Title:
NOVEL THIOPHENE COMPOUND AND PROCESS FOR PRODUCING CAFFENOFURAN OR ANALOGUE THEREOF FROM THE SAME
Document Type and Number:
WIPO Patent Application WO/2006/090716
Kind Code:
A1
Abstract:
A novel thiophene compound which is an intermediate useful for the efficient production of caffenofuran or an analogue thereof. Also provided is a process for producing caffenofuran or an analogue thereof via the novel thiophene compound as an intermediate. The novel thiophene compound is represented by the following formula (1): [wherein R1 represents hydrogen or C1-4 alkyl; R2 represents hydrogen or an alcohol-protecting group; and R3 represents hydrogen or a group represented by -COR4 or -C(OH)R5 (wherein R4 and R5 each represents C1-4 alkyl), provided that when R2 and R3 are hydrogen, then R1 is none of hydrogen, methyl, and n-propyl]. A thiophene compound represented by the following formula (2), among the compounds of the formula (1), is reduced and cyclized in the presence of a transition metal catalyst to produce caffenofuran or an analogue thereof (3a) as shown below. [Chemical formula 2] H2 (2) → (3) (In the formulae, R1 represents hydrogen or C1-4 alkyl; and R4 represents C1-4 alkyl.)
Inventors:
KATSUMURA SHIGEO (JP)
LI YANWU (JP)
IWABUCHI HISAKATSU (JP)
ONISHI MASANOBU (JP)
MURAKAMI YUSUKE (JP)
LI YANWU (JP)
IWABUCHI HISAKATSU (JP)
ONISHI MASANOBU (JP)
MURAKAMI YUSUKE (JP)
Application Number:
PCT/JP2006/303122
Publication Date:
August 31, 2006
Filing Date:
February 22, 2006
Export Citation:
Assignee:
SAN EI GEN FFI INC (JP)
KATSUMURA SHIGEO (JP)
LI YANWU (JP)
IWABUCHI HISAKATSU (JP)
ONISHI MASANOBU (JP)
MURAKAMI YUSUKE (JP)
KATSUMURA SHIGEO (JP)
LI YANWU (JP)
IWABUCHI HISAKATSU (JP)
ONISHI MASANOBU (JP)
MURAKAMI YUSUKE (JP)
International Classes:
A23L27/14; C07D333/16; A23L27/20; A61K8/49; A61Q13/00; C07D333/22; C07D495/04; C11B9/00
Domestic Patent References:
| WO2004031109A2 | 2004-04-15 |
Foreign References:
| JPS4814067B1 | 1973-05-02 | |||
| JP2003212867A | 2003-07-30 |
Other References:
SATO I. ET AL.: "1-Phenyl-2-(1-pyrrolidinyl)-1-propanol as a chiral catalyst for the highly enantioselective additon of dialkylzincs to five-membered heterocyclic aldehydes", HETEROCYCLES, vol. 51, no. 11, 1999, pages 2753 - 2758, XP002999687
HOLMES J.M. ET AL.: "Synthesis and Carbonic Anhydrase Inhibitory Activity of 4-Substituted 2-Thiophenesulfonamides", JOURNAL OF MEDICINAL CHEMISTRY, vol. 37, no. 11, 1994, pages 1646 - 1651, XP002999688
NUGARA P.N. ET AL.: "A convenient reduction of thienyl alcohols", SULFUR LETTERS, vol. 14, no. 6, 1992, pages 269 - 273, XP002999689
GRONOWITZ S. ET AL.: "Infrared absorption of heteroaromatic five-membered monocyclic nuclei. IV. 3-Monosubstituted thiophenes", JOURNAL OF THE CHEMICAL SOCIETY, 1963, pages 3881 - 3882, XP002999690
GORZYNSKI M. AND REWICKI D.: "Synthesis of alkyl-2,3-dihydrothieno[2,3-c]furans. Aromatic compounds of coffee", LIEBIGS ANNALEN DER CHEMIE, no. 4, 1986, pages 625 - 637, XP002999691
TRESSL R. AND SILWAR R.: "Investigation of sulfur-containing components in roasted coffee", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 29, no. 5, 1981, pages 1078 - 1082, XP002999692
LIARDON R. AND OTT U.: "Application of multivariate statistics for the classification of coffee headspace profiles", LEBENSMITTEL-WISSENSCHAFT UND -TECHNOLOGIE, vol. 17, no. 1, 1984, pages 32 - 38, XP002999693
HOLMES J.M. ET AL.: "Synthesis and Carbonic Anhydrase Inhibitory Activity of 4-Substituted 2-Thiophenesulfonamides", JOURNAL OF MEDICINAL CHEMISTRY, vol. 37, no. 11, 1994, pages 1646 - 1651, XP002999688
NUGARA P.N. ET AL.: "A convenient reduction of thienyl alcohols", SULFUR LETTERS, vol. 14, no. 6, 1992, pages 269 - 273, XP002999689
GRONOWITZ S. ET AL.: "Infrared absorption of heteroaromatic five-membered monocyclic nuclei. IV. 3-Monosubstituted thiophenes", JOURNAL OF THE CHEMICAL SOCIETY, 1963, pages 3881 - 3882, XP002999690
GORZYNSKI M. AND REWICKI D.: "Synthesis of alkyl-2,3-dihydrothieno[2,3-c]furans. Aromatic compounds of coffee", LIEBIGS ANNALEN DER CHEMIE, no. 4, 1986, pages 625 - 637, XP002999691
TRESSL R. AND SILWAR R.: "Investigation of sulfur-containing components in roasted coffee", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 29, no. 5, 1981, pages 1078 - 1082, XP002999692
LIARDON R. AND OTT U.: "Application of multivariate statistics for the classification of coffee headspace profiles", LEBENSMITTEL-WISSENSCHAFT UND -TECHNOLOGIE, vol. 17, no. 1, 1984, pages 32 - 38, XP002999693
Attorney, Agent or Firm:
Saegusa, Eiji (Doshomachi Chuo-k, Osaka-shi Osaka 45, JP)
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