ES2112151A1 - Homochiral compounds for the preparation of ketoconazole, terconazole and related antifungal drugs - Google Patents
Homochiral compounds for the preparation of ketoconazole, terconazole and related antifungal drugsInfo
- Publication number
- ES2112151A1 ES2112151A1 ES09500553A ES9500553A ES2112151A1 ES 2112151 A1 ES2112151 A1 ES 2112151A1 ES 09500553 A ES09500553 A ES 09500553A ES 9500553 A ES9500553 A ES 9500553A ES 2112151 A1 ES2112151 A1 ES 2112151A1
- Authority
- ES
- Spain
- Prior art keywords
- terconazole
- preparation
- compounds
- ketoconazole
- antifungal drugs
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/24—Radicals substituted by singly bound oxygen or sulfur atoms esterified
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The present invention relates to novel homochiral compounds which are intermediates for the preparation of a number of azole antifungal drugs of formula (V), in an enantiomerically pure form, wherein Ar is a phenyl or substituted phenyl group, so that the substituted phenyl group can contain one to three substituents, which can independently be fluorine, chlorine, bromine, (C1-C4)-alkyl or (C1-C4)-alkyloxy Y is a CH group or a nitrogen atom Z is a group COCH3, CH(CH3)2 or (a). The present invention also relates to the compounds (+)-terconazole and (-)-terconazole. Said compounds show antifungal and antibacterial activities and they can be used in human and veterinary therapies.
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES9500553A ES2112151B1 (en) | 1995-03-17 | 1995-03-17 | NEW HOMOQUIRAL COMPOUNDS FOR THE PREPARATION OF KETOCONAZOLE, THERONAZOLE AND RELATED ANTIFUNGICS, PROCEDURE FOR THEIR MANUFACTURE AND USE OF THEM. |
PCT/EP1996/000972 WO1996029325A1 (en) | 1995-03-17 | 1996-03-07 | Homochiral compounds for the preparation of ketoconazole, terconazole and related antifungal drugs |
AU50039/96A AU5003996A (en) | 1995-03-17 | 1996-03-07 | Homochiral compounds for the preparation of ketoconazole, terconazole and related antifungal drugs |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES9500553A ES2112151B1 (en) | 1995-03-17 | 1995-03-17 | NEW HOMOQUIRAL COMPOUNDS FOR THE PREPARATION OF KETOCONAZOLE, THERONAZOLE AND RELATED ANTIFUNGICS, PROCEDURE FOR THEIR MANUFACTURE AND USE OF THEM. |
Publications (2)
Publication Number | Publication Date |
---|---|
ES2112151A1 true ES2112151A1 (en) | 1998-03-16 |
ES2112151B1 ES2112151B1 (en) | 1999-09-16 |
Family
ID=8289834
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES9500553A Expired - Lifetime ES2112151B1 (en) | 1995-03-17 | 1995-03-17 | NEW HOMOQUIRAL COMPOUNDS FOR THE PREPARATION OF KETOCONAZOLE, THERONAZOLE AND RELATED ANTIFUNGICS, PROCEDURE FOR THEIR MANUFACTURE AND USE OF THEM. |
Country Status (3)
Country | Link |
---|---|
AU (1) | AU5003996A (en) |
ES (1) | ES2112151B1 (en) |
WO (1) | WO1996029325A1 (en) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001504465A (en) | 1996-11-12 | 2001-04-03 | セプラコール,インク. | 2R, 4S, S, S- and 2S, 4R, S, S-hydroxyitraconazole |
EP0942907A1 (en) * | 1996-11-12 | 1999-09-22 | Sepracor, Inc. | 2r, 4s, s, r- and 2s, 4r, s, r-hydroxyitraconazole |
