Solid forms of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide
Solid forms of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide are described herein, including crystalline forms thereof.
1. A method of making crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide·XX, the method comprising:
dissolving N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide in XX and then cooling the solution of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide and XX to provide crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide·XX, wherein XX is selected from 2-methylbutyric acid, propylene glycol, isobutyric acid, propionic acid, and 2-propanol.
2. A method of making crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide.PEG 400.KOAc, the method comprising
dissolving N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide in a mixture of PEG and KOAc, and then cooling the resulting mixture to provide crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide.PEG 400.KOAc.
3. A method of making crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide.lactic acid, the method comprising dissolving N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide and lactic acid in acetonitrile, and evaporating at least a portion of the acetonitrile to provide crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide.lactic acid.
4. A method of making crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide.H 2 O, the method comprising suspending N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide in H 2 O, and stirring the suspension of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide and H 2 O to provide crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide.H 2 O.
5. A method of making crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide.besylate, the method comprising:
mixing N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide, benzenesulfonic acid and an aprotic solvent; and
heating the mixture.
6. The method of claim 5 further comprising cooling the heated mixture and filtering the cooled mixture to provide crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide.besylate.
7. The method of claim 5 , wherein the aprotic solvent comprises a solvent selected from an aprotic ether, an aprotic ester or a nitrile.
8. The method of claim 5 , wherein the aprotic solvent comprises a solvent selected from dimethoxy methane, t-butyl methyl ether, anisole, tetrahydrofuran, 2-methyltetrahydrofican, ethyl acetate, isopropyl acetate, n-butyl acetate, n-propyl acetate, t-butyl acetate, acetonitrile or mixtures thereof.
9. The method of claim 5 , wherein the aprotic solvent comprises a mixture of aprotic ether and aprotic ester solvents.
10. A method of making crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide.besylate.H 2 O, the method comprising:
mixing N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide.besylate, benzenesulfonic acid hydrate and an aprotic acetate solvent.
11. The method of claim 10 , wherein the aprotic acetate solvent comprises a mixture of ethyl acetate and isopropyl acetate.