SI9010243B - Substituirani 1,3-oksatiolani z antivirusnimi lastnostmi - Google Patents

Substituirani 1,3-oksatiolani z antivirusnimi lastnostmi Download PDF

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Publication number
SI9010243B
SI9010243B SI9010243A SI9010243A SI9010243B SI 9010243 B SI9010243 B SI 9010243B SI 9010243 A SI9010243 A SI 9010243A SI 9010243 A SI9010243 A SI 9010243A SI 9010243 B SI9010243 B SI 9010243B
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Prior art keywords
oxathiolane
compound
formula
group
hydroxymethyl
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SI9010243A
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English (en)
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SI9010243A (en
Inventor
Bernard Belleau
Pierette Belleau
Nghe Nguyen-Ba
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Biochem Pharma Inc.
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Application filed by Biochem Pharma Inc. filed Critical Biochem Pharma Inc.
Priority claimed from CA002152269A external-priority patent/CA2152269C/en
Publication of SI9010243A publication Critical patent/SI9010243A/sl
Publication of SI9010243B publication Critical patent/SI9010243B/sl

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    • 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
    • C07D411/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing three or more hetero 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
    • A61P31/12—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
    • C07D327/04—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/40—Heterocyclic compounds containing purine ring systems with halogen atoms or perhalogeno-alkyl radicals directly attached in position 2 or 6
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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

Claims (12)

