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Acetylene derivatives as stearoyl coa desaturase inhibitors

A solvate and compound technology, applied in the field of stearoyl CoA desaturase inhibitors, can solve problems such as weak non-specific SCD1 inhibitors

Inactive Publication Date: 2009-11-18
GLENMARK PHARMACEUTICALS LIMITED
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, all of these substances are weak non-specific inhibitors of SCD1

Method used

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  • Acetylene derivatives as stearoyl coa desaturase inhibitors
  • Acetylene derivatives as stearoyl coa desaturase inhibitors
  • Acetylene derivatives as stearoyl coa desaturase inhibitors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach

[0058] According to a preferred embodiment of the present invention, the SCD1 inhibitor is selected from

[0059]

[0060] Formula II Formula III

[0061]

[0062] Formula IV Formula V

[0063]

[0064] Formula VI Formula VIII

[0065]

[0066] Formula VII

[0067] or a pharmaceutically acceptable salt, solvate, stereoisomer, prodrug or N-oxide thereof, wherein:

[0068] R' is selected from substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkylalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted cycloalkenylalkyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted Heteroarylalkyl, substituted or unsubstituted heterocycle and substituted or unsubstituted heterocyclylalkyl;

[0069] R is selected from hydroge...

Embodiment 1

[0498] 4-[5-(3-Hydroxy-1-propynyl)-2-pyridyl]piperazin-1-yl-2-trifluoromethyl phenyl ketone

[0499]

[0500] The product is obtained by the presence of PdCl 2 (PPh 3 ) 2 (20mg, 0.0284mmol) and CuI (16mg, 0.084mmol) in the case of intermediate 1 (1.1g, 2.827mmol) and prop-1-yn-1-ol (317mg, 5.655mmol) in triethylamine in Preparation was carried out by Sonogashira coupling reaction under nitrogen for 18 hours. The crude product obtained after extractive workup with chloroform was purified by column chromatography on silica gel, eluting with 30% EtOAc in chloroform, to give 270 mg of the product as an off-white solid; IR (KBr) 3298, 2851, 2240, 1626, 1497, 1242, 1010, 769cm -1 ; 1 H NMR (300MHz, CDCl 3 )δ1.81(br s, 1H, can be compared with D 2 O exchange), 3.28 (br s, 2H), 3.54-3.68 (m, 4H), 3.88-3.95 (m, 2H), 4.48 (s, 2H), 6.58 (d, J=8.4Hz, 1H), 7.36 (d, J=6.9Hz, 1H), 7.52-7.62(m, 3H), 7.74(d, J=7.2Hz, 1H), 8.26(s, 1H); ESI-MS (m / z) 390.30(M +H) + .

Embodiment 2

[0502] 4-[5-(3-Hydroxy-1-propynyl)-2-pyridyl]piperazin-1-yl-2,5-dichlorophenyl ketone

[0503]

[0504] Prepared by Sonogashira coupling of intermediate 3 with prop-1-yn-1-ol to give the product as a white solid; IR (KBr) 3351, 2846, 2237, 1628, 1495, 1239, 1012, 822cm -1 ; 1 H NMR (300MHz, CDCl 3 )δ1.71(t, J=6.3Hz, 1H, can be compared with D 2 O exchange), 3.30-3.39 (m, 2H), 3.60-3.69 (m, 4H), 3.85-3.96 (m, 2H), 4.49 (d, J=6.0Hz, 2H), 6.59 (d, J=9.0 Hz, 1H), 7.31-7.35 (m, 3H), 7.53 (d, J=8.7Hz, 1H), 8.27 (s, 1H); ESI-MS (m / z) 390.61 [100%, (M+H ) + ].

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Abstract

The present invention provides Stearoyl CoA Desaturase (SCD) inhibitors, hi particular, compounds described herein are useful for treating or preventing diseases, conditions and / or disorders modulated by Stearoyl CoA Desaturase 1 (SCD 1) inhibitors. Also provided herein are processes for preparing compounds described herein, intermediates used in their synthesis, pharmaceutical compositions thereof, and methods for treating or preventing diseases, conditions and / or disorders modulated by Stearoyl CoA Desaturase (SCD) inhibitors.

Description

[0001] This application claims Indian Patent Application 1917 / MUM / 2006 filed on November 20, 2006, Indian Patent Application 2175 / MUM / 2006 filed on December 29, 2006 and Indian Patent Application on July 17, 2007 Application 1375 / MUM / 2007 and the priority of US Patent Application Serial No. 60 / 954,108, filed August 6, 2007, are hereby incorporated by reference. field of invention [0002] The present invention provides stearoyl-CoA desaturase (SCD) inhibitors. In particular, the compounds described herein are useful in the treatment or prevention of diseases, conditions and / or disorders modulated by stearoyl CoA desaturase 1 (SCD 1 ) inhibitors. Also provided herein are processes for the preparation of the compounds described herein, intermediates for their synthesis, pharmaceutical compositions thereof and for use in the treatment or prevention of diseases, conditions and / or conditions modulated by stearoyl-CoA desaturase (SCD) inhibitors way of obstacles. Background of th...

Claims

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Application Information

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IPC IPC(8): C07D213/74C07D237/20C07D239/42C07D277/18C07D401/10C07D401/12C07D405/06C07D405/10A61K31/426A61K31/44A61K31/506A61K31/501A61P3/00
Inventor A·托马斯V·S·P·R·林加姆S·K·帕坦加瑞N·凯拉特卡尔-裘西D·M·沙阿D·V·乌基尔德D·A·莫尔N·凯拉特卡尔－裘西
Owner GLENMARK PHARMACEUTICALS LIMITED
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