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Benzophenones as inhibitors of IL-1 beta and TNF-alpha

A solvate, C1-C6 technology, applied in the direction of anti-inflammatory agents, antiviral agents, amine active ingredients, etc., can solve problems such as undocumented potential therapeutic uses

Inactive Publication Date: 2006-02-01
LEO PHARMA AS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in this publication, there is no mention of any potential therapeutic use of this class of compounds

Method used

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  • Benzophenones as inhibitors of IL-1 beta and TNF-alpha
  • Benzophenones as inhibitors of IL-1 beta and TNF-alpha
  • Benzophenones as inhibitors of IL-1 beta and TNF-alpha

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach

[0033] In compounds of formula I:

[0034] R 1 Preferred representatives are selected from the group consisting of halogen, hydroxy, mercapto, trifluoromethyl, amino, (C 1 -C 6 ) Alkyl, (C 2 -C 6 ) alkenyl, (C 1 -C 6 ) alkoxy, (C 1 -C 6 ) Alkylthio, (C 1 -C 6 ) Alkylamino, (C 1 -C 6 ) alkoxycarbonyl, cyano, -CONH 2 , phenyl and nitro substituents; especially fluorine, chlorine, bromine, hydroxyl, trifluoromethyl, amino, (C 1 -C 3 ) Alkyl, (C 2 -C 3 ) alkenyl, (C 1 -C 3 ) alkoxy, (C 1 -C 3 ) alkoxycarbonyl, cyano or -CONH 2 ;

[0035] R 2 Represents one or more identical or different substituents selected from hydrogen, halogen, hydroxyl, mercapto, trifluoromethyl, amino, (C 1 -C 6 ) Alkyl, (C 2 -C 6 ) alkenyl, (C 1 -C 6 ) alkoxy, (C 1 -C 6 ) Alkylthio, (C 1 -C 6 ) Alkylamino, (C 1 -C 6 ) alkoxycarbonyl, cyano, -CONH 2 , phenyl and nitro; especially hydrogen, fluorine, chlorine, bromine, hydroxyl, trifluoromethyl, amino, (C 1 -C 3 ) Alkyl, (...

Embodiment 1

[0498] Example 1 : 2-chloro-2'-methyl-4-(4-pyridylamino)benzophenone (compound 101),

[0499] General steps: 2

[0500] Starting compound II: 4-chloro-pyridine hydrochloride (0.30 g, 2.0 mmol)

[0501] Starting compound III: 4-amino-2-chloro-2'-methylbenzophenone (compound 2) (0.49g, 2.0mmol)

[0502] Solvent: DMSO (15mL)

[0503] Base: Potassium tert-butoxide (0.67 g, 6.0 mmol) in DMSO (10 mL)

[0504] Response time: 22 hours

[0505] Reaction temperature: 150°C

[0506] Purification: chromatography using EtOAc:MeOH 15:1

[0507] Product: Compound 101, 0.20 g oil

[0508] 1 H NMR (CDCl 3 ): δ8.39(d, 1H), 7.43(d, 1H), 7.40-7.20(m, 5H), 7.08(dd, 1H), 6.97(d, 3H), 2.50(s, 3H)

Embodiment 2

[0509] Example 2 : 2-chloro-2'-methyl-4-(2-pyridylamino)benzophenone (compound 102),

[0510] General steps: 2

[0511] Starting compound II: 2-chloro-pyridine (0.19 mL, 2.0 mmol)

[0512] Starting compound III: 4-amino-2-chloro-2'-methylbenzophenone (compound 2) (0.49g, 2.0mmol)

[0513] Solvent: DMSO (15mL)

[0514] Base: Potassium tert-butoxide (0.45 g, 4.0 mmol) in DMSO (10 mL)

[0515] Response time: 22 hours

[0516] Reaction temperature: 150°C

[0517] Purification: Chromatography using EtOAc:petroleum ether 1:5

[0518] Product: Compound 102, 0.21 g oil

[0519] 1 H NMR (CDCl 3 ): 88.28(d, 1H), 7.65(d, 1H), 7.58(t, 1H), 7.41(d, 1H), 7.40-7.25(m, 4H), 7.19(t, 1H), 6.95(s, 1H), 6.86(m, 2H), 2.47(s, 3H)

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PUM

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Abstract

Heteroaryl aminobenzophenones of general formula (I) inhibit interleukin-1 beta and TNF-alpha and may therefore be useful in the therapy of inflammatory diseases and conditions.

Description

field of invention [0001] The present invention relates to a new class of compounds, including heteroarylaminobenzophenone derivatives, exhibiting anti-inflammatory effects, to pharmaceutical compositions containing these compounds and to their use in the treatment and prophylaxis of inflammatory diseases. Background of the invention [0002] A series of aminobenzophenones (e.g. 4-(2-amino-4-nitrophenylamino)benzophenone) have been described previously (Hussein, F.A. et al., Iraqi J.Sci. , 22, 54-66 (1981)). However, in this publication there is no mention of any potential therapeutic use of such compounds. WO 98 / 32730 discloses aminobenzophenone inhibitors of interleukin 1β (IL1-1β) and tumor necrosis factor α (TNF-α) secreted in vitro and demonstrates the potential use of these compounds in the treatment of inflammatory diseases, Pro-inflammatory cytokine production is implicated in the pathogenesis of inflammatory diseases such as asthma, rheumatoid arthritis, psoriasis...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/74C07D215/38C07D217/22C07D209/40A61K31/44A61K31/47A61K31/404A61P29/00C07D249/14A61K31/136A61K31/15A61K31/403A61K31/4184A61K31/4196A61K31/423A61K31/426A61K31/428A61K31/4402A61K31/4406A61K31/4409A61K31/4706A61K31/472A61K31/505A61K31/52A61K45/00A61K45/06A61P1/00A61P7/00A61P9/10A61P11/06A61P17/00A61P17/06A61P19/02A61P19/06A61P19/10A61P27/02A61P31/04A61P31/18A61P37/02A61P37/08C07D209/08C07D213/79C07D213/80C07D213/84C07D213/85C07D213/89C07D215/40C07D215/42C07D235/30C07D239/42C07D241/20C07D249/10C07D263/58C07D277/20C07D277/58C07D277/64C07D277/82C07D473/34C07D487/04
CPCA61K31/47C07D239/42C07D235/30C07D277/82A61K31/136C07D241/20C07D213/85C07D213/89C07D209/08C07D215/38C07D277/64A61K31/403C07D249/10A61K45/06C07D213/79C07D277/58C07D473/34C07D213/80C07D217/22C07D215/40C07D213/74C07D263/58A61K31/15A61P1/00A61P11/06A61P17/00A61P17/06A61P19/02A61P19/06A61P19/10A61P27/02A61P29/00A61P31/04A61P31/18A61P37/02A61P37/08A61P7/00A61P9/10
Inventor A·M·霍尼曼
Owner LEO PHARMA AS