SI9110745B - Anti-viral compounds. - Google Patents

Anti-viral compounds. Download PDF

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SI9110745B
SI9110745B SI9110745A SI9110745A SI9110745B SI 9110745 B SI9110745 B SI 9110745B SI 9110745 A SI9110745 A SI 9110745A SI 9110745 A SI9110745 A SI 9110745A SI 9110745 B SI9110745 B SI 9110745B
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compound
formula
group
glycero
pharmaceutically acceptable
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SI9110745A
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SI9110745A (en
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Itzstein Laurence Mark Von
Tho Van Phan
Betty Jin
Wen-Yang Wu
Basil Danylec
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Biota Scient Management
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/30—Oxygen atoms, e.g. delta-lactones
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms

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

Claims (34)

  1. \ PATENTNI ZAHTEVKI 1. Spojina s formulo (I) ali s formulo (la)
    Q9) označena s tem, da je v splošni formuli (I) A kisik, ogljik ali žveplo, v splošni formuli (la) pa je A dušik ali ogljik; R1 pomeni COOH, P(0)(0H),, NO,, SOOH, S03H, tetrazol, CH2CHO, CHO ali CH(CHO),, R2 pomeni H, OR", F, Cl, Br, CN, NHR6, SR" ali CH,X, kjer je X NHR6, halogen ali OR6 in R6 je vodik; acilna skupina z 1 do 4 atomi ogljika; ravna ali ciklična alkilna skupina z 1 do 6 atomi ogljika ali njen s halogenom substituiran analog, alilna skupina ali nesubstituirana arilna skupina ali arilna skupina, substituirana s halogenom, skupina OH, skupina NO„ skupina NH, ali skupina COOH, R3 in R3’ sta enaka ali različna in vsak pomeni vodik, CN, NHR6, Ny SR6, =N-OR6, OR6, gvanidino,
    z R4 pomeni NHR6, SR6, OR°, C00R6, NOr C(R% CH,COOR6, CH2N02 ali CH2NHR6, in R5 pomeni CH,YR'\ CHYR6CH,YR6 ali CHYR6CHYR6CH2YR6 ali CHYR6CHYR6CH,CN, kjer je Y O, S. NH ali H, zaporedni Y deli v skupini R5 pa so enaki ali različni, in njihove farmacevtsko sprejemljive soli ali derivate, pod pogojem, da v splošni formuli (I), (i) kadar je R3 ali R3 OR6 ali vodik in je A kisik ali žveplo, takrat navedena spojina ne moremo imeti tudi (a) R2, ki je vodik in (b) R4, kije O-acil ali NH-acil, in (ii) R6 predstavlja kovalento vez, kadar je Y vodik, in kadar v splošni formuli (la), (i) kadar je R3 ali Rr OR6 ali vodik in A dušik, takrat navedena spojina ne more imeti oba tudi (a) R2, kije vodik in (b) R4, kije NH-acil, in (ii) R6 predstavlja kovalentno vez, kadar je Y vodik.
  2. 2. Spojina po zahtevku 1, označena s tem, da je spojina spojina s formulo (II) HO OH
    kjer je R3 je vodik ali R3’, kjer Ry pomeni -Ny -CN, -CH2NH2, ali -N.R8.R9; R8 in R9 sta enaka ali različna in vsak pomeni vodik, ravno ali ciklično alkilno skupino z 1 do 6 atomi ogljika, acilno ali substituirano acilno skupino z 1 do 6 atomi ogljika, -C(NH).NH2, -CH2.COOH, -CH2CH2-OH ali -CHrCH.(R10)(Ru), R10 in R11 sta enaka ali različna in vsak pomeni kisik ali Rl2N=, in R12 pomeni vodik, -OH, -OCHv -NH, ali (CH.,),N-, ali njena farmacevtsko sprejemljiva sol ali derivat.