  1. -λ" PATENTNI ZAHTEVKI 1. Postopek za pridobivanje spojine s formulo (I)
    (I) kjer je Rj vodik; I^ je purinska ali pirimidinska baza ali njen analog ali derivat; Z je S, S=0 ali S02; in njenih farmacevtsko sprejemljivih derivatov, označen s tem, da obsega: (a) reakcijo spojine s formulo (VIII)
    (VIII) v kateri je R; vodik ali zaščitna skupina za hidroksilno skupino in je L zamenljiv atom ali skupina z bazno R^H skupino; (b) bazno interkonverzijo spojine s formulo (I) v drugo spojino s formulo (I); (c) reakcijo spojine s formulo (IX)
  2. 2. Postopek po zahtevku 1, označen s tem, da spojino s formulo (I) dobimo v obliki tis izomera.
    2 (IX) *
    s spojino s formulo (X) PO
    CHO v kateri je P zaščitna skupina; ali (X) -Z' (d) konverzijo spojine s formulo (XII)
    (XII) v spojino s formulo (I), in če je potrebno ali želeno, izpostavitev spojine, dobljene v katerekoli stopnji od (a) do (d), eni ali dvem nadaljnjim reakcijam, ki obsegata: (i) odstranjevanje katerekoli zaščitne skupine; (ii) pretvorbo spojine s formulo (I) ali njene soli v njeno farmacevtsko sprejemljivo sol.
  3. 3. Postopek po zahtevku 1 ali 2, označen s tem, da Z predstavlja S.
  4. 4. Postopek po kateremkoli od zahtevkov 1 do 3, označen s tem, da je R2:
    'N -'b-
    o
    je R3 izbran iz skupine, ki jo sestavljajo vodik, trifluorometil ali nasičena ali nenasičena C16alkilna skupina; ·* R4 in R. sta neodvisno izbrana iz skupine, ki jo sestavljajo vodik, hidroksimetil. tri-tluorometil, substituiran ali nesubstituiran, nasičen ali nenasičen Ct 6alkil, brom. klor, fluor ali jod; R6 je izbran iz skupine, ki jo sestavljajo vodik, ciano, karboksi, etoksikarbonil. kar* bamoil ali tiokarbamoil; in sta X in Y sta neodvisno izbrana iz skupine, ki jo sestavljajo vodik, brom. klor. tluor, jod. amino ali hidroksilna skupina.
  5. 5. Postopek po kateremkoli od zahtevkov 1 do 3, označen s tem, daje R2: -Ni
    kjer je R3 izbran iz skupine, ki jo sestavljajo vodik, trifluorometil ali nasičena ali nenasičena C16alkilna skupina in je R4 izbran iz skupine, ki jo sestavljajo vodik, hidroksimetil, trifluorometil, substituirana ali nesubstituirana, nasičena ali nenasičena C3 6alkilna skupina, brom, klor, fluor ali jod.
  6. 6. Postopek po kateremkoli od zahtevkov 1 do 5, označen s tem, da spojino s formulo (I) izberemo izmed: Cis-2-hidroksimetil-5-(citozin-Γ-il)-1.3-oksatiolana, trans-2-hidroksimetil-5 -f citozin-l’-il)-l,3-oksatiolana in njunih zmesi; Cis-2-benzoilksimetil-5-(citozin-l’-il)-l,3-oksatiolana, trans-2-benzoiloksimetil-5-(citozin-l’-il)-l,3-oksatioIana in njunih zmesi; Cis-2-hidroksimetil-5-(N4’-acetil-citozin-l’-il)-l,3-oksatiolana, trans-2-hidroksimetil-5-(N4’-acetil-citozin-l’-il)-l,3-oksatiolana in njunih zmesi; Cis-2-benzoiloksimetil-5-(N4’-acetil-citozin-l’-il)-l,3-oksatiolana, trans-2-benzoiloksimetil-5-(N4’-acetil-citozin-l’-il)-l,3-oksatiolana in njunih zmesi; in Qs-2-hidroksimetil-5-(citozin-l’-il-3-okso-l,3-oksatiolana); Cis-2-hidroksimetil-5-(N-dimetilamino-metilen citozin-l’-il)-l,3-oksatiolana; Bis-cis-2-sukciniloksimetil-5-(citozin-r-iD-l,3-oksatiolana; Cis-2-benzoiloksimetil-5-(6’-kloropurin-N-9’-il)-l,3-oksatiolana; trans-2-benzoiloksimetil-5-(6’-kloropurin-N-9’-il)-l,3-oksatiolana in njunih zmesi; Cis-2-hidroksimetil-5-(6’-hidroksipurin-N-9’-il)-l,3-oksatiolana; Cis-2-benzoiloksimetil-5-(uracil-N-r*il)-l,3-oksatiolana, trans-2-benzoiloksimetil-5- -5 " (uracil-N-l’-il)-l,3-oksatiolana in njunih zmesi; Cis-2-hidroksimetil-5-(uraciI-N-r-iQ-l,3-oksatiolana; Cis-2-benzoiloksimetil-5-(timin-N-r-il)-l,3-oksatiolana, trans-2-benzoiloksimetil-5-(timin-N-l’-il)-l,3-oksatiolana in njunih zmesi; Qs-2-hidroksimetil-5-(timin-N-l’-il)-l,3-oksatiolana; in njihovih farmacevtsko sprejemljivih derivatov v obliki racemnih zmesi ali posameznih enantiomerov.
  7. 7. Postopek po kateremkoli od zahtevkov 1 do 5, označen s tem, da je spojina s formulo (I) Cis-2-hidroksimetil-5-(citozin-r-il)-l,3-oksatiolan in njegovi farmacevtsko sprejemljivi derivati.
  8. 8. Postopek po kateremkoli od zahtevkov 1 do 7, označen s tem, da spojino s formulo (I) dobimo v obliki racemne zmesi.
  9. 9. Postopek po kateremkoli od zahtevkov 1 do 7, označen s tem, da spojino s formulo (I) dobimo v obliki posameznega enantiomera.
  10. 10. Postopek po kateremkoli od zahtevkov 1 do 9, označen s tem, da v stopnji (a) skupino L izberemo iz skupine, ki jo sestavljajo alkoksikarbonil, jod, brom, klor ali -OR, kjer je R substituirana ali nesubstituirana, nasičena ali nenasičena alkilna skupina ali je R substituirana ali nesubstituirana alifatska ali aromatska acilna skupina.
  11. 11. Postopek po kateremkoli od zahtevkov 1 do 10, označen s tem, da v stopnji (a) spojina s formulo (VIII) reagira s sililirano purinsko ali pirimidinsko bazo v ustreznem topilu v prisotnosti Lewisove kisline ali trimetilsililtriflata.
  12. 12. Postopek za pripravo farmacevtskega pripravka, označen s tem, da obsega mešanje spojine s formulo (I), kot je definirana v zahtevku 1, ali njenega farmacevtsko sprejemljivega derivata s farmacevtsko sprejemljivim nosilcem. Za BioChem Pharma Inc.:
SI9010243A 1989-02-08 1990-02-08 Substituirani 1,3-oksatiolani z antivirusnimi lastnostmi SI9010243B (sl)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US07/308,101 US5047407A (en) 1989-02-08 1989-02-08 2-substituted-5-substituted-1,3-oxathiolanes with antiviral properties
YU24390A YU48840B (sh) 1989-02-08 1990-02-08 Postupak za dobijanje substituisanih 1,3-oksatiolana sa antivirusnim osobinama
CA002152269A CA2152269C (en) 1989-02-08 1992-12-21 Process for preparing substituted 1,3-oxathiolanes with antiviral properties

Publications (2)

Publication Number Publication Date
SI9010243A SI9010243A (en) 1996-10-31
SI9010243B true SI9010243B (sl) 1998-08-31

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SI9010243A SI9010243B (sl) 1989-02-08 1990-02-08 Substituirani 1,3-oksatiolani z antivirusnimi lastnostmi

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EP (2) EP0382526B1 (sl)
JP (4) JP2644357B2 (sl)
KR (1) KR960007531B1 (sl)
CN (1) CN1033640C (sl)
AP (1) AP136A (sl)
AT (2) ATE138065T1 (sl)
AU (1) AU630913B2 (sl)
CA (1) CA2009637C (sl)
CY (1) CY2036A (sl)
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