DK2343304T3 - Biocide boronophthalidforbindelser - Google Patents

Biocide boronophthalidforbindelser Download PDF

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DK2343304T3
DK2343304T3 DK11154575.2T DK11154575T DK2343304T3 DK 2343304 T3 DK2343304 T3 DK 2343304T3 DK 11154575 T DK11154575 T DK 11154575T DK 2343304 T3 DK2343304 T3 DK 2343304T3
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benzoxaborol
hydroxy
compound
dihydro
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Stephen Baker
Tsutomu Akama
Carolyn Bellinger-Kawahara
Vincent Hernandez
Karin Hold
James Leyden
Kirk Maples
Jacob Plattner
Virginia Sanders
Yong-Kang Zhang
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Anacor Pharmaceuticals Inc
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Claims (38)

  1. (Ilb) PATENTKRAV 1. Forbindelse til terapeutisk anvendelse, hvilken forbindelse har en struktur ifølge formel (Ilb):
    hvor R7b er et element udvalgt fra H, methyl, ethyl og phenyl; R10b er et element udvalgt fra H, OH, NH2, SH, halogen, substitueret eller ikke-substitueret phenoxy, substitueret eller ikke-substitueret phenylalkyloxy, substitueret eller ikke-substitueret phenylthio og substitueret eller ikke-substitueret phenylalkylthio; og Rllb er et element udvalgt fra H, OH, NH2, SH, methyl, substitueret eller ikke-substitueret phenoxy, substitueret eller ikke-substitueret phenylalkyloxy, substitueret eller ikke-substitueret phenylthio og substitueret eller ikke-substitueret phenylalkylthio, hvor begrebet "alkyl" en en Ci-Cio-alkylgruppe; hvor substituenter for de forskellige opførte alkylgrupper er udvalgt fra: -OR', =0, =NR', =N-OR’, -NR'R", -SR’, -halogen, -0C(0)R’, -C(0)R', -C02R', -CONR'R", -0C(0)NR’R", -NR"C(0)R', -NR'-C(0)NR"R"', -NR"C(0)2R’, -NR-C(NR’R"R'")=NR"", -NR-C(NR'R")=NR"', -S(0)R', -S(0)2R', -S(0)2NR'R", -NRS02R', -CN og -N02 i et antal, der ligger fra nul til (2m'+l), hvor m’ er det totale antal carbonatomer i en sådan radikal, og hvor R', R", R"' og R"" hver uafhængigt henviser til hydrogen-, heteroalkyl-, aryl-, alkyl-, alkoxy-, thioalkoxy- eller arylalkylgrupper; og hvor substituenter for de forskellige opførte substituerede arylgrupper er udvalgt fra gruppen bestående af: halogen, -OR’, =0, =NR', =N-OR’, -NR’R", -SR’, -0C(0)R’, -C(0)R’, -C02R’, -CONR'R", -0C(0)NR'R", -NR"C(0)R', -NR'-C(0)NR"R"', - NR"C(0)2R', -NR- C(NR'R"R"’)=NR"", -NR-C(NR'R")=NR"', -S(0)R’, -S(0)2R’, - S(0)2NR’R", -NRS02R’, -CN og -N02, -R', -N3, -CH(Ph)2, fluor(Ci-C4)alkoxy og fluor(Ci-C4)alkyl, i et antal, der ligger fra nul til det totale antal åbne valenser; og hvor R', R", R"' og R"" uafhængigt er udvalgt fra hydrogen, alkyl, heteroalkyl, aryl og heteroaryl.
  2. 2. Forbindelse til anvendelse ifølge krav 1, hvor R10b er et element udvalgt fra OH, NH2, SH, halogen, substitueret eller ikke-substitueret phenoxy, substitueret eller ikke-substitueret phenylalkyloxy, substitueret eller ikke-substitueret phenylthio og substitueret eller ikke-substitueret phenylalkylthio.
  3. 3. Forbindelse til anvendelse ifølge krav 1, hvor ét element udvalgt Ira R10b og Rllb er H og det andet element udvalgt fra R10b og Rllb er et element udvalgt fra halo, methyl og p-cyanphenyloxy.
  4. 4. Forbindelse til anvendelse ifølge krav 1, hvor R7b er H.
  5. 5. Forbindelse til anvendelse ifølge krav 1, hvor R10b er substitueret phenoxy.
