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Sulfonamide compound, preparation method, and applications thereof

A technology of compounds and oxides, applied in the field of medicine

Active Publication Date: 2020-03-10
SICHUAN KELUN BIOTECH BIOPHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the therapeutic drugs for tumors are not effective for all cancer patients

Method used

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  • Sulfonamide compound, preparation method, and applications thereof
  • Sulfonamide compound, preparation method, and applications thereof
  • Sulfonamide compound, preparation method, and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0211] Intermediate Preparation Example 1: Preparation of N-ethyl-N-(3-hydroxy-2,3-dihydro-1H-inden-5-yl)-3-(trifluoromethyl)benzenesulfonamide

[0212]

[0213] Step 1: Preparation of N-(3-oxo-2,3-dihydro-1H-inden-5-yl)-3-(trifluoromethyl)benzenesulfonamide

[0214] Add 6-amino-1-indanone (8.5g, 57.8mmol) and 3-trifluoromethylbenzenesulfonyl chloride (15.5g, 63.6mmol) into pyridine (100mL) and heat to 55°C for 12 hours. The reaction solution was concentrated under reduced pressure, poured into water (500mL), extracted three times with ethyl acetate, combined the organic phases, dried over anhydrous sodium sulfate, filtered and concentrated the filtrate under reduced pressure to obtain the title compound of this step (19.4g, yield : 94.5%).

[0215] MS m / z(ESI):373.1[M+NH 4 ] + .

[0216] The second step: the preparation of N-ethyl-N-(3-oxo-2,3-dihydro-1H-inden-5-yl)-3-(trifluoromethyl)benzenesulfonamide

[0217] N-(3-oxo-2,3-dihydro-1H-inden-5-yl)-3-(trifluoromethyl)ben...

Embodiment 1

[0223] Example 1: N-(3-(2-chloro-6-(trifluoromethyl)phenoxy)-2,3-dihydro-1H-inden-5-yl)-N-ethyl-3- (Trifluoromethyl)benzenesulfonamide (Compound 1)

[0224]

[0225] Triphenylphosphine (204.2 mg, 778.4 μmol), N-ethyl-N-(3-hydroxy-2,3-dihydro-1H-inden-5-yl)-3-(trifluoromethyl)benzene Sulfonamide (100mg, 259.5μmol) and 2-chloro-6-trifluoromethylphenol (76.5mg, 389.2μmol) were mixed in a 100mL reaction flask, under nitrogen protection, anhydrous tetrahydrofuran (5mL) was added, and stirred in an ice bath for 0.5 hours Finally, a solution of diisopropyl azodicarboxylate (157.4 mg, 778.4 μmol) in anhydrous tetrahydrofuran (1 mL) was added, stirring was continued for 0.5 hours in an ice bath, and the reaction was continued at room temperature for about 2 hours. The reaction solution was concentrated and poured into water (100 mL), extracted three times with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, filtered and the filtrate was concent...

Embodiment 2

[0228] Example 2: N-(3-(2-cyanophenoxy)-2,3-dihydro-1H-inden-5-yl)-N-ethyl-3-(trifluoromethyl)benzenesulfonate Amide (compound 2)

[0229]

[0230] Using the synthetic route of Example 1, replacing the raw material 2-chloro-6-trifluoromethylphenol with 2-cyanophenol, the title compound (52.0 mg, yield: 33.4%) was obtained.

[0231] MS m / z(ESI):504.1[M+NH 4 ] + .

[0232] 1 H-NMR (400MHz, CDCl 3 )δ:8.08-8.06(m,1H),7.87-7.79(m,3H),7.74-7.66(m,2H),7.45-7.43(m,1H),7.38-7.36(m,1H),7.15- 7.11(m,1H),7.04-7.02(m,2H),5.97-5.94(m,1H),3.65-3.52(m,2H),3.11-3.06(m,1H),2.96-2.92(m,1H ), 2.69-2.61 (m, 1H), 2.15-2.07 (m, 1H), 0.96 (t, J=8.0Hz, 3H).

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Abstract

The invention relates to a series of sulfonamide compounds, a preparation method, and applications thereof, and a medicine composition containing such compounds, especially to the compound of the formula (I), the preparation method thereof, the applications of the compound of the formula (I) for preventing and / or treating diseases as a ROR[gamma] conditioning agent, and a medicine composition containing the compound of the formula (I).

Description

[0001] field of invention [0002] The invention belongs to the field of medicine, and specifically relates to a class of sulfonamide compounds, a preparation method and application thereof, and a pharmaceutical composition containing the compound. In particular, the present invention relates to the compound of formula I, its preparation method, the use of the compound of formula I as a RORγ modulator for preventing and / or treating diseases, and the pharmaceutical composition containing the compound of formula I. [0003] Background of the invention [0004] Retinoic acid receptor-related orphan nuclear receptors (ROR) play a regulatory role in a variety of physiological processes, including three subtypes of RORα, RORβ and RORγ. Recent studies have found that compared with retinoic acid, RORs have a higher affinity with oxidized steroid derivatives and are regulated by them. RORs are widely distributed in various tissues of the body, can directly enter the nucleus to regulate...

Claims

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Application Information

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IPC IPC(8): C07C311/21C07C303/40C07C317/14C07C315/04C07D335/02C07D213/71C07D231/18C07D261/10C07D213/64C07D213/85C07D307/83C07D311/22C07D215/233C07D209/08C07D209/34C07D231/56C07D235/06C07D263/58C07D265/36C07D241/44C07D215/227C07D215/38C07D215/42A61P35/00A61P35/02
CPCC07C311/21C07C317/14C07D335/02C07D213/71C07D231/18C07D261/10C07D213/64C07D213/85C07D307/83C07D311/22C07D215/233C07D209/08C07D209/34C07D231/56C07D235/06C07D263/58C07D265/36C07D241/44C07D215/227C07D215/38C07D215/42A61P35/00A61P35/02C07C2602/08C07C2602/10
Inventor 任云刘金明蔡家强王利春王晶翼
Owner SICHUAN KELUN BIOTECH BIOPHARMACEUTICAL CO LTD