Derivatives of 2-aminopyridine as adenosine a2b receptor antagonists and ligands of the melatonin mt3 receptors

A technology of pyridine and alkyl, applied in the field of pyridine derivatives, can solve problems such as limiting the pro-inflammatory effect of adenosine

Active Publication Date: 2017-11-28
PALOBIOFARMA SL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Antagonists of this receptor would likely limit the pro-inflammatory effects of adenosine

Method used

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  • Derivatives of 2-aminopyridine as adenosine a2b receptor antagonists and ligands of the melatonin mt3 receptors
  • Derivatives of 2-aminopyridine as adenosine a2b receptor antagonists and ligands of the melatonin mt3 receptors
  • Derivatives of 2-aminopyridine as adenosine a2b receptor antagonists and ligands of the melatonin mt3 receptors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0262] Example 1 : 5-(pyridin-4-yl)-6-(pyrimidin-5-yl)pyridin-2-amine

[0263]

[0264] 5-Iodo-6-(pyrimidin-5-yl)pyridin-2-amine (0.53 g, 1.77 mmol) and (pyridin-4-yl)boronic acid pinacol ester (0.91 g, 4.42 mmoles), [1, 1'bis(diphenylphosphino)ferrocene]dichloropalladium(II) - complexed with dichloromethane (0.087g, 0.107mmoles), and 1,4-bis A mixture of 2M aqueous cesium carbonate solution (3.6 mL) in alkanes (14.3 mL) was heated to 110 °C and left to stir for 20 hours. The mixture was cooled and then partitioned between ethyl acetate and 1M aqueous sodium hydroxide solution. Partition the organic phase with sodium bicarbonate and brine. dry (MgSO 4 ) and evaporate the final organic layer. The residue precipitated as a pale pink fine solid which was rinsed with cold diethyl ether and dried (0.286 g, 54.8%).

[0265] 1 H-NMR (400MHz, DMSO-d 6 ): δ=6.52(s, 2H), 6.64(d, 1H), 7.13(d, 2H), 7.58(d, 1H), 8.44(d, 2H), 8.61(s, 2H), 9.09(s, 1H).

[0266] HPLC-MS: Rt 1.886...

Embodiment 2

[0267] Example 2 : 5-(3-fluoropyridin-4-yl)-6-(pyrimidin-5-yl)pyridin-2-amine

[0268] Following the procedure described in Example 1, this product was synthesized from 6-(pyrimidin-5-yl)pyridin-2-amine and 3-fluoropyridine-4-boronic acid.

[0269] 1 H-NMR (400MHz, DMSO-d 6 ): δ=6.61(s, 2H), 6.65(d, 1H), 7.38(dd, 1H), 7.57(d, 1H), 8.39(d, 1H), 8.43(d, 1H), 8.62(s, 2H), 9.10(s, 1H).

[0270] HPLC-MS: Rt 2.082m / z 268.0 (MH + ).

Embodiment 3

[0271] Example 3 : 6-(pyridin-3-yl)-5-(pyridin-4-yl)pyridin-2-amine

[0272] Following the procedure described in Example 1, this product was synthesized from 6-(pyridin-3-yl)pyridin-2-amine and pyridine-4-boronic acid.

[0273] 1 H-NMR (400MHz, DMSO-d 6 ): δ=6.42(s, 2H), 6.59(d, 1H), 7.06(d, 2H), 7.30(dd, 1H), 7.55(d, 1H), 7.63(d, 1H), 8.37(d, 1H), 8.39(d, 2H), 8.46(d, 1H).

[0274] HPLC-MS: Rt 2.804m / z 249.1 (MH + ).

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Abstract

The present invention relates to novel pyridine derivatives of formula (I) as A2B adenosine receptor antagonists and ligands of MT3 melatonin receptor, to processes for their preparation, to pharmaceutical compositions comprising said compounds and to the use of said for manufacturing a medicament for the treatment of pathological conditions or diseases that can improve by antagonizing the adenosine A2B receptor and by inhibition of MT3 melatonin receptor, such as respiratory disease, metabolic disorders, neurological disorders and cancer.

Description

technical field [0001] The present invention relates to as A 2B Adenosine receptor antagonists and MT 3 Novel pyridine derivatives of ligands for the melatonin receptor. [0002] Other objects of the present invention are to provide a method for preparing said compound; a pharmaceutical composition comprising an effective amount of said compound; 2B receptor and by inhibiting MT 3 Use in medicine for pathological conditions or diseases which are ameliorated by melatonin receptors, such as respiratory diseases, metabolic disorders, neurological disorders and cancers. Background technique [0003] Adenosine passes through four subtypes of receptors—A 1 、A 2A 、A 2B and A 3 - adjust its function. These receptors are grouped according to their action on adenylate cyclase. A 1 and A 3 Receptors inhibit cAMP production by coupling to G proteins. A 2A and A 2B The receptor increases cAMP levels by stimulating an enzyme - adenylate cyclase - and also by coupling to G pr...

Claims

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Application Information

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IPC IPC(8): C07D401/14A61K31/444A61K31/506A61P11/06A61P11/00A61P3/04A61P3/10A61P9/10A61P25/16A61P25/28A61P35/00
CPCC07D401/14A61K31/444A61K31/506A61K45/06A61P11/00A61P11/06A61P11/08A61P25/16A61P25/28A61P3/04A61P35/00A61P3/06A61P3/08A61P43/00A61P9/10A61P3/10C07D213/73A61K31/4412A61K2300/00
Inventor J·C·卡斯特罗-巴洛米诺马拉里亚J·A·卡马乔古梅兹A·门多萨里咂尔德斯
Owner PALOBIOFARMA SL
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