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Novel cannabinoid receptor ligands, pharmaceutical compositions containing them, and process for their preparation

A compound and stereoisomer technology, applied in the field of cannabinoid receptor modulators, can solve problems such as poor compliance and liver toxicity

Inactive Publication Date: 2008-08-06
GLENMARK PHARMACEUTICALS LIMITED
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0019] Current treatments for alcohol abuse or dependence often suffer from poor adherence or potential hepatotoxicity

Method used

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  • Novel cannabinoid receptor ligands, pharmaceutical compositions containing them, and process for their preparation
  • Novel cannabinoid receptor ligands, pharmaceutical compositions containing them, and process for their preparation
  • Novel cannabinoid receptor ligands, pharmaceutical compositions containing them, and process for their preparation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 101

[0777] N(7)-piperidin-1-yl-5-(2-bromophenyl)-5,6-diazatetracyclo[7.3.1.1 3，11 .0 4，8 ] Fourteen carbon-4(8),6-diene-7-carboxamide

[0778] The solution of Intermediate 1 (300mg, 0.78mmol) in DMF (3ml) was used at room temperature with BOP reagent (319mg, 0.72mmol) and Et 3 N (0.10 ml, 0.99 mmol) was treated for 15 minutes, after which, N-aminopiperidine (80 μl, 0.90 mmol) was added to the mixture and stirred at room temperature for 1 hour. The mixture was poured into water, the formed precipitate was collected by filtration, dried and purified by flash silica gel chromatography to obtain the pure title compound (270 mg, 74%). M.P.: 244°C. 1H-NMR(δppm, CDCl 3 , 300MHz): 7.72 (d, J = 7.6, 1H); 7.65 (br.s, 1H); 7.50-7.30 (m, 3H; 3.97 (br.s, 1H); 2.85 (br.s, 4H); 2.51 (br.s, 1H); 2.16 (br.s, 2H); 2.10-1.50 (m, 14H); 1.40 (br.s, 2H). IR (cm -1 , KBr): 3311(w), 2913(s), 2844(m), 2793(m), 1687(s), 1570(w), 1522(s), 1489(m), 1479(m), 1440 (m), 1352(m), 1227(m), 1214(m). MS(m / z)469.4([M+H1...

Embodiment 102

[0780] N(7)-Benzyl-5-(2-bromophenyl)-5,6-diazatetracyclo[7.3.1.1 3，11 .0 4，8 ] Fourteen carbon-4(8),6-diene-7-carboxamide

[0781] The title compound was synthesized by a method similar to that described in Example 101. Use Intermediate 1 (300mg, 0.78mmol), DMF (3ml), Et 3 N (0.10ml, 0.99mmol), BOP reagent (319mg, 0.72mmol) and benzylamine (80μl, 0.72mmol) gave the title compound (280mg, 76%). M.P.: 201°C. 1 H-NMR(δppm, CDCl 3 , 300MHz): 7.70 (d, J=7.5, 1H); 7.44 (dd, J=7.5, 1.5, 1H); 7.41-7.20 (m, 8H); 4.63 (dd, J=14.4, 6.0, 1H); 4.50 (dd, J=16.5, 5.4, 1H); 4.00 (br.t, J=5.1, 1H); 2.52 (br.t, J=5.1, 1H); 2.13 (br.s, 2H); 2.13 1.92 (m, 4H); 1.92-1.65 (m, 6H). IR(cm -1 , KBr): 3428(m), 2908(s), 2845(m), 1672(s), 1566(m), 1522(s), 1498(s), 1472(s), 1351(m), 1087 (m), 1024 (m), 1010 (m), 778 (m), 763 (m), 726 (m), 698 (m). MS(m / z): 476.4([M+H] + ).

Embodiment 103

[0783] N(7)-morpholino-5-(4-chlorophenyl)-5,6-diazatetracyclo[7.3.1.1 3，11 .0 4，8 ] Fourteen carbon-4(8),6-diene-7-carboxamide

[0784] The title compound was synthesized by a method similar to that described in Example 101. Use Intermediate 2 (100mg, 0.29mmol), DMF (1.0ml), Et 3 N (40 μl, 0.29 mmol), BOP reagent (129 mg, 0.29 mmol) and N-aminomorpholine (28 μl, 0.29 mmol) gave the title compound (97 mg, 78%). M.P.: 220°C. 1 H-NMR(δppm, CDCl 3 , 300MHz): 7.75 (br.s, 1H); 7.47 (d, J = 8.1, 2H); 7.29 (d, J = 8.1, 2H); 3.96 (br.s, 1H); 3.85 (t, J = 4.5, 4H); 2.99 (br.s, 1H); 2.95 (t, J=4.5, 5H); 2.20 (br.s, 2H); 2.10-1.76 (m, 10H). IR(KBr, cm -1 ): 2915(s), 2848(m), 1674(s), 1532(m), 1498(s), 1304(m), 1267(m), 1219(m), 1112(s), 1091(s) ), 895(m), 838(s). MS(m / z): 427.3([M+H] + ).

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Abstract

The present invention relates to novel cannabinoid receptor modulators, in particular cannahinoid I (CB1) or cannabinoid 2 (CH2) receptor modulators, and uses thereof for treating diseases, conditions and / or disorders modulated by a cannabinoid receptor (such as pain, neurodegenerative disorders, eating disorders, weight loss or control, and obesity).

Description

[0001] This application requires Indian Patent Application No. 659 / MUM / 2005 (filed on June 2, 2005), U.S. Provisional Application No. 60 / 696,433 (filed on July 1, 2005), and Indian Patent Application No. 370 / MUM / 2005 No. (filed on October 10, 2005), Indian Patent Application No. 344 / MUM / 2006 (filed on March 9, 2006), U.S. Provisional Application No. 60 / 744,071 (filed on March 31, 2006) and India Benefits of Patent Application No. 689 / MUM / 2006 (filed on May 3, 2006), all of these patent applications are incorporated herein by reference. Invention field [0002] The present invention relates to new cannabinoid receptor modulators, especially cannabinoid 1 (CB1) or cannabinoid 2 (CB2) receptor modulators, and their use in the treatment of diseases, conditions and / or diseases modulated by cannabinoid receptors. Or abnormal (such as pain, neurodegenerative diseases, eating disorders, weight loss or control, and obesity). Background of the invention [0003] The endocannabinoid system i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/54A61K31/416
Inventor M·穆图帕拉尼亚帕恩G·巴拉苏布拉马尼安S·古拉帕利N·K·乔希S·纳拉亚南
Owner GLENMARK PHARMACEUTICALS LIMITED
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