  6. 6. Forbindelse til anvendelse ifølge krav 1, hvor R1 lb er H.
  7. 7. Forbindelse til anvendelse ifølge krav 1, der er et element udvalgt fra 5-(4-cyanphenoxy)-l,3- dihydro-l-hydroxy-2,l-benzoxaborol, 6-(4-cyanphenoxy)-l,3-dihydro-l-hydroxy-2,l- benzoxaborol, 6-(3 -cyanphenoxy)-1,3 -dihydro-1 -hydroxy-2,1 -benzoxaborol, 6-(4- chlorphenoxy)-1,3-dihydro-1 -hydroxy-2,1 -benzoxaborol, 5-(4-cyanobenzyloxy)-l,3-dihydro-l -hydroxy-2,1-benzoxaborol, 5-(2-cyanphenoxy)-l,3-dihydro-l-hydroxy-2,1-benzoxaborol, 5-[4-(N,N-diethylcarbamoyl)phenoxy]-l,3-dihydro-l -hydroxy-2,1 -benzoxaborol, 1,3-dihydro-l - hydroxy-5-[4-(morpholincarbonyl)phenoxy]-2,l-benzoxaborol, 5-(3,4-dicyanphenoxy)-l,3-dihydro-1 -hydroxy-2,1 -benzoxaborol, 6-phenylthio-1,3 -dihydro-1 -hydroxy-2,1 -benzoxaborol, 6-(4-trifluormethoxyphenoxy)-1,3 -dihydro-1 -hydroxy-2,1 -benzoxaborol, 6-(4- methoxyphenoxy)-l,3-dihydro-l-hydroxy-2,1-benzoxaborol, 6-(4-methoxyphenylthio)-l,3-dihydro-1 -hydroxy-2,1 -benzoxaborol, 5-(3 -cyanphenoxy)-1,3-dihydro-1 -hydroxy-2,1 - benzoxaborol, 5-(4-carboxyphenoxy)-1 -hydroxy-2,1 -benzoxaborol, 1 -hydroxy-5-[4-(tetrazol-1 -yl)phenoxy]-2,1 -benzoxaborol.
  8. 8. Forbindelse til anvendelse ifølge krav 1, der er et element udvalgt fra 5-(4-cyanphenoxy)-l,3- dihydro-1 -hydroxy-2,1 -benzoxaborol, 6-(4-cyanphenoxy)-l ,3-dihydro-1 -hydroxy-2,1 - benzoxaborol, 6-(3 -cyanphenoxy)-1,3 -dihydro-1 -hydroxy-2,1 -benzoxaborol, 5-(2- cyanphenoxy)-l,3-dihydro-l-hydroxy-2,1-benzoxaborol, 5-(3,4-dicyanphenoxy)-l,3-dihydro-l-hydroxy-2,1 -benzoxaborol og 5-(3-cyanphenoxy)-l,3-dihydro-1 -hydroxy-2,1 -benzoxaborol.
  9. 9. Forbindelse til anvendelse ifølge krav 1, der er 5-(4-cyanphenoxy)-1,3-dihydro-1-hydroxy-2,1-benzoxaborol.
  10. 10. Forbindelse til anvendelse ifølge krav 1, der er 5-(3,4-dicyanphenoxy)-l,3-dihydro-l-hydroxy-2, 1 -benzoxaborol.
  11. 11. Forbindelse til anvendelse ifølge et hvilket som helst af de foregående krav i en form, der er et element udvalgt lfa et hydrat med vand, et solvat med en alkohol, et addukt med en aminoforbindelse og et addukt med en syre.
  12. 12. Forbindelse til terapeutisk anvendelse, hvilken forbindelse er som defineret i et hvilket som helst af kravene 1 til 10 i form af et farmaceutisk acceptabelt salt, eventuelt hvor saltet er et baseadditionssalt opnået ved at etablere kontakt mellem den neutrale form af en sådan forbindelse med en tilstrækkelig mængde af den ønskede base i et egnet inert opløsningsmiddel.
  13. 13. Farmaceutisk formulering omfattende: a) en forbindelse som defineret i et hvilket som helst af kravene 1 til 10; og b) en farmaceutisk acceptabel excipiens deraf.
  14. 14. Farmaceutisk formulering ifølge krav 13, hvor excipiensen er et farmaceutisk acceptabelt topisk bærestof.
