Mixtures of cannabinoid compounds, and production and use thereof

Patent metadata

Field	Value
Publication number	US-10913729-B2
Application number	US-201816181503-A
Country	US
Kind code	B2
Filing date	Nov 6, 2018
Priority date	Feb 26, 2015
Publication date	Feb 9, 2021
Grant date	Feb 9, 2021

Abstract

Described are also corresponding pharmaceutical formulations, cosmetic preparations and preparations for pleasure and/or nutrition, suitable for consumption, as well as methods for producing CBDV and THCV.

First claim

The invention claimed is:

1. A mixture comprising one or more compounds of formula (A) and/or salts thereof

wherein R 1 is a C 1 -C 15 aliphatic substituent optionally substituted with one or more hydroxyl groups, wherein the aliphatic substituent is
saturated or unsaturated,
branched or linear, and
acyclic or cyclic,
provided that if R 1 is an aliphatic substituent with no hydroxyl groups, the one or more compounds of formula (A) is/are selected from cyclohexylcannabidivarinolat, hexylcannabidivarinolat, salts thereof, and a mixture thereof.

2. The mixture according to claim 1 , wherein the aliphatic substituent is saturated and/or linear.

3. The mixture according to claim 1 comprising a compound of formula (A-I)

wherein,
each R 1 is independently H, a C 1 -C 2 alkyl, or OH,
R 2 is H or OH,
n is an integer from 2 to 10,
provided that at least one of R 1 or R 2 is OH.

4. The mixture according to claim 1 comprising a compound of formula (A-II)

wherein,
each R 1 is independently H, a C 1 -C 2 alkyl, or OH,
R 2 is H or OH,
n is an integer from 2 to 10,
provided that at least one of R 1 or R 2 is OH.

5. A mixture according to claim 1 comprising a compound of formula (A-III)

wherein,
each R 1 is independently H, a C 1 -C 2 alkyl, or OH,
R 2 is H or OH,
n is an integer from 2 to 10,
provided that least one of R 1 or R 2 is OH.

6. The mixture according to claim 1 comprising a compound of formula (A-IV)

wherein
each R 1 is independently H, a C 1 -C 2 alkyl, or OH, and
n is an integer from 2 to 10.

7. A mixture according to claim 3 , wherein each R 1 of the compound of formula (A-I) is independently H or OH.

8. A mixture according to claim 4 , wherein each R 1 of the compound of formula (A-II) is independently H or OH.

9. A mixture according to claim 5 , wherein each R 1 of the compound of formula (A-III) is independently H or OH.

10. A mixture according to claim 6 , wherein each R 1 of the compound of formula (A-IV) is independently H or OH.

11. A mixture according to claim 1 , wherein the compound of the formula (A) is a compound of formula (IV):

12. A method for producing a mixture according to claim 1 comprising:
reacting an ester of the formula (IX)

wherein Y is an organic substituent, with an alcohol of the formula HO—X,
wherein X is a C 1 -C 15 aliphatic substituent optionally substituted with one or more hydroxyl groups, wherein the aliphatic substituent is
saturated or unsaturated,
branched or linear, and
acyclic or cyclic,
provided that if X is an aliphatic substituent with no hydroxyl groups, the alcohol of formula HO-X is selected from cyclohexanol and hexanol;

wherein Y is different from X and selected such that the alcohol of formula HO—Y formed during the reaction boils at 1013 hPa at a lower temperature than the alcohol of formula HO—X.

13. A pharmaceutical or cosmetic formulation comprising a mixture according to claim 1 .

14. A formulation suitable for consumption comprising a mixture according to claim 1 .

15. The mixture according to claim 1 comprising a compound of formula (V) (cannabidivarin, CBDV):

and/or a compound of formula (III) ((−)-trans-methylcannabidivarinolat):

wherein if the mixture comprises a compound of formula (V), a molar ratio of a total amount of the one or more compounds of formula (A) and/or salts thereof to a total amount of the compound of formula (V) is greater than 1:1, and if the mixture comprises a compound of formula (III), a molar ratio of a total amount of the one or more compounds of formula (A) and/or salts thereof to a total amount of the compound of formula (III) is greater than 1:1.

Assignees

• Symrise Ag

Inventors

• Koch Oskar
• Götz Marcus Rudolf

Classifications

• A61K31/658

  o-phenolic cannabinoids, e.g. cannabidiol, cannabigerolic acid, cannabichromene or tetrahydrocannabinol · CPC title

• C07C69/94

  of polycyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of six-membered aromatic rings · CPC title

• A61K31/235 Primary

  having an aromatic ring attached to a carboxyl group · CPC title

• C07C67/03

  by reacting an ester group with a hydroxy group · CPC title

• A61P9/12

  Antihypertensives · CPC title