LV10104B - Antiviral pyrimidine nucleosides - Google Patents

Antiviral pyrimidine nucleosides Download PDF

Info

Publication number
LV10104B
LV10104B LVP-93-177A LV930177A LV10104B LV 10104 B LV10104 B LV 10104B LV 930177 A LV930177 A LV 930177A LV 10104 B LV10104 B LV 10104B
Authority
LV
Latvia
Prior art keywords
formula
compound
deoxy
derivative
thiouridine
Prior art date
Application number
LVP-93-177A
Other languages
English (en)
Other versions
LV10104A (lv
Inventor
Walker Richard
Coe Paul
Original Assignee
Univ Birmingham
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
Priority claimed from GB898916323A external-priority patent/GB8916323D0/en
Priority claimed from GB898922393A external-priority patent/GB8922393D0/en
Application filed by Univ Birmingham filed Critical Univ Birmingham
Publication of LV10104A publication Critical patent/LV10104A/lv
Publication of LV10104B publication Critical patent/LV10104B/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • C07H19/073—Pyrimidine radicals with 2-deoxyribosyl as the saccharide radical
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/18—Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Oncology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Virology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Communicable Diseases (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Claims (13)

  1. LV10104 PATENTA FORMULA I. Pirimidīn- 4'-tionukleozīds, formula (I), ī
    kur Y ir hidroksi- vai amīnogrupa un X-hlors, broms, jods, trifluormetīl-, C2-C6 alkīl-, C2-C6 alkenīl-j C2-C6 halogēnalkenīl- vai C2-C6 alkinīlgrupa, vai tā fizioloģiski funkcionāls atvasinājums.
  2. 2. Savienojums pēc I.p., kas atšķiras ar to, ka X ir: C2-C3 alkīl-, C3-C4 alkenil-, halogēnvinīl- vai C3-C4 alkinīlgrupa.
  3. 3. Savienojums pēc I. vai 2 p., kas atšķiras ar to, ka pirimidīn- 4'-tionukleozīds ir: E-5-(2-bromvinīl)-2'- dezoksi- 4'-tiouridīns, 2'- dezoksi-5-jod- 4'-tiouridīns, 2'- dezoksi-5-etīl- 4'-tiouridīns, 5-brom-2'- dezoksi - 4'-tiouridīns, 2'- dezoksi-5-propinīl- 4'-tiouridīns, 5-hlor -2'- dezoksi - 4'-tiouridīns, 2'- dezoksi-5-trifluormetīl- 4'-tiouridīns, 2'- dezoksi-5-etinīl- 4'-tiouridīns, E-5-(2-bromvinīl)-2'- dezoksi- 4'-tiocitidīns, 2'- dezoksi-5-propil- 4'-tiouridīns, vai E-2'- dezoksi-5-(propēn-I-il)- 4'-tiouridīns. 2
  4. 4. Savienojums pēc jebkura p. 1-3., kas atšķiras ar to, ka pirimidīn-4'-tionukleozīds ir β-anomērs. 5. E-5- (2-bromvinīl)-2'- dezoksi- 4'-tio - β-uridīns, 6.2'- dezoksi-5-etīl- 4'-tio - β-uridīns.
  5. 7. Pirimidīnnukleozīda (formula I) fizioloģiski funkcionāls atvasinājums pēc jebkura p. 1-6.
  6. 8. Atvasinājums pēc 7. p., kas atšķiras ar to, ka ir sārmu metāla, sārmzemju metāla, amonija, tetra (Cļ-C4 alkil)amonija, hlorhidrāta vai acetāta sāls, vai mono-vai dikarbonskābes ēsteris, vai tā sārmu metāla, sārmzemju metāla, amonija vai tetra (CrC4 alkil) amonija sāls.
  7. 9. Kompozīcija, kas satur savienojumu pēc jebkura p. 1-8., maisījumā ar farmaceitiski pieņemamu vidi vai atšķaidītāju.
