Title:
PROCESS FOR PRODUCING 2'-DEOXY-2'-FLUOROURIDINE
Document Type and Number:
WIPO Patent Application WO/2004/089968
Kind Code:
A1
Abstract:
1-ß-D-Arabinofuranosyluracil in a 3',5'-hydroxy-protected form is reacted with a trifluoromethanesulfonylating agent in the presence of an organic base to convert it into a 2'-triflate form, and this compound is reacted with a fluorinating agent comprising 'a salt or complex comprising an organic base and hydrofluoric acid' to produce 2'-deoxy-2'-fluorouridine in a 3',5'-hydroxy-protected form. An agent for eliminating the protective groups is further caused to act on the protected compound to obtain 2'-deoxy-2'-fluorouridine. The 2'-deoxy-2'-fluorouridine obtained can be efficiently purified by temporarily converting it into a 3',5'-diacetyl form, recrystallizing the 3',5'-diacetyl form, and then deacetylating it. Thus, high-purity 2'-deoxy-2'-fluorouridine can be produced.
Inventors:
ISHI AKIHIRO (JP)
OOTSUKA TAKASHI (JP)
KANAI MASATOMI (JP)
KURIYAMA YOKUSU (JP)
YASUMOTO MANABU (JP)
INOMIYA KENJIN (JP)
UEDA KOJI (JP)
OOTSUKA TAKASHI (JP)
KANAI MASATOMI (JP)
KURIYAMA YOKUSU (JP)
YASUMOTO MANABU (JP)
INOMIYA KENJIN (JP)
UEDA KOJI (JP)
Application Number:
PCT/JP2004/005109
Publication Date:
October 21, 2004
Filing Date:
April 09, 2004
Export Citation:
Assignee:
CENTRAL GLASS CO LTD (JP)
ISHI AKIHIRO (JP)
OOTSUKA TAKASHI (JP)
KANAI MASATOMI (JP)
KURIYAMA YOKUSU (JP)
YASUMOTO MANABU (JP)
INOMIYA KENJIN (JP)
UEDA KOJI (JP)
ISHI AKIHIRO (JP)
OOTSUKA TAKASHI (JP)
KANAI MASATOMI (JP)
KURIYAMA YOKUSU (JP)
YASUMOTO MANABU (JP)
INOMIYA KENJIN (JP)
UEDA KOJI (JP)
International Classes:
C07H19/067; (IPC1-7): C07H19/067
Foreign References:
| JPH01272595A | 1989-10-31 | |||
| JPS57102889A | 1982-06-26 |
Other References:
SATO Y. ET AL: "Synthesis and Hypnotic and Anti-Human Immunodeficiency Virus-1 Activities of N3-Substituted 2'-Deoxy-2'-fluorourdines", CHEM. PHARM. BULL., vol. 42, no. 3, 1994, pages 595 - 598, XP002980856
IKEHARA M. ET AL: "Sudies on Nucleosides and Nucleotides. LXXXIX. Purine Cyclonucleosides. (43) Synthesis and Properties of 2'-Halogeno-2'-deoxyguanosines", CHEM. PHARM. BULL., vol. 29, no. 11, 1981, pages 3281 - 3285, XP002980857
IKEHARA M. ET AL: "Studies on Nucleosides and Nucleotides. LXXXVII. Purine Cyclonucleosides. XLII. Synthesis of 2'-deoxy-2'-fluoroguanosine", CHEM. PHARM. BULL., vol. 29, no. 4, 1981, pages 1034 - 1038, XP002030866
IKEHARA M. ET AL: "Sudies on Nucleosides and Nucleotides. LXXXIX. Purine Cyclonucleosides. (43) Synthesis and Properties of 2'-Halogeno-2'-deoxyguanosines", CHEM. PHARM. BULL., vol. 29, no. 11, 1981, pages 3281 - 3285, XP002980857
IKEHARA M. ET AL: "Studies on Nucleosides and Nucleotides. LXXXVII. Purine Cyclonucleosides. XLII. Synthesis of 2'-deoxy-2'-fluoroguanosine", CHEM. PHARM. BULL., vol. 29, no. 4, 1981, pages 1034 - 1038, XP002030866
Attorney, Agent or Firm:
Hashimoto, Takeshi c/o Shiga, Patent Office Ekisaikai Bldg (1-29 Akashi-cho, Chuo-k, Tokyo 44, JP)
Download PDF: