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Preparation method of polymerase inhibitor used for tumor-related diseases

An inhibitor, polymerase technology, used in antitumor drugs, drug combinations, organic chemistry, etc.

Inactive Publication Date: 2019-11-05
福建拓烯新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] No small-molecule inhibitors of tankyrase have yet entered clinical research

Method used

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  • Preparation method of polymerase inhibitor used for tumor-related diseases
  • Preparation method of polymerase inhibitor used for tumor-related diseases
  • Preparation method of polymerase inhibitor used for tumor-related diseases

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] 2-[3-Methyl-4-(4-piperazin-1-yl-benzenesulfonyl)-phenyl]-1,2,3,5,7,8-hexahydropyrano[4,3 - d] pyrimidin-4-one

[0025] Step I: Preparation of (2-mercapto-pyridin-5-yl)piperazine

[0026] 2-Mercapto-5-chloropyridine (0.725g, 5mmol), piperazine (0.43g, 5mmol) and N,N-diisopropylethylamine (0.65g, 5mmol) were added into DMSO (20mL) solvent, React overnight at 100°C under nitrogen protection. Ethyl acetate (200 mL) and water (100 mL) were added to the system, the layers were separated, and the organic phase was dried over anhydrous sodium sulfate and dried under reduced pressure to obtain 0.7 g of the title compound with a yield of 73.5%.

[0027] Step II: Preparation of methyl 4-oxotetrahydro-2H-pyran-3-carboxylate

[0028] NaH (60% by mass, 5 g, 125 mmol) was slowly added to tetrahydrofuran (200 mL) at room temperature, and tetrahydro-4H-pyran-4-one (5.0 g, 50 mmol) and dimethyl carbonate were added after the addition was complete (10 mL, 125 mmol). The temper...

Embodiment 2

[0038]2-[3-Methyl-4-(4-piperidin-1-yl-benzenesulfonyl)-phenyl]-1,2,3,5,7,8-hexahydropyrano[4,3 -d] Preparation of pyrimidin-4-one

[0039] Step I: Preparation of (5-mercapto-pyridin-2-yl)piperidine

[0040] 5-Mercapto-2-chloropyridine (0.725g, 5mmol), piperidine (0.42g, 5mmol) and N,N-diisopropylethylamine (0.65g, 5mmol) were added to DMSO (20mL) solvent, React overnight at 100°C under nitrogen protection. Ethyl acetate (200 mL) and water (100 mL) were added to the system, the layers were separated, and the organic phase was dried over anhydrous sodium sulfate and dried under reduced pressure to obtain 0.62 g of the title compound with a yield of 65.1%.

[0041] Step II: 2-[3-Methyl-4-(4-piperidin-1-yl-phenylmercapto)-phenyl]-1,2,3,5,7,8-hexahydropyrano Preparation of [4,3-d]pyrimidin-4-one

[0042] (5-Mercapto-pyridin-2-yl)piperidine (193mg, 1mmol) prepared in step I and 2-(4-bromophenyl)-3,5,7,8 prepared in step III of Example 1 -Tetrahydro-4H-pyrano[4,3-d]pyrimidi...

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Abstract

The invention belongs to the field of medicinal chemistry, and particularly relates to a preparation method of a terminal anchor polymerase inhibitor with a structure shown in a formula I. The prepared compound has certain inhibitory activity against both PARP1 and PARP2.

Description

technical field [0001] The invention belongs to the field of medicines, and in particular relates to a preparation method of a polymerase inhibitor. Background technique [0002] Poly(ADP-ribose) polymerase (poly(ADP-ribose) polymerase, PARP) is a nuclear enzyme that catalyzes poly-ADP ribosylation in eukaryotic cells. One of the most important modification methods in the end. PARP has been discovered for more than 40 years, and its important role in DNA damage repair and genome stability has attracted the attention of many scholars. Encouraging results. [0003] So far, no small-molecule inhibitors of tankyrase have entered clinical research. Therefore, there is an urgent need to develop anti-tumor drugs with new structures, high efficiency and low toxicity for tankyrase targets. The purpose of the present invention is to provide a preparation method of a novel tankyrase inhibitor. Contents of the invention [0004] The present invention provides a preparation method ...

Claims

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Application Information

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IPC IPC(8): C07D491/052A61P35/00
CPCA61P35/00C07D491/052
Inventor 翁松青
Owner 福建拓烯新材料科技有限公司
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