  8. 10. Savienojums pēc jebkura p. 1-8., vai kompozīcija pēc 9. p., kas izmantojams vīrusu infekciju ārstēšanai vai profilaksei.
  9. 11. Savienojums pēc jebkura p. 1-8., vai kompozīcijas pēc 9. p. lietošana zāļu izgatavošanai vīrusu infekciju ārstēšanai vai profilaksei.
  10. 12. Pirimidīn- 4'-tionukleozīda, formula (I) iegūšanas paņēmiens,
    LV 10104 kur Y ir hidroksi- vai amīnogrupa un X ir hlors, broms, jods, trifluormetīl-, C2-C6 alkīl-, C2-C6 alkenīl-, C2-C6 halogēnalkenīl- vai C2-C6 alkinīlgrupa, vai tā fizioloģiski funkcionāla atvasinājuma iegūšanas paņēmiens, kas atšķiras ar to, ka veic: A) - savienojuma (formula Π) reakciju: γ
    kur X1 ir X grupas "priekštecis", aprēķināts saskaņā ar formulu (1); Y nozīmes ir saskaņā ar formulu (1); Z un Z ir vienādi vai dažādi un katrs ir ūdeņradis vai hidroksi- aizsarggrupa, iedarbojoties ar reaģentu vai reaģentiem, kas kalpo, lai pārvērstu grupu X1 par X, vai B) savienojumu (formula III) reakciju, γ
    (III) kur X un Y nozīmes ir saskaņā ar formulu (I), ar 4- tiocukura atvasinājumu aizsargātās formas (kalpo 4- tiocukura fragmenta ievešanai), vai tā I. pozīcijā (formula I) savienojuma (III) aizsargāto formu, un pēc tam pie nepieciešamības, vai pēc vēlēšanās var veikt vienu vai vairākas sekojošas papildus stadijas jebkurā vēlamā vai nepieciešamā sacība: a) vienas vai vairāku aizsarggrupu izslēgšana, 4 b) savienojuma ai formulu (I), vai tā aizsargātās formas pārvēršana par citu atvasinājumu ar formulu (I) vai par tā aizsargāto formu, c) savienojuma ar formulu (I) vai tā aizsargātās formas pārvēršana par fizioloģiski funkcionālu savienojuma ar formulu (I) atvasinājumu, vai par tā aizsargāto formu, d) fizioloģiski funkcionālu savienojuma ar formulu (I) atvasinājuma, vai tā aizsargātās formas pārvēršana par citu fizioloģiski pieņemamu savienojuma ar formulu (I) atvasinājumu, e) fizioloģiski funkcionāla savienojuma ar formulu (I) atvasinājuma vai tā aizsargātās formas pārvēršana par savienojumu ar formulu (I) vai tā aizsargāto formu, f) savienojuma ar formulu (I) vai tā aizsargātās formas, vai fizioloģiski funkcionālā savienojuma ar formulu (I) atvasinājuma a-un β-anomēru sadalīšana.
  11. 13. Paņēmiens pēc 12. p. savienojuma iegūšanai pēc jebkura p. 2-8.
  12. 14. Paņēmiens pēc 12. p. vai 13. p., kas atšķiras ar to, ka 4- tiocukura atvasinājums ir savienojums ar formulu (IV), kur Z3 un Z5 ir hidroksi-aizsarggrupas un L-izslēdzamā grupa.
  13. 15. Paņēmiens pēc jebkura p.12-14, kas atšķiras ar to, ka 4-tiocukura atvasinājums ir I-acetoksi-4-tiocukura atvasinājums.
LVP-93-177A 1989-07-17 1993-03-10 Antiviral pyrimidine nucleosides LV10104B (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB898916323A GB8916323D0 (en) 1989-07-17 1989-07-17 Nucleosides
GB898922393A GB8922393D0 (en) 1989-10-04 1989-10-04 Antiviral pyrimidines
PCT/GB1990/001099 WO1991001326A1 (en) 1989-07-17 1990-07-17 Antiviral pyrimidine nucleosides

