Medical use of (S)-3-fluoro-2-(4-isobutyl phenyl) propionic acid

A kind of technology of isobutylbenzene and propionic acid, applied in the field of pharmacy

Inactive Publication Date: 2012-05-23
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the limitations of chiral asymmetric synthesis or resolution techniques, most of the commercially available products are still in the form of racemates

Method used

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  • Medical use of (S)-3-fluoro-2-(4-isobutyl phenyl) propionic acid
  • Medical use of (S)-3-fluoro-2-(4-isobutyl phenyl) propionic acid
  • Medical use of (S)-3-fluoro-2-(4-isobutyl phenyl) propionic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Example 1 Synthesis of (S)-3-fluoro-2-(4-isobutylbenzene)propionic acid

[0019]

[0020] In a round bottom flask, combine optically pure (R)-1-(1-fluoro-3-enyl-2-butyl)-4-isobutylbenzene (41.7 mg) and sodium periodate (213.8 mg) ) Was dissolved in 2 ml of a mixed solvent of carbon tetrachloride and acetonitrile (1:1), then an aqueous solution (1.5 ml) of hydrated ruthenium trichloride (2.1 mg) was added, stirred at room temperature for 1.5 hours, and ether (5 ml ) And saturated aqueous sodium bicarbonate solution (5 mL). Extract with aqueous sodium bicarbonate solution (5 mL x 5), combine the aqueous phases, slowly add concentrated hydrochloric acid at zero degrees Celsius to adjust the pH to 1, then extract with dichloromethane (5 mL x 4), combine the organic phases, and anhydrous After drying over sodium sulfate, the solvent was removed under reduced pressure to obtain the target product (S)-3-fluoro-2-(4-isobutylbenzene)propionic acid. White solid, 91% yield, [α] D 2...

Embodiment 2

[0021] Example 2 Anti-inflammatory effect of (S)-3-fluoro-2-(4-isobutylbenzene)propionic acid

[0022] Model selection: carrageenan-induced acute inflammation model of rat foot swelling

[0023] Basic principle: Carrageenan increases the synthesis of prostaglandin (PG) in the inflamed area, and induces edema together with vasoactive amines such as histamine, 5-HT and kinins.

[0024] Sample preparation:

[0025] Positive control drug: ibuprofen

[0026] Preparation method: Dissolve and dilute with 0.5% CMC into a white turbid liquid.

[0027] Drug administration dose: 30mg / kg

[0028] Drug administration volume: 1ml / 100g

[0029] Drug administration method: i.g.

[0030] Test drug: (S)-3-fluoro-2-(4-isobutylbenzene)propionic acid

[0031] Preparation method: Dissolve and dilute with 0.5% CMC to a pale yellow turbid liquid.

[0032] Drug administration dose: 33.6mg / kg

[0033] Drug administration volume: 1ml / 100g

[0034] Drug administration method: i.g

[0035] Carrageenan (λCarrageenan) was pur...

Embodiment 3

[0058] Example 3 Analgesic effect of (S)-3-fluoro-2-(4-isobutylbenzene)propionic acid

[0059] Model selection: chemical stimulation method

[0060] Basic principle: Many chemical substances, such as strong acids, strong bases, potassium ions, bradykinin, etc., cause pain when they come into contact with intact skin and mucous membranes. Therefore, certain chemical substances can be injected into animals to produce pain and cause pain models, which are used as methods for studying pain physiology and screening analgesic drugs. The mouse writhing method is one of the commonly used methods for screening analgesics. Some chemical stimulants are injected into the abdominal cavity of mice, causing deep, large-area and longer-lasting painful stimulation, causing the mice to have a "writhing" response ( The abdomen is recessed, the trunk and hind legs are stretched, and the buttocks are raised). Observe the number of "writhing" in mice that have a "writhing" reaction within 10 minutes o...

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Abstract

The invention discloses a medical use of (S)-3-fluoro-2-(4-isobutyl phenyl) propionic acid. Further, the (S)-3-fluoro-2-(4-isobutyl phenyl) propionic acid can be used for preparing analgesic and anti-inflammatory or anti-tumor medicaments containing the (S)-3-fluoro-2-(4-isobutyl phenyl) propionic acid or pharmaceutical acceptable salts thereof.

Description

Technical field [0001] The present invention belongs to the field of pharmacy, and provides a medicinal use of (S)-3-fluoro-2-(4-isobutylbenzene)propionic acid, which can be used to prepare anti-inflammatory and analgesic or anti-tumor drugs, which are oral or Formulations for parenteral administration. Background technique [0002] Non-steroidal anti-inflammatory drugs (NSAIDs) have good anti-inflammatory, antipyretic and analgesic effects, and are widely used to treat pain caused by osteoarthritis, rheumatoid arthritis and various inflammations. It blocks the metabolism of arachidonic acid by inhibiting cyclooxygenase, thereby blocking the production of prostaglandins. [0003] In the late 1960s, when studying plant growth hormones, some aryl acetic acid compounds were found to have anti-inflammatory effects, and then their derivatives were studied. 4-Isobutylphenylacetic acid has been used clinically, but after long-term high-dose use, it will cause aspartate aminotransferase ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/192A61P29/00A61P35/00
Inventor 苏红谢雨礼游书力刘文博
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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