Title:
PROCESS FOR PRODUCING (5&agr ,7&agr )-3-SPIRO-2'-(1',3'-DIOXOLAN) -24-OXOCHOLEST-22-EN-7-YL BENZOATE
Document Type and Number:
WIPO Patent Application WO/2006/062129
Kind Code:
A1
Abstract:
A process for producing (5&agr ,7&agr )-3-spiro-2'-(1',3'-dioxolan)-24-oxocholest-22-en-7-yl benzoate (unsaturated ketone (I)), which is represented by the formula (I), (I) characterized by dissolving in methanol a crude reaction product which contains the unsaturated ketone (I) and has been obtained in a reaction step, the amount by mass of the methanol being 1.5-3 times the amount by mass of the unsaturated ketone (I) contained, to obtain a solution, adding the solution to water, the amount by mass of the water being 5-30 times the amount by mass of the unsaturated ketone (I) contained, to thereby obtain a suspension containing the unsaturated ketone (I) which has been solidified, separating the solid from the suspension, and drying the solid obtained. The unsaturated ketone (I) obtained is useful as an intermediate for squalamine, which has potent antibacterial activity and anticancer activity.
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Inventors:
KOYAKUMARU KENICHI (JP)
UJITA KATSUJI (JP)
UJITA KATSUJI (JP)
Application Number:
PCT/JP2005/022457
Publication Date:
June 15, 2006
Filing Date:
December 07, 2005
Export Citation:
Assignee:
KURARAY CO (JP)
KOYAKUMARU KENICHI (JP)
UJITA KATSUJI (JP)
KOYAKUMARU KENICHI (JP)
UJITA KATSUJI (JP)
International Classes:
C07J21/00
Domestic Patent References:
| WO2003011228A2 | 2003-02-13 |
Foreign References:
| JP2001505207A | 2001-04-17 | |||
| JP2003512892A | 2003-04-08 |
Other References:
JONES S.R. ET AL.: "Efficient Route to 7alpha-(Benzoyloxy) -3-dioxolane Cholestan-24(R)-ol, a Key Intermediate in the Synthesis of Squalamine", J. ORG. CHEM., vol. 63, no. 11, 1998, pages 3786 - 3789, XP002269175
KITAMURA M. ET AL.: "Anti-solvent crystallization and transformation of thiazole-derivative Polymorphs- I: effect of addition rate and initial concentrations", J. CRYST. GROWTH, vol. 257, 2003, pages 177 - 184, XP004450900
BORISSOVA A. ET AL.: "Examination of the Semi-Batch Crystallization of Benzophene from Saturated Methanol Solution via Aqueous Antisolvent Drowing-Out as Monitored In-Process Using ATR FTIR Spectroscopy", CRYST. GROWTH DES., vol. 4, no. 5, 2004, pages 1053 - 1060, XP002996569
See also references of EP 1837343A4
KITAMURA M. ET AL.: "Anti-solvent crystallization and transformation of thiazole-derivative Polymorphs- I: effect of addition rate and initial concentrations", J. CRYST. GROWTH, vol. 257, 2003, pages 177 - 184, XP004450900
BORISSOVA A. ET AL.: "Examination of the Semi-Batch Crystallization of Benzophene from Saturated Methanol Solution via Aqueous Antisolvent Drowing-Out as Monitored In-Process Using ATR FTIR Spectroscopy", CRYST. GROWTH DES., vol. 4, no. 5, 2004, pages 1053 - 1060, XP002996569
See also references of EP 1837343A4
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