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3-aminocyclopentanecarboxamides as modulators of chemotactic factor receptors

An alkyl and compound technology, applied in organic chemistry, active ingredients of heterocyclic compounds, etc., can solve the problem of cell infection and no effect.

Inactive Publication Date: 2007-06-06
INCYTE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This compound specifically inhibits CCR5-mediated HIV-1 infection in U-87 astroglioma, but has no effect on cell infection expressing CXCR4 (Strizki et al., Proc.Natl.Acad.Sci.USA, 2001, 98 (22), 12718 or Tremblay et al., Antimicrobial Agents and Chemotherapy, 2002, 46(5), 1336)

Method used

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  • 3-aminocyclopentanecarboxamides as modulators of chemotactic factor receptors
  • 3-aminocyclopentanecarboxamides as modulators of chemotactic factor receptors
  • 3-aminocyclopentanecarboxamides as modulators of chemotactic factor receptors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0284]

[0285] N-[(1R,3S)-3-isopropyl-3-9{4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}carbonyl]cyclopentyl]tetrahydro-2H - Preparation of pyran-4-amine

[0286] Step A-1

[0287]

[0288] (1R,4S)-4-[(tert-butoxycarbonyl)amino]cyclopent-2-ene-1-carboxylic acid methyl ester

[0289] To a solution of (1R,4S)-4-[(tert-butoxycarbonyl)amino]cyclopent-2-ene-1-carboxylic acid (10.0 g, 44 mmol) in DMF (25 mL) was added potassium carbonate (6.33 g, 45.8 mmol), followed by the addition of methyl iodide (4.0 mL, 64 mmol). After stirring overnight at room temperature, the reaction mixture was diluted with EtOAc. The solution was washed 4 times with water and 1 time with brine, dried (MgSO 4 ) and concentrate. The residue was dried under high vacuum overnight to give the title compound (11 g, 99%). C 12 h 19 NO 4 Calculated MS value: (M+H) + 242; Found 142.1 (M-Boc+H) + . 1 H NMR (CDCl 3 )δ5.86(m, 2H), 4.90(m, 1H), 4.80(m, 1H), 3.72(s, 3H), 3.50(m, 1H), 2.51(m, 1H), 1.86...

Embodiment 2

[0315] N-[(1R,3S)-3-isopropyl-3-({4-[4-(trifluoromethyl)phenyl]piperazin-1-yl}carbonyl)cyclopentyl]tetrahydro-2H - Preparation of pyran-4-amine

[0316]

[0317] The title compound was prepared in a manner similar to that described for Example 1 starting from N-(4-trifluoromethylphenyl)piperazine. C 25 h 36 f 3 N 3 o 2 MS calculated for: (M+H) 468; found 468.2.

Embodiment 3

[0319] N-[(1R,3S)-3-isopropyl-3-({4-[2-(trifluoromethyl)phenyl]piperazin-1-yl}carbonyl)cyclopentyl]tetrahydro-2H - Preparation of pyran-4-amine

[0320]

[0321] The title compound was prepared in a manner similar to that described for Example 1 starting from N-(2-trifluoromethylphenyl)piperazine. C 25 h 36 f 3 N 3 o 2 MS calculated for: (M+H) 468; found 468.2.

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Abstract

The present invention is directed to compounds of formula (I) : which are modulators of chemokine receptors. The compounds of the invention, and compositions thereof, are useful in the treatment of diseases related to chemokine receptor expression and / or activity.

Description

field of invention [0001] The present invention relates to compounds that modulate the activity of chemokine receptors, such as CCR2. In certain embodiments, the compounds are selective for CCR2. For example, these compounds can be used to treat diseases associated with chemokine receptor expression or activity, such as inflammatory diseases, immune diseases, and cancer. Background of the invention [0002] Migration and transport of leukocytes from blood vessels into diseased tissues is involved in initiating normal anti-disease inflammatory responses. This process, also known as the leukocyte recruitment response, is also involved in the onset and progression of inflammatory and autoimmune diseases. These diseases produce pathological conditions that result from an attack by the body's immune system on apparently normal tissues. Therefore, preventing and blocking leukocyte recruitment to target tissues in inflammatory diseases, metabolic diseases, autoimmune diseases an...

Claims

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Application Information

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IPC IPC(8): A61K31/497C07D403/14A61K31/445C07D241/04A61K31/44C07D401/10
Inventor 薛楚标郑长胜冯皓M·夏J·戈兰恩曹敢峰B·W·迈特卡夫
Owner INCYTE