Cannabigerol quinone acid and salts thereof

A process to obtain a compound of formula I:

• wherein said process comprises the steps of:
• a. oxidizing cannabigerolic acid (CBGA) with an oxidizing agent in an aprotic solvent, in the presence of a base having a pKa of at least 11.5, wherein said pKa is measured in water at 25° C., to obtain a compound of formula I:
• and
• b. isolating the compound of formula I.

A process to obtain a pharmaceutical salt of formula II:

• wherein R1n+ is:
• a metal cation;
• an amino acid cation;
• an ammonium cation of formula III:
• wherein R2, R3, R4 and R5 are each independently selected from the group consisting of:
• H, alkyl, alkenyl, alkynyl, hydroxyalkyl, poly(hydroxy)alkyl, cycloalkyl, alkylaryl, arylalkyl, aminoaryl, aminoalkyl, aminoalkenyl, aminoalkynyl, arylalkylaminoalkyl and alkylaminoaryl;
• or two of R2, R3, R4 and R5 are linked to form a heterocyclic group;
• and
• a guanidinium cation of formula (IV):
• wherein R′2, R′3, R′4, R′5 and R′6 are each independently selected from the group consisting of:
• H, alkyl, alkenyl, alkynyl, hydroxyalkyl, poly(hydroxy)alkyl, cycloalkyl, alkylaryl, arylalkyl, aminoaryl, aminoalkyl, aminoalkenyl, aminoalkynyl, arylalkylaminoalkyl and alkylaminoaryl;
• or wherein two of R′2, R′3, R′4, R′5 and R′6 are linked to form a heterocyclic group;
• and wherein said process comprises:
• i. when R1n+ is a metal cation:
• i.a. contacting a solution of the compound of formula I with said metal cation;
• i.b. contacting a solution of the compound of formula I with a first cation to form a salt of the compound of formula I and said first cation;
• and contacting said salt of the compound of formula I and said first cation with said metal cation;
• or
• i.c. contacting a solution of the compound of formula I with the metal from which said metal cation is derived or an inorganic compound of said metal;
• ii. when R1n+ is an amino acid cation:
• ii.a contacting a solution of the compound of formula I with said amino acid cation;
• ii.b. contacting a solution of the compound of formula I with a first cation to form a salt of the compound of formula I and said first cation;
• and contacting said salt of the compound of formula I and said first cation with said amino acid cation;
• or
• ii.c contacting a solution of the compound of formula I with the amino acid from which said amino acid cation is derived by protonation;
• iii. when R1n+ is an ammonium cation of formula III:
• iii.a. contacting a solution of the compound of formula I with said ammonium cation of formula III;
• iii.b contacting as solution of the compound of formula I with a first cation to form a salt of the compound of formula I and said first cation;
• and contacting said salt of the compound of formula I and said first cation with said ammonium cation of formula III;
• or
• iii.c. and when R5 is H, contacting a solution of the compound of formula I with the amine of formula V from which said ammonium cation of formula III is derived by protonation:
• iv. when R1n+ is a guanidinium cation of a guanidine derivative of formula IV:
• iv.a. contacting the compound of formula I with said guanidinium cation of formula IV;
• iv.b. contacting as solution of the compound of formula I with a first cation to form a salt of the compound of formula I and said first cation;
• and contacting said salt of the compound of formula I and said first cation with said guanidinium cation of formula IV;
• or
• iv.c. contacting a solution of the compound of formula I with said guanidine derivative of formula IVb from which said guanidium cation of formula IV is derived by protonation:
• wherein n is a number selected from the group consisting of:
• 1, 2, 3 and 4.