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Antimicrobial compounds and methods of use

a technology which is applied in the field of antibacterial compounds and antifungal compounds, can solve the problems that many previously useful antibiotics are no longer effective against infectious organisms isolated from human and animal subjects

Inactive Publication Date: 2014-12-04
NEXMED HLDG INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present patent provides antimicrobial compounds that can be used to treat hospital-acquired infections caused by resistant bacteria, fungus, and virus. The compounds can be used in various compositions such as antibacterial, antifungal, antiseptic, and disinfectant compositions. The compounds can inhibit the growth of a range of bacteria and fungi, including genera such as Acinetobacter, Bacillus, Enterobacter, Enterococcus, Escherichia, Klebsiella, Corynebacterium, and Aspergillus. The compounds can be used as adjuncts in existing antibacterial compositions or as the main ingredient. The compounds have been found to be effective against a range of bacteria, fungus, and virus. The patent also provides methods for making the compounds and pharmaceutically acceptable salts thereof.

Problems solved by technology

Many previously useful antibiotics are no longer effective against infectious organisms isolated from human and animal subjects.

Method used

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  • Antimicrobial compounds and methods of use
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  • Antimicrobial compounds and methods of use

Examples

Experimental program
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working examples

[0166]The following non-limiting examples further illustrate the various embodiments described herein. Example 1 provides a method of synthesizing dodecyl 2-(dimethylamino)propanoate (DDAIP) and dodecyl 2-(dimethylamino)propanoate hydrochloride salt. Examples 2-12 disclose methods of synthesizing other salts of DDAIP. The salts of DDAIP that were prepared include the sulfate, the phosphate, and organic salts including the 4-methylbenzenesulfonate, the 2-hydroxypropane-1,2,3-tricarboxylate, benzenesulfonate, the maleate, the methanesulfonate, the ethanesulfonate, the heminaphthalene-1,5-disulfonate, and the 2-hydroxyethanesulfonate. Examples 13-32 describe the methods of making and the characterization of related compounds and their hydrochloride salts. In view of the teachings of Examples 2-12 and the knowledge of the skilled artisan, the production of salts disclosed herein, as well as other salts, of the antimicrobial compounds is routine.

example 1

Synthesis of Dodecyl 2-(dimethylamino)propanoate and Dodecyl 2-(dimethylamino)propanoate Hydrochloride salt

[0167]

Synthesis of Dodecyl 2-aminopropanoate (3)

[0168]To a stirred solution of DL-alanine 1 (5 g, 56.1 mmol) in toluene (100 mL) was added dodecanol 2 (9.42 g, 50.5 mmol) in one lot, followed by pTSA (11.75 g, 61.7 mmol). After addition, the temperature of the reaction mixture was slowly raised to reflux temperature, the water was separated azeotropically, and the reaction mixture was monitored by TLC. The reaction mixture was concentrated under vacuum, the obtained residue was taken in ethyl acetate (200 mL) and washed with aqueous 5% Na2CO3 (3×50 mL) followed by brine solution. The organic layer was dried over Na2SO4 and concentrated under vacuum to afford crude dodecyl 2-aminopropanoate 3 (14.4 g, yield: 100%) as a liquid.

Synthesis of Dodecyl 2-(dimethylamino)Propanoate (DDAIP) (4)

[0169]To a stirred solution of dodecyl 2-aminopropanoate 3 (5 g, 19.4 mmol) in DCM (100 mL) was...

example 2

Synthesis of Dodecyl 2-(dimethylamino)propanoate p-toluene sulfonate salt (Nex-01)

[0174]

Synthesis of Dodecyl 2-(dimethylamino)propanoatep-toluene sulfonate salt

[0175](7, Nex-01): A stirred solution of DDAIP base 4 (80 g, 280 mmol) in ethyl acetate (500 mL) was cooled to 0° C. then p-toluene sulfonic acid H2O 6 (53.4 g, 280 mmol) was added in one lot. After addition, the temperature of the reaction mixture was slowly raised to RT and stirred at RT for 12 h; the reaction mixture was monitored by TLC. The reaction mixture was concentrated under vacuum and flushed with hexane. The obtained residue was taken in n-hexane (20 mL) and stirred at RT for 2 h (No solid). The obtained sticky solid kept in a deep freezer for 12 h to afford dodecyl 2-(dimethylamino)propanoate PTSA salt (7, Nex-01) (130 g, yield: 97.4%) as a hygroscopic solid, Mp: 60-65° C. 1H-NMR (400 MHz, CDCl3): δ 0.9 (t, 3H), 1.3 (m, 18H), 1.6 (d, 3H), 1.6 (q, 2H), 2.35 (s, 3H), 3 (m, 6H), 4.1 (t, 2H), 4.25 (q, 1H), 7.18 (d, 2...

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Abstract

The present disclosure provides antimicrobial compounds, compositions comprising such antimicrobial compounds, and methods of their use, in particular, antibacterial compounds and antifungal compounds. In certain aspects, the antimicrobial compounds are effective against pathogens of hospital-acquired infections. In certain aspects, the antimicrobial compounds are effective against pathogens that are resistant to antibiotics. The antimicrobial compounds can be used in antibacterial compositions, antifungal compositions, antiseptic compositions and disinfectant compositions. The antimicrobial compounds can be used as adjuncts in antibacterial compositions and antifungal compositions.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This application claims benefit under 35 U.S.C. §119 of U.S. Provisional Application Ser. No. 61 / 737,761, filed Dec. 15, 2012, the contents of which are hereby incorporated by reference.BACKGROUND OF THE INVENTION[0002]1. Field of the Invention[0003]The present disclosure relates to antimicrobial compounds, in particular to antibacterial compounds and antifungal compounds. In certain embodiments, the antimicrobial compounds are effective against pathogens of hospital-acquired infections. In certain embodiments, the antimicrobial compounds are effective against pathogens that are resistant to antibiotics.[0004]2. Description of the Background[0005]Widespread use of antibiotics in recent decades has led to proliferation of pathogens having multiple drug resistance, often encoded by transmissible plasmids, and therefore capable of spreading rapidly between species. Many previously useful antibiotics are no longer effective against infectious...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A01N37/44
CPCA01N37/44C07C229/12A61K9/00A61K31/216A61K31/223A61K31/7008C07B2200/07C07C229/16C07C229/22C07C229/36C07C309/30
Inventor DAMAJ, BASSAM B.MARTIN, RICHARD
Owner NEXMED HLDG INC
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