LV12188B - 1,4-dihidro-1,4-diokso-1h-naftalīna triciklisku atvasinājumu pielietojums jaunu savienojumu iegūšanai un to izmantošana terapijā - Google Patents

1,4-dihidro-1,4-diokso-1h-naftalīna triciklisku atvasinājumu pielietojums jaunu savienojumu iegūšanai un to izmantošana terapijā Download PDF

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LV12188B
LV12188B LVP-98-136A LV980136A LV12188B LV 12188 B LV12188 B LV 12188B LV 980136 A LV980136 A LV 980136A LV 12188 B LV12188 B LV 12188B
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dihydro
dioxo
thiazole
naphtho
new product
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LV12188A (lv
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Odile Boutherin-Falson
Stephanie Desquand-Billiald
Anita Favrou
Michel Finet
Olivier Tembo
Jean-Luc Torregrosa
Sylvie Yannic-Arnoult
Florence Domagala-Le Marguer
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Laboratoire Innothera
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D235/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/41641,3-Diazoles
    • A61K31/41841,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
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    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/42Oxazoles
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    • A61K31/41Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425Thiazoles
    • A61K31/428Thiazoles condensed with carbocyclic rings
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    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/06Antimigraine agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/14Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
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    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C225/00Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
    • C07C225/24Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings
    • C07C225/26Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings having amino groups bound to carbon atoms of quinone rings or of condensed ring systems containing quinone rings
    • C07C225/30Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings having amino groups bound to carbon atoms of quinone rings or of condensed ring systems containing quinone rings of condensed quinone ring systems formed by two rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C46/00Preparation of quinones
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    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C50/00Quinones
    • C07C50/24Quinones containing halogen
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    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C50/00Quinones
    • C07C50/26Quinones containing groups having oxygen atoms singly bound to carbon atoms
    • C07C50/32Quinones containing groups having oxygen atoms singly bound to carbon atoms the quinoid structure being part of a condensed ring system having two rings
