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Heterocyclic piperidines as modulators of chemokine receptor activity

a technology heterocyclic piperidines, which is applied in the field of modulators of chemokine receptor activity, can solve the problems of not being disclosed nor suggested in the prior ar

Inactive Publication Date: 2007-12-27
BRISTOL MYERS SQUIBB PHARMA CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

"The present invention provides novel compounds that can act as agonists or antagonists of CCR-3, a protein involved in allergic disorders. These compounds can be used to develop pharmaceutical compositions for the treatment of allergic disorders. The invention is based on the discovery that certain compounds can effectively modulate the activity of chemokines, which are proteins involved in the immune system."

Problems solved by technology

The prior art does not disclose nor suggest the unique combination of structural fragments which embody these novel piperidines and pyrrolidines as having activity toward the chemokine receptors.

Method used

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  • Heterocyclic piperidines as modulators of chemokine receptor activity
  • Heterocyclic piperidines as modulators of chemokine receptor activity
  • Heterocyclic piperidines as modulators of chemokine receptor activity

Examples

Experimental program
Comparison scheme
Effect test

example 1

Preparation of (+ / −)-N-phenyl-2-[[4-[(4-fluorophenyl)methyl]-1-piperidinyl]methyl]-1-piperidinecarboxamide

Step A. Preparation of N-(t-butoxycarbonyl)-4-(4-fluorophenylmethalene)piperidine.

[0587] To a stirring solution of 4-fluorobenzyl-triphenylphosphonium chloride (61.3 g, 150.6 mmol, Fluka) in dry THF (500 mL) was added a 1M solution of potassium t-butoxide (138 mL). The reaction was stirred for 5 min and then a solution of N-(t-butoxycarbonyl)-4-piperidone (25 g, 125.5 mmol) in dry THF (100 mL) was added. After 10 min, the reaction was warmed to reflux for 16 h. After cooling to room temperature, the reaction was conc. in vacuo to an oil. The oil was dissolved in EtOAc and hexanes was added to form a white precipatate. The precipatate was filtered off and the filtrate conc. in vacuo to an oil. The oil was purified by flash chromatography (SiO2, 0-35% EtOAc in hexanes) to yield 27 grams (74%) of the product as a white solid. MS (ESI) 314 (M+Na).

Step B. Preparation of N-(t-but...

example 2

Preparation of (+ / −)-N-(3-cyanophenyl)-2-[[4-[(4-fluorophenyl)methyl]-1-piperidinyl]methyl]-1-piperidinecarboxamide

[0595] Prepared according to procedures described in Example 1 with modification at Step H. MS (ESI) 435 (M+H).

example 3

Preparation of (+ / −)-N-(3-methoxyphenyl)-2-[[4-[(4-fluorophenyl)methyl]-1-piperidinyl]methyl]-1-piperidinecarboxamide

[0596] Prepared according to procedures described in Example 1 with modification at Step H. MS (ESI) 440 (M+H).

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Abstract

The present application describes modulators of CCR3 of formula (I): or pharmaceutically acceptable salt forms thereof, useful for the prevention of asthma and other allergic diseases.

Description

FIELD OF THE INVENTION [0001] This invention relates generally to modulators of chemokine receptor activity, pharmaceutical compositions containing the same, and methods of using the same as agents for treatment and prevention of asthma and allergic diseases, as well as autoimmune pathologies such as rheumatoid arthritis and atherosclerosis. BACKGROUND OF THE INVENTION [0002] Chemokines are chemotactic cytokines, of molecular weight 6-15 kDa, that are released by a wide variety of cells to attract and activate, among other cell types, macrophages, T and B lymphocytes, eosinophils, basophils and neutrophils (reviewed in Luster, New Eng. J Med., 338, 436-445 (1998) and Rollins, Blood, 90, 909-928 (1997)). There are two major classes of chemokines, CXC and CC, depending on whether the first two cysteines in the amino acid sequence are separated by a single amino acid (CXC) or are adjacent (CC). The CXC chemokines, such as interleukin-8 (IL-8), neutrophil-activating protein-2 (NAP-2) an...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K31/55A61K31/445A61K31/497A61K31/40C07D211/26C07D401/06C07D401/14C07D405/14C07D409/14C07D413/06C07D413/14C07D417/14
CPCC07D211/26C07D401/06C07D401/14C07D417/14C07D409/14C07D413/06C07D413/14C07D405/14
Inventor KO, SOO S.DELUCCA, GEORGE V.DUNCIA, JOHN V.SANTELLA, JOSEPH B. IIIWACKER, DEAN A.
Owner BRISTOL MYERS SQUIBB PHARMA CO
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