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Novel dihydropyranopyrimidinone derivatives and uses thereof

A pyrimidine and pyran technology, applied in the field of novel dihydropyranopyrimidinone derivatives, can solve problems such as increased concentration of axin, decreased Wnt signal transduction, and concentration of destruction complexes

Active Publication Date: 2021-04-16
ST PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Thus, it is expected that in the presence of inhibitors of tankyrase catalytic activity, Axin concentrations will increase, leading to higher concentrations of destruction complexes, decreased concentrations of unphosphorylated intracellular β-catenin and Wnt signaling reduce

Method used

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  • Novel dihydropyranopyrimidinone derivatives and uses thereof
  • Novel dihydropyranopyrimidinone derivatives and uses thereof
  • Novel dihydropyranopyrimidinone derivatives and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0119] Preparation 1: 4-(benzyloxy)-2-methylsulfonyl)-7,8-dihydro-5H-pyrano[4,3- d] pyrimidine (I-7)

[0120] 4-(Benzyloxy)-2-methylsulfonyl)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidine (I-7) was prepared as an intermediate based on the following reaction scheme For the synthesis of dihydropyranopyrimidinone derivatives.

[0121]

[0122] 1.1. 4-Oxotetrahydro-2H-pyran-3-carboxylic acid methyl ester (I-1)

[0123] To a mixture of NaH (1.97 g, 44.96 mmol) in THF (100 ml) was added dihydro-2H-pyran-4(3H)-one (3 g, 29.96 mmol) dropwise in an ice bath. After stirring for 20 min, dimethyl carbonate (3.8 ml, 44.96 mmol) was added. The reaction mixture was stirred at room temperature for 3 h. The reaction mixture was poured into a mixture of diethyl ether / 1N HCl with stirring. The organic layer was separated and washed with Na 2 SO 4 It was dried, concentrated under reduced pressure, and the residue was purified by column chromatography to give the desired product I-1 (1.5 g...

preparation example 2

[0143] Preparation 2: 1-(2,6-difluoro-4-(2-methoxyethoxy)phenyl)piperazine hydrochloride (I-8a) and 1-(2,6- Difluoro-4-(2-(piperidin-1-yl)ethoxy)phenyl)piperazine dihydrochloride (I-8b)

[0144]

[0145] 2.1. tert-butyl 4-(2,6-difluoro-4-(2-methoxyethoxy)phenyl)piperazine-1-carboxylate

[0146] tert-butyl 4-(2,6-difluoro-4-hydroxyphenyl)piperazine-1-carboxylate (2 g, 6.363 mmol), 1-bromo-2-methoxyethane (0.72 ml, 7.635mmol) and K 2 CO 3 (2.64g, 19.09mmol) was heated to 60°C to 65°C. After stirring for 16 h, the mixture was cooled to room temperature, diluted with EtOAc, and washed three times with water. The organic layer was washed with Na 2SO 4 Drying and concentration under reduced pressure gave the desired product (2.39 g) as a yellow solid.

[0147] LC-MS (ESI, m / z) = 373.2 (M+H + ).

[0148] 2.2-1. 1-(2,6-Difluoro-4-(2-methoxyethoxy)phenyl)piperazine hydrochloride

[0149] To a solution of the compound obtained in Preparation 2.1 (2.39 g, 6.363 mmol) ...

preparation example 3

[0154] Preparation 3: 3,5-difluoro-4-(piperazin-1-yl)phenol hydrochloride

[0155] By removing the protecting group of tert-butyl 4-(2,6-difluoro-4-hydroxyphenyl)piperazine-1-carboxylate, the desired product was prepared following a method similar to that described in Preparation 2.2-1.

[0156] LC-MS (ESI, m / z) = 215.1 (M+H + ).

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Abstract

The present invention relates to a novel dihydropyranopyrimidinone derivative, its tautomer, its stereoisomer and their mixture, or a pharmaceutically acceptable salt thereof; and a method for preventing or treating A pharmaceutical composition for tankyrase-associated diseases, comprising as an active ingredient said dihydropyranopyrimidinone derivatives, tautomers thereof, stereoisomers thereof and mixtures thereof, or Pharmaceutically acceptable salts.

Description

technical field [0001] The present invention relates to a novel dihydropyranopyrimidinone derivative, its tautomer, its stereoisomer and their mixture, or a pharmaceutically acceptable salt thereof; and a method for preventing or treating Pharmaceutical composition for tankyrase-associated diseases comprising said dihydropyranopyrimidinone derivatives, tautomers thereof, stereoisomers thereof and mixtures thereof as active ingredients , or a pharmaceutically acceptable salt thereof; and its use; A pharmaceutically acceptable salt, a method of treating or preventing a disease associated with tankyrase. Background technique [0002] Human tankyrase belongs to the poly(ADP-ribose) polymerase (PARP) protein family, which consists of 17 members that share a catalytic PARP domain. [0003] PARP family proteins are promising therapeutic targets. PARP1 and PARP2 play a role in the DNA damage response, and PARP inhibitors sensitize cancer cells to drugs and radiation therapy. In ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/052C07D403/04C07D401/14C07D413/14A61K31/519A61K31/497A61K31/5377
CPCC07D491/052A61P35/00
Inventor 金庆镇金旭镒尹志惠
Owner ST PHARM CO LTD
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