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A new peptide deformylase inhibitor compound and manufacturing process thereof

A compound, methyl technology, applied in the field of new antibacterial compounds, can solve the problem of not producing compounds and so on

Inactive Publication Date: 2010-06-02
IL DONG PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] Although a variety of compounds that have been described in the prior art have been developed as inhibitors of peptide deformylase, no compounds for clinical use have been produced

Method used

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  • A new peptide deformylase inhibitor compound and manufacturing process thereof
  • A new peptide deformylase inhibitor compound and manufacturing process thereof
  • A new peptide deformylase inhibitor compound and manufacturing process thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0250] (R)-2-Cyclopentylmethyl-N 1 -{(S)-2,2-Dimethyl-1-[4-(4-methyl-benzylamino)-piperidine-1-carbonyl]-propyl}-N 4 -Hydroxy-succinic acid amide

[0251]

[0252] The title compound was prepared from (R)-2-cyclopentylmethyl-succinic acid 4-tert-butyl ester 5-a according to general method V (R 2 = Cyclopentylmethyl, R 13 = tert-butyl) and [1-((S)-2-amino-3,3-dimethyl-butyryl)-piperidin-4-yl]-(4-methyl-benzyl)-amino Benzyl formate hydrochloride 1-g (prepared from general method I. R 3 = tert-butyl, R 6 = benzyloxycarbonyl, R 8 =R 9 =R 11 =R 12 =X=H,R 10 =Me, Q=C, n=1).

[0253] 1 H-NMR (CDCl 3 ): δ6.93-7.20(m, 4H), 6.10-6.22(m, 1H), 4.96-5.06(m, 1H), 4.72-4.93(m, 2H), 4.61-4.71(m, 1H), 4.05 -4.35(m, 4H), 3.71-3.85(s, 2H), 2.70-2.91(m, 1H), 2.42-2.62(m, 2H), 2.33(s, 3H), 1.31-1.84(m, 12H) , 1.00 (m, 9H).

Embodiment 2

[0255] (R)-2-cyclopentylmethyl-N-{(S)-2,2-dimethyl-1-[4-(4-methyl-benzylamino)-piperidine-1-carbonyl ]-Propyl}-3-(formyl-hydroxy-amino)-propionamide

[0256]

[0257] The title compound was prepared from (R)-3-(benzyloxy-formyl-amino)-2-cyclopentylmethyl-propionic acid 6-a (R) according to general method VI 2 = Cyclopentylmethyl, R 13 = benzyl) and [1-((S)-2-amino-3,3-dimethyl-butyryl)-piperidin-4-yl]-(4-methyl-benzyl)-amino Benzyl formate hydrochloride 1-g (prepared by general method I. R 3 = tert-butyl, R 6 = benzyloxycarbonyl, R 8 = R 9 = R 11 = R 12 =X=H,R 10 =Me, Q=C, n=1).

[0258] 1 H-NMR (CDCl 3 ): δ8.39(s, 0.4H), 7.80(s, 0.6H), 7.18-7.22(m, 2H), 7.11-7.17(m, 2H), 4.87-4.97(m, 1H), 4.20-4.54 (m, 1H), 3.79(s, 2H), 3.73-4.14(m, 1H), 3.42-3.58(m, 1H), 2.93-3.17(m, 1H), 2.63-2.90(m, 3H), 2.34 (s, 3H), 1.19-2.06 (m, 14H), 0.87-1.13 (m, 11H).

Embodiment 3

[0260] (R)-N-{(S)-1-[4-(4-cyano-benzylamino)-piperidine-1-carbonyl]-2,2-dimethyl-propyl}-2- Cyclopentylmethyl-3-(formyl-hydroxy-amino)-propionamide

[0261]

[0262] The title compound was prepared from (R)-3-(benzyloxy-formyl-amino)-2-cyclopentylmethyl-propionic acid 6-a (R) according to general method VI 2 = Cyclopentylmethyl, R 13 = benzyl) and [1-((S)-2-amino-3,3-dimethyl-butyryl)-piperidin-4-yl]-(4-cyano-benzyl)-amino Benzyl formate hydrochloride 1-g (prepared by general method I. R 3 = tert-butyl, R 6 = benzyloxycarbonyl, R 8 = R 9 = R 11 = R 12 =X=H,R 10 =CN, Q=C, n=1).

[0263] 1 H-NMR (CDCl 3 ): δ8.39(s, 0.3H), 7.81(s, 0.7H), 7.57-7.65(m, 2H), 7.40-7.49(m, 2H), 4.85-4.97(m, 1H), 4.18-4.56 (m, 1H), 3.96-4.16(m, 1H), 3.89(s, 2H), 3.40-3.57(m, 1H), 2.95-3.18(m, 1H), 2.65-2.92(m, 3H), 1.17 -2.06 (m, 14H), 0.83-1.13 (m, 11H).

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Abstract

The present invention relates to the novel antibacterial compounds having potent antibacterial activity as inhibitors of peptide deformylase. This invention further relates to pharmaceutically acceptable salts thereof, to processes for their preparation, and to pharmaceutical compositions containing them as an active ingredient.

Description

technical field [0001] The present invention relates to novel antibacterial compounds with potential antibacterial activity as peptide deformylase inhibitors. The present invention also relates to their pharmaceutically acceptable salts, processes for their preparation, and pharmaceutical compositions containing them as active ingredients. Background technique [0002] Since Flemming's accidental discovery of penicillin in 1920, it has been developed for therapeutic injection in the 1940s, and many antibiotics have been systematically developed since then. Many classes of antibiotics such as β-lactams, including penicillins and cephalosporins from natural products, aminoglycosides, phenylpropanes, tetracyclines, macrolides, glycopeptides, phosphonates, lipopeptides, and Quinolones and oxazolidinones from synthetic products (Christopher T. Walsh et al., Chem. Review, 2005, 105, 391-395.). [0003] But these antibiotics lead to severe resistance to existing antibiotics. Rec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/58
CPCC07D401/12C07D405/12C07D211/58A61P31/04A61P43/00A61K31/435
Inventor 康在勋柳承祐李喜烈安敬美赵埄唤
Owner IL DONG PHARMA CO LTD
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