DE69525742T2 - Substituierte 1,3-oxathiolane mit antiviralen eigenschaften - Google Patents

Substituierte 1,3-oxathiolane mit antiviralen eigenschaften

Info

Publication number
DE69525742T2
DE69525742T2 DE69525742T DE69525742T DE69525742T2 DE 69525742 T2 DE69525742 T2 DE 69525742T2 DE 69525742 T DE69525742 T DE 69525742T DE 69525742 T DE69525742 T DE 69525742T DE 69525742 T2 DE69525742 T2 DE 69525742T2
Authority
DE
Germany
Prior art keywords
oxathiolane
mmol
nmr
compounds
acid
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
DE69525742T
Other languages
English (en)
Other versions
DE69525742D1 (de
Inventor
Haolun Jin
S. Mansour
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.)
Shire Canada Inc
Original Assignee
Shire BioChem Inc
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 Shire BioChem Inc filed Critical Shire BioChem Inc
Application granted granted Critical
Publication of DE69525742D1 publication Critical patent/DE69525742D1/de
Publication of DE69525742T2 publication Critical patent/DE69525742T2/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • 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
    • A61P31/12—Antivirals
    • 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
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/04—Immunostimulants
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D411/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Molecular Biology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Virology (AREA)
  • Immunology (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • AIDS & HIV (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Claims (6)

1. Verwendung von
(i) 2R-Hydroxymethyl-4R-(cytosin-1'-yl)-1,3-oxathiolan oder eines pharmazeutisch unbedenklichen Salzes oder Esters davon;
(ii) 2S-Hydroxymethyl-4S-(cytosin-1'-yl)-1,3-oxathiolan oder eines pharmazeutisch unbedenklichen Salzes oder Esters davon;
(iii) einer beliebigen Kombination der Isomeren (i) und (ii);
(iv) 2R-Hydroxymethyl-4R-(5'-fluorcytosin-1'-yl)-1,3- oxathiolan oder eines pharmazeutisch unbedenklichen Salzes oder Esters davon;
(v) 2S-Hydroxymethyl-4S-(5'-fluorcytosin-1'-yl)-1,3- oxathiolan oder eines pharmazeutisch unbedenklichen Salzes oder Esters davon; oder
(vi) einer beliebigen Kombination der Isomeren (iii) und (iv)
zur Herstellung eines Medikaments zur Behandlung von Infektionen mit 3TCTM-resistenten bzw. FTC-resistenten Human Immunodeficiency Virus in Säugetieren.
2. Verwendung der Mittel nach Anspruch 1, worin für die Behandlung ein zusätzliches therapeutisches Agens verabreicht wird.
3. Verwendung der Mittel nach Anspruch 1, worin das zusätzliche therapeutische Agens ein weiteres antivirales Agens ist.
4. Verwendung der Mittel nach Anspruch 3, worin das weitere antivirale therapeutische Agens aus der Gruppe AZT, 3TCTM, ddC und ddl ausgewählt wird, mit AZT gleich 3'-azido-3'deoxythymidin, ddc gleich 2',3'-dideoxycytidin und ddl gleich 2',3'-dideoxyinosin.
5. Verwendung der Mittel nach Anspruch 4, worin das weitere antivirale Agens 3TCTM ist.
6. Verwendung der Mittel nach einem der voranstehenden Ansprüche, worin das Säugetier ein Mensch ist.
DE69525742T 1994-04-20 1995-04-19 Substituierte 1,3-oxathiolane mit antiviralen eigenschaften Expired - Lifetime DE69525742T2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US08/230,317 US5587480A (en) 1990-11-13 1994-04-20 Substituted 1,3-oxathiolanes and substituted 1,3-dithiolanes with antiviral properties
PCT/CA1995/000212 WO1995029176A1 (en) 1994-04-20 1995-04-19 Substituted 1,3-oxathiolanes with antiviral properties

Publications (2)

Publication Number Publication Date
DE69525742D1 DE69525742D1 (de) 2002-04-11
DE69525742T2 true DE69525742T2 (de) 2002-09-26

Family

ID=22864746

Family Applications (3)

