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Fused pyrrolopyridine derivative

A kind of technology of pyridine and compound, applied in the field of condensed pyrrolopyridine derivatives, can solve problems such as undisclosed skeleton compounds

Inactive Publication Date: 2012-03-28
ASTELLAS PHARMA INC
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0019] In addition, International Publication No. WO 2009 / 152133 pamphlet published after the priority date of the present application describes that a group of compounds having a dihydrodipyrrolopyridine skeleton is effective as various kinase inhibitors, but this Specific compounds having this skeleton are not disclosed in the specification (Patent Document 4)

Method used

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  • Fused pyrrolopyridine derivative
  • Fused pyrrolopyridine derivative
  • Fused pyrrolopyridine derivative

Examples

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Embodiment

[0391] The preparation method of the compound represented by formula (I) will be described in more detail below based on the examples. In addition, the present invention is not limited to the preparation methods shown in the following specific examples and preparation examples, and the compound represented by formula (I) can also be prepared by a combination of these preparation methods or methods obvious to those skilled in the art.

[0392] In addition, the following symbols are used in Examples, preparation examples, and the table|surface mentioned later.

[0393] Pr: Preparation number

[0394] Ex: Example number

[0395] No: compound number

[0396] Data: physical and chemical data

[0397] ESI+: m / z value in ESI-MS (positive ion)

[0398] ESI-: m / z value in ESI-MS (anion)

[0399] APCI+: m / z value in APCI-MS (positive ion)

[0400] NMR-DMSO-d 6 : DMSO-d 6 middle 1 δ(ppm) of H-NMR

[0401] rac-: the racemate of the compound described in the text or in the struct...

preparation example 1

[0423] (methoxymethyl)triphenylphosphine chloride THF (10.6 mL) was added to (1.00 g), and sodium bis(trimethylsilyl)amide (1.07M THF solution, 3.22 mL) was added dropwise under ice cooling, and stirred for 30 minutes. Add dropwise rac-4-{[(3R,4R)-1-benzyl-4-methylpiperidin-3-yl]amino}-1-{[2-(trimethylsilyl ) ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (1.27 g) in THF (10.0 mL), and stirred at room temperature for 4 hours. After adding saturated aqueous ammonium chloride solution to the reaction mixture, the mixture was extracted with EtOAc, and washed with saturated brine. use Na 2 SO 4 After drying the organic layer, it was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (EtOAc / Hx=10 / 90~30 / 70) to obtain rac-N-[(3R,4R)-1-benzyl-4-methylpiperidin-3-yl] -5-(2-Methoxyvinyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-4- Amine (1.34g).

[0424] Compounds of Prep...

preparation example 2

[0426] By continuously carrying out the same method as Preparation Example 1 and Preparation Example 3, the compounds of Preparation Example 2 and Preparation Example 2-1 shown in the following tables were prepared.

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Abstract

Disclosed is a fused pyrrolopyridine derivative which is useful as an active ingredient for a pharmaceutical composition, in particular a pharmaceutical composition for prevention or treatment of diseases that are caused by undesirable cytokine signaling or diseases that are caused by abnormal cytokine signaling. The inventors have intensively studied on compounds having JAK inhibitory activity, and found that the compound of the present invention, namely a fused pyrrolopyridine derivative has excellent JAK inhibitory activity and is thus useful as an agent for prevention or treatment of diseases that are caused by undesirable cytokine signaling or diseases that are caused by abnormal cytokine signaling.

Description

technical field [0001] The present invention relates to a condensed active ingredient useful as a pharmaceutical composition, especially a pharmaceutical composition for preventing or treating a disease caused by unfavorable cytokine signal transduction, or a disease caused by abnormal cytokine signal transduction Pyrrolopyridine derivatives. Background technique [0002] Janus kinase (hereinafter referred to as JAK) 3 is one of the Janus family of protein kinases. Although other kinases in this family besides JAK3 are expressed in many tissues, JAK3 is only expressed in hematopoietic cells. This is in conjunction with JAK3 in the signal transduction mediated by various receptors such as interleukin (hereinafter referred to as IL)-2, IL-4, IL-7, IL-9, IL-15 and IL-21, by cooperating with It is consistent that the non-covalent binding of the γ chain plays an important role (see Non-Patent Document 1 and Non-Patent Document 2). [0003] It has been found that in XSCID (X-li...

Claims

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Application Information

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IPC IPC(8): C07D471/14A61K31/437A61K31/439A61K31/4545A61K31/497A61K31/541A61K31/55A61P1/04A61P1/16A61P3/10A61P7/00A61P9/00A61P9/10A61P11/00A61P11/02A61P11/06A61P17/00A61P17/02A61P17/04A61P17/06A61P17/08A61P17/10A61P17/14A61P19/02A61P21/04A61P25/00A61P25/06A61P25/28A61P27/02A61P29/00A61P35/00A61P35/02A61P37/00A61P37/06A61P43/00C07D519/00
CPCC07D471/14C07D519/00A61P1/04A61P1/16A61P11/00A61P11/02A61P11/06A61P17/00A61P17/02A61P17/04A61P17/06A61P17/08A61P17/10A61P17/14A61P19/02A61P21/04A61P25/00A61P25/06A61P25/28A61P27/02A61P29/00A61P3/04A61P35/00A61P35/02A61P37/00A61P37/02A61P37/06A61P37/08A61P43/00A61P7/00A61P7/10A61P9/00A61P9/10A61P3/10A61K31/437
Inventor 白神升平中岛丰前田纯富永博章山岸寻亮本渡猛稻见真伦森尾浩树井上隆幸水谷刚石冈裕贵
Owner ASTELLAS PHARMA INC
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