WO1999029702A3 - METHOD FOR SYNTHESIZING 9-(2,3-DIDEOXY-2-FLUORO-β-D-THREO-PENTOFURANOSYL)ADENINE (β-FddA) - Google Patents

METHOD FOR SYNTHESIZING 9-(2,3-DIDEOXY-2-FLUORO-β-D-THREO-PENTOFURANOSYL)ADENINE (β-FddA) Download PDF

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Publication number
WO1999029702A3
WO1999029702A3 PCT/US1998/026109 US9826109W WO9929702A3 WO 1999029702 A3 WO1999029702 A3 WO 1999029702A3 US 9826109 W US9826109 W US 9826109W WO 9929702 A3 WO9929702 A3 WO 9929702A3
Authority
WO
WIPO (PCT)
Prior art keywords
dideoxy
fluoro
pentofuranosyl
threo
adenine
Prior art date
Application number
PCT/US1998/026109
Other languages
French (fr)
Other versions
WO1999029702A2 (en
Inventor
Victor E Marquez
Maqbool A Siddiqui
John S Driscoll
Original Assignee
Us Health
Victor E Marquez
Maqbool A Siddiqui
John S Driscoll
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Us Health, Victor E Marquez, Maqbool A Siddiqui, John S Driscoll filed Critical Us Health
Priority to AU18103/99A priority Critical patent/AU1810399A/en
Publication of WO1999029702A2 publication Critical patent/WO1999029702A2/en
Publication of WO1999029702A3 publication Critical patent/WO1999029702A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/16—Purine radicals

Abstract

A new method for the preparation of the anti-HIV antiviral compound 9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)adenine (β-FddA) is provided. The method relies upon the stereospecific hydrogenation of 9-[2,3-dideoxy-2-fluoro-β-D-glycero-pent-2-enofuranosyl]adenine or various derivatives thereof. The methods are expected to be suitable for the preparation of other antiviral 9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)purines, such as β-FddG and β-FddI.
PCT/US1998/026109 1997-12-10 1998-12-09 METHOD FOR SYNTHESIZING 9-(2,3-DIDEOXY-2-FLUORO-β-D-THREO-PENTOFURANOSYL)ADENINE (β-FddA) WO1999029702A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU18103/99A AU1810399A (en) 1997-12-10 1998-12-09 Method for synthesizing

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US6776597P 1997-12-10 1997-12-10
US60/067,765 1997-12-10

Publications (2)

Publication Number Publication Date
WO1999029702A2 WO1999029702A2 (en) 1999-06-17
WO1999029702A3 true WO1999029702A3 (en) 1999-09-02

Family

ID=22078266

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1998/026109 WO1999029702A2 (en) 1997-12-10 1998-12-09 METHOD FOR SYNTHESIZING 9-(2,3-DIDEOXY-2-FLUORO-β-D-THREO-PENTOFURANOSYL)ADENINE (β-FddA)

Country Status (2)

Country Link
AU (1) AU1810399A (en)
WO (1) WO1999029702A2 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9579332B2 (en) 2004-07-27 2017-02-28 Gilead Sciences, Inc. Phosphonate analogs of HIV inhibitor compounds

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SG182849A1 (en) 2003-04-25 2012-08-30 Gilead Sciences Inc Antiviral phosphonate analogs
CN100334101C (en) * 2004-01-17 2007-08-29 杭州富邦生物制药有限公司 Method for synthesizing 2',3'-dideoxy cytidine
BRPI0915878A2 (en) 2008-07-08 2015-11-03 Gilead Sciences Inc salts or hydrates of HIV-inhibiting compounds, their use and pharmaceutical composition comprising them
US8975394B2 (en) 2010-02-15 2015-03-10 Nissan Chemical Industries, Ltd. Process for preparation of β-glycoside compounds
CN102741237B (en) * 2010-02-15 2015-04-29 日产化学工业株式会社 Method for producing beta-dihydrofuran deriving compound
EP3661937B1 (en) 2017-08-01 2021-07-28 Gilead Sciences, Inc. Crystalline forms of ethyl ((s)-((((2r,5r)-5-(6-amino-9h-purin-9-yl)-4-fluoro-2,5-dihydrofuran-2-yl)oxy)methyl)(phenoxy)phosphoryl)-l-alaninate (gs-9131) for treating viral infections

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
CHEN S H ET AL: "Synthesis and biological evaluation of a series of 2'-fluorinated-2',3'-dideoxy-2',3'-didehydro-(L)-nucleosides", BIOORG. MED. CHEM. LETT. (BMCLE8,0960894X);1998; VOL.8 (13); PP.1589-1594, Vion Pharmaceuticals, Inc., Four Science Park;New Haven; 06511; CT; USA (US), XP004137090 *
CHOI Y ET AL: "Synthesis and anti-HIV activity of L-2'-fluoro-2',3'-unsaturated purine nucleosides", TETRAHEDRON LETT. (TELEAY,00404039);1998; VOL.39 (25); PP.4437-4440, Univ. Georgia;Center for Drug Discovery, Dep. Pharmaceutical and Biomedical Sciences, Coll. Pharmacy; Athens; 30602; GA; USA (US), XP004120707 *
K.W.PANKIEWICZ ET AL.: "A Synthesis of 9-(2-Deoxy-2-fluoro-B-D-arabinofuranosyl)adenine and Hypoxanthine.", JOURNAL OF ORGANIC CHEMISTRY., vol. 57, 1992, EASTON US, pages 553 - 559, XP002107309 *
K.X.PANKIWICZ ET AL.: "Synthesis of 2'-B-Fluoro and 3'-a-Fluoro-Substituted Guanine Nucleosides. Effetcs of Sugar Conformational Shifts of Nucleophilic Displacement of the 2'-Hydroxy and 3'-Hydroxy Group with DAST.", JOURNAL OF ORGANIC CHEMISTRY., vol. 57, 1992, EASTON US, pages 7315 - 7321, XP002107308 *
R.Z.STERZYCKI ET AL.: "Synthesis and Anti-HIV Activity of Several 2'-Fluoro-Containing Pyrimidine Nucleosides.", JOURNAL OF MEDICINAL CHEMISTRY., vol. 33, 1990, WASHINGTON US, pages 2150 - 2157, XP002107310 *
SIDDIQUI M A ET AL: "A new synthetic approach to the clinically useful, anti-HIV-active nucleoside, 9-(2,3-dideoxy-2-fluoro-.beta.-D-threo-pentofuranosyl)ad enine (.beta.-FddA). Introduction of a 2'-.beta.-fluoro substituent via inversion of a readily obtainable 2'-.alpha.-fluoro isomer.", TETRAHEDRON LETT. (TELEAY,00404039);1998; VOL.39 (13); PP.1657-1660, National Institutes of Health;Laboratory of Medicinal Chemistry, Division of Basic Sciences, National Cancer Institute; Bethesda; 20892; MD; USA (US), XP004108441 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9579332B2 (en) 2004-07-27 2017-02-28 Gilead Sciences, Inc. Phosphonate analogs of HIV inhibitor compounds

Also Published As

Publication number Publication date
AU1810399A (en) 1999-06-28
WO1999029702A2 (en) 1999-06-17

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