Method for obtaining pure tetrahydrocannabinol
The invention relates to a method for obtaining pure tetrahydrocannabinol from reaction mixtures containing tetrahydrocannabinol compounds or from raw products containing tetrahydrocannabinol compounds. According to said method, the tetrahydrocannabinol compounds in the reaction mixture or in the raw product are converted into crystallisable derivatives, preferably using a suitable solvent, said derivatives are then crystallised and isolated, and the pure tetrahydrocannabinol compounds are then obtained from the crystallised derivatives. The invention also related to the use of compounds produced in this way for the production of a medicament for human therapy, and to the medicaments thus produced.
1. Process for obtaining pure tetrahydrocannabinol from reaction mixtures containing tetrahydrocannabinol compounds or from crude product containing tetrahydrocannabinol compounds, characterized in that the tetrahydrocannabinol compound in the reaction mixture or in the crude product is converted to a crystallizable derivative of formulae (III) and (IIIA):
in which
R 1 is hydrogen, chlorine or (C 1-10 )-alkyl;
X is —O— (oxygen) or —NH—; and
R 2 is an optionally substituted aliphatic or aromatic radical which optionally carries a substituent capable of salt formation; or a heterocyclic radical which optionally is itself capable of salt formation and/or optionally carries a substituent capable of salt formation; or a radical of an aliphatic or aromatic polybasic acid; whereby said derivative is crystallized out and isolated and the pure tetrahydrocannabinol compound is then obtained from the crystallized derivative.
2. Process according to claim 1 , characterized in that pure Δ 8 -THC or Δ 9 -THC are obtained from a reaction mixture or crude product containing Δ 8 -THC and/or Δ 9 -THC.
3. Process according to claim 1 , characterized in that compounds of formulae (I) and (IA) are prepared:
in which R 1 is hydrogen, chlorine or (C 1-10 )-alkyl.
4. Process according to claim 3 , characterized in that compounds of formulae (I′) and (I′A) are prepared:
in which R 1 is hydrogen, chlorine or (C 1-10 )-alkyl.
5. Process according to claim 1 , characterized in that R 1 is n-C 5 H 11 .
6. The pure crystallizable and the crystallized tetrahydrocannabinol compounds prepared according to claim 1 .
7. The compounds of claim 1 for the preparation of a drug for human therapy.
8. The drugs prepared according to claim 7 .
9. Process according to claim 1 , characterized in that X is —O—(oxygen).
10. Process according to claim 1 , characterized in that R 1 is n-C 5 H 11 , and R 2 is phenyl optionally substituted by nitro, halogen, methyl or sulfonyl, or naphthyl, optionally substituted by nitro, halogen, methyl or sulfonyl.
11. Process according to claim 1 , characterized in that R 1 is n-C 5 H 11 , and R 2 is unsubstituted naphthyl.
12. Process according to claim 1 , characterized in that R 2 is a heterocyclic radical that is itself capable of salt formation or optionally carries a substituent capable of salt formation and is a 2-pyridyl, 3-pyridyl or 4-pyridyl derivative or a corresponding picoline, pyrazine, pyrazole, pyrrole or indole derivative.
13. Process according to claim 1 , characterized in that R 2 is a substituent derived from pyridinecarboxylic acid or pyridine.
14. Process according to claim 1 characterized in that R 2 is a residue of phthalic acid or terephthalic acid, wherein the acid group not bonded to the THC derivative is optionally bonded to a radical capable of salt formation.
15. Process according to claim 1 characterized in that R 2 is a residue of 1-naphthoic acid, 2-naphthoic acid, 1-naphthylacetic acid or 2-naphthylacetic acid.
16. Process accordin. to claim 1 characterized in that R 2 is a residue of 9-anthracenecarboxylic acid or 9-phenanthrenecarboxylic acid.
17. Process according to claim 1 , characterized in that stereospecifically (enantiomerically) pure Δ 8 -THC and stereospecifically (enantiomerically) pure Δ 9 -THC, are obtained from a reaction mixture or crude product containing Δ 8 -THC and/or Δ 9 -THC.