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Title:
PROCESS AND INTERMEDIATES FOR THE PREPARATION OF ISOXAZOLECAROXAMIDES AND ANALOGUES
Document Type and Number:
WIPO Patent Application WO2001014576
Kind Code:
A3
Abstract:
Efficient synthetic routes for the preparation of rhinovirus protease inhibitors of formula (I), particulary (I'), key intermediates useful in those synthetic routes, as well as a continuous membrane reactor useful for those synthetic routes. These compounds of formula (I), as well as pharmaceutical compositions that contain these compounds, are suitable for treating patients or hosts infected with one or more picornaviruses.

Inventors:
TAO JUNHUA
BABU SRINIVASAN
DAGNINO RAYMOND JR
TIAN QINGPING
REMARCHUK TRAVIS PAUL
MCGEE KEVIN SCOTT
NAYYAR NARESH K
MORAN TERENCE JAROLD
Application Number:
PCT/US2000/023032
Publication Date:
August 30, 2001
Filing Date:
August 23, 2000
Export Citation:
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Assignee:
AGOURON PHARMA (US)
International Classes:
A61K31/422; A61P31/14; B01J19/24; C07C69/732; C07C229/34; C07C271/22; C07C303/28; C07D207/26; C07D261/18; C07D413/12; C12M1/12; C12P7/42; C12P17/14; C07C309/65; (IPC1-7): C07D413/12; C07D261/18; C07C309/65; C07C303/28; C07C69/732; C07C59/56; C07C271/22; C07C229/36; C07C51/347; C12P17/14; C12P7/42; C12P1/00
Foreign References:
DE2426651A11975-12-11
US4326031A1982-04-20
US5360927A1994-11-01
US5869697A1999-02-09
FR2686897A11993-08-06
Other References:
LEFKER B A ET AL: "An efficient synthesis of enantiomerically enriched aryllactic esters", TETRAHEDRON LETTERS, vol. 35, no. 29, 18 July 1994 (1994-07-18), pages 5205 - 5208, XP002153921
HAIGH D ET AL: "Anomalous fluorination of 3-aryl-2-hydroxypropanoic esters by diethylaminosulfur trifluoride (DAST)", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1, no. 24, 1996, pages 2895 - 2900, XP002153922
SHAW J P ET AL: "Selective bromination of alpha-chloro and alpha-bromo carboxylic acid derivatives", JOURNAL OF ORGANIC CHEMISTRY, vol. 61, no. 16, 9 August 1996 (1996-08-09), pages 5635 - 5637, XP002153923
O'HAGAN D ET AL: "Fluorinated tropane alkaloids generated by direct biosynthesis in transormed root cultures of Datura stramonium", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1, no. 15, 28 July 1999 (1999-07-28), pages 2117 - 2120, XP002153924
THEODORIDIS G ET AL: "A new approach to the synthesis of substituted 2(1H)-quinolinones", JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 28, 1 June 1991 (1991-06-01), pages 849 - 852, XP002046545, ISSN: 0022-152X
KAKUSAWA N ET AL: "Photochemically Induced Coupling Reaction of Triarylstibines with Olefins", TETRAHEDRON LETTERS, vol. 39, no. 52, 24 December 1998 (1998-12-24), pages 9743 - 9746, XP004144307, ISSN: 0040-4039
BRUNNER H ET AL: "Asymmetric catalysis, part 108 Copper catalysts with optically active ligands in the enantioselective Meerwein arylation of activated olefins", JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 541, no. 1-2, 15 August 1997 (1997-08-15), pages 89 - 95, XP004093706, ISSN: 0022-328X
KAMINSKI Z J: "2-Chloro-4,6-dimethoxy-1,3,5-triazine. A new coupling reagent for peptide synthesis", SYNTHESIS, no. 10, October 1987 (1987-10-01), pages 917 - 920, XP002153925
MEYER R F ET AL: "Novel synthesis of (S)-1-[5-(benzoylamino)-1,4-dioxo-6-phenylhexyl]-L-proline and analogues: potent angiotensin converting enzyme inhibitors", JOURNAL OF MEDICINAL CHEMISTRY, vol. 24, no. 8, August 1981 (1981-08-01), pages 964 - 969, XP002153926
DRAGOVICH P S ET AL: "Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 4. Incorporation of P1 lactam moieties as L-glutamine replacements", JOURNAL OF MEDICINAL CHEMISTRY, vol. 42, no. 7, 8 April 1999 (1999-04-08), pages 1213 - 1224, XP002153928
DRAGOVICH P S ET AL: "Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 3. Structure-activity studies of ketomethylene-containing peptidomimetics", JOURNAL OF MEDICINAL CHEMISTRY, vol. 42, no. 7, 8 April 1999 (1999-04-08), pages 1203 - 1212, XP002153927
DATABASE WPI Derwent World Patents Index; AN 1986-097896, XP002161553
CHEMICAL ABSTRACTS, vol. 109, no. 3, 18 July 1988, Columbus, Ohio, US; abstract no. 22654n, page 584; XP002161552
SUTHERLAND J K ET AL: "1 -> 6 Oxygen transposition of a cyclohex-2-enone", TETRAHEDRON LETTERS, vol. 25, no. 8, 1984, pages 881 - 884, XP002161550
KANG S-K ET AL: "Highly regioselective nucleophilic substitution of cyclic carbonates of threo-2,3-dihydroxy esters: synthesis of optically pure beta-hydroxy esters", JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS 1, no. 24, 21 December 1994 (1994-12-21), pages 3513 - 3514, XP002161551
WOO G-J ET AL: "Maltotetraose production using Pseudomonas stutzeri exo-alpha-amylase in a membrane recycle bioreactor", JOURNAL OF FOOD SCIENCE, vol. 56, no. 4, 1991, pages 1019 - 1023, 1033, XP002161549
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