Title:
PROCESS FOR PRODUCING TRIAZOLE DERIVATIVE
Document Type and Number:
WIPO Patent Application WO/1995/028374
Kind Code:
A1
Abstract:
A novel glycerol derivative and a process for producing the same, and a process for producing a triazole derivative. Specifically the invention provides an optically active 2-arylglycerol derivative that is novel and useful as an intermediate for drug synthesis, and the invention process can provide (R)-2-(2,4-difluorophenyl)-3-(1H-1,2,4-triazole-1-yl)propane-1,2-diol useful as an antifungal agent.
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Inventors:
YASOHARA YOSHIHIKO (JP)
MIYAMOTO KENJI (JP)
KIZAKI NORIYUKI (JP)
KAWANO SHIGERU (JP)
HASEGAWA JUNZO (JP)
MIYAMOTO KENJI (JP)
KIZAKI NORIYUKI (JP)
KAWANO SHIGERU (JP)
HASEGAWA JUNZO (JP)
Application Number:
PCT/JP1995/000749
Publication Date:
October 26, 1995
Filing Date:
April 17, 1995
Export Citation:
Assignee:
KANEGAFUCHI CHEMICAL IND (JP)
YASOHARA YOSHIHIKO (JP)
MIYAMOTO KENJI (JP)
KIZAKI NORIYUKI (JP)
KAWANO SHIGERU (JP)
HASEGAWA JUNZO (JP)
YASOHARA YOSHIHIKO (JP)
MIYAMOTO KENJI (JP)
KIZAKI NORIYUKI (JP)
KAWANO SHIGERU (JP)
HASEGAWA JUNZO (JP)
International Classes:
C07C33/26; C07C33/46; C07C69/28; C07C69/30; C07C69/63; C07C309/66; C07C309/73; C07D249/08; C07D301/30; C07D303/14; C07D521/00; C12P7/20; C12P7/62; C12P41/00; (IPC1-7): C07C33/26; C07C67/14; C07C67/26; C07C67/30; C07C69/02; C07C69/52; C07C69/76; C07C303/26; C07C309/63; C07D251/12; C07D301/02; C07D301/27; C12P7/02; C12P7/62
Foreign References:
| JPH05186372A | 1993-07-27 | |||
| JPH03500767A | 1991-02-21 | |||
| US4851439A | 1989-07-25 | |||
| EP0124004A2 | 1984-11-07 | |||
| JPS55141436A | 1980-11-05 | |||
| US4178299A | 1979-12-11 | |||
| JPS5165706A | 1976-06-07 |
Other References:
DELLE MONACHE, G. et al., "Thymol derivatives from Eupatorium glechnophyllum", PHYTOCHEMISTRY, 1984, Vol. 23, No. 9, pages 1947-1950.
MARCO, J.A. et al., "Chlorinated thymol derivatives from Inula crithmoides", PHYTOCHEMISTRY, 1993, Vol. 33, No. 4, pages 875-878.
GONZALES, A.G. et al., "Thymol derivatives from Schizogyne glaberrima", PHYTOCHEMISTRY, 1986, Vol. 25, No. 12, pages 2889-2891.
TAMAYO-CASTILLO, G. et al., "Germacranolides and other constituents from Ageratina species", PHYTOCHEMISTRY, 1988, Vol. 27, No. 9, pages 2893-2897.
MARTINEZ, M.M. et al., "Thymol derivatives from Calea nelsonii", PHYTOCHEMISTRY, 1987, Vol. 26, No. 9, pages 2577-2579.
BOHLMANN, F. et al., "Constituents of the genus Oxylobus", PHYTOCHEMISTRY, 1985, Vol. 24, No. 5, pages 1111-1112.
KOTANI, E. et al., "Preparation and reactivities of hexakisacetonitrile iron(III)perchlorate and related complexes as strong oxidizing reagents", CHEM. PHARM BULL., 1984, Vol. 32, No. 11, pages 4281-4291.
BOHLMANN, E. et al., "New guaianolides from Centipeda minima", KEXUE TONGBAO (Foreign Lang. Ed), 1984, Vol. 29, No. 7, pages 900-903.
COCKMAN, S.J. et al., "The synthesis of some esters of glycerol with special attention to the problem of acyl migration", AUST. J. CHEM., 1990, Vol. 43, No. 12, pages 2093-2097.
AWL, R.A. et al., "Synthesis and characterization of triacylglycerols containing linoleate and linolenate", LIPIDS, 1989, Vol. 24, No. 10, pages 866-872.
NISHIZAWA, M. et al., "Cyanolipid. Part II, Synthesis of types II and III cyanolipids", THETRAHEDRON LETT., 1983, Vol. 24, No. 41, pages 4447-4450.
STEVENS, R.W. et al., "Diastereoselection in a directed crossed aldol reaction between two polyoxygenated Ketones employing tin(II) enolates. A facile stereoselective synthesis of tehyl 2-C-methyl-DL-lyxofuranoside", CHEM. LETT., 1983, No. 4, pages 595-598.
ANDERSON, R.J. et al., "Farnesic acid glycerides from the nudibranch Archidoris odhneri", TETRAHEDRON LETT., 1980, Vol. 21, No. 9, pages 797-800.
MEIDANI, J. et al., "The identification of radiolytic decomposition products from tributyrin", J. AM. OIL CHEM. SOC., 1977, Vol. 54 No. 11, pages 496-501.
SHINDO, M. et al., "Sulfonamides. III. Synthesis of 1,2,4,-benzothiadiazine 1,1-dioxides", YAKUGAKU ZASSHI, 1971, Vol. 91, No. 6, pages 641-649.
