Mixtures of cannabinoid compounds, and production and use thereof

Patent metadata

Field	Value
Publication number	US-2021107885-A1
Application number	US-202017113248-A
Country	US
Kind code	A1
Filing date	Dec 7, 2020
Priority date	Feb 26, 2015
Publication date	Apr 15, 2021
Grant date	—

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

1 - 18 . (canceled)

19 . A method for producing 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;
the method comprising:
transesterification of a divarin acid ester, and
reacting the divarinacid ester with menthadienol to produce a compound of formula (A).

20 . The method of claim 19 , wherein the transesterification is carried out by reacting the divarin acid ester with an alcohol of formula HO-X, wherein X is an aliphatic substituent optionally substituted one or more hydroxyl groups.

21 . The method of claim 19 , wherein the divarin acid ester is a divarinacidmethyl ester.

22 . The method of claim 19 , wherein the compound of formula (A) is cyclohexylcannabidivarinolat, hexylcannabidivarinolat, or 2-hydroxyethylcannabidivarinolat.

23 . A method for producing 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 le 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;
the method comprising:
reacting an ester of the formula (IX)

wherein Y is an alkylgroup, 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.

24 . The method of claim 23 , wherein Y is an alkylgroup selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-buty, tert-butyl.

25 . The method of claim 23 , wherein the ester of formula (IX) is an ester of formula (III)

26 . The method of claim 25 , wherein the ester of formula (III) is obtained by reacting menthadienol of formula (I) with a divarin acid ester of formula (II)

27 . The method of claim 23 , wherein the aliphatic substituent of R 1 is saturated and/or linear.

28 . The method of claim 23 , wherein the compound of formula (A) is 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.

29 . The method of claim 23 , wherein the compound of formula (A) is 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.

30 . A method of claim 23 , wherein the compound of formula (A) is 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.

31 . The mixture according to claim 23 wherein the compound of formula (A) is 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.

32 . The method of claim 28 , wherein each R 1 of the compound of formula (A-I) is independently H or OH.

33 . The method of claim 29 , wherein each R 1 of the compound of formula (A-II) is independently H or OH.

34 . The method of claim 30 , wherein each R 1 of the compound of formula (A-III) is independently H or OH.

35 . The method of claim 31 , wherein each R 1 of the compound of formula (A-IV) is independently H or OH.

36 . The method of claim 23 , wherein the compound of the formula (A) is a compound of formula (IV):

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

• C07C37/50

  by reactions decreasing the number of carbon atoms (C07C37/04, C07C37/045, C07C37/055, C07C37/08 take precedence) · CPC title

• C07C2601/16

  the ring being unsaturated · CPC title

• C07C67/03

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

• A61P9/12

  Antihypertensives · CPC title