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Naphthlamide derivative used as protein kinase inhibitor and histone deacetylase inhibitor and preparation method of naphthlamide derivative

A technology of protein kinase inhibitor and sirtuin, which is applied in the field of preparation of naphthalene amide derivatives, can solve the problems of large pollution, high price, harsh reaction conditions, etc.

Inactive Publication Date: 2013-02-06
福建太平洋制药有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In this type of method, i) the cesium carbonate used in the ether-forming reaction catalyst of the first step 6-hydroxynaphthoic acid and 4-chloroquinoline is expensive, and the toxicity is relatively large, and the pollution to the environment is large; ii) the reaction conditions are harsh and the product low rate
Therefore, this preparation method is not easy to industrialize

Method used

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  • Naphthlamide derivative used as protein kinase inhibitor and histone deacetylase inhibitor and preparation method of naphthlamide derivative
  • Naphthlamide derivative used as protein kinase inhibitor and histone deacetylase inhibitor and preparation method of naphthlamide derivative
  • Naphthlamide derivative used as protein kinase inhibitor and histone deacetylase inhibitor and preparation method of naphthlamide derivative

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Embodiment

[0030] Dissolve 1.88 g (10 mmol) of compound 6-hydroxynaphthalic acid in 80 ml of ethanol, add 4 drops of concentrated sulfuric acid, heat and reflux at 80 ℃ for 5 hours, then remove the solvent under reduced pressure to obtain compound 6-hydroxynaphthalate ethyl Ester 1.98 g (9.2 mmol), yield 91.7%; compound 1.98 g (9.2 mmol) ethyl 6-hydroxynaphthalate was dissolved in 10 ml DMF, stirred under ice bath, slowly added dropwise containing 0.52 g (21.7 mmol) ) NaH in DMF solution, stir for half an hour in an ice bath, remove the ice bath, wait for the temperature to return to room temperature, slowly drop in 2.19 g (11.1 mmol) 4,7-dichloroquinoline, and 0.3 g (1.8 mmol) 10 ml of DMF solution of KI, stirred for half an hour, reacted at 11 ℃ for 8 hours, then removed the solvent under reduced pressure to obtain the reaction mixture, separated by silica gel column chromatography, the gradient of the mobile phase was: V (n-hexane): V (ethyl acetate Ester)=4.5:1 to obtain compound 6-(7...

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Abstract

The invention relates to a naphthlamide derivative used as a protein kinase inhibitor and a histone deacetylase inhibitor. The structure of the naphthlamide derivative is as shown as a formula I, wherein a position 7 is provided with substituent groups R which include F, Cl, Br, I, OCH3 and other substituent groups as shown in the accompanying drawings, and the names of the substituent groups are fluorine, chlorine, bromine, iodine, methoxyl, 4-morpholinyl ethyoxyl, 4-morpholinyl methyl phenyl, acryloyl amino and 2-beuteamide. The naphthlamide derivative used as the protein kinase inhibitor and the histone deacetylase inhibitor can be used for curing cardiovascular diseases, metabolic diseases, allergy, cancers and hormone-related diseases. The invention additionally provides a synthesis method of the compound. The method has the advantages that the raw materials are easy to obtain, the method is simple to operate and the method is suitable for large-scale industrial production.

Description

Technical field: [0001] The invention relates to a method for preparing medicine. Specifically, it relates to a method for preparing naphthylamide derivatives of protein kinase inhibitors and histone deacetylase inhibitors. Background technique: [0002] The naphthylamide derivatives of protein kinase inhibitors and histone deacetylase inhibitors are useful for the treatment of cardiovascular diseases, metabolic diseases, allergies, cancer, and hormone-related diseases. The chemical name of the patented compound is: N-(2-anilino)-6-(7-substituted quinoline-4-etheroxy)-2-naphthylamide (the 7-position has a substituent R=Cl) (Note: The Chinese name of the substituent R is: chloro), and the structural formula is as follows: [0003] [0004] A large number of clinical trials have shown that these compounds have both protein kinase inhibitory activity and histone deacetylase inhibitory activity, and can be used to treat diseases related to abnormal protein kinase activity or abnormal...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/233C07D215/22C07D215/38A61P9/00A61P3/00A61P37/08A61P35/00A61P5/00
Inventor 王立强
Owner 福建太平洋制药有限公司
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