Title:
PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE COMPOUND
Document Type and Number:
WIPO Patent Application WO/2010/013510
Kind Code:
A1
Abstract:
A 2-aryl-2-halomethyl-4-chloromethyl-1,3-dioxolane (A) can be produced conveniently without decreasing its optical purity by reacting an optically active monochlorohydrin and an aryl (halomethyl) ketone (starting materials) with each other in the presence of an acid catalyst. From the optically active compound (A) thus produced, an optically active carboxylic acid (2-aryl-2-halomethyl-1,3-dioxolan-4-yl) methyl ester and an optically active sulfonic acid (2-aryl-2-halomethyl-1,3-dioxolan-4-yl) methyl ester (both of which are useful intermediates for the production of ketoconazole) can be produced with good efficiency. An optically active trans-carboxylic acid (2-aryl-2-halomethyl-1,3-dioxolan-4-yl) methyl ester can be isomerized into its cis-form in the presence of an acid catalyst.
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Inventors:
ISHII YUTAKA (JP)
IWASHINA SHINGO (JP)
KAWASE TAKAHIRO (JP)
HORI YUMIKO (JP)
IWASHINA SHINGO (JP)
KAWASE TAKAHIRO (JP)
HORI YUMIKO (JP)
Application Number:
PCT/JP2009/055714
Publication Date:
February 04, 2010
Filing Date:
March 23, 2009
Export Citation:
Assignee:
DAISO CO LTD (JP)
ISHII YUTAKA (JP)
IWASHINA SHINGO (JP)
KAWASE TAKAHIRO (JP)
HORI YUMIKO (JP)
ISHII YUTAKA (JP)
IWASHINA SHINGO (JP)
KAWASE TAKAHIRO (JP)
HORI YUMIKO (JP)
International Classes:
C07D317/16; C07D317/18; C07D409/04
Domestic Patent References:
| WO1996029325A1 | 1996-09-26 |
Foreign References:
| JP2002535328A | 2002-10-22 |
Other References:
CISZEWNSKI, L.: "Effect of reaction conditions on the nucleophilic substitution of R, S, cis- trans-trisubstituted 1, 3-dioxolane", POLISH JOURNAL OF CHEMISTRY, vol. 62, no. 1/3, 1988, pages 179 - 186, XP009151452
WOLINSKI, J. ET AL.: "Search for anticholinergic agents", ACTA POLON. PHARM., vol. 33, no. 6, 1976, pages 695 - 700, XP008144108
ISAO TAKEUCHI ET AL.: "cis-l-[2-Phenyl-4- (phenoxy or Phenylthio)methyl-1, 3- dioxolan-2- ylmethyl]-1H-imidazole Yudotai no Gosei to Sono Kokin Sayo ni Tsuite", JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAP, vol. 105, no. 6, 1985, pages 554 - 561, XP008144086
ROTSTEIN, D.M. ET AL.: "Stereoisomers of Ketoconazole: Preparation and Biological Activity", J. MED. CHEM., vol. 35, no. 15, 1992, pages 2818 - 2825, XP002003770
ROTSTEIN, D.M. ET AL., JOURNAL OF MEDICINAL CHEMISTRY, vol. 35, 1992, pages 2818 - 2825
CAMPS, P. ET AL., TETRAHEDRON ASYMMETRY, vol. 6, 1995, pages 1283 - 1294
JACOBSEN, E.N., SCIENCE, vol. 277, 1997, pages 936 - 938
BAUER, L. ET AL., J. HETEROCYCL. CHEM., vol. 27, 1990, pages 2053 - 2061
See also references of EP 2325178A4
WOLINSKI, J. ET AL.: "Search for anticholinergic agents", ACTA POLON. PHARM., vol. 33, no. 6, 1976, pages 695 - 700, XP008144108
ISAO TAKEUCHI ET AL.: "cis-l-[2-Phenyl-4- (phenoxy or Phenylthio)methyl-1, 3- dioxolan-2- ylmethyl]-1H-imidazole Yudotai no Gosei to Sono Kokin Sayo ni Tsuite", JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAP, vol. 105, no. 6, 1985, pages 554 - 561, XP008144086
ROTSTEIN, D.M. ET AL.: "Stereoisomers of Ketoconazole: Preparation and Biological Activity", J. MED. CHEM., vol. 35, no. 15, 1992, pages 2818 - 2825, XP002003770
ROTSTEIN, D.M. ET AL., JOURNAL OF MEDICINAL CHEMISTRY, vol. 35, 1992, pages 2818 - 2825
CAMPS, P. ET AL., TETRAHEDRON ASYMMETRY, vol. 6, 1995, pages 1283 - 1294
JACOBSEN, E.N., SCIENCE, vol. 277, 1997, pages 936 - 938
BAUER, L. ET AL., J. HETEROCYCL. CHEM., vol. 27, 1990, pages 2053 - 2061
See also references of EP 2325178A4
Attorney, Agent or Firm:
TAKASHIMA, HAJIME (JP)
Takashima 1 (JP)
Takashima 1 (JP)
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