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D263/00Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/60Naphthoxazoles; Hydrogenated naphthoxazoles
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    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00Systems containing two condensed rings
    • C07C2602/02Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04One of the condensed rings being a six-membered aromatic ring
    • C07C2602/12One of the condensed rings being a six-membered aromatic ring the other ring being at least seven-membered

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  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Claims (6)

  1. LV 12188 IZGUDROJUMA FORMULA 1. Triciklisku atvasinājumu un to farmaceitiski pieņemamu sāļu ar vispārējo formulu (I) o
    c kur A ir sēra vai skābekļa atoms; R3N-grupa, kur R3 ir ūdeņraža atoms, CV C5alkilgrupa; aizvietots vai neaizvietots aromātisks gredzens; vai aizvietots vai neaizvietots heteroaromātisks gredzens; Rļ ir CrC5alkilgrupa vai R4NH-grupa, kur R4 ir ūdeņraža atoms; C,-C5alkilgrupa; aizvietots vai neaizvietots aromātisks gredzens; aizvietots vai neaizvietots heteroaromātisks gredzens; aromātisks gredzens, kas var būt aizvietots vai neaizvietots ar vienu vai vairākām akceptora vai donora grupām; vai heteroaromātisks gredzens ar vienu vai vairākiem heteroatomiem, kas var būt aizvietots vai neaizvietots ar akceptora vai donora grupām; R2 ir ūdeņraža vai halogēna atoms, Cļ-Csalkilgrupa; skābekļa atoms, kas var būt aizvietots vai neaizvietots ar C^Csalkilgrupu; vai NR5R5.-grupa, kur R5 un R5· neatkarīgi viena no otras ir ūdeņraža vai skābekļa atoms vai vienvērtīga C,-C5 organiska grupa; pielietojums ārstniecisku preparātu iegūšanā, kas paredzēti slimību, kas saistītas ar venozo funkciju maiņu un/vai iekaisuma tūskas ārstēšanai. 2. 4,9-Dihidro-4,9-diokso-1,2-dimetil-1 H-nafto[2,3-d][sic2,3-d-agrākais]imidazola sulfāts kā jauns produkts. 3. 4,9-Dihidro-4,9-diokso-2-(2-fluorfenil)-1 H-nafto[2,3-d]imidazols kā jauns produkts. 4. 4,9-Dihidro-4,9-diokso-2-(2-fluorfenil)-nafto[2,3-d]oksazols kā jauns produkts. 2 5. 4,9-Dihidro-4,9-diokso-2-(3-fluorfenil)- nafto[2,3-d]oksazols kā jauns produkts. 6. 4,9-Dihidro-4,9-diokso-2-(4-fluorfenil)- nafto[2,3-d]oksazols kā jauns produkts. 7. 4,9-Dihidro-4,9-diokso-2-(2-metilfenil)- nafto[2,3-d]oksazols kā jauns produkts. 8. 4,9-Dihidro-4,9-diokso-2-(3-metilfenil)- nafto[2,3-d]oksazols kā jauns produkts. 9. 4,9-Dihidro-4,9-diokso-2-(4-metilfenil)-nafto[2,3-d]oksazols kā jauns produkts. 10. 2-(2-Hlorfenil)-4,9-dihidro-4,9-diokso-nafto[2,3-d]oksazols kā jauns produkts. 11.2-(4-Hlorfenil)-4,9-dihidro-4,9-diokso-nafto[2,3-d]oksazols kā jauns produkts. 12. 4,9-Dihidro-4,9-diokso-2-(2-tienil)- nafto[2,3-d]oksazols kā jauns produkts. 13. 4,9-Dihidro-4,9-diokso-2-(2-fluorfenil)-nafto[2,3-d]tiazols kā jauns produkts. 14. 4,9-Dihidro-4,9-diokso-2-(3-fluorfenil)-nafto[2I3-d]tiazols kā jauns produkts. 15. 4,9-Dihidro-4,9-diokso-2-(4-fluorfenil)-nafto[2,3-d]tiazols kā jauns produkts. 16. 2-(2,4-Difluorfenil)-4,9-dihidro-4,9-diokso-nafto[2,3-d]tiazols kā jauns produkts. 