Title:
PROCESS AND INTERMEDIATE COMPOUNDS USEFUL IN THE PREPARATION OF STATINS, PARTICULARLY ROSUVASTATIN
Document Type and Number:
WIPO Patent Application WO2005092867
Kind Code:
A3
Abstract:
There is provided a process for the preparation of a compound of formula (7) wherein R<1> represents an alkyl group; R<2> represents an aryl group; R<3> represents hydrogen, a protecting group or an alkyl group; and R<4> represents hydrogen, a protecting group or a SO2R<5> group where R<5> is an alkyl group, which comprises a) hydroxylating a compound of formula (1) wherein Y represents a halo group; P<1> represents hydrogen or a protecting group, and W represents =O or -OP<2>, in which P<2> represents hydrogen or a protecting group, to give a compound of formula (2), b) oxidising the compound of formula (2) to give a compound of formula (3), c) coupling the compound of formula (3) with a compound of formula (4), wherein R<3> represents a protecting group or an alkyl group; R<4> represents a protecting group or a SO2R<5> group where R<5> is an alkyl group; and R<6> represents (PR<7>R<8>)<+>X<-> or P(=O)R<7>R<8> in which X is an anion and R<7> and R<8> each independently is an alkyl, aryl.
Inventors:
MOODY DAVID JOHN (GB)
WIFFEN JONATHAN WILLIAM (GB)
WIFFEN JONATHAN WILLIAM (GB)
Application Number:
PCT/GB2005/001099
Publication Date:
November 10, 2005
Filing Date:
March 23, 2005
Export Citation:
Assignee:
AVECIA PHARMACEUTICALS LTD (GB)
MOODY DAVID JOHN (GB)
WIFFEN JONATHAN WILLIAM (GB)
MOODY DAVID JOHN (GB)
WIFFEN JONATHAN WILLIAM (GB)
International Classes:
C07D309/10; C07D309/30; C07D405/06; (IPC1-7): A61K31/505; C07D405/06; C07D309/10; C07D309/30
Domestic Patent References:
| WO2001085702A1 | 2001-11-15 | |||
| WO2005047276A2 | 2005-05-26 | |||
| WO2005040134A1 | 2005-05-06 | |||
| WO2005030758A1 | 2005-04-07 |
Foreign References:
| US20030232989A1 | 2003-12-18 | |||
| US4677211A | 1987-06-30 | |||
| US4625039A | 1986-11-25 | |||
| US4474971A | 1984-10-02 |
Other References:
BARTH M ET AL: "TOWARDS A NEW TYPE OF HMG-COA REDUCTASE INHIBITOR", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 46, no. 19, 1990, pages 6731 - 6740, XP000942264, ISSN: 0040-4020
DURAND-REVILLE, THOMAS ET AL: "Highly Selective Entry to the Azadirachtin Skeleton via a Claisen Rearrangement/Radical Cyclization Sequence", ORGANIC LETTERS , 4(22), 3847-3850 CODEN: ORLEF7; ISSN: 1523-7060, 2002, XP002343425
YANG, YUH LIN ET AL: "Mevinic acids and analogs: preparation of a key chiral intermediate", TETRAHEDRON LETTERS , 23(42), 4305-8 CODEN: TELEAY; ISSN: 0040-4039, 1982, XP002343426
ROSEN T ET AL: "SYNTHETIC AND BIOLOGICAL STUDIES OF COMPACTIN AND RELATED COMPOUNDSSYNTHESIS OF THE LACTONE MOIETY OF COMPACTIN", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 49, 19 October 1994 (1994-10-19), pages 3994 - 4003, XP000996454, ISSN: 0022-3263
BECK G ET AL: "Synthesis and Biological Activity of New HMG-CoA Reductase Inhibitors. 1. Lactones of Pyridine- and Pyrimidine-Substituted 3,5-Dihydroxy-6-heptenoic (-heptanoic) Acids", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, US, vol. 33, no. 1, 1990, pages 52 - 60, XP002324910, ISSN: 0022-2623
PATERSON, IAN ET AL: "Phorboxazole B synthetic studies: construction of C(1-32) and C(33-46) subtargets", ORGANIC & BIOMOLECULAR CHEMISTRY , 2(20), 3026-3038 CODEN: OBCRAK; ISSN: 1477-0520, 2004, XP002343427
DURAND-REVILLE, THOMAS ET AL: "Highly Selective Entry to the Azadirachtin Skeleton via a Claisen Rearrangement/Radical Cyclization Sequence", ORGANIC LETTERS , 4(22), 3847-3850 CODEN: ORLEF7; ISSN: 1523-7060, 2002, XP002343425
YANG, YUH LIN ET AL: "Mevinic acids and analogs: preparation of a key chiral intermediate", TETRAHEDRON LETTERS , 23(42), 4305-8 CODEN: TELEAY; ISSN: 0040-4039, 1982, XP002343426
ROSEN T ET AL: "SYNTHETIC AND BIOLOGICAL STUDIES OF COMPACTIN AND RELATED COMPOUNDSSYNTHESIS OF THE LACTONE MOIETY OF COMPACTIN", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 49, 19 October 1994 (1994-10-19), pages 3994 - 4003, XP000996454, ISSN: 0022-3263
BECK G ET AL: "Synthesis and Biological Activity of New HMG-CoA Reductase Inhibitors. 1. Lactones of Pyridine- and Pyrimidine-Substituted 3,5-Dihydroxy-6-heptenoic (-heptanoic) Acids", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, US, vol. 33, no. 1, 1990, pages 52 - 60, XP002324910, ISSN: 0022-2623
PATERSON, IAN ET AL: "Phorboxazole B synthetic studies: construction of C(1-32) and C(33-46) subtargets", ORGANIC & BIOMOLECULAR CHEMISTRY , 2(20), 3026-3038 CODEN: OBCRAK; ISSN: 1477-0520, 2004, XP002343427
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