3-HYDROXY-3-(2-THIENYL)PROPIONAMIDE COMPOUND, PROCESS FOR PRODUCING THE SAME, AND PROCESS FOR PRODUCING 3-AMINO-1-(2-THIENYL)-1-PROPANOL COMPOUND THEREFROM

Title:

3-HYDROXY-3-(2-THIENYL)PROPIONAMIDE COMPOUND, PROCESS FOR PRODUCING THE SAME, AND PROCESS FOR PRODUCING 3-AMINO-1-(2-THIENYL)-1-PROPANOL COMPOUND THEREFROM

Document Type and Number:

WIPO Patent Application WO/2003/078418

Kind Code:

A1

Abstract:

A 3-hydroxy-3-(2-thienyl)propionamide compound represented by the following general formula (1), which is useful as an intermediate for medicines, etc.; and a process for industrially producing at low cost an optically active 3-amino-1-(2-thienyl)-1-propanol compound from the propionamide compound in a high reaction yield and high optical yield. The process comprises subjecting a ß-ketocarbonyl compound having a thiophene ring to asymmetric reduction either in the presence of a catalyst comprising a compound of a Group 8 or 9 metal of the Periodic Table (e.g., ruthenium compound) and an asymmetric ligand represented by a specific optically active diamine derivative (e.g., diphenylethylenediamine derivative) or using cells of a microorganism, a product of treatment of the cells, etc. According to need, the product of the asymmetric reduction is subjected to ester group amidation and then amide group reduction. Thus, a 3-amino-1-(2-thienyl)-1-propanol compound is obtained.

Inventors:

TAKEHARA JUN (JP)
QU JINGPING (JP)
KANNO KAZUAKI (JP)
KAWABATA HIROSHI (JP)
DEKISHIMA YASUMASA (JP)
UEDA MAKOTO (JP)
ENDO KYOKO (JP)
MURAKAMI TAKESHI (JP)
SASAKI TOMOKO (JP)
UEHARA HISATOSHI (JP)
MATSUMOTO YOUICHI (JP)
SUZUKI SHIHOMI (JP)

Application Number:

PCT/JP2003/003170

Publication Date:

September 25, 2003

Filing Date:

March 17, 2003

Export Citation:

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Assignee:

MITSUBISHI CHEM CORP (JP)
TAKEHARA JUN (JP)
QU JINGPING (JP)
KANNO KAZUAKI (JP)
KAWABATA HIROSHI (JP)
DEKISHIMA YASUMASA (JP)
UEDA MAKOTO (JP)
ENDO KYOKO (JP)
MURAKAMI TAKESHI (JP)
SASAKI TOMOKO (JP)
UEHARA HISATOSHI (JP)
MATSUMOTO YOUICHI (JP)
SUZUKI SHIHOMI (JP)

International Classes:

B01J31/18; C07D333/20; C07D333/24; C12P7/04; C12P17/00; (IPC1-7): C07D333/24; B01J31/18; C07B53/00; C07D333/20; C12P17/00

Domestic Patent References:

WO1991016889A1

1991-11-14

Foreign References:

EP0650965A1	1995-05-03
EP0457559A2	1991-11-21
EP0273658A1	1988-07-06
EP0571685A1	1993-12-01
EP0562343A1	1993-09-29
JPS59163382A	1984-09-14
JPS6363398A	1988-03-19
JP2001058999A	2001-03-06
JP2001199928A	2001-07-24
US20020187961A1	2002-12-12

Other References:

AKITA,H, MATSUKURA H, OISHI T.: "Lipase catalyzed enantioselective hydrolysis of 2-methyl 3-acetoxy esters.", TETRAHEDRON LETT., vol. 27, no. 43, 1986, pages 5241 - 5244, XP002968890
FURUICHI,A ET AL.: "The Use of Microorganisms in Oraganic Synthesis. V. Microbiological Asymetric Reduction of Methyl 2-Methyl-3-(2-thienyl)-3-oxopropionate.", CHEM. PHARM. BULL., vol. 32, no. 4, 1984, pages 1619 - 1623, XP002968891
GENET JP ET AL, TETRAHEDRON LETTERS, vol. 36, no. 27, 1995, pages 4801 - 4804, XP004027772
MADEC J ET AL, TETRAHEDRON, vol. 57, no. 13, 2001, pages 2563 - 2568, XP004232215
GUERREIRO P ET AL, C.R. ACAD. SCI. PARIS, T.2, SERIE IIC, vol. 2, no. 3, 1999, pages 175 - 179, XP001106883
See also references of EP 1486493A4

Attorney, Agent or Firm:

Oguri, Shohei (28th Floor ARK Mori Building, 12-32, Akasaka 1-chom, Minato-ku Tokyo, JP)

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