WO1998021205A1 (en) * | 1996-11-12 | 1998-05-22 | Sepracor, Inc. | 2r,4s,r,r- and 2s,4r,r,r-hydroxyitraconazole |
CA2572223C (en) | 2004-06-25 | 2014-08-12 | The Johns Hopkins University | Angiogenesis inhibitors |
JP5350367B2 (en) * | 2007-05-25 | 2013-11-27 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | Improved synthesis of (2S-cis) -2- (bromomethyl) -2- (4-chlorophenyl) -1,3-dioxolane-4-methanol methanesulfonate (ester) |
WO2010013510A1 (en) * | 2008-08-01 | 2010-02-04 | ダイソー株式会社 | Process for production of optically active compound |
EP3858357A1 (en) | 2020-01-28 | 2021-08-04 | Diaccurate | Use of azole compounds to stimulate the immune system and as inhibitors for s-pla2gib |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5208331A (en) * | 1992-06-18 | 1993-05-04 | Syntex (U.S.A.) Inc. | Process for preparing 1,3-dioxolane derivatives |
WO1993019061A1 (en) * | 1992-03-18 | 1993-09-30 | Janssen Pharmaceutica N.V. | Itraconazole and saperconazole stereoisomers |
WO1994025452A1 (en) * | 1993-04-30 | 1994-11-10 | Schering Corporation | Process for preparing intermediates for the synthesis of antifungal agents |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3039087A1 (en) * | 1980-10-16 | 1982-05-19 | Hoechst Ag, 6000 Frankfurt | 1- (1,3-DIOXOLAN-2-YLMETHYL) -AZOLES, THEIR SALTS, METHOD FOR THE PRODUCTION AND THEIR USE |
DE3166517D1 (en) * | 1980-11-24 | 1984-11-08 | Janssen Pharmaceutica Nv | NOVEL (2-ARYL-4-PHENYLTHIOALKYL-1,3-DIOXOLAN-2-YL-METHYL) AZOLE DERIVATIVES |
-
1995
- 1995-03-17 ES ES9500553A patent/ES2112151B1/en not_active Expired - Lifetime
-
1996
- 1996-03-07 AU AU50039/96A patent/AU5003996A/en not_active Abandoned
- 1996-03-07 WO PCT/EP1996/000972 patent/WO1996029325A1/en active Application Filing
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1993019061A1 (en) * | 1992-03-18 | 1993-09-30 | Janssen Pharmaceutica N.V. | Itraconazole and saperconazole stereoisomers |
US5208331A (en) * | 1992-06-18 | 1993-05-04 | Syntex (U.S.A.) Inc. | Process for preparing 1,3-dioxolane derivatives |
WO1994025452A1 (en) * | 1993-04-30 | 1994-11-10 | Schering Corporation | Process for preparing intermediates for the synthesis of antifungal agents |
Non-Patent Citations (3)
Title |
---|
CHAPMAN, D.R y BAUER, L. Synthesis and 13C NMR Spectra of cis- and trans-{2-(haloaryl)-2-[(1H-imidazol)-1-yl]methyl}-1,3 dioxolane-4-methanols. J. Heterocyclic. Chem., 1990, Vol. 27, pßginas 2053-2061 * |
HEERES, J. et al. Antimycotic Azoles. 6. Synthesis and antifungal Properties of terconazole, a novel triazole ketal. J. Med. Chem., 1983, Vol 26, páginas 611-613 * Página 612, fórmula 7 * * |
ROTSTEIN, D.M et al. Stereoisomers of ketoconazole: Preparation and biological activity. J. Med. Chem., 1992, Vol. 35, pßginas 2818-2825 * Todo el documento * * |
Also Published As
Publication number | Publication date |
---|---|
WO1996029325A1 (en) | 1996-09-26 |
AU5003996A (en) | 1996-10-08 |
ES2112151B1 (en) | 1999-09-16 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EC2A | Search report published |
Date of ref document: 19980316 Kind code of ref document: A1 Effective date: 19980316 |
|
FA2A | Application withdrawn |
Effective date: 20001102 |