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Triazolopyridine compound as well as preparation method and application thereof

A technology of azolopyridines and compounds, which is applied in the field of triazolopyridine compounds and their preparation, can solve problems such as infection, malignant tumors and lymphoma, and achieve a good inhibitory effect

Pending Publication Date: 2022-04-26
深圳市乐土生物医药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Existing JAK inhibitors mainly include tofacitinib and Filgotinib from the Belgian Galapagos company. However, tofacitinib can also bring some side effects while relieving the symptoms of rheumatoid arthritis (RA), causing certain infections, Occurrence of Malignant Tumors and Lymphomas

Method used

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  • Triazolopyridine compound as well as preparation method and application thereof
  • Triazolopyridine compound as well as preparation method and application thereof
  • Triazolopyridine compound as well as preparation method and application thereof

Examples

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preparation example Construction

[0119] According to the second aspect, in some embodiments, the preparation method of the triazolopyridine compound described in the first aspect is provided, including at least one of the following methods:

[0120] 1) When P=0, R 8 When it is oxygen, the compound shown in general formula I is prepared by the bromide Ia containing boric acid pinacol ester through coupling, iodo, and carbonyl insertion steps, and the main reaction process is as follows:

[0121]

[0122] 2) When P=1, Q is imino, R 8 When it is oxygen, the compound shown in the general formula II is obtained from the triazolo[1,5-a]pyridin-2-amine compound Ic through acylation, alkylation and coupling steps. The main reaction process is as follows:

[0123]

[0124] 3) When P=1, Q is imino, R 8 When it is oxygen, the compound shown in the general formula II is prepared from the intermediate Ib through the steps of coupling, acylation and alkylation, and the main reaction process is as follows:

[0125]...

Embodiment 1

[0172] The synthetic compound of present embodiment is as follows:

[0173]

[0174] The synthetic route of the present embodiment is as follows:

[0175]

[0176] The synthesis of compound 1 comprises the following steps:

[0177] Step 1: Preparation of 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzyl)thiomorpholine-1, 1-Dioxide, ie Intermediate 1A.

[0178] 4-Bromomethylphenylboronic acid pinacol ester (25.00g, 8.42mmol), 1,1-dioxide thiomorpholine (13.68g, 10.12mol, also known as thiomorpholine-1,1-di Oxide, CAS number: 39093-93-1, chemical formula C 4 h 5 NO 2 S), potassium carbonate (13.96g, 10.10mmol) was added to the reaction flask, 250mL of N,N-dimethylformamide was added, and the reaction was stirred at 80°C for 4 hours. After cooling to room temperature, the reaction solution was poured into 625 mL of ice water, stirred for 30 minutes, and suction-filtered to obtain the product, intermediate 1A, 24.1 g of white solid, with a yield of 81%.

[017...

Embodiment 2

[0187] The compound prepared in this embodiment is as follows:

[0188]

[0189] The same preparation method as in Example 1, in step 4, 2-aminopyridine was used instead of benzylamine to obtain compound 2.

[0190] ESI-MS[M+H](m / z):463.2.

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PUM

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Abstract

The invention relates to a triazolopyridine compound as well as a preparation method and application thereof. The triazolopyridine compound is a compound as shown in a general formula A or at least one of a meso-mer, a raceme, an enantiomer, a diastereoisomer, a tautomer, a prodrug and a medicinal salt of the compound. The compound can effectively inhibit kinase activity, especially has a good inhibition effect on protein tyrosine kinase activity, has a clinical application prospect, and can be used for preparing drugs for preventing and / or treating related diseases.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to triazolopyridine compounds and their preparation methods and uses. Background technique [0002] The intracellular signal transmission process is an effective way for cells to respond to external stimuli and ultimately trigger specific biological effects. Cytokines can conduct intracellular signal transmission through a variety of signal transduction pathways, and thus participate in the regulation of many important biological functions related to hematopoietic function and immunity. The Janus kinase (JAK) family of protein tyrosine kinases and the activator of transcription (STAT) play an important role in the process of cytokine signal transduction. [0003] Existing JAK inhibitors mainly include tofacitinib and Filgotinib from the Belgian Galapagos company. However, tofacitinib can also bring some side effects while relieving the symptoms of rheumatoid arthritis (RA), causin...

Claims

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Application Information

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IPC IPC(8): C07D471/04C07D519/00A61K31/541A61K31/4545A61K31/496A61K31/444A61K31/5377A61K31/438A61K31/437A61K31/519A61K31/4709A61P29/00A61P37/00A61P35/00A61P19/02A61P1/00A61P17/06A61P9/10A61P37/02A61P35/02
CPCC07D471/04C07D519/00A61P29/00A61P37/00A61P35/00A61P19/02A61P1/00A61P17/06A61P9/10A61P37/02A61P35/02
Inventor 邢青峰郭凯李光磊罗钦宏苏彦景叶春强朱锡祯
Owner 深圳市乐土生物医药有限公司
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