LV10104B - Antiviral pyrimidine nucleosides - Google Patents

Antiviral pyrimidine nucleosides Download PDF

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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
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LV
Latvia
Prior art keywords
formula
compound
deoxy
derivative
thiouridine
Prior art date
Application number
LVP-93-177A
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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

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06Pyrimidine radicals
    • C07H19/073Pyrimidine radicals with 2-deoxyribosyl as the saccharide radical
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D333/00Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04Heterocyclic 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
    • C07D333/06Heterocyclic 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
    • C07D333/14Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/16Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D333/00Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04Heterocyclic 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
    • C07D333/06Heterocyclic 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
    • C07D333/14Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/18Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04Heterocyclic 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

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  • 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)

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WO1994001117A1 (en) * 1992-07-02 1994-01-20 The Wellcome Foundation Limited Therapeutic nucleosides
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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
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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

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