Polycannabinoids, compounds, compositions and methods of use

Patent metadata

Field	Value
Publication number	US-12491199-B2
Application number	US-202117232432-A
Country	US
Kind code	B2
Filing date	Apr 16, 2021
Priority date	Apr 17, 2020
Publication date	Dec 9, 2025
Grant date	Dec 9, 2025

Abstract

Polymers comprising a plurality of cannabinoids, methods of preparation thereof, and methods of use to treat a number of disease conditions are reported. Also provided are polymer coatings, films, fibers, and non-woven fabrics for a variety of topical applications including stents, bandages, sutures, and transdermal patches.

First claim

The invention claimed is:

1 . A polymer having the formula:

wherein:
CNB is a CNB cannabinoid unit;
L is an adipic acid linker; and
n represents the number of repeat units, wherein n is at least 2, and

wherein the polymer further comprises one or more endcapping groups,
wherein the one or more endcapping groups are selected from a cannabinoid unit having one hydroxyl group, an acid group, or an ester group before reaction with the polymer.

2 . The polymer according to claim 1 , wherein each CNB cannabinoid unit is independently derived from: CBG, CBD, CBND, dihydro-DHCBD, CBG-V, CBD-V, CBND-V, or dihydro-DHCBD-V, and
wherein each CNB cannabinoid unit is bound to the adipic acid linker via hydroxyl groups, acid groups, or ester groups on the CNB cannabinoid unit before polymerization.

3 . The polymer according to claim 2 , wherein each CNB cannabinoid unit has one of the following structures before polymerization:

and
wherein the R group is: C 1 -C 10 alkyl optionally substituted with one or more heteroatoms, a heterocycloalkyl group, or a heteroaryl group; specifically methyl, ethyl, propyl, butyl, pentyl, hexyl, 4′-(3-carboxypropyl)-, 4′-(4-hydroxybutyl), 1,1-dimethylheptyl, 4′-[2-(1H-1,2,3-triazol-yl)ethyl]-, 4′-(2-morpholinoethyl)-, or 4′-(2-ethoxyethyl)-.

4 . The polymer according to claim 1 , wherein the one or more endcapping groups have the following structure before reaction with the polymer:

5 . The polymer according to claim 1 , wherein the average molecular weight is about 1,000 daltons to about 60,000 daltons.

6 . The polymer according to claim 1 , wherein the average molecular weight is about 15,000 daltons to about 50,000 daltons.

7 . A pharmaceutical composition comprising a polymer as described in claim 1 and a pharmaceutically acceptable carrier.

8 . The polymer according to claim 1 , wherein the polymer comprises a temperature for onset of thermal degradation of greater than 300 degrees Celsius when measured by non-isothermal TGA.

9 . The polymer of claim 1 , wherein the polymer is a linear polymer.

10 . The polymer of claim 1 , wherein the polymer is a branched polymer.

11 . The polymer of claim 1 , wherein polymer comprises poly(CBD-adipate).

12 . The polymer of claim 1 , wherein polymer comprises poly(CBG-adipate).

13 . The polymer of claim 1 , wherein the plurality of CNB cannabinoid unit comprises structurally identical cannabinoid units.

14 . The polymer of claim 1 , wherein the plurality of CNB cannabinoid unit comprises structurally different cannabinoid units.

15 . A polymer that comprises a plurality of cannabinoid units wherein the polymer has the formula:

wherein:
CNB is a CNB cannabinoid unit,
L is a linking group; and
n represents the number of repeat units wherein n is at least 2;

wherein the linking group comprises a di- or tri-carboxylic acid linking group comprising citric acid, fumaric acid, glutamic acid, maleic acid, malic acid, malonic acid, oxalic acid, succinic acid, glutaric acid, terephthalic acid, isophthalic acid, oxaloacetic acid, phthalic acid, adipic acid, or butanedioic acid, and wherein the polymer further comprises one or more endcapping groups, wherein the one or more endcapping groups are selected from a cannabinoid unit having one hydroxyl group, an acid group, or an ester group before reaction with the polymer.

16 . The polymer according to claim 15 , wherein each CNB cannabinoid unit is independently derived from: CBG, CBD, CBC, CBND, dihydro-DHCBD, CBG-V, CBD-V, CBC-V, CBND-V, or dihydro-DHCBD-V, and
wherein each CNB cannabinoid unit is bound to the linking group via hydroxyl groups, acid groups, or ester groups on the CNB cannabinoid unit before polymerization.

17 . The polymer according to claim 15 , wherein each CNB cannabinoid unit has one of the following structures before polymerization:

and
wherein the R group is: C 1 -C 10 alkyl optionally substituted with one or more heteroatoms, a heterocycloalkyl group, or a heteroaryl group; specifically methyl, ethyl, propyl, butyl, pentyl, hexyl, 4′-(3-carboxypropyl)-, 4′-(4-hydroxybutyl), 1,1-dimethylheptyl, 4′-[2-(1H-1,2,3-triazol-yl)ethyl]-, 4′-(2-morpholinoethyl)-, or 4′-(2-ethoxyethyl)-.

18 . The polymer according to claim 15 , wherein the one or more endcapping groups have the following structure before reaction with the polymer:

19 . The polymer according to claim 15 , wherein the number average molecular weight is about 1,000 daltons to about 60,000 daltons.

20 . The polymer of claim 15 , wherein the CNB cannabinoid units comprises structurally identical cannabinoid units.

21 . The polymer of claim 15 , wherein the CNB cannabinoid units comprises structurally different cannabinoid units.

22 . A pharmaceutical composition comprising the polymer according to claim 15 and a pharmaceutically acceptable carrier.

23 . A cosmetic composition comprising the polymer according to claim 15 and a cosmetically acceptable carrier.

24 . An article comprising the polymer according to claim 15 , wherein the article is a microsphere, a film, a fiber, a fiber matrix, a nonwoven fabric, a woven fabric, a wound dressing, a medical device, a stent, a catheter, a catheter coating, or a transdermal patch.

25 . A cosmetic composition comprising the polymer according to claim 1 and a cosmetically acceptable carrier.

26 . An article comprising the polymer according to claim 1 , wherein the article is a microsphere, a film, a fiber, a fiber matrix, a nonwoven fabric, a woven fabric, a wound dressing, a medical device, a stent, a catheter, a catheter coating, or a transdermal patch.

Assignees

• Univ Connecticut

Inventors

• Sotzing Gregory Allen

Classifications

• A61K9/7007

  Drug-containing films, membranes or sheets (A61K9/0041, A61K9/0043, A61K9/006, A61K9/0063 take precedence) · CPC title

• A61L31/16

  Biologically active materials, e.g. therapeutic substances {(A61L31/047 takes precedence)} · CPC title

• A61L29/16

  Biologically active materials, e.g. therapeutic substances {(A61L29/048 takes precedence)} · CPC title

• A61L29/06

  obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds · CPC title

• A61L29/085

  Macromolecular materials · CPC title