17. 4,9-Dihidro-4,9-diokso-2-(3-piridil)-nafto[213-d]tiazols kā jauns produkts. 18. 4,9-Dihidro-4,9-diokso-2-(4-piridil)-nafto[2,3-d]tiazola sulfāts kā jauns produkts 19. 4,9-Dihidro-4,9-diokso-2-(3-furil)nafto[213-d]tiazols kā jauns produkts. 20. 2-(5-Hlorfuran-2-ii)-4,9-dihidro-4,9-diokso-nafto[2,3-d]tiazola sulfāts kā jauns produkts. 3 LV 12188 21.4,9*Dihidro-419-diokso-2-(2-tienil)-nafto[213-d]tiazo!s kā jauns produkts. 22. 4,9-Dihidro-4,9-diokso-2-(3-tienil)-nafto[2,3-d]tiazols kā jauns produkts. 23. 4,9-Dihidro-4,9-diokso-2-fenilamino-nafto[2,3-d]tiazols kā jauns produkts. 24. 4,9-Dihidro-4,9-diokso-8-metoksi-2-fenilnafto[2,3-d]tiazols kā jauns produkts. 25. 4,9-Dihidro-4,9-diokso-5-metoksi-2-fenilnafto[2,3-d]tiazols kā jauns produkts. 26. 4,9-Dihidro-4,9-diokso-7-metoksi-2-fenilnafto[2,3-d]tiazols kā jauns produkts. 27. 4,9-Dihidro-4,9-diokso-6-metoksi-2-fenilnafto[2,3-d]tiazols kā jauns produkts. 28. 4,9-Dihidro-4,9-diokso-8-oksi-2-fenilnafto[2,3-d]tiazols kā jauns produkts. 29. 4,9-Dihidro-4,9-diokso-2-(1-pirolil)-nafto[2,3-d]tiazols kā jauns produkts. 30. 2-(5-Bromfuran-2-il)-4,9-dihidro-4,9-diokso-nafto[2)3-d]tiazols kā jauns produkts. 31.2-(4,5-Dibromfuran-2-il)-4,9-dihidro-4,9-diokso-nafto[2,3-d]tiazols kā jauns produkts. 32. 2-(3-Bromfuran-2-il)-4,9-dihidro-4,9-diokso-nafto[2,3-d]tiazols kā jauns produkts. 33. 2-(4-Bromfuran-2-il)-4,9-dihidro-4,9-diokso-nafto[2,3-d]tiazols kā jauns produkts. 34. 4,9-Dihidro-4,9-diokso-2-(5-nitrofuran-2-il)-nafto[2,3-d]tiazols kā jauns produkts. 35. 2-(5-Aminofuran-2-il)-4,9-dihidro-4,9-diokso-nafto[2,3-d]tiazols kā jauns produkts. 4 36. 2-(5-Acetamidofuran-2-il)-4,9-dihidro-4,9-diokso-nafto[2I3-d]tiazols kā jauns produkts. 37. 4,9-Dihidro-4,9-diokso-2-(5-oksimetilfuran-2-il)-nafto[2,3-d]tiazols kā jauns produkts. 38. 2-(5-Acetoksimetilfuran-2-il)-4,9-dihidro-4,9-diokso-nafto[2,3-d]tiazols kā jauns produkts. 39. 4,9-Dihidro-4,9-diokso-2-(5-metil-2-furil)-nafto[2,3-d]tiazols kā jauns produkts. 40. 4,9-Dihidro-4,9-diokso-2-(4,5-dimetil-2-furil)-nafto[2,3-d]tiazols kā jauns produkts. 41.4,9-Dihidro-4,9-diokso-2-(5-fenil-2-oksazolil)-nafto[2,3-d]tiazols kā jauns produkts. 42. 4,9-Dihidro-4,9-diokso-2-(2-tiazolil)-nafto[2,3-d]tiazois kā jauns produkts. 43. 4,9-Dihidro-4I9-diokso-6-fluor-2-(2-furil)-nafto[2,3-d]tiazols kā jauns produkts. 44. 4,9-Dihidro-4I9-diokso-7-fluor-2-(2-furil)-nafto[2,3-d]tiazols kā jauns produkts. 45. 4,9-Dihidro-4I9-diokso-6-fluor-2-fenilnafto[2,3-d]tiazols kā jauns produkts. 46. 4,9-Dihidro-4,9-diokso-7-fluor-2-fenilnafto[2)3-d]tiazols kā jauns produkts. 47. 419-Dihidro-4,9-diokso-6-fluor-2-(5-metil-2-furil)nafto[2,3-d]tĪazols kā jauns produkts. 48. 4,9-Dihidro-4,9-diokso-7-fluor-2-(5-metil-2-furil)-nafto[2,3-d]tiazols kā jauns produkts. 5 LV 12188 49. 4,9-Dihidro-4,9-diokso-6-fluor-2-(4-fluorfenil)-nafto[2,3-d]tiazols kā jauns produkts. 50. 4,9-Dihidro-4,9-diokso-7-fluor-2-(4-fluorfenil)-nafto[2,3-d]tiazols kā jauns produkts. 51.4.9- Dihidro-4,9-diokso-6-fluor-2-(4-metilfenil)-nafto[2,3-d]tiazols kā jauns produkts. 