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Substituted pyrrolopyrimidine compound and application thereof

A technology of compounds and compositions, applied in the field of substituted pyrrolopyrimidine compounds and their preparation, prevention and treatment of diseases mediated by C-Kit and/or PDGFR, capable of solving problems such as fast metabolism, achieving slow metabolism and high-quality drugs Kinetic properties, long half-life effects

Active Publication Date: 2022-06-03
CHENGDU SHIBEIKANG BIOLOGICAL MEDICINE TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this compound is metabolized quickly in the body, and

Method used

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  • Substituted pyrrolopyrimidine compound and application thereof
  • Substituted pyrrolopyrimidine compound and application thereof
  • Substituted pyrrolopyrimidine compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: Preparation of Compound 1

Step 1: Synthesis of Compound c

Add compound a (2.86 g, 10 mmol) and anhydrous THF (200 mL) to a single product bottle, stir the solution, add compound b (2.42 g, 20 mmol) and tetraethyl titanate (6.83 g, 30 mmol) , the temperature was raised to 70 °C under nitrogen protection, and stirred overnight. After monitoring the reaction by TLC, water (100 mL) was added, extracted with ethyl acetate (300 mL) three times, the organic phases were combined, washed twice with water, twice with saturated sodium chloride, dried over anhydrous sodium sulfate, filtered, and concentrated. The product was separated by column chromatography to obtain 2.43 g of a yellow solid. Yield: 62.5%.

[0026] MS: m / z (ES): 390.5 [M+1].

[0027] Step 2: Synthesis of Compound D

Magnesium powder (280 mg, 11.6 mmol) was added to a 50 mL double-necked flask, evacuated and protected by nitrogen, ether (10 mL) was added, and deuterated iodomethane CD3I (1.44...

Embodiment 2

[0035] Example 2: Preparation of Compound 2

100 mg of compound 1 was taken and separated by chiral HPLC to obtain 40 mg of white solid, which was the isomer compound 2.

[0036] MS m / z (ES): 502.5 [M+1].

[0037] 1 H NMR (300MHz, DMSO -d6 ): 8.59 (m, 2H), 8.21 (m, 1H), 7.91-7.96 (m, 2H), 7.19-7.28 (m, 4H), 6.41(s, 1H), 5.10 (t, 2H), 5.01( s, 1H), 3.95 (m, 3H), 3.26 (m, 4H), 3.18-3.21 ((m, 4H)).

Embodiment 3

[0038] Example 3: Preparation of Compound 3

100 mg of compound 1 was taken and separated by chiral HPLC to obtain 40 mg of white solid, which was the isomer compound 3.

[0039] MS m / z (ES): 502.5 [M+1].

[0040] 1 H NMR (300MHz, DMSO -d6 ): 8.59 (m, 2H), 8.21 (m, 1H), 7.91-7.96 (m, 2H), 7.19-7.28 (m, 4H), 6.41(s, 1H), 5.10 (t, 2H), 5.01( s, 1H), 3.95 (m, 3H), 3.26 (m, 4H), 3.18-3.21 (m, 4H).

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PUM

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Abstract

The invention discloses a pyrrolopyrimidine compound as shown in a formula (I), and a stereoisomer or a pharmaceutically acceptable salt of the pyrrolopyrimidine compound. The invention also provides a preparation method of the compound, the stereoisomer or the pharmaceutically acceptable salt thereof, and application of the compound, the stereoisomer or the pharmaceutically acceptable salt thereof in preparation of drugs for preventing or treating C-Kit and/or PDGFR, especially mutant C-Kit and/or mutant PDGFR mediated diseases. The compound provided by the invention has better pharmacokinetic properties and stronger clinical medication compliance.

Description

technical field [0001] The invention belongs to the field of medicine, in particular to a substituted pyrrolopyrimidine compound, a preparation method thereof, and use thereof in the prevention and treatment of diseases mediated by C-Kit and / or PDGFR. Background technique [0002] KIT belongs to the type III receptor tyrosine kinase family members encoded by the proto-oncogene C-kit. The kit protein encoded by the C-kit gene is composed of an intracellular tyrosine kinase domain, a transmembrane domain and an extracellular domain with a ligand binding site. After the KIT receptor binds to the ligand SCF (stem cell factor), it forms a Dimers activate downstream signals, including Ras, Raf, MAPK pathways, etc., and ultimately activate transcription factors in cells, thereby regulating gene expression and controlling cell growth and proliferation. [0003] Imatinib is a tyrosine protease inhibitor that blocks the function of the tyrosine protein kinase KIT receptor, thereby in...

Claims

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Application Information

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IPC IPC(8): C07D487/04A61P1/00A61P35/02A61P35/00A61P19/02A61P29/00A61P1/18A61P25/02A61P21/00A61P25/14A61K31/519
CPCC07D487/04A61P1/00A61P35/02A61P35/00A61P19/02A61P29/00A61P1/18A61P25/02A61P21/00A61P25/14C07B2200/05
Inventor 曾燕群黄龙周广林朱绪成付海霞牟霞
Owner CHENGDU SHIBEIKANG BIOLOGICAL MEDICINE TECH CO LTD
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