Application Number Title Priority Date Filing Date
DE69525742T Expired - Lifetime DE69525742T2 (de) 1994-04-20 1995-04-19 Substituierte 1,3-oxathiolane mit antiviralen eigenschaften
DE69535476T Expired - Lifetime DE69535476T2 (de) 1994-04-20 1995-04-19 Substituierte 1,3-Oxathiolane mit antviralen Eigenschaften
DE69533458T Expired - Lifetime DE69533458T2 (de) 1994-04-20 1995-04-19 Substituierte 1,3-Oxathiolane mit antiviralen Eigenschaften

Family Applications After (2)

Application Number Title Priority Date Filing Date
DE69535476T Expired - Lifetime DE69535476T2 (de) 1994-04-20 1995-04-19 Substituierte 1,3-Oxathiolane mit antviralen Eigenschaften
DE69533458T Expired - Lifetime DE69533458T2 (de) 1994-04-20 1995-04-19 Substituierte 1,3-Oxathiolane mit antiviralen Eigenschaften

Country Status (12)

Country Link
US (1) US5587480A (de)
EP (3) EP1473294B1 (de)
JP (1) JPH09512526A (de)
AT (3) ATE275144T1 (de)
AU (1) AU693884B2 (de)
CA (1) CA2188283C (de)
DE (3) DE69525742T2 (de)
DK (3) DK1473294T3 (de)
ES (3) ES2172580T3 (de)
HK (3) HK1041487B (de)
PT (3) PT1473294E (de)
WO (1) WO1995029176A1 (de)

Families Citing this family (30)

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US5914331A (en) * 1990-02-01 1999-06-22 Emory University Antiviral activity and resolution of 2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane
US6069252A (en) * 1990-02-01 2000-05-30 Emory University Method of resolution and antiviral activity of 1,3-oxathiolane nucleoside enantiomers
US5276151A (en) * 1990-02-01 1994-01-04 Emory University Method of synthesis of 1,3-dioxolane nucleosides
US5204466A (en) * 1990-02-01 1993-04-20 Emory University Method and compositions for the synthesis of bch-189 and related compounds
US6369066B1 (en) 1990-11-13 2002-04-09 Biochem Pharma, Inc. Substituted 1,3-oxathiolanes with antiviral properties
US6228860B1 (en) * 1990-11-13 2001-05-08 Biochem Pharma Inc. Substituted 1,3-oxathiolanes with antiviral properties
US20050192299A1 (en) * 1992-04-16 2005-09-01 Yung-Chi Cheng Method of treating or preventing hepatitis B virus
US20020120130A1 (en) * 1993-09-10 2002-08-29 Gilles Gosselin 2' or 3' -deoxy and 2', 3' -dideoxy-beta-L-pentofuranonucleo-side compounds, method of preparation and application in therapy, especially as anti- viral agents
IL113432A (en) 1994-04-23 2000-11-21 Glaxo Group Ltd Process for the diastereoselective synthesis of nucleoside analogues
AU722214B2 (en) 1995-06-07 2000-07-27 Centre National De La Recherche Scientifique (Cnrs) Nucleosides with anti-hepatitis B virus activity
RU2439069C2 (ru) 1998-08-12 2012-01-10 Гайлид Сайенсиз, Инк. Способ получения 1,3-оксатиолановых нуклеозидов
US6979561B1 (en) 1998-10-09 2005-12-27 Gilead Sciences, Inc. Non-homogeneous systems for the resolution of enantiomeric mixtures
EP1178051B1 (de) * 2000-02-10 2008-05-28 Mitsui Chemicals, Inc. Verfahren zur selektiven herstellung eines 1-phosphoryliertem zuckerderivativ-anomers und verfahren zur herstellung von nukleosiden
WO2002051852A1 (fr) * 2000-12-27 2002-07-04 Mitsui Chemicals, Inc. Procede de production d'un derive de saccharide non naturel
EP1406896B8 (de) * 2001-06-15 2006-11-15 Shire Biochem Inc. Stereoselektives verfahren zur herstellung von nukleosidanaloga
ATE398455T1 (de) 2003-01-14 2008-07-15 Gilead Sciences Inc Zusammensetzungen und verfahren zur antiviralen kombinationstherapie
US7501514B1 (en) 2003-10-15 2009-03-10 Shire Biochem, Inc. Enantiomeric resolution of 2-substituted 4-substituted 1,3-oxathiolanes nucleosides
US7968703B2 (en) 2005-03-07 2011-06-28 Shire Canada Inc. Process and methods for the preparation of optically active cis-2-hydroxymethyl-4- (cytosin-1'-yl)-1,3-oxathiolane or pharmaceutically acceptable salts thereof
EP1866303B1 (de) * 2005-03-14 2013-11-27 Shire Canada Inc. Verfahren und methoden zur herstellung von optisch aktivem cis-2-hydroxymethyl-4-(cytosin-1-yl)-1,3-oxathiolan oder pharmazeutisch unbedenklichen salzen davon
TWI375560B (en) 2005-06-13 2012-11-01 Gilead Sciences Inc Composition comprising dry granulated emtricitabine and tenofovir df and method for making the same
TWI471145B (zh) 2005-06-13 2015-02-01 Bristol Myers Squibb & Gilead Sciences Llc 單一式藥學劑量型
WO2008118879A2 (en) * 2007-03-23 2008-10-02 Ardea Biosciences, Inc. Antiviral compositions comprising 2 compounds
NZ584193A (en) * 2007-09-28 2011-07-29 Avexa Ltd A process for chiral resolution of 2-substituted 4-substituted 1,3-oxathiolanes
KR101556815B1 (ko) * 2008-09-05 2015-10-01 샤이어 캐나다 인코포레이티드 2,4-이치환된 1,3-옥사티올란 뉴클레오사이드의 거울상이성질체 분리
US8153416B2 (en) 2008-12-10 2012-04-10 Thesis Chemistry, Llc Process for manufacture of optically active 2-(acyloxymethyl)-1,3-oxathiolanes using enzymatic resolution
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Also Published As

