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Compounds and methods for treating bacterial infections

a technology for bacterial infections and compounds, applied in the field of compounds and methods for treating bacterial infections, can solve the problems of serious recurrence and significant problems in recurrent infections, and achieve the effect of reducing the resistance of a bacterium and preventing a urinary tract infection

Inactive Publication Date: 2018-07-12
WASHINGTON UNIV IN SAINT LOUIS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention relates to a compound with a specific formula (I) that can be used in various applications. The compound has specific features such as X, R2, n, and Z, which can be selected from specific options. The compound can have different forms such as O, CH(OH), CH(OR5), and CH2, S, and NR5R6, which can also be selected from specific options. The compound can have various properties such as being a hydrogen bond acceptor, a hydrogen bond donor, a Lewis acid, a Lewis base, a proton donor, a proton acceptor, an electron donor, an electron acceptor, and a solvent. The compound can be used in various applications such as in the field of electronics, sensors, and biomedicine.

Problems solved by technology

Further, recurrent infections are a significant problem despite appropriate antibiotic therapy of the index case.
Recurrence is a serious problem for many women.

Method used

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  • Compounds and methods for treating bacterial infections
  • Compounds and methods for treating bacterial infections
  • Compounds and methods for treating bacterial infections

Examples

Experimental program
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Effect test

example 1

[3-methyl-4-[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]benzoate

[0684](Han et. al., J. Med. Chem. 2012, 55, 3945-3959).

[0685]To a round-bottomed flask equipped with a reflux condenser and N2 line was added [(2R,3R,4S,5R,6S)-4,5-diacetoxy-6-(acetoxymethyl)-2-(4-bromo-2-methyl-phenoxy)tetrahydropyran-3-yl] acetate (0.52 g, 1.0 mmol), (3-methoxycarbonylphenyl)boronic acid (0.22 g, 1.2 mmol), Cs2CO3 (0.98 g, 3 mmol) and Pd(Ph3)4 (0.12 g, 0.1 mmol) followed by 5:1 mixture of 1,4-dioxane / water (30 mL). The reaction flask was placed under high vacuum and then repressurized with N2 repeated 3 times. The reaction was heated to 80° C. under a N2 atmosphere for 1 h. The solvent was removed in vacuo and the residue was dissolved in CHCl3 and filtered. The filtrate was purified by silica gel chromatography (ISCO MPLC, MeOH / CH2Cl2, 0-10% gradient). Pure fractions as determined by TLC and LCMS were combined and then concentrated in vacuo. The residue was dis...

example 2.3

Example 2. 3-[3-methyl-4-[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]benzoic acid

[0686]To a solution of methyl 3-[3-methyl-4-[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]benzoate (0.222 g, 0.55 mmol) in MeOH (70 mL) was added 0.2 M NaOH (30 mL). The reaction was stirred overnight at RT. DOWEX 50WX4-100 ion exchange resin was added. After 15 minutes, the resin was filtered, washed with MeOH and then the filtrate was concentrated in vacuo to yield the title compound (0.2025 g, 94%) as a white solid. LCMS (ESI, M+Na+=413.3); 1H NMR δ ppm (d3-MeOD; 2.31 (s, 3H) 3.61 (ddd, J=9.78, 5.09, 2.74 Hz, 1H) 3.69-3.84 (m, 3H) 3.97 (dd, J=9.39, 3.52 Hz, 1H) 4.08 (dd, J=3.33, 1.76 Hz, 1H) 5.56 (d, J=1.96 Hz, 1H) 7.31 (d, J=8.22 Hz, 1H) 7.39-7.48 (m, 2H) 7.51 (t, J=7.83 Hz, 1H) 7.76-7.84 (m, 1H) 7.95 (dt, J=7.83, 1.37 Hz, 1H) 8.21 (t, J=1.76 Hz, 1H)).

example 3.3

Example 3. 3-[3-methyl-4-[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]-N-(4-pyridyl)benzamide

[0687]To a stirred solution of 3-[3-methyl-4-[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]benzoic acid (0.039 g, 0.1 mmol) and HATU (0.046 g, 0.12 mmol) in DMF (5 mL) under a N2 atmosphere and cooled to 0° C. was added 4-aminopyridine (0.011 g, 0.12 mmol), and DIPEA (0.054 mL, 0.3 mmol). The reaction was allowed to warm to RT and then stirred overnight. The solvent was removed in vacuo and the residue purified by reversed phase HPLC (5-85% acetonitrile / water / 0.05% TFA). Pure fractions were combined and lyophilized to give the title compound as a white powder (0.047 g, 100%). LCMS (ESI, M+H+=467.3); 1H NMR δ ppm (d3-MeOD; 2.34 (s, 3H) 3.60 (ddd, J=9.78, 5.28, 2.54 Hz, 1H) 3.68-3.85 (m, 3H) 3.98 (dd, J=9.59, 3.33 Hz, 1H) 4.09 (dd, J=3.33, 1.76 Hz, 1H) 5.58 (d, J=1.57 Hz, 1H) 7.34 (d, J=8.61 Hz, 1H) 7.44-7.58 (m, 2H) ...

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Abstract

The present invention encompasses compounds and methods for treating and preventing bacterial infections specifically urinary tract infections and those caused by bacteria containing type 1 pili and FimH. The present invention also encompasses compounds and methods for treating inflammatory bowel disease specifically Crohn's Disease.

Description

CROSS REFERENCE TO RELATED APPLICATIONS[0001]This application is a continuation of U.S. application Ser. No. 14 / 894,927, filed Nov. 30, 2015, which claims the benefit of PCT International Patent Application No. PCT / US2014 / 040355, filed May 30, 2014, which claims the priority of U.S. provisional application No. 61 / 828,954, filed May 30, 2013, each of the disclosures of which are hereby incorporated by reference in its entirety.GOVERNMENTAL RIGHTS[0002]This invention was made with government support under RO1AI029549, P50DK064540 and RO1BK051406-12 awarded by the NIH. The government has certain rights in the invention.FIELD OF THE INVENTION[0003]The present invention encompasses compounds and methods for inhibiting the adhesin protein FimH and treating and preventing urinary tract infections and inflammatory bowel disease (e.g. Crohn's disease and ulcerative colitis).BACKGROUND OF THE INVENTION[0004]Urinary tract infection (UTI) caused by uropathogenic Escherichia coli (UPEC) is one o...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07H15/203C07H15/26A61K45/06A61K31/7064A61K31/7034A61K31/7056A61K31/7042A61K31/706
CPCA61K45/06A61K31/7064A61K31/706C07H15/203A61K31/7042A61K31/7034C07H15/26A61K31/7056A61P1/00A61P1/04A61P13/02A61P31/00A61P31/04Y02A50/30
Inventor JANETKA, JAMES W.HAN, ZHENFUHULTGREN, SCOTTPINKNER, JERRYCUSUMANO, CORINNE
Owner WASHINGTON UNIV IN SAINT LOUIS
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