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US 12,281,091 B1Granted
Methods of preparing cannabinoids or derivatives thereof
AssigneeFloraScience Inc.
InventorsRobert Paul Jensen, Vaughn Hartung
Life of this patent
Estimating the term…
Abstract
Provided are methods of preparing cannabinoids and cannabinoid derivatives and compositions containing the cannabinoids and derivatives.
Claims29
A method of preparing a compound of Formula (I):
- or a pharmaceutically acceptable salt thereof, wherein:
- R1 is hydrogen, C1-C10 alkyl, C(═O)—(C1-C10 alkyl), or Si(C1-C10 alkyl)3;
- R2 is hydrogen or C1-C10 alkyl;
- R3 is hydrogen, C1-C6 alkyl, or C1-C6 hydroxyalkyl;
- R4 is hydrogen, C1-C10 alkyl, or C2-C10 alkenyl;
- R5 is hydrogen, C1-C10 alkyl, or C2-C10 alkenyl;
- and
- R6 is hydrogen, C1-C6 alkyl, C(═O)(OH), or C(═O)—(C1-C6 alkyl);
- the method comprising:
- admixing a catalyst, an oxidizing agent, and a compound of Formula (II):
- wherein each is independently a single bond or a double bond, and wherein only one is a double bond, to form a compound of Formula (I), or a pharmaceutically acceptable salt thereof,
- wherein the catalyst is I2, Br2, or Cl2;
- and
- the oxidizing agent comprises one or more of O2, S8, benzoquinone, chloranil, hydrogen peroxide, peracetic acid, diacetyl peroxide, ditertbutyl peroxide, dicumyl peroxide, peroxybenzoic acid, benzoyl peroxide, and dimethyl sulfoxide.
11 more elements
A method of preparing a compound of Formula (I):
- or a pharmaceutically acceptable salt thereof, wherein:
- R1 is hydrogen, C1-C10 alkyl, or C(═O)—(C1-C10 alkyl);
- R2 is hydrogen or C1-C10 alkyl;
- R3 is hydrogen, C1-C6 alkyl, or C1-C6 hydroxyalkyl;
- R4 is hydrogen, C1-C10 alkyl, or C2-C10 alkenyl;
- R5 is hydrogen, C1-C10 alkyl or C2-C10 alkenyl;
- and
- R6 is hydrogen, C1-C6 alkyl, C(═O)(OH), or C(═O)—(C1-C6 alkyl);
- the method comprising:
- admixing a catalyst, an oxidizing agent, and a compound of Formula (III)
- to form the compound of Formula (I), or a pharmaceutically acceptable salt thereof,
- wherein each is independently a single bond or a double bond, and wherein only one is a double bond;
- and
- wherein the catalyst is I2, Br2, or Cl2;
- and
- the oxidizing agent comprises one or more of O2, S8, benzoquinone, chloranil, hydrogen peroxide, peracetic acid, diacetyl peroxide, ditertbutyl peroxide, dicumyl peroxide, peroxybenzoic acid, benzoyl peroxide, and dimethyl sulfoxide.
13 more elements
Dependencies are inferred from the claim text.