Solid forms of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide
The present invention relates to solid state forms of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide (Compound 1), pharmaceutical compositions thereof and methods therewith.
1. A solid dispersion comprising amorphous N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide and a polymer, wherein the polymer is polyvinylpyrrolidones (PVP), polyvinyl alcohols (PVA), polymethacrylate, β-cyclodextin, or vinylpyrrolidone/vinyl acetate copolymer (PVP/VA).
2. The solid dispersion of claim 1 , wherein the polymer is polyvinylpyrrolidones (PVP).
3. The solid dispersion of claim 2 , wherein the polymer is present in an amount of from about 10% by weight to about 80% by weight.
4. The solid dispersion of claim 3 , wherein the polymer is present in an amount of less than about 70% by weight.
5. The solid dispersion of claim 1 , wherein the N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide is present in an amount of from about 10% by weight to about 80% by weight.
6. The solid dispersion of claim 1 , further comprising a surfactant.
7. The solid dispersion of claim 6 , wherein the surfactant is sodium lauryl sulfate.
8. The solid dispersion of claim 7 , wherein the surfactant is present in an amount from about 0.1 to about 5%.
9. The solid dispersion of claim 8 , wherein the surfactant is present in 0.5%.
10. The solid dispersion according to claim 1 , wherein the solid dispersion is obtained by spray drying.
11. A pharmaceutical composition comprising amorphous N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide and a polymer as a solid dispersion, wherein the polymer is polyvinylpyrrolidones (PVP), polyvinyl alcohols (PVA), polymethacrylate, β-cyclodextin, or vinylpyrrolidone/vinyl acetate copolymer (PVP/VA).
12. The pharmaceutical composition of claim 11 , wherein the polymer is polyvinylpyrrolidones (PVP).
13. A solid dispersion comprising N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide, a polymer and sodium lauryl sulfate, wherein the polymer is polyvinylpyrrolidones (PVP), polyvinyl alcohols (PVA), polymethacrylate, β-cyclodextin, or vinylpyrrolidone/vinyl acetate copolymer (PVP/VA).
14. The solid dispersion of claim 13 , wherein the polymer is polyvinylpyrrolidones (PVP).
15. A pharmaceutical composition comprising the solid dispersion of claim 13 .
16. Solid amorphous N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide.
17. Solid amorphous N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide comprising less than about 15% crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide.
18. A pharmaceutical composition comprising solid amorphous N -[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide.