated by reference in its entirety. technical field [0003] The present invention relates to deuterated secnidazole, a pharmaceutical composition comprising deuterated secnidazole, and using deuterated secnidazole or a pharmaceutical composition comprising deuterated secnidazole to treat bacterial vaginosis or trichomonas disease method. [0004] All references and products cited in this application and their disclosures therein are incorporated by reference in their entirety. Background technique [0005] Secnidazole (second generation 5-nitroimidazole) is a well-known antiprotozoal and antimicrobial drug (Gillis and Wiseman, "Secnidazole: A Review of its Antimicrobial Activity, Pharmacokinetic Properties, and Therapeutic Use in the Management of Prot...

Claims

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Application Information

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IPC IPC(8): A61K31/4164C07D233/94
CPCA61K31/4164C07D233/94A61K31/567Y02A50/30A61K2300/00A61K31/565A61P33/04A61P31/04A61K31/57
Inventor R·J·霍尔K·尼尔森J·加雷加尼
Owner 루핀인코포레이티드
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