DE69535476D1 - Substituierte 1,3-Oxathiolane mit antviralen Eigenschaften - Google Patents

Substituierte 1,3-Oxathiolane mit antviralen Eigenschaften

Info

Publication number
DE69535476D1
DE69535476D1 DE69535476T DE69535476T DE69535476D1 DE 69535476 D1 DE69535476 D1 DE 69535476D1 DE 69535476 T DE69535476 T DE 69535476T DE 69535476 T DE69535476 T DE 69535476T DE 69535476 D1 DE69535476 D1 DE 69535476D1
Authority
DE
Germany
Prior art keywords
oxathiolanes
substituted
antiviral properties
relates
fluorocytosine
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
DE69535476T
Other languages
English (en)
Other versions
DE69535476T2 (de
Inventor
Tarek S Mansour
Jin Haolun
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 DE69535476D1 publication Critical patent/DE69535476D1/de
Publication of DE69535476T2 publication Critical patent/DE69535476T2/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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 System
    • 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
DE69535476T 1994-04-20 1995-04-19 Substituierte 1,3-Oxathiolane mit antviralen Eigenschaften Expired - Lifetime DE69535476T2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US230317 1994-04-20
US08/230,317 US5587480A (en) 1990-11-13 1994-04-20 Substituted 1,3-oxathiolanes and substituted 1,3-dithiolanes with antiviral properties

Publications (2)

Publication Number Publication Date
DE69535476D1 true DE69535476D1 (de) 2007-05-31
DE69535476T2 DE69535476T2 (de) 2008-01-03

Family

ID=22864746

Family Applications (3)

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
DE69525742T Expired - Lifetime DE69525742T2 (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
DE69533458T Expired - Lifetime DE69533458T2 (de) 1994-04-20 1995-04-19 Substituierte 1,3-Oxathiolane mit antiviralen Eigenschaften
DE69525742T Expired - Lifetime DE69525742T2 (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) EP1153924B1 (de)
JP (1) JPH09512526A (de)
AT (3) ATE214066T1 (de)
AU (1) AU693884B2 (de)
CA (1) CA2188283C (de)
DE (3) DE69535476T2 (de)
DK (3) DK0756595T3 (de)
ES (3) ES2286542T3 (de)
HK (3) HK1041487B (de)
PT (3) PT756595E (de)
WO (1) WO1995029176A1 (de)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5276151A (en) * 1990-02-01 1994-01-04 Emory University Method of synthesis of 1,3-dioxolane nucleosides
US6069252A (en) * 1990-02-01 2000-05-30 Emory University Method of resolution and antiviral activity of 1,3-oxathiolane nucleoside enantiomers
US6642245B1 (en) 1990-02-01 2003-11-04 Emory University Antiviral activity and resolution of 2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane
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
EP1655033A1 (de) * 1995-06-07 2006-05-10 Emory University Nucleoside mit anti-hepatitis B virus Wirksamkeit
US6215004B1 (en) 1998-08-12 2001-04-10 Emory University Method of manufacture of 1,3-oxathiolane nucleosides
US6979561B1 (en) 1998-10-09 2005-12-27 Gilead Sciences, Inc. Non-homogeneous systems for the resolution of enantiomeric mixtures
CN1372564A (zh) * 2000-02-10 2002-10-02 三井化学株式会社 选择性制备1－磷酸化糖衍生物端基异构体的方法和制备核苷的方法
WO2002051852A1 (fr) * 2000-12-27 2002-07-04 Mitsui Chemicals, Inc. Procede de production d'un derive de saccharide non naturel
DK1406896T3 (da) * 2001-06-15 2006-05-08 Shire Biochem Inc Stereoselektiv fremgangsmåde til fremstillingen af nukleosidanaloger
PT1583542E (pt) 2003-01-14 2008-09-17 Gilead Sciences Inc Composições e métodos para terapia de combinação antiviral
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
KR100993031B1 (ko) * 2005-03-14 2010-11-08 샤이어 캐나다 인코포레이티드 광학적으로 활성인시스-2-하이드록시메틸-4-(사이토신-1'-일)-1,3-옥사티올란또는 그의 약제학적으로 허용가능한 염의 제조공정과 방법
TWI471145B (zh) 2005-06-13 2015-02-01 Bristol Myers Squibb & Gilead Sciences Llc 單一式藥學劑量型
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
US20080249066A1 (en) * 2007-03-23 2008-10-09 Ardea Biosciences, Inc. Antiviral compounds and compositions
AU2008303073B2 (en) * 2007-09-28 2012-08-09 Avexa Limited A process for chiral resolution of 2-substituted 4-substituted 1,3-oxathiolanes
AU2008361409B2 (en) 2008-09-05 2015-02-12 Shire Biochem Inc. Enantiomeric resolution of 2,4-disubstituted 1,3-oxathiolane nucleosides
WO2010068756A2 (en) * 2008-12-10 2010-06-17 Thesis Chemistry, Llc Process for manufacture of optically active 2-(acyloxymethyl)-1, 3 oxathiolanes
US8431699B2 (en) 2009-02-27 2013-04-30 Vertichem Corporation Method for manufacture of 2-oxoimidazolidines
TW201131192A (en) * 2010-03-01 2011-09-16 Univ Nat Central A co-crystal compound of optical devices
CA2854946A1 (en) * 2011-11-18 2013-05-23 Avexa Limited Apricitabine and pi combination therapy
JP2012136526A (ja) * 2012-02-09 2012-07-19 Shire Canada Inc 光学的に活性なｃｉｓ−２−ヒドロキシメチル−４−（シトシン−１’−イル）−１，３−オキサチオランまたはその薬学的に許容される塩の製造方法
WO2024016639A1 (zh) * 2022-07-21 2024-01-25 华创合成制药股份有限公司 一种抗病毒感染的化合物及其制备方法和用途

