Sufonic aniline derivatives and their medicinal use

A drug and compound technology, applied in the field of sulfonyl anilide derivatives, can solve problems such as liver toxicity

Inactive Publication Date: 2004-07-14
RADIOLOGY INST ACAD OF MILITARY MEDICINE SCI PLA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in recent years, it has been found that even nimesulide, it still has considerable liver toxicity

Method used

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  • Sufonic aniline derivatives and their medicinal use
  • Sufonic aniline derivatives and their medicinal use
  • Sufonic aniline derivatives and their medicinal use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] The preparation of embodiment 1 compound

[0021] A: Preparation of trans-4-methyl-cyclohexylamine salt of 4-nitro-2-phenoxymethanesulfonanilide

[0022] Dissolve 6.17 g of 4-nitro-2-phenoxy-methanesulfonanilide in 25 ml of acetone, add 2.37 g of trans-4-methyl-cyclohexylamine dropwise under stirring at room temperature, and heat for 1 hour , part of the solvent was removed under reduced pressure, and the residue was left overnight, and bright yellow needle-like crystals were precipitated, which were collected by filtration. Recrystallized from ethanol to obtain 6.54 g of trans-4-methyl-cyclohexylamine salt of 4-nitro-2-phenoxy-methanesulfonanilide (yield 77.6%), melting point 149-151°C.

[0023] Molecular formula C 20 h 27 N 3 o 5 S molecular weight 421.51

[0024] Elemental analysis: theoretical value C 56.99%, H 6.46%, N 9.97%

[0025] Experimental value C 57.00%, H 6.49%, N 9.92%

[0026] B: Preparation of 4-nitro-2-(4′-methoxy-phenoxy)-methanesulf...

Embodiment 2

[0040] Example 2 Biological Evaluation

[0041] In the following biological experiments, the effects of each compound on mouse acetic acid writhing analgesic response and anti-mouse carrageenan foot inflammation were mainly observed. Nimesulide was used as a positive control drug to conduct a preliminary study on its therapeutic effect. evaluate. The results are shown in the table below:

[0042] Table 1 The effect of oral nimesulide and its derivatives on antagonizing the writhing response of mice with acetic acid

[0043] Drug Dose Number of animals Number of writhes

[0044] Mm / kg (M±SD)

[0045] DMSO control 14 32.4±24.1

[0046] Nimesulide 0.32 9 22.0±1 6.9

[0047]0.97 9 14.7±11.3*

[0048] S 1 0.97 10 11.7±14.2*

[0049] S 2 0.32 10 20.6±18.8

[0050] S 3 0.97 10 5.3±6.4**#

[0051] S 5 0.97 10 34.5±16.2

[0052] Compared with DMSO control, *P<0.05 **P<0.01

[0053] Compared with Nimesuli, #P<0.05

[0054] ...

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Abstract

The present invention discloses the preparation process and medicinal use of sulfonyl aniline derivatives as non-steroid antiphlogistic and analgetic compounds. These compounds have antiphlogistic and analgetic effects, so that they may be used in preparing medicine for clinically treating various inflammations, tumors, thrombotic angeitis, post-operation pain, menstrual pain, otorhinolaryngological diseases, wound pain, inflammation, etc.

Description

technical field [0001] The invention belongs to non-steroidal anti-inflammatory and analgesic compounds, and the invention relates to a new application in the preparation of anti-inflammatory and analgesic drugs, which is a sulfonyl anilide derivative. technical background [0002] Non-steroidal anti-inflammatory drugs (NSAIDs) have anti-inflammatory and analgesic effects, and have been widely used clinically to treat various inflammations (such as osteoarthritis, respiratory inflammation) or tumors, thromboangiitis, postoperative pain, menstrual pain, Otolaryngology diseases, as well as post-traumatic pain, inflammation and fever symptoms, especially arthritis is more commonly used. The role of prostaglandins in causing inflammatory pathogenesis has been discovered since 1970, and the related cyclooxygenase is a prostaglandin synthase. Of course, the beneficial effects of prostaglandins have also been confirmed by people, such as protecting the cells of the gastrointestina...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K9/00A61K31/18A61K47/32A61K47/40A61P29/00C07C311/08
CPCA61K9/0019A61K47/40A61K31/18C07C311/08A61K9/0014A61K47/32A61P29/00
Inventor 孙庄蓉吴祖泽刘爱全唐仲雄
Owner RADIOLOGY INST ACAD OF MILITARY MEDICINE SCI PLA
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