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Water-soluble prodrugs of florfenicol and its analogs

A pharmacy and compound technology, applied in the field of nitrogen-containing esters, can solve the problems of slow dissolution of florfenicol and low water solubility of florfenicol

Inactive Publication Date: 2009-12-16
SCHERING PLOUGH ANIMAL HEALTH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, as mentioned above, Florfenicol has very low water solubility; thus Florfenicol dissolves very slowly in water

Method used

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  • Water-soluble prodrugs of florfenicol and its analogs
  • Water-soluble prodrugs of florfenicol and its analogs
  • Water-soluble prodrugs of florfenicol and its analogs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0127] The title hydrochloride salt was obtained from 20 g of Florfenicol by general procedures I and III and purified by stirring the solid in a mixture of ethyl acetate and hexane overnight to give 28 g (quantitative yield) of a white powder. h 1 -NMR (DMSO-d 6 ), δ=3.1ppm (t, 2H), 3.2ppm (s, 3H), 4.3ppm (m, 2H), 4.4-4.7 (m, 3H), 5.9ppm (d, 1H), 6.6ppm (s, 1H), 7.6 ppm (d, 2H), 7.9 ppm (d, 2H), 8.2 ppm (br, 3H), 9.2 (d, 1H).

Embodiment 2

[0128] The title hydrochloride salt was obtained from 20 g of Florfenicol by general procedures I and III without further purification to give 25 g (91% yield) of a white powder. h 1 -NMR (DMSO-d 6 ), δ=2.5ppm (s, 3H), 3.2ppm (s, 5H), 4.3ppm (m, 2H), 4.3-4.7 (m, 5H), 5.9ppm (d, 1H), 6.6ppm (s, 1H), 7.6 ppm (d, 2H), 7.9 ppm (d, 2H), 9.1 ppm (br, 2H), 9.3 (d, 1H).

Embodiment 3

[0129] The title hydrochloride salt was obtained from 9 g of Florfenicol by general procedures II and III and dried under reduced pressure at 65° C. for 2 days to give 7 g (56% yield) of a white powder. h 1 -NMR (DMSO-d 6 ), δ=1.8ppm (p, 2H), 2.5ppm (t, 2H), 2.8ppm (t, 2H), 3.2ppm (s, 3H), 4.3-4.7 (m, 3H), 6.0ppm (d, 1H), 6.6 ppm (s, 1H), 7.6 ppm (d, 2H), 7.9 ppm (d, 2H), 8.1 ppm (br, 3H), 9.2 (d, 1H).

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Abstract

The present invention discloses certain novel prodrugs of florfenicol and / or of florfenicol analogs, including prodrugs of salts pharmaceutically acceptable salts of florfenicol and its analogs, including nitrogen-containing esters of the secondary alcohol group of florfenicol and of its analogs, and pharmaceutically acceptable salts thereof, compositions containing them, and methods of administering them to subjects. In particular embodiments the prodrugs are sufficiently water-soluble to serve the functions needed of a water-soluble prodrug of florfenicol or of a water-soluble prodrug of a florfenicol analog. A certain subclass of the compounds also possesses the hydrolytic stability needed to maintain the prodrug in solution in the subject's system until appropriate conditions exist when the prodrug can hydrolyze, releasing florfenicol or the florfenicol analog in question.

Description

[0001] Cross References to Related Applications [0002] This application is a non-provisional application claiming priority under 35 U.S.C. §119(e) to US Provisional Application 60 / 874,864, filed December 13, 2006, which is hereby incorporated by reference in its entirety. field of invention [0001] The present invention relates to novel prodrugs of florfenicol and its analogs. In a specific aspect, the present invention relates to charged nitrogen-containing esters of florfenicol and analogs thereof exhibiting improved water solubility and hydrolytic stability. In particular embodiments of this aspect, the invention relates to certain charged nitrogen-containing esters of Florfenicol. Background of the invention [0002] Florfenicol (2,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4-(methylsulfonyl)phenyl)propan-2-yl)acetamide ) has the following chemical structure Florfenicol [0003] Florfenicol is a broad-spectrum antibiotic active against a wide variety of Gram...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/16C07C237/06C07D233/54A61K31/16A61K31/4166A61P31/04
CPCC07D233/60C07D233/54C07C317/32C07K5/06191A61P31/04
Inventor T·W·格林卡J·张
Owner SCHERING PLOUGH ANIMAL HEALTH
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