Optically active azole derivative and process for producing...

Details Optically active azole derivative and process for producing... Optically active azole derivative and process for producing...

2007-09-18

2007-09-18

Anderson, Rebecca (Department: 1626)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C514S383000, C548S255000, C548S262200

Reexamination Certificate

active

10503469

ABSTRACT:
A method for producing an optically active 2-phenyl-2,3,-dihydroxypropyl azole derivative, which is a useful compound in various fields. An optically active α-hydroxycarboxylic acid derivative represented by general formula (1) is used as a starting material and is allowed to react with an azole acetic acid derivative (2) to produce a new, optically active azole-alkyl ketone derivative (3). Subsequently, a new, optically active azole-methyl alcohol derivative (5) is produced by highly diastereoselective alkylation by an appropriate combination of a protective group and an organometallic reagent (4). Furthermore, the optically active azole-methyl alcohol derivative (5) is selectively deprotected to produce an optically active 2-phenyl-2,3-dihydroxypropyl azole derivative (6)

REFERENCES:
patent: 5004494 (1991-04-01), Sugavanam et al.
patent: 5204363 (1993-04-01), Sugavanam et al.
patent: 5648372 (1997-07-01), Naito et al.
patent: 6300522 (2001-10-01), Crosby et al.
patent: 7060657 (2006-06-01), Hacker et al.
patent: 753513 (1997-01-01), None
patent: 97/31903 (1997-09-01), None
Patani et al., “Bioisosterism: A Rational Approach in Drug Design,” Chem. Rev. , 1996, 96, 3147-3176, especially p. 3157, Table 22.
Bartroli et al., “New Azole Antifungals. 3. Synthesis and Antifungal Activity of 3-Substituted-4(3H-quinazoliones1,2,”J. Med. Chem., 1998, pp. 1869-1882, vol. 41, No. 11, American Chemical Society*.
Tasaka et al., “Optically Activity Antifungal Azoles. I. Synthesis and Antifungal Activity of (2R,3R)-2-(2,4-Difluorophenyl)-3-mercapto-1-(1H-1,2,4-triazol-1-yl)-2-butanol and Its Stereoisomers,”Chem. Pharm. Bull., Jun. 1993, pp. 1035-1042, vol. 41, No. 6*.
Girijavallabhan et al., “Synthesis of the Antifungal Agent SCH 424271(SM 9164),”Bioorganic&Medicinal Chemistry Letters, 1991, pp. 349-352, vol. 1, No. 7, Pergamon Press plc, Great Britain*.
Adam et al., “Synthesis of Optically Active α-Hydroxycarbonyl Compounds by (Salen)Mn(III)-Catalyzed Oxidation of Silyl Enol Ethers and Silyl Ketene Acetals,”Tetrahedron Letters, 1996, pp. 6531-6534, vol. 37, No. 36, Elsevier Science Ltd., Great Britain*.
“New Antifungal Agents,”Iyaku Journal, 2001, pp. 115-119 (2105-2109), vol. 37, No. 7 (English abstract).

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