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Antibacterial agents

A solvate, bacterial infection technology, applied in the field of antimicrobial agents, which can solve the problems of undesired pharmacological properties, low potency, unknown specificity, etc.

Active Publication Date: 2009-04-08
BIOTA SCI MANAGEMENT PTI LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Unfortunately, most of the compounds described to date are either less potent, have undesired pharmacological properties, or unknown specificities

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0179] Example 1: 3-Nonyloxy-benzenecarboxamide.

[0180]

[0181] Add K 2 CO 3 (302mg, 2.19mmol, 1.5eq) and NaI (43.5mg, 0.29mmol, 0.2eq). The suspension was stirred for 5 minutes before n-nonyl chloride (0.32ml, 1.61mmol, 1.1eq) was introduced. The resulting mixture was heated to 60°C for 16 hours. Afterwards, the reaction was cooled to room temperature and partitioned between EtOAc and water. The organic phase was separated, washed with additional water (x2), dried (MgSO 4 ), filtered and concentrated in vacuo to give a colorless solid. For 3-n-nonyloxybenzamide, the colorless solid was stirred with MeOH (~0.5 ml) for 5 minutes [NB: 3-n-nonyloxybenzamide was partially dissolved in MeOH], then filtered to give The desired compound was obtained as a colored solid (116 mg, 30%). HPLC-MS (Method 3): m / z 264 [M+H] + , Rt = 1.80 min. 1 HNMR(d 6 -DMSO) δ=7.95(s, 1H), 7.44-7.31(m, 4H), 7.06(ddd, J=8Hz, J=2Hz, J=1Hz, 1H), 3.99(t, J=6.5Hz, 2H ), 1.72 (quintet, J=6.5Hz...

Embodiment 2-44

[0187] Examples 2-44 (Table A)

[0188] Examples 2-44 were prepared according to Method B, Scheme 2

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202] List of product compound names; Examples 2-44:

[0203] Example

Compound name

2

3-Propoxybenzenecarboxamide

3

3-Isopropoxybenzenecarboxamide

4

3-(cyclopropylmethoxy)benzenecarboxamide

5

3-(pentyloxy)benzenecarboxamide

6

3-(allyloxy)benzenecarboxamide

7

3-butoxybenzenecarboxamide

8

3-(Hexyloxy)benzenecarboxamide

9

3-(2-Methoxyethoxy)benzenecarboxamide

10

3-(4-phenoxybutoxy)benzenecarboxamide

11

3-[(2-Methyl-2-propenyl)oxy(oxy)]benzenecarboxamide

12

3-(7-octenyloxy)benzenecarboxamide

13

3-(Isoamyloxy)benzenecarboxamide

14

3-[(4-Methylpenty...

Embodiment 45

[0208] Example 45 3-[(Z)-5-Decenyloxy]benzenecarboxamide

[0209]

[0210] In a polymer-supported suspension of triphenylphosphine (1.4 g, 3 mmol, 2.15 mmol / g based on loading [purchased from Argonaut], 1.5 equivalents) swollen in THF (20 ml) at room temperature, Diisopropylazodicarboxylate (0.47ml, 2.4mmol, 1.2eq) was added. The mixture was shaken for 5 minutes, then 3-hydroxybenzamide (274mg, 2mmol, 1eq), triethylamine (0.28ml, 2mmol, 1eq) and cis-5-decenol (313mg, 2mmol, 1eq) were added. equivalent). The resulting suspension was shaken at room temperature for 16 hours, then filtered. The resin was washed with additional THF (x 3), then the combined filtrate and washings were concentrated under reduced pressure to give the crude product as a colorless semi-solid. Column chromatography on a silica gel column eluting with EtOAc / hexanes (20%-40% gradient) afforded the desired compound (390 mg, 71%) as a white solid, mp 98-100 °C. HPLC-MS (Method 1): m / z 276 [M+H] + ,...

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Abstract

Compounds of formula (I) have antibacterial activity wherein R represents hydrogen or 1, 2 or 3 optional substituents; W is =C(R1)- or =N-; R1 is hydrogen or an optional substituent and R2 is hydrogen, methyl, or fluorine; or R1 and R2 taken together are -CH2-, -CH2CH2-, -O-, or, in either orientation, -O- CH2- Or -OCH2CH2-; R3 is a radical of formula -(Alk<1>)m-(Z)p-(Alk<2>)n-Q wherein m, p and n are independently 0 or 1, provided that at least one of m, p and n is 1, Z is -O-, -S-, -S(O)-, -S(O2)-, -NH-, -N(CH3)-, -N(CH2CH3)-, -C(=O)-, -O-(C=O)-, -C(=O)-O-, or an optionally substituted divalent monocyclic carbocyclic or heterocyclic radical having 3 to 6 ring atoms; or an optionally substituted divalent bicyclic heterocyclic radical having 5 to 10 ring atoms; Alk<1> and Alk<2> are optionally substituted C1C6 alkylene, C2-C6 alkenylene, or C2-C6 alkynylene radicals, which may optionally terminate with or be interrupted by -O-, -S-, -S(O)-, -S(O2)-, -NH-, -N(CH3)-, or -N(CH2CH3)-; and Q is hydrogen, halogen, nitrile, or hydroxyl or an optionally substituted monocyclic carbocyclic or heterocyclic radical having 3 to 6 ring atoms; or an optionally substituted bicyclic heterocyclic radical having 5 to 10 ring atoms.

Description

field of invention [0001] The present invention relates to the use of substituted benzamides and pyridinamides as antibacterial agents, to new members of this class of compounds, and to pharmaceutical compositions comprising these compounds. Background technique [0002] Many antimicrobial classes are known, including penicillins and cephalosporins, tetracyclines, sulfonamides, monocyclic beta-lactams, fluoroquinolones and quinolones, aminoglycosides, glycopeptides, macrolides , polymyxins, lincosamides, trimethoprim and chloramphenicol. The mechanisms of action of these antimicrobials vary. [0003] Bacterial resistance to many known antimicrobial agents is an increasing problem. Accordingly, there is a continuing need in the art for alternative antimicrobial agents, especially those substances whose mechanism of action differs from known classes of antimicrobial agents. [0004] Among Gram-positive pathogens, such as staphylococci, streptococci, mycobacteria, and entero...

Claims

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Application Information

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IPC IPC(8): A61K31/166A61K31/341A61K31/343A61K31/352A61K31/381A61K31/4025A61K31/4155A61K31/4184A61K31/4192A61K31/422A61K31/423A61K31/4245A61K31/427A61K31/428A61K31/429
Inventor D·R·布朗I·克林斯L·G·洽普勒斯基D·J·海登
Owner BIOTA SCI MANAGEMENT PTI LTD
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