Publications (2)

Publication Number Publication Date
LV10104A LV10104A (lv) 1994-05-10
LV10104B true LV10104B (en) 1995-08-20

Family

ID=26295621

Family Applications (1)

Application Number Title Priority Date Filing Date
LVP-93-177A LV10104B (en) 1989-07-17 1993-03-10 Antiviral pyrimidine nucleosides

Country Status (19)

Country Link
US (1) US5356882A (lv)
EP (1) EP0409575A1 (lv)
JP (1) JP2502813B2 (lv)
KR (1) KR927003616A (lv)
AT (1) ATE161267T1 (lv)
AU (3) AU648746B2 (lv)
CA (1) CA2065279A1 (lv)
FI (1) FI920197A0 (lv)
HU (1) HUT59694A (lv)
IE (1) IE902574A1 (lv)
IL (1) IL95103A (lv)
LV (1) LV10104B (lv)
MX (1) MX9203668A (lv)
MY (1) MY105944A (lv)
NO (1) NO178930C (lv)
NZ (1) NZ234534A (lv)
PL (1) PL167317B1 (lv)
PT (1) PT94731B (lv)
WO (1) WO1991001326A1 (lv)

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6903224B2 (en) 1988-04-11 2005-06-07 Biochem Pharma Inc. Substituted 1,3-oxathiolanes
US7119202B1 (en) 1989-02-08 2006-10-10 Glaxo Wellcome Inc. Substituted-1,3-oxathiolanes and substituted-1,3-dioxolanes with antiviral properties
US5270315A (en) * 1988-04-11 1993-12-14 Biochem Pharma Inc. 4-(purinyl bases)-substituted-1,3-dioxlanes
US6350753B1 (en) 1988-04-11 2002-02-26 Biochem Pharma Inc. 2-Substituted-4-substituted-1,3-dioxolanes and use thereof
UA45942A (uk) * 1989-02-08 2002-05-15 Біокем Фарма, Інк. 1,3-оксатіолан, його похідні, спосіб (варіанти) його одержання та фармацевтична композиція
GB9009861D0 (en) 1990-05-02 1990-06-27 Glaxo Group Ltd Chemical compounds
US5521163A (en) * 1990-07-13 1996-05-28 University Of Birmingham Antiviral pyrimidine nucleosides and methods for using same
US5643913A (en) * 1990-07-19 1997-07-01 Glaxo Wellcome Inc. Pharmaceutical compositions of 5-substituted uracil compounds
ATE161722T1 (de) 1990-07-19 1998-01-15 Wellcome Found Enzyminaktivatoren
GB9020930D0 (en) * 1990-09-26 1990-11-07 Wellcome Found Pharmaceutical combinations
US5587480A (en) * 1990-11-13 1996-12-24 Biochem Pharma, Inc. Substituted 1,3-oxathiolanes and substituted 1,3-dithiolanes with antiviral properties
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
IL100502A (en) * 1991-01-03 1995-12-08 Iaf Biochem Int PHARMACEUTICAL PREPARATIONS CONTAINING CIS-4-AMINO-1-) 2-HYDROXIMETHIL-1,3-OXETYOLEN-5-IL (-
DE4110977A1 (de) * 1991-04-05 1992-10-08 Bayer Ag Substituierte 2',3'-didesoxy-5-trifluormethyluridine, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln
GB9109186D0 (en) * 1991-04-29 1991-06-19 Wellcome Found Preparation of thionucleosides
GB9110874D0 (en) * 1991-05-20 1991-07-10 Iaf Biochem Int Medicaments
ZA923641B (en) * 1991-05-21 1993-02-24 Iaf Biochem Int Processes for the diastereoselective synthesis of nucleosides
WO1994001117A1 (en) * 1992-07-02 1994-01-20 The Wellcome Foundation Limited Therapeutic nucleosides
CN1087089A (zh) * 1992-07-02 1994-05-25 惠尔康基金会集团公司 治疗核苷
GB9218810D0 (en) * 1992-09-04 1992-10-21 Univ Birmingham Antiviral pyrimidine nucleosides
AU4125099A (en) * 1998-06-01 1999-12-20 S & T Science And Technology Inc. Antiviral phosphorus derivatives of 4'-thio-5-ethyl-2'-deoxyuridine
KR20000008131A (ko) * 1998-07-10 2000-02-07 정낙신 치오뉴클레오시드 유도체 및 그들의 제조방법
US6653318B1 (en) 1999-07-21 2003-11-25 Yale University 5-(E)-Bromovinyl uracil analogues and related pyrimidine nucleosides as anti-viral agents and methods of use
US7589077B2 (en) 2001-05-18 2009-09-15 Rakesh Kumar Antiviral nucleosides
US7211570B2 (en) * 2001-12-20 2007-05-01 Pharmasset, Inc. Treatment of EBV and KHSV infection
JP3677510B2 (ja) * 2002-08-22 2005-08-03 株式会社ジェネティックラボ ４’−チオヌクレオチド
WO2009034945A1 (ja) * 2007-09-10 2009-03-19 Yamasa Corporation エプスタイン・バールウイルス関連疾患に対する薬剤およびそのスクリーニング法
WO2022008025A1 (en) * 2020-07-05 2022-01-13 Since & Technology Development Fund Authority 2-hydroxyiminopyrimidine nucleosides and derivitives and antiviral uses thereto