  3. 3. Spojina po zahtevku 1 ali zahtevku 2, označena s tem, da je R3 NHR6.
  4. 4. Spojina po enem od zahtevkov 1 do 3, označena s tem, da je R3 NH NH2 ali nh-c-nh2
  5. 5. Spojina po zahtevku 1, označena s tem, dajo izberemo iz skupine, v kateri so: natrijev 5-acetamido-4-azido-2,3,4,5-tetradezoksi-D-glicero-D-galakto-non-2-enopiranozonat (4-azido-Neu5Ac2en); natrijev 5-acetamido-4-N-aIilamino-2,3,4,5-tetra-dezoksi-D-glicero-D-galakto-non-2-enopiranozonat natrijev 5-acetamido-4-amino-2,3,4,5-tetradezoksi-D-glicero-D-talo-non-2-enopiranozonat; (4-epi-amino-Neu4Ac2en); metil 5-acetamido-7,8,9-tri-0-acetiI-4-N,N-dialil-amino-2,3,4,5- tetradezoksi-D-glicero-D-galakto-non-2-enopiranozonat (4-N,N-dialilamino-Neu5,7,8,9Ac^2enlMe); natrijev 5-acetamidO“4-N,N-dialilamino-2,3,4,5-tetradezoksi-D-glicero-D-galakto-non-2-enopiranozonat k metil5-acetamido-7,8,9-tri-0-acetil-4-N-alilamino-2,3,4,5- tetradezoksi-D-glicero-D-galakto-non-2-enopiranozonat (4-N-alilamino-Neu5,7,8,9Ac,2enlMe); natrijev 5-acetamido-4-N,N-dimetilamino-2,3,4,5-tetradezoksi-D-glicero-D-galakto-non-2-enopiranozonat; natrijev 2,3-didezoksi-D-glicero-D-galakto-non-2-enopiranozonat; metil 5-acetamido-7,8,9-tri-0-acetil-4-azido-2,3,4,5- tetradezoksi-D-glicero-D-talo-non-2-enopiranozonat (4-epiazido-Neu5,7,8,9Ac42enlMe).
  6. 6. Farmacevtski preparat, označen s tem, da obsega spojino s formulo (I) ali (la), kot je definirano v zahtevkih 1 do 5, ali njeno farmacevtsko sprejemljivo sol ali derivat skupaj s farmacevtsko sprejemljivim nosilcem za ta namen.
  7. 7. Farmacevtski preparat po zahtevku 6, označen s tem, da je preparat prilagojen za intranazalno dajanje.
  8. 8. Uporaba spojine s formulo (I) ali (la), kot je definirana v zahtevku 1, za pripravo zdravil za zdravljenje virusnih infekcij.
  9. 9. Uporaba spojin po zahtevku 8, označena s tem, da je virusna infekcija influenca.
  10. 10. Uporaba spojine s formulo (I) ali s formulo (la)
    kjer je v splošni formuli (I) A kisik, ogljik ali žveplo, v splošni formuli (la) pa je A dušik ali ogljik; R1 pomeni COOH, P(0)(OH)2, N02, SOOH, S03H, tetrazol, CP^CHO ali CH(CHO)2, R2 pomeni H, OR6, F, Cl, Br, CN, NHR6, SR6 ali Ο^Χ, kjer je X NHR6, halogen ali OR6 in R6 je vodik; acilna skupina z 1 do 4 atomi ogljika; ravna ali ciklična alkilna skupina z 1 do 6 atomi ogljika ali njen s halogenom substituiran analog, alilna skupina ali nesubstituirana arilna skupina ali arilna skupina, substituirana s halogenom, skupina OH, skupina N02, skupina Nl·^ ali skupina COOH, R3 in R3’ sta enaka ali različna in vsak pomeni vodik, CN, NHR6, Ny SR6, =N-OR6, OR6, gvanidino,
