CA2122270C - Tri-substituted tetrahydrofuran antifungals - Google Patents

Tri-substituted tetrahydrofuran antifungals Download PDF

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Publication number
CA2122270C
CA2122270C CA002122270A CA2122270A CA2122270C CA 2122270 C CA2122270 C CA 2122270C CA 002122270 A CA002122270 A CA 002122270A CA 2122270 A CA2122270 A CA 2122270A CA 2122270 C CA2122270 C CA 2122270C
Authority
CA
Canada
Prior art keywords
compound
triazol
formula
mixture
phenyl
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.)
Expired - Lifetime
Application number
CA002122270A
Other languages
English (en)
French (fr)
Other versions
CA2122270A1 (en
Inventor
Anil K. Saksena
Viyyoor M. Girijavallabhan
Ashit K. Ganguly
Raymond G. Lovey
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.)
Merck Sharp and Dohme LLC
Original Assignee
Schering Corp
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 Schering Corp filed Critical Schering Corp
Publication of CA2122270A1 publication Critical patent/CA2122270A1/en
Application granted granted Critical
Publication of CA2122270C publication Critical patent/CA2122270C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • 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
    • 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
    • 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
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Oncology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Communicable Diseases (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CA002122270A 1991-10-30 1992-10-28 Tri-substituted tetrahydrofuran antifungals Expired - Lifetime CA2122270C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US78535791A 1991-10-30 1991-10-30
US785,357 1991-10-30
US90726292A 1992-07-01 1992-07-01
US907,262 1992-07-01
PCT/US1992/008981 WO1993009114A1 (en) 1991-10-30 1992-10-28 Tri-substituted tetrahydrofuran antifungals

Publications (2)

Publication Number Publication Date
CA2122270A1 CA2122270A1 (en) 1993-05-13
CA2122270C true CA2122270C (en) 2006-05-23

Family

ID=27120397

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002122270A Expired - Lifetime CA2122270C (en) 1991-10-30 1992-10-28 Tri-substituted tetrahydrofuran antifungals

Country Status (22)

Country Link
EP (2) EP0610377B1 (cg-RX-API-DMAC10.html)
JP (1) JP3210017B2 (cg-RX-API-DMAC10.html)
CN (1) CN1037267C (cg-RX-API-DMAC10.html)
AT (1) ATE198888T1 (cg-RX-API-DMAC10.html)
AU (1) AU665218B2 (cg-RX-API-DMAC10.html)
CA (1) CA2122270C (cg-RX-API-DMAC10.html)
CZ (1) CZ102794A3 (cg-RX-API-DMAC10.html)
DE (1) DE69231661T2 (cg-RX-API-DMAC10.html)
ES (1) ES2153364T3 (cg-RX-API-DMAC10.html)
FI (1) FI941986A0 (cg-RX-API-DMAC10.html)
HR (1) HRP921145A2 (cg-RX-API-DMAC10.html)
HU (1) HUT70742A (cg-RX-API-DMAC10.html)
IL (1) IL103558A0 (cg-RX-API-DMAC10.html)
MX (1) MX9206222A (cg-RX-API-DMAC10.html)
MY (1) MY109529A (cg-RX-API-DMAC10.html)
NO (1) NO941589L (cg-RX-API-DMAC10.html)
NZ (1) NZ244910A (cg-RX-API-DMAC10.html)
SG (1) SG42920A1 (cg-RX-API-DMAC10.html)
SI (1) SI9200285A (cg-RX-API-DMAC10.html)
SK (1) SK48894A3 (cg-RX-API-DMAC10.html)
WO (1) WO1993009114A1 (cg-RX-API-DMAC10.html)
YU (1) YU94792A (cg-RX-API-DMAC10.html)

