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Pyridin-4-yl derivatives

An ethyl and alkyl technology, applied in the field of pyridine-4-yl derivatives, can solve the problems of accelerating organ damage, weakening the immune system's defense against infection and malignant diseases, etc. Effects of end organ damage

Active Publication Date: 2017-12-26
IDORSIA PHARM LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Beneficial effects of broad immunosuppressive therapy are associated with their effects; however, the systemic immunosuppression produced by these drugs weakens the immune system's defenses against infection and malignancy
In addition, standard immunosuppressive drugs are often used in high doses and can cause or accelerate organ damage

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0144] (S)-N-(3-(2-Ethyl-4-(5-(2-ethylpyridin-4-yl)-1,2,4-oxadiazol-3-yl)-6-methanol Base-phenoxy)-2-hydroxypropyl)-2-glycolamide

[0145]

[0146] EDC HCl (307mg, 1.60mmol) and HOBt (216mg, 1.60mmol) were added to N-((S)-3-[2-ethyl-4-(N-hydroxyformamidoyl)-6-methyl- A solution of phenoxy]-2-hydroxy-propyl)-2-hydroxy-acetamide (290 mg, 1.60 mmol) in DMF (15 mL). The mixture was stirred at room temperature for 20 minutes, then 2-ethyl-isonicotinic acid (347 mg, 1.07 mmol) was added. Stirring was continued for 1 hour at room temperature. The mixture was diluted with ethyl acetate (50 mL) and washed with NaHCO 3It was washed twice with saturated aqueous solution (2×10 mL) and brine (1×10 mL). The organic extract was subjected to MgSO 4 Dry, filter and concentrate. The remaining residue was dissolved in dioxane (8 mL) and the mixture was stirred at 120 °C for 1 hr. The mixture was concentrated and the crude product was purified by preparative HPLC (Waters XBridge 10 μm, ...

example 2

[0148] (S)-N-(3-(2-Ethyl-4-(5-(2-propylpyridin-4-yl)-1,2,4-oxadiazol-3-yl)-6-methanol Base-phenoxy)-2-hydroxypropyl)-2-glycolamide

[0149]

[0150] Preparation is carried out analogously to Example 1. Beige solid; LC-MS: t R =0.68min,[M+1] + =455.22; 1 H NMR (CDCl 3 ):δ8.77(d,J=5.1Hz,1H),7.93(s,1H),7.84-7.89(m,3H),7.20(t br,J=5.8Hz,1H),4.18-4.25(m ,3H),3.90(dd,J 1 =9.6Hz,J 2 =4.7Hz,1H),3.85(dd,J 1 =9.5Hz,J 2 =6.1Hz,1H),3.79(ddd,J 1 =14.1Hz,J 2 =6.5Hz,J 3 =3.0Hz,1H),3.49-3.58(m,1H),2.90-2.96(m,2H),2.75(q,J=7.5Hz,2H),2.39(s,3H),1.81-1.91(m, 2H), 1.32(t, J=7.5Hz, 3H), 1.04(t, J=7.3Hz, 3H); 13 C NMR (CDCl 3 ): δ173.8, 173.7, 168.9, 164.0, 157.4, 150.2, 137.7, 131.7, 131.5, 128.3, 126.6, 122.3, 120.5, 118.7, 74.2, 70.0, 62.1, 42.3, 40.3, 23.0, 22, 31.8, 16.5

example 3

[0152] (S)-N-(3-(2-Ethyl-4-(5-(2-isopropylpyridin-4-yl)-1,2,4-oxadiazol-3-yl)-6- Methylphenoxy)-2-hydroxypropyl)-2-glycolamide

[0153]

[0154] Preparation is carried out analogously to Example 1. Beige solid; LC-MS: t R =0.71min,[M+1] + = 455.20; 1 H NMR (CDCl 3 ):δ8.75(d,J=5.1Hz,1H),7.93(s,1H),7.81-7.86(m,3H),7.37(t,J=5.8Hz,1H),4.16-4.24(m, 3H),3.82-3.92(m,2H),3.78(ddd,J 1 =14.0Hz,J 2 =6.5Hz,J 3 =3.1Hz, 1H), 3.48-3.57(m, 1H), 3.22(septet, J=7.0Hz, 1H), 2.73(q, J=7.5Hz, 2H), 2.37(s, 3H), 1.40( d, J=6.9Hz, 6H), 1.30(t, J=7.5Hz, 3H); 13 C NMR (CDCl 3 ): δ174.0, 173.4, 169.04, 168.99, 157.4, 150.2, 137.7, 131.70, 131.67, 128.4, 126.7, 122.4, 118.9, 118.6, 74.1, 70.1, 62.2, 42.3, 36.5, 22.9, 22.5

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Abstract

The present invention relates to compounds of formula (I), wherein R1 and R2 are as described in the description, their preparation and their use as pharmaceutically active compounds. Said compounds are especially useful as immunomodulators.

Description

technical field [0001] The present invention relates to S1P of formula (I) 1 / EDG1 receptor agonists and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also relates to related aspects, including processes for the preparation of said compounds, pharmaceutical compositions containing compounds of formula (I), and their use alone or in combination with other active compounds or therapies to improve vascular function and as immunomodulators. Background technique [0002] The human immune system is designed to protect the body from foreign microorganisms and substances that cause infection or disease. Complex regulatory mechanisms ensure that the immune response targets the invading substance or organism rather than the host. In some instances, such control mechanisms are not regulated and an autoimmune response can occur. The consequence of an uncontrolled inflammatory response is severe organ, cell, tissue or joint damage. W...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/04A61K31/4433A61P37/00
CPCC07D413/04A61P1/04A61P11/02A61P11/06A61P13/12A61P17/06A61P19/02A61P25/00A61P27/14A61P29/00A61P35/00A61P35/04A61P37/00A61P37/02A61P37/06A61P37/08A61P5/14A61P3/10
Inventor 马丁·博利西里尔·莱斯高普奥利弗·内勒比特·斯坦纳
Owner IDORSIA PHARM LTD
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