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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 drugs

Info

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
Application number
ES09500553A
Other languages
Spanish (es)
Other versions
ES2112151B1 (en
Inventor
Garcia Pelayo Camps
Torrecabota Xavier Farres
Casellas David Mauleon
Germano Carganico
Perez M Luisa Garcia
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Laboratorios Menarini SA
Original Assignee
Laboratorios Menarini SA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Laboratorios Menarini SA filed Critical Laboratorios Menarini SA
Priority to ES9500553A priority Critical patent/ES2112151B1/en
Priority to PCT/EP1996/000972 priority patent/WO1996029325A1/en
Priority to AU50039/96A priority patent/AU5003996A/en
Publication of ES2112151A1 publication Critical patent/ES2112151A1/en
Application granted granted Critical
Publication of ES2112151B1 publication Critical patent/ES2112151B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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.
ES9500553A 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. Expired - Lifetime ES2112151B1 (en)

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 (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0938484A1 (en) * 1996-11-12 1999-09-01 Sepracor, Inc. 2r,4s,r,r- and 2s,4r,r,r-hydroxyitraconazole
WO1998021204A1 (en) * 1996-11-12 1998-05-22 Sepracor, Inc. 2r,4s,s,s- and 2s,4r,s,s-hydroxyitraconazole
CA2269616A1 (en) * 1996-11-12 1998-05-22 Gerald J. Tanoury 2r,4s,s,r- and 2s,4r,s,r-hydroxyitraconazole
EP1765336A4 (en) 2004-06-25 2010-03-10 Univ Johns Hopkins INHIBITORS OF ANGIOGENESIS
MX2009012739A (en) * 2007-05-25 2009-12-10 Janssen Pharmaceutica Nv 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
EP4619398A1 (en) * 2022-11-14 2025-09-24 Piramal Pharma Limited A process for the preparation of levoketoconazole
CN116854657A (en) * 2023-07-04 2023-10-10 浙江东亚药业股份有限公司 Preparation method of ketoconazole intermediate cis-bromo-ester

Citations (3)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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
EP0052905B1 (en) * 1980-11-24 1984-10-03 Janssen Pharmaceutica N.V. Novel (2-aryl-4-phenylthioalkyl-1,3-dioxolan-2-yl-methyl)azole derivatives

Patent Citations (3)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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
ES2112151B1 (en) 1999-09-16
AU5003996A (en) 1996-10-08

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