Title:
METHOD OF OBTAINING INHIBITORS OF TYPE II DEHYDROQUINASE ENZYME AND PRECURSORS THEREOF
Document Type and Number:
WIPO Patent Application WO2005009330
Kind Code:
A3
Abstract:
The invention relates to a method of obtaining inhibitors of the type II dehydroquinase enzyme and the precursors thereof from (-)-quinic acid, the aforementioned compounds having a carboxycyclohexene structure. More specifically, the invention relates to the method of preparing said compounds and to the use of same as compositions with pharmacological and herbicidal properties.
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Inventors:
GONZALEZ BELLO CONCEPCION (ES)
CASTEDO EXPOSTIO LUIS (ES)
CASTEDO EXPOSTIO LUIS (ES)
Application Number:
PCT/ES2004/000337
Publication Date:
March 17, 2005
Filing Date:
July 16, 2004
Export Citation:
Assignee:
UNIV SANTIAGO COMPOSTELA (ES)
GONZALEZ BELLO CONCEPCION (ES)
CASTEDO EXPOSTIO LUIS (ES)
GONZALEZ BELLO CONCEPCION (ES)
CASTEDO EXPOSTIO LUIS (ES)
International Classes:
A01N37/30; A01N37/36; A01N37/40; A01N43/12; A61K31/19; C07C61/22; C07C62/34; A61K; (IPC1-7): C07C61/22; A01N37/36; A61K31/19
Other References:
GONZALEZ-BELLO, C. ET AL.: "Parallel solid-phase synthesis and evaluation of inhibitors of Streptomyces coelicolor type II dehydroquinase", J.MED.CHEM., vol. 46, no. 26, 2003, pages 5735 - 5744, XP002995435
FREDERICKSON, M. ET AL.: "Selective inhibition of type II dehydroquinase", J.ORG.CHEM., vol. 64, no. 8, 1999, pages 2612 - 2613, XP002995436
GONZALEZ-BELLO, C. ET AL.: "Synthesis of polyhydroxy cyclohexanes and relatives from (-)-quinic acid", J.ORG.CHEM., vol. 68, no. 6, 2003, pages 2248 - 2255, XP002995437
MONTCHAMP, J.L. ET AL.: "Cyclohexenyl and cyclohexylidene inhibitors of 3-dehydroquinate synthase: Active site interacions relevant to enzime mechanism and inhibitor design", J.AM.CHEM.SOC., vol. 119, no. 33, 1997, pages 7645 - 7653, XP002995438
SUTHERLAND, J.K. ET AL.: "The synthesis of 6a- and 6b-fluoroshikimic acids", J.CHEM.SOC.CHEM.COMMUN., vol. 18, 1989, pages 1386 - 1387, XP002995445
HARRIS, J.M. ET AL: "Comparison of the substrate specifity of type I and type II dehydroquinases with 5-deoxy- and 4,5-dideoxy-dehydroquinic acid", J.CHEM.SOC.PERKIN TRANS 1: ORG. & BIO-ORG.CHEM, vol. 19, 1996, pages 2371 - 2377, XP002995446
CARBALLIDO, M. ET AL.: "Synthesis of carba-sugars from (-)-quinic acid", TETRAHEDRON LETT., vol. 42, no. 24, 2001, pages 3973 - 3976, XP004240831
PHOON, C.W. ET AL.: "Use of quinic acid as template in solid-phase combinatorial synthesis", J.COMB.CHEM., vol. 1, 1999, pages 485 - 492, XP002995439
FREDERICKSON, M. ET AL.: "Selective inhibition of type II dehydroquinase", J.ORG.CHEM., vol. 64, no. 8, 1999, pages 2612 - 2613, XP002995436
GONZALEZ-BELLO, C. ET AL.: "Synthesis of polyhydroxy cyclohexanes and relatives from (-)-quinic acid", J.ORG.CHEM., vol. 68, no. 6, 2003, pages 2248 - 2255, XP002995437
MONTCHAMP, J.L. ET AL.: "Cyclohexenyl and cyclohexylidene inhibitors of 3-dehydroquinate synthase: Active site interacions relevant to enzime mechanism and inhibitor design", J.AM.CHEM.SOC., vol. 119, no. 33, 1997, pages 7645 - 7653, XP002995438
SUTHERLAND, J.K. ET AL.: "The synthesis of 6a- and 6b-fluoroshikimic acids", J.CHEM.SOC.CHEM.COMMUN., vol. 18, 1989, pages 1386 - 1387, XP002995445
HARRIS, J.M. ET AL: "Comparison of the substrate specifity of type I and type II dehydroquinases with 5-deoxy- and 4,5-dideoxy-dehydroquinic acid", J.CHEM.SOC.PERKIN TRANS 1: ORG. & BIO-ORG.CHEM, vol. 19, 1996, pages 2371 - 2377, XP002995446
CARBALLIDO, M. ET AL.: "Synthesis of carba-sugars from (-)-quinic acid", TETRAHEDRON LETT., vol. 42, no. 24, 2001, pages 3973 - 3976, XP004240831
PHOON, C.W. ET AL.: "Use of quinic acid as template in solid-phase combinatorial synthesis", J.COMB.CHEM., vol. 1, 1999, pages 485 - 492, XP002995439
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