2-oxo-1,2-dihydrobenzo[cd]indole-6-sulfonamide compounds and their compositions and applications

A technology of dihydrobenzene and sulfonamide, applied in the field of chemical medicine

Active Publication Date: 2018-03-20
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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  • 2-oxo-1,2-dihydrobenzo[cd]indole-6-sulfonamide compounds and their compositions and applications
  • 2-oxo-1,2-dihydrobenzo[cd]indole-6-sulfonamide compounds and their compositions and applications
  • 2-oxo-1,2-dihydrobenzo[cd]indole-6-sulfonamide compounds and their compositions and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] 1-Ethyl-2-oxo-N-(2-oxo-2-(pyrrolidine-1-substituted)ethyl)-1,2-dihydrobenzo[cd]indole-6-sulfonamide (E1)

[0069] (1-ethyl-2-oxo-N-(2-oxo-2-(pyrrolidin-1-yl)ethyl)-1,2-dihydrobenzo[cd]indole-6-sulfonamide)(E1)

[0070]

[0071] Step 1. 1,3-Dioxo-2,3-dihydro-1H-phenalen-2-yl 4-methylbenzenesulfonate

[0072] (1,3-dioxo-2,3-dihydro-1H-phenalen-2-yl 4-methylbenzenesulfonate)

[0073]

[0074] 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 sol...

Embodiment 2

[0092] N-((1-acetylpiperidine-4-substituted)methyl)-1-ethyl-2-oxo-1,2-dihydrobenzo[cd]indole-6-sulfonamide (E2)

[0093] (N-((1-acetylpiperidin-4-yl)methyl)-1-ethyl-2-oxo-1,2-dihydrobenzo[cd]indole-6-sulfonamide)(E2)

[0094]

[0095] The synthesis method is as in Example 1.

[0096] 1 H-NMR (400MHz, d-DMSO) δ8.69 (d, J = 8.4Hz, 1H), 8.16 (d, J = 6.8Hz, 1H), 8.07 (d, J = 7.6Hz, 1H), 7.96 ( t,J=7.2Hz,1H),7.86(t,J=6.0Hz,1H),7.31(d,J=7.6Hz,1H),4.24(d,J=8.0Hz,1H),3.93(q, J=6.8Hz, 2H), 3.69(d, J=12.4Hz, 1H), 2.87(t, J=13.2Hz, 1H), 2.64(t, J=6.0Hz, 2H), 2.36(t, J= 12.0Hz,1H).1.92(s,3H),1.56-1.51(m,3H),1.28(t,J=7.2Hz,3H).

[0097] MS(ESI),m / z:M + 417.0; M - 415.0.

Embodiment 3

[0099] 1-(1-Ethyl-2-oxo-1,2-dihydrobenzo[cd]indole-6-sulfinylamino)cyclohexanecarboxamide (E3)

[0100] (N-(1-acetylcyclohexyl)-1-ethyl-2-oxo-1,2-dihydrobenzo[cd]indole-6-sulfonamide)(E3)

[0101]

[0102] The synthesis method is as in Example 1.

[0103] 1H-NMR (400MHz, d-DMSO) δ8.58 (d, J = 8.4Hz, 1H), 8.15 (d, J = 7.2Hz, 1H), 8.09 (d, J = 7.6Hz, 1H), 7.96 ( t,J=8.0Hz,1H),7.31(d,J=7.6Hz,1H),3.92(q,J=6.8Hz,2H),3.26-3.21(m,4H),1.25(t,J=7.2 Hz,3H),1.01-0.98(m,6H).MS(ESI),m / z:M - 400.8.

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Abstract

Provided in the present invention are a compound having a structural feature of the general formula I as a novel retinoic acid orphan nuclear receptor γ subtype (RORγ) inhibitor, and the uses of the compound and a pharmaceutically acceptable salt, isomer, racemate, prodrug co-crystallizing complex, hydrate and solvate in the drug for treating or preventing a disease associated with RORγ regulation and control.

Description

technical field [0001] The invention belongs to the technical field of chemistry and medicine, and in particular relates to a class of 2-oxo-1,2-dihydrobenzo[cd]indole-6-sulfonamide derivatives and pharmaceutically acceptable salts or stereoisomers thereof. Constructs and prodrug molecules and preparation methods thereof, as well as the application of such compounds in the preparation of drugs for the treatment of immune-related diseases regulated by RORγ. Background technique [0002] Retinoic acid-related orphan nuclear receptor (ROR) is a member of the nuclear receptor family, which can regulate a variety of physiological and biochemical processes. The ROR family includes three types RORα, RORβ, and RORγ. Three different RORs can be expressed in different tissues and regulate different physiological processes. RORα is mainly distributed in liver, skeletal muscle, skin, lung, adipose tissue, kidney, thymus, and brain. RORβ has a small range of action and mainly acts on t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/12C07D401/12C07D209/92C07D413/12C07D405/12C07D409/12A61K31/403A61K31/454A61K31/5377A61K31/422A61K31/416A61K31/506A61K31/4184A61K31/4045A61K31/4439A61K31/496A61K31/4725A61K31/404A61P19/02A61P29/00A61P17/06A61P11/06A61P35/00A61P31/14
CPCC07D209/92C07D401/12C07D403/12C07D405/12C07D409/12C07D413/12A61K31/403A61K31/4045A61K31/416A61K31/4184A61K31/422A61K31/4439A61K31/454A61K31/4725A61K31/496A61K31/506A61K31/5377A61P11/06A61P17/06A61P19/02A61P25/00A61P29/00A61P31/14A61P35/00A61P43/00
Inventor 许永薛晓纤张岩李静金翔宇罗小雨宋宇
Owner GUANGZHOU INST OF BIOMEDICINE & HEALTH CHINESE ACAD OF SCI
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