  15. 15. Farmaceutisk formulering ifølge krav 13 eller krav 14, hvor formuleringen er et element udvalgt fra en lak, lotion, cream, gel, salve, stick, pasta, skum, mousse og spray, eventuelt hvor formuleringen er en salve og endvidere eventuelt hvor sprayen tilvejebringer forbindelsen ifølge et hvilket som helst af kravene 1 til 10 i en vandig og/eller alkoholopløsning.
  16. 16. Farmaceutisk formulering ifølge et hvilket som helst af kravene 13 til 15, hvor formuleringen endvidere omfatter ét eller flere elementer udvalgt fra et emulgeringsmiddel, blødgøringsmiddel, antioxidant, konserveringsmiddel, chelateringsmiddel, neutraliseringsmiddel, viskocitetsforbedrende middel, penetrationsforbedrende middel, antiinflammatorisk middel, vitamin, antiældningsmiddel, en solcreme og et acnebehandlingsmiddel, og/eller hvor formuleringen endvidere omfatter et element udvalgt fra gruppen bestående af et fortykningsmiddel, en gelfasebærer, neglepenetrationsforbedrende middel og et viskocitetsforbedrende middel.
  17. 17. Farmaceutisk formulering ifølge et hvilket som helst af kravene 13 til 16, hvor formuleringen omfatter et chelateringsmiddel, eventuelt hvor chelateringsmidlet er udvalgt fra gruppen udvalgt fra citronsyre, ethylendiamintetraeddikesyre (EDTA), ethylenglycol-bis(beta-aminoethylether)- N, N,N',N'tetraeddikesyre (EGTA) og 8-amino-2-[(2-amino-5-methylphenoxy)methyl]-6-methoxyquinolin-N,N,N',N'-tetraeddikesyre, tetrakaliumsalt (QUIN-2), og/eller hvor chelateringsmidlet er til stede i en mængde på mellem 0,005 % til 2 vægt-%.
  18. 18. Farmaceutisk formulering ifølge krav 17, hvor chelateringsmidlet er ethylendiamintetraeddikesyre.
  19. 19. Farmaceutisk formulering ifølge et hvilket som helst af kravene 13 til 18, hvor formuleringen omfatter en antioxidant, eventuelt hvor antioxidanten er udvalgt fra gruppen bestående af butyleret hydroxytoluen, ascorbinsyre, natriumascorbat, calciumascorbat, ascorbinpalmitat, butyleret hydroxyanisol, 2,4,5-trihydroxybutyrophenon, 4-hydroxymethyl-2,6-di-fert-butylphenol, erythorbinsyre, guajakharpiks, propylgallat, thiodipropionsyre, dilaurylthiodipropionat, tert-butylhydroquinon og tocopheroler, såsom vitamin E, og lignende, indbefattende farmaceutisk acceptable salte og estere af disse forbindelser, eventuelt hvor antioxidanten er butyleret hydroxytoluen, og endvidere eventuelt hvor antioxidanten er til stede i en mængde på fra ca. 0,001 til 0,5 vægt-%, fortrinsvis 0,05 til ca. 0,5 vægt-%, mere fortrinsvis O, 1 %.
  20. 20. Farmaceutisk formulering ifølge et hvilket som helst af kravene 13 til 19, hvor formuleringen omfatter petroleum eller petroleumderivat, og/eller hvor formuleringen omfatter et element udvalgt fra cetearylalkohol, cetylalkohol, stearylalkohol, emulgerende voks, glycerylmonostearat, glyceryldistearat, ethylenglycoldistearat, sorbitantristearat, propylenglycolmonostearat, sorbitanmonooleat, sorbitanmonostearat, diethylenglycolmonolaurat, sorbitanmonopalmitat, saccharosedioleat, saccharosestearat, polyoxyethylenlaurylether, polyoxyethylen (2) stearylether, polyoxyethylen (21) stearylether, polyoxyethylenmonostearat, polyoxyethylensorbitanmonostearat, polyoxyethylensorbitanmonooleat, polyoxyethylensorbitanmonolaurat og natriumoleat, og/eller hvor formuleringen omfatter glycerylmonostearat eller glyceryldistearat, og/eller hvor formuleringen omfatter voks, og/eller hvor formuleringen omfatter alkohol og/eller hvor formuleringen omfatter alkohol og vand.
