Title:
SYNTHESIS OF TETRACYCLINES AND INTERMEDIATES THERETO
Document Type and Number:
WIPO Patent Application WO/2010/126607
Kind Code:
A3
Abstract:
Efficient method for preparing the enone intermediate (VII) used in the synthesis of tetracyclines derivatives. In particular, the invention provides a synthesis which allows for substituents at positions 4a, 5, 5a, and 12a of the tetracycline ring system.
Inventors:
MYERS ANDREW G (US)
KUMMER DAVID A (US)
LI DERUN (US)
HECKER EVAN (US)
DION AMELIE (US)
WRIGHT PETER MAUGHAN (US)
KUMMER DAVID A (US)
LI DERUN (US)
HECKER EVAN (US)
DION AMELIE (US)
WRIGHT PETER MAUGHAN (US)
Application Number:
PCT/US2010/001284
Publication Date:
July 21, 2011
Filing Date:
April 30, 2010
Export Citation:
Assignee:
HARVARD COLLEGE (US)
MYERS ANDREW G (US)
KUMMER DAVID A (US)
LI DERUN (US)
HECKER EVAN (US)
DION AMELIE (US)
WRIGHT PETER MAUGHAN (US)
MYERS ANDREW G (US)
KUMMER DAVID A (US)
LI DERUN (US)
HECKER EVAN (US)
DION AMELIE (US)
WRIGHT PETER MAUGHAN (US)
International Classes:
C07C237/26; A61K31/165; A61K31/18; A61K31/401; A61K31/4164; A61K31/495; C07C49/637; C07C311/05; C07D207/06; C07D207/16; C07D211/06; C07D213/74; C07D233/61; C07D295/15; C07D295/155
Domestic Patent References:
| WO2007067807A1 | 2007-06-14 | |||
| WO2002085303A2 | 2002-10-31 | |||
| WO2007112121A2 | 2007-10-04 | |||
| WO2008127361A2 | 2008-10-23 |
Foreign References:
| US3914299A | 1975-10-21 | |||
| GB1100885A | 1968-01-24 |
Other References:
NELSON M L ET AL: "MOLECULAR REQUIREMENTS FOR THE INHIBITION OF THE TETRACYCLINE ANTIPORT PROTEIN AND THE EFFECT OF POTENT INHIBITORS ON THE GROWTH OF TETRACYCLINE-RESISTANT BACTERIA", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, US, vol. 37, no. 9, 1 January 1994 (1994-01-01), pages 1355 - 1361, XP001010609, ISSN: 0022-2623, DOI: DOI:10.1021/JM00035A016
DATABASE REAXYS [online] Elsevier Properties SA; XP002618138, Database accession no. Reaxys RN:7453524
A. A. TYMIAK ET AL: "Dactylocyclines: Novel Tatracycline Glycosides Active against Tetracycline-Resistant Bacteria", J.ORG.CHEM., vol. 58, no. 3, 1993, pages 535 - 537, XP002618139
G. J. PALENIK ET AL: "Structural Studies of Tetracyclines. Crystal and Molecular Structures of Anhydrotetracycline Hydrobromide Monohydrate and 6-Demethyl-7-chlorotetracycline Hydrochloride Trihydrate", J. AM. CHEM. SOC., vol. 100, no. 14, 1978, pages 4458 - 4464, XP002618140
H. URBACH ET AL: "Totalsynthese von d,l 4-Amino-7-chlor-2-N-methylcarbamyl-2-descarbamyl-4-des-dimethylamino-6-desmethyl-6-desoxytetracyclin", TETRAHEDRON LETT., vol. 49, 1973, pages 4907 - 4910, XP002618141
W. MARTIN ET AL: "Totalsynthese von d,l-7-Chlor-6-desoxytetracyclinen und d,l-7-Chlor-6-desmethyl-6-desoxytetracyclinen der natürlichen, der 5a-epi- und der 6-epi-Reihe", TETRAHEDRON LETT., no. 36, 1973, pages 3513 - 3516, XP002618142
M. SCHACH ET AL: "Proton Magnetic Resonance Spectra of Tetracyclines", J. CHEM. SOC., vol. 31, February 1966 (1966-02-01), pages 613 - 615, XP002618143
DATABASE REAXYS [online] Elsevier Properties SA; XP002618144, Database accession no. Reaxys RN: 6796420
R. D. CURTIS ET AL: "A nitrogen-15 nuclear magnetic resonance study of the tetracycline antibiotics", CAN. J. CHEM., vol. 69, 1991, pages 834 - 838, XP002618145
DATABASE REAXYS [online] Elsevier Properties SA; XP002618138, Database accession no. Reaxys RN:7453524
A. A. TYMIAK ET AL: "Dactylocyclines: Novel Tatracycline Glycosides Active against Tetracycline-Resistant Bacteria", J.ORG.CHEM., vol. 58, no. 3, 1993, pages 535 - 537, XP002618139
G. J. PALENIK ET AL: "Structural Studies of Tetracyclines. Crystal and Molecular Structures of Anhydrotetracycline Hydrobromide Monohydrate and 6-Demethyl-7-chlorotetracycline Hydrochloride Trihydrate", J. AM. CHEM. SOC., vol. 100, no. 14, 1978, pages 4458 - 4464, XP002618140
H. URBACH ET AL: "Totalsynthese von d,l 4-Amino-7-chlor-2-N-methylcarbamyl-2-descarbamyl-4-des-dimethylamino-6-desmethyl-6-desoxytetracyclin", TETRAHEDRON LETT., vol. 49, 1973, pages 4907 - 4910, XP002618141
W. MARTIN ET AL: "Totalsynthese von d,l-7-Chlor-6-desoxytetracyclinen und d,l-7-Chlor-6-desmethyl-6-desoxytetracyclinen der natürlichen, der 5a-epi- und der 6-epi-Reihe", TETRAHEDRON LETT., no. 36, 1973, pages 3513 - 3516, XP002618142
M. SCHACH ET AL: "Proton Magnetic Resonance Spectra of Tetracyclines", J. CHEM. SOC., vol. 31, February 1966 (1966-02-01), pages 613 - 615, XP002618143
DATABASE REAXYS [online] Elsevier Properties SA; XP002618144, Database accession no. Reaxys RN: 6796420
R. D. CURTIS ET AL: "A nitrogen-15 nuclear magnetic resonance study of the tetracycline antibiotics", CAN. J. CHEM., vol. 69, 1991, pages 834 - 838, XP002618145
Attorney, Agent or Firm:
BAKER, Hunter, C. (Greenfield & Sacks P.C.,600 Atlantic Avenu, Boston MA, US)
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