Unlock instant, AI-driven research and patent intelligence for your innovation.

2-Mercapto-4,5-Diarylimidazole Derivatives and the use thereof as Cyclooxygenase Inhibitors

a technology of diarylimidazole and cyclooxygenase inhibitor, which is applied in the field of 2mercapto4, 5diarylimidazole derivatives, can solve the problems of inability to fully understand the biochemical inability to fully elucidate the biological mode of action of the two enzymes, and inability to stabilize known compounds, etc., to achieve high cyclooxygenase inhibitor activity, stable cox ratio ratio

Inactive Publication Date: 2007-08-09
BEIERSDORF AG
View PDF7 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0012] Surprisingly, it has now been found that certain 2-mercapto-4,5-diarylimidazole derivatives are stable compounds which are easy to process, and which have a high cyclooxygenase-inhibiting action with a variable COX-1 / COX-2 selectivity.

Problems solved by technology

Despite numerous investigations, the biochemical mode of action of the two enzymes is not yet completely elucidated.
It is known that the conventional nonsteroidal antiinflammatories have a number of undesired side effects, in particular gastrointestinal side effects, nephrotoxicity and allergic reactions.
It was further found that the known compounds are not stable and are difficult to process or have a low activity.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 2-Mercapto-4,5-Diarylimidazole Derivatives and the use thereof as Cyclooxygenase Inhibitors
  • 2-Mercapto-4,5-Diarylimidazole Derivatives and the use thereof as Cyclooxygenase Inhibitors
  • 2-Mercapto-4,5-Diarylimidazole Derivatives and the use thereof as Cyclooxygenase Inhibitors

Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis of 1,2-bis(4-chlorophenyl)-2-hydroxyethanone (4,4′-dichloro-benzoin) (Z1)

[0140] 42.2 g of 4-chlorobenzaldehyde and 5 g of KCN were heated under reflux in 300 ml of a 1:1 mixture of ethanol and water for 6 hours. After cooling, the ethanol was stripped off, the residue was cooled in an ice bath and the supernatant aqueous phase was decanted off. The product was recrystallized from ethanol / petroleum ether and dried. 22 g of the compound Z1 mentioned in the title were obtained.

example 2

Synthesis of 1,2-bis(4-fluorophenyl)-2-hydroxyethanone (4,4′-dichloro-benzoin) (Z2)

[0141] 50 g of 4-fluorobenzaldehyde were reacted by the same process as in example 1. 29 g were obtained.

example 3

Synthesis of 1,2-bis[4-(trifluoromethyl)phenyl]-2-hydroxyethanone (4,4′-trifluoromethylbenzoin) (Z3)

[0142] 50 g of 4-fluorobenzaldehyde were reacted by the same process as in example 1. The yield was 28 g.

[0143] b) Synthesis of Unsymmetrical Benzoins

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
temperatureaaaaaaaaaa
temperatureaaaaaaaaaa
polarityaaaaaaaaaa
Login to View More

Abstract

The invention relates to the 2-mercapto-4,5-diarylimidazole derivatives of formula (I), wherein R1, R2, R3 and R4 are defined as in the description. The inventive compounds have an immunomodulatory and cyclooxygenase-inhibiting activity and are therefore suitable for the treatment of disease that are associated with a disturbed immune system.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS [0001] This is a continuation application of U.S. patent application Ser. No. 10 / 672,613, filed Sep. 26, 2003, which is a continuation application of PCT / EP02 / 03264, filed Mar. 22, 2002, which are incorporated herein by reference in their entirety, and also claims the benefit of German Priority Application No. 101 14 775.9, filed Mar. 26, 2001.FIELD OF THE INVENTION [0002] The present invention relates to 2-mercapto-4,5-diarylimidazole derivatives having immunomodulating and cyclooxygenase-inhibiting action, pharmaceutical compositions which contain the compound, and their use in pharmacy. BACKGROUND OF THE INVENTION [0003] The action of conventional nonsteroidal antiinflammatories, such as acetylsalicylic acid, is essentially based on the inhibition of cyclooxygenase, an enzyme of the arachidonic acid cascade, which is also known as prostaglandin G / H synthase. Meanwhile, two different forms of cyclooxygenase have been found, which are designa...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(United States)
IPC IPC(8): A61K31/4439C07D403/02A61K8/49A61K31/4164A61K31/4178A61K31/4184A61K31/4709A61K31/5377A61P1/04A61P1/18A61P9/10A61P9/14A61P11/00A61P15/06A61P17/06A61P17/14A61P17/16A61P19/02A61P19/06A61P19/10A61P25/04A61P25/28A61P29/00A61P31/04A61P35/00A61P35/04A61P37/00A61P37/02A61P37/06A61P37/08A61P43/00C07D233/84C07D401/12C07D403/12C07D405/12C07D409/12
CPCA61K8/4946A61K2800/782A61Q19/00C07D409/12C07D401/12C07D403/12C07D405/12C07D233/84A61P1/04A61P1/18A61P11/00A61P15/06A61P17/06A61P17/14A61P17/16A61P19/02A61P19/06A61P19/10A61P25/04A61P25/28A61P29/00A61P31/04A61P35/00A61P35/04A61P37/00A61P37/02A61P37/06A61P37/08A61P43/00A61P9/10A61P9/14
Inventor DANNHARDT, GERDHAHN, LINDA
Owner BEIERSDORF AG