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US5403937A (en) * 1993-04-30 1995-04-04 Schering Corporation Process for preparing intermediates for the synthesis of antifungal agents
US5349099A (en) * 1993-12-13 1994-09-20 Schering Corporation Process for preparing intermediates for the synthesis of antifungal agents
DE69428125T2 (de) * 1993-12-21 2002-05-02 Schering Corp., Kenilworth Fungizide tetrahydrofurane
US5693626A (en) * 1993-12-21 1997-12-02 Schering Corporation Tetrahydrofuran antifungals
US5661151A (en) * 1993-12-21 1997-08-26 Schering Corporation Tetrahydrofuran antifungals
US5703236A (en) * 1993-12-21 1997-12-30 Schering Corporation Tetrahydrofuran antifungals
US5714490A (en) * 1993-12-21 1998-02-03 Schering Corporation Tetrahydrofuran antifungals
US5710154A (en) * 1993-12-21 1998-01-20 Schering Corporation Tetrahydrofuran antifungals
US5703079A (en) * 1993-12-21 1997-12-30 Schering Corporation Tetrahydrofuran antifungals
JP3764750B2 (ja) * 1994-01-24 2006-04-12 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 水溶性アゾール抗真菌剤
CN1126987A (zh) * 1994-04-19 1996-07-17 钟渊化学工业株式会社 三唑衍生物的制造方法
US5442093A (en) * 1994-05-09 1995-08-15 Schering Corporation Process for preparing intermediates for the synthesis of antifungal agents
US5486625A (en) * 1994-07-08 1996-01-23 Schering Corporation Process for the preparation of chiral intermediates useful for the synthesis of antifungal agents
EP0725146A4 (en) * 1994-07-18 1998-12-23 Daicel Chem METHOD FOR PRODUCING OPTICALLY ACTIVE TRIAZOLE COMPOUNDS AND METHOD FOR RAZEMIZING OPTICALLY ACTIVE TRIAZOLE COMPOUNDS
US5616777A (en) * 1995-04-19 1997-04-01 Schering Corporation Chiral hydrazine derivatives
US5625064A (en) * 1995-04-19 1997-04-29 Schering Corporation Process for the preparation of triazolones
MX9701229A (es) * 1995-06-02 1997-05-31 Schering Corp Antifungicos de tetrahidrofurano.
US5698557A (en) * 1995-06-19 1997-12-16 Schering Corporation Hydroxy-substituted antifungals
EP0837859B1 (en) * 1995-06-19 2003-08-13 Schering Corporation Tetrahydrofuran antifungals
US5834472A (en) * 1996-05-24 1998-11-10 Schering Corporation Antifungal composition with enhanced bioavailability
US5846971A (en) * 1996-06-28 1998-12-08 Schering Corporation Oral antifungal composition
TW593312B (en) * 1997-07-11 2004-06-21 Janssen Pharmaceutica Nv 2,4,4-trisubstituted-1,3-dioxolane antifungals
HU225233B1 (en) * 1997-10-07 2006-08-28 Schering Corp Crystalline polymorph of antifungal triazole derivative, pharmaceuticals containing the same and its use
AU2002253440A1 (en) * 2002-04-12 2003-10-27 Ranbaxy Laboratories Limited Derivatives of 2,2,4-trisubstituted tetrahydrofuran as antifungal agents
RU2580318C2 (ru) 2010-05-19 2016-04-10 Сандоз Аг Получение промежуточных продуктов для синтеза позаконазола
AU2011254658B2 (en) 2010-05-19 2016-02-18 Sandoz Ag Purification of posaconazole and of posaconazole intermediates
JP5956980B2 (ja) 2010-05-19 2016-07-27 サンド・アクチエンゲゼルシヤフト キラル化合物の調製の方法
WO2011144653A1 (en) 2010-05-19 2011-11-24 Sandoz Ag Process for the preparation of chiral triazolones
US9493428B2 (en) 2011-06-16 2016-11-15 Sandoz Ag Process for the preparation of a chiral compound
DK3003038T3 (da) * 2013-06-07 2019-11-11 Scripps Research Inst 2h-1,2,3-triazolderivater som inhibitorer af fibrose
CN106397417A (zh) * 2016-08-30 2017-02-15 甘肃皓天化学科技有限公司 用于制备泊沙康唑的中间体的制备方法