52. 4,9-Dihidro-4,9-diokso-7-fluor-2-(4-metilfenil)-nafto[2,3-d]tiazols kā jauns produkts. 53. 4,9-Dihidro-4,9-diokso-5-fluor-2-(2-furil)-nafto[2,3-d]tiazols kā jauns produkts. 54. 4,9-Dihidro-4,9-diokso-8-fluor-2-(2-furil)-nafto[2,3-d]tiazols kā jauns produkts. 55. 6-Hlor-4,9-dihidro-4,9-diokso-2-(2-furil)-nafto[2,3-d]tiazols kā jauns produkts. 56. 7-Hlor-4,9-dihidro-4)9-diokso-2-(2-furil)-nafto[2,3-d]tiazols kā jauns produkts. 57. 4,9-Dihidro-4,9-diokso-2-(2-furil)-5-metoksinafto[2,3-d]tiazols kā jauns produkts. 58. 419-Dihidro-4>9-diokso-2-(2-furil)-8-metoksinafto[2,3-d]tiazols kā jauns produkts. 59. 4,9-Dihidro-4,9-diokso-2-(2-furil)-5-oksinafto[2,3-d]tiazols kā jauns produkts. 60. 4,9-Dihidro-4,9-diokso-2-(2-furil)-8-oksinafto[2,3-d]tiazols kā jauns produkts. 61.4.9- Dihidro-4,9-diokso-2-(2-furil)-6-metoksinafto[2.3-d]tiazols kā jauns produkts. 62. 4,9-Dihidro-4,9-diokso-2-(2-furil)-7-metoksinafto[2.3-d]tiazols kā jauns produkts. 6 63. 4,9-Dihidro-4,9-diokso-2-furil-6-metilnafto[2,3-d]tiazols kā jauns produkts. 64. 4,9-Dihidro-4,9-diokso-2-furil-7-metilnafto[2,3-d]tiazols kā jauns produkts. 65. 4,9-Dihidro-4,9-diokso-6-metil-2-fenilnafto[2,3-d]tiazols kā jauns produkts. 66. 4,9-Dihidro-4,9-diokso-7-metil-2*fenilnafto[2,3-d]tiazols kā jauns produkts. 67. 4,9-Dihidro-4>9-diokso-2-furil-5-metilnafto[2,3-d]tiazols kā jauns produkts. 68. 4,9-Dihidro-4,9-diokso-2-furil-8-metilnafto[2,3-d]tiazols kā jauns produkts. 69. 4)9-Dihidro-4,9-diokso-5-metil-2-fenilnafto[2,3-d]tiazols kā jauns produkts. 70. 4,9-Dihidro-4,9-diokso-8-metil-2-fenilnafto[2,3-d]tiazols kā jauns produkts. 71. 1,4-Dihidro-1,4-diokso-5-metoksinaftalīns kā jauns starpprodukts. 72. 2,3-Dibrom-1,4-dihidro-1,4-diokso-5-metoksinaftalīns kā jauns starpprodukts. 73. 2-Amino-3-brom-1,4-dihidro-1,4-diokso-5-metoksinaftalīns kā jauns starpprodukts. 74. 2-Amino-3-brom-1,4-dihidro-1,4-diokso-8-metoksinaftalīns kā jauns starpprodukts. 75. 2,3-Dibrom-1,4-dihidro-1,4-diokso-6-fluornaftalīns kā jauns starpprodukts. 76. 2-Amino-3-brom-l,4-dihidro-1,4-diokso-6-fluornaftalīns kā jauns starpprodukts. 77. 2-Amino-3-brom-7-fluor-1,4-dihidro-1,4-diokso-7-fIuornaftalīns kā jauns starpprodukts. 7 LV 12188 78. 2,3-Dibrom-1,4-dihidro-1,4-diokso-5-fluornaftalTns kā jauns starpprodukts. 79. 2-Amino-3-brom-5-fluor-1,4-dihidro-1,4-diokso-naftalīns kā jauns starpprodukts. 80. 2-Amino-3-brom-8-fluor-1,4-dihidro-1,4-diokso-naftalīns kā jauns starpprodukts. 81. 2-Amino-3-hlor-1,4-dihidro-1,4-diokso-6-metilnaftalīns kā jauns starpprodukts. 82. 2-Amino-3-hlor-1,4-dihidro-1,4-diokso-7-metilnaftalīns kā jauns starpprodukts. 83. 2,3-Dibrom-1,4-dihidro-1,4-diokso-5-metilnaftalīns kā jauns starpprodukts. 84. 2-Amino-3-brom-1,4-dihidro-l ,4-diokso-5-metilnaftalīns kā jauns starpprodukts. 85. 2-Amino-3-brom-1,4-dihidro-1,4-diokso-8-metilnaftalīns kā jauns starpprodukts.
  2. 86. Savienojumu saskaņā ar vienu no 1 .-70. punktiem pielietojums ārstnieciska preparāta iegūšanai, kas paredzēts funkcionālās vai organiskās venozās nepietiekamības ārstēšanai.