  21. 21. Farmaceutisk formulering ifølge et hvilket som helst af kravene 13 til 20, hvor formuleringen omfatter ét eller flere elementer udvalgt fra ethanol og propylenglycol.
  22. 22. Farmaceutisk formulering ifølge krav 13, hvilken formulering omfatter: ca. 20 % propylenglycol; ca. 70 % ethanol og ca. 10 % af forbindelsen; eller ca. 70 % ethanol; ca. 20 % poly(vinylmethylether-alt-maleinsyre monobutylester) og ca. 10 % af forbindelsen, eller ca. 56 % ethanol; ca. 14 % vand; ca. 15 % poly(2-hydroxyethylmethacrylat); ca. 5 % dibutylsebacat og ca. 10 % af forbindelsen, eller ca. 55 % ethanol; ca. 15 % ethylacetat; ca. 15 % poly(vinylacetat); ca. 5 % dibutylsebacat og ca. 10 % af forbindelsen.
  23. 23. Farmaceutisk formulering ifølge et hvilket som helst af kravene 13 til 21, hvor forbindelsen er til stede i formuleringen i en koncentration fra ca. 0,5 % til ca. 15 % vægt/volumen, eventuelt, fra ca. 0,1 % til ca. 12,5 % vægt/vo lumen, eventuelt, fra ca. 1 % til ca. 5 % vægt/vo lumen, eventuelt, fra ca. 2 % til ca. 8 % vægt/volumen, og eventuelt, fra ca. 4 % til ca. 9 % vægt/volumen.
  24. 24. Farmaceutisk formulering ifølge et hvilket som helst af kravene 13 til 21, hvor forbindelsen er til stede i en form, der er et element udvalgt fra et hydrat med vand, et solvat med en alkohol, et addukt med en aminoforbindelse og et addukt med en syre.
  25. 25. Farmaceutisk formulering ifølge et hvilket som helst af kravene 13 til 24, hvor den farmaceutiske formulering er beregnet til administration på et sted, der er hud eller negl, eller hår, eller hud, der omgiver neglen, eller hud, der omgiver håret.
  26. 26. Farmaceutisk formulering ifølge et hvilket som helst af kravene 13 til 24, hvor den farmaceutiske formulering administreres til et dyr, der er udvalgt fra gruppen bestående af et menneske, kvæg, ged, gris, får, hest, ko, tyr, hund, marsvin, løbemus, kanin, kat, kylling og kalkun, eventuelt hvor dyret er et menneske.
  27. 27. Farmaceutisk formulering ifølge et hvilket som helst af kravene 13 til 26, hvilken formulering endvidere indbefatter et supplerende farmaceutisk effektivt middel, hvor formuleringen er en topisk farmaceutisk formulering, og hvor formuleringen endvidere indbefatter et anti-inflammatorisk middel udvalgt fra gruppen bestående af: bisabolol, mentholatum, dapson, aloe og hydrocortison.
  28. 28. Forbindelse der er et element udvalgt fra 5-(4-cyanphenoxy)-l,3-dihydro-l-hydroxy-2,1- benzoxaborol, 6-(4-cyanphenoxy)-1,3 -dihydro-1 -hydroxy-2,1 -benzoxaborol, 6-(3- cyanphenoxy)-1,3-dihydro-1 -hydroxy-2,1 -benzoxaborol, 6-(4-chlorphenoxy)-1,3-dihydro-1 - hydroxy-2,1 -benzoxaborol, 5-(4-cyanobenzyloxy)-1,3 -dihydro-1 -hydroxy-2,1 -benzoxaborol, 5- (2- cyanphenoxy)-l ,3-dihydro-l-hydroxy-2,l-benzoxaborol, 5-[4-(N,N- diethylcarbamoyl)phenoxy]-l ,3-dihydro-l -hydroxy-2,1 -benzoxaborol, 1,3-dihydro-l -hydroxy-5-[4-(morpholincarbonyl)phenoxy] -2,1 -benzoxaborol, 5-(3,4-dicyanphenoxy)-1,3 -dihydro-1 - hydroxy-2,1 -benzoxaborol, 6-phenylthio-1,3 -dihydro-1 -hydroxy-2,1 -benzoxaborol, 6-(4- trifluormethoxyphenoxy)-l,3-dihydro-l-hydroxy-2,1-benzoxaborol, 6-(4-methoxyphenoxy)- 1,3 -dihydro-1 -hydroxy-2,1 -benzoxaborol, 6-(4-methoxyphenylthio)-1,3 -dihydro-1 -hydroxy- 2, 1 -benzoxaborol, 5-(3 -cyanphenoxy)-l ,3-dihydro-1 -hydroxy-2,1 -benzoxaborol, 5-(4- carboxyphenoxy)-l -hydroxy-2,1 -benzoxaborol, 1 -hydroxy-5-[4-(tetrazol-1 -yl)phenoxy] -2,1 - benzoxaborol.
