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Novel compound and pharmaceutically acceptable salt thereof

A compound and pharmaceutical technology, applied in organic chemistry, drug combination, anti-tumor drugs, etc., can solve the problems of brain cancer treatment effect to be improved, limited anti-cancer effect, etc.

Active Publication Date: 2020-09-29
HANGZHOU PUSH KANG BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the anticancer effect of elemene and temozolomide alone is limited, especially for the treatment of brain cancer, which needs to be improved

Method used

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  • Novel compound and pharmaceutically acceptable salt thereof
  • Novel compound and pharmaceutically acceptable salt thereof
  • Novel compound and pharmaceutically acceptable salt thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0088] The preparation of compounds of the present application may involve the protection and deprotection of various chemical groups. Those skilled in the art can readily determine the need for protection and deprotection and select appropriate protecting groups. Protecting group chemistry can be found in, eg, T.W. Greene and P.G.M. Wuts, Protective Groups in Organic Synthesis, 3rd Ed., Wiley & Sons, Inc., New York (1999), the entire contents of which are incorporated herein by reference.

[0089] Reactions may be monitored or purified according to any suitable method known in the art. For example, spectroscopic methods such as nuclear magnetic resonance spectroscopy (e.g. 1 H or 13 C) Infrared spectroscopy, spectrophotometry (e.g. UV-visible), mass spectrometry, or chromatographic methods such as high performance liquid chromatography (HPLC), liquid chromatography-mass spectrometry (LCMS) or thin layer chromatography (TLC) for the product formation is monitored. Those sk...

Embodiment 1

[0114] The synthesis of embodiment 1 compound I

[0115] Dissolve 1-methyl-2,4-bis(prop-1-en-2-yl)-1-vinylcyclohexane (2g) in 10mL of dichloromethane, add 2mL of acetic acid at 0°C, stir for ten minute. Then, slowly add 15 mL of sodium hypochlorite solution to the system at 0°C. The reaction solution was stirred under ice bath for 5 hours. The reaction solution was extracted three times with dichloromethane, the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was removed to obtain 4-(3-chloroprop-1-en-2-yl)-1-methyl-2 -(prop-1-en-2-yl)-1-vinylcyclohexane and 2-(3-chloroprop-1-en-2-yl)-1-methyl-4-(prop-1- En-2-yl)-1-vinylcyclohexane mixture 1g, light yellow liquid, was directly used in the next step without purification, yield 42.1%.

[0116]

[0117] 1 g of the mixture obtained in the previous step was dissolved in 20 mL of acetonitrile, and 570 mg of methylamine hydrochloride and 670 mg of sodium hydroxide were added ...

Embodiment 2

[0122] The preparation of embodiment 2 compound II

[0123] Dissolve 1-methyl-2,4-di(prop-1-en-2-yl)-1-vinylcyclohexane (2 g) in 50 mL of acetonitrile, add 2.76 g of potassium carbonate, and stir for ten minutes. Then, slowly add 2 g of m-chloroperoxybenzoic acid in batches to the system under ice-cooling. The reaction solution was stirred under ice bath for 2 hours, then raised to room temperature and stirred overnight. After filtration, the filter cake was washed with dichloromethane, and the filtrate was concentrated to obtain crude product 1, which was purified by silica gel column (petroleum ether: ethyl acetate = 5:1) to obtain compound 2, 1.1 g of light yellow liquid, with a yield of 50%.

[0124] Dissolve 1.1 g of the mixture obtained in the previous step in 20 mL of tetrahydrofuran, slowly add LDA (10 mmol) at 0°C, stir for 1 hour, quench the reaction with saturated ammonium chloride, extract the organic phase with ethyl acetate, and dry over anhydrous sodium sulfate...

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Abstract

The invention discloses a compound or a pharmaceutically acceptable salt thereof. The compound includes a moiety derived from temozolomide and a moiety derived from elemene, and the moiety derived from temozolomide and the moiety derived from elemene are directly covalently linked or covalently linked via a linker. The invention also discloses a composition comprising the above compound, and a method of treating cancers.

Description

technical field [0001] The present invention relates to the field of medicinal chemistry, in particular to a novel compound or a pharmaceutically acceptable salt thereof, wherein the compound includes a part derived from temozolomide and a part derived from elemene. Background technique [0002] Elemene belongs to the sesquiterpenes. It is a natural medicine with clear anticancer activity extracted from the rhizome of Zingiberaceae Wenyujin (Ezhu) in China. It is a new type of anticancer drug. Elemene is mainly β-elemene, with a small amount of α-elemene, γ-elemene and δ-elemene. Elemene is a kind of volatile oil, so it has strong volatility and fat solubility. It is mainly used clinically for various cancers such as esophageal cancer, lung cancer, brain tumor, liver cancer, cervical cancer, cancerous chest, and cancer-related diseases. Symptoms (such as ascites). Among them, β-elemene is the main anti-cancer substance, and also has the functions of relieving cancer pain, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A61K31/495A61P35/00
CPCC07D487/04A61P35/00
Inventor 余波张晓敏姚举张英新李梦颖
Owner HANGZHOU PUSH KANG BIOTECH CO LTD
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