High-water-solubility florfenicol prodrug quickly released in vivo

A technology of florfenicol and florfenicol succinic acid, which is applied in the field of pharmaceutically acceptable salts of florfenicol succinic acid monoester and its preparation, and can solve the problems of difficult promotion, harsh synthesis conditions, cumbersome process, etc. problem, to achieve the effect of maintaining antibacterial activity, convenient medication, and simple synthesis process

Inactive Publication Date: 2008-10-22
SOUTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, its synthesis conditions are harsh, the process is cumbersome, and it is not easy to promote

Method used

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  • High-water-solubility florfenicol prodrug quickly released in vivo
  • High-water-solubility florfenicol prodrug quickly released in vivo
  • High-water-solubility florfenicol prodrug quickly released in vivo

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] The preparation of embodiment 1 florfenicol succinic acid monoester

[0018] Under nitrogen flow, 10.0 g of florfenicol and 4.7 g of succinic anhydride were added to 50 mL of acetonitrile, and 1 mL of catalyst was added. Reflux at 80°C for 10 hours. Concentrate to dryness under reduced pressure, add 100 mL of ethyl acetate to dissolve, wash with dilute hydrochloric acid, wash with water, and evaporate to dryness under reduced pressure. The crude product was crystallized with ethanol, water, acetone, petroleum ether or their mixed solvents to obtain a solid, which was suction filtered and dried to obtain 9.7 g of white solid, mp 129.6-130.0°C, yield 75.8%.

[0019] IR (cm -1 ): 1672.95, 1702.21, 1741.50 (C=O);

[0020] 1 H-NMR (d 6 -DMSO, 400MHz) δ: 8.91 (1H, d), 7.60 ~ 7.89 (Ar-H, dd), 6.43 (1H, d), 6.01 (1H, d), 4.30 ~ 4.63 (3H, m), 3.19 ( 3H, s), 2.49 ~ 2.67 (4H, m);

[0021] 13 C-NMR (d 6 -DMSO, 400MHz) δ: 173.2, 171.1, 163.8, 126.8~142.6 (Ar-C), 82.7, 81.0,...

Embodiment 2

[0023] Embodiment 2 The preparation of florfenicol monosodium succinate (1)

[0024] Dissolve 0.84g of sodium bicarbonate in 10mL of water, and add 4.58g of florfenicol succinic acid monoester under stirring. When it is completely dissolved and no bubbles are released, add 5-15 times the amount of ethanol or acetone to form a precipitate. Suction filtration, vacuum drying of the solid at 90°C, yielded 3.96 g of florfenicol monosodium succinate, mp 157.4-158.3°C, yield 82.5%.

Embodiment 3

[0025] The preparation of embodiment 3 florfenicol succinate monoester sodium (2)

[0026] Dissolve 4.58g of florfenicol succinic acid monoester in 30mL of methanol, then add 0.53g of sodium carbonate and stir until no bubbles are released, put in activated carbon for decolorization and filtration, distill the filtrate under reduced pressure, crystallize the residue in 90% ethanol, and filter with suction The solid was dried to obtain 3.85 g of florfenicol monosodium succinate, with a yield of 80.2%.

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PUM

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Abstract

The invention relates to a florenicol succinic acid monoester and a preparation method thereof, and the florenicol succinic acid monoester can be obtained by the esterification of the florenicol and succinic anhydride. Simultaneously, the invention also relates to acceptable salts and preparation methods thereof of the florenicol succinic acid monoester pharmacy, such as sodium salt, potassium salt, calcium salt and magnesium salt etc., and salts that are formed with basic amino acids and comprises lysine and arginine salts. By testing, the water-solubility of the corresponding salt is more than 500 mg / ml. The water-soluble derivatives disclosed by the invention quickly release the florenicol after being hydrolyzed in bodies and the derivatives can be used as high water-soluble prodrugs of the florenicol.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and relates to florfenicol succinic acid monoester and a preparation method thereof. At the same time, the invention also relates to a pharmaceutically acceptable salt of florfenicol succinic acid monoester and a preparation method thereof, such as sodium salt, potassium salt Salts, calcium salts and magnesium salts, etc., and salts formed with basic amino acids include lysine salts and arginine salts. The prodrug verification test showed that the derivatives were rapidly transformed into florfenicol after entering the body. Background technique [0002] Florfenicol is a veterinary broad-spectrum antibacterial drug developed by the American Schering-Plough Company in the late 1970s. Florfenicol is a new type of broad-spectrum chloramphenicol antibacterial drug, which is the 3-position derivative of thiamphenicol in the broad-spectrum antibacterial drug of chloramphenicol. It is characterized by ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/32C07C315/04A61P31/00
Inventor 李逐波杨鹏何小燕秦光成余虹田金凤任方奎王艳凤
Owner SOUTHWEST UNIV
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