    R4 pomeni NHR6, SR6, OR6, COOR6, NO,, C(R6)3, CHjCOOR6, CH2N02 ali CP^NHR6, in R5 pomeni CP^VR6, CHVR^VR6 ali CHYR6CHYR6CH2YR6, Iger je Y O, S, NH ali H, zaporedni Y deli v skupini R5 pa so enaki ali različni, ali njene farmacevtsko sprejemljive soli ali derivata skupaj s farmacevtsko sprejemljivim nosilcem za pripravo zdravila za zdravljenje sesalca, vključno tudi človeka, z virusnimi infekcijami.
  11. 11. Uporaba spojine s formulo (I) ali (la), kot je definirano v zahtevku 1, za 6 pripravo zdravila za zdravljenje sesalca, vključno tudi človeka, z virusnimi infekcijami.
  12. 12. Uporaba po zahtevku 11, označen s tem, da je virusna infekcija influenca.
  13. 13. Uporaba po zahtevku 10 ali 11, označena s tem, da gre za infekcijo z respiratornim virusom.
  14. 14. Uporaba po kateremkoli od zahtevku 10 do 13, označena s tem, da aktivno komponento dajemo v respiratorni trakt.
  15. 15. Uporaba po kateremkoli od zahtevku 10 do 14, označena s tem, da aktivno komponento dajemo intranazalno.
  16. 16. Postopek za pripravo spojine s formulo (I), kot je definirana v zahtevku 1, označen s tem, da obsega stopnje, kot so (A) reakcija spojine s formulo (III) OL
    v kateri so R1, R2, R4 in R5 definirani v zahtevku 1, L pa je odhodna skupina, z nuk-leofilom; ali (B) interkonverzija ene spojine s formulo (I) v drugo spojino s formulo (I) in po potrebi ali po želji dobljeno spojino podvržemo eni ali dvema nadaljnjima reakcijama, ki obsegata: (i) odstranjevanje katerihkoli zaščitnih skupin; (ii) pretvorbo spojine s formulo (I) ali njene soli v njeno farmacevtsko sprejemljivo soL
  17. 17. Spojina, označena s tem, da ima formulo (Ib)
    kjer je R3b CN ali N3, kjer je alk nesubstituiran ali substituiran metilen, xje 0 ali 1, R6b je vodik, C^alkil, aril, aralkil, amidin, NR7bR8b ali nenasičen ali nasičen obroč, ki vsebuje enega ali več heteroatomov (kot so dušik, kisik ali žveplo), R7b je vodik, C16alkil ali alil; R8b je vodik ali C16alkil in je qsR4b NHCOR9b, kjer je R9b vodik, substituiran ali nesubstituiran C14alkil ali aril, ali njena farmacevtsko sprejemljiva sol ali derivat.
  18. 18. Spojina po zahtevku 17, označena s tem, daje R3b NH2 ali NHC(=NH)NHr 19. 5-acetamido-4-amino-2,3,4,5-tetradezoksi-D-glicero-D-galakto-non-2-enopiranozonska kislina ter njene farmacevtsko sprejemljive soli in derivati.
  19. 20. Natrijev 5-acetamido-4-amino-2,3,4,5-tetradezoksi-D-glicero-D-galakto-non-2-enopiranozonat. 21. 5-acetamido-4-gvanidino-2,3,4,5-tetradezoksi-D-glicero-D-galakto-non-2-enopiranozonska kislina in njene farmacevtsko sprejemljive soli in derivati.
  20. 22. Amonijev 5-acetamido-4-gvanidino-2,3,4,5-tetradezoksi-D-glicero-D-galakto-non-2-enopiranozonat.
  21. 23. Farmacevtski preparat, označen s tem, da obsega spojino po kateremkoli od zahtevkov 17 do 22, kot aktivno komponento skupaj s farmacevtsko sprejemljivim nosilcem za ta namen. t
  22. 24. Farmacevtski preparat, označen s tem, da je primeren za nazalno dajanje, ki obsega spojino po kateremkoli od zahtevkov 17 do 22, kot aktivno komponento skupaj s farmacevtsko sprejemljivim nosilcem za ta namen.
