Resveratrol-piperazine co-crystals
The present document is directed to co-crystals of resveratrol and/or curcumin with piperazine and their use in medicine and/or as food and feed supplements.
1. A method for producing a resveratrol-piperazine co-crystal, Form 1, characterized by having an XRPD pattern comprising peaks at 4.48, 13.32, 16.96, 18.88, 19.16, and 22.84 °28±0.2 °28, or Form 2, characterized by having an XRPD pattern comprising peaks at 5.87, 12.74, 17.43, 17.70, 20.55, and 21.32 °28±0.2 °28, said method comprising the steps of:
a) grinding a mixture comprising resveratrol, piperazine and a solvent selected from ethanol or tetrahydrofuran;
b) allowing the mixture of step a) to dry thereby providing a further mixture comprising Form 1 when the solvent is ethanol in step a) or Form 2 when the solvent is tetrahydrofuran in step a); and
c) optionally subjecting the further mixture to further grinding.
2. The method according to claim 1 , wherein said method consists of steps a), b) and optionally step c).
3. The method according to claim 1 , wherein said grinding of the mixture takes place in a ball mill.
4. The method according to claim 1 , wherein the solvent is ethanol and the grinding of the mixture takes place in a mixer mill steel container equipped with stainless steel knives in cross position.
5. The method according to claim 2 wherein said grinding of the mixture takes place in a ball mill.
6. The method according to claim 2 , wherein the solvent is ethanol and the grinding takes place in a mixer mill steel container equipped with stainless steel knives in cross position.
7. A resveratrol-piperazine co-crystal, Form 2, obtained by the method of claim 1 , wherein said resveratrol-piperazine co-crystal Form 2 has a fusion temperature Tfus of 199° C.±5° C.
8. The method according to claim 1 , wherein the method produces Form 1.
9. The method according to claim 1 , wherein the method produces Form 2.
10. The method according to claim 1 , wherein the method comprises grinding the further mixture.
11. The method according to claim 8 , wherein the method comprises grinding the further mixture comprising Form 1.
12. The method according to claim 9 , wherein the method comprises grinding the further mixture comprising Form 2.
13. The method according to claim 1 , wherein the solvent is tetrahydrofuran and the grinding of the mixture takes place in a mixer mill steel container equipped with stainless steel knives in cross position.
14. The method according to claim 2 , wherein the solvent is tetrahydrofuran and the grinding of the mixture takes place in a mixer mill steel container equipped with stainless steel knives in cross position.