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Title:
NOVEL 2’,5’-OLIGOADENYLIC ACID ANALOGUES
Document Type and Number:
WIPO Patent Application WO/2004/046161
Kind Code:
A1
Abstract:
2-5A Analogues represented by the general formula (1) and pharmacologically acceptable salts thereof: (1) wherein m is 0 or 1; n is 0 to 2; R1 is optionally substituted C1-6 alkoxy, mercapto, mercapto blocked with a protecting group for synthesis of nucleic acid, or optionally substituted C1-4 alkylthio; R2, R3, R4, R5 and R6 are each hydroxyl, hydroxyl blocked with a protecting group for synthesis of nucleic acid, optionally substituted C1-6 alkoxy, mercapto, mercapto blocked with a protecting group for synthesis of nucleic acid, or optionally substituted C1-4 alkylthio; R7 is oxygen or -O(CH2CH2O)q- (wherein q is 2 to 6); R8 is hydrogen, optionally substituted C1-6 alkyl, or a 5’-phosphorylated oligonucleotide analogue lacking one hydroxyl group on the 5’-phosphate group; and E1, E2, E3 and E4 are each a natural or modified nucleic acid unit.

Inventors:
KOIZUMI MAKOTO (JP)
MORITA KOJI (JP)
Application Number:
PCT/JP2003/014748
Publication Date:
June 03, 2004
Filing Date:
November 19, 2003
Export Citation:
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Assignee:
SANKYO CO (JP)
KOIZUMI MAKOTO (JP)
MORITA KOJI (JP)
International Classes:
A61P31/12; A61P35/00; A61P43/00; C07H21/00; C12N15/113; (IPC1-7): C07H21/00; A61K31/7125; A61K48/00; A61P31/12; A61P35/00; A61P43/00
Domestic Patent References:
WO2001022970A12001-04-05
WO1989012380A21989-12-28
Foreign References:
JP2002249497A2002-09-06
EP1013661A12000-06-28
EP1152009A12001-11-07
Other References:
MASAMITU SHIMAZU, ET AL: "REGIO- AND STEREOCONTROLLED SYNTHESIS OF 2'-5' LINKED PHOSPHOROTHIOATE OLIGOADENYLATES BY URANYL ION CATALYST IN AQUEOUS SOLUTION", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1, no. 15, 7 August 2002 (2002-08-07), pages 1778 - 1785, XP002976428
SHARON NAIK, ET AL: "RNASE L DIMERIZATION IN A MAMMALIAN TWO-HYBRID SYSTEM IN RESPONSE TO 2', 5'-OLIGOADENYLATES", NUCLEIC ACIDS RESEARCH, vol. 26, no. 6, 1998, pages 1522 - 1527, XP002976429
WEI XIAO, ET AL: "SYNTHESIS OF A 5'-THIOPHOSPHATE ANALOGUE OF 2-5A, A PHOSPHATASE RESISTANT ACTIVATOR OF THE 2-5A-DEPENDENT RIBONUCLEASE", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 4, no. 21, 1994, pages 2609 - 2614, XP002976430
D WATLING, ET AL: "ANALOGUE INHIBITOR OF 2-5A ACTION: EFFECT ON THE INTERFERON-MEDIATED INHIBITION OF ENCEPHALOMYOCARDITIS VIRUS REPLICATION", THE EMBO JOURNAL, vol. 4, no. 2, 1985, pages 431 - 436, XP002976431
PAUL F TORRENCE, ET AL: "OLIGONUCLEOTIDE STRUCTURAL PARAMETERS THAT INFLUENCE BINDING OF 5'-0-TRIPHOSPHOADENYLYL-(2'- 5')-ADENYLYL-(2'- 5')-ADENOSINE TO THE 5'-0-TRIPHOSPHOADENYLYL-(2'-5')-ADENYLYL-(2'- 5')-ADENOSINE DEPENDENT ENDORIBONUCLEASE: CHAIN LENGTH, PHOSPHORYLATION STATE, AND HETEROCYCLIC BASE", JOURNAL OF MEDICINAL CHEMISTRY, vol. 27, no. 6, 1984, pages 726 - 733, XP009003873
MARGARET C HAUGH, ET AL: "ANALOGUES AND ANALOGUE INHIBITORS OF PPP(A2'P)NA. THEIR STABILITY AND BIOLOGICAL ACTIVITY", EUROPEAN JOURNAL OF BIOCHEMISTRY, vol. 132, no. 1, 1983, pages 77 - 84, XP000602615
SIMON S JONES, ET AL: "CHEMICAL SYNTHESIS OF 5'-0-TRIPHOSPHORYLADENYLYL-(2'- 5')-ADENYLYL-(2'- 5')-ADENOSINE (2-5A)", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 101, no. 2, 1979, pages 7399 - 7401, XP002976432
YING XIANG, ET AL: "EFFECTS OF RNASE L MUTATIONS ASSOCIATED WITH PROSTATE CANCER ON APOPTOSIS INDUCED BY 2', 5'-OLIGOADENYLATES", CANCER RESEARCH, vol. 63, no. 20, 15 October 2003 (2003-10-15), pages 6795 - 6801, XP002976433
YOSHIHITO UENO, ET AL: "SYNTHESIS OF THE ANTISENSE OLIGONUCLEOTIDES CARRYING THE MODIFIED 2-5A MOLECULES AT THEIR 5'-TERMINI AND THEIR PROPERTIES", NUCLEIC ACIDS RESEARCH SUPPLEMENT, no. 2, November 2002 (2002-11-01), pages 45 - 46, XP002976434
See also references of EP 1568704A4
Attorney, Agent or Firm:
Ohno, Akio c/o SANKYO COMPANY (LIMITED 2-58, Hiromachi 1-chom, Shinagawa-ku Tokyo, JP)
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