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

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

Inactive Publication Date: 2011-05-25
SHANGHAI INST OF ORGANIC CHEMISTRY - 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 of hydrated ruthenium trichloride (2.1 mg) (1.5 mL) was added, stirred at room temperature for 1.5 hours, and ether (5 mL) was added. ) and saturated aqueous sodium bicarbonate (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, extract with dichloromethane (5 mL x 4), combine the organic phases, anhydrous Dry with sodium sulfate, remove the solvent under reduced pressure, and obtain the synthesis of the target product (S)-3-fluoro-2-(4-isobutylbenzene)propionic acid. White solid, 91% yield, [...

Embodiment 2

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

[0022] Model Selection: Carrageenan-Induced Acute Inflammation Model of Paw Swelling in Rats

[0023] Rationale: Carrageenan increases prostaglandin (PG) synthesis in the inflammatory locale, and together with vasoactive amines such as histamine, 5-HT, and kinins, induces edema.

[0024] Sample preparation:

[0025] Positive control drug: ibuprofen

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

[0027] Drug dosage: 30mg / kg

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

[0029] Drug Administration Mode: i.g.

[0030] Drug under test: (S)-3-fluoro-2-(4-isobutylphenyl)propionic acid

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

[0032] Drug dosage: 33.6mg / kg

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

[0034] Drug Administration Mode: i.g

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

Embodiment 3

[0058] The analgesic effect of embodiment 3 (S)-3-fluoro-2-(4-isobutylphenyl) propionic acid

[0059] Model Selection: Chemical Stimulation

[0060] Basic principle: Many chemical substances, such as strong acid, strong alkali, potassium ion, bradykinin, etc., will cause pain when they come into contact with intact skin and mucous membranes. Therefore, administering certain chemical substances into animals can produce pain and create a pain model as a method 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 to cause deep, large-scale and long-lasting pain stimulation, causing the mice to produce a "writhing" response ( Belly concave, torso and hind legs extended, rump high). Observe the "writhing" times of mice or mice that have "writhing" reactions within 10 minutes of being given chemical stimulants, and c...

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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 invention belongs to the field of pharmacy, and provides a medicinal use of (S)-3-fluoro-2-(4-isobutylphenyl)propionic acid, which can be used for preparing anti-inflammatory, analgesic or anti-tumor drugs, and is for oral or oral administration. 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, some arylacetic compounds were found to have anti-inflammatory properties when studying plant growth hormones, and their derivatives were subsequently studied. 4-Isobutylphenylacetic acid has been used clinically, but after long-term high-dose use, aspartate aminotra...

Claims

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Application Information

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IPC IPC(8): A61K31/192A61P29/00A61P35/00
Inventor 苏红谢雨礼游书力刘文博
Owner SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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