QUINTANA, R.P. et al., "Monomolecular films of compounds with potential dermophilic and prophylactic properties. Esters of dihydroxyacetone", CAN. J. CHEM., 1969, Vol. 47, No. 5, pages 853-856.
REINHOUDT, D.N. et al., "Synthesis of some derivatives of cephalosporamini. II. Synthesis of cephalosporine antibiotics", RECL. TRAV. CHEM. Pays-Bas, 1968, Vol. 87, No. 11, pages 1153-1164.
NGUYEN THI DIEM TRANG et al., "New acetophenone and thymol derivatives from Eupatorium stoechadosmum", PLANTA MED., 1993, Vol. 59, No. 5, pages 480-481.
WANG, ZHI MIN et al., "Asymmetric dihydroxylation of Alpha-substituted styrene derivatives", SYNLETT, 1993, No. 8, pages 603-604.
BOHLMANN, F. et al., "A further guaianolide from Kaunia arbuscularis", PLANTA MED., 1984, Vol. 50, No. 3, page 284.
DELLE MONACHE, G. et al., "Tinifoline and tinifoline diol: two new thymol derivatives from Eupatorium tinifolium H.B.K.", FARMACO, ED. SCI., 1981, Vol 36, No. 11, pages 960-970.
See also references of EP 0704419A4
MARCO, J.A. et al., "Chlorinated thymol derivatives from Inula crithmoides", PHYTOCHEMISTRY, 1993, Vol. 33, No. 4, pages 875-878.
GONZALES, A.G. et al., "Thymol derivatives from Schizogyne glaberrima", PHYTOCHEMISTRY, 1986, Vol. 25, No. 12, pages 2889-2891.
TAMAYO-CASTILLO, G. et al., "Germacranolides and other constituents from Ageratina species", PHYTOCHEMISTRY, 1988, Vol. 27, No. 9, pages 2893-2897.
MARTINEZ, M.M. et al., "Thymol derivatives from Calea nelsonii", PHYTOCHEMISTRY, 1987, Vol. 26, No. 9, pages 2577-2579.
BOHLMANN, F. et al., "Constituents of the genus Oxylobus", PHYTOCHEMISTRY, 1985, Vol. 24, No. 5, pages 1111-1112.
KOTANI, E. et al., "Preparation and reactivities of hexakisacetonitrile iron(III)perchlorate and related complexes as strong oxidizing reagents", CHEM. PHARM BULL., 1984, Vol. 32, No. 11, pages 4281-4291.
BOHLMANN, E. et al., "New guaianolides from Centipeda minima", KEXUE TONGBAO (Foreign Lang. Ed), 1984, Vol. 29, No. 7, pages 900-903.
COCKMAN, S.J. et al., "The synthesis of some esters of glycerol with special attention to the problem of acyl migration", AUST. J. CHEM., 1990, Vol. 43, No. 12, pages 2093-2097.
AWL, R.A. et al., "Synthesis and characterization of triacylglycerols containing linoleate and linolenate", LIPIDS, 1989, Vol. 24, No. 10, pages 866-872.
NISHIZAWA, M. et al., "Cyanolipid. Part II, Synthesis of types II and III cyanolipids", THETRAHEDRON LETT., 1983, Vol. 24, No. 41, pages 4447-4450.
STEVENS, R.W. et al., "Diastereoselection in a directed crossed aldol reaction between two polyoxygenated Ketones employing tin(II) enolates. A facile stereoselective synthesis of tehyl 2-C-methyl-DL-lyxofuranoside", CHEM. LETT., 1983, No. 4, pages 595-598.
ANDERSON, R.J. et al., "Farnesic acid glycerides from the nudibranch Archidoris odhneri", TETRAHEDRON LETT., 1980, Vol. 21, No. 9, pages 797-800.
MEIDANI, J. et al., "The identification of radiolytic decomposition products from tributyrin", J. AM. OIL CHEM. SOC., 1977, Vol. 54 No. 11, pages 496-501.
SHINDO, M. et al., "Sulfonamides. III. Synthesis of 1,2,4,-benzothiadiazine 1,1-dioxides", YAKUGAKU ZASSHI, 1971, Vol. 91, No. 6, pages 641-649.
QUINTANA, R.P. et al., "Monomolecular films of compounds with potential dermophilic and prophylactic properties. Esters of dihydroxyacetone", CAN. J. CHEM., 1969, Vol. 47, No. 5, pages 853-856.
REINHOUDT, D.N. et al., "Synthesis of some derivatives of cephalosporamini. II. Synthesis of cephalosporine antibiotics", RECL. TRAV. CHEM. Pays-Bas, 1968, Vol. 87, No. 11, pages 1153-1164.
NGUYEN THI DIEM TRANG et al., "New acetophenone and thymol derivatives from Eupatorium stoechadosmum", PLANTA MED., 1993, Vol. 59, No. 5, pages 480-481.
WANG, ZHI MIN et al., "Asymmetric dihydroxylation of Alpha-substituted styrene derivatives", SYNLETT, 1993, No. 8, pages 603-604.
BOHLMANN, F. et al., "A further guaianolide from Kaunia arbuscularis", PLANTA MED., 1984, Vol. 50, No. 3, page 284.
DELLE MONACHE, G. et al., "Tinifoline and tinifoline diol: two new thymol derivatives from Eupatorium tinifolium H.B.K.", FARMACO, ED. SCI., 1981, Vol 36, No. 11, pages 960-970.
See also references of EP 0704419A4
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