  23. 25. Farmacevtski preparat po zahtevku 23, ali 24, označen s tem, daje aktivna komponenta 5-acetamido-4-amino-2,3,4,5-tetradezoksi-D-glicero-D-galakto-non-2-enopiranozonska kislina ali njena farmacevtsko sprejemljiva sol.
  24. 26. Farmacevtski preparat po zahtevku 23 ali zahtevku 24, označen s tem, da je aktivna komponenta 5-acetamido-4-gvanidino-2,3,4,5-tetradezoksi-D-glicero-D-galakto-non-2-enopiranozonska kislina ali njena farmacevtsko sprejemljiva sol.
  25. 27. Uporaba spojine po kateremkoli od zahtevkov 17 do 22 za pripravo zdravila za zdravljenje sesalca, vključno tudi človeka, ki ima virusno infekcijo.
  26. 28. Uporaba po zahtevku 27, označena s tem, da je infekcija virusna respiratorna infekcija.
  27. 29. Uporaba po zahtevku 27 ali 28, označena s tem, da je virusna infekcija influenca.
  28. 30. Uporaba po kateremkoli od zahtevkov 27 do 29, označena s tem, da aktivno komponento dajemo v respiratorni trakt.
  29. 31. Uporaba po kateremkoli od zahtevkov 27 do 30, označena s tem, da aktivno komponento dajemo intranazalno.
  30. 32. Uporaba po kateremkoli od zahtevkov 27 do 31, označena s tem, daje spojina 5-acetamido-4-amino-2,3,4,5-tetradezoksi-D-glicero-D-galakto-non-2-enopiranozon-ska kislina ali njena farmacevtsko sprejemljiva sol.
  31. 33. Uporaba po kateremkoli od zahtevkov 27 do 31, označena s tem, da je spojina 5-acetamido-4-gvanidino-2,3,4,5-tetradezoksi-D-glicero-D-galakto-non-2-enopirano-zonska kislina ali njena farmacevtsko sprejemljiva sol.
  32. 34. Uporaba spojine po kateremkoli od zahtevkov 17 do 22 za pripravo zdravil za 4 zdravljenje virusnih infekcij.
  33. 35. Spojina po kateremkoli od zahtevkov 17 do 22 za uporabo za zdravljenje virusnih infekcij.
  34. 36. Postopek za pripravo spojin s formulo (Ib), kot je definirano v kateremkoli od zahtevkov 17 do 22, označen s tem, da obsega stopnje, kot so (A) reakcija spojine s formulo (Illb) CH OL·
    v kateri je R4b, kot je definirano v zahtevku 17, L pa je odhodna skupina, ali zaščitenega derivata navedene spojine z nukleofilom; ali (B) interkonverzija ene spojine s formulo (Ib) v drugo spojino s formulo (Ib) in po potrebi dobljeno spojino podvržemo eni ali dvema nadaljnjima reakcijama, ki obsegata: (i) odstranjevanje katerihkoli zaščitnih skupin; (ii) pretvorbo spojine s formulo (Ib) ali njene soli v njeno farmacevtsko sprejemljivo sol. Za BIOTA SCIENTIFIC MANAGEMENT ΡΤΥ LTD psT-' " "·'..... ·,·8 io*.
SI9110745A 1990-04-24 1991-04-24 Anti-viral compounds. SI9110745B (en)

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AUPJ980090 1990-04-24
AUPK289690 1990-10-19
AUPK453791 1991-02-11
YU74591A YU48741B (sh) 1990-04-24 1991-04-24 Derivati i analozi 2-dezoksi-2,3-didehidro-n-acetil-neuraminske kiseline i postupak za njihovo dobijanje

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SI9110745B true SI9110745B (en) 2001-06-30

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