Publication number Publication date
ES2286542T3 (es) 2007-12-01
EP1473294A2 (de) 2004-11-03
EP1473294A3 (de) 2004-11-17
DE69533458D1 (de) 2004-10-07
EP1153924A3 (de) 2001-11-21
ES2172580T3 (es) 2002-10-01
WO1995029176A1 (en) 1995-11-02
HK1041487A1 (en) 2002-07-12
EP1153924A2 (de) 2001-11-14
ES2228714T3 (es) 2005-04-16
DE69533458T2 (de) 2005-10-27
DE69535476D1 (de) 2007-05-31
AU693884B2 (en) 1998-07-09
DK0756595T3 (da) 2002-06-17
ATE214066T1 (de) 2002-03-15
EP0756595A1 (de) 1997-02-05
CA2188283A1 (en) 1995-11-02
AU2211895A (en) 1995-11-16
JPH09512526A (ja) 1997-12-16
DK1473294T3 (da) 2007-09-17
DK1224940T4 (da) 2010-10-25
EP0756595B1 (de) 2002-03-06
PT756595E (pt) 2002-08-30
US5587480A (en) 1996-12-24
DE69535476T2 (de) 2008-01-03
ATE275144T1 (de) 2004-09-15
DK1224940T3 (da) 2004-12-27
EP1153924B1 (de) 2004-09-01
CA2188283C (en) 2003-11-04
PT1153924E (pt) 2005-01-31
DE69525742D1 (de) 2002-04-11
EP1473294B1 (de) 2007-04-18
HK1073460A1 (en) 2005-10-07
HK1041487B (zh) 2005-01-07
ATE360019T1 (de) 2007-05-15
HK1005544A1 (en) 1999-01-15
PT1473294E (pt) 2007-06-11

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Legal Events

Date Code Title Description
8364 No opposition during term of opposition
8327 Change in the person/name/address of the patent owner

Owner name: SHIRE BIOCHEM INC., VILLE ST-LAURENT, QUEBEC, CA

8327 Change in the person/name/address of the patent owner

Owner name: SHIRE CANADA INC., ST. LAURENT, QUEBEC, CA