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Processes for preparing enantiomerically pure diol and dioxolane compounds

A technology of dioxolane and pure compounds, applied in the field of preparation of optically pure diols and dioxolane compounds, can solve the problem of high cytotoxic effect, ineffectiveness, inappropriate pharmacological properties, and narrow activity spectrum of drug-drug interactions And other issues

Inactive Publication Date: 2011-04-13
STIEFEL LABORATORIES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Antifungal agents commonly used in the clinic are limited by their ineffectiveness and inappropriate pharmacological properties, including unanticipated drug-drug interactions and narrow activity spectrum, and by high overall cytotoxic effects [White et al., 1998 ]

Method used

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  • Processes for preparing enantiomerically pure diol and dioxolane compounds
  • Processes for preparing enantiomerically pure diol and dioxolane compounds
  • Processes for preparing enantiomerically pure diol and dioxolane compounds

Examples

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preparation example Construction

[0067] Other antifungal compounds that can be prepared by the method of the present invention for preparing optically pure compounds such as compounds of formulas (1), (2), (5) and (6) include but are not limited to ketoconazole, itraconazole, Isoconazole, miconazole, econazole, sulconazole, fluconazole, fenticonazole, sertaconazole, tioconazole, fluconazole, voriconazole, and ravconazole.

[0068] Optically pure compounds of formula (1) and formula (2) may exist in the form of pharmaceutically acceptable salts, either alone or as part of a larger molecule. Suitable pharmaceutically acceptable salts are organic or inorganic acids, including but not limited to hydrochloric, hydrobromic, hydroiodic, sulfuric, nitric, trifluoroacetic, phosphoric, acetic, succinic, oxalic, malic, trans Salts of butenedioic acid and its analogues.

[0069] If the moiety of formula (1) exists in optically pure form, the therapeutic activity of compounds such as praconazole comprising moieties shown...

Embodiment 1

[0088]

[0089]Add approximately 4,000 mL of vinyl acetate to the round bottom flask. Measure the initial moisture content of the vinyl acetate and adjust to 0.8 to 1.0% by adding water. At 30 to 35 ° C, about 100 g of compound 2 was added to vinyl acetate, and after stirring for 5 to 10 minutes, 3.6 g of 2,6-lutidine was added at 30 to 35 ° C, and stirred for 5 to 10 minutes. About 5 g of CAL-B enzyme was then added to the round bottom flask and the reaction mixture was maintained at 30 to 35°C for 10 hours. After 10 hours, the reaction was monitored periodically by HPLC to determine the progress of the resolution reaction. When the enantiomeric excess of compound 3 exceeded 98, the enzyme was filtered from the reaction mixture, and the vinyl acetate was evaporated at a temperature below 45 °C until approximately 500 mL of the reaction mixture remained. About 1,500 mL of demineralized water was added, and the remaining vinyl acetate was removed under reduced pressure at...

Embodiment 2

[0091]

[0092] About 50 g of compound 3 was mixed with 500 mL of dichloromethane in a round bottom flask at 25 to 35 °C. At 25 to 35°C, about 34 g of triethylamine was added, the reaction mixture was cooled to 0 to 10°C, and then 29 mL of methanesulfonyl chloride was added dropwise at 0 to 10°C. After stirring at 0 to 10° C. for 2 to 3 hours, the reaction mixture was diluted with 150 mL of demineralized water and stirred for 5 to 10 minutes. The phases were separated, and extracted twice successively with 150 mL of dichloromethane. The organic phases were combined and washed three times with 150 mL of water. The organic layer was concentrated to minimum volume, 500 mL of isopropylamine was added and concentrated in vacuo. The resulting mass was cooled to 25 to 35°C and held for 2 to 3 hours, then cooled to 8 to 12°C for an additional 2 to 3 hours. Filter and wash the solid with 100 mL of isopropylamine that has been cooled to 8 to 12°C. Yield of compound 4: 75 to 85%. ...

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Abstract

The present invention relates to novel processes for preparing enantiomerically pure diol and dioxolane compounds from racemic starting materials and the use of these compounds for preparing therapeutically active agents.

Description

technical field [0001] The present invention relates to novel processes for the preparation of optically pure diol and dioxolane compounds from racemic starting materials, and the use of these compounds in the preparation of therapeutically active agents. Background technique [0002] The incidence of systemic fungal and gram-positive bacterial infections is increasing worldwide, most likely due to advances in medical technology and organ transplantation, increased use of cytotoxic chemotherapeutic interventions in general, broad-spectrum antimicrobial agents, and indwelling catheters. Widespread use and increasing numbers of immunocompromised patients. [0003] The most common fungal infections are caused by Candida spp., of which C. albicans accounts for approximately 50%, and filamentous fungi such as Aspergillus spp. [Kremery and Barnes, 2002] . Mortality associated with invasive Candida species is approximately 40% [Edmond et al., 1999], whereas Aspergillus-associated...

Claims

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Application Information

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IPC IPC(8): C07B57/00C12P41/00C07D405/06C07D405/14
CPCC07D405/06C07D405/14A61P31/10
Inventor 帕撒·巴纳吉
Owner STIEFEL LABORATORIES
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