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Novel 16,17-ketal intermediate for preparing ciclesonide

A technology of ciclesonide and cyclohexyl, which is applied to the application field in the preparation of ciclesonide, and can solve problems such as difficulty and high content

Active Publication Date: 2014-06-11
TIANJIN JINYAO GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] (1) Calatayud (US5482934) reported the first route of triisobutyl esterification by tetrahydroxyl, it is difficult to obtain high content of 22 (R) optical body

Method used

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  • Novel 16,17-ketal intermediate for preparing ciclesonide
  • Novel 16,17-ketal intermediate for preparing ciclesonide
  • Novel 16,17-ketal intermediate for preparing ciclesonide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Add 10mmol of the compound of formula (I), 15ml of nitromethane, and 13mmol of cyclohexylformaldehyde into a three-necked flask, stir, add 30mmol of perchloric acid dropwise at -5 to 0°C, drop it in 2 hours, then stir overnight at 15°C, and find A large amount of solids were precipitated, filtered, and the filter cake was dissolved with N, N-dimethylformamide (DMF). Under ice bath refrigeration, 10% NaHCO3 aqueous solution was added dropwise to neutralize, then extracted with ethyl acetate, organic The phase was dried over sodium sulfate and concentrated under reduced pressure, recrystallized with methanol, suction filtered, washed with water, dried to constant weight to obtain 8.6 mmol of the compound of formula (Ⅲ), 22R:22S=95:5.

[0068] Elemental analysis: C, 70.95; H, 8.24; O, 20.81

Embodiment 2

[0070] Add 50ml of dichloromethane, 15mmol of p-toluenesulfonic acid, and 15mmol of cyclohexylformaldehyde into a three-necked flask, stir, slowly add 10mmol of the compound of formula (I) at room temperature within 1h, stir for 5h, add 10% NaHCO3 aqueous solution to adjust the pH value to 7, The layers were separated, the aqueous layer was washed with 5ml of chloroform X 3 times, the chloroform was combined, concentrated by rotary distillation, recrystallized from methanol, filtered with suction, washed with water, dried to constant weight to obtain 8.4 mmol of the compound of formula (III), 22R:22S=92:8. ,

Embodiment 3

[0072] Add 10mmol of the compound of formula (I), 20ml of acetonitrile, 20ml of dichloromethane, and 18mmol of hydrofluoric acid into a three-neck flask, stir, and slowly add 20mmol of cyclohexylformaldehyde dropwise at 25°C, and after stirring for 4 hours, adjust the pH value with 10% NaHCO3 aqueous solution To 7, add 20ml of water, let stand to separate the layers, extract the water layer three times with dichloromethane, 10ml each time, combine the dichloromethane and concentrate by rotary distillation, recrystallize with methanol, suction filter, dry to constant weight, and obtain the formula ( III) Compound 8.1 mmol, 22R:22S=93:7.

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PUM

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Abstract

The invention relates to a novel 16,17-ketal intermediate for preparing ciclesonide, which discloses a compound of formula (III), a method for synthesizing the compound of formula (III) from a compound of formula (I), and a method for synthesizing ciclesonide from the compound of formula (III).

Description

Technical field: [0001] The invention relates to a new pregnant compound and the application of the compound in preparing ciclesonide. Background technique: [0002] In March 2004, the new asthma drug ciclesonide (ciclesonide) of the German pharmaceutical manufacturer Altana was approved for marketing in Australia. Soon they were listed in the UK, Brazil, Mexico and other places. Ciclesonide, chemical name 16α,17α-22R-cyclohexylmethylene-11β,21-dihydroxy-1,4-pregnadiene-3,20-dione-21-isobutyrate, The molecular formula is C32H44O7. [0003] [0004] ciclesonide [0005] Ciclesonide is a new generation of inhaled non-halogenase glucocorticosteroid with high local anti-inflammatory ability. It is an ester prodrug with little oral bioavailability and is activated by cleavage by endogenous esterases. Advantages of "on-site-activation" include targeted activation in the lung and thus minimal systemic and pharyngeal side effects. [0006] In...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J71/00A61K31/58A61P29/00A61P37/08A61P17/00A61P17/06A61P17/04A61P11/06A61P11/00A61P11/02A61P27/02A61P1/04A61P19/02A61P37/00
Inventor 李静李金禄卢彦昌
Owner TIANJIN JINYAO GRP
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