Title:
PROCESS AND INTERMEDIATES FOR PREPARING PHENYLTHIOMETHYL-THIAZOLES OR OXAZOLES
Document Type and Number:
WIPO Patent Application WO2003074504
Kind Code:
A3
Abstract:
A process for the preparation of a compound of formula (IV), wherein, one of Y and Z is N and the other is S or O; comprising the steps of; a) treating of a compound of formula (I) with an alkyl lithium reagent, magnesium (0), or magnesium (0) followed by treating with a dihalo zinc (II) reagent, X<1> is selected from the group consisting of CI, Br, and I; b) followed by treating with sulfur; and c) followed by treating with a compound of formula (III), R<11> is CI, Br, I or- OS(O)2R<12>.
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Inventors:
INGOLD KENNETH (US)
LIU BING (US)
LIU BING (US)
Application Number:
PCT/US2003/005723
Publication Date:
December 18, 2003
Filing Date:
February 25, 2003
Export Citation:
Assignee:
SMITHKLINE BEECHAM CORP (US)
INGOLD KENNETH (US)
LIU BING (US)
INGOLD KENNETH (US)
LIU BING (US)
International Classes:
A61K31/426; A61P3/06; A61P3/10; A61P43/00; C07D263/32; C07D277/24; C07D277/26; C07D413/02; C07D417/02; C07F1/02; C07F7/04; C07F7/18; C11D3/37; C11D17/00; (IPC1-7): C07D277/26; C07D263/32; C07D277/24; C07F7/18
Domestic Patent References:
| WO2001000603A1 | 2001-01-04 |
Other References:
BEBBINGTON D ET AL: "3,5-Disubstituted-4-hydroxyphenyls linked to 3-hydroxy-2-methyl-4(1H)-pyridinone: potent inhibitors of lipid peroxidation and cell toxicity", JOURNAL OF MEDICINAL CHEMISTRY, vol. 43, no. 15, 27 July 2000 (2000-07-27), pages 2779 - 2782, XP002243103
SATO R ET AL: "Efficient synthesis and biological properties of new benzopentathiepins", HETEROCYCLES, vol. 41, no. 5, 1 May 1995 (1995-05-01), pages 893 - 896, XP002243104
TERCIO J ET AL: "Synthesis of 2,2-dimethyl-2H-thiochromenes, the sulfur analogs of precocenes", SYNTHESIS, no. 2, February 1987 (1987-02-01), pages 149 - 153, XP002139430
ENGMAN L ET AL: "A general procedure for the synthesis of methylthio-, methylseleno- and methyltelluro- substituted aromatic compounds", JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 296, no. 3, 3 December 1985 (1985-12-03), pages 357 - 366, XP002243105
MALMSTRÖM J ET AL: "Novel antioxidants: unexpected rearrangements in the radical cyclization approach to 2,3-dihydrobenzo[b]thiophene-5-ol derivatives", JOURNAL OF ORGANIC CHEMISTRY, vol. 63, no. 10, 15 May 1998 (1998-05-15), pages 3318 - 3323, XP002243106
GAUTHIER J Y ET AL: "A remarkably simple conversion of nitriles to thioamides", PHOSPHORUS, SULFUR AND SILICON AND THE RELATED ELEMENTS, vol. 95/96, no. 1/4, 1994, pages 325 - 326, XP000654912
SATO R ET AL: "Efficient synthesis and biological properties of new benzopentathiepins", HETEROCYCLES, vol. 41, no. 5, 1 May 1995 (1995-05-01), pages 893 - 896, XP002243104
TERCIO J ET AL: "Synthesis of 2,2-dimethyl-2H-thiochromenes, the sulfur analogs of precocenes", SYNTHESIS, no. 2, February 1987 (1987-02-01), pages 149 - 153, XP002139430
ENGMAN L ET AL: "A general procedure for the synthesis of methylthio-, methylseleno- and methyltelluro- substituted aromatic compounds", JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 296, no. 3, 3 December 1985 (1985-12-03), pages 357 - 366, XP002243105
MALMSTRÖM J ET AL: "Novel antioxidants: unexpected rearrangements in the radical cyclization approach to 2,3-dihydrobenzo[b]thiophene-5-ol derivatives", JOURNAL OF ORGANIC CHEMISTRY, vol. 63, no. 10, 15 May 1998 (1998-05-15), pages 3318 - 3323, XP002243106
GAUTHIER J Y ET AL: "A remarkably simple conversion of nitriles to thioamides", PHOSPHORUS, SULFUR AND SILICON AND THE RELATED ELEMENTS, vol. 95/96, no. 1/4, 1994, pages 325 - 326, XP000654912
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