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4-(1-amino-ethyl)-cyclohexylamine derivatives

A technology of cyclohexyl and cyclohexylamino, applied in the field of 4-(1-amino-ethyl)-cyclohexylamine derivatives, can solve difficult problems such as treatment

Inactive Publication Date: 2009-10-21
IDORSIA PHARM LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In hospital settings, increasing numbers of strains of Staphylococcus aureus, Streptococcus pneumoniae, Enterococcus spp., and Pseudomonas aeruginosa (major sources of infection) are Become multidrug resistant and therefore difficult, if not impossible, to treat:

Method used

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  • 4-(1-amino-ethyl)-cyclohexylamine derivatives
  • 4-(1-amino-ethyl)-cyclohexylamine derivatives
  • 4-(1-amino-ethyl)-cyclohexylamine derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0645] Example 1: 6-(trans-{4-[(1R)-1-amino-2-(6-methoxy-[1,5]naphthyridin-4-yl)-ethyl]-cyclohexylamino }-methyl)-4H-pyrido[3,2-b][1,4]thiazin-3-one:

[0646] 1.i. Toluene-4-sulfonic acid trans-4-tert-butoxycarbonylamino-cyclohexylmethyl ester:

[0647] TEA (8.5 mL, 2 eq.) and p-TsCl (7 g, 1.2 eq.) were added to trans-(4-hydroxymethyl-cyclohexyl)-carbamate tert-butyl ester (7.06 g, 30.8 mmol) in DCM ( 120 mL) and THF (30 mL) in ice-cooled solution. The mixture was then stirred overnight at room temperature. DMAP (1 g) was added and the reaction was allowed to proceed for 2 hours. Add saturated NaHCO 3 (100ml). The organic layer was washed with saturated CuSO 4 (2 x 100 mL), water (100 mL) and brine for further washing. The organic layer was then concentrated to dryness. The resulting solid was filtered off, washed with water and dried under vacuum. The title tosylate was obtained as a white solid (11.7 g, 99% yield).

[0648] MS (ESI, m / z): 384.3 [M+H] + .

[0649] ...

Embodiment 2

[0697] Example 2: 6-(trans-{4-[(1S)-1-amino-2-(6-methoxy-[1,5]naphthyridin-4-yl)-ethyl]-cyclohexylamino }-methyl)-4H-pyrido[3,2-b][1,4]thiazin-3-one:

[0698] The compound of Example 2 was obtained using 2 different preparation methods.

[0699] Method A:

[0700] Starting from intermediate 1.xiv.b (0.023 g), the title enantiomer (0.018 g) was obtained as an off-white solid using the procedure described in Example 1, step 1.xv. The compound was triturated in ether.

[0701] MS (ESI, m / z): 479.2 [M+H + ].

[0702] Method B:

[0703] 2.B.i. Methanesulfonic acid (1R)-trans-1-(4-benzyloxycarbonylamino-cyclohexyl)-2-(6-methoxy-[1,5]naphthyridin-4-yl)-ethyl ester:

[0704] TEA (0.83 mL, 2 eq.), DMAP (0.036 g, 0.1 eq.) and MsCl (0.3 mL, 1.3 eq.) were added to intermediate 1.ix (1.3 g, 2.98 mmol) in DCM (30 mL) in the ice-cooled mixture. The reaction was stirred at 0 °C for 15 minutes and then at room temperature for 1 hour. Add saturated NaHCO 3 (100 mL). The two layers we...

Embodiment 3

[0718] Embodiment 3: 6-(anti-{4-[(1R ＊ , 2R ＊)-1-amino-2-hydroxyl-2-(6-methoxy-[1,5]naphthyridin-4-yl)-ethyl]-cyclohexylamino}-methyl)-4H-pyrido[ 3,2-b][1,4]thiazin-3-one:

[0719] 3.i. trans-2-(4-tert-butoxycarbonylamino-cyclohexyl)-3-hydroxy-3-(6-methoxy-[1,5]naphthyridin-4-yl)-propionic acid Methyl esters:

[0720] LiHMDS (1M in THF, 17.1 mL) was added dropwise to trans-(4-tert-butoxycarbonylaminocyclohexyl)-acetic acid methyl ester (1.80 g, 6.63 mmol; prepared according to WO 2000 / 024717) over 10 minutes ) in THF (20 mL) cooled to -78°C. The resulting solution was stirred in a dry ice bath (set the temperature at -40°C) for 1.5 hours. The reaction was recooled to -78°C and 6-methoxy-[1,5]naphthyridine-4-carbaldehyde (3.35 g, 17.82 mmol; prepared according to WO 2006 / 032466) was added rapidly as a solid (2 mL was also added THF for washing) and stirring was continued at -78°C for 1.75 hours. Add NH 4 Cl (50 mL) and EA (50 mL). The two layers were separated and the ...

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Abstract

The invention relates to compounds of formula (I) wherein R0 represents H or OH; R1 represents alkoxy; U and W represent N, V represents CH and R2 represents H or F, or U and V represent CH, W represents N and R2 represents H or F, or U and V represent N, W represents CH and R2 represents H, or U represents N, V represents CH, W represents CRa and R2 represents H; Ra represents CH2OH oralkoxycarbonyl; A represents the group CH=CH-B or a binuclear heterocyclic system D, B representing a mono- or di-substituted phenyl group wherein the substituents are halogen atoms and D representing one of the following groups wherein Z represents CH or N, and Q represents O or S; and to salts of such compounds. These compounds are useful as antibacterial agents.

Description

technical field [0001] The present invention relates to novel 4-(1-amino-ethyl)-cyclohexylamine derivatives, pharmaceutical antibacterial compositions containing them and the use of these compounds for the preparation of medicaments for the treatment of infections, such as bacterial infections. These compounds are useful antimicrobial agents effective against a wide variety of human and veterinary pathogens including, inter alia, Gram positive and Gram negative aerobic and anaerobic bacteria and mycobacteria . Background technique [0002] The extensive use of antibiotics has exerted selective evolutionary pressure on microorganisms resulting in genetic-based resistance mechanisms. The problem of resistance development is exacerbated by modern medicine and socioeconomic practices that create slow-growing environments for pathogenic microorganisms (eg in artificial joints) and support long-term reservoir hosts (eg in immunocompromised patients). [0003] In hospital setting...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/4375A61P31/04
CPCC07D471/04C07D513/04C07D215/20C07D413/12C07D215/48C07D215/227A61P31/00A61P31/04C07D487/04C07D487/02A61K31/4375
Inventor 克里斯蒂安·哈伯舒兰乔治·吕迪吉恩-菲利普·苏里维特科内丽亚·扎姆布朗恩·埃科林
Owner IDORSIA PHARM LTD
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