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Antifungal agents

A compound, pharmaceutical technology, applied in the direction of antifungal, biocide, animal repellent, etc., can solve problems such as secondary tolerance

Active Publication Date: 2011-09-07
SCYNEXIS INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

secondary tolerance

Method used

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Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0318]

[0319] 2-Isopropyl-2-methyl-1-[(4-methylphenyl)sulfonyl]aziridine

[0320] To a solution of 2,3-dimethylbutene (300 mL, 2.42 mol) in 7.8 L of dry acetonitrile was added chloramine-T (749.9 g, 1.1 eq) in portions over 90 minutes. The temperature was maintained at about 20°C. To the reaction mixture was added phenyltrimethylammonium tribromide (91.4 g, 0.1 eq) in 10 g portions over 90 minutes, raising the reaction temperature to 26°C during the addition. The reaction mixture was stirred at room temperature for two days. The reaction mixture was concentrated to approximately 15% of the original volume, then filtered, washing the solids with 1 L of acetonitrile. The organic liquid phase was concentrated, and the residue was dissolved in 2.5 liters of ethyl acetate. The remaining solution was washed twice with water using MgSO 4 Dry and concentrate to yield a solid. The crude product was purified over a large volume of Celite using serial dilutions from 5% to 25%...

preparation example 2

[0322]

[0323] (2R)-2-Isopropyl-2-methyl-1-[(4-methylphenyl)sulfonyl]aziridine alkyl

[0324] step 1

[0325] To LiAlH 4 A small portion of (R)-α-methylvaline (8.05 g, 61.4 mmol) was added to a cooled solution of THF (1M, 123 mL, 123 mmol), maintaining the reaction temperature below 15°C. The reaction was stirred at 0°C for several minutes, then heated to reflux for 4 hours. The reaction mixture was cooled to room temperature and then quenched by adding sodium sulfate dodecahydrate / celite (1:1 mass ratio) until gas evolution ceased. The reaction mixture was filtered, washed with THF and methanol. The filtrate was concentrated under reduced pressure to yield 4.7 g of the aminoalcohol as a colorless oil.

[0326] step 2

[0327] At 0°C, to the aminoalcohol product (4.70 g, 40.1 mmol) of step 1, Et 3 N (22.36 mL, 160 mmol) and 4-dimethylaminopyridine (0.490 g, 4.01 mmol) in anhydrous CH 2 Cl 2 (200 mL), p-toluenesulfonyl chloride (22.94 g, 120 mmol) was added ...

preparation example 3

[0330]

[0331] (2S)-2-Isopropyl-2-methyl-1-[(4-methylphenyl)sulfonyl]aziridine alkyl

[0332] step 1:

[0333] A 5 L three-necked flask containing 540 mL of dry THF was charged with NaBH 4 (94.5 g, 2.498 mol). The resulting solution was cooled in an ice bath, and (S)-methylvaline (75 g, 0.572 mol) was added to the solution. The resulting mixture was stirred under nitrogen for 20 min, then H was added dropwise over a period of 3.5 h. 2 SO 4 (66.7 mL, 1.252 mol) in 160 mL of dry ether. The reaction mixture was heated for one hour while in an ice bath, then allowed to warm to room temperature overnight. in CH 2 Cl 2 TLC in MeOH (70 / 30) showed the reaction was complete. The reaction was cooled in an ice bath, then quenched by the slow addition of 250 mL of methanol over a period of 45 minutes. The reaction mixture was then stirred at room temperature for 15 min, then NaOH (5N, 700 mL) was added very slowly. A distillation head was fitted to the flask and heated...

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Abstract

Novel derivatives of enfumafungin are disclosed herein, along with' their pharmaceutically acceptable salts, hydrates and prodrugs. Also disclosed are compositions comprising such compounds, methods of preparing such compounds and method of using such compounds as antifungal agents and / or inhibitors of (l,3)-beta-D-glucan synthase. The disclosed compounds, their pharmaceutically acceptable salts, hydrates and prodrugs, as well as compositions comprising such compounds, salts, hydrates and prodrugs, are useful for treating and / or preventing fungal infections and associated diseases and conditions.

Description

[0001] joint research agreement [0002] Claimed subject matter is presented as a result of activities undertaken within the scope of a joint research agreement between Merck & Co., Inc. and Scynexis, Inc. field of invention [0003] The claimed subject matter relates to novel compounds and their pharmaceutically acceptable salts, hydrates and prodrugs, compositions containing such compounds, methods of synthesizing such compounds, and such compounds as antifungal preparations and / or Use of (1,3)-β-D-glucan synthase inhibitors. The compounds described in the present invention are derivatives of enfumafungin. The novel compounds described in the present disclosure, their pharmaceutically acceptable salts, hydrates and prodrugs, and compositions comprising such compounds, salts, hydrates and / or prodrugs, can effectively For the treatment and / or prevention of fungal infections and related diseases and conditions. Background technique [0004] Fungal infections are an importa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N43/64A61K31/21A61K31/41
CPCA61K31/41C07D405/04A61K31/21A61P31/10A61P43/00
Inventor M·L·格林李R·威尔克宁J·阿普加D·斯珀尔贝克K·J·维尔登格孟东方小D·L·帕克A·玛麦
Owner SCYNEXIS INC
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