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US4000137A (en) * 1975-06-10 1976-12-28 American Home Products Corporation Antitumor derivatives of periodate-oxidized nucleosides
JPS5668674A (en) * 1979-11-08 1981-06-09 Shionogi & Co Ltd 5-fluorouracil derivative
DE3529263A1 (de) * 1985-08-16 1987-02-19 Hoechst Ag Verfahren zur herstellung von 2-oxo-1,3-dioxolanen
US5159067A (en) * 1987-01-28 1992-10-27 University Of Georgia Research Foundation Inc. 5'-Diphosphohexose nucleoside pharmaceutical compositions
SE8701605D0 (sv) * 1987-04-16 1987-04-16 Astra Ab Novel medicinal compounds
US5039667A (en) * 1987-08-07 1991-08-13 The Governors Of The University Of Alberta Antiviral therapy for hepatitis B with 2',3'-dideoxypurine nucleosides
US4997926A (en) * 1987-11-18 1991-03-05 Scripps Clinic And Research Foundation Deaminase-stable anti-retroviral 2-halo-2',3'-dideoxy
NZ228645A (en) * 1988-04-11 1991-09-25 Iaf Biochem Int 1,3-dioxolane derivatives substituted in the 5th position by a purine or pyrimidine radical; treatment of viral infections
US5047407A (en) * 1989-02-08 1991-09-10 Iaf Biochem International, Inc. 2-substituted-5-substituted-1,3-oxathiolanes with antiviral properties
GB8815265D0 (en) * 1988-06-27 1988-08-03 Wellcome Found Therapeutic nucleosides
DE3827134A1 (de) * 1988-08-10 1990-03-15 Bayer Ag Substituierte triazolyl- bzw. imidazolyl-hydroxyalkyldioxolane, verfahren zu ihrer herstellung und ihre verwendung als mikrobizide, oxiranyldioxolane, dioxolanylketone, oxiranylketone und (alpha)-halogenketone als zwischenprodukte und verfahren zu deren herstellung
NZ233197A (en) * 1989-04-13 1991-11-26 Richard Thomas Walker Aromatically substituted nucleotide derivatives, intermediates therefor and pharmaceutical compositions
US5118672A (en) * 1989-07-10 1992-06-02 University Of Georgia Research Foundation 5'-diphosphohexose nucleoside pharmaceutical compositions
IE902574A1 (en) * 1989-07-17 1991-02-27 Univ Birmingham Antiviral pyrimidine nucleosides
JP2960164B2 (ja) * 1990-11-13 1999-10-06 バイオケム ファーマ インコーポレイテッド 抗ウイルス特性を有する置換１，３−オキサチオラン類および置換１，３−ジチオラン類
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Also Published As

Publication number Publication date
PT1153924E (pt) 2005-01-31
US5587480A (en) 1996-12-24
EP1473294A3 (de) 2004-11-17
DK1224940T3 (da) 2004-12-27
DK1224940T4 (da) 2010-10-25
EP1473294A2 (de) 2004-11-03
EP1153924B1 (de) 2004-09-01
ES2228714T3 (es) 2005-04-16
ES2172580T3 (es) 2002-10-01
CA2188283C (en) 2003-11-04
HK1073460A1 (en) 2005-10-07
ATE275144T1 (de) 2004-09-15
PT756595E (pt) 2002-08-30
AU693884B2 (en) 1998-07-09
HK1041487B (zh) 2005-01-07
EP1473294B1 (de) 2007-04-18
DE69533458T2 (de) 2005-10-27
HK1005544A1 (en) 1999-01-15
HK1041487A1 (en) 2002-07-12
DK1473294T3 (da) 2007-09-17
ATE360019T1 (de) 2007-05-15
ATE214066T1 (de) 2002-03-15
DE69535476T2 (de) 2008-01-03
EP0756595A1 (de) 1997-02-05
DE69533458D1 (de) 2004-10-07
CA2188283A1 (en) 1995-11-02
EP1153924A2 (de) 2001-11-14
PT1473294E (pt) 2007-06-11
WO1995029176A1 (en) 1995-11-02
DE69525742T2 (de) 2002-09-26
DE69525742D1 (de) 2002-04-11
ES2286542T3 (es) 2007-12-01
AU2211895A (en) 1995-11-16
JPH09512526A (ja) 1997-12-16
EP1153924A3 (de) 2001-11-21
DK0756595T3 (da) 2002-06-17
EP0756595B1 (de) 2002-03-06

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Legal Events

Date Code Title Description
8381 Inventor (new situation)

Inventor name: MANSOUR, TAREK S., NEW-CITY NN 10956, US

Inventor name: JIN, HAOLUN, FOSTER CITY CA 94404, US

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

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

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

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