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4211773A (en) * 1978-10-02 1980-07-08 Sloan Kettering Institute For Cancer Research 5-Substituted 1-(2'-Deoxy-2'-substituted-β-D-arabinofuranosyl)pyrimidine nucleosides
US4383990A (en) * 1980-10-01 1983-05-17 Beecham Group Limited Antiviral agents, their preparation and use
DE3102136A1 (de) * 1981-01-23 1982-08-19 Bayer Ag, 5090 Leverkusen Neue verbindung bay i 3265 komponente a, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE3236389A1 (de) * 1982-10-01 1984-04-05 Bayer Ag, 5090 Leverkusen Neue nucleosidverbindungen, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE3341571A1 (de) * 1983-11-17 1985-05-30 Bayer Ag, 5090 Leverkusen Neue antibiotika, verfahren zu ihrer herstellung, ihre verwendung als arzneimittel und zwischenprodukte zu ihrer herstellung
GB8629892D0 (en) * 1986-12-15 1987-01-28 Wellcome Found Antiviral compounds
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
US5215970A (en) * 1987-04-16 1993-06-01 Medivir Ab Nucleosides and nucleotide analogues, pharmaceutical composition and processes for the preparation of the compounds
EP0516186A3 (en) * 1987-04-16 1993-01-13 Medivir Aktiebolag Nucleosides and nucleoside analogues, pharmaceutical composition and processes for the preparation of the compounds
DE3725554A1 (de) * 1987-08-01 1989-02-09 Hoechst Ag Pharmazeutisches kombinationspraeparat sowie dessen herstellung und verwendung
ZA898567B (en) * 1988-11-15 1990-08-29 Merrell Dow Pharma Novel 2'-halomethylidene,2'-ethenylidene and 2'-ethynyl cytidine,uridine and guanosine derivatives
ES2253732T3 (es) * 1989-09-15 2006-06-01 Southern Research Institute 2'-deoxi-4'-tioribonucleosidos como agentes antivirales y anticancerosos.
IE74701B1 (en) * 1989-10-04 1997-07-30 Univ Birmingham Further antiviral pyrimidine nucleosides
US5128458A (en) * 1990-04-20 1992-07-07 Southern Research Institute 2',3'-dideoxy-4'-thioribonucleosides as antiviral agents
DE4021006A1 (de) * 1990-07-02 1992-01-09 Hoechst Ag Pyrimidin-derivate, deren herstellung und verwendung sowie diese enthaltende arzneimittel
SE9003151D0 (sv) * 1990-10-02 1990-10-02 Medivir Ab Nucleoside derivatives
FR2668153B1 (fr) * 1990-10-22 1995-03-31 Pasteur Merieux Serums Vacc Nouveaux composes ribonucleosides, leur procede de preparation et les medicaments les contenant.

Also Published As

Publication number Publication date
PT94731B (pt) 1997-04-30
AU669040B2 (en) 1996-05-23
KR927003616A (ko) 1992-12-18
NO178930C (no) 1996-07-03
JPH04506661A (ja) 1992-11-19
HU9200143D0 (en) 1992-04-28
AU5963490A (en) 1991-02-22
NO920210L (no) 1992-01-16
AU5635294A (en) 1994-05-19
IL95103A (en) 1996-03-31
NO920210D0 (no) 1992-01-16
AU668270B2 (en) 1996-04-26
EP0409575A1 (en) 1991-01-23
AU5635394A (en) 1994-05-05
HUT59694A (en) 1992-06-29
NZ234534A (en) 1994-12-22
MX9203668A (es) 1992-09-01
IE902574A1 (en) 1991-02-27
US5356882A (en) 1994-10-18
WO1991001326A1 (en) 1991-02-07
MY105944A (en) 1995-02-28
NO178930B (no) 1996-03-25
FI920197A0 (fi) 1992-01-16
CA2065279A1 (en) 1991-01-18
ATE161267T1 (de) 1998-01-15
LV10104A (lv) 1994-05-10
PT94731A (pt) 1991-03-20
JP2502813B2 (ja) 1996-05-29
PL286088A1 (en) 1991-11-04
IL95103A0 (en) 1991-06-10
AU648746B2 (en) 1994-05-05
PL167317B1 (pl) 1995-08-31

Similar Documents

Publication Publication Date Title
US5356882A (en) Antiviral pyrimidine nucleosides
AU656122B2 (en) Further antiviral pyrimidine nucleosides
US5079235A (en) Antiviral compounds
US5070078A (en) Antiviral compounds
CA2143834A1 (en) Antiviral pyrimidine nucleosides
US4863906A (en) 2'-deoxy-5-ethynyluridine-3',5'-diestens for treatment of VZV and CMV infections
JP4076114B2 (ja) ４’−ｃ−エチニルプリンヌクレオシド化合物
US5521163A (en) Antiviral pyrimidine nucleosides and methods for using same
AU635834B2 (en) Antiviral compounds
NZ247461A (en) 2'-deoxy-5-ethyl-4'-thio-beta-uridine, preparation and pharmaceutical compositions
NZ244365A (en) 4-thio sugar derivatives and their preparation; use as intermediates
US5028596A (en) 1-(β-D-arabinofuranosyl)-5-propynyluracil for treatment of VZV infections
JP4039790B2 (ja) ４’−ｃ−エチニルピリミジンヌクレオシド化合物
LT3466B (en) Pyrimidine nucleosides, process for their preparation, compositions and intermediates
JPH05331184A (ja) 抗ウイルス化合物
EP0195805A1 (en) Process for making a 2-deoxyuridine