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US4267179A (en) * 1978-06-23 1981-05-12 Janssen Pharmaceutica, N.V. Heterocyclic derivatives of (4-phenylpiperazin-1-yl-aryloxymethyl-1,3-dioxolan-2-yl)methyl-1H-imidazoles and 1H-1,2,4-triazoles
US4619931A (en) * 1983-02-28 1986-10-28 Janssen Pharmaceutica, N.V. [[4-[4-(4-phenyl-1-piperazinyl)phenoxymethyl]-1,3-dioxolan-2-yl]methyl]-1H-imidazoles and 1H-1,2,4-triazoles
DE3346123A1 (de) 1983-12-21 1985-06-27 Janssen Pharmaceutica, N.V., Beerse Pharmazeutische praeparate von in wasser schwerloeslichen oder instabilen arzneistoffen und verfahren zu ihrer herstellung
US4727064A (en) 1984-04-25 1988-02-23 The United States Of America As Represented By The Department Of Health And Human Services Pharmaceutical preparations containing cyclodextrin derivatives
DK354185A (da) * 1984-08-31 1986-03-01 Hoffmann La Roche 1,3-dioxolanderivater
NZ223799A (en) * 1987-03-25 1989-12-21 Janssen Pharmaceutica Nv Azolylmethyl-dioxolanylmethoxyphenyl-piperazinyl-phenyl-triazolones and antimicrobial compositions
US5006513A (en) 1987-11-09 1991-04-09 Miles Inc. Antimycotic compositions of nikkomycin compounds and azole antimycotica
DE3852477T2 (de) * 1987-11-20 1995-05-04 Schering Corp Tri- und tetrasubstituierte Oxetane und Tetrahydrofurane und deren Zwischenprodukte.
US5002935A (en) 1987-12-30 1991-03-26 University Of Florida Improvements in redox systems for brain-targeted drug delivery
CA1331757C (en) * 1988-02-29 1994-08-30 Janssen Pharmaceutica Naamloze Vennootschap 5-lipoxygenase inhibiting 4-(4-phenyl-1-piperazinyl)phenols
NZ233502A (en) * 1989-06-09 1991-11-26 Janssen Pharmaceutica Nv 4-(1,2,4-triazole- or imidazole-phenyl-substituted) -1-(1,3-dioxolan-4-ylmethoxyphenyl) piperazine derivatives; preparatory processes: fungicidal and antiviral compositions
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Also Published As

Publication number Publication date
WO1993009114A1 (en) 1993-05-13
HUT70742A (en) 1995-10-30
IL103558A0 (en) 1993-03-15
AU2916992A (en) 1993-06-07
NZ244910A (en) 1996-01-26
SG42920A1 (en) 1997-10-17
DE69231661D1 (de) 2001-03-01
CZ102794A3 (en) 1995-03-15
NO941589D0 (cg-RX-API-DMAC10.html) 1994-04-29
SI9200285A (en) 1993-06-30
MY109529A (en) 1997-02-28
DE69231661T2 (de) 2001-08-02
ATE198888T1 (de) 2001-02-15
YU94792A (sh) 1995-12-04
MX9206222A (es) 1993-04-01
JPH07500605A (ja) 1995-01-19
EP0610377A1 (en) 1994-08-17
CN1073944A (zh) 1993-07-07
NO941589L (cg-RX-API-DMAC10.html) 1994-06-23
AU665218B2 (en) 1995-12-21
CN1037267C (zh) 1998-02-04
HRP921145A2 (en) 1994-08-31
JP3210017B2 (ja) 2001-09-17
ES2153364T3 (es) 2001-03-01
CA2122270A1 (en) 1993-05-13
HU9401256D0 (en) 1994-08-29
EP0610377B1 (en) 2001-01-24
FI941986A7 (fi) 1994-04-29
SK48894A3 (en) 1995-02-08
EP0539938A1 (en) 1993-05-05
FI941986A0 (fi) 1994-04-29

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Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed
MKEC Expiry (correction)

Effective date: 20121210