N-pheny-lamide compounds and applications thereof

A compound, phenyl technology, applied in the field of chemical medicine

Active Publication Date: 2016-01-27
GUANGZHOU INST OF BIOMEDICINE & HEALTH CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, further studies have shown that digoxin has strong side effects and that ursolic acid also acts on glucocorticoid receptors

Method used

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  • N-pheny-lamide compounds and applications thereof
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  • N-pheny-lamide compounds and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0153] 1-ethyl-N-(2-fluoro-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)-2-oxo-1, Preparation of 2-dihydrobenzo[cd]indole-6-sulfonamide

[0154]

[0155] Step 1. Preparation of 1,3-dioxo-2,3-dihydro-1H-phenalen-2-yl 4-methylbenzenesulfonate

[0156]

[0157] Add 1,8-naphthalic anhydride (1-1) (11.9 g, 0.06 mol), hydroxylamine hydrochloride (4.18 g, 0.06 mol) and pyridine (70 mL) into a round bottom flask, and heat to reflux for 1 hour. After cooling to 80°C, 4-toluenesulfonyl chloride (22.88 g, 0.12 mol) was quickly added, and the temperature was raised to reflux for 1.5 hours. After cooling to room temperature, the mixture was poured into 200 g of ice water, and a yellow precipitate precipitated out after stirring. Stand still, filter with suction, wash with water three times, stir and wash with saturated sodium bicarbonate solution, filter with suction, wash with water three times to obtain 17g of intermediate compound 1-1 (78%).

[0158] Step 2. Preparatio...

Embodiment 2

[0174] N-(2-fluoro-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)-4,4-dimethyl-2-oxo Preparation of -1,2,3,4-tetrahydroquinoline-6-sulfonamide

[0175]

[0176] Step 1. Preparation of 3-methyl-N-phenyl-2-propenylamine

[0177]

[0178] Take aniline (1 g, 0.01 mol), add 6 mL of pyridine, stir at 0°C, and slowly drop into 3-methylcrotonyl chloride (1.44 mL). After evacuating, use argon to keep room temperature and react for 1h. Dilute hydrochloric acid was added until there was no white precipitate, filtered with suction, the filter cake was washed with water and petroleum ether, and recrystallized from isopropanol to obtain 1.65 g of a solid (compound 2-1), with a yield of 88%.

[0179] Step 2. Preparation of 4,4-dimethyl-2-oxo-1,2,3,4-tetrahydroquinoline

[0180]

[0181] Take compound 2-1 (1.65 g, 0.009 g), add dichloromethane (20 mL), and place at 0°C. Aluminum trichloride (5 g, 0.037 mol) was added in portions. Reaction at room temperature for 2h. Was...

Embodiment 3

[0189] N-(2-fluoro-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)-2-oxo-1-propyl-1, Preparation of 2,3,4-tetrahydroquinoline-6-sulfonamide

[0190]

[0191] Step 1. Preparation of 1-propyl-3,4-dihydroquinolin-2(1H)-one

[0192]

[0193] Take 3,4-dihydroquinolin-2(1H)-one (1g, 6.8mmol), add anhydrous DMF, stir at -5°C for 5min, add sodium hydride (0.5g, 0.02 mol), stirred for 5 min after the addition, added iodopropane (1.75 g, 0.01 mol) dropwise, and reacted overnight at room temperature. It was quenched with water and extracted three times with ethyl acetate. The organic layers were combined, washed with saturated sodium chloride, and dried over anhydrous sodium sulfate. Column chromatography: PE; EA=10:1 to obtain 1.2 g of product (compound 3-1), yield 95%.

[0194] Step 2. Preparation of 2-oxo-1-propyl-1,2,3,4-tetrahydroquinoline-6-sulfonyl chloride

[0195]

[0196] Take compound 3-1 (0.5g, 2.64mmol), add 15mL of chloroform to dissolve it, slowly add ...

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Abstract

The invention relates to the chemical and medicinal technology field, and provides compounds with a structural characteristic in formula I and applications of the compounds and pharmaceutically acceptable salts, isomers, racemes, prodrug cocrystallization compounds, hydrates and solvates in preparation of medicines treating or preventing relative diseases with ROR regulation and control. Importantly, the compounds can be used for reducing generation of immunological factors relative to immunological diseases and alleviating immunologic derangement symptoms.

Description

technical field [0001] The invention relates to the technical field of chemistry and medicine, in particular to an N-phenylamide compound and its application. Background technique [0002] Retinoic acid receptor-related orphan receptor (ROR) is an important class of orphan receptors in the nuclear receptor family. This receptor family includes 3 subtypes, RORα, RORβ and RORγ. RORα is widely expressed in liver, skeletal muscle, skin, lung, adipocyte tissue, kidney, thymus and brain. The RORβ expression site is very limited, only expressed in the central nervous system. RORγ is expressed in liver, skeletal muscle, and adipocyte tissues, especially in key cells in the immune system. [0003] In the past few years, RORα and RORγ have been promoted due to their role in helper T cells 17 (T H 17) has played an important role in the differentiation and development of 17) and has attracted widespread attention. The study found that T H 17 cells are key regulators of immunopath...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/90C07D215/227C07D263/58C07D209/34C07D239/96C07D263/56C07D239/80C07D209/08C07D279/16C07C311/21C07D319/18C07D333/34C07D295/096C07C311/29C07C233/15C07C235/38C07C311/13A61P3/06A61P3/10A61P19/02A61P17/06A61P11/06A61P11/00A61P1/00A61P35/00A61P25/00A61P37/02A61P31/14
Inventor 许永罗小雨张岩薛晓纤武春宋明金翔宇宋宇周洋
Owner GUANGZHOU INST OF BIOMEDICINE & HEALTH CHINESE ACAD OF SCI
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