  29. 29. Forbindelse ifølge krav 28, der er et element udvalgt fra -(4-cyanphenoxy)-l,3-dihydro-l-hydroxy-2,1 -benzoxaborol, 6-(4-cyanphenoxy)-l,3-dihydro-l -hydroxy-2,1 -benzoxaborol, 6-(3-cyanphenoxy)-l,3-dihydro-l-hydroxy-2,l-benzoxaborol, 5-(2-cyanphenoxy)-l,3-dihydro-l-hydroxy-2,1 -benzoxaborol, 5-(3,4-dicyanphenoxy)-l ,3-dihydro-l -hydroxy-2,1 -benzoxaborol og 5-(3 -cyanphenoxy)-1,3 -dihydro-1 -hydroxy-2,1 -benzoxaborol.
  30. 30. Forbindelse ifølge krav 28, der er 5-(4- cyanphenoxy)-l,3-dihydro-l-hydroxy-2,l- benzoxaborol.
  31. 31. Forbindelse ifølge krav 28, der er 5-(3,4-dicyanphenoxy)-l,3-dihydro-l-hydroxy-2,l- benzoxaborol.
  32. 32. Forbindelse ifølge et hvilket som helst af kravene 28 til 31 i en form, der er et element udvalgt fra et hydrat med vand, et solvat med en alkohol, et addukt med en aminoforbindelse og et addukt med en syre.
  33. 33. Forbindelse som defineret i et hvilket som helst af kravene 28 til 31 i form af et farmaceutisk acceptabelt salt, eventuelt hvor saltet er et baseadditionssalt opnået ved at etablere kontakt mellem den neutrale form af en sådan forbindelse med en tilstrækkelig mængde af den ønskede base i et egnet inert opløsningsmiddel
  34. 34. Topisk gelformulering omfattende: (a) en forbindelse som defineret i et hvilket som helst af kravene 1 til 10 og (b) en gelfasebærer.
  35. 35. Forbindelse som defineret i et hvilket som helst af kravene 1 til 12 eller a farmaceutisk formulering ifølge et hvilket som helst af kravene 13 til 27 til topisk administration.
  36. 36. Forbindelse som defineret i et hvilket som helst af kravene 1 til 12 eller farmaceutisk formulering ifølge et hvilket som helst af kravene 13 til 27 til anvendelse i behandlingen af inflammation.
  37. 37. Anvendelse af 5-(4-cyanphenoxy)-l,3-dihydro-l-hydroxy-2,l-benzoxaborol, eller et farmaceutisk acceptabelt salt deraf, og en farmaceutisk acceptabel excipiens deraf til fremstilling af en farmaceutisk formulering comprising 5-(4-cyanphenoxy)-l,3-dihydro-l-hydroxy-2,l-benzoxaborol, eller et farmaceutisk acceptabelt salt deraf, og den farmaceutisk acceptable excipiens, eventuelt hvor saltet er et baseadditionssalt opnået ved at etablere kontakt mellem den neutrale form af forbindelsen og en tilstrækkelig mængde af den ønskede base i et egnet inert opløsningsmiddel.
  38. 38. Anvendelse af 5-(3,4-dicyanphenoxy)-l,3-dihydro-l-hydroxy-2,l-benzoxaborol, eller et farmaceutisk acceptabelt salt deraf, og en farmaceutisk acceptabel excipiens deraf til fremstilling af en farmaceutisk formulering omfattende 5-(3,4-dicyanphenoxy)-l,3-dihydro-l-hydroxy-2,l-benzoxaborol, eller et farmaceutisk acceptabelt salt deraf, og den farmaceutisk acceptable excipiens, eventuelt hvor saltet er et baseadditionssalt opnået ved at etablere kontakt mellem den neutrale form af forbindelsen og en tilstrækkelig mængde af den ønskede base i et egnet inert opløsningsmiddel.
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