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2-oxo-1,2-dihydrobenzo[cd] indole-6-sulfamide compound and composition and application thereof

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

Active Publication Date: 2015-04-22
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-sulfamide compound and composition and application thereof
  • 2-oxo-1,2-dihydrobenzo[cd] indole-6-sulfamide compound and composition and application thereof
  • 2-oxo-1,2-dihydrobenzo[cd] indole-6-sulfamide compound and composition and application thereof

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-finalen-2-yl 4-methylbenzenesulfonate

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

[0073]

[0074] Add 1,8-naphthalenedicarboxylic anhydride (1-1) (11.9g, 0.06mol), hydroxylamine hydrochloride (4.18g, 0.06mol) and pyridine (70mL) in a round bottom flask, and heat to reflux for 1 hour. After cooling to 80°C, 4-toluenesulfonyl chloride (22.88g, 0.12mol) was added quickly, 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 was precipitated after stirring. Standing, filtering with suction, washing with water three times, stirring and washing with saturated sodium bicarbonate solut...

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 = 12.4 Hz, 1H), 2.87 (t, J = 13.2 Hz, 1H), 2.64 (t, J = 6.0 Hz, 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-sulfenamido)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] 1 H-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

The invention relates to a 2-oxo-1,2-dihydrobenzo[cd] indole-6-sulfamide compound and a composition and application thereof. The invention provides a compound with the structural characteristics of the general formula I in the specification serving as a novel retinoic acid orphan nuclear receptor gamma subtype (RORgamma) inhibitor, as well as an application of the compounds and pharmaceutically acceptable salts, isomers, racemes, pro-drug co-crystallization compounds, hydrates and solvates thereof in medicines for treating or preventing RORgamma-regulated related diseases. More importantly, the compounds are possibly used for reducing generation of immune factors related to immunological diseases and alleviating symptoms of immunologic derangement and cancers.

Description

Technical field [0001] The invention belongs to the technical field of chemical medicine, and specifically relates to a class of 2-oxo-1,2-dihydrobenzo[cd]indole-6-sulfonamide derivatives and pharmaceutically acceptable salts or stereoisomers thereof The construct, its prodrug molecule and preparation method, and the application of the compound in the preparation of drugs for treating 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 the central nervous system. RORγ can...

Claims

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Application Information

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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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