  3. 87. Savienojumu saskaņā ar vienu no 1 .-70. punktiem pielietojums ārstnieciska preparāta iegūšanā, kas paredzēts hemoroīdu ārstēšanai.
  4. 88. Savienojumu saskaņā ar vienu no 1.-70. punktiem pielietojums ārstnieciska preparāta iegūšanā, kas paredzēts migrēnas ārstēšanai.
  5. 89. Savienojumu saskaņā ar vienu no 1.-70. punktiem pielietojums ārstnieciska preparāta iegūšanā, kas paredzēts dermatoloģijas un sirds asinsvadu un kaulu-locītavu iekaisumu ārstēšanai. 8
  6. 90. Savienojumu saskaņā ar vienu no 1 .-70. punktiem pielietojums ārstnieciska preparāta iegūšanā, kas paredzēts šoka stāvokļa, kas saistīts ar arteriāla spiediena lielu kritumu, it īpaši septiska šoka stāvokļa ārstēšanai.
LVP-98-136A 1995-12-12 1998-06-12 1,4-dihidro-1,4-diokso-1h-naftalīna triciklisku atvasinājumu pielietojums jaunu savienojumu iegūšanai un to izmantošana terapijā LV12188B (lv)

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FR9514683A FR2742153B1 (fr) 1995-12-12 1995-12-12 Utilisation de derives tricycliques du 1,4-dihydro-1,4- dioxo-1h-naphtalene, nouveaux composes obtenus et leur application en therapeutique
PCT/FR1996/001973 WO1997021684A1 (fr) 1995-12-12 1996-12-10 Utilisation de derives tricycliques du 1,4-dihydro-1,4-dioxo-1h-naphtalene, nouveaux composes obtenus et leur application en therapeutique

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US7754463B2 (en) 2006-06-20 2010-07-13 Dana-Farber Cancer Institute Inhibitors of USP1 Deubiquitinating Enzyme Complex
CA2797719C (en) 2010-04-30 2019-11-26 Dana-Farber Cancer Institute, Inc. Small molecule inhibitors of usp1 deubiquitinating enzyme activity
US9040713B2 (en) * 2010-09-27 2015-05-26 Emory University Methods of managing blood sugar levels and compositions related thereto
US9725425B1 (en) 2014-02-25 2017-08-08 Dana-Farber Cancer Institute, Inc. Compounds and methods for treating cancer
RU2545091C1 (ru) * 2014-03-18 2015-03-27 Федеральное государственное бюджетное учреждение "Российский онкологический научный центр имени Н.Н. Блохина" Российской академии медицинских наук (ФГБУ "РОНЦ им. Н.Н. Блохина" РАМН) 1-R-4,9-ДИОКСО-1H-НАФТО[2,3-d][1,2,3]ТРИАЗОЛ-4-ОКСИМ-2-ОКСИДЫ И ИХ ПРОИЗВОДНЫЕ, ОБЛАДАЮЩИЕ ЦИТОТОКСИЧЕСКОЙ АКТИВНОСТЬЮ
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EP0876356B1 (fr) 2001-10-31
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NO982696L (no) 1998-08-11
NO982696D0 (no) 1998-06-11
HUP9901247A3 (en) 2000-08-28
LV12188A (lv) 1998-12-20
HUP9901247A2 (hu) 1999-08-30
AU716199B2 (en) 2000-02-24
RU2178791C2 (ru) 2002-01-27
WO1997021684A1 (fr) 1997-06-19
KR19990072080A (ko) 1999-09-27
LT4491B (lt) 1999-04-26
AP9801275A0 (en) 1998-06-30
OA10696A (fr) 2002-11-26
US6262095B1 (en) 2001-07-17
CA2240279A1 (fr) 1997-06-19
LT98085A (en) 1998-11-25
ID16081A (id) 1997-09-04
FR2742153B1 (fr) 1998-02-13
NZ323967A (en) 2000-06-23
AP889A (en) 2000-11-17
EP0876356A1 (fr) 1998-11-11
FR2